WO2006098120A1 - Organic electroluminescent device material and organic electroluminescent device - Google Patents

Organic electroluminescent device material and organic electroluminescent device Download PDF

Info

Publication number
WO2006098120A1
WO2006098120A1 PCT/JP2006/303110 JP2006303110W WO2006098120A1 WO 2006098120 A1 WO2006098120 A1 WO 2006098120A1 JP 2006303110 W JP2006303110 W JP 2006303110W WO 2006098120 A1 WO2006098120 A1 WO 2006098120A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
ring
organic
general formula
represented
Prior art date
Application number
PCT/JP2006/303110
Other languages
French (fr)
Japanese (ja)
Inventor
Masato Nishizeki
Tomohiro Oshiyama
Original Assignee
Konica Minolta Holdings, Inc.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Konica Minolta Holdings, Inc. filed Critical Konica Minolta Holdings, Inc.
Priority to JP2007508045A priority Critical patent/JP5125502B2/en
Publication of WO2006098120A1 publication Critical patent/WO2006098120A1/en

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
    • C07F15/0006Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
    • C07F15/002Osmium compounds
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
    • C07F15/0006Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
    • C07F15/0033Iridium compounds
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
    • C07F15/0006Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
    • C07F15/006Palladium compounds
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
    • C07F15/0006Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
    • C07F15/0073Rhodium compounds
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
    • C07F15/0006Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
    • C07F15/0086Platinum compounds
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • HELECTRICITY
    • H05ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05BELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00Electroluminescent light sources
    • H05B33/12Light sources with substantially two-dimensional radiating surfaces
    • H05B33/14Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30Coordination compounds
    • H10K85/341Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30Coordination compounds
    • H10K85/341Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/346Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising platinum
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60Organic compounds having low molecular weight
    • H10K85/649Aromatic compounds comprising a hetero atom
    • H10K85/657Polycyclic condensed heteroaromatic hydrocarbons
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10Non-macromolecular compounds
    • C09K2211/1003Carbocyclic compounds
    • C09K2211/1007Non-condensed systems
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10Non-macromolecular compounds
    • C09K2211/1018Heterocyclic compounds
    • C09K2211/1022Heterocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10Non-macromolecular compounds
    • C09K2211/1018Heterocyclic compounds
    • C09K2211/1025Heterocyclic compounds characterised by ligands
    • C09K2211/1029Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10Non-macromolecular compounds
    • C09K2211/1018Heterocyclic compounds
    • C09K2211/1025Heterocyclic compounds characterised by ligands
    • C09K2211/1029Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/1033Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10Non-macromolecular compounds
    • C09K2211/1018Heterocyclic compounds
    • C09K2211/1025Heterocyclic compounds characterised by ligands
    • C09K2211/1029Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/1037Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10Non-macromolecular compounds
    • C09K2211/1018Heterocyclic compounds
    • C09K2211/1025Heterocyclic compounds characterised by ligands
    • C09K2211/1044Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10Non-macromolecular compounds
    • C09K2211/1018Heterocyclic compounds
    • C09K2211/1025Heterocyclic compounds characterised by ligands
    • C09K2211/1059Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10Non-macromolecular compounds
    • C09K2211/1018Heterocyclic compounds
    • C09K2211/1025Heterocyclic compounds characterised by ligands
    • C09K2211/1074Heterocyclic compounds characterised by ligands containing more than three nitrogen atoms as heteroatoms
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10Non-macromolecular compounds
    • C09K2211/1018Heterocyclic compounds
    • C09K2211/1025Heterocyclic compounds characterised by ligands
    • C09K2211/1088Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10Non-macromolecular compounds
    • C09K2211/1018Heterocyclic compounds
    • C09K2211/1025Heterocyclic compounds characterised by ligands
    • C09K2211/1092Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10Non-macromolecular compounds
    • C09K2211/1018Heterocyclic compounds
    • C09K2211/1025Heterocyclic compounds characterised by ligands
    • C09K2211/1096Heterocyclic compounds characterised by ligands containing other heteroatoms
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/18Metal complexes
    • C09K2211/185Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/18Metal complexes
    • C09K2211/186Metal complexes of the light metals other than alkali metals and alkaline earth metals, i.e. Be, Al or Mg
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00Properties of the organic materials covered by group H10K85/00
    • H10K2101/10Triplet emission
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00Organic light-emitting devices
    • H10K50/10OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K59/00Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
    • H10K59/10OLED displays
    • H10K59/12Active-matrix OLED [AMOLED] displays
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K59/00Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
    • H10K59/80Constructional details
    • H10K59/87Passivation; Containers; Encapsulations
    • H10K59/871Self-supporting sealing arrangements
    • H10K59/872Containers
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/10Organic polymers or oligomers
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/10Organic polymers or oligomers
    • H10K85/111Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/10Organic polymers or oligomers
    • H10K85/141Organic polymers or oligomers comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/10Organic polymers or oligomers
    • H10K85/141Organic polymers or oligomers comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE
    • H10K85/146Organic polymers or oligomers comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE poly N-vinylcarbazol; Derivatives thereof
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/10Organic polymers or oligomers
    • H10K85/151Copolymers
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60Organic compounds having low molecular weight
    • H10K85/649Aromatic compounds comprising a hetero atom

Definitions

  • the present invention relates to an organic electoluminescence device material, an organic electroluminescence device, a display device, and a lighting device.
  • ELD electoric luminescence display
  • examples of ELD constituent elements include inorganic electoluminescence elements and organic electroluminescence elements (hereinafter referred to as organic EL elements).
  • Inorganic electoric luminescence elements have been used as planar light sources, but in order to drive the light emitting elements, an alternating high voltage is required.
  • An organic EL device has a structure in which a light-emitting layer containing a compound that emits light is sandwiched between a cathode and an anode, and excitons (excitons) are generated by injecting electrons and holes into the light-emitting layer and recombining them.
  • the device emits light using the emission of light (fluorescence 'phosphorescence) when this exciton is deactivated, and can emit light at a voltage of several V to several tens of V. For this reason, it is a thin-film, completely solid element that has a wide viewing angle and high visibility, and is attracting attention from the viewpoints of space saving and portability.
  • organic EL elements for practical use in the future, it is desired to develop organic EL elements that emit light efficiently and with high luminance with lower power consumption.
  • an organic EL device material As an organic electoluminescence device material (hereinafter referred to as an organic EL device material). Doping improves the emission brightness and extends the lifetime of organic EL devices.
  • an organic EL device having an organic light emitting layer in which an 8-hydroxyquinoline aluminum complex is used as a host compound and a small amount of a phosphor is doped therein for example, Japanese Patent Laid-Open No. 63-264692
  • 8 —An organic EL device having an organic light-emitting layer in which a hydroxyquinoline aluminum complex is used as a host compound and doped with a quinatalidone dye see, for example, JP-A-3-255. No. 190 is known.
  • the upper limit of the internal quantum efficiency is 100%. Therefore, in principle, the luminous efficiency is doubled compared to the case of the excited singlet, and almost the same performance as a cold cathode tube is obtained. It is also attracting attention as a lighting application.
  • the light emission brightness and the light emission efficiency in the case of a light emitting element are greatly improved compared to conventional organic EL elements because the emitted light is derived from phosphorescence.
  • the light emission life of the organic EL device was lower than that of the conventional organic EL device.
  • phosphorescent high-efficiency light-emitting materials are currently unable to achieve sufficient performance for practical use because it is difficult to shorten the emission wavelength and improve the light-emitting lifetime of organic EL elements. .
  • Patent Document 1 Japanese Patent Laid-Open No. 2002-332291
  • Patent Document 2 Japanese Patent Laid-Open No. 2002-332292
  • Patent Document 3 Japanese Patent Laid-Open No. 2002-338588
  • Patent Document 4 Japanese Patent Laid-Open No. 2002-226495
  • Patent Document 5 Japanese Patent Laid-Open No. 2002-234894
  • Patent Document 6 WO02Zl5645 specification
  • Patent Document 7 Japanese Unexamined Patent Publication No. 2003-123982
  • Patent Document 8 Japanese Patent Application Laid-Open No. 2002-117978
  • Patent Document 9 Japanese Patent Laid-Open No. 2003-146996
  • Patent Document 10 WO04Z016711 Specification
  • Non-Patent Document 1 Inorganic Chemistry, No. 41, No. 12, pp. 3055-3066 (2002)
  • Non-Patent Document 2 Aplied Physics Letters, 79, 2082 (2001)
  • Non-patent Document 3 Aplied Physics Letters, 83, 3818 (2003)
  • Non-Patent Document 4 New Journal of Chemistry, 26 ⁇ , page 1171 (2002) Disclosure of invention
  • the present invention has been made in view of the related problems, and an object of the present invention is to provide an organic EL element material, an organic EL element, an illumination device, and a display device that exhibit high light emission efficiency and have a long light emission lifetime. Is to provide.
  • represents a metal element belonging to Groups 8 to 10 in the periodic table.
  • L and L ′ represent different bidentate ligands, m is 1 or 2, and n is 1 Or 2. However, m + n is 2 or 3, which matches the charge of M.
  • Partial structure ML in which bidentate ligands L and L 'are coordinated to metal M is represented by the following general formula (2), and partial structure ML' is represented by the following general formula (3) or (4) Is done. [0024] [Chemical 2]
  • X represents a carbon atom or a nitrogen atom
  • Q represents a 6-membered aromatic together with the carbon atom and X.
  • X is 0, S, CH, CHR, CR, NR, P
  • R is an alkyl group, cycloalkyl
  • X represents a carbon atom or a nitrogen atom
  • Q represents a 6-membered aromatic together with the carbon atom and X.
  • X is 0, S, CH, CHR, CR, NR, P
  • R is an alkyl group, cycloalkyl
  • X and X represent a nitrogen atom or a phosphorus atom, and X is coordinated to M through X and X
  • a group of atoms forming a bidentate ligand is represented. )
  • M represents a metal element of Groups 8 to 10 in the periodic table.
  • Ml is 1 or 2
  • nl is 1 or 2
  • ml + nl is 2 or 3.
  • Yes Matches the charge of M.
  • X represents a carbon or nitrogen atom
  • Q represents a 6-membered aromatic with carbon atom and X
  • X is 0, S, CH, CHR, CR, NR, P
  • R is an alkyl group, cycloalkyl
  • X represents a carbon atom or a nitrogen atom
  • Q represents a 6-membered aromatic together with the carbon atom and X.
  • X represents a carbon atom or a nitrogen atom
  • Q represents a 5- to 6-membered fragrance together with the nitrogen atom and X
  • X is 0, S, CH, CHR, CR, NR,
  • R is an alkyl group, cycloalkyl
  • At least one of the aromatic heterocycle B or the aromatic heterocycle D is a 6-membered ring, and the other is a 5-membered ring
  • M represents a metal element of Groups 8 to 10 in the periodic table of elements.
  • M2 is 1 or 2
  • n2 is 1 or 2.
  • m2 + n2 is 2 or 3.
  • Yes Matches the charge of M.
  • X represents a carbon or nitrogen atom
  • Q represents a 6-membered aromatic with carbon atom and X
  • X is 0, S, CH, CHR, CR, NR, P
  • R is an alkyl group, cycloalkyl
  • a group, an alkyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group; X and X are
  • 31 represents an atomic group forming a bidentate ligand coordinated to M through 32.
  • M represents a metal element belonging to Groups 8 to 10 in the periodic table.
  • Nl l and nl2 each represents an integer selected from 0 to 2; X and X are each> N
  • R is an alkyl group, cycloalkyl group, alkenyl
  • R is a hydrogen atom, alkyl group, cycloalkyl
  • X, X , X each represents CH or N, and any one or two of them are N.
  • X is 0, S, C b 19c 0
  • M represents a metal element belonging to Groups 8 to 10 in the periodic table.
  • n21 and n22 each represents an integer selected from 0 to 2.
  • X is> N—R, —O—
  • S R is an alkyl group, cycloalkyl group, alkenyl group, aryl
  • X and X are> N-R, —O or
  • R is a hydrogen atom, alkyl group, cycloalkyl group, alkenyl group, aryl
  • X, X, X are each CH or N
  • X is 0, S, CH, CHR, CR, NR, PR,
  • R is an alkyl group, a cycloalkyl group,
  • M represents a metal element of Groups 8 to 10 in the periodic table.
  • n31 and n32 represent an integer selected from 0 to 2.
  • X is> N—R, —O—
  • S R is an alkyl group, cycloalkyl group, alkenyl group, aryl
  • X and X are> N-R, —O or
  • R is a hydrogen atom, alkyl group, cycloalkyl group, alkenyl group, alkyl
  • X, X, X are each CH or N
  • X is 0, S, CH, CHR, CR, NR, PR,
  • R is an alkyl group, a cycloalkyl group,
  • M represents a metal element of Groups 8 to 10 in the periodic table.
  • X represents a carbon atom.
  • a group of atoms forming ring E which is a 5- to 6-membered aromatic heterocycle.
  • R represents a substituent, and n
  • Xa represents —N (Ra), —O—Ra or —S—Ra
  • the Ra represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. If Xa is — N (Ra), the two Ras are the same but different
  • R is an alkyl group, cycloalkyl group, alkenyl group, aryl group
  • M represents a metal element of Groups 8 to 10 in the periodic table of elements.
  • R 1, R 2, R 3, R 5 Each represents a hydrogen atom or an electron-donating substituent, and at least one is an electron-donating substituent.
  • At least one of 56 58 is an electron-withdrawing substituent.
  • R 1 and R 2 represent a substituent, n51, n5
  • Xa represents —N (Ra), —O—Ra or —S—Ra
  • the Ra represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. If Xa is — N (Ra), the two Ras are the same but different
  • R is an alkyl group, cycloalkyl group, alkenyl group, aryl group
  • M represents a metal element of Groups 8 to 10 in the periodic table.
  • 61 is a carbon atom and X, X
  • 61 represents a group of atoms forming a ring F which is a 6-membered aromatic hydrocarbon ring or a 5- to 6-membered aromatic heterocycle with 63 63, Q is a nitrogen atom and a 5- to 6-membered aromatic together with X and X Form a ring G that is a heterocycle
  • X and X represent substituents whose van der Waals volume is 20 A 3 or more bc
  • m6 and n6 each represents 0 or 1. However, m6 + n6 ⁇ l.
  • X is 0, S, CH, CHR,
  • R is an alkyl group
  • M represents a metal element of Groups 8 to 10 in the periodic table.
  • 71 is a carbon atom, X, X
  • 71 73 represents a group of atoms forming a ring H which is a 6-membered aromatic hydrocarbon ring or a 5- to 6-membered aromatic heterocycle, Q is a nitrogen atom, and a 5- to 6-membered aromatic together with X and X Atom that forms ring K, a heterocycle
  • 74 represents an atomic group forming an aromatic heterocyclic ring with a nitrogen atom.
  • R represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group.
  • the ligand is a partial structure represented by the following general formulas (41) to (433) or tautomers thereof:
  • R represents R —CO— or R —SO—
  • R represents an alkyl group, cycloalkyl
  • R, R, R, R, R, R Represents an alkyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group.
  • n represents an integer of 0 to 3
  • n and n represent an integer of 0 to 2.
  • R is an alkyl group, a cycloalkyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group
  • Q represents an atomic group that forms a 5- or 6-membered aromatic heterocycle with carbon and nitrogen
  • Q and Q represent an atomic group that forms a 5-membered aromatic heterocycle with carbon and nitrogen.
  • the organic electoluminescence device material according to item 1.
  • An organic electroluminescent device comprising the organic electroluminescent device according to (1) to (14), wherein the organic electroluminescent device is described above.
  • a light emitting layer is included as a constituent layer, and the light emitting layer contains the organic electoluminescence device material described in any one of (1) to (14) above. Organic electroreductive element.
  • the organic electoluminescence device according to any one of (17).
  • Z represents an aromatic heterocyclic ring
  • Z represents an aromatic heterocyclic ring or an aromatic hydrocarbon ring.
  • Z represents a divalent linking group or a simple bond.
  • R represents a hydrogen atom or a substituent.
  • R 1 to R 4 each independently represents a hydrogen atom or a substituent.
  • R 1 to R 4 each independently represents a hydrogen atom or a substituent.
  • R to R each independently represent a hydrogen atom or a substituent.
  • R 1 to R 4 each independently represents a hydrogen atom or a substituent.
  • R 1 to R 4 each independently represents a hydrogen atom or a substituent.
  • R 1 to R 3 each independently represents a hydrogen atom or a substituent.
  • R 1 to R 4 each independently represents a hydrogen atom or a substituent.
  • R represents a hydrogen atom or a substituent. Also, a plurality of R may be the same or different.
  • R represents a hydrogen atom or a substituent. Further, a plurality of R may be the same or different from each other.
  • the compound represented by the general formula (1A) has at least one group represented by any one of the following general formulas (2A-1) to (2A-10): The organic electoluminescence device according to any one of (1) to (22).
  • R ⁇ R, R ⁇ R, R ⁇ R, R ⁇ R each independently represents a hydrogen atom or a substituent.
  • the substituents may be the same or different.
  • 601 606 are each independently a force representing a hydrogen atom or a substituent R
  • At least one of 601 606 represents at least one group selected from the basic forces represented by the general formulas (2-1) to (2-10). )
  • R to R each independently represents a hydrogen atom or a substituent having a small force R to R
  • At least one represents at least one group selected from the groups represented by the general formulas (2A-1) to (2A-10). )
  • R to R each independently represents a hydrogen atom or a substituent having a small force R to R
  • At least one represents at least one group selected from the groups represented by the general formulas (2A-1) to (2A-10).
  • At least one of 645 represents at least one group selected from the groups represented by the general formulas (2A-1) to (2A-10). )
  • R 1 to R 4 each independently represents a hydrogen atom or a substituent having a small force
  • R 1 to R 5 each independently represents a hydrogen atom or a substituent having a small force
  • At least one represents at least one group selected from the basic forces represented by the general formulas (2-1) to (2-10).
  • na represents an integer from 0 to 5
  • nb represents an integer from 1 to 6, but the sum of na and nb is 6.
  • R to R each independently represents a hydrogen atom or a substituent having a small force R to R
  • At least one represents at least one group selected from the groups represented by the general formulas (2A-1) to (2A-10). )
  • At least one represents at least one group selected from the basic forces represented by the general formulas (2A-1) to (2A-10).
  • the organic elect described in any one of (18) to (22) above, wherein the compound represented by the general formula (1A) is represented by the following general formula (10A): Mouth luminescence element.
  • R to R each independently represents a hydrogen atom or a substituent
  • L represents a divalent linking group
  • At least one of R 1 to R 4 is represented by the general formulas (2A-1) to (2A-10)
  • R and R each independently represent a hydrogen atom or a substituent.
  • N and m are each an integer of 1 to 2.
  • R and R each independently represent a hydrogen atom or a substituent.
  • N and m are each an integer of 1 to 2.
  • R and R each independently represent a hydrogen atom or a substituent.
  • N and m are each an integer of 1 to 2.
  • R and R each independently represent a hydrogen atom or a substituent.
  • N and m are each an integer of 1 to 2.
  • R and R each independently represent a hydrogen atom or a substituent.
  • N and m are each an integer of 1 to 2.
  • Z, Z and Z each represents a 6-membered aromatic heterocyclic ring containing at least one nitrogen atom.
  • o and p each represent an integer of 1 to 3
  • Ar and Ar each represent an arylene group or a divalent aromatic group.
  • Z and Z are each a 6-membered aromatic compound containing at least one nitrogen atom.
  • ⁇ and ⁇ each represent an integer of 1 to 3
  • Ar and Ar each represent an arylene group or a divalent aromatic group.
  • Z, Z, Z, and Z are each a 6-membered good containing at least one nitrogen atom.
  • a display device comprising the organic electroluminescent device according to any one of (15) to (48).
  • an organic EL element material it is possible to provide an organic EL element material, an organic EL element, an illumination device, and a display device that exhibit high luminous efficiency and have a long emission lifetime.
  • Fig. 1 is a schematic diagram showing an example of a display device that also has organic EL element power.
  • FIG. 2 is a schematic diagram of display unit A.
  • FIG. 3 is a schematic diagram of a pixel.
  • FIG. 4 is a schematic diagram of a passive matrix display device.
  • FIG. 5 is a schematic view of a lighting device.
  • FIG. 6 is a cross-sectional view of the lighting device.
  • the organic EL element containing the organic EL element material means that the organic EL element material forms any organic layer constituting the organic EL element, or the organic layer. This represents the organic EL element contained in.
  • the layer structure of the organic EL element of the present invention will be described separately in detail.
  • a light emitting layer and / or a hole blocking layer are preferable.
  • it When it is contained in the light emitting layer, it can be used as a light emitting dopant in the light emitting layer to achieve a long emission life of the organic EL device which is the object of the present invention.
  • organic EL element material of the present invention and preferred embodiment (1) of the present invention is an ortho metal complex represented by the general formula (1).
  • M represents a metal element of Groups 8 to 10 in the periodic table.
  • L and 1 / represent different bidentate ligands, m is 1 or 2, and n is 1 or 2. However, m + n is 2 or 3, which matches the charge of M.
  • the partial structure ML is represented by the general formula (2), and the partial structure ML 'is represented by the general formula (3) or Is represented by (4).
  • X represents a carbon atom or a nitrogen atom
  • Q represents a 6-membered aromatic together with the carbon atom and X.
  • X is 0, S, CH, CHR, CR, NR, P
  • R is an alkyl group, cycloalkyl
  • X represents a carbon atom or a nitrogen atom
  • Q represents a 6-membered aromatic together with the carbon atom and X.
  • X is 0, S, CH, CHR, CR, NR, P
  • R is an alkyl group, cycloalkyl
  • X and X represent a nitrogen atom or a phosphorus atom, and X is coordinated to M through X and X
  • a group of atoms forming a bidentate ligand is represented.
  • Examples of the 6-membered aromatic hydrocarbon ring include a benzene ring.
  • Examples of the 5- to 6-membered aromatic heterocycle include oxazole ring, thiophene ring, furan ring, pyrrole ring, pyridine ring, pyridazine ring, pyrimidine ring, pyrazine ring, triazine ring, imidazole ring, pyrazole ring, And a triazole ring.
  • 6-membered aromatic hydrocarbon rings and 5- to 6-membered aromatic heterocycles are alkyl groups (eg, methyl group, ethyl group, propyl group, isopropyl group, (t) butyl group, pentyl group).
  • cycloalkyl group eg, cyclopentyl group, cyclohexyl group, etc.
  • alkenyl group eg, vinyl group, aryl) Group
  • alkynyl group for example, propargyl group, etc.
  • aryl group also called aromatic hydrocarbon ring group, for example, phenyl group, tolyl group, xylyl group, naphthyl group, biphenyl-allyl group, anthryl group, phenanthryl
  • heterocyclic group for example, pyrrolidyl group, imidazolidyl group, morpholyl group, oxazolidyl group, etc.
  • aromatic heterocyclic group for example, pyridyl group, Rimijiniru group,
  • acetyl, ethyl carbo, propyl carbo Group pentyl carbo yl group, cyclohexyl carbo yl group, octyl carbo ol group, 2-ethyl hexyl carbo yl group, dodecyl carbo carb yl group, vinyl carbo yl group, naphthyl carbo yl group, Pyridyl carbon Group), acyloxy group (for example, acetyloxy group, ethylcarbo-loxy group, butylcarbo-loxy group, octylcarbonyl-oxyl group, dodecylcarbonyloxy group, phenylcarbonyloxy group, etc.), amido group (for example, methyl Carbonylamino group, ethyl carbolumino group, dimethyl carbolumino group, propyl carbolumino group
  • Forced rubamoyl groups for example, aminoamino group, methylaminocarbol group, dimethylaminocarbole group, open pyraminocarbol group, pentylaminocarbo ol group, cyclohexylamino
  • Carbon group Octylaminocarbol group, 2-Ethylhexylaminocarbol group, Dodecylaminocarbol group, Phenylaminocarbol group, Naphtylaminocarbol group, 2— Pyridylaminocarbol group, etc.
  • sulfier groups eg methylsulfur
  • the alkyl group, cycloalkyl group, alkyl group, aryl group, bicyclic group, and aromatic heterocyclic group represented by R are each a 6-membered aromatic hydrocarbon ring, a 5- to 6-membered group, respectively. These are synonymous with the alkyl group, cycloalkyl group, alkenyl group, aryl group, heterocyclic group, and aromatic heterocyclic group described as the substituent of the aromatic heterocyclic group.
  • the organic EL device material of the aspect (2) is an ortho metal complex represented by the general formula (5).
  • M represents a metal element of Groups 8 to 10 in the periodic table.
  • ml is 1 or 2 and nl is 1 or 2.
  • nl + nl is 2 or 3, which matches the charge of M.
  • X represents a carbon atom or a nitrogen atom
  • Q represents a 6-membered aromatic together with the carbon atom and X
  • X is 0, S, CH, CHR, CR, NR, P
  • R is an alkyl group, cycloalkyl
  • X represents a carbon atom or a nitrogen atom
  • Q represents a 6-membered aromatic together with the carbon atom and X.
  • X is 0, S, CH, CHR, CR, NR,
  • R is an alkyl group, cycloalkyl
  • 6-membered aromatic hydrocarbon ring 5- to 6-membered aromatic heterocycle, and R have the same meanings as described in the embodiment (1).
  • At least one of the aromatic heterocycle B or the aromatic heterocycle D is preferably a 6-membered ring and the other is preferably a 5-membered ring.
  • the organic EL device material of the aspect (4) is an ortho metal complex represented by the general formula (6).
  • M represents a metal element of Groups 8 to 10 in the periodic table.
  • m2 is 1 or 2
  • n2 is 1 or 2.
  • m2 + n2 is 2 or 3, which matches the charge of M
  • X represents a carbon atom or a nitrogen atom
  • Q represents a 6-membered aromatic together with the carbon atom and X
  • Q is a 5- to 6-membered aromatic together with the nitrogen atom and X A group of atoms forming ring B which is a heterocyclic ring.
  • X is 0, S, CH, CHR, CR, NR, P
  • R is an alkyl group, cycloalkyl
  • a group, an alkyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group; X and X are
  • 6-membered aromatic hydrocarbon ring 5- to 6-membered aromatic heterocycle, and R have the same meanings as described in the embodiment (1).
  • the aromatic heterocycle B is preferably a 6-membered ring.
  • the organic EL device material of the aspect (6) is an ortho metal complex having a partial structure represented by the general formulas (1-1) to (1-150) or a tautomer thereof as a partial structure. It is characterized by being.
  • M represents a metal element of Groups 8 to 10 in the periodic table.
  • R and R are
  • nl l and nl2 each represents an integer selected from 0 to 2.
  • X and X are each> N
  • R represents one O or S.
  • R is an alkyl group, cycloalkyl group, alkenyl
  • R is a hydrogen atom, alkyl group, cycloalkyl
  • X each represents CH or N, and any one or two of them are N.
  • X is 0, S, C b 19c 0
  • R 1 and R 2 is the 6-membered aromatic hydrocarbon described in the embodiment (1).
  • alkyl group, cycloalkyl group, alkenyl group, aryl group, heterocyclic group or aromatic heterocyclic group has the same meaning as described in the embodiment (1).
  • the organic EL device material of the aspect (7) is an ortho metal complex having a partial structure represented by the general formulas (2-1) to (2-50) or a tautomer thereof as a partial structure. It is characterized by being. [0160] In the formula, M represents a metal element of Groups 8 to 10 in the periodic table. R and R are
  • n21 and n22 each represents an integer selected from 0 to 2.
  • X is> N—R, —O—
  • S R is an alkyl group, cycloalkyl group, alkenyl group, aryl
  • X and X are> N-R, —O or
  • R is a hydrogen atom, alkyl group, cycloalkyl group, alkenyl group, aryl
  • X, X, X are each CH or N
  • X is 0, S, CH, CHR, CR, NR, PR,
  • R is an alkyl group, a cycloalkyl group,
  • R 1 and R 2 is the 6-membered aromatic hydrocarbon described in the embodiment (1).
  • alkyl group, cycloalkyl group, alkenyl group, aryl group, heterocyclic group or aromatic heterocyclic group has the same meaning as described in the embodiment (1).
  • the organic EL device material of the aspect (8) is an ortho metal complex having a partial structure represented by the general formulas (3-1) to (3-10) or a tautomer thereof as a partial structure. It is characterized by being.
  • M represents a metal element of Groups 8 to 10 in the periodic table.
  • R and R are
  • n31 and n32 represent an integer selected from 0 to 2.
  • X is> N—R, —O—
  • S R is an alkyl group, cycloalkyl group, alkenyl group, aryl
  • X and X are> N-R, —O or
  • R is a hydrogen atom, alkyl group, cycloalkyl group, alkenyl group, aryl
  • X, X, X are each CH or N
  • X is 0, S, CH, CHR, CR, NR, PR,
  • R is an alkyl group, a cycloalkyl group,
  • R 1 and R 2 is the 6-membered aromatic hydrocarbon described in the embodiment (1).
  • alkyl group, cycloalkyl group, alkenyl group, aryl group, heterocyclic group or aromatic heterocyclic group is the same as the above-described embodiment (1 ) Is synonymous with that described above.
  • the organic EL device material of the aspect (9) is an ortho metal complex having a partial structure represented by the general formula (7) or a tautomer thereof as a partial structure.
  • M represents a metal element of Groups 8 to 10 in the periodic table.
  • X is a carbon atom
  • Q is a carbon atom and X together with a 6-membered aromatic hydrocarbon ring or
  • a group of atoms forming ring E which is a 5- to 6-membered aromatic heterocycle.
  • R represents a substituent, and n
  • Xa represents —N (Ra), —O—Ra or —S—Ra
  • the Ra represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. If Xa is — N (Ra), the two Ras are the same but different
  • R is an alkyl group, cycloalkyl group, alkenyl group, aryl group
  • R 1 is a 6-membered aromatic hydrocarbon ring described in the embodiment (1),
  • alkyl group, cycloalkyl group, alkenyl group, aryl group, heterocyclic group or aromatic heterocyclic group has the same meaning as described in the embodiment (1).
  • the orthometal complex having a partial structure represented by the general formula (7) or a tautomer thereof as a partial structure is a partial structure represented by the general formula (8) or (9) or a tautomer thereof. It is preferable that it is an ortho metal complex which has an active substance as a partial structure.
  • M represents a metal element of Groups 8 to 10 in the periodic table.
  • At least one of 56 58 is an electron-withdrawing substituent.
  • R 1 and R 2 represent a substituent, n51, n5
  • Xa represents —N (Ra), —O—Ra or —S—Ra
  • the Ra represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. If Xa is — N (Ra), the two Ras are the same but different
  • R is an alkyl group, cycloalkyl group, alkenyl group, aryl group Represents a heterocyclic group or an aromatic heterocyclic group.
  • the electron-donating substituent is a substituent having a negative Hammett ⁇ ⁇ value described below, and such a substituent has an electron closer to the bonding atom side than a hydrogen atom. It is easy to give.
  • substituent exhibiting an electron donating property include a hydroxyl group, an alkoxy group (for example, methoxy group,), an acetyloxy group, an amino group, a dimethylamino group, an acetylamino group, an alkyl group (for example, a methyl group, Ethyl group, propyl group, tert-butyl group, etc.) and aryl group (eg, phenyl group, mesityl group, etc.).
  • a cycloprovir group (one 0.21), a cyclohexyl group (—0.22), a tert-butyl group (—0.0. 20), — CH Si (CH) (— 0.
  • ⁇ ⁇ value of Met and Met refers to Hammett's substituent constant ⁇ ⁇ .
  • Hammett's ⁇ ⁇ value is the substituent constant determined by Hammett et al. For the electronic effect of the substituents on the hydrolysis of ethyl benzoate. “Structure-activity relationship of drugs” (Nanedo: 1979) , Rsubstituent Constants for Correlation Analysis chemistry and biology (C. Hansch and A. Leo, John Wiley & Sons, New York, 1979), etc. can be cited.
  • the electron-donating substituent is most preferably an alkyl group, an alkoxy group, or an alkylamino group.
  • the substituent is synonymous with the substituent of the 6-membered aromatic hydrocarbon ring or 5- to 6-membered aromatic heterocycle described in the embodiment (1).
  • the alkyl group, cycloalkyl group, alkyl group, aryl group, heterocyclic group or aromatic heterocyclic group is the same as described in the embodiment (1). It is synonymous with.
  • the organic EL device material of the aspect (11) is an ortho metal complex having a partial structure represented by the general formula (10) or a tautomer thereof as a partial structure.
  • M represents a metal element of Groups 8 to 10 in the periodic table.
  • 61 is a carbon atom and X, X
  • 61 represents a group of atoms that together with 63 form ring F, which is a 6-membered aromatic hydrocarbon ring or a 5- to 6-membered aromatic heterocyclic ring.
  • Q forms a ring G, which is a 5- to 6-membered aromatic heterocycle, together with the nitrogen atom and X ⁇ ilO—L, X.
  • k A represents a substituent that is 3 or more h
  • M6 each represents 0 or 1. However, m6 + n6 ⁇ l.
  • X is 0, S, CH, CHR,
  • R is an alkyl group
  • the 6-membered aromatic hydrocarbon ring and the 5- to 6-membered aromatic heterocyclic ring have the same meanings as described in the embodiment (1).
  • VDW van der Waals
  • alkyl group, cycloalkyl group, alkyl group, aryl group, heterocyclic group or aromatic heterocyclic group has the same meaning as described in the embodiment (1).
  • the orthometal complex having a partial structure represented by the general formula (10) or a tautomer thereof as a partial structure is a partial structure represented by the general formulas (11) to (14) or a tautomer thereof. It is preferable that it is an ortho metal complex which has an active substance as a partial structure.
  • M represents a metal element of Groups 8 to 10 in the periodic table.
  • 71 71 73 represents a group of atoms forming ring H which is a 6-membered aromatic hydrocarbon ring or a 5- to 6-membered aromatic heterocyclic ring, Q is a nitrogen atom, and 5 to 6-membered aromatic together with X and X Atoms forming ring K, a heterocyclic ring
  • 74 represents an atomic group forming an aromatic heterocyclic ring with a nitrogen atom.
  • R represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group.
  • the 6-membered aromatic hydrocarbon ring and the 5- to 6-membered aromatic heterocyclic ring have the same meanings as described in the embodiment (1).
  • alkyl group, cycloalkyl group, alkyl group, aryl group, heterocyclic group or aromatic heterocyclic group has the same meaning as described in the embodiment (1).
  • the organic EL device material of the embodiment (13) is X — X of the general formula (4) or the general formula (6).
  • the bidentate ligand formed by -X is represented by the general formulas (4 1) to (4 31)
  • R represents R —CO— or R —SO—
  • R represents an alkyl group, cycloalkyl
  • R, R, R, R, R, R Represents an alkyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group.
  • n represents an integer of 0 to 3
  • n and n represent an integer of 0 to 2.
  • R is an alkyl group, a cycloalkyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group
  • Q represents an atomic group that forms a 5- or 6-membered aromatic heterocycle with carbon and nitrogen
  • Q 1 and Q 2 represent an atomic group that forms a 5-membered aromatic heterocycle with carbon and nitrogen.
  • the 5- to 6-membered aromatic heterocyclic ring has the same meaning as described in the embodiment (1).
  • alkyl group, cycloalkyl group, alkyl group, aryl group, heterocyclic group or aromatic heterocyclic group has the same meaning as described in the embodiment (1).
  • the organic EL device material of the aspect (14) is characterized in that, in all the general formulas, it is an orthometallic complex which is M force iridium or platinum.
  • the organic EL element material is contained in any of the constituent layers (organic layers) constituting the organic EL element to produce an organic EL element.
  • the organic EL element preferably has a light emitting layer as a constituent layer, and the light emitting layer preferably contains the organic EL element material. When it is contained in the light emitting layer, it can be used as a light emitting dopant in the light emitting layer to achieve a long emission life of the organic EL device which is the object of the present invention.
  • the organic EL element has a hole blocking layer as a constituent layer, and the hole blocking layer includes the organic E
  • the organic EL device of the aspect (18) is characterized by containing the compound represented by the general formula (1A).
  • Z represents an aromatic heterocyclic ring
  • Z represents an aromatic heterocyclic ring or an aromatic hydrocarbon ring.
  • Z represents a divalent linking group or a simple bond.
  • R is a hydrogen atom or a substituent
  • Z may have a substituent! Represents an aromatic heterocyclic ring, and Z is
  • R 3 represents a divalent linking group or a simple bond.
  • 101 represents a hydrogen atom or a substituent.
  • Aromatic heterocycles represented by Z and Z include furan ring, thiophene ring, pyridine ring,
  • Examples of the aromatic hydrocarbon ring represented by Z include a benzene ring, biphenyl ring, and naphthalene ring.
  • the aromatic hydrocarbon ring is represented by R described later.
  • Examples of the substituent represented by R include an alkyl group (for example, methyl group, ethyl group, propyl group).
  • cycloalkyl group for example, cyclopentyl group, cyclohexyl group, etc.
  • Alkenyl group for example, buyl group, allyl group, etc.
  • alkynyl group for example, ethynyl group, propargyl group, etc.
  • aryl group for example,
  • aromatic heterocyclic group e.g. furyl group, chael group, pyridyl group, pyridazyl group, pyrimidyl group, pyrazyl group, triazinyl group, imidazolyl group, Pyrazolyl group, thiazolyl group, quinazolyl group, phthalazinyl group, etc.
  • heterocyclic group eg, pyrrolidyl group, imidazolidyl group, morpholyl group, oxazolidyl group, etc.
  • alkoxyl group eg, methoxy group, ethoxy group, propyloxy group
  • cycloalkoxyl group eg, cyclopentyloxy group, cyclohexyloxy group, etc.
  • substituents may be further substituted with the above substituents.
  • a plurality of these substituents may be bonded to each other to form a ring.
  • the substituent is an alkyl group, a cycloalkyl group, a fluorinated hydrocarbon group, an aryl group, or an aromatic heterocyclic group.
  • Examples of the divalent linking group represented by Z include alkylene, alkylene, alkylene, and aryl.
  • heteroatoms In addition to hydrocarbon groups such as mono-ene, compounds containing heteroatoms may also be used, and compounds having aromatic heterocycles such as thiophene 2, 5 diyl group or pyrazine 2, 3 diyl group (heteroaromatics) It may be a divalent linking group derived from a compound) or a chalcogen atom such as oxygen or sulfur. Further, it may be a group in which heteroatoms such as an alkylimino group, dialkylsilane diyl group or diarylgermandyl group are linked to each other.
  • a mere bond is a bond that directly bonds the linking substituents together.
  • the Z-membered ring represented by the general formula (1A) is preferable. This is because the Z-membered ring represented by the general formula (1A) is preferable. This is because the Z-membered ring represented by the general formula (1A) is preferable.
  • the luminous efficiency can be further increased. Further, the life can be extended.
  • a Z-membered ring is preferable. This increases the luminous efficiency.
  • both 2 are 6-membered rings because the luminous efficiency can be further increased. Further, it is preferable because the lifetime can be further increased.
  • the compound represented by the general formula (1A) has a molecular weight of 450 or more, which can increase the luminous efficiency and prolong the life.
  • the compound represented by the general formula (1A) is preferably a compound represented by the general formula (1A-1) to (: LA
  • R to R each independently represent a hydrogen atom or a substituent.
  • R to R each independently represent a hydrogen atom or a substituent.
  • R to R each independently represent a hydrogen atom or a substituent.
  • R to R each independently represent a hydrogen atom or a substituent.
  • R to R each independently represent a hydrogen atom or a substituent.
  • R to R each independently represent a hydrogen atom or a substituent.
  • R to R each independently represent a hydrogen atom or a substituent.
  • R to R each independently represent a hydrogen atom or a substituent.
  • R represents a hydrogen atom or a substituent.
  • the plurality of R may be the same or different.
  • R represents a hydrogen atom or a substituent.
  • the plurality of R may be the same or different.
  • Compound represented by general formula (1 A-10) By using, an organic EL element with higher luminous efficiency can be obtained. Furthermore, it can be a long-life organic EL device.
  • the compound represented by the general formula (1A) is preferably a compound having at least one group represented by any one of the general formulas (2A-1) to (2A-10). It is. In particular, it is more preferable to have 2 to 4 groups represented by the deviations of the general formulas (2A-1) to (2A-10) in the molecule.
  • the structure represented by the general formula (1A) includes a case where R is removed and the part is replaced by the general formulas (2A-1) to (2A-10).
  • R to R represent a hydrogen atom or a substituent.
  • At least one R is a group represented by any of the formulas (2A-1) to (2A-10).
  • R to R represent a hydrogen atom or a substituent.
  • At least one R is a group represented by any of the formulas (2A-1) to (2A-10).
  • R to R represent a hydrogen atom or a substituent.
  • At least one R is a group represented by any of the formulas (2A-1) to (2A-10).
  • R to R represent a hydrogen atom or a substituent.
  • At least one R is a group represented by any of the formulas (2A-1) to (2A-10).
  • R to R represent a hydrogen atom or a substituent.
  • At least one R is a group represented by any of the formulas (2A-1) to (2A-10).
  • na represents an integer from 0 to 5
  • nb represents an integer from 1 to 6, but the sum of na and nb is 6.
  • R to R represent a hydrogen atom or a substituent.
  • At least one R is a group represented by any of the formulas (2A-1) to (2A-10).
  • R ⁇ R represents a hydrogen atom or a force representing a substituent R ⁇
  • At least one R is a group represented by any of the formulas (2A-1) to (2A-10).
  • R 1 to R 4 represent a hydrogen atom or a force representing a substituent R
  • At least one of ⁇ R is represented by! /, Deviation of the general formulas (2A-1) to (2A-10)
  • Examples of the divalent linking group represented by L include an alkylene group (for example, ethylene group, trimethylene).
  • At least one of carbon atoms constituting the divalent linking group is a chalcogen atom (oxygen, sulfur, etc.) N (R) —may be substituted with a group or the like.
  • the divalent linking group represented by L for example, a group having a divalent heterocyclic group is used.
  • a group having a divalent heterocyclic group is used.
  • the alkylimino group, the dialkylsilane diyl group, and the diarylgermandyl group may be a group that connects and connects hetero atoms
  • each of Z, Z, Z, and Z each represents a small number of nitrogen atoms.
  • 6-membered aromatic heterocycle containing at least one examples include a pyridine ring, a pyridazine ring, a pyrimidine ring, and a pyrazine ring.
  • each of the nitrogen atoms represented by Z and Z is at least
  • 6-membered aromatic heterocycle including one pyridine examples include a pyridine ring, a pyridazine ring, a pyrimidine ring, and a pyrazine ring.
  • the arylene groups represented by Ar and Ar include o-phenylene group and m-phenylene group, respectively.
  • P phenylene group naphthalene diyl group, anthracenedyl group, naphthacene diyl group, pyrene diyl group, naphthyl naphthalene diyl group, biphenyl group (for example, 3, 3'-biphenyl group, 3, 6-biphenyl group) Etc.), terfelsyl group, quaterfel group, kink feldsyl group, sexiphenyl group, septiphenyl group, octaphenyl group, nobiphenyl group, decyl group and the like.
  • the arylene group may further have a substituent described later.
  • the divalent aromatic heterocyclic groups represented by Ar and Ar are respectively a furan ring, a thiophene ring,
  • Examples of the divalent linking group represented by L include those represented by L in the general formula (10A).
  • Power that is synonymous with a valent linking group is preferably an alkylene group or a divalent group containing a chalcogen atom such as OS or the like, and most preferably an alkylene group.
  • the aromatic heterocyclic group represented by 1 2 1 2 is represented by Ar and Ar in the general formula (16A).
  • 6-membered aromatics each represented by Z, Z, Z, Z, each containing at least one nitrogen atom
  • heterocyclic ring examples include a pyridine ring, a pyridazine ring, a pyrimidine ring, and a pyrazine ring.
  • the divalent linking group represented by L is represented by L 2 in the general formula (10A).
  • Power that is synonymous with a valent linking group is preferably an alkylene group, a divalent group containing a chalcogen atom such as os-, and most preferably an alkylene group.
  • the compound according to the present invention preferably has a molecular weight of 00 or more, more preferably 450 or more, still more preferably 600 or more, and particularly preferably a molecular weight of 800 or more. As a result, the glass transition temperature is raised, the thermal stability is improved, and the life can be further extended.
  • Z electron transport layer Z cathode (m) anode Z hole transport layer Z light emitting layer Z hole blocking layer Z electron transport layer Z cathode transport layer Z cathode Gv) anode Z hole transport layer Z light emitting layer Z hole blocking layer Z electron transport layer Z Cathode buffer layer Z cathode (V) anode Z anode buffer layer Z hole transport layer Z light-emitting layer Z hole blocking layer Z electron transport layer Z cathode buffer layer Z cathode
  • an electrode material made of a metal, an alloy, an electrically conductive compound or a mixture thereof having a high work function (4 eV or more) is preferably used.
  • electrode materials include metals such as Au, conductive transparent materials such as Cul, indium tinoxide (ITO), SnO, and ZnO. IDIXO (In O—ZnO) etc.
  • the anode if these electrode materials are formed into a thin film by a method such as vapor deposition or sputtering and a pattern of a desired shape can be formed by a photolithography method, or the pattern accuracy is not so required (About 100 ⁇ m or more), the pattern may be formed through a mask of a desired shape during the deposition or sputtering of the electrode material. In the case of taking out light emission from this anode, it is desirable to make the transmittance larger than 10%, and the sheet resistance as the anode is preferably several hundred ⁇ Z or less. Further, the film thickness is a force depending on the material. Usually, 10 to: LOOOnm, preferably 10 to 2 OOnm is selected.
  • a cathode having a work function (4 eV or less) metal referred to as an electron injecting metal
  • an alloy referred to as an electrically conductive compound
  • a mixture thereof is used.
  • electrode materials include sodium, sodium-potassium alloy, magnesium, lithium, magnesium Z copper mixture, magnesium Z silver mixture, magnesium Z aluminum mixture, magnesium Z indium mixture, aluminum Z acid aluminum UM (Al 2 O 3) mixture, indium, lithium
  • the cathode can be produced by forming a thin film of these electrode materials by a method such as vapor deposition or sputtering. Also, the sheet resistance as a cathode is several hundred ⁇ / mouth or less, and the preferred film thickness is usually ⁇ ! ⁇ 5 ⁇ m, preferably selected in the range of 50 to 200 nm. In addition, since the emitted light is transmitted, it is convenient that either the anode or the cathode of the organic EL element is transparent or semi-transparent to improve the emission luminance.

Abstract

Disclosed is an organic EL device material exhibiting high luminous efficiency while having long emission life. Also disclosed are an organic EL device, an illuminating device, and a display. Specifically disclosed is an organic EL device material characterized by being composed of an orthometal complex represented by the following general formula (1). MLmL'n (1) (In the formula, M represents a group 8-10 metal element of the periodic table; L and L' respectively represent a bidentate ligand different from each other; m represents 1 or 2; and n represents 1 or 2. In this connection, m + n is 2 or 3 and equal to the electric charge of M. The partial structure ML is represented by the general formula (2) below, and the partial structure ML' is represented by the general formula (3) or (4) below.)

Description

明 細 書  Specification
有機エレクト口ルミネッセンス素子材料、有機エレクト口ルミネッセンス素子 技術分野  Organic Electrical Luminescence Element Materials, Organic Electric Luminescence Element Technical Field
[0001] 本発明は、有機エレクト口ルミネッセンス素子材料、有機エレクト口ルミネッセンス素 子、表示装置及び照明装置に関する。  TECHNICAL FIELD [0001] The present invention relates to an organic electoluminescence device material, an organic electroluminescence device, a display device, and a lighting device.
背景技術  Background art
[0002] 従来、発光型の電子ディスプレイデバイスとして、エレクト口ルミネッセンスディスプレ ィ(以下、 ELDという)がある。 ELDの構成要素としては、無機エレクト口ルミネッセン ス素子や有機エレクト口ルミネッセンス素子(以下、有機 EL素子という)が挙げられる 。無機エレクト口ルミネッセンス素子は平面型光源として使用されてきたが、発光素子 を駆動させるためには交流の高電圧が必要である。有機 EL素子は、発光する化合 物を含有する発光層を陰極と陽極で挟んだ構成を有し、発光層に電子及び正孔を 注入して、再結合させることにより励起子 (エキシトン)を生成させ、このエキシトンが 失活する際の光の放出 (蛍光'燐光)を利用して発光する素子であり、数 V〜数十 V 程度の電圧で発光が可能であり、さらに、自己発光型であるために視野角に富み、 視認性が高ぐ薄膜型の完全固体素子であるために省スペース、携帯性等の観点か ら注目されている。  [0002] Conventionally, as a light-emitting electronic display device, there is an electoric luminescence display (hereinafter referred to as ELD). Examples of ELD constituent elements include inorganic electoluminescence elements and organic electroluminescence elements (hereinafter referred to as organic EL elements). Inorganic electoric luminescence elements have been used as planar light sources, but in order to drive the light emitting elements, an alternating high voltage is required. An organic EL device has a structure in which a light-emitting layer containing a compound that emits light is sandwiched between a cathode and an anode, and excitons (excitons) are generated by injecting electrons and holes into the light-emitting layer and recombining them. The device emits light using the emission of light (fluorescence 'phosphorescence) when this exciton is deactivated, and can emit light at a voltage of several V to several tens of V. For this reason, it is a thin-film, completely solid element that has a wide viewing angle and high visibility, and is attracting attention from the viewpoints of space saving and portability.
[0003] し力しながら、今後の実用化に向けた有機 EL素子においては、さらに低消費電力 で効率よく高輝度に発光する有機 EL素子の開発が望まれている。  However, for organic EL elements for practical use in the future, it is desired to develop organic EL elements that emit light efficiently and with high luminance with lower power consumption.
[0004] 特許第 3093796号明細書では、有機エレクト口ルミネッセンス素子材料 (以下、有 機 EL素子材料という)として、スチルベン誘導体、ジスチリルァリーレン誘導体または トリススチリルァリーレン誘導体に、微量の蛍光体をドープし、発光輝度の向上、有機 EL素子の長寿命化を達成して 、る。  In the specification of Japanese Patent No. 3093796, a small amount of phosphor is added to a stilbene derivative, a distyrylarylene derivative or a tristyrylarylene derivative as an organic electoluminescence device material (hereinafter referred to as an organic EL device material). Doping improves the emission brightness and extends the lifetime of organic EL devices.
[0005] また、 8—ヒドロキシキノリンアルミニウム錯体をホストイ匕合物として、これに微量の蛍 光体をドープした有機発光層を有する有機 EL素子 (例えば、特開昭 63— 264692 号公報)、 8—ヒドロキシキノリンアルミニウム錯体をホストイ匕合物として、これにキナタリ ドン系色素をドープした有機発光層を有する有機 EL素子 (例えば、特開平 3— 255 190号公報)等が知られている。 [0005] Further, an organic EL device having an organic light emitting layer in which an 8-hydroxyquinoline aluminum complex is used as a host compound and a small amount of a phosphor is doped therein (for example, Japanese Patent Laid-Open No. 63-264692), 8 —An organic EL device having an organic light-emitting layer in which a hydroxyquinoline aluminum complex is used as a host compound and doped with a quinatalidone dye (see, for example, JP-A-3-255). No. 190) is known.
[0006] 以上のように、励起一重項力 の発光を用いる場合、一重項励起子と三重項励起 子の生成比が 1 : 3であるため発光性励起種の生成確率が 25%であり、光の取り出し 効率が約 20%であるため、外部取り出し量子効率( r? ext)の限界は 5%とされてい た。 [0006] As described above, when the emission of excited singlet force is used, the generation ratio of singlet excitons and triplet excitons is 1: 3, so the generation probability of luminescent excited species is 25%. Since the light extraction efficiency is about 20%, the limit of the external extraction quantum efficiency (r? Ext) was set at 5%.
[0007] ところが、プリンストン大より励起三重項力もの燐光発光を用いる有機 EL素子の報 告(M. A. Baldo et al. , nature, 395卷、 151— 154ページ(1998年))力され て以来、室温で燐光を示す材料の研究が活発になってきて 、る。  [0007] However, since the report of OLED devices using excited phosphorescent light emission from Princeton University (MA Baldo et al., Nature, 395 卷, 151–154 (1998)) Research on materials that exhibit phosphorescence has become active.
[0008] 例えば M. A. Baldo et al. , nature, 403卷、 17号、 750— 753ページ(2000 年)、また米国特許第 6, 097, 147号明細書等にも開示されている。 [0008] For example, it is disclosed in M. A. Baldo et al., Nature, 403 卷, 17, 750-753 (2000), US Pat. No. 6,097, 147, and the like.
[0009] 励起三重項を使用すると、内部量子効率の上限が 100%となるため、励起一重項 の場合に比べて原理的に発光効率力 倍となり、冷陰極管とほぼ同等の性能が得ら れる可能性があることから照明用途としても注目されている。 [0009] When the excited triplet is used, the upper limit of the internal quantum efficiency is 100%. Therefore, in principle, the luminous efficiency is doubled compared to the case of the excited singlet, and almost the same performance as a cold cathode tube is obtained. It is also attracting attention as a lighting application.
[0010] 例えば、 S. Lamansky et al. , J. Am. Chem. Soc. , 123卷, 4304ページ(2[0010] For example, S. Lamansky et al., J. Am. Chem. Soc., 123 卷, page 4304 (2
001年)等においては、多くの化合物がイリジウム錯体系等重金属錯体を中心に合 成検討されている。 (001), etc., many compounds are being studied focusing on heavy metal complexes such as iridium complexes.
[0011] また、前述の M. A. Baldo et al. , nature, 403卷, 17号, 750— 753ページ( 2000年)においては、ドーパントとして、トリス(2—フエ-ルビリジン)イリジウムを用い た検討がされている。  [0011] In addition, in the above-mentioned MA Baldo et al., Nature, 403 卷, 17, 750-753 (2000), a study using tris (2-phenol-lysine) iridium as a dopant was conducted. ing.
[0012] その他、 M. E. Tompson等は、 The 10th International Workshop on In organic and Organic Electroluminescence (EL ' 00、浜松)【こお ヽて、ド ~~ノヽ ントとして L Ir (acac)例えば(ppy) Ir (acac)を、また、 Moon— Jae Youn. 0g、 Te  [0012] In addition, ME Tompson et al., The 10th International Workshop on In organic and Organic Electroluminescence (EL '00, Hamamatsu) acac), Moon— Jae Youn. 0g, Te
2 2  twenty two
tsuo Tsutsui等 ίま、や ίまり、 The 10th International Workshop on Inorga nic and Organic Electroluminescence (EL, 00、浜松)【こお ヽて、ドーノ ント として、トリス(2— (p—トリル)ピリジン)イリジウム (Ir (ptpy) ) ,トリス (ベンゾ [h]キノリ  tsuo Tsutsui et al. The 10th International Workshop on Inorganic and Organic Electroluminescence (EL, 00, Hamamatsu) Ir (ptpy)), Tris (benzo [h] quinori
3  Three
ン)イリジウム (Ir (bzq) )等を用いた検討を行って 、る (なおこれらの金属錯体は一般  ) Iridium (Ir (bzq)) etc.
3  Three
にオルトメタル化イリジウム錯体と呼ばれて 、る。)。  It is called an ortho-metalated iridium complex. ).
[0013] また、前記、 S. Lamanskv et al. , J. Am. Chem. Soc. , 123卷, 4304ぺー ジ(2001年)等にぉ 、ても、各種イリジウム錯体を用いて素子化する試みがされて!/ヽ る。 [0013] In addition, the aforementioned S. Lamanskv et al., J. Am. Chem. Soc., 123, 4304 Even in the case of Di (2001), attempts have been made to make devices using various iridium complexes!
[0014] また、高い発光効率を得るために、 The 10th International Workshop on Inorganic and Organic Electroluminescence (EL ' 00、浜松)では、 Ikai等 はホール輸送性の化合物を燐光性ィ匕合物のホストとして用いている。また、 M. E. T ompson等は、各種電子輸送性材料を燐光性ィ匕合物のホストとして、これらに新規な イリジウム錯体をドープして用いて!/、る。  [0014] In order to obtain high luminous efficiency, in the 10th International Workshop on Inorganic and Organic Electroluminescence (EL '00, Hamamatsu), Ikai et al. Used a hole-transporting compound as a host for phosphorescent compounds. ing. M. E. Thompson et al. Use various electron transport materials as hosts for phosphorescent compounds and dope these with new iridium complexes.
[0015] 中心金属をイリジウムの代わりに白金としたオルトメタルイ匕錯体も注目されて 、る。こ の種の錯体に関しては、配位子に特徴を持たせた例が多数知られている(例えば、 特許文献 1〜5及び非特許文献 1参照。 ) 0 [0015] An ortho-metal complex containing a central metal platinum instead of iridium is also attracting attention. Regarding this type of complex, examples which gave characterized ligands are known a number (e.g., Patent Documents 1-5 and Non-Patent Reference 1.) 0
[0016] 何れの場合も発光素子とした場合の発光輝度や発光効率は、その発光する光が燐 光に由来することから、従来の有機 EL素子に比べ大幅に改良されるものであるが、 有機 EL素子の発光寿命にっ 、ては従来の有機 EL素子よりも低 、と 、う問題点があ つた。このように、りん光性の高効率の発光材料は、発光波長の短波化と有機 EL素 子の発光寿命の改善が難しく実用に耐えうる性能を十分に達成できていないのが現 状である。  [0016] In any case, the light emission brightness and the light emission efficiency in the case of a light emitting element are greatly improved compared to conventional organic EL elements because the emitted light is derived from phosphorescence. There was a problem that the light emission life of the organic EL device was lower than that of the conventional organic EL device. Thus, phosphorescent high-efficiency light-emitting materials are currently unable to achieve sufficient performance for practical use because it is difficult to shorten the emission wavelength and improve the light-emitting lifetime of organic EL elements. .
[0017] 波長の短波化に関しては、これまでフエニルピリジンにフッ素原子、トリフルォロメチ ル基、シァノ基等の電子吸引基を置換基として導入すること、配位子としてピコリン酸 やビラザボール系の配位子を導入することが知られている(例えば、特許文献 6〜: L0 及び非特許文献 1〜4参照。)が、これらの配位子では発光材料の発光波長が短波 化して青色を達成し、高効率の素子を達成できる一方、有機 EL素子の発光寿命は 大幅に劣化するため、その改善が求められていた。  [0017] Regarding wavelength shortening, introduction of an electron-withdrawing group such as a fluorine atom, a trifluoromethyl group, and a cyano group as a substituent into phenylpyridine, and coordination of picolinic acid or virazaball as a ligand. It is known to introduce a child (see, for example, Patent Document 6 to: L0 and Non-Patent Documents 1 to 4), but with these ligands, the emission wavelength of the light emitting material is shortened to achieve blue. However, while high-efficiency devices can be achieved, the light-emitting lifetime of organic EL devices is greatly deteriorated, so improvements were required.
特許文献 1 :特開 2002— 332291号公報  Patent Document 1: Japanese Patent Laid-Open No. 2002-332291
特許文献 2:特開 2002— 332292号公報  Patent Document 2: Japanese Patent Laid-Open No. 2002-332292
特許文献 3:特開 2002— 338588号公報  Patent Document 3: Japanese Patent Laid-Open No. 2002-338588
特許文献 4:特開 2002 - 226495号公報  Patent Document 4: Japanese Patent Laid-Open No. 2002-226495
特許文献 5:特開 2002— 234894号公報  Patent Document 5: Japanese Patent Laid-Open No. 2002-234894
特許文献 6 :WO02Zl5645号明細書 特許文献 7:特開 2003— 123982号公報 Patent Document 6: WO02Zl5645 specification Patent Document 7: Japanese Unexamined Patent Publication No. 2003-123982
特許文献 8:特開 2002— 117978号公報  Patent Document 8: Japanese Patent Application Laid-Open No. 2002-117978
特許文献 9:特開 2003 - 146996号公報  Patent Document 9: Japanese Patent Laid-Open No. 2003-146996
特許文献 10 :WO04Z016711号明細書  Patent Document 10: WO04Z016711 Specification
非特許文献 1 : Inorganic Chemistry,第 41卷,第 12号, 3055〜3066ページ(2 002年)  Non-Patent Document 1: Inorganic Chemistry, No. 41, No. 12, pp. 3055-3066 (2002)
非特許文献 2 :Aplied Physics Letters,第 79卷, 2082ページ(2001年) 非特許文献 3 :Aplied Physics Letters,第 83卷, 3818ページ(2003年) 非特許文献 4:New Journal of Chemistry,第 26卷, 1171ページ(2002年) 発明の開示  Non-Patent Document 2: Aplied Physics Letters, 79, 2082 (2001) Non-patent Document 3: Aplied Physics Letters, 83, 3818 (2003) Non-Patent Document 4: New Journal of Chemistry, 26卷, page 1171 (2002) Disclosure of invention
発明が解決しょうとする課題  Problems to be solved by the invention
[0018] 本発明は係る課題に鑑みてなされたものであり、本発明の目的は、高い発光効率 を示し、かつ、発光寿命の長い有機 EL素子材料、有機 EL素子、照明装置及び表示 装置を提供することである。 [0018] The present invention has been made in view of the related problems, and an object of the present invention is to provide an organic EL element material, an organic EL element, an illumination device, and a display device that exhibit high light emission efficiency and have a long light emission lifetime. Is to provide.
課題を解決するための手段  Means for solving the problem
[0019] 本発明の上記課題は、以下の構成により達成される。 [0019] The above object of the present invention is achieved by the following configurations.
本発明及び本発明の好ましい態様について以下に示す。  The present invention and preferred embodiments of the present invention are shown below.
[0020] (1)下記一般式(1)で表されるオルトメタル錯体であることを特徴とする有機エレクト 口ルミネッセンス素子材料。 [0020] (1) An organic electoluminescence device material which is an ortho metal complex represented by the following general formula (1).
[0021] [化 1] 一般式 (1) [0021] [Chemical formula 1] General formula (1)
MLmL' π ML m L ' π
[0022] (式中、 Μは元素周期表における第 8〜10族の金属元素を表す。 L、 L' は互いに 異なる二座配位子を表し、 mは 1または 2であり、 nは 1または 2である。ただし、 m+n は 2または 3であり Mの電荷と一致する。 [In the formula, Μ represents a metal element belonging to Groups 8 to 10 in the periodic table. L and L ′ represent different bidentate ligands, m is 1 or 2, and n is 1 Or 2. However, m + n is 2 or 3, which matches the charge of M.
[0023] 二座配位子 L、L' が金属 Mに配位した部分構造 MLは下記一般式(2)で表され、 部分構造 ML' は下記一般式(3)または (4)で表される。 [0024] [化 2] [0023] Partial structure ML in which bidentate ligands L and L 'are coordinated to metal M is represented by the following general formula (2), and partial structure ML' is represented by the following general formula (3) or (4) Is done. [0024] [Chemical 2]
-般式 (3) -般式 (4) -General formula (3) -General formula (4)
M严、 …、 X3 M 严,…, X 3
ズ 一ノ Ichino
[0025] X は炭素原子または窒素原子を表し、 Q は炭素原子及び X と共に 6員の芳香族 [0025] X represents a carbon atom or a nitrogen atom, and Q represents a 6-membered aromatic together with the carbon atom and X.
11 11 11  11 11 11
炭化水素環または 5〜6員の芳香族複素環である環 Aを形成する原子群を表す。 X  A group of atoms forming a ring A which is a hydrocarbon ring or a 5- to 6-membered aromatic heterocycle. X
12 は炭素原子または窒素原子を表し、 Q  12 represents a carbon atom or a nitrogen atom, and Q
12は窒素原子及び X  12 is nitrogen atom and X
12と共に 5〜6員の芳香族 複素環である環 Bを形成する原子群を表す。 Xは 0、 S、 CH、 CHR、 CR、 NR、 P  A group of atoms that together with 12 forms ring B, which is a 5- to 6-membered aromatic heterocycle. X is 0, S, CH, CHR, CR, NR, P
1 2 2  1 2 2
R、 SiR、 C = 0、 C=NR、 SOまたは SOを表す。 Rはアルキル基、シクロアルキル R, SiR, C = 0, C = NR, SO or SO. R is an alkyl group, cycloalkyl
2 2 twenty two
基、アルケニル基、ァリール基、複素環基または芳香族複素環基を表す。  Represents a group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group.
[0026] X は炭素原子または窒素原子を表し、 Q は炭素原子及び X と共に 6員の芳香族 [0026] X represents a carbon atom or a nitrogen atom, and Q represents a 6-membered aromatic together with the carbon atom and X.
21 21 21  21 21 21
炭化水素環または 5〜6員の芳香族複素環である環 Cを形成する原子群を表す。 X  A group of atoms forming a ring C which is a hydrocarbon ring or a 5- to 6-membered aromatic heterocycle. X
22 は炭素原子または窒素原子を表し、 Q 〜6  22 represents a carbon atom or a nitrogen atom, and Q to 6
22は窒素原子及び X  22 is nitrogen atom and X
22と共に 5 員の芳香族 複素環である環 Dを形成する原子群を表す。 Xは 0、 S、 CH、 CHR、 CR、 NR、 P  This represents the group of atoms that together with 22 form ring D, a 5-membered aromatic heterocycle. X is 0, S, CH, CHR, CR, NR, P
2 2 2  2 2 2
R、 SiR、 C = 0、 C=NR、 SOまたは SOを表す。 Rはアルキル基、シクロアルキル R, SiR, C = 0, C = NR, SO or SO. R is an alkyl group, cycloalkyl
2 2 twenty two
基、アルケニル基、ァリール基、複素環基または芳香族複素環基を表す。  Represents a group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group.
[0027] X 、 X は窒素原子またはリン原子を表し、 Xは X 、X を介して Mに配位している [0027] X and X represent a nitrogen atom or a phosphorus atom, and X is coordinated to M through X and X
31 32 3 31 32  31 32 3 31 32
二座配位子を形成する原子群を表す。 )  A group of atoms forming a bidentate ligand is represented. )
(2)下記一般式(5)で表されるオルトメタル錯体であることを特徴とする前記(1)に 記載の有機エレクト口ルミネッセンス素子材料。  (2) The organic electroluminescent device material according to (1) above, which is an ortho metal complex represented by the following general formula (5).
[0028] [化 3] 般式 (5) [0028] [Chemical 3] General formula (5)
[0029] (式中、 Mは元素周期表における第 8〜10族の金属元素を表す。 mlは 1または 2で あり、 nlは 1または 2である。ただし、 ml +nlは 2または 3であり Mの電荷と一致する 。 X は炭素原子または窒素原子を表し、 Q は炭素原子及び X と共に 6員の芳香族[In the formula, M represents a metal element of Groups 8 to 10 in the periodic table. Ml is 1 or 2, nl is 1 or 2, provided that ml + nl is 2 or 3. Yes Matches the charge of M. X represents a carbon or nitrogen atom, Q represents a 6-membered aromatic with carbon atom and X
11 11 11 11 11 11
炭化水素環または 5〜6員の芳香族複素環である環 Aを形成する原子群を表す。 X  A group of atoms forming a ring A which is a hydrocarbon ring or a 5- to 6-membered aromatic heterocycle. X
12 は炭素原子または窒素原子を表し、 Q  12 represents a carbon atom or a nitrogen atom, and Q
12は窒素原子及び X  12 is nitrogen atom and X
12と共に 5〜6員の芳香族 複素環である環 Bを形成する原子群を表す。 Xは 0、 S、 CH、 CHR、 CR、 NR、 P  A group of atoms that together with 12 forms ring B, which is a 5- to 6-membered aromatic heterocycle. X is 0, S, CH, CHR, CR, NR, P
1 2 2  1 2 2
R、 SiR、 C = 0、 C=NR、 SOまたは SOを表す。 Rはアルキル基、シクロアルキル R, SiR, C = 0, C = NR, SO or SO. R is an alkyl group, cycloalkyl
2 2 twenty two
基、アルケニル基、ァリール基、複素環基または芳香族複素環基を表す。  Represents a group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group.
[0030] X は、炭素原子または窒素原子を表し、 Q は炭素原子及び X と共に 6員の芳香 [0030] X represents a carbon atom or a nitrogen atom, and Q represents a 6-membered aromatic together with the carbon atom and X.
21 21 21  21 21 21
族炭化水素環または 5〜6員の芳香族複素環である環 Cを形成する原子群を表す。 X は炭素原子または窒素原子を表し、 Q は窒素原子及び X と共に 5〜6員の芳香 Represents an atomic group forming a ring C which is a hydrocarbon ring or a 5- to 6-membered aromatic heterocycle. X represents a carbon atom or a nitrogen atom, Q represents a 5- to 6-membered fragrance together with the nitrogen atom and X
22 22 22 22 22 22
族複素環である環 Dを形成する原子群を表す。 Xは 0、 S、 CH、 CHR、 CR、 NR、  Represents a group of atoms forming ring D, a heterocyclic ring. X is 0, S, CH, CHR, CR, NR,
2 2 2 2 2 2
PR、 SiR、 C = 0、 C=NR、 SOまたは SOを表す。 Rはアルキル基、シクロアルキル PR, SiR, C = 0, C = NR, SO or SO. R is an alkyl group, cycloalkyl
2 2  twenty two
基、アルケニル基、ァリール基、複素環基または芳香族複素環基を表す。ただし、環 Represents a group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. However, the ring
Aと環 C、環 Bと環 Dが同時に同じものになることはない。 ) A and ring C, and ring B and ring D cannot be the same at the same time. )
(3)前記一般式 (5)において、芳香族複素環 Bまたは芳香族複素環 Dのうち少なく とも一方が 6員環であり、他方が 5員環であることを特徴とする前記(2)に記載の有機 エレクトロノレミネッセンス素子材料。  (3) In the general formula (5), at least one of the aromatic heterocycle B or the aromatic heterocycle D is a 6-membered ring, and the other is a 5-membered ring (2) The organic electroreluminescence element material described in 1.
[0031] (4)下記一般式 (6)で表されるオルトメタル錯体であることを特徴とする前記(1)に 記載の有機エレクト口ルミネッセンス素子材料。  [0031] (4) The organic electoluminescence device material as described in (1) above, which is an ortho metal complex represented by the following general formula (6).
[0032] [化 4] —般式 (6) [0032] [Chemical 4] —General formula (6)
[0033] (式中、 Mは元素周期表における第 8〜10族の金属元素を表す。 m2は 1または 2で あり、 n2は 1または 2である。ただし、 m2+n2は 2または 3であり Mの電荷と一致する 。 X は炭素原子または窒素原子を表し、 Q は炭素原子及び X と共に 6員の芳香族[In the formula, M represents a metal element of Groups 8 to 10 in the periodic table of elements. M2 is 1 or 2, n2 is 1 or 2. However, m2 + n2 is 2 or 3. Yes Matches the charge of M. X represents a carbon or nitrogen atom, Q represents a 6-membered aromatic with carbon atom and X
11 11 11 11 11 11
炭化水素環または 5〜6員の芳香族複素環である環 Aを形成する原子群を表す。 X  A group of atoms forming a ring A which is a hydrocarbon ring or a 5- to 6-membered aromatic heterocycle. X
12 は炭素原子または窒素原子を表し、 Q  12 represents a carbon atom or a nitrogen atom, and Q
12は窒素原子及び X  12 is nitrogen atom and X
12と共に 5〜6員の芳香族 複素環である環 Bを形成する原子群を表す。 Xは 0、 S、 CH、 CHR、 CR、 NR、 P  A group of atoms that together with 12 forms ring B, which is a 5- to 6-membered aromatic heterocycle. X is 0, S, CH, CHR, CR, NR, P
1 2 2  1 2 2
R、 SiR、 C = 0、 C=NR、 SOまたは SOを表す。 Rはアルキル基、シクロアルキル R, SiR, C = 0, C = NR, SO or SO. R is an alkyl group, cycloalkyl
2 2 twenty two
基、ァルケ-ル基、ァリール基、複素環基または芳香族複素環基を表す。 X 、 X は  A group, an alkyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group; X and X are
31 32 窒素原子またはリン原子を表し、 X 、X  31 32 Represents a nitrogen or phosphorus atom, X, X
3は X  3 is X
31 32を介して Mに配位している二座配位子 を形成する原子群を表す。 )  31 represents an atomic group forming a bidentate ligand coordinated to M through 32. )
(5)前記一般式 (6)において、芳香族複素環 Bが 6員環であることを特徴とする前 記 (4)に記載の有機エレクト口ルミネッセンス素子材料。  (5) The organic electoluminescence device material as described in (4) above, wherein in the general formula (6), the aromatic heterocycle B is a 6-membered ring.
[0034] (6)下記一般式(1 1)〜(1 150)で表される部分構造またはその互変異性体を 部分構造として有するオルトメタル錯体であることを特徴とする前記( 1)〜 (4)の ヽず れカ 1項に記載の有機エレクト口ルミネッセンス素子材料。 [0034] (6) An ortho metal complex having a partial structure represented by the following general formulas (11) to (1150) or a tautomer thereof as a partial structure: The organic electoluminescence device material according to item 1 of (4).
[0035] [化 5] [9εοο] [0035] [Chemical 5] [9εοο]
Oi-- l Oi-- l
OlieOC/900Zdf/I3d 8 0Ζϊ860/900ί OAV llC0C/900Zdf/X3d 6 0ΖΪ860/900Ζ OAV ] OlieOC / 900Zdf / I3d 8 0Ζϊ860 / 900ί OAV llC0C / 900Zdf / X3d 6 0ΖΪ860 / 900Ζ OAV ]
[6^>] [6C00] [6 ^>] [6C00]
V V
Les
llC0£/900Zdf/X3d 0Π860/900Ζ OAV llC0 £ / 900Zdf / X3d 0Π860 / 900Ζ OAV
1] 2] 1] 2]
] ]
] ]
(式中、 Mは元素周期表における第 8〜10族の金属元素を表す。 R 、R は各々置 (In the formula, M represents a metal element belonging to Groups 8 to 10 in the periodic table.
11 12  11 12
換基を表し、 nl l、nl2は各々 0〜2から選ばれる整数を表す。 X 、X は各々〉 N Nl l and nl2 each represents an integer selected from 0 to 2; X and X are each> N
13 14  13 14
-R 、—O—または—S—を表す。 R はアルキル基、シクロアルキル基、アルケニル  It represents -R, -O- or -S-. R is an alkyl group, cycloalkyl group, alkenyl
13 13  13 13
基、ァリール基、複素環基または芳香族複素環基を表す。 X 、 X 、 X 、 X は、各々 Represents a group, aryl group, heterocyclic group or aromatic heterocyclic group. X, X, X, X are each
15 16 17 18  15 16 17 18
>N-R 、—O—または—S—を表す。 R は水素原子、アルキル基、シクロアルキ  > N—R, —O— or —S—. R is a hydrogen atom, alkyl group, cycloalkyl
16 16  16 16
ル基、アルケニル基、ァリール基、複素環基または芳香族複素環基を表す。 X 、 X 、 X は、各々 CHまたは Nを表し、任意の 1つまたは 2つが Nである。 Xは 0、 S、 C b 19c 0 Represents an alkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. X, X , X each represents CH or N, and any one or two of them are N. X is 0, S, C b 19c 0
H 、 CHR、 CR 、 NR、 PR、 SiR 、 C = 0、 C = NR、 SOまたは SOを表す。 Rはアル H, CHR, CR, NR, PR, SiR, C = 0, C = NR, SO or SO. R is al
2 2 2 2 2 2 2 2
キル基、シクロアルキル基、ァルケ-ル基、ァリール基、複素環基または芳香族複素 環基を表す。 )  Represents a kill group, a cycloalkyl group, an alkyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group; )
(7)下記一般式 (2— 1)〜(2— 50)で表される部分構造またはその互変異性体を 部分構造として有するオルトメタル錯体であることを特徴とする前記(1)〜(5)の 、ず れカ 1項に記載の有機エレクト口ルミネッセンス素子材料。  (7) An ortho metal complex having a partial structure represented by the following general formulas (2-1) to (2-50) or a tautomer thereof as a partial structure: The organic electoluminescence element material according to item 1 of 5).
[0046] [化 15] [0046] [Chemical 15]
[0047] [化 16] [0047] [Chemical 16]
[Ζΐ^ ] [8W)0] [Ζΐ ^] [8W) 0]
OllCOC/900Zdf/X3d 61· 0ΖΪ860/900Ζ OAV -21 <R2,〉n2x« "22(R21)N2, 2— 23(R21>N2, XOllCOC / 900Zdf / X3d 61 · 0ΖΪ860 / 900Ζ OAV -21 <R 2 ,> n2 , x «" 22 (R 21 ) N2 , 2-23 (R 21 > N2 , X
,
Ν'' Ν
( 2)π: (2) π:
] ]
] ]
(式中、 Mは元素周期表における第 8〜10族の金属元素を表す。 R 、R は各々置 (In the formula, M represents a metal element belonging to Groups 8 to 10 in the periodic table.
21 22 換基を表し、 n21、n22は 0〜2から選ばれる整数を表す。 X は、〉N— R 、— O—  21 22 represents a substituent, and n21 and n22 each represents an integer selected from 0 to 2. X is> N—R, —O—
23 23 または S を表す。 R は、アルキル基、シクロアルキル基、アルケニル基、ァリール  23 represents 23 or S R is an alkyl group, cycloalkyl group, alkenyl group, aryl
23  twenty three
基、複素環基または芳香族複素環基を表す。 X 、X は、 >N-R 、—O または Represents a group, a heterocyclic group or an aromatic heterocyclic group. X and X are> N-R, —O or
24 25 24  24 25 24
S を表す。 R は水素原子、アルキル基、シクロアルキル基、アルケニル基、ァリ  Represents S. R is a hydrogen atom, alkyl group, cycloalkyl group, alkenyl group, aryl
24  twenty four
ール基、複素環基または芳香族複素環基を表す。 X 、X 、X は各々 CHまたは N Represents an aryl group, a heterocyclic group or an aromatic heterocyclic group. X, X, X are each CH or N
26 27 28  26 27 28
を表し、任意の 1つまたは 2つが Nである。 Xは 0、 S、 CH、 CHR、 CR、 NR、 PR、 And any one or two is N. X is 0, S, CH, CHR, CR, NR, PR,
0 2 2  0 2 2
SiR、 C = 0、 C=NR、 SOまたは SOを表す。 Rはアルキル基、シクロアルキル基、 Represents SiR, C = 0, C = NR, SO or SO. R is an alkyl group, a cycloalkyl group,
2 2 twenty two
アルケニル基、ァリール基、複素環基または芳香族複素環基を表す。 ) An alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group; )
(8)下記一般式 (3— 1)〜(3— 10)で表される部分構造またはその互変異性体を 部分構造として有するオルトメタル錯体であることを特徴とする前記(1)〜(5)の ヽず れカ 1項の記載の有機エレクト口ルミネッセンス素子材料。 [0052] [化 20] (8) The orthometal complex having a partial structure represented by the following general formulas (3-1) to (3-10) or a tautomer thereof as a partial structure: 5. Organic electroluminescence element material according to item 1 of 5). [0052] [Chemical 20]
[0053] (式中、 Mは元素周期表における第 8〜10族の金属元素を表す。 R 、R は各々置 [In the formula, M represents a metal element of Groups 8 to 10 in the periodic table.
31 32 換基を表し、 n31、n32は 0〜2から選ばれる整数を表す。 X は、〉N— R 、— O—  31 32 represents a substituent, and n31 and n32 represent an integer selected from 0 to 2. X is> N—R, —O—
31 33 または S を表す。 R はアルキル基、シクロアルキル基、アルケニル基、ァリール  31 represents 33 or S R is an alkyl group, cycloalkyl group, alkenyl group, aryl
33  33
基、複素環基または芳香族複素環基を表す。 X 、X は、 >N-R 、—O または  Represents a group, a heterocyclic group or an aromatic heterocyclic group. X and X are> N-R, —O or
32 33 34  32 33 34
S を表す。 R は水素原子、アルキル基、シクロアルキル基、アルケニル基、ァリ  Represents S. R is a hydrogen atom, alkyl group, cycloalkyl group, alkenyl group, alkyl
34  34
ール基、複素環基または芳香族複素環基を表す。 X 、X 、X は各々 CHまたは N  Represents an aryl group, a heterocyclic group or an aromatic heterocyclic group. X, X, X are each CH or N
34 35 36  34 35 36
を表し、任意の 1つまたは 2つが Nである。 Xは 0、 S、 CH、 CHR、 CR、 NR、 PR、  And any one or two is N. X is 0, S, CH, CHR, CR, NR, PR,
0 2 2  0 2 2
SiR、 C = 0、 C=NR、 SOまたは SOを表す。 Rはアルキル基、シクロアルキル基、 Represents SiR, C = 0, C = NR, SO or SO. R is an alkyl group, a cycloalkyl group,
2 2 twenty two
アルケニル基、ァリール基、複素環基または芳香族複素環基を表す。 )  An alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group; )
(9)下記一般式 (7)で表される部分構造またはその互変異性体を部分構造として 有するオルトメタル錯体であることを特徴とする前記(1)〜(5)、 (8)の 、ずれか 1項 に記載の有機エレクト口ルミネッセンス素子材料。 [0054] [化 21] 一般式《7) (9) The orthometal complex having a partial structure represented by the following general formula (7) or a tautomer thereof as a partial structure: (1) to (5), The organic electoluminescence device material according to claim 1. [0054] [Chemical Formula 21] General formula << 7
[0055] (式中、 Mは元素周期表における第 8〜10族の金属元素を表す。 X は炭素原子ま [0055] (In the formula, M represents a metal element of Groups 8 to 10 in the periodic table. X represents a carbon atom.
41  41
たは窒素原子を表し、 Q 6員の  Or a nitrogen atom, Q 6-membered
41は炭素原子及び X  41 is carbon atom and X
41と共に 芳香族炭化水素環または With 41 aromatic hydrocarbon ring or
5〜6員の芳香族複素環である環 Eを形成する原子群を表す。 R は置換基を表し、 n A group of atoms forming ring E, which is a 5- to 6-membered aromatic heterocycle. R represents a substituent, and n
41  41
4は 0〜3から選ばれる整数を表す。 Xaは— N (Ra)、— O— Raまたは— S— Raを表  4 represents an integer selected from 0 to 3. Xa represents —N (Ra), —O—Ra or —S—Ra
2  2
す。 Raはアルキル基、シクロアルキル基、アルケニル基、ァリール基、複素環基また は芳香族複素環基を表す。 Xaが— N (Ra)の場合、 2つの Raは同じであっても異な  The Ra represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. If Xa is — N (Ra), the two Ras are the same but different
2  2
つていてもよい。 Xは 0、 S、 CH、 CHR、 CR、 NR、 PR、 SiR、 C = 0、 C=NR、 S  You may go on. X is 0, S, CH, CHR, CR, NR, PR, SiR, C = 0, C = NR, S
4 2 2 2  4 2 2 2
Oまたは SOを表す。 Rはアルキル基、シクロアルキル基、アルケニル基、ァリール基  Represents O or SO. R is an alkyl group, cycloalkyl group, alkenyl group, aryl group
2  2
、複素環基または芳香族複素環基を表す。 )  Represents a heterocyclic group or an aromatic heterocyclic group. )
(10)下記一般式 (8)または(9)で表される部分構造またはその互変異性体を部分 構造として有するオルトメタル錯体であることを特徴とする前記(9)に記載の有機エレ タトロルミネッセンス素子材料。  (10) The organic eletro described in (9) above, which is an ortho metal complex having a partial structure represented by the following general formula (8) or (9) or a tautomer thereof as a partial structure: Luminescence element material.
[0056] [化 22]  [0056] [Chemical 22]
[0057] (式中、 Mは元素周期表における第 8〜10族の金属元素を表す。 R 、R 、R 、R は、各々水素原子または電子供与性の置換基を表し、少なくとも 1つは電子供与性 の置換基である。 R 、R 、R 、R [In the formula, M represents a metal element of Groups 8 to 10 in the periodic table of elements. R 1, R 2, R 3, R 5 Each represents a hydrogen atom or an electron-donating substituent, and at least one is an electron-donating substituent. R, R, R, R
56 57 58 59は、各々水素原子または置換基を表し、 R 、R  56 57 58 59 each represents a hydrogen atom or a substituent, and R 1, R 2
56 58 の少なくとも一方は電子吸引性の置換基である。 R 、 R は置換基を表し、 n51、 n5  At least one of 56 58 is an electron-withdrawing substituent. R 1 and R 2 represent a substituent, n51, n5
50 55  50 55
2は 0〜3から選ばれる整数を表す。 Xaは— N (Ra)、— O— Raまたは— S— Raを表  2 represents an integer selected from 0 to 3. Xa represents —N (Ra), —O—Ra or —S—Ra
2  2
す。 Raはアルキル基、シクロアルキル基、アルケニル基、ァリール基、複素環基また は芳香族複素環基を表す。 Xaが— N (Ra)の場合、 2つの Raは同じであっても異な  The Ra represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. If Xa is — N (Ra), the two Ras are the same but different
2  2
つていてもよい。 Xは 0、 S、 CH、 CHR、 CR、 NR、 PR、 SiR、 C = 0、 C=NR、 S  You may go on. X is 0, S, CH, CHR, CR, NR, PR, SiR, C = 0, C = NR, S
5 2 2 2  5 2 2 2
Oまたは SOを表す。 Rはアルキル基、シクロアルキル基、アルケニル基、ァリール基  Represents O or SO. R is an alkyl group, cycloalkyl group, alkenyl group, aryl group
2  2
、複素環基または芳香族複素環基を表す。 )  Represents a heterocyclic group or an aromatic heterocyclic group. )
(11)下記一般式 (10)で表される部分構造またはその互変異性体を部分構造とし て有するオルトメタル錯体であることを特徴とする前記(1)〜(10)のいずれか 1項に 記載の有機エレクト口ルミネッセンス素子材料。  (11) Any one of the above (1) to (10), which is an orthometal complex having a partial structure represented by the following general formula (10) or a tautomer thereof as a partial structure: The organic electoluminescence device material described in 1.
[0058] [化 23]  [0058] [Chemical 23]
[0059] (式中、 Mは元素周期表における第 8〜10族の金属元素を表す。 X 、X 、X 、X (In the formula, M represents a metal element of Groups 8 to 10 in the periodic table. X 1, X 2, X 3, X 4
61 62 63 64 は、各々炭素原子または窒素原子を表し、 Q  61 62 63 64 each represents a carbon atom or a nitrogen atom, and Q
61は炭素原子及び X 、X  61 is a carbon atom and X, X
61 63と共に 6員の 芳香族炭化水素環または 5〜6員の芳香族複素環である環 Fを形成する原子群を表 し、 Q は窒素原子及び X 、 X と共に 5〜6員の芳香族複素環である環 Gを形成す 61 represents a group of atoms forming a ring F which is a 6-membered aromatic hydrocarbon ring or a 5- to 6-membered aromatic heterocycle with 63 63, Q is a nitrogen atom and a 5- to 6-membered aromatic together with X and X Form a ring G that is a heterocycle
62 62 64 62 62 64
る原子群を表す。 X、 Xはファンデルワールス体積が 20 A3以上である置換基を表し b c Represents an atomic group. X and X represent substituents whose van der Waals volume is 20 A 3 or more bc
。 m6、 n6は 0または 1を表す。ただし、 m6 +n6≥lである。 Xは 0、 S、 CH、 CHR、  . m6 and n6 each represents 0 or 1. However, m6 + n6≥l. X is 0, S, CH, CHR,
6 2 6 2
CR、 NR、 PR、 SiR、 C = 0、 C=NR、 SOまたは SOを表す。 Rはアルキル基、シクCR, NR, PR, SiR, C = 0, C = NR, SO or SO. R is an alkyl group,
2 2 2 2 2 2
口アルキル基、アルケニル基、ァリール基、複素環基または芳香族複素環基を表す。 ) (12)下記一般式 (11)〜(14)で表される部分構造またはその互変異性体を部分 構造として有するオルトメタル錯体であることを特徴とする前記(10)に記載の有機ェ レクト口ルミネッセンス素子材料。 It represents a mouth alkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. ) (12) The organic elector according to (10) above, which is an orthometal complex having a partial structure represented by the following general formulas (11) to (14) or a tautomer thereof as a partial structure: Mouth luminescence element material.
[化 24]  [Chemical 24]
一般式 (13) -般式 (14) General formula (13)-General formula (14)
7 7
(式中、 Mは元素周期表における第 8〜10族の金属元素を表す。 X 、X 、X 、X (In the formula, M represents a metal element of Groups 8 to 10 in the periodic table. X 1, X 2, X 3, X 4
71 72 73 74 は、各々炭素原子または窒素原子を表し、 Q  71 72 73 74 each represents a carbon atom or a nitrogen atom, and Q
71は炭素原子、 X 、X  71 is a carbon atom, X, X
71 73と共に 6員の芳 香族炭化水素環または 5〜6員の芳香族複素環である環 Hを形成する原子群を表し 、 Q は窒素原子、 X 、 X と共に 5〜6員の芳香族複素環である環 Kを形成する原子 71 73 represents a group of atoms forming a ring H which is a 6-membered aromatic hydrocarbon ring or a 5- to 6-membered aromatic heterocycle, Q is a nitrogen atom, and a 5- to 6-membered aromatic together with X and X Atom that forms ring K, a heterocycle
72 72 74 72 72 74
群を表す。 Q Represents a group. Q
73は炭素原子と共に芳香族炭化水素環または芳香族複素環を形成する 原子群を表す。 Q  73 represents an atomic group that forms an aromatic hydrocarbon ring or an aromatic heterocycle with carbon atoms. Q
74は窒素原子と共に芳香族複素環を形成する原子群を表す。 X  74 represents an atomic group forming an aromatic heterocyclic ring with a nitrogen atom. X
7は 7
0、 S、 CH、 CHR、 CR、 NR、 PR、 SiR、 C = 0、 C=NR、 SOまたは SOを表す。 0, S, CH, CHR, CR, NR, PR, SiR, C = 0, C = NR, SO or SO.
2 2 2 2 2 2 2 2
Rはアルキル基、シクロアルキル基、アルケニル基、ァリール基、複素環基または芳 香族複素環基を表す。 ) R represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. )
( 13)前記一般式 (4)または一般式 (6)の X — X— X によって形成される二座配  (13) Bidentate formed by X — X— X in general formula (4) or general formula (6)
31 3 32  31 3 32
位子が、下記一般式 (4 1)〜 (4 31)で表される部分構造またはまたはその互変 異性体を部分構造として有することを特徴とする前記(1)、(4)〜(12)のいずれか 1 項に記載の有機エレクト口ルミネッセンス素子材料。 The ligand is a partial structure represented by the following general formulas (41) to (433) or tautomers thereof: The organic electroluminescent device material according to any one of (1) and (4) to (12) above, which has an isomer as a partial structure.
[0062] [化 25] [0062] [Chemical 25]
4-1 4-2 4-3 4-1 4-2 4-3
、- -«¾2 、 Q'8'2 、、- <¾'2 ,-«¾ 2 , Q'8'2,-<¾ ' 2
[0063] [化 26] 4-20 4-21 4-22 4-23 [0063] [Chemical 26] 4-20 4-21 4-22 4-23
[0064] (式中、 R は R —CO—または R —SO—を表し、 R はアルキル基、シクロアルキ [0064] (wherein R represents R —CO— or R —SO—, R represents an alkyl group, cycloalkyl,
81 80 80 2 80  81 80 80 2 80
ル基、ァリール基、複素環基または芳香族複素環基を表す。 R 、 R 、 R 、 R  Represents an alkyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. R, R, R, R
82 83 86 87は置 換基を表し、 n は 0〜3の整数を表し、 n 、n は 0〜2の整数を表す。 R 、R 、R 、  82 83 86 87 represents a substituent, n represents an integer of 0 to 3, and n and n represent an integer of 0 to 2. R, R, R,
81 82 83 84 85 88 81 82 83 84 85 88
R はアルキル基、シクロアルキル基、ァリール基、複素環基または芳香族複素環基R is an alkyl group, a cycloalkyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group
89 89
を表す。 Q は炭素、窒素と共に 5〜6員の芳香族複素環を形成する原子群を表し、  Represents. Q represents an atomic group that forms a 5- or 6-membered aromatic heterocycle with carbon and nitrogen,
81  81
Q 、 Q は炭素、窒素と共に 5員の芳香族複素環を形成する原子群を表す。)  Q and Q represent an atomic group that forms a 5-membered aromatic heterocycle with carbon and nitrogen. )
82 83  82 83
(14) M力イリジウムまたは白金であることを特徴とする前記(1)〜(13)のいずれか (14) Any one of (1) to (13) above, which is M force iridium or platinum
1項に記載の有機エレクト口ルミネッセンス素子材料。 The organic electoluminescence device material according to item 1.
[0065] ( 15)前記( 1)〜( 14)の!、ずれか 1項に記載の有機エレクト口ルミネッセンス素子材 料を含有することを特徴とする有機エレクト口ルミネッセンス素子。 [0065] (15) An organic electroluminescent device comprising the organic electroluminescent device according to (1) to (14), wherein the organic electroluminescent device is described above.
[0066] (16)構成層として発光層を有し、該発光層が前記(1)〜(14)のいずれ力 1項に記 載の有機エレクト口ルミネッセンス素子材料を含有することを特徴とする有機エレクト ロノレミネッセンス素子。 [0066] (16) A light emitting layer is included as a constituent layer, and the light emitting layer contains the organic electoluminescence device material described in any one of (1) to (14) above. Organic electroreductive element.
[0067] (17)構成層として正孔阻止層を有し、該正孔阻止層が前記(1)〜(14)のいずれ 力 1項に記載の有機エレクト口ルミネッセンス素子材料を含有することを特徴とする有 機エレクト口ルミネッセンス素子。 [0067] (17) It has a hole blocking layer as a constituent layer, and the hole blocking layer is any of the above (1) to (14) Force An organic electoluminescence device comprising the organic electroluminescence device described in item 1.
[0068] ( 18)下記一般式( 1 A)で表される化合物を含有することを特徴とする前記( 15)〜  [0068] (18) A compound represented by the following general formula (1A):
(17)のいずれ力 1項に記載の有機エレクト口ルミネッセンス素子。  The organic electoluminescence device according to any one of (17).
[0069] [化 27] [0069] [Chemical 27]
—般式 (1A} —General formula (1A}
',' ----z3- - -c、 1 ',' ---- z 3 ---c, 1
[0070] (式中、 Zは芳香族複素環を表し、 Zは芳香族複素環または芳香族炭化水素環を表 [0070] (In the formula, Z represents an aromatic heterocyclic ring, Z represents an aromatic heterocyclic ring or an aromatic hydrocarbon ring.
1 2  1 2
し、 Zは 2価の連結基または単なる結合手を表す。 R は水素原子または置換基を表 Z represents a divalent linking group or a simple bond. R represents a hydrogen atom or a substituent.
3 101 3 101
す。)  The )
( 19)前記一般式( 1 A)で表される化合物の Zが 6員環であることを特徴とする前記  (19) The compound represented by the general formula (1A), wherein Z is a 6-membered ring
1  1
(18)に記載の有機エレクト口ルミネッセンス素子。  (18) The organic electoluminescence device according to (18).
[0071] (20)前記一般式(1A)で表される化合物の Zが 6員環であることを特徴とする前記  (20) The compound represented by the general formula (1A) is characterized in that Z is a 6-membered ring
2  2
( 18)または( 19)に記載の有機エレクト口ルミネッセンス素子。  (18) or (19) The organic electoluminescence device according to (19).
[0072] (21)前記一般式(1A)で表される化合物の Zが結合手であることを特徴とする前 [0072] (21) The compound represented by the general formula (1A) is characterized in that Z is a bond.
3  Three
記(18)〜(20)の!、ずれ力 1項に記載の有機エレクト口ルミネッセンス素子。  (18) to (20) !, shift force The organic electoluminescence device according to item 1.
[0073] (22)前記一般式(1A)で表される化合物が分子量 450以上であることを特徴とす る前記(18)〜(21)の 、ずれ力 1項に記載の有機エレクト口ルミネッセンス素子。 [0073] (22) The organic electoluminescence according to item (18), wherein the compound represented by the general formula (1A) has a molecular weight of 450 or more. element.
[0074] (23)前記一般式(1A)で表される化合物が下記一般式(1 A— 1)で表されることを 特徴とする前記(18)〜(22)の 、ずれか 1項に記載の有機エレクト口ルミネッセンス 素子。 [0074] (23) The compound represented by the general formula (1A) is represented by the following general formula (1A-1), wherein any one of the above (18) to (22) The organic electoluminous luminescence element of description.
[0075] [化 28] 般式 (1A— 1> [0075] [Chemical 28] General formula (1A— 1>
[0076] (式中、 R 〜R は各々独立に水素原子または置換基を表す。) [In the formula, R 1 to R 4 each independently represents a hydrogen atom or a substituent.]
501 507  501 507
(24)前記一般式(1A)で表される化合物が下記一般式(1 A— 2)で表されることを 特徴とする前記(18)〜(22)の 、ずれか 1項に記載の有機エレクト口ルミネッセンス 素子。  (24) The compound represented by the general formula (1A) is represented by the following general formula (1A-2), wherein any one of the above (18) to (22) Organic-elect mouth luminescence element.
[0077] [化 29] [0077] [Chemical 29]
—般式 (1A— 2> —General formula (1A— 2>
[0078] (式中、 R 〜R は各々独立に水素原子または置換基を表す。) [In the formula, R 1 to R 4 each independently represents a hydrogen atom or a substituent.]
511 517  511 517
(25)前記一般式(1A)で表される化合物が下記一般式(1 A— 3)で表されることを 特徴とする前記(18)〜(22)の 、ずれか 1項に記載の有機エレクト口ルミネッセンス 素子。  (25) The compound represented by the general formula (1A) is represented by the following general formula (1 A-3), wherein any one of the above (18) to (22) Organic-elect mouth luminescence element.
[0079] [化 30] 一般式 (1A - 3) [0079] [Chemical 30] General formula (1A-3)
(式中、 R 〜R は各々独立に水素原子または置換基を表す。) (In the formula, R to R each independently represent a hydrogen atom or a substituent.)
521 527  521 527
(26)前記一般式(1A)で表される化合物が下記一般式(1A— 4)で表されることを 特徴とする前記(18)〜(22)の 、ずれか 1項に記載の有機エレクト口ルミネッセンス 素子。 (26) The organic compound according to any one of (18) to (22), wherein the compound represented by the general formula (1A) is represented by the following general formula (1A-4): Elect mouth luminescence element.
[0081] [化 31] 一般式 (1A_4> [0081] [Chemical 31] General formula (1A_4>
[0082] (式中、 R 〜R は各々独立に水素原子または置換基を表す。) [In the formula, R 1 to R 4 each independently represents a hydrogen atom or a substituent.]
531 537  531 537
(27)前記一般式(1A)で表される化合物が下記一般式(1 A— 5)で表されることを 特徴とする前記(18)〜(22)の 、ずれか 1項に記載の有機エレクト口ルミネッセンス 素子。  (27) The compound represented by the general formula (1A) is represented by the following general formula (1A-5), wherein any one of the above (18) to (22) Organic-elect mouth luminescence element.
[0083] [化 32] [0083] [Chemical 32]
—般式 (1A- S) —General formula (1A-S)
[0084] (式中、 R 〜R は各々独立に水素原子または置換基を表す。) [In the formula, R 1 to R 4 each independently represents a hydrogen atom or a substituent.]
541 548  541 548
(28)前記一般式(1A)で表される化合物が下記一般式(1 A— 6)で表されることを 特徴とする前記(18)〜(22)の 、ずれか 1項に記載の有機エレクト口ルミネッセンス 素子。  (28) The compound represented by the general formula (1A) is represented by the following general formula (1A-6), wherein any one of the above (18) to (22) Organic-elect mouth luminescence element.
[0085] [化 33] 一般式 ΠΑ— 6} [0085] [Chemical formula 33] General formula ΠΑ— 6}
[0086] (式中、 R 〜R は各々独立に水素原子または置換基を表す。) (29)前記一般式(1 A)で表される化合物が下記一般式(1 A— 7)で表されることを 特徴とする前記(18)〜(22)の 、ずれか 1項に記載の有機エレクト口ルミネッセンス 素子。 [0086] (wherein R 1 to R 4 each independently represents a hydrogen atom or a substituent) (29) The compound represented by the general formula (1A) is represented by the following general formula (1A-7), or any one of the above (18) to (22), Organic-elect luminescence element.
[0087] [化 34] 一般式《1A_7) [0087] [Chemical Formula 34] General Formula << 1A_7)
[0088] (式中、 R 〜R は各々独立に水素原子または置換基を表す。) [In the formula, R 1 to R 3 each independently represents a hydrogen atom or a substituent.]
561 567  561 567
(30)前記一般式(1A)で表される化合物が下記一般式(1 A— 8)で表されることを 特徴とする前記(18)〜(22)の 、ずれか 1項に記載の有機エレクト口ルミネッセンス 素子。  (30) The compound represented by the general formula (1A) is represented by the following general formula (1A-8), wherein any one of the above (18) to (22) Organic-elect mouth luminescence element.
[0089] [化 35] [0089] [Chemical 35]
—般式 <1A_8) —General formula <1A_8)
[0090] (式中、 R 〜R は各々独立に水素原子または置換基を表す。) [In the formula, R 1 to R 4 each independently represents a hydrogen atom or a substituent.]
571 577  571 577
(31)前記一般式(1A)で表される化合物が下記一般式(1 A— 9)で表されることを 特徴とする前記(18)〜(22)の 、ずれか 1項に記載の有機エレクト口ルミネッセンス 素子。  (31) The compound represented by the general formula (1A) is represented by the following general formula (1A-9), wherein any one of the above (18) to (22) Organic-elect mouth luminescence element.
[0091] [化 36] —般式 (1A—9) [0091] [Chemical 36] —General formula (1A-9)
[0092] (式中、 Rは水素原子または置換基を表す。また、複数の Rは各々同一でもよぐ異な つていてもよい。 ) [In the formula, R represents a hydrogen atom or a substituent. Also, a plurality of R may be the same or different.)
(32)前記一般式(1A)で表される化合物が下記一般式(1 A— 10)で表されること を特徴とする前記(18)〜(22)の 、ずれ力 1項に記載の有機エレクト口ルミネッセンス 素子。  (32) The compound represented by the general formula (1A) is represented by the following general formula (1A-10): Organic-elect mouth luminescence element.
[0093] [化 37] [0093] [Chemical 37]
—般式 (1A_10> —General formula (1A_10>
[0094] (式中、 Rは水素原子または置換基を表す。また、複数の Rは各々同一でもよぐ異な つていてもよい。 ) [In the formula, R represents a hydrogen atom or a substituent. Further, a plurality of R may be the same or different from each other.)
(33)前記一般式(1A)で表される化合物が下記一般式(2A— 1)〜(2A— 10)の いずれかで表される基を少なくとも一つ有することを特徴とする前記(18)〜(22)の いずれか 1項に記載の有機エレクト口ルミネッセンス素子。  (33) The compound represented by the general formula (1A) has at least one group represented by any one of the following general formulas (2A-1) to (2A-10): The organic electoluminescence device according to any one of (1) to (22).
[0095] [化 38] -般式 (2A— 1 ) —般式 (2A— 2>[0095] [Chemical 38] -General formula (2A— 1) — General formula (2A— 2>
(式中、 R 〜R 、R 〜R 、R 〜R 、 R 〜R 、 R 〜 R 、R 〜R 、R (Wherein R to R, R to R, R to R, R to R, R to R, R to R, R
502 507 512 517 522 527 532 537 552  502 507 512 517 522 527 532 537 552
〜R 、R 〜R 、R 〜R 、R 〜R は各々独立に水素原子または置換基を表 ~ R, R ~ R, R ~ R, R ~ R each independently represents a hydrogen atom or a substituent.
567 572 577 582 588 592 598 567 572 577 582 588 592 598
し、該置換基は各々同一でもよぐ異なっていてもよい。 ) The substituents may be the same or different. )
(34)前記一般式( 1 A)で表される化合物が下記一般式 (3A)で表されることを特徴 とする前記(18)〜(22)のいずれか 1項に記載の有機エレクト口ルミネッセンス素子。 [0097] [化 39] (34) The organic elect mouth according to any one of (18) to (22), wherein the compound represented by the general formula (1A) is represented by the following general formula (3A): Luminescence element. [0097] [Chemical 39]
般式 (3A) General formula (3A)
[0098] (式中、 R 〜R 〜R [0098] (wherein R to R to R
601 606は各々独立に水素原子または置換基を表す力 R  601 606 are each independently a force representing a hydrogen atom or a substituent R
601 606の少な くとも一つは前記一般式(2— 1)〜(2— 10)で表される基力 選ばれる少なくとも一 つの基を表す。 )  At least one of 601 606 represents at least one group selected from the basic forces represented by the general formulas (2-1) to (2-10). )
(35)前記一般式( 1 A)で表される化合物が下記一般式 (4A)で表されることを特徴 とする前記(18)〜(22)の 、ずれか 1項に記載の有機エレクト口ルミネッセンス素子。  (35) The organic elect according to any one of (18) to (22) above, wherein the compound represented by the general formula (1A) is represented by the following general formula (4A): Mouth luminescence element.
[0099] [化 40] [0099] [Chemical 40]
'般式 (4A) 'General formula (4A)
[0100] (式中、 R 〜R は各々独立に水素原子または置換基を表す力 R 〜R の少な [0100] (wherein R to R each independently represents a hydrogen atom or a substituent having a small force R to R)
611 620 611 620 くとも一つは前記一般式(2A— 1)〜(2A— 10)で表される基から選ばれる少なくとも 一つの基を表す。 )  611 620 611 620 At least one represents at least one group selected from the groups represented by the general formulas (2A-1) to (2A-10). )
(36)前記一般式(1A)で表される化合物が下記一般式(5A)で表されることを特徴 とする前記(18)〜(22)の 、ずれか 1項に記載の有機エレクト口ルミネッセンス素子。  (36) The organic elect mouth according to any one of (18) to (22) above, wherein the compound represented by the general formula (1A) is represented by the following general formula (5A): Luminescence element.
[0101] [化 41] 一般式 (5A) [0101] [Chemical 41] General formula (5A)
N人 N  N people N
π 人人 '  π people ''
[0102] (式中、 R 〜R は各々独立に水素原子または置換基を表す力 R 〜R の少な くとも一つは前記一般式(2A— 1)〜(2A— 10)で表される基から選ばれる少なくとも 一つの基を表す。 ) [0102] (wherein R to R each independently represents a hydrogen atom or a substituent having a small force R to R) At least one represents at least one group selected from the groups represented by the general formulas (2A-1) to (2A-10). )
(37)前記一般式( 1 A)で表される化合物が下記一般式 (6A)で表されることを特徴 とする前記(18)〜(22)の 、ずれか 1項に記載の有機エレクト口ルミネッセンス素子。  (37) The organic elect described in any one of (18) to (22) above, wherein the compound represented by the general formula (1A) is represented by the following general formula (6A): Mouth luminescence element.
[化 42] 一般式 (6A)  [Chemical Formula 42] General formula (6A)
[0104] (式中、 R [0104] (where R
631〜R  631-R
645は各々独立に水素原子または置換基を表す力 R  645 is a force representing a hydrogen atom or a substituent each independently R
631〜R  631-R
645の少な くとも一つは前記一般式(2A— 1)〜(2A— 10)で表される基から選ばれる少なくとも 一つの基を表す。 )  At least one of 645 represents at least one group selected from the groups represented by the general formulas (2A-1) to (2A-10). )
(38)前記一般式( 1 A)で表される化合物が下記一般式 (7A)で表されることを特徴 とする前記(18)〜(22)の 、ずれか 1項に記載の有機エレクト口ルミネッセンス素子。  (38) The organic elect described in any one of (18) to (22) above, wherein the compound represented by the general formula (1A) is represented by the following general formula (7A): Mouth luminescence element.
[0105] [化 43] 一般式 (7A) [0105] [Chemical formula 43] General formula (7A)
[0106] (式中、 R 〜R は各々独立に水素原子または置換基を表す力 R 〜R の少な [Wherein R 1 to R 4 each independently represents a hydrogen atom or a substituent having a small force R 1 to R 5
651 656 651 656 くとも一つは前記一般式(2— 1)〜(2— 10)で表される基力 選ばれる少なくとも一 つの基を表す。 naは 0〜5の整数を表し、 nbは 1〜6の整数を表すが、 naと nbの和は 6である。) 651 656 651 656 At least one represents at least one group selected from the basic forces represented by the general formulas (2-1) to (2-10). na represents an integer from 0 to 5, nb represents an integer from 1 to 6, but the sum of na and nb is 6. )
(39)前記一般式(1 A)で表される化合物が下記一般式 (8A)で表されることを特徴 とする前記(18)〜(22)の 、ずれか 1項に記載の有機エレクト口ルミネッセンス素子。  (39) The organic elect according to any one of (18) to (22) above, wherein the compound represented by the general formula (1A) is represented by the following general formula (8A): Mouth luminescence element.
[化 44] 一般式 <8AJ  [Chemical formula 44] General formula <8AJ
[0108] (式中、 R 〜R は各々独立に水素原子または置換基を表す力 R 〜R の少な [0108] (wherein R to R each independently represents a hydrogen atom or a substituent having a small force R to R)
661 672 661 672 くとも一つは前記一般式(2A— 1)〜(2A— 10)で表される基から選ばれる少なくとも 一つの基を表す。 )  661 672 661 672 At least one represents at least one group selected from the groups represented by the general formulas (2A-1) to (2A-10). )
(40)前記一般式( 1 A)で表される化合物が下記一般式 (9A)で表されることを特徴 とする前記(18)〜(22)の 、ずれか 1項に記載の有機エレクト口ルミネッセンス素子。  (40) The organic elect according to any one of (18) to (22) above, wherein the compound represented by the general formula (1A) is represented by the following general formula (9A): Mouth luminescence element.
[0109] [化 45] 一般式 (9A) [0109] [Chemical 45] General formula (9A)
くとも一つは前記一般式(2A— 1)〜(2A— 10)で表される基力 選ばれる少なくとも 一つの基を表す。 ) (41)前記一般式(1A)で表される化合物が下記一般式(10A)で表されることを特 徴とする前記(18)〜(22)の 、ずれか 1項に記載の有機エレクト口ルミネッセンス素 子。 At least one represents at least one group selected from the basic forces represented by the general formulas (2A-1) to (2A-10). ) (41) The organic elect described in any one of (18) to (22) above, wherein the compound represented by the general formula (1A) is represented by the following general formula (10A): Mouth luminescence element.
[0111] [化 46] 一般式 (10A> [0111] [Chemical 46] General formula (10A>
[0112] (式中、 R 〜R は各々独立に水素原子または置換基を表すが、 Lは 2価の連結基 [0112] (wherein R to R each independently represents a hydrogen atom or a substituent, L represents a divalent linking group.
691 700 1  691 700 1
を表す。 R 〜R の少なくとも一つは前記一般式(2A— 1)〜(2A— 10)で表される  Represents. At least one of R 1 to R 4 is represented by the general formulas (2A-1) to (2A-10)
691 700  691 700
基カゝら選ばれる少なくとも一つの基を表す。 )  It represents at least one group selected from the group. )
(42)前記一般式( 1 A)で表される化合物が下記一般式( 11 A)で表されることを特 徴とする前記(18)〜(22)の 、ずれか 1項に記載の有機エレクト口ルミネッセンス素 子。  (42) The compound according to any one of (18) to (22) above, wherein the compound represented by the general formula (1A) is represented by the following general formula (11A): Organic-elect mouth luminescence element.
[0113] [化 47] 般式 (11 A) [0113] [Chemical formula 47] General formula (11 A)
[0114] (式中、 R、 Rは各々独立に水素原子または置換基を表す。 n、 mは各々 1〜2の整 [In the formula, R and R each independently represent a hydrogen atom or a substituent. N and m are each an integer of 1 to 2.
1 2  1 2
数を表し、 k、 1は各々 3〜4の整数を表す。但し、 n+k= 5、かつ l+m= 5である。 ) K and 1 each represent an integer of 3 to 4. However, n + k = 5 and l + m = 5. )
(43)前記一般式(1A)で表される化合物が下記一般式(12A)で表されることを特 徴とする前記(18)〜(22)の 、ずれか 1項に記載の有機エレクト口ルミネッセンス素 子。 (43) The organic elect described in any one of (18) to (22) above, wherein the compound represented by the general formula (1A) is represented by the following general formula (12A): Mouth luminescence element.
[0115] [化 48] —般式 (12A) [0115] [Chemical 48] —General formula (12A)
[0116] (式中、 R、 Rは各々独立に水素原子または置換基を表す。 n、 mは各々 1〜2の整 [In the formula, R and R each independently represent a hydrogen atom or a substituent. N and m are each an integer of 1 to 2.
1 2  1 2
数を表し、 k、 1は各々 3〜4の整数を表す。但し、 n+k= 5、かつ l+m= 5である。 ) K and 1 each represent an integer of 3 to 4. However, n + k = 5 and l + m = 5. )
(44)前記一般式(1A)で表される化合物が下記一般式(13A)で表されることを特 徴とする前記(18)〜(22)の 、ずれか 1項に記載の有機エレクト口ルミネッセンス素 子。 (44) The organic elect described in any one of (18) to (22) above, wherein the compound represented by the general formula (1A) is represented by the following general formula (13A): Mouth luminescence element.
[0117] [化 49] 一般式 (13A) [0117] [Chemical formula 49] General formula (13A)
[0118] (式中、 R、 Rは各々独立に水素原子または置換基を表す。 n、 mは各々 1〜2の整 [In the formula, R and R each independently represent a hydrogen atom or a substituent. N and m are each an integer of 1 to 2.
1 2  1 2
数を表し、 k、 1は各々 3〜4の整数を表す。但し、 n+k= 5、かつ l+m= 5である。 ) K and 1 each represent an integer of 3 to 4. However, n + k = 5 and l + m = 5. )
(45)前記一般式(1A)で表される化合物が下記一般式(14A)で表されることを特 徴とする前記(18)〜(22)の 、ずれか 1項に記載の有機エレクト口ルミネッセンス素 子。 (45) The organic elect described in any one of (18) to (22) above, wherein the compound represented by the general formula (1A) is represented by the following general formula (14A): Mouth luminescence element.
[0119] [化 50] -般式 (14A) [0119] [Chemical 50] -General formula (14A)
[0120] (式中、 R、 Rは各々独立に水素原子または置換基を表す。 n、 mは各々 1〜2の整 [In the formula, R and R each independently represent a hydrogen atom or a substituent. N and m are each an integer of 1 to 2.
1 2  1 2
数を表し、 k、 1は各々 3〜4の整数を表す。但し、 n+k= 5、かつ l+m= 5である。 ) K and 1 each represent an integer of 3 to 4. However, n + k = 5 and l + m = 5. )
(46)前記一般式(1A)で表される化合物が下記一般式(15A)で表されることを特 徴とする前記(18)〜(22)の 、ずれか 1項に記載の有機エレクト口ルミネッセンス素 子。 (46) The organic elect described in any one of (18) to (22) above, wherein the compound represented by the general formula (1A) is represented by the following general formula (15A): Mouth luminescence element.
[0121] [化 51]  [0121] [Chemical 51]
-般式 5A) -General formula 5A)
[0122] (式中、 R、 Rは各々独立に水素原子または置換基を表す。 n、 mは各々 1〜2の整 [In the formula, R and R each independently represent a hydrogen atom or a substituent. N and m are each an integer of 1 to 2.
1 2  1 2
数を表し、 k、 1は各々 3〜4の整数を表す。但し、 n+k= 5、かつ l+m= 5である。 Z  K and 1 each represent an integer of 3 to 4. However, n + k = 5 and l + m = 5. Z
1 1
、 Z、 Z、 Zは各々窒素原子を少なくとも一つ含む 6員の芳香族複素環を表す。 ), Z, Z and Z each represents a 6-membered aromatic heterocyclic ring containing at least one nitrogen atom. )
2 3 4 2 3 4
(47)前記一般式(1A)で表される化合物が下記一般式(16A)で表されることを特 徴とする前記(18)〜(22)の 、ずれか 1項に記載の有機エレクト口ルミネッセンス素 子。  (47) The organic elect described in any one of (18) to (22) above, wherein the compound represented by the general formula (1A) is represented by the following general formula (16A) Mouth luminescence element.
[0123] [化 52] 一般式 (16A) [0123] [Chemical 52] General formula (16A)
[0124] (式中、 o、 pは各々 1〜3の整数を表し、 Ar、 Arは各々ァリーレン基または 2価の芳 [0124] (In the formula, o and p each represent an integer of 1 to 3, Ar and Ar each represent an arylene group or a divalent aromatic group.
1 2  1 2
香族複素環基を表す。 Z、 Zは各々窒素原子を少なくとも一つ含む 6員の芳香族複  Represents an aromatic heterocyclic group. Z and Z are each a 6-membered aromatic compound containing at least one nitrogen atom.
1 2  1 2
素環を表し、 Lは 2価の連結基を表す。 )  Represents a prime ring, and L represents a divalent linking group. )
(48)前記一般式(1A)で表される化合物が下記一般式(17A)で表されることを特 徴とする前記(18)〜(22)の 、ずれか 1項に記載の有機エレクト口ルミネッセンス素 子。  (48) The organic elect of any one of (18) to (22) above, wherein the compound represented by the general formula (1A) is represented by the following general formula (17A) Mouth luminescence element.
[0125] [化 53] 一般式 Π7Α)  [0125] [Chemical formula 53] General formula Π7Α)
[0126] (式中、 ο、 ρは各々 1〜3の整数を表し、 Ar、 Arは各々ァリーレン基または 2価の芳 [0126] (In the formula, ο and ρ each represent an integer of 1 to 3, Ar and Ar each represent an arylene group or a divalent aromatic group.
1 2  1 2
香族複素環基を表す。 Z、 Z、 Z、 Zは各々窒素原子を少なくとも一つ含む 6員の芳  Represents an aromatic heterocyclic group. Z, Z, Z, and Z are each a 6-membered good containing at least one nitrogen atom.
1 2 3 4  1 2 3 4
香族複素環を表し、 Lは 2価の連結基を表す。 )  Represents an aromatic heterocycle, and L represents a divalent linking group. )
(49)前記(15)〜(48)の!、ずれか 1項に記載の有機エレクトルミネッセンス素子を 有することを特徴とする表示装置。  (49) A display device comprising the organic electroluminescent device according to any one of (15) to (48).
[0127] (50)前記(15)〜(48)のいずれか 1項に記載の有機エレクトルミネッセンス素子を 有することを特徴とする照明装置。 発明の効果 [0127] (50) An illumination device comprising the organic electroluminescent element according to any one of (15) to (48). The invention's effect
[0128] 本発明により、高い発光効率を示し、かつ、発光寿命の長い有機 EL素子材料、有 機 EL素子、照明装置及び表示装置を提供することができる。  [0128] According to the present invention, it is possible to provide an organic EL element material, an organic EL element, an illumination device, and a display device that exhibit high luminous efficiency and have a long emission lifetime.
図面の簡単な説明  Brief Description of Drawings
[0129] [図 1]有機 EL素子力も構成される表示装置の一例を示した模式図である。 [0129] Fig. 1 is a schematic diagram showing an example of a display device that also has organic EL element power.
[図 2]表示部 Aの模式図である。  FIG. 2 is a schematic diagram of display unit A.
[図 3]画素の模式図である。  FIG. 3 is a schematic diagram of a pixel.
[図 4]パッシブマトリックス方式による表示装置の模式図である。  FIG. 4 is a schematic diagram of a passive matrix display device.
[図 5]照明装置の概略図である。  FIG. 5 is a schematic view of a lighting device.
[図 6]照明装置の断面図である。  FIG. 6 is a cross-sectional view of the lighting device.
符号の説明  Explanation of symbols
[0130] 1 ディスプレイ [0130] 1 display
3 画素  3 pixels
5 走査線  5 scan lines
6 データ線  6 Data line
7 電源ライン  7 Power line
10 有機 EL素子  10 Organic EL devices
11 スイッチングトランジスタ  11 Switching transistor
12 馬区動トランジスタ  12 Ma District Motion Transistor
13 コンデンサ  13 Capacitor
A 表示部  A Display section
B 制御部  B Control unit
101 有機 EL素子  101 organic EL devices
102 ガラスカバー  102 Glass cover
105 陰極  105 cathode
106 有機 EL層  106 OLED layer
107 透明電極付きガラス基板  107 Glass substrate with transparent electrode
108 窒素ガス 109 捕水剤 108 nitrogen gas 109 Water catcher
発明を実施するための最良の形態  BEST MODE FOR CARRYING OUT THE INVENTION
[0131] 本発明者等は、従来のオルトメタル錯体の問題点について鋭意検討を行った結果 、オルトメタル錯体の配位子として特定の構造を有する異なった配位子を複数組み 合わせたィ匕合物を用いて作製した有機 EL素子は、従来よりも高い発光効率を示し、 かつ、発光寿命が大幅に改善されることを見出した。この有機 EL素子を用いて作製 した照明装置及び表示装置は同様に優れた特性を示した。  [0131] As a result of intensive studies on the problems of conventional ortho metal complexes, the present inventors have found that a combination of a plurality of different ligands having a specific structure as a ligand of the ortho metal complex. It has been found that organic EL devices fabricated using the compound show higher luminous efficiency than before and have a significantly improved luminous lifetime. The lighting device and display device fabricated using this organic EL element showed excellent characteristics as well.
[0132] このような効果が得られる機構にっ 、ては解明して!/、な 、が、異なった配位子を複 数組み合わせることにより、発光中心となる有機 EL素子材料の自己組織化あるいは 自己集合ィ匕によるエキシマー発光が抑制され、高い発光効率を達成するものと推定 している。  [0132] Elucidate the mechanism by which such effects can be obtained! /, But by combining multiple different ligands, self-organization of the organic EL device material that becomes the emission center Or, it is presumed that excimer emission due to self-assembly is suppressed and high luminous efficiency is achieved.
[0133] 以下、本発明に係る各構成要素の詳細について、順次説明する。  [0133] Details of each component according to the present invention will be sequentially described below.
[0134] 本発明にお ヽて、上記有機 EL素子材料を含有する有機 EL素子とは、有機 EL素 子材料が有機 EL素子を構成する ヽずれかの有機層を形成するか、または有機層に 含有された有機 EL素子を表す。本発明の有機 EL素子の層構成については、別途、 詳細に説明する。 [0134] In the present invention, the organic EL element containing the organic EL element material means that the organic EL element material forms any organic layer constituting the organic EL element, or the organic layer. This represents the organic EL element contained in. The layer structure of the organic EL element of the present invention will be described separately in detail.
[0135] 本発明に係る前記金属錯体 (有機 EL素子材料)の含有層としては、発光層及び/ または正孔阻止層が好ましい。発光層に含有する場合は、発光層中の発光ドーパン トとして用いることにより、本発明の目的である有機 EL素子の発光寿命の長寿命化を 達成することができる。  [0135] As the containing layer of the metal complex (organic EL device material) according to the present invention, a light emitting layer and / or a hole blocking layer are preferable. When it is contained in the light emitting layer, it can be used as a light emitting dopant in the light emitting layer to achieve a long emission life of the organic EL device which is the object of the present invention.
[0136] 〔金属錯体〕  [Metal complexes]
本発明に係る前記一般式で表される金属錯体にっ 、て説明する。  The metal complex represented by the general formula according to the present invention will be described.
[0137] 本発明及び本発明の好ましい態様(1)の有機 EL素子材料は、前記一般式(1)で 表されるオルトメタル錯体であることを特徴とする。  [0137] The organic EL element material of the present invention and preferred embodiment (1) of the present invention is an ortho metal complex represented by the general formula (1).
[0138] 式中、 Mは元素周期表における第 8〜10族の金属元素を表す。 L、 1/ は互いに 異なる二座配位子を表し、 mは 1または 2であり、 nは 1または 2である。ただし、 m+n は 2または 3であり Mの電荷と一致する。  [0138] In the formula, M represents a metal element of Groups 8 to 10 in the periodic table. L and 1 / represent different bidentate ligands, m is 1 or 2, and n is 1 or 2. However, m + n is 2 or 3, which matches the charge of M.
[0139] 部分構造 MLは前記一般式 (2)で表され、部分構造 ML' は前記一般式 (3)また は (4)で表される。 [0139] The partial structure ML is represented by the general formula (2), and the partial structure ML 'is represented by the general formula (3) or Is represented by (4).
[0140] X は炭素原子または窒素原子を表し、 Q は炭素原子及び X と共に 6員の芳香族  [0140] X represents a carbon atom or a nitrogen atom, and Q represents a 6-membered aromatic together with the carbon atom and X.
11 11 11  11 11 11
炭化水素環または 5〜6員の芳香族複素環である環 Aを形成する原子群を表す。 X  A group of atoms forming a ring A which is a hydrocarbon ring or a 5- to 6-membered aromatic heterocycle. X
12 は炭素原子または窒素原子を表し、 Q は窒素原子及び X と共に 5〜6員の芳香族  12 represents a carbon atom or a nitrogen atom, Q is a 5- to 6-membered aromatic together with the nitrogen atom and X
12 12  12 12
複素環である環 Bを形成する原子群を表す。 Xは 0、 S、 CH、 CHR、 CR、 NR、 P  A group of atoms forming ring B which is a heterocyclic ring. X is 0, S, CH, CHR, CR, NR, P
1 2 2  1 2 2
R、 SiR、 C = 0、 C=NR、 SOまたは SOを表す。 Rはアルキル基、シクロアルキル R, SiR, C = 0, C = NR, SO or SO. R is an alkyl group, cycloalkyl
2 2 twenty two
基、アルケニル基、ァリール基、複素環基または芳香族複素環基を表す。  Represents a group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group.
[0141] X は炭素原子または窒素原子を表し、 Q は炭素原子及び X と共に 6員の芳香族 [0141] X represents a carbon atom or a nitrogen atom, and Q represents a 6-membered aromatic together with the carbon atom and X.
21 21 21  21 21 21
炭化水素環または 5〜6員の芳香族複素環である環 Cを形成する原子群を表す。 X  A group of atoms forming a ring C which is a hydrocarbon ring or a 5- to 6-membered aromatic heterocycle. X
22 は炭素原子または窒素原子を表し、 Q は窒素原子及び X と共に 5〜6員の芳香族  22 represents a carbon atom or a nitrogen atom, Q represents a 5- or 6-membered aromatic together with the nitrogen atom and X
22 22  22 22
複素環である環 Dを形成する原子群を表す。 Xは 0、 S、 CH、 CHR、 CR、 NR、 P  A group of atoms forming ring D which is a heterocyclic ring. X is 0, S, CH, CHR, CR, NR, P
2 2 2  2 2 2
R、 SiR、 C = 0、 C=NR、 SOまたは SOを表す。 Rはアルキル基、シクロアルキル R, SiR, C = 0, C = NR, SO or SO. R is an alkyl group, cycloalkyl
2 2 twenty two
基、アルケニル基、ァリール基、複素環基または芳香族複素環基を表す。  Represents a group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group.
[0142] X 、X は窒素原子またはリン原子を表し、 Xは X 、X を介して Mに配位している [0142] X and X represent a nitrogen atom or a phosphorus atom, and X is coordinated to M through X and X
31 32 3 31 32  31 32 3 31 32
二座配位子を形成する原子群を表す。  A group of atoms forming a bidentate ligand is represented.
[0143] 前記 6員の芳香族炭化水素環としては、ベンゼン環が挙げられる。 [0143] Examples of the 6-membered aromatic hydrocarbon ring include a benzene ring.
[0144] 前記 5〜6員の芳香族複素環としては、ォキサゾール環、チォフェン環、フラン環、 ピロール環、ピリジン環、ピリダジン環、ピリミジン環、ピラジン環、トリアジン環、イミダ ゾール環、ピラゾール環、トリァゾール環等が挙げられる。 [0144] Examples of the 5- to 6-membered aromatic heterocycle include oxazole ring, thiophene ring, furan ring, pyrrole ring, pyridine ring, pyridazine ring, pyrimidine ring, pyrazine ring, triazine ring, imidazole ring, pyrazole ring, And a triazole ring.
[0145] これらの 6員の芳香族炭化水素環、 5〜6員の芳香族複素環は、アルキル基 (例え ば、メチル基、ェチル基、プロピル基、イソプロピル基、(t)ブチル基、ペンチル基、へ キシル基、ォクチル基、ドデシル基、トリデシル基、テトラデシル基、ペンタデシル基 等)、シクロアルキル基 (例えば、シクロペンチル基、シクロへキシル基等)、ァルケ- ル基 (例えば、ビニル基、ァリル基等)、アルキニル基 (例えば、プロパルギル基等)、 ァリール基 (芳香族炭化水素環基ともいい、例えば、フ ニル基、トリル基、キシリル 基、ナフチル基、ビフヱ-リル基、アントリル基、フエナントリル基等)、複素環基 (例え ば、ピロリジル基、イミダゾリジル基、モルホリル基、ォキサゾリジル基等)、芳香族複 素環基 (例えば、例えば、ピリジル基、ピリミジニル基、フリル基、ピロリル基、イミダゾリ ル基、ベンゾイミダゾリル基、ピラゾリル基、ピラジュル基、トリァゾリル基 (例えば、 1, 2, 4—トリァゾール— 1—ィル基、 1, 2, 3—トリァゾール— 1—ィル基等)、ォキサゾリ ル基、ベンゾォキサゾリル基、チアゾリル基、イソォキサゾリル基、イソチアゾリル基、 フラザ-ル基、チェ-ル基、キノリル基、ベンゾフリル基、ジベンゾフリル基、ベンゾチ ェ-ル基、ジベンゾチェ-ル基、インドリル基、カルバゾリル基、カルボリニル基、ジァ ザカルバゾリル基 (カルボリン環を構成する炭素原子の一つが窒素原子で置き換わ つたものを示す)、キノキサリニル基、ピリダジニル基、トリアジニル基、キナゾリニル基 、フタラジュル基等)、アルコキシル基 (例えば、メトキシ基、エトキシ基、プロピルォキ シ基、ペンチルォキシ基、へキシルォキシ基、ォクチルォキシ基、ドデシルォキシ基 等)、シクロアルコキシル基(例えば、シクロペンチルォキシ基、シクロへキシルォキシ 基等)、ァリールォキシ基 (例えば、フエノキシ基、ナフチルォキシ基等)、アルキルチ ォ基(例えば、メチルチオ基、ェチルチオ基、プロピルチオ基、ペンチルチオ基、へ キシルチオ基、ォクチルチオ基、ドデシルチオ基等)、シクロアルキルチオ基 (例えば 、シクロペンチルチオ基、シクロへキシルチオ基等)、ァリールチオ基 (例えば、フエ二 ルチオ基、ナフチルチオ基等)、アルコキシカルボ-ル基 (例えば、メチルォキシカル ボ-ル基、ェチルォキシカルボ-ル基、ブチルォキシカルボ-ル基、ォクチルォキシ カルボ-ル基、ドデシルォキシカルボ-ル基等)、ァリールォキシカルボ-ル基(例え ば、フエ-ルォキシカルボ-ル基、ナフチルォキシカルボ-ル基等)、スルファモイル 基(例えば、アミノスルホ -ル基、メチルアミノスルホ -ル基、ジメチルアミノスルホ -ル 基、ブチルアミノスルホ -ル基、へキシルアミノスルホ -ル基、シクロへキシルアミノス ルホ-ル基、ォクチルアミノスルホ -ル基、ドデシルアミノスルホ-ル基、フエ-ルアミ ノスルホ -ル基、ナフチルアミノスルホ -ル基、 2—ピリジルアミノスルホ -ル基等)、ゥ レイド基(例えば、メチルウレイド基、ェチルウレイド基、ペンチルゥレイド基、シクロへ キシルウレイド基、ォクチルゥレイド基、ドデシルウレイド基、フエニルウレイド基、ナフ チルウレイド基、 2—ピリジルアミノウレイド基等)、ァシル基 (例えば、ァセチル基、ェ チルカルボ-ル基、プロピルカルボ-ル基、ペンチルカルボ-ル基、シクロへキシル カルボ-ル基、ォクチルカルポ-ル基、 2—ェチルへキシルカルボ-ル基、ドデシル カルボ-ル基、フヱ-ルカルボ-ル基、ナフチルカルボ-ル基、ピリジルカルボ-ル 基等)、ァシルォキシ基 (例えば、ァセチルォキシ基、ェチルカルボ-ルォキシ基、ブ チルカルボ-ルォキシ基、ォクチルカルポ-ルォキシ基、ドデシルカルボニルォキシ 基、フエ-ルカルポニルォキシ基等)、アミド基 (例えば、メチルカルボニルァミノ基、 ェチルカルボ-ルァミノ基、ジメチルカルボ-ルァミノ基、プロピルカルボ-ルァミノ基[0145] These 6-membered aromatic hydrocarbon rings and 5- to 6-membered aromatic heterocycles are alkyl groups (eg, methyl group, ethyl group, propyl group, isopropyl group, (t) butyl group, pentyl group). Group, hexyl group, octyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, etc.), cycloalkyl group (eg, cyclopentyl group, cyclohexyl group, etc.), alkenyl group (eg, vinyl group, aryl) Group), alkynyl group (for example, propargyl group, etc.), aryl group (also called aromatic hydrocarbon ring group, for example, phenyl group, tolyl group, xylyl group, naphthyl group, biphenyl-allyl group, anthryl group, phenanthryl) Group), heterocyclic group (for example, pyrrolidyl group, imidazolidyl group, morpholyl group, oxazolidyl group, etc.), aromatic heterocyclic group (for example, pyridyl group, Rimijiniru group, a furyl group, a pyrrolyl group, imidazol Group, benzimidazolyl group, pyrazolyl group, pyrajur group, triazolyl group (for example, 1, 2, 4-triazole-1-yl group, 1, 2, 3-triazole-1-yl group, etc.), oxazolyl group , Benzoxazolyl group, thiazolyl group, isoxazolyl group, isothiazolyl group, furazal group, chael group, quinolyl group, benzofuryl group, dibenzofuryl group, benzochel group, dibenzochel group, indolyl group , Carbazolyl group, carbolinyl group, diazacarbazolyl group (in which one of the carbon atoms constituting the carboline ring is replaced by a nitrogen atom), quinoxalinyl group, pyridazinyl group, triazinyl group, quinazolinyl group, phthalazyl group, etc.) , Alkoxyl groups (for example, methoxy group, ethoxy group, propyloxy group, pentyloxy group, hexyl group) Oxy group, octyloxy group, dodecyloxy group, etc.), cycloalkoxyl group (eg, cyclopentyloxy group, cyclohexyloxy group, etc.), aryloxy group (eg, phenoxy group, naphthyloxy group, etc.), alkylthio group (eg, methylthio group) , Ethylthio group, propylthio group, pentylthio group, hexylthio group, octylthio group, dodecylthio group, etc.), cycloalkylthio group (eg, cyclopentylthio group, cyclohexylthio group, etc.), arylthio group (eg, phenylthio group, naphthylthio group, etc.) Group), alkoxy carbo yl group (for example, methyl oxy carboxy group, eth oxy carbo yl group, butyl oxy carbo ol group, octyl oxy carbo ol group, dodecyl oxy carbo ol group, etc.) , Aryloxy groups (eg A phenyl group, a naphthyl group, etc.), a sulfamoyl group (for example, an aminosulfol group, a methylaminosulfol group, a dimethylaminosulfol group, a butylaminosulfol group, a hexyl group) Aminosulfol group, cyclohexylaminosulfol group, octylaminosulfol group, dodecylaminosulfol group, phenolaminosulfol group, naphthylaminosulfol group, 2-pyridylaminosulfol group Group), urea group (eg, methylureido group, ethylureido group, pentylureido group, cyclohexylureido group, octylureido group, dodecylureido group, phenylureido group, naphthylureido group, 2-pyridylaminoureido group, etc.), acyl Groups (e.g. acetyl, ethyl carbo, propyl carbo Group, pentyl carbo yl group, cyclohexyl carbo yl group, octyl carbo ol group, 2-ethyl hexyl carbo yl group, dodecyl carbo carb yl group, vinyl carbo yl group, naphthyl carbo yl group, Pyridyl carbon Group), acyloxy group (for example, acetyloxy group, ethylcarbo-loxy group, butylcarbo-loxy group, octylcarbonyl-oxyl group, dodecylcarbonyloxy group, phenylcarbonyloxy group, etc.), amido group (for example, methyl Carbonylamino group, ethyl carbolumino group, dimethyl carbolumino group, propyl carbolumino group
、ペンチルカルボ-ルァミノ基、シクロへキシルカルボ-ルァミノ基、 2—ェチルへキ シルカルボ-ルァミノ基、ォクチルカルボ-ルァミノ基、ドデシルカルボ-ルァミノ基、 フエ-ルカルポ-ルァミノ基、ナフチルカルボ-ルァミノ基等)、力ルバモイル基(例え ば、ァミノカルボ-ル基、メチルァミノカルボ-ル基、ジメチルァミノカルボ-ル基、プ 口ピルアミノカルボ-ル基、ペンチルァミノカルボ-ル基、シクロへキシルァミノカルボ -ル基、ォクチルァミノカルボ-ル基、 2—ェチルへキシルァミノカルボ-ル基、ドデ シルァミノカルボ-ル基、フエ-ルァミノカルボ-ル基、ナフチルァミノカルボ-ル基、 2—ピリジルァミノカルボ-ル基等)、スルフィエル基(例えば、メチルスルフィ-ル基、 ェチルスルフィ-ル基、ブチルスルフィ-ル基、シクロへキシルスルフィ-ル基、 2— ェチルへキシルスルフィ-ル基、ドデシルスルフィ-ル基、フエ-ルスルフィ-ル基、 ナフチルスルフィエル基、 2—ピリジルスルフィエル基等)、アルキルスルホ -ル基ま たはァリールスルホ -ル基(例えば、メチルスルホ -ル基、ェチルスルホ -ル基、ブチ ルスルホ -ル基、シクロへキシルスルホ -ル基、 2—ェチルへキシルスルホ -ル基、ド デシルスルホ -ル基、フエ-ルスルホ-ル基、ナフチルスルホ-ル基、 2—ピリジルス ルホ -ル基等)、アミノ基 (例えば、アミノ基、ェチルァミノ基、ジメチルァミノ基、プチ ルァミノ基、シクロペンチルァミノ基、 2—ェチルへキシルァミノ基、ドデシルァミノ基、 ァ-リノ基、ナフチルァミノ基、 2—ピリジルァミノ基等)、ニトロ基、シァノ基等の置換 基を有していてもよぐさらに、上記芳香族炭化水素環や芳香族複素環上の置換基 同士が環構造を形成して、もう一つの芳香族炭化水素環や芳香族複素環が付いた 縮環構造をとることも可能である。 Pentyl carbolumino group, cyclohexyl carbolumino group, 2-ethyl hexyl carbolumino group, octyl carbolumino group, dodecyl carbolumino group, phenyl carbolumino group, naphthyl carbolumino group, etc.) Forced rubamoyl groups (for example, aminoamino group, methylaminocarbol group, dimethylaminocarbole group, open pyraminocarbol group, pentylaminocarbo ol group, cyclohexylamino) Carbon group, Octylaminocarbol group, 2-Ethylhexylaminocarbol group, Dodecylaminocarbol group, Phenylaminocarbol group, Naphtylaminocarbol group, 2— Pyridylaminocarbol group, etc.), sulfier groups (eg methylsulfuryl group, ethylsulfuryl group, butylsulfuryl group, cyclohexyl) Sulfyl group, 2-ethylhexylsulfyl group, dodecylsulfyl group, phenolsulfuryl group, naphthylsulfuryl group, 2-pyridylsulfuryl group, etc.), alkylsulfol group or Arylsulfol groups (eg, methylsulfol group, ethylsulfol group, butylsulfol group, cyclohexylsulfol group, 2-ethylhexylsulfol group, dodecylsulfol group, phenylsulfol group) Group, naphthylsulfol group, 2-pyridylsulfol group, etc.), amino group (for example, amino group, ethylamino group, dimethylamino group, propylamino group, cyclopentylamino group, 2-ethylhexylamino group, dodecylamino group) , A-lino group, a naphthylamino group, a 2-pyridylamino group, etc.), a nitro group, a cyano group and the like. It is also possible to form a condensed ring structure with another aromatic hydrocarbon ring or aromatic heterocyclic ring by forming substituents on the aromatic hydrocarbon ring or aromatic heterocyclic ring. .
前記 Rで表される、アルキル基、シクロアルキル基、ァルケ-ル基、ァリール基、複 素環基、芳香族複素環基は、各々、前記 6員の芳香族炭化水素環、 5〜6員の芳香 族複素環の置換基として述べたアルキル基、シクロアルキル基、アルケニル基、ァリ ール基、複素環基、芳香族複素環基と同義である。 [0147] 前記態様 (2)の有機 EL素子材料は、前記一般式 (5)で表されるオルトメタル錯体 であることを特徴とする。 The alkyl group, cycloalkyl group, alkyl group, aryl group, bicyclic group, and aromatic heterocyclic group represented by R are each a 6-membered aromatic hydrocarbon ring, a 5- to 6-membered group, respectively. These are synonymous with the alkyl group, cycloalkyl group, alkenyl group, aryl group, heterocyclic group, and aromatic heterocyclic group described as the substituent of the aromatic heterocyclic group. [0147] The organic EL device material of the aspect (2) is an ortho metal complex represented by the general formula (5).
[0148] 式中、 Mは元素周期表における第 8〜10族の金属元素を表す。 mlは 1または 2で あり、 nlは 1または 2である。ただし、 ml +nlは 2または 3であり Mの電荷と一致する 。 X は炭素原子または窒素原子を表し、 Q は炭素原子及び X と共に 6員の芳香族 [0148] In the formula, M represents a metal element of Groups 8 to 10 in the periodic table. ml is 1 or 2 and nl is 1 or 2. However, ml + nl is 2 or 3, which matches the charge of M. X represents a carbon atom or a nitrogen atom, Q represents a 6-membered aromatic together with the carbon atom and X
11 11 11 11 11 11
炭化水素環または 5〜6員の芳香族複素環である環 Aを形成する原子群を表す。 X  A group of atoms forming a ring A which is a hydrocarbon ring or a 5- to 6-membered aromatic heterocycle. X
12 は炭素原子または窒素原子を表し、 Q 5〜  12 represents a carbon atom or a nitrogen atom, Q 5 ~
12は窒素原子及び X  12 is nitrogen atom and X
12と共に 6員の芳香族 複素環である環 Bを形成する原子群を表す。 Xは 0、 S、 CH、 CHR、 CR、 NR、 P  A group of atoms that together with 12 form ring B, a 6-membered aromatic heterocycle. X is 0, S, CH, CHR, CR, NR, P
1 2 2  1 2 2
R、 SiR、 C = 0、 C=NR、 SOまたは SOを表す。 Rはアルキル基、シクロアルキル R, SiR, C = 0, C = NR, SO or SO. R is an alkyl group, cycloalkyl
2 2 twenty two
基、アルケニル基、ァリール基、複素環基または芳香族複素環基を表す。  Represents a group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group.
[0149] X は、炭素原子または窒素原子を表し、 Q は炭素原子及び X と共に 6員の芳香 [0149] X represents a carbon atom or a nitrogen atom, and Q represents a 6-membered aromatic together with the carbon atom and X.
21 21 21  21 21 21
族炭化水素環または 5〜6員の芳香族複素環である環 Cを形成する原子群を表す。 X  Represents an atomic group forming a ring C which is a hydrocarbon ring or a 5- to 6-membered aromatic heterocycle. X
22は炭素原子または窒素原子を表し、 Q  22 represents a carbon atom or a nitrogen atom, Q
22は窒素原子及び X  22 is nitrogen atom and X
22と共に 5〜6員の芳香 族複素環である環 Dを形成する原子群を表す。 Xは 0、 S、 CH、 CHR、 CR、 NR、  This represents a group of atoms that together with 22 form ring D, which is a 5- to 6-membered aromatic heterocycle. X is 0, S, CH, CHR, CR, NR,
2 2 2 2 2 2
PR、 SiR、 C = 0、 C=NR、 SOまたは SOを表す。 Rはアルキル基、シクロアルキル PR, SiR, C = 0, C = NR, SO or SO. R is an alkyl group, cycloalkyl
2 2  twenty two
基、アルケニル基、ァリール基、複素環基または芳香族複素環基を表す。ただし、環 Represents a group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. However, the ring
Aと環 C、環 Bと環 Dが同時に同じものになることはない。 A and ring C, and ring B and ring D cannot be the same at the same time.
[0150] 前記 6員の芳香族炭化水素環、 5〜6員の芳香族複素環、 Rは、前記態様 (1)で述 ベたものと同義である。 [0150] The 6-membered aromatic hydrocarbon ring, 5- to 6-membered aromatic heterocycle, and R have the same meanings as described in the embodiment (1).
[0151] 前記一般式 (5)において、芳香族複素環 Bまたは芳香族複素環 Dのうち少なくとも 一方が 6員環であり、他方が 5員環であることが好ましい。  [0151] In the general formula (5), at least one of the aromatic heterocycle B or the aromatic heterocycle D is preferably a 6-membered ring and the other is preferably a 5-membered ring.
[0152] 前記態様 (4)の有機 EL素子材料は、前記一般式 (6)で表されるオルトメタル錯体 であることを特徴とする。 [0152] The organic EL device material of the aspect (4) is an ortho metal complex represented by the general formula (6).
[0153] 式中、 Mは元素周期表における第 8〜10族の金属元素を表す。 m2は 1または 2で あり、 n2は 1または 2である。ただし、 m2+n2は 2または 3であり Mの電荷と一致する[0153] In the formula, M represents a metal element of Groups 8 to 10 in the periodic table. m2 is 1 or 2, and n2 is 1 or 2. However, m2 + n2 is 2 or 3, which matches the charge of M
。 X は炭素原子または窒素原子を表し、 Q は炭素原子及び X と共に 6員の芳香族. X represents a carbon atom or a nitrogen atom, Q represents a 6-membered aromatic together with the carbon atom and X
11 11 11 11 11 11
炭化水素環または 5〜6員の芳香族複素環である環 Aを形成する原子群を表す。 X  A group of atoms forming a ring A which is a hydrocarbon ring or a 5- to 6-membered aromatic heterocycle. X
12 は炭素原子または窒素原子を表し、 Q は窒素原子及び X と共に 5〜6員の芳香族 複素環である環 Bを形成する原子群を表す。 Xは 0、 S、 CH 、 CHR、 CR 、 NR、 P 12 represents a carbon atom or a nitrogen atom, Q is a 5- to 6-membered aromatic together with the nitrogen atom and X A group of atoms forming ring B which is a heterocyclic ring. X is 0, S, CH, CHR, CR, NR, P
1 2 2  1 2 2
R、 SiR、 C = 0、 C=NR、 SOまたは SOを表す。 Rはアルキル基、シクロアルキル R, SiR, C = 0, C = NR, SO or SO. R is an alkyl group, cycloalkyl
2 2 twenty two
基、ァルケ-ル基、ァリール基、複素環基または芳香族複素環基を表す。 X 、 X は  A group, an alkyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group; X and X are
31 32 窒素原子またはリン原子を表し、 Xは X 、 X を介して Mに配位している二座配位子  31 32 A bidentate ligand that represents a nitrogen atom or a phosphorus atom, and X is coordinated to M via X and X
3 31 32  3 31 32
を形成する原子群を表す。  Represents an atomic group forming
[0154] 前記 6員の芳香族炭化水素環、 5〜6員の芳香族複素環、 Rは、前記態様 (1)で述 ベたものと同義である。 [0154] The 6-membered aromatic hydrocarbon ring, 5- to 6-membered aromatic heterocycle, and R have the same meanings as described in the embodiment (1).
[0155] 前記一般式 (6)にお 、て、芳香族複素環 Bが 6員環であることが好ま 、。 [0155] In the general formula (6), the aromatic heterocycle B is preferably a 6-membered ring.
[0156] 前記態様 (6)の有機 EL素子材料は、前記一般式(1— 1)〜(1— 150)で表される 部分構造またはその互変異性体を部分構造として有するオルトメタル錯体であること を特徴とする。 [0156] The organic EL device material of the aspect (6) is an ortho metal complex having a partial structure represented by the general formulas (1-1) to (1-150) or a tautomer thereof as a partial structure. It is characterized by being.
[0157] 式中、 Mは元素周期表における第 8〜10族の金属元素を表す。 R 、 R は各々置  [0157] In the formula, M represents a metal element of Groups 8 to 10 in the periodic table. R and R are
11 12 換基を表し、 nl l、nl2は各々 0〜2から選ばれる整数を表す。 X 、X は各々〉 N  11 12 represents a substituent, and nl l and nl2 each represents an integer selected from 0 to 2. X and X are each> N
13 14  13 14
R 、 一 O または S を表す。 R はアルキル基、シクロアルキル基、アルケニル R represents one O or S. R is an alkyl group, cycloalkyl group, alkenyl
13 13 13 13
基、ァリール基、複素環基または芳香族複素環基を表す。 X 、 X 、 X 、 X は、各々  Represents a group, aryl group, heterocyclic group or aromatic heterocyclic group. X, X, X, X are each
15 16 17 18 15 16 17 18
〉N—R 、—O または—S—を表す。 R は水素原子、アルキル基、シクロアルキ> N—R, —O or —S—. R is a hydrogen atom, alkyl group, cycloalkyl
16 16 16 16
ル基、アルケニル基、ァリール基、複素環基または芳香族複素環基を表す。 X 、 X  Represents an alkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. X, X
19a 19 19a 19
、 X は、各々 CHまたは Nを表し、任意の 1つまたは 2つが Nである。 Xは 0、 S、 C b 19c 0 , X each represents CH or N, and any one or two of them are N. X is 0, S, C b 19c 0
H、 CHR、 CR、 NR、 PR、 SiR、 C = 0、 C=NR、 SOまたは SOを表す。 Rはアル H, CHR, CR, NR, PR, SiR, C = 0, C = NR, SO or SO. R is al
2 2 2 2 2 2 2 2
キル基、シクロアルキル基、ァルケ-ル基、ァリール基、複素環基または芳香族複素 環基を表す。  Represents a kill group, a cycloalkyl group, an alkyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group;
[0158] 前記 R 、 R で表される置換基は、前記態様(1)で述べた 6員の芳香族炭化水素  [0158] The substituent represented by R 1 and R 2 is the 6-membered aromatic hydrocarbon described in the embodiment (1).
11 12  11 12
環、 5〜6員の芳香族複素環の置換基と同義である。前記アルキル基、シクロアルキ ル基、アルケニル基、ァリール基、複素環基または芳香族複素環基は、前記態様(1 )で述べたものと同義である。  It is synonymous with the substituent of a ring and a 5-6 membered aromatic heterocyclic ring. The alkyl group, cycloalkyl group, alkenyl group, aryl group, heterocyclic group or aromatic heterocyclic group has the same meaning as described in the embodiment (1).
[0159] 前記態様 (7)の有機 EL素子材料は、前記一般式 (2— 1)〜(2— 50)で表される部 分構造またはその互変異性体を部分構造として有するオルトメタル錯体であることを 特徴とする。 [0160] 式中、 Mは元素周期表における第 8〜10族の金属元素を表す。 R 、R は各々置 [0159] The organic EL device material of the aspect (7) is an ortho metal complex having a partial structure represented by the general formulas (2-1) to (2-50) or a tautomer thereof as a partial structure. It is characterized by being. [0160] In the formula, M represents a metal element of Groups 8 to 10 in the periodic table. R and R are
21 22 換基を表し、 n21、n22は 0〜2から選ばれる整数を表す。 X は、〉N— R 、— O—  21 22 represents a substituent, and n21 and n22 each represents an integer selected from 0 to 2. X is> N—R, —O—
23 23 または S を表す。 R は、アルキル基、シクロアルキル基、アルケニル基、ァリール  23 represents 23 or S R is an alkyl group, cycloalkyl group, alkenyl group, aryl
23  twenty three
基、複素環基または芳香族複素環基を表す。 X 、X は、 >N-R 、—O または  Represents a group, a heterocyclic group or an aromatic heterocyclic group. X and X are> N-R, —O or
24 25 24  24 25 24
S を表す。 R は水素原子、アルキル基、シクロアルキル基、アルケニル基、ァリ  Represents S. R is a hydrogen atom, alkyl group, cycloalkyl group, alkenyl group, aryl
24  twenty four
ール基、複素環基または芳香族複素環基を表す。 X 、X 、X は各々 CHまたは N  Represents an aryl group, a heterocyclic group or an aromatic heterocyclic group. X, X, X are each CH or N
26 27 28  26 27 28
を表し、任意の 1つまたは 2つが Nである。 Xは 0、 S、 CH、 CHR、 CR、 NR、 PR、  And any one or two is N. X is 0, S, CH, CHR, CR, NR, PR,
0 2 2  0 2 2
SiR、 C = 0、 C=NR、 SOまたは SOを表す。 Rはアルキル基、シクロアルキル基、 Represents SiR, C = 0, C = NR, SO or SO. R is an alkyl group, a cycloalkyl group,
2 2 twenty two
アルケニル基、ァリール基、複素環基または芳香族複素環基を表す。  An alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group;
[0161] 前記 R 、R で表される置換基は、前記態様(1)で述べた 6員の芳香族炭化水素 [0161] The substituent represented by R 1 and R 2 is the 6-membered aromatic hydrocarbon described in the embodiment (1).
21 22  21 22
環、 5〜6員の芳香族複素環の置換基と同義である。前記アルキル基、シクロアルキ ル基、アルケニル基、ァリール基、複素環基または芳香族複素環基は、前記態様(1 )で述べたものと同義である。  It is synonymous with the substituent of a ring and a 5-6 membered aromatic heterocyclic ring. The alkyl group, cycloalkyl group, alkenyl group, aryl group, heterocyclic group or aromatic heterocyclic group has the same meaning as described in the embodiment (1).
[0162] 前記態様 (8)の有機 EL素子材料は、前記一般式 (3— 1)〜(3— 10)で表される部 分構造またはその互変異性体を部分構造として有するオルトメタル錯体であることを 特徴とする。 [0162] The organic EL device material of the aspect (8) is an ortho metal complex having a partial structure represented by the general formulas (3-1) to (3-10) or a tautomer thereof as a partial structure. It is characterized by being.
[0163] 式中、 Mは元素周期表における第 8〜10族の金属元素を表す。 R 、R は各々置  [0163] In the formula, M represents a metal element of Groups 8 to 10 in the periodic table. R and R are
31 32 換基を表し、 n31、n32は 0〜2から選ばれる整数を表す。 X は、〉N— R 、— O—  31 32 represents a substituent, and n31 and n32 represent an integer selected from 0 to 2. X is> N—R, —O—
31 33 または S を表す。 R はアルキル基、シクロアルキル基、アルケニル基、ァリール  31 represents 33 or S R is an alkyl group, cycloalkyl group, alkenyl group, aryl
33  33
基、複素環基または芳香族複素環基を表す。 X 、X は、 >N-R 、—O または  Represents a group, a heterocyclic group or an aromatic heterocyclic group. X and X are> N-R, —O or
32 33 34  32 33 34
S を表す。 R は水素原子、アルキル基、シクロアルキル基、アルケニル基、ァリ  Represents S. R is a hydrogen atom, alkyl group, cycloalkyl group, alkenyl group, aryl
25  twenty five
ール基、複素環基または芳香族複素環基を表す。 X 、X 、X は各々 CHまたは N  Represents an aryl group, a heterocyclic group or an aromatic heterocyclic group. X, X, X are each CH or N
34 35 36  34 35 36
を表し、任意の 1つまたは 2つが Nである。 Xは 0、 S、 CH、 CHR、 CR、 NR、 PR、  And any one or two is N. X is 0, S, CH, CHR, CR, NR, PR,
0 2 2  0 2 2
SiR、 C = 0、 C=NR、 SOまたは SOを表す。 Rはアルキル基、シクロアルキル基、 Represents SiR, C = 0, C = NR, SO or SO. R is an alkyl group, a cycloalkyl group,
2 2 twenty two
アルケニル基、ァリール基、複素環基または芳香族複素環基を表す。  An alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group;
[0164] 前記 R 、R で表される置換基は、前記態様(1)で述べた 6員の芳香族炭化水素 [0164] The substituent represented by R 1 and R 2 is the 6-membered aromatic hydrocarbon described in the embodiment (1).
31 32  31 32
環、 5〜6員の芳香族複素環の置換基と同義である。前記アルキル基、シクロアルキ ル基、アルケニル基、ァリール基、複素環基または芳香族複素環基は、前記態様(1 )で述べたものと同義である。 It is synonymous with the substituent of a ring and a 5-6 membered aromatic heterocyclic ring. The alkyl group, cycloalkyl group, alkenyl group, aryl group, heterocyclic group or aromatic heterocyclic group is the same as the above-described embodiment (1 ) Is synonymous with that described above.
[0165] 前記態様 (9)の有機 EL素子材料は、前記一般式 (7)で表される部分構造または その互変異性体を部分構造として有するオルトメタル錯体であることを特徴とする。  [0165] The organic EL device material of the aspect (9) is an ortho metal complex having a partial structure represented by the general formula (7) or a tautomer thereof as a partial structure.
[0166] 式中、 Mは元素周期表における第 8〜10族の金属元素を表す。 X は炭素原子ま [0166] In the formula, M represents a metal element of Groups 8 to 10 in the periodic table. X is a carbon atom
41  41
たは窒素原子を表し、 Q は炭素原子及び X と共に 6員の芳香族炭化水素環または  Or a nitrogen atom, Q is a carbon atom and X together with a 6-membered aromatic hydrocarbon ring or
41 41  41 41
5〜6員の芳香族複素環である環 Eを形成する原子群を表す。 R は置換基を表し、 n  A group of atoms forming ring E, which is a 5- to 6-membered aromatic heterocycle. R represents a substituent, and n
41  41
4は 0〜3から選ばれる整数を表す。 Xaは— N (Ra)、— O— Raまたは— S— Raを表  4 represents an integer selected from 0 to 3. Xa represents —N (Ra), —O—Ra or —S—Ra
2  2
す。 Raはアルキル基、シクロアルキル基、アルケニル基、ァリール基、複素環基また は芳香族複素環基を表す。 Xaが— N (Ra)の場合、 2つの Raは同じであっても異な  The Ra represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. If Xa is — N (Ra), the two Ras are the same but different
2  2
つていてもよい。 Xは 0、 S、 CH、 CHR、 CR、 NR、 PR、 SiR、 C = 0、 C=NR、 S  You may go on. X is 0, S, CH, CHR, CR, NR, PR, SiR, C = 0, C = NR, S
4 2 2 2  4 2 2 2
Oまたは SOを表す。 Rはアルキル基、シクロアルキル基、アルケニル基、ァリール基  Represents O or SO. R is an alkyl group, cycloalkyl group, alkenyl group, aryl group
2  2
、複素環基または芳香族複素環基を表す。  Represents a heterocyclic group or an aromatic heterocyclic group.
[0167] 前記 R で表される置換基は、前記態様(1)で述べた 6員の芳香族炭化水素環、 5 [0167] The substituent represented by R 1 is a 6-membered aromatic hydrocarbon ring described in the embodiment (1),
41  41
〜6員の芳香族複素環の置換基と同義である。前記アルキル基、シクロアルキル基、 アルケニル基、ァリール基、複素環基または芳香族複素環基は、前記態様(1)で述 ベたものと同義である。  Synonymous with a substituent of a 6-membered aromatic heterocyclic ring. The alkyl group, cycloalkyl group, alkenyl group, aryl group, heterocyclic group or aromatic heterocyclic group has the same meaning as described in the embodiment (1).
[0168] 一般式 (7)で表される部分構造またはその互変異性体を部分構造として有するォ ルトメタル錯体は、前記一般式 (8)または(9)で表される部分構造またはその互変異 性体を部分構造として有するオルトメタル錯体であることが好ましい。  [0168] The orthometal complex having a partial structure represented by the general formula (7) or a tautomer thereof as a partial structure is a partial structure represented by the general formula (8) or (9) or a tautomer thereof. It is preferable that it is an ortho metal complex which has an active substance as a partial structure.
[0169] 式中、 Mは元素周期表における第 8〜10族の金属元素を表す。 R 、R 、R 、R  [0169] In the formula, M represents a metal element of Groups 8 to 10 in the periodic table. R, R, R, R
51 52 53 54 は、各々水素原子または電子供与性の置換基を表し、少なくとも 1つは電子供与性 の置換基である。 R 、R 、R 、R  51 52 53 54 each represents a hydrogen atom or an electron-donating substituent, and at least one of them is an electron-donating substituent. R, R, R, R
56 57 58 59は、各々水素原子または置換基を表し、 R 、R  56 57 58 59 each represents a hydrogen atom or a substituent, and R 1, R 2
56 58 の少なくとも一方は電子吸引性の置換基である。 R 、 R は置換基を表し、 n51、 n5  At least one of 56 58 is an electron-withdrawing substituent. R 1 and R 2 represent a substituent, n51, n5
50 55  50 55
2は 0〜3から選ばれる整数を表す。 Xaは— N (Ra)、— O— Raまたは— S— Raを表  2 represents an integer selected from 0 to 3. Xa represents —N (Ra), —O—Ra or —S—Ra
2  2
す。 Raはアルキル基、シクロアルキル基、アルケニル基、ァリール基、複素環基また は芳香族複素環基を表す。 Xaが— N (Ra)の場合、 2つの Raは同じであっても異な  The Ra represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. If Xa is — N (Ra), the two Ras are the same but different
2  2
つていてもよい。 Xは 0、 S、 CH、 CHR、 CR、 NR、 PR、 SiR、 C = 0、 C=NR、 S  You may go on. X is 0, S, CH, CHR, CR, NR, PR, SiR, C = 0, C = NR, S
5 2 2 2  5 2 2 2
Oまたは SOを表す。 Rはアルキル基、シクロアルキル基、アルケニル基、ァリール基 、複素環基または芳香族複素環基を表す。 Represents O or SO. R is an alkyl group, cycloalkyl group, alkenyl group, aryl group Represents a heterocyclic group or an aromatic heterocyclic group.
[0170] 前記電子供与性の置換基は、下記に記載のハメットの σ ρ値が負の値を示す置換 基のことであり、そのような置換基は水素原子と比べて結合原子側に電子を与えや すい特性を有する。  [0170] The electron-donating substituent is a substituent having a negative Hammett σ ρ value described below, and such a substituent has an electron closer to the bonding atom side than a hydrogen atom. It is easy to give.
[0171] 電子供与性を示す置換基の具体例としては、ヒドロキシル基、アルコキシ基 (例えば 、メトキシ基、 )、ァセチルォキシ基、アミノ基、ジメチルァミノ基、ァセチルァミノ基、ァ ルキル基(例えば、メチル基、ェチル基、プロピル基、 tert—ブチル基等)、ァリール 基 (例えば、フ ニル基、メシチル基等)が挙げられる。  [0171] Specific examples of the substituent exhibiting an electron donating property include a hydroxyl group, an alkoxy group (for example, methoxy group,), an acetyloxy group, an amino group, a dimethylamino group, an acetylamino group, an alkyl group (for example, a methyl group, Ethyl group, propyl group, tert-butyl group, etc.) and aryl group (eg, phenyl group, mesityl group, etc.).
[0172] 例えば、び カ ー0. 20以下の電子供与性基としては、シクロプロビル基(一 0. 21) 、シクロへキシル基(— 0. 22)、 tert—ブチル基(— 0. 20)、— CH Si (CH ) (— 0.  [0172] For example, as an electron donating group having a molecular weight of 0.20 or less, a cycloprovir group (one 0.21), a cyclohexyl group (—0.22), a tert-butyl group (—0.0. 20), — CH Si (CH) (— 0.
2 3 3 2 3 3
21)、アミノ基(一0. 66)、ヒドロキシルァミノ基(一0. 34)、 -NHNH (— 0. 55)、 21), amino group (one 0.666), hydroxylamino group (one 0.34), -NHNH (—0.55),
2  2
-NHCONH (一 0. 24)、一 NHCH (— 0. 84)、一 NHC H (— 0. 61)、一 NHC  -NHCONH (1 0. 24), 1 NHCH (— 0. 84), 1 NHC H (— 0. 61), 1 NHC
2 3 2 5  2 3 2 5
ONHC H (-0. 26)、 -NHC H (— 0. 51)、 一 NHC H (— 0. 40)、 一 N = CH ONHC H (-0. 26), -NHC H (— 0. 51), 1 NHC H (— 0. 40), 1 N = CH
2 5 4 9 6 5 2 5 4 9 6 5
C H (— 0. 55)、一 OH (— 0. 37)、一 OCH (— 0. 27)、一 OCH COOH (— 0. 3 C H (— 0.55), 1 OH (— 0. 37), 1 OCH (— 0. 27), 1 OCH COOH (— 0. 3)
6 5 3 2 6 5 3 2
3)、 -OC H (-0. 24)、 -OC H (— 0. 25)、一OCH (CH ) (— 0. 45)、一OC  3), -OC H (-0. 24), -OC H (—0.25), one OCH (CH 2) (—0.45), one OC
2 5 3 7 3 2 2 5 3 7 3 2
H (一 0. 34)、一OCH C H (— 0. 42)等が挙げられる。 H (one 0.34), one OCH C H (—0.42) and the like.
5 11 2 6 5  5 11 2 6 5
[0173] また、ハメットの σ ρ値については、例えば、下記文献等が参照できる。  [0173] For Hammett's σ ρ value, for example, the following documents can be referred to.
[0174] ノ、メットの σ ρ値とは、ハメットの置換基定数 σ ρを指す。ハメットの σ ρの値は、 Ham mett等によって安息香酸ェチルの加水分解に及ぼす置換基の電子的効果力 求 められた置換基定数であり、「薬物の構造活性相関」(南江堂:1979年)、 rsubstitu ent Constants for Correlation Analysis m chemistry and biologyj ( C. Hansch and A. Leo, John Wiley & Sons, New York, 1979年)等に記 載の基を引用することができる。  [0174] The σ ρ value of Met and Met refers to Hammett's substituent constant σ ρ. Hammett's σ ρ value is the substituent constant determined by Hammett et al. For the electronic effect of the substituents on the hydrolysis of ethyl benzoate. “Structure-activity relationship of drugs” (Nanedo: 1979) , Rsubstituent Constants for Correlation Analysis chemistry and biology (C. Hansch and A. Leo, John Wiley & Sons, New York, 1979), etc. can be cited.
[0175] 電子供与性の置換基としては、前記の基の中、最も好ましくはアルキル基、アルコ キシ基、アルキルアミノ基が挙げられる。  [0175] Among the above groups, the electron-donating substituent is most preferably an alkyl group, an alkoxy group, or an alkylamino group.
[0176] 前記置換基としては、前記態様 (1)で述べた 6員の芳香族炭化水素環、 5〜6員の 芳香族複素環の置換基と同義である。前記アルキル基、シクロアルキル基、ァルケ- ル基、ァリール基、複素環基または芳香族複素環基は、前記態様(1)で述べたもの と同義である。 [0176] The substituent is synonymous with the substituent of the 6-membered aromatic hydrocarbon ring or 5- to 6-membered aromatic heterocycle described in the embodiment (1). The alkyl group, cycloalkyl group, alkyl group, aryl group, heterocyclic group or aromatic heterocyclic group is the same as described in the embodiment (1). It is synonymous with.
[0177] 前記態様(11)の有機 EL素子材料は、前記一般式(10)で表される部分構造また はその互変異性体を部分構造として有するオルトメタル錯体であることを特徴とする。  [0177] The organic EL device material of the aspect (11) is an ortho metal complex having a partial structure represented by the general formula (10) or a tautomer thereof as a partial structure.
[0178] 式中、 Mは元素周期表における第 8〜10族の金属元素を表す。 X 、X 、X 、X [0178] In the formula, M represents a metal element of Groups 8 to 10 in the periodic table. X, X, X, X
61 62 63 64 は、各々炭素原子または窒素原子を表し、 Q  61 62 63 64 each represents a carbon atom or a nitrogen atom, and Q
61は炭素原子及び X 、X  61 is a carbon atom and X, X
61 63と共に 6員の 芳香族炭化水素環または 5〜6員の芳香族複素環である環 Fを形成する原子群を表 61 represents a group of atoms that together with 63 form ring F, which is a 6-membered aromatic hydrocarbon ring or a 5- to 6-membered aromatic heterocyclic ring.
O C  O C
し、 Q は窒素原子及び X卜 ilO— L、 X と共に 5〜6員の芳香族複素環である環 Gを形成す Q forms a ring G, which is a 5- to 6-membered aromatic heterocycle, together with the nitrogen atom and X 卜 ilO—L, X.
62 62 64 62 62 64
 Yes
る原子群を表す。 卜  Represents an atomic group.卜
X、 Xはファンデルワールス体積が 20  X, X has a van der Waals volume of 20
k A3以上である置換基を表し h k A represents a substituent that is 3 or more h
、 m6、 n6は 0または 1を表す。ただし、 m6 +n6≥lである。 Xは 0、 S、 CH、 CHR、  , M6, and n6 each represents 0 or 1. However, m6 + n6≥l. X is 0, S, CH, CHR,
6 2 6 2
CR、 NR、 PR、 SiR、 C = 0、 C=NR、 SOまたは SOを表す。 Rはアルキル基、シクCR, NR, PR, SiR, C = 0, C = NR, SO or SO. R is an alkyl group,
2 2 2 2 2 2
口アルキル基、アルケニル基、ァリール基、複素環基または芳香族複素環基を表す。  It represents a mouth alkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group.
[0179] 前記 6員の芳香族炭化水素環、 5〜6員の芳香族複素環は前記態様 (1)で述べた ものと同義である。 [0179] The 6-membered aromatic hydrocarbon ring and the 5- to 6-membered aromatic heterocyclic ring have the same meanings as described in the embodiment (1).
[0180] 置換基のファンデルワールス (VDW)体積とは、アクセルリス社製分子シミュレーシ ヨンソフト Cerius2を用いて求められるパラメーターを用いる力 ベンゼン環に置換基 を導入し、 Dreiding Force Fieldを用いて、 MM計算で分子構造を最適化して、 Connoly Surfaceを用いて求めた Volume値と定義する。具体的な置換基のファ ンデノレヮーノレス (VDW)体積を下記に示す。  [0180] The van der Waals (VDW) volume of a substituent is a force that uses parameters obtained using the molecular simulation software Cerius2 manufactured by Accelrys, Inc. A substituent is introduced into the benzene ring, and a Dreiding Force Field is used. Optimize the molecular structure by MM calculation and define it as the volume value obtained using Connoly Surface. The specific fandenolenoless (VDW) volume of the substituent is shown below.
置換基 A3 Substituent A 3
メチル基 25. 4  Methyl group 25.4
ェチル基  Ethyl group
イソプロピノレ基  Isopropinole group
tert—ブチノレ基 tert-Butinole group
フエニル基  Phenyl group
メトキシ基  Methoxy group
アミノ基 22. 2  Amino group 22.2
ヒドロキシル基  Hydroxyl group
塩素原子 22. 4 臭素原子 26. 5 Chlorine atom 22.4 Bromine atom 26.5
フッ素原子 13. 3  Fluorine atom 13.3
トリフルォロメチル基 42. 5  Trifluoromethyl group 42.5
前記アルキル基、シクロアルキル基、ァルケ-ル基、ァリール基、複素環基または 芳香族複素環基は、前記態様(1)で述べたものと同義である。  The alkyl group, cycloalkyl group, alkyl group, aryl group, heterocyclic group or aromatic heterocyclic group has the same meaning as described in the embodiment (1).
[0182] 一般式(10)で表される部分構造またはその互変異性体を部分構造として有するォ ルトメタル錯体は、前記一般式(11)〜(14)で表される部分構造またはその互変異 性体を部分構造として有するオルトメタル錯体であることが好ましい。  [0182] The orthometal complex having a partial structure represented by the general formula (10) or a tautomer thereof as a partial structure is a partial structure represented by the general formulas (11) to (14) or a tautomer thereof. It is preferable that it is an ortho metal complex which has an active substance as a partial structure.
[0183] 式中、 Mは元素周期表における第 8〜10族の金属元素を表す。 X 、X 、X 、X  [0183] In the formula, M represents a metal element of Groups 8 to 10 in the periodic table. X, X, X, X
71 72 73 74 は、各々炭素原子または窒素原子を表し、 Q は炭素原子、 X 、X  71 72 73 74 each represents a carbon atom or a nitrogen atom, Q is a carbon atom, X, X
71 71 73と共に 6員の芳 香族炭化水素環または 5〜6員の芳香族複素環である環 Hを形成する原子群を表し 、 Q は窒素原子、 X 、 X と共に 5〜6員の芳香族複素環である環 Kを形成する原子 71 71 73 represents a group of atoms forming ring H which is a 6-membered aromatic hydrocarbon ring or a 5- to 6-membered aromatic heterocyclic ring, Q is a nitrogen atom, and 5 to 6-membered aromatic together with X and X Atoms forming ring K, a heterocyclic ring
23 72 74 23 72 74
群を表す。 Q  Represents a group. Q
73は炭素原子と共に芳香族炭化水素環または芳香族複素環を形成する 原子群を表す。 Q  73 represents an atomic group that forms an aromatic hydrocarbon ring or an aromatic heterocycle with carbon atoms. Q
74は窒素原子と共に芳香族複素環を形成する原子群を表す。 X  74 represents an atomic group forming an aromatic heterocyclic ring with a nitrogen atom. X
7は 7
0、 S、 CH、 CHR、 CR、 NR、 PR、 SiR、 C = 0、 C=NR、 SOまたは SOを表す。 0, S, CH, CHR, CR, NR, PR, SiR, C = 0, C = NR, SO or SO.
2 2 2 2 2 2 2 2
Rはアルキル基、シクロアルキル基、アルケニル基、ァリール基、複素環基または芳 香族複素環基を表す。 R represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group.
[0184] 前記 6員の芳香族炭化水素環、 5〜6員の芳香族複素環は前記態様 (1)で述べた ものと同義である。  [0184] The 6-membered aromatic hydrocarbon ring and the 5- to 6-membered aromatic heterocyclic ring have the same meanings as described in the embodiment (1).
[0185] 前記アルキル基、シクロアルキル基、ァルケ-ル基、ァリール基、複素環基または 芳香族複素環基は、前記態様(1)で述べたものと同義である。  [0185] The alkyl group, cycloalkyl group, alkyl group, aryl group, heterocyclic group or aromatic heterocyclic group has the same meaning as described in the embodiment (1).
[0186] 前記態様(13)の有機 EL素子材料は、前記一般式 (4)または一般式 (6)の X — X [0186] The organic EL device material of the embodiment (13) is X — X of the general formula (4) or the general formula (6).
31 31
-X によって形成される二座配位子が、前記一般式 (4 1)〜 (4 31)で表されるThe bidentate ligand formed by -X is represented by the general formulas (4 1) to (4 31)
3 32 3 32
部分構造またはまたはその互変異性体を部分構造として有するオルトメタル錯体で あることを特徴とする。  It is an ortho metal complex having a partial structure or a tautomer thereof as a partial structure.
[0187] 式中、 R は R —CO—または R —SO—を表し、 R はアルキル基、シクロアルキ  [0187] In the formula, R represents R —CO— or R —SO—, R represents an alkyl group, cycloalkyl
81 80 80 2 80  81 80 80 2 80
ル基、ァリール基、複素環基または芳香族複素環基を表す。 R 、 R 、 R 、 R  Represents an alkyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. R, R, R, R
82 83 86 87は置 換基を表し、 n は 0〜3の整数を表し、 n 、n は 0〜2の整数を表す。 R 、R 、R 、  82 83 86 87 represents a substituent, n represents an integer of 0 to 3, and n and n represent an integer of 0 to 2. R, R, R,
81 82 83 84 85 88 R はアルキル基、シクロアルキル基、ァリール基、複素環基または芳香族複素環基81 82 83 84 85 88 R is an alkyl group, a cycloalkyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group
89 89
を表す。 Q は炭素、窒素と共に 5〜6員の芳香族複素環を形成する原子群を表し、  Represents. Q represents an atomic group that forms a 5- or 6-membered aromatic heterocycle with carbon and nitrogen,
81  81
Q 、Q は炭素、窒素と共に 5員の芳香族複素環を形成する原子群を表す。  Q 1 and Q 2 represent an atomic group that forms a 5-membered aromatic heterocycle with carbon and nitrogen.
82 83  82 83
[0188] 前記 5〜6員の芳香族複素環は前記態様(1)で述べたものと同義である。  [0188] The 5- to 6-membered aromatic heterocyclic ring has the same meaning as described in the embodiment (1).
[0189] 前記アルキル基、シクロアルキル基、ァルケ-ル基、ァリール基、複素環基または 芳香族複素環基は、前記態様(1)で述べたものと同義である。 [0189] The alkyl group, cycloalkyl group, alkyl group, aryl group, heterocyclic group or aromatic heterocyclic group has the same meaning as described in the embodiment (1).
[0190] 前記態様(14)の有機 EL素子材料は、前記全ての一般式において、 M力イリジゥ ムまたは白金であるオルトメタル錯体であることを特徴とする。 [0190] The organic EL device material of the aspect (14) is characterized in that, in all the general formulas, it is an orthometallic complex which is M force iridium or platinum.
[0191] 本発明に好ましく用いられるオルトメタル錯体を下記に示す。 [0191] Ortho metal complexes preferably used in the present invention are shown below.
[0192] [化 54] [0192] [Chemical 54]
[0193] [化 55] [0193] [Chemical 55]
[0194] [化 56] [0194] [Chemical 56]
[0195] [化 57] [0195] [Chemical 57]
[0196] [化 58] [0196] [Chemical 58]
[0197] [化 59] [09^ ] [8610] [0197] [Chemical 59] [09 ^] [8610]
llC0C/900Zdf/X3d 09 0ΖΪ860/900Ζ OAV llC0C / 900Zdf / X3d 09 0ΖΪ860 / 900Ζ OAV
[0199] [化 61] [0199] [Chemical 61]
[0200] [化 62] [0200] [Chemical 62]
[0201] [化 63] [0201] [Chemical 63]
[0202] [化 64] [0202] [Chemical 64]
[0203] [化 65] [99^ ] 0] [0203] [Chemical 65] [99 ^] 0]
[0205] [化 67] [0205] [Chemical 67]
[0206] [化 68] [0206] [Chemical 68]
[0209] [ィ匕 71] [0209] [Yi 71]
[0210] [化 72] [0210] [Chemical 72]
[0211] [化 73] [0211] [Chemical 73]
[0212] [化 74] [0212] [Chemical 74]
[0213] [化 75] [0213] [Chemical 75]
[0214] [化 76] [0214] [Chemical 76]
[0215] [化 77] [0215] [Chemical 77]
これらのィ匕合物は、例えば、 Organic Leter, voll3, No. 16, p2579〜2581 (2 These compounds are, for example, Organic Leter, voll3, No. 16, p2579-2581 (2
001)、 Inorganic Chemistry, vol30, No. 8, pl685〜1687 (1991)、 J. Am. Chem. Soc. , voll23, p4304 (2001) , Inorganic Chemistry, vol41, No. 1 2, pl3056〜3066 (2002)、 New Jounal of Chemistry, vol26, pi 171 (20001), Inorganic Chemistry, vol30, No. 8, pl685-1687 (1991), J. Am. Chem. Soc., Voll23, p4304 (2001), Inorganic Chemistry, vol41, No. 1 2, pl3056-3066 (2002) ), New Jounal of Chemistry, vol26, pi 171 (20
02)、さらにこれらの文献中に記載の参考文献等の方法を適用することにより合成で きる。 02), and by applying methods such as references described in these documents, wear.
[0217] 本発明においては、上記有機 EL素子材料を、有機 EL素子を構成するいずれかの 構成層 (有機層)に含有させ有機 EL素子を作製する。  In the present invention, the organic EL element material is contained in any of the constituent layers (organic layers) constituting the organic EL element to produce an organic EL element.
[0218] 有機 EL素子が構成層として発光層を有し、該発光層が上記有機 EL素子材料を含 有することが好ましい。発光層に含有する場合は、発光層中の発光ドーパントとして 用いることにより、本発明の目的である有機 EL素子の発光寿命の長寿命化を達成す ることがでさる。 [0218] The organic EL element preferably has a light emitting layer as a constituent layer, and the light emitting layer preferably contains the organic EL element material. When it is contained in the light emitting layer, it can be used as a light emitting dopant in the light emitting layer to achieve a long emission life of the organic EL device which is the object of the present invention.
[0219] また、有機 EL素子が構成層として正孔阻止層を有し、該正孔阻止層が上記有機 E [0219] Further, the organic EL element has a hole blocking layer as a constituent layer, and the hole blocking layer includes the organic E
L素子材料を含有することが好ま 、。 It is preferable to contain L element material.
[0220] 前記態様(18)の有機 EL素子は、前記一般式(1A)で表される化合物を含有する ことを特徴とする。 [0220] The organic EL device of the aspect (18) is characterized by containing the compound represented by the general formula (1A).
[0221] 式中、 Zは芳香族複素環を表し、 Zは芳香族複素環または芳香族炭化水素環を  [0221] In the formula, Z represents an aromatic heterocyclic ring, Z represents an aromatic heterocyclic ring or an aromatic hydrocarbon ring.
1 2  1 2
表し、 Zは 2価の連結基または単なる結合手を表す。 R は水素原子または置換基を Z represents a divalent linking group or a simple bond. R is a hydrogen atom or a substituent
3 101 3 101
表す。  To express.
[0222] 前記一般式( 1 A)にお 、て、 Zは置換基を有してもよ!、芳香族複素環を表し、 Zは  [0222] In the general formula (1A), Z may have a substituent! Represents an aromatic heterocyclic ring, and Z is
1 2 置換基を有してもよい芳香族複素環、もしくは芳香族炭化水素環を表し、 Z  1 2 represents an aromatic heterocycle or an aromatic hydrocarbon ring which may have a substituent, Z
3は 2価の 連結基、もしくは単なる結合手を表す。 R  3 represents a divalent linking group or a simple bond. R
101は水素原子、もしくは置換基を表す。  101 represents a hydrogen atom or a substituent.
[0223] Z、 Zで表される芳香族複素環としては、フラン環、チォフェン環、ピリジン環、ピリ  [0223] Aromatic heterocycles represented by Z and Z include furan ring, thiophene ring, pyridine ring,
1 2  1 2
ダジン環、ピリミジン環、ピラジン環、トリアジン環、ベンゾイミダゾール環、ォキサジァ ゾール環、トリァゾール環、イミダゾール環、ピラゾール環、チアゾール環、インドール 環、ベンゾイミダゾール環、ベンゾチアゾール環、ベンゾォキサゾール環、キノキサリ ン環、キナゾリン環、フタラジン環、力ルバゾール環、カルボリン環、ジァザカルバゾー ル環 (カルボリン環を構成する炭化水素環の炭素原子の一つがさらに窒素原子で置 換されている環を示す)等が挙げられる。さらに前記芳香族複素環は、後述する R  Dazine ring, pyrimidine ring, pyrazine ring, triazine ring, benzimidazole ring, oxadiazole ring, triazole ring, imidazole ring, pyrazole ring, thiazole ring, indole ring, benzimidazole ring, benzothiazole ring, benzoxazole ring, quinoxari Ring, quinazoline ring, phthalazine ring, force rubazole ring, carboline ring, diazacarbazole ring (showing a ring in which one of the carbon atoms of the hydrocarbon ring constituting the carboline ring is further replaced by a nitrogen atom), etc. It is done. Further, the aromatic heterocycle is R described later.
101 で表される置換基を有してもょ ヽ。  It may have a substituent represented by 101.
[0224] Zで表される芳香族炭化水素環としては、ベンゼン環、ビフヱ-ル環、ナフタレン環  [0224] Examples of the aromatic hydrocarbon ring represented by Z include a benzene ring, biphenyl ring, and naphthalene ring.
2  2
、ァズレン環、アントラセン環、フエナントレン環、ピレン環、タリセン環、ナフタセン環、 トリフエ-レン環、 o—テルフエ-ル環、 m—テルフエ-ル環、 p—テルフエ-ル環、ァ セナフテン環、コロネン環、フルオレン環、フルオラントレン環、ナフタセン環、ペンタ セン環、ペリレン環、ペンタフェン環、ピセン環、ピレン環、ピラントレン環、アンスラァ ントレン環等が挙げられる。さらに前記芳香族炭化水素環は、後述する R で表され , Azulene ring, anthracene ring, phenanthrene ring, pyrene ring, taricene ring, naphthacene ring, triphenylene ring, o-terfel ring, m-terfel ring, p-terfel ring, a Examples include a naphthenic ring, a coronene ring, a fluorene ring, a fluoranthrene ring, a naphthacene ring, a pentacene ring, a perylene ring, a pentaphen ring, a picene ring, a pyrene ring, a pyranthrene ring, and an anthanthrene ring. Further, the aromatic hydrocarbon ring is represented by R described later.
101 る置換基を有してちょい。  101 substituents.
R で表される置換基としては、アルキル基 (例えば、メチル基、ェチル基、プロピル Examples of the substituent represented by R include an alkyl group (for example, methyl group, ethyl group, propyl group).
101 101
基、イソプロピル基、 tert—ブチル基、ペンチル基、へキシル基、ォクチル基、ドデシ ル基、トリデシル基、テトラデシル基、ペンタデシル基等)、シクロアルキル基 (例えば 、シクロペンチル基、シクロへキシル基等)、ァルケ-ル基 (例えば、ビュル基、ァリル 基等)、アルキニル基 (例えば、ェチニル基、プロパルギル基等)、ァリール基 (例えばGroup, isopropyl group, tert-butyl group, pentyl group, hexyl group, octyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, etc.), cycloalkyl group (for example, cyclopentyl group, cyclohexyl group, etc.) Alkenyl group (for example, buyl group, allyl group, etc.), alkynyl group (for example, ethynyl group, propargyl group, etc.), aryl group (for example,
、フエ-ル基、ナフチル基等)、芳香族複素環基 (例えば、フリル基、チェ-ル基、ピリ ジル基、ピリダジ -ル基、ピリミジ -ル基、ピラジュル基、トリアジニル基、イミダゾリル 基、ピラゾリル基、チアゾリル基、キナゾリ-ル基、フタラジニル基等)、複素環基 (例 えば、ピロリジル基、イミダゾリジル基、モルホリル基、ォキサゾリジル基等)、アルコキ シル基 (例えば、メトキシ基、エトキシ基、プロピルォキシ基、ペンチルォキシ基、へキ シルォキシ基、ォクチルォキシ基、ドデシルォキシ基等)、シクロアルコキシル基 (例 えば、シクロペンチルォキシ基、シクロへキシルォキシ基等)、ァリールォキシ基 (例え ば、フエノキシ基、ナフチルォキシ基等)、アルキルチオ基 (例えば、メチルチオ基、ェ チルチオ基、プロピルチオ基、ペンチルチオ基、へキシルチオ基、ォクチルチオ基、 ドデシルチオ基等)、シクロアルキルチオ基 (例えば、シクロペンチルチオ基、シクロ へキシルチオ基等)、ァリールチオ基 (例えば、フエ-ルチオ基、ナフチルチオ基等) 、アルコキシカルボ-ル基(例えば、メチルォキシカルボ-ル基、ェチルォキシカルボ ニル基、ブチルォキシカルボ-ル基、ォクチルォキシカルボ-ル基、ドデシルォキシ カルボ-ル基等)、ァリールォキシカルボ-ル基(例えば、フエ-ルォキシカルボ-ル 基、ナフチルォキシカルボ-ル基等)、スルファモイル基(例えば、アミノスルホ -ル基 、メチルアミノスルホ -ル基、ジメチルアミノスルホ -ル基、ブチルアミノスルホ -ル基 、へキシルアミノスルホ -ル基、シクロへキシルアミノスルホ -ル基、ォクチルアミノス ルホ-ル基、ドデシルアミノスルホ-ル基、フエ-ルアミノスルホ -ル基、ナフチルアミ ノスルホ -ル基、 2—ピリジルアミノスルホ -ル基等)、ァシル基 (例えば、ァセチル基 、ェチルカルボ-ル基、プロピルカルボ-ル基、ペンチルカルボ-ル基、シクロへキ シルカルボ-ル基、ォクチルカルポ-ル基、 2—ェチルへキシルカルボ-ル基、ドデ シルカルボ-ル基、フ -ルカルポ-ル基、ナフチルカルボ-ル基、ピリジルカルボ -ル基等)、ァシルォキシ基 (例えば、ァセチルォキシ基、ェチルカルボニルォキシ 基、ブチルカルボ-ルォキシ基、ォクチルカルボ-ルォキシ基、ドデシルカルボ -ル ォキシ基、フエニルカルボ-ルォキシ基等)、アミド基 (例えば、メチルカルボ-ルアミ ノ基、ェチルカルボ-ルァミノ基、ジメチルカルボ-ルァミノ基、プロピルカルボ-ルァ ミノ基、ペンチルカルボ-ルァミノ基、シクロへキシルカルボ-ルァミノ基、 2—ェチル へキシルカルボ-ルァミノ基、ォクチルカルボ-ルァミノ基、ドデシルカルボ-ルァミノ 基、フ -ルカルポ-ルァミノ基、ナフチルカルボ-ルァミノ基等)、力ルバモイル基( 例えば、ァミノカルボ-ル基、メチルァミノカルボ-ル基、ジメチルァミノカルボ-ル基 、プロピルアミノカルボ-ル基、ペンチルァミノカルボ-ル基、シクロへキシルァミノ力 ルポ-ル基、ォクチルァミノカルボ-ル基、 2—ェチルへキシルァミノカルボ-ル基、 ドデシルァミノカルボ-ル基、フエ-ルァミノカルボ-ル基、ナフチルァミノカルボ-ル 基、 2—ピリジルァミノカルボニル基等)、ウレイド基 (例えば、メチルウレイド基、ェチ ルゥレイド基、ペンチルゥレイド基、シクロへキシルウレイド基、ォクチルゥレイド基、ド デシルゥレイド基、フ ニルゥレイド基ナフチルウレイド基、 2—ピリジルアミノウレイド 基等)、スルフィエル基(例えば、メチルスルフィ-ル基、ェチルスルフィ-ル基、プチ ルスルフィ-ル基、シクロへキシルスルフィエル基、 2—ェチルへキシルスルフィエル 基、ドデシルスルフィエル基、フヱニルスルフィ-ル基、ナフチルスルフィ-ル基、 2— ピリジルスルフィ -ル基等)、アルキルスルホ -ル基(例えば、メチルスルホ -ル基、ェ チルスルホ-ル基、ブチルスルホ -ル基、シクロへキシルスルホ -ル基、 2—ェチル へキシルスルホ -ル基、ドデシルスルホ -ル基等)、ァリールスルホ -ル基(フエ-ル スルホ-ル基、ナフチルスルホ-ル基、 2—ピリジルスルホ -ル基等)、アミノ基(例え ば、アミノ基、ェチルァミノ基、ジメチルァミノ基、ブチルァミノ基、シクロペンチルァミノ 基、 2—ェチルへキシルァミノ基、ドデシルァミノ基、ァ-リノ基、ナフチルァミノ基、 2 ピリジルァミノ基等)、ハロゲン原子 (例えば、フッ素原子、塩素原子、臭素原子等) 、フッ化炭化水素基(例えば、フルォロメチル基、トリフルォロメチル基、ペンタフルォ 口ェチル基、ペンタフルォロフエ-ル基等)、シァノ基、ニトロ基、ヒドロキシル基、メル カプト基、シリル基 (例えば、トリメチルシリル基、トリイソプロビルシリル基、トリフエ-ル シリル基、フエ二ルジェチルシリル基等)、等が挙げられる。 , Phenyl group, naphthyl group, etc.), aromatic heterocyclic group (e.g. furyl group, chael group, pyridyl group, pyridazyl group, pyrimidyl group, pyrazyl group, triazinyl group, imidazolyl group, Pyrazolyl group, thiazolyl group, quinazolyl group, phthalazinyl group, etc.), heterocyclic group (eg, pyrrolidyl group, imidazolidyl group, morpholyl group, oxazolidyl group, etc.), alkoxyl group (eg, methoxy group, ethoxy group, propyloxy group) Group, pentyloxy group, hexyloxy group, octyloxy group, dodecyloxy group, etc.), cycloalkoxyl group (eg, cyclopentyloxy group, cyclohexyloxy group, etc.), aryloxy group (eg, phenoxy group, naphthyloxy group, etc.) An alkylthio group (e.g., methylthio group, ethylthio group, propylthio group, Nylthio group, hexylthio group, octylthio group, dodecylthio group, etc.), cycloalkylthio group (eg, cyclopentylthio group, cyclohexylthio group, etc.), arylthio group (eg, phenylthio group, naphthylthio group, etc.), alkoxycarbo- Group (for example, methyloxycarbonyl group, ethyloxycarbonyl group, butoxycarbonyl group, octyloxycarbonyl group, dodecyloxycarbonyl group, etc.), aryloxy Carbon groups (for example, phenyl carbonate groups, naphthyloxy carbonate groups, etc.), sulfamoyl groups (for example, aminosulfol groups, methylaminosulfol groups, dimethylaminosulfol groups, butylamino) Sulfol group, Hexylaminosulfol group, Cyclohexylaminosulfol group, Octylaminosulfo- Group, dodecyl aminosulfonyl - group, Hue - Ruaminosuruho - group, naphthylamine Nosuruho - group, 2-pyridyl aminosulfonyl - Le group), Ashiru group (e.g., Asechiru group , Ethylcarbol group, propylcarbol group, pentylcarbol group, cyclohexylcarbol group, octylcarlool group, 2-ethylhexylcarbol group, dodecylcarbol group, fullcarporo Group, naphthylcarbol group, pyridylcarbol group, etc.), acyloxy group (for example, acetyloxy group, ethylcarbonyloxy group, butylcarboxoxy group, octylcarboxoxy group, dodecylcarboxoxy group, Phenylcarbo-loxy group, etc.), amide group (for example, methyl carboamino group, ethyl carbolumino group, dimethyl carbolumino group, propyl carbolumino group, pentyl carbolumino group, cyclohexyl carbolumino group, 2 —Ethyl hexyl carbolumino group, octyl carbolumino group, dodecyl carbolua group Group, full-carbon group, naphthyl carbo-amino group, etc., rubamoyl group (for example, amino-carbo group, methyl-amino group, dimethyl-amino group, propylamino-carbo group) Group, pentylaminocarbol group, cyclohexylamino group, octylaminocarbol group, 2-ethylhexylaminocarbol group, dodecylaminocarbol group, phenol Ruaminocarbol group, naphthylaminocarbole group, 2-pyridylaminocarbonyl group, etc., ureido group (for example, methylureido group, ethylureido group, pentylureido group, cyclohexylureido group, octylureido group, Dodecylureido group, phenylureido group, naphthylureido group, 2-pyridylaminoureido group, etc.), sulfiel group (eg methyl Rufyl group, ethylsulfuric group, propylsulfuryl group, cyclohexylsulfuryl group, 2-ethylhexylsulfuryl group, dodecylsulfuryl group, phenylsulfyl group, naphthylsulfuric group, 2 — Pyridylsulfyl group, etc.), alkylsulfol groups (eg methylsulfol group, ethylsulfol group, butylsulfol group, cyclohexylsulfol group, 2-ethylhexylsulfol group, Dodecyl sulfol group, etc.), aryl sulfol group (phenol sulfol group, naphthyl sulfol group, 2-pyridyl sulfol group etc.), amino group (eg amino group, ethylamino group, dimethylamino) Group, butyramino group, cyclopentylamino group, 2-ethylhexylamino group, dodecylamino group, linrino group, naphthylamino group, 2 pyridyl group Ruamino group), a halogen atom (e.g., fluorine atom, chlorine atom, bromine atom), fluorinated hydrocarbon radicals (e.g., Furuoromechiru group, triflate Ruo Russia methyl, Pentafuruo Phthalyl group, pentafluorophenyl group, etc.), cyano group, nitro group, hydroxyl group, mercapto group, silyl group (for example, trimethylsilyl group, triisopropyl silyl group, triphenylsilyl group, phenyl group) Rugetylsilyl group, etc.).
[0226] これらの置換基は上記の置換基によってさらに置換されていてもよい。また、これら の置換基は複数が互いに結合して環を形成して 、てもよ 、。好ま 、置換基としては 、アルキル基、シクロアルキル基、フッ化炭化水素基、ァリール基、芳香族複素環基 である。  [0226] These substituents may be further substituted with the above substituents. In addition, a plurality of these substituents may be bonded to each other to form a ring. Preferably, the substituent is an alkyl group, a cycloalkyl group, a fluorinated hydrocarbon group, an aryl group, or an aromatic heterocyclic group.
[0227] Zで表される 2価の連結基としては、アルキレン、ァルケ-レン、アルキ-レン、ァリ  [0227] Examples of the divalent linking group represented by Z include alkylene, alkylene, alkylene, and aryl.
3  Three
一レン等の炭化水素基の他、ヘテロ原子を含むものであってもよぐまたチォフェン 2, 5 ジィル基ゃピラジン 2, 3 ジィル基のような芳香族複素環を有する化合 物(ヘテロ芳香族化合物ともいう)に由来する 2価の連結基であってもよいし、酸素や 硫黄等のカルコゲン原子であってもよい。また、アルキルイミノ基、ジアルキルシラン ジィル基ゃジァリールゲルマンジィル基のようなヘテロ原子を会して連結する基でも よい。  In addition to hydrocarbon groups such as mono-ene, compounds containing heteroatoms may also be used, and compounds having aromatic heterocycles such as thiophene 2, 5 diyl group or pyrazine 2, 3 diyl group (heteroaromatics) It may be a divalent linking group derived from a compound) or a chalcogen atom such as oxygen or sulfur. Further, it may be a group in which heteroatoms such as an alkylimino group, dialkylsilane diyl group or diarylgermandyl group are linked to each other.
[0228] 単なる結合手とは、連結する置換基同士を直接結合する結合手である。  [0228] A mere bond is a bond that directly bonds the linking substituents together.
[0229] 本発明においては、前記一般式(1A)の Z力 ½員環であることが好ましい。これによ  [0229] In the present invention, the Z-membered ring represented by the general formula (1A) is preferable. This
1  1
り、より発光効率を高くすることができる。さらに一層長寿命化させることができる。また 、本発明においては、 Z力 ½員環であることが好ましい。これにより、より発光効率を高  Thus, the luminous efficiency can be further increased. Further, the life can be extended. In the present invention, a Z-membered ring is preferable. This increases the luminous efficiency.
2  2
くすることができる。さらにより一層長寿命化させることができる。さらに Z  Can be used. Further, the lifetime can be further increased. Z
1と Z  1 and Z
2を共に 6 員環とすることで、より一層発光効率と高くすることができるので好ましい。さらにより 一層長寿命化させることができるので好ましい。また、 z  It is preferable that both 2 are 6-membered rings because the luminous efficiency can be further increased. Further, it is preferable because the lifetime can be further increased. Z
3は結合手であることが好まし い。これによりより発光効率を高くすることができ、一層長寿命化させることができる。 更に一般式(1A)で表される化合物は分子量が 450以上であることが好ましぐこれ により発光効率を高くすることができ、長寿命化することができる。  3 is preferably a bond. Thereby, the luminous efficiency can be further increased and the life can be further extended. Furthermore, it is preferable that the compound represented by the general formula (1A) has a molecular weight of 450 or more, which can increase the luminous efficiency and prolong the life.
[0230] 前記一般式(1A)で表される化合物で好ましいのは、前記一般式(1A— 1)〜(: LA  [0230] The compound represented by the general formula (1A) is preferably a compound represented by the general formula (1A-1) to (: LA
10)で各々表される化合物である。  It is a compound represented by each of 10).
[0231] 前記一般式(1A— 1)において、 R 〜R は各々独立に水素原子もしくは置換基  [0231] In the general formula (1A-1), R to R each independently represent a hydrogen atom or a substituent.
501 507  501 507
を表す。一般式(1A— 1)で表される化合物を用いることで、より発光効率の高い有 機 EL素子とすることができる。さらにより長寿命の有機 EL素子とすることができる。 Represents. By using the compound represented by the general formula (1A-1), It can be an EL element. Furthermore, it is possible to obtain a longer-life organic EL device.
[0232] 前記一般式(1A— 2)において、 R 〜R は各々独立に水素原子もしくは置換基 [0232] In the general formula (1A-2), R to R each independently represent a hydrogen atom or a substituent.
511 517  511 517
を表す。一般式(1A— 2)で表される化合物を用いることで、より発光効率の高い有 機 EL素子とすることができる。さらにより長寿命の有機 EL素子とすることができる。  Represents. By using the compound represented by the general formula (1A-2), an organic EL device with higher luminous efficiency can be obtained. Furthermore, it is possible to obtain a longer-life organic EL device.
[0233] 前記一般式(1A— 3)において、 R 〜R は各々独立に水素原子もしくは置換基 [0233] In the general formula (1A-3), R to R each independently represent a hydrogen atom or a substituent.
521 527  521 527
を表す。一般式(1A— 3)で表される化合物を用いることで、より発光効率の高い有 機 EL素子とすることができる。さらにより長寿命の有機 EL素子とすることができる。  Represents. By using the compound represented by the general formula (1A-3), an organic EL element with higher luminous efficiency can be obtained. Furthermore, it is possible to obtain a longer-life organic EL device.
[0234] 前記一般式(1A— 4)において、 R 〜R は各々独立に水素原子もしくは置換基 [0234] In the general formula (1A-4), R to R each independently represent a hydrogen atom or a substituent.
531 537  531 537
を表す。一般式(1A— 4)で表される化合物を用いることで、より発光効率の高い有 機 EL素子とすることができる。さらにより長寿命の有機 EL素子とすることができる。  Represents. By using the compound represented by the general formula (1A-4), an organic EL device with higher luminous efficiency can be obtained. Furthermore, it is possible to obtain a longer-life organic EL device.
[0235] 前記一般式(1A— 5)において、 R 〜R は各々独立に水素原子もしくは置換基 [0235] In the general formula (1A-5), R to R each independently represent a hydrogen atom or a substituent.
541 548  541 548
を表す。一般式(1A— 5)で表される化合物を用いることで、より発光効率の高い有 機 EL素子とすることができる。さらにより長寿命の有機 EL素子とすることができる。  Represents. By using the compound represented by the general formula (1A-5), an organic EL device with higher luminous efficiency can be obtained. Furthermore, it is possible to obtain a longer-life organic EL device.
[0236] 前記一般式(1A— 6)において、 R 〜R は各々独立に水素原子もしくは置換基 [0236] In the general formula (1A-6), R to R each independently represent a hydrogen atom or a substituent.
551 558  551 558
を表す。一般式(1A— 6)で表される化合物を用いることで、より発光効率の高い有 機 EL素子とすることができる。さらにより長寿命の有機 EL素子とすることができる。  Represents. By using the compound represented by the general formula (1A-6), an organic EL device with higher luminous efficiency can be obtained. Furthermore, it is possible to obtain a longer-life organic EL device.
[0237] 前記一般式(1A— 7)において、 R 〜R は各々独立に水素原子もしくは置換基 [0237] In the general formula (1A-7), R to R each independently represent a hydrogen atom or a substituent.
561 567  561 567
を表す。一般式(1A— 7)で表される化合物を用いることで、より発光効率の高い有 機 EL素子とすることができる。さらにより長寿命の有機 EL素子とすることができる。  Represents. By using the compound represented by the general formula (1A-7), an organic EL element with higher luminous efficiency can be obtained. Furthermore, it is possible to obtain a longer-life organic EL device.
[0238] 前記一般式(1A— 8)において、 R 〜R は各々独立に水素原子もしくは置換基 [0238] In the general formula (1A-8), R to R each independently represent a hydrogen atom or a substituent.
571 577  571 577
を表す。一般式(1A— 8)で表される化合物を用いることで、より発光効率の高い有 機 EL素子とすることができる。さらにより長寿命の有機 EL素子とすることができる。  Represents. By using the compound represented by the general formula (1A-8), an organic EL element with higher luminous efficiency can be obtained. Furthermore, it is possible to obtain a longer-life organic EL device.
[0239] 前記一般式(1A— 9)において、 Rは水素原子もしくは置換基を表す。また、複数の Rは各々同一でもよぐ異なっていてもよい。一般式(1 A— 9)で表される化合物を用 いることで、より発光効率の高い有機 EL素子とすることができる。さらにより長寿命の 有機 EL素子とすることができる。  In the general formula (1A-9), R represents a hydrogen atom or a substituent. The plurality of R may be the same or different. By using the compound represented by the general formula (1 A-9), an organic EL device with higher luminous efficiency can be obtained. Furthermore, it is possible to make an organic EL element with a longer life.
[0240] 前記一般式(1A— 10)において、 Rは水素原子もしくは置換基を表す。また、複数 の Rは各々同一でもよぐ異なっていてもよい。一般式(1 A— 10)で表される化合物 を用いることで、より発光効率の高い有機 EL素子とすることができる。さらに長寿命の 有機 EL素子とすることができる。 In the general formula (1A-10), R represents a hydrogen atom or a substituent. The plurality of R may be the same or different. Compound represented by general formula (1 A-10) By using, an organic EL element with higher luminous efficiency can be obtained. Furthermore, it can be a long-life organic EL device.
[0241] また、前記一般式(1A)で表される化合物で好ましいものは、前記一般式(2A— 1) 〜(2A— 10)のいずれかで表される基を少なくとも一つを有する化合物である。特に 、分子内に前記一般式(2A— 1)〜(2A— 10)の 、ずれかで表される基を 2つから 4 つ有することがより好ましい。このとき、前記一般式(1A)で表される構造において、 R を除 、た部分が前記一般式 (2A— 1)〜(2A— 10)に置き換わる場合を含む。[0241] The compound represented by the general formula (1A) is preferably a compound having at least one group represented by any one of the general formulas (2A-1) to (2A-10). It is. In particular, it is more preferable to have 2 to 4 groups represented by the deviations of the general formulas (2A-1) to (2A-10) in the molecule. In this case, the structure represented by the general formula (1A) includes a case where R is removed and the part is replaced by the general formulas (2A-1) to (2A-10).
101 101
[0242] このとき、特に前記一般式(3A)〜(17A)で表される化合物であることが本発明の 効果を得る上で好ましい。  [0242] At this time, the compounds represented by the general formulas (3A) to (17A) are particularly preferable for obtaining the effects of the present invention.
[0243] 前記一般式(3A)において、 R 〜R は水素原子もしくは置換基を表すが、 R 〜 [0243] In the general formula (3A), R to R represent a hydrogen atom or a substituent.
601 606 601 601 606 601
R の少なくとも一つは前記一般式(2A— 1)〜(2A— 10)の 、ずれかで表される基At least one R is a group represented by any of the formulas (2A-1) to (2A-10).
606 606
を表す。一般式 (3A)で表される化合物を用いることにより、より発光効率の高い有機 EL素子とすることができる。さらにより長寿命の有機 EL素子とすることができる。  Represents. By using the compound represented by the general formula (3A), an organic EL device with higher luminous efficiency can be obtained. Furthermore, it is possible to obtain a longer-life organic EL device.
[0244] 前記一般式 (4A)において、 R 〜R は水素原子もしくは置換基を表すが、 R 〜 [0244] In the general formula (4A), R to R represent a hydrogen atom or a substituent.
611 620 611 611 620 611
R の少なくとも一つは前記一般式(2A— 1)〜(2A— 10)の 、ずれかで表される基At least one R is a group represented by any of the formulas (2A-1) to (2A-10).
620 620
を表す。一般式 (4A)で表される化合物を用いることで、より発光効率の高い有機 EL 素子とすることができる。さらにより長寿命の有機 EL素子とすることができる。  Represents. By using the compound represented by the general formula (4A), an organic EL device with higher luminous efficiency can be obtained. Furthermore, it is possible to obtain a longer-life organic EL device.
[0245] 前記一般式(5A)において、 R 〜R は水素原子もしくは置換基を表すが、 R 〜 [0245] In the general formula (5A), R to R represent a hydrogen atom or a substituent.
621 623 621 621 623 621
R の少なくとも一つは前記一般式(2A— 1)〜(2A— 10)の 、ずれかで表される基At least one R is a group represented by any of the formulas (2A-1) to (2A-10).
623 623
を表す。一般式 (5A)で表される化合物を用いることで、より発光効率の高い有機 EL 素子とすることができる。さらにより長寿命の有機 EL素子とすることができる。  Represents. By using the compound represented by the general formula (5A), an organic EL device with higher luminous efficiency can be obtained. Furthermore, it is possible to obtain a longer-life organic EL device.
[0246] 前記一般式 (6A)において、 R 〜R は水素原子もしくは置換基を表すが、 R 〜 [0246] In the general formula (6A), R to R represent a hydrogen atom or a substituent.
631 645 631 631 645 631
R の少なくとも一つは前記一般式(2A— 1)〜(2A— 10)の 、ずれかで表される基At least one R is a group represented by any of the formulas (2A-1) to (2A-10).
645 645
を表す。一般式 (6A)で表される化合物を用いることで、より発光効率の高い有機 EL 素子とすることができる。さらにより長寿命の有機 EL素子とすることができる。  Represents. By using the compound represented by the general formula (6A), an organic EL device with higher luminous efficiency can be obtained. Furthermore, it is possible to obtain a longer-life organic EL device.
[0247] 前記一般式(7A)において、 R 〜R は水素原子もしくは置換基を表すが、 R 〜 [0247] In the general formula (7A), R to R represent a hydrogen atom or a substituent.
651 656 651 651 656 651
R の少なくとも一つは前記一般式(2A— 1)〜(2A— 10)の 、ずれかで表される基At least one R is a group represented by any of the formulas (2A-1) to (2A-10).
656 656
を表す。 naは 0〜5の整数を表し、 nbは 1〜6の整数を表すが、 naと nbの和が 6であ る。一般式 (7A)で表される化合物を用いることで、より発光効率の高い有機 EL素子 とすることができる。さらにより長寿命の有機 EL素子とすることができる。 Represents. na represents an integer from 0 to 5, nb represents an integer from 1 to 6, but the sum of na and nb is 6. The By using the compound represented by the general formula (7A), an organic EL device with higher luminous efficiency can be obtained. Furthermore, it is possible to obtain a longer-life organic EL device.
[0248] 前記一般式 (8A)において、 R 〜R は水素原子もしくは置換基を表すが、 R 〜 [0248] In the general formula (8A), R to R represent a hydrogen atom or a substituent.
661 672 661 661 672 661
R の少なくとも一つは前記一般式(2A— 1)〜(2A— 10)の 、ずれかで表される基At least one R is a group represented by any of the formulas (2A-1) to (2A-10).
672 672
を表す。一般式 (8A)で表される化合物を用いることで、より発光効率の高い有機 EL 素子とすることができる。さらにより長寿命の有機 EL素子とすることができる。  Represents. By using the compound represented by the general formula (8A), an organic EL device with higher luminous efficiency can be obtained. Furthermore, it is possible to obtain a longer-life organic EL device.
[0249] 前記一般式(9A)において、 R 〜R は水素原子もしくは置換基を表す力 R 〜 [0249] In the general formula (9A), R ~ R represents a hydrogen atom or a force representing a substituent R ~
681 688 681 681 688 681
R の少なくとも一つは前記一般式(2A— 1)〜(2A— 10)の 、ずれかで表される基At least one R is a group represented by any of the formulas (2A-1) to (2A-10).
688 688
を表す。一般式 (9A)で表される化合物を用いることで、より発光効率の高い有機 EL 素子とすることができる。さらにより長寿命の有機 EL素子とすることができる。  Represents. By using the compound represented by the general formula (9A), an organic EL device with higher luminous efficiency can be obtained. Furthermore, it is possible to obtain a longer-life organic EL device.
[0250] 前記一般式(10A)において、 R 〜R は水素原子もしくは置換基を表す力 R [0250] In the general formula (10A), R 1 to R 4 represent a hydrogen atom or a force representing a substituent R
691 700 691 691 700 691
〜R の少なくとも一つは前記一般式(2A— 1)〜(2A— 10)の!/、ずれかで表されるAt least one of ~ R is represented by! /, Deviation of the general formulas (2A-1) to (2A-10)
700 700
基を表す。  Represents a group.
[0251] Lで表される 2価の連結基としては、アルキレン基 (例えば、エチレン基、トリメチレ  [0251] Examples of the divalent linking group represented by L include an alkylene group (for example, ethylene group, trimethylene).
1  1
ン基、テトラメチレン基、プロピレン基、ェチルエチレン基、ペンタメチレン基、へキサ メチレン基、 2, 2, 4 トリメチルへキサメチレン基、ヘプタメチレン基、オタタメチレン 基、ノナメチレン基、デカメチレン基、ゥンデカメチレン基、ドデカメチレン基、シクロへ キシレン基 (例えば、 1, 6 シクロへキサンジィル基等)、シクロペンチレン基 (例えば 、 1, 5 シクロペンタンジィル基等)等)、ァルケ-レン基 (例えば、ビ-レン基、プロ ベ-レン基等)、アルキ-レン基 (例えば、ェチ-レン基、 3—ペンチ-レン基等)、ァ リーレン基等の炭化水素基の他、ヘテロ原子を含む基 (例えば、 O 、一 S 等の カルコゲン原子を含む 2価の基、 N (R)—基、ここで Rは水素原子またはアルキル 基を表し、該アルキル基は、前記一般式(1A)にお 、て R で表されるアルキル基と  Group, tetramethylene group, propylene group, ethylethylene group, pentamethylene group, hexamethylene group, 2, 2, 4 trimethylhexamethylene group, heptamethylene group, otatamethylene group, nonamethylene group, decamethylene group, undecamethylene group, dodecamethylene group Group, cyclohexylene group (for example, 1,6-cyclohexanediyl group, etc.), cyclopentylene group (for example, 1,5-cyclopentanediyl group, etc.), alk-lene group (for example, beylene group, In addition to hydrocarbon groups such as propylene groups, alkylene groups (eg, ethylene groups, 3-pentylene groups, etc.), arylene groups, etc., groups containing heteroatoms (eg, O A divalent group containing a chalcogen atom such as 1 S, N (R) — group, wherein R represents a hydrogen atom or an alkyl group, and the alkyl group is represented by R in the general formula (1A) Represented Alkyl group
101  101
同義である)等が挙げられる。また、上記のアルキレン基、ァルケ-レン基、アルキ- レン基、ァリーレン基の各々においては、 2価の連結基を構成する炭素原子の少なく とも一つが、カルコゲン原子 (酸素、硫黄等)や前記 N (R)—基等で置換されてい てもよい。  And the like). Further, in each of the above alkylene group, alkene group, alkylene group, and arylene group, at least one of carbon atoms constituting the divalent linking group is a chalcogen atom (oxygen, sulfur, etc.) N (R) —may be substituted with a group or the like.
[0252] さらに Lで表される 2価の連結基としては、例えば、 2価の複素環基を有する基が用 いられ、例えば、ォキサゾールジィル基、ピリミジンジィル基、ピリダジンジィル基、ピ ランジィル基、ピロリンジィル基、イミダゾリンジィル基、イミダゾリジンジィル基、ピラゾ リジンジィル基、ピラゾリンジィル基、ピぺリジンジィル基、ピぺラジンジィル基、モル ホリンジィル基、キヌクリジンジィル基等が挙げられ、またチォフェン 2, 5 ジィル 基や、ピラジン 2, 3 ジィル基のような、芳香族複素環を有する化合物 (ヘテロ芳 香族化合物ともいう)に由来する 2価の連結基であってもよい。また、アルキルイミノ基 、ジアルキルシランジィル基ゃジァリールゲルマンジィル基のようなヘテロ原子を会し て連結する基であってもよ 、。 [0252] Further, as the divalent linking group represented by L, for example, a group having a divalent heterocyclic group is used. For example, oxazole diyl group, pyrimidine diyl group, pyridazine diyl group, pyrandyl group, pyrrolin diyl group, imidazoline diyl group, imidazolidine diyl group, pyrazolidine diyl group, pyrazoline diyl group, piperidine diyl group, piperazine diyl Group, morpholine diyl group, quinuclidine diyl group, etc., and compounds having an aromatic heterocycle such as thiophene 2,5 diyl group and pyrazine 2,3 diyl group (also called heteroaromatic compounds) ) Derived from a divalent linking group. In addition, the alkylimino group, the dialkylsilane diyl group, and the diarylgermandyl group may be a group that connects and connects hetero atoms.
[0253] 前記一般式(10A)で表される化合物を用いることで、より発光効率の高い有機 EL 素子とすることができる。さらにより長寿命の有機 EL素子とすることができる。  [0253] By using the compound represented by the general formula (10A), an organic EL device with higher luminous efficiency can be obtained. Furthermore, it is possible to obtain a longer-life organic EL device.
[0254] 前記一般式(11A)〜一般式(15A)で各々表される化合物において、 R、 Rで各  [0254] In the compounds represented by the general formula (11A) to the general formula (15A),
1 2 々表される置換基としては、前記一般式(1A)において R で表される置換基と同義  1 The substituent represented by 2 is synonymous with the substituent represented by R in the general formula (1A).
101  101
である。  It is.
[0255] 前記一般式(15A)において、 Z、 Z、 Z、 Zで各々表される、各々窒素原子を少な  [0255] In the general formula (15A), each of Z, Z, Z, and Z each represents a small number of nitrogen atoms.
1 2 3 4  1 2 3 4
くとも一つ含む 6員の芳香族複素環としては、例えば、ピリジン環、ピリダジン環、ピリ ミジン環、ピラジン環等が挙げられる。  Examples of the 6-membered aromatic heterocycle containing at least one include a pyridine ring, a pyridazine ring, a pyrimidine ring, and a pyrazine ring.
[0256] 前記一般式(16A)において、 Z、 Zで各々表される、各々窒素原子を少なくとも [0256] In the general formula (16A), each of the nitrogen atoms represented by Z and Z is at least
1 2 一 つ含む 6員の芳香族複素環としては、例えば、ピリジン環、ピリダジン環、ピリミジン環 、ピラジン環等が挙げられる。  Examples of the 6-membered aromatic heterocycle including one pyridine include a pyridine ring, a pyridazine ring, a pyrimidine ring, and a pyrazine ring.
[0257] Ar、 Arで各々表されるァリーレン基としては、 o フエ-レン基、 m—フエ-レン基 [0257] The arylene groups represented by Ar and Ar include o-phenylene group and m-phenylene group, respectively.
1 2  1 2
、 p フエ-レン基、ナフタレンジィル基、アントラセンジィル基、ナフタセンジィル基、 ピレンジィル基、ナフチルナフタレンジィル基、ビフエ-ルジィル基(例えば、 3, 3' ービフヱ-ルジィル基、 3, 6—ビフヱ-ルジィル基等)、テルフエ-ルジィル基、クァ テルフエ-ルジィル基、キンクフエ-ルジィル基、セキシフエ-ルジィル基、セプチフ ェ-ルジィル基、ォクチフエ-ルジィル基、ノビフエ-ルジィル基、デシフエ-ルジィ ル基等が挙げられる。また前記ァリーレン基は、さらに後述する置換基を有していて もよい。 Ar、 Arで各々表される 2価の芳香族複素環基は、フラン環、チォフェン環、  , P phenylene group, naphthalene diyl group, anthracenedyl group, naphthacene diyl group, pyrene diyl group, naphthyl naphthalene diyl group, biphenyl group (for example, 3, 3'-biphenyl group, 3, 6-biphenyl group) Etc.), terfelsyl group, quaterfel group, kink feldsyl group, sexiphenyl group, septiphenyl group, octaphenyl group, nobiphenyl group, decyl group and the like. The arylene group may further have a substituent described later. The divalent aromatic heterocyclic groups represented by Ar and Ar are respectively a furan ring, a thiophene ring,
1 2  1 2
ピリジン環、ピリダジン環、ピリミジン環、ピラジン環、トリアジン環、ベンゾイミダゾール 環、ォキサジァゾール環、トリァゾール環、イミダゾール環、ピラゾール環、チアゾール 環、インドール環、ベンゾイミダゾール環、ベンゾチアゾール環、ベンゾォキサゾール 環、キノキサリン環、キナゾリン環、フタラジン環、力ルバゾール環、カルボリン環、力 ルポリン環を構成する炭化水素環の炭素原子がさらに窒素原子で置換されている環 等力 導出される 2価の基等が挙げられる。さらに前記芳香族複素環基は、前記 R Pyridine ring, pyridazine ring, pyrimidine ring, pyrazine ring, triazine ring, benzimidazole Ring, oxaziazole ring, triazole ring, imidazole ring, pyrazole ring, thiazole ring, indole ring, benzimidazole ring, benzothiazole ring, benzoxazole ring, quinoxaline ring, quinazoline ring, phthalazine ring, force rubazole ring, carboline ring, A ring in which the carbon atom of the hydrocarbon ring that constitutes a ruporin ring is further substituted with a nitrogen atom. Further, the aromatic heterocyclic group is the R
101 で表される置換基を有してもょ ヽ。  It may have a substituent represented by 101.
[0258] Lで表される 2価の連結基としては、前記一般式(10A)において、 Lで表される 2  [0258] Examples of the divalent linking group represented by L include those represented by L in the general formula (10A).
1  1
価の連結基と同義である力 好ましくはアルキレン基、 O S 等のカルコゲン 原子を含む 2価の基であり、最も好ましくはアルキレン基である。  Power that is synonymous with a valent linking group is preferably an alkylene group or a divalent group containing a chalcogen atom such as OS or the like, and most preferably an alkylene group.
[0259] 前記一般式(17A)において、 Ar、 Arで各々表されるァリーレン基は、前記一般 [0259] In the general formula (17A), the arylene groups represented by Ar and Ar are
1 2  1 2
式(16A)において Ar、 Arで各々表されるァリーレン基と同義である。 Ar、 Arで各  In formula (16A), these are synonymous with the arylene groups represented by Ar and Ar, respectively. Ar, Ar
1 2 1 2 々表される芳香族複素環基は、前記一般式(16A)において Ar、 Arで各々表され  The aromatic heterocyclic group represented by 1 2 1 2 is represented by Ar and Ar in the general formula (16A).
1 2  1 2
る 2価の芳香族複素環基と同義である。  It is synonymous with a divalent aromatic heterocyclic group.
[0260] Z、 Z、 Z、 Zで各々表される、各々窒素原子を少なくとも一つ含む 6員の芳香族 [0260] 6-membered aromatics each represented by Z, Z, Z, Z, each containing at least one nitrogen atom
1 2 3 4  1 2 3 4
複素環としては、例えば、ピリジン環、ピリダジン環、ピリミジン環、ピラジン環等が挙 げられる。  Examples of the heterocyclic ring include a pyridine ring, a pyridazine ring, a pyrimidine ring, and a pyrazine ring.
[0261] Lで表される 2価の連結基としては、前記一般式(10A)において、 Lで表される 2  [0261] The divalent linking group represented by L is represented by L 2 in the general formula (10A).
1  1
価の連結基と同義である力 好ましくはアルキレン基、 o s—等のカルコゲン 原子を含む 2価の基であり、最も好ましくはアルキレン基である。  Power that is synonymous with a valent linking group is preferably an alkylene group, a divalent group containing a chalcogen atom such as os-, and most preferably an alkylene group.
[0262] 以下に、本発明に係る一般式(1A)で表される化合物の具体例を示すが、本発明 はこれらに限定されない。 [0262] Specific examples of the compound represented by formula (1A) according to the present invention are shown below, but the present invention is not limited thereto.
[0263] [化 78] [0263] [Chemical 78]
[0264] [化 79] 化合物 中心骨格 A [0264] [Chemical 79] Compound Central skeleton A
0] 0]
化合物 中心骨格 A Compound Central skeleton A
1] 1]
[0267] [化 82] 化合物 中心骨格 A [0267] [Chemical 82] Compound Central skeleton A
83] 83]
[0269] [化 84] 化合物 中心骨格 [0269] [Chemical 84] Compound Central skeleton
5] 化合物 中心骨格 A Five] Compound Central skeleton A
6] 化合物 中心骨格 6] Compound Central skeleton
87] 化合物 中心骨格 A 87] Compound Central skeleton A
88] 88]
[0274] [化 89] [0274] [Chemical 89]
[0275] [化 90] [0275] [Chemical 90]
[0276] [化 91] [0276] [Chemical 91]
[26^ ] [ίίΖΟΙ [26 ^] [ίίΖΟΙ
ll£0£/900IJf/13d !■01· 0Π860/900Ζ OAV ll £ 0 £ / 900IJf / 13d! ■ 01 · 0Π860 / 900Ζ OAV
[0278] [化 93] [0278] [Chemical 93]
[0279] [化 94] [0279] [Chemical 94]
[0280] [化 95] [0280] [Chemical 95]
[0281] [化 96] [0281] [Chemical 96]
[0282] [化 97] [0282] [Chemical 97]
[0283] [化 98] [0283] [Chemical 98]
A— 105 A- 106 A—105 A-106
9] A— 114 9] A—114
00] A— 121 00] A—121
01] 01]
[0287] [化 102] 112 [0287] [Chemical 102] 112
[0288] [化 [0288]
[0289] [化 104] [0289] [Chemical 104]
[0290] [化 105] [0290] [Chemical 105]
A-147 A-147
106] 106]
107] 107]
[0293] [化 108] [0293] [Chemical 108]
A— 158 A— 159 A— 158 A— 159
109] 109]
[0295] [化 110] [0295] [Chem 110]
A -170 A -170
[0296] [化 111] [0296] [Chem 111]
112] 112]
[0298] 以下に、本発明に係る化合物の代表的な合成例を示すが、本発明はこれらに限定 されない。  [0298] Typical synthesis examples of the compounds according to the present invention are shown below, but the present invention is not limited thereto.
[0299] (例示化合物 A— 73の合成)  [0299] (Synthesis of Exemplified Compound A-73)
[0300] [化 113] [0300] [Chemical 113]
[0301] 4, 4' —ジョードビフエ-ル 6. 87g、 β—カルボリン 6. OOgを Ν, N—ジメチルァセ トアミド 50ml中に添加した混合液に、銅粉 4. 5g、炭酸カリウム 7. 36gをカ卩え、 15時 間加熱還流した。放冷後水クロ口ホルムを加え、不溶物を濾去した。有機層を分離し 、水、飽和食塩水で洗浄した後、減圧下に濃縮し、得られた残渣を酢酸に溶解し、活 性炭処理後、再結晶して,例示化合物 A— 73の無色結晶 4. 2gを得た。  [0301] 4, 4 '— Jodhbi-Fell 6.87g, β-carboline 6. OOg in 50ml of N, N-dimethylacetamide, 4.5g of copper powder and 7.36g of potassium carbonate were added. It was heated and refluxed for 15 hours. After standing to cool, water-cold form was added and insolubles were removed by filtration. The organic layer is separated, washed with water and saturated brine, and concentrated under reduced pressure. The resulting residue is dissolved in acetic acid, treated with activated charcoal, and recrystallized to give colorless compound of Exemplified Compound A-73. 4.2 g of crystals were obtained.
[0302] 例示化合物 A— 73の構造は1 H—NMR ^ベクトル及び質量分析スペクトルによつ て確認した。例示化合物 A— 73の物性データ、スペクトルデータを下記に示す。 [0302] The structure of Exemplified Compound A-73 was confirmed by 1 H-NMR ^ vector and mass spectrometry spectrum. The physical property data and spectral data of Exemplified Compound A-73 are shown below.
[0303] 無色結晶、融点 200°C  [0303] Colorless crystals, melting point 200 ° C
MS (FAB) m/z: 487 (M+ 1)  MS (FAB) m / z: 487 (M + 1)
'H-NMR (400MHz, CDC1 ): δ /ppm 7. 3— 7. 5 (m、2H)、7. 5— 7. 6 (  'H-NMR (400MHz, CDC1): δ / ppm 7.3—7.5 (m, 2H), 7.5—7.6 (
3  Three
m, 4H)、 7. 7- 7. 8 (m, 4H)、 7. 9— 8. 0 (m, 4H)、 8. 06 (d, J= 5. 1Hz, 2H) 、 8. 24 (d, J = 7. 8Hz, 2H)、 8. 56 (d, J = 5. 1Hz, 2H)、 8. 96 (s, 2H)  m, 4H), 7. 7- 7.8 (m, 4H), 7.9—8.00 (m, 4H), 8.06 (d, J = 5.1 Hz, 2H), 8. 24 ( d, J = 7.8Hz, 2H), 8.56 (d, J = 5.1Hz, 2H), 8.96 (s, 2H)
(例示化合物 A— 74の合成)  (Synthesis of Exemplified Compound A-74)
[0304] [化 114] [0304] [Chemical 114]
[0305] 酢酸パラジウム 0. 32g、トリ— tert ブチルホスフィン 1. 17gを無水トルエン 10ml に溶解し、水素化ホウ素ナトリウム 50mgを添加し、室温で 10分間攪拌した後、 δ - カルボリン 5. OOg、 4, 4' ージョードビフエ-ル 5. 87g、ナトリウム tert ブトキシ ド 3. 42gを無水キシレン 50ml中に分散し、窒素雰囲気下、還流温度にて 10時間撹 拌した。得られた反応混合物を放冷後クロ口ホルムと水を加えて有機層を分離し、有 機層を、水、飽和食塩水で洗浄した後、減圧下に濃縮し、得られた残渣をテトラヒドロ フランに溶解し、活性炭処理を施した後、再結晶して例示化合物 A— 74の無色結晶 5. Ogを得た。  [0305] Palladium acetate 0.32 g, tri-tert butylphosphine 1. 17 g dissolved in anhydrous toluene 10 ml, sodium borohydride 50 mg was added and stirred for 10 minutes at room temperature, then δ-carboline 5. OOg, 4 , 4′-Jordobiphal 5.87 g and sodium tert butoxide 3.42 g were dispersed in 50 ml of anhydrous xylene and stirred at reflux temperature for 10 hours under a nitrogen atmosphere. The resulting reaction mixture was allowed to cool and then added with chloroform and water to separate the organic layer. The organic layer was washed with water and saturated brine, and then concentrated under reduced pressure. After being dissolved in furan and treated with activated carbon, recrystallization gave colorless crystals of Exemplified Compound A-74 5. Og.
[0306] 例示化合物 A— 74の構造は1 H— NMRスぺクトル及び質量分析スぺクトルによつ て確認した。例示化合物 A— 74の物性データ、スペクトルデータを下記に示す。 [0306] The structure of Exemplified Compound A-74 was confirmed by 1 H-NMR spectrum and mass spectrometry spectrum. The physical property data and spectral data of Exemplified Compound A-74 are shown below.
[0307] MS (FAB) m/z: 487 (M+ 1) [0307] MS (FAB) m / z: 487 (M + 1)
JH- NMR (400MHz, CDC1 ): δ /ppm 7. 37 (dd, J=4. 7Hz, J = 8. 3Hz, J H-NMR (400MHz, CDC1): δ / ppm 7.37 (dd, J = 4.7Hz, J = 8.3Hz,
3  Three
2H)、 7. 4- 7. 5 (m, 2H)、 7. 5— 7. 6 (m, 4H)、 7. 7— 7. 8 (m, 4H)、 7. 81 (d d, J= l. 2Hz, J = 8. 3Hz, 2H)、 7. 9— 8. 0 (m, 4H)、 8. 48 (d, J = 7. 8Hz, 2 H) , 8. 65 (dd, J= l. 2Hz, J=4. 6Hz, 2H)  2H), 7. 4-7.5 (m, 2H), 7.5—7.6 (m, 4H), 7.7—7.8 (m, 4H), 7.81 (dd, J = l. 2Hz, J = 8. 3Hz, 2H), 7. 9—8.0 (m, 4H), 8. 48 (d, J = 7.8Hz, 2 H), 8. 65 (dd, J = l. 2Hz, J = 4.6 Hz, 2H)
(例示化合物 A— 60の合成)  (Synthesis of Exemplified Compound A-60)
[0308] [化 115] [0308] [Chemical 115]
[0309] 4, 4' —ジョードビフエ-ル 6. 87g、 y—カルボリン 6. OOgを N, N—ジメチルァセ トアミド 50ml中に添加した混合液に、銅粉 4. 5g、炭酸カリウム 7. 36gをカ卩え、 15時 間加熱還流した。放冷後水クロ口ホルムを加え、不溶物を濾去した。有機層を分離し 、水、飽和食塩水で洗浄した後、減圧下に濃縮し、得られた残渣をシリカゲルクロマト グラフィ一に付した後、ジクロロメタン Zシクロへキサン中で結晶化させ、例示化合物 A— 60の無色結晶 4. 3gを得た。  [0309] 4, 4'—Jodobi-Fell 6.87g, y-carboline 6. OOg in 50ml of N, N-dimethylacetamide was added to a mixture of copper powder 4.5g and potassium carbonate 7.36g. It was heated and refluxed for 15 hours. After standing to cool, water-cold form was added and insolubles were removed by filtration. The organic layer is separated, washed with water and saturated brine, and concentrated under reduced pressure. The resulting residue is subjected to silica gel chromatography, crystallized in dichloromethane Z cyclohexane, and exemplified compound A — 60 g of colorless crystals were obtained.
[0310] 例示化合物 A— 60の構造は、 iH— NMRスペクトル及び質量分析スペクトルによつ て確認した。例示化合物 A— 60の物性データ、スペクトルデータを下記に示す。  [0310] The structure of Exemplified Compound A-60 was confirmed by iH-NMR spectrum and mass spectrometry spectrum. The physical property data and spectral data of Exemplified Compound A-60 are shown below.
[0311] MS (FAB) m/z: 487 (M+ 1)  [0311] MS (FAB) m / z: 487 (M + 1)
'H-NMR (400MHz, CDC1 ): δ /ppm 7. 4— 7. 4 (m, 4H)、 7. 4— 7. 5 (  'H-NMR (400MHz, CDC1): δ / ppm 7.4—7.4 (m, 4H), 7.4—7.5 (
3  Three
m, 4H)、 7. 7- 7. 8 (m, 4H) 7. 9— 8. 0 (m, 4H)、 8. 25 (d, J = 7. 8Hz, 2H)、 8. 57 (d, J = 5. 6Hz, 2H)、 9. 42 (s, 1H)  m, 4H), 7. 7- 7.8 (m, 4H) 7.9—8.0 (m, 4H), 8.25 (d, J = 7.8Hz, 2H), 8.57 (d , J = 5.6Hz, 2H), 9.42 (s, 1H)
(例示化合物 A— 144の合成)  (Synthesis of Exemplified Compound A—144)
[0312] [化 116] [0312] [Chem 116]
[0313] 酢酸パラジウム 0. 16g、トリ— tert—ブチルホスフィン 0. 58gを無水トルエン 10ml に溶解し、水素化ホウ素ナトリウム 25mgを添加し、室温で 10分間攪拌した後、 δ - カルボリン 2. OOg、中間体 a3. 20g、ナトリウム— tert—ブ卜キシド 1. 37gを無水キシ レン 50ml中に分散し、窒素雰囲気下、還流温度にて 10時間撹拌した。放冷後クロ口 ホルムと水を加えて有機層を分離し、有機層を水、飽和食塩水で洗浄した後減圧下 に濃縮し、得られた残渣を酢酸力 再結晶して例示化合物 A— 144の無色結晶 1. 5 gを得た。 [0313] 0.16 g of palladium acetate and 0.58 g of tri-tert-butylphosphine were dissolved in 10 ml of anhydrous toluene, 25 mg of sodium borohydride was added, and the mixture was stirred at room temperature for 10 minutes, and then δ-carboline 2. OOg, Intermediate a3. 20 g and sodium-tert-butoxide 1.37 g were dispersed in 50 ml of anhydrous xylene and stirred at reflux temperature for 10 hours under a nitrogen atmosphere. After standing to cool, the organic layer is separated by adding chloroform and water, and the organic layer is washed with water and saturated brine and then concentrated under reduced pressure. 144 colorless crystals of 1.5 g were obtained.
[0314] 例示化合物 A— 144の構造は、 iH—NMRスペクトル及び質量分析スペクトルによ つて確認した。例示化合物 A— 144のスペクトルデータは以下の通りである。  [0314] The structure of Exemplified Compound A-144 was confirmed by iH-NMR spectrum and mass spectrometry spectrum. The spectral data of Example Compound A-144 are as follows.
[0315] MS (FAB) m/z: 647 (M + 1) [0315] MS (FAB) m / z: 647 (M + 1)
'H-NMR (400MHz, CDC1 ): δ /ppm 1. 80 (S, 12H)、 7. 27 (S, 4H)、 7  'H-NMR (400MHz, CDC1): δ / ppm 1.80 (S, 12H), 7.27 (S, 4H), 7
3  Three
. 34 (dd, J=4. 9Hz, J = 8. 3Hz, 2H)、 7. 3— 7. 4 (m, 2H)、 7. 4— 7. 5 (m, 1 2H)、 7. 76 (dd, J= l. 3Hz, J = 8. 3Hz、 2H)、 8. 45 (d, J = 7. 8Hz, 2H)、 8. 6 3 (dd, J= l. 3Hz, J=4. 9Hz, 2H)  34 (dd, J = 4.9 Hz, J = 8.3 Hz, 2H), 7.3—7.4 (m, 2H), 7.4—7.5 (m, 1 2H), 7.76 (dd, J = l. 3Hz, J = 8.3Hz, 2H), 8.45 (d, J = 7.8Hz, 2H), 8.6 3 (dd, J = l. 3Hz, J = 4. (9Hz, 2H)
(例示化合物 A— 143の合成)  (Synthesis of Exemplified Compound A-143)
[0316] [化 117] [0316] [Chemical 117]
[0317] 4, 4' —ジクロ口一 3, 3' —ビビリジル 0. 85g、ジァミン bO. 59g、ジベンジリデン アセトンパラジウム 44mg、イミダゾリゥム塩 36mg、ナトリウム tert ブトキシド 1. 09 gをジメトキシェタン 5mlに添加し、 80°Cで 24時間加温攪拌した。放冷後クロ口ホルム と水を加えて有機層を分離し、有機層を水、飽和食塩水で洗浄した後減圧下に濃縮 し、得られた残渣を酢酸ェチルカ 再結晶して例示化合物 A— 143の無色結晶 0. 3 gを得た。 [0317] 4, 4 '— Diclomental 1, 3' — Bibilidil 0.85g, Diamine bO. 59g, Dibenzylidene Acetonepalladium 44mg, Imidazolium salt 36mg, Sodium tert Butoxide 1.09g added to 5ml dimethoxyethane The mixture was heated and stirred at 80 ° C for 24 hours. After cooling, the organic layer is separated by adding chloroform and water, and the organic layer is washed with water and saturated brine and concentrated under reduced pressure. The resulting residue is recrystallized from ethyl acetate to give Exemplified Compound A— 143 colorless crystals of 143 were obtained.
[0318] 例示化合物 A— 143の構造は、 iH—NMRスペクトル及び質量分析スペクトルによ つて確認した。例示化合物 A— 143のスペクトルデータを下記に示す。  [0318] The structure of Exemplified Compound A-143 was confirmed by iH-NMR spectrum and mass spectrometry spectrum. The spectral data of Exemplified Compound A-143 is shown below.
[0319] MS (FAB) m/z: 639 (M+ 1) [0319] MS (FAB) m / z: 639 (M + 1)
iH—NMR (400MHz, CDC1 ): δ /ppm 7. 46 (d, J = 5. 7Hz, 4H)、 7. 6—  iH—NMR (400MHz, CDC1): δ / ppm 7.46 (d, J = 5.7Hz, 4H), 7. 6—
3  Three
7. 7 (m, 4H)、 7. 8— 7. 9 (m, 4H)、 8. 67 (d, J = 5. 7Hz, 4H)、 9. 51 (S, 4H) (例示化合物 A— 145の合成)  7. 7 (m, 4H), 7.8—7.9 (m, 4H), 8.67 (d, J = 5.7 Hz, 4H), 9.51 (S, 4H) (Exemplary Compound A— 145 synthesis)
例示化合物 A— 143の合成において、 4, 4' ージクロロー 3, 3' —ビビリジルの一 方のピリジン環をベンゼンに変更した、 3— (2 クロ口フエ二ノレ) 4 クロ口ピリジン を用いた以外は同様にして、例示化合物 A— 145を合成した。  In the synthesis of Exemplified Compound A—143, except that 4—4′-dichloro-3,3′—bibilidyl has one pyridine ring replaced with benzene, 3— (2) In the same manner, Exemplified Compound A-145 was synthesized.
[0320] 例示化合物 A— 145の構造は、 iH—NMRスペクトル及び質量分析スペクトルによ つて確認した。例示化合物 A— 145のスペクトルデータを下記に示す。 [0320] The structure of Exemplified Compound A-145 was confirmed by iH-NMR spectrum and mass spectrometry spectrum. The spectral data of Exemplified Compound A-145 is shown below.
[0321] MS (FAB) m/z: 637 (M+ 1) [0321] MS (FAB) m / z: 637 (M + 1)
'H-NMR (400MHz, CDC1 ): δ /ppm 7. 3— 7. 4 (m, 2H)、 7. 6— 7. 7 ( m, 4H)、 7. 7- 7. 8 (m, 4H) 7. 8— 7. 9 (m, 4H)、 8. 06 (d, J = 5. 3Hz, 2H)、 8. 23 (d, J = 7. 8Hz, 2H)、8. 56 (d, J = 5. 3Hz, 2H) , 8. 96 (S, 2H) 'H-NMR (400MHz, CDC1): δ / ppm 7.3—7.4 (m, 2H), 7.6—7.7 ( m, 4H), 7. 7- 7.8 (m, 4H) 7.8—7.9 (m, 4H), 8.06 (d, J = 5.3 Hz, 2H), 8.23 (d , J = 7.8Hz, 2H), 8.56 (d, J = 5.3Hz, 2H), 8.96 (S, 2H)
なお、上記の合成例以外に、これらの化合物のァザカルバゾール環やその類緑体 ίま、 J. Chem. Soc. , Perkin Trans. 1, 1505— 1510 (1999)、 Pol. J. Chem. , 54, 1585 (1980)、 (Tetrahedron  In addition to the above synthesis examples, the azacarbazole ring of these compounds and their chloroplasts, J. Chem. Soc., Perkin Trans. 1, 1505-1510 (1999), Pol. J. Chem. , 54, 1585 (1980), (Tetrahedron
Lett. 41 (2000) , 481— 484)に記載される合成法に従って合成することができる 。合成されたァザカルバゾール環やその類緑体と、芳香環、複素環、アルキル基等 の、コア、連結基への導入は、ウルマンカップリング、 Pd触媒を用いたカップリング、 スズキカップリング等公知の方法を用いることができる。  Lett. 41 (2000), 481-484). Introduction of the synthesized azacarbazole ring or its chloroplast to the core or linking group of aromatic ring, heterocycle, alkyl group, etc., Ullman coupling, coupling using Pd catalyst, Suzuki coupling, etc. A known method can be used.
[0322] 本発明に係る化合物は分子量力 00以上であることが好ましぐ 450以上であるこ とがより好ましぐさらに好ましくは 600以上であり、特に好ましくは分子量が 800以上 である。これによりガラス転移温度を上昇させ熱安定性が向上し、より一層長寿命化 をさせることができる。 [0322] The compound according to the present invention preferably has a molecular weight of 00 or more, more preferably 450 or more, still more preferably 600 or more, and particularly preferably a molecular weight of 800 or more. As a result, the glass transition temperature is raised, the thermal stability is improved, and the life can be further extended.
[0323] 次に、本発明の有機 EL素子の構成層について詳細に説明する。本発明において 、有機 EL素子の層構成の好ましい具体例を以下に示すが、本発明はこれらに限定 されな ヽ。 (i)陽極 Z発光層 Z電子輸送層 Z陰極 (ϋ)陽極 Z正孔輸送層 Z発光層 Next, the constituent layers of the organic EL device of the present invention will be described in detail. In the present invention, preferred specific examples of the layer structure of the organic EL device are shown below, but the present invention is not limited thereto. (i) Anode Z light emitting layer Z electron transport layer Z cathode (i) Anode Z hole transport layer Z light emitting layer
Z電子輸送層 Z陰極 (m)陽極 Z正孔輸送層 Z発光層 Z正孔阻止層 Z電子輸送層 Z陰極 Gv)陽極 Z正孔輸送層 Z発光層 Z正孔阻止層 Z電子輸送層 Z陰極バッフ ァ一層 Z陰極 (V)陽極 Z陽極バッファ一層 Z正孔輸送層 Z発光層 Z正孔阻止層 Z 電子輸送層 Z陰極バッファ一層 Z陰極 Z electron transport layer Z cathode (m) anode Z hole transport layer Z light emitting layer Z hole blocking layer Z electron transport layer Z cathode transport layer Z cathode Gv) anode Z hole transport layer Z light emitting layer Z hole blocking layer Z electron transport layer Z Cathode buffer layer Z cathode (V) anode Z anode buffer layer Z hole transport layer Z light-emitting layer Z hole blocking layer Z electron transport layer Z cathode buffer layer Z cathode
《陽極》  《Anode》
有機 EL素子における陽極としては、仕事関数の大きい (4eV以上)金属、合金、電 気伝導性化合物及びこれらの混合物を電極物質とするものが好ましく用いられる。こ のような電極物質の具体例としては Au等の金属、 Cul、インジウムチンォキシド (ITO ) , SnO、 ZnO等の導電性透明材料が挙げられる。また、 IDIXO (In O— ZnO)等 As the anode in the organic EL device, an electrode material made of a metal, an alloy, an electrically conductive compound or a mixture thereof having a high work function (4 eV or more) is preferably used. Specific examples of such electrode materials include metals such as Au, conductive transparent materials such as Cul, indium tinoxide (ITO), SnO, and ZnO. IDIXO (In O—ZnO) etc.
2 2 3 非晶質で透明導電膜を作製可能な材料を用いてもょ ヽ。陽極はこれらの電極物質を 蒸着やスパッタリング等の方法により、薄膜を形成させ、フォトリソグラフィ一法で所望 の形状のパターンを形成してもよぐあるいはパターン精度をあまり必要としない場合 は(100 μ m以上程度)、上記電極物質の蒸着やスパッタリング時に所望の形状のマ スクを介してパターンを形成してもよい。この陽極より発光を取り出す場合には、透過 率を 10%より大きくすることが望ましぐまた陽極としてのシート抵抗は数百 Ω Zロ以 下が好ましい。さらに膜厚は材料にもよる力 通常 10〜: LOOOnm、好ましくは 10〜2 OOnmの範囲で選ばれる。 2 2 3 Use an amorphous material that can produce a transparent conductive film. For the anode, if these electrode materials are formed into a thin film by a method such as vapor deposition or sputtering and a pattern of a desired shape can be formed by a photolithography method, or the pattern accuracy is not so required (About 100 μm or more), the pattern may be formed through a mask of a desired shape during the deposition or sputtering of the electrode material. In the case of taking out light emission from this anode, it is desirable to make the transmittance larger than 10%, and the sheet resistance as the anode is preferably several hundred ΩZ or less. Further, the film thickness is a force depending on the material. Usually, 10 to: LOOOnm, preferably 10 to 2 OOnm is selected.
[0324] 《陰極》 [0324] 《Cathode》
一方、陰極としては、仕事関数の小さい (4eV以下)金属 (電子注入性金属と称する )、合金、電気伝導性化合物及びこれらの混合物を電極物質とするものが用いられる 。このような電極物質の具体例としては、ナトリウム、ナトリウム一カリウム合金、マグネ シゥム、リチウム、マグネシウム Z銅混合物、マグネシウム Z銀混合物、マグネシウム Zアルミニウム混合物、マグネシウム Zインジウム混合物、アルミニウム Z酸ィ匕アルミ -ゥム (Al O )混合物、インジウム、リチウム  On the other hand, a cathode having a work function (4 eV or less) metal (referred to as an electron injecting metal), an alloy, an electrically conductive compound, and a mixture thereof is used. Specific examples of such electrode materials include sodium, sodium-potassium alloy, magnesium, lithium, magnesium Z copper mixture, magnesium Z silver mixture, magnesium Z aluminum mixture, magnesium Z indium mixture, aluminum Z acid aluminum UM (Al 2 O 3) mixture, indium, lithium
2 3 Zアルミニウム混合物、希土類金属等が 挙げられる。これらの中で、電子注入性及び酸ィ匕等に対する耐久性の点から、電子 注入性金属とこれより仕事関数の値が大きく安定な金属である第二金属との混合物 、例えば、マグネシウム Z銀混合物、マグネシウム Zアルミニウム混合物、マグネシゥ ム Zインジウム混合物、アルミニウム Z酸ィ匕アルミニウム (Al O )混合物、リチウム  2 3 Z aluminum mixture, rare earth metal, etc. Among these, a mixture of an electron injecting metal and a second metal, which is a stable metal having a larger work function than this, for example, magnesium Z silver, from the viewpoint of electron injecting property and durability against acids, etc. Mixture, Magnesium Z Aluminum Mixture, Magnesium Z Indium Mixture, Aluminum Z Oxide Aluminum (Al 2 O 3) Mixture, Lithium
2 3 Z アルミニウム混合物、アルミニウム等が好適である。陰極はこれらの電極物質を蒸着 やスパッタリング等の方法により薄膜を形成させることにより、作製することができる。 また、陰極としてのシート抵抗は数百 Ω /口以下が好ましぐ膜厚は通常 ΙΟηπ!〜 5 μ m、好ましくは 50〜200nmの範囲で選ばれる。なお、発光した光を透過させるた め、有機 EL素子の陽極または陰極のいずれか一方力 透明または半透明であれば 発光輝度が向上し好都合である。  A 2 3 Z aluminum mixture, aluminum or the like is preferred. The cathode can be produced by forming a thin film of these electrode materials by a method such as vapor deposition or sputtering. Also, the sheet resistance as a cathode is several hundred Ω / mouth or less, and the preferred film thickness is usually ΙΟηπ! ˜5 μm, preferably selected in the range of 50 to 200 nm. In addition, since the emitted light is transmitted, it is convenient that either the anode or the cathode of the organic EL element is transparent or semi-transparent to improve the emission luminance.
[0325] また、陰極に上記金属を l〜20nmの膜厚で作製した後に、陽極の説明で挙げた 導電性透明材料をその上に作製することで、透明または半透明の陰極を作製するこ とができ、これを応用することで陽極と陰極の両方が透過性を有する素子を作製する ことができる。 [0325] Further, after the metal is formed to a thickness of 1 to 20 nm on the cathode, the transparent conductive material described in the description of the anode is formed thereon, whereby a transparent or translucent cathode is manufactured. By applying this, an element in which both the anode and the cathode are transmissive can be manufactured.
[0326] 次に、本発明の有機 EL素子の構成層として用いられる、注入層、阻止層、電子輸 送層等について説明する。 [0327] 《注入層:電子注入層、正孔注入層》 [0326] Next, an injection layer, a blocking layer, an electron transport layer, and the like used as a constituent layer of the organic EL element of the present invention will be described. [0327] <Injection layer: electron injection layer, hole injection layer>
注入層は必要に応じて設け、電子注入層と正孔注入層があり、上記のごとく陽極と 発光層または正孔輸送層の間、及び陰極と発光層または電子輸送層との間に存在 させてちょい。  The injection layer is provided as necessary, and has an electron injection layer and a hole injection layer, and as described above, exists between the anode and the light emitting layer or hole transport layer and between the cathode and the light emitting layer or electron transport layer. Hey.
[0328] 注入層とは、駆動電圧低下や発光輝度向上のために電極と有機層間に設けられる 層のことで、「有機 EL素子とその工業化最前線( 1998年 11月 30日ェヌ'ティー ·ェ ス社発行)」の第 2編第 2章「電極材料」(123〜166頁)に詳細に記載されており、正 孔注入層(陽極バッファ一層)と電子注入層(陰極バッファ一層)とがある。  [0328] The injection layer is a layer provided between the electrode and the organic layer in order to lower the driving voltage and improve the light emission luminance. “The organic EL element and the forefront of its industrialization (November 30, 1998) (Published by ES Co., Ltd.) ”, Chapter 2“ Chapter 2 Electrode Materials ”(pages 123-166) in detail, the hole injection layer (anode buffer layer) and electron injection layer (cathode buffer layer) There is.
[0329] 陽極バッファ一層(正孔注入層)は、特開平 9— 45479号公報、同 9 260062号 公報、同 8— 288069号公報等にもその詳細が記載されており、具体例として、銅フ タロシアニンに代表されるフタロシアニンバッファ一層、酸ィ匕バナジウムに代表される 酸化物バッファ一層、アモルファスカーボンバッファ一層、ポリア-リン(ェメラルディ ン)やポリチォフェン等の導電性高分子を用いた高分子バッファ一層等が挙げられる  [0329] The details of the anode buffer layer (hole injection layer) are also described in JP-A-9-45479, JP-A-9 260062, JP-A-8-288069 and the like. A phthalocyanine buffer layer typified by phthalocyanine, an oxide buffer layer typified by vanadium oxide, an amorphous carbon buffer layer, a polymer buffer layer using a conductive polymer such as polyarene (emeraldine) or polythiophene Etc.
[0330] 陰極バッファ一層(電子注入層)は、特開平 6— 325871号公報、同 9— 17574号 公報、同 10— 74586号公報等にもその詳細が記載されており、具体的にはストロン チウムゃアルミニウム等に代表される金属バッファ一層、フッ化リチウムに代表される アルカリ金属化合物バッファ一層、フッ化マグネシウムに代表されるアルカリ土類金 属化合物バッファ一層、酸ィヒアルミニウムに代表される酸ィヒ物バッファ一層等が挙げ られる。上記バッファ一層(注入層)はごく薄い膜であることが望ましぐ素材にもよる がその膜厚は 0. lnm〜5 mの範囲が好ましい。 [0330] The details of the cathode buffer layer (electron injection layer) are described in JP-A-6-325871, JP-A-9-17574, JP-A-10-74586, and the like. Metal buffer layer typified by aluminum or titanium, alkali metal compound buffer layer typified by lithium fluoride, alkaline earth metal compound buffer layer typified by magnesium fluoride, acid typified by acid aluminum One thing buffer. The thickness of the buffer layer (injection layer) is preferably in the range of 0.1 nm to 5 m, although it depends on the material desired to be a very thin film.
[0331] 《阻止層:正孔阻止層、電子阻止層》  [0331] 《Blocking layer: hole blocking layer, electron blocking layer》
阻止層は、上記のごとぐ有機化合物薄膜の基本構成層の他に必要に応じて設け られるものである。例えば、特開平 11 204258号公報、同 11 204359号公報、 及び「有機 EL素子とその工業化最前線( 1998年 11月 30日ェヌ'ティー ·エス社発 行)」の 237頁等に記載されている正孔阻止(ホールブロック)層がある。  The blocking layer is provided as necessary in addition to the basic constituent layer of the organic compound thin film as described above. For example, it is described in Japanese Patent Application Laid-Open Nos. 11 204258 and 11 204359, and “Organic EL device and its forefront of industrialization” (issued on November 30, 1998 by NTS). There is a hole blocking layer.
[0332] 正孔阻止層とは広い意味では電子輸送層であり、電子を輸送する機能を有しつつ 正孔を輸送する能力が著しく小さい正孔阻止材料からなり、電子を輸送しつつ正孔 を阻止することで電子と正孔の再結合確率を向上させることができる。 [0332] The hole blocking layer is an electron transporting layer in a broad sense, and is made of a hole blocking material that has a function of transporting electrons and has a very small ability to transport holes. The probability of recombination of electrons and holes can be improved by blocking.
[0333] 本発明の有機 EL素子の正孔阻止層は、発光層に隣接して設けられている。  [0333] The hole blocking layer of the organic EL device of the present invention is provided adjacent to the light emitting layer.
[0334] 本発明では、正孔阻止層の正孔阻止材料として前述した本発明に係る化合物を含 有させることが好ましい。これにより、より一層発光効率の高い有機 EL素子とすること ができる。さらにより一層長寿命化させることができる。 [0334] In the present invention, the above-described compound according to the present invention is preferably contained as a hole blocking material of the hole blocking layer. As a result, an organic EL device with even higher luminous efficiency can be obtained. Further, the lifetime can be further increased.
[0335] 一方、電子阻止層とは広い意味では正孔輸送層であり、正孔を輸送する機能を有 しつつ電子を輸送する能力が著しく小さい材料力 なり、正孔を輸送しつつ電子を阻 止することで電子と正孔の再結合確率を向上させることができる。 [0335] On the other hand, the electron blocking layer is a hole transport layer in a broad sense, and has a material force that has a function of transporting holes and has a remarkably small ability to transport electrons. By blocking, the recombination probability of electrons and holes can be improved.
[0336] 《発光層》 [0336] <Light emitting layer>
本発明に係る発光層は、電極または電子輸送層、正孔輸送層カゝら注入されてくる 電子及び正孔が再結合して発光する層であり、発光する部分は発光層の層内であつ ても発光層と隣接層との界面であってもよ 、。  The light emitting layer according to the present invention is a layer that emits light by recombination of electrons and holes injected from an electrode, an electron transport layer, or a hole transport layer, and the light emitting portion is within the layer of the light emitting layer. It may be the interface between the light emitting layer and the adjacent layer.
[0337] (ホストイ匕合物)  [0337] (Hosty compound)
本発明の有機 EL素子の発光層には、以下に示す、ホストイ匕合物とリン光性ィ匕合物 (リン光発光性ィ匕合物ともいう)が含有されることが好ましぐ本発明においては、ホス ト化合物として前述した本発明に係る化合物を用いることが好ましい。これにより、より 一層発光効率を高くすることができる。また、ホストイ匕合物として、上記の本発明に係 る化合物以外の化合物を含有してもよ ヽ。  It is preferable that the light emitting layer of the organic EL device of the present invention contains a host compound and a phosphorescent compound (also referred to as a phosphorescent compound) shown below. In the invention, the compound according to the present invention described above is preferably used as the host compound. As a result, the luminous efficiency can be further increased. Further, the host compound may contain a compound other than the compound according to the present invention.
[0338] ここで、本発明にお 、てホストイ匕合物とは、発光層に含有される化合物のうちで室 温(25°C)においてリン光発光のリン光量子収率が、 0. 01未満の化合物と定義され る。  Here, in the present invention, the host compound is a phosphorescence quantum yield of phosphorescence emission at room temperature (25 ° C.) among compounds contained in the light emitting layer. Defined as less than
[0339] さらに公知のホストイ匕合物を複数種併用して用いてもよい。ホスト化合物を複数種 用いることで、電荷の移動を調整することが可能であり、有機 EL素子を高効率化す ることができる。また、リン光性ィ匕合物を複数種用いることで、異なる発光を混ぜること が可能となり、これにより任意の発光色を得ることができる。リン光性化合物の種類、ド 一プ量を調整することで白色発光が可能であり、照明、バックライトへの応用もできる  [0339] Further, a plurality of known host compounds may be used in combination. By using multiple types of host compounds, it is possible to adjust the movement of charges, and the organic EL device can be made highly efficient. In addition, by using a plurality of phosphorescent compounds, it is possible to mix different light emission, thereby obtaining an arbitrary emission color. White light emission is possible by adjusting the type and amount of phosphorescent compound, and it can also be used for lighting and backlighting.
[0340] これらの公知のホスト化合物としては、正孔輸送能、電子輸送能を有しつつ、かつ 発光の長波長化を防ぎ、なおかつ高 Tg (ガラス転移温度)である化合物が好ま 、。 [0340] As these known host compounds, while having a hole transport ability and an electron transport ability, Preference is given to compounds that prevent the emission of longer wavelengths and that have a high Tg (glass transition temperature).
[0341] 公知のホストイ匕合物の具体例としては、以下の文献に記載されている化合物が挙 げられる。 [0341] Specific examples of known host compounds include the compounds described in the following documents.
[0342] 特開 2001— 257076号公報、同 2002— 308855号公報、同 2001— 313179号 公報、同 2002— 319491号公報、同 2001— 357977号公報、同 2002— 334786 号公報、同 2002— 8860号公報、同 2002— 334787号公報、同 2002— 15871号 公報、同 2002— 334788号公報、同 2002— 43056号公報、同 2002— 334789 号公報、同 2002— 75645号公報、同 2002— 338579号公報、同 2002— 10544 5号公報、同 2002— 343568号公報、同 2002— 141173号公報、同 2002— 352 957号公報、同 2002— 203683号公報、同 2002— 363227号公報、同 2002— 2 31453号公報、同 2003— 3165号公報、同 2002— 234888号公報、同 2003— 2 7048号公報、同 2002— 255934号公報、同 2002— 260861号公報、同 2002— 280183号公報、同 2002— 299060号公報、同 2002— 302516号公報、同 2002 — 305083号公報、同 2002— 305084号公報、同 2002— 308837号公報等。  [0342] JP 2001-257076, 2002-308855, 2001-313179, 2002-319491, 2001-357977, 2002-334786, 2002-8860 No., 2002-334787, 2002-15871, 2002-334788, 2002-43056, 2002-334789, 2002-75645, 2002-338579 Publication No. 2002-10544 5, Publication No. 2002-343568 Publication No. 2002-141173 Publication No. 2002-352 957 Publication No. 2002-203683 Publication No. 2002-363227 Publication No. 2002-363227 Publication No. 2002-2 31453, 2003-3165, 2002-234888, 2003-2 7048, 2002-255934, 2002-260861, 2002-280183, 2002- No. 299060, No. 2002-302516, No. 2002-305083, No. 2002-305084, No. 2002-308837, etc.
[0343] また、発光層は、ホストイ匕合物としてさらに蛍光極大波長を有するホストイ匕合物を含 有していてもよい。この場合、他のホスト化合物とリン光性化合物から蛍光性化合物 へのエネルギー移動で、有機 EL素子としての電界発光は蛍光極大波長を有する他 のホストイ匕合物力 の発光も得られる。蛍光極大波長を有するホストイ匕合物として好 ましいのは、溶液状態で蛍光量子収率が高いものである。ここで、蛍光量子収率は 1 0%以上、特に 30%以上が好ましい。具体的な蛍光極大波長を有するホスト化合物 としては、クマリン系色素、ピラン系色素、シァニン系色素、クロコニゥム系色素、スク ァリウム系色素、ォキソベンツアントラセン系色素、フルォレセイン系色素、ローダミン 系色素、ピリリウム系色素、ペリレン系色素、スチルベン系色素、ポリチォフェン系色 素等が挙げられる。蛍光量子収率は、前記第 4版実験化学講座 7の分光 IIの 362頁 ( 1992年版、丸善)に記載の方法により測定することができる。  [0343] The light emitting layer may further contain a host compound having a fluorescence maximum wavelength as the host compound. In this case, the energy transfer from the other host compound and the phosphorescent compound to the fluorescent compound allows the electroluminescence as an organic EL device to emit light of another host compound having a fluorescence maximum wavelength. A preferred host compound having a fluorescence maximum wavelength is a compound having a high fluorescence quantum yield in a solution state. Here, the fluorescence quantum yield is preferably 10% or more, particularly preferably 30% or more. Specific host compounds having a fluorescence maximum wavelength include coumarin dyes, pyran dyes, cyanine dyes, croconium dyes, squalium dyes, oxobenzanthracene dyes, fluorescein dyes, rhodamine dyes, pyrylium. Pigments, perylene pigments, stilbene pigments, polythiophene pigments, and the like. The fluorescence quantum yield can be measured by the method described in the fourth edition of Experimental Chemistry Course 7, Spectroscopy II, page 362 (1992 edition, Maruzen).
[0344] (リン光性化合物)  [0344] (Phosphorescent compound)
発光層に使用される材料 (以下、発光材料という)としては、上記のホスト化合物を 含有すると同時に、リン光性ィ匕合物を含有することが好ましい。これにより、より発光 効率の高!、有機 EL素子とすることができる。 The material used for the light emitting layer (hereinafter referred to as the light emitting material) preferably contains the above-mentioned host compound and at the same time contains a phosphorescent compound. This makes it more luminescent Highly efficient and can be an organic EL device.
[0345] 本発明に係るリン光性ィ匕合物は、励起三重項力もの発光が観測される化合物であ り、室温(25°C)にてリン光発光する化合物であり、リン光量子収率が、 25°Cにおいて 0. 01以上の化合物である。リン光量子収率は好ましくは 0. 1以上である。上記リン 光量子収率は、第 4版実験化学講座 7の分光 IIの 398頁(1992年版、丸善)に記載 の方法により測定できる。溶液中でのリン光量子収率は種々の溶媒を用いて測定で きるが、本発明に用いられるリン光性ィ匕合物は、任意の溶媒のいずれかにおいて上 記リン光量子収率が達成されればよい。  [0345] The phosphorescent compound according to the present invention is a compound in which luminescence with an excited triplet force is observed, is a compound that emits phosphorescence at room temperature (25 ° C), and is a phosphorescent quantum-contained compound. A compound having a rate of 0.01 or more at 25 ° C. The phosphorescence quantum yield is preferably 0.1 or more. The phosphorescent quantum yield can be measured by the method described in Spectra II, page 398 (1992 edition, Maruzen) of 4th edition, Experimental Chemistry Course 7. The phosphorescence quantum yield in a solution can be measured using various solvents, but the phosphorescent compound used in the present invention achieves the above phosphorescence quantum yield in any solvent. Just do it.
[0346] リン光性ィ匕合物の発光は原理としては 2種挙げられ、一つはキャリアが輸送されるホ ストィ匕合物上でキャリアの再結合が起こってホストイ匕合物の励起状態が生成し、この エネルギーをリン光性ィ匕合物に移動させることでリン光性ィ匕合物力 の発光を得ると いうエネルギー移動型、もう一つはリン光性ィ匕合物がキャリアトラップとなり、リン光性 化合物上でキャリアの再結合が起こりリン光性ィ匕合物力もの発光が得られるというキ ャリアトラップ型であるが、いずれの場合においても、リン光性化合物の励起状態の エネルギーはホストイ匕合物の励起状態のエネルギーよりも低いことが条件である。  [0346] There are two types of luminescence of phosphorescent compounds, and one is the excited state of the host compound due to carrier recombination on the host compound to which carriers are transported. The energy transfer type is to obtain light emission of phosphorescent compound force by transferring this energy to the phosphorescent compound, and the other is that the phosphorescent compound is a carrier trap. This is a carrier trap type in which recombination of carriers occurs on the phosphorescent compound and light emission of a phosphorescent compound power is obtained. In either case, the excited state energy of the phosphorescent compound is The condition is that the energy is lower than the excited state energy of the host compound.
[0347] リン光性ィ匕合物は、有機 EL素子の発光層に使用される公知のものの中から適宜選 択して用いることができる。  [0347] The phosphorescent compound can be appropriately selected from known materials used for the light-emitting layer of the organic EL device.
[0348] 本発明で用いられるリン光性ィ匕合物としては、好ましくは元素の周期表で 8族〜 10 族の金属を含有する錯体系化合物であり、さらに好ましくはイリジウム化合物、ォスミ ゥム化合物、または白金化合物(白金錯体系化合物)、希土類錯体であり、中でも最 も好まし 、のはイリジウム化合物である。  [0348] The phosphorescent compound used in the present invention is preferably a complex compound containing a group 8 to group 10 metal in the periodic table of elements, more preferably an iridium compound or osmium. Compounds, platinum compounds (platinum complex compounds), and rare earth complexes, with iridium compounds being most preferred among them.
[0349] 以下に、リン光性化合物の具体例を示すが、本発明はこれらに限定されない。これ らの化合物は、例えば、 Inorg. Chem. 40卷、 1704〜1711に記載の方法等により 合成できる。  [0349] Specific examples of the phosphorescent compound are shown below, but the present invention is not limited thereto. These compounds can be synthesized, for example, by the method described in Inorg. Chem. 40 卷, 1704-1711.
[0350] [化 118] lr-2 [0350] [Chemical 118] lr-2
[0351] [化 119] [0351] [Chemical 119]
lr-11 ir-12 lr-11 ir-12
120]120]
[0353] [化 121] [0353] [Chemical 121]
Pd-1 Pd-2 Pd-3 Pd-1 Pd-2 Pd-3
[0354] [化 122] [0354] [Chemical 122]
[0356] [化 124] [0356] [Chemical 124]
[0357] 本発明においては、リン光性ィ匕合物のリン光発光極大波長としては特に制限される ものではなぐ原理的には中心金属、配位子、配位子の置換基等を選択することで 得られる発光波長を変化させることができるが、リン光性ィ匕合物のリン光発光波長が 3 80〜480nmにリン光発光の極大波長を有することが好まし!/、。このような青色リン光 発光の有機 EL素子や、白色リン光発光の有機 EL素子で、より一層発光効率を高め ることがでさる。 [0357] In the present invention, the phosphorescent maximum wavelength of the phosphorescent compound is not particularly limited. In principle, a central metal, a ligand, a ligand substituent, and the like are selected. The emission wavelength obtained can be changed, but it is preferable that the phosphorescence emission compound has a phosphorescence emission maximum wavelength of 380 to 480 nm! /. With such blue phosphorescent organic EL elements and white phosphorescent organic EL elements, the luminous efficiency can be further improved.
[0358] 本発明の有機 EL素子や本発明に係る化合物の発光する色は、「新編色彩科学ノヽ ンドブック」(日本色彩学会編、東京大学出版会、 1985)の 108頁の図 4. 16におい て、分光放射輝度計 CS - 1000 (コ-力ミノルタセンシング社製)で測定した結果を C IE色度座標に当てはめたときの色で決定される。  [0358] The light emission color of the organic EL device of the present invention and the compound according to the present invention is shown in Fig. 4.16 on page 108 of "New Color Science Nord Book" (edited by the Japan Society for Color Science, University of Tokyo Press, 1985). Therefore, it is determined by the color when the result measured with the spectral radiance meter CS-1000 (manufactured by Co-Force Minolta Sensing) is applied to the C IE chromaticity coordinates.
[0359] 発光層は上記化合物を、例えば真空蒸着法、スピンコート法、キャスト法、 LB法、ィ ンクジェット法等の公知の薄膜ィ匕法により製膜して形成することができる。発光層とし ての膜厚は特に制限はないが、通常は 5ηπ!〜 5 μ m、好ましくは 5〜200nmの範囲 で選ばれる。この発光層はこれらのリン光性化合物やホスト化合物が 1種または 2種 以上力もなる一層構造であってもよいし、あるいは同一組成または異種組成の複数 層からなる積層構造であってもよ 、。 [0359] The light emitting layer can be formed by depositing the above compound by a known thin film method such as a vacuum deposition method, a spin coating method, a casting method, an LB method, or an ink jet method. The film thickness of the light emitting layer is not particularly limited, but is usually 5ηπ! It is selected in the range of ˜5 μm, preferably 5 to 200 nm. This light emitting layer may have a single layer structure in which these phosphorescent compounds and host compounds have one or more powers, or a plurality of same or different compositions. Even a laminated structure consisting of layers.
[0360] 《正孔輸送層》  [0360] 《Hole transport layer》
正孔輸送層とは正孔を輸送する機能を有する正孔輸送材料力 なり、広い意味で 正孔注入層、電子阻止層も正孔輸送層に含まれる。正孔輸送層は単層または複数 層設けることができる。  The hole transport layer is a hole transport material having a function of transporting holes. In a broad sense, a hole injection layer and an electron blocking layer are also included in the hole transport layer. The hole transport layer can be provided as a single layer or a plurality of layers.
[0361] 正孔輸送材料としては、正孔の注入または輸送、電子の障壁性の!/、ずれかを有す るものであり、有機物、無機物のいずれであってもよい。例えば、トリァゾール誘導体 、ォキサジァゾール誘導体、イミダゾール誘導体、ポリアリールアルカン誘導体、ビラ ゾリン誘導体及びピラゾロン誘導体、フ -レンジァミン誘導体、ァリールァミン誘導 体、ァミノ置換カルコン誘導体、ォキサゾール誘導体、スチリルアントラセン誘導体、 フルォレノン誘導体、ヒドラゾン誘導体、スチルベン誘導体、シラザン誘導体、ァニリ ン系共重合体、また導電性高分子オリゴマー、特にチォフェンオリゴマー等が挙げら れる。  [0361] The hole transport material has either injection or transport of holes and / or a barrier property of electrons, and may be either organic or inorganic. For example, triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, violazoline derivatives and pyrazolone derivatives, fluorenedamine derivatives, arylene amine derivatives, amino substituted chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, Examples thereof include stilbene derivatives, silazane derivatives, aniline copolymers, and conductive polymer oligomers, particularly thiophene oligomers.
[0362] 正孔輸送材料としては上記のものを使用することができる力 ボルフイリンィ匕合物、 芳香族第三級ァミン化合物及びスチリルアミン化合物、特に芳香族第三級アミンィ匕 合物を用いることが好まし 、。  [0362] The ability to use the above-described materials as the hole transport material [0362] It is possible to use a borfilin compound, an aromatic tertiary amine compound and a styrylamine compound, particularly an aromatic tertiary amine compound. I like it.
[0363] 芳香族第三級アミンィ匕合物及びスチリルアミンィ匕合物の代表例としては、 N, N, N ' , N' —テトラフエニル一 4, 4' —ジァミノフエ-ル; N, N' —ジフエ-ル一 N, N ' —ビス(3—メチルフエ-ル)一〔1, 1' —ビフエ-ル〕一 4, 4' —ジァミン(TPD) ; 2, 2 ビス(4 ジ一 p トリルァミノフエ-ル)プロパン; 1, 1—ビス(4 ジ一 p トリ ルァミノフエ-ル)シクロへキサン; N, N, N' , N' —テトラ一 p トリル一 4, 4' - ジアミノビフエ-ル; 1 , 1 ビス(4 ジ一 p トリルァミノフエ-ル) 4 フエ-ルシク 口へキサン;ビス(4 -ジメチルァミノ 2 メチルフエ-ル)フエニルメタン;ビス(4 -ジ —p トリルァミノフエ-ル)フエ-ルメタン; N, N' —ジフエ-ル一 N, N' —ジ(4— メトキシフエ-ル) 4, 4' ージアミノビフエニル; N, N, N' , N' —テトラフエ-ル —4, 4' ージアミノジフエ-ルエーテル; 4, 4' ビス(ジフエ-ルァミノ)クオ一ドリフ ェ -ル; N, N, N トリ(p トリル)ァミン; 4— (ジ— p トリルァミノ)— 4' —〔4— (ジ —p トリルァミノ)スチリル〕スチルベン; 4— N, N ジフエ-ルァミノ—(2 ジフエ- ルビ-ル)ベンゼン; 3—メトキシ一 4' — N, N ジフエニルアミノスチルベンゼン; N フエ-ルカルバゾール、さらには米国特許第 5, 061 , 569号明細書に記載されて いる 2個の縮合芳香族環を分子内に有するもの、例えば、 4, 4' ビス〔N—(1ーナ フチル) N フエ-ルァミノ〕ビフヱ-ル(NPD)、特開平 4 308688号公報に記 載されているトリフエ-ルァミンユニットが 3つスターバースト型に連結された 4, 4' , A" —トリス〔?^— (3—メチルフエ-ル) N フエ-ルァミノ〕トリフエ-ルァミン(MTD ATA)等が挙げられる。 [0363] Representative examples of aromatic tertiary amine compounds and styrylamine compounds include N, N, N ', N'-tetraphenyl-1,4'-diamineamino; N, N' —Diphenyl N, N '— Bis (3-methylphenol) 1 [1, 1' — Biphenyl] 1, 4, 4 '— Diamine (TPD); 2, 2 Bis (4 1, 1-bis (4 di-l-tri-laminophenol) cyclohexane; N, N, N ', N'—tetra-l-tolyl-1,4,4'-diaminobiphenyl; 1 Bis (4 di-p-triaminophenol) 4 Phenol mouth hexane; Bis (4-dimethylamino 2-methylphenol) phenylmethane; Bis (4-di-p-triaminophenol) phenol; N, N ' —Diphenyl N, N '—Di (4-methoxyphenyl) 4, 4'diaminobiphenyl; N, N, N ', N' — Tetraphenyl —4, 4 'Diaminodiphenyl -Luether; 4, 4 'Bis (diphenylamino) quadryl; N, N, N Tri (p tolyl) amine; 4— (Di-p-tolylamino) — 4 ′ — [4— (Di — p-tolylamino) styryl] stilbene; 4-N, N diphenylamino (2 diphenyl) Ruby) benzene; 3-methoxy 1 4′—N, N diphenylaminostilbenzene; N phenolcarbazole, and also two condensations described in US Pat. No. 5,061,569 Those having an aromatic ring in the molecule, for example, 4, 4 'bis [N- (1-naphthyl) N ferroamino] biphenyl (NPD), described in JP-A-4308688 3, 4 ', A "—Tris [? ^ — (3-methylphenol) N-phenylamine] Triphenylamine (MTD ATA) It is done.
[0364] さらに、これらの材料を高分子鎖に導入した、またはこれらの材料を高分子の主鎖 とした高分子材料を用いることもできる。また、 p型— Si、 p型— SiC等の無機化合物 も正孔注入材料、正孔輸送材料として使用することができる。  [0364] Furthermore, a polymer material in which these materials are introduced into a polymer chain or these materials as a polymer main chain can also be used. In addition, inorganic compounds such as p-type—Si and p-type—SiC can also be used as the hole injection material and the hole transport material.
[0365] 正孔輸送層は上記正孔輸送材料を、例えば、真空蒸着法、スピンコート法、キャス ト法、インクジェット法を含む印刷法、 LB法等の公知の方法により、薄膜ィ匕することに より形成することができる。正孔輸送層の膜厚については特に制限はないが、通常は 5nm〜5 μ m程度、好ましくは 5〜200nmである。この正孔輸送層は上記材料の 1 種または 2種以上力もなる一層構造であってもよ 、。  [0365] The hole transport layer is formed by thinning the hole transport material by a known method such as a vacuum deposition method, a spin coating method, a casting method, a printing method including an ink jet method, or an LB method. Can be formed. Although there is no restriction | limiting in particular about the film thickness of a positive hole transport layer, Usually, 5 nm-about 5 micrometers, Preferably it is 5-200 nm. The hole transport layer may have a single layer structure that can be one or more of the above materials.
[0366] 《電子輸送層》  [0366] 《Electron Transport Layer》
電子輸送層とは電子を輸送する機能を有する材料力 なり、広い意味で電子注入 層、正孔阻止層も電子輸送層に含まれる。電子輸送層は単層または複数層設けるこ とがでさる。  The electron transport layer is a material force having a function of transporting electrons, and in a broad sense, an electron injection layer and a hole blocking layer are also included in the electron transport layer. An electron transport layer may be provided as a single layer or multiple layers.
[0367] 従来、単層の電子輸送層、及び複数層とする場合は発光層に対して陰極側に隣 接する電子輸送層に用いられる電子輸送材料 (正孔阻止材料を兼ねる)としては、陰 極より注入された電子を発光層に伝達する機能を有していればよぐその材料として は従来公知の化合物の中から任意のものを選択して用いることができ、例えば、 -ト 口置換フルオレン誘導体、ジフヱ-ルキノン誘導体、チォピランジオキシド誘導体、力 ルボジイミド、フレオレニリデンメタン誘導体、アントラキノジメタン及びアントロン誘導 体、ォキサジァゾール誘導体等が挙げられる。さらに、上記ォキサジァゾール誘導体 にお 、て、ォキサジァゾール環の酸素原子を硫黄原子に置換したチアジアゾール誘 導体、電子吸引基として知られているキノキサリン環を有するキノキサリン誘導体も、 電子輸送材料として用いることができる。さらにこれらの材料を高分子鎖に導入した、 またはこれらの材料を高分子の主鎖とした高分子材料を用いることもできる。 [0367] Conventionally, in the case of a single electron transport layer and a plurality of layers, as an electron transport material (also serving as a hole blocking material) used for an electron transport layer adjacent to the light emitting layer on the cathode side, Any material can be selected from conventionally known compounds as long as it has a function of transmitting electrons injected from the electrode to the light-emitting layer. Examples include fluorene derivatives, diphenylquinone derivatives, thiopyran dioxide oxide derivatives, strength rubodiimides, fluorenylidenemethane derivatives, anthraquinodimethane and anthrone derivatives, oxadiazole derivatives, and the like. Further, in the above oxadiazole derivative, a thiadiazole derivative in which the oxygen atom of the oxaziazole ring is substituted with a sulfur atom, and a quinoxaline derivative having a quinoxaline ring known as an electron withdrawing group are also provided. It can be used as an electron transport material. Furthermore, a polymer material in which these materials are introduced into a polymer chain or these materials are used as a polymer main chain can also be used.
[0368] また、 8 キノリノール誘導体の金属錯体、例えば、トリス(8 キノリノール)アルミ- ゥム(Alq)、トリス(5, 7—ジクロロ一 8—キノリノール)アルミニウム、トリス(5, 7—ジブ ロモ一 8 キノリノール)アルミニウム、トリス(2 メチル 8 -キノリノール)アルミ-ゥ ム、トリス(5—メチル 8—キノリノール)アルミニウム、ビス(8—キノリノール)亜鉛(Zn q)等、及びこれらの金属錯体の中心金属が In、 Mg、 Cu、 Ca、 Sn、 Gaまたは Pbに 置き替わった金属錯体も、電子輸送材料として用いることができる。その他、メタルフ リーもしくはメタルフタロシアニン、またはそれらの末端がアルキル基ゃスルホン酸基 等で置換されているものも、電子輸送材料として好ましく用いることができる。また、発 光層の材料として例示したジスチリルビラジン誘導体も、電子輸送材料として用いる ことができるし、正孔注入層、正孔輸送層と同様に、 n型— Si、 n型— SiC等の無機半 導体も電子輸送材料として用いることができる。  [0368] In addition, metal complexes of 8 quinolinol derivatives such as tris (8 quinolinol) aluminum (Alq), tris (5,7-dichloro-1-8-quinolinol) aluminum, tris (5,7-dibromone) 8quinolinol) aluminum, tris (2methyl 8-quinolinol) aluminum, tris (5-methyl 8-quinolinol) aluminum, bis (8-quinolinol) zinc (Zn q), etc., and the central metal of these metal complexes Metal complexes in which is replaced with In, Mg, Cu, Ca, Sn, Ga or Pb can also be used as electron transport materials. In addition, metal free or metal phthalocyanine, or those having terminal ends substituted with an alkyl group or a sulfonic acid group can be preferably used as the electron transporting material. In addition, the distyrylvirazine derivative exemplified as the material of the light emitting layer can also be used as an electron transport material, and, like the hole injection layer and the hole transport layer, n-type—Si, n-type—SiC, etc. These inorganic semiconductors can also be used as electron transport materials.
[0369] 電子輸送層は上記電子輸送材料を、例えば、真空蒸着法、スピンコート法、キャス ト法、インクジェット法を含む印刷法、 LB法等の公知の方法により、薄膜ィ匕することに より形成することができる。電子輸送層の膜厚については特に制限はないが、通常は 5nm〜5 μ m程度、好ましくは 5〜200nmである。電子輸送層は上記材料の 1種ま たは 2種以上力もなる一層構造であってもよ 、。  [0369] The electron transport layer is obtained by thin-filming the electron transport material by a known method such as a vacuum deposition method, a spin coating method, a casting method, a printing method including an ink jet method, or an LB method. Can be formed. Although there is no restriction | limiting in particular about the film thickness of an electron carrying layer, Usually, 5 nm-about 5 micrometers, Preferably it is 5-200 nm. The electron transport layer may be a single layer structure having one or more of the above materials.
[0370] 《基体》  [0370] << Substrate >>
本発明の有機 EL素子は、基体上に形成されているのが好ましい。  The organic EL device of the present invention is preferably formed on a substrate.
[0371] 本発明の有機 EL素子に用いることのできる基体 (以下、基板、基材、支持体等とも いう)としては、ガラス、プラスチック等の種類には特に限定はなぐまた、透明のもの であれば特に制限はないが、好ましく用いられる基板としては、例えば、ガラス、石英 、光透過性榭脂フィルムを挙げることができる。特に好ましい基体は、有機 EL素子に フレキシブル性を与えることが可能な榭脂フィルムである。  [0371] The substrate (hereinafter also referred to as a substrate, substrate, support, etc.) that can be used in the organic EL device of the present invention is not particularly limited in the type of glass, plastic and the like, and is transparent. The substrate is not particularly limited as long as it is used, but preferred examples of the substrate include glass, quartz, and a light-transmitting resin film. A particularly preferable substrate is a resin film capable of imparting flexibility to the organic EL element.
[0372] 榭脂フィルムとしては、例えば、ポリエチレンテレフタレート(PET)、ポリエチレンナ フタレート(PEN)、ポリエーテルスルホン(PES)、ポリエーテルイミド、ポリエーテル エーテルケトン、ポリフエ-レンスルフイド、ポリアリレート、ポリイミド、ポリカーボネート (PC)、セルローストリアセテート (TAC)、セルロースアセテートプロピオネート(CAP )等力もなるフィルム等が挙げられる。榭脂フィルムの表面には、無機物、有機物の被 膜またはその両者のハイブリッド被膜が形成されて 、てもよ 、。 [0372] Examples of the resin film include polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyethersulfone (PES), polyetherimide, polyether etherketone, polyphenylene sulfide, polyarylate, polyimide, and polycarbonate. (PC), cellulose triacetate (TAC), cellulose acetate propionate (CAP) and the like. On the surface of the resin film, an inorganic film, an organic film, or a hybrid film of the both may be formed.
[0373] 本発明の有機 EL素子の発光の室温における外部取り出し効率は 1%以上であるこ と力 子ましく、より好ましくは 5%以上である。ここに、外部取り出し量子効率(%) =有 機 EL素子外部に発光した光子数 Z有機 EL素子に流した電子数 X 100である。  [0373] The external extraction efficiency at room temperature of light emission of the organic EL device of the present invention is preferably 1% or more, more preferably 5% or more. Here, the external extraction quantum efficiency (%) = the number of photons emitted outside the organic EL element Z the number of electrons X 100 flowing through the organic EL element.
[0374] また、カラーフィルタ一等の色相改良フィルタ一等を併用しても、有機 EL素子から の発光色を蛍光体を用いて多色へ変換する色変換フィルターを併用してもよ ヽ。色 変換フィルターを用いる場合においては、有機 EL素子の発光の λ maxは 480nm以 下が好ましい。  [0374] In addition, a hue improvement filter such as a color filter may be used in combination, or a color conversion filter that converts light emitted from an organic EL element into multiple colors using a phosphor may be used in combination. In the case of using a color conversion filter, the λ max of light emission of the organic EL element is preferably 480 nm or less.
[0375] 《有機 EL素子の作製方法》  [0375] <Method for manufacturing organic EL element>
本発明の有機 EL素子の作製方法の一例として、陽極/正孔注入層/正孔輸送層 Z発光層 Z電子輸送層 Z電子注入層 Z陰極からなる有機 EL素子の作製法につい て説明する。  As an example of the method for producing the organic EL device of the present invention, a method for producing an organic EL device comprising an anode / hole injection layer / hole transport layer Z light emitting layer Z electron transport layer Z electron injection layer Z cathode will be described.
[0376] まず適当な基体上に所望の電極物質、例えば、陽極用物質力 なる薄膜を 1 μ m 以下、好ましくは 10〜200nmの膜厚になるように、蒸着やスパッタリング等の方法に より形成させ、陽極を作製する。次に、この上に有機 EL素子材料である正孔注入層 、正孔輸送層、発光層、電子輸送層、電子注入層、正孔阻止層の有機化合物薄膜 を形成させる。  [0376] First, a desired electrode material, for example, a thin film having a material force for an anode is formed on a suitable substrate by a method such as vapor deposition or sputtering so as to have a thickness of 1 μm or less, preferably 10 to 200 nm. To produce an anode. Next, an organic compound thin film of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and a hole blocking layer, which is an organic EL element material, is formed thereon.
[0377] この有機化合物薄膜の薄膜ィ匕の方法としては、前記の如く蒸着法、ウエットプロセス  [0377] As a method of thin film formation of this organic compound thin film, as described above, vapor deposition method, wet process
(スピンコート法、キャスト法、インクジェット法、印刷法)等があるが、均質な膜が得ら れやすぐかつピンホールが生成しにくい等の点から、真空蒸着法、スピンコート法、 インクジェット法、印刷法が特に好ましい。さらに層ごとに異なる製膜法を適用してもよ い。製膜に蒸着法を採用する場合、その蒸着条件は使用する化合物の種類等により 異なるが、一般にボート加熱温度 50〜450°C、真空度 10—6〜10—2Pa、蒸着速度 0. 01〜50nmZ秒、基板温度— 50〜300。C、膜厚 0. lnm〜5 μ m、好ましくは 5〜2 OOnmの範囲で適宜選ぶことが望まし!/、。 (Spin coating method, casting method, ink jet method, printing method) etc., but vacuum deposition method, spin coating method, ink jet method from the point that a homogeneous film can be obtained and pinholes are not easily generated. The printing method is particularly preferred. Furthermore, different film forming methods may be applied for each layer. When employing the vapor deposition film, the depositing conditions thereof are varied according to kinds of materials used, generally boat temperature 50 to 450 ° C, vacuum degree of 10- 6 to 10-2 Pa, deposition rate 0.01 ~ 50nmZ seconds, substrate temperature-50 ~ 300. C, film thickness of 0.1 nm to 5 μm, preferably 5 to 2 OOnm is preferable.
[0378] これらの層を形成後、その上に陰極用物質力もなる薄膜を、 1 μ m以下好ましくは 5 0nm〜200nmの範囲の膜厚になるように、例えば、蒸着やスパッタリング等の方法 により形成させ、陰極を設けることにより所望の有機 EL素子が得られる。この有機 EL 素子の作製は、一回の真空引きで一貫して正孔注入層から陰極まで作製するのが 好ましいが、途中で取り出して異なる製膜法を施しても構わない。その際、作業を乾 燥不活性ガス雰囲気下で行う等の配慮が必要となる。 [0378] After these layers are formed, a thin film having a material force for a cathode is formed on the layer to a thickness of 1 μm or less, preferably 5 For example, a desired organic EL device can be obtained by forming the film so as to have a film thickness in the range of 0 nm to 200 nm by a method such as vapor deposition or sputtering and providing a cathode. The organic EL device is preferably manufactured from the hole injection layer to the cathode consistently by a single evacuation, but it may be taken out halfway and subjected to different film forming methods. At that time, it is necessary to consider that the work is performed in a dry inert gas atmosphere.
[0379] 本発明の多色の表示装置は発光層形成時のみシャドーマスクを設け、他層は共通 であるのでシャドーマスク等のパターユングは不要であり、一面に蒸着法、キャスト法 、スピンコート法、インクジェット法、印刷法等で膜を形成できる。発光層のみパター- ングを行う場合、その方法に限定はないが、好ましくは蒸着法、インクジェット法、印 刷法である。蒸着法を用いる場合においては、シャドーマスクを用いたパターユング が好ましい。 [0379] The multicolor display device of the present invention is provided with a shadow mask only at the time of forming a light emitting layer, and the other layers are common, so there is no need for patterning such as a shadow mask. A film can be formed by a method, an inkjet method, a printing method, or the like. When patterning only the light emitting layer, the method is not limited, but the vapor deposition method, the ink jet method, and the printing method are preferable. When using the vapor deposition method, patterning using a shadow mask is preferred.
[0380] また作製順序を逆にして、陰極、電子注入層、電子輸送層、発光層、正孔輸送層、 正孔注入層、陽極の順に作製することも可能である。このようにして得られた多色の 表示装置に、直流電圧を印加する場合には、陽極を +、陰極を一の極性として電圧 2〜40V程度を印加すると、発光が観測できる。また交流電圧を印加してもよい。な お、印加する交流の波形は任意でよい。  [0380] Alternatively, the order of production may be reversed, and the cathode, the electron injection layer, the electron transport layer, the light emitting layer, the hole transport layer, the hole injection layer, and the anode may be produced in this order. When a DC voltage is applied to the multi-color display device thus obtained, light emission can be observed by applying a voltage of about 2 to 40 V with the anode as + and the cathode as one polarity. An alternating voltage may be applied. The AC waveform to be applied may be arbitrary.
[0381] 本発明の表示装置は、表示デバイス、ディスプレイ、各種発光光源として用いること ができる。表示デバイス、ディスプレイにおいて、青、赤、緑発光の 3種の有機 EL素 子を用いることにより、フルカラーの表示が可能となる。  [0381] The display device of the present invention can be used as a display device, a display, and various light sources. Display devices and displays can be displayed in full color by using three types of organic EL elements that emit blue, red, and green light.
[0382] 表示デバイス、ディスプレイとしてはテレビ、ノ ソコン、モパイル機器、 AV機器、文 字放送表示、自動車内の情報表示等が挙げられる。特に静止画像や動画像を再生 する表示装置として使用してもよぐ動画再生用の表示装置として使用する場合の駆 動方式は単純マトリックス (パッシブマトリックス)方式でもアクティブマトリックス方式で もどちらでもよい。  [0382] Examples of display devices and displays include televisions, computers, mopile devices, AV devices, text broadcast displays, and information displays in automobiles. In particular, the driving method when used as a display device for reproducing moving images, which may be used as a display device for reproducing still images or moving images, may be either a simple matrix (passive matrix) method or an active matrix method.
[0383] 本発明の照明装置は家庭用照明、車内照明、時計や液晶用のバックライト、看板 広告、信号機、光記憶媒体の光源、電子写真複写機の光源、光通信処理機の光源 、光センサの光源等が挙げられるがこれに限定するものではない。  [0383] The lighting device of the present invention includes home lighting, interior lighting, backlights for clocks and liquid crystals, billboard advertisements, traffic lights, light sources of optical storage media, light sources of electrophotographic copying machines, light sources of optical communication processors, light Examples include, but are not limited to, the light source of the sensor.
[0384] また、本発明の有機 EL素子に共振器構造を持たせた有機 EL素子として用いても よい。このような共振器構造を有した有機 EL素子の使用目的としては、光記憶媒体 の光源、電子写真複写機の光源、光通信処理機の光源、光センサの光源等が挙げ られる力 これらに限定されない。また、レーザ発振をさせることにより、上記用途に使 用してちょい。 [0384] The organic EL device of the present invention may be used as an organic EL device having a resonator structure. Good. The purpose of using an organic EL element having such a resonator structure includes a light source of an optical storage medium, a light source of an electrophotographic copying machine, a light source of an optical communication processor, a light source of an optical sensor, etc. Not. It can also be used for the above applications by causing laser oscillation.
[0385] 本発明の有機 EL素子は、照明用や露光光源のような 1種のランプとして使用しても よいし、画像を投影するタイプのプロジェクシヨン装置や、静止画像や動画像を直接 視認するタイプの表示装置 (ディスプレイ)として使用してもよい。動画再生用の表示 装置として使用する場合の駆動方式は単純マトリックス (パッシブマトリックス)方式で もアクティブマトリックス方式でもどちらでもよい。または、異なる発光色を有する本発 明の有機 EL素子を 3種以上使用することにより、フルカラー表示装置を作製すること が可能である。または、一色の発光色、例えば、白色発光を、カラーフィルターを用 いて BGRにし、フルカラー化することも可能である。さらに有機 ELの発光色を、色変 換フィルターを用いて他色に変換しフルカラー化することも可能であるが、その場合、 有機 EL発光の λ maxは 480nm以下であることが好ましい。  [0385] The organic EL device of the present invention may be used as a kind of lamp for illumination or exposure light source, or a projection device of a type for projecting an image, or directly viewing a still image or a moving image. It may be used as a type of display device (display). When used as a display device for video playback, the drive method may be either a simple matrix (passive matrix) method or an active matrix method. Alternatively, a full-color display device can be manufactured by using three or more organic EL elements of the present invention having different emission colors. Alternatively, it is possible to make a single color emission color, for example, white emission, into a BGR by using a color filter to achieve full color. Furthermore, the emission color of the organic EL can be converted into another color by using a color conversion filter, and in this case, the λ max of the organic EL emission is preferably 480 nm or less.
[0386] 有機 EL素子力も構成される表示装置の一例を図面に基づいて以下に説明する。 [0386] An example of a display device that also has organic EL element power will be described below with reference to the drawings.
[0387] 図 1は、有機 EL素子力 構成される表示装置の一例を示した模式図である。有機 EL素子の発光により画像情報の表示を行う、例えば、携帯電話等のディスプレイの 模式図である。 FIG. 1 is a schematic view showing an example of a display device configured with organic EL element power. FIG. 2 is a schematic diagram of a display such as a mobile phone that displays image information by light emission of an organic EL element.
[0388] ディスプレイ 1は、複数の画素を有する表示部 A、画像情報に基づ!/、て表示部 Aの 画像走査を行う制御部 B等力もなる。  [0388] The display 1 also includes a display unit A having a plurality of pixels, a control unit B that performs image scanning of the display unit A based on image information!
[0389] 制御部 Bは、表示部 Aと電気的に接続され、複数の画素それぞれに外部からの画 像情報に基づいて走査信号と画像データ信号を送り、走査信号により走査線毎の画 素が画像データ信号に応じて順次発光して画像走査を行って画像情報を表示部 A に表示する。 [0389] The control unit B is electrically connected to the display unit A, and sends a scanning signal and an image data signal to each of a plurality of pixels based on image information from the outside. Sequentially emit light according to the image data signal, scan the image, and display the image information on the display unit A.
[0390] 図 2は、表示部 Aの模式図である。 FIG. 2 is a schematic diagram of the display unit A.
[0391] 表示部 Aは基板上に、複数の走査線 5及びデータ線 6を含む配線部と、複数の画 素 3等とを有する。表示部 Aの主要な部材の説明を以下に行う。図 2においては、画 素 3の発光した光が、白矢印方向(下方向)へ取り出される場合を示して 、る。 [0392] 配線部の走査線 5及び複数のデータ線 6は、各々導電材料からなり、走査線 5とデ ータ線 6は格子状に直交して、直交する位置で画素 3に接続している(詳細は図示せ ず)。 [0391] The display unit A includes a wiring unit including a plurality of scanning lines 5 and data lines 6, a plurality of pixels 3 and the like on a substrate. The main members of the display unit A will be described below. FIG. 2 shows the case where the light emitted from pixel 3 is extracted in the direction of the white arrow (downward). [0392] The scanning lines 5 and the plurality of data lines 6 in the wiring portion are each made of a conductive material, and the scanning lines 5 and the data lines 6 are orthogonal to each other in a grid pattern and are connected to the pixels 3 at the orthogonal positions. (Details not shown).
[0393] 画素 3は、走査線 5から走査信号が印加されると、データ線 6から画像データ信号を 受け取り、受け取った画像データに応じて発光する。発光の色が赤領域の画素、緑 領域の画素、青領域の画素を、適宜、同一基板上に並置することによって、フルカラ 一表示が可能となる。  [0393] When a scanning signal is applied from the scanning line 5, the pixel 3 receives an image data signal from the data line 6, and emits light according to the received image data. Full color display is possible by appropriately arranging pixels in the red region, the green region, and the blue region on the same substrate.
[0394] 次に、画素の発光プロセスを説明する。  Next, the light emission process of the pixel will be described.
[0395] 図 3は、画素の模式図である。  FIG. 3 is a schematic diagram of a pixel.
[0396] 画素は、有機 EL素子 10、スイッチングトランジスタ 11、駆動トランジスタ 12、コンデ ンサ 13等を備えている。複数の画素に有機 EL素子 10として、赤色、緑色、青色発 光の有機 EL素子を用い、これらを同一基板上に並置することでフルカラー表示を行 うことができる。  [0396] The pixel includes an organic EL element 10, a switching transistor 11, a driving transistor 12, a capacitor 13, and the like. Full-color display can be performed by using organic EL elements of red, green, and blue light emission as organic EL elements 10 in a plurality of pixels and arranging them on the same substrate.
[0397] 図 3において、制御部 B力もデータ線 6を介してスイッチングトランジスタ 11のドレイ ンに画像データ信号が印加される。そして、制御部 B力 走査線 5を介してスィッチン グトランジスタ 11のゲートに走査信号が印加されると、スイッチングトランジスタ 11の 駆動がオンし、ドレインに印加された画像データ信号がコンデンサ 13と駆動トランジ スタ 12のゲートに伝達される。  In FIG. 3, an image data signal is also applied to the drain of the switching transistor 11 via the data line 6 in the control unit B force. When a scanning signal is applied to the gate of the switching transistor 11 via the control unit B force scanning line 5, the driving of the switching transistor 11 is turned on, and the image data signal applied to the drain is transferred to the capacitor 13 and the driving transistor. It is transmitted to the gate of the star 12.
[0398] 画像データ信号の伝達により、コンデンサ 13が画像データ信号の電位に応じて充 電されるとともに、駆動トランジスタ 12の駆動がオンする。駆動トランジスタ 12は、ドレ インが電源ライン 7に接続され、ソースが有機 EL素子 10の電極に接続されており、ゲ 一トに印加された画像データ信号の電位に応じて電源ライン 7から有機 EL素子 10に 電流が供給される。  By transmitting the image data signal, the capacitor 13 is charged according to the potential of the image data signal, and the drive of the drive transistor 12 is turned on. The drive transistor 12 has a drain connected to the power supply line 7 and a source connected to the electrode of the organic EL element 10, and the organic EL element is connected from the power supply line 7 according to the potential of the image data signal applied to the gate. Current is supplied to element 10.
[0399] 制御部 Bの順次走査により走査信号が次の走査線 5に移ると、スイッチングトランジ スタ 11の駆動がオフする。しかし、スイッチングトランジスタ 11の駆動がオフしてもコン デンサ 13は充電された画像データ信号の電位を保持するので、駆動トランジスタ 12 の駆動はオン状態が保たれて、次の走査信号の印加が行われるまで有機 EL素子 1 0の発光が継続する。順次走査により次に走査信号が印加されたとき、走査信号に 同期した次の画像データ信号の電位に応じて駆動トランジスタ 12が駆動して有機 E L素子 10が発光する。 [0399] When the scanning signal is moved to the next scanning line 5 by the sequential scanning of the control unit B, the driving of the switching transistor 11 is turned off. However, even if the driving of the switching transistor 11 is turned off, the capacitor 13 holds the potential of the charged image data signal, so that the driving of the driving transistor 12 is kept on and the next scanning signal is applied. The organic EL device 10 continues to emit light until it is seen. When the scanning signal is next applied by sequential scanning, The drive transistor 12 is driven according to the potential of the next synchronized image data signal, and the organic EL element 10 emits light.
[0400] 即ち、有機 EL素子 10の発光は、複数の画素それぞれの有機 EL素子 10に対して 、アクティブ素子であるスイッチングトランジスタ 11と駆動トランジスタ 12を設けて、複 数の画素 3それぞれの有機 EL素子 10の発光を行って 、る。このような発光方法をァ クティブマトリックス方式と呼んで 、る。  That is, the organic EL element 10 emits light by providing a switching transistor 11 and a driving transistor 12 as active elements for each of the organic EL elements 10 of each of the plurality of pixels, thereby providing organic EL for each of the plurality of pixels 3. The device 10 emits light. Such a light emission method is called an active matrix method.
[0401] ここで、有機 EL素子 10の発光は、複数の階調電位を持つ多値の画像データ信号 による複数の階調の発光でもよ 、し、 2値の画像データ信号による所定の発光量の オン、才フでもよ!/、。  [0401] Here, the light emission of the organic EL element 10 may be light emission of a plurality of gradations by a multi-value image data signal having a plurality of gradation potentials, or a predetermined light emission amount by the binary image data signal. On, even a talent! /.
[0402] また、コンデンサ 13の電位の保持は、次の走査信号の印加まで継続して保持して もよ 、し、次の走査信号が印加される直前に放電させてもょ 、。  [0402] Further, the potential of the capacitor 13 may be maintained until the next scanning signal is applied, or may be discharged immediately before the next scanning signal is applied.
[0403] 本発明にお 、ては、上述したアクティブマトリックス方式に限らず、走査信号が走査 されたときのみデータ信号に応じて有機 EL素子を発光させるパッシブマトリックス方 式の発光駆動でもよい。 [0403] In the present invention, not only the active matrix method described above, but also a passive matrix method of light emission driving in which an organic EL element emits light according to a data signal only when a scanning signal is scanned.
[0404] 図 4は、パッシブマトリックス方式による表示装置の模式図である。図 4において、複 数の走査線 5と複数の画像データ線 6が画素 3を挟んで対向して格子状に設けられ ている。 [0404] FIG. 4 is a schematic view of a passive matrix display device. In FIG. 4, a plurality of scanning lines 5 and a plurality of image data lines 6 are provided in a lattice shape so as to face each other with the pixel 3 interposed therebetween.
[0405] 順次走査により走査線 5の走査信号が印加されたとき、印加された走査線 5に接続 して 、る画素 3が画像データ信号に応じて発光する。ノ ッシブマトリックス方式では画 素 3にアクティブ素子がなく、製造コストの低減が計れる。  [0405] When the scanning signal of the scanning line 5 is applied by sequential scanning, the pixel 3 connected to the applied scanning line 5 emits light according to the image data signal. With the noisy matrix method, pixel 3 has no active elements, and manufacturing costs can be reduced.
[0406] 本発明に係る有機 EL材料は、また照明装置として、実質白色の発光を生じる有機 EL素子に適用できる。複数の発光材料により複数の発光色を同時に発光させて混 色により白色発光を得る。複数の発光色の組み合わせとしては、青色、緑色、青色の 3原色の 3つの発光極大波長を含有させたものでもよいし、青色と黄色、青緑と橙色 等の補色の関係を利用した 2つの発光極大波長を含有したものでもよい。  [0406] The organic EL material according to the present invention can also be applied to an organic EL element that emits substantially white light as a lighting device. A plurality of light-emitting materials emit light of a plurality of light-emitting colors at the same time to obtain white light emission by mixing colors. The combination of multiple emission colors may include three emission maximum wavelengths of the three primary colors of blue, green, and blue, or two using the relationship of complementary colors such as blue and yellow, blue green and orange, etc. The thing containing the light emission maximum wavelength may be used.
[0407] また、複数の発光色を得るための発光材料の組み合わせは、複数のリン光または 蛍光を発光する材料 (発光ドーパント)を、複数組み合わせたもの、蛍光またはリン光 を発光する発光材料と、該発光材料からの光を励起光として発光する色素材料とを 組み合わせたものの 、ずれでもよ!/ヽが、本発明に係わる白色有機エレクト口ルミネッ センス素子においては、発光ドーパントを複数組み合わせる方式が好ましい。 [0407] In addition, a combination of light emitting materials for obtaining a plurality of emission colors includes a combination of a plurality of phosphorescent or fluorescent materials (light emitting dopants), a light emitting material that emits fluorescent or phosphorescent light, and A dye material that emits light from the light emitting material as excitation light Although they are combined, they may be misaligned. However, in the white organic electoluminescence device according to the present invention, a method of combining a plurality of light emitting dopants is preferable.
[0408] 複数の発光色を得るための有機エレクト口ルミネッセンス素子の層構成としては、複 数の発光ドーパントを、一つの発光層中に複数存在させる方法、複数の発光層を有 し、各発光層中に発光波長の異なるドーパントをそれぞれ存在させる方法、異なる波 長に発光する微小画素をマトリックス状に形成する方法等が挙げられる。  [0408] As the layer structure of the organic electoluminescence device for obtaining a plurality of emission colors, a method in which a plurality of emission dopants exist in one emission layer, a plurality of emission layers, and each emission Examples thereof include a method in which dopants having different emission wavelengths are present in the layer, and a method in which minute pixels emitting light of different wavelengths are formed in a matrix.
[0409] 本発明に係る白色有機エレクト口ルミネッセンス素子においては、必要に応じ製膜 時にメタルマスクやインクジェットプリンティング法等でパター-ングを施してもよい。 パター-ングする場合は、電極のみをパター-ングしてもいいし、電極と発光層をパ ターニングしても 、 、し、素子全層をパター-ングしても 、 、。  [0409] In the white organic electoluminescence device according to the present invention, patterning may be performed by a metal mask, an ink-jet printing method, or the like as needed during film formation. In the case of patterning, only the electrode may be patterned, the electrode and the light emitting layer may be patterned, or the entire device layer may be patterned.
[0410] 発光層に用いる発光材料としては特に制限はなぐ例えば、液晶表示素子におけ るノ ックライトであれば、 CF (カラーフィルター)特性に対応した波長範囲に適合する ように、本発明に係る白金錯体、また公知の発光材料の中から任意のものを選択して 組み合わせて白色化すればよ!、。  [0410] The light emitting material used for the light emitting layer is not particularly limited. For example, in the case of a knocklight in a liquid crystal display element, the light emitting material according to the present invention is adapted to the wavelength range corresponding to the CF (color filter) characteristics. Choose any one of platinum complexes and other known luminescent materials and combine them to make them white!
[0411] このように、白色発光する本発明の発光有機 EL素子は、前記表示デバイス、デイス プレイに加えて、各種発光光源、照明装置として、家庭用照明、車内照明、また露光 光源のような一種のランプとして、また液晶表示装置のノ ックライト等、表示装置にも 有用に用いられる。  [0411] As described above, the light-emitting organic EL element of the present invention that emits white light can be used for various lighting sources and lighting devices such as home lighting, interior lighting, and exposure light sources in addition to the display device and the display. It is also useful as a kind of lamp and for display devices such as knock lights for liquid crystal display devices.
[0412] その他、時計等のバックライト、看板広告、信号機、光記憶媒体等の光源、電子写 真複写機の光源、光通信処理機の光源、光センサの光源等、さらには表示装置を必 要とする一般の家庭用電気器具等広い範囲の用途が挙げられる。  [0412] Other backlights such as watches, signboard advertisements, traffic lights, optical storage media, light sources for electronic photocopiers, light sources for optical communication processors, light sources for optical sensors, and display devices are also required. There are a wide range of uses such as general household appliances.
実施例  Example
[0413] 実施例 1 [0413] Example 1
《有機 EL素子 1—1の作製》  << Production of organic EL element 1-1 >>
陽極としてガラス上に ITOを 150nm成膜した基板 (NHテクノグラス社製: NA— 45 )にパターユングを行った後、この ITO透明電極を設けた透明支持基板を iso—プロ ピルアルコールで超音波洗净し、乾燥窒素ガスで乾燥し、 UVオゾン洗浄を 5分間行 つた o [0414] この透明支持基板を、市販の真空蒸着装置の基板ホルダーに固定し、一方、 5つ のタンタル製抵抗力卩熱ボートに、 a—NPD、 CBP、 Ir 12、 BCP、 Alqをそれぞれ After patterning on a substrate (NH Techno Glass: NA-45) with a 150 nm ITO film on glass as the anode, the transparent support substrate with this ITO transparent electrode was ultrasonicated with iso-propyl alcohol. Washed, dried with dry nitrogen gas and UV ozone cleaned for 5 minutes o [0414] This transparent support substrate is fixed to the substrate holder of a commercially available vacuum evaporation system, while a-NPD, CBP, Ir12, BCP, and Alq are placed on each of the five tantalum resistance-fired thermal boats.
3 入れて、真空蒸着装置 (第 1真空槽)に取付けた。  3 was installed and attached to the vacuum evaporation system (first vacuum chamber).
[0415] [化 125] [0415] [Chemical 125]
CBP  CBP
[0416] さらに、タンタル製抵抗加熱ボートにフッ化リチウムを、タングステン製抵抗加熱ボ ートにアルミニウムをそれぞれ入れ、真空蒸着装置の第 2真空槽に取り付けた。 [0416] Further, lithium fluoride was put in a resistance heating boat made of tantalum, and aluminum was put in a resistance heating boat made of tungsten, respectively, and attached to the second vacuum chamber of the vacuum evaporation apparatus.
[0417] まず、第 1の真空槽を 4 X 10—4Paまで減圧した後、 a—NPDの入った前記加熱ボ ートに通電して加熱し、蒸着速度 0. 1〜0. 2nmZ秒で透明支持基板に膜厚 25nm の厚さになるように蒸着し、正孔注入 Z輸送層を設けた。 [0417] First, after the vacuum of the first vacuum chamber to 4 X 10- 4 Pa, and heated by supplying an electric current to the baud preparative containing the a-NPD, deposition rate 0. 1~0. 2nmZ seconds Then, vapor deposition was performed on the transparent support substrate to a thickness of 25 nm, and a hole injection Z transport layer was provided.
[0418] さらに、 CBPの入った前記加熱ボートと Ir 12の入ったボートをそれぞれ独立に通 電して発光ホストである CBPと発光ドーパントである Ir— 12の蒸着速度が 100: 7にな るように調節し膜厚 30nmの厚さになるように蒸着し、発光層を設けた。  [0418] Furthermore, the heating boat containing CBP and the boat containing Ir 12 are independently energized, so that the deposition rate of CBP as the luminescent host and Ir-12 as the luminescent dopant becomes 100: 7. The light-emitting layer was provided by vapor-depositing to a thickness of 30 nm.
[0419] ついで、 BCPの入った前記加熱ボートに通電して加熱し、蒸着速度 0. 1〜0. 2n mZ秒で厚さ 10nmの正孔阻止層を設けた。さらに、 Alqの入った前記加熱ボートを [0419] Next, the heating boat containing BCP was energized and heated, and the deposition rate was 0.1 to 0.2n. A hole blocking layer having a thickness of 10 nm was formed in mZ seconds. Furthermore, the heated boat containing Alq
3  Three
通電して加熱し、蒸着速度 0. 1〜0. 2nmZ秒で膜厚 40nmの電子輸送層を設けた  Heated by energization, and provided an electron transport layer with a film thickness of 40 nm at a deposition rate of 0.1 to 0.2 nmZ seconds.
[0420] 次に、前記の如く電子輸送層まで製膜した素子を真空のまま第 2真空槽に移した 後、電子輸送層の上にステンレス鋼製の長方形穴あきマスクが配置されるように装置 外部からリモートコントロールして設置した。 [0420] Next, after the element formed up to the electron transport layer as described above is transferred to the second vacuum chamber while being vacuumed, a rectangular perforated mask made of stainless steel is placed on the electron transport layer. Equipment Remotely installed from outside.
[0421] 第 2真空槽を 2 X 10—4Paまで減圧した後、フッ化リチウム入りのボートに通電して蒸 着速度 0. 01-0. 02nmZ秒で膜厚 0. 5nmの陰極バッファ一層を設け、次いでァ ルミ-ゥムの入つたボートに通電して蒸着速度 1〜 2nmZ秒で膜厚 150nmの陰極を つけ、有機 EL素子 1—1を作製した。 [0421] After decompression of the second vacuum chamber up to 2 X 10- 4 Pa, evaporation Chakusokudo 0. 01-0. 02nmZ sec more cathode buffer layer thickness 0. 5 nm by supplying an electric current to the boat lithium fluoride-containing Then, a boat with an aluminum film was energized, and a cathode with a film thickness of 150 nm was attached at a deposition rate of 1 to 2 nm Z seconds to produce an organic EL device 1-1.
[0422] 《有機 EL素子 1 2〜1 20の作製》 [0422] << Production of organic EL elements 1 2 to 1 20 >>
上記の有機 EL素子 1 1の作製において、表 1に記載のように発光ドーパント、発 光ホスト、正孔阻止材料を変更した以外は同様にして、有機 EL素子 1— 2〜1— 20 を作製した。  In the production of the organic EL device 11 described above, organic EL devices 1-2 to 1-20 were produced in the same manner except that the light emitting dopant, light emitting host, and hole blocking material were changed as shown in Table 1. did.
[0423] 得られた有機 EL素子 1 1〜1 20につ 、て下記のような評価を行った。  [0423] The obtained organic EL devices 11 to 120 were evaluated as follows.
[0424] 《外部取り出し量子効率》  [0424] 《External quantum efficiency》
有機 EL素子 1 1〜1 20を室温(約 23〜25°C)、 2. 5mAZcm2の定電流条件 下による点灯を行い、点灯開始直後の発光輝度 (L) [cdZm2]を測定することにより 、外部取り出し量子効率( r? )を算出した。ここで、発光輝度の測定は、 CS— 1000 ( ミノルタ製)を用いた。 The organic EL element 1 1 to 1 20 room temperature (about 23~25 ° C), 2. performs lighting by under constant current conditions 5mAZcm 2, measuring the lighting start immediately after the emission luminance (L) [cdZm 2] Thus, the external extraction quantum efficiency (r?) Was calculated. Here, CS-1000 (manufactured by Minolta) was used for measurement of light emission luminance.
[0425] また、外部取り出し量子効率は、有機 EL素子 1 1を 100とした時の相対値で表し た。  [0425] Further, the external extraction quantum efficiency was expressed as a relative value when the organic EL element 11 was 100.
[0426] 《発光寿命》  [0426] <Luminescence lifetime>
有機 EL素子 1—1〜 1— 20を室温下、 2. 5mAZcm2の定電流条件下による連続 点灯を行い、初期輝度の半分の輝度になるのに要する時間( τ Ζ )を測定した。ま The organic EL elements 1-1 to 1-20 were continuously lit under a constant current condition of 2.5 mAZcm 2 at room temperature, and the time (τΖ) required to reach half the initial luminance was measured. Ma
1 2  1 2
た、発光寿命は、有機 EL素子 1—1を 100とした時の相対値で表した。  The emission lifetime is expressed as a relative value when the organic EL element 1-1 is set to 100.
[0427] 得られた結果を表 1に示す。 [0427] The results obtained are shown in Table 1.
[0428] [表 1] 有機 EL素子 正孔阻止外部取り出し [0428] [Table 1] Organic EL element Hole blocking external extraction
発光ホスト発光ドーパント 備 考 Mo. 材料 量子効率 ( τ Emission host emission dopant Remarks Mo. Material Quantum efficiency (τ
1 - 1 C B P lr-12 B C P 100 簡 比較例  1-1 C B P lr-12 B C P 100
1一 2 C B P lr-11 B C P 102 103 比較例  1 1 2 C B P lr-11 B C P 102 103 Comparative example
1 -3 C B P 2 BC P 126 198 本発明  1 -3 C B P 2 BC P 126 198 The present invention
1 ― 4 C B P 3 BC P 124 205 本発明  1 ― 4 C B P 3 BC P 124 205 The present invention
1一 5 C B P 14 B C P 125 193 本発明  1 1 5 C B P 14 B C P 125 193 The present invention
1一 6 C B P 30 B C P 123 195 本発明  1 1 6 C B P 30 B C P 123 195 The present invention
1一 7 C P 47 B C P 124 203 本発明  1 1 7 C P 47 B C P 124 203 The present invention
1 ― 8 C B P 50 B C P 125 198 本発明  1 ― 8 C B P 50 B C P 125 198 The present invention
1一 9 A C Z 1 43 B C P 133 217 本発明  1 1 9 A C Z 1 43 B C P 133 217 The present invention
1一 10 A C Z 1 44 B C P 136 221 本発明  1 1 10 A C Z 1 44 B C P 136 221 The present invention
1 —11 A C Z 2 49 B C P 134 232 本発明  1 -11 A C Z 2 49 B C P 134 232
1 -12 A C Z 2 53 BC P 135 235 本発明  1 -12 A C Z 2 53 BC P 135 235 The present invention
1 一 C B P 57 A C Z 1 142 246 本発明  1 1 C B P 57 A C Z 1 142 246
1 -14 C B P 63 A C Z 2 141 248 本発明  1 -14 C B P 63 A C Z 2 141 248
1 -15 C B P 87 B C P 120 191 本発明  1 -15 C B P 87 B C P 120 191 The present invention
1 -16 C B P 89 B C P 121 185 本発明  1 -16 C B P 89 B C P 121 185 The present invention
1 一】 7 A C Z 1 103 B C P !31 209 本発明  1 1] 7 A C Z 1 103 B C P! 31 209 The present invention
1一 18 A C Z 2 116 B C P 133 210 本発明  1 1 18 A C Z 2 116 B C P 133 210 The present invention
1一 19 C B P 118 A C Z 1 HO 234 本発明  1 1 19 C B P 118 A C Z 1 HO 234 The present invention
1一 20 C B P 120 A C Z 2 141 231 本発明 化 126]  1 1 20 C B P 120 A C Z 2 141 231 Invention 126]
ACZ1 ACZ1
表 1から、本発明に係る金属錯体を用いて作製した有機 EL素子は、比較の有機 E L素子に比べ、高い発光効率と発光寿命の長寿命化が達成できることが明らかであ る。 From Table 1, it is clear that the organic EL device fabricated using the metal complex according to the present invention can achieve higher luminous efficiency and longer lifetime compared to the comparative organic EL device. The
[0431] カルボリン誘導体または該カルボリン誘導体のカルボリン環を構成する炭化水素環 の炭素原子の少なくとも一つがさらに窒素原子で置換されている環構造を有する誘 導体を発光層に併用することにより、また、カルボリン誘導体または該カルボリン誘導 体のカルボリン環を構成する炭化水素環の炭素原子の少なくとも一つがさらに窒素 原子で置換されている環構造を有する誘導体を正孔阻止層に使用することにより、さ らに本発明に記載の効果の向上が見られた。  [0431] A carboline derivative or a derivative having a ring structure in which at least one carbon atom of a hydrocarbon ring constituting the carboline ring of the carboline derivative is further substituted with a nitrogen atom is used in combination with the light-emitting layer, By further using a carboline derivative or a derivative having a ring structure in which at least one of the carbon atoms of the hydrocarbon ring constituting the carboline ring of the carboline derivative is further substituted with a nitrogen atom in the hole blocking layer, The improvement of the effect described in the present invention was observed.
[0432] 実施例 2 [0432] Example 2
《フルカラー表示装置の作製》  <Production of full-color display device>
(青色発光素子の作製)  (Production of blue light-emitting elements)
実施例 1の有機 EL素子 1 6を青色発光素子として用 、た。  The organic EL element 16 of Example 1 was used as a blue light emitting element.
[0433] (緑色発光素子の作製) [0433] (Production of green light-emitting element)
実施例 1の有機 EL素子 1— 6において、 Ir— 1を緑色発光ドーパントとして用 、緑 色発光素子とした。  In the organic EL device 1-6 of Example 1, Ir-1 was used as a green light emitting dopant to obtain a green light emitting device.
[0434] (赤色発光素子の作製) [0434] (Production of red light-emitting element)
実施例 1の有機 EL素子 1 6にお 、て、 Ir 9を赤色発光ドーパントとして用い赤 色発光素子とした。  In the organic EL element 16 of Example 1, Ir 9 was used as a red light emitting dopant to obtain a red light emitting element.
[0435] 上記で作製した、各々赤色、緑色、青色発光有機 EL素子を同一基板上に並置し、 図 1に記載のような形態を有するアクティブマトリクス方式フルカラー表示装置を作製 し、図 2には、作製した前記表示装置の表示部 Aの模式図のみを示した。即ち、同一 基板上に、複数の走査線 5及びデータ線 6を含む配線部と、並置した複数の画素 3 ( 発光の色が赤領域の画素、緑領域の画素、青領域の画素等)とを有し、配線部の走 查線 5及び複数のデータ線 6はそれぞれ導電材料からなり、走査線 5とデータ線 6は 格子状に直交して、直交する位置で画素 3に接続している(詳細は図示せず)。前記 複数画素 3は、それぞれの発光色に対応した有機 EL素子、アクティブ素子であるス イッチングトランジスタと駆動トランジスタそれぞれが設けられたアクティブマトリクス方 式で駆動されており、走査線 5から走査信号が印加されると、データ線 6から画像デ ータ信号を受け取り、受け取った画像データに応じて発光する。この様に各赤、緑、 青の画素を適宜、並置することによって、フルカラー表示装置を作製した。 [0435] The red, green, and blue light-emitting organic EL elements produced above were juxtaposed on the same substrate to produce an active matrix type full-color display device having the configuration shown in FIG. 1, and FIG. Only the schematic view of the display part A of the produced display device is shown. That is, on the same substrate, a wiring portion including a plurality of scanning lines 5 and data lines 6 and a plurality of juxtaposed pixels 3 (emission color is a red region pixel, a green region pixel, a blue region pixel, etc.) The scanning line 5 and the plurality of data lines 6 in the wiring portion are each made of a conductive material, and the scanning lines 5 and the data lines 6 are orthogonal to each other in a grid pattern and are connected to the pixels 3 at the orthogonal positions. (Details not shown). The plurality of pixels 3 are driven by an active matrix system provided with an organic EL element corresponding to each emission color, a switching transistor as an active element, and a driving transistor, and a scanning signal is applied from a scanning line 5. Then, an image data signal is received from the data line 6 and light is emitted according to the received image data. In this way, each red, green, A full color display device was produced by juxtaposing the blue pixels appropriately.
[0436] 該フルカラー表示装置を駆動することにより、輝度が高ぐ高耐久性を有し、かつ、 鮮明なフルカラー動画表示が得られることが分力つた。  [0436] By driving the full-color display device, it was possible to obtain a clear and full-color moving image display having high luminance and high durability.
[0437] 実施例 3 [0437] Example 3
《フルカラー表示装置の作製》  <Production of full-color display device>
実施例 2の青色発光素子の作製にぉ 、て、有機 EL素子 1 6を有機 EL素子 1 8 に変更した以外は実施例 2と同様にしてフルカラー表示装置を作製した。  A full-color display device was produced in the same manner as in Example 2 except that the organic EL element 16 was changed to the organic EL element 18 before producing the blue light emitting element of Example 2.
[0438] 該フルカラー表示装置を駆動することにより、輝度が高ぐ高耐久性を有し、かつ、 鮮明なフルカラー動画表示が得られることが分力つた。 [0438] By driving the full-color display device, it was possible to obtain a clear full-color moving image display having high luminance and high durability.
[0439] 実施例 4 [0439] Example 4
《フルカラー表示装置の作製》  <Production of full-color display device>
実施例 2の青色発光素子の作製にぉ 、て、有機 EL素子 1 6を有機 EL素子 1 1 3に変更した以外は実施例 2と同様にしてフルカラー表示装置を作製した。  A full-color display device was produced in the same manner as in Example 2 except that the organic EL element 16 was changed to the organic EL element 11 13 for producing the blue light-emitting element of Example 2.
[0440] 該フルカラー表示装置を駆動することにより、輝度が高ぐ高耐久性を有し、かつ、 鮮明なフルカラー動画表示が得られることが分力つた。 [0440] It was found that by driving the full-color display device, a bright full-color moving image display having high luminance and high durability can be obtained.
[0441] 実施例 5 [0441] Example 5
《フルカラー表示装置の作製》  <Production of full-color display device>
実施例 2の青色発光素子の作製にぉ 、て、有機 EL素子 1 6を有機 EL素子 1 1 4に変更した以外は実施例 2と同様にしてフルカラー表示装置を作製した。  A full-color display device was produced in the same manner as in Example 2 except that the organic EL element 16 was changed to the organic EL element 114 in producing the blue light-emitting element in Example 2.
[0442] 該フルカラー表示装置を駆動することにより、輝度が高ぐ高耐久性を有し、かつ、 鮮明なフルカラー動画表示が得られることが分力つた。 [0442] By driving the full-color display device, it was possible to obtain a clear and full-color moving image display having high luminance and high durability.
[0443] 実施例 6 [0443] Example 6
《白色発光素子及び白色照明装置の作製》  << Preparation of white light emitting element and white lighting device >>
実施例 1の透明電極基板の電極を 20mm X 20mmにパターユングし、その上に実 施例 1と同様に正孔注入/輸送層として α— NPDを 25nmの厚さで製膜し、さらに、 CBPの入った前記加熱ボートと本発明の化合物 44の入ったボート及び Ir 9の入つ たボートをそれぞれ独立に通電して発光ホストである CBPと発光ドーパントである本 発明の化合物 44及び Ir— 9の蒸着速度が 100 : 5 : 0. 6になるように調節し膜厚 30η mの厚さになるように蒸着し、発光層を設けた。 The electrode of the transparent electrode substrate of Example 1 was patterned to 20 mm × 20 mm, and α-NPD was deposited to a thickness of 25 nm as a hole injection / transport layer in the same manner as in Example 1, The heated boat containing CBP, the boat containing Compound 44 of the present invention, and the boat containing Ir 9 were energized independently to provide CBP as a luminescent host and Compound 44 of the present invention and Ir— The deposition rate of 9 is adjusted to 100: 5: 0.6, and the film thickness is 30η Evaporation was performed to a thickness of m, and a light emitting layer was provided.
[0444] っ 、で、 BCPを lOnm製膜して正孔阻止層を設けた。さらに、 Alqを 40nmで製膜 [0444] Thus, a hole blocking layer was formed by forming BCP into lOnm. Furthermore, Alq is deposited at 40nm
3  Three
し電子輸送層を設けた。  An electron transport layer was provided.
[0445] 次に、実施例 1と同様に、電子注入層の上にステンレス鋼製の透明電極とほぼ同じ 形状の正方形穴あきマスクを設置し、陰極バッファ一層としてフッ化リチウム 0. 5nm 及び陰極としてアルミニウム 150nmを蒸着製膜した。  [0445] Next, as in Example 1, a square perforated mask having substantially the same shape as the transparent electrode made of stainless steel was placed on the electron injection layer, and lithium fluoride 0.5 nm and the cathode were used as a cathode buffer layer. As a film, 150 nm of aluminum was deposited.
[0446] この有機 EL素子の非発光面をガラスケースで覆 、、照明装置とした。照明装置は 、発光効率が高く発光寿命の長い白色光を発する薄型の照明装置として使用するこ とができた。図 5は照明装置の概略図で、図 6は照明装置の断面図である。有機 EL 素子 101をガラスカバー 102で覆った。 105は陰極で 106は有機 EL層、 107は透明 電極付きガラス基板である。なおガラスカバー 102内には窒素ガス 108が充填され、 捕水剤 109が設けられている。  [0446] The non-light-emitting surface of the organic EL element was covered with a glass case to obtain a lighting device. The illuminating device could be used as a thin illuminating device that emits white light with high luminous efficiency and long emission life. FIG. 5 is a schematic view of the lighting device, and FIG. 6 is a cross-sectional view of the lighting device. The organic EL element 101 was covered with a glass cover 102. 105 is a cathode, 106 is an organic EL layer, and 107 is a glass substrate with a transparent electrode. The glass cover 102 is filled with nitrogen gas 108 and a water catching agent 109 is provided.
[0447] 実施例 7  [0447] Example 7
《白色発光素子及び白色照明装置の作製》  << Preparation of white light emitting element and white lighting device >>
実施例 6の白色発光素子の作製において、本発明の化合物 44を 47に変更した以 外は実施例 6と同様にして白色照明装置を作製した。  A white illumination device was produced in the same manner as in Example 6 except that the compound 44 of the present invention was changed to 47 in the production of the white light emitting device of Example 6.
[0448] この照明装置に通電したところほぼ白色の光が得られ、照明装置として使用できる ことが分力つた。 [0448] When this lighting device was energized, almost white light was obtained, and it was possible to use it as a lighting device.
[0449] 実施例 8 [0449] Example 8
《白色発光素子及び白色照明装置の作製》  << Preparation of white light emitting element and white lighting device >>
実施例 6の白色発光素子の作製において、本発明の化合物 44を 49に変更した以 外は実施例 6と同様にして白色照明装置を作製した。  A white illumination device was produced in the same manner as in Example 6 except that Compound 44 of the present invention was changed to 49 in the production of the white light emitting device of Example 6.
[0450] この照明装置に通電したところほぼ白色の光が得られ、照明装置として使用できる ことが分力つた。 [0450] When this lighting device was energized, almost white light was obtained, and it was possible to use it as a lighting device.
[0451] 実施例 9 [0451] Example 9
《塗布法による白色発光素子及び白色照明装置の作製》  << Preparation of white light emitting element and white illumination device by coating method >>
25mm X 25mm X O. 5mmのガラス支持基板上に直流電源を用い、スパッタ法に てインジウム錫酸ィ匕物(ITO、インジウム Ζ錫 = 95Ζ5モル比)の陽極を形成した (厚 み 200nm)。この陽極の表面抵抗は 10 Ω ロであった。これにポリビュルカルバゾ ール (正孔輸送性バインダーポリマー) /本発明の化合物 44 (青発光性オルトメタル 化錯体) Ζトリス(2—フエ-ルビリジン)イリジウム錯体 (緑発光性オルトメタル化錯体: Ir- 1) Zビス(2—ベンゾチォフェン [b]— 2—ィルーピリジン)ァセチルァセトナート イリジウム錯体 (赤発光性オルトメタルイ匕錯体: Ir— 9) /2— (4 ビフエ-リル) 5— (4 t ブチルフエ-ル) 1, 3, 4ーォキサジァゾール(電子輸送材) =200Z2Z 5/2/50 (質量比)を溶解したジクロロエタン溶液をスピンコ一タ一で塗布し、 100η mの発光層を得た。この有機化合物層の上にパタ ユングしたマスク (発光面積が 5 mm X 5mmとなるマスク)を設置し、蒸着装置内で陰極バッファ一層としてフッ化リチ ゥム 0. 5nm及び陰極としてアルミニウム 150nmを蒸着して陰極を設けた。陽極、陰 極よりそれぞれアルミニウムのリード線を出して発光素子を作製した。該素子を窒素 ガスで置換したグロ ブボックス内に入れ、ガラス製の封止容器で紫外線硬化型接 着剤 (長瀬チバ製、 XNR5493)を用いて封止して照明装置を作製した。 25mm X 25mm X O. Using a direct current power source on a 5mm glass support substrate, an anode of indium stannate (ITO, indium Ζ tin = 95 Ζ 5 mole ratio) was formed by sputtering (thickness) Only 200nm). The surface resistance of this anode was 10 Ω. Polyburcarbazole (Hole-transporting binder polymer) / Compound of the present invention 44 (Blue light-emitting orthometalated complex) ス Tris (2-phenylpyridine) iridium complex (Green light-emitting orthometalated complex) : Ir-1) Z bis (2-benzothiophene [b] — 2-ylupyridine) acetylylatetonate iridium complex (red luminescent ortho-metal complex: Ir— 9) / 2— (4 biphenyl) 5— ( 4 t-butyl-fell) 1, 3, 4-oxadiazole (electron transport material) = 200Z2Z 5/2/50 (mass ratio) dissolved dichloroethane solution was applied with a spin coater, 100ηm A light emitting layer was obtained. A patterned mask (a mask with a light emitting area of 5 mm x 5 mm) is placed on this organic compound layer, and 0.5 nm of lithium fluoride is deposited as a cathode buffer layer and 150 nm of aluminum is deposited as a cathode in a deposition apparatus. Then, a cathode was provided. A light emitting element was produced by providing aluminum lead wires from the anode and the cathode, respectively. The device was placed in a glove box substituted with nitrogen gas, and sealed with a glass sealing container using an ultraviolet curable adhesive (XNR5493, manufactured by CHI Nagase) to produce a lighting device.
[0452] この照明装置に通電したところほぼ白色の光が得られ、照明装置として使用できる ことが分力つた。  [0452] When this lighting device was energized, almost white light was obtained, and it was possible to use it as a lighting device.
[0453] 実施例 10  [0453] Example 10
《塗布法による白色発光素子及び白色照明装置の作製》  << Preparation of white light emitting element and white illumination device by coating method >>
実施例 9の白色発光素子の作製において、本発明の化合物 44を 53に変更した以 外は実施例 9と同様にして白色照明装置を作製した。  A white lighting device was produced in the same manner as in Example 9 except that the compound 44 of the present invention was changed to 53 in the production of the white light emitting device of Example 9.
[0454] この照明装置に通電したところほぼ白色の光が得られ、照明装置として使用できる ことが分力つた。 [0454] When this lighting device was energized, almost white light was obtained, and it was possible to use it as a lighting device.
[0455] 実施例 11 [0455] Example 11
《塗布法による白色発光素子及び白色照明装置の作製》  << Preparation of white light emitting element and white illumination device by coating method >>
実施例 9の白色発光素子の作製において、本発明の化合物 44を 118に変更した 以外は実施例 9と同様にして白色照明装置を作製した。  A white lighting device was produced in the same manner as in Example 9 except that Compound 44 of the present invention was changed to 118 in the production of the white light-emitting device of Example 9.
[0456] この照明装置に通電したところほぼ白色の光が得られ、照明装置として使用できる ことが分力つた。 [0456] When this lighting device was energized, almost white light was obtained, and it was possible to use it as a lighting device.
[0457] 実施例 12 《塗布法による白色発光素子及び白色照明装置の作製》 [0457] Example 12 << Preparation of white light emitting element and white illumination device by coating method >>
25mm X 25mm X O. 5mmのガラス支持基板上に直流電源を用い、スパッタ法に てインジウム錫酸ィ匕物(ITO、インジウム Ζ錫 = 95Ζ5モル比)の陽極を形成した (厚 み 200nm)。この陽極の表面抵抗は 10 Ω ロであった。これにポリビュルカルバゾ ール (正孔輸送性バインダーポリマー) ZACZ1 (正孔輸送制御材) Z本発明の化合 物 57 (青発光性オルトメタルィ匕錯体) Zトリス(2 フエ-ルビリジン)イリジウム錯体 ( 緑発光性オルトメタル化錯体: Ir 1 ) Zビス ( 2 ベンゾチォフェン [b]— 2—ィルー ピリジン)ァセチルァセトナ トイリジウム錯体 (赤発光性オルトメタルイ匕錯体: Ir— 9) 72—(4ービフェ-リル)ー5—(4 1;ーブチルフェ-ル)ー1, 3, 4 ォキサジァゾ ル (電子輸送材) = 150/50/2/5/2/50 (質量比)を溶解したジクロロエタン溶 液をスピンコ―タ—で塗布し、 lOOnmの発光層を得た。この有機化合物層の上にパ タ ユングしたマスク (発光面積が 5mm X 5mmとなるマスク)を設置し、蒸着装置内 で陰極バッファ一層としてフッ化リチウム 0. 5nm及び陰極としてアルミニウム 150nm を蒸着して陰極を設けた。陽極、陰極よりそれぞれアルミニウムのリード線を出して発 光素子を作成した。該素子を窒素ガスで置換したグローブボックス内に入れ、ガラス 製の封止容器で紫外線硬化型接着剤 (長瀬チバ製、 XNR5493)を用いて封止して 照明装置を作製した。  An anode of indium stannate (ITO, indium Ζ tin = 95 Ζ 5 mole ratio) was formed on a glass support substrate of 25 mm X 25 mm X O. 5 mm using a DC power source by sputtering (thickness 200 nm). The surface resistance of this anode was 10 Ω. Polyburcarbazole (Hole transporting binder polymer) ZACZ1 (Hole transport control material) Z Compound of the present invention 57 (Blue light emitting ortho-metal complex) Z Tris (2 ferro-lysine) iridium complex ( Green luminescent ortho-metalated complex: Ir 1) Z bis (2 benzothiophene [b] — 2-yl pyridine) acetylacetona toridium complex (red luminescent ortho-metalated complex: Ir— 9) 72— (4-bipheryl) 5— (4 1; -Butyl ferrule) -1, 3, 4 oxadiazole (electron transport material) = 150/50/2/5/2/50 (mass ratio) dissolved in dichloroethane solution as spin coater Was applied to obtain a light emitting layer of lOOnm. A patterned mask (a mask with an emission area of 5 mm x 5 mm) is placed on the organic compound layer, and 0.5 nm of lithium fluoride is deposited as a cathode buffer layer and 150 nm of aluminum is deposited as a cathode in a deposition apparatus. A cathode was provided. Light emitting elements were prepared by emitting aluminum lead wires from the anode and cathode, respectively. The device was placed in a glove box substituted with nitrogen gas, and sealed with a glass sealing container using an ultraviolet curable adhesive (XNR5493, manufactured by CHI Nagase) to produce a lighting device.
[0458] この照明装置に通電したところほぼ白色の光が得られ、照明装置として使用できる ことが分力つた。  [0458] When this illuminator was energized, almost white light was obtained, and it was possible to use it as an illuminator.
[0459] 実施例 13 [0459] Example 13
《白色発光素子及び白色照明装置の作製》  << Preparation of white light emitting element and white lighting device >>
実施例 12の白色発光素子の作製において、本発明の化合物 57を 61に変更した 以外は実施例 12と同様にして白色照明装置を作製した。  A white lighting device was produced in the same manner as in Example 12 except that Compound 57 of the present invention was changed to 61 in the production of the white light emitting device of Example 12.
[0460] この照明装置に通電したところほぼ白色の光が得られ、照明装置として使用できる ことが分力つた。 [0460] When this lighting device was energized, almost white light was obtained, and it was possible to use it as a lighting device.
[0461] 実施例 14 [0461] Example 14
《白色発光素子及び白色照明装置の作製》  << Preparation of white light emitting element and white lighting device >>
実施例 12の白色発光素子の作製において、正孔輸送制御材 ACZ1を ACZ2に変 更した以外は実施例 12と同様にして白色照明装置を作製した。 In the manufacture of the white light emitting device of Example 12, the hole transport control material ACZ1 was changed to ACZ2. A white lighting device was produced in the same manner as in Example 12 except for the above.
[0462] この照明装置に通電したところほぼ白色の光が得られ、照明装置として使用できる ことが分力つた。 [0462] When this lighting device was energized, almost white light was obtained, and it was possible to use it as a lighting device.
[0463] 実施例 15 [0463] Example 15
《有機 EL素子 2— 1〜2— 13の作製》  << Preparation of organic EL elements 2-1 to 2-13 >>
実施例 1の有機 EL素子 1—1において、発光ドーパントを Ir 1に変更し、正孔阻 止材料を表 2に記載のように、変更した以外は同様にして、実施例 1と同様にして有 機 EL素子 2—;!〜 2— 13を作製した。  In the same manner as in Example 1 except that the emission dopant was changed to Ir 1 and the hole blocking material was changed as shown in Table 2 in the organic EL device 1-1 of Example 1. Organic EL device 2 — ;! ~ 2-13 were produced.
[0464] 得られた各々の素子の外部取り出し量子効率、発光寿命の測定を実施例 1に記載 の方法と同様にして行った。 [0464] The external extraction quantum efficiency and the light emission lifetime of each of the obtained devices were measured in the same manner as described in Example 1.
[0465] この時、いずれも有機 EL素子 2—1の値を 100として、各有機 EL素子試料の値を 相対値で表した。得られた結果を表 2に示す。 [0465] At this time, the value of the organic EL element 2-1 was set to 100, and the value of each organic EL element sample was expressed as a relative value. Table 2 shows the results obtained.
[0466] [表 2] [0466] [Table 2]
表 2から、本発明の有機 EL素子材料を正孔阻止材料に用いた有機 EL素子は比 較の有機 EL素子に比べ、高い発光効率と発光寿命が得られることが分かった。なお 、本発明の有機 EL素子の発光色は全て緑色だった。 From Table 2, it was found that the organic EL device using the organic EL device material of the present invention as the hole blocking material can obtain higher luminous efficiency and longer lifetime than the comparative organic EL device. The emission color of the organic EL device of the present invention was all green.

Claims

請求の範囲 下記一般式(1)で表されるオルトメタル錯体であることを特徴とする有機エレクト口 ルミネッセンス素子材料。 An organic electoluminescence element material characterized by being an ortho metal complex represented by the following general formula (1).
[化 1] 一般式 (1 )  [Chemical formula 1] General formula (1)
(式中、 Mは元素周期表における第 8〜10族の金属元素を表す。 L、 V は互いに 異なる二座配位子を表し、 mは 1または 2であり、 nは 1または 2である。ただし、 m+n は 2または 3であり Mの電荷と一致する。 (In the formula, M represents a metal element belonging to Groups 8 to 10 in the periodic table. L and V represent different bidentate ligands, m is 1 or 2, and n is 1 or 2. However, m + n is 2 or 3, which matches the charge of M.
二座配位子 L、 U が金属 Mに配位した部分構造 MLは下記一般式 (2)で表され、 部分構造 ML' は下記一般式(3)または (4)で表される。  The partial structure ML in which the bidentate ligands L and U are coordinated to the metal M is represented by the following general formula (2), and the partial structure ML ′ is represented by the following general formula (3) or (4).
[化 2] [Chemical 2]
-般式 (2) -般式 (31 一般式 (4) -General formula (2) -General formula (31 General formula (4)
X X
11は炭素原子または窒素原子を表し、 Q に 6  11 represents a carbon atom or a nitrogen atom, and Q is 6
11は炭素原子及び X  11 is carbon atom and X
11と共 員の芳香族 炭化水素環または 5〜6員の芳香族複素環である環 Aを形成する原子群を表す。 X  11 represents a group of atoms forming ring A which is an aromatic hydrocarbon ring or a 5- to 6-membered aromatic heterocyclic ring. X
12 は炭素原子または窒素原子を表し、 Q  12 represents a carbon atom or a nitrogen atom, and Q
12は窒素原子及び X  12 is nitrogen atom and X
12と共に 5〜6員の芳香族 複素環である環 Bを形成する原子群を表す。 Xは 0、 S、 CH、 CHR、 CR、 NR、 P  A group of atoms that together with 12 forms ring B, which is a 5- to 6-membered aromatic heterocycle. X is 0, S, CH, CHR, CR, NR, P
1 2 2  1 2 2
R、 SiR、 C = 0、 C=NR、 SOまたは SOを表す。 Rはアルキル基、シクロアルキル  R, SiR, C = 0, C = NR, SO or SO. R is an alkyl group, cycloalkyl
2 2  twenty two
基、アルケニル基、ァリール基、複素環基または芳香族複素環基を表す。 Represents a group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group.
X は炭素原子または窒素原子を表し、 Q は炭素原子及び X と共に 6員の芳香族 X represents a carbon atom or a nitrogen atom, Q represents a 6-membered aromatic together with the carbon atom and X
21 21 21 21 21 21
炭化水素環または 5〜6員の芳香族複素環である環 Cを形成する原子群を表す。 X A group of atoms forming a ring C which is a hydrocarbon ring or a 5- to 6-membered aromatic heterocycle. X
22 は炭素原子または窒素原子を表し、 Q twenty two Represents a carbon atom or a nitrogen atom, and Q
22は窒素原子及び X  22 is nitrogen atom and X
22と共に 5〜6員の芳香族 複素環である環 Dを形成する原子群を表す。 Xは 0、 S、 CH、 CHR、 CR、 NR、 P  This represents a group of atoms that together with 22 forms ring D, which is a 5- to 6-membered aromatic heterocyclic ring. X is 0, S, CH, CHR, CR, NR, P
2 2 2  2 2 2
R、 SiR、 C = 0、 C=NR、 SOまたは SOを表す。 Rはアルキル基、シクロアルキル R, SiR, C = 0, C = NR, SO or SO. R is an alkyl group, cycloalkyl
2 2 twenty two
基、アルケニル基、ァリール基、複素環基または芳香族複素環基を表す。 Represents a group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group.
X 、X は窒素原子またはリン原子を表し、 Xは X 、X を介して Mに配位している X and X represent a nitrogen atom or a phosphorus atom, and X is coordinated to M through X and X
31 32 3 31 32 31 32 3 31 32
二座配位子を形成する原子群を表す。 ) A group of atoms forming a bidentate ligand is represented. )
下記一般式 (5)で表されるオルトメタル錯体であることを特徴とする請求の範囲第 1 項に記載の有機エレクト口ルミネッセンス素子材料。 2. The organic electroluminescent device material according to claim 1, which is an ortho metal complex represented by the following general formula (5).
[化 3] 一般式 ) [Chemical formula 3] General formula)
(式中、 Mは元素周期表における第 8〜10族の金属元素を表す。 mlは 1または 2で あり、 nlは 1または 2である。ただし、 ml +nlは 2または 3であり Mの電荷と一致する 。 X は炭素原子または窒素原子を表し、 Q は炭素原子及び X と共に 6員の芳香族(In the formula, M represents a metal element of Groups 8 to 10 in the periodic table. Ml is 1 or 2, nl is 1 or 2, provided that ml + nl is 2 or 3 and M Corresponds to the charge X represents a carbon or nitrogen atom, Q represents a 6-membered aromatic together with the carbon atom and X
11 11 11 11 11 11
炭化水素環または 5〜6員の芳香族複素環である環 Aを形成する原子群を表す。 X A group of atoms forming a ring A which is a hydrocarbon ring or a 5- to 6-membered aromatic heterocycle. X
12 は炭素原子または窒素原子を表し、 Q  12 represents a carbon atom or a nitrogen atom, and Q
12は窒素原子及び X  12 is nitrogen atom and X
12と共に 5〜6員の芳香族 複素環である環 Bを形成する原子群を表す。 Xは 0、 S、 CH、 CHR、 CR、 NR、 P  A group of atoms that together with 12 forms ring B, which is a 5- to 6-membered aromatic heterocycle. X is 0, S, CH, CHR, CR, NR, P
1 2 2  1 2 2
R、 SiR、 C = 0、 C=NR、 SOまたは SOを表す。 Rはアルキル基、シクロアルキル R, SiR, C = 0, C = NR, SO or SO. R is an alkyl group, cycloalkyl
2 2 twenty two
基、アルケニル基、ァリール基、複素環基または芳香族複素環基を表す。 Represents a group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group.
X  X
21は、炭素原子または窒素原子を表し、 Q  21 represents a carbon atom or a nitrogen atom, Q
21は炭素原子及び X  21 is carbon atom and X
21と共に 6員の芳香 族炭化水素環または 5〜6員の芳香族複素環である環 Cを形成する原子群を表す。 X は炭素原子または窒素原子を表し、 Q 〜6  21 represents an atomic group forming ring C together with 21 which is a 6-membered aromatic hydrocarbon ring or a 5- to 6-membered aromatic heterocyclic ring. X represents a carbon atom or a nitrogen atom, and Q to 6
22 22は窒素原子及び X  22 22 is nitrogen atom and X
22と共に 5 員の芳香 族複素環である環 Dを形成する原子群を表す。 Xは 0、 S、 CH、 CHR、 CR、 NR、 PR、 SiR、 C = 0、 C=NR、 SOまたは SOを表す。 Rはアルキル基、シクロアルキルA group of atoms that together with 22 form ring D, a 5-membered aromatic heterocycle. X is 0, S, CH, CHR, CR, NR, PR, SiR, C = 0, C = NR, SO or SO. R is an alkyl group, cycloalkyl
2 2 twenty two
基、アルケニル基、ァリール基、複素環基または芳香族複素環基を表す。ただし、環 Represents a group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. However, the ring
Aと環 C、環 Bと環 Dが同時に同じものになることはない。 ) A and ring C, and ring B and ring D cannot be the same at the same time. )
下記一般式 (6)で表されるオルトメタル錯体であることを特徴とする請求の範囲第 1 項に記載の有機エレクト口ルミネッセンス素子材料。  2. The organic electroluminescence device material according to claim 1, which is an ortho metal complex represented by the following general formula (6).
[化 4] 一般式 (6)  [Chemical formula 4] General formula (6)
(式中、 Mは元素周期表における第 8〜10族の金属元素を表す。 m2は 1または 2で あり、 n2は 1または 2である。ただし、 m2+n2は 2または 3であり Mの電荷と一致する 。 X は炭素原子または窒素原子を表し、 Q は炭素原子及び X と共に 6員の芳香族(In the formula, M represents a metal element of Group 8 to 10 in the periodic table. M2 is 1 or 2, n2 is 1 or 2, provided that m2 + n2 is 2 or 3, and M2 Corresponds to the charge X represents a carbon or nitrogen atom, Q represents a 6-membered aromatic together with the carbon atom and X
11 11 11 11 11 11
炭化水素環または 5〜6員の芳香族複素環である環 Aを形成する原子群を表す。 X  A group of atoms forming a ring A which is a hydrocarbon ring or a 5- to 6-membered aromatic heterocycle. X
12 は炭素原子または窒素原子を表し、 Q  12 represents a carbon atom or a nitrogen atom, and Q
12は窒素原子及び X  12 is nitrogen atom and X
12と共に 5〜6員の芳香族 複素環である環 Bを形成する原子群を表す。 Xは 0、 S、 CH、 CHR、 CR、 NR、 P  A group of atoms that together with 12 forms ring B, which is a 5- to 6-membered aromatic heterocycle. X is 0, S, CH, CHR, CR, NR, P
1 2 2  1 2 2
R、 SiR、 C = 0、 C=NR、 SOまたは SOを表す。 Rはアルキル基、シクロアルキル R, SiR, C = 0, C = NR, SO or SO. R is an alkyl group, cycloalkyl
2 2 twenty two
基、ァルケ-ル基、ァリール基、複素環基または芳香族複素環基を表す。 X 、 X は  A group, an alkyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group; X and X are
31 32 窒素原子またはリン原子を表し、 X X  31 32 Represents a nitrogen or phosphorus atom, X X
3は X 、  3 is X,
31 32を介して Mに配位している二座配位子 を形成する原子群を表す。 )  31 represents an atomic group forming a bidentate ligand coordinated to M through 32. )
[4] 前記一般式 (6)にお 、て、芳香族複素環 Bが 6員環であることを特徴とする請求の 範囲第 3項に記載の有機エレクト口ルミネッセンス素子材料。 [4] The organic electroluminescent device material according to claim 3, wherein the aromatic heterocyclic ring B is a 6-membered ring in the general formula (6).
[5] 下記一般式 (7)で表される部分構造またはその互変異性体を部分構造として有す るオルトメタル錯体であることを特徴とする請求の範囲第 1〜4項のいずれか 1項に記 載の有機エレクト口ルミネッセンス素子材料。 [化 5] 一般式 (7) [5] The orthometal complex having a partial structure represented by the following general formula (7) or a tautomer thereof as a partial structure: Organic electroluminescent element material described in the paragraph. [Chemical formula 5] General formula (7)
(式中、 Mは元素周期表における第 8〜10族の金属元素を表す。 X は炭素原子ま (In the formula, M represents a metal element of Groups 8 to 10 in the periodic table. X represents a carbon atom.
41  41
たは窒素原子を表し、 Q Or a nitrogen atom, Q
41は炭素原子及び X  41 is carbon atom and X
41と共に 6員の芳香族炭化水素環または 41 with 6-membered aromatic hydrocarbon ring or
5〜6員の芳香族複素環である環 Eを形成する原子群を表す。 R は置換基を表し、 n A group of atoms forming ring E, which is a 5- to 6-membered aromatic heterocycle. R represents a substituent, and n
41  41
4は 0〜3から選ばれる整数を表す。 Xaは— N (Ra)、— O— Raまたは— S— Raを表  4 represents an integer selected from 0 to 3. Xa represents —N (Ra), —O—Ra or —S—Ra
2  2
す。 Raはアルキル基、シクロアルキル基、アルケニル基、ァリール基、複素環基また は芳香族複素環基を表す。 Xaが— N (Ra)の場合、 2つの Raは同じであっても異な The Ra represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. If Xa is — N (Ra), the two Ras are the same but different
2  2
つていてもよい。 Xは 0、 S、 CH、 CHR、 CR、 NR、 PR、 SiR、 C = 0、 C=NR、 S You may go on. X is 0, S, CH, CHR, CR, NR, PR, SiR, C = 0, C = NR, S
4 2 2 2  4 2 2 2
Oまたは SOを表す。 Rはアルキル基、シクロアルキル基、アルケニル基、ァリール基  Represents O or SO. R is an alkyl group, cycloalkyl group, alkenyl group, aryl group
2  2
、複素環基または芳香族複素環基を表す。 )  Represents a heterocyclic group or an aromatic heterocyclic group. )
下記一般式 (8)または (9)で表される部分構造またはその互変異性体を部分構造と して有するオルトメタル錯体であることを特徴とする請求の範囲第 5項に記載の有機 エレクトロノレミネッセンス素子材料。 6. The organic electro according to claim 5, which is an orthometal complex having a partial structure represented by the following general formula (8) or (9) or a tautomer thereof as a partial structure: Nominescence element material.
[化 6] [Chemical 6]
(式中、 Mは元素周期表における第 8〜10族の金属元素を表す。 R 、R 、R 、R (In the formula, M represents a metal element of Groups 8 to 10 in the periodic table. R 1, R 2, R 3, R 4
51 52 53 54 は、各々水素原子または電子供与性の置換基を表し、少なくとも 1つは電子供与性 の置換基である。 R 、R 、R 、R  51 52 53 54 each represents a hydrogen atom or an electron-donating substituent, and at least one of them is an electron-donating substituent. R, R, R, R
56 57 58 59は、各々水素原子または置換基を表し、 R 、R  56 57 58 59 each represents a hydrogen atom or a substituent, and R 1, R 2
56 58 の少なくとも一方は電子吸引性の置換基である。 R 、 R  At least one of 56 58 is an electron-withdrawing substituent. R, R
50 55は置換基を表し、 n51、 n5 50 55 represents a substituent, n51, n5
2は 0〜3から選ばれる整数を表す。 Xaは— N (Ra)、— O— Raまたは— S— Raを表 2 represents an integer selected from 0 to 3. Xa represents —N (Ra), —O—Ra or —S—Ra
2  2
す。 Raはアルキル基、シクロアルキル基、アルケニル基、ァリール基、複素環基また は芳香族複素環基を表す。 Xaが— N (Ra)の場合、 2つの Raは同じであっても異な The Ra represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. If Xa is — N (Ra), the two Ras are the same but different
2  2
つていてもよい。 Xは 0、 S、 CH、 CHR、 CR、 NR、 PR、 SiR、 C = 0、 C=NR、 S You may go on. X is 0, S, CH, CHR, CR, NR, PR, SiR, C = 0, C = NR, S
5 2 2 2  5 2 2 2
Oまたは SOを表す。 Rはアルキル基、シクロアルキル基、アルケニル基、ァリール基  Represents O or SO. R is an alkyl group, cycloalkyl group, alkenyl group, aryl group
2  2
、複素環基または芳香族複素環基を表す。 )  Represents a heterocyclic group or an aromatic heterocyclic group. )
下記一般式(10)で表される部分構造またはその互変異性体を部分構造として有す るオルトメタル錯体であることを特徴とする請求の範囲第 1〜6項のいずれか 1項に記 載の有機エレクト口ルミネッセンス素子材料。 7. An orthometal complex having a partial structure represented by the following general formula (10) or a tautomer thereof as a partial structure, according to any one of claims 1 to 6. Organic-elect mouth luminescence element material listed.
[化 7] 一般式 (10) Q6 [Chemical formula 7] General formula (10) Q 6
Ϊ)ΙΪΙ6一ズ6 ^3 F _ !  Ϊ) ΙΪΙ6 Ones 6 ^ 3 F _!
 :
X6 M X 6 M
\  \
(Ac)n6 -¾4 G : ( A c) n6 -¾4 G:
- - Qi (式中、 Mは元素周期表における第 8〜10族の金属元素を表す。 X 、X 、X 、X --Qi (In the formula, M represents a metal element of Groups 8 to 10 in the periodic table. X 1, X 2, X 3, X 4
61 62 63 64 は、各々炭素原子または窒素原子を表し、 Q  61 62 63 64 each represents a carbon atom or a nitrogen atom, and Q
61は炭素原子及び X 、X  61 is a carbon atom and X, X
61 63と共に 6員の 芳香族炭化水素環または 5〜6員の芳香族複素環である環 Fを形成する原子群を表 し、 Q は窒素原子及び X 、 X と共に 5〜6員の芳香族複素環である環 Gを形成す 61 represents a group of atoms forming a ring F which is a 6-membered aromatic hydrocarbon ring or a 5- to 6-membered aromatic heterocycle with 63 63, Q is a nitrogen atom and a 5- to 6-membered aromatic together with X and X Form a ring G that is a heterocycle
62 62 64 62 62 64
る原子群を表す。 X、 Xはファンデルワールス体積が 20 A3以上である置換基を表し b c Represents an atomic group. X and X represent substituents whose van der Waals volume is 20 A 3 or more bc
。 m6、 n6は 0または 1を表す。ただし、 m6 +n6≥lである。 Xは 0、 S、 CH、 CHR、  . m6 and n6 each represents 0 or 1. However, m6 + n6≥l. X is 0, S, CH, CHR,
6 2 6 2
CR、 NR、 PR、 SiR、 C = 0、 C=NR、 SOまたは SOを表す。 Rはアルキル基、シクCR, NR, PR, SiR, C = 0, C = NR, SO or SO. R is an alkyl group,
2 2 2 2 2 2
口アルキル基、アルケニル基、ァリール基、複素環基または芳香族複素環基を表す。 )  It represents a mouth alkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. )
[8] M力イリジウムまたは白金であることを特徴とする請求の範囲第 1〜7項のいずれ力 1 項に記載の有機エレクト口ルミネッセンス素子材料。  [8] The organic electoluminescence device material according to any one of [1] to [7], which is M force iridium or platinum.
[9] 請求の範囲第 1〜8項のいずれか 1項に記載の有機エレクト口ルミネッセンス素子材 料を含有することを特徴とする有機エレクト口ルミネッセンス素子。 [9] An organic electoluminescence device comprising the organic electroluminescence device material according to any one of claims 1 to 8.
[10] 構成層として発光層を有し、該発光層が請求の範囲第 1〜8項のいずれか 1項に記 載の有機エレクト口ルミネッセンス素子材料を含有することを特徴とする有機エレクト ロノレミネッセンス素子 n [10] An organic electroluminescent device comprising a light emitting layer as a constituent layer, wherein the light emitting layer contains the organic electroluminescent device material according to any one of claims 1 to 8. Reminescence element n
PCT/JP2006/303110 2005-03-16 2006-02-22 Organic electroluminescent device material and organic electroluminescent device WO2006098120A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2007508045A JP5125502B2 (en) 2005-03-16 2006-02-22 Organic electroluminescence element material, organic electroluminescence element

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2005-075061 2005-03-16
JP2005075061 2005-03-16

Publications (1)

Publication Number Publication Date
WO2006098120A1 true WO2006098120A1 (en) 2006-09-21

Family

ID=36991474

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2006/303110 WO2006098120A1 (en) 2005-03-16 2006-02-22 Organic electroluminescent device material and organic electroluminescent device

Country Status (2)

Country Link
JP (1) JP5125502B2 (en)
WO (1) WO2006098120A1 (en)

Cited By (483)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1647554A2 (en) * 2003-07-22 2006-04-19 Idemitsu Kosan Co., Ltd. Metal complex compound and organic electroluminescent device using same
JP2008160098A (en) * 2006-11-30 2008-07-10 Semiconductor Energy Lab Co Ltd Light emitting element, light emitting device, and electronic equipment
DE102007046445A1 (en) 2007-09-28 2009-04-16 Osram Opto Semiconductors Gmbh Organic radiation-emitting component, useful as organic light-emitting diode, comprises substrate, lower electrode layer, organic radiation-emitting layer with matrix containing radiation emitting metal complex and upper electrode layer
DE102008033929A1 (en) 2008-07-18 2010-01-21 Siemens Aktiengesellschaft Phosphorescent metal complex compound, process for the preparation thereof and radiation-emitting component
WO2010006666A1 (en) * 2008-07-17 2010-01-21 Merck Patent Gmbh Organic electroluminescence device
JP2010516040A (en) * 2007-01-16 2010-05-13 エルジー・ケム・リミテッド Electrolyte containing eutectic mixture and secondary battery using the same
WO2010054731A1 (en) * 2008-11-13 2010-05-20 Merck Patent Gmbh Materials for organic electroluminescent devices
DE102009031683A1 (en) 2009-07-03 2011-03-24 Siemens Aktiengesellschaft Phophorescent metal complex compound, process for the preparation thereof and radiation-emitting component
DE102010005632A1 (en) 2010-01-25 2011-07-28 Siemens Aktiengesellschaft, 80333 Phosphorescent metal complex compound, method of preparation and light emitting device
DE102010005634A1 (en) 2010-01-25 2011-07-28 Siemens Aktiengesellschaft, 80333 Novel use of guanidinium cation and light-emitting device
US8007927B2 (en) 2007-12-28 2011-08-30 Universal Display Corporation Dibenzothiophene-containing materials in phosphorescent light emitting diodes
US8030490B2 (en) * 2006-12-29 2011-10-04 National Tsing Hua University Phosphorescent iridium complex with non-conjugated cyclometalated ligands, synthetic method of preparing the same and phosphorescent organic light emitting diode thereof
US8040053B2 (en) 2008-02-09 2011-10-18 Universal Display Corporation Organic light emitting device architecture for reducing the number of organic materials
US8053770B2 (en) 2008-10-14 2011-11-08 Universal Display Corporation Emissive layer patterning for OLED
US8221905B2 (en) 2007-12-28 2012-07-17 Universal Display Corporation Carbazole-containing materials in phosphorescent light emitting diodes
WO2012124622A1 (en) 2011-03-14 2012-09-20 東レ株式会社 Light-emitting element material and light-emitting element
WO2012153725A1 (en) 2011-05-12 2012-11-15 東レ株式会社 Light-emitting element material and light-emitting element
EP2623508A1 (en) 2012-02-02 2013-08-07 Konica Minolta Advanced Layers, Inc. Iridium complex compound, organic electroluminescent element material, organic electroluminescent element, illumination device and display device
US8513658B2 (en) 2008-09-04 2013-08-20 Universal Display Corporation White phosphorescent organic light emitting devices
US8519384B2 (en) 2008-09-03 2013-08-27 Universal Display Corporation Phosphorescent materials
US8557400B2 (en) 2009-04-28 2013-10-15 Universal Display Corporation Iridium complex with methyl-D3 substitution
US8586204B2 (en) 2007-12-28 2013-11-19 Universal Display Corporation Phosphorescent emitters and host materials with improved stability
TWI421329B (en) * 2009-05-27 2014-01-01 Nat Univ Tsing Hua Iridium complexes and organic light-emitting diodes comprising the same
WO2014017484A1 (en) 2012-07-25 2014-01-30 東レ株式会社 Light emitting element material and light emitting element
US8692241B1 (en) 2012-11-08 2014-04-08 Universal Display Corporation Transition metal complexes containing triazole and tetrazole carbene ligands
US8709615B2 (en) 2011-07-28 2014-04-29 Universal Display Corporation Heteroleptic iridium complexes as dopants
US8716484B1 (en) 2012-12-05 2014-05-06 Universal Display Corporation Hole transporting materials with twisted aryl groups
US8722205B2 (en) 2009-03-23 2014-05-13 Universal Display Corporation Heteroleptic iridium complex
US8734962B2 (en) 2007-05-21 2014-05-27 Osram Opto Semiconductors Gmbh Phosphorescent metal complex compound radiation emitting component comprising a phosphorescent metal complex compound and method for production of a phosphorescent metal complex compound
US8754232B2 (en) 2011-02-23 2014-06-17 Universal Display Corporation Methods of making bis-tridentate carbene complexes of ruthenium and osmium
US8778511B2 (en) 2008-12-12 2014-07-15 Universal Display Corporation OLED stability via doped hole transport layer
US8815415B2 (en) 2008-12-12 2014-08-26 Universal Display Corporation Blue emitter with high efficiency based on imidazo[1,2-f] phenanthridine iridium complexes
US8822708B2 (en) 2007-08-08 2014-09-02 Universal Display Corporation Benzo-fused thiophene / triphenylene hybrid materials
US8866377B2 (en) 2006-12-28 2014-10-21 Universal Display Corporation Long lifetime phosphorescent organic light emitting device (OLED) structures
US8871361B2 (en) 2011-02-23 2014-10-28 Universal Display Corporation Tetradentate platinum complexes
US8883322B2 (en) 2011-03-08 2014-11-11 Universal Display Corporation Pyridyl carbene phosphorescent emitters
US8884316B2 (en) 2011-06-17 2014-11-11 Universal Display Corporation Non-common capping layer on an organic device
US8889864B2 (en) 2006-02-10 2014-11-18 Universal Display Corporation Metal complexes of cyclometallated imidazo[1,2-f]phenanthridine and diimidazo[1,2-a:1′,2′-c]quinazoline ligands and isoelectronic and benzannulated analogs thereof
US8927749B2 (en) 2013-03-07 2015-01-06 Universal Display Corporation Organic electroluminescent materials and devices
US8926119B2 (en) 2011-08-04 2015-01-06 Universal Display Corporation Extendable light source with variable light emitting area
US8927308B2 (en) 2011-05-12 2015-01-06 Universal Display Corporation Method of forming bus line designs for large-area OLED lighting
US8932734B2 (en) 2010-10-08 2015-01-13 Universal Display Corporation Organic electroluminescent materials and devices
US8946697B1 (en) 2012-11-09 2015-02-03 Universal Display Corporation Iridium complexes with aza-benzo fused ligands
US8952362B2 (en) 2012-08-31 2015-02-10 The Regents Of The University Of Michigan High efficiency and brightness fluorescent organic light emitting diode by triplet-triplet fusion
US8952363B2 (en) 2009-01-16 2015-02-10 Universal Display Corporation Organic electroluminescent materials and devices
US8963132B2 (en) 2010-03-25 2015-02-24 Universal Display Corporation Solution processable doped triarylamine hole injection materials
US8969592B2 (en) 2012-01-10 2015-03-03 Universal Display Corporation Heterocyclic host materials
US8968887B2 (en) 2010-04-28 2015-03-03 Universal Display Corporation Triphenylene-benzofuran/benzothiophene/benzoselenophene compounds with substituents joining to form fused rings
US8987451B2 (en) 2012-01-03 2015-03-24 Universal Display Corporation Synthesis of cyclometallated platinum(II) complexes
US9005772B2 (en) 2011-02-23 2015-04-14 Universal Display Corporation Thioazole and oxazole carbene metal complexes as phosphorescent OLED materials
US9005771B2 (en) 2009-05-12 2015-04-14 Universal Display Corporation 2-azatriphenylene materials for organic light emitting diodes
US9034483B2 (en) 2008-09-16 2015-05-19 Universal Display Corporation Phosphorescent materials
US9040962B2 (en) 2010-04-28 2015-05-26 Universal Display Corporation Depositing premixed materials
US9054343B2 (en) 2011-06-17 2015-06-09 Universal Display Corporation Fine tuning of emission spectra by combination of multiple emitter spectra
US9054323B2 (en) 2012-03-15 2015-06-09 Universal Display Corporation Secondary hole transporting layer with diarylamino-phenyl-carbazole compounds
US9054344B2 (en) 2010-01-20 2015-06-09 Universal Display Corporation Electroluminescent devices for lighting applications
US9059412B2 (en) 2012-07-19 2015-06-16 Universal Display Corporation Transition metal complexes containing substituted imidazole carbene as ligands and their application in OLEDs
US9118017B2 (en) 2012-02-27 2015-08-25 Universal Display Corporation Host compounds for red phosphorescent OLEDs
US9130177B2 (en) 2011-01-13 2015-09-08 Universal Display Corporation 5-substituted 2 phenylquinoline complexes materials for light emitting diode
US9140428B2 (en) 2010-06-11 2015-09-22 Universal Display Corporation Triplet-triplet annihilation up-conversation for display and lighting applications
US9142788B2 (en) 2011-11-14 2015-09-22 Universal Display Corporation Host materials for OLEDs
US9142786B2 (en) 2007-03-08 2015-09-22 Universal Display Corporation Phosphorescent materials
US9139764B2 (en) 2007-09-28 2015-09-22 Osram Opto Semiconductors Gmbh Organic radiation-emitting component
US9156870B2 (en) 2010-02-25 2015-10-13 Universal Display Corporation Phosphorescent emitters
US9163174B2 (en) 2012-01-04 2015-10-20 Universal Display Corporation Highly efficient phosphorescent materials
US9166175B2 (en) 2012-11-27 2015-10-20 Universal Display Corporation Organic electroluminescent materials and devices
US9175211B2 (en) 2010-03-03 2015-11-03 Universal Display Corporation Phosphorescent materials
US9181270B2 (en) 2014-02-28 2015-11-10 Universal Display Corporation Method of making sulfide compounds
US9184399B2 (en) 2012-05-04 2015-11-10 Universal Display Corporation Asymmetric hosts with triaryl silane side chains
US9190621B2 (en) 2007-03-08 2015-11-17 Universal Display Corporation Materials for organic light emitting diode
US9190620B2 (en) 2014-03-01 2015-11-17 Universal Display Corporation Organic electroluminescent materials and devices
US9190623B2 (en) 2012-11-20 2015-11-17 Universal Display Corporation Organic electroluminescent materials and devices
US9193745B2 (en) 2011-11-15 2015-11-24 Universal Display Corporation Heteroleptic iridium complex
US9196860B2 (en) 2012-12-04 2015-11-24 Universal Display Corporation Compounds for triplet-triplet annihilation upconversion
US9209411B2 (en) 2012-12-07 2015-12-08 Universal Display Corporation Organic electroluminescent materials and devices
US9212197B2 (en) 2011-05-19 2015-12-15 Universal Display Corporation Phosphorescent heteroleptic phenylbenzimidazole dopants
US9217004B2 (en) 2011-11-21 2015-12-22 Universal Display Corporation Organic light emitting materials
US9224958B2 (en) 2013-07-19 2015-12-29 Universal Display Corporation Organic electroluminescent materials and devices
US9231218B2 (en) 2012-07-10 2016-01-05 Universal Display Corporation Phosphorescent emitters containing dibenzo[1,4]azaborinine structure
US9252377B2 (en) 2011-07-14 2016-02-02 Universal Display Corporation Inorganic hosts in OLEDs
US9252363B2 (en) 2012-10-04 2016-02-02 Universal Display Corporation Aryloxyalkylcarboxylate solvent compositions for inkjet printing of organic layers
US9257658B2 (en) 2011-05-19 2016-02-09 Universal Display Corporation Method of making organic electroluminescent materials
US9287513B2 (en) 2012-09-24 2016-03-15 Universal Display Corporation Organic electroluminescent materials and devices
US9293712B2 (en) 2013-10-11 2016-03-22 Universal Display Corporation Disubstituted pyrene compounds with amino group containing ortho aryl group and devices containing the same
US9306179B2 (en) 2013-11-08 2016-04-05 Universal Display Corporation Organic electroluminescent materials and devices
US9312499B1 (en) 2015-01-05 2016-04-12 Universal Display Corporation Organic electroluminescent materials and devices
US9312505B2 (en) 2012-09-25 2016-04-12 Universal Display Corporation Organic electroluminescent materials and devices
US9318710B2 (en) 2012-07-30 2016-04-19 Universal Display Corporation Organic electroluminescent materials and devices
US9324949B2 (en) 2013-07-16 2016-04-26 Universal Display Corporation Organic electroluminescent materials and devices
US9359549B2 (en) 2009-04-06 2016-06-07 Universal Display Corporation Organic electroluminescent materials and devices
US9386657B2 (en) 2012-03-15 2016-07-05 Universal Display Corporation Organic Electroluminescent materials and devices
US9397310B2 (en) 2011-07-14 2016-07-19 Universal Display Corporation Organice electroluminescent materials and devices
US9397302B2 (en) 2014-10-08 2016-07-19 Universal Display Corporation Organic electroluminescent materials and devices
US9397312B2 (en) 2011-05-11 2016-07-19 Universal Display Corporation Process for fabricating metal bus lines for OLED lighting panels
US9397309B2 (en) 2014-03-13 2016-07-19 Universal Display Corporation Organic electroluminescent devices
US9406892B2 (en) 2015-01-07 2016-08-02 Universal Display Corporation Organic electroluminescent materials and devices
US9419225B2 (en) 2013-03-14 2016-08-16 Universal Display Corporation Organic electroluminescent materials and devices
US9435021B2 (en) 2010-07-29 2016-09-06 University Of Southern California Co-deposition methods for the fabrication of organic optoelectronic devices
US9444075B2 (en) 2014-11-26 2016-09-13 Universal Display Corporation Emissive display with photo-switchable polarization
US9450198B2 (en) 2014-04-15 2016-09-20 Universal Display Corporation Organic electroluminescent materials and devices
US9450195B2 (en) 2014-12-17 2016-09-20 Universal Display Corporation Organic electroluminescent materials and devices
US9455411B2 (en) 2008-09-25 2016-09-27 Universal Display Corporation Organic electroluminescent materials and devices
US9455417B2 (en) 2011-12-13 2016-09-27 Universal Display Corporation Split electrode for organic devices
US9461254B2 (en) 2012-01-03 2016-10-04 Universal Display Corporation Organic electroluminescent materials and devices
US9478758B1 (en) 2015-05-08 2016-10-25 Universal Display Corporation Organic electroluminescent materials and devices
US9484541B2 (en) 2014-10-20 2016-11-01 Universal Display Corporation Organic electroluminescent materials and devices
US9493698B2 (en) 2011-08-31 2016-11-15 Universal Display Corporation Organic electroluminescent materials and devices
US9502656B2 (en) 2014-02-24 2016-11-22 Universal Display Corporation Organic electroluminescent materials and devices
US9502672B2 (en) 2012-06-21 2016-11-22 Universal Display Corporation Organic electroluminescent materials and devices
US20160343951A1 (en) * 2015-05-21 2016-11-24 Universal Display Corporation Organic electroluminescent materials and devices
US9512136B2 (en) 2012-11-26 2016-12-06 Universal Display Corporation Organic electroluminescent materials and devices
US9512355B2 (en) 2011-12-09 2016-12-06 Universal Display Corporation Organic light emitting materials
US9537106B2 (en) 2013-05-09 2017-01-03 Universal Display Corporation Organic electroluminescent materials and devices
US9540329B2 (en) 2012-07-19 2017-01-10 Universal Display Corporation Organic electroluminescent materials and devices
US9543532B2 (en) 2010-06-11 2017-01-10 Universal Display Corporation Organic electroluminescent materials and devices
US9553274B2 (en) 2013-07-16 2017-01-24 Universal Display Corporation Organic electroluminescent materials and devices
US9590195B2 (en) 2014-02-28 2017-03-07 Universal Display Corporation Organic electroluminescent materials and devices
US9590194B2 (en) 2014-02-14 2017-03-07 Universal Display Corporation Organic electroluminescent materials and devices
US9590180B2 (en) 2007-06-23 2017-03-07 Universal Display Corporation Organic electroluminescent materials and devices
US20170077409A1 (en) * 2015-05-21 2017-03-16 Universal Display Corporation Organic electroluminescent materials and devices
US9634264B2 (en) 2012-11-09 2017-04-25 Universal Display Corporation Organic electroluminescent materials and devices
US9647218B2 (en) 2013-11-14 2017-05-09 Universal Display Corporation Organic electroluminescent materials and devices
US9647227B2 (en) 2005-04-13 2017-05-09 Universal Display Corporation Organic light emitting devices
US9647221B2 (en) 2011-07-14 2017-05-09 Universal Display Corporation Organic light-emitting devices
US9647217B2 (en) 2014-02-24 2017-05-09 Universal Display Corporation Organic electroluminescent materials and devices
US9653691B2 (en) 2012-12-12 2017-05-16 Universal Display Corporation Phosphorescence-sensitizing fluorescence material system
US9663544B2 (en) 2012-07-25 2017-05-30 Universal Display Corporation Organic electroluminescent materials and devices
US9673401B2 (en) 2013-06-28 2017-06-06 Universal Display Corporation Organic electroluminescent materials and devices
US9673407B2 (en) 2014-02-28 2017-06-06 Universal Display Corporation Organic electroluminescent materials and devices
US9673406B2 (en) 2009-05-20 2017-06-06 Universal Display Corporation Metal complexes with boron-nitrogen heterocycle containing ligands
US9670404B2 (en) 2012-06-06 2017-06-06 Universal Display Corporation Organic electroluminescent materials and devices
US9685617B2 (en) 2012-11-09 2017-06-20 Universal Display Corporation Organic electronuminescent materials and devices
US9691993B2 (en) 2014-04-09 2017-06-27 Universal Display Corporation Organic electroluminescent materials and devices
US9711730B2 (en) 2015-01-25 2017-07-18 Universal Display Corporation Organic electroluminescent materials and devices
US9725476B2 (en) 2012-07-09 2017-08-08 Universal Display Corporation Silylated metal complexes
US9735378B2 (en) 2013-09-09 2017-08-15 Universal Display Corporation Organic electroluminescent materials and devices
US9735373B2 (en) 2013-06-10 2017-08-15 Universal Display Corporation Organic electroluminescent materials and devices
US9741941B2 (en) 2014-04-29 2017-08-22 Universal Display Corporation Organic electroluminescent materials and devices
US9748503B2 (en) 2013-09-13 2017-08-29 Universal Display Corporation Organic electroluminescent materials and devices
US9748504B2 (en) 2014-03-25 2017-08-29 Universal Display Corporation Organic electroluminescent materials and devices
US9748500B2 (en) 2015-01-15 2017-08-29 Universal Display Corporation Organic light emitting materials
US9755159B2 (en) 2014-01-23 2017-09-05 Universal Display Corporation Organic materials for OLEDs
US9755164B2 (en) 2011-06-08 2017-09-05 Universal Display Corporation Organic electroluminescent materials and devices
US9761814B2 (en) 2014-11-18 2017-09-12 Universal Display Corporation Organic light-emitting materials and devices
US9761807B2 (en) 2013-07-15 2017-09-12 Universal Display Corporation Organic light emitting diode materials
US9773986B2 (en) 2009-11-19 2017-09-26 The University Of Southern California Copper(I)-carbene complexes and organic electroluminescent devices
US9773985B2 (en) 2012-05-21 2017-09-26 Universal Display Corporation Organic electroluminescent materials and devices
US9780316B2 (en) 2015-03-16 2017-10-03 Universal Display Corporation Organic electroluminescent materials and devices
US9783564B2 (en) 2011-07-25 2017-10-10 Universal Display Corporation Organic electroluminescent materials and devices
US9831447B2 (en) 2013-10-08 2017-11-28 Universal Display Corporation Organic electroluminescent materials and devices
US9831437B2 (en) 2013-08-20 2017-11-28 Universal Display Corporation Organic electroluminescent materials and devices
US9847498B2 (en) 2014-04-14 2017-12-19 Universal Display Corporation Organic electroluminescent materials and devices
US9847496B2 (en) 2013-12-23 2017-12-19 Universal Display Corporation Organic electroluminescent materials and devices
US9847497B2 (en) 2014-02-18 2017-12-19 Universal Display Corporation Organic electroluminescent materials and devices
US9853229B2 (en) 2013-10-23 2017-12-26 University Of Southern California Organic electroluminescent materials and devices
US9859510B2 (en) 2015-05-15 2018-01-02 Universal Display Corporation Organic electroluminescent materials and devices
US9871212B2 (en) 2014-11-14 2018-01-16 Universal Display Corporation Organic electroluminescent materials and devices
US9876173B2 (en) 2013-12-09 2018-01-23 Universal Display Corporation Organic electroluminescent materials and devices
US9882151B2 (en) 2014-11-14 2018-01-30 Universal Display Corporation Organic electroluminescent materials and devices
US9899612B2 (en) 2006-12-08 2018-02-20 Universal Display Corporation Organic electroluminescent materials and devices
US9905784B2 (en) 2013-11-15 2018-02-27 Universal Display Corporation Organic electroluminescent materials and devices
US9911931B2 (en) 2014-06-26 2018-03-06 Universal Display Corporation Organic electroluminescent materials and devices
US9911928B2 (en) 2015-03-19 2018-03-06 Universal Display Corporation Organic electroluminescent materials and devices
US9929357B2 (en) 2014-07-22 2018-03-27 Universal Display Corporation Organic electroluminescent materials and devices
US9929353B2 (en) 2014-04-02 2018-03-27 Universal Display Corporation Organic electroluminescent materials and devices
US9929360B2 (en) 2016-07-08 2018-03-27 Universal Display Corporation Organic electroluminescent materials and devices
US9929361B2 (en) 2015-02-16 2018-03-27 Universal Display Corporation Organic electroluminescent materials and devices
US9932359B2 (en) 2013-08-30 2018-04-03 University Of Southern California Organic electroluminescent materials and devices
US9935276B2 (en) 2013-02-21 2018-04-03 Universal Display Corporation Organic electroluminescent materials and devices
US9935277B2 (en) 2014-01-30 2018-04-03 Universal Display Corporation Organic electroluminescent materials and devices
US9954180B2 (en) 2010-08-20 2018-04-24 Universal Display Corporation Bicarbazole compounds for OLEDs
US9978961B2 (en) 2014-01-08 2018-05-22 Universal Display Corporation Organic electroluminescent materials and devices
US9978958B2 (en) 2012-08-24 2018-05-22 Universal Display Corporation Phosphorescent emitters with phenylimidazole ligands
US9997712B2 (en) 2013-03-27 2018-06-12 Universal Display Corporation Organic electroluminescent materials and devices
US9997716B2 (en) 2014-05-27 2018-06-12 Universal Display Corporation Organic electroluminescent materials and devices
US10003033B2 (en) 2014-02-18 2018-06-19 Universal Display Corporation Organic electroluminescent materials and devices
US10003034B2 (en) 2013-09-30 2018-06-19 Universal Display Corporation Organic electroluminescent materials and devices
US10008677B2 (en) 2011-01-13 2018-06-26 Universal Display Corporation Materials for organic light emitting diode
US10008679B2 (en) 2014-04-14 2018-06-26 Universal Display Corporation Organic electroluminescent materials and devices
US10033004B2 (en) 2015-06-01 2018-07-24 Universal Display Corporation Organic electroluminescent materials and devices
US10038151B2 (en) 2014-11-12 2018-07-31 Universal Display Corporation Organic electroluminescent materials and devices
US10043987B2 (en) 2014-09-29 2018-08-07 Universal Display Corporation Organic electroluminescent materials and devices
US10056565B2 (en) 2013-11-20 2018-08-21 Universal Display Corporation Organic electroluminescent materials and devices
US10069090B2 (en) 2012-11-20 2018-09-04 Universal Display Corporation Organic electroluminescent materials and devices
US10074806B2 (en) 2013-08-20 2018-09-11 Universal Display Corporation Organic electroluminescent materials and devices
US10079349B2 (en) 2011-05-27 2018-09-18 Universal Display Corporation Organic electroluminescent materials and devices
US10121975B2 (en) 2013-07-03 2018-11-06 Universal Display Corporation Organic electroluminescent materials and devices
US10135008B2 (en) 2014-01-07 2018-11-20 Universal Display Corporation Organic electroluminescent materials and devices
US10135007B2 (en) 2014-09-29 2018-11-20 Universal Display Corporation Organic electroluminescent materials and devices
US10135006B2 (en) 2016-01-04 2018-11-20 Universal Display Corporation Organic electroluminescent materials and devices
US10144867B2 (en) 2015-02-13 2018-12-04 Universal Display Corporation Organic electroluminescent materials and devices
US10147892B2 (en) 2010-12-07 2018-12-04 The University Of Southern California Organic electroluminescent materials and devices
US10153443B2 (en) 2016-07-19 2018-12-11 Universal Display Corporation Organic electroluminescent materials and devices
US10153445B2 (en) 2016-11-21 2018-12-11 Universal Display Corporation Organic electroluminescent materials and devices
US10158089B2 (en) 2011-05-27 2018-12-18 Universal Display Corporation Organic electroluminescent materials and devices
US10177316B2 (en) 2015-02-09 2019-01-08 Universal Display Corporation Organic electroluminescent materials and devices
US10177318B2 (en) 2015-10-29 2019-01-08 Universal Display Corporation Organic electroluminescent materials and devices
US10181564B2 (en) 2015-08-26 2019-01-15 Universal Display Corporation Organic electroluminescent materials and devices
CN109280063A (en) * 2017-07-21 2019-01-29 三星显示有限公司 Organo-metallic compound and organic luminescent device including it
US10199581B2 (en) 2013-07-01 2019-02-05 Universal Display Corporation Organic electroluminescent materials and devices
US10199582B2 (en) 2013-09-03 2019-02-05 University Of Southern California Organic electroluminescent materials and devices
US10205105B2 (en) 2016-08-15 2019-02-12 Universal Display Corporation Organic electroluminescent materials and devices
US10208026B2 (en) 2014-03-18 2019-02-19 Universal Display Corporation Organic electroluminescent materials and devices
US10211413B2 (en) 2012-01-17 2019-02-19 Universal Display Corporation Organic electroluminescent materials and devices
US10236456B2 (en) 2016-04-11 2019-03-19 Universal Display Corporation Organic electroluminescent materials and devices
US10236458B2 (en) 2016-10-24 2019-03-19 Universal Display Corporation Organic electroluminescent materials and devices
US10256427B2 (en) 2014-04-15 2019-04-09 Universal Display Corporation Efficient organic electroluminescent devices
US10253252B2 (en) 2014-12-30 2019-04-09 Universal Display Corporation Organic electroluminescent materials and devices
US10256419B2 (en) 2014-05-08 2019-04-09 Universal Display Corporation Organic electroluminescent materials and devices
US10270046B2 (en) 2015-03-06 2019-04-23 Universal Display Corporation Organic electroluminescent materials and devices
US10276809B2 (en) 2016-04-05 2019-04-30 Universal Display Corporation Organic electroluminescent materials and devices
US10297770B2 (en) 2015-03-27 2019-05-21 Universal Display Corporation Organic electroluminescent materials and devices
US10297762B2 (en) 2014-07-09 2019-05-21 Universal Display Corporation Organic electroluminescent materials and devices
US10301338B2 (en) 2014-05-08 2019-05-28 Universal Display Corporation Organic electroluminescent materials and devices
US10340464B2 (en) 2016-11-10 2019-07-02 Universal Display Corporation Organic electroluminescent materials and devices
US10355227B2 (en) 2013-12-16 2019-07-16 Universal Display Corporation Metal complex for phosphorescent OLED
US10355222B2 (en) 2015-02-06 2019-07-16 Universal Display Corporation Organic electroluminescent materials and devices
US10361375B2 (en) 2014-10-06 2019-07-23 Universal Display Corporation Organic electroluminescent materials and devices
US10361381B2 (en) 2015-09-03 2019-07-23 Universal Display Corporation Organic electroluminescent materials and devices
US10388892B2 (en) 2015-10-29 2019-08-20 Universal Display Corporation Organic electroluminescent materials and devices
US10388893B2 (en) 2015-10-29 2019-08-20 Universal Display Corporation Organic electroluminescent materials and devices
US10403826B2 (en) 2015-05-07 2019-09-03 Universal Display Corporation Organic electroluminescent materials and devices
US10403825B2 (en) 2014-02-27 2019-09-03 Universal Display Corporation Organic electroluminescent materials and devices
US10403830B2 (en) 2014-05-08 2019-09-03 Universal Display Corporation Organic electroluminescent materials and devices
US10400163B2 (en) 2013-02-08 2019-09-03 Universal Display Corporation Organic electroluminescent materials and devices
US10411200B2 (en) 2014-08-07 2019-09-10 Universal Display Corporation Electroluminescent (2-phenylpyridine)iridium complexes and devices
US10411201B2 (en) 2014-11-12 2019-09-10 Universal Display Corporation Organic electroluminescent materials and devices
US10418562B2 (en) 2015-02-06 2019-09-17 Universal Display Corporation Organic electroluminescent materials and devices
US10418568B2 (en) 2015-06-01 2019-09-17 Universal Display Corporation Organic electroluminescent materials and devices
US10418569B2 (en) 2015-01-25 2019-09-17 Universal Display Corporation Organic electroluminescent materials and devices
US10457699B2 (en) 2014-05-02 2019-10-29 Universal Display Corporation Organic electroluminescent materials and devices
US10457864B2 (en) 2016-02-09 2019-10-29 Universal Display Corporation Organic electroluminescent materials and devices
US10461260B2 (en) 2014-06-03 2019-10-29 Universal Display Corporation Organic electroluminescent materials and devices
US10468609B2 (en) 2016-06-02 2019-11-05 Universal Display Corporation Organic electroluminescent materials and devices
US10476010B2 (en) 2015-11-30 2019-11-12 Universal Display Corporation Organic electroluminescent materials and devices
US10490753B2 (en) 2016-12-15 2019-11-26 Universal Display Corporation Organic electroluminescent materials and devices
US10505127B2 (en) 2016-09-19 2019-12-10 Universal Display Corporation Organic electroluminescent materials and devices
US10522769B2 (en) 2015-08-18 2019-12-31 Universal Display Corporation Organic electroluminescent materials and devices
US10529931B2 (en) 2015-03-24 2020-01-07 Universal Display Corporation Organic Electroluminescent materials and devices
US10566546B2 (en) 2014-07-14 2020-02-18 Universal Display Corporation Organic electroluminescent materials and devices
US10566552B2 (en) 2016-04-13 2020-02-18 Universal Display Corporation Organic electroluminescent materials and devices
US10566547B2 (en) 2016-07-11 2020-02-18 Universal Display Corporation Organic electroluminescent materials and devices
CN110872327A (en) * 2018-08-31 2020-03-10 三星电子株式会社 Organometallic compound, organic light emitting device including the same, and diagnostic composition
US10593892B2 (en) 2015-10-01 2020-03-17 Universal Display Corporation Organic electroluminescent materials and devices
US10593890B2 (en) 2015-04-06 2020-03-17 Universal Display Corporation Organic electroluminescent materials and devices
US10600967B2 (en) 2016-02-18 2020-03-24 Universal Display Corporation Organic electroluminescent materials and devices
US10600966B2 (en) 2015-02-27 2020-03-24 Universal Display Corporation Organic electroluminescent materials and devices
US10608185B2 (en) 2016-10-17 2020-03-31 Univeral Display Corporation Organic electroluminescent materials and devices
US10608186B2 (en) 2016-09-14 2020-03-31 Universal Display Corporation Organic electroluminescent materials and devices
US10608188B2 (en) 2017-09-11 2020-03-31 Universal Display Corporation Organic electroluminescent materials and devices
US10629820B2 (en) 2017-01-18 2020-04-21 Universal Display Corporation Organic electroluminescent materials and devices
US10636983B2 (en) 2014-05-08 2020-04-28 Universal Display Corporation Organic electroluminescent materials and devices
US10636978B2 (en) 2014-12-30 2020-04-28 Universal Display Corporation Organic electroluminescent materials and devices
US10644247B2 (en) 2015-02-06 2020-05-05 Universal Display Corporation Organic electroluminescent materials and devices
US10644251B2 (en) 2013-12-04 2020-05-05 Universal Display Corporation Organic electroluminescent materials and devices
US10651403B2 (en) 2016-06-20 2020-05-12 Universal Display Corporation Organic electroluminescent materials and devices
US10662196B2 (en) 2016-11-17 2020-05-26 Universal Display Corporation Organic electroluminescent materials and devices
US10672998B2 (en) 2017-03-23 2020-06-02 Universal Display Corporation Organic electroluminescent materials and devices
US10672997B2 (en) 2016-06-20 2020-06-02 Universal Display Corporation Organic electroluminescent materials and devices
US10680187B2 (en) 2016-09-23 2020-06-09 Universal Display Corporation Organic electroluminescent materials and devices
US10680188B2 (en) 2016-11-11 2020-06-09 Universal Display Corporation Organic electroluminescent materials and devices
US10680183B2 (en) 2015-02-15 2020-06-09 Universal Display Corporation Organic electroluminescent materials and devices
US10686140B2 (en) 2016-06-20 2020-06-16 Universal Display Corporation Organic electroluminescent materials and devices
US10686143B2 (en) 2015-03-05 2020-06-16 Universal Display Corporation Organic electroluminescent materials and devices
DE102013200085B4 (en) 2012-01-06 2020-06-18 Universal Display Corporation Highly efficient phosphorescent materials
US10707423B2 (en) 2014-02-21 2020-07-07 Universal Display Corporation Organic electroluminescent materials and devices
US10707427B2 (en) 2016-02-09 2020-07-07 Universal Display Corporation Organic electroluminescent materials and devices
US10720587B2 (en) 2016-07-19 2020-07-21 Universal Display Corporation Organic electroluminescent materials and devices
US10727423B2 (en) 2016-06-20 2020-07-28 Universal Display Corporation Organic electroluminescent materials and devices
US10741780B2 (en) 2017-03-10 2020-08-11 Universal Display Corporation Organic electroluminescent materials and devices
US10745431B2 (en) 2017-03-08 2020-08-18 Universal Display Corporation Organic electroluminescent materials and devices
US10749113B2 (en) 2014-09-29 2020-08-18 Universal Display Corporation Organic electroluminescent materials and devices
US10770664B2 (en) 2015-09-21 2020-09-08 Universal Display Corporation Organic electroluminescent materials and devices
US10777754B2 (en) 2017-04-11 2020-09-15 Universal Display Corporation Organic electroluminescent materials and devices
US10777749B2 (en) 2015-05-07 2020-09-15 Universal Display Corporation Organic electroluminescent materials and devices
US10790455B2 (en) 2017-05-18 2020-09-29 Universal Display Corporation Organic electroluminescent materials and devices
US10804475B2 (en) 2017-01-11 2020-10-13 Universal Display Corporation Organic electroluminescent materials and devices
US10811618B2 (en) 2016-12-19 2020-10-20 Universal Display Corporation Organic electroluminescent materials and devices
US10825997B2 (en) 2015-06-25 2020-11-03 Universal Display Corporation Organic electroluminescent materials and devices
US10822361B2 (en) 2017-02-22 2020-11-03 Universal Display Corporation Organic electroluminescent materials and devices
US10822362B2 (en) 2017-05-11 2020-11-03 Universal Display Corporation Organic electroluminescent materials and devices
US10833276B2 (en) 2016-11-21 2020-11-10 Universal Display Corporation Organic electroluminescent materials and devices
US10840458B2 (en) 2016-05-25 2020-11-17 Universal Display Corporation Organic electroluminescent materials and devices
US10840459B2 (en) 2017-05-18 2020-11-17 Universal Display Corporation Organic electroluminescent materials and devices
US10844085B2 (en) 2017-03-29 2020-11-24 Universal Display Corporation Organic electroluminescent materials and devices
US10847728B2 (en) 2015-10-01 2020-11-24 Universal Display Corporation Organic electroluminescent materials and devices
US10854826B2 (en) 2014-10-08 2020-12-01 Universal Display Corporation Organic electroluminescent compounds, compositions and devices
US10862054B2 (en) 2016-06-20 2020-12-08 Universal Display Corporation Organic electroluminescent materials and devices
US10862046B2 (en) 2017-03-30 2020-12-08 Universal Display Corporation Organic electroluminescent materials and devices
US10862055B2 (en) 2017-05-05 2020-12-08 Universal Display Corporation Organic electroluminescent materials and devices
US10868261B2 (en) 2014-11-10 2020-12-15 Universal Display Corporation Organic electroluminescent materials and devices
US10873037B2 (en) 2017-03-28 2020-12-22 Universal Display Corporation Organic electroluminescent materials and devices
US10873036B2 (en) 2015-07-07 2020-12-22 Universal Display Corporation Organic electroluminescent materials and devices
US10870668B2 (en) 2017-05-05 2020-12-22 Universal Display Corporation Organic electroluminescent materials and devices
US10897016B2 (en) 2016-11-14 2021-01-19 Universal Display Corporation Organic electroluminescent materials and devices
US10910570B2 (en) 2017-04-28 2021-02-02 Universal Display Corporation Organic electroluminescent materials and devices
US10910577B2 (en) 2017-03-28 2021-02-02 Universal Display Corporation Organic electroluminescent materials and devices
US10930866B2 (en) 2013-07-25 2021-02-23 Universal Display Corporation Organic electroluminescent materials and devices
US10930864B2 (en) 2017-05-10 2021-02-23 Universal Display Corporation Organic electroluminescent materials and devices
US10930862B2 (en) 2017-06-01 2021-02-23 Universal Display Corporation Organic electroluminescent materials and devices
US10934293B2 (en) 2017-05-18 2021-03-02 Universal Display Corporation Organic electroluminescent materials and devices
US10944062B2 (en) 2017-05-18 2021-03-09 Universal Display Corporation Organic electroluminescent materials and devices
US10944060B2 (en) 2017-05-11 2021-03-09 Universal Display Corporation Organic electroluminescent materials and devices
US10941170B2 (en) 2017-05-03 2021-03-09 Universal Display Corporation Organic electroluminescent materials and devices
US10950803B2 (en) 2014-10-13 2021-03-16 Universal Display Corporation Compounds and uses in devices
US10957861B2 (en) 2015-12-29 2021-03-23 Universal Display Corporation Organic electroluminescent materials and devices
US10957866B2 (en) 2016-06-30 2021-03-23 Universal Display Corporation Organic electroluminescent materials and devices
US10957870B2 (en) 2012-09-07 2021-03-23 Universal Display Corporation Organic light emitting device
US10964904B2 (en) 2017-01-20 2021-03-30 Universal Display Corporation Organic electroluminescent materials and devices
US10964893B2 (en) 2016-11-17 2021-03-30 Universal Display Corporation Organic electroluminescent materials and devices
US10971687B2 (en) 2017-12-14 2021-04-06 Universal Display Corporation Organic electroluminescent materials and devices
US10968226B2 (en) 2017-06-23 2021-04-06 Universal Display Corporation Organic electroluminescent materials and devices
US10978647B2 (en) 2017-02-15 2021-04-13 Universal Display Corporation Organic electroluminescent materials and devices
US10975113B2 (en) 2017-04-21 2021-04-13 Universal Display Corporation Organic electroluminescent materials and devices
US10991895B2 (en) 2015-10-06 2021-04-27 Universal Display Corporation Organic electroluminescent materials and devices
US10998507B2 (en) 2015-11-23 2021-05-04 Universal Display Corporation Organic electroluminescent materials and devices
US11011709B2 (en) 2016-10-07 2021-05-18 Universal Display Corporation Organic electroluminescent materials and devices
US11018309B2 (en) 2015-08-03 2021-05-25 Universal Display Corporation Organic electroluminescent materials and devices
US11024808B2 (en) 2015-12-29 2021-06-01 Universal Display Corporation Organic electroluminescent materials and devices
US11038117B2 (en) 2017-04-11 2021-06-15 Universal Display Corporation Organic electroluminescent materials and devices
US11038115B2 (en) 2017-05-18 2021-06-15 Universal Display Corporation Organic electroluminescent materials and device
US11038137B2 (en) 2017-04-28 2021-06-15 Universal Display Corporation Organic electroluminescent materials and devices
US11050028B2 (en) 2017-01-24 2021-06-29 Universal Display Corporation Organic electroluminescent materials and devices
US11053268B2 (en) 2017-01-20 2021-07-06 Universal Display Corporation Organic electroluminescent materials and devices
US11056658B2 (en) 2017-03-29 2021-07-06 Universal Display Corporation Organic electroluminescent materials and devices
US11056657B2 (en) 2015-02-27 2021-07-06 University Display Corporation Organic electroluminescent materials and devices
US11081647B2 (en) 2016-04-22 2021-08-03 Universal Display Corporation Organic electroluminescent materials and devices
US11081659B2 (en) 2018-01-10 2021-08-03 Universal Display Corporation Organic electroluminescent materials and devices
US11081658B2 (en) 2016-10-03 2021-08-03 Universal Display Corporation Organic electroluminescent materials and devices
US11084838B2 (en) 2017-04-21 2021-08-10 Universal Display Corporation Organic electroluminescent materials and device
US11094891B2 (en) 2016-03-16 2021-08-17 Universal Display Corporation Organic electroluminescent materials and devices
US11101434B2 (en) 2017-04-21 2021-08-24 Universal Display Corporation Organic electroluminescent materials and devices
US11108000B2 (en) 2014-08-07 2021-08-31 Unniversal Display Corporation Organic electroluminescent materials and devices
US11117897B2 (en) 2017-05-01 2021-09-14 Universal Display Corporation Organic electroluminescent materials and devices
US11127906B2 (en) 2016-10-03 2021-09-21 Universal Display Corporation Organic electroluminescent materials and devices
US11127905B2 (en) 2015-07-29 2021-09-21 Universal Display Corporation Organic electroluminescent materials and devices
US11139443B2 (en) 2017-03-31 2021-10-05 Universal Display Corporation Organic electroluminescent materials and devices
US11142538B2 (en) 2018-03-12 2021-10-12 Universal Display Corporation Organic electroluminescent materials and devices
US11152579B2 (en) 2016-12-28 2021-10-19 Universal Display Corporation Organic electroluminescent materials and devices
US11158820B2 (en) 2017-03-29 2021-10-26 Universal Display Corporation Organic electroluminescent materials and devices
US11165028B2 (en) 2018-03-12 2021-11-02 Universal Display Corporation Organic electroluminescent materials and devices
US11168103B2 (en) 2017-11-17 2021-11-09 Universal Display Corporation Organic electroluminescent materials and devices
US11174259B2 (en) 2017-06-23 2021-11-16 Universal Display Corporation Organic electroluminescent materials and devices
US11183642B2 (en) 2016-10-03 2021-11-23 Universal Display Corporation Organic electroluminescent materials and devices
US11183646B2 (en) 2017-11-07 2021-11-23 Universal Display Corporation Organic electroluminescent materials and devices
US11180519B2 (en) 2018-02-09 2021-11-23 Universal Display Corporation Organic electroluminescent materials and devices
US11189804B2 (en) 2016-10-03 2021-11-30 Universal Display Corporation Organic electroluminescent materials and devices
US11196010B2 (en) 2016-10-03 2021-12-07 Universal Display Corporation Organic electroluminescent materials and devices
US11201298B2 (en) 2017-01-09 2021-12-14 Universal Display Corporation Organic electroluminescent materials and devices
US11201299B2 (en) 2017-05-04 2021-12-14 Universal Display Corporation Organic electroluminescent materials and devices
US11217757B2 (en) 2018-03-12 2022-01-04 Universal Display Corporation Host materials for electroluminescent devices
US11214587B2 (en) 2017-11-07 2022-01-04 Universal Display Corporation Organic electroluminescent materials and devices
US11228010B2 (en) 2017-07-26 2022-01-18 Universal Display Corporation Organic electroluminescent materials and devices
US11228003B2 (en) 2016-04-22 2022-01-18 Universal Display Corporation Organic electroluminescent materials and devices
US11228004B2 (en) 2018-06-22 2022-01-18 Universal Display Corporation Organic electroluminescent materials and devices
US11228002B2 (en) 2016-04-22 2022-01-18 Universal Display Corporation Organic electroluminescent materials and devices
US11233203B2 (en) 2018-09-06 2022-01-25 Universal Display Corporation Organic electroluminescent materials and devices
US11233205B2 (en) 2017-12-14 2022-01-25 Universal Display Corporation Organic electroluminescent materials and devices
US11233204B2 (en) 2017-12-14 2022-01-25 Universal Display Corporation Organic electroluminescent materials and devices
US11239432B2 (en) 2016-10-14 2022-02-01 Universal Display Corporation Organic electroluminescent materials and devices
US11239434B2 (en) 2018-02-09 2022-02-01 Universal Display Corporation Organic electroluminescent materials and devices
US11239433B2 (en) 2017-07-26 2022-02-01 Universal Display Corporation Organic electroluminescent materials and devices
US11261207B2 (en) 2018-06-25 2022-03-01 Universal Display Corporation Organic electroluminescent materials and devices
US11271177B2 (en) 2018-01-11 2022-03-08 Universal Display Corporation Organic electroluminescent materials and devices
US11276829B2 (en) 2017-03-31 2022-03-15 Universal Display Corporation Organic electroluminescent materials and devices
US11279722B2 (en) 2018-03-12 2022-03-22 Universal Display Corporation Organic electroluminescent materials and devices
US11296283B2 (en) 2018-06-04 2022-04-05 Universal Display Corporation Organic electroluminescent materials and devices
US11302872B2 (en) 2015-09-09 2022-04-12 Universal Display Corporation Organic electroluminescent materials and devices
US11322691B2 (en) 2017-07-26 2022-05-03 Universal Display Corporation Organic electroluminescent materials and devices
US11325932B2 (en) 2019-02-08 2022-05-10 Universal Display Corporation Organic electroluminescent materials and devices
US11342509B2 (en) 2018-02-09 2022-05-24 Universal Display Corporation Organic electroluminescent materials and devices
US11339182B2 (en) 2018-06-07 2022-05-24 Universal Display Corporation Organic electroluminescent materials and devices
US11342513B2 (en) 2018-05-04 2022-05-24 Universal Display Corporation Organic electroluminescent materials and devices
US11349083B2 (en) 2017-08-10 2022-05-31 Universal Display Corporation Organic electroluminescent materials and devices
US11367840B2 (en) 2018-01-26 2022-06-21 Universal Display Corporation Organic electroluminescent materials and devices
US11370809B2 (en) 2019-02-08 2022-06-28 Universal Display Corporation Organic electroluminescent materials and devices
US11374181B2 (en) 2019-08-14 2022-06-28 Universal Display Corporation Organic electroluminescent materials and devices
US11390639B2 (en) 2018-04-13 2022-07-19 Universal Display Corporation Organic electroluminescent materials and devices
US11424420B2 (en) 2017-09-07 2022-08-23 Universal Display Corporation Organic electroluminescent materials and devices
US11437591B2 (en) 2017-08-24 2022-09-06 Universal Display Corporation Organic electroluminescent materials and devices
US11444249B2 (en) 2017-09-07 2022-09-13 Universal Display Corporation Organic electroluminescent materials and devices
US11450822B2 (en) 2018-05-25 2022-09-20 Universal Display Corporation Organic electroluminescent materials and devices
US11459349B2 (en) 2018-05-25 2022-10-04 Universal Display Corporation Organic electroluminescent materials and devices
US11462697B2 (en) 2017-08-22 2022-10-04 Universal Display Corporation Organic electroluminescent materials and devices
US11469382B2 (en) 2017-07-12 2022-10-11 Universal Display Corporation Organic electroluminescent materials and devices
US11469383B2 (en) 2018-10-08 2022-10-11 Universal Display Corporation Organic electroluminescent materials and devices
US11469384B2 (en) 2018-11-02 2022-10-11 Universal Display Corporation Organic electroluminescent materials and devices
US11476430B2 (en) 2018-10-15 2022-10-18 Universal Display Corporation Organic electroluminescent materials and devices
US11482683B2 (en) 2016-06-20 2022-10-25 Universal Display Corporation Organic electroluminescent materials and devices
US11485706B2 (en) 2018-09-11 2022-11-01 Universal Display Corporation Organic electroluminescent materials and devices
US11495752B2 (en) 2018-10-08 2022-11-08 Universal Display Corporation Organic electroluminescent materials and devices
US11495756B2 (en) 2019-05-07 2022-11-08 Universal Display Corporation Organic electroluminescent materials and devices
US11495757B2 (en) 2017-06-23 2022-11-08 Universal Display Corporation Organic electroluminescent materials and devices
US11495749B2 (en) 2015-04-06 2022-11-08 Universal Display Corporation Organic electroluminescent materials and devices
US11508913B2 (en) 2017-08-10 2022-11-22 Universal Display Corporation Organic electroluminescent materials and devices
US11512093B2 (en) 2019-03-04 2022-11-29 Universal Display Corporation Compound used for organic light emitting device (OLED), consumer product and formulation
US11515489B2 (en) 2018-11-28 2022-11-29 Universal Display Corporation Host materials for electroluminescent devices
US11515482B2 (en) 2018-10-23 2022-11-29 Universal Display Corporation Deep HOMO (highest occupied molecular orbital) emitter device structures
US11515494B2 (en) 2018-05-04 2022-11-29 Universal Display Corporation Organic electroluminescent materials and devices
US11515493B2 (en) 2018-01-11 2022-11-29 Universal Display Corporation Organic electroluminescent materials and devices
US11522140B2 (en) 2015-08-17 2022-12-06 Universal Display Corporation Organic electroluminescent materials and devices
DE112012002237B4 (en) 2011-05-25 2022-12-22 Universal Display Corporation Host Materials for OLEDS
US11545636B2 (en) 2016-12-15 2023-01-03 Universal Display Corporation Organic electroluminescent materials and devices
US11542289B2 (en) 2018-01-26 2023-01-03 Universal Display Corporation Organic electroluminescent materials and devices
US11545637B2 (en) 2017-01-13 2023-01-03 Universal Display Corporation Organic electroluminescent materials and devices
US11552261B2 (en) 2017-06-23 2023-01-10 Universal Display Corporation Organic electroluminescent materials and devices
US11548905B2 (en) 2016-12-15 2023-01-10 Universal Display Corporation Organic electroluminescent materials and devices
US11555048B2 (en) 2016-12-01 2023-01-17 Universal Display Corporation Organic electroluminescent materials and devices
US11557738B2 (en) 2019-02-22 2023-01-17 Universal Display Corporation Organic electroluminescent materials and devices
US11557733B2 (en) 2018-03-12 2023-01-17 Universal Display Corporation Organic electroluminescent materials and devices
US11560398B2 (en) 2019-05-07 2023-01-24 Universal Display Corporation Organic electroluminescent materials and devices
US11569480B2 (en) 2019-03-12 2023-01-31 Universal Display Corporation Plasmonic OLEDs and vertical dipole emitters
US11600787B2 (en) 2019-08-30 2023-03-07 Universal Display Corporation Organic electroluminescent materials and devices
US11605791B2 (en) 2017-09-01 2023-03-14 Universal Display Corporation Organic electroluminescent materials and devices
US11608321B2 (en) 2017-06-23 2023-03-21 Universal Display Corporation Organic electroluminescent materials and devices
US11616203B2 (en) 2018-04-17 2023-03-28 Universal Display Corporation Organic electroluminescent materials and devices
US11613550B2 (en) 2019-04-30 2023-03-28 Universal Display Corporation Organic electroluminescent materials and devices comprising benzimidazole-containing metal complexes
US11623936B2 (en) 2018-12-11 2023-04-11 Universal Display Corporation Organic electroluminescent materials and devices
US11637261B2 (en) 2019-03-12 2023-04-25 Universal Display Corporation Nanopatch antenna outcoupling structure for use in OLEDs
US11634445B2 (en) 2019-05-21 2023-04-25 Universal Display Corporation Organic electroluminescent materials and devices
US11639363B2 (en) 2019-04-22 2023-05-02 Universal Display Corporation Organic electroluminescent materials and devices
US11647667B2 (en) 2019-06-14 2023-05-09 Universal Display Corporation Organic electroluminescent compounds and organic light emitting devices using the same
US11672165B2 (en) 2018-11-28 2023-06-06 Universal Display Corporation Organic electroluminescent materials and devices
US11672176B2 (en) 2018-11-28 2023-06-06 Universal Display Corporation Host materials for electroluminescent devices
US11678565B2 (en) 2017-06-23 2023-06-13 Universal Display Corporation Organic electroluminescent materials and devices
US11685754B2 (en) 2019-07-22 2023-06-27 Universal Display Corporation Heteroleptic organic electroluminescent materials
US11690285B2 (en) 2018-11-28 2023-06-27 Universal Display Corporation Electroluminescent devices
US11696492B2 (en) 2017-09-07 2023-07-04 Universal Display Corporation Organic electroluminescent materials and devices
US11700765B2 (en) 2018-01-10 2023-07-11 Universal Display Corporation Organic electroluminescent materials and devices
US11697653B2 (en) 2019-10-21 2023-07-11 Universal Display Corporation Organic electroluminescent materials and devices
US11706972B2 (en) 2015-09-08 2023-07-18 Universal Display Corporation Organic electroluminescent materials and devices
US11708355B2 (en) 2019-08-01 2023-07-25 Universal Display Corporation Organic electroluminescent materials and devices
US11716900B2 (en) 2018-05-30 2023-08-01 Universal Display Corporation Host materials for electroluminescent devices
US11716899B2 (en) 2018-11-28 2023-08-01 Universal Display Corporation Organic electroluminescent materials and devices
US11718634B2 (en) 2018-09-14 2023-08-08 Universal Display Corporation Organic electroluminescent materials and devices
US11723269B2 (en) 2017-08-22 2023-08-08 Universal Display Corporation Organic electroluminescent materials and devices
US11725022B2 (en) 2017-06-23 2023-08-15 Universal Display Corporation Organic electroluminescent materials and devices
US11737349B2 (en) 2018-12-12 2023-08-22 Universal Display Corporation Organic electroluminescent materials and devices
US11744141B2 (en) 2017-08-09 2023-08-29 Universal Display Corporation Organic electroluminescent materials and devices
US11739081B2 (en) 2019-03-11 2023-08-29 Universal Display Corporation Organic electroluminescent materials and devices
US11744142B2 (en) 2017-08-10 2023-08-29 Universal Display Corporation Organic electroluminescent materials and devices
US11753427B2 (en) 2018-05-04 2023-09-12 Universal Display Corporation Organic electroluminescent materials and devices
US11753425B2 (en) 2018-07-11 2023-09-12 Universal Display Corporation Organic electroluminescent materials and devices
US11758804B2 (en) 2017-06-23 2023-09-12 Universal Display Corporation Organic electroluminescent materials and devices
US11765968B2 (en) 2017-01-23 2023-09-19 Universal Display Corporation Organic electroluminescent materials and devices
US11765965B2 (en) 2019-10-30 2023-09-19 Universal Display Corporation Organic electroluminescent materials and devices
US11765970B2 (en) 2017-07-26 2023-09-19 Universal Display Corporation Organic electroluminescent materials and devices
US11773320B2 (en) 2019-02-21 2023-10-03 Universal Display Corporation Organic electroluminescent materials and devices
US11778895B2 (en) 2020-01-13 2023-10-03 Universal Display Corporation Organic electroluminescent materials and devices
US11778897B2 (en) 2017-09-20 2023-10-03 Universal Display Corporation Organic electroluminescent materials and devices
US11780865B2 (en) 2017-01-09 2023-10-10 Universal Display Corporation Organic electroluminescent materials and devices
US11780829B2 (en) 2019-01-30 2023-10-10 The University Of Southern California Organic electroluminescent materials and devices
US11793073B2 (en) 2018-05-06 2023-10-17 Universal Display Corporation Host materials for electroluminescent devices
US11802136B2 (en) 2017-06-23 2023-10-31 Universal Display Corporation Organic electroluminescent materials and devices
US11812624B2 (en) 2019-01-30 2023-11-07 The University Of Southern California Organic electroluminescent materials and devices
US11812622B2 (en) 2015-09-25 2023-11-07 Universal Display Corporation Organic electroluminescent compounds and devices
US11814403B2 (en) 2017-06-23 2023-11-14 Universal Display Corporation Organic electroluminescent materials and devices
US11818949B2 (en) 2015-04-06 2023-11-14 Universal Display Corporation Organic electroluminescent materials and devices
US11820783B2 (en) 2019-09-06 2023-11-21 Universal Display Corporation Organic electroluminescent materials and devices
US11825735B2 (en) 2017-11-28 2023-11-21 Universal Display Corporation Organic electroluminescent materials and devices
US11825736B2 (en) 2018-11-19 2023-11-21 Universal Display Corporation Organic electroluminescent materials and devices
US11827651B2 (en) 2019-05-13 2023-11-28 Universal Display Corporation Organic electroluminescent materials and devices
US11832510B2 (en) 2017-06-23 2023-11-28 Universal Display Corporation Organic electroluminescent materials and devices
US11834459B2 (en) 2018-12-12 2023-12-05 Universal Display Corporation Host materials for electroluminescent devices
US11845764B2 (en) 2018-01-26 2023-12-19 Universal Display Corporation Organic electroluminescent materials and devices
US11864458B2 (en) 2019-10-08 2024-01-02 Universal Display Corporation Organic electroluminescent materials and devices
US11871653B2 (en) 2019-02-22 2024-01-09 Universal Display Corporation Organic electroluminescent materials and devices
US11882759B2 (en) 2018-04-13 2024-01-23 Universal Display Corporation Organic electroluminescent materials and devices
US11889708B2 (en) 2019-11-14 2024-01-30 Universal Display Corporation Organic electroluminescent materials and devices
US11903305B2 (en) 2018-09-24 2024-02-13 Universal Display Corporation Organic electroluminescent materials and devices
US11910700B2 (en) 2009-03-23 2024-02-20 Universal Display Corporation Heteroleptic iridium complexes as dopants
US11910702B2 (en) 2017-11-07 2024-02-20 Universal Display Corporation Organic electroluminescent devices
US11910699B2 (en) 2017-08-10 2024-02-20 Universal Display Corporation Organic electroluminescent materials and devices
US11917900B2 (en) 2020-01-28 2024-02-27 Universal Display Corporation Organic electroluminescent materials and devices
US11917843B2 (en) 2017-07-26 2024-02-27 Universal Display Corporation Organic electroluminescent materials and devices
US11925102B2 (en) 2015-06-04 2024-03-05 Universal Display Corporation Organic electroluminescent materials and devices
US11919914B2 (en) 2019-10-25 2024-03-05 Universal Display Corporation Organic electroluminescent materials and devices
US11925105B2 (en) 2019-08-26 2024-03-05 Universal Display Corporation Organic electroluminescent materials and devices
US11920070B2 (en) 2019-07-12 2024-03-05 The University Of Southern California Luminescent janus-type, two-coordinated metal complexes
US11925103B2 (en) 2018-06-05 2024-03-05 Universal Display Corporation Organic electroluminescent materials and devices
US11926638B2 (en) 2019-07-22 2024-03-12 Universal Display Corporation Organic electroluminescent materials and devices
US11930699B2 (en) 2019-08-15 2024-03-12 Universal Display Corporation Organic electroluminescent materials and devices
US11932660B2 (en) 2021-01-04 2024-03-19 Universal Display Corporation Organic electroluminescent materials and devices

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001123982A (en) * 1999-10-25 2001-05-08 Hitachi Ltd Horizontal shaft pump device
JP2002117978A (en) * 2000-07-17 2002-04-19 Fuji Photo Film Co Ltd Luminescent element and iridium complex
JP2002226495A (en) * 2000-11-29 2002-08-14 Canon Inc Metal coordination compound, light emitting element and display device
JP2002234894A (en) * 2000-11-29 2002-08-23 Canon Inc Metal coordination compound, light emission element and display device
JP2002332992A (en) * 2001-05-11 2002-11-22 Toyota Central Res & Dev Lab Inc Impeller of centrifugal compressor
JP2002332291A (en) * 2001-03-08 2002-11-22 Canon Inc Metal coordination compound, electroluminescent device, and display unit
JP2002338588A (en) * 2001-03-14 2002-11-27 Canon Inc Metal coordinated compound, electroluminescent element and display device
JP2003146996A (en) * 2000-09-26 2003-05-21 Canon Inc Light emission element, display and metal coordination compound for the light emission element
WO2004016711A1 (en) * 2002-08-16 2004-02-26 The University Of Southern California Organic light emitting materials and devices

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4460743B2 (en) * 2000-09-29 2010-05-12 富士フイルム株式会社 Method for producing iridium complex or tautomer thereof
JP4154145B2 (en) * 2000-12-01 2008-09-24 キヤノン株式会社 Metal coordination compound, light emitting device and display device
JP2002359079A (en) * 2001-05-31 2002-12-13 Canon Inc Light emitting element and display device
JP2003123982A (en) * 2001-08-07 2003-04-25 Fuji Photo Film Co Ltd Light emitting element and novel iridium complex
JP2003342284A (en) * 2002-05-30 2003-12-03 Canon Inc Metal coordination compound, light-generating element and display device
US8178214B2 (en) * 2004-02-26 2012-05-15 Konica Minolta Holdings, Inc. Material for organic electroluminescence element, organic electroluminescence element, display device and illumination device

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001123982A (en) * 1999-10-25 2001-05-08 Hitachi Ltd Horizontal shaft pump device
JP2002117978A (en) * 2000-07-17 2002-04-19 Fuji Photo Film Co Ltd Luminescent element and iridium complex
JP2003146996A (en) * 2000-09-26 2003-05-21 Canon Inc Light emission element, display and metal coordination compound for the light emission element
JP2002226495A (en) * 2000-11-29 2002-08-14 Canon Inc Metal coordination compound, light emitting element and display device
JP2002234894A (en) * 2000-11-29 2002-08-23 Canon Inc Metal coordination compound, light emission element and display device
JP2002332291A (en) * 2001-03-08 2002-11-22 Canon Inc Metal coordination compound, electroluminescent device, and display unit
JP2002338588A (en) * 2001-03-14 2002-11-27 Canon Inc Metal coordinated compound, electroluminescent element and display device
JP2002332992A (en) * 2001-05-11 2002-11-22 Toyota Central Res & Dev Lab Inc Impeller of centrifugal compressor
WO2004016711A1 (en) * 2002-08-16 2004-02-26 The University Of Southern California Organic light emitting materials and devices

Cited By (695)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1647554A2 (en) * 2003-07-22 2006-04-19 Idemitsu Kosan Co., Ltd. Metal complex compound and organic electroluminescent device using same
EP1647554A4 (en) * 2003-07-22 2008-02-20 Idemitsu Kosan Co Metal complex compound and organic electroluminescent device using same
US8178874B2 (en) 2003-07-22 2012-05-15 Idemitsu Kosan Co., Ltd. Metal complex compound and organic electroluminescent device using same
US8106390B2 (en) 2003-07-22 2012-01-31 Idemitsu Kosan Co., Ltd. Metal complex compound and organic electroluminescent device using same
US7667228B2 (en) 2003-07-22 2010-02-23 Idemitsu Kosan Co., Ltd. Metal complex compound and organic electroluminescent device using same
US9871219B2 (en) 2005-04-13 2018-01-16 Universal Display Corporation Organic light emitting devices
US9647227B2 (en) 2005-04-13 2017-05-09 Universal Display Corporation Organic light emitting devices
US9735377B2 (en) 2005-05-06 2017-08-15 Universal Display Corporation Phosphorescent emitters and host materials with improved stability
US9548462B2 (en) 2006-02-10 2017-01-17 Universal Display Corporation Organic electroluminescent materials and devices
US10403831B2 (en) 2006-02-10 2019-09-03 Universal Display Corporation Organic electroluminescent materials and devices
US9065063B2 (en) 2006-02-10 2015-06-23 Universal Display Corporation Metal complexes of cyclometallated imidazo[1,2-f]phenanthridine and diimidazo[1,2-a:1′,2′-c]quinazoline ligands and isoelectronic and benzannulated analogs thereof
US9893306B2 (en) 2006-02-10 2018-02-13 Universal Display Corporation Organic electroluminescent materials and devices
US10158090B2 (en) 2006-02-10 2018-12-18 Universal Display Corporation Organic electroluminescent materials and devices
US9281483B2 (en) 2006-02-10 2016-03-08 Universal Display Corporation Organic electroluminescent materials and devices
US10978649B2 (en) 2006-02-10 2021-04-13 Universal Display Corporation Organic electroluminescent materials and devices
US8889864B2 (en) 2006-02-10 2014-11-18 Universal Display Corporation Metal complexes of cyclometallated imidazo[1,2-f]phenanthridine and diimidazo[1,2-a:1′,2′-c]quinazoline ligands and isoelectronic and benzannulated analogs thereof
US10749121B2 (en) 2006-02-10 2020-08-18 Universal Display Corporation Organic electroluminescent materials and devices
JP2008160098A (en) * 2006-11-30 2008-07-10 Semiconductor Energy Lab Co Ltd Light emitting element, light emitting device, and electronic equipment
TWI558264B (en) * 2006-11-30 2016-11-11 半導體能源研究所股份有限公司 Light-emitting device
US10764974B2 (en) 2006-11-30 2020-09-01 Semiconductor Energy Laboratory Co., Ltd. Light-emitting device using organometallic complex having a pyrazine skeleton
US10129947B2 (en) 2006-11-30 2018-11-13 Semiconductor Energy Laboratory Co., Ltd. Light-emitting device using organometallic complex
US9899612B2 (en) 2006-12-08 2018-02-20 Universal Display Corporation Organic electroluminescent materials and devices
US8866377B2 (en) 2006-12-28 2014-10-21 Universal Display Corporation Long lifetime phosphorescent organic light emitting device (OLED) structures
US8030490B2 (en) * 2006-12-29 2011-10-04 National Tsing Hua University Phosphorescent iridium complex with non-conjugated cyclometalated ligands, synthetic method of preparing the same and phosphorescent organic light emitting diode thereof
US8592585B2 (en) 2006-12-29 2013-11-26 National Tsing Hua University Phosphorescent iridium complex with non-conjugated cyclometalated ligands, synthetic method of preparing the same and phosphorescent organic light emitting diode thereof
US8410269B2 (en) 2006-12-29 2013-04-02 National Tsing Hua University Phosphorescent iridium complex with non-conjugated cyclometalated ligands, synthetic method of preparing the same and phosphorescent organic light emitting diode thereof
JP2010516040A (en) * 2007-01-16 2010-05-13 エルジー・ケム・リミテッド Electrolyte containing eutectic mixture and secondary battery using the same
US9577201B2 (en) 2007-03-08 2017-02-21 Universal Display Corporation Organic electroluminescent materials and devices
US11495755B2 (en) 2007-03-08 2022-11-08 Universal Display Corporation Organic electroluminescent materials and devices
US9853227B2 (en) 2007-03-08 2017-12-26 Universal Display Corporation Organic electroluminescent materials and devices
US10230060B2 (en) 2007-03-08 2019-03-12 Universal Display Corporation Organic electroluminescent materials and devices
US9190621B2 (en) 2007-03-08 2015-11-17 Universal Display Corporation Materials for organic light emitting diode
US9142786B2 (en) 2007-03-08 2015-09-22 Universal Display Corporation Phosphorescent materials
US10600975B2 (en) 2007-03-08 2020-03-24 Universal Display Corporation Organic electroluminescent materials and devices
US9911930B2 (en) 2007-03-08 2018-03-06 Universal Display Corporation Organic electroluminescent materials and devices
US8734962B2 (en) 2007-05-21 2014-05-27 Osram Opto Semiconductors Gmbh Phosphorescent metal complex compound radiation emitting component comprising a phosphorescent metal complex compound and method for production of a phosphorescent metal complex compound
US9966544B2 (en) 2007-05-21 2018-05-08 Osram Oled Gmbh Phosphorescent metal complex compound radiation emitting component comprising a phosphorescent metal complex compound and method for production of a phosphorescent metal complex compound
US9590180B2 (en) 2007-06-23 2017-03-07 Universal Display Corporation Organic electroluminescent materials and devices
US10957858B2 (en) 2007-08-08 2021-03-23 Universal Display Corporation Organic electroluminescent materials and devices
US9153786B2 (en) 2007-08-08 2015-10-06 Universal Display Corporation Organic electroluminescent materials and devices
US9608206B2 (en) 2007-08-08 2017-03-28 Universal Display Corporation Organic electroluminescent materials and devices
US9997727B2 (en) 2007-08-08 2018-06-12 Universal Display Corporation Organic electroluminescent materials and devices
US11690286B2 (en) 2007-08-08 2023-06-27 Universal Display Corporation Organic electroluminescent materials and devices
US10312450B2 (en) 2007-08-08 2019-06-04 Universal Display Corporation Organic electroluminescent materials and devices
US8822708B2 (en) 2007-08-08 2014-09-02 Universal Display Corporation Benzo-fused thiophene / triphenylene hybrid materials
US9577200B2 (en) 2007-08-08 2017-02-21 Universal Display Corporation Organic electroluminescent materials and devices
US10374171B2 (en) 2007-08-08 2019-08-06 Universal Display Corporation Organic electroluminescent materials and devices
US9139764B2 (en) 2007-09-28 2015-09-22 Osram Opto Semiconductors Gmbh Organic radiation-emitting component
DE102007046445A1 (en) 2007-09-28 2009-04-16 Osram Opto Semiconductors Gmbh Organic radiation-emitting component, useful as organic light-emitting diode, comprises substrate, lower electrode layer, organic radiation-emitting layer with matrix containing radiation emitting metal complex and upper electrode layer
US9123903B2 (en) 2007-12-28 2015-09-01 Universal Display Corporation Dibenzothiophene-containing materials in phosphorescent light emitting diodes
US8221905B2 (en) 2007-12-28 2012-07-17 Universal Display Corporation Carbazole-containing materials in phosphorescent light emitting diodes
US8580402B2 (en) 2007-12-28 2013-11-12 Universal Display Corporation Dibenzothiophene-containing materials in phosphorescent light emitting diodes
US8586204B2 (en) 2007-12-28 2013-11-19 Universal Display Corporation Phosphorescent emitters and host materials with improved stability
US8007927B2 (en) 2007-12-28 2011-08-30 Universal Display Corporation Dibenzothiophene-containing materials in phosphorescent light emitting diodes
US9997726B2 (en) 2007-12-28 2018-06-12 Universal Display Corporation Dibenzothiophene-containing materials in phosphorescent light emitting diodes
US8040053B2 (en) 2008-02-09 2011-10-18 Universal Display Corporation Organic light emitting device architecture for reducing the number of organic materials
WO2010006666A1 (en) * 2008-07-17 2010-01-21 Merck Patent Gmbh Organic electroluminescence device
US8618317B2 (en) 2008-07-17 2013-12-31 Merck Patent Gmbh Organic electroluminescence device
WO2010007107A1 (en) 2008-07-18 2010-01-21 Siemens Aktiengesellschaft Phosphorescent metal complex compound, method for the preparation thereof and radiating component
US9012038B2 (en) 2008-07-18 2015-04-21 Osram Gmbh Phosphorescent metal complex compound, method for the preparation thereof and radiating component
DE102008033929A1 (en) 2008-07-18 2010-01-21 Siemens Aktiengesellschaft Phosphorescent metal complex compound, process for the preparation thereof and radiation-emitting component
US9630983B2 (en) 2008-09-03 2017-04-25 Universal Display Corporation Organic electroluminescent material and devices
US10186672B2 (en) 2008-09-03 2019-01-22 Universal Display Corporation Organic electroluminescent materials and devices
US11482685B2 (en) 2008-09-03 2022-10-25 Universal Display Corporation Organic electroluminescent materials and devices
US10892426B2 (en) 2008-09-03 2021-01-12 Universal Display Corporation Organic electroluminescent materials and devices
US8519384B2 (en) 2008-09-03 2013-08-27 Universal Display Corporation Phosphorescent materials
US10593896B2 (en) 2008-09-03 2020-03-17 Universal Display Corporation Organic electroluminescent materials and devices
US9076973B2 (en) 2008-09-03 2015-07-07 Universal Display Corporation Phosphorescent materials
US8513658B2 (en) 2008-09-04 2013-08-20 Universal Display Corporation White phosphorescent organic light emitting devices
US9034483B2 (en) 2008-09-16 2015-05-19 Universal Display Corporation Phosphorescent materials
US10084143B2 (en) 2008-09-16 2018-09-25 Universal Display Corporation Phosphorescent materials
US9455411B2 (en) 2008-09-25 2016-09-27 Universal Display Corporation Organic electroluminescent materials and devices
US8053770B2 (en) 2008-10-14 2011-11-08 Universal Display Corporation Emissive layer patterning for OLED
US8597798B2 (en) 2008-11-13 2013-12-03 Merck Patent Gmbh Materials for organic electroluminescent devices
JP2012508700A (en) * 2008-11-13 2012-04-12 メルク パテント ゲーエムベーハー Materials for organic electroluminescent devices
WO2010054731A1 (en) * 2008-11-13 2010-05-20 Merck Patent Gmbh Materials for organic electroluminescent devices
US8815415B2 (en) 2008-12-12 2014-08-26 Universal Display Corporation Blue emitter with high efficiency based on imidazo[1,2-f] phenanthridine iridium complexes
US10008678B2 (en) 2008-12-12 2018-06-26 Universal Display Corporation Organic electroluminescent materials and devices
US8778511B2 (en) 2008-12-12 2014-07-15 Universal Display Corporation OLED stability via doped hole transport layer
US9518063B2 (en) 2009-01-16 2016-12-13 Universal Display Corporation Organic electroluminescent materials and devices
US9067947B2 (en) 2009-01-16 2015-06-30 Universal Display Corporation Organic electroluminescent materials and devices
US9831442B2 (en) 2009-01-16 2017-11-28 Universal Display Corporation Organic electroluminescent materials and devices
US8952363B2 (en) 2009-01-16 2015-02-10 Universal Display Corporation Organic electroluminescent materials and devices
US10312458B2 (en) 2009-03-23 2019-06-04 Universal Display Corporation Organic electroluminescent materials and devices
US10056566B2 (en) 2009-03-23 2018-08-21 Universal Display Corporation Organic electroluminescent materials and devices
US11380854B2 (en) 2009-03-23 2022-07-05 Universal Display Corporation Heteroleptic iridium complexes as dopants
US9184397B2 (en) 2009-03-23 2015-11-10 Universal Display Corporation Heteroleptic iridium complexes as dopants
US8722205B2 (en) 2009-03-23 2014-05-13 Universal Display Corporation Heteroleptic iridium complex
US11910701B2 (en) 2009-03-23 2024-02-20 Universal Display Corporation Organic electroluminescent materials and devices
US11637251B2 (en) 2009-03-23 2023-04-25 Universal Display Corporation Organic electroluminescent materials and devices
US11910700B2 (en) 2009-03-23 2024-02-20 Universal Display Corporation Heteroleptic iridium complexes as dopants
US9359549B2 (en) 2009-04-06 2016-06-07 Universal Display Corporation Organic electroluminescent materials and devices
US8557400B2 (en) 2009-04-28 2013-10-15 Universal Display Corporation Iridium complex with methyl-D3 substitution
US10374173B2 (en) 2009-04-28 2019-08-06 Universal Display Corporation Organic electroluminescent materials and devices
US9634265B2 (en) 2009-04-28 2017-04-25 Universal Display Corporation Organic electroluminescent materials and devices
US9005771B2 (en) 2009-05-12 2015-04-14 Universal Display Corporation 2-azatriphenylene materials for organic light emitting diodes
US9673406B2 (en) 2009-05-20 2017-06-06 Universal Display Corporation Metal complexes with boron-nitrogen heterocycle containing ligands
TWI421329B (en) * 2009-05-27 2014-01-01 Nat Univ Tsing Hua Iridium complexes and organic light-emitting diodes comprising the same
DE102009031683A1 (en) 2009-07-03 2011-03-24 Siemens Aktiengesellschaft Phophorescent metal complex compound, process for the preparation thereof and radiation-emitting component
US9773986B2 (en) 2009-11-19 2017-09-26 The University Of Southern California Copper(I)-carbene complexes and organic electroluminescent devices
US9054344B2 (en) 2010-01-20 2015-06-09 Universal Display Corporation Electroluminescent devices for lighting applications
WO2011088918A1 (en) 2010-01-25 2011-07-28 Siemens Aktiengesellschaft Use of a guanidinium cation in a light-emitting component
US9375392B2 (en) 2010-01-25 2016-06-28 Osram Ag Use of the guanidinium cation and light-emitting component
US9169434B2 (en) 2010-01-25 2015-10-27 Osram Ag Phosphorescent metal complex, process for production and light-emitting component
DE102010005632A1 (en) 2010-01-25 2011-07-28 Siemens Aktiengesellschaft, 80333 Phosphorescent metal complex compound, method of preparation and light emitting device
DE102010005634A1 (en) 2010-01-25 2011-07-28 Siemens Aktiengesellschaft, 80333 Novel use of guanidinium cation and light-emitting device
US9156870B2 (en) 2010-02-25 2015-10-13 Universal Display Corporation Phosphorescent emitters
US9175211B2 (en) 2010-03-03 2015-11-03 Universal Display Corporation Phosphorescent materials
US8963132B2 (en) 2010-03-25 2015-02-24 Universal Display Corporation Solution processable doped triarylamine hole injection materials
US8968887B2 (en) 2010-04-28 2015-03-03 Universal Display Corporation Triphenylene-benzofuran/benzothiophene/benzoselenophene compounds with substituents joining to form fused rings
US9040962B2 (en) 2010-04-28 2015-05-26 Universal Display Corporation Depositing premixed materials
US9140428B2 (en) 2010-06-11 2015-09-22 Universal Display Corporation Triplet-triplet annihilation up-conversation for display and lighting applications
US9543532B2 (en) 2010-06-11 2017-01-10 Universal Display Corporation Organic electroluminescent materials and devices
US9435021B2 (en) 2010-07-29 2016-09-06 University Of Southern California Co-deposition methods for the fabrication of organic optoelectronic devices
US11316113B2 (en) 2010-08-20 2022-04-26 Universal Display Corporation Organic electroluminescent materials and devices
US11289659B2 (en) 2010-08-20 2022-03-29 Universal Display Corporation Organic electroluminescent materials and devices
US9954180B2 (en) 2010-08-20 2018-04-24 Universal Display Corporation Bicarbazole compounds for OLEDs
US8932734B2 (en) 2010-10-08 2015-01-13 Universal Display Corporation Organic electroluminescent materials and devices
US9401482B2 (en) 2010-10-08 2016-07-26 Universal Display Corporation Organic electroluminescent materials and devices
US10147892B2 (en) 2010-12-07 2018-12-04 The University Of Southern California Organic electroluminescent materials and devices
US10680189B2 (en) 2011-01-13 2020-06-09 Universal Display Corporation Materials for organic light emitting diodes
US10008677B2 (en) 2011-01-13 2018-06-26 Universal Display Corporation Materials for organic light emitting diode
US11374180B2 (en) 2011-01-13 2022-06-28 Universal Display Corporation Organic electroluminescent materials and devices
US9130177B2 (en) 2011-01-13 2015-09-08 Universal Display Corporation 5-substituted 2 phenylquinoline complexes materials for light emitting diode
US9005772B2 (en) 2011-02-23 2015-04-14 Universal Display Corporation Thioazole and oxazole carbene metal complexes as phosphorescent OLED materials
US10388890B2 (en) 2011-02-23 2019-08-20 Universal Display Corporation Organic electroluminescent heterocyclic carbene metal complexes and devices containing the same
US9947880B2 (en) 2011-02-23 2018-04-17 Universal Display Corporation Organic electroluminescent materials and devices
US8871361B2 (en) 2011-02-23 2014-10-28 Universal Display Corporation Tetradentate platinum complexes
US10381580B2 (en) 2011-02-23 2019-08-13 Universal Display Corporation Organic electroluminescent materials and devices
US8754232B2 (en) 2011-02-23 2014-06-17 Universal Display Corporation Methods of making bis-tridentate carbene complexes of ruthenium and osmium
US9972793B2 (en) 2011-03-08 2018-05-15 Universal Display Corporation Organic electroluminescent materials and devices
US8883322B2 (en) 2011-03-08 2014-11-11 Universal Display Corporation Pyridyl carbene phosphorescent emitters
US10873038B2 (en) 2011-03-08 2020-12-22 Universal Display Corporation Organic electroluminescent materials and devices
US11600791B2 (en) 2011-03-08 2023-03-07 Universal Display Corporation Organic electroluminescent materials and devices
WO2012124622A1 (en) 2011-03-14 2012-09-20 東レ株式会社 Light-emitting element material and light-emitting element
US9397312B2 (en) 2011-05-11 2016-07-19 Universal Display Corporation Process for fabricating metal bus lines for OLED lighting panels
US8927308B2 (en) 2011-05-12 2015-01-06 Universal Display Corporation Method of forming bus line designs for large-area OLED lighting
WO2012153725A1 (en) 2011-05-12 2012-11-15 東レ株式会社 Light-emitting element material and light-emitting element
US9450027B2 (en) 2011-05-12 2016-09-20 Universal Display Corporation Method of forming bus line designs for large-area OLED lighting
US9257658B2 (en) 2011-05-19 2016-02-09 Universal Display Corporation Method of making organic electroluminescent materials
US9212197B2 (en) 2011-05-19 2015-12-15 Universal Display Corporation Phosphorescent heteroleptic phenylbenzimidazole dopants
DE112012002237B4 (en) 2011-05-25 2022-12-22 Universal Display Corporation Host Materials for OLEDS
US11189805B2 (en) 2011-05-27 2021-11-30 Universal Display Corporation Organic electroluminescent materials and devices
US10079349B2 (en) 2011-05-27 2018-09-18 Universal Display Corporation Organic electroluminescent materials and devices
US10158089B2 (en) 2011-05-27 2018-12-18 Universal Display Corporation Organic electroluminescent materials and devices
US10297769B2 (en) 2011-06-08 2019-05-21 Universal Display Corporation Organic electroluminescent materials and devices
US11063229B2 (en) 2011-06-08 2021-07-13 Universal Display Corporation Organic electroluminescent materials and devices
US9812656B2 (en) 2011-06-08 2017-11-07 Universal Display Corporation Organic electroluminescent materials and devices
US9847495B2 (en) 2011-06-08 2017-12-19 Universal Display Corporation Organic electroluminescent materials and devices
US9755164B2 (en) 2011-06-08 2017-09-05 Universal Display Corporation Organic electroluminescent materials and devices
US10978648B2 (en) 2011-06-08 2021-04-13 Universal Display Corporation Organic electroluminescent materials and devices
US11751455B2 (en) 2011-06-17 2023-09-05 Universal Display Corporation Non-common capping layer on an organic device
US10340313B2 (en) 2011-06-17 2019-07-02 Universal Display Corporation Non-common capping layer on an organic device
US9054343B2 (en) 2011-06-17 2015-06-09 Universal Display Corporation Fine tuning of emission spectra by combination of multiple emitter spectra
US8884316B2 (en) 2011-06-17 2014-11-11 Universal Display Corporation Non-common capping layer on an organic device
US9647221B2 (en) 2011-07-14 2017-05-09 Universal Display Corporation Organic light-emitting devices
US9252377B2 (en) 2011-07-14 2016-02-02 Universal Display Corporation Inorganic hosts in OLEDs
US9397310B2 (en) 2011-07-14 2016-07-19 Universal Display Corporation Organice electroluminescent materials and devices
US10214551B2 (en) 2011-07-25 2019-02-26 Universal Display Corporation Organic electroluminescent materials and devices
US9783564B2 (en) 2011-07-25 2017-10-10 Universal Display Corporation Organic electroluminescent materials and devices
US8709615B2 (en) 2011-07-28 2014-04-29 Universal Display Corporation Heteroleptic iridium complexes as dopants
US9313857B2 (en) 2011-08-04 2016-04-12 Universal Display Corporation Organic electroluminescent materials and devices
US8926119B2 (en) 2011-08-04 2015-01-06 Universal Display Corporation Extendable light source with variable light emitting area
US9493698B2 (en) 2011-08-31 2016-11-15 Universal Display Corporation Organic electroluminescent materials and devices
US9142788B2 (en) 2011-11-14 2015-09-22 Universal Display Corporation Host materials for OLEDs
US9193745B2 (en) 2011-11-15 2015-11-24 Universal Display Corporation Heteroleptic iridium complex
US9217004B2 (en) 2011-11-21 2015-12-22 Universal Display Corporation Organic light emitting materials
US11482684B2 (en) 2011-12-09 2022-10-25 Universal Display Corporation Organic electroluminescent materials and devices
US9512355B2 (en) 2011-12-09 2016-12-06 Universal Display Corporation Organic light emitting materials
US10454046B2 (en) 2011-12-09 2019-10-22 Universal Display Corporation Organic electroluminescent materials and devices
US9455417B2 (en) 2011-12-13 2016-09-27 Universal Display Corporation Split electrode for organic devices
US9461254B2 (en) 2012-01-03 2016-10-04 Universal Display Corporation Organic electroluminescent materials and devices
US8987451B2 (en) 2012-01-03 2015-03-24 Universal Display Corporation Synthesis of cyclometallated platinum(II) complexes
US9163174B2 (en) 2012-01-04 2015-10-20 Universal Display Corporation Highly efficient phosphorescent materials
DE102013200085B4 (en) 2012-01-06 2020-06-18 Universal Display Corporation Highly efficient phosphorescent materials
US8969592B2 (en) 2012-01-10 2015-03-03 Universal Display Corporation Heterocyclic host materials
US9447113B2 (en) 2012-01-10 2016-09-20 Universal Display Corporation Organic electroluminescent materials and devices
US10211413B2 (en) 2012-01-17 2019-02-19 Universal Display Corporation Organic electroluminescent materials and devices
EP2623508A1 (en) 2012-02-02 2013-08-07 Konica Minolta Advanced Layers, Inc. Iridium complex compound, organic electroluminescent element material, organic electroluminescent element, illumination device and display device
US9118017B2 (en) 2012-02-27 2015-08-25 Universal Display Corporation Host compounds for red phosphorescent OLEDs
US9386657B2 (en) 2012-03-15 2016-07-05 Universal Display Corporation Organic Electroluminescent materials and devices
US9548459B2 (en) 2012-03-15 2017-01-17 Universal Display Corporation Organic materials for organic light emitting devices
US9054323B2 (en) 2012-03-15 2015-06-09 Universal Display Corporation Secondary hole transporting layer with diarylamino-phenyl-carbazole compounds
DE102013003605B4 (en) 2012-03-15 2023-08-17 Universal Display Corporation Secondary hole transport layer with tricarbazole compounds
US9184399B2 (en) 2012-05-04 2015-11-10 Universal Display Corporation Asymmetric hosts with triaryl silane side chains
US9773985B2 (en) 2012-05-21 2017-09-26 Universal Display Corporation Organic electroluminescent materials and devices
US9670404B2 (en) 2012-06-06 2017-06-06 Universal Display Corporation Organic electroluminescent materials and devices
US9502672B2 (en) 2012-06-21 2016-11-22 Universal Display Corporation Organic electroluminescent materials and devices
US9725476B2 (en) 2012-07-09 2017-08-08 Universal Display Corporation Silylated metal complexes
US9231218B2 (en) 2012-07-10 2016-01-05 Universal Display Corporation Phosphorescent emitters containing dibenzo[1,4]azaborinine structure
DE102013214144B4 (en) 2012-07-19 2023-02-16 Universal Display Corp. Diarylamino-substituted metal complexes
US9540329B2 (en) 2012-07-19 2017-01-10 Universal Display Corporation Organic electroluminescent materials and devices
US9059412B2 (en) 2012-07-19 2015-06-16 Universal Display Corporation Transition metal complexes containing substituted imidazole carbene as ligands and their application in OLEDs
WO2014017484A1 (en) 2012-07-25 2014-01-30 東レ株式会社 Light emitting element material and light emitting element
US9663544B2 (en) 2012-07-25 2017-05-30 Universal Display Corporation Organic electroluminescent materials and devices
US9627631B2 (en) 2012-07-30 2017-04-18 Universal Display Corporation Organic electroluminescent materials and devices
US9318710B2 (en) 2012-07-30 2016-04-19 Universal Display Corporation Organic electroluminescent materials and devices
US9978958B2 (en) 2012-08-24 2018-05-22 Universal Display Corporation Phosphorescent emitters with phenylimidazole ligands
US8952362B2 (en) 2012-08-31 2015-02-10 The Regents Of The University Of Michigan High efficiency and brightness fluorescent organic light emitting diode by triplet-triplet fusion
US11696459B2 (en) 2012-09-07 2023-07-04 Universal Display Corporation Phosphorescence-sensitized delayed fluorescence light emitting system
US10957870B2 (en) 2012-09-07 2021-03-23 Universal Display Corporation Organic light emitting device
US9287513B2 (en) 2012-09-24 2016-03-15 Universal Display Corporation Organic electroluminescent materials and devices
US10388894B2 (en) 2012-09-25 2019-08-20 Universal Display Corporation Organic electroluminescent materials and devices
US11917902B2 (en) 2012-09-25 2024-02-27 Universal Display Corporation Organic electroluminescent materials and devices
US9312505B2 (en) 2012-09-25 2016-04-12 Universal Display Corporation Organic electroluminescent materials and devices
US9252363B2 (en) 2012-10-04 2016-02-02 Universal Display Corporation Aryloxyalkylcarboxylate solvent compositions for inkjet printing of organic layers
US8692241B1 (en) 2012-11-08 2014-04-08 Universal Display Corporation Transition metal complexes containing triazole and tetrazole carbene ligands
US10510968B2 (en) 2012-11-09 2019-12-17 Universal Display Corporation Organic electroluminescent materials and devices
US9685617B2 (en) 2012-11-09 2017-06-20 Universal Display Corporation Organic electronuminescent materials and devices
US10033002B2 (en) 2012-11-09 2018-07-24 Universal Display Corporation Organic electroluminescent materials and devices
US9634264B2 (en) 2012-11-09 2017-04-25 Universal Display Corporation Organic electroluminescent materials and devices
US8946697B1 (en) 2012-11-09 2015-02-03 Universal Display Corporation Iridium complexes with aza-benzo fused ligands
US11380855B2 (en) 2012-11-09 2022-07-05 Universal Display Corporation Organic electroluminescent materials and devices
US10069090B2 (en) 2012-11-20 2018-09-04 Universal Display Corporation Organic electroluminescent materials and devices
US10847729B2 (en) 2012-11-20 2020-11-24 Universal Display Corporation Organic electroluminescent materials and devices
US9190623B2 (en) 2012-11-20 2015-11-17 Universal Display Corporation Organic electroluminescent materials and devices
US11145831B2 (en) 2012-11-20 2021-10-12 Universal Display Corporation Osmium(IV) complexes for OLED materials
US9512136B2 (en) 2012-11-26 2016-12-06 Universal Display Corporation Organic electroluminescent materials and devices
US9166175B2 (en) 2012-11-27 2015-10-20 Universal Display Corporation Organic electroluminescent materials and devices
US9196860B2 (en) 2012-12-04 2015-11-24 Universal Display Corporation Compounds for triplet-triplet annihilation upconversion
US8716484B1 (en) 2012-12-05 2014-05-06 Universal Display Corporation Hole transporting materials with twisted aryl groups
US11716902B2 (en) 2012-12-07 2023-08-01 Universal Display Corporation Organic electroluminescent materials and devices
US9670185B2 (en) 2012-12-07 2017-06-06 Universal Display Corporation Organic electroluminescent materials and devices
US10910564B2 (en) 2012-12-07 2021-02-02 Universal Display Corporation Organic electroluminescent materials and devices
US9209411B2 (en) 2012-12-07 2015-12-08 Universal Display Corporation Organic electroluminescent materials and devices
US10069081B2 (en) 2012-12-07 2018-09-04 Universal Display Corporation Organic electroluminescent materials and devices
US9653691B2 (en) 2012-12-12 2017-05-16 Universal Display Corporation Phosphorescence-sensitizing fluorescence material system
US10400163B2 (en) 2013-02-08 2019-09-03 Universal Display Corporation Organic electroluminescent materials and devices
US10367154B2 (en) 2013-02-21 2019-07-30 Universal Display Corporation Organic electroluminescent materials and devices
US11871652B2 (en) 2013-02-21 2024-01-09 Universal Display Corporation Organic electroluminescent materials and devices
US9935276B2 (en) 2013-02-21 2018-04-03 Universal Display Corporation Organic electroluminescent materials and devices
US8927749B2 (en) 2013-03-07 2015-01-06 Universal Display Corporation Organic electroluminescent materials and devices
US9419225B2 (en) 2013-03-14 2016-08-16 Universal Display Corporation Organic electroluminescent materials and devices
US9997712B2 (en) 2013-03-27 2018-06-12 Universal Display Corporation Organic electroluminescent materials and devices
US9537106B2 (en) 2013-05-09 2017-01-03 Universal Display Corporation Organic electroluminescent materials and devices
US9735373B2 (en) 2013-06-10 2017-08-15 Universal Display Corporation Organic electroluminescent materials and devices
US9673401B2 (en) 2013-06-28 2017-06-06 Universal Display Corporation Organic electroluminescent materials and devices
US10199581B2 (en) 2013-07-01 2019-02-05 Universal Display Corporation Organic electroluminescent materials and devices
US10991896B2 (en) 2013-07-01 2021-04-27 Universal Display Corporation Organic electroluminescent materials and devices
US10121975B2 (en) 2013-07-03 2018-11-06 Universal Display Corporation Organic electroluminescent materials and devices
US9761807B2 (en) 2013-07-15 2017-09-12 Universal Display Corporation Organic light emitting diode materials
US9324949B2 (en) 2013-07-16 2016-04-26 Universal Display Corporation Organic electroluminescent materials and devices
US9553274B2 (en) 2013-07-16 2017-01-24 Universal Display Corporation Organic electroluminescent materials and devices
US9224958B2 (en) 2013-07-19 2015-12-29 Universal Display Corporation Organic electroluminescent materials and devices
US10930866B2 (en) 2013-07-25 2021-02-23 Universal Display Corporation Organic electroluminescent materials and devices
US10074806B2 (en) 2013-08-20 2018-09-11 Universal Display Corporation Organic electroluminescent materials and devices
US10749114B2 (en) 2013-08-20 2020-08-18 Universal Display Corporation Organic electroluminescent materials and devices
US11611042B2 (en) 2013-08-20 2023-03-21 Universal Display Corporation Organic electroluminescent materials and devices
US9831437B2 (en) 2013-08-20 2017-11-28 Universal Display Corporation Organic electroluminescent materials and devices
US9932359B2 (en) 2013-08-30 2018-04-03 University Of Southern California Organic electroluminescent materials and devices
US10199582B2 (en) 2013-09-03 2019-02-05 University Of Southern California Organic electroluminescent materials and devices
US9735378B2 (en) 2013-09-09 2017-08-15 Universal Display Corporation Organic electroluminescent materials and devices
US9748503B2 (en) 2013-09-13 2017-08-29 Universal Display Corporation Organic electroluminescent materials and devices
US10003034B2 (en) 2013-09-30 2018-06-19 Universal Display Corporation Organic electroluminescent materials and devices
US9831447B2 (en) 2013-10-08 2017-11-28 Universal Display Corporation Organic electroluminescent materials and devices
US9293712B2 (en) 2013-10-11 2016-03-22 Universal Display Corporation Disubstituted pyrene compounds with amino group containing ortho aryl group and devices containing the same
US9853229B2 (en) 2013-10-23 2017-12-26 University Of Southern California Organic electroluminescent materials and devices
US10128450B2 (en) 2013-10-23 2018-11-13 University Of Southern California Organic electroluminescent materials and devices
US9306179B2 (en) 2013-11-08 2016-04-05 Universal Display Corporation Organic electroluminescent materials and devices
US9647218B2 (en) 2013-11-14 2017-05-09 Universal Display Corporation Organic electroluminescent materials and devices
US9905784B2 (en) 2013-11-15 2018-02-27 Universal Display Corporation Organic electroluminescent materials and devices
US10033000B2 (en) 2013-11-15 2018-07-24 Universal Display Corporation Organic electroluminescent materials and devices
US10056565B2 (en) 2013-11-20 2018-08-21 Universal Display Corporation Organic electroluminescent materials and devices
US10644251B2 (en) 2013-12-04 2020-05-05 Universal Display Corporation Organic electroluminescent materials and devices
US9876173B2 (en) 2013-12-09 2018-01-23 Universal Display Corporation Organic electroluminescent materials and devices
US11653558B2 (en) 2013-12-16 2023-05-16 Universal Display Corporation Organic electroluminescent materials and devices
US10355227B2 (en) 2013-12-16 2019-07-16 Universal Display Corporation Metal complex for phosphorescent OLED
US9847496B2 (en) 2013-12-23 2017-12-19 Universal Display Corporation Organic electroluminescent materials and devices
US10749122B2 (en) 2014-01-07 2020-08-18 Universal Display Corporation Organic electroluminescent materials and devices
US10985331B2 (en) 2014-01-07 2021-04-20 Universal Display Corporation Organic electroluminescent materials and devices
US10135008B2 (en) 2014-01-07 2018-11-20 Universal Display Corporation Organic electroluminescent materials and devices
US11005051B2 (en) 2014-01-08 2021-05-11 Universal Display Corporation Organic electroluminescent materials and devices
US9978961B2 (en) 2014-01-08 2018-05-22 Universal Display Corporation Organic electroluminescent materials and devices
US9755159B2 (en) 2014-01-23 2017-09-05 Universal Display Corporation Organic materials for OLEDs
US9935277B2 (en) 2014-01-30 2018-04-03 Universal Display Corporation Organic electroluminescent materials and devices
US9590194B2 (en) 2014-02-14 2017-03-07 Universal Display Corporation Organic electroluminescent materials and devices
US9847497B2 (en) 2014-02-18 2017-12-19 Universal Display Corporation Organic electroluminescent materials and devices
US11024816B2 (en) 2014-02-18 2021-06-01 Universal Display Corporation Organic electroluminescent materials and devices
US10003033B2 (en) 2014-02-18 2018-06-19 Universal Display Corporation Organic electroluminescent materials and devices
US10707423B2 (en) 2014-02-21 2020-07-07 Universal Display Corporation Organic electroluminescent materials and devices
US9647217B2 (en) 2014-02-24 2017-05-09 Universal Display Corporation Organic electroluminescent materials and devices
US9502656B2 (en) 2014-02-24 2016-11-22 Universal Display Corporation Organic electroluminescent materials and devices
US10403825B2 (en) 2014-02-27 2019-09-03 Universal Display Corporation Organic electroluminescent materials and devices
US11600782B2 (en) 2014-02-27 2023-03-07 Universal Display Corporation Organic electroluminescent materials and devices
US9181270B2 (en) 2014-02-28 2015-11-10 Universal Display Corporation Method of making sulfide compounds
US9673407B2 (en) 2014-02-28 2017-06-06 Universal Display Corporation Organic electroluminescent materials and devices
US9590195B2 (en) 2014-02-28 2017-03-07 Universal Display Corporation Organic electroluminescent materials and devices
US9190620B2 (en) 2014-03-01 2015-11-17 Universal Display Corporation Organic electroluminescent materials and devices
US9397309B2 (en) 2014-03-13 2016-07-19 Universal Display Corporation Organic electroluminescent devices
US10208026B2 (en) 2014-03-18 2019-02-19 Universal Display Corporation Organic electroluminescent materials and devices
US9748504B2 (en) 2014-03-25 2017-08-29 Universal Display Corporation Organic electroluminescent materials and devices
US9929353B2 (en) 2014-04-02 2018-03-27 Universal Display Corporation Organic electroluminescent materials and devices
US9691993B2 (en) 2014-04-09 2017-06-27 Universal Display Corporation Organic electroluminescent materials and devices
US10825998B2 (en) 2014-04-14 2020-11-03 Universal Display Corporation Organic electroluminescent materials and devices
US9905785B2 (en) 2014-04-14 2018-02-27 Universal Display Corporation Organic electroluminescent materials and devices
US11005052B2 (en) 2014-04-14 2021-05-11 Universal Display Corporation Organic electroluminescent materials and devices
US9847498B2 (en) 2014-04-14 2017-12-19 Universal Display Corporation Organic electroluminescent materials and devices
US11793066B2 (en) 2014-04-14 2023-10-17 Universal Display Corporation Organic electroluminescent materials and devices
US10008679B2 (en) 2014-04-14 2018-06-26 Universal Display Corporation Organic electroluminescent materials and devices
US10256427B2 (en) 2014-04-15 2019-04-09 Universal Display Corporation Efficient organic electroluminescent devices
US9450198B2 (en) 2014-04-15 2016-09-20 Universal Display Corporation Organic electroluminescent materials and devices
US9741941B2 (en) 2014-04-29 2017-08-22 Universal Display Corporation Organic electroluminescent materials and devices
US11919916B2 (en) 2014-05-02 2024-03-05 Universal Display Corporation Organic electroluminescent materials and devices
US10457699B2 (en) 2014-05-02 2019-10-29 Universal Display Corporation Organic electroluminescent materials and devices
US11427607B2 (en) 2014-05-02 2022-08-30 Universal Display Corporation Organic electroluminescent materials and devices
US10636983B2 (en) 2014-05-08 2020-04-28 Universal Display Corporation Organic electroluminescent materials and devices
US10263198B2 (en) 2014-05-08 2019-04-16 Universal Display Corporation Organic electroluminescent materials and devices
US10256419B2 (en) 2014-05-08 2019-04-09 Universal Display Corporation Organic electroluminescent materials and devices
US10301338B2 (en) 2014-05-08 2019-05-28 Universal Display Corporation Organic electroluminescent materials and devices
US10276805B2 (en) 2014-05-08 2019-04-30 Universal Display Corporation Organic electroluminescent materials and devices
US11495754B2 (en) 2014-05-08 2022-11-08 Universal Display Corporation Organic electroluminescent materials and devices
US10403830B2 (en) 2014-05-08 2019-09-03 Universal Display Corporation Organic electroluminescent materials and devices
US9997716B2 (en) 2014-05-27 2018-06-12 Universal Display Corporation Organic electroluminescent materials and devices
US10461260B2 (en) 2014-06-03 2019-10-29 Universal Display Corporation Organic electroluminescent materials and devices
US10700293B2 (en) 2014-06-26 2020-06-30 Universal Display Corporation Organic electroluminescent materials and devices
US9911931B2 (en) 2014-06-26 2018-03-06 Universal Display Corporation Organic electroluminescent materials and devices
US10297762B2 (en) 2014-07-09 2019-05-21 Universal Display Corporation Organic electroluminescent materials and devices
US11456423B2 (en) 2014-07-09 2022-09-27 Universal Display Corporation Organic electroluminescent materials and devices
US11024811B2 (en) 2014-07-09 2021-06-01 Universal Display Corporation Organic electroluminescent materials and devices
US10566546B2 (en) 2014-07-14 2020-02-18 Universal Display Corporation Organic electroluminescent materials and devices
US9929357B2 (en) 2014-07-22 2018-03-27 Universal Display Corporation Organic electroluminescent materials and devices
US11108000B2 (en) 2014-08-07 2021-08-31 Unniversal Display Corporation Organic electroluminescent materials and devices
US10411200B2 (en) 2014-08-07 2019-09-10 Universal Display Corporation Electroluminescent (2-phenylpyridine)iridium complexes and devices
US10749113B2 (en) 2014-09-29 2020-08-18 Universal Display Corporation Organic electroluminescent materials and devices
US10135007B2 (en) 2014-09-29 2018-11-20 Universal Display Corporation Organic electroluminescent materials and devices
US10043987B2 (en) 2014-09-29 2018-08-07 Universal Display Corporation Organic electroluminescent materials and devices
US11641774B2 (en) 2014-09-29 2023-05-02 Universal Display Corporation Organic electroluminescent materials and devices
US11342510B2 (en) 2014-10-06 2022-05-24 Universal Display Corporation Organic electroluminescent materials and devices
US10361375B2 (en) 2014-10-06 2019-07-23 Universal Display Corporation Organic electroluminescent materials and devices
US9397302B2 (en) 2014-10-08 2016-07-19 Universal Display Corporation Organic electroluminescent materials and devices
US10998508B2 (en) 2014-10-08 2021-05-04 Universal Display Corporation Organic electroluminescent materials and devices
US10854826B2 (en) 2014-10-08 2020-12-01 Universal Display Corporation Organic electroluminescent compounds, compositions and devices
US11342516B2 (en) 2014-10-08 2022-05-24 Universal Display Corporation Organic electroluminescent materials and devices
US9799838B2 (en) 2014-10-08 2017-10-24 Universal Display Corporation Fluorinated organic electroluminescent materials and devices
US10950803B2 (en) 2014-10-13 2021-03-16 Universal Display Corporation Compounds and uses in devices
US9484541B2 (en) 2014-10-20 2016-11-01 Universal Display Corporation Organic electroluminescent materials and devices
US10868261B2 (en) 2014-11-10 2020-12-15 Universal Display Corporation Organic electroluminescent materials and devices
US11043641B2 (en) 2014-11-12 2021-06-22 Universal Display Corporation Organic electroluminescent materials and devices
US10038151B2 (en) 2014-11-12 2018-07-31 Universal Display Corporation Organic electroluminescent materials and devices
US10411201B2 (en) 2014-11-12 2019-09-10 Universal Display Corporation Organic electroluminescent materials and devices
US11832507B2 (en) 2014-11-12 2023-11-28 Universal Display Corporation Organic electroluminescent materials and devices
US9871212B2 (en) 2014-11-14 2018-01-16 Universal Display Corporation Organic electroluminescent materials and devices
US9882151B2 (en) 2014-11-14 2018-01-30 Universal Display Corporation Organic electroluminescent materials and devices
US9761814B2 (en) 2014-11-18 2017-09-12 Universal Display Corporation Organic light-emitting materials and devices
US9444075B2 (en) 2014-11-26 2016-09-13 Universal Display Corporation Emissive display with photo-switchable polarization
US9825260B2 (en) 2014-11-26 2017-11-21 Universal Display Corporation Emissive display with photo-switchable polarization
US10000517B2 (en) 2014-12-17 2018-06-19 Universal Display Corporation Organic electroluminescent materials and devices
US9680113B2 (en) 2014-12-17 2017-06-13 Universal Display Corporation Organic electroluminescent materials and devices
US9450195B2 (en) 2014-12-17 2016-09-20 Universal Display Corporation Organic electroluminescent materials and devices
US10253252B2 (en) 2014-12-30 2019-04-09 Universal Display Corporation Organic electroluminescent materials and devices
US10636978B2 (en) 2014-12-30 2020-04-28 Universal Display Corporation Organic electroluminescent materials and devices
US9312499B1 (en) 2015-01-05 2016-04-12 Universal Display Corporation Organic electroluminescent materials and devices
US9406892B2 (en) 2015-01-07 2016-08-02 Universal Display Corporation Organic electroluminescent materials and devices
US9748500B2 (en) 2015-01-15 2017-08-29 Universal Display Corporation Organic light emitting materials
US10418569B2 (en) 2015-01-25 2019-09-17 Universal Display Corporation Organic electroluminescent materials and devices
US9711730B2 (en) 2015-01-25 2017-07-18 Universal Display Corporation Organic electroluminescent materials and devices
US11245081B2 (en) 2015-02-06 2022-02-08 Universal Display Corporation Organic electroluminescent materials and devices
US10418562B2 (en) 2015-02-06 2019-09-17 Universal Display Corporation Organic electroluminescent materials and devices
US10355222B2 (en) 2015-02-06 2019-07-16 Universal Display Corporation Organic electroluminescent materials and devices
US10644247B2 (en) 2015-02-06 2020-05-05 Universal Display Corporation Organic electroluminescent materials and devices
US10177316B2 (en) 2015-02-09 2019-01-08 Universal Display Corporation Organic electroluminescent materials and devices
US11535797B2 (en) 2015-02-13 2022-12-27 Universal Display Corporation Organic electroluminescent materials and devices
US10144867B2 (en) 2015-02-13 2018-12-04 Universal Display Corporation Organic electroluminescent materials and devices
US11795385B2 (en) 2015-02-13 2023-10-24 Universal Display Corporation Organic electroluminescent materials and devices
US10889754B2 (en) 2015-02-13 2021-01-12 Universal Display Corporation Organic electroluminescent materials and devices
US10680183B2 (en) 2015-02-15 2020-06-09 Universal Display Corporation Organic electroluminescent materials and devices
US9929361B2 (en) 2015-02-16 2018-03-27 Universal Display Corporation Organic electroluminescent materials and devices
US10600966B2 (en) 2015-02-27 2020-03-24 Universal Display Corporation Organic electroluminescent materials and devices
US11678567B2 (en) 2015-02-27 2023-06-13 Universal Display Corporation Organic electroluminescent materials and devices
US11056657B2 (en) 2015-02-27 2021-07-06 University Display Corporation Organic electroluminescent materials and devices
US10686143B2 (en) 2015-03-05 2020-06-16 Universal Display Corporation Organic electroluminescent materials and devices
US10270046B2 (en) 2015-03-06 2019-04-23 Universal Display Corporation Organic electroluminescent materials and devices
US9780316B2 (en) 2015-03-16 2017-10-03 Universal Display Corporation Organic electroluminescent materials and devices
US9911928B2 (en) 2015-03-19 2018-03-06 Universal Display Corporation Organic electroluminescent materials and devices
US10529931B2 (en) 2015-03-24 2020-01-07 Universal Display Corporation Organic Electroluminescent materials and devices
US10297770B2 (en) 2015-03-27 2019-05-21 Universal Display Corporation Organic electroluminescent materials and devices
US11672175B2 (en) 2015-04-06 2023-06-06 Universal Display Corporation Organic electroluminescent materials and devices
US11245080B2 (en) 2015-04-06 2022-02-08 Universal Display Corporation Organic electroluminescent materials and devices
US10693082B2 (en) 2015-04-06 2020-06-23 Universal Display Corporation Organic electroluminescent materials and devices
US11818949B2 (en) 2015-04-06 2023-11-14 Universal Display Corporation Organic electroluminescent materials and devices
US11495749B2 (en) 2015-04-06 2022-11-08 Universal Display Corporation Organic electroluminescent materials and devices
US10593890B2 (en) 2015-04-06 2020-03-17 Universal Display Corporation Organic electroluminescent materials and devices
US10403826B2 (en) 2015-05-07 2019-09-03 Universal Display Corporation Organic electroluminescent materials and devices
US10777749B2 (en) 2015-05-07 2020-09-15 Universal Display Corporation Organic electroluminescent materials and devices
US11744151B2 (en) 2015-05-07 2023-08-29 Universal Display Corporation Organic electroluminescent materials and devices
US9478758B1 (en) 2015-05-08 2016-10-25 Universal Display Corporation Organic electroluminescent materials and devices
US10547013B2 (en) 2015-05-15 2020-01-28 Universal Display Corporation Organic electroluminescent materials and devices
US11335864B2 (en) 2015-05-15 2022-05-17 Universal Display Corporation Organic electroluminescent materials and devices
US9859510B2 (en) 2015-05-15 2018-01-02 Universal Display Corporation Organic electroluminescent materials and devices
USRE48809E1 (en) 2015-05-15 2021-11-02 Universal Display Corporation Organic electroluminescent materials and devices
US20160343951A1 (en) * 2015-05-21 2016-11-24 Universal Display Corporation Organic electroluminescent materials and devices
US20170077409A1 (en) * 2015-05-21 2017-03-16 Universal Display Corporation Organic electroluminescent materials and devices
US10109799B2 (en) 2015-05-21 2018-10-23 Universal Display Corporation Organic electroluminescent materials and devices
US10256411B2 (en) 2015-05-21 2019-04-09 Universal Display Corporation Organic electroluminescent materials and devices
US10033004B2 (en) 2015-06-01 2018-07-24 Universal Display Corporation Organic electroluminescent materials and devices
US10418568B2 (en) 2015-06-01 2019-09-17 Universal Display Corporation Organic electroluminescent materials and devices
US11925102B2 (en) 2015-06-04 2024-03-05 Universal Display Corporation Organic electroluminescent materials and devices
US10825997B2 (en) 2015-06-25 2020-11-03 Universal Display Corporation Organic electroluminescent materials and devices
US10873036B2 (en) 2015-07-07 2020-12-22 Universal Display Corporation Organic electroluminescent materials and devices
US11127905B2 (en) 2015-07-29 2021-09-21 Universal Display Corporation Organic electroluminescent materials and devices
US11018309B2 (en) 2015-08-03 2021-05-25 Universal Display Corporation Organic electroluminescent materials and devices
US11522140B2 (en) 2015-08-17 2022-12-06 Universal Display Corporation Organic electroluminescent materials and devices
US10522769B2 (en) 2015-08-18 2019-12-31 Universal Display Corporation Organic electroluminescent materials and devices
US10181564B2 (en) 2015-08-26 2019-01-15 Universal Display Corporation Organic electroluminescent materials and devices
US10361381B2 (en) 2015-09-03 2019-07-23 Universal Display Corporation Organic electroluminescent materials and devices
US10672996B2 (en) 2015-09-03 2020-06-02 Universal Display Corporation Organic electroluminescent materials and devices
US11605789B2 (en) 2015-09-03 2023-03-14 Universal Display Corporation Organic electroluminescent materials and devices
US11626563B2 (en) 2015-09-03 2023-04-11 Universal Display Corporation Organic electroluminescent materials and devices
US11706972B2 (en) 2015-09-08 2023-07-18 Universal Display Corporation Organic electroluminescent materials and devices
US11302872B2 (en) 2015-09-09 2022-04-12 Universal Display Corporation Organic electroluminescent materials and devices
US10770664B2 (en) 2015-09-21 2020-09-08 Universal Display Corporation Organic electroluminescent materials and devices
US11812622B2 (en) 2015-09-25 2023-11-07 Universal Display Corporation Organic electroluminescent compounds and devices
US11889747B2 (en) 2015-10-01 2024-01-30 Universal Display Corporation Organic electroluminescent materials and devices
US10847728B2 (en) 2015-10-01 2020-11-24 Universal Display Corporation Organic electroluminescent materials and devices
US10593892B2 (en) 2015-10-01 2020-03-17 Universal Display Corporation Organic electroluminescent materials and devices
US10991895B2 (en) 2015-10-06 2021-04-27 Universal Display Corporation Organic electroluminescent materials and devices
US11349087B2 (en) 2015-10-29 2022-05-31 Universal Display Corporation Organic electroluminescent materials and devices
US10388892B2 (en) 2015-10-29 2019-08-20 Universal Display Corporation Organic electroluminescent materials and devices
US10388893B2 (en) 2015-10-29 2019-08-20 Universal Display Corporation Organic electroluminescent materials and devices
US10177318B2 (en) 2015-10-29 2019-01-08 Universal Display Corporation Organic electroluminescent materials and devices
US11832456B2 (en) 2015-11-23 2023-11-28 Universal Display Corporation Organic electroluminescent materials and devices
US10998507B2 (en) 2015-11-23 2021-05-04 Universal Display Corporation Organic electroluminescent materials and devices
US10476010B2 (en) 2015-11-30 2019-11-12 Universal Display Corporation Organic electroluminescent materials and devices
US11818948B2 (en) 2015-12-29 2023-11-14 Universal Display Corporation Organic electroluminescent materials and devices
US10957861B2 (en) 2015-12-29 2021-03-23 Universal Display Corporation Organic electroluminescent materials and devices
US11024808B2 (en) 2015-12-29 2021-06-01 Universal Display Corporation Organic electroluminescent materials and devices
US10135006B2 (en) 2016-01-04 2018-11-20 Universal Display Corporation Organic electroluminescent materials and devices
US11692132B2 (en) 2016-02-09 2023-07-04 Universal Display Corporation Organic electroluminescent materials and devices
US11098245B2 (en) 2016-02-09 2021-08-24 Universal Display Corporation Organic electroluminescent materials and devices
US11716898B2 (en) 2016-02-09 2023-08-01 Universal Display Corporation Organic electroluminescent materials and devices
US10457864B2 (en) 2016-02-09 2019-10-29 Universal Display Corporation Organic electroluminescent materials and devices
US10707427B2 (en) 2016-02-09 2020-07-07 Universal Display Corporation Organic electroluminescent materials and devices
US10600967B2 (en) 2016-02-18 2020-03-24 Universal Display Corporation Organic electroluminescent materials and devices
US11094891B2 (en) 2016-03-16 2021-08-17 Universal Display Corporation Organic electroluminescent materials and devices
US10276809B2 (en) 2016-04-05 2019-04-30 Universal Display Corporation Organic electroluminescent materials and devices
US10236456B2 (en) 2016-04-11 2019-03-19 Universal Display Corporation Organic electroluminescent materials and devices
US10566552B2 (en) 2016-04-13 2020-02-18 Universal Display Corporation Organic electroluminescent materials and devices
US11342515B2 (en) 2016-04-13 2022-05-24 Universal Display Corporation Organic electroluminescent materials and devices
US11825734B2 (en) 2016-04-13 2023-11-21 Universal Display Corporation Organic electroluminescent materials and devices
US11228003B2 (en) 2016-04-22 2022-01-18 Universal Display Corporation Organic electroluminescent materials and devices
US11081647B2 (en) 2016-04-22 2021-08-03 Universal Display Corporation Organic electroluminescent materials and devices
US11228002B2 (en) 2016-04-22 2022-01-18 Universal Display Corporation Organic electroluminescent materials and devices
US10985328B2 (en) 2016-05-25 2021-04-20 Universal Display Corporation Organic electroluminescent materials and devices
US11711977B2 (en) 2016-05-25 2023-07-25 Universal Display Corporation Organic electroluminescent materials and devices
US10840458B2 (en) 2016-05-25 2020-11-17 Universal Display Corporation Organic electroluminescent materials and devices
US10468609B2 (en) 2016-06-02 2019-11-05 Universal Display Corporation Organic electroluminescent materials and devices
US10672997B2 (en) 2016-06-20 2020-06-02 Universal Display Corporation Organic electroluminescent materials and devices
US11588121B2 (en) 2016-06-20 2023-02-21 Universal Display Corporation Organic electroluminescent materials and devices
US10651403B2 (en) 2016-06-20 2020-05-12 Universal Display Corporation Organic electroluminescent materials and devices
US10862054B2 (en) 2016-06-20 2020-12-08 Universal Display Corporation Organic electroluminescent materials and devices
US10686140B2 (en) 2016-06-20 2020-06-16 Universal Display Corporation Organic electroluminescent materials and devices
US11839139B2 (en) 2016-06-20 2023-12-05 Universal Display Corporation Organic electroluminescent materials and devices
US10727423B2 (en) 2016-06-20 2020-07-28 Universal Display Corporation Organic electroluminescent materials and devices
US11683981B2 (en) 2016-06-20 2023-06-20 Universal Display Corporation Organic electroluminescent materials and devices
US11114624B2 (en) 2016-06-20 2021-09-07 Universal Display Corporation Organic electroluminescent materials and devices
US11690284B2 (en) 2016-06-20 2023-06-27 Universal Display Corporation Organic electroluminescent materials and devices
US11903306B2 (en) 2016-06-20 2024-02-13 Universal Display Corporation Organic electroluminescent materials and devices
US11424419B2 (en) 2016-06-20 2022-08-23 Universal Display Corporation Organic electroluminescent materials and devices
US11482683B2 (en) 2016-06-20 2022-10-25 Universal Display Corporation Organic electroluminescent materials and devices
US10957866B2 (en) 2016-06-30 2021-03-23 Universal Display Corporation Organic electroluminescent materials and devices
US9929360B2 (en) 2016-07-08 2018-03-27 Universal Display Corporation Organic electroluminescent materials and devices
US10680184B2 (en) 2016-07-11 2020-06-09 Universal Display Corporation Organic electroluminescent materials and devices
US10566547B2 (en) 2016-07-11 2020-02-18 Universal Display Corporation Organic electroluminescent materials and devices
US10153443B2 (en) 2016-07-19 2018-12-11 Universal Display Corporation Organic electroluminescent materials and devices
US10720587B2 (en) 2016-07-19 2020-07-21 Universal Display Corporation Organic electroluminescent materials and devices
US10205105B2 (en) 2016-08-15 2019-02-12 Universal Display Corporation Organic electroluminescent materials and devices
US11024807B2 (en) 2016-09-14 2021-06-01 Universal Display Corporation Organic electroluminescent materials and devices
US10608186B2 (en) 2016-09-14 2020-03-31 Universal Display Corporation Organic electroluminescent materials and devices
US10505127B2 (en) 2016-09-19 2019-12-10 Universal Display Corporation Organic electroluminescent materials and devices
US10680187B2 (en) 2016-09-23 2020-06-09 Universal Display Corporation Organic electroluminescent materials and devices
US11711969B2 (en) 2016-10-03 2023-07-25 Universal Display Corporation Organic electroluminescent materials and devices
US11189804B2 (en) 2016-10-03 2021-11-30 Universal Display Corporation Organic electroluminescent materials and devices
US11196010B2 (en) 2016-10-03 2021-12-07 Universal Display Corporation Organic electroluminescent materials and devices
US11127906B2 (en) 2016-10-03 2021-09-21 Universal Display Corporation Organic electroluminescent materials and devices
US11183642B2 (en) 2016-10-03 2021-11-23 Universal Display Corporation Organic electroluminescent materials and devices
US11081658B2 (en) 2016-10-03 2021-08-03 Universal Display Corporation Organic electroluminescent materials and devices
US11011709B2 (en) 2016-10-07 2021-05-18 Universal Display Corporation Organic electroluminescent materials and devices
US11711968B2 (en) 2016-10-07 2023-07-25 Universal Display Corporation Organic electroluminescent materials and devices
US11239432B2 (en) 2016-10-14 2022-02-01 Universal Display Corporation Organic electroluminescent materials and devices
US10608185B2 (en) 2016-10-17 2020-03-31 Univeral Display Corporation Organic electroluminescent materials and devices
US10236458B2 (en) 2016-10-24 2019-03-19 Universal Display Corporation Organic electroluminescent materials and devices
US10340464B2 (en) 2016-11-10 2019-07-02 Universal Display Corporation Organic electroluminescent materials and devices
US10680188B2 (en) 2016-11-11 2020-06-09 Universal Display Corporation Organic electroluminescent materials and devices
US11069864B2 (en) 2016-11-11 2021-07-20 Universal Display Corporation Organic electroluminescent materials and devices
US10897016B2 (en) 2016-11-14 2021-01-19 Universal Display Corporation Organic electroluminescent materials and devices
US10662196B2 (en) 2016-11-17 2020-05-26 Universal Display Corporation Organic electroluminescent materials and devices
US10964893B2 (en) 2016-11-17 2021-03-30 Universal Display Corporation Organic electroluminescent materials and devices
US10153445B2 (en) 2016-11-21 2018-12-11 Universal Display Corporation Organic electroluminescent materials and devices
US10833276B2 (en) 2016-11-21 2020-11-10 Universal Display Corporation Organic electroluminescent materials and devices
US11555048B2 (en) 2016-12-01 2023-01-17 Universal Display Corporation Organic electroluminescent materials and devices
US10490753B2 (en) 2016-12-15 2019-11-26 Universal Display Corporation Organic electroluminescent materials and devices
US11545636B2 (en) 2016-12-15 2023-01-03 Universal Display Corporation Organic electroluminescent materials and devices
US11548905B2 (en) 2016-12-15 2023-01-10 Universal Display Corporation Organic electroluminescent materials and devices
US10811618B2 (en) 2016-12-19 2020-10-20 Universal Display Corporation Organic electroluminescent materials and devices
US11152579B2 (en) 2016-12-28 2021-10-19 Universal Display Corporation Organic electroluminescent materials and devices
US11201298B2 (en) 2017-01-09 2021-12-14 Universal Display Corporation Organic electroluminescent materials and devices
US11780865B2 (en) 2017-01-09 2023-10-10 Universal Display Corporation Organic electroluminescent materials and devices
US10804475B2 (en) 2017-01-11 2020-10-13 Universal Display Corporation Organic electroluminescent materials and devices
US11545637B2 (en) 2017-01-13 2023-01-03 Universal Display Corporation Organic electroluminescent materials and devices
US10629820B2 (en) 2017-01-18 2020-04-21 Universal Display Corporation Organic electroluminescent materials and devices
US11566034B2 (en) 2017-01-20 2023-01-31 Universal Display Corporation Organic electroluminescent materials and devices
US11053268B2 (en) 2017-01-20 2021-07-06 Universal Display Corporation Organic electroluminescent materials and devices
US10964904B2 (en) 2017-01-20 2021-03-30 Universal Display Corporation Organic electroluminescent materials and devices
US11765968B2 (en) 2017-01-23 2023-09-19 Universal Display Corporation Organic electroluminescent materials and devices
US11765966B2 (en) 2017-01-24 2023-09-19 Universal Display Corporation Organic electroluminescent materials and devices
US11050028B2 (en) 2017-01-24 2021-06-29 Universal Display Corporation Organic electroluminescent materials and devices
US10978647B2 (en) 2017-02-15 2021-04-13 Universal Display Corporation Organic electroluminescent materials and devices
US10822361B2 (en) 2017-02-22 2020-11-03 Universal Display Corporation Organic electroluminescent materials and devices
US11254697B2 (en) 2017-02-22 2022-02-22 Universal Display Corporation Organic electroluminescent materials and devices
US11697661B2 (en) 2017-02-22 2023-07-11 Universal Display Corporation Organic electroluminescent materials and devices
US10844084B2 (en) 2017-02-22 2020-11-24 Universal Display Corporation Organic electroluminescent materials and devices
US11760770B2 (en) 2017-02-22 2023-09-19 Universal Display Corporation Organic electroluminescent materials and devices
US10745431B2 (en) 2017-03-08 2020-08-18 Universal Display Corporation Organic electroluminescent materials and devices
US10741780B2 (en) 2017-03-10 2020-08-11 Universal Display Corporation Organic electroluminescent materials and devices
US10672998B2 (en) 2017-03-23 2020-06-02 Universal Display Corporation Organic electroluminescent materials and devices
US10910577B2 (en) 2017-03-28 2021-02-02 Universal Display Corporation Organic electroluminescent materials and devices
US10873037B2 (en) 2017-03-28 2020-12-22 Universal Display Corporation Organic electroluminescent materials and devices
US11158820B2 (en) 2017-03-29 2021-10-26 Universal Display Corporation Organic electroluminescent materials and devices
US11725021B2 (en) 2017-03-29 2023-08-15 Universal Display Corporation Organic electroluminescent materials and devices
US10844085B2 (en) 2017-03-29 2020-11-24 Universal Display Corporation Organic electroluminescent materials and devices
US11678563B2 (en) 2017-03-29 2023-06-13 Universal Display Corporation Organic electroluminescent materials and devices
US11192910B2 (en) 2017-03-29 2021-12-07 Universal Display Corporation Organic electroluminescent materials and devices
US11056658B2 (en) 2017-03-29 2021-07-06 Universal Display Corporation Organic electroluminescent materials and devices
US10862046B2 (en) 2017-03-30 2020-12-08 Universal Display Corporation Organic electroluminescent materials and devices
US11276829B2 (en) 2017-03-31 2022-03-15 Universal Display Corporation Organic electroluminescent materials and devices
US11139443B2 (en) 2017-03-31 2021-10-05 Universal Display Corporation Organic electroluminescent materials and devices
US11038117B2 (en) 2017-04-11 2021-06-15 Universal Display Corporation Organic electroluminescent materials and devices
US10777754B2 (en) 2017-04-11 2020-09-15 Universal Display Corporation Organic electroluminescent materials and devices
US10975113B2 (en) 2017-04-21 2021-04-13 Universal Display Corporation Organic electroluminescent materials and devices
US11566035B2 (en) 2017-04-21 2023-01-31 Universal Display Corporation Organic electroluminescent materials and devices
US11101434B2 (en) 2017-04-21 2021-08-24 Universal Display Corporation Organic electroluminescent materials and devices
US11084838B2 (en) 2017-04-21 2021-08-10 Universal Display Corporation Organic electroluminescent materials and device
US11591356B2 (en) 2017-04-21 2023-02-28 Universal Display Corporation Organic electroluminescent materials and devices
US11038137B2 (en) 2017-04-28 2021-06-15 Universal Display Corporation Organic electroluminescent materials and devices
US10910570B2 (en) 2017-04-28 2021-02-02 Universal Display Corporation Organic electroluminescent materials and devices
US11702420B2 (en) 2017-05-01 2023-07-18 Universal Display Corporation Organic electroluminescent materials and devices
US11117897B2 (en) 2017-05-01 2021-09-14 Universal Display Corporation Organic electroluminescent materials and devices
US10941170B2 (en) 2017-05-03 2021-03-09 Universal Display Corporation Organic electroluminescent materials and devices
US11201299B2 (en) 2017-05-04 2021-12-14 Universal Display Corporation Organic electroluminescent materials and devices
US11377459B2 (en) 2017-05-05 2022-07-05 Universal Display Corporation Organic electroluminescent materials and devices
US10870668B2 (en) 2017-05-05 2020-12-22 Universal Display Corporation Organic electroluminescent materials and devices
US10862055B2 (en) 2017-05-05 2020-12-08 Universal Display Corporation Organic electroluminescent materials and devices
US10930864B2 (en) 2017-05-10 2021-02-23 Universal Display Corporation Organic electroluminescent materials and devices
US10822362B2 (en) 2017-05-11 2020-11-03 Universal Display Corporation Organic electroluminescent materials and devices
US10944060B2 (en) 2017-05-11 2021-03-09 Universal Display Corporation Organic electroluminescent materials and devices
US11038115B2 (en) 2017-05-18 2021-06-15 Universal Display Corporation Organic electroluminescent materials and device
US10934293B2 (en) 2017-05-18 2021-03-02 Universal Display Corporation Organic electroluminescent materials and devices
US10790455B2 (en) 2017-05-18 2020-09-29 Universal Display Corporation Organic electroluminescent materials and devices
US10944062B2 (en) 2017-05-18 2021-03-09 Universal Display Corporation Organic electroluminescent materials and devices
US10840459B2 (en) 2017-05-18 2020-11-17 Universal Display Corporation Organic electroluminescent materials and devices
US10930862B2 (en) 2017-06-01 2021-02-23 Universal Display Corporation Organic electroluminescent materials and devices
US11608321B2 (en) 2017-06-23 2023-03-21 Universal Display Corporation Organic electroluminescent materials and devices
US11814403B2 (en) 2017-06-23 2023-11-14 Universal Display Corporation Organic electroluminescent materials and devices
US11678565B2 (en) 2017-06-23 2023-06-13 Universal Display Corporation Organic electroluminescent materials and devices
US11552261B2 (en) 2017-06-23 2023-01-10 Universal Display Corporation Organic electroluminescent materials and devices
US11725022B2 (en) 2017-06-23 2023-08-15 Universal Display Corporation Organic electroluminescent materials and devices
US11731975B2 (en) 2017-06-23 2023-08-22 Universal Display Corporation Organic electroluminescent materials and devices
US11174259B2 (en) 2017-06-23 2021-11-16 Universal Display Corporation Organic electroluminescent materials and devices
US10968226B2 (en) 2017-06-23 2021-04-06 Universal Display Corporation Organic electroluminescent materials and devices
US11758804B2 (en) 2017-06-23 2023-09-12 Universal Display Corporation Organic electroluminescent materials and devices
US11832510B2 (en) 2017-06-23 2023-11-28 Universal Display Corporation Organic electroluminescent materials and devices
US11495757B2 (en) 2017-06-23 2022-11-08 Universal Display Corporation Organic electroluminescent materials and devices
US11802136B2 (en) 2017-06-23 2023-10-31 Universal Display Corporation Organic electroluminescent materials and devices
US11469382B2 (en) 2017-07-12 2022-10-11 Universal Display Corporation Organic electroluminescent materials and devices
JP7224125B2 (en) 2017-07-21 2023-02-17 三星ディスプレイ株式會社 Organometallic compound and organic light-emitting device containing the same
CN109280063B (en) * 2017-07-21 2023-12-12 三星显示有限公司 Organometallic compound and organic light emitting device including the same
JP2019023186A (en) * 2017-07-21 2019-02-14 三星ディスプレイ株式會社Samsung Display Co.,Ltd. Organometallic compound, and organic light emitting element containing the same
CN109280063A (en) * 2017-07-21 2019-01-29 三星显示有限公司 Organo-metallic compound and organic luminescent device including it
US11925104B2 (en) 2017-07-21 2024-03-05 Samsung Display Co., Ltd. Organometallic compound and organic light-emitting device including the same
US11228010B2 (en) 2017-07-26 2022-01-18 Universal Display Corporation Organic electroluminescent materials and devices
US11765970B2 (en) 2017-07-26 2023-09-19 Universal Display Corporation Organic electroluminescent materials and devices
US11239433B2 (en) 2017-07-26 2022-02-01 Universal Display Corporation Organic electroluminescent materials and devices
US11917843B2 (en) 2017-07-26 2024-02-27 Universal Display Corporation Organic electroluminescent materials and devices
US11322691B2 (en) 2017-07-26 2022-05-03 Universal Display Corporation Organic electroluminescent materials and devices
US11744141B2 (en) 2017-08-09 2023-08-29 Universal Display Corporation Organic electroluminescent materials and devices
US11508913B2 (en) 2017-08-10 2022-11-22 Universal Display Corporation Organic electroluminescent materials and devices
US11744142B2 (en) 2017-08-10 2023-08-29 Universal Display Corporation Organic electroluminescent materials and devices
US11349083B2 (en) 2017-08-10 2022-05-31 Universal Display Corporation Organic electroluminescent materials and devices
US11910699B2 (en) 2017-08-10 2024-02-20 Universal Display Corporation Organic electroluminescent materials and devices
US11723269B2 (en) 2017-08-22 2023-08-08 Universal Display Corporation Organic electroluminescent materials and devices
US11462697B2 (en) 2017-08-22 2022-10-04 Universal Display Corporation Organic electroluminescent materials and devices
US11437591B2 (en) 2017-08-24 2022-09-06 Universal Display Corporation Organic electroluminescent materials and devices
US11605791B2 (en) 2017-09-01 2023-03-14 Universal Display Corporation Organic electroluminescent materials and devices
US11696492B2 (en) 2017-09-07 2023-07-04 Universal Display Corporation Organic electroluminescent materials and devices
US11424420B2 (en) 2017-09-07 2022-08-23 Universal Display Corporation Organic electroluminescent materials and devices
US11444249B2 (en) 2017-09-07 2022-09-13 Universal Display Corporation Organic electroluminescent materials and devices
US10608188B2 (en) 2017-09-11 2020-03-31 Universal Display Corporation Organic electroluminescent materials and devices
US10964895B2 (en) 2017-09-11 2021-03-30 Universal Display Corporation Organic electroluminescent materials and devices
US11778897B2 (en) 2017-09-20 2023-10-03 Universal Display Corporation Organic electroluminescent materials and devices
US11183646B2 (en) 2017-11-07 2021-11-23 Universal Display Corporation Organic electroluminescent materials and devices
US11910702B2 (en) 2017-11-07 2024-02-20 Universal Display Corporation Organic electroluminescent devices
US11214587B2 (en) 2017-11-07 2022-01-04 Universal Display Corporation Organic electroluminescent materials and devices
US11685756B2 (en) 2017-11-07 2023-06-27 Universal Display Corporation Organic electroluminescent materials and devices
US11168103B2 (en) 2017-11-17 2021-11-09 Universal Display Corporation Organic electroluminescent materials and devices
US11825735B2 (en) 2017-11-28 2023-11-21 Universal Display Corporation Organic electroluminescent materials and devices
US11233204B2 (en) 2017-12-14 2022-01-25 Universal Display Corporation Organic electroluminescent materials and devices
US11233205B2 (en) 2017-12-14 2022-01-25 Universal Display Corporation Organic electroluminescent materials and devices
US10971687B2 (en) 2017-12-14 2021-04-06 Universal Display Corporation Organic electroluminescent materials and devices
US11700765B2 (en) 2018-01-10 2023-07-11 Universal Display Corporation Organic electroluminescent materials and devices
US11081659B2 (en) 2018-01-10 2021-08-03 Universal Display Corporation Organic electroluminescent materials and devices
US11818946B2 (en) 2018-01-11 2023-11-14 Universal Display Corporation Organic electroluminescent materials and devices
US11271177B2 (en) 2018-01-11 2022-03-08 Universal Display Corporation Organic electroluminescent materials and devices
US11515493B2 (en) 2018-01-11 2022-11-29 Universal Display Corporation Organic electroluminescent materials and devices
US11542289B2 (en) 2018-01-26 2023-01-03 Universal Display Corporation Organic electroluminescent materials and devices
US11367840B2 (en) 2018-01-26 2022-06-21 Universal Display Corporation Organic electroluminescent materials and devices
US11845764B2 (en) 2018-01-26 2023-12-19 Universal Display Corporation Organic electroluminescent materials and devices
US11910708B2 (en) 2018-02-09 2024-02-20 Universal Display Corporation Organic electroluminescent materials and devices
US11180519B2 (en) 2018-02-09 2021-11-23 Universal Display Corporation Organic electroluminescent materials and devices
US11342509B2 (en) 2018-02-09 2022-05-24 Universal Display Corporation Organic electroluminescent materials and devices
US11239434B2 (en) 2018-02-09 2022-02-01 Universal Display Corporation Organic electroluminescent materials and devices
US11217757B2 (en) 2018-03-12 2022-01-04 Universal Display Corporation Host materials for electroluminescent devices
US11557733B2 (en) 2018-03-12 2023-01-17 Universal Display Corporation Organic electroluminescent materials and devices
US11746122B2 (en) 2018-03-12 2023-09-05 Universal Display Corporation Organic electroluminescent materials and devices
US11279722B2 (en) 2018-03-12 2022-03-22 Universal Display Corporation Organic electroluminescent materials and devices
US11700766B2 (en) 2018-03-12 2023-07-11 Universal Display Corporation Host materials for electroluminescent devices
US11142538B2 (en) 2018-03-12 2021-10-12 Universal Display Corporation Organic electroluminescent materials and devices
US11165028B2 (en) 2018-03-12 2021-11-02 Universal Display Corporation Organic electroluminescent materials and devices
US11390639B2 (en) 2018-04-13 2022-07-19 Universal Display Corporation Organic electroluminescent materials and devices
US11882759B2 (en) 2018-04-13 2024-01-23 Universal Display Corporation Organic electroluminescent materials and devices
US11616203B2 (en) 2018-04-17 2023-03-28 Universal Display Corporation Organic electroluminescent materials and devices
US11342513B2 (en) 2018-05-04 2022-05-24 Universal Display Corporation Organic electroluminescent materials and devices
US11753427B2 (en) 2018-05-04 2023-09-12 Universal Display Corporation Organic electroluminescent materials and devices
US11839142B2 (en) 2018-05-04 2023-12-05 Universal Display Corporation Organic electroluminescent materials and devices
US11515494B2 (en) 2018-05-04 2022-11-29 Universal Display Corporation Organic electroluminescent materials and devices
US11793073B2 (en) 2018-05-06 2023-10-17 Universal Display Corporation Host materials for electroluminescent devices
US11844267B2 (en) 2018-05-25 2023-12-12 Universal Display Corporation Organic electroluminescent materials and devices
US11450822B2 (en) 2018-05-25 2022-09-20 Universal Display Corporation Organic electroluminescent materials and devices
US11459349B2 (en) 2018-05-25 2022-10-04 Universal Display Corporation Organic electroluminescent materials and devices
US11716900B2 (en) 2018-05-30 2023-08-01 Universal Display Corporation Host materials for electroluminescent devices
US11296283B2 (en) 2018-06-04 2022-04-05 Universal Display Corporation Organic electroluminescent materials and devices
US11404653B2 (en) 2018-06-04 2022-08-02 Universal Display Corporation Organic electroluminescent materials and devices
US11925103B2 (en) 2018-06-05 2024-03-05 Universal Display Corporation Organic electroluminescent materials and devices
US11339182B2 (en) 2018-06-07 2022-05-24 Universal Display Corporation Organic electroluminescent materials and devices
US11228004B2 (en) 2018-06-22 2022-01-18 Universal Display Corporation Organic electroluminescent materials and devices
US11261207B2 (en) 2018-06-25 2022-03-01 Universal Display Corporation Organic electroluminescent materials and devices
US11753425B2 (en) 2018-07-11 2023-09-12 Universal Display Corporation Organic electroluminescent materials and devices
CN110872327A (en) * 2018-08-31 2020-03-10 三星电子株式会社 Organometallic compound, organic light emitting device including the same, and diagnostic composition
US11233203B2 (en) 2018-09-06 2022-01-25 Universal Display Corporation Organic electroluminescent materials and devices
US11485706B2 (en) 2018-09-11 2022-11-01 Universal Display Corporation Organic electroluminescent materials and devices
US11718634B2 (en) 2018-09-14 2023-08-08 Universal Display Corporation Organic electroluminescent materials and devices
US11903305B2 (en) 2018-09-24 2024-02-13 Universal Display Corporation Organic electroluminescent materials and devices
US11469383B2 (en) 2018-10-08 2022-10-11 Universal Display Corporation Organic electroluminescent materials and devices
US11495752B2 (en) 2018-10-08 2022-11-08 Universal Display Corporation Organic electroluminescent materials and devices
US11476430B2 (en) 2018-10-15 2022-10-18 Universal Display Corporation Organic electroluminescent materials and devices
US11515482B2 (en) 2018-10-23 2022-11-29 Universal Display Corporation Deep HOMO (highest occupied molecular orbital) emitter device structures
US11937503B2 (en) 2018-10-23 2024-03-19 Universal Display Corporation Organic electroluminescent materials and devices
US11469384B2 (en) 2018-11-02 2022-10-11 Universal Display Corporation Organic electroluminescent materials and devices
US11839141B2 (en) 2018-11-02 2023-12-05 Universal Display Corporation Organic electroluminescent materials and devices
US11825736B2 (en) 2018-11-19 2023-11-21 Universal Display Corporation Organic electroluminescent materials and devices
US11716899B2 (en) 2018-11-28 2023-08-01 Universal Display Corporation Organic electroluminescent materials and devices
US11706980B2 (en) 2018-11-28 2023-07-18 Universal Display Corporation Host materials for electroluminescent devices
US11672165B2 (en) 2018-11-28 2023-06-06 Universal Display Corporation Organic electroluminescent materials and devices
US11515489B2 (en) 2018-11-28 2022-11-29 Universal Display Corporation Host materials for electroluminescent devices
US11672176B2 (en) 2018-11-28 2023-06-06 Universal Display Corporation Host materials for electroluminescent devices
US11690285B2 (en) 2018-11-28 2023-06-27 Universal Display Corporation Electroluminescent devices
US11623936B2 (en) 2018-12-11 2023-04-11 Universal Display Corporation Organic electroluminescent materials and devices
US11737349B2 (en) 2018-12-12 2023-08-22 Universal Display Corporation Organic electroluminescent materials and devices
US11834459B2 (en) 2018-12-12 2023-12-05 Universal Display Corporation Host materials for electroluminescent devices
US11812624B2 (en) 2019-01-30 2023-11-07 The University Of Southern California Organic electroluminescent materials and devices
US11780829B2 (en) 2019-01-30 2023-10-10 The University Of Southern California Organic electroluminescent materials and devices
US11325932B2 (en) 2019-02-08 2022-05-10 Universal Display Corporation Organic electroluminescent materials and devices
US11370809B2 (en) 2019-02-08 2022-06-28 Universal Display Corporation Organic electroluminescent materials and devices
US11773320B2 (en) 2019-02-21 2023-10-03 Universal Display Corporation Organic electroluminescent materials and devices
US11871653B2 (en) 2019-02-22 2024-01-09 Universal Display Corporation Organic electroluminescent materials and devices
US11758807B2 (en) 2019-02-22 2023-09-12 Universal Display Corporation Organic electroluminescent materials and devices
US11557738B2 (en) 2019-02-22 2023-01-17 Universal Display Corporation Organic electroluminescent materials and devices
US11512093B2 (en) 2019-03-04 2022-11-29 Universal Display Corporation Compound used for organic light emitting device (OLED), consumer product and formulation
US11739081B2 (en) 2019-03-11 2023-08-29 Universal Display Corporation Organic electroluminescent materials and devices
US11569480B2 (en) 2019-03-12 2023-01-31 Universal Display Corporation Plasmonic OLEDs and vertical dipole emitters
US11637261B2 (en) 2019-03-12 2023-04-25 Universal Display Corporation Nanopatch antenna outcoupling structure for use in OLEDs
US11639363B2 (en) 2019-04-22 2023-05-02 Universal Display Corporation Organic electroluminescent materials and devices
US11613550B2 (en) 2019-04-30 2023-03-28 Universal Display Corporation Organic electroluminescent materials and devices comprising benzimidazole-containing metal complexes
US11495756B2 (en) 2019-05-07 2022-11-08 Universal Display Corporation Organic electroluminescent materials and devices
US11560398B2 (en) 2019-05-07 2023-01-24 Universal Display Corporation Organic electroluminescent materials and devices
US11827651B2 (en) 2019-05-13 2023-11-28 Universal Display Corporation Organic electroluminescent materials and devices
US11634445B2 (en) 2019-05-21 2023-04-25 Universal Display Corporation Organic electroluminescent materials and devices
US11647667B2 (en) 2019-06-14 2023-05-09 Universal Display Corporation Organic electroluminescent compounds and organic light emitting devices using the same
US11920070B2 (en) 2019-07-12 2024-03-05 The University Of Southern California Luminescent janus-type, two-coordinated metal complexes
US11926638B2 (en) 2019-07-22 2024-03-12 Universal Display Corporation Organic electroluminescent materials and devices
US11685754B2 (en) 2019-07-22 2023-06-27 Universal Display Corporation Heteroleptic organic electroluminescent materials
US11708355B2 (en) 2019-08-01 2023-07-25 Universal Display Corporation Organic electroluminescent materials and devices
US11374181B2 (en) 2019-08-14 2022-06-28 Universal Display Corporation Organic electroluminescent materials and devices
US11930699B2 (en) 2019-08-15 2024-03-12 Universal Display Corporation Organic electroluminescent materials and devices
US11925105B2 (en) 2019-08-26 2024-03-05 Universal Display Corporation Organic electroluminescent materials and devices
US11600787B2 (en) 2019-08-30 2023-03-07 Universal Display Corporation Organic electroluminescent materials and devices
US11820783B2 (en) 2019-09-06 2023-11-21 Universal Display Corporation Organic electroluminescent materials and devices
US11864458B2 (en) 2019-10-08 2024-01-02 Universal Display Corporation Organic electroluminescent materials and devices
US11697653B2 (en) 2019-10-21 2023-07-11 Universal Display Corporation Organic electroluminescent materials and devices
US11919914B2 (en) 2019-10-25 2024-03-05 Universal Display Corporation Organic electroluminescent materials and devices
US11765965B2 (en) 2019-10-30 2023-09-19 Universal Display Corporation Organic electroluminescent materials and devices
US11889708B2 (en) 2019-11-14 2024-01-30 Universal Display Corporation Organic electroluminescent materials and devices
US11778895B2 (en) 2020-01-13 2023-10-03 Universal Display Corporation Organic electroluminescent materials and devices
US11917900B2 (en) 2020-01-28 2024-02-27 Universal Display Corporation Organic electroluminescent materials and devices
US11937494B2 (en) 2020-07-31 2024-03-19 Universal Display Corporation Organic electroluminescent materials and devices
US11932660B2 (en) 2021-01-04 2024-03-19 Universal Display Corporation Organic electroluminescent materials and devices

Also Published As

Publication number Publication date
JPWO2006098120A1 (en) 2008-08-21
JP5125502B2 (en) 2013-01-23

Similar Documents

Publication Publication Date Title
JP5125502B2 (en) Organic electroluminescence element material, organic electroluminescence element
JP5076900B2 (en) Organic electroluminescence element, display device and lighting device
JP5733294B2 (en) Organic electroluminescence device
JP4962613B2 (en) Organic electroluminescence element, display device and lighting device
JP5556012B2 (en) Organic electroluminescence element, display device and lighting device
JP5782836B2 (en) ORGANIC ELECTROLUMINESCENT ELEMENT MATERIAL, ORGANIC ELECTROLUMINESCENT ELEMENT, DISPLAY DEVICE, LIGHTING DEVICE, AND COMPOUND
JP5601036B2 (en) ORGANIC ELECTROLUMINESCENT ELEMENT, ORGANIC ELECTROLUMINESCENT ELEMENT MATERIAL, DISPLAY DEVICE AND LIGHTING DEVICE
WO2007097149A1 (en) Organic electroluminescence element, white light emitting element, display device and illuminating device
WO2007004380A1 (en) Organic electroluminescent element material, organic electroluminescent element, display device, and lighting equipment
WO2006082742A1 (en) Organic electroluminescent device material, organic electroluminescent device, display and illuminating device
WO2007029533A1 (en) Organic electroluminescence element, display device and illuminating device
WO2006013739A1 (en) Organic electroluminescent device, illuminating device and display
WO2006103874A1 (en) Organic electroluminescent device material, organic electroluminescent device, display and illuminating device
WO2007119816A1 (en) Organic electroluminescence element material, organic electroluminescence element, display device and lighting apparatus
JPWO2004095889A1 (en) Organic electroluminescence element and display device
WO2007108459A1 (en) Organic electroluminescent device, display and illuminating device
WO2008035664A1 (en) Organic electroluminescent device material, organic electroluminescent device, display and illuminating device
JP2005347160A (en) Organic electroluminescent element, lighting device, and display device
WO2007023659A1 (en) Organic electroluminescence device material, organic electroluminescence device, display device, and lighting device
WO2006126389A1 (en) Organic electroluminescent device material, organic electroluminescent device, display and illuminating device
JP2007294720A (en) Organic electroluminescent device, display device, and illuminating device
JP4967284B2 (en) Organic electroluminescence element, display device and lighting device
JP4622218B2 (en) Organic electroluminescence element, display device and lighting device
WO2006100925A1 (en) Material for organic el device, organic el device, display and illuminating device
WO2006043440A1 (en) Organic electroluminescent device, display and illuminating device

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application
WWE Wipo information: entry into national phase

Ref document number: 2007508045

Country of ref document: JP

NENP Non-entry into the national phase

Ref country code: DE

NENP Non-entry into the national phase

Ref country code: RU

122 Ep: pct application non-entry in european phase

Ref document number: 06714250

Country of ref document: EP

Kind code of ref document: A1