US20090066234A1 - Light emitting devices and compositions - Google Patents

Light emitting devices and compositions Download PDF

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US20090066234A1
US20090066234A1 US12/167,127 US16712708A US2009066234A1 US 20090066234 A1 US20090066234 A1 US 20090066234A1 US 16712708 A US16712708 A US 16712708A US 2009066234 A1 US2009066234 A1 US 2009066234A1
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light
bis
emitting
emitting device
phenyl
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Hyun Sik Chae
Yutaka Ohmori
Jesse Froehlich
Sheng Li
Amane Mochizuki
Ghassan Jabbour
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Nitto Denko Corp
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Nitto Denko Corp
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Assigned to NITTO DENKO CORPORATION reassignment NITTO DENKO CORPORATION ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: CHAE, HYUN SIK, FROEHLICH, JESSE, LI, SHENG, MOCHIZUKI, AMANE, JABBOUR, GHASSAN, OHMORI, YUTAKA
Publication of US20090066234A1 publication Critical patent/US20090066234A1/en
Priority to US13/460,661 priority patent/US8609258B2/en
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y20/00—Nanooptics, e.g. quantum optics or photonic crystals
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y30/00—Nanotechnology for materials or surface science, e.g. nanocomposites
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
    • C07F15/0033—Iridium compounds
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/14—Light 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/11—Compounds covalently bound to a solid support
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/18—Metal complexes
    • C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/10—Triplet emission
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02B—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO BUILDINGS, e.g. HOUSING, HOUSE APPLIANCES OR RELATED END-USER APPLICATIONS
    • Y02B20/00—Energy efficient lighting technologies, e.g. halogen lamps or gas discharge lamps

Definitions

  • This invention relates to light emitting compositions and light-emitting devices that include the light-emitting compositions. Specifically, this invention relates to light emitting compositions and light-emitting devices that include iridium-functionalized nanoparticles.
  • Organic electroluminescent devices capable of emitting white light are desirable because of their potential utility as backplane lights for displays, overhead lighting and other lightweight, low profile, low power lighting applications.
  • White light-emitting Organic Light-Emitting Diode (OLED) devices with high color purity and brightness exceeding 2000 cd/m 2 have been demonstrated at least since 1994. (1, 2)
  • OLED Organic Light-Emitting Diode
  • there is considerable difficulty in preparing white emitting OLEDs because it is generally quite difficult to prepare a device with a single layer that can emit white light.
  • Several ineffective strategies have been employed to generate white light by electroluminescence including: preparation of devices with multiple emitting layers, e.g.
  • red, green and blue (2) use of a single emitting layer doped with multiple small molecule emitters of different colors (1, 3, 4); blends of different color emitting polymers (5, 6); excimer (7) or “electromer” (8) emission from a semiconducting polymer; excimer emission from an interface (9); and broad emission from metal chelates (10).
  • phosphorescent dyes have been used as a source of emission in OLEDs because of their potential for achieving high degrees of luminescence efficiency.
  • phosphorescence can achieve 100% quantum efficiency by emitting from both the singlet and triplet state as compared to fluorescence which only emits from the singlet state and is thus limited to a theoretical efficiency of 25% (11).
  • Some embodiments described herein relate to an iridium-functionalized nanoparticle that can include a nanoparticle core and an iridium-complex.
  • the iridium-functionalized nanoparticles described herein are light-emitting, e.g., white light-emitting.
  • Various embodiments provide a composition that comprises an iridium-functionalized nanoparticle as described herein.
  • An embodiment described herein relates to a light emitting composition that can include one or more compound of formula (I):
  • the core can be a nanoparticle core
  • n can be 2
  • X is a single bond
  • the one or more compound of formula (I) may further comprise at least one host attached to the core, wherein the at least one host comprises a hole transport material, an electron transport material or a mixture thereof.
  • the first optionally substituted bidentate ligand can be selected from:
  • the first optionally substituted bidentate ligand can be selected from:
  • the first bidentate ligands can be selected from:
  • the first bidentate ligands can be the same as one another.
  • a light emitting device that can include: an anode layer comprising a high work function metal; a cathode layer comprising a low work function metal; and a light-emitting layer positioned between, and electrically connected to, the anode layer and the cathode layer, wherein the light-emitting layer can include an iridium-functionalized nanoparticle or composition thereof as described herein.
  • the iridium-functionalized nanoparticle is represented by Formula (I).
  • the iridium-functionalized nanoparticle is an organic-inorganic iridium-functionalized nanoparticle.
  • the organic-inorganic iridium-functionalized nanoparticle comprises a nanoparticle core that comprises inorganic elements such as phosphorous (P), silicon (Si), and/or a metal.
  • a nanoparticle core comprises a moiety selected from the group consisting of a silsesquioxane, a cyclophosphazene, a triazine, a cyclodextrin, a calumblene, a phthalocyanine, and a silica particle.
  • the light-emitting compositions described herein can include one or more iridium-functionalized nanoparticles and/or other materials in addition to the iridium-functionalized nanoparticle(s).
  • the light-emitting composition is configured to emit light such as blue, green, orange, red and white.
  • the process for making the light-emitting devices described herein include forming the light-emitting layer by a wet process.
  • FIG. 1 shows an exemplary configuration of an organic light-emitting device.
  • FIG. 2 is exemplary configuration of a single layer device structure.
  • FIG. 3 shows the photoluminescence spectra (PL) of (POSS)(Ir Compound I) in diluted CHCl 3 .
  • FIG. 4 shows an absorption (Abs) and photoluminescence spectra (PL) of (POSS)(Ir Compound II) in diluted CHCl 3 .
  • FIG. 5 shows an absorption (Abs) and shows photoluminescence spectra (PL) of (POSS)(Ir Compound III) in diluted CHCl 3 .
  • FIG. 6 shows an absorption (Abs) and photoluminescence spectra (PL) of (POSS)(Ir Compound IV) in diluted CH 2 Cl 2 .
  • FIG. 7 shows electroluminescent spectra (EL) of a device incorporating (POSS)(Ir Compound I), indicated by squares, and a device incorporating (POSS)(Ir Compound II), indicated by circles, in which the devices have the configuration of ITO/PEDOT:PSS/PVK+PBD+(POSS)(Ir Compound I)/CsF/Al or ITO/PEDOT:PSS/PVK+PBD+(POSS)(Ir Compound II)/CsF/Al, respectively.
  • FIG. 8 shows the current density of a device incorporating (POSS)(Ir Compound I), indicated by closed squares, and a device incorporating (POSS)(Ir Compound II), indicated by closed circles; and the brightness of a device incorporating (POSS)(Ir Compound I), indicated by open squares, and a device incorporating (POSS)(Ir Compound II), indicated by open circles.
  • FIG. 9 shows the external quantum efficiency (EQE) of a device incorporating (POSS)(Ir Compound I) indicated by closed squares and a device incorporating (POSS)(Ir Compound II) indicated by closed circles; the power efficiency PE of a device incorporating (POSS)(Ir Compound I) indicated by open squares and a device incorporating (POSS)(Ir Compound II) indicated by open circles.
  • EQE external quantum efficiency
  • FIG. 10 shows comparison data (EQE, and power efficiency) between POSS(Ir Compound V) and POSS(Ir-ppy)1(carbazole)7.
  • FIG. 11 shows the current density-voltage curve of a device incorporating 0.2 wt % of (POSS)(Ir compound I), 0.4 wt % of (POSS)(Ir compound III) and 5 wt % of (POSS)(Ir compound IV), as indicated by closed squares, and the brightness of the same device as a function of voltage as indicated by open squares.
  • FIG. 12 shows the EQE (indicated by closed squares) and luminous efficiency (indicated by open squares) of a device incorporating 0.2 wt % of (POSS)(Ir compound I), 0.4 wt % of (POSS)(Ir compound III) and 5 wt % of (POSS)(Ir compound IV) as a function of current density.
  • FIG. 13 shows the electroluminescence (EL) spectrum of a device incorporating 0.2 wt % of (POSS)(Ir compound I), 0.4 wt % of (POSS)(Ir compound III) and 5 wt % of (POSS)(Ir compound IV) as a function of wavelength.
  • the CIE coordinate is (0.23, 0.35).
  • FIG. 14 shows the current density-voltage curve of a device incorporating 0.2 wt % of (POSS)(Ir compound I), 0.6 wt % of (POSS)(Ir compound III) and 5 wt % of (POSS)(Ir compound IV) and an additional electron injection layer, as indicated by closed squares, and the brightness of the same device as a function of voltage as indicated by open squares.
  • FIG. 15 shows the EQE (indicated by closed squares) and luminous efficiency (indicated by open squares) of a device incorporating 0.2 wt % of (POSS)(Ir compound I), 0.6 wt % of (POSS)(Ir compound III) and 5 wt % of (POSS)(Ir compound IV) and an additional electron injection layer as a function of current density.
  • FIG. 16 shows the electroluminescence (EL) spectrum of a device incorporating 0.2 wt % of (POSS)(Ir compound I), 0.6 wt % of (POSS)(Ir compound III) and 5 wt % of (POSS)(Ir compound IV) and an additional electron injection layer as a function of wavelength at 7V and 11V.
  • the CIE coordinate is (0.253, 0.354) at 7V and (0.253, 0.349) at 11V.
  • a nanoparticle is a particle having a cross-sectional measurement (e.g., diameter if spherical) of about 100 nm or less.
  • Dendrimers are examples of nanoparticles.
  • Nanoparticles may be soluble or insoluble polymers (copolymers, hyperbranched polymers, etc), having the ability to aggregate, accumulate and/or self-assemble into particles of about 100 nm or less.
  • the silsesquioxane group of the formula (II) is an example of a nanoparticle.
  • Dendrimers are branched molecular materials that exhibit useful properties of both small molecules and polymers. See e.g. Frechet, J. M. J.; Hawker, C. J. Comprehensive Polymer Science, 2nd Supplement; Pergamon: Oxford, England, 1996; pp 140-206.
  • a dendrimer is a substantially monodisperse synthetic macromolecule possessing a three-dimensional architecture that comprises a central core, highly branched but substantially regular iterative building units, and numerous peripheral ending groups. A more detailed description of these terms is found in G. Odian, Principles of Polymerization, John Wiley, New York, 2 nd Ed., 1981, pp. 177-179 and in W. R. Sorenson, F. Sweeney and T. W.
  • substituent when a substituent referred to as being “optionally substituted,” or “substituted” it is meant that the substituent is a group that may be substituted with one or more group(s) containing about 1 to about 20 atoms individually and independently selected from alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkynyl, aryl, heteroaryl, heteroalicyclyl, aralkyl, heteroaralkyl, (heteroalicyclyl)alkyl, hydroxy, protected hydroxyl, alkoxy, aryloxy, acyl, ester, mercapto, alkylthio, arylthio, cyano, halogen, carbonyl, thiocarbonyl, O-carbamyl, N-carbamyl, O-thiocarbamyl, N-thiocarbamyl, C-amido, N-amido, S-sulf
  • aryl refers to single C 3-20 carbocyclic and poly-C 3-20 carbocyclic ring systems with a fully delocalized pi-system.
  • exemplary aryl groups are phenyl and naphthyl.
  • alkyl as used herein is a linear or branched chain of one to thirty-five carbon atoms.
  • alkyl groups include but are not limited to methyl, ethyl, propyl, isopropyl, n-butyl, iso-butyl, tert-butyl, and the like.
  • cycloalkyl refers to fully saturated single carbocyclic and poly-carbocyclic ring systems with three to thirty five carbon atoms.
  • a “monodentate ligand” refers to a ligand which forms one bond (e.g., a coordinate covalent bond and/or covalent bond) to a central atom, such as a metal ion, A monodentate ligand can be a neutral molecule or an ion with a lone pair.
  • a “bidentate” ligand refers to a ligand which forms two bonds (e.g., a coordinate covalent bond and/or covalent bond) to a central atom.
  • phosphorescence refers to emission from a triplet excited state of an organic molecule.
  • fluorescence refers to emission from a singlet excited state of an organic molecule.
  • An “aggregate emitter” comprises two or more light-emitting compounds that are bound in the ground state and/or in the excited state.
  • An “excimer” is a dimer with an excited state wavefunction that extends over two identical molecules, and is formed when the light-emitting compounds comprising the aggregate emitters are bound in the excited state but not in the ground state.
  • sisesquioxane is the general name for a family of polycyclic compounds consisting of silicon and oxygen. Silsesquioxanes are also known as silasesquioxanes and polyhedral oligomeric silsesquioxanes (POSS).
  • the “work function” of a metal is a measure of the minimum energy required to extract an electron from the surface of the metal.
  • a “high work function metal” is a metal or alloy that easily injects holes and typically has a work function greater than or equal to 4.5.
  • a “low work function metal” is a metal or alloy that easily loses electrons and typically has a work function less than 4.3.
  • a “wet process” is used herein in its ordinary sense as understood by those skilled in the art and includes a process of laying down a layer where the materials that are included in the layer are in aqueous or organic solution. Examples of wet processes include but are not limited to spraying, spin coating, drop casting, inkjet printing and screen printing.
  • a material is white light-emitting if it emits white light.
  • the X and Y color coordinates are weights applied to the CIE primaries to match a color.
  • the color rendering index refers to the ability to render various colors and has values ranging from 0 to 100, with 100 being the best.
  • an embodiment provides an iridium complex attached to the nanoparticle core.
  • the iridium-complex can be a phosphorescent emitter.
  • the iridium-functionalized nanoparticle is represented by Formula (I) as follows:
  • the core in Formula (I) represents the nanoparticle core, while
  • the X in Formula (I) may be a single bond or
  • the iridium-functionalized nanoparticle of Formula (I) further comprises at least one host having the formula
  • k is 0 or an integer selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 and 20.
  • the host may comprise a hole transport material or an electron transport material, and a mixture of the hole transport and electron transport hosts can be attached to the core.
  • the iridium-functionalized nanoparticle may be represented by the following formulas:
  • R′ is represented by
  • the R 3 is a second optionally substituted bidentate ligand.
  • R 3 may be a host, and each R 5 in Formula (I), (II), and (III) can be independently selected from the following:
  • a light-emitting composition may comprise a plurality of the iridium-functionalized nanoparticles independently selected from the compounds of Formula (I), (II) or (III).
  • the first optionally substituted bidentate ligand may be independently selected from the following:
  • the first optionally substituted bidentate ligand may also be independently selected from substituted derivatives of the following:
  • the first bidentate ligand may be independently selected from the following:
  • the two bidentate ligands or the two optionally substituted bidentate ligands may be the same.
  • the second optionally substituted bidentate ligand may be selected from the following group:
  • R 1 is selected from alkyl, substituted alkyl, aryl and substituted aryl
  • R 2 is selected from: alkyl, substituted alkyl, aryl and substituted aryl
  • * indicates a point of attachment to the core or X.
  • An embodiment described herein relates to a light-emitting composition that comprises one or more compound of formula (I) selected from:
  • R 3 is the host having one of the following formulas
  • R 5 can be selected from the following:
  • R is independently selected from H or alkyl, and * indicates a point of attachment to the Si or the alkyl group in R 3 .
  • the iridium-functionalized nanoparticles can be prepared in various ways, e.g., by attaching the iridium-based complex to a nanoparticle core. A preferred method for making nanoparticles that emit light is illustrated herein.
  • the covalent attachment of the iridium-complexes to the a silsesquioxane nanoparticle core is preferably carried out in the general manner as described herein and in PCT WO 02/05971, which is hereby incorporated by reference.
  • a preferred nanoparticle core is a silsesquioxane as shown in Formula (II), more preferably a 1,3,5,7,9,11,13,15-octakis(dimethylsilyloxy)pentacyclo-[9.5.1.1 3,9 .1 5,15 .1 7,13 ]octasiloxane as shown in Formula (III), both formulas are shown above.
  • Light-emitting nanoparticles that emit various colors may be created by attaching one or more iridium-complexes to a nanoparticle core.
  • An exemplary method for preparing the iridium-functionalized nanoparticles described herein is shown in Schemes 1a-c and 2a-d.
  • q can be 0 or an integer in the range of 1 to 18.
  • R 1 are the same as described above, p and q can be 0 or an integer in the range of 1 to 18, and R 5 can be selected from the following:
  • R is independently selected from H or alkyl, and * indicates a point of attachment to the Si or the alkyl group in R 4 .
  • Suitable bases are known to those skilled in the art. In one embodiment, an exemplary base is imidazole.
  • suitable [Pt] catalysts are known to those skilled in the art. In one embodiment, an exemplary [Pt] catalyst is platinum divinyltetramethyldisiloxane (Pt(dvs)).
  • Iridium-functionalized nanoparticles may be configured to emit various colors, depending on the identities of the iridium complexes.
  • the iridium complex is preferably selected so that the resulting iridium-functionalized nanoparticles emit the desired color, (e.g., white light).
  • the desired color e.g., white light.
  • the nanoparticle core can be a single silsesquioxane with a silsesquioxane core represented by Formula (II).
  • the silsesquioxane core shown in Formula (II) has a relatively stiff cubical structure and the iridium complexes, represented by R′ groups in Formula (II), can be attached at the vertices of the silsesquioxane.
  • an embodiment provides a light-emitting device, comprising: an anode layer comprising a high work function metal; a cathode layer comprising a low work function metal; and a light-emitting layer positioned between, and electrically connected to, the anode layer and the cathode layer.
  • the light-emitting layer comprises an iridium-functionalized nanoparticle or composition thereof, as described herein.
  • the light-emitting layer comprises phosphorescent emitting-functionalized nanoparticles such as iridium-functionalized nanoparticles.
  • the iridium-functionalized nanoparticle is represented by Formula (I).
  • the iridium-functionalized nanoparticle is an organic-inorganic iridium-functionalized nanoparticle.
  • the organic-inorganic iridium-functionalized nanoparticle comprises a nanoparticle core that comprises inorganic elements such as phosphorous (P), silicon (Si), and/or a metal.
  • a nanoparticle core comprises a moiety selected from the group consisting of a silsesquioxane, a cyclophosphazene, a triazine, a cyclodextrin, a calumblene, a phthalocyanine, and a silica particle.
  • the light-emitting compositions described herein can include one or more iridium-functionalized nanoparticles and/or other materials in addition to the iridium-functionalized nanoparticle(s).
  • An anode layer may comprise a conventional material such as a metal, mixed metal, alloy, metal oxide or mixed-metal oxide, or a conductive polymer.
  • suitable metals include the Group 1 metals, the metals in Groups 4, 5, 6, and the Group 8-10 transition metals. If the anode layer is to be light-transmitting, mixed-metal oxides of Group 12, 13, and 14 metals or alloys thereof, such as Au, Pt, and indium-tin-oxide (ITO), may be used.
  • the anode layer may include an organic material such as polyaniline, e.g., as described in “Flexible light-emitting diodes made from soluble conducting polymer,” Nature, vol. 357, pp. 477-479 (11 Jun.
  • the anode layer can have a thickness in the range of about 1 nm to about 1000 nm.
  • a cathode layer may include a material having a lower work function than the anode layer.
  • suitable materials for the cathode layer include those selected from alkali metals of Group 1, Group 2 metals, Group 12 metals including rare earth elements, lanthanides and actinides, materials such as aluminum, indium, calcium, barium, samarium and magnesium, and combinations thereof.
  • Li-containing organometallic compounds, LiF, and Li 2 O may also be deposited between the organic layer and the cathode layer to lower the operating voltage.
  • Suitable low work function metals include but are not limited to Al, Ag, Mg, Ca, Cu, Mg/Ag, LiF/Al, CsF, CsF/Al or alloys thereof.
  • the cathode layer can have a thickness in the range of about 1 nm to about 1000 nm.
  • the amount of the iridium-functionalized nanoparticle(s) in the light-emitting composition can vary. In some embodiments, the amount of iridium-functionalized nanoparticles in the light-emitting composition layer can be in the range of from about 1% to about 100% by weight based on total weight of the light-emitting layer. In an embodiment, the amount of iridium-functionalized nanoparticles in the light-emitting layer can be in the range of from about 30% to about 70% by weight based on total weight of the light-emitting layer.
  • the amount of iridium-functionalized nanoparticles in the light-emitting layer can be in the range of from about 1% to about 10% by weight based on total weight of the light-emitting layer. In some embodiments, the light-emitting layer can have a thickness in the range of about 20 nm to about 150 nm.
  • the light-emitting layer can further include a host material.
  • exemplary host materials are known to those skilled in the art.
  • the host material included in the light-emitting layer can be an optionally substituted compound selected from: an aromatic-substituted amine, an aromatic-substituted phosphine, a thiophene, an oxadiazole, 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (PBD), 1,3-bis(N,N-t-butyl-phenyl)-1,3,4-oxadiazole (OXD-7), a triazole, 3-phenyl-4-(1′-naphthyl)-5-phenyl-1,2,4-triazole (TAZ), 3,4,5-Triphenyl-1,2,3-triazole, 3,5-Bis(4-tert-butyl-phenyl)-4-phenyl
  • Exemplary hole-transport materials include 4,4′-bis[N-(naphthyl)-N-phenyl-amino]biphenyl ( ⁇ -NPD), N,N′-bis(3-methylphenyl)N,N′-diphenyl-[1,1′-biphenyl]-4,4′-diamine (TPD), 4,4′-bis[N,N′-(3-tolyl)amino]-3,3′-dimethylbiphenyl (M14), 4,4′,4′-tris(3-methylphenylphenylamino)triphenylamine (MTDATA), 4,4′-bis[N,N′-(3-tolyl)amino]-3,3′-dimethylbiphenyl (HMTPD), N,N′N′′-1,3,5-tricarbazoloylbenzene (t)
  • electron-transport materials include aluminum tris(8-hydroxyquinolate) (Alq3), 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (PBD), 1,3-bis(N,N-t-butyl-phenyl)-1,3,4-oxadiazole (OXD-7), 3-phenyl-4-(1′-naphthyl)-5-phenyl-1,2,4-triazole (TAZ), 2,9-dimethyl-4,7-diphenyl-phenanthroline (bathocuproine or BCP), and 1,3,5-tris[2-N-phenylbenzimidazol-z-yl]benzene (TPBI).
  • Alq3 aluminum tris(8-hydroxyquinolate)
  • PBD 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole
  • OXD-7 1,
  • additional layers may be included in the light-emitting device. Additional layers that may be included include an electron injection layer (EIL), electron transport layer (ETL), hole blocking layer (HBL), exciton blocking layer (EBL), hole transport layer (HTL), and/or hole injection layer (HIL).
  • EIL electron injection layer
  • ETL electron transport layer
  • HBL hole blocking layer
  • EBL exciton blocking layer
  • HTL hole transport layer
  • HIL hole injection layer
  • the light-emitting device can include an electron injection layer e.g., between the cathode layer and the light emitting layer.
  • the lowest un-occupied molecular orbital (LUMO) energy level of the material(s) that can be included in the electron injection layer is preferably high enough to prevent it from receiving an electron from the light emitting layer.
  • the energy difference between the LUMO of the material(s) that can be included in the electron injection layer and the work function of the cathode layer is preferably small enough to allow efficient electron injection from the cathode.
  • suitable electron injection materials are known to those skilled in the art.
  • suitable material(s) that can be included in the electron injection layer include but are not limited to, an optionally substituted compound selected from the following: aluminum quinolate (Alq3), 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (PBD), phenanthroline, quinoxaline, 1,3,5-tris[N-phenylbenzimidazol-z-yl]benzene (TPBI) a triazine, a metal chelate of 8-hydroxyquinoline such as tris(8-hydroxyquinoliate) aluminum, and a metal thioxinoid compound such as bis(8-quinolinethiolato) zinc.
  • Alq3 aluminum quinolate
  • PBD 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole
  • TPBI 1,3,5-tris[N-phenylbenzimidazol-z
  • Some embodiments described herein can include an electron transport layer positioned between the cathode and light-emitting layer.
  • Suitable electron transport materials are known to those skilled in the art.
  • Exemplary electron transport materials that can be included in the electron transport layer are an optionally substituted compound selected from: aluminum tris(8-hydroxyquinolate) (Alq3), 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (PBD), 1,3-bis(N,N-t-butyl-phenyl)-1,3,4-oxadiazole (OXD-7), 3-phenyl-4-(1′-naphthyl)-5-phenyl-1,2,4-triazole (TAZ), 2,9-dimethyl-4,7-diphenyl-phenanthroline (bathocuproine or BCP), and 1,3,5-tris[2-N-phenylbenzimidazol-z-yl]benzene (
  • the device can include a hole blocking layer, e.g., between the cathode and the light-emitting layer.
  • a hole blocking layer e.g., between the cathode and the light-emitting layer.
  • suitable hole blocking materials that can be included in the hole blocking layer are known to those skilled in the art.
  • Suitable hole blocking material(s) include but are not limited to, an optionally substituted compound selected from the following: bathocuproine (BCP), 3,4,5-triphenyl-1,2,4-triazole, 3,5-bis(4-tert-butyl-phenyl)-4-phenyl-[1,2,4]triazole, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline, and 1,1-bis(4-bis(4-methylphenyl)aminophenyl)-cyclohexane.
  • BCP bathocuproine
  • 3,4,5-triphenyl-1,2,4-triazole 3,5-bis(4
  • the light-emitting device can include an exciton blocking layer, e.g., between the light-emitting layer and the anode.
  • the band gap of the material(s) that comprise exciton blocking layer is preferably large enough to substantially prevent the diffusion of excitons.
  • suitable exciton blocking materials that can be included in the exciton blocking layer are known to those skilled in the art.
  • Examples of material(s) that can compose an exciton blocking layer include an optionally substituted compound selected from the following: aluminum quinolate (Alq 3 ), 4,4′-bis[N-(naphthyl)-N-phenyl-amino]biphenyl ( ⁇ -NPD), 4,4′-N,N′-dicarbazole-biphenyl (CBP), and bathocuproine (BCP), and any other material(s) that have a large enough band gap to substantially prevent the diffusion of excitons.
  • Alq 3 aluminum quinolate
  • ⁇ -NPD 4,4′-bis[N-(naphthyl)-N-phenyl-amino]biphenyl
  • CBP 4,4′-N,N′-dicarbazole-biphenyl
  • BCP bathocuproine
  • the light-emitting device can include a hole transport layer, e.g., between the light-emitting layer and the anode.
  • Suitable hole transport materials that can be included in the hole transport layer are known those skilled in the art.
  • hole transport material(s) that can be included in the hole transport layer are 4,4′-bis[N-(naphthyl)-N-phenyl-amino]biphenyl ( ⁇ -NPD), N,N′-bis(3-methylphenyl)N,N′-diphenyl-[11′-biphenyl]-4,4′-diamine (TPD), 4,4′-bis[N,N′-(3-tolyl)amino]-3,3′-dimethylbiphenyl (M14), 4,4′,4′-tris(3-methylphenylphenylamino)triphenylamine (MTDATA), 4,4′-bis[N,N′-(3-tolyl)
  • the light-emitting device can include a hole injection layer, e.g., between the light-emitting layer and the anode.
  • a hole injection layer e.g., between the light-emitting layer and the anode.
  • Various suitable hole injection materials that can be included in the hole injection layer are known to those skilled in the art.
  • Exemplary hole injection material(s) include an optionally substituted compound selected from the following: a polythiophene derivative such as poly(3,4-ethylenedioxythiophene (PEDOT)/polystyrene sulphonic acid (PSS), a benzidine derivative such as N,N,N′,N′-tetraphenylbenzidine, poly(N,N′-bis(4-butylphenyl)-N,N′-bis(phenyl)benzidine), a triphenylamine or phenylenediamine derivative such as N,N′-bis(4-methylphenyl)-N,N′-bis(
  • EIL electron injection layer
  • ETL electron transport layer
  • HBL hole blocking layer
  • EBL exciton blocking layer
  • HTL hole transport layer
  • HIL hole injection layer
  • Light-emitting devices comprising iridium-functionalized nanoparticles can be fabricated using techniques known in the art, as informed by the guidance provided herein.
  • a glass substrate can be coated with a high work functioning metal such as ITO which can act as an anode.
  • a light-emitting composition layer that includes the iridium-functionalized nanoparticles can be deposited on the anode.
  • the cathode layer comprising a low work functioning metal (e.g., Mg:Ag), can then be vapor evaporated onto the light-emitting composition layer.
  • the device can also include an electron transport/injection layer, a hole blocking layer, a hole injection layer, an exciton blocking layer and/or a second light-emitting layer that can be added to the device using techniques known in the art, as informed by the guidance provided herein.
  • an advantage of the light-emitting compositions described herein is that their molecular weights are large enough to allow for spray, dip, printing, and/or spray coating.
  • the lighting-emitting device can be produced without having to employ complicated and expensive multilayer vapor deposition.
  • the iridium-functionalized nanoparticles described herein can be easily spun off onto a hard or flexible substrate. As a result, the manufacture of the OLED device becomes much easier.
  • the light emitting devices described herein can be configured to emit various colors of light.
  • two or more iridium-functionalized nanoparticles can be combined in different ratios to produce a color of light.
  • one or more iridium-functionalized nanoparticles can be combined with one or more light emitting compounds to produce a color of light.
  • blue emitting iridium-functionalized nanoparticles and orange emitting compound(s) e.g., orange iridium-functionalized nanoparticles
  • the light-emitting composition is configured to emit light such as blue, green, orange, red and white.
  • lumophore-functionalized nanoparticles may be configured to emit various colors, depending on the identities of the lumophores and host groups.
  • the relative ratio of host groups to lumophores are selected so as to have a high level of energy transfer from the host(s) to the lumophore(s) and/or so that light is emitted when energy is transferred to the lumophore(s) from the host(s).
  • White light can be obtained by the appropriate choice of lumophores and/or hosts, and/or the relative ratios of host groups to lumophores.
  • the chosen lumophores have Commission Internationale de L'Eclairage (CIE) color coordinates that lie on a line which substantially intersects the achromatic point.
  • CIE Commission Internationale de L'Eclairage
  • the incorporation of hole-transport or electron-transport moieties onto the nanoparticle core as hosts can increase the charge mobility, and/or balance the hole-transport or electron-transport inside the device.
  • the direct attachment of the host to the nanoparticle core can further improve the compatibility between hole-transport or electron-transport moieties (i.e., host) and emissive dopant (i.e., Ir complex) or reduce the possibility of phase separation.
  • exemplary lumophore-functionalized nanoparticles with a silsesquioxane core are shown below:
  • the Ir-complex-A, Ir-complex-B and Ir-complex-C represent three different Ir-complexes that can be any of the Ir-complexes described above.
  • the “host” is also the same as defined above. By mixing different ratio of the three red-green-blue host/lumophore-functionalized nanoparticles, one embodiment of light-emitting device may emit white or near white light.
  • An embodiment provides a light-emitting composition that includes a mixture of different host/lumophore-functionalized nanoparticles.
  • the light-emitting composition may comprise one or more compound of formula (I) as defined above.
  • the light emitting composition may be a mixture of two or more compounds selected from the following group:
  • R 3 is the host having the formula
  • R 5 can be selected from the following:
  • R is independently selected from H or alkyl, and * indicates a point of attachment to the Si or the alkyl group in R 3 .
  • the identities of the lumophores and the relative ratio of lumophores to host groups can be selected to as to have a CRI value in the range of about 60 to about 100, about 80 to about 100, or greater than 70.
  • Dimer I was synthesized in accordance with the procedures described in J. Am. Chem. Soc., 1984, 106, 6647 and Bull. Chem. Soc. Jpn., 1974, 47, 767, which are both hereby incorporated by reference in their entireties.
  • Iridium trichloride hydrate (1 mmol) was combined with 2-phenylpyridine (4.46 mmol) dissolved in a mixture of 2-ethoxyethanol and water (3/1). The mixture was refluxed for 24 h. The solution was then cooled to room temperature, and the yellow precipitate was washed with 95% ethanol and acetone. The yellow precipitate was then dissolved in dichloromethane and filtered. Toluene and hexane were added to the filtrate, which was then reduced in volume by evaporation. After cooling, crystals of dimer I was obtained.
  • dimer II was synthesized in a similar manner as described with respect to dimer I in Example 2.
  • Ir compound III was synthesized in a similar manner as described with respect to Ir compound I and Ir compound II in Examples 3 and 6, respectively.
  • Dimer IV [(dfppy) 2 Ir( ⁇ -Cl)] 2 Dimer IV was synthesized in accordance to the procedures disclosed in J. Am. Chem. Soc., 2005, 127, 12438, which is hereby incorporated by reference in its entirety. Yield of dimer IV was 76%.
  • Dec-9-ene-2,4-dione was synthesized using a similar procedure as described in Example 1 or following the literature procedure described in Helv. Chim. Acta., 1977, 60, 638.
  • Ir compound IX is synthesized in a similar manner as described with respect to Ir compound V in Example 15. The synthesis of Dimer V was adopted from literature: Adv. Mater. 2003, 15, 884.
  • N-allylcarbazole (1.00 g, 4.83 mmol) was added and the reaction mixture was allowed to stir at room temperature for 2 hours. The toluene was evaporated in vacuo and the product was separated chromatographically using 1:1 dichloromethane:hexanes to yield 301 mg (20%).
  • N-allylcarbazole (1.00 g, 4.83 mmol) was added and the reaction mixture was allowed to stir at room temperature for 2 hours. The toluene was evaporated in vacuo and the product was separated chromatographically using 1:1 dichloromethane:hexanes to yield 299 mg (19%).
  • the ITO coated glass substrates were cleaned by ultrasound in acetone and 2-propanol, followed by treatment with oxygen plasma.
  • a layer of PEDOT: PSS (Baytron P purchased from H. C. Starck) was spin-coated at 3000 rpm and annealed at 180° C. for 10 min onto the pre-cleaned and O 2 -plasma treated (ITO)-substrate, yielding a thickness of around 40 nm.
  • PVK/PBD or PVK/OXD-7) (weight ratio 70:30), and iridium complexes (1-6 wt %) in chlorobenzene solution were spin-coated on top of the PEDOT:PSS layer, yielding a 70 nm thick film.
  • the samples were annealed at 80° C. for 30 minutes.
  • a cathode layer comprising an ultra-thin CsF interface layer with a nominal thickness of 1 nm and a ca. 70 nm thick Al layer was deposited by thermal evaporation at a base pressure of 10 ⁇ 6 mbar onto the annealed blend.
  • Spectra were measured with an ocean optics HR4000 spectrometer and I-V light output measurements were taken with a Keithley 2400 SourceMeter and Newport 2832-C power meter and 818 UV detector. All device operation was carried out inside a nitrogen-filled glove-box. Individual devices had area of about 0.14 cm 2 . An exemplary configuration of the device is shown in FIG. 2 .
  • Light-emitting composition containing a mixture of host/lumophore-functionalized nanoparticles A light-emitting device comprising a mixture of host/lumophore-functionalized nanoparticles can be fabricated using the technique described in EXAMPLE 31. Instead of using one iridium complex, three different Ir complex-functionalized POSS were used to form the light-emitting layer.
  • the light-emitting layer of device A was made by using a mixture of the following Ir complex-functionalized POSS—0.2 wt % of (POSS)(Ir compound I), 0.4 wt % of (POSS)(Ir compound III) and 5 wt % of (POSS)(Ir compound IV).
  • FIG. 11 shows Current-Voltage-Brightness chart of device A.
  • FIG. 12 shows the external quantum efficiency (EQE) and luminous efficiency as a function of current density of device A.
  • FIG. 13 shows the CIE chart of device A.
  • the light-emitting layer of device B was made by using a mixture of 0.2 wt % of (POSS)(Ir compound I), 0.6 wt % of (POSS)(Ir compound III) and 5 wt % of (POSS)(Ir compound IV).
  • the device also has an additional electron injection layer, which was made of 30 nm of TPBI spin-coated on top of the light-emitting layer.
  • FIG. 14 shows Current-Voltage-Brightness chart of device B.
  • FIG. 15 shows the external quantum efficiency (EQE) and luminous efficiency as a function of current density of device B.
  • FIG. 16 shows the CIE chart of device B at 7V and 11V. The color stability of device B is very good as the CIE coordinates varied only (0, 0.005) between 7V (1 cd/m 2 ) and 11V (2400 cd/m 2 ).
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US8609258B2 (en) 2013-12-17

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