CN1631890A

CN1631890A - Tetraphenyl porphyrin derivative and its application in organic electroluminescent device

Info

Publication number: CN1631890A
Application number: CN 200410011333
Authority: CN
Inventors: 王悦; 霍成; 郭建华
Original assignee: Jilin University
Current assignee: Jilin Jida Photoelectric Technology Co., Ltd.
Priority date: 2004-12-10
Filing date: 2004-12-10
Publication date: 2005-06-29
Anticipated expiration: 2024-12-10
Also published as: CN100361994C

Abstract

The invention relates to a (1) or (2) and its application in preparation of organic EL device. M is Zn or Pt; three substituent group or R1, R2, R3 are different or the same and at least one of them is alkoxy substituent carbazole derivative shown as (3); R10 and R11 are different or the same, as alkyl of C1-4 (n=4-12); the other two substituent group is H and alkoxy and alkyl (C1-C4) or alkoxy substituent carbazole derivative shown as (3). The device made by the invention has high efficiency of EL, outstanding solubility and filmibility, easy to be mixed with polymer, benefiting for research to EL device, can be used to prepare red luminous, with simple technique, benefit for industrialized batch production .

Description

Tetraphenylporphyrin derivative and the application in organic electroluminescence device thereof

Technical field

The present invention relates to a kind of electroluminescent organic material and application thereof, be specifically related to a kind of tetraphenylporphyrin derivative and as the application of luminescent material in organic electroluminescence device.

Background technology

The organic electroluminescent phenomenon is found the time of existing three more than ten years, before 1987, because the great drawback (cut-in voltage＞200V), limited its application that organic electroluminescence device exists.Because the continuous breakthrough of material and device technology, organic electroluminescent has been reached or since nearly ten years near the practicability stage.

Nineteen sixty-five Gurnee etc. has delivered the patent (U.S.Pat.No.3,172,862,3,173,050) about organic electroluminescence device first.Dresner in 1973 have also delivered the patent (U.S.Pat.No.3,170,167) of organic electroluminescence device aspect.Many aromatic rings organic compound such as anthracene, four acenes, five acenes etc. are used to electroluminescent organic material in these inventions.Early stage device primary structure is characterized as single layer structure, and the thickness of organic luminous layer is greater than 1mm, and the cut-in voltage of device is more than 200v.

The eighties, the smell etc. of company of Kodak was at first found ultra-thin multilayer device structure, the cut-in voltage of device was reduced greatly (U.S.Pat.No.4,356,429).The essential characteristic of its device is to be substrate with the conductive glass, elder generation's evaporation last layer hole injection layer (100nm), also be transport layer simultaneously, spin coating last layer organic electron transport layer then, also be electroluminescence layer simultaneously, plate layer of metal at last as negative pole, this device cut-in voltage is 20v, and brightness is 5cd/m ²Employing aromatic multi-amine such as the VanSlyke of company of Kodak is that hole transmission layer carries out the device preparation afterwards, and device performance is improved greatly, and brightness can reach 340cd/m2.

The VanSlyke of company of Kodak and smell find that at first Alq3 (oxine aluminium) has after the good electroluminescent properties, people have synthesized a series of electroluminescent materials with oxine and derivative thereof with Al3+, Zn2+, Ga3+, Be2+ etc. in succession, the most of jaundice of these materials green glow, some blue light-emitting (is seen U.S.Pat.No.4,720,432; U.S.Pat.No.4,539,507; C.W.Tang, S.A.VanSlyke, Appl.Phys.1987,51,913; U.S.Pat.No.5,151,629; Hamada, Jpn.J.Appl.Phys., part 2., 1992,32, L 514; Matsumura, Jpn.J.Appl.Phys., 1996,35,5357; The cave, J.Appys., 1996,79,7991).The Sano of Japan Sanyo company etc. are at U.S.Pat.5, in 432,014 with the west not alkali-Zn complex prepared blue-light device as luminescent layer.Hamada of it should be noted that Japanese Sanyo company etc. synthesizes 10-hydroxy benzo quinoline compound, and its electroluminescent properties has surpassed Alq3 (Hamadadeng Chem.lett., 1993,950).

Because the discovery of electroluminescent material and the continuing to optimize of device architecture of some excellent propertys make organic electroluminescent obtain some breakthroughs.(see U.S.Pat.No.5,151,629; 5,150,006; 5,141,671; 5,073,446; 5,061,569; 5,059,862; 5,059,861; 5,047,687; 4,950,950; 5,104,740; 5,227,252; 5,256,945; 5,069,957; 5,122,711; 5,554,450; 5,683,823; 5,593,788; 5,645,948; 5,451,343; 5,623,080; 5,395,862).

Porphyrin compound is applied in the electroluminescent field mainly since 1998 as luminescent material.The research group of Princeton university in 1998 adopts phosphor material octaethylporphyrin platinum as dopant material, and electron transport material Alq3 has prepared the red emission device as material of main part and (seen U.S.Pat.No.6,303,238; S.R.Forrest, character, 1998,395,151), maximum external quantum efficiency is 4%.From then on opened up the beginning that the phosphorescence porphyrin compound is used aspect electroluminescent.The scientific research group of American South University of California in 1999 and Princeton University has developed porphyrin platinic compound PtDPP, the PtOX of two kinds of different substituents groups again, has prepared the red emission device and (has seen U.S.Pat.No.6,413,656; S.R.Forrest, Chem.Mater, 1999,11,3709).But their external quantum efficiency is all lower, and less stable, does not have carrier transmission performance.Therefore seek efficient height, good stability, have carrier transmission performance simultaneously, can realize that high efficiency electroluminous material is a problem that presses for solution.

Summary of the invention

The purpose of this invention is to provide a class can realize luminous efficiency height, good stability, have carrier transmission performance in the broad concentration range electroluminescent organic material, and the application of this material in organic electroluminescence device.

Find that after deliberation the tetraphenylporphyrin derivative has good electroluminescence characters.Of the present invention to liking structural formula as (1)

(2) compounds shown in.

General formula (1) and (2) representative are the tetraphenylporphyrin derivative of basic structure skeleton with the tetraphenylporphyrin, and wherein M is zinc (Zn) or Pt; R ₁, R ₂, R ₃Three substituted radicals can be identical or different, and wherein having a substituted radical at least is (the R wherein of the alkoxyl group substituted carbazole derivative shown in the formula (3) ₁₀And R ₁₁Can be identical or different, can be H or C _1-4Alkyl, n=4-12), all the other two substituted radicals are H, C ₁-C ₄Alkoxyl group, alkyl or formula (3) shown in alkoxyl group substituted carbazole derivative.

Formula of the present invention (1) and (2) are new tetraphenylporphyrin derivative.The compound of formula of the present invention (1) and (2) is applicable to the high performance organic electroluminescence device of preparation.The device advantage of using material preparation of the present invention is the electroluminescent efficiency height, solvability, good film-forming property, thus be easy to carry out the research of device with polymer blending, device technology is become simply, help the devices in batches suitability for industrialized production.

At first prepare alkoxyl group substituted carbazole derivative:

For preparation tetraphenylporphyrin derivative is undertaken by following reaction pattern 1:

Reaction pattern 1:1-1 works as R ₁, R ₂, R ₃When three substituted radicals had one to be alkoxyl group substituted carbazole derivative, the preparation mode of preparation tetraphenylporphyrin derivative was as follows:

Pattern 1-2: work as R ₁, R ₂, R ₃When three substituted radicals had two to be alkoxyl group substituted carbazole derivative, the preparation mode of preparation tetraphenylporphyrin derivative was as follows:

Pattern 1-3: work as R ₁, R ₂, R ₃When three substituted radicals all were alkoxyl group substituted carbazole derivative, the preparation mode of preparation tetraphenylporphyrin derivative was as follows:

Owing to have big C by reaction pattern 1 (1-1,1-2,1-3) institute synthetic tetraphenylporphyrin derivative ₄-C ₁₂N-carbazole substituted alcoxyl group, the porphyrin core has been played the function of spatial separation, therefore weakened the concentration quenching effect when luminous, increased the solvability and the film-forming properties of material simultaneously, thereby helped carrying out device research with polymer blending.

Because the fluorescence emission peak of carbazole and porphyrin absorb and have very big overlappingly, the excited energy that produces on the carbazole group can be delivered to the center porphyrin and examine, thereby causes better red emission; Carbazole has good carrier transmission performance simultaneously, and therefore the device with these material preparations has higher electroluminescent efficiency.

The raw material that reaction pattern 1 adopts is carbazole or substituted carbazole, C ₄-C ₁₂Two bromoalkanes, pyrroles, substituted benzaldehyde.Preceding two kinds of raw materials are at N, (under the NaH existence condition) back flow reaction generates compound (3) in the dinethylformamide solution, the two kinds of raw materials in back are at N, reacting generating compound (A) under the reflux conditions in the dinethylformamide solution, (B), (D), compound (B), (D) back flow reaction obtains compound (C) in methyl alcohol and boron tribromide mixing solutions, (E), compound (C), (E) at N, dinethylformamide, triethylamine, reaction obtains target compound (1) in compound (3) mixing solutions, and compound (1) is at propionic acid, reacting by heating or at acetonitrile in the zinc acetate mixing solutions, reacting by heating obtains target compound (2) in the platinum dichloride mixing solutions.

Compound of the present invention can be used as electroluminescent material and is used to prepare electroluminescent device, especially can be used for the active coating of electroluminescent device.So-called active coating is exactly can be luminous under certain driving voltage or have that electric charge injects, the organic thin film layer of transmission performance.Therefore object of the present invention also be formula of the present invention (1) and (2) compound as the application of electroluminescent material and contain formula (1) and the mixture of (2) compound as the application of electroluminescent material.

By device electroluminescent spectrum, brightness, current/voltage characteristic analytical procedure test material and device performance, its characteristic of electroluminescent device of using formula of the present invention (1) and (2) compound is as follows: about cut-in voltage 4.5V, high-high brightness reaches 240cd/m ², maximum external quantum efficiency reaches 5.68%.This shows that the synthetic method of the compound of formula of the present invention (1) and (2) is simple, purification is convenient, be applied to the electroluminescent red light material has characteristics such as cut-in voltage is low, brightness is high, luminous efficiency is high, good stability.

Description of drawings

Fig. 1: the electroluminescent device structural representation of using organic materials of the present invention.

Formula of the present invention (1) and the application of (2) compound in electroluminescent device now are described in conjunction with the accompanying drawings.Object of the present invention can be used for preparing the electroluminescent device that has one or more active coatings, and in these active coatings at least one deck contain one or more compounds of the present invention.Active coating can be a light-emitting layer and/or a migrating layer and/or a charge injection layer.The basic structure of this type of luminescent device as shown in Figure 1, this figure is the electroluminescent device of a multilayered structure, it is by attached to the ITO on the transparent glass 1 (tin indium oxide) conductive layer (positive pole) 2 and metal (Al, the Mg:Ag alloy, Ca, Na, K) layer (negative pole) 7 and be clipped in two carrier injection layer (hole injection layer 3 and electron injecting layer 6) and two active coatings formations between the two poles of the earth, these two active coatings also are simultaneously that electron transport material 5 constitutes by hole mobile material (as NPB) 4 and luminescent material respectively, material therefor is an electroluminescent organic material of the present invention in 5, or comprises electroluminescent organic material of the present invention.Hole and electronics inject from positive and negative polarities respectively, transmission in hole transmission layer and electron transfer layer (also being luminescent layer) respectively in two-layer near interface zone electronics and hole-recombination, and produces exciton, exciton is got back to ground state by radiative transition, just has light to send.

This radiative color can be used material of the present invention and can prepare the emitting red light device by changing the compound change of using as luminescent layer.Between electroluminescence layer and negative electrode, can add pack into one deck electronics injecting layer and/or electron transfer layer and improve device performance.

These el light emitting devices can as on self luminous indicator elment such as signal lamp, aplhanumeric visual display, direction board, the photoelectronic coupler, the application in the various flat-panel monitor (display screens of mobile phone, Digital Video, Digit camera, palm PC etc.).

Embodiment

Further illustrate the preparation and the application of The compounds of this invention below by example, rather than will limit the present invention with these examples, all raw materials all can obtain from the commercial channel.

Example 1: compound 1-1-01's is synthetic

With 150 milliliters of N, dinethylformamide is made solvent, adds hydrogenation of compounds sodium 3.0 grams, carbazole 10 grams and 1,4-dibromobutane 20.0 grams, back flow reaction 6 hours.Cooling adds 50 ml methanol and fully stirs after-filtration, and the filtrate of collection concentrates evaporate to dryness, and the crude product hexanaphthene promptly gets product N-(4-brombutyl) carbazole 8.2 grams for the eluent aluminium sesquioxide is the stationary phase column chromatography.Productive rate 45.4%.

With compound 3-methoxyl group-4-hydroxy benzaldehyde 10.0 grams, pyrroles 4.4 gram and N, 600 milliliters of reflux of dinethylformamide 2 hours, cool off static, add 200 ml distilled waters, filtering, is that eluent, aluminium sesquioxide are the stationary phase column chromatography with the crude product methylene dichloride, promptly gets product four-(3-methoxyl group-4-hydroxyl) phenyl porphyrin 3.5 grams.Productive rate 26.7%.

Compound four-(3-methoxyl group-4-hydroxyl) phenyl porphyrin 1.0 grams are added N-(4-brombutyl) carbazole 3.0 grams, 2.0 milliliters of triethylamines, N, 600 milliliters of dinethylformamides, heated and stirred reaction 12 hours.Product concentrates with distilled water and dichloromethane extraction, dichloromethane extraction liquid, is that the stationary phase column chromatography promptly gets product four-[3-methoxyl group-4-(N-carbazole) butoxy] phenyl porphyrin 1.9 grams with methylene dichloride for the eluent aluminium sesquioxide.Productive rate: 90.1%.Mass spectrum molecular ion peak: 1683.Chemical formula C is pressed in ultimate analysis ₁₁₂H ₉₈N ₈O ₈Calculate: C:79.9%; H:5.9%; N:6.6%; O:7.6% experimental value: C:79.8%; H:5.8%; N:6.7%; O:7.4%.

Four-[3-methoxyl group-4-(N-carbazole) butoxy] phenyl porphyrins

1-1-01

Example 2: compound 1-1-02's is synthetic

Compound 1-1-02's is synthetic the same with example 1.Just usefulness is that pentamethylene bromide replaces 1, the 4-dibromobutane.Product four-[3-methoxyl group-4-(N-carbazole) pentyloxy] phenyl porphyrin.Mass spectrum molecular ion peak: 1739.Chemical formula C is pressed in ultimate analysis ₁₁₆H ₁₀₆N ₈O ₈Calculate: C:80.0%; H:6.1%; N:6.4%; O:7.4%; Experimental value: C:79.8%; H:6.2%; N:6.5%; O:7.5%.

Example 3: compound 1-1-03's is synthetic

Compound 1-1-03's is synthetic the same with example 1.Just usefulness is 1, and the 6-dibromo-hexane replaces 1, the 4-dibromobutane.Product four-[3-methoxyl group-4-(N-carbazole) hexyloxy] phenyl porphyrin.Mass spectrum molecular ion peak: 1795.Chemical formula C is pressed in ultimate analysis ₁₂₀H ₁₁₄N ₈O ₈Calculate: C:80.0%; H:6.4%; N:6.2%; O:7.1%; Experimental value: C:80.2%; H:6.3%; N:6.1%; O:7.2%.

Example 4: compound 1-1-04's is synthetic

Compound 1-1-04's is synthetic the same with example 1.Just usefulness is 1, and the 7-dibromo-heptane replaces 1, the 4-dibromobutane.Product four-[3-methoxyl group-4-(N-carbazole) oxygen base in heptan] phenyl porphyrin.Mass spectrum molecular ion peak: 1851.Chemical formula C is pressed in ultimate analysis ₁₂₄H ₁₂₂N ₈O ₈Calculate: C:80.4%; H:6.6%; N:6.1%; O:6.9%; Experimental value: C:80.2%; H:6.5%; N:6.0%; O:7.0%.

Example 5: compound 1-1-05's is synthetic

Compound 1-1-05's is synthetic the same with example 1.Just usefulness is 1, and 8-two bromooctanes replace 1, the 4-dibromobutane.Product four-[3-methoxyl group-4-(N-carbazole) octyloxy] phenyl porphyrin.Mass spectrum molecular ion peak: 1907.Chemical formula C is pressed in ultimate analysis ₁₂₈H ₁₃₀N ₈O ₈Calculate: C:80.6%; H:6.9%; N:5.9%; O:6.7%; Experimental value: C:80.9%; H:6.8%; N:6.1%; O:7.0%.

Example 6: compound 1-1-06's is synthetic

Compound 1-1-06's is synthetic the same with example 1.Just usefulness is 1, and 9-two bromononanes replace 1, the 4-dibromobutane.Product four-[3-methoxyl group-4-(N-carbazole) oxygen base in the ninth of the ten Heavenly Stems] phenyl porphyrin.Mass spectrum molecular ion peak: 1963.Chemical formula C is pressed in ultimate analysis ₁₃₂H ₁₃₈N ₈O ₈Calculate: C:80.7%; H:7.1%; N:5.7%; O:6.5%; Experimental value: C:80.8%; H:6.9%; N:6.0%; O:6.4%.

Example 7: compound 1-1-07's is synthetic

Compound 1-1-07's is synthetic the same with example 1.Just usefulness is 1, and the 10-dibromo-decane replaces 1, the 4-dibromobutane.Product four-[3-methoxyl group-4-(N-carbazole) oxygen base in the last of the ten Heavenly stems] phenyl porphyrin.Mass spectrum molecular ion peak: 2019.Chemical formula C is pressed in ultimate analysis ₁₃₆H ₁₄₆N ₈O ₈Calculate: C:80.8%; H:7.3%; N:5.6%; O:6.3%; Experimental value: C:80.5%; H:7.4%; N:5.8%; O:6.2%.

Example 8: compound 1-1-08's is synthetic

Compound 1-1-08's is synthetic the same with example 1.Just usefulness is 1, and 11-two bromo-n-11s replace 1, the 4-dibromobutane.Product four-[3-methoxyl group-4-(N-carbazole) undecane oxygen base] phenyl porphyrin.Mass spectrum molecular ion peak: 2075.Chemical formula C is pressed in ultimate analysis ₁₄₀H ₁₅₄N ₈O ₈Calculate: C:81.0%; H:7.5%; N:5.4%; O:6.2%; Experimental value: C:81.2%; H:7.3%; N:5.1%; O:6.5%.

Example 9: compound 1-1-09's is synthetic

Compound 1-1-09's is synthetic the same with example 1.Just usefulness is 1, and the 12-dibromo-dodecane replaces 1, the 4-dibromobutane.Product four-[3-methoxyl group-4-(N-carbazole) dodecyloxy] phenyl porphyrin.Mass spectrum molecular ion peak: 2131.Chemical formula C is pressed in ultimate analysis ₁₄₄H ₁₆₂N ₈O ₈Calculate: C:81.1%; H:7.7%; N:5.3%; O:6.0%; Experimental value: C:81.2%; H:7.3%; N:5.1%; O:6.2%.

Example 10: compound 1-1-10's is synthetic

Compound 1-1-10's is synthetic the same with example 1.Just usefulness is that vanirom replaces 3-methoxyl group-4-hydroxy benzaldehyde.Product four-[3-oxyethyl group-4-(N-carbazole) butoxy] phenyl porphyrin.Mass spectrum molecular ion peak: 1739.Chemical formula C is pressed in ultimate analysis ₁₁₆H ₁₀₆N ₈O ₈Calculate: C:80.0%; H:6.1%; N:6.4%; O:7.4%; Experimental value: C:79.6%; H:6.2%; N:6.5%; O:7.6%.

Four-[3-oxyethyl group-4-(N-carbazole) butoxy] phenyl porphyrins four-[3-propoxy--4-(N-carbazole) butoxy] phenyl porphyrin

1-1-10 1-1-11

Example 11: compound 1-1-11's is synthetic

Compound 1-1-11's is synthetic the same with example 1.Just usefulness is that 3-propoxy--4-hydroxy benzaldehyde replaces 3-methoxyl group-4-hydroxy benzaldehyde.Product four-[3-propoxy--4-(N-carbazole) butoxy] phenyl porphyrin.Mass spectrum molecular ion peak: 1795.Chemical formula C is pressed in ultimate analysis ₁₂₀H ₁₁₄N ₈O ₈Calculate: C:80.0%; H:6.4%; N:6.2%; O:7.1%; Experimental value: C:80.3%; H:6.3%; N:6.3%; O:7.2%.

Example 12: compound 1-1-12's is synthetic

Compound 1-1-12's is synthetic the same with example 1.Just usefulness is that 3-butoxy-4-hydroxy benzaldehyde replaces 3-methoxyl group-4-hydroxy benzaldehyde.Product four-[3-butoxy-4-(N-carbazole) butoxy] phenyl porphyrin.Mass spectrum molecular ion peak: 1851.Chemical formula C is pressed in ultimate analysis ₁₂₄H ₁₂₂N ₈O ₈Calculate: C:80.4%; H:6.6%; N:6.1%; O:6.9%; Experimental value: C:80.6%; H:6.7%; N:6.0%; O:7.1%.

Four-[3-butoxy-4-(N-carbazole) butoxy] phenyl porphyrins four-[3-tert.-butoxy-4-(N-carbazole) butoxy] phenyl porphyrin

1-1-12 1-1-13

Example 13: compound 1-1-13's is synthetic

Compound 1-1-13's is synthetic the same with example 1.Just usefulness is that 3-tert.-butoxy-4-hydroxy benzaldehyde replaces 3-methoxyl group-4-hydroxy benzaldehyde.Product four-[3-tert.-butoxy-4-(N-carbazole) butoxy] phenyl porphyrin.Mass spectrum molecular ion peak: 1851.Chemical formula C is pressed in ultimate analysis ₁₂₄H ₁₂₂N ₈O ₈Calculate: C:80.4%; H:6.6%; N:6.1%; O:6.9%; Experimental value: C:80.3%; H:6.9%; N:6.4%; O:7.1%.

Example 14: compound 1-1-14's is synthetic

Compound 1-1-14's is synthetic the same with example 1.Just usefulness is that the 4-hydroxy benzaldehyde replaces 3-methoxyl group-4-hydroxy benzaldehyde.Product four-[4-(N-carbazole) butoxy] phenyl porphyrin.Mass spectrum molecular ion peak: 1562.Chemical formula C is pressed in ultimate analysis ₁₀₈H ₉₀N ₈O ₈Calculate: C:82.9%; H:5.8%; N:7.2%; O:4.1%; Experimental value: C:83.3%; H:5.9%; N:7.4%; O:4.2%.

Four-[4-(N-carbazole) butoxy] phenyl porphyrins four-[3-(N-carbazole) butoxy] phenyl porphyrin

1-1-14 1-1-15

Example 15: compound 1-1-15's is synthetic

Compound 1-1-15's is synthetic the same with example 1.Just usefulness is that the 3-hydroxy benzaldehyde replaces 3-methoxyl group-4-hydroxy benzaldehyde.Product four-[3-(N-carbazole) butoxy] phenyl porphyrin.Mass spectrum molecular ion peak: 1562.Chemical formula C is pressed in ultimate analysis ₁₀₈H ₉₀N ₈O ₈Calculate: C:82.9%; H:5.8%; N:7.2%; O:4.1%; Experimental value: C:83.1%; H:5.9%; N:7.0%; O:4.2%.

Example 16: compound 1-1-16's is synthetic

Compound 1-1-16's is synthetic the same with example 1.Just usefulness is that 3.5-dimethoxy-4 '-hydroxy benzaldehyde replaces 3-methoxyl group-4-hydroxy benzaldehyde.Product four-[2.5-dimethoxy-4 '-(N-carbazole) butoxy] phenyl porphyrin.Mass spectrum molecular ion peak: 1803.Chemical formula C is pressed in ultimate analysis ₁₁₆H ₁₀₆N ₈O ₁₂Calculate: C:77.2%; H:5.9%; N:6.2%; O:10.6%; Experimental value: C:77.3%; H:6.2%; N:6.4%; O:10.1%.

Four-[3.5-dimethoxy-4 '-(N-carbazole) butoxy] phenyl porphyrins four-[2.5-dimethoxy-4 '-(N-carbazole) butoxy] phenyl porphyrin

1-1-16 1-1-17

Example 17: compound 1-1-17's is synthetic

Compound 1-1-17's is synthetic the same with example 1.Just usefulness is that 2.5-dimethoxy-4 '-hydroxy benzaldehyde replaces 3-methoxyl group-4-hydroxy benzaldehyde.Product four-[2.5-dimethoxy-4 '-(N-carbazole) butoxy] phenyl porphyrin.Mass spectrum molecular ion peak: 1803.Chemical formula C is pressed in ultimate analysis ₁₁₆H ₁₀₆N ₈O ₁₂Calculate: C:77.2%; H:5.9%; N:6.2%; O:10.6%; Experimental value: C:77.5%; H:6.0%; N:6.1%; O:10.8%.

Example 18: compound 1-1-18's is synthetic

Compound 1-1-18's is synthetic the same with example 1.Just usefulness is 3, and 6-di-t-butyl carbazole replaces carbazole.Product four-[3-methoxyl group-4-(3,6-di-t-butyl-N-carbazyl) butoxy] phenyl porphyrin.Mass spectrum molecular ion peak: 2131.Chemical formula C is pressed in ultimate analysis ₁₄₄H ₁₆₂N ₈O ₈Calculate: C:81.1%; H:7.7%; N:5.3%; O:6.0%; Experimental value: C:81.4%; H:7.5%; N:5.1%; O:5.8%.

Four-[3-methoxyl group-4-(3,6-di-t-butyl-N-carbazyl) butoxy] phenyl porphyrins four-[3-methoxyl group-4-(1,3,6,8-tetra-tert-N-carbazyl) butoxy] phenyl porphyrin

1-1-18 1-1-19

Example 19: compound 1-1-19's is synthetic

Compound 1-1-19's is synthetic the same with example 1.Just usefulness is 1,3,6, and 8-tetra-tert carbazole replaces carbazole.Product four-[3-methoxyl group-4-(1,3,6,8-tetra-tert-N-carbazyl) butoxy] phenyl porphyrin.Mass spectrum molecular ion peak: 2580.Chemical formula C is pressed in ultimate analysis ₁₇₆H ₂₂₆N ₈O ₈Calculate: C:81.9%; H:8.8%; N:4.3%; O:5.0%; Experimental value: C:81.4%; H:8.9%; N:4.1%; O:5.1%.

Example 20: compound 1-2-01's is synthetic

With compound 3.5-dimethoxy benzaldehyde 10.0 grams, pyrroles 4.0 gram and N, 600 milliliters of reflux of dinethylformamide 2 hours, cool off static, add 200 ml distilled waters, filter, the crude product methylene dichloride for the eluent aluminium sesquioxide is the stationary phase column chromatography, is promptly got product four-(3.5-dimethoxy) phenyl porphyrin 2.8 grams.Productive rate 21.8%.

Compound four-(3.5-dimethoxy) phenyl porphyrin 2.0 grams are added 1 milliliter of boron tribromide, 100 milliliters of methyl alcohol, heating reflux reaction 3 hours, cool off static, add 100 milliliters of 0.1M dilute hydrochloric acid, the underpressure distillation solvent evaporated, washed with dichloromethane promptly gets product four-(3.5-dihydroxyl) phenyl porphyrin 1.7 grams.Productive rate 98%.

Compound four-(3.5-dihydroxyl) phenyl porphyrin 1.0 grams are added N-(4-brombutyl) carbazole 6.0 grams, 2.0 milliliters of triethylamines, N, 600 milliliters of dinethylformamides, heated and stirred reaction 12 hours.Product concentrates with distilled water and dichloromethane extraction, dichloromethane extraction liquid, is that the stationary phase column chromatography promptly gets product four-[3.5-two (N-carbazole) butoxy] phenyl porphyrin 2.9 grams with methylene dichloride for the eluent aluminium sesquioxide.Productive rate: 85.6%.Mass spectrum molecular ion peak: 2511.Chemical formula C is pressed in ultimate analysis ₁₇₂H ₁₅₀N ₁₂O ₈Calculate: C:82.2%; H:6.0%; N:6.7%; O:5.1% experimental value: C:81.8%; H:5.8%; N:6.5%; O:5.4%.

Four-[3.5-two (N-carbazole) butoxy] phenyl porphyrins

1-2-01

Example 21: compound 1-2-02's is synthetic

Compound 1-2-02's is synthetic the same with example 20.Just usefulness is that pentamethylene bromide replaces 1, the 4-dibromobutane.Product four-[3.5-two (N-carbazole) pentyloxy] phenyl porphyrin.Mass spectrum molecular ion peak: 2623.Chemical formula C is pressed in ultimate analysis ₁₈₀H ₁₆₆N ₁₂O ₈Calculate: C:82.4%; H:6.4%; N:6.4%; O:4.9%; Experimental value: C:82.8%; H:6.2%; N:6.5%; O:4.7%.

Example 22: compound 1-2-03's is synthetic

Compound 1-2-03's is synthetic the same with example 20.Just usefulness is 1, and the 6-dibromo-hexane replaces 1, the 4-dibromobutane.Product four-[3.5-two (N-carbazole) hexyloxy] phenyl porphyrin.Mass spectrum molecular ion peak: 2735.Chemical formula C is pressed in ultimate analysis ₁₈₈H ₁₈₂N ₁₂O ₈Calculate: C:82.5%; H:6.7%; N:6.1%; O:4.7%; Experimental value: C:82.2%; H:6.8%; N:6.3%; O:4.9%.

Example 23: compound 1-2-04's is synthetic

Compound 1-2-04's is synthetic the same with example 20.Just usefulness is 1, and the 7-dibromo-heptane replaces 1, the 4-dibromobutane.Product four-[3.5-two (N-carbazole) oxygen base in heptan] phenyl porphyrin.Mass spectrum molecular ion peak: 2848.Chemical formula C is pressed in ultimate analysis ₁₉₆H ₁₉₈N ₁₂O ₈Calculate: C:82.6%; H:7.0%; N:5.9%; O:4.5%; Experimental value: C:82.2%; H:6.9%; N:6.0%; O:4.7%.

Example 24: compound 1-2-05's is synthetic

Compound 1-2-05's is synthetic the same with example 20.Just usefulness is 1, and 8-two bromooctanes replace 1, the 4-dibromobutane.Product four-[3.5-two (N-carbazole) octyloxy] phenyl porphyrin.Mass spectrum molecular ion peak: 2960.Chemical formula C is pressed in ultimate analysis ₂₀₄H ₂₁₄N ₁₂O ₈Calculate: C:82.7%; H:7.3%; N:5.7%; O:4.3%; Experimental value: C:82.9%; H:7.2%; N:6.0%; O:4.4%.

Example 25: compound 1-2-06's is synthetic

Compound 1-2-06's is synthetic the same with example 20.Just usefulness is 1, and 9-two bromononanes replace 1, the 4-dibromobutane.Product four-[3.5-two (N-carbazole) oxygen base in the ninth of the ten Heavenly Stems] phenyl porphyrin.Mass spectrum molecular ion peak: 3072.Chemical formula C is pressed in ultimate analysis ₂₁₂H ₂₃₀N ₁₂O ₈Calculate: C:82.8%; H:7.5%; N:5.5%; O:4.2%; Experimental value: C:83.1%; H:7.9%; N:5.4%; O:4.4%.

Example 26: compound 1-2-07's is synthetic

Compound 1-2-07's is synthetic the same with example 20.Just usefulness is 1, and the 10-dibromo-decane replaces 1, the 4-dibromobutane.Product four-[3.5-two (N-carbazole) oxygen base in the last of the ten Heavenly stems] phenyl porphyrin.Mass spectrum molecular ion peak: 3184.Chemical formula C is pressed in ultimate analysis ₂₂₀H ₂₄₆N ₁₂O ₈Calculate: C:82.9%; H:7.8%; N:5.3%; O:4.0%; Experimental value: C:82.5%; H:7.9%; N:5.5%; O:4.2%.

Example 27: compound 1-2-08's is synthetic

Compound 1-2-08's is synthetic the same with example 20.Just usefulness is 1, and 11-two bromo-n-11s replace 1, the 4-dibromobutane.Product four-[3.5-two (N-carbazole) undecane oxygen base] phenyl porphyrin.Mass spectrum molecular ion peak: 3296.Chemical formula C is pressed in ultimate analysis ₂₂₈H ₂₆₂N ₁₂O ₈Calculate: C:83.0%; H:8.0%; N:5.1%; O:3.9%; Experimental value: C:83.2%; H:8.3%; N:5.0%; O:3.7%.

Example 28: compound 1-2-09's is synthetic

Compound 1-2-09's is synthetic the same with example 20.Just usefulness is 1, and the 12-dibromo-dodecane replaces 1, the 4-dibromobutane.Product four-[3.5-two (N-carbazole) dodecyloxy] phenyl porphyrin.Mass spectrum molecular ion peak: 3408.Chemical formula C is pressed in ultimate analysis ₂₃₆H ₂₇₈N ₁₂O ₈Calculate: C:83.1%; H:8.2%; N:4.9%; O:3.8%; Experimental value: C:83.2%; H:8.3%; N:5.1%; O:4.0%.

Example 29: compound 1-2-10's is synthetic

Compound 1-2-10's is synthetic the same with example 20.Just usefulness is that the 3.4-dimethoxy benzaldehyde replaces the 3.5-dimethoxy benzaldehyde.Product four-[3.4-two (N-carbazole) butoxy] phenyl porphyrin.Mass spectrum molecular ion peak: 2511.Chemical formula C is pressed in ultimate analysis ₁₇₂H ₁₅₀N ₁₂O ₈Calculate: C:82.2%; H:6.0%; N:6.7%; O:5.1% experimental value: C:82.4%; H:5.8%; N:6.5%; O:5.2%.

Four-[3.4-two (N-carbazole) butoxy] phenyl porphyrins four-[2.5-two (N-carbazole) butoxy] phenyl porphyrin

1-2-10 1-2-11

Example 30: compound 1-2-11's is synthetic

Compound 1-2-11's is synthetic the same with example 20.Just usefulness is that the 2.5-dimethoxy benzaldehyde replaces the 3.5-dimethoxy benzaldehyde.Product four-[2.5-two (N-carbazole) butoxy] phenyl porphyrin.Mass spectrum molecular ion peak: 2511.Chemical formula C is pressed in ultimate analysis ₁₇₂H ₁₅₀N ₁₂O ₈Calculate: C:82.2%; H:6.0%; N:6.7%; O:5.1% experimental value: C:82.5%; H:5.7%; N:6.5%; O:5.2%.

Example 31: compound 1-2-12's is synthetic

Compound 1-2-12's is synthetic the same with example 20.Just usefulness is that the 2.4-dimethoxy benzaldehyde replaces the 3.5-dimethoxy benzaldehyde.Product four-[2.4-two (N-carbazole) butoxy] phenyl porphyrin.Mass spectrum molecular ion peak: 2511.Chemical formula C is pressed in ultimate analysis ₁₇₂H ₁₅₀N ₁₂O ₈Calculate: C:82.2%; H:6.0%; N:6.7%; O:5.1% experimental value: C:82.4%; H:5.7%; N:6.9%; O:5.0%.

Four-[2.4-two (N-carbazole) butoxy] phenyl porphyrins four-[2.6-two (N-carbazole) butoxy] phenyl porphyrin

1-2-12 1-2-13

Example 32: compound 1-2-13's is synthetic

Compound 1-2-13's is synthetic the same with example 20.Just usefulness is that the 2.6-dimethoxy benzaldehyde replaces the 3.5-dimethoxy benzaldehyde.Product four-[2.6-two (N-carbazole) butoxy] phenyl porphyrin.Mass spectrum molecular ion peak: 2511.Chemical formula C is pressed in ultimate analysis ₁₇₂H ₁₅₀N ₁₂O ₈Calculate: C:82.2%; H:6.0%; N:6.7%; O:5.1% experimental value: C:82.0%; H:5.7%; N:6.9%; O:5.4%.

Example 33: compound 1-2-14's is synthetic

Compound 1-2-14's is synthetic the same with example 20.Just usefulness is 3, and 6-di-t-butyl carbazole replaces carbazole.Product four-[3,5-two (3,6-di-t-butyl-N-carbazyl) butoxy] phenyl porphyrin.Mass spectrum molecular ion peak: 3408.Chemical formula C is pressed in ultimate analysis ₂₃₆H ₂₇₈N ₁₂O ₈Calculate: C:83.1%; H:8.2%; N:4.9%; O:3.8% experimental value: C:83.0%; H:8.4%; N:4.8%; O:4.0%.

Four-[3.5-two (3,6-di-t-butyl-N-carbazyl) butoxy] phenyl porphyrins four-[3.5-two (1,3,6,8-tetra-tert-N-carbazyl) butoxy] phenyl porphyrin

1-2-14 1-2-15

Example 34: compound 1-2-15's is synthetic

Compound 1-2-15's is synthetic the same with example 20.Just usefulness is 1,3,6, and 8-tetra-tert carbazole replaces carbazole.Product four-[3,5-two (1,3,6,8-tetra-tert-N-carbazyl) butoxy] phenyl porphyrin.Mass spectrum molecular ion peak: 4305.Chemical formula C is pressed in ultimate analysis ₃₀₀H ₄₀₆N ₁₂O ₈Calculate: C:83.6%; H:9.5%; N:3.9%; O:3.0% experimental value: C:83.3%; H:9.4%; N:3.8%; O:3.2%.

Example 35: compound 1-3-01's is synthetic

Compound 1-3-01's is synthetic the same with example 20.Just usefulness is that the 2.4.6-TMB replaces the 3.5-dimethoxy benzaldehyde.Product four-[2.4.6-three (N-carbazole) butoxy] phenyl porphyrin.Mass spectrum molecular ion peak: 3460.Chemical formula C is pressed in ultimate analysis ₂₃₆H ₂₁₀N ₁₆O ₁₂Calculate: C:81.9%; H:6.1%; N:6.5%; O:5.6% experimental value: C:82.3%; H:6.0%; N:6.3%; O:5.8%.

Four-[2.4.6-three (N-carbazole) butoxy] phenyl porphyrins four-[2.4.6-three (1,3,6,8-tetra-tert-N-carbazyl) butoxy] phenyl porphyrin

1-3-01 1-3-02

Example 36: compound 1-3-02's is synthetic

Compound 1-3-02's is synthetic the same with example 20.Just usefulness is 1,3,6, and 8-tetra-tert carbazole replaces carbazole, and the 2.4.6-TMB replaces the 3.5-dimethoxy benzaldehyde.Product four-[2.4.6-three (1,3,6,8-tetra-tert N-carbazyl) butoxy] phenyl porphyrin.Mass spectrum molecular ion peak: 6151.Chemical formula C is pressed in ultimate analysis ₄₂₈H ₅₉₄N ₁₆O ₁₂Calculate: C:83.5%; H:9.7%; N:3.6%; O:3.1% experimental value: C:83.3%; H:9.4%; N:3.8%; O:3.2%.

Example 37: compound 2-1-01's is synthetic

With compound 3-methoxyl group-4-hydroxy benzaldehyde 10.0 grams, pyrroles 4.4 gram and N, 600 milliliters of reflux of dinethylformamide 2 hours, cool off static, add 200 ml distilled waters, filter, the crude product methylene dichloride for the eluent aluminium sesquioxide is the stationary phase column chromatography, is promptly got product four-(3-methoxyl group-4-hydroxyl) phenyl porphyrin 3.5 grams.Productive rate 26.7%.

Compound four-(3-methoxyl group 4-hydroxyl) phenyl porphyrin 1.0 grams are added N-(4-brombutyl) carbazole 3.0 grams, 2.0 milliliters of triethylamines, N, 600 milliliters of dinethylformamides, heated and stirred reaction 12 hours.Product concentrates with distilled water and dichloromethane extraction, dichloromethane extraction liquid, is that the stationary phase column chromatography promptly gets product four-[3-methoxyl group-4-(N-carbazole) butoxy] phenyl porphyrin (H with methylene dichloride for the eluent aluminium sesquioxide ₂TCBOPP) 1.9 grams.Productive rate: 90.1%.

Compound four-[3-methoxyl group-4-(N-carbazole) butoxy] phenyl porphyrin 1.0 grams are added zinc acetate 1.0 grams, 600 milliliters of propionic acid, heated and stirred reaction 12 hours.Product concentrates with distilled water and dichloromethane extraction, dichloromethane extraction liquid, is that the stationary phase column chromatography promptly gets product four-[3-methoxyl group-4-(N-carbazole) butoxy] phenyl porphyrin zinc 0.9 gram with methylene dichloride for the eluent aluminium sesquioxide.Productive rate: 86.9%.Mass spectrum molecular ion peak: 1745.Chemical formula C is pressed in ultimate analysis ₁₁₂H ₉₆N ₈O ₈Zn calculates: C:77.0%;

Four-[3-methoxyl group-4-(N-carbazole) butoxy] phenyl porphyrin zinc

2-1-01

H:5.5%; N:6.4%; O:7.3% experimental value: C:76.8%; H:5.8%; N:6.7%; O:7.4%.

Example 38: compound 2-1-02's is synthetic

Compound 2-1-02's is synthetic the same with example 37.Just usefulness is that pentamethylene bromide replaces 1, the 4-dibromobutane.Product four-[3-methoxyl group-4-(N-carbazole) pentyloxy] phenyl porphyrin zinc.Mass spectrum molecular ion peak: 1801.Chemical formula C is pressed in ultimate analysis ₁₁₆H ₁₀₄N ₈O ₈Zn calculates: C:77.3%; H:5.8%; N:6.2%; O:7.1%; Experimental value: C:77.8%; H:6.0%; N:6.5%; O:7.0%.

Example 39: compound 2-1-03's is synthetic

Compound 2-1-03's is synthetic the same with example 37.Just usefulness is 1, and the 6-dibromo-hexane replaces 1, the 4-dibromobutane.Product four-[3-methoxyl group-4-(N-carbazole) hexyloxy] phenyl porphyrin zinc.Mass spectrum molecular ion peak: 1857.Chemical formula C is pressed in ultimate analysis ₁₂₀H ₁₁₂N ₈O ₈Zn calculates: C:77.5%; H:6.1%; N:6.0%; O:6.9%; Experimental value: C:77.2%; H:6.3%; N:6.1%; O:7.0%.

Example 40: compound 2-1-04's is synthetic

Compound 2-1-04's is synthetic the same with example 37.Just usefulness is 1, and the 7-dibromo-heptane replaces 1, the 4-dibromobutane.Product four-[3-methoxyl group-4-(N-carbazole) oxygen base in heptan] phenyl porphyrin zinc.Mass spectrum molecular ion peak: 1913.Chemical formula C is pressed in ultimate analysis ₁₂₄H ₁₂₀N ₈O ₈Zn calculates: C:77.7%; H:6.3%; N:5.9%; O:6.7%; Experimental value: C:77.9%; H:6.2%; N:6.1%; O:7.0%.

Example 41: compound 2-1-05's is synthetic

Compound 2-1-05's is synthetic the same with example 37.Just usefulness is 1, and 8-two bromooctanes replace 1, the 4-dibromobutane.Product four-[3-methoxyl group-4-(N-carbazole) octyloxy] phenyl porphyrin zinc.Mass spectrum molecular ion peak: 1969.Chemical formula C is pressed in ultimate analysis ₁₂₈H ₁₂₈N ₈O ₈Zn calculates: C:78.0%; H:6.5%; N:5.7%; O:6.5%; Experimental value: C:77.9%; H:6.2%; N:6.0%; O:6.4%.

Example 42: compound 2-1-06's is synthetic

Compound 2-1-06's is synthetic the same with example 37.Just usefulness is 1, and 9-two bromononanes replace 1, the 4-dibromobutane.Product four-[3-methoxyl group-4-(N-carbazole) oxygen base in the ninth of the ten Heavenly Stems] phenyl porphyrin zinc.Mass spectrum molecular ion peak: 2025.Chemical formula C is pressed in ultimate analysis ₁₃₂H ₁₃₆N ₈O ₈Zn calculates: C:78.2%; H:6.8%; N:5.5%; O:6.3%; Experimental value: C:77.8%; H:6.9%; N:5.4%; O:6.4%.

Example 43: compound 2-1-07's is synthetic

Compound 2-1-07's is synthetic the same with example 37.Just usefulness is 1, and the 10-dibromo-decane replaces 1, the 4-dibromobutane.Product four-[3-methoxyl group-4-(N-carbazole) oxygen base in the last of the ten Heavenly stems] phenyl porphyrin zinc.Mass spectrum molecular ion peak: 2081.Chemical formula C is pressed in ultimate analysis ₁₃₆H ₁₄₄N ₈O ₈Zn calculates: C:78.4%; H:7.0%; N:5.4%; O:6.1%; Experimental value: C:78.5%; H:7.2%; N:5.5%; O:6.2%.

Example 44: compound 2-1-08's is synthetic

Compound 2-1-08's is synthetic the same with example 37.Just usefulness is 1, and 11-two bromo-n-11s replace 1, the 4-dibromobutane.Product four-[3-methoxyl group-4-(N-carbazole) undecane oxygen base] phenyl porphyrin zinc.Mass spectrum molecular ion peak: 2137.Chemical formula C is pressed in ultimate analysis ₁₄₀H ₁₅₂N ₈O ₈Zn calculates: C:78.6%; H:7.2%; N:5.2%; O:6.0%; Experimental value: C:79.1%; H:7.3%; N:5.1%; O:6.2%.

Example 45: compound 2-1-09's is synthetic

Compound 2-1-09's is synthetic the same with example 37.Just usefulness is 1, and the 12-dibromo-dodecane replaces 1, the 4-dibromobutane.Product four-[3-methoxyl group-4-(N-carbazole) dodecyloxy] phenyl porphyrin zinc.Mass spectrum molecular ion peak: 2193.Chemical formula C is pressed in ultimate analysis ₁₄₄H ₁₆₀N ₈O ₈Zn calculates: C:78.8%; H:7.3%; N:5.1%; O:5.8%; Experimental value: C:79.2%; H:7.1%; N:5.2%; O:6.0%.

Example 46: compound 2-1-10's is synthetic

Compound 2-1-10's is synthetic the same with example 37.Just usefulness is that 3-oxyethyl group 4-hydroxy benzaldehyde replaces 3-methoxyl group-4-hydroxy benzaldehyde.Product four-[3-oxyethyl group-4-(N-carbazole) butoxy] phenyl porphyrin zinc.Mass spectrum molecular ion peak: 1801.Chemical formula C is pressed in ultimate analysis ₁₁₆H ₁₀₄N ₈O ₈Zn calculates: C:77.3%; H:5.8%; N:6.2%; O:7.1%; Experimental value: C:77.1%; H:6.0%; N:6.5%; O:7.3%.

Four-[3-oxyethyl group-4-(N-carbazole) butoxy] phenyl porphyrin zinc four-[3-propoxy--4-(N-carbazole) butoxy] phenyl porphyrin zinc

2-1-10 2-1-11

Example 47: compound 2-1-11's is synthetic

Compound 2-1-11's is synthetic the same with example 37.Just usefulness is that 3-propoxy--4-hydroxy benzaldehyde replaces 3-methoxyl group-4-hydroxy benzaldehyde.Product four-[3-propoxy--4-(N-carbazole) butoxy] phenyl porphyrin zinc.Mass spectrum molecular ion peak: 1857.Chemical formula C is pressed in ultimate analysis ₁₂₀H ₁₁₂N ₈O ₈Zn calculates: C:77.5%; H:6.1%; N:6.0%; O:6.9%; Experimental value: C:77.7%; H:6.3%; N:6.1%; O:7.1%.

Example 48: compound 2-1-12's is synthetic

Compound 2-1-12's is synthetic the same with example 37.Just usefulness is that 3-butoxy-4-hydroxy benzaldehyde replaces 3-methoxyl group-4-hydroxy benzaldehyde.Product four-[3-butoxy-4-(N-carbazole) butoxy] phenyl porphyrin zinc.Mass spectrum molecular ion peak: 1913.Chemical formula C is pressed in ultimate analysis ₁₂₄H ₁₂₀N ₈O ₈Zn calculates: C:77.7%; H:6.3%; N:5.9%; O:6.7%; Experimental value: C:77.2%; H:6.2%; N:6.1%; O:6.6%.

Example 49: compound 2-1-13's is synthetic

Compound 2-1-13's is synthetic the same with example 37.Just usefulness is that 3-tert.-butoxy 4-hydroxy benzaldehyde replaces 3-methoxyl group-4-hydroxy benzaldehyde.Product four-[3-tert.-butoxy-4-(N-carbazole) butoxy] phenyl porphyrin zinc.Mass spectrum molecular ion peak: 1913.Chemical formula C is pressed in ultimate analysis ₁₂₄H ₁₂₀N ₈O ₈Zn calculates: C:77.7%; H:6.3%; N:5.9%; O:6.7%; Experimental value: C:77.8%;

Four-[3-butoxy-4-(N-carbazole) butoxy] phenyl porphyrin zinc four-[3-tert.-butoxy-4-(N-carbazole) butoxy] phenyl porphyrin zinc

2-1-12 2-1-13

H：6.2％；N：6.1％；O：6.9％。

Example 50: compound 2-1-14's is synthetic

Compound 2-1-14's is synthetic the same with example 37.Just usefulness is that the 4-hydroxy benzaldehyde replaces 3-methoxyl group-4-hydroxy benzaldehyde.Product four-[4-(N-carbazole) butoxy] phenyl porphyrin zinc.Mass spectrum molecular ion peak: 1625.Chemical formula C is pressed in ultimate analysis ₁₀₈H ₈₈N ₈O ₈Zn calculates: C:79.7%; H:5.5%; N:6.9%; O:3.9%; Experimental value: C:79.3%; H:5.4%; N:7.0%; O:4.1%.

Example 51: compound 2-1-15's is synthetic

Compound 2-1-15's is synthetic the same with example 37.Just usefulness is that the 3-hydroxy benzaldehyde replaces 3-methoxyl group-4-hydroxy benzaldehyde.Product four-[3-(N-carbazole) butoxy] phenyl porphyrin zinc.Mass spectrum molecular ion peak: 1625.Chemical formula C is pressed in ultimate analysis ₁₀₈H ₈₈N ₈O ₈Zn calculates: C:79.7%; H:5.5%; N:6.9%; O:3.9%; Experimental value: C:79.9%; H:5.4%; N:7.0%; O:3.7%.

Four-[4-(N-carbazole) butoxy] phenyl porphyrin zinc four-[3-(N-carbazole) butoxy] phenyl porphyrin zinc

2-1-14 2-1-15

Example 52: compound 2-1-16's is synthetic

Compound 2-1-16's is synthetic the same with example 37.Just usefulness is that 3.5-dimethoxy-4 '-hydroxy benzaldehyde replaces 3-methoxyl group-4-hydroxy benzaldehyde.Product four-[2.5-dimethoxy-4 '-(N-carbazole) butoxy] phenyl porphyrin zinc.Mass spectrum molecular ion peak: 1865.Chemical formula C is pressed in ultimate analysis ₁₁₆H ₁₀₄N ₈O ₁₂Zn calculates: C:74.6%; H:5.6%; N:6.0%; O:10.3%; Experimental value: C:74.3%; H:5.8%; N:6.1%:O:10.1%.

Example 53: compound 2-1-17's is synthetic

Compound 2-1-17's is synthetic the same with example 37.Just usefulness is that 2.5-dimethoxy-4 '-hydroxy benzaldehyde replaces 3-methoxyl group-4-hydroxy benzaldehyde.Product four-[2.5-dimethoxy-4 '-(N-carbazole) butoxy] phenyl porphyrin zinc.Mass spectrum molecular ion peak: 1803.Chemical formula C is pressed in ultimate analysis ₁₁₆H ₁₀₄N ₈O ₁₂Zn calculates: C:74.6%; H:5.6%; N:6.0%; O:10.3%; Real

Four-[3.5-dimethoxy-4 '-(N-carbazole) butoxy] phenyl porphyrin zinc four-[2.5-dimethoxy-4 '-(N-carbazole) butoxy] phenyl porphyrin zinc

2-1-16 2-1-17

The value of testing: C:74.8%; H:5.8%; N:6.1%; O:10.4%.

Example 54: compound 2-1-18's is synthetic

Compound 2-1-18's is synthetic the same with example 37.Just usefulness is 3, and 6-di-t-butyl carbazole replaces carbazole.Product four-[3-methoxyl group-4-(3,6-di-t-butyl-N-carbazyl) butoxy] phenyl porphyrin zinc.Mass spectrum molecular ion peak: 2193.Chemical formula C is pressed in ultimate analysis ₁₄₄H ₁₆₀N ₈O ₈Zn calculates: C:78.8%; H:7.3%; N:5.1%; O:5.8%; Experimental value: C:78.4%; H:7.5%; N:5.0%; O:5.9%.

Example 55: compound 2-1-19's is synthetic

Compound 2-1-19's is synthetic the same with example 37.Just usefulness is 1,3,6, and 8-tetra-tert carbazole replaces carbazole.Product four-[3-methoxyl group-4-(1,3,6,8-tetra-tert-N-carbazyl) butoxy] phenyl porphyrin zinc.Mass spectrum molecular ion peak: 2642.Chemical formula C is pressed in ultimate analysis ₁₇₆H ₂₂₄N ₈O ₈Zn calculates: C:79.9%; H:8.5%; N:4.2%; O:4.8%; Experimental value: C:80.4%; H:8.3%; N:4.1%; O:5.0%.

Four-[3-methoxyl group-4-(3,6-di-t-butyl-N-carbazyl) butoxy] phenyl porphyrin zinc four-[3-methoxyl group-4-(1,3,6,8-tetra-tert-N-carbazyl) butoxy] phenyl porphyrin zinc

2-1-18 2-1-19

Example 56: compound 2-2-01's is synthetic

Compound four-(3.5-dihydroxyl) phenyl porphyrin 1.0 grams are added N-(4-brombutyl) carbazole 6.0 grams, 2.0 milliliters of triethylamines, N, 600 milliliters of dinethylformamides, heated and stirred reaction 12 hours.Product concentrates with distilled water and dichloromethane extraction, dichloromethane extraction liquid, is that the stationary phase column chromatography promptly gets product four-[3.5-two (N-carbazole) butoxy] phenyl porphyrin 2.9 grams with methylene dichloride for the eluent aluminium sesquioxide.Productive rate: 85.6%.

Compound four-[3.5-two (N-carbazole) butoxy] phenyl porphyrin 1.0 grams are added zinc acetate 1.0 grams, 600 milliliters of propionic acid, heated and stirred reaction 12 hours.Product concentrates with distilled water and dichloromethane extraction, dichloromethane extraction liquid, is that the stationary phase column chromatography promptly gets product four-[3.5-two (N-carbazole) butoxy] phenyl porphyrin zinc 0.8 gram with methylene dichloride for the eluent aluminium sesquioxide.Productive rate: 78.1%.Mass spectrum molecular ion peak: 2573.Chemical formula C is pressed in ultimate analysis ₁₇₂H ₁₄₈N ₁₂O ₈Zn calculates: C:80.2%; H:5.8%; N:6.5%; O:5.0% experimental value: C:79.9%; H:5.6%; N:6.4%; O:5.1%.

Four-[3.5-two (N-carbazole) butoxy] phenyl porphyrin zinc

2-2-01

Example 57: compound 2-2-02's is synthetic

Compound 2-2-02's is synthetic the same with example 56.Just usefulness is that pentamethylene bromide replaces 1, the 4-dibromobutane.Product four-[3.5-two (N-carbazole) pentyloxy] phenyl porphyrin zinc.Mass spectrum molecular ion peak: 2685.Chemical formula C is pressed in ultimate analysis ₁₈₀H ₁₆₄N ₁₂O ₈Zn calculates: C:80.4%; H:6.2%; N:6.3%; O:4.8%; Experimental value: C:80.8%; H:6.1%; N:6.5%; O:4.7%.

Example 58: compound 2-2-03's is synthetic

Compound 2-2-03's is synthetic the same with example 56.Just usefulness is 1, and the 6-dibromo-hexane replaces 1, the 4-dibromobutane.Product four-[3.5-two (N-carbazole) hexyloxy] phenyl porphyrin zinc.Mass spectrum molecular ion peak: 2797.Chemical formula C is pressed in ultimate analysis ₁₈₈H ₁₈₀N ₁₂O ₈Zn calculates: C:80.6%; H:6.5%; N:6.0%; O:4.3%; Experimental value: C:80.2%; H:6.2%; N:6.1%; O:4.2%.

Example 59: compound 2-2-04's is synthetic

Compound 2-2-04's is synthetic the same with example 56.Just usefulness is 1, and the 7-dibromo-heptane replaces 1, the 4-dibromobutane.Product four-[3.5-two (N-carbazole) oxygen base in heptan] phenyl porphyrin zinc.Mass spectrum molecular ion peak: 2909.Chemical formula C is pressed in ultimate analysis ₁₉₆H ₁₉₆N ₁₂O ₈Zn calculates: C:80.8%; H:6.8%; N:5.8%; O:4.4%; Experimental value: C:81.2%; H:6.9%; N:6.0%; O:4.2%.

Example 60: compound 2-2-05's is synthetic

Compound 2-2-05's is synthetic the same with example 56.Just usefulness is 1, and 8-two bromooctanes replace 1, the 4-dibromobutane.Product four-[3.5-two (N-carbazole) octyloxy] phenyl porphyrin zinc.Mass spectrum molecular ion peak: 3022.Chemical formula C is pressed in ultimate analysis ₂₀₄H ₂₁₂N ₁₂O ₈Zn calculates: C:81.0%; H:7.1%; N:5.6%; O:4.2%; Experimental value: C:80.9%; H:7.2%; N:5.3%; O:4.4%.

Example 61: compound 2-2-06's is synthetic

Compound 2-2-06's is synthetic the same with example 56.Just usefulness is 1, and 9-two bromononanes replace 1, the 4-dibromobutane.Product four-[3.5-two (N-carbazole) oxygen base in the ninth of the ten Heavenly Stems] phenyl porphyrin zinc.Mass spectrum molecular ion peak: 3134.Chemical formula C is pressed in ultimate analysis ₂₁₂H ₂₂₈N ₁₂O ₈Zn calculates: C:81.2%; H:7.3%; N:5.4%; O:4.1%; Experimental value: C:81.1%; H:7.4%; N:5.5%; O:4.0%.

Example 62: compound 2-2-07's is synthetic

Compound 2-2-07's is synthetic the same with example 56.Just usefulness is 1, and the 10-dibromo-decane replaces 1, the 4-dibromobutane.Product four-[3.5-two (N-carbazole) oxygen base in the last of the ten Heavenly stems] phenyl porphyrin zinc.Mass spectrum molecular ion peak: 3246.Chemical formula C is pressed in ultimate analysis ₂₂₀H ₂₄₄N ₁₂O ₈Zn calculates: C:81.3%; H:7.6%; N:5.2%; O:3.9%; Experimental value: C:81.5%; H:7.9%; N:5.0%; O:4.0%.

Example 63: compound 2-2-08's is synthetic

Compound 2-2-08's is synthetic the same with example 56.Just usefulness is 1, and 11-two bromo-n-11s replace 1, the 4-dibromobutane.Product four-[3.5-two (N-carbazole) undecane oxygen base] phenyl porphyrin zinc.Mass spectrum molecular ion peak: 3358.Chemical formula C is pressed in ultimate analysis ₂₂₈H ₂₆₀N ₁₂O ₈Zn calculates: C:81.5%; H:7.8%; N:5.0%; O:3.8%; Experimental value: C:81.2%; H:8.0%; N:5.2%; O:3.7%.

Example 64: compound 2-2-09's is synthetic

Compound 2-2-09's is synthetic the same with example 56.Just usefulness is 1, and the 12-dibromo-dodecane replaces 1, the 4-dibromobutane.Product four-[3.5-two (N-carbazole) dodecyloxy] phenyl porphyrin zinc.Mass spectrum molecular ion peak: 3470.Chemical formula C is pressed in ultimate analysis ₂₃₆H ₂₇₆N ₁₂O ₈Zn calculates: C:81.6%; H:8.0%; N:4.8%; O:3.7%; Experimental value: C:81.2%; H:8.3%; N:5.0%; O:3.8%.

Example 65: compound 2-2-10's is synthetic

Compound 2-2-10's is synthetic the same with example 56.Just usefulness is that the 3.4-dimethoxy benzaldehyde replaces the 3.5-dimethoxy benzaldehyde.Product four-[3.4-two (N-carbazole) butoxy] phenyl porphyrin zinc.Mass spectrum molecular ion peak: 2573.Chemical formula C is pressed in ultimate analysis ₁₇₂H ₁₄₈N ₁₂O ₈Zn calculates: C:80.2%; H:5.8%; N:6.5%; O:5.0% experimental value: C:79.9%; H:5.7%; N:6.4%; O:5.2%.

Four-[3.4-two (N-carbazole) butoxy] phenyl porphyrin zinc four-[2.5-two (N-carbazole) butoxy] phenyl porphyrin zinc

2-2-10 2-2-11

Example 66: compound 2-2-11's is synthetic

Compound 2-2-11's is synthetic the same with example 56.Just usefulness is that the 2.5-dimethoxy benzaldehyde replaces the 3.5-dimethoxy benzaldehyde.Product four-[2.5-two (N-carbazole) butoxy] phenyl porphyrin zinc.Mass spectrum molecular ion peak: 2573.Chemical formula C is pressed in ultimate analysis ₁₇₂H ₁₄₈N ₁₂O ₈Zn calculates: C:80.2%; H:5.8%; N:6.5%; O:5.0% experimental value: C:79.9%; H:5.6%; N:6.2%; O:4.9%.

Example 67: compound 2-2-12's is synthetic

Compound 2-2-12's is synthetic the same with example 56.Just usefulness is that the 2.4-dimethoxy benzaldehyde replaces the 3.5-dimethoxy benzaldehyde.Product four-[2.4-two (N-carbazole) butoxy] phenyl porphyrin zinc.Mass spectrum molecular ion peak: 2573.Ultimate analysis is by changing

Four-[2.4-two (N-carbazole) butoxy] phenyl porphyrin zinc four-[2.6-two (N-carbazole) butoxy] phenyl porphyrin zinc

2-2-12 2-2-13

Formula C ₁₇₂H ₁₄₈N ₁₂O ₈Zn calculates: C:80.2%; H:5.8%; N:6.5%; O:5.0% experimental value: C:79.7%; H:5.6%; N:6.8%; O:5.1%.

Example 68: compound 2-2-13's is synthetic

Compound 2-2-13's is synthetic the same with example 56.Just usefulness is that the 2.6-dimethoxy benzaldehyde replaces the 3.5-dimethoxy benzaldehyde.Product four-[2.6-two (N-carbazole) butoxy] phenyl porphyrin zinc.Mass spectrum molecular ion peak: 2573.Chemical formula C is pressed in ultimate analysis ₁₇₂H ₁₄₈N ₁₂O ₈Zn calculates: C:80.2%; H:5.8%; N:6.5%; O:5.0% experimental value: C:80.5%; H:5.7%; N:6.4%; O:5.1%.

Example 69: compound 2-2-14's is synthetic

Compound 2-2-14's is synthetic the same with example 56.Just usefulness is 3, and 6-di-t-butyl carbazole replaces carbazole.Product four-[3,5-two (3,6-di-t-butyl-N-carbazyl) butoxy] phenyl porphyrin zinc.Mass spectrum molecular ion peak: 3470.Chemical formula C is pressed in ultimate analysis ₂₃₆H ₂₇₆N ₁₂O ₈Zn calculates: C:81.6%; H:8.0%; N:4.8%; O:3.7% experimental value: C:82.0%; H:8.1%; N:4.6%; O:3.9%.

Four-[3.5-two (3,6-di-t-butyl-N-carbazyl) butoxy] phenyl porphyrin zinc four-[3.5-two (1,3,6,8-tetra-tert-N-carbazyl) butoxy] phenyl porphyrin zinc

2-2-14 2-2-15

Example 70: compound 2-2-15's is synthetic

Compound 2-2-15's is synthetic the same with example 56.Just usefulness is 1,3,6, and 8-tetra-tert carbazole replaces carbazole.Product four-[3,5-two (1,3,6,8-tetra-tert N-carbazyl) butoxy] phenyl porphyrin zinc.Mass spectrum molecular ion peak: 4367.Chemical formula C is pressed in ultimate analysis ₃₀₀H ₄₀₄N ₁₂O ₈Zn calculates: C:82.4%; H:9.3%; N:3.8%; O:2.9% experimental value: C:82.3%; H:9.4%; N:3.7%; O:3.0%.

Example 71: compound 2-3-01's is synthetic

Compound 2-3-01's is synthetic the same with example 56.Just usefulness is that the 2.4.6-TMB replaces the 3.5-dimethoxy benzaldehyde.Product four-[2.4.6-three (N-carbazole) butoxy] phenyl porphyrin zinc.Mass spectrum molecular ion peak: 3522.Ultimate analysis

Four-[2.4.6-three (N-carbazole) butoxy] phenyl porphyrin zinc four-[2.4.6-three (1,3,6,8-tetra-tert-N-carbazyl) butoxy] phenyl porphyrin zinc

2-3-01 2-3-02

Press chemical formula C ₂₃₆H ₂₀₈N ₁₆O ₁₂Zn calculates: C:80.4%; H:6.0%; N:6.4%; O:5.5% experimental value: C:80.3%; H:6.2%; N:6.3%; O:5.4%.

Example 72: compound 2-3-02's is synthetic

Compound 2-3-02's is synthetic the same with example 56.Just usefulness is 1,3,6, and 8-tetra-tert carbazole replaces carbazole, and the 2.4.6-TMB replaces the 3.5-dimethoxy benzaldehyde.Product four-[2.4.6-three (1,3,6,8-tetra-tert-N-carbazyl) butoxy] phenyl porphyrin zinc.Mass spectrum molecular ion peak: 6213.Chemical formula C is pressed in ultimate analysis ₄₂₈H ₅₉₂N ₁₆O ₁₂Zn calculates: C:82.7%; H:9.6%; N:3.6%; O:3.1% experimental value: C:83.0%; H:9.4%; N:3.8%; O:3.2%.

Example 73: compound 2-1-20's is synthetic

Four-[3-methoxyl group-4-(N-carbazole) butoxy] phenyl porphyrin platinum

2-1-20

With compound 3-methoxyl group 4-hydroxy benzaldehyde 10.0 grams, pyrroles 4.4 gram and N, 600 milliliters of reflux of N-dimethyl formyl 2 hours, cool off static, add 200 ml distilled waters, filter, the crude product methylene dichloride for the eluent aluminium sesquioxide is the stationary phase column chromatography, is promptly got product four-(3-methoxyl group-4-hydroxyl) phenyl porphyrin 3.5 grams.Productive rate 26.7%.

Compound four-(3-methoxyl group-4-hydroxyl) phenyl porphyrin 1.0 grams are added N-(4-brombutyl) carbazole 3.0 grams, 2.0 milliliters of triethylamines, N, 600 milliliters of dinethylformamides, heated and stirred reaction 12 hours.Product concentrates with distilled water and dichloromethane extraction, dichloromethane extraction liquid, is that the stationary phase column chromatography promptly gets product four-[3-methoxyl group-4-(N-carbazole) butoxy] phenyl porphyrin 1.9 grams with methylene dichloride for the eluent aluminium sesquioxide.Productive rate: 90.1%.

Compound four-[3-methoxyl group-4-(N-carbazole) butoxy] phenyl porphyrin is added 50 milligrams of platinum dichloride, 600 milliliters of acetonitriles, reacting by heating 12 hours for 100 milligrams.Underpressure distillation steams acetonitrile, and the crude product methylene dichloride for the eluent aluminium sesquioxide is the stationary phase column chromatography, is promptly got 110 milligrams of products four-[3-methoxyl group-4-(N-carbazole) butoxy] phenyl porphyrin platinum.Productive rate: 98.7%.Mass spectrum molecular ion peak: 1876.Chemical formula C is pressed in ultimate analysis ₁₁₂H ₉₆N ₈O ₈Pt calculates: C:71.7%; H:5.2%; N:6.2%; O:6.8% experimental value: C:71.8%; H:5.0%; N:6.3%; O:7.0%.

Example 74: compound 2-1-21's is synthetic

Compound 2-1-21's is synthetic the same with example 73.Just usefulness is that pentamethylene bromide replaces 1, the 4-dibromobutane.Product four-[3-methoxyl group-4-(N-carbazole) pentyloxy] phenyl porphyrin platinum.Mass spectrum molecular ion peak: 1932.Chemical formula C is pressed in ultimate analysis ₁₁₆H ₁₀₄N ₈O ₈Pt calculates: C:72.1%; H:5.4%; N:5.8%; O:6.6%; Experimental value: C:71.8%; H:5.5%; N:5.5%; O:6.8%.

Example 75: compound 2-1-22's is synthetic

Compound 2-1-22's is synthetic the same with example 73.Just usefulness is 1, and the 6-dibromo-hexane replaces 1, the 4-dibromobutane.Product four-[3-methoxyl group-4-(N-carbazole) hexyloxy] phenyl porphyrin platinum.Mass spectrum molecular ion peak: 1988.Chemical formula C is pressed in ultimate analysis ₁₂₀H ₁₁₂N ₈O ₈Pt calculates: C:72.5%; H:5.7%; N:5.6%; O:6.4%; Experimental value: C:72.2%; H:5.5%; N:5.8%; O:6.2%.

Example 76: compound 2-1-23's is synthetic

Compound 2-1-23's is synthetic the same with example 73.Just usefulness is 1, and the 7-dibromo-heptane replaces 1, the 4-dibromobutane.Product four-[3-methoxyl group-4-(N-carbazole) oxygen base in heptan] phenyl porphyrin platinum.Mass spectrum molecular ion peak: 2044.Chemical formula C is pressed in ultimate analysis ₁₂₄H ₁₂₀N ₈O ₈Pt calculates: C:72.8%; H:5.9%; N:5.5%; O:6.3%; Experimental value: C:72.9%; H:6.0%; N:5.3%; O:6.4%.

Example 77: compound 2-1-24's is synthetic

Compound 2-1-24's is synthetic the same with example 73.Just usefulness is 1, and 8-two bromooctanes replace 1, the 4-dibromobutane.Product four-[3-methoxyl group-4-(N-carbazole) octyloxy] phenyl porphyrin platinum.Mass spectrum molecular ion peak: 2100.Chemical formula C is pressed in ultimate analysis ₁₂₈H ₁₂₈N ₈O ₈Pt calculates: C:73.2%; H:6.1%; N:5.3%; O:6.1%; Experimental value: C:72.9%; H:6.2%; N:5.0%; O:6.2%.

Example 78: compound 2-1-25's is synthetic

Compound 2-1-25's is synthetic the same with example 73.Just usefulness is 1, and 9-two bromononanes replace 1, the 4-dibromobutane.Product four-[3-methoxyl group-4-(N-carbazole) oxygen base in the ninth of the ten Heavenly Stems] phenyl porphyrin platinum.Mass spectrum molecular ion peak: 2156.Chemical formula C is pressed in ultimate analysis ₁₃₂H ₁₃₆N ₈O ₈Pt calculates: C:73.5%; H:6.4%; N:5.2%; O:5.9%; Experimental value: C:73.8%; H:6.2%; N:5.4%; O:6.0%.

Example 79: compound 2-1-26's is synthetic

Compound 2-1-26's is synthetic the same with example 73.Just usefulness is 1, and the 10-dibromo-decane replaces 1, the 4-dibromobutane.Product four-[3-methoxyl group-4-(N-carbazole) oxygen base in the last of the ten Heavenly stems] phenyl porphyrin platinum.Mass spectrum molecular ion peak: 2212.Chemical formula C is pressed in ultimate analysis ₁₃₆H ₁₄₄N ₈O ₈Pt calculates: C:73.8%; H:6.6%; N:5.1%; O:5.8%; Experimental value: C:73.5%; H:6.8%; N:5.0%; O:6.1%.

Example 80: compound 2-1-27's is synthetic

Compound 2-1-27's is synthetic the same with example 73.Just usefulness is 1, and 11-two bromo-n-11s replace 1, the 4-dibromobutane.Product four-[3-methoxyl group-4-(N-carbazole) undecane oxygen base] phenyl porphyrin platinum.Mass spectrum molecular ion peak: 2268.Chemical formula C is pressed in ultimate analysis ₁₄₀H ₁₅₂N ₈O ₈Pt calculates: C:74.1%; H:6.8%; N:4.9%; O:5.6%; Experimental value: C:74.4%; H:7.0%; N:5.1%; O:5.5%.

Example 81: compound 2-1-28's is synthetic

Compound 2-1-28's is synthetic the same with example 73.Just usefulness is 1, and the 12-dibromo-dodecane replaces 1, the 4-dibromobutane.Product four-[3-methoxyl group-4-(N-carbazole) dodecyloxy] phenyl porphyrin platinum.Mass spectrum molecular ion peak: 2324.Chemical formula C is pressed in ultimate analysis ₁₄₄H ₁₆₀N ₈O ₈Pt calculates: C:74.4%; H:6.9%; N:4.8%; O:5.5%; Experimental value: C:74.2%; H:7.1%; N:5.1%; O:5.4%.

Example 82: compound 2-1-29's is synthetic

Compound 2-1-29's is synthetic the same with example 73.Just usefulness is that vanirom replaces 3-methoxyl group-4-hydroxy benzaldehyde.Product four-[3-oxyethyl group-4-(N-carbazole) butoxy] phenyl porphyrin platinum.Mass spectrum molecular ion peak: 1932.Chemical formula C is pressed in ultimate analysis ₁₁₆H ₁₀₄N ₈O ₈Pt calculates: C:72.1%; H:5.4%; N:5.8%; O:6.6%; Experimental value: C:72.4%; H:5.3%; N:5.5%; O:6.7%.

Four-[3-oxyethyl group-4-(N-carbazole) butoxy] phenyl porphyrin platinum four-[3-propoxy--4-(N-carbazole) butoxy] phenyl porphyrin platinum

2-1-29 2-1-30

Example 83: compound 2-1-30's is synthetic

Compound 2-1-30's is synthetic the same with example 73.Just usefulness is that 3-propoxy--4-hydroxy benzaldehyde replaces 3-methoxyl group-4-hydroxy benzaldehyde.Product four-[3-propoxy--4-(N-carbazole) butoxy] phenyl porphyrin platinum.Mass spectrum molecular ion peak: 1988.Chemical formula C is pressed in ultimate analysis ₁₂₀H ₁₁₂N ₈O ₈Pt calculates: C:72.5%; H:5.7%; N:5.6%; O:6.4%; Experimental value: C:72.7%; H:5.6%; N:5.4%; O:6.1%.

Example 84: compound 2-1-31's is synthetic

Compound 2-1-31's is synthetic the same with example 73.Just usefulness is that 3-butoxy-4-hydroxy benzaldehyde replaces 3-methoxyl group-4-hydroxy benzaldehyde.Product four-[3-butoxy-4-(N-carbazole) butoxy] phenyl porphyrin platinum.Mass spectrum molecular ion peak: 2044.Chemical formula C is pressed in ultimate analysis ₁₂₄H ₁₂₀N ₈O ₈Pt calculates: C:72.8%; H:5.9%; N:5.5%; O:6.3%; Experimental value: C:73.2%; H:6.0%; N:5.3%; O:6.6%.

Four-[3-butoxy-4-(N-carbazole) butoxy] phenyl porphyrin platinum four-[3-tert.-butoxy-4-(N-carbazole) butoxy] phenyl porphyrin platinum

2-1-31 2-1-32

Example 85: compound 2-1-32's is synthetic

Compound 2-1-32's is synthetic the same with example 73.Just usefulness is that 3-tert.-butoxy-4-hydroxy benzaldehyde replaces 3-methoxyl group-4-hydroxy benzaldehyde.Product four-[3-tert.-butoxy-4-(N-carbazole) butoxy] phenyl porphyrin platinum.Mass spectrum molecular ion peak: 2044.Chemical formula C is pressed in ultimate analysis ₁₂₄H ₁₂₀N ₈O ₈Pt calculates: C:72.8%; H:5.9%; N:5.5%; O:6.3%; Experimental value: C:73.2%; H:6.0%; N:5.3%; O:6.6%.

Example 86: compound 2-1-33's is synthetic

Compound 2-1-33's is synthetic the same with example 73.Just usefulness is that the 4-hydroxy benzaldehyde replaces 3-methoxyl group-4-hydroxy benzaldehyde.Product four-[4-(N-carbazole) butoxy] phenyl porphyrin platinum.Mass spectrum molecular ion peak: 1756.Chemical formula C is pressed in ultimate analysis ₁₀₈H ₈₈N ₈O ₄Pt calculates: C:73.8%; H:5.1%; N:6.4%; O:3.6%; Experimental value: C:73.3%; H:4.9%; N:6.5%; O:3.7%.

Four-[4-(N-carbazole) butoxy] phenyl porphyrin platinum four-[3-(N-carbazole) butoxy] phenyl porphyrin platinum

2-1-33 2-1-34

Example 87: compound 2-1-34's is synthetic

Compound 2-1-34's is synthetic the same with example 73.Just usefulness is that the 3-hydroxy benzaldehyde replaces 3-methoxyl group-4-hydroxy benzaldehyde.Product four-[3-(N-carbazole) butoxy] phenyl porphyrin platinum.Mass spectrum molecular ion peak: 1756.Chemical formula C is pressed in ultimate analysis ₁₀₈H ₈₈N ₈O ₄Pt calculates: C:73.8%; H:5.1%; N:6.4%; O:3.6%; Experimental value: C:73.9%; H:5.1%; N:6.5%; O:3.7%.

Example 88: compound 2-1-35's is synthetic

Compound 2-1-35's is synthetic the same with example 73.Just usefulness is that 3.5-dimethoxy-4 '-hydroxy benzaldehyde replaces 3-methoxyl group-4-hydroxy benzaldehyde.Product four-[2.5-dimethoxy-4 '-(N-carbazole) butoxy] phenyl porphyrin platinum.Mass spectrum molecular ion peak: 1993.Chemical formula C is pressed in ultimate analysis ₁₁₆H ₁₀₄N ₈O ₁₂Pt calculates: C:69.8%; H:5.3%; N:5.6%; O:9.6%; Experimental value: C:70.1%; H:5.2%; N:5.4%; O:9.9%.

Four-[3.5-dimethoxy-4 '-(N-carbazole) butoxy] phenyl porphyrin platinum four-[2.5-dimethoxy-4 '-(N-carbazole) butoxy] phenyl porphyrin platinum

2-1-35 2-1-36

Example 89: compound 2-1-36's is synthetic

Compound 2-1-36's is synthetic the same with example 73.Just usefulness is that 2.5-dimethoxy-4 '-hydroxy benzaldehyde replaces 3-methoxyl group-4-hydroxy benzaldehyde.Product four-[2.5-dimethoxy-4 '-(N-carbazole) butoxy] phenyl porphyrin platinum.Mass spectrum molecular ion peak: 1993.Chemical formula C is pressed in ultimate analysis ₁₁₆H ₁₀₄N ₈O ₁₂Pt calculates: C:69.8%; H:5.3%; N:5.6%; O:9.6%; Experimental value: C:70.1%; H:5.2%; N:5.7%; O:9.7%.

Example 90: compound 2-1-37's is synthetic

Compound 2-1-37's is synthetic the same with example 73.Just usefulness is 3, and 6-di-t-butyl carbazole replaces carbazole.Product four-[3-methoxyl group-4-(3,6-di-t-butyl N-carbazyl) butoxy] phenyl porphyrin platinum.Mass spectrum molecular ion peak: 2324.Chemical formula C is pressed in ultimate analysis ₁₄₄H ₁₆₀N ₈O ₈Pt calculates: C:74.4%; H:6.9%; N:4.8%; O:5.5%; Experimental value: C:74.7%; H:7.0%; N:4.6%; O:5.7%.

Four-[3-methoxyl group-4-(3,6-di-t-butyl-N-carbazyl) butoxy] phenyl porphyrin platinum four-[3-methoxyl group-4-(1,3,6,8-tetra-tert-N-carbazyl) butoxy] phenyl porphyrin platinum

2-1-37 2-1-38

Example 91: compound 2-1-38's is synthetic

Compound 2-1-38's is synthetic the same with example 73.Just usefulness is 1,3,6, and 8-tetra-tert carbazole replaces carbazole.Product four-[3-methoxyl group-4-(1,3,6,8-tetra-tert-N-carbazyl) butoxy] phenyl porphyrin platinum.Mass spectrum molecular ion peak: 2773.Chemical formula C is pressed in ultimate analysis ₁₇₆H ₂₂₄N ₈O ₈Pt calculates: C:76.2%; H:8.1%; N:4.0%; O:4.6%; Experimental value: C:76.4%; H:8.3%; N:4.1%; O:4.5%.

Example 92: compound 2-2-16's is synthetic

With 150 milliliters of N, dinethylformamide is made solvent, adds hydrogenation of compounds sodium 3.0 grams, carbazole 10 grams and 1,4-dibromobutane 20.0 grams, heating reflux reaction 6 hours.Cooling adds 50 ml methanol and fully stirs after-filtration, and the filtrate of collection concentrates evaporate to dryness, and the crude product hexanaphthene promptly gets product N-(4-brombutyl) carbazole 8.2 grams for the eluent aluminium sesquioxide is the stationary phase column chromatography.Productive rate 45.4%.

Compound four-[3.5-two (N-carbazole) butoxy] phenyl porphyrin is added 50 milligrams of platinum dichloride, 600 milliliters of acetonitriles, heating reflux reaction 12 hours for 100 milligrams.Underpressure distillation steams acetonitrile, and the crude product methylene dichloride for the eluent aluminium sesquioxide is the stationary phase column chromatography, is promptly got 106 milligrams of products four-[3.5-two (N-carbazole) butoxy] phenyl porphyrin platinum.Productive rate: 98.4%.Mass spectrum molecular ion peak: 2704.Chemical formula C is pressed in ultimate analysis ₁₇₂H ₁₄₈N ₁₂O ₈Pt calculates: C:76.3%; H:5.5%; N:6.2%;

Four-[3.5-two (N-carbazole) butoxy] phenyl porphyrin platinum

2-2-16

O:4.7% experimental value: C:75.9%; H:5.6%; N:6.4%; O:4.9%.

Example 93: compound 2-2-17's is synthetic

Compound 2-2-17's is synthetic the same with example 92.Just usefulness is that pentamethylene bromide replaces 1, the 4-dibromobutane.Product four-[3.5-two (N-carbazole) pentyloxy] phenyl porphyrin platinum.Mass spectrum molecular ion peak: 2816.Chemical formula C is pressed in ultimate analysis ₁₈₀H ₁₆₄N ₁₂O ₈Pt calculates: C:76.7%; H:5.9%; N:6.0%; O:4.5%; Experimental value: C:76.8%; H:6.2%; N:6.1%; O:4.7%.

Example 94: compound 2-2-18's is synthetic

Compound 2-2-18's is synthetic the same with example 92.Just usefulness is 1, and the 6-dibromo-hexane replaces 1, the 4-dibromobutane.Product four-[3.5-two (N-carbazole) hexyloxy] phenyl porphyrin platinum.Mass spectrum molecular ion peak: 2928.Chemical formula C is pressed in ultimate analysis ₁₈₈H ₁₈₀N ₁₂O ₈Pt calculates: C:77.1%; H:6.2%; N:5.7%; O:4.4%; Experimental value: C:77.2%; H:6.4%; N:6.0%; O:4.2%.

Example 95: compound 2-2-19's is synthetic

Compound 2-2-19's is synthetic the same with example 92.Just usefulness is 1, and the 7-dibromo-heptane replaces 1, the 4-dibromobutane.Product four-[3.5-two (N-carbazole) oxygen base in heptan] phenyl porphyrin platinum.Mass spectrum molecular ion peak: 3040.Chemical formula C is pressed in ultimate analysis ₁₉₆H ₁₉₆N ₁₂O ₈Pt calculates: C:77.4%; H:6.5%; N:5.5%; O:4.2%; Experimental value: C:77.2%; H:6.7%; N:5.4%:O:4.1%.

Example 96: compound 2-2-20's is synthetic

Compound 2-2-20's is synthetic the same with example 92.Just usefulness is 1, and 8-two bromooctanes replace 1, the 4-dibromobutane.Product four-[3.5-two (N-carbazole) octyloxy] phenyl porphyrin platinum.Mass spectrum molecular ion peak: 3153.Chemical formula C is pressed in ultimate analysis ₂₀₄H ₂₁₂N ₁₂O ₈Pt calculates: C:77.7%; H:6.8%; N:5.3%; O:4.1%; Experimental value: C:77.9%; H:7.0%; N:5.2%; O:4.2%.

Example 97: compound 2-2-21's is synthetic

Compound 2-2-21's is synthetic the same with example 92.Just usefulness is 1, and 9-two bromononanes replace 1, the 4-dibromobutane.Product four-[3.5-two (N-carbazole) oxygen base in the ninth of the ten Heavenly Stems] phenyl porphyrin platinum.Mass spectrum molecular ion peak: 3265.Chemical formula C is pressed in ultimate analysis ₂₁₂H ₂₂₈N ₁₂O ₈Pt calculates: C:77.9%; H:7.0%; N:5.1%; O:3.9%; Experimental value: C:78.1%; H:6.9%; N:5.3%; O:4.0%.

Example 98: compound 2-2-22's is synthetic

Compound 2-2-22's is synthetic the same with example 92.Just usefulness is 1, and the 10-dibromo-decane replaces 1, the 4-dibromobutane.Product four-[3.5-two (N-carbazole) oxygen base in the last of the ten Heavenly stems] phenyl porphyrin platinum.Mass spectrum molecular ion peak: 3377.Chemical formula C is pressed in ultimate analysis ₂₂₀H ₂₄₄N ₁₂O ₈Pt calculates: C:78.2%; H:7.3%; N:5.0%; O:3.8%; Experimental value: C:78.5%; H:7.1%; N:5.2%; O:3.7%.

Example 99: compound 2-2-23's is synthetic

Compound 2-2-23's is synthetic the same with example 92.Just usefulness is 1, and 11-two bromo-n-11s replace 1, the 4-dibromobutane.Product four-[3.5-two (N-carbazole) undecane oxygen base] phenyl porphyrin platinum.Mass spectrum molecular ion peak: 3489.Chemical formula C is pressed in ultimate analysis ₂₂₈H ₂₆₀N ₁₂O ₈Pt calculates: C:78.4%; H:7.5%; N:4.8%; O:3.7%; Experimental value: C:78.2%; H:7.3%; N:5.0%; O:3.8%.

Example 100: compound 2-2-24's is synthetic

Compound 2-2-24's is synthetic the same with example 92.Just usefulness is 1, and the 12-dibromo-dodecane replaces 1, the 4-dibromobutane.Product four-[3.5-two (N-carbazole) dodecyloxy] phenyl porphyrin platinum.Mass spectrum molecular ion peak: 3601.Chemical formula C is pressed in ultimate analysis ₂₃₆H ₂₇₆N ₁₂O ₈Pt calculates: C:78.7%; H:7.7%; N:4.7%; O:3.6%; Experimental value: C:79.2%; H:7.6%; N:4.6%; O:3.8%.

Four-[3.4-two (N-carbazole) butoxy] phenyl porphyrin platinum four-[2.5-two (N-carbazole) butoxy] phenyl porphyrin platinum

2-2-25 2-2-26

Example 101: compound 2-2-25's is synthetic

The synthetic of compound 2-2-25 is synthetic the same with example 92.Just usefulness is that the 3.4-dimethoxy benzaldehyde replaces the 3.5-dimethoxy benzaldehyde.Product four-[3.4-two (N-carbazole) butoxy] phenyl porphyrin platinum.Mass spectrum molecular ion peak: 2704.Chemical formula C is pressed in ultimate analysis ₁₇₂H ₁₄₈N ₁₂O ₈Pt calculates: C:76.3%; H:5.5%; N:6.2%; O:4.7% experimental value: C:76.0%; H:5.6%; N:6.4%; O:4.5%.

Example 102: compound 2-2-26's is synthetic

Compound 2-2-26's is synthetic the same with example 92.Just usefulness is that the 2.5-dimethoxy benzaldehyde replaces the 3.5-dimethoxy benzaldehyde.Product four-[2.5-two (N-carbazole) butoxy] phenyl porphyrin platinum.Mass spectrum molecular ion peak: 2704.Chemical formula C is pressed in ultimate analysis ₁₇₂H ₁₄₈N ₁₂O ₈Pt calculates: C:76.3%; H:5.5%; N:6.2%; O:4.7% experimental value: C:75.9%; H:5.6%; N:6.1%; O:4.9%.

Example 103: compound 2-2-27's is synthetic

The synthetic of compound 2-2-27 is synthetic the same with example 92.Just usefulness is that the 2.4-dimethoxy benzaldehyde replaces the 3.5-dimethoxy benzaldehyde.Product four-[2.4-two (N-carbazole) butoxy] phenyl porphyrin platinum.Mass spectrum molecular ion peak: 2704.Chemical formula C is pressed in ultimate analysis ₁₇₂H ₁₄₈N ₁₂O ₈Pt calculates: C:76.3%; H:5.5%; N:6.2%; O:4.7% experimental value: C:75.9%; H:5.6%; N:6.4%; O:4.8%.

Example 104: compound 2-2-28's is synthetic

Compound 2-2-28's is synthetic the same with example 92.Just usefulness is that the 2.6-dimethoxy benzaldehyde replaces the 3.5-dimethoxy benzaldehyde.Product four-[2.6-two (N-carbazole) butoxy] phenyl porphyrin platinum.Mass spectrum molecular ion peak: 2704.Chemical formula C is pressed in ultimate analysis ₁₇₂H ₁₄₈N ₁₂O ₈Pt calculates: C:76.3%; H:5.5%; N:6.2%; O:4.7% experimental value: C:76.5%; H:5.3%; N:6.4%; O:4.9%.

Four-[2.4-two (N-carbazole) butoxy] phenyl porphyrin platinum four-[2.6-two (N-carbazole) butoxy] phenyl porphyrin platinum

2-2-27 2-2-28

Example 105: compound 2-2-29's is synthetic

Compound 2-2-29's is synthetic the same with example 92.Just usefulness is 3, and 6-di-t-butyl carbazole replaces carbazole.Product four-[3,5-two (3,6-di-t-butyl-N-carbazyl) butoxy] phenyl porphyrin platinum.Mass spectrum molecular ion peak: 3601.Chemical formula C is pressed in ultimate analysis ₂₃₆H ₂₇₆N ₁₂O ₈Pt calculates: C:78.7%; H:7.7%; N:4.7%; O:3.6% experimental value: C:79.0%; H:7.5%; N:4.6%; O:3.8%.

Example 106: compound 2-2-30's is synthetic

Compound 2-2-30's is synthetic the same with example 92.Just usefulness is 1,3,6, and 8-tetra-tert carbazole replaces carbazole.Product four-[3,5-two (1,3,6,8-tetra-tert-N-carbazyl) butoxy] phenyl porphyrin platinum.Mass spectrum molecular ion peak: 4498.Chemical formula C is pressed in ultimate analysis ₃₀₀H ₄₀₄N ₁₂O ₈Pt calculates: C:80.0%; H:9.1%; N:3.7%; O:2.8% experimental value: C:80.3%; H:9.0%; N:3.9%:O:3.0%.

Four-[3.5-two (3,6-di-t-butyl-N-carbazyl) butoxy] phenyl porphyrin platinum four-[3.5-two (1,3,6,8-tetra-tert-N-carbazyl) butoxy] phenyl porphyrin platinum

2-2-29 2-2-30

Example 107: compound 2-3-03's is synthetic

Compound 2-3-03's is synthetic the same with example 92.Just usefulness is that the 2.4.6-TMB replaces the 3.5-dimethoxy benzaldehyde.Product four-[2.4.6-three (N-carbazole) butoxy] phenyl porphyrin platinum.Mass spectrum molecular ion peak: 3653.Chemical formula C is pressed in ultimate analysis ₂₃₆H ₂₀₈N ₁₆O ₁₂Pt calculates: C:77.5%; H:5.7%; N:6.1%; O:5.3% experimental value: C:77.3%; H:5.8%; N:6.3%; O:5.2%.

Example 108: compound 2-3-04's is synthetic

Compound 2-3-04's is synthetic the same with example 92.Just usefulness is 1,3,6, and 8-tetra-tert carbazole replaces carbazole, and the 2.4.6-TMB replaces the 3.5-dimethoxy benzaldehyde.Product four-[2.4.6-three (1,3,6,8-tetra-tert-N-carbazyl) butoxy] phenyl porphyrin platinum.Mass spectrum molecular ion peak: 6344.Chemical formula C is pressed in ultimate analysis ₄₂₈H ₅₉₂N ₁₆O ₁₂Pt calculates: C:81.0%; H:9.4%; N:3.5%; O:3.0% experimental value: C:81.2%:H:9.3%; N:3.6%; O:3.1%.

Four-[2.4.6-three (N-carbazole) butoxy] phenyl porphyrin platinum four-[2.4.6-three (1,3,6,8-tetra-tert-N-carbazyl) butoxy] phenyl porphyrin platinum

2-3-03 2-3-04

Example 109: with compound 1-1-01 is the luminescent device of luminescent layer

The luminescent device structure is [ITO/PEDOT/1-1-01:ADS129/Ba/Al], and the doping content of luminescent material 1-1-01 in ADS129 is 4wt%, and the cut-in voltage of device is about 6.5V, and high-high brightness reaches 100cd/m ², maximum external quantum efficiency 0.14%.The luminous peak position of device is emitting red light at 663.4nm.

Example 110: with compound 1-1-19 is the luminescent device of luminescent layer

The luminescent device structure is [ITO/PEDOT/1-1-19:ADS129/Ba/Al], and the doping content of luminescent material 1-1-19 in ADS129 is 4wt%, and the cut-in voltage of device is about 6.0V, and high-high brightness reaches 100cd/m ², maximum external quantum efficiency 0.15%.The luminous peak position of device is emitting red light at 663.8nm.

Example 111: with compound 1-2-01 is the luminescent device of luminescent layer

The luminescent device structure is [ITO/PEDOT/1-2-01:ADS129/Ba/Al], and the doping content of luminescent material 1-2-01 in ADS129 is 4wt%, and the cut-in voltage of device is about 6.5V, and high-high brightness reaches 100cd/m ², maximum external quantum efficiency 0.12%.The luminous peak position of device is emitting red light at 662.5nm.

Example 112: with compound 1-2-15 is the luminescent device of luminescent layer

The luminescent device structure is [ITO/PEDOT/1-2-15:ADS129/Ba/Al], and the doping content of luminescent material 1-2-15 in ADS129 is 4wt%, and the cut-in voltage of device is about 6.8V, and high-high brightness reaches 100cd/m ², maximum external quantum efficiency 0.13%.The luminous peak position of device is emitting red light at 665.1nm.

Example 113: with compound 1-3-01 is the luminescent device of luminescent layer

The luminescent device structure is [ITO/PEDOT/1-3-01:ADS129/Ba/Al], and the doping content of luminescent material 1-3-01 in ADS129 is 4wt%, and the cut-in voltage of device is about 6.7V, and high-high brightness reaches 100cd/m ², maximum external quantum efficiency 0.15%.The luminous peak position of device is emitting red light at 663.5nm.

Example 114: with compound 1-3-02 is the luminescent device of luminescent layer

The luminescent device structure is [ITO/PEDOT/1-3-02:ADS129/Ba/Al], and the doping content of luminescent material 1-3-02 in ADS129 is 4wt%, and the cut-in voltage of device is about 6.6V, and high-high brightness reaches 100cd/m ², maximum external quantum efficiency 0.15%.The luminous peak position of device is emitting red light at 665.0nm.

Example 115: with compound 2-1-01 is the luminescent device of luminescent layer

The luminescent device structure is [ITO/PEDOT/2-1-01:ADS129/Ba/Al], and the doping content of luminescent material 2-1-01 in ADS129 is 4wt%, and the cut-in voltage of device is about 8.5V, and high-high brightness reaches 240cd/m ², maximum external quantum efficiency 0.27%.The luminous peak position of device is emitting red light at 607.6nm.

Example 116: with compound 2-1-19 is the luminescent device of luminescent layer

The luminescent device structure is [ITO/PEDOT/2-1-19:ADS129/Ba/Al], and the doping content of luminescent material 2-1-19 in ADS129 is 4wt%, and the cut-in voltage of device is about 8.0V, and high-high brightness reaches 240cd/m ², maximum external quantum efficiency 0.27%.The luminous peak position of device is emitting red light at 608.6nm.

Example 117: with compound 2-2-01 is the luminescent device of luminescent layer

The luminescent device structure is [ITO/PEDOT/2-2-01:ADS129/Ba/Al], and the doping content of luminescent material 2-2-01 in ADS129 is 4wt%, and the cut-in voltage of device is about 8.2V, and high-high brightness reaches 230cd/m ², maximum external quantum efficiency 0.25%.The luminous peak position of device is emitting red light at 607.6nm.

Example 118: with compound 2-2-15 is the luminescent device of luminescent layer

The luminescent device structure is [ITO/PEDOT/2-2-15:ADS129/Ba/Al], and the doping content of luminescent material 2-2-15 in ADS129 is 4wt%, and the cut-in voltage of device is about 8.5V, and high-high brightness reaches 240cd/m ², maximum external quantum efficiency 0.28%.The luminous peak position of device is emitting red light at 604.2nm.

Example 119: with compound 2-3-01 is the luminescent device of luminescent layer

The luminescent device structure is [ITO/PEDOT/2-3-01:ADS129/Ba/Al], and the doping content of luminescent material 2-3-01 in ADS129 is 4wt%, and the cut-in voltage of device is about 8.0V, and high-high brightness reaches 260cd/m ², maximum external quantum efficiency 0.26%.The luminous peak position of device is emitting red light at 607.2nm.

Example 120: with compound 2-3-02 is the luminescent device of luminescent layer

The luminescent device structure is [ITO/PEDOT/2-3-02:ADS129/Ba/Al], and the doping content of luminescent material 2-3-02 in ADS129 is 4wt%, and the cut-in voltage of device is about 8.9V, and high-high brightness reaches 220cd/m ², maximum external quantum efficiency 0.29%.The luminous peak position of device is emitting red light at 606.5nm.

Example 121: with compound 2-1-20 is the luminescent device (A) of luminescent layer

The luminescent device structure is [ITO/PEDOT/PVK/2-1-20:ADS129/Ba/Al], and the doping content of luminescent material 2-1-20 in ADS129 is 4wt%, and the cut-in voltage of device is about 8.5V, and high-high brightness reaches 70cd/m ², maximum external quantum efficiency 1.4%.The luminous peak position of device is emitting red light at 682.8nm.

Example 122: with compound 2-1-20 is the luminescent device (B) of luminescent layer

The luminescent device structure is [ITO/PEDOT/PVK/2-1-20:ADS129:PBD/Ba/Al], the doping content of luminescent material 2-1-20 in ADS129 is 4wt%, the doping content of hole barrier materials PBD in ADS129 is 30wt%, the cut-in voltage of device is about 4.5V, and high-high brightness reaches 100cd/m ², maximum external quantum efficiency 5.68%.The luminous peak position of device is emitting red light at 675.2nm.

Example 123: with compound 2-1-38 is the luminescent device (A) of luminescent layer

The luminescent device structure is [ITO/PEDOT/PVK/2-1-38:ADS129/Ba/Al], and the doping content of luminescent material 2-1-38 in ADS129 is 4wt%, and the cut-in voltage of device is about 8.4V, and high-high brightness reaches 75cd/m ², maximum external quantum efficiency 1.3%.The luminous peak position of device is emitting red light at 682.8nm.

Example 124: with compound 2-1-38 is the luminescent device (B) of luminescent layer

The luminescent device structure is [ITO/PEDOT/PVK/2-1-38:ADS129:PBD/Ba/Al], the doping content of luminescent material 2-1-20 in ADS129 is 4wt%, the doping content of hole barrier materials PBD in ADS129 is 30wt%, the cut-in voltage of device is about 4.0V, and high-high brightness reaches 100cd/m ², maximum external quantum efficiency 5.60%.The luminous peak position of device is emitting red light at 675.2nm.

Example 125: with compound 2-2-16 is the luminescent device (A) of luminescent layer

The luminescent device structure is [ITO/PEDOT/PVK/2-2-16:ADS129/Ba/Al], and the doping content of luminescent material 2-2-16 in ADS129 is 4wt%, and the cut-in voltage of device is about 8.8V, and high-high brightness reaches 70cd/m ², maximum external quantum efficiency 1.2%.The luminous peak position of device is emitting red light at 682.0nm.

Example 126: with compound 2-2-16 is the luminescent device (B) of luminescent layer

The luminescent device structure is [ITO/PEDOT/PVK/2-2-16:ADS129:PBD/Ba/Al], the doping content of luminescent material 2-2-16 in ADS129 is 4wt%, the doping content of hole barrier materials PBD in ADS129 is 30wt%, the cut-in voltage of device is about 4.5V, and high-high brightness reaches 100cd/m ², maximum external quantum efficiency 5.5%.The luminous peak position of device is emitting red light at 675.5nm.

Example 127: with compound 2-2-30 is the luminescent device (A) of luminescent layer

The luminescent device structure is [ITO/PEDOT/PVK/2-1-20:ADS129/Ba/Al], and the doping content of luminescent material 2-2-30 in ADS129 is 4wt%, and the cut-in voltage of device is about 8.5V, and high-high brightness reaches 70cd/m ², maximum external quantum efficiency 1.4%.The luminous peak position of device is emitting red light at 682.8nm.

Example 128: with compound 2-2-30 is the luminescent device (B) of luminescent layer

The luminescent device structure is [ITO/PEDOT/PVK/2-2-30:ADS129:PBD/Ba/Al], the doping content of luminescent material 2-2-30 in ADS129 is 4wt%, the doping content of hole barrier materials PBD in ADS129 is 30wt%, the cut-in voltage of device is about 4.5V, and high-high brightness reaches 100cd/m ², maximum external quantum efficiency 5.68%.The luminous peak position of device is emitting red light at 676.2nm.

Example 129: with compound 2-3-03 is the luminescent device (A) of luminescent layer

The luminescent device structure is [ITO/PEDOT/PVK/2-3-03:ADS129/Ba/Al], and the doping content of luminescent material 2-3-03 in ADS129 is 4wt%, and the cut-in voltage of device is about 8.0V, and high-high brightness reaches 60cd/m ², maximum external quantum efficiency 1.2%.The luminous peak position of device is emitting red light at 681.8nm.

Example 130: with compound 2-3-03 is the luminescent device (B) of luminescent layer

The luminescent device structure is [ITO/PEDOT/PVK/2-3-03:ADS129:PBD/Ba/Al], the doping content of luminescent material 2-3-03 in ADS129 is 4wt%, the doping content of hole barrier materials PBD in ADS129 is 30wt%, the cut-in voltage of device is about 4.0V, and high-high brightness reaches 110cd/m ², maximum external quantum efficiency 5.75%.The luminous peak position of device is emitting red light at 675.0nm.

Example 131: with compound 2-3-04 is the luminescent device (A) of luminescent layer

The luminescent device structure is [ITO/PEDOT/PVK/2-3-04:ADS129/Ba/Al], and the doping content of luminescent material 2-3-04 in ADS129 is 4wt%, and the cut-in voltage of device is about 8.5V, and high-high brightness reaches 72cd/m ², maximum external quantum efficiency 1.6%.The luminous peak position of device is emitting red light at 684.0nm.

Example 132: with compound 2-3-04 is the luminescent device (B) of luminescent layer

The luminescent device structure is [ITO/PEDOT/PVK/2-3-04:ADS129:PBD/Ba/Al], the doping content of luminescent material 2-3-04 in ADS129 is 4wt%, the doping content of hole barrier materials PBD in ADS129 is 30wt%, the cut-in voltage of device is about 4.4V, and high-high brightness reaches 100cd/m ², maximum external quantum efficiency 5.66%.The luminous peak position of device is emitting red light at 675.5nm.

Claims

1, with the tetraphenylporphyrin tetraphenylporphyrin derivative of basic structure skeleton shown in general formula (1) or (2),

M is Zn or Pt, R ₁, R ₂, R ₃Three substituted radicals are identical or different, and wherein having a substituted radical at least is the alkoxyl group substituted carbazole derivative shown in the formula (3), R ₁₀And R ₁₁Identical or different, be H or C _1-4Alkyl, n=4-12; All the other two substituted radicals are H, C ₁-C ₄Alkoxyl group, alkyl or formula (3) shown in alkoxyl group substituted carbazole derivative.

2, the application of the described tetraphenylporphyrin derivative of claim 1 aspect the preparation organic electroluminescence device.

3, the application of tetraphenylporphyrin derivative as claimed in claim 2 aspect the preparation organic electroluminescence device, it is characterized in that: electroluminescent device has one or more active coatings, has at least one deck to contain one or more compound of the present invention (1) or (2) in these active coatings.

4, the application of tetraphenylporphyrin derivative as claimed in claim 3 aspect the preparation organic electroluminescence device, it is characterized in that: active coating is a light-emitting layer and/or a migrating layer and/or an electric charge injection layer.