CN104649954A - Phenanthrocarbazole derivative and application of phenanthrocarbazole derivative in organic electroluminescence devices - Google Patents

Phenanthrocarbazole derivative and application of phenanthrocarbazole derivative in organic electroluminescence devices Download PDF

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CN104649954A
CN104649954A CN201310594859.5A CN201310594859A CN104649954A CN 104649954 A CN104649954 A CN 104649954A CN 201310594859 A CN201310594859 A CN 201310594859A CN 104649954 A CN104649954 A CN 104649954A
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boric acid
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CN104649954B (en
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李银奎
范洪涛
李艳蕊
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Beijing Eternal Material Technology Co Ltd
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Beijing Eternal Material Technology Co Ltd
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Abstract

The invention provides a phenanthrocarbazole derivative which has a structure as shown in the formula (I), wherein Ar1-Ar8 are independently selected from one of H, C6-C30 substituted or unsubstituted aromatic group, C6-C30 substituted or unsubstituted fused ring aromatic group, C6-C30 substituted or unsubstituted fused heterocyclic group, pentabasic and hexabasic heterocyclic ring or substituted heterocyclic ring, triarylated amine group, arylether group and C1-C12 substituted or unsubstituted aliphatic alkyl group; and Ar9 is selected from one of C6-C30 substituted or unsubstituted aromatic group, C6-C30 substituted or unsubstituted fused ring aromatic group and C1-C12 substituted or unsubstituted aliphatic alkyl group. The phenanthrocarbazole derivative can be used as a hole-injection material, a hole-transmission material, a fluorescence host material or a luminescent material in an organic electroluminescence device.

Description

A kind of phenanthro-carbazole derivative and the application in organic electroluminescence device thereof
Technical field
The present invention relates to a class new organic materials, and the application in ORGANIC ELECTROLUMINESCENCE DISPLAYS technical field.
Background technology
The hole always used in organic electroluminescent device is injected and transport material is generally an aromatic amino-derivative (such as bright dipping patent: publication number CN1152607C, publication date 2004,6,2), its general constructional feature is, as injecting material, in a molecule, one arylamine structural unit is at least more than one, and separate with a phenyl ring between two N, see formula 1; As transport material, in a molecule, one arylamine structural unit is generally two, and separates with biphenyl between two N, and in this kind of material, typical example is NPB, and its structure is shown in formula 2.
In recent years, the research of this kind of material has had some new progresses, introduce one or more thienyl in the molecule, or introduce one or more benzothienyl, see Fig. 3 and Fig. 4 (bright dipping patent: publication number CN101506191A, publication date 2009,8,12), result is the Hole injection capacity considerably increasing material; As transport material, when the arylamine structural unit carbazole of in material or diphenylene-oxide being replaced, the transmittability of material all has a more substantial increase.See Fig. 5 and Fig. 6 (bright dipping patent: publication number CN102334210A, the applying date 2012,1,25; Publication number: WO2010/114017A1, publication date 2010,10,7).
Summary of the invention
The object of the invention is to the phenanthro-carbazoles derivative that proposition one class is novel, this compounds may be used for ORGANIC ELECTROLUMINESCENCE DISPLAYS field.Particularly, this compounds, in display of organic electroluminescence, as hole-injecting material or as hole mobile material, also can be used as light emitting host material or luminescent material in fluorescent device.
Especially, we find, in material of the present invention, if phenanthro-carbazole precursor structure only connects condensed-nuclei aromatics, instead of connect triaryl amine or fused heterocycle aromatic hydrocarbons, such as carbazole group, dibenzothiophene group, diphenylene-oxide group etc., such material is suitable as light emitting host material, device light emitting efficiency is improved a lot, and device lifetime is longer.And on phenanthro-carbazole precursor structure, being connected with triaryl amine or fused heterocycle aromatic hydrocarbons, such as carbazole group, dibenzothiophene group, diphenylene-oxide group etc., such material is suitable as hole mobile material.In a word, the use of material of the present invention, what reduce device opens bright voltage, improves the luminous efficiency of device, adds the work-ing life of device.
For this reason, the technical scheme that the present invention takes is:
A kind of phenanthro-carbazole derivative, has structure as shown in the formula (I):
Wherein: Ar 1-Ar 8independently be selected from the substituted or non-substituted aromatic hydrocarbon group of H, C6 ~ C30, the condensed-nuclei aromatics group of the substituted or non-substituted of C6 ~ C30, the substituted or non-substituted of C6 ~ C30 fused heterocycle group, five yuan, hexa-atomic heterocycle or substituted heterocycle, triarylamine group, aryl oxide group base group, C1 ~ C12 substituted or non-substituted aliphatic alkyl group in one;
Ar 9be selected from the substituted or non-substituted aromatic hydrocarbon group of C6 ~ C30, the condensed-nuclei aromatics group of the substituted or non-substituted of C6 ~ C30, the substituted or non-substituted of C1 ~ C12 aliphatic alkyl group in one.
Further, described Ar 1, Ar 4, Ar 5, Ar 6, Ar 7, Ar 8be H simultaneously.
Further, described Ar 9be selected from phenyl, aminomethyl phenyl, ethylphenyl, p-methoxy-phenyl, xenyl, naphthyl, anthryl, phenanthryl, perylene base, pyrenyl.
Further, described Ar 2or Ar 3be selected from phenyl, naphthyl, anthryl, phenyl anthryl, phenanthryl, perylene base, pyrenyl, base, carbazyl, fluoranthene base, triarylamine, hexichol amido, N-phenyl carbazole base, N-phenylnaphthalene amido, dibenzothiophene base, dibenzofuran group.
Further, Ar 2or Ar 3selected group can by phenyl, naphthyl, C 1-6alkyl, carbazyl replace.
In order to be illustrated more clearly in content of the present invention, lower mask body describes the phenanthro-carbazole derivative preferred structure that the present invention relates to:
The invention provides a kind of phenanthro-carbazole derivative that can be applicable in organic electroluminescence device.
Phenanthro-carbazole derivative of the present invention has higher hole migration ability, and described phenanthro-carbazole derivative can be used as hole-injecting material, hole mobile material or material of main part in organic electroluminescence device.
Present invention also offers a kind of organic electroluminescence device, comprise substrate, and form anode layer, organic luminescence function layer and cathode layer on the substrate successively;
Described organic luminescence function layer comprises hole transmission layer, organic luminous layer and electron transfer layer;
The hole mobile material of described hole transmission layer is described phenanthro-carbazole derivative.
Present invention also offers a kind of organic electroluminescence device, comprise substrate, and form anode layer, organic luminescence function layer and cathode layer on the substrate successively;
Described organic luminescence function layer comprises hole transmission layer, organic luminous layer and electron transfer layer;
The material of main part of described organic luminous layer contains described phenanthro-carbazole derivative.
The invention also discloses a kind of method preparing a kind of intermediate of described compound, mainly comprise the steps:
(1) the bromo-triphenylene of 2-shown in structural formula (X) is issued unboiled water solution in normal-butyl reason and the existence of triisopropyl boric acid ester catalyzer and be obtained by reacting the boric acid derivatives shown in structural formula (Y);
(2) compound shown in structural formula (Y) is added triphenylene-2-boric acid, 2,4-bis-bromo nitrobenzene, Pd (PPh 3) 4, sodium carbonate, toluene, and ethanol, after argon replaces, backflow, completely, cooling separates organic layer, carries out post separation, obtain the compound shown in structural formula (Z) by ethyl acetate/petroleum ether,
(3) by the compound shown in structural formula (Z) and triphenylphosphine, and orthodichlorobenzene, mixture is heated to 175 DEG C, has reacted rear cooling, solvent evaporation in vacuo, washing, dry, obtains compound shown in structural formula (P) with pillar layer separation,
The invention also discloses the method preparing another kind of intermediate, mainly comprise the steps:
(1) the bromo-triphenylene of 2-shown in structural formula (X) is issued unboiled water solution in normal-butyl reason and the existence of triisopropyl boric acid ester catalyzer and be obtained by reacting the boric acid derivatives shown in structural formula (Y);
(2) compound shown in structural formula (Y) is added triphenylene-2-boric acid, 2,5-bis-bromo nitrobenzenes, Pd (PPh 3) 4, sodium carbonate, toluene and ethanol, after argon replaces, backflow, completely, cooling separates organic layer, carries out post separation by ethyl acetate/petroleum ether, obtains the compound shown in structural formula (Z '),
(3) by the compound shown in structural formula (Z ') and triphenylphosphine, and orthodichlorobenzene, mixture is heated to 175 DEG C, has reacted rear cooling, solvent evaporation in vacuo, washing, dry, obtains compound shown in structural formula (P ') with pillar layer separation,
Accompanying drawing explanation
In order to make content of the present invention more easily be understood, below according to a particular embodiment of the invention and by reference to the accompanying drawings, the present invention is further detailed explanation; With Gaussian03B3LYP/6-31G(d) method tries to achieve the highest occupied molecular orbital(HOMO) (HOMO) of compound, lowest unoccupied molecular orbital (LUMO) and triplet (T1) respectively.Wherein:
Fig. 1 is the highest occupied molecular orbital(HOMO) of compound 16 of the present invention, and HOMO energy level is-5.055ev, triplet T1=1.7307ev;
Fig. 2 is the lowest unoccupied molecular orbital of compound 16 of the present invention, and lumo energy is-1.579ev;
Fig. 3 is that compound 16 of the present invention is through Gaussian03B3LYP/6-31G(d) method optimize after each atom and the three-dimensional distribution map of group, phenanthro-carbazole parent has good coplanarity as seen from the figure.
Fig. 4 is the highest occupied molecular orbital(HOMO) of compound 1 of the present invention, and HOMO energy level is-4.787ev, triplet T1=2.5201ev;
Fig. 5 is the lowest unoccupied molecular orbital of compound 1 of the present invention, and lumo energy is-1.345ev;
Embodiment
Basic raw material used in the present invention, 2-bromine triphenylene, 2,4-bis-bromo nitrobenzene, 2,5-bis-bromo nitrobenzene, and bromo carbazole derivative, bromo diphenylene-oxide, bromo dibenzothiophene, bromo Chrysene, bromo phenanthrene, bromo pyrene etc., can buy in each large industrial chemicals market at home.
Embodiment
The synthesis of main intermediate triphenylene boric acid:
Be dissolved in the THF of 100ml drying by bromo-for the 2-of 6.12g triphenylene (molecular weight 306,0.02mol) ,-80 DEG C drip normal-butyl reason 10ml(2.5M, 0.025mol), stir 15min, then drip triisopropyl boric acid ester 18ml.Hydrolysis, regulate pH to separate out white boric acid derivatives 5.5g to neutral, productive rate is close to 100%.
Embodiment 1
The synthesis of compound 1
(1) the first step,
1000 milliliters of a bite bottles, join magnetic agitation, add triphenylene-2-boric acid 5.5g(molecular weight 272,0.02mol), 2,4-bis-bromo nitrobenzene 5.28g(molecular weight 278,0.019mol), Pd (PPh 3) 4usage quantity 1.3g(molecular weight 1154,0.001265mol), sodium carbonate 140ml(2M), toluene 140ml, ethanol 140ml.After argon replaces, backflow, with TLC monitoring reaction, react completely after 2 hours, cooling, separated basic unit, evaporate to dryness, the ethyl acetate/petroleum ether with 1/10 carries out post separation, obtains 7.58g product, molecular weight 427, productive rate 93.5%.
(2) second step,
150 milliliters of a bite bottles, join magnetic agitation, add the final product 7.58g(molecular weight 427,0.0178mol of the first step), triphenylphosphine 10.4g(molecular weight 262,0.0395mol), orthodichlorobenzene 70ml.Mixture is heated to 175 DEG C, stirs, by TCL board monitoring reaction process, reacts and complete for 15 hours.Cooling, solvent evaporation in vacuo, washing, dry, with pillar layer separation, ethyl acetate and petroleum ether mixtures drip washing, obtain target molecule 5.9g, molecular weight 395, productive rate 83.8%
(3) the 3rd steps,
150 milliliters of a bite bottles, join magnetic agitation, add second step final product 5.9g(molecular weight 395,0.015mol), 2-naphthalene iodide 5.1g(molecular weight 254,0.02mol), cuprous iodide 0.4g(molecular weight 190,0.0021mol) and, DMPU solvent 60ml.Mixture is heated to 1750C, stirs, by TCL board monitoring reaction process, reacts and complete for 8 hours.Cooling, in impouring water, leaches, and dry, with pillar layer separation, ethyl acetate and petroleum ether mixtures drip washing, obtain target molecule 7.11g, molecular weight 521, productive rate 91%
(4) the 4th steps,
1000 milliliters of a bite bottles, join magnetic agitation, add above-mentioned 3rd step final product 7.11g(molecular weight 521,0.0136mol), 4-(N-phenyl-N-(2-naphthyl) amino) phenylo boric acid 5.1g(molecular weight 339,0.015mol), Pd (PPh 3) 4usage quantity 1.3g(molecular weight 1154,0.001126mol), sodium carbonate 140ml(2M), toluene 140ml, ethanol 140ml.After argon replaces, backflow, with TLC monitoring reaction, reacts completely after 3 hours, cooling, and product solid major part is separated out, and filters, and purifies (also can purify with post separation method if desired), obtain 8.22g product, molecular weight 736, productive rate 83% with recrystallization method.
Product MS(m/e): 736, ultimate analysis (C 56h 36n 2): theoretical value C:91.27%, H:4.92%, N:3.80%; Measured value C:91.25%, H:4.90%, N:3.85%.
Embodiment 2
The synthesis of compound 2
Synthesis step is same as the four-step reaction in embodiment 1, and just in the 3rd step, 2-naphthalene iodide changes into phenyl-iodide, obtains compound 2.
Product MS(m/e): 686, ultimate analysis (C 52h 34n 2): theoretical value C:90.93%, H:4.99%, N:4.08%; Measured value C:90.95%, H:4.98%, N:4.07%.
Embodiment 3
The synthesis of compound 3
Synthesis step is same as the four-step reaction in embodiment 1, and just in the 3rd step, 2-naphthalene iodide changes into phenyl-iodide; In the 4th step, 4-(N-phenyl-N-(2-naphthyl) amino) phenylo boric acid changes into 4-(N, N-diphenylamino) phenylo boric acid, obtain compound 3.
Product MS(m/e): 636, ultimate analysis (C 49h 32n 2): theoretical value C:90.54%, H:5.07%, N:4.40%; Measured value C:90.57%, H:5.08%, N:4.35%.
Embodiment 4
The synthesis of compound 4
Synthesis step is same as the four-step reaction in embodiment 1, just in the 4th step, 4-(N-phenyl-N-(2-naphthyl) amino) phenylo boric acid changes into 4-(carbazole-9-base) phenylo boric acid, obtain compound 4.
Product MS(m/e): 684, ultimate analysis (C 52h 32n 2): theoretical value C:91.20%, H:4.71%, N:4.09%; Measured value C:91.21%, H:4.74%, N:4.05%.
Embodiment 5
The synthesis of compound 5
Synthesis step is same as the four-step reaction in embodiment 1, just in the 4th step, 4-(N, N-diphenylamino) phenylo boric acid changes into 4-(3-phenyl-carbazole-9-base) phenylo boric acid, obtain compound 5.
Product MS(m/e): 760, ultimate analysis (C 58h 36n 2): theoretical value C:91.55%, H:4.77%, N:3.68%; Measured value C:91.52%, H:4.75%, N:3.73%.
Embodiment 6
The synthesis of compound 6
Synthesis step is same as the four-step reaction in embodiment 1, just in the 4th step, will, 4-(N, N-diphenylamino) phenylo boric acid changes into N-phenyl carbazole-3-boric acid, obtains compound 6.
Product MS(m/e): 684, ultimate analysis (C 52h 32n 2): theoretical value C:91.20%, H:4.71%, N:4.09%; Measured value C:91.22%, H:4.73%, N:4.05%.
Embodiment 7
The synthesis of compound 7
Synthesis step is same as the four-step reaction in embodiment 1, just in the 4th step, 4-(N, N-diphenylamino) phenylo boric acid changes into 6,9-phenylbenzene-carbazole-3-boric acid, obtains compound 7.
Product MS(m/e): 760, ultimate analysis (C 58h 36n 2): theoretical value C:91.55%, H:4.77%, N:3.68%; Measured value C:91.55%, H:4.75%, N:3.70%.
Embodiment 8
The synthesis of compound 8
Synthesis step is same as the four-step reaction in embodiment 1, just in the 4th step, 4-(N, N-diphenylamino) phenylo boric acid changes into dibenzothiophene-2-boric acid, obtains compound 8.
Product MS(m/e): 625, ultimate analysis (C 46h 27nS): theoretical value C:88.29%, H:4.35%, N:2.24%, S:5.12%; Measured value C:88.27%, H:4.33%, N:2.26%, S:5.14%.
Embodiment 9
The synthesis of compound 9
Synthesis step is same as the four-step reaction in embodiment 1, just in the 4th step, 4-(N, N-diphenylamino) phenylo boric acid changes into 8-phenyl dibenzothiophene-2-boric acid, obtains compound 9.
Product MS(m/e): 701, ultimate analysis (C 52h 31nS): theoretical value C:88.98%, H:4.45%, N:2.00%, S:4.57%; Measured value C:88.95%, H:4.46%, N:2.03%, S:4.56%.
Embodiment 10
The synthesis of compound 10
Synthesis step is same as the four-step reaction in embodiment 1, just in the 4th step, 4-(N, N-diphenylamino) phenylo boric acid changes into diphenylene-oxide-2-boric acid, obtains compound 10.
Product MS(m/e): 609, ultimate analysis (C 46h 27nO): theoretical value C:90.62%, H:4.46%, N:2.30%, O:2.62%; Measured value C:90.64%, H:4.45%, N:2.32%, O:2.59%.
Embodiment 11
The synthesis of compound 11
Synthesis step is same as the four-step reaction in embodiment 1, just in the 4th step, 4-(N, N-diphenylamino) phenylo boric acid changes into 8-phenyl diphenylene-oxide-2-boric acid, obtains compound 11.
Product MS(m/e): 685, ultimate analysis (C 52h 31nO): theoretical value C:91.07%, H:4.56%, N:2.04%, O:2.33%; Measured value C:91.05%, H:4.54%, N:2.05%, O:2.36%.
Embodiment 12
The synthesis of compound 12
Synthesis step is divided into four steps, and first three walks the front three-step reaction be same as in embodiment 1, and the four-step reaction of just this experiment is same as the three-step reaction in embodiment, is just replaced by 2-naphthalene iodide carbazole, obtains compound 12.
Product MS(m/e): 608, ultimate analysis (C 46h 28n 2): theoretical value C:90.76%, H:4.64%, N:4.60%; Measured value C:90.75%, H:4.63%, N:4.62%.
Embodiment 13
The synthesis of compound 13
Synthesis step is divided into four steps, and first three walks the front three-step reaction be same as in embodiment 1, and the four-step reaction of just this experiment is same as the three-step reaction in embodiment, is just replaced by 2-naphthalene iodide 3-phenyl carbazole, obtains compound 13.
Product MS(m/e): 684, ultimate analysis (C 52h 32n 2): theoretical value C:91.20%, H:4.71%, N:4.09%; Measured value C:91.22%, H:4.72%, N:4.06%.
Embodiment 14
The synthesis of compound 14
Synthesis step is same as the four-step reaction in embodiment 1, just in the 4th step, 4-(N, N-diphenylamino) phenylo boric acid changes into dibenzothiophene-4-boric acid, obtains compound 14.
Product MS(m/e): 625, ultimate analysis (C 46h 27nS): theoretical value C:88.29%, H:4.35%, N:2.24%, S:5.12%; Measured value C:88.26%, H:4.36%, N:2.25%, S:5.13%.
Embodiment 15
The synthesis of compound 15
Synthesis step is same as the four-step reaction in embodiment 1, just in the 4th step, 4-(N, N-diphenylamino) phenylo boric acid changes into 10-phenylanthracene-9-boric acid, obtains compound 15.
Product MS(m/e): 695, ultimate analysis (C 54h 33n): theoretical value C:93.21%, H:4.78%, N:2.01%; Measured value C:93.23%, H:4.75%, N:2.02%.
Embodiment 16
The synthesis of compound 16
Synthesis step is same as the four-step reaction in embodiment 1, just in the 4th step, 4-(N, N-diphenylamino) phenylo boric acid changes into 10-(2-naphthyl) anthracene-9-boric acid, obtain compound 16.
Product MS(m/e): 745, ultimate analysis (C 58h 35n): theoretical value C:93.39%, H:4.73%, N:1.88%; Measured value C:93.37%, H:4.72%, N:1.91%.
Embodiment 17
The synthesis of compound 17
Synthesis step is same as the four-step reaction in embodiment 1, just in the 4th step, 4-(N, N-diphenylamino) phenylo boric acid changes into 10-(1-naphthyl) anthracene-9-boric acid, obtain compound 17.
Product MS(m/e): 745, ultimate analysis (C 58h 35n): theoretical value C:93.39%, H:4.73%, N:1.88%; Measured value C:93.38%, H:4.70%, N:1.92%.
Embodiment 18
The synthesis of compound 18
Synthesis step is same as the four-step reaction in embodiment 1, just in the 4th step, 4-(N, N-diphenylamino) phenylo boric acid changes into 4-(10-phenylanthracene-9-base) phenylo boric acid, obtain compound 18.
Product MS(m/e): 771, ultimate analysis (C 60h 37n): theoretical value C:93.35%, H:4.83%, N:1.81%; Measured value C:93.32%, H:4.82%, N:1.86%.
Embodiment 19
The synthesis of compound 19
Synthesis step is same as the four-step reaction in embodiment 1, just in the 4th step, 4-(N, N-diphenylamino) phenylo boric acid changes into-1-boric acid in the wrong, obtains compound 19.
Product MS(m/e): 669, ultimate analysis (C 52h 31n): theoretical value C:93.24%, H:4.66%, N:2.09%; Measured value C:93.21%, H:4.64%, N:2.15%.
Embodiment 20
The synthesis of compound 20
Synthesis step is same as the four-step reaction in embodiment 1, just in the 4th step, 4-(N, N-diphenylamino) phenylo boric acid changes into triphenylene-2-boric acid, obtains compound 20.
Product MS(m/e): 669, ultimate analysis (C 52h 31n): theoretical value C:93.24%, H:4.66%, N:2.09%; Measured value C:93.23%, H:4.65%, N:2.12%.
Embodiment 21
The synthesis of compound 21
Synthesis step is same as the four-step reaction in embodiment 1, just in the 4th step, 4-(N, N-diphenylamino) phenylo boric acid changes into pyrene-1-boric acid, obtains compound 21.
Product MS(m/e): 643, ultimate analysis (C 50h 29n): theoretical value C:93.28%, H:4.54%, N:2.18%; Measured value C:93.25%, H:4.56%, N:2.19%.
Embodiment 22
The synthesis of compound 22
Synthesis step is same as the four-step reaction in embodiment 1, just in the 4th step, 4-(N, N-diphenylamino) phenylo boric acid changes into benzophenanthrene-5-boric acid, obtains compound 22.
Product MS(m/e): 669, ultimate analysis (C 52h 31n): theoretical value C:93.24%, H:4.66%, N:2.09%; Measured value C:93.26%, H:4.64%, N:2.10%.
Embodiment 23
The synthesis of compound 23
Synthesis step is same as the four-step reaction in embodiment 1, just in the 4th step, 4-(N, N-diphenylamino) phenylo boric acid changes into phenanthrene-9-boric acid, obtains compound 23.
Product MS(m/e): 619, ultimate analysis (C 48h 29n): theoretical value C:93.02%, H:4.72%, N:2.26%; Measured value C:93.04%, H:4.73%, N:2.23%.
Embodiment 24
The synthesis of compound 24
Synthesis step is same as the four-step reaction in embodiment 1, just in the 4th step, 4-(N, N-diphenylamino) phenylo boric acid changes into phenanthrene-3-boric acid, obtains compound 23.
Product MS(m/e): 619, ultimate analysis (C 48h 29n): theoretical value C:93.02%, H:4.72%, N:2.26%; Measured value C:93.03%, H:4.75%, N:2.22%.
Embodiment 25
The synthesis of compound 25
Synthesis step is divided into four steps, and first three walks the front three-step reaction be same as in embodiment 1, just in the first step reaction, replaces 2,4-bis-bromo nitrobenzene with 2,5-bis-bromo nitrobenzene.In addition, the four-step reaction of this experiment is same as the three-step reaction in embodiment, is just replaced by 2-naphthalene iodide N-phenyl-2-naphthylamine, obtains compound 25.
Product MS(m/e): 660, ultimate analysis (C 46h 28n 2): theoretical value C:90.88%, H:4.88%, N:4.24%; Measured value C:90.85%, H:4.86%, N:4.29%.
Embodiment 26
The synthesis of compound 26
Synthesis step is same as the four-step reaction in embodiment 1, just in the first step reaction, replaces 2,4-bis-bromo nitrobenzene with 2,5-bis-bromo nitrobenzene; In the 4th step, 4-(N-phenyl-N-(2-naphthyl) amino) phenylo boric acid changes into triphenylamine-4-boric acid, obtains compound 26.
Product MS(m/e): 686, ultimate analysis (C 52h 34n 2): theoretical value C:90.93%, H:4.99%, N:4.08%; Measured value C:90.95%, H:4.96%, N:4.09%.
Embodiment 27
The synthesis of compound 27
Synthesis step is same as the four-step reaction in embodiment 1, just in the first step reaction, replaces 2,4-bis-bromo nitrobenzene with 2,5-bis-bromo nitrobenzene; In the 4th step, 4-(N-phenyl-N-(2-naphthyl) amino) phenylo boric acid changes into 4-(carbazole-9-base) phenylo boric acid, obtain compound 27.
Product MS(m/e): 684, ultimate analysis (C 52h 32n 2): theoretical value C:91.20%, H:4.71%, N:4.09%; Measured value C:91.22%, H:4.74%, N:4.04%.
Embodiment 28
The synthesis of compound 28
Synthesis step is same as the four-step reaction in embodiment 1, just in the first step reaction, replaces 2,4-bis-bromo nitrobenzene with 2,5-bis-bromo nitrobenzene; In the 4th step, 4-(N, N-diphenylamino) phenylo boric acid changes into 4-(3-phenyl-carbazole-9-base) phenylo boric acid, obtain compound 28.
Product MS(m/e): 760, ultimate analysis (C 58h 36n 2): theoretical value C:91.55%, H:4.77%, N:3.68%; Measured value C:91.51%, H:4.75%, N:3.74%.
Embodiment 29
The synthesis of compound 29
Synthesis step is same as the four-step reaction in embodiment 1, just in the first step reaction, replaces 2,4-bis-bromo nitrobenzene with 2,5-bis-bromo nitrobenzene; In the 4th step, will, 4-(N, N-diphenylamino) phenylo boric acid changes into N-phenyl carbazole-3-boric acid, obtains compound 6.
Product MS(m/e): 684, ultimate analysis (C 52h 32n 2): theoretical value C:91.20%, H:4.71%, N:4.09%; Measured value C:91.23%, H:4.72%, N:4.05%.
Embodiment 30
The synthesis of compound 30
Synthesis step is same as the four-step reaction in embodiment 1, just in the first step reaction, replaces 2,4-bis-bromo nitrobenzene with 2,5-bis-bromo nitrobenzene; In the 4th step, 4-(N, N-diphenylamino) phenylo boric acid changes into 6,9-phenylbenzene carbazole-3-boric acid, obtains compound 30.
Product MS(m/e): 760, ultimate analysis (C 58h 36n 2): theoretical value C:91.55%, H:4.77%, N:3.68%; Measured value C:91.54%, H:4.75%, N:3.71%.
Embodiment 31
The synthesis of compound 31
Synthesis step is same as the four-step reaction in embodiment 1, just in the first step reaction, replaces 2,4-bis-bromo nitrobenzene with 2,5-bis-bromo nitrobenzene; In the 4th step, 4-(N, N-diphenylamino) phenylo boric acid changes into dibenzothiophene-2-boric acid, obtains compound 31.
Product MS(m/e): 625, ultimate analysis (C 46h 27nS): theoretical value C:88.29%, H:4.35%, N:2.24%, S:5.12%; Measured value C:88.27%, H:4.36%, N:2.26%, S:5.11%.
Embodiment 32
The synthesis of compound 32
Synthesis step is same as the four-step reaction in embodiment 1, just in the first step reaction, replaces 2,4-bis-bromo nitrobenzene with 2,5-bis-bromo nitrobenzene; In the 4th step, 4-(N, N-diphenylamino) phenylo boric acid changes into 8-phenyl dibenzothiophene-2-boric acid, obtains compound 32.
Product MS(m/e): 701, ultimate analysis (C 52h 31nS): theoretical value C:88.98%, H:4.45%, N:2.00%, S:4.57%; Measured value C:88.96%, H:4.46%, N:2.03%, S:4.55%.
Embodiment 33
The synthesis of compound 33
Synthesis step is same as the four-step reaction in embodiment 1, just in the first step reaction, replaces 2,4-bis-bromo nitrobenzene with 2,5-bis-bromo nitrobenzene; In the 4th step, 4-(N, N-diphenylamino) phenylo boric acid changes into diphenylene-oxide-2-boric acid, obtains compound 33.
Product MS(m/e): 609, ultimate analysis (C 46h 27nO): theoretical value C:90.62%, H:4.46%, N:2.30%, O:2.62%; Measured value C:90.65%, H:4.44%, N:2.33%, O:2.58%.
Embodiment 34
The synthesis of compound 34
Synthesis step is same as the four-step reaction in embodiment 1, just in the first step reaction, replaces 2,4-bis-bromo nitrobenzene with 2,5-bis-bromo nitrobenzene; In the 4th step, 4-(N, N-diphenylamino) phenylo boric acid changes into 8-phenyl diphenylene-oxide-2-boric acid, obtains compound 34.
Product MS(m/e): 685, ultimate analysis (C 52h 31nO): theoretical value C:91.07%, H:4.56%, N:2.04%, O:2.33%; Measured value C:91.04%, H:4.54%, N:2.06%, O:2.36%.
Embodiment 35
The synthesis of compound 35
Synthesis step is same as the four-step reaction in embodiment 1, just in the first step reaction, replaces 2,4-bis-bromo nitrobenzene with 2,5-bis-bromo nitrobenzene; In the 4th step, 4-(N, N-diphenylamino) phenylo boric acid changes into dibenzothiophene-4-boric acid, obtains compound 35.
Product MS(m/e): 625, ultimate analysis (C 46h 27nS): theoretical value C:88.29%, H:4.35%, N:2.24%, S:5.12%; Measured value C:88.28%, H:4.37%, N:2.26%, S:5.09%.
Embodiment 36
The synthesis of compound 36
Synthesis step is same as the four-step reaction in embodiment 1, just in the first step reaction, replaces 2,4-bis-bromo nitrobenzene with 2,5-bis-bromo nitrobenzene; In the 4th step, 4-(N, N-diphenylamino) phenylo boric acid changes into 10-(2-naphthyl) anthracene-9-boric acid, obtain compound 36.
Product MS(m/e): 745, ultimate analysis (C 58h 35n): theoretical value C:93.39%, H:4.73%, N:1.88%; Measured value C:93.37%, H:4.71%, N:1.92%.
Embodiment 37
The synthesis of compound 37
Synthesis step is same as the four-step reaction in embodiment 1, just in the first step reaction, replaces 2,4-bis-bromo nitrobenzene with 2,5-bis-bromo nitrobenzene; In the 4th step, 4-(N, N-diphenylamino) phenylo boric acid changes into 4-(10-(2-naphthyl) anthracene-9-base) phenylo boric acid, obtain compound 37.
Product MS(m/e): 821, ultimate analysis (C 64h 39n): theoretical value C:93.51%, H:4.78%, N:1.70%; Measured value C:93.53%, H:4.75%, N:1.72%.
Embodiment 38
The synthesis of compound 38
Synthesis step is same as the four-step reaction in embodiment 1, just in the first step reaction, is replacing 2,4-bis-bromo nitrobenzene with 2,5-bis-bromo nitrobenzene; 4th step, 4-(N, N-diphenylamino) phenylo boric acid changes into-1-boric acid in the wrong, obtains compound 38.
Product MS(m/e): 669, ultimate analysis (C 52h 31n): theoretical value C:93.24%, H:4.66%, N:2.09%; Measured value C:93.22%, H:4.63%, N:2.15%.
Embodiment 39
The synthesis of compound 39
Synthesis step is same as the four-step reaction in embodiment 1, just in the first step reaction, replaces 2,4-bis-bromo nitrobenzene with 2,5-bis-bromo nitrobenzene; In the 4th step, 4-(N, N-diphenylamino) phenylo boric acid changes into benzophenanthrene-5-boric acid, obtains compound 39.
Product MS(m/e): 669, ultimate analysis (C 52h 31n): theoretical value C:93.24%, H:4.66%, N:2.09%; Measured value C:93.21%, H:4.65%, N:2.13%.
Embodiment 40
The synthesis of compound 40
Synthesis step is same as the four-step reaction in embodiment 1, just in the first step reaction, replaces 2,4-bis-bromo nitrobenzene with 2,5-bis-bromo nitrobenzene; In the 4th step, 4-(N, N-diphenylamino) phenylo boric acid changes into pyrene-1-boric acid, obtains compound 40.
Product MS(m/e): 643, ultimate analysis (C 50h 29n): theoretical value C:93.28%, H:4.54%, N:2.18%; Measured value C:93.26%, H:4.57%, N:2.17%.
Embodiment 41
The synthesis of compound 41
Synthesis step is same as the four-step reaction in embodiment 1, just in the first step reaction, replaces 2,4-bis-bromo nitrobenzene with 2,5-bis-bromo nitrobenzene; In the 4th step, 4-(N, N-diphenylamino) phenylo boric acid changes into phenanthrene-3-boric acid, obtains compound 41.
Product MS(m/e): 619, ultimate analysis (C 48h 29n): theoretical value C:93.02%, H:4.72%, N:2.26%; Measured value C:93.01%, H:4.75%, N:2.24%.
Embodiment 42
The synthesis of compound 42
Synthesis step is same as the four-step reaction in embodiment 1, just in the first step reaction, replaces 2,4-bis-bromo nitrobenzene with 2,5-bis-bromo nitrobenzene; In the 4th step, 4-(N, N-diphenylamino) phenylo boric acid changes into phenanthrene-3-boric acid, obtains compound 23.
Product MS(m/e): 619, ultimate analysis (C 48h 29n): theoretical value C:93.02%, H:4.72%, N:2.26%; Measured value C:93.03%, H:4.74%, N:2.23%.
Here is the Application Example of each compound of the present invention:
Conveniently compare the performance that these electroluminescent organic materials can be used as hole-injecting material, hole mobile material and fluorescent host material, the present invention devises a simple electroluminescent device, hole injection layer (HIL) material we select 2-TNATA, hole mobile material we select NPB as comparative material.Organic luminous layer is made up of light emitting host material and dopant material, and we use traditional light emitting host material EM1 as comparative material, and EM2 is as luminescent dopant material, and wherein the structure of 2-TNATA, NPB, EM1 and EM2 is respectively:
In the embodiment of the present invention, the structure of organic electroluminescence device is:
Substrate/anode/hole injection layer (HIL)/hole transmission layer (HTL)/organic luminous layer (EL)/electron transfer layer (ETL)/negative electrode.
Substrate can use the substrate in conventional organic luminescence device, such as: glass or plastics.In organic electroluminescence device of the present invention makes, select glass substrate, ITO makes anode material.
Hole-injecting material can use the various many arylamine very easily providing electronics, and the material of stating in the present invention can be used as hole-injecting material in electroluminescent device, and the hole-injecting material of contrast is 2-TNATA.
Hole transmission layer can adopt various tri-arylamine group material.The material of stating in the present invention can be used as hole mobile material in electroluminescent device, compares with traditional hole mobile material NPB.
Emitting layer material has many kinds, and the material of stating in the present invention can be used as light emitting host material in electroluminescence device, and contrast main body is EM1, and luminescent dopant material is EM2.
Electron transport layer materials has many kinds, and in order to characterize the material of stating in the present invention, we use common AlQ here 3as electron transport material, object compares material property in the present invention, do not lie in the excellence pursuing device performance.
Negative electrode can adopt metal and composition thereof structure, as Mg:Ag, Ca:Ag etc., can be also electron injecting layer/metal-layer structure, as LiF/Al, Li 2the common cathode structures such as O/Al.Cathode material selected in organic electroluminescence device of the present invention makes is LiF/Al.
In the present embodiment, organic electroluminescence device preparation process is as follows:
Sheet glass supersound process in commercial detergent of ITO transparency conducting layer will be coated with, rinse in deionized water, at acetone: ultrasonic oil removing in alcohol mixed solvent, be baked under clean environment and remove moisture content completely, by UV-light and ozone clean, and with low energy positively charged ion bundle bombarded surface;
The above-mentioned glass substrate with anode is placed in vacuum chamber, is evacuated to 2 × 10 -5~ 2 × 10 -4pa, on above-mentioned anode tunic, vacuum evaporation 2-TNATA or particular compound of the present invention are as hole injection layer, and evaporation rate is 0.1nm/s, and evaporation thickness is 50nm;
Particular compound on hole injection layer again in evaporation one deck NPB or the present invention is as hole transmission layer, and evaporation rate is 0.1nm/s, and evaporation thickness is 40nm;
Mode vacuum evaporation light emitting host layer EM1 and the EM2(ratio 95%:5% of codoped is adopted on hole transmission layer), or particular compound in the present invention and EM2(ratio 95%:5%), evaporation rate is 0.1nm/s, and evaporation total film thickness is 30nm;
Difference vacuum evaporation one deck AlQ on luminescent layer 3as electron transport material, its evaporation rate is 0.1nm/s, and evaporation total film thickness is 20nm;
The upper vacuum evaporation thickness of electron transfer layer (ETL) be the LiF of 0.5nm as electron injecting layer, thickness is the negative electrode of Al layer as device of 150nm.
Embodiment 43
In the present embodiment, compound is as the hole-injecting material in organic electroluminescence device, and prepared multiple organic electroluminescence device altogether, its structure is: ITO/ hole-injecting material (50nm)/NPB(40nm)/EM1:EM2 (30nm)/Alq 3(20nm)/LiF(0.5nm)/Al(150nm).
In contrast organic electroluminescence device, hole-injecting material selects 2-TNATA, and all the other organic electroluminescence devices select material of the present invention.
Organic electroluminescence device performance sees the following form:
Compound number Require brightness cd/m 2 Voltage V Current efficiency cd/A
NPB 1000.00 5.9 6.0
1 1000.00 5.4 6.3
2 1000.00 5.5 6.3
3 1000.00 5.4 6.4
25 1000.00 5.5 6.4
26 1000.00 5.4 6.3
Above result shows, new organic materials of the present invention is used for organic electroluminescence device, can effectively reduce landing voltage, and improving current efficiency, is hole-injecting material of good performance.
Embodiment 44
In the present embodiment, compound is as the hole mobile material in organic electroluminescence device, and prepared multiple organic electroluminescence device altogether, its structure is: ITO/2-TNATA(50nm)/hole mobile material (40nm)/EM1:EM2 (30nm)/Alq 3(20nm)/LiF(0.5nm)/Al(150nm).
In contrast organic electroluminescence device, hole mobile material selects NPB, and all the other organic electroluminescence devices select material of the present invention.
Organic electroluminescence device performance sees the following form:
Compound number Require brightness cd/m 2 Voltage V Current efficiency cd/A
NPB 1000.00 5.9 6.0
4 1000.00 5.5 6.3
5 1000.00 5.6 6.3
6 1000.00 5.5 6.4
7 1000.00 5.6 6.5
8 1000.00 5.4 6.5
9 1000.00 5.4 6.4
10 1000.00 5.5 6.6
11 1000.00 5.4 6.6
12 1000.00 5.6 6.4
13 1000.00 5.4 6.4
14 1000.00 5.3 6.4
27 1000.00 5.4 6,.5
28 1000.00 5.4 6.5
29 1000.00 5.5 6.6
30 1000.00 5.5 6.4
31 1000.00 5.4 6.4
32 1000.00 5.4 6.5
33 1000.00 5.5 6.5
34 1000.00 5.5 6.4
35 1000.00 5.4 6.4
Above result shows, new organic materials of the present invention is used for organic electroluminescence device, can effectively reduce landing voltage, and improving current efficiency, is hole mobile material of good performance
Embodiment 45
Compound in the present embodiment is as the material of main part in organic electroluminescence device, prepare multiple organic electroluminescence device altogether, its structure is: ITO/2-TNATA(50nm)/NPB(40nm)/light emitting host material: EM2 (85%:15%, 30nm)/Alq 3(20nm)/LiF(0.5nm)/Al(150nm);
In contrast organic electroluminescence device, light emitting host material selection EM1, all the other organic electroluminescence devices select material of the present invention.
Luminescent device performance sees the following form:
Compound number Require brightness cd/m 2 Voltage V Current efficiency cd/A
EM1 1000.00 5.9 6.0
15 1000.00 5.4 6.4
16 1000.00 5.4 6.5
17 1000.00 5.5 6.5
18 1000.00 5.5 6.4
19 1000.00 5.4 6.5
20 1000.00 5.4 6.5
21 1000.00 5.5 6.5
22 1000.00 5.4 6.6
23 1000.00 5.4 6.4
24 1000.00 5.5 6.6
36 1000.00 5.6 6.4
37 1000.00 5.4 6.7
38 1000.00 5.5 6.8
39 1000.00 5.5 6.6
40 1000.00 5.6 6.4
41 1000.00 5.6 6.6
41 1000.00 5.4 6.4
Above result shows, new organic materials of the present invention is used for organic electroluminescence device, can effectively reduce landing voltage, and improving current efficiency, is light emitting host material of good performance.
Although describe the present invention in conjunction with the embodiments, the present invention is not limited to above-described embodiment, should be appreciated that, under the guiding of the present invention's design, those skilled in the art can carry out various amendment and improvement, and claims summarise scope of the present invention.

Claims (12)

1. a phenanthro-carbazole derivative, is characterized in that, has structure as shown in the formula (I):
Wherein: Ar 1-Ar 8independently be selected from the substituted or non-substituted aromatic hydrocarbon group of H, C6 ~ C30, the condensed-nuclei aromatics group of the substituted or non-substituted of C6 ~ C30, the substituted or non-substituted of C6 ~ C30 fused heterocycle group, five yuan, hexa-atomic heterocycle or substituted heterocycle, triarylamine group, aryl oxide group base group, C1 ~ C12 substituted or non-substituted aliphatic alkyl group in one;
Ar 9be selected from the substituted or non-substituted aromatic hydrocarbon group of C6 ~ C30, the condensed-nuclei aromatics group of the substituted or non-substituted of C6 ~ C30, the substituted or non-substituted of C1 ~ C12 aliphatic alkyl group in one.
2. phenanthro-carbazole derivative according to claim 1, is characterized in that, described Ar 1, Ar 4, Ar 5, Ar 6, Ar 7, Ar 8be H simultaneously.
3. phenanthro-carbazole derivative according to claim 1, is characterized in that, described Ar 9be selected from phenyl, aminomethyl phenyl, ethylphenyl, p-methoxy-phenyl, xenyl, naphthyl, anthryl, phenanthryl, perylene base, pyrenyl.
4. phenanthro-carbazole derivative according to claim 1, is characterized in that, described Ar 2or Ar 3be selected from phenyl, naphthyl, anthryl, phenyl anthryl, phenanthryl, perylene base, pyrenyl, base, carbazyl, fluoranthene base, triarylamine, hexichol amido, N-phenyl carbazole base, N-phenylnaphthalene amido, dibenzothiophene base, dibenzofuran group.
5. phenanthro-carbazole derivative according to claim 4, is characterized in that, Ar 2or Ar 3selected group can by phenyl, naphthyl, C 1-6alkyl, carbazyl replace.
6. the phenanthro-carbazole derivative according to any one of claim 1-5, is characterized in that, described compound is selected from following structural formula:
7. the phenanthro-carbazole derivative described in any one of claim 1-6, is applied in organic electroluminescence device.
8. a kind of phenanthro-carbazole derivative being applied to organic electroluminescence device according to claim 7, it is characterized in that, described phenanthro-carbazole derivative can be used as hole-injecting material, hole mobile material or material of main part.
9. an organic electroluminescence device, comprises substrate, and forms anode layer, organic luminescence function layer and cathode layer on the substrate successively; Described organic luminescence function layer comprises hole transmission layer, organic luminous layer and electron transfer layer, it is characterized in that:
The phenanthro-carbazole derivative of hole mobile material according to any one of claim 1-6 of described hole transmission layer.
10. an organic electroluminescence device, comprises substrate, and forms anode layer, organic luminescence function layer and cathode layer on the substrate successively; Described organic luminescence function layer comprises hole transmission layer, organic luminous layer and electron transfer layer, it is characterized in that:
The material of main part of described organic luminous layer contains the phenanthro-carbazole derivative according to any one of claim 1-6.
11. 1 kinds of methods preparing the arbitrary described compound intermediate of claim 1-6, is characterized in that: comprise the steps:
(1) the bromo-triphenylene of 2-shown in structural formula (X) is issued unboiled water solution in normal-butyl reason and the existence of triisopropyl boric acid ester catalyzer and be obtained by reacting the boric acid derivatives shown in structural formula (Y);
(2) compound shown in structural formula (Y) is added triphenylene-2-boric acid, 2,4-bis-bromo nitrobenzenes, Pd (PPh 3) 4, sodium carbonate, toluene and ethanol, after argon replaces, backflow, completely, cooling separates organic layer, carries out post separation, obtain the compound shown in structural formula (Z) by ethyl acetate/petroleum ether,
(3) by the compound shown in structural formula (Z) and triphenylphosphine, and orthodichlorobenzene, mixture is heated to 175 DEG C, has reacted rear cooling, solvent evaporation in vacuo, washing, dry, obtains compound shown in structural formula (P) with pillar layer separation,
12. 1 kinds of methods preparing the arbitrary described intermediate of claim 1-6, is characterized in that comprising the steps:
(1) the bromo-triphenylene of 2-shown in structural formula (X) is issued unboiled water solution in normal-butyl reason and the existence of triisopropyl boric acid ester catalyzer and be obtained by reacting the boric acid derivatives shown in structural formula (Y);
(2) compound shown in structural formula (Y) is added triphenylene-2-boric acid, 2,5-bis-bromo nitrobenzene, Pd (PPh 3) 4, sodium carbonate, toluene, and ethanol, after argon replaces, backflow, completely, cooling separates organic layer, carries out post separation by ethyl acetate/petroleum ether, obtains the compound shown in structural formula (Z '),
(3) by the compound shown in structural formula (Z ') and triphenylphosphine, and orthodichlorobenzene, mixture is heated to 175 DEG C, has reacted rear cooling, solvent evaporation in vacuo, washing, dry, obtains compound shown in structural formula (P ') with pillar layer separation,
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CN111303056A (en) * 2015-09-30 2020-06-19 北京鼎材科技有限公司 Phenazine group-substituted polycyclic aromatic hydrocarbon derivative and application thereof
KR101856586B1 (en) * 2017-06-13 2018-05-10 (주)위즈켐 Preparation method of 13-Bromo-10H-phenanthro[9,10-b]carbazole
US11108001B2 (en) * 2019-01-17 2021-08-31 Luminescence Technology Corp. Organic compound and organic electroluminescence device using the same
TWI747141B (en) * 2019-01-17 2021-11-21 機光科技股份有限公司 Organic compound and organic electroluminescence device using the same
CN110041165A (en) * 2019-05-10 2019-07-23 安徽秀朗新材料科技有限公司 A kind of preparation method of 2- bromine triphenylene

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