WO2020125240A1 - 有机电致发光材料及其应用 - Google Patents
有机电致发光材料及其应用 Download PDFInfo
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- WO2020125240A1 WO2020125240A1 PCT/CN2019/115179 CN2019115179W WO2020125240A1 WO 2020125240 A1 WO2020125240 A1 WO 2020125240A1 CN 2019115179 W CN2019115179 W CN 2019115179W WO 2020125240 A1 WO2020125240 A1 WO 2020125240A1
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- organic electroluminescent
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- 239000000463 material Substances 0.000 title claims abstract description 23
- 150000001875 compounds Chemical class 0.000 claims abstract description 17
- 239000010410 layer Substances 0.000 claims description 52
- 238000002347 injection Methods 0.000 claims description 20
- 239000007924 injection Substances 0.000 claims description 20
- 239000012044 organic layer Substances 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 230000005525 hole transport Effects 0.000 claims description 7
- 239000000243 solution Substances 0.000 claims description 6
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 5
- 229910052805 deuterium Inorganic materials 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 230000000903 blocking effect Effects 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 238000001704 evaporation Methods 0.000 claims description 2
- 230000008020 evaporation Effects 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 239000010409 thin film Substances 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 abstract description 6
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 abstract description 3
- 125000004093 cyano group Chemical group *C#N 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 6
- 229940125904 compound 1 Drugs 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- HIHOEGPXVVKJPP-JTQLQIEISA-N 5-fluoro-2-[[(1s)-1-(5-fluoropyridin-2-yl)ethyl]amino]-6-[(5-methyl-1h-pyrazol-3-yl)amino]pyridine-3-carbonitrile Chemical compound N([C@@H](C)C=1N=CC(F)=CC=1)C(C(=CC=1F)C#N)=NC=1NC=1C=C(C)NN=1 HIHOEGPXVVKJPP-JTQLQIEISA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000006798 recombination Effects 0.000 description 2
- 238000005215 recombination Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- PHDIJLFSKNMCMI-ITGJKDDRSA-N (3R,4S,5R,6R)-6-(hydroxymethyl)-4-(8-quinolin-6-yloxyoctoxy)oxane-2,3,5-triol Chemical compound OC[C@@H]1[C@H]([C@@H]([C@H](C(O1)O)O)OCCCCCCCCOC=1C=C2C=CC=NC2=CC=1)O PHDIJLFSKNMCMI-ITGJKDDRSA-N 0.000 description 1
- PKRRNTJIHGOMRC-UHFFFAOYSA-N 1-benzofuran-2-ylboronic acid Chemical compound C1=CC=C2OC(B(O)O)=CC2=C1 PKRRNTJIHGOMRC-UHFFFAOYSA-N 0.000 description 1
- IXHWGNYCZPISET-UHFFFAOYSA-N 2-[4-(dicyanomethylidene)-2,3,5,6-tetrafluorocyclohexa-2,5-dien-1-ylidene]propanedinitrile Chemical compound FC1=C(F)C(=C(C#N)C#N)C(F)=C(F)C1=C(C#N)C#N IXHWGNYCZPISET-UHFFFAOYSA-N 0.000 description 1
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 1
- JSWDWMBIBSINSL-UHFFFAOYSA-N CC1(C)OB(c2c[o]c3ccccc23)OC1(C)C Chemical compound CC1(C)OB(c2c[o]c3ccccc23)OC1(C)C JSWDWMBIBSINSL-UHFFFAOYSA-N 0.000 description 1
- WOWCMFYHTIUTOS-UHFFFAOYSA-N N#CC(C#N)=C1c([o]c2ccccc22)c2-c2nc(C(c3c-4c(cccc5)c5[o]3)=C(C#N)C#N)c-4nc12 Chemical compound N#CC(C#N)=C1c([o]c2ccccc22)c2-c2nc(C(c3c-4c(cccc5)c5[o]3)=C(C#N)C#N)c-4nc12 WOWCMFYHTIUTOS-UHFFFAOYSA-N 0.000 description 1
- NTDREVCIIWPSIR-UHFFFAOYSA-N O=C1c([o]c2c3cccc2)c3-c2c1nc(-c1c(C3=O)[o]c4ccccc14)c3n2 Chemical compound O=C1c([o]c2c3cccc2)c3-c2c1nc(-c1c(C3=O)[o]c4ccccc14)c3n2 NTDREVCIIWPSIR-UHFFFAOYSA-N 0.000 description 1
- OTOXOECUQSLPBP-UHFFFAOYSA-N OC(c1nc(-c2c[o]c3c2cccc3)c(C(O)=O)nc1-c1c[o]c2ccccc12)=O Chemical compound OC(c1nc(-c2c[o]c3c2cccc3)c(C(O)=O)nc1-c1c[o]c2ccccc12)=O OTOXOECUQSLPBP-UHFFFAOYSA-N 0.000 description 1
- RQRIPQYTFAYYMX-UHFFFAOYSA-N OC(c1nc(Br)c(C(O)=O)nc1Br)=O Chemical compound OC(c1nc(Br)c(C(O)=O)nc1Br)=O RQRIPQYTFAYYMX-UHFFFAOYSA-N 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- -1 cooled to 0°C Chemical compound 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
- 230000005669 field effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- GGQOPZKTDHXXON-UHFFFAOYSA-N hexane;methanol Chemical compound OC.CCCCCC GGQOPZKTDHXXON-UHFFFAOYSA-N 0.000 description 1
- 238000003402 intramolecular cyclocondensation reaction Methods 0.000 description 1
- 239000002346 layers by function Substances 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- GVOISEJVFFIGQE-YCZSINBZSA-N n-[(1r,2s,5r)-5-[methyl(propan-2-yl)amino]-2-[(3s)-2-oxo-3-[[6-(trifluoromethyl)quinazolin-4-yl]amino]pyrrolidin-1-yl]cyclohexyl]acetamide Chemical compound CC(=O)N[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(=CC=C3N=CN=2)C(F)(F)F)CC1 GVOISEJVFFIGQE-YCZSINBZSA-N 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- SWGJCIMEBVHMTA-UHFFFAOYSA-K trisodium;6-oxido-4-sulfo-5-[(4-sulfonatonaphthalen-1-yl)diazenyl]naphthalene-2-sulfonate Chemical compound [Na+].[Na+].[Na+].C1=CC=C2C(N=NC3=C4C(=CC(=CC4=CC=C3O)S([O-])(=O)=O)S([O-])(=O)=O)=CC=C(S([O-])(=O)=O)C2=C1 SWGJCIMEBVHMTA-UHFFFAOYSA-K 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 238000005019 vapor deposition process Methods 0.000 description 1
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- C07D471/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed systems contains four or more hetero rings
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- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
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- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/14—Ortho-condensed systems
- C07D491/153—Ortho-condensed systems the condensed system containing two rings with oxygen as ring hetero atom and one ring with nitrogen as ring hetero atom
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- C07D491/22—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains four or more hetero rings
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
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- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
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- H10K50/15—Hole transporting layers
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Definitions
- the invention relates to the field of organic electroluminescent materials, in particular to an electroluminescent material containing pyrazine and cyano group and its application.
- OLEDs organic light-emitting diodes
- OLED devices have the characteristics of self-luminescence, wide viewing angle, short reaction time and flexible devices that can be prepared, and have become a strong competitor of next-generation display and lighting technologies.
- OLED still has the problems of low efficiency and short life, which need to be further studied.
- a high-efficiency PHOLED device usually has a multilayer structure, including a cathode, an anode, and an organic layer, the organic layer being one of a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer, an electron injection layer, and an electron transport layer
- the advantage is that it can easily adjust the process of carrier injection, transmission and recombination to improve carrier transmission and recombination efficiency.
- TCNQF4 is often used as a hole injection layer, which can effectively promote the injection of holes and reduce the driving voltage.
- TCNQF4 due to its small molecular weight and good volatility, it is easy to contaminate the vapor deposition instrument and devices during the vapor deposition process.
- the purpose of the present invention is to provide an organic electroluminescent material containing pyrazine and cyano, which can effectively reduce the device voltage and improve the efficiency.
- Organic electroluminescent materials are compounds with the structure of formula (I):
- B is selected from O, S, NR 1 , R 1 is selected from C1-C6 alkyl, C3-C40 heteroaryl, C6-C40 aromatic;
- X 1 -X 4 are independently selected from N, CR 2 , and R 2 is selected from hydrogen, deuterium, C1-C6 alkyl, C3-C40 heteroaryl, C6-C40 aromatic.
- B is selected from O, S, NR 1 , R 1 is selected from C1-C6 alkyl, C3-C9 heteroaryl, C6-C14 aromatic;
- X 1 -X 4 are independently selected from N, CR 2 , R 2 is selected from hydrogen, deuterium, C1-C6 alkyl, C3-C9 heteroaryl, C6-C14 aromatic.
- B is selected from O, S, NR 1 , R 1 is selected from methyl, phenyl, tolyl, naphthyl, pyridyl;
- X 1 -X 4 are independently selected from N and CH.
- B is selected from O, S, NR 1 , R 1 is selected from methyl, phenyl, pyridyl;
- X 1 -X 4 are independently selected from N, CH.
- B is selected from O, S, NR 1 , R 1 is selected from methyl, phenyl, pyridyl;
- 0-2 of X1-X4 are N, and the rest are CH.
- the light-emitting material of the formula (I) of the present invention is the following 1-18 compounds, but is not limited to the listed structures:
- the above compounds can be used in organic electroluminescent devices, electroluminescent devices, organic field effect transistors, organic solar cells and chemical sensors.
- the present invention does not specifically limit the preparation method of the compound described in the chemical formula (I).
- Typical but non-limiting compounds are As an illustrative example, its synthesis and preparation methods are as follows:
- the organic electroluminescent device of the present invention includes a cathode, an anode, and an organic layer.
- the organic layer is a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer, an electron injection layer, and an electron transport layer.
- One or more layers, these organic layers need not be present in every layer.
- At least one layer of the hole injection layer, hole transport layer, hole blocking layer, light emitting layer and/or electron transport layer contains the compound of formula (I).
- the layer of the compound described in structural formula (1) is a hole injection layer or an electron transport layer.
- the total thickness of the organic layer of the device of the present invention is 1-1000 nm, preferably 1-500 nm, and more preferably 5-300 nm.
- the organic layer can be formed into a thin film by evaporation or solution method.
- the experimental results show that the organic electroluminescent material in the present invention can effectively reduce the device voltage while improving the photoelectric efficiency of the device, and has the potential to be applied to the field of organic electroluminescent devices.
- FIG. 1 is a structural diagram of an organic electroluminescent device of the present invention
- 10 represents a glass substrate
- 20 represents an anode
- 30 represents a hole injection layer
- 40 represents a hole transport layer
- 50 represents a light emitting layer
- 60 represents an electron transport layer
- 70 represents an electron injection layer
- 80 represents a cathode.
- compound 1a (3.3g, 10.0mmol) (synthesis with reference to WO2007/149478), benzofuran-2-borate 1b (5.2g, 21.0mmol) (synthesis with reference to US2009/54454), Pd (PPh 3 ) 4 (0.58 g, 0.5 mmol), K 2 CO 3 (6.9 g, 50.0 mmol), tetrahydrofuran (30 mL), and water (5 mL) were sequentially added to the Schlenk tube. Heat to 80°C and react for 24 hours.
- compound 1c (1.5 g, 3.8 mmol) was dissolved in oxalyl chloride (20 mL), and DMF (0.5 mL) was added dropwise and heated to reflux for 6 hours.
- the oxalyl chloride was distilled off under reduced pressure, the residue was dissolved in dichloromethane, cooled to 0°C, aluminum trichloride (20.0 g, 15 mmol) was added, and gradually raised to room temperature and stirred for 24 hours.
- the reaction solution was added to hydrochloric acid (2M, 20 mL), stirred for 1 hour, and filtered to obtain a purple-red solid (1.1 g, yield 80%).
- the organic light-emitting material of the present invention is used to prepare an electroluminescent device.
- the device structure is shown in FIG.
- the transparent conductive ITO glass substrate 10 (with the anode 20 on it) is sequentially washed with detergent solution and deionized water, ethanol, acetone, and deionized water, and then treated with oxygen plasma for 30 seconds.
- a hole injection layer 30 with a thickness of 10 nm was evaporated on ITO.
- the hole injection layer was composed of compound 1 (3%) and HT1 (97%) mixed and doped.
- the compound HT1 was evaporated to form a hole transport layer 40 having a thickness of 40 nm.
- the light-emitting layer was composed of Ir(PPy) 3 (10%) and CBP (90%) mixed and doped.
- the compound AlQ 3 having a thickness of 50 nm was evaporated as the electron transport layer 60 on the light-emitting layer.
- LiF is used as the electron injection layer 70 and 100 nm Al as the device cathode 80.
- HT1 with a thickness of 10 nm was deposited as a hole injection layer, and the remaining layers were the same as those described in Example 2, and organic light-emitting devices were prepared according to the same method.
- the power efficiency of the organic electroluminescent device prepared by using the compound doping of the present invention is significantly better than that of the comparative example, and the turn-on voltage can be reduced, which is of great significance for optimizing the performance of organic optoelectronic devices.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Electroluminescent Light Sources (AREA)
- Optics & Photonics (AREA)
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Abstract
Description
发光器件 | 空穴注入层 | 最大功率效率(lm/W) | 启亮电压(V) | 发光颜色 |
实施例2 | 化合物1(3%)/HT1(97%) | 51.2 | 3.2 | 绿光 |
对比例 | HT1 | 37.8 | 3.9 | 绿光 |
Claims (10)
- 根据权利要求1所述的有机电致发光材料,其中B选自O、S、NR 1,R 1选自C1-C6的烷基、C3-C9的杂芳基、C6-C14的芳香基;X 1-X 4独立地选自N、CR 2,R 2选自氢、氘、C1-C6的烷基、C3-C9的杂芳基、C6-C14的芳香基。
- 根据权利要求2所述的有机电致发光材料,其中B选自O、S、NR 1,R 1选自甲基、苯基、甲苯基、萘基、吡啶;X 1-X 4独立地选自N、CR 2,R 2选自氢、氘、C1-C6的烷基、C3-C9的杂芳基、C6-C14的芳香基。
- 根据权利要求3所述的有机电致发光材料,其中B选自O、S、NR 1,R 1选自甲基、苯基、吡啶基;X 1-X 4独立地选自N、CH。
- 根据权利要求4所述的有机电致发光材料,其中X 1-X 4中有0-2个为N,其余的为CH。
- 有机电致发光器件,包括阴极、阳极和有机层,所述有机层为空穴注入层、空穴传输层、发光层、空穴阻挡层、电子注入层、电子传输层中的一层或多层,所述有机层中含有权利要求1-7任一所述的有机电致发光材料。
- 根据权利要求8所述的有机电致发光器件,权利要求1-7任一所述的有机电致发光材料所在层为空穴注入层或电子传输层;权利要求1-7任一所述的有机电致发光材料单独使用,或与其它化合物混合使用。
- 根据权利要求8所述的有机电致发光器件,所述有机层的总厚度为1-1000nm,所述有机层通过蒸渡或溶液法形成薄膜。
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US17/298,003 US20220115599A1 (en) | 2018-12-19 | 2019-11-02 | Organic electroluminescent material and application thereof |
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