CN102341396A - 磷光发光元件用材料及使用其的有机电致发光元件 - Google Patents
磷光发光元件用材料及使用其的有机电致发光元件 Download PDFInfo
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- CN102341396A CN102341396A CN2010800093190A CN201080009319A CN102341396A CN 102341396 A CN102341396 A CN 102341396A CN 2010800093190 A CN2010800093190 A CN 2010800093190A CN 201080009319 A CN201080009319 A CN 201080009319A CN 102341396 A CN102341396 A CN 102341396A
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- 239000000463 material Substances 0.000 title claims abstract description 89
- PJVZQNVOUCOJGE-CALCHBBNSA-N chembl289853 Chemical compound N1([C@H]2CC[C@H](O2)N2[C]3C=CC=CC3=C3C2=C11)C2=CC=C[CH]C2=C1C1=C3C(=O)N(C)C1=O PJVZQNVOUCOJGE-CALCHBBNSA-N 0.000 claims abstract description 32
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 19
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 15
- 239000000758 substrate Substances 0.000 claims abstract description 14
- 239000002019 doping agent Substances 0.000 claims abstract description 12
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims abstract description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 2
- 239000010410 layer Substances 0.000 claims description 131
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 51
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- 239000012044 organic layer Substances 0.000 claims description 30
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 27
- 125000003118 aryl group Chemical group 0.000 claims description 26
- 230000005540 biological transmission Effects 0.000 claims description 24
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- 238000009833 condensation Methods 0.000 claims description 14
- 230000005494 condensation Effects 0.000 claims description 14
- 125000004122 cyclic group Chemical group 0.000 claims description 9
- 230000000903 blocking effect Effects 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
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- 150000001875 compounds Chemical class 0.000 abstract description 55
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract description 2
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- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 abstract 1
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- 238000003756 stirring Methods 0.000 description 17
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- 230000000052 comparative effect Effects 0.000 description 7
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 229910052741 iridium Inorganic materials 0.000 description 6
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- 125000001424 substituent group Chemical group 0.000 description 6
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- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 5
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- ZXAQFYZQHPGMMN-BZSJEYESSA-N (3R)-3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-phenylcyclohexane-1-carboxamide Chemical compound C1C[C@H](CC(C1)C(=O)NC2=CC=CC=C2)OC3=CC(=CC(=N3)C(F)(F)F)CN ZXAQFYZQHPGMMN-BZSJEYESSA-N 0.000 description 4
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 4
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- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 4
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
- 125000002524 organometallic group Chemical group 0.000 description 4
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 238000001269 time-of-flight mass spectrometry Methods 0.000 description 4
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 4
- XIYPPJVLAAXYAB-UHFFFAOYSA-N 2-bromo-6-phenylpyridine Chemical compound BrC1=CC=CC(C=2C=CC=CC=2)=N1 XIYPPJVLAAXYAB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
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- 241001597008 Nomeidae Species 0.000 description 3
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- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 3
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- LQWHPYPUHPQSRX-UHFFFAOYSA-N 1,1'-biphenyl;pyridine Chemical compound C1=CC=NC=C1.C1=CC=CC=C1C1=CC=CC=C1 LQWHPYPUHPQSRX-UHFFFAOYSA-N 0.000 description 2
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- IYDMICQAKLQHLA-UHFFFAOYSA-N 1-phenylnaphthalene Chemical compound C1=CC=CC=C1C1=CC=CC2=CC=CC=C12 IYDMICQAKLQHLA-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
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- 0 Cc1cccc(N(c2ccccc2)c(cc2)ccc2-c(cc2)ccc2-[n]2c(cc(c3ccccc3[n]3-c(cc4)ccc4-c(cc4)ccc4N(c4ccccc4)c4cccc(*)c4)c3c3)c3c3ccccc23)c1 Chemical compound Cc1cccc(N(c2ccccc2)c(cc2)ccc2-c(cc2)ccc2-[n]2c(cc(c3ccccc3[n]3-c(cc4)ccc4-c(cc4)ccc4N(c4ccccc4)c4cccc(*)c4)c3c3)c3c3ccccc23)c1 0.000 description 1
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- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
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- 229940054051 antipsychotic indole derivative Drugs 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
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- 230000018044 dehydration Effects 0.000 description 1
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- 230000000694 effects Effects 0.000 description 1
- 230000005518 electrochemistry Effects 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
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- 230000005281 excited state Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 230000005525 hole transport Effects 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- ZKYQRJXGGLVQML-UHFFFAOYSA-N iridium(3+);2-phenylpyridine Chemical compound [Ir+3].C1=CC=CC=C1C1=CC=CC=N1 ZKYQRJXGGLVQML-UHFFFAOYSA-N 0.000 description 1
- RTRAMYYYHJZWQK-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1 RTRAMYYYHJZWQK-UHFFFAOYSA-N 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- GIFAOSNIDJTPNL-UHFFFAOYSA-N n-phenyl-n-(2-phenylphenyl)naphthalen-1-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=CC=C1C1=CC=CC=C1 GIFAOSNIDJTPNL-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 150000005054 naphthyridines Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000005053 phenanthridines Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- JOVOSQBPPZZESK-UHFFFAOYSA-N phenylhydrazine hydrochloride Chemical compound Cl.NNC1=CC=CC=C1 JOVOSQBPPZZESK-UHFFFAOYSA-N 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 1
- 229920000548 poly(silane) polymer Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 150000003252 quinoxalines Chemical class 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N sec-butylidene Natural products CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 235000019798 tripotassium phosphate Nutrition 0.000 description 1
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- C07D487/02—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 two hetero rings
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- C07D487/22—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 four or more hetero rings
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Abstract
Description
Claims (8)
Applications Claiming Priority (3)
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JP2009085709 | 2009-03-31 | ||
JP2009-085709 | 2009-03-31 | ||
PCT/JP2010/055115 WO2010113726A1 (ja) | 2009-03-31 | 2010-03-24 | 燐光発光素子用材料及びこれを用いた有機電界発光素子 |
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CN102341396B CN102341396B (zh) | 2014-03-12 |
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US (1) | US8389131B2 (zh) |
EP (1) | EP2415772B1 (zh) |
JP (1) | JP5027947B2 (zh) |
KR (1) | KR101302099B1 (zh) |
CN (1) | CN102341396B (zh) |
TW (1) | TWI471405B (zh) |
WO (1) | WO2010113726A1 (zh) |
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CN107531716A (zh) * | 2015-05-19 | 2018-01-02 | 罗门哈斯电子材料韩国有限公司 | 发磷光的主体材料和包含所述发磷光的主体材料的有机电致发光装置 |
CN107771206A (zh) * | 2015-06-26 | 2018-03-06 | 罗门哈斯电子材料韩国有限公司 | 多组分主体材料和包括此材料的有机电致发光装置 |
CN108148088A (zh) * | 2016-11-21 | 2018-06-12 | 环球展览公司 | 有机电致发光材料和装置 |
CN109942581A (zh) * | 2017-12-21 | 2019-06-28 | 武汉尚赛光电科技有限公司 | 二氢吲哚[3,2-a]咔唑与吡啶类衍生物及其制备方法、应用和器件 |
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Publication number | Priority date | Publication date | Assignee | Title |
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KR101477613B1 (ko) * | 2009-03-31 | 2014-12-30 | 롬엔드하스전자재료코리아유한회사 | 신규한 유기 전자재료용 화합물 및 이를 포함하는 유기 전자 소자 |
CN103229324B (zh) * | 2010-11-25 | 2016-08-10 | 新日铁住金化学株式会社 | 有机电致发光元件 |
JP6271417B2 (ja) * | 2011-04-13 | 2018-01-31 | メルク パテント ゲーエムベーハー | 電子素子のための材料 |
KR101497124B1 (ko) * | 2011-11-28 | 2015-03-06 | 덕산네오룩스 주식회사 | 유기전기소자용 화합물, 이를 포함하는 유기전기소자 및 그 전자 장치 |
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US20160276599A1 (en) * | 2012-01-18 | 2016-09-22 | Duk San Neolux Co., Ltd. | Compound for organic electric element, organic electric element comprising the same and electronic device thereof |
WO2013133575A1 (ko) * | 2012-03-09 | 2013-09-12 | 주식회사 두산 | 신규 화합물 및 이를 포함하는 유기 전계 발광 소자 |
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KR101603372B1 (ko) * | 2012-09-19 | 2016-03-14 | 주식회사 두산 | 에틸렌 고리가 형성된 카바졸계 유기발광 화합물 및 이를 이용한 유기 전계 발광 소자 |
US9825239B2 (en) * | 2012-10-18 | 2017-11-21 | Toray Industries, Inc. | Benzindolocarbazole derivative, light-emitting element material produced using same, and light-emitting element |
EP2933851B1 (en) * | 2012-12-17 | 2017-05-10 | Nippon Steel & Sumikin Chemical Co., Ltd. | Organic electroluminescent device |
JP2015020953A (ja) * | 2013-07-17 | 2015-02-02 | 三星ディスプレイ株式會社Samsung Display Co.,Ltd. | ビピリジン部位を有するインドロカルバゾール誘導体及びそれを用いた有機電界発光素子 |
JP2015118958A (ja) * | 2013-12-16 | 2015-06-25 | 三星ディスプレイ株式會社Samsung Display Co.,Ltd. | 有機エレクトロルミネッセンス素子用材料及びそれを用いた有機エレクトロルミネッセンス素子 |
KR101802861B1 (ko) | 2014-02-14 | 2017-11-30 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
KR101920101B1 (ko) * | 2014-04-24 | 2018-11-19 | 주식회사 두산 | 신규 화합물 및 이를 포함하는 유기 전계 발광 소자 |
WO2016208873A1 (en) | 2015-06-26 | 2016-12-29 | Rohm And Haas Electronic Materials Korea Ltd. | Multi-component host material and organic electroluminescent device comprising the same |
CN112830900B (zh) * | 2021-01-07 | 2022-12-02 | 吉林奥来德光电材料股份有限公司 | 磷光化合物及其制备方法和包含它的有机电致发光器件 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2007063754A1 (ja) * | 2005-12-01 | 2007-06-07 | Nippon Steel Chemical Co., Ltd. | 有機電界発光素子用化合物及び有機電界発光素子 |
WO2008056746A1 (fr) * | 2006-11-09 | 2008-05-15 | Nippon Steel Chemical Co., Ltd. | Composé pour un dispositif électroluminescent organique et dispositif électroluminescent organique |
WO2009136596A1 (ja) * | 2008-05-08 | 2009-11-12 | 新日鐵化学株式会社 | 有機電界発光素子 |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5942340A (en) * | 1997-10-02 | 1999-08-24 | Xerox Corporation | Indolocarbazole electroluminescent devices |
US5952115A (en) | 1997-10-02 | 1999-09-14 | Xerox Corporation | Electroluminescent devices |
EP1933395B2 (en) | 1999-12-01 | 2019-08-07 | The Trustees of Princeton University | Complexes of form L2IrX |
JP2001313178A (ja) | 2000-04-28 | 2001-11-09 | Pioneer Electronic Corp | 有機エレクトロルミネッセンス素子 |
WO2007145975A2 (en) * | 2006-06-05 | 2007-12-21 | E. I. Du Pont De Nemours And Company | Process for forming an organic light-emitting diode and devices made by the process |
TWI468489B (zh) * | 2007-05-29 | 2015-01-11 | Nippon Steel & Sumikin Chem Co | Organic electroluminescent element compounds and organic electroluminescent elements |
KR101005160B1 (ko) * | 2007-05-30 | 2011-01-04 | 신닛테츠가가쿠 가부시키가이샤 | 유기 전계 발광 소자용 화합물 및 유기 전계 발광 소자 |
TWI472074B (zh) * | 2008-03-17 | 2015-02-01 | Nippon Steel & Sumikin Chem Co | Organic electroluminescent elements |
-
2010
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- 2010-03-24 EP EP10758500.2A patent/EP2415772B1/en active Active
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- 2010-03-24 US US13/255,193 patent/US8389131B2/en active Active
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Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2007063754A1 (ja) * | 2005-12-01 | 2007-06-07 | Nippon Steel Chemical Co., Ltd. | 有機電界発光素子用化合物及び有機電界発光素子 |
WO2008056746A1 (fr) * | 2006-11-09 | 2008-05-15 | Nippon Steel Chemical Co., Ltd. | Composé pour un dispositif électroluminescent organique et dispositif électroluminescent organique |
WO2009136596A1 (ja) * | 2008-05-08 | 2009-11-12 | 新日鐵化学株式会社 | 有機電界発光素子 |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107531716A (zh) * | 2015-05-19 | 2018-01-02 | 罗门哈斯电子材料韩国有限公司 | 发磷光的主体材料和包含所述发磷光的主体材料的有机电致发光装置 |
CN107531716B (zh) * | 2015-05-19 | 2021-06-22 | 罗门哈斯电子材料韩国有限公司 | 发磷光的主体材料和包含所述发磷光的主体材料的有机电致发光装置 |
CN107771206A (zh) * | 2015-06-26 | 2018-03-06 | 罗门哈斯电子材料韩国有限公司 | 多组分主体材料和包括此材料的有机电致发光装置 |
CN108148088A (zh) * | 2016-11-21 | 2018-06-12 | 环球展览公司 | 有机电致发光材料和装置 |
CN109942581A (zh) * | 2017-12-21 | 2019-06-28 | 武汉尚赛光电科技有限公司 | 二氢吲哚[3,2-a]咔唑与吡啶类衍生物及其制备方法、应用和器件 |
CN109942581B (zh) * | 2017-12-21 | 2020-09-04 | 武汉尚赛光电科技有限公司 | 二氢吲哚[3,2-a]咔唑与吡啶类衍生物及其制备方法、应用和器件 |
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Publication number | Publication date |
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KR101302099B1 (ko) | 2013-08-30 |
EP2415772B1 (en) | 2018-05-16 |
US20110315975A1 (en) | 2011-12-29 |
US8389131B2 (en) | 2013-03-05 |
WO2010113726A1 (ja) | 2010-10-07 |
TWI471405B (zh) | 2015-02-01 |
TW201105771A (en) | 2011-02-16 |
KR20110134923A (ko) | 2011-12-15 |
EP2415772A1 (en) | 2012-02-08 |
CN102341396B (zh) | 2014-03-12 |
JPWO2010113726A1 (ja) | 2012-10-11 |
EP2415772A4 (en) | 2013-05-29 |
JP5027947B2 (ja) | 2012-09-19 |
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