CN101959857B - 有机场致发光元件用化合物及使用其的有机场致发光元件 - Google Patents
有机场致发光元件用化合物及使用其的有机场致发光元件 Download PDFInfo
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- CN101959857B CN101959857B CN200980106721.8A CN200980106721A CN101959857B CN 101959857 B CN101959857 B CN 101959857B CN 200980106721 A CN200980106721 A CN 200980106721A CN 101959857 B CN101959857 B CN 101959857B
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 58
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 239000000463 material Substances 0.000 abstract description 46
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 abstract description 11
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 abstract 1
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- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 26
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- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 6
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- -1 carbazole compound Chemical class 0.000 description 5
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
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- 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 5
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- HIHYAKDOWUFGBK-UHFFFAOYSA-N Brc1cc(Br)cc(-c2ccccc2)c1 Chemical compound Brc1cc(Br)cc(-c2ccccc2)c1 HIHYAKDOWUFGBK-UHFFFAOYSA-N 0.000 description 1
- 241000284156 Clerodendrum quadriloculare Species 0.000 description 1
- 229910052693 Europium Inorganic materials 0.000 description 1
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- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 1
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- 238000005859 coupling reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000006056 electrooxidation reaction Methods 0.000 description 1
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 1
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
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- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
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- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
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- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000003550 marker Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
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- 125000002950 monocyclic group Chemical group 0.000 description 1
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- 229910000510 noble metal Inorganic materials 0.000 description 1
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- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 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
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- 229910052697 platinum Inorganic materials 0.000 description 1
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- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
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- 230000000452 restraining effect Effects 0.000 description 1
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- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- GVIJJXMXTUZIOD-UHFFFAOYSA-N thianthrene Chemical compound C1=CC=C2SC3=CC=CC=C3SC2=C1 GVIJJXMXTUZIOD-UHFFFAOYSA-N 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
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- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
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- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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Abstract
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JP5330429B2 (ja) * | 2011-03-08 | 2013-10-30 | 株式会社東芝 | 有機電界発光素子、表示装置および照明装置 |
JPWO2013069242A1 (ja) | 2011-11-07 | 2015-04-02 | 出光興産株式会社 | 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 |
TWI585091B (zh) * | 2012-03-30 | 2017-06-01 | 新日鐵住金化學股份有限公司 | Organic electroluminescent elements |
US9013997B2 (en) * | 2012-06-01 | 2015-04-21 | Broadcom Corporation | System for performing distributed data cut-through |
KR102218412B1 (ko) * | 2014-07-31 | 2021-02-22 | 메르크 파텐트 게엠베하 | 유기 일렉트로루미네센스 소자, 발광성 박막, 표시 장치 및 조명 장치 |
KR101997057B1 (ko) * | 2016-05-27 | 2019-07-08 | 주식회사 엘지화학 | 유기 발광 소자 |
JP2018104359A (ja) * | 2016-12-27 | 2018-07-05 | 株式会社半導体エネルギー研究所 | 有機化合物、発光素子、発光装置、電子機器、および照明装置 |
KR102270125B1 (ko) * | 2017-04-13 | 2021-06-25 | 시노라 게엠베하 | 유기 분자, 특히 광전자 장치에 사용하기 위한 유기 분자 |
EP3399004B1 (de) * | 2017-05-04 | 2019-08-21 | Cynora Gmbh | Organische moleküle, insbesondere zur verwendung in optoelektronischen vorrichtungen |
EP3459943B1 (en) * | 2017-09-26 | 2020-07-22 | Cynora Gmbh | Pyrimidine-based organic molecules, in particular for use in optoelectronic devices |
EP3694850B1 (en) * | 2017-10-13 | 2023-10-11 | Samsung Display Co., Ltd. | Organic molecules for use in optoelectronic devices |
KR102400585B1 (ko) * | 2017-10-27 | 2022-05-23 | 삼성디스플레이 주식회사 | 함질소 화합물 및 이를 포함하는 유기 전계 발광 소자 |
WO2020020602A1 (en) * | 2018-07-22 | 2020-01-30 | Cynora Gmbh | Organic molecules for optoelectronic devices |
EP3837254B1 (en) * | 2018-08-13 | 2022-10-19 | Samsung Display Co., Ltd. | Organic molecules for optoelectronic devices |
EP3674299B1 (en) * | 2018-12-28 | 2021-11-24 | cynora GmbH | Organic molecules for optoelectronic devices |
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CN1728908A (zh) * | 2004-06-25 | 2006-02-01 | 三星Sdi株式会社 | 有机电致发光装置 |
CN101087776A (zh) * | 2004-12-24 | 2007-12-12 | 先锋公司 | 有机化合物、电荷传输材料和有机电致发光元件 |
CN101107244A (zh) * | 2005-01-25 | 2008-01-16 | 先锋公司 | 有机化合物、电荷传输材料和有机电致发光元件 |
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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 |
JP2003031371A (ja) * | 2001-07-17 | 2003-01-31 | Mitsubishi Chemicals Corp | 有機電界発光素子及び青色発光素子 |
JP4552382B2 (ja) | 2003-03-06 | 2010-09-29 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子、有機エレクトロルミネッセンス素子材料、表示装置及び照明装置 |
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JP4351935B2 (ja) | 2004-03-10 | 2009-10-28 | 富士フイルム株式会社 | 有機電界発光素子 |
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2009
- 2009-02-05 JP JP2010505426A patent/JP5421242B2/ja active Active
- 2009-02-05 WO PCT/JP2009/051973 patent/WO2009119163A1/ja active Application Filing
- 2009-02-05 CN CN200980106721.8A patent/CN101959857B/zh active Active
- 2009-02-05 EP EP09724917.1A patent/EP2272828B1/en active Active
- 2009-02-05 KR KR1020107023069A patent/KR101598931B1/ko active IP Right Grant
- 2009-02-05 US US12/934,078 patent/US8859109B2/en active Active
- 2009-02-11 TW TW098104354A patent/TWI447206B/zh not_active IP Right Cessation
Patent Citations (3)
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CN1728908A (zh) * | 2004-06-25 | 2006-02-01 | 三星Sdi株式会社 | 有机电致发光装置 |
CN101087776A (zh) * | 2004-12-24 | 2007-12-12 | 先锋公司 | 有机化合物、电荷传输材料和有机电致发光元件 |
CN101107244A (zh) * | 2005-01-25 | 2008-01-16 | 先锋公司 | 有机化合物、电荷传输材料和有机电致发光元件 |
Also Published As
Publication number | Publication date |
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TWI447206B (zh) | 2014-08-01 |
EP2272828B1 (en) | 2018-06-27 |
JPWO2009119163A1 (ja) | 2011-07-21 |
TW200946641A (en) | 2009-11-16 |
EP2272828A1 (en) | 2011-01-12 |
US20110024735A1 (en) | 2011-02-03 |
KR101598931B1 (ko) | 2016-03-02 |
JP5421242B2 (ja) | 2014-02-19 |
US8859109B2 (en) | 2014-10-14 |
KR20100135815A (ko) | 2010-12-27 |
CN101959857A (zh) | 2011-01-26 |
EP2272828A4 (en) | 2012-04-18 |
WO2009119163A1 (ja) | 2009-10-01 |
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