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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- 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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- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
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- 239000004973 liquid crystal related substance Substances 0.000 description 1
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- 239000000126 substance Substances 0.000 description 1
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- C07D209/56—Ring systems containing three or more rings
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- C07D209/82—Carbazoles; Hydrogenated carbazoles
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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 |
WO2016017760A1 (ja) | 2014-07-31 | 2016-02-04 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス素子、発光性薄膜、表示装置及び照明装置 |
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 |
WO2019073075A1 (en) * | 2017-10-13 | 2019-04-18 | Cynora Gmbh | 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 |
WO2020035365A1 (en) | 2018-08-13 | 2020-02-20 | Cynora Gmbh | Organic molecules for optoelectronic devices |
EP3674299B1 (en) * | 2018-12-28 | 2021-11-24 | cynora GmbH | Organic molecules for optoelectronic devices |
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Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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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EP2270895A3 (en) | 1999-12-01 | 2011-03-30 | The Trustees of Princeton University | Complexes for OLEDs |
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 |
KR20060096980A (ko) * | 2003-07-31 | 2006-09-13 | 미쓰비시 가가꾸 가부시키가이샤 | 화합물, 전하 수송 재료 및 유기 전계 발광 소자 |
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 |
JP4810669B2 (ja) * | 2004-11-25 | 2011-11-09 | 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、表示装置及び照明装置 |
US8178215B2 (en) * | 2004-12-10 | 2012-05-15 | Pioneer Corporation | Organic compound containing at least two carbazolyl-substituted phenyl structures; charge-transporting material and organic el element containing the compound |
JP5098177B2 (ja) * | 2005-01-25 | 2012-12-12 | パイオニア株式会社 | 有機化合物、電荷輸送材料及び有機電界発光素子 |
KR20070009306A (ko) * | 2005-07-15 | 2007-01-18 | 삼성에스디아이 주식회사 | 백색 유기 발광 소자의 제조 방법 |
JP5168840B2 (ja) * | 2005-08-04 | 2013-03-27 | 三菱化学株式会社 | 電荷輸送材料、有機電界発光素子用組成物及び有機電界発光素子 |
JP4871607B2 (ja) * | 2006-02-23 | 2012-02-08 | 富士フイルム株式会社 | 有機電界発光素子 |
-
2009
- 2009-02-05 WO PCT/JP2009/051973 patent/WO2009119163A1/ja active Application Filing
- 2009-02-05 KR KR1020107023069A patent/KR101598931B1/ko active IP Right Grant
- 2009-02-05 JP JP2010505426A patent/JP5421242B2/ja active Active
- 2009-02-05 US US12/934,078 patent/US8859109B2/en active Active
- 2009-02-05 CN CN200980106721.8A patent/CN101959857B/zh active Active
- 2009-02-05 EP EP09724917.1A patent/EP2272828B1/en active Active
- 2009-02-11 TW TW098104354A patent/TWI447206B/zh not_active IP Right Cessation
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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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US8859109B2 (en) | 2014-10-14 |
KR101598931B1 (ko) | 2016-03-02 |
EP2272828B1 (en) | 2018-06-27 |
JPWO2009119163A1 (ja) | 2011-07-21 |
EP2272828A1 (en) | 2011-01-12 |
JP5421242B2 (ja) | 2014-02-19 |
EP2272828A4 (en) | 2012-04-18 |
KR20100135815A (ko) | 2010-12-27 |
TW200946641A (en) | 2009-11-16 |
WO2009119163A1 (ja) | 2009-10-01 |
TWI447206B (zh) | 2014-08-01 |
CN101959857A (zh) | 2011-01-26 |
US20110024735A1 (en) | 2011-02-03 |
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