JP3969152B2 - 有機発光素子および発光材料 - Google Patents
有機発光素子および発光材料 Download PDFInfo
- Publication number
- JP3969152B2 JP3969152B2 JP2002090590A JP2002090590A JP3969152B2 JP 3969152 B2 JP3969152 B2 JP 3969152B2 JP 2002090590 A JP2002090590 A JP 2002090590A JP 2002090590 A JP2002090590 A JP 2002090590A JP 3969152 B2 JP3969152 B2 JP 3969152B2
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- JP
- Japan
- Prior art keywords
- light
- emitting
- polymerizable
- compound
- light emitting
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- 239000000463 material Substances 0.000 title claims description 97
- 150000001875 compounds Chemical class 0.000 claims description 97
- 229920000642 polymer Polymers 0.000 claims description 50
- 239000000203 mixture Substances 0.000 claims description 38
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- 238000000576 coating method Methods 0.000 claims description 9
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- 125000002252 acyl group Chemical group 0.000 claims 1
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- 125000000524 functional group Chemical group 0.000 description 18
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- 239000000243 solution Substances 0.000 description 14
- 230000007704 transition Effects 0.000 description 13
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- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
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- HLYTZTFNIRBLNA-LNTINUHCSA-K iridium(3+);(z)-4-oxopent-2-en-2-olate Chemical compound [Ir+3].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O HLYTZTFNIRBLNA-LNTINUHCSA-K 0.000 description 3
- 229910021645 metal ion Inorganic materials 0.000 description 3
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- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical group C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 3
- FVQMJJQUGGVLEP-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOOC(C)(C)C FVQMJJQUGGVLEP-UHFFFAOYSA-N 0.000 description 2
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- SZNYYWIUQFZLLT-UHFFFAOYSA-N 2-methyl-1-(2-methylpropoxy)propane Chemical compound CC(C)COCC(C)C SZNYYWIUQFZLLT-UHFFFAOYSA-N 0.000 description 2
- VFZKVQVQOMDJEG-UHFFFAOYSA-N 2-prop-2-enoyloxypropyl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(=O)C=C VFZKVQVQOMDJEG-UHFFFAOYSA-N 0.000 description 2
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 2
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 2
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- 235000008411 Sumatra benzointree Nutrition 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
- 239000010405 anode material Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
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- 239000012975 dibutyltin dilaurate Substances 0.000 description 2
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- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 2
- JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 description 2
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- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 2
- FKUUDDGRDRPAQQ-UHFFFAOYSA-M magnesium;methoxybenzene;bromide Chemical compound [Mg+2].[Br-].COC1=CC=C[C-]=C1 FKUUDDGRDRPAQQ-UHFFFAOYSA-M 0.000 description 2
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
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- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
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- NONOKGVFTBWRLD-UHFFFAOYSA-N thioisocyanate group Chemical group S(N=C=O)N=C=O NONOKGVFTBWRLD-UHFFFAOYSA-N 0.000 description 2
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- HCXVPNKIBYLBIT-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 3,5,5-trimethylhexaneperoxoate Chemical compound CC(C)(C)CC(C)CC(=O)OOOC(C)(C)C HCXVPNKIBYLBIT-UHFFFAOYSA-N 0.000 description 1
- QEQBMZQFDDDTPN-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy benzenecarboperoxoate Chemical compound CC(C)(C)OOOC(=O)C1=CC=CC=C1 QEQBMZQFDDDTPN-UHFFFAOYSA-N 0.000 description 1
- KDGNCLDCOVTOCS-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy propan-2-yl carbonate Chemical compound CC(C)OC(=O)OOC(C)(C)C KDGNCLDCOVTOCS-UHFFFAOYSA-N 0.000 description 1
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- FYRCDEARNUVZRG-UHFFFAOYSA-N 1,1,5-trimethyl-3,3-bis(2-methylpentan-2-ylperoxy)cyclohexane Chemical compound CCCC(C)(C)OOC1(OOC(C)(C)CCC)CC(C)CC(C)(C)C1 FYRCDEARNUVZRG-UHFFFAOYSA-N 0.000 description 1
- QFMZQPDHXULLKC-UHFFFAOYSA-N 1,2-bis(diphenylphosphino)ethane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1 QFMZQPDHXULLKC-UHFFFAOYSA-N 0.000 description 1
- MSAHTMIQULFMRG-UHFFFAOYSA-N 1,2-diphenyl-2-propan-2-yloxyethanone Chemical compound C=1C=CC=CC=1C(OC(C)C)C(=O)C1=CC=CC=C1 MSAHTMIQULFMRG-UHFFFAOYSA-N 0.000 description 1
- QWQFVUQPHUKAMY-UHFFFAOYSA-N 1,2-diphenyl-2-propoxyethanone Chemical compound C=1C=CC=CC=1C(OCCC)C(=O)C1=CC=CC=C1 QWQFVUQPHUKAMY-UHFFFAOYSA-N 0.000 description 1
- AYMDJPGTQFHDSA-UHFFFAOYSA-N 1-(2-ethenoxyethoxy)-2-ethoxyethane Chemical compound CCOCCOCCOC=C AYMDJPGTQFHDSA-UHFFFAOYSA-N 0.000 description 1
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- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 description 1
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- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 0.000 description 1
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- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
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- 229940126062 Compound A Drugs 0.000 description 1
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- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
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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 1
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Landscapes
- Electroluminescent Light Sources (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2002090590A JP3969152B2 (ja) | 2001-06-21 | 2002-03-28 | 有機発光素子および発光材料 |
| AU2002345362A AU2002345362A1 (en) | 2001-06-20 | 2002-06-20 | Light emitting material and organic light-emitting device |
| DE60232415T DE60232415D1 (de) | 2001-06-20 | 2002-06-20 | Licht emittierendes material und organische leuchtdiode |
| EP02743651A EP1407501B1 (en) | 2001-06-20 | 2002-06-20 | Light emitting material and organic light-emitting device |
| AT02743651T ATE431970T1 (de) | 2001-06-20 | 2002-06-20 | Licht emittierendes material und organische leuchtdiode |
| US10/481,442 US7396598B2 (en) | 2001-06-20 | 2002-06-20 | Light emitting material and organic light-emitting device |
| KR1020037016625A KR100925409B1 (ko) | 2001-06-20 | 2002-06-20 | 발광재료 및 유기발광소자 |
| PCT/JP2002/006139 WO2003001616A2 (en) | 2001-06-20 | 2002-06-20 | Light emitting material and organic light-emitting device |
| CNB028123123A CN100440568C (zh) | 2001-06-20 | 2002-06-20 | 发光材料和有机发光装置 |
| US12/026,798 US7763365B2 (en) | 2001-06-20 | 2008-02-06 | Light emitting material and organic light-emitting device |
| US12/026,854 US7635527B2 (en) | 2001-06-20 | 2008-02-06 | Light emitting material and organic light-emitting device |
| US12/026,877 US7736757B2 (en) | 2001-06-20 | 2008-02-06 | Light emitting material and organic light-emitting device |
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| Application Number | Priority Date | Filing Date | Title |
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| JP2001188183 | 2001-06-21 | ||
| JP2001-188183 | 2001-06-21 | ||
| JP2002090590A JP3969152B2 (ja) | 2001-06-21 | 2002-03-28 | 有機発光素子および発光材料 |
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| JP2007102490A Division JP4611335B2 (ja) | 2001-06-21 | 2007-04-10 | 有機発光素子および発光材料 |
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| JP2003073666A JP2003073666A (ja) | 2003-03-12 |
| JP2003073666A5 JP2003073666A5 (enExample) | 2005-08-25 |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007273995A (ja) * | 2001-06-21 | 2007-10-18 | Showa Denko Kk | 有機発光素子および発光材料 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100353581C (zh) * | 2002-06-04 | 2007-12-05 | H·C·施塔克股份有限公司 | 磷光和发光共轭聚合物及其在电致发光组件中的应用 |
| US7090929B2 (en) * | 2002-07-30 | 2006-08-15 | E.I. Du Pont De Nemours And Company | Metallic complexes covalently bound to conjugated polymers and electronic devices containing such compositions |
| JP4666338B2 (ja) * | 2003-04-30 | 2011-04-06 | 昭和電工株式会社 | 金錯体構造を有する有機高分子発光素子材料および有機高分子発光素子 |
| GB0321781D0 (en) * | 2003-09-17 | 2003-10-15 | Toppan Printing Company Ltd | Electroluminescent device |
| KR100544138B1 (ko) | 2003-11-12 | 2006-01-23 | 삼성에스디아이 주식회사 | 액티브 매트릭스형 유기전계발광소자 |
| JP4649842B2 (ja) * | 2004-02-20 | 2011-03-16 | 富士ゼロックス株式会社 | 有機電界発光素子 |
| JP4649843B2 (ja) * | 2004-02-20 | 2011-03-16 | 富士ゼロックス株式会社 | 有機電界発光素子 |
| JP4882261B2 (ja) * | 2004-03-31 | 2012-02-22 | 住友化学株式会社 | 高分子錯体化合物およびそれを用いた高分子発光素子 |
| EP1753839B1 (en) * | 2004-05-21 | 2011-07-20 | Showa Denko K.K. | Polymer light-emitting material and organic light emitting element |
| KR100736521B1 (ko) * | 2004-06-09 | 2007-07-06 | 삼성전자주식회사 | 나노 결정 전기발광 소자 및 그의 제조방법 |
| DE102004032527A1 (de) * | 2004-07-06 | 2006-02-02 | Covion Organic Semiconductors Gmbh | Elektrolumineszierende Polymere |
| JPWO2006092943A1 (ja) | 2005-03-02 | 2008-08-07 | 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 |
| EP1885009A4 (en) * | 2005-05-17 | 2009-12-30 | Sumitomo Chemical Co | POLYMERIC COMPOSITION FOR ORGANIC ELECTROLUMINESCENCE |
| JP2007257897A (ja) * | 2006-03-20 | 2007-10-04 | Seiko Epson Corp | 発光素子の製造方法、発光装置の製造方法および電子機器の製造方法 |
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| KR101282400B1 (ko) * | 2006-08-24 | 2013-07-04 | 한국과학기술원 | 유기 발광 표시 장치 |
| JP5332614B2 (ja) | 2006-09-08 | 2013-11-06 | 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、照明装置及び表示装置 |
| US7851579B2 (en) * | 2006-12-11 | 2010-12-14 | General Electric Company | Carbazolyl polymers for organic electronic devices |
| EP2112702B2 (en) * | 2007-02-15 | 2017-12-13 | Mitsubishi Chemical Corporation | Method for manufacturing an organic electroluminescence device |
| JP2008280524A (ja) * | 2007-04-13 | 2008-11-20 | Hitachi Chem Co Ltd | 有機エレクトロニクス用材料、有機エレクトロニクス素子および有機エレクトロルミネセンス素子 |
| JP2007284684A (ja) * | 2007-05-28 | 2007-11-01 | Idemitsu Kosan 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 |
| WO2008146838A1 (ja) | 2007-05-30 | 2008-12-04 | Konica Minolta Holdings, Inc. | 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 |
| US8569087B2 (en) * | 2007-11-12 | 2013-10-29 | Konica Minolta Holdings, Inc. | Method for manufacturing organic electronic element |
| JP2009152033A (ja) * | 2007-12-20 | 2009-07-09 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子の製造方法、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 |
| JP5293120B2 (ja) * | 2008-11-28 | 2013-09-18 | 住友化学株式会社 | 有機エレクトロルミネッセンス素子およびその製造方法 |
| DE102010046412B4 (de) * | 2010-09-23 | 2022-01-13 | Merck Patent Gmbh | Metall-Ligand Koordinationsverbindungen |
| EP2543671A1 (de) * | 2011-07-08 | 2013-01-09 | cynora GmbH | Querverknüpfung und Stabilisierung von organischen Metallkomplexen in Netzwerken |
| JP2014215416A (ja) * | 2013-04-25 | 2014-11-17 | Jsr株式会社 | 着色組成物、着色硬化膜及び表示素子 |
-
2002
- 2002-03-28 JP JP2002090590A patent/JP3969152B2/ja not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007273995A (ja) * | 2001-06-21 | 2007-10-18 | Showa Denko Kk | 有機発光素子および発光材料 |
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| JP2003073666A (ja) | 2003-03-12 |
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