JP2010515260A5 - - Google Patents
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- Publication number
- JP2010515260A5 JP2010515260A5 JP2009544122A JP2009544122A JP2010515260A5 JP 2010515260 A5 JP2010515260 A5 JP 2010515260A5 JP 2009544122 A JP2009544122 A JP 2009544122A JP 2009544122 A JP2009544122 A JP 2009544122A JP 2010515260 A5 JP2010515260 A5 JP 2010515260A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- copolymer
- hole transport
- dialkylfluorene
- electroluminescent
- 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.)
- Pending
Links
- 239000000463 material Substances 0.000 claims description 62
- 229920001577 copolymer Polymers 0.000 claims description 38
- 230000005525 hole transport Effects 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 31
- 229920000642 polymer Polymers 0.000 claims description 21
- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical compound C12=C3C(C4=C56)=C7C8=C5C5=C9C%10=C6C6=C4C1=C1C4=C6C6=C%10C%10=C9C9=C%11C5=C8C5=C8C7=C3C3=C7C2=C1C1=C2C4=C6C4=C%10C6=C9C9=C%11C5=C5C8=C3C3=C7C1=C1C2=C4C6=C2C9=C5C3=C12 XMWRBQBLMFGWIX-UHFFFAOYSA-N 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 12
- 229910003472 fullerene Inorganic materials 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 238000002347 injection Methods 0.000 claims description 10
- 239000007924 injection Substances 0.000 claims description 10
- 239000007788 liquid Substances 0.000 claims description 9
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 8
- 125000004407 fluoroaryl group Chemical group 0.000 claims description 8
- 229920001940 conductive polymer Polymers 0.000 claims description 7
- -1 polycyclic aromatic compound Chemical class 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- 235000010290 biphenyl Nutrition 0.000 claims description 6
- 239000004305 biphenyl Substances 0.000 claims description 6
- 125000006616 biphenylamine group Chemical group 0.000 claims description 6
- 239000000178 monomer Substances 0.000 claims description 6
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 claims description 6
- IVOCRVRJPIXBHQ-UHFFFAOYSA-N 9,9-bis(1-phenylprop-2-enyl)fluorene Chemical compound C12=CC=CC=C2C2=CC=CC=C2C1(C(C=C)C=1C=CC=CC=1)C(C=C)C1=CC=CC=C1 IVOCRVRJPIXBHQ-UHFFFAOYSA-N 0.000 claims description 4
- KMNWMVDEUAICJH-UHFFFAOYSA-N 9,9-bis(2-phenylethenyl)fluorene Chemical compound C=1C=CC=CC=1C=CC1(C2=CC=CC=C2C2=CC=CC=C21)C=CC1=CC=CC=C1 KMNWMVDEUAICJH-UHFFFAOYSA-N 0.000 claims description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 230000008021 deposition Effects 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- TULWUZJYDBGXMY-UHFFFAOYSA-N tellurophene Chemical compound [Te]1C=CC=C1 TULWUZJYDBGXMY-UHFFFAOYSA-N 0.000 claims description 4
- BKTWCYHMBXXJBX-UHFFFAOYSA-N 2-ethenyl-n,n-diphenylaniline Chemical compound C=CC1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 BKTWCYHMBXXJBX-UHFFFAOYSA-N 0.000 claims description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000000732 arylene group Chemical group 0.000 claims description 2
- 229920006037 cross link polymer Polymers 0.000 claims description 2
- 238000005401 electroluminescence Methods 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 229920000767 polyaniline Polymers 0.000 claims description 2
- 229920000128 polypyrrole Polymers 0.000 claims description 2
- 229920000123 polythiophene Polymers 0.000 claims description 2
- 239000002243 precursor Substances 0.000 claims description 2
- 229910052711 selenium Inorganic materials 0.000 claims description 2
- MABNMNVCOAICNO-UHFFFAOYSA-N selenophene Chemical compound C=1C=C[se]C=1 MABNMNVCOAICNO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 229930192474 thiophene Natural products 0.000 claims description 2
- 238000007740 vapor deposition Methods 0.000 claims description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US87772306P | 2006-12-29 | 2006-12-29 | |
| PCT/US2007/026516 WO2008082665A2 (en) | 2006-12-29 | 2007-12-28 | Process for forming an organic light-emitting diode and devices made by the process |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2010515260A JP2010515260A (ja) | 2010-05-06 |
| JP2010515260A5 true JP2010515260A5 (enExample) | 2011-02-17 |
Family
ID=39387396
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009544122A Pending JP2010515260A (ja) | 2006-12-29 | 2007-12-28 | 有機発光ダイオードの形成方法およびこの方法によって製造されるデバイス |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US20080166566A1 (enExample) |
| EP (1) | EP2122707A2 (enExample) |
| JP (1) | JP2010515260A (enExample) |
| KR (1) | KR20090104079A (enExample) |
| WO (1) | WO2008082665A2 (enExample) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5061184B2 (ja) * | 2006-06-05 | 2012-10-31 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 有機発光ダイオードの形成方法、およびその方法によって製造されたデバイス |
| US20090140219A1 (en) * | 2007-07-13 | 2009-06-04 | Air Products And Chemicals, Inc. | Selenium Containing Electrically Conductive Polymers and Method of Making Electrically Conductive Polymers |
| US8343381B1 (en) * | 2008-05-16 | 2013-01-01 | E I Du Pont De Nemours And Company | Hole transport composition |
| US20120187382A1 (en) * | 2008-12-22 | 2012-07-26 | E.I. Dupont De Nemours And Company | Electronic devices having long lifetime |
| US8759818B2 (en) | 2009-02-27 | 2014-06-24 | E I Du Pont De Nemours And Company | Deuterated compounds for electronic applications |
| WO2010114583A1 (en) * | 2009-04-03 | 2010-10-07 | E. I. Du Pont De Nemours And Company | Electroactive materials |
| KR20120038413A (ko) * | 2009-06-23 | 2012-04-23 | 스미또모 가가꾸 가부시키가이샤 | 유기 전계발광 소자 |
| EP2455992A4 (en) * | 2009-07-14 | 2015-07-22 | Sumitomo Chemical Co | ORGANIC ELECTROLUMINESCENT ELEMENT AND LIGHT EMITTING COMPOSITION HAVING HIGH MOLECULAR WEIGHT |
| EP2471123A2 (en) * | 2009-08-24 | 2012-07-04 | E. I. du Pont de Nemours and Company | Organic light-emitting diode luminaires |
| CN102484217A (zh) * | 2009-08-24 | 2012-05-30 | E.I.内穆尔杜邦公司 | 有机发光二极管灯具 |
| KR20120066025A (ko) * | 2009-08-24 | 2012-06-21 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 유기 발광 다이오드 조명기구 |
| CN102484214A (zh) * | 2009-08-24 | 2012-05-30 | E.I.内穆尔杜邦公司 | 有机发光二极管灯具 |
| JP2013502701A (ja) * | 2009-08-24 | 2013-01-24 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 有機発光ダイオード照明器具 |
| EP2471120A2 (en) * | 2009-08-24 | 2012-07-04 | E. I. du Pont de Nemours and Company | Organic light-emitting diode luminaires |
| CN102510889B (zh) | 2009-09-29 | 2015-11-25 | E.I.内穆尔杜邦公司 | 用于发光应用的氘代化合物 |
| EP2493887A4 (en) | 2009-10-29 | 2013-06-19 | Du Pont | DEUTERIZED CONNECTIONS FOR ELECTRONIC APPLICATIONS |
| EP2354207B1 (en) * | 2010-01-20 | 2016-10-12 | Hitachi, Ltd. | Organic luminescent materials, coating solution using same for organic emitting layer, organic light emitting device using coating solution and light source device using organic light emitting device |
| KR101708847B1 (ko) * | 2010-04-08 | 2017-02-22 | 삼성디스플레이 주식회사 | 유기 발광 표시 장치 및 이의 제조 방법 |
| WO2012011412A1 (ja) * | 2010-07-22 | 2012-01-26 | 住友化学株式会社 | 有機エレクトロルミネッセンス素子 |
| EP2655547A1 (en) | 2010-12-20 | 2013-10-30 | E.I. Du Pont De Nemours And Company | Compositions for electronic applications |
| GB201105582D0 (en) * | 2011-04-01 | 2011-05-18 | Cambridge Display Tech Ltd | Organic light-emitting device and method |
| EP2610240A1 (en) * | 2011-12-28 | 2013-07-03 | Solvay Sa | Crosslinkable arylamine compounds |
| JP5321700B2 (ja) * | 2012-01-17 | 2013-10-23 | 三菱化学株式会社 | 有機電界発光素子、有機ｅｌ照明および有機ｅｌ表示装置 |
| GB201200823D0 (en) | 2012-01-18 | 2012-02-29 | Cambridge Display Tech Ltd | Electroluminescence |
| JP5955660B2 (ja) * | 2012-06-20 | 2016-07-20 | 住友化学株式会社 | 組成物、高分子化合物およびそれらを用いた発光素子 |
| US20140346468A1 (en) * | 2013-05-27 | 2014-11-27 | Samsung Display Co., Ltd. | Organic light emitting display device having a channel in pixel defining layer |
| JP5569630B2 (ja) * | 2013-07-16 | 2014-08-13 | 三菱化学株式会社 | 有機電界発光素子、有機ｅｌ照明および有機ｅｌ表示装置 |
| CN103715367B (zh) * | 2013-12-24 | 2016-03-30 | 合肥京东方光电科技有限公司 | 有机发光二极管及电子设备 |
| JP6567856B2 (ja) * | 2014-04-18 | 2019-08-28 | 株式会社半導体エネルギー研究所 | 発光装置 |
| CN106019760B (zh) * | 2016-07-07 | 2018-08-10 | 熊昆立 | 全彩色电子纸的生产方法 |
| KR102057763B1 (ko) | 2016-11-25 | 2019-12-19 | 주식회사 엘지화학 | 플루오렌 유도체, 이를 이용한 유기 발광 소자 및 이의 제조방법 |
| CN108059863B (zh) * | 2018-01-02 | 2019-12-03 | 广东至诚紫光新材料有限公司 | 一种环保导电涂料及其制备方法 |
Family Cites Families (46)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3282875A (en) * | 1964-07-22 | 1966-11-01 | Du Pont | Fluorocarbon vinyl ether polymers |
| US3718627A (en) * | 1968-11-26 | 1973-02-27 | Du Pont | Cf{11 {32 cfcf{11 cf{11 so{11 {11 f and derivatives and polymers thereof |
| US4275225A (en) * | 1979-03-14 | 1981-06-23 | E. I. Du Pont De Nemours And Company | Polyfluoroallyloxy compounds, their preparation and copolymers therefrom |
| US4358545A (en) * | 1980-06-11 | 1982-11-09 | The Dow Chemical Company | Sulfonic acid electrolytic cell having flourinated polymer membrane with hydration product less than 22,000 |
| US4433082A (en) * | 1981-05-01 | 1984-02-21 | E. I. Du Pont De Nemours And Company | Process for making liquid composition of perfluorinated ion exchange polymer, and product thereof |
| US4940525A (en) * | 1987-05-08 | 1990-07-10 | The Dow Chemical Company | Low equivalent weight sulfonic fluoropolymers |
| US5463005A (en) * | 1992-01-03 | 1995-10-31 | Gas Research Institute | Copolymers of tetrafluoroethylene and perfluorinated sulfonyl monomers and membranes made therefrom |
| US5708130A (en) * | 1995-07-28 | 1998-01-13 | The Dow Chemical Company | 2,7-aryl-9-substituted fluorenes and 9-substituted fluorene oligomers and polymers |
| US5796170A (en) * | 1996-02-15 | 1998-08-18 | Northern Telecom Limited | Ball grid array (BGA) integrated circuit packages |
| AU745585B2 (en) * | 1996-10-15 | 2002-03-21 | E.I. Du Pont De Nemours And Company | Compositions containing particles of highly fluorinated ion exchange polymer |
| JP3899566B2 (ja) * | 1996-11-25 | 2007-03-28 | セイコーエプソン株式会社 | 有機ｅｌ表示装置の製造方法 |
| JP3861400B2 (ja) * | 1997-09-01 | 2006-12-20 | セイコーエプソン株式会社 | 電界発光素子およびその製造方法 |
| US6303238B1 (en) * | 1997-12-01 | 2001-10-16 | The Trustees Of Princeton University | OLEDs doped with phosphorescent compounds |
| JP3206646B2 (ja) * | 1998-01-22 | 2001-09-10 | 日本電気株式会社 | 多色発光有機ｅｌパネルおよびその製造方法 |
| US6087196A (en) * | 1998-01-30 | 2000-07-11 | The Trustees Of Princeton University | Fabrication of organic semiconductor devices using ink jet printing |
| JP2000091076A (ja) * | 1998-09-11 | 2000-03-31 | Sony Corp | 有機電界発光素子 |
| US6566153B1 (en) * | 1998-10-14 | 2003-05-20 | The Regents Of The University Of California | Process for fabricating organic semiconductor devices using ink-jet printing technology and device and system employing same |
| US6048573A (en) * | 1998-11-13 | 2000-04-11 | Eastman Kodak Company | Method of making an organic light-emitting device |
| TW468269B (en) * | 1999-01-28 | 2001-12-11 | Semiconductor Energy Lab | Serial-to-parallel conversion circuit, and semiconductor display device employing the same |
| TW512543B (en) * | 1999-06-28 | 2002-12-01 | Semiconductor Energy Lab | Method of manufacturing an electro-optical device |
| US6633121B2 (en) * | 2000-01-31 | 2003-10-14 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence display device and method of manufacturing same |
| US20020121638A1 (en) * | 2000-06-30 | 2002-09-05 | Vladimir Grushin | Electroluminescent iridium compounds with fluorinated phenylpyridines, phenylpyrimidines, and phenylquinolines and devices made with such compounds |
| US6670645B2 (en) * | 2000-06-30 | 2003-12-30 | E. I. Du Pont De Nemours And Company | Electroluminescent iridium compounds with fluorinated phenylpyridines, phenylpyrimidines, and phenylquinolines and devices made with such compounds |
| US7075102B2 (en) * | 2000-06-30 | 2006-07-11 | E.I. Du Pont De Nemours And Company | Electroluminescent iridium compounds with fluorinated phenylpyridines, phenylpyrimidines, and phenylquinolines and devices made with such compounds |
| TW565604B (en) * | 2001-04-25 | 2003-12-11 | Toray Industries | Pyrromethene metal complex, material of luminescent element using it and luminescent element |
| KR100491144B1 (ko) * | 2001-12-26 | 2005-05-24 | 삼성에스디아이 주식회사 | 평판표시장치 및 그의 제조방법 |
| KR100437533B1 (ko) * | 2002-05-29 | 2004-06-30 | 엘지.필립스 엘시디 주식회사 | 액티브 매트릭스형 유기전계발광 소자 및 그의 제조방법 |
| CN100483785C (zh) * | 2002-07-01 | 2009-04-29 | 精工爱普生株式会社 | 组合物、成膜方法及成膜装置、电光学装置及其制造方法 |
| US6747618B2 (en) * | 2002-08-20 | 2004-06-08 | Eastman Kodak Company | Color organic light emitting diode display with improved lifetime |
| US7098060B2 (en) * | 2002-09-06 | 2006-08-29 | E.I. Du Pont De Nemours And Company | Methods for producing full-color organic electroluminescent devices |
| US6891326B2 (en) * | 2002-11-15 | 2005-05-10 | Universal Display Corporation | Structure and method of fabricating organic devices |
| US6737800B1 (en) * | 2003-02-18 | 2004-05-18 | Eastman Kodak Company | White-emitting organic electroluminescent device with color filters and reflective layer for causing colored light constructive interference |
| US6844215B1 (en) * | 2003-08-25 | 2005-01-18 | Eastman Kodak Company | Method of forming tapered drain-to-anode connectors in a back plane for an active matrix OLED device |
| KR20050050487A (ko) * | 2003-11-25 | 2005-05-31 | 삼성에스디아이 주식회사 | 풀칼라 유기 전계 발광 소자 |
| US7449509B2 (en) * | 2003-12-10 | 2008-11-11 | Northwestern University | Hole transport layer compositions and related diode devices |
| US7030554B2 (en) * | 2004-02-06 | 2006-04-18 | Eastman Kodak Company | Full-color organic display having improved blue emission |
| US7365230B2 (en) * | 2004-02-20 | 2008-04-29 | E.I. Du Pont De Nemours And Company | Cross-linkable polymers and electronic devices made with such polymers |
| US7351358B2 (en) * | 2004-03-17 | 2008-04-01 | E.I. Du Pont De Nemours And Company | Water dispersible polypyrroles made with polymeric acid colloids for electronics applications |
| WO2005099312A2 (en) * | 2004-03-31 | 2005-10-20 | E. I. Du Pont De Nemours And Company | Triarylamine compounds for use as charge transport materials |
| JP5050312B2 (ja) * | 2004-07-23 | 2012-10-17 | 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 |
| DE602005003425T2 (de) * | 2004-10-11 | 2008-10-02 | Samsung SDI Co., Ltd., Suwon | Organische elektrolumineszierende Vorrichtung und deren Herstellungsmethode |
| US7569158B2 (en) * | 2004-10-13 | 2009-08-04 | Air Products And Chemicals, Inc. | Aqueous dispersions of polythienothiophenes with fluorinated ion exchange polymers as dopants |
| GB0423528D0 (en) * | 2004-10-22 | 2004-11-24 | Cambridge Display Tech Ltd | Monomer for making a crosslinked polymer |
| US20060105200A1 (en) * | 2004-11-17 | 2006-05-18 | Dmytro Poplavskyy | Organic electroluminescent device |
| KR100729089B1 (ko) * | 2005-08-26 | 2007-06-14 | 삼성에스디아이 주식회사 | 유기 발광표시장치 및 그 제조방법 |
| JP5061184B2 (ja) * | 2006-06-05 | 2012-10-31 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 有機発光ダイオードの形成方法、およびその方法によって製造されたデバイス |
-
2007
- 2007-12-20 US US11/961,540 patent/US20080166566A1/en not_active Abandoned
- 2007-12-28 KR KR1020097015819A patent/KR20090104079A/ko not_active Ceased
- 2007-12-28 EP EP20070868147 patent/EP2122707A2/en not_active Withdrawn
- 2007-12-28 WO PCT/US2007/026516 patent/WO2008082665A2/en not_active Ceased
- 2007-12-28 JP JP2009544122A patent/JP2010515260A/ja active Pending
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