JP2013526636A5 - - Google Patents
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- Publication number
- JP2013526636A5 JP2013526636A5 JP2013510236A JP2013510236A JP2013526636A5 JP 2013526636 A5 JP2013526636 A5 JP 2013526636A5 JP 2013510236 A JP2013510236 A JP 2013510236A JP 2013510236 A JP2013510236 A JP 2013510236A JP 2013526636 A5 JP2013526636 A5 JP 2013526636A5
- Authority
- JP
- Japan
- Prior art keywords
- composition
- dopant
- hole transport
- transport material
- polymer
- 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.)
- Granted
Links
- 239000000203 mixture Substances 0.000 claims description 87
- 239000002019 doping agent Substances 0.000 claims description 24
- 230000005525 hole transport Effects 0.000 claims description 22
- 239000000463 material Substances 0.000 claims description 19
- 229920000547 conjugated polymer Polymers 0.000 claims description 13
- 229920000642 polymer Polymers 0.000 claims description 13
- 229920000123 polythiophene Polymers 0.000 claims description 13
- 150000008040 ionic compounds Chemical class 0.000 claims description 12
- 239000007795 chemical reaction product Substances 0.000 claims description 11
- 239000011159 matrix material Substances 0.000 claims description 11
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 10
- 229910052796 boron Inorganic materials 0.000 claims description 10
- 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 claims description 10
- 150000001768 cations Chemical class 0.000 claims description 9
- 239000000843 powder Substances 0.000 claims description 9
- 239000007787 solid Substances 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- 150000001450 anions Chemical class 0.000 claims description 8
- 229910052751 metal Inorganic materials 0.000 claims description 8
- 239000002184 metal Substances 0.000 claims description 8
- YAMJITULHOEKMI-UHFFFAOYSA-N B([O-])([O-])[O-].[Ag+3] Chemical compound B([O-])([O-])[O-].[Ag+3] YAMJITULHOEKMI-UHFFFAOYSA-N 0.000 claims description 7
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims description 7
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 7
- 229910052787 antimony Inorganic materials 0.000 claims description 7
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 7
- 150000001502 aryl halides Chemical class 0.000 claims description 7
- 229910052733 gallium Inorganic materials 0.000 claims description 7
- 229910052698 phosphorus Inorganic materials 0.000 claims description 7
- 239000011574 phosphorus Substances 0.000 claims description 7
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 6
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 229910052742 iron Inorganic materials 0.000 claims description 6
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 229920000570 polyether Polymers 0.000 claims description 6
- 229910052702 rhenium Inorganic materials 0.000 claims description 6
- 229910052709 silver Inorganic materials 0.000 claims description 6
- 239000004332 silver Substances 0.000 claims description 6
- 229910052804 chromium Inorganic materials 0.000 claims description 4
- 229910052802 copper Inorganic materials 0.000 claims description 4
- 238000002347 injection Methods 0.000 claims description 4
- 239000007924 injection Substances 0.000 claims description 4
- 229910052741 iridium Inorganic materials 0.000 claims description 4
- 229910052748 manganese Inorganic materials 0.000 claims description 4
- 229910052750 molybdenum Inorganic materials 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 229910052759 nickel Inorganic materials 0.000 claims description 4
- 229910052758 niobium Inorganic materials 0.000 claims description 4
- 229910052762 osmium Inorganic materials 0.000 claims description 4
- 229910052763 palladium Inorganic materials 0.000 claims description 4
- 229910052697 platinum Inorganic materials 0.000 claims description 4
- 229910052703 rhodium Inorganic materials 0.000 claims description 4
- 229910052707 ruthenium Inorganic materials 0.000 claims description 4
- 229920005613 synthetic organic polymer Polymers 0.000 claims description 4
- 229910052713 technetium Inorganic materials 0.000 claims description 4
- 229910052721 tungsten Inorganic materials 0.000 claims description 4
- 229910052720 vanadium Inorganic materials 0.000 claims description 4
- LWNGJAHMBMVCJR-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenoxy)boronic acid Chemical compound OB(O)OC1=C(F)C(F)=C(F)C(F)=C1F LWNGJAHMBMVCJR-UHFFFAOYSA-N 0.000 claims description 3
- NTAAWOAYVRMQOQ-UHFFFAOYSA-N FC1=C(C(=C(C(=C1[Ag](C1=C(C(=C(C(=C1F)F)F)F)F)(C1=C(C(=C(C(=C1F)F)F)F)F)C1=C(C(=C(C(=C1F)F)F)F)F)F)F)F)F.B(O)(O)O Chemical group FC1=C(C(=C(C(=C1[Ag](C1=C(C(=C(C(=C1F)F)F)F)F)(C1=C(C(=C(C(=C1F)F)F)F)F)C1=C(C(=C(C(=C1F)F)F)F)F)F)F)F)F.B(O)(O)O NTAAWOAYVRMQOQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 2
- 239000004327 boric acid Substances 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 0 CC(C)(*)c1c(*)c(C(*)[C@](*=CC)C(*)=C2*)c2[s]1 Chemical compound CC(C)(*)c1c(*)c(C(*)[C@](*=CC)C(*)=C2*)c2[s]1 0.000 description 18
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- CHLICZRVGGXEOD-UHFFFAOYSA-N 1-Methoxy-4-methylbenzene Chemical compound COC1=CC=C(C)C=C1 CHLICZRVGGXEOD-UHFFFAOYSA-N 0.000 description 2
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 1
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
- DCWQZPJHHVLHSV-UHFFFAOYSA-N 3-ethoxypropanenitrile Chemical compound CCOCCC#N DCWQZPJHHVLHSV-UHFFFAOYSA-N 0.000 description 1
- OOWFYDWAMOKVSF-UHFFFAOYSA-N 3-methoxypropanenitrile Chemical compound COCCC#N OOWFYDWAMOKVSF-UHFFFAOYSA-N 0.000 description 1
- 229940077398 4-methyl anisole Drugs 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US33365710P | 2010-05-11 | 2010-05-11 | |
| US61/333,657 | 2010-05-11 | ||
| US201161446974P | 2011-02-25 | 2011-02-25 | |
| US61/446,974 | 2011-02-25 | ||
| PCT/US2011/035897 WO2011143196A1 (en) | 2010-05-11 | 2011-05-10 | Doping conjugated polymers and devices |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013526636A JP2013526636A (ja) | 2013-06-24 |
| JP2013526636A5 true JP2013526636A5 (https=) | 2014-06-05 |
| JP5770268B2 JP5770268B2 (ja) | 2015-08-26 |
Family
ID=44315243
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013510236A Active JP5770268B2 (ja) | 2010-05-11 | 2011-05-10 | 共役ポリマーおよびデバイスのドーピング |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US8674047B2 (https=) |
| EP (1) | EP2569347A1 (https=) |
| JP (1) | JP5770268B2 (https=) |
| KR (1) | KR101848523B1 (https=) |
| CN (2) | CN102884102A (https=) |
| TW (1) | TWI637004B (https=) |
| WO (1) | WO2011143196A1 (https=) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8674047B2 (en) * | 2010-05-11 | 2014-03-18 | Plextronics, Inc. | Doping conjugated polymers and devices |
| US9203030B2 (en) * | 2011-05-16 | 2015-12-01 | Georgia Tech Research Corporation | Recyclable organic solar cells on substrates comprising cellulose nanocrystals (CNC) |
| EP2764518A1 (en) | 2011-10-04 | 2014-08-13 | Plextronics, Inc. | Improved doping methods for hole injection and transport layers |
| JP6098042B2 (ja) * | 2012-04-24 | 2017-03-22 | 日立化成株式会社 | 色変化防止剤、該色変化防止剤を含むインク組成物、該インク組成物を用いて形成した有機薄膜、有機エレクトロニクス素子、有機エレクトロルミネセンス素子、表示素子、照明装置、及び表示装置 |
| WO2014039687A1 (en) | 2012-09-06 | 2014-03-13 | Plextronics, Inc. | Electroluminescent devices comprising insulator-free metal grids |
| JP6545619B2 (ja) * | 2012-09-27 | 2019-07-17 | メルク パテント ゲーエムベーハー | 有機エレクトロルミッセンス素子のための材料 |
| JP6152648B2 (ja) * | 2013-01-25 | 2017-06-28 | 日本ケミコン株式会社 | 有機エレクトロルミネッセンス素子及びその製造方法 |
| WO2014141367A1 (ja) * | 2013-03-11 | 2014-09-18 | 昭和電工株式会社 | 導電性重合体含有分散液の製造方法 |
| WO2015179665A1 (en) * | 2014-05-22 | 2015-11-26 | Rhodia Operations | Polymer compositions, polymer films, and electronic devices containing such films |
| KR102399386B1 (ko) * | 2014-12-15 | 2022-05-17 | 닛산 가가쿠 가부시키가이샤 | 정공 캐리어 물질 및 폴리(아릴 에테르 술폰)을 함유하는 조성물 및 그의 용도 |
| JP6620816B2 (ja) * | 2014-12-15 | 2019-12-18 | 日産化学株式会社 | 正孔輸送材料とフルオロポリマーとを含有する組成物及びその使用 |
| EP3325560A4 (en) | 2015-07-17 | 2019-03-27 | Nissan Chemical Corporation | Nonaqueous ink compositions containing metal nanoparticles for use in organic electronics |
| JP7082984B2 (ja) * | 2017-02-20 | 2022-06-09 | ノヴァレッド ゲーエムベーハー | 電子半導体デバイスおよびその電子半導体デバイスの製造方法および化合物 |
| EP3364475B1 (en) * | 2017-02-20 | 2024-05-29 | Novaled GmbH | Electronic semiconducting device, method for preparing the electronic semiconducting device and compound |
| JP2018203889A (ja) * | 2017-06-06 | 2018-12-27 | 日立化成株式会社 | 硬化性重合体、重合液、導電性膜及び有機発光素子 |
| CN108032641B (zh) * | 2017-12-07 | 2020-01-17 | 南京邮电大学 | 一种印刷制备大面积图案化有机发光薄膜的方法 |
| JP7289059B2 (ja) * | 2017-12-28 | 2023-06-09 | パナソニックＩｐマネジメント株式会社 | 電解コンデンサおよびその製造方法 |
| JP7517337B2 (ja) * | 2019-06-26 | 2024-07-17 | 日産化学株式会社 | 電荷輸送性ワニス |
| CN111192966B (zh) * | 2020-01-09 | 2023-07-25 | 通威太阳能(眉山)有限公司 | 钙钛矿太阳能电池及其制备方法 |
| US12073957B2 (en) * | 2020-05-01 | 2024-08-27 | The University Of Tokyo | Conductor material |
| EP4106034B1 (en) * | 2021-06-18 | 2025-01-08 | Novaled GmbH | Organic electronic device comprising a metal compound comprising metal cation and at least one borate anion of formula (i), display device comprising the organic electronic device, use of the metal compound in an organic electronic device, and method for preparation of the organic electronic device |
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| US4356429A (en) | 1980-07-17 | 1982-10-26 | Eastman Kodak Company | Organic electroluminescent cell |
| US4539507A (en) | 1983-03-25 | 1985-09-03 | Eastman Kodak Company | Organic electroluminescent devices having improved power conversion efficiencies |
| US4737557A (en) | 1986-03-20 | 1988-04-12 | Agency Of Industrial Science And Technology | 3-N-higher alkylthiophene polymer and composition thereof |
| FR2596566B1 (fr) | 1986-04-01 | 1989-03-10 | Solvay | Polymeres conducteurs derives de 3-alkylthiophenes, procede pour leur fabrication et dispositifs electroconducteurs les contenant |
| GB8909011D0 (en) | 1989-04-20 | 1989-06-07 | Friend Richard H | Electroluminescent devices |
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| US5331183A (en) | 1992-08-17 | 1994-07-19 | The Regents Of The University Of California | Conjugated polymer - acceptor heterojunctions; diodes, photodiodes, and photovoltaic cells |
| US5834080A (en) | 1994-10-18 | 1998-11-10 | Xerox Corporation | Controllably conductive polymer compositions for development systems |
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| AT411306B (de) | 2000-04-27 | 2003-11-25 | Qsel Quantum Solar Energy Linz | Photovoltaische zelle mit einer photoaktiven schicht aus zwei molekularen organischen komponenten |
| AT410729B (de) | 2000-04-27 | 2003-07-25 | Qsel Quantum Solar Energy Linz | Photovoltaische zelle mit einer photoaktiven schicht aus zwei molekularen organischen komponenten |
| US6602974B1 (en) | 2001-12-04 | 2003-08-05 | Carnegie Mellon University | Polythiophenes, block copolymers made therefrom, and methods of forming the same |
| JP2003238773A (ja) * | 2002-02-14 | 2003-08-27 | Nippon Telegr & Teleph Corp <Ntt> | 導電性組成物 |
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| US7070867B2 (en) | 2003-12-05 | 2006-07-04 | The University Of Southern California | OLEDs having n-type doping |
| CN1906704A (zh) | 2003-12-10 | 2007-01-31 | 西北大学 | 空穴传输层组合物和相关的二极管装置 |
| KR100834327B1 (ko) | 2004-03-11 | 2008-06-02 | 미쓰비시 가가꾸 가부시키가이샤 | 전하 수송막용 조성물 및 이온 화합물, 이를 이용한 전하수송막 및 유기 전계 발광 장치, 및 유기 전계 발광 장치의제조 방법 및 전하 수송막의 제조 방법 |
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| KR101269256B1 (ko) | 2004-09-24 | 2013-05-29 | 플렉스트로닉스, 인크 | 헤테로 원자를 갖는 위치 규칙적 폴리(3-치환 티오펜)를 포함하는 전기발광 소자 |
| KR20070102661A (ko) | 2004-09-24 | 2007-10-19 | 플렉스트로닉스, 인크 | 광기전 전지에서의 헤테로 원자를 갖는 위치 규칙적폴리(3-치환 티오펜) |
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| WO2006086480A2 (en) | 2005-02-10 | 2006-08-17 | Plextronics, Inc. | Hole injection/transport layer compositions and devices |
| EP2537874B1 (en) | 2006-07-21 | 2021-05-19 | Nissan Chemical Corporation | Sulfonation of conducting polymers and oled, photovoltaic, and esd devices |
| KR100860411B1 (ko) | 2006-12-08 | 2008-09-26 | 한국전자통신연구원 | 멀티캐스트를 이용한 양방향 지역 광고 시스템 및 방법 |
| CN107266679B (zh) | 2008-02-15 | 2021-07-06 | 三菱化学株式会社 | 共轭聚合物、有机场致发光元件材料、有机场致发光元件用组合物、有机场致发光元件 |
| EP2250207B1 (en) | 2008-02-29 | 2012-01-04 | Plextronics, Inc. | Planarizing agents and devices |
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| CA2720694C (en) * | 2008-04-11 | 2017-05-23 | Plextronics, Inc. | Doped conjugated polymers, devices, and methods of making devices |
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| JP2011525918A (ja) | 2008-06-27 | 2011-09-29 | ユニバーサル ディスプレイ コーポレイション | 架橋可能なイオンドーパント |
| WO2010051259A1 (en) | 2008-10-27 | 2010-05-06 | Plextronics, Inc. | Polyarylamine ketones |
| US8283002B2 (en) | 2008-11-18 | 2012-10-09 | Plextronics, Inc. | Aminobenzene compositions and related devices and methods |
| KR20110099230A (ko) | 2008-12-01 | 2011-09-07 | 스미또모 가가꾸 가부시키가이샤 | 발광성 은 착체 |
| JP2010198793A (ja) * | 2009-02-23 | 2010-09-09 | Fujifilm Corp | 導電性膜、導電性ポリマー組成物、導電性ポリマー材料、デバイス、及び抵抗膜式タッチパネル |
| US8674047B2 (en) * | 2010-05-11 | 2014-03-18 | Plextronics, Inc. | Doping conjugated polymers and devices |
| CN202676329U (zh) | 2012-07-04 | 2013-01-16 | 永运电子有限公司 | 一种压力传感器 |
-
2011
- 2011-05-10 US US13/104,598 patent/US8674047B2/en not_active Expired - Fee Related
- 2011-05-10 CN CN2011800225508A patent/CN102884102A/zh active Pending
- 2011-05-10 KR KR1020127031717A patent/KR101848523B1/ko active Active
- 2011-05-10 TW TW100116358A patent/TWI637004B/zh active
- 2011-05-10 CN CN201710388821.0A patent/CN107236258A/zh active Pending
- 2011-05-10 EP EP11720688A patent/EP2569347A1/en not_active Withdrawn
- 2011-05-10 WO PCT/US2011/035897 patent/WO2011143196A1/en not_active Ceased
- 2011-05-10 JP JP2013510236A patent/JP5770268B2/ja active Active
-
2014
- 2014-02-10 US US14/176,951 patent/US20140217334A1/en not_active Abandoned
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