TWI637004B - 摻雜共軛聚合物及裝置 - Google Patents
摻雜共軛聚合物及裝置 Download PDFInfo
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- TWI637004B TWI637004B TW100116358A TW100116358A TWI637004B TW I637004 B TWI637004 B TW I637004B TW 100116358 A TW100116358 A TW 100116358A TW 100116358 A TW100116358 A TW 100116358A TW I637004 B TWI637004 B TW I637004B
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- Prior art keywords
- composition
- polymer
- conjugated polymer
- dopant
- polythiophene
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- 229920000547 conjugated polymer Polymers 0.000 title claims abstract description 122
- 239000000203 mixture Substances 0.000 claims abstract description 160
- -1 silver tetrakis(pentafluorophenyl)borate Chemical compound 0.000 claims abstract description 110
- 239000002019 doping agent Substances 0.000 claims abstract description 108
- 229920000123 polythiophene Polymers 0.000 claims abstract description 71
- 239000000463 material Substances 0.000 claims abstract description 50
- 230000005525 hole transport Effects 0.000 claims abstract description 21
- 239000002904 solvent Substances 0.000 claims description 78
- 229920000642 polymer Polymers 0.000 claims description 72
- 239000011159 matrix material Substances 0.000 claims description 55
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 36
- 229910052709 silver Inorganic materials 0.000 claims description 35
- 239000004332 silver Substances 0.000 claims description 34
- 150000001450 anions Chemical class 0.000 claims description 30
- 239000007787 solid Substances 0.000 claims description 30
- 229910052751 metal Inorganic materials 0.000 claims description 29
- 239000002184 metal Substances 0.000 claims description 29
- 238000002347 injection Methods 0.000 claims description 24
- 239000007924 injection Substances 0.000 claims description 24
- 239000000843 powder Substances 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 22
- 229910052794 bromium Inorganic materials 0.000 claims description 19
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 18
- 229910052801 chlorine Inorganic materials 0.000 claims description 18
- 229910052731 fluorine Inorganic materials 0.000 claims description 17
- 229910052740 iodine Inorganic materials 0.000 claims description 17
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 14
- 229910052796 boron Inorganic materials 0.000 claims description 14
- 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 11
- 239000007795 chemical reaction product Substances 0.000 claims description 9
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 229920005613 synthetic organic polymer Polymers 0.000 claims description 2
- URSLCTBXQMKCFE-UHFFFAOYSA-N dihydrogenborate Chemical compound OB(O)[O-] URSLCTBXQMKCFE-UHFFFAOYSA-N 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 239000000758 substrate Substances 0.000 abstract description 30
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 abstract description 20
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- 238000000034 method Methods 0.000 description 34
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 23
- 125000001424 substituent group Chemical group 0.000 description 22
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 21
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- 125000003118 aryl group Chemical group 0.000 description 20
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- 150000003839 salts Chemical class 0.000 description 13
- 229910052787 antimony Inorganic materials 0.000 description 12
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 12
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Classifications
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- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
- C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
- C08G61/126—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one sulfur atom in the ring
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/322—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising boron
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- C08G2261/322—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed
- C08G2261/3223—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed containing one or more sulfur atoms as the only heteroatom, e.g. thiophene
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- C08G2261/70—Post-treatment
- C08G2261/79—Post-treatment doping
- C08G2261/792—Post-treatment doping with low-molecular weight dopants
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- C08G2261/90—Applications
- C08G2261/91—Photovoltaic applications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08G2261/90—Applications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08G2261/94—Applications in sensors, e.g. biosensors
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- C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
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| EP2569347A1 (en) * | 2010-05-11 | 2013-03-20 | 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) |
| TW201329196A (zh) * | 2011-10-04 | 2013-07-16 | 普雷克科技公司 | 用於電洞注射及傳送層之改良摻雜之方法 |
| 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 |
| DE112013004753A5 (de) * | 2012-09-27 | 2015-08-27 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
| 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 |
| JP6737276B2 (ja) * | 2014-12-15 | 2020-08-05 | 日産化学株式会社 | 正孔輸送材料とポリ（アリールエーテルスルホン）とを含有する組成物及びその使用 |
| 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 |
| CN107849376B (zh) | 2015-07-17 | 2021-11-30 | 日产化学工业株式会社 | 适用于有机电子的包含金属纳米颗粒的非水性油墨组合物 |
| US11539014B2 (en) * | 2017-02-20 | 2022-12-27 | Novaled Gmbh | Electronic semiconducting device, method for preparing the electronic semiconducting device and compound |
| 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 |
| KR102794329B1 (ko) * | 2019-06-26 | 2025-04-14 | 닛산 가가쿠 가부시키가이샤 | 전하 수송성 바니시 |
| 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 |
| EP4144802A4 (en) * | 2020-05-01 | 2024-07-10 | 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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| JP2003238773A (ja) * | 2002-02-14 | 2003-08-27 | Nippon Telegr & Teleph Corp <Ntt> | 導電性組成物 |
| WO2009126918A1 (en) * | 2008-04-11 | 2009-10-15 | Plextronics, Inc. | Doped conjugated polymers, devices, and methods of making devices |
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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 |
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| 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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| GB9018698D0 (en) | 1990-08-24 | 1990-10-10 | Lynxvale Ltd | Semiconductive copolymers for use in electroluminescent devices |
| JP2998268B2 (ja) * | 1991-04-19 | 2000-01-11 | 三菱化学株式会社 | 有機電界発光素子 |
| 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 |
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| US6602974B1 (en) | 2001-12-04 | 2003-08-05 | Carnegie Mellon University | Polythiophenes, block copolymers made therefrom, and methods of forming the same |
| US20040113127A1 (en) | 2002-12-17 | 2004-06-17 | Min Gary Yonggang | Resistor compositions having a substantially neutral temperature coefficient of resistance and methods and compositions relating thereto |
| US7070867B2 (en) | 2003-12-05 | 2006-07-04 | The University Of Southern California | OLEDs having n-type doping |
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- 2011-05-10 KR KR1020127031717A patent/KR101848523B1/ko active Active
- 2011-05-10 US US13/104,598 patent/US8674047B2/en not_active Expired - Fee Related
- 2011-05-10 WO PCT/US2011/035897 patent/WO2011143196A1/en not_active Ceased
- 2011-05-10 CN CN2011800225508A patent/CN102884102A/zh active Pending
- 2011-05-10 TW TW100116358A patent/TWI637004B/zh active
- 2011-05-10 CN CN201710388821.0A patent/CN107236258A/zh active Pending
- 2011-05-10 JP JP2013510236A patent/JP5770268B2/ja active Active
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2014
- 2014-02-10 US US14/176,951 patent/US20140217334A1/en not_active Abandoned
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| JP2003238773A (ja) * | 2002-02-14 | 2003-08-27 | Nippon Telegr & Teleph Corp <Ntt> | 導電性組成物 |
| WO2009126918A1 (en) * | 2008-04-11 | 2009-10-15 | Plextronics, Inc. | Doped conjugated polymers, devices, and methods of making devices |
Also Published As
| Publication number | Publication date |
|---|---|
| US20140217334A1 (en) | 2014-08-07 |
| US20110278559A1 (en) | 2011-11-17 |
| CN102884102A (zh) | 2013-01-16 |
| JP2013526636A (ja) | 2013-06-24 |
| US8674047B2 (en) | 2014-03-18 |
| TW201200537A (en) | 2012-01-01 |
| WO2011143196A1 (en) | 2011-11-17 |
| EP2569347A1 (en) | 2013-03-20 |
| CN107236258A (zh) | 2017-10-10 |
| KR20130113930A (ko) | 2013-10-16 |
| JP5770268B2 (ja) | 2015-08-26 |
| KR101848523B1 (ko) | 2018-04-12 |
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