CN102906151A - 基于苯唑二噻吩和噻吩并吡嗪的共轭聚合物及其制备方法和应用 - Google Patents
基于苯唑二噻吩和噻吩并吡嗪的共轭聚合物及其制备方法和应用 Download PDFInfo
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- CN102906151A CN102906151A CN2010800668785A CN201080066878A CN102906151A CN 102906151 A CN102906151 A CN 102906151A CN 2010800668785 A CN2010800668785 A CN 2010800668785A CN 201080066878 A CN201080066878 A CN 201080066878A CN 102906151 A CN102906151 A CN 102906151A
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/02—Polythioethers
- C08G75/06—Polythioethers from cyclic thioethers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- 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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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
- C09B69/109—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing other specific dyes
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- H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
- H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
- H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
- H01B1/124—Intrinsically conductive polymers
- H01B1/127—Intrinsically conductive polymers comprising five-membered aromatic rings in the main chain, e.g. polypyrroles, polythiophenes
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/151—Copolymers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
- C08G2261/14—Side-groups
- C08G2261/141—Side-chains having aliphatic units
- C08G2261/1412—Saturated aliphatic units
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- C—CHEMISTRY; METALLURGY
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Abstract
Description
PCT国内申请,说明书已公开。
Claims (1)
- PCT国内申请,权利要求书已公开。
Applications Claiming Priority (1)
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PCT/CN2010/074454 WO2011160302A1 (zh) | 2010-06-25 | 2010-06-25 | 基于苯唑二噻吩和噻吩并吡嗪的共轭聚合物及其制备方法和应用 |
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CN102906151A true CN102906151A (zh) | 2013-01-30 |
CN102906151B CN102906151B (zh) | 2014-05-07 |
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Country Status (5)
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US (1) | US20130102746A1 (zh) |
EP (1) | EP2586810A4 (zh) |
JP (1) | JP5638695B2 (zh) |
CN (1) | CN102906151B (zh) |
WO (1) | WO2011160302A1 (zh) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104119504A (zh) * | 2013-04-25 | 2014-10-29 | 海洋王照明科技股份有限公司 | 含吡咯吲哚并二噻吩-二噻吩并苯并噻二唑共轭聚合物材料及其制备方法和应用 |
CN111154075A (zh) * | 2019-04-30 | 2020-05-15 | 天津理工大学 | 氟代喹喔啉-噻吩共聚物及其制备方法 |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2014086722A1 (en) | 2012-12-04 | 2014-06-12 | Basf Se | Functionnalized benzodithiophene polymers for electronic application |
KR102110990B1 (ko) * | 2017-11-03 | 2020-05-14 | 삼성에스디아이 주식회사 | 중합체, 유기막 조성물 및 패턴 형성 방법 |
CN109545981A (zh) * | 2018-11-27 | 2019-03-29 | 江苏拓正茂源新能源有限公司 | 一种有机太阳能电池及其制备方法 |
CN111647140B (zh) * | 2020-05-25 | 2022-05-03 | 湘潭大学 | 一种聚合咔唑衍生物合镉配合物及其制备方法与用途 |
CN113896866B (zh) * | 2021-11-24 | 2023-10-17 | 中国石油大学(华东) | 一种砜修饰的共轭有机聚合物、其制备方法及应用 |
CN114591477B (zh) * | 2022-04-15 | 2023-10-24 | 福州大学 | 亚胺连接的二苯并噻吩砜基共价有机框架材料的制备和应用 |
CN114933693B (zh) * | 2022-06-17 | 2023-08-22 | 嘉应学院 | 一种共轭聚合物材料及其制备方法和应用 |
CN115572372B (zh) * | 2022-10-12 | 2024-05-07 | 潍坊医学院 | 一种基于π-共轭型供受体的类结构聚合物材料及其制备方法、应用 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101407574A (zh) * | 2008-12-01 | 2009-04-15 | 中国科学院长春应用化学研究所 | 含二噻吩并吡咯的给体-受体型共轭聚合物及制法和应用 |
US20100078074A1 (en) * | 2008-09-29 | 2010-04-01 | The Regents Of The University Of California | Active materials for photoelectric devices and devices that use the materials |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2000506914A (ja) * | 1996-03-06 | 2000-06-06 | ビーエーエスエフ アクチェンゲゼルシャフト | 置換ポリチオフェン、その製造及びその用途 |
JP2001019947A (ja) * | 1999-07-06 | 2001-01-23 | Fuji Photo Film Co Ltd | 新規重合体、発光素子材料およびそれを使用した発光素子 |
JP2007067230A (ja) * | 2005-08-31 | 2007-03-15 | Nara Institute Of Science & Technology | フタロシアニン薄膜層を有するデバイスおよびその製造方法 |
JP5164134B2 (ja) * | 2006-03-10 | 2013-03-13 | 住友化学株式会社 | 縮合環化合物及びその製造方法、重合体、これらを含む有機薄膜、並びに、これを備える有機薄膜素子及び有機薄膜トランジスタ |
CN101415715B (zh) * | 2006-03-10 | 2012-10-10 | 住友化学株式会社 | 稠环化合物及其制造方法、聚合物、含有它们的有机薄膜,有机薄膜元件及有机薄膜晶体管 |
JP5773568B2 (ja) * | 2006-10-11 | 2015-09-02 | メルク パテント ゲーエムベーハー | シロール含有ポリマーを用いた光電池 |
US20080262183A1 (en) * | 2007-04-17 | 2008-10-23 | Lutz Uwe Lehmann | Dithienopyrrole-containing copolymers |
KR101561323B1 (ko) * | 2008-07-02 | 2015-10-16 | 바스프 에스이 | 폴리(5,5'-비스(티오펜-2-일)-벤조[2,1-b;3,4-b']디티오펜) 및 이의 고성능 용액 가공가능한 반전도성 중합체로서의 용도 |
JP2010083785A (ja) * | 2008-09-30 | 2010-04-15 | Chisso Corp | 平面性の高い分子構造を有する化合物およびこれを用いた有機トランジスタ |
CN102227439B (zh) * | 2008-10-02 | 2015-08-19 | 巴斯夫欧洲公司 | 络盐 |
US8440785B2 (en) * | 2009-06-30 | 2013-05-14 | Plextronics, Inc. | Compositions, methods and polymers |
JP5501526B2 (ja) * | 2010-05-24 | 2014-05-21 | ▲海▼洋王照明科技股▲ふん▼有限公司 | 縮合環チオフェン単位を含むキノキサリン共役重合体、該共役重合体の製造方法及びその応用 |
-
2010
- 2010-06-25 CN CN201080066878.5A patent/CN102906151B/zh not_active Expired - Fee Related
- 2010-06-25 WO PCT/CN2010/074454 patent/WO2011160302A1/zh active Application Filing
- 2010-06-25 EP EP10853445.4A patent/EP2586810A4/en not_active Withdrawn
- 2010-06-25 JP JP2013515661A patent/JP5638695B2/ja active Active
- 2010-06-26 US US13/704,687 patent/US20130102746A1/en not_active Abandoned
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20100078074A1 (en) * | 2008-09-29 | 2010-04-01 | The Regents Of The University Of California | Active materials for photoelectric devices and devices that use the materials |
CN101407574A (zh) * | 2008-12-01 | 2009-04-15 | 中国科学院长春应用化学研究所 | 含二噻吩并吡咯的给体-受体型共轭聚合物及制法和应用 |
Non-Patent Citations (3)
Title |
---|
《Chemical Reviews》 20091130 Yen-Ju Cheng,Sheng-Hsiung Yang,Chain-Shu Hsu "Synthesis of Conjugated Polymers for Organic Solar Cell Applications" 第109卷, 第11期 * |
YEN-JU CHENG,SHENG-HSIUNG YANG,CHAIN-SHU HSU: ""Synthesis of Conjugated Polymers for Organic Solar Cell Applications"", 《CHEMICAL REVIEWS》 * |
项睿: "《STN检索报告》", 28 June 2013 * |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104119504A (zh) * | 2013-04-25 | 2014-10-29 | 海洋王照明科技股份有限公司 | 含吡咯吲哚并二噻吩-二噻吩并苯并噻二唑共轭聚合物材料及其制备方法和应用 |
CN111154075A (zh) * | 2019-04-30 | 2020-05-15 | 天津理工大学 | 氟代喹喔啉-噻吩共聚物及其制备方法 |
CN111154075B (zh) * | 2019-04-30 | 2022-09-30 | 天津理工大学 | 氟代喹喔啉-噻吩共聚物及其制备方法 |
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EP2586810A1 (en) | 2013-05-01 |
JP2013537564A (ja) | 2013-10-03 |
JP5638695B2 (ja) | 2014-12-10 |
WO2011160302A1 (zh) | 2011-12-29 |
EP2586810A4 (en) | 2014-01-29 |
CN102906151B (zh) | 2014-05-07 |
US20130102746A1 (en) | 2013-04-25 |
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