CN102449023B - 多环联噻吩 - Google Patents

多环联噻吩 Download PDF

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Publication number
CN102449023B
CN102449023B CN201080023293.5A CN201080023293A CN102449023B CN 102449023 B CN102449023 B CN 102449023B CN 201080023293 A CN201080023293 A CN 201080023293A CN 102449023 B CN102449023 B CN 102449023B
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alkyl
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aryl
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substituted
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CN102449023A (zh
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H·J·吉尔尼尔
N·舍博塔莱瓦
O·F·埃比谢尔
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Clap Co Ltd
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BASF SE
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  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
  • Thin Film Transistor (AREA)
  • Photovoltaic Devices (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Electroluminescent Light Sources (AREA)
CN201080023293.5A 2009-05-27 2010-05-21 多环联噻吩 Expired - Fee Related CN102449023B (zh)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
EP09161243 2009-05-27
EP09161243.2 2009-05-27
EP09170185 2009-09-14
EP09170185.4 2009-09-14
PCT/EP2010/057038 WO2010136401A2 (en) 2009-05-27 2010-05-21 Polycyclic dithiophenes

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CN102449023A CN102449023A (zh) 2012-05-09
CN102449023B true CN102449023B (zh) 2015-10-07

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US (2) US9233930B2 (enExample)
EP (1) EP2435497B1 (enExample)
JP (1) JP5886190B2 (enExample)
KR (1) KR101805203B1 (enExample)
CN (1) CN102449023B (enExample)
WO (1) WO2010136401A2 (enExample)

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US8859714B1 (en) 2009-07-01 2014-10-14 Northwestern University Polymeric semiconductors and related devices
US8946688B2 (en) * 2009-12-14 2015-02-03 Idemitsu Kosan Co., Ltd. Polycyclic ring-fused compound and organic thin film transistor utilizing the same
US8895693B2 (en) 2010-06-25 2014-11-25 Samsung Electronics Co., Ltd. Electron-donating polymers and organic solar cells including the same
WO2012083510A1 (zh) * 2010-12-20 2012-06-28 海洋王照明科技股份有限公司 有机半导体材料及其制备方法和应用
JP2012162514A (ja) * 2011-01-20 2012-08-30 Kuraray Co Ltd ジチエノゲルモール重合体及びそれを含有した有機半導体デバイス
US9748496B2 (en) 2011-02-02 2017-08-29 Idemitsu Kosan Co., Ltd. Nitrogenated heterocyclic derivative, electron-transporting material for organic electroluminescent elements, and organic electroluminescent element using same
GB201105482D0 (en) * 2011-03-31 2011-05-18 Imp Innovations Ltd Polymers
WO2012146504A1 (en) * 2011-04-27 2012-11-01 Basf Se Semiconductor materials based on dithienopyridone copolymers
KR101853395B1 (ko) 2011-05-23 2018-04-30 삼성전자주식회사 전자 공여체 고분자 및 이를 포함하는 태양 전지
US10316135B2 (en) * 2011-06-17 2019-06-11 The Regents Of The University Of California Fluorine substitution influence on benzo[2,1,3]thiodiazole based polymers for field-effect transistor applications
KR101777326B1 (ko) 2011-10-05 2017-09-12 삼성전자주식회사 전자 공여체 고분자 및 이를 포함하는 유기 태양 전지
CN103917575A (zh) 2011-11-02 2014-07-09 三菱化学株式会社 共轭高分子的制造方法、共轭高分子、光电转换元件、太阳能电池以及太阳能电池模块
JP6040939B2 (ja) 2011-11-02 2016-12-07 三菱化学株式会社 縮合多環芳香族化合物の製造方法及び共役高分子
US8835598B2 (en) * 2012-03-22 2014-09-16 Polyera Corporation Conjugated polymers and their use in optoelectronic devices
KR101424978B1 (ko) * 2012-05-24 2014-07-31 경상대학교산학협력단 길만시약 화합물을 이용한 헤테로 융합고리 화합물의 신규한 제조방법
US9359470B2 (en) 2012-07-23 2016-06-07 Basf Se Dithienobenzofuran polymers and small molecules for electronic application
EP2928940B1 (en) 2012-12-04 2021-03-03 CLAP Co., Ltd. Functionalized benzodithiophene polymers for electronic application
US9472764B2 (en) * 2012-12-04 2016-10-18 Northwestern University Conjugated polymers and their use in optoelectronic devices
JP6112717B2 (ja) * 2013-05-13 2017-04-12 国立大学法人東京工業大学 ジチエノゲルモール骨格を有する有機ヘテロ高分子およびその製造方法
CA2953681A1 (en) * 2013-06-28 2015-04-02 Solarwindow Technologies, Inc. Preparation and coating of pilot equipment with organic photovoltaic films to produce electricity for emergency power supply systems for pilots
JP6184234B2 (ja) * 2013-08-02 2017-08-23 富士フイルム株式会社 有機薄膜トランジスタ、有機半導体薄膜および有機半導体材料
CN103601740B (zh) * 2013-09-17 2016-02-24 武汉工程大学 一种2,1,3-苯并噻二唑并二噻吩衍生溴代物及其合成方法
JP6209099B2 (ja) * 2014-02-10 2017-10-04 富士フイルム株式会社 光電変換素子およびその使用方法、光センサ、撮像素子、化合物およびその製造方法
KR20170056600A (ko) 2014-09-09 2017-05-23 메르크 파텐트 게엠베하 공액 중합체
US10875957B2 (en) * 2015-11-11 2020-12-29 The Regents Of The University Of California Fluorine substitution influence on benzo[2,1,3]thiodiazole based polymers for field-effect transistor applications
CN105906788B (zh) * 2016-06-12 2018-06-29 南京邮电大学 含有吩嗪结构的聚合物及其制备方法和应用
JP6676181B2 (ja) * 2016-09-29 2020-04-08 富士フイルム株式会社 微結晶有機半導体膜、有機半導体トランジスタ、及び有機半導体トランジスタの製造方法
US10312444B2 (en) 2016-10-06 2019-06-04 International Business Machines Corporation Organic semiconductors with dithienofuran core monomers
CN106967096B (zh) * 2017-05-17 2019-01-29 中节能万润股份有限公司 一种含噻吩结构的二唑类杂环化合物及其应用
US20210009604A1 (en) * 2018-05-07 2021-01-14 Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd Bifuran-imide-based materials and uses thereof
US11332579B1 (en) 2021-11-19 2022-05-17 Phillips 66 Company Fused dithieno benzothiadiazole polymers for organic photovoltaics
US11849629B2 (en) 2021-11-19 2023-12-19 Phillips 66 Company Fused dithieno benzothiadiazole polymers for organic photovolatics
US11326019B1 (en) 2021-11-19 2022-05-10 Phillips 66 Company Fused dithieno benzothiadiazole polymers for organic photovoltaics
US11690283B2 (en) 2021-11-19 2023-06-27 Phillips 66 Company Fused dithieno benzothiadiazole polymers for organic photovoltaics
CN114349766B (zh) * 2021-12-20 2023-04-07 淮阴工学院 一种d-a-d型有机半导体材料及其制备方法和应用
CN114507337A (zh) * 2022-02-21 2022-05-17 东华大学 含有喹喔啉结构的共轭聚合物及其合成方法与应用
CN115724873B (zh) * 2022-11-01 2025-10-28 汕头大学 基于苯并二噻吩的稠环单体、其聚合物及制备方法和应用

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003052841A1 (en) * 2001-12-19 2003-06-26 Avecia Limited Organic field effect transistor with an organic dielectric
WO2005003126A1 (en) * 2003-07-07 2005-01-13 The University Of Hong Kong Photochromic diarylethene-containing coordination compounds and the production thereof
EP2006291A1 (en) * 2006-03-10 2008-12-24 Osaka University Fused ring compound and method for producing same, polymer, organic thin film containing those, and organic thin film device and organic thin film transistor comprising such organic thin film
WO2009115413A2 (en) * 2008-03-17 2009-09-24 Basf Se Substituted oligo- or polythiophenes

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2339128T3 (es) * 2004-03-04 2010-05-17 The Procter And Gamble Company Composiones cosmeticas para teñir el cabello que los contienen y uso de las mismas.
KR101546985B1 (ko) 2007-10-09 2015-08-24 바스프 에스이 피롤로피롤 유도체, 그의 제조 및 용도
EP2205657B1 (en) 2007-10-25 2017-04-05 Basf Se Ketopyrroles as organic semiconductors
WO2009092671A2 (en) 2008-01-25 2009-07-30 Basf Se Organic light emitting systems
JP5535208B2 (ja) 2008-07-18 2014-07-02 ビーエーエスエフ ソシエタス・ヨーロピア 電子用途のためのアザピレン
WO2010046259A1 (en) 2008-10-21 2010-04-29 Basf Se Polycyclic compounds for electronic applications
CN102272192B (zh) 2008-10-31 2016-12-07 巴斯夫欧洲公司 用于有机场效应晶体管的二酮吡咯并吡咯聚合物
CN102203160B (zh) 2008-10-31 2013-07-17 巴斯夫欧洲公司 用于有机半导体器件的二酮吡咯并吡咯聚合物
JP5675787B2 (ja) * 2009-05-27 2015-02-25 ビーエーエスエフ ソシエタス・ヨーロピアBasf Se 有機半導体装置で使用するためのジケトピロロピロールポリマー
JP5763632B2 (ja) 2009-06-30 2015-08-12 ソルベイ ユーエスエイ インコーポレイテッド 少なくとも1つのビチオフェン繰り返し単位を含むポリマー、該ポリマーを合成する方法、およびそれを含む組成物
US20110006287A1 (en) * 2009-07-10 2011-01-13 Wei You Polymers with tunable band gaps for photonic and electronic applications
US8624232B2 (en) * 2009-08-28 2014-01-07 Prashant Sonar Ambipolar polymeric semiconductor materials and organic electronic devices

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003052841A1 (en) * 2001-12-19 2003-06-26 Avecia Limited Organic field effect transistor with an organic dielectric
WO2005003126A1 (en) * 2003-07-07 2005-01-13 The University Of Hong Kong Photochromic diarylethene-containing coordination compounds and the production thereof
EP2006291A1 (en) * 2006-03-10 2008-12-24 Osaka University Fused ring compound and method for producing same, polymer, organic thin film containing those, and organic thin film device and organic thin film transistor comprising such organic thin film
WO2009115413A2 (en) * 2008-03-17 2009-09-24 Basf Se Substituted oligo- or polythiophenes

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
"Highly conjugated acrylate-functionalized polythiophenes from anodic coupling of thiophene- and bithiophene-hexyl acrylates";G.Zotti,et al;《Synthetic Metals》;19990830;第105卷(第2期);第135–139页 *
"Synthesis of oligomers having a pendant dithienosilole unit and their applications to EL device materials";Kwang-Hoi Lee,et al;《Journal of Organometallic Chemistry》;20050117;第690卷(第2期);第333-337页 *
Joseph A. Letizia,et al."n-Channel Polymers by Design:Optimizing the Interplay of Solubilizing Substituents,Crystal Packing,and Field-Effect Transistor Characteristics in Polymeric Bithiophene-Imide Semiconductors".《J. Am. Chem. Soc.》.2008,第130卷(第30期),第9679-9694页. *
Thomas Baumgartner,et al."The Dithieno[3,2-b:2’,3’-d]phosphole System:A Novel Building Block for Highly Luminescent π-Conjugated Materials".《Angewandte Chemie International Edition》.2004,第43卷(第45期),第6197-6201页. *

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