CA2655076A1 - Diketopyrrolopyrrole polymers as organic semiconductors - Google Patents

Diketopyrrolopyrrole polymers as organic semiconductors Download PDF

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Publication number
CA2655076A1
CA2655076A1 CA002655076A CA2655076A CA2655076A1 CA 2655076 A1 CA2655076 A1 CA 2655076A1 CA 002655076 A CA002655076 A CA 002655076A CA 2655076 A CA2655076 A CA 2655076A CA 2655076 A1 CA2655076 A1 CA 2655076A1
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substituted
group
formula
optionally
interrupted
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English (en)
French (fr)
Inventor
Mathieu G. R. Turbiez
Rene Albert Johan Janssen
Martinus Maria Wienk
Hans Juerg Kirner
Mathias Dueggeli
Bernd Tieke
Yu Zhu
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BASF Schweiz AG
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    • C08G61/12Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
    • C08G61/122Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
    • C08G61/123Macromolecular 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
    • BPERFORMING OPERATIONS; TRANSPORTING
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    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D487/00Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
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    • C08G2261/10Definition of the polymer structure
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    • C08G2261/324Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed
    • C08G2261/3241Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed containing one or more nitrogen atoms as the only heteroatom, e.g. carbazole
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    • YGENERAL 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
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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Materials Engineering (AREA)
  • Nanotechnology (AREA)
  • Physics & Mathematics (AREA)
  • Mathematical Physics (AREA)
  • Theoretical Computer Science (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Electromagnetism (AREA)
  • Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
  • Electroluminescent Light Sources (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Thin Film Transistor (AREA)
CA002655076A 2006-06-30 2007-06-20 Diketopyrrolopyrrole polymers as organic semiconductors Abandoned CA2655076A1 (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
EP06116391.1 2006-06-30
EP06116391 2006-06-30
EP06119228 2006-08-21
EP06119228.2 2006-08-21
PCT/EP2007/056102 WO2008000664A1 (en) 2006-06-30 2007-06-20 Diketopyrrolopyrrole polymers as organic semiconductors

Publications (1)

Publication Number Publication Date
CA2655076A1 true CA2655076A1 (en) 2008-01-03

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
CA002655076A Abandoned CA2655076A1 (en) 2006-06-30 2007-06-20 Diketopyrrolopyrrole polymers as organic semiconductors

Country Status (9)

Country Link
US (3) US20090302311A1 (enExample)
EP (1) EP2035428B1 (enExample)
JP (1) JP5374367B2 (enExample)
KR (1) KR101422054B1 (enExample)
AU (1) AU2007263828B2 (enExample)
BR (1) BRPI0713952A2 (enExample)
CA (1) CA2655076A1 (enExample)
TW (1) TWI444402B (enExample)
WO (1) WO2008000664A1 (enExample)

Families Citing this family (107)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070181179A1 (en) 2005-12-21 2007-08-09 Konarka Technologies, Inc. Tandem photovoltaic cells
US7781673B2 (en) 2005-07-14 2010-08-24 Konarka Technologies, Inc. Polymers with low band gaps and high charge mobility
AU2007263828B2 (en) 2006-06-30 2012-03-15 Basf Se Diketopyrrolopyrrole polymers as organic semiconductors
US8008424B2 (en) 2006-10-11 2011-08-30 Konarka Technologies, Inc. Photovoltaic cell with thiazole-containing polymer
US8008421B2 (en) 2006-10-11 2011-08-30 Konarka Technologies, Inc. Photovoltaic cell with silole-containing polymer
US7910684B2 (en) 2007-09-06 2011-03-22 Xerox Corporation Diketopyrrolopyrrole-based derivatives for thin film transistors
US7932344B2 (en) 2007-09-06 2011-04-26 Xerox Corporation Diketopyrrolopyrrole-based polymers
US8758880B2 (en) * 2007-10-25 2014-06-24 Basf Se Ketopyrroles as organic semiconductors
EP2114085A1 (en) * 2008-04-28 2009-11-04 Nederlandse Centrale Organisatie Voor Toegepast Natuurwetenschappelijk Onderzoek TNO Composite microphone, microphone assembly and method of manufacturing those
KR101830592B1 (ko) 2008-07-18 2018-02-20 유디씨 아일랜드 리미티드 전자 용품을 위한 아자피렌
US10224484B2 (en) 2008-10-31 2019-03-05 Basf Se Diketopyrrolopyrrole polymers for use in organic field effect transistors
US8912305B2 (en) * 2008-10-31 2014-12-16 Basf Se Diketopyrrolopyrrole polymers for use in organic field effect transistors
WO2010049323A1 (en) * 2008-10-31 2010-05-06 Basf Se Diketopyrrolopyrrole polymers for use in organic semiconductor devices
RU2011142634A (ru) 2009-03-23 2013-04-27 Басф Се Дикетопирролопиррольные полимеры для применения в органических полупроводниковых устройствах
US20100326525A1 (en) * 2009-03-26 2010-12-30 Thuc-Quyen Nguyen Molecular semiconductors containing diketopyrrolopyrrole and dithioketopyrrolopyrrole chromophores for small molecule or vapor processed solar cells
JP5396128B2 (ja) * 2009-03-31 2014-01-22 大阪瓦斯株式会社 ジケトピロロピロール骨格を有するポリマーおよび白色発光材料
US9067942B2 (en) * 2009-04-08 2015-06-30 Basf Se Pyrrolopyrrole derivatives, their manufacture and use as semiconductors
WO2010135701A1 (en) * 2009-05-21 2010-11-25 Polyera Corporation Conjugated polymers and their use in optoelectronic devices
WO2010138566A2 (en) * 2009-05-26 2010-12-02 University Of Florida Research Foundation, Inc. Green soluble conjugated polymers with high charge carrier mobilities
US8835579B2 (en) 2009-05-27 2014-09-16 Basf Se Process for polymerising (hetero)aromatic compounds
WO2010136353A1 (en) * 2009-05-27 2010-12-02 Basf Se Diketopyrrolopyrrole polymers for use in organic semiconductor devices
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
CN102640316B (zh) * 2009-08-28 2015-03-25 新加坡科技研究局 P型材料及有机电子器件
JP5653436B2 (ja) 2009-08-28 2015-01-14 エージェンシー フォー サイエンス, テクノロジー アンド リサーチ ポリマー半導体、デバイス、および関連する方法
EP2467412A2 (en) 2009-09-04 2012-06-27 Plextronics, Inc. Organic electronic devices and polymers, including photovoltaic cells and diketone-based and diketopyrrolopyrrole-based polymers
JP5782703B2 (ja) * 2009-10-29 2015-09-24 住友化学株式会社 高分子化合物及びそれを用いた電子素子
JP5588559B2 (ja) * 2010-03-20 2014-09-10 ポリエラ コーポレイション ピロロ[3,2−b]ピロール半導体化合物およびそれを組み込んだデバイス
US10050201B2 (en) 2010-04-19 2018-08-14 Merck Patent Gmbh Polymers of benzodithiophene and their use as organic semiconductors
EP2571919B1 (en) * 2010-05-19 2018-07-11 Basf Se Diketopyrrolopyrrole polymers for use in organic semiconductor devices
US20110315967A1 (en) * 2010-06-24 2011-12-29 Basf Se Organic field effect transistor with improved current on/off ratio and controllable threshold shift
JP6406824B2 (ja) 2010-06-24 2018-10-17 ビーエーエスエフ ソシエタス・ヨーロピアBasf Se 改良された電流オン/オフ比及び制御可能な閾値変動を有する有機電界効果トランジスタ
EP2599621B1 (en) 2010-07-27 2016-03-02 Konica Minolta Holdings, Inc. Gas barrier film, process for production of gas barrier film, and electronic device
WO2012017005A2 (en) 2010-08-05 2012-02-09 Basf Se Polymers based on benzodiones
GB201013820D0 (en) * 2010-08-18 2010-09-29 Cambridge Display Tech Ltd Low contact resistance organic thin film transistors
JP5853954B2 (ja) 2010-08-25 2016-02-09 コニカミノルタ株式会社 ガスバリア性フィルムの製造方法
CN103097431A (zh) * 2010-09-10 2013-05-08 住友化学株式会社 高分子化合物和有机光电转换装置
US8946376B2 (en) 2010-09-29 2015-02-03 Basf Se Semiconductors based on diketopyrrolopyrroles
WO2012050070A1 (ja) * 2010-10-13 2012-04-19 住友化学株式会社 高分子化合物及びそれを用いた有機光電変換素子
WO2012059386A1 (en) 2010-11-01 2012-05-10 Basf Se Polyimides as dielectric
US9187600B2 (en) 2010-11-01 2015-11-17 Basf Se Polyimides as dielectric
WO2012060283A1 (ja) * 2010-11-02 2012-05-10 住友化学株式会社 高分子化合物及びそれを用いた有機光電変換素子
US8598450B2 (en) * 2010-11-24 2013-12-03 Polyera Corporation Conjugated polymers and their use in optoelectronic devices
JP6005057B2 (ja) * 2010-12-22 2016-10-12 ビーエーエスエフ ソシエタス・ヨーロピアBasf Se 半導体構造およびその製造方法
JP5761203B2 (ja) 2010-12-27 2015-08-12 コニカミノルタ株式会社 ガスバリア性フィルム及び電子デバイス
WO2012090665A1 (ja) 2010-12-27 2012-07-05 コニカミノルタホールディングス株式会社 ガスバリアフィルムの製造方法、ガスバリアフィルムおよび電子デバイス
KR20140023923A (ko) 2011-03-11 2014-02-27 메르크 파텐트 게엠베하 공액 중합체
WO2012130365A1 (en) 2011-03-25 2012-10-04 Merck Patent Gmbh Pyrrolo[3,2-b]pyrrole-2,5-diones and their use as organic semiconductors
WO2012165128A1 (ja) * 2011-05-27 2012-12-06 住友化学株式会社 高分子化合物及び有機光電変換素子
KR20140043761A (ko) * 2011-05-30 2014-04-10 바스프 에스이 커플링 반응을 이용한 폴리머의 제조 방법
WO2012175530A1 (en) 2011-06-22 2012-12-27 Basf Se Diketopyrrolopyrrole oligomers for use in organic semiconductor devices
JP5928469B2 (ja) 2011-08-09 2016-06-01 コニカミノルタ株式会社 有機光電変換素子、およびそれを用いた有機太陽電池
JP2013055322A (ja) * 2011-08-11 2013-03-21 Mitsubishi Chemicals Corp 光電変換素子、太陽電池及び太陽電池モジュール
WO2013028441A2 (en) 2011-08-19 2013-02-28 University Of Washington New poly(heteroarylene vinylene)s based on diketopyrrolopyrrole
KR102030859B1 (ko) * 2011-09-02 2019-10-10 바스프 에스이 디케토피롤로피롤 올리고머, 및 디케토피롤로피롤 올리고머를 포함하는 조성물
US9543521B2 (en) * 2011-11-15 2017-01-10 Basf Se Organic semiconductor device and process for its production
EP2783846A4 (en) 2011-11-24 2015-09-02 Konica Minolta Inc GAS BARRIER LAYER AND ELECTRONIC DEVICE THEREFOR
US8598299B2 (en) * 2011-12-06 2013-12-03 Xerox Corporation Semiconductor composition
US9978943B2 (en) 2011-12-07 2018-05-22 Basf Se Organic field effect transistor
EP2789024B1 (en) 2011-12-07 2015-11-18 Basf Se Diketopyrrolopyrrole polymers for use in organic semiconductor devices
JP5952551B2 (ja) 2011-12-12 2016-07-13 Necトーキン株式会社 導電性高分子組成物およびその製造方法、導電性高分子材料の製造方法、導電性基材の製造方法、電極の製造方法、電子デバイスの製造方法並びに固体電解コンデンサの製造方法
JP5872872B2 (ja) * 2011-12-12 2016-03-01 Necトーキン株式会社 導電性高分子組成物の製造方法、導電性高分子材料の製造方法、導電性基材の製造方法、電極の製造方法および固体電解コンデンサの製造方法
WO2013149897A1 (en) 2012-04-02 2013-10-10 Basf Se Phenanthro[9,10-b]furan polymers and small molecules for electronic applications
CN104334610A (zh) * 2012-04-04 2015-02-04 巴斯夫欧洲公司 二酮基吡咯并吡咯聚合物和小分子
US9379335B2 (en) 2012-04-08 2016-06-28 The Regents Of The University Of California Benzodipyrrolidones and their polymers: synthesis and applications for organic electronics and optoelectronics
WO2013172359A1 (ja) 2012-05-14 2013-11-21 コニカミノルタ株式会社 ガスバリア性フィルム、ガスバリア性フィルムの製造方法及び電子デバイス
WO2013182262A1 (en) * 2012-06-04 2013-12-12 Merck Patent Gmbh Organic semiconductors
WO2014016219A1 (en) 2012-07-23 2014-01-30 Basf Se Dithienobenzofuran polymers and small molecules for electronic application
WO2014031733A1 (en) * 2012-08-22 2014-02-27 University Of Washington Through Its Center For Commercialization Diketopyrrolopyrrole polymers for electronics and optoelectronics
CN104703685B (zh) * 2012-08-27 2017-03-15 康宁股份有限公司 半导体稠合噻吩聚合物油墨制剂
US9550791B2 (en) 2012-12-04 2017-01-24 Basf Se Functionnalized benzodithiophene polymers for electronic application
KR101589048B1 (ko) * 2012-12-14 2016-01-27 경상대학교산학협력단 신규한 유기반도체 화합물 및 이를 포함하는 유기전자소자
KR101514207B1 (ko) * 2013-04-15 2015-06-05 한국과학기술연구원 낮은 밴드갭을 갖는 고분자 화합물, 이를 포함하는 유기태양전지 및 이의 제조방법
EP2994945A1 (en) 2013-05-06 2016-03-16 Basf Se Soluble cyclic imides containing polymers as dielectrics in organic electronic applications
KR101485398B1 (ko) * 2013-05-07 2015-01-26 경상대학교산학협력단 다이케토피롤로피롤 중합체 및 이를 함유하는 유기 전자 소자
EP3013906B1 (en) * 2013-06-24 2020-03-25 Basf Se Polymers based on fused diketopyrrolopyrroles
EP2818493A1 (en) 2013-06-25 2014-12-31 Basf Se Near infrared absorbing polymers for electronic applications
US9786409B2 (en) 2013-06-27 2017-10-10 Basf Se Metathesis polymers as dielectrics
CN105849170B (zh) 2013-07-08 2018-10-19 巴斯夫欧洲公司 基于叠氮化物的交联剂
US9761803B2 (en) 2013-07-22 2017-09-12 Xerox Corporation Semiconductor composition
DE112014005330T5 (de) 2013-11-21 2016-08-04 Daicel Corporation Lösungsmittel zum Herstellen eines organischen Transistors
JP6354157B2 (ja) * 2013-12-26 2018-07-11 日立化成株式会社 電荷輸送性材料、該材料を用いたインク組成物、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、表示装置及び照明装置
KR101704110B1 (ko) * 2014-01-17 2017-02-07 주식회사 엘지화학 신규한 화합물 및 이를 포함하는 유기 태양 전지
KR101630173B1 (ko) 2014-01-17 2016-06-24 경상대학교산학협력단 비대칭 헤테로고리-비닐렌-헤테로고리계 다이케토피롤로피롤 중합체, 이를 채용하고 있는 유기 전자 소자 및 이를 제조하기 위한 단량체
US9399698B2 (en) 2014-01-31 2016-07-26 Xerox Corporation Processes for purifying diketopyrrolopyrrole copolymers
KR101513883B1 (ko) * 2014-02-07 2015-04-21 경상대학교산학협력단 신규한 중합체 및 이를 포함하는 유기전자소자
KR101600031B1 (ko) 2014-03-24 2016-03-07 경상대학교산학협력단 비대칭 다이케토피롤로피롤 중합체 및 이를 함유하는 유기 전자 소자
KR102143429B1 (ko) 2014-03-25 2020-08-11 경상대학교산학협력단 다이케토피롤로피롤 중합체 및 이를 채용하고 있는 유기 전자 소자
KR102099612B1 (ko) 2014-03-27 2020-04-10 경상대학교산학협력단 다이케토피롤로피롤 중합체 및 이를 채용하고 있는 유기 전자 소자
US10020456B2 (en) 2014-09-25 2018-07-10 Basf Se Ether-based polymers as photo-crosslinkable dielectrics
CN104774318B (zh) * 2015-04-08 2017-02-01 中国科学院化学研究所 一种2,2’‑二(苯并噻吩)乙烯聚合物及其制备方法与应用
US10109798B2 (en) * 2015-05-26 2018-10-23 Purdue Research Foundation Methods and compositions for enhancing processability and charge transport of polymer semiconductors
JP6463475B2 (ja) 2015-07-07 2019-02-06 富士フイルム株式会社 有機半導体素子、化合物、有機半導体組成物、および、有機半導体膜の製造方法
JP6442057B2 (ja) * 2015-07-07 2018-12-19 富士フイルム株式会社 有機半導体素子、化合物、有機半導体組成物、並びに、有機半導体膜及びその製造方法
EP3346515A4 (en) * 2015-09-02 2018-10-17 FUJIFILM Corporation Organic thin-film transistor, organic thin-film transistor manufacturing method, organic semiconductor composition, organic semiconductor film, and organic semiconductor film manufacturing method
KR20160088257A (ko) 2016-02-05 2016-07-25 경상대학교산학협력단 비대칭 헤테로고리-비닐렌-헤테로고리계 다이케토피롤로피롤 중합체, 이를 채용하고 있는 유기 전자 소자 및 이를 제조하기 위한 단량체
US10741766B2 (en) * 2016-05-12 2020-08-11 Samsung Electronics Co., Ltd. Organic semiconductor thin film and method of manufacturing the same and thin film transistor and electronic device
JP7026391B2 (ja) 2016-05-25 2022-02-28 クラップ カンパニー リミテッド 半導体ポリマー
WO2018060015A1 (en) 2016-09-27 2018-04-05 Basf Se Star-shaped styrene polymers with enhanced glass transition temperature
EP3519488A1 (en) 2016-09-27 2019-08-07 Basf Se Star-shaped and triblock polymers with enhanced crosslinkability
WO2018068722A1 (en) * 2016-10-11 2018-04-19 The Hong Kong University Of Science And Technology Ternary blend organic solar cells based on one donor polymer and two acceptors
JP7046395B2 (ja) 2018-03-07 2022-04-04 クラップ カンパニー リミテッド トップゲート・ボトムコンタクト有機電界効果トランジスタを製造するためのパターニング方法
KR102341687B1 (ko) 2018-03-08 2021-12-21 주식회사 클랩 반도체성 단일벽 탄소 나노튜브 및 유기 반도체 물질을 포함하는 유기 전계효과 트랜지스터
CN112074548B (zh) 2018-06-26 2023-07-25 Clap有限公司 作为电介质的乙烯醚类聚合物
CN111045296B (zh) * 2018-10-12 2024-12-27 康宁股份有限公司 用于有机薄膜晶体管的可uv图案化的聚合物掺混物
JP7151468B2 (ja) * 2018-12-25 2022-10-12 東洋インキScホールディングス株式会社 蛍光標識剤
EP3933949A1 (en) 2020-06-30 2022-01-05 Basf Se Composition comprising an organic semiconducting polymer and a crosslinking agent and organic photodiode thereof
WO2024035888A1 (en) * 2022-08-10 2024-02-15 Kennesaw State University Research And Service Foundation, Inc. Pyrrole derived compositions and sythesis methods

Family Cites Families (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR920002741A (ko) * 1990-07-20 1992-02-28 베르너 발데크 디케토피롤로피롤을 기재로 하는 전기 발색 조성물
DE59404868D1 (de) * 1993-07-20 1998-02-05 Ciba Geigy Ag In der Masse mit Diketopyrrolopyrrolpigmenten gefärbte Polyamide
EP0648770B1 (de) * 1993-10-13 2000-05-17 Ciba SC Holding AG Pyrrolo[3,4-c]pyrrole
US5492564A (en) * 1994-03-16 1996-02-20 Ciba-Geigy Corporation Diketopyrrolopyrrole pigment with high chroma
DE59507427D1 (de) * 1994-09-28 2000-01-20 Ciba Sc Holding Ag Mischkristalle und feste Lösungen von 1,4-Diketopyrrolopyrrolen
EP0718697B1 (en) * 1994-12-22 2001-11-21 Ciba SC Holding AG Electrophotographic photoreceptor
JP3704748B2 (ja) * 1995-06-23 2005-10-12 東洋インキ製造株式会社 有機エレクトロルミネッセンス素子用電子輸送材料およびそれを用いた有機エレクトロルミネッセンス素子
TW341572B (en) * 1995-09-20 1998-10-01 Ciba Sc Holding Ag Preparation of mixed crystals and solid solutions of 1,4-diketopyrrolopyrroles
DE59704157D1 (de) * 1996-01-30 2001-09-06 Ciba Sc Holding Ag Polymerisierbare Diketopyrrolopyrrole und damit hergestellte Polymere
DE69704084T2 (de) * 1996-12-10 2001-06-07 Ciba Specialty Chemicals Holding Inc., Basel Flüssigkristalline diketopyrrolopyrrole
DE69800715T2 (de) * 1997-01-27 2001-08-09 Ciba Speciality Chemicals Holding Inc., Basel Lösliche chromophore enthaltend gruppen mit verbesserter löslichkeit
TWI290164B (en) * 1999-08-26 2007-11-21 Ciba Sc Holding Ag DPP-containing conjugated polymers and electroluminescent devices
EP1087006B1 (en) * 1999-09-27 2003-10-15 Ciba SC Holding AG Electroluminescent devices comprising diketopyrrolopyrroles
EP1087005B1 (en) * 1999-09-27 2004-02-25 Ciba SC Holding AG Fluorescent diketopyrrolopyrroles
EP1101800B1 (en) * 1999-11-17 2003-06-25 Ciba SC Holding AG Diketopyrrolopyrrole
US6388093B1 (en) * 2001-01-05 2002-05-14 Sun Chemical Corporation Syntheses for preparing 1,4-diketopyrrolo [3,4-c]pyrroles
US6878505B2 (en) * 2001-05-28 2005-04-12 Fuji Photo Film Co., Ltd. Photosensitive composition
WO2003048268A1 (fr) * 2001-12-03 2003-06-12 Toyo Ink Mfg. Co., Ltd. Composition pour element electroluminescent organique et element electroluminescent organique utilisant cette composition
EP1478713A1 (en) * 2002-02-01 2004-11-24 Ciba SC Holding AG Fluorescent compositions comprising diketopyrrolopyrroles
JP4093083B2 (ja) * 2003-03-10 2008-05-28 東洋インキ製造株式会社 有機エレクトロルミネッセンス素子材料およびそれを使用した有機エレクトロルミネッセンス素子
MXPA05010866A (es) * 2003-04-10 2006-06-05 Ciba Sc Holding Ag Dicetopirrolopirroles fluorescentes.
CN100572419C (zh) * 2003-10-28 2009-12-23 西巴特殊化学品控股有限公司 新颖的二酮基吡咯并吡咯聚合物
JP4911486B2 (ja) 2005-04-13 2012-04-04 東洋インキScホールディングス株式会社 有機トランジスタ
AU2007263828B2 (en) 2006-06-30 2012-03-15 Basf Se Diketopyrrolopyrrole polymers as organic semiconductors
US7932344B2 (en) * 2007-09-06 2011-04-26 Xerox Corporation Diketopyrrolopyrrole-based polymers
US7910684B2 (en) 2007-09-06 2011-03-22 Xerox Corporation Diketopyrrolopyrrole-based derivatives for thin film transistors
US8404864B2 (en) 2007-10-09 2013-03-26 Basf Se Pyrrolopyrrole derivatives, their manufacture and use
US8912305B2 (en) 2008-10-31 2014-12-16 Basf Se Diketopyrrolopyrrole polymers for use in organic field effect transistors
WO2010049323A1 (en) 2008-10-31 2010-05-06 Basf Se Diketopyrrolopyrrole polymers for use in organic semiconductor devices
CN102640316B (zh) 2009-08-28 2015-03-25 新加坡科技研究局 P型材料及有机电子器件
US8946376B2 (en) * 2010-09-29 2015-02-03 Basf Se Semiconductors based on diketopyrrolopyrroles

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