CA2613719C - Thiophene electronic devices - Google Patents

Thiophene electronic devices Download PDF

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Publication number
CA2613719C
CA2613719C CA2613719A CA2613719A CA2613719C CA 2613719 C CA2613719 C CA 2613719C CA 2613719 A CA2613719 A CA 2613719A CA 2613719 A CA2613719 A CA 2613719A CA 2613719 C CA2613719 C CA 2613719C
Authority
CA
Canada
Prior art keywords
aryl
alkoxy
semiconductor
carbon atoms
alkyl
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.)
Expired - Fee Related
Application number
CA2613719A
Other languages
English (en)
French (fr)
Other versions
CA2613719A1 (en
Inventor
Ping Liu
Beng S. Ong
Yiliang Wu
Yuning Li
Hualong Pan
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Samsung Electronics Co Ltd
Original Assignee
Xerox Corp
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Xerox Corp filed Critical Xerox Corp
Publication of CA2613719A1 publication Critical patent/CA2613719A1/en
Application granted granted Critical
Publication of CA2613719C publication Critical patent/CA2613719C/en
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • 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
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/655—Aromatic compounds comprising a hetero atom comprising only sulfur as heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
    • H10K10/40—Organic transistors
    • H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
    • H10K10/462—Insulated gate field-effect transistors [IGFETs]
    • H10K10/464—Lateral top-gate IGFETs comprising only a single gate
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
    • H10K10/40—Organic transistors
    • H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
    • H10K10/462—Insulated gate field-effect transistors [IGFETs]
    • H10K10/466—Lateral bottom-gate IGFETs comprising only a single gate
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
    • H10K10/40—Organic transistors
    • H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
    • H10K10/462—Insulated gate field-effect transistors [IGFETs]
    • H10K10/484—Insulated gate field-effect transistors [IGFETs] characterised by the channel regions
    • 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
    • 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

Landscapes

  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Thin Film Transistor (AREA)
  • Electroluminescent Light Sources (AREA)
CA2613719A 2006-12-14 2007-12-07 Thiophene electronic devices Expired - Fee Related CA2613719C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US11/638,725 2006-12-14
US11/638,725 US7718998B2 (en) 2006-12-14 2006-12-14 Thiophene electronic devices

Publications (2)

Publication Number Publication Date
CA2613719A1 CA2613719A1 (en) 2008-06-14
CA2613719C true CA2613719C (en) 2013-02-19

Family

ID=39204957

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2613719A Expired - Fee Related CA2613719C (en) 2006-12-14 2007-12-07 Thiophene electronic devices

Country Status (6)

Country Link
US (1) US7718998B2 (enExample)
EP (1) EP1933394B1 (enExample)
JP (1) JP2008153666A (enExample)
CN (1) CN101207182B (enExample)
CA (1) CA2613719C (enExample)
TW (1) TW200840105A (enExample)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20090181509A1 (en) * 2008-01-14 2009-07-16 Xerox Corporation Polymer semiconductors with high mobility
JP5487655B2 (ja) * 2008-04-17 2014-05-07 株式会社リコー ［１］ベンゾチエノ［３，２‐ｂ］［１］ベンゾチオフェン化合物およびその製造方法、それを用いた有機電子デバイス
CN102224619A (zh) * 2008-10-21 2011-10-19 江森自控帅福得先进能源动力系统有限责任公司 电池的改善电极结构
US7872258B2 (en) * 2008-11-19 2011-01-18 Xerox Corporation Organic thin-film transistors
CN106479239A (zh) * 2008-12-19 2017-03-08 沃尔贝克材料有限公司 包含多链脂质的油墨和涂料
US7919634B2 (en) * 2009-05-28 2011-04-05 Corning Incorporated Fused thiophenes, articles, and methods thereof
US20110031475A1 (en) * 2009-08-10 2011-02-10 Xerox Corporation Semiconductor Composition
US8513374B2 (en) 2009-09-30 2013-08-20 Falguni Dasgupta Biocompatible and biodegradable polymers from renewable natural polyphenols
US7956199B2 (en) * 2009-10-08 2011-06-07 Xerox Corporation Methods for preparing benzodithiophenes
US8304512B2 (en) * 2010-01-19 2012-11-06 Xerox Corporation Benzodithiophene based materials compositions
JP5725494B2 (ja) * 2010-08-18 2015-05-27 国立大学法人岩手大学 有機半導体材料並びに有機半導体装置及びその製造方法
US8742403B2 (en) 2011-03-08 2014-06-03 Samsung Electronics Co., Ltd. Xanthene based semiconductor compositions
WO2012156500A1 (en) * 2011-05-18 2012-11-22 Université Libre de Bruxelles Semiconducting compound for gas sensing
CN102643290A (zh) * 2012-04-17 2012-08-22 中国科学院化学研究所 二苯并并四噻吩化合物及其制备方法与应用
TWI580683B (zh) * 2012-08-15 2017-05-01 Teijin Ltd Organic semiconductor solutions and organic semiconductor films
JP6364878B2 (ja) * 2014-03-31 2018-08-01 東ソー株式会社 有機薄膜トランジスタ
JP2017059651A (ja) * 2015-09-16 2017-03-23 株式会社東芝 光電変換材料分散液とその製造方法、光電変換膜の製造方法と製造装置、および光電変換素子
CN112819125A (zh) * 2021-01-27 2021-05-18 北京印刷学院 一种导电油墨、rfid织物标签及其制备方法

Family Cites Families (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3151997B2 (ja) * 1993-03-18 2001-04-03 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
US5619357A (en) 1995-06-06 1997-04-08 International Business Machines Corporation Flat panel display containing black matrix polymer
US5969376A (en) 1996-08-23 1999-10-19 Lucent Technologies Inc. Organic thin film transistor having a phthalocyanine semiconductor layer
US6107117A (en) 1996-12-20 2000-08-22 Lucent Technologies Inc. Method of making an organic thin film transistor
JPH10340786A (ja) * 1997-06-09 1998-12-22 Toyo Ink Mfg Co Ltd 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
US5777070A (en) 1997-10-23 1998-07-07 The Dow Chemical Company Process for preparing conjugated polymers
JP4963754B2 (ja) * 1997-10-23 2012-06-27 イシス イノベイション リミテッド 光放射デンドリマー及び光放射装置
JP4061561B2 (ja) * 1998-10-21 2008-03-19 富士電機ホールディングス株式会社 有機分子配向薄膜用材料及び有機分子配向薄膜の製造方法
US6770904B2 (en) 2002-01-11 2004-08-03 Xerox Corporation Polythiophenes and electronic devices generated therefrom
US7250625B2 (en) 2002-01-11 2007-07-31 Xerox Corporation Polythiophenes and electronic devices generated therefrom
US20030227014A1 (en) 2002-06-11 2003-12-11 Xerox Corporation. Process for forming semiconductor layer of micro-and nano-electronic devices
US20070069197A1 (en) * 2003-08-15 2007-03-29 Universite Laval Monomers, oligomers and polymers of 2-functionalized and 2,7-difunctionalized carbzoles
DE602004024629D1 (de) * 2003-10-15 2010-01-28 Merck Patent Gmbh Polybenzodithiophene
US7402681B2 (en) 2004-12-14 2008-07-22 Xerox Corporation Compound with indolocarbazole moieties and devices containing such compound
US20060124921A1 (en) 2004-12-14 2006-06-15 Xerox Corporation Compound with indolocarbazole moieties and devices containing such compound
JP4614272B2 (ja) * 2004-12-28 2011-01-19 国立大学法人京都大学 新規チオフェン誘導体及びそれを用いたトランジスタ素子
FR2881745A1 (fr) * 2005-02-08 2006-08-11 Univ Aix Marseille Ii Derives d'oligothiophenes et leur application en electronique organique
WO2006113205A2 (en) * 2005-04-15 2006-10-26 E. I. Du Pont De Nemours And Company Aryl-ethylene substituted aromatic compounds and their use as organic semiconductors
US8044219B2 (en) * 2005-05-13 2011-10-25 Agc Seimi Chemical., Ltd. Amino group-containing heterocyclic derivatives and sensitizing dyes for photoelectric conversion containing the heterocyclic derivatives
KR20070017692A (ko) * 2005-08-08 2007-02-13 삼성전자주식회사 저분자 공액 질소 화합물 및 이를 이용한 소자
KR20090080522A (ko) * 2006-11-14 2009-07-24 이데미쓰 고산 가부시키가이샤 유기 박막 트랜지스터 및 유기 박막 발광 트랜지스터
JP5308164B2 (ja) * 2006-12-04 2013-10-09 出光興産株式会社 有機薄膜トランジスタ及び有機薄膜発光トランジスタ

Also Published As

Publication number Publication date
US20080146776A1 (en) 2008-06-19
EP1933394A2 (en) 2008-06-18
JP2008153666A (ja) 2008-07-03
CN101207182B (zh) 2012-02-08
US7718998B2 (en) 2010-05-18
TW200840105A (en) 2008-10-01
CN101207182A (zh) 2008-06-25
CA2613719A1 (en) 2008-06-14
EP1933394A3 (en) 2010-06-23
EP1933394B1 (en) 2019-06-26

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Effective date: 20141208

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Effective date: 20240802