CN102084436B - 聚(5,5′-二(噻吩-2-基)苯并[2,1-b;3,4-b′]二噻吩)及其作为高性能可溶液加工半导体聚合物的用途 - Google Patents

聚(5,5′-二(噻吩-2-基)苯并[2,1-b;3,4-b′]二噻吩)及其作为高性能可溶液加工半导体聚合物的用途 Download PDF

Info

Publication number
CN102084436B
CN102084436B CN2009801259716A CN200980125971A CN102084436B CN 102084436 B CN102084436 B CN 102084436B CN 2009801259716 A CN2009801259716 A CN 2009801259716A CN 200980125971 A CN200980125971 A CN 200980125971A CN 102084436 B CN102084436 B CN 102084436B
Authority
CN
China
Prior art keywords
group
alkyl
aryl
thin film
independently selected
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
CN2009801259716A
Other languages
English (en)
Chinese (zh)
Other versions
CN102084436A (zh
Inventor
M·卡斯特勒
S·克勒
K·米伦
M·刘
D·贝克曼
R·里格尔
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.)
Max Planck Gesellschaft zur Foerderung der Wissenschaften
Clap Co Ltd
Original Assignee
BASF SE
Max Planck Gesellschaft zur Foerderung der Wissenschaften
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 BASF SE, Max Planck Gesellschaft zur Foerderung der Wissenschaften filed Critical BASF SE
Publication of CN102084436A publication Critical patent/CN102084436A/zh
Application granted granted Critical
Publication of CN102084436B publication Critical patent/CN102084436B/zh
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Images

Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/12Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D495/00Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D495/00Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04Ortho-condensed systems
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • 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
    • C08G61/126Macromolecular 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
    • HELECTRICITY
    • H01ELECTRIC ELEMENTS
    • H01BCABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B1/00Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
    • H01B1/06Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
    • H01B1/12Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
    • HELECTRICITY
    • H01ELECTRIC ELEMENTS
    • H01BCABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B1/00Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
    • H01B1/06Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
    • H01B1/12Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
    • H01B1/124Intrinsically conductive polymers
    • H01B1/127Intrinsically conductive polymers comprising five-membered aromatic rings in the main chain, e.g. polypyrroles, polythiophenes
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K10/00Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/10Organic polymers or oligomers
    • H10K85/111Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • H10K85/113Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K10/00Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
    • H10K10/40Organic transistors
    • H10K10/46Field-effect transistors, e.g. organic thin-film transistors [OTFT]
    • H10K10/462Insulated gate field-effect transistors [IGFETs]
    • H10K10/464Lateral top-gate IGFETs comprising only a single gate
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K10/00Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
    • H10K10/40Organic transistors
    • H10K10/46Field-effect transistors, e.g. organic thin-film transistors [OTFT]
    • H10K10/462Insulated gate field-effect transistors [IGFETs]
    • H10K10/466Lateral bottom-gate IGFETs comprising only a single gate
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/10Organic polymers or oligomers
    • H10K85/151Copolymers
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60Organic compounds having low molecular weight
    • H10K85/649Aromatic compounds comprising a hetero atom
    • H10K85/657Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • 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
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02EREDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00Energy generation through renewable energy sources
    • Y02E10/50Photovoltaic [PV] energy
    • Y02E10/549Organic PV cells

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Thin Film Transistor (AREA)
  • Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
  • Photovoltaic Devices (AREA)
CN2009801259716A 2008-07-02 2009-06-25 聚(5,5′-二(噻吩-2-基)苯并[2,1-b;3,4-b′]二噻吩)及其作为高性能可溶液加工半导体聚合物的用途 Expired - Fee Related CN102084436B (zh)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
EP08159524.1 2008-07-02
EP08159524 2008-07-02
EP09153369 2009-02-20
EP09153369.5 2009-02-20
PCT/EP2009/057984 WO2010000669A1 (en) 2008-07-02 2009-06-25 Poly(5,5'bis(thiophen-2-yl)-benzo[2,1-b;3,4-b']dithiophene) and its use as high performance solution processable semiconducting polymer

Publications (2)

Publication Number Publication Date
CN102084436A CN102084436A (zh) 2011-06-01
CN102084436B true CN102084436B (zh) 2012-10-17

Family

ID=40999846

Family Applications (1)

Application Number Title Priority Date Filing Date
CN2009801259716A Expired - Fee Related CN102084436B (zh) 2008-07-02 2009-06-25 聚(5,5′-二(噻吩-2-基)苯并[2,1-b;3,4-b′]二噻吩)及其作为高性能可溶液加工半导体聚合物的用途

Country Status (7)

Country Link
US (1) US8598304B2 (enExample)
EP (1) EP2297748B1 (enExample)
JP (1) JP5735418B2 (enExample)
KR (1) KR101561323B1 (enExample)
CN (1) CN102084436B (enExample)
TW (1) TWI476225B (enExample)
WO (1) WO2010000669A1 (enExample)

Families Citing this family (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9221944B2 (en) 2008-12-18 2015-12-29 Basf Se Semiconductor materials prepared from dithienylvinylene copolymers
WO2010125011A2 (de) 2009-04-28 2010-11-04 Basf Se Verfahren zur herstellung von halbleitenden schichten
KR101772711B1 (ko) 2009-06-05 2017-09-12 바스프 에스이 비티오펜-비닐렌 융합 중합체
JP5634509B2 (ja) 2009-06-15 2014-12-03 ビーエーエスエフ ソシエタス・ヨーロピアBasf Se 位置規則性のポリ−(3−置換)チオフェン、セレノフェン、チアゾール及びセレナゾールの製造方法
US8440785B2 (en) 2009-06-30 2013-05-14 Plextronics, Inc. Compositions, methods and polymers
JP5774599B2 (ja) 2009-12-02 2015-09-09 ビーエーエスエフ ソシエタス・ヨーロピアBasf Se ジチエノベンゾ−チエノ[3,2−b]チオフェン−コポリマーとその溶液加工可能な高機能性半導電性ポリマーとしての利用
US8729220B2 (en) 2010-03-31 2014-05-20 Basf Se Annellated dithiophene copolymers
WO2011120951A1 (en) 2010-03-31 2011-10-06 Basf Se Annealed dithiophene copolymers
DE112011101363T5 (de) 2010-04-19 2013-02-07 Merck Patent Gmbh Polymere des Benzodithiophens und ihre Verwendung als organische Halbleiter
JP5638695B2 (ja) * 2010-06-25 2014-12-10 オーシャンズ キング ライティング サイエンス アンド テクノロジー シーオー.,エルティーディー ベンゾジチオフェン及びチエノピラジンをベースとした共役ポリマー、その調製方法及びその使用
US10753023B2 (en) 2010-08-13 2020-08-25 Kimberly-Clark Worldwide, Inc. Toughened polylactic acid fibers
US8394918B2 (en) 2011-02-28 2013-03-12 Corning Incorporated Five-ring fused heteroaromatic compounds and conjugated polymers thereof
EP2699617A1 (en) * 2011-04-18 2014-02-26 Merck Patent GmbH Conjugated polymers
US9573158B2 (en) 2014-01-03 2017-02-21 The Regents Of The University Of California High mobility polymer thin-film transistors with capillarity-mediated self-assembly
US10186661B2 (en) 2015-03-02 2019-01-22 The Regents Of The University Of California Blade coating on nanogrooved substrates yielding aligned thin films of high mobility semiconducting polymers
KR101424978B1 (ko) * 2012-05-24 2014-07-31 경상대학교산학협력단 길만시약 화합물을 이용한 헤테로 융합고리 화합물의 신규한 제조방법
US9881712B2 (en) * 2012-07-20 2018-01-30 Rohm And Haas Electronic Materials Llc Highly crystalline electrically conducting polymers, methods of manufacture thereof and articles comprising the same
CN103664994A (zh) * 2012-08-31 2014-03-26 昆山维信诺显示技术有限公司 苯并二噻吩类衍生物有机电致发光材料及其应用
US10128441B2 (en) 2012-09-07 2018-11-13 The Regents Of The University Of California Field-effect transistors based on macroscopically oriented polymers
US9559306B2 (en) 2012-09-07 2017-01-31 The Regents Of The University Of California Field-effect transistors based on macroscopically oriented polymers with high saturation mobility
CN103848969B (zh) * 2012-11-28 2016-03-30 海洋王照明科技股份有限公司 一种含噻唑并噻唑-二苯并噻吩苯并二噻吩聚合物及其制备与应用
US9515273B2 (en) 2012-12-24 2016-12-06 Indian Institute Of Technology Kanpur Thin film transistor with a current-induced channel
JP6488616B2 (ja) * 2013-10-04 2019-03-27 日産化学株式会社 電荷輸送性薄膜形成用ワニス、電荷輸送性薄膜及び有機エレクトロルミネッセンス素子
TWI508993B (zh) * 2013-10-30 2015-11-21 Univ Nat Taiwan 予體-受體交替共軛高分子及使用其所製成之太陽能電池元件
US20170077405A1 (en) * 2014-03-21 2017-03-16 Lg Chem, Ltd. Polymer and organic solar cell comprising same
KR101698666B1 (ko) * 2014-03-27 2017-01-23 주식회사 엘지화학 공중합체 및 이를 포함하는 유기 태양 전지
CN105914052B (zh) * 2016-04-18 2018-03-09 深圳清华大学研究院 聚合物电极膜及其制备方法
US11296290B2 (en) 2018-03-07 2022-04-05 Clap Co., Ltd. Patterning method for preparing top-gate, bottom-contact organic field effect transistors
EP3762980B1 (en) 2018-03-08 2023-08-09 Clap Co., Ltd. Organic field effect transistor comprising semiconducting single-walled carbon nanotubes and organic semiconducting material
KR102457044B1 (ko) 2018-06-26 2022-10-21 주식회사 클랩 유전체로서의 비닐에테르계 고분자
DE102018008146A1 (de) * 2018-10-15 2020-04-16 Giesecke+Devrient Currency Technology Gmbh Sicherheitselement mit Mikroreflektoren zur perspektivischen Darstellung eines Motivs

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101170161A (zh) * 2006-10-25 2008-04-30 施乐公司 电子器件

Family Cites Families (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US388744A (en) * 1888-08-28 Anvil heel-shouldering machine in the manufacture of lasts
US373276A (en) * 1887-11-15 Toaster
US5198153A (en) * 1989-05-26 1993-03-30 International Business Machines Corporation Electrically conductive polymeric
JP3224829B2 (ja) 1991-08-15 2001-11-05 株式会社東芝 有機電界効果型素子
JPH07188399A (ja) * 1993-12-27 1995-07-25 Unitika Ltd 光照射部が導電性に変化する成形性またはフィルム形成性組成物
WO1996021659A1 (en) 1995-01-10 1996-07-18 University Of Technology, Sydney Organic semiconductor
DE602004024629D1 (de) * 2003-10-15 2010-01-28 Merck Patent Gmbh Polybenzodithiophene
KR20070112791A (ko) 2005-03-11 2007-11-27 메르크 파텐트 게엠베하 티오펜 및 셀레노펜 함유 단량체, 올리고머 및 중합체
ATE465166T1 (de) 2005-06-09 2010-05-15 Merck Patent Gmbh Monomere, oligomere und polymere von thieno ä3,4- dü thiazol
JP4889085B2 (ja) * 2005-10-07 2012-02-29 株式会社リコー ベンゾジチオフェン化合物
EP2192123B1 (en) * 2006-03-10 2012-11-21 Sumitomo Chemical Company, Limited Fused tricyclic compounds useful in organic thin film devices such as transistors
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
CA2606985C (en) * 2006-10-25 2011-02-01 Xerox Corporation Electronic devices
US7834132B2 (en) * 2006-10-25 2010-11-16 Xerox Corporation Electronic devices
WO2009016107A1 (en) 2007-07-30 2009-02-05 Basf Se Method for depositing a semiconducting layer from a liquid

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101170161A (zh) * 2006-10-25 2008-04-30 施乐公司 电子器件

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
3,4-b`]dithiophene-Containing Polymers for Organic Field-Effect Transistors.《Adv. Mater.》.2009,第22卷83-86. *
Ralph Rieger et al..Rational Optimization of Benzo[2,1-b *

Also Published As

Publication number Publication date
TWI476225B (zh) 2015-03-11
WO2010000669A1 (en) 2010-01-07
KR101561323B1 (ko) 2015-10-16
KR20110043631A (ko) 2011-04-27
CN102084436A (zh) 2011-06-01
JP5735418B2 (ja) 2015-06-17
TW201008978A (en) 2010-03-01
US20110168264A1 (en) 2011-07-14
JP2011526631A (ja) 2011-10-13
EP2297748B1 (en) 2017-01-04
US8598304B2 (en) 2013-12-03
EP2297748A1 (en) 2011-03-23

Similar Documents

Publication Publication Date Title
CN102084436B (zh) 聚(5,5′-二(噻吩-2-基)苯并[2,1-b;3,4-b′]二噻吩)及其作为高性能可溶液加工半导体聚合物的用途
CN102639591B (zh) 二噻吩并苯并噻吩并[3,2-b]噻吩共聚物及其作为高性能可溶液加工半导体聚合物的用途
CN102083838B (zh) 基于二噻吩并[2,3-d:2′,3′-d′]苯并[1,2-b:4,5-b′]二噻吩的高性能可溶液加工半导体
CN102317345B (zh) 由二噻吩基亚乙烯基共聚物制备的半导体材料
TWI523884B (zh) 以交替式供體受體共聚物為主之高效溶液可加工半傳導性聚合物
CN102459398B (zh) 稠合的联噻吩-亚乙烯基共聚物
KR20130040830A (ko) 어닐링된 디티오펜 공중합체

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
C14 Grant of patent or utility model
GR01 Patent grant
TR01 Transfer of patent right
TR01 Transfer of patent right

Effective date of registration: 20211028

Address after: Seoul, South Kerean

Patentee after: Clap Ltd.

Patentee after: MAX-PLANCK-GESELLSCHAFT ZUR FORDERUNG DER WISSENSCHAFT E.V.

Address before: Ludwigshafen, Germany

Patentee before: BASF SE

Patentee before: MAX-PLANCK-GESELLSCHAFT ZUR FORDERUNG DER WISSENSCHAFT E.V.

CF01 Termination of patent right due to non-payment of annual fee
CF01 Termination of patent right due to non-payment of annual fee

Granted publication date: 20121017