JP6875991B2 - 分岐アルキル鎖を有するｄｐｐまたは（および）分岐アルキル鎖を有する縮合チオフェン、並びにそれらの半導体コポリマーの分子量を増加させるための設計戦略 - Google Patents

分岐アルキル鎖を有するｄｐｐまたは（および）分岐アルキル鎖を有する縮合チオフェン、並びにそれらの半導体コポリマーの分子量を増加させるための設計戦略 Download PDF

Info

Publication number
JP6875991B2
JP6875991B2 JP2017540154A JP2017540154A JP6875991B2 JP 6875991 B2 JP6875991 B2 JP 6875991B2 JP 2017540154 A JP2017540154 A JP 2017540154A JP 2017540154 A JP2017540154 A JP 2017540154A JP 6875991 B2 JP6875991 B2 JP 6875991B2
Authority
JP
Japan
Prior art keywords
substituted
unsubstituted
polymer
molecular weight
equal
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.)
Active
Application number
JP2017540154A
Other languages
English (en)
Japanese (ja)
Other versions
JP2018507289A5 (enExample
JP2018507289A (ja
Inventor
ハァ，ミンチエン
ニウ，ウェイジュン
ロバート マシューズ，ジェイムズ
ロバート マシューズ，ジェイムズ
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.)
Corning Inc
Original Assignee
Corning Inc
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 Corning Inc filed Critical Corning Inc
Publication of JP2018507289A publication Critical patent/JP2018507289A/ja
Publication of JP2018507289A5 publication Critical patent/JP2018507289A5/ja
Application granted granted Critical
Publication of JP6875991B2 publication Critical patent/JP6875991B2/ja
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Images

Classifications

    • 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
    • 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
    • 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
    • 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
    • C08G61/124—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 nitrogen atom in the ring
    • 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
    • C08G61/125—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 oxygen atom in the ring
    • 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
    • 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
    • H10K85/151—Copolymers
    • 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
    • C08G2261/12—Copolymers
    • C08G2261/124—Copolymers alternating
    • 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
    • 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
    • C08G2261/21—Stereochemical aspects
    • 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
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
    • C08G2261/322—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed
    • C08G2261/3223—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed containing one or more sulfur atoms as the only heteroatom, e.g. thiophene
    • 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
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
    • C08G2261/324—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed
    • C08G2261/3243—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed containing one or more sulfur atoms as the only heteroatom, e.g. benzothiophene
    • 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
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/33—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain
    • C08G2261/334—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain containing heteroatoms
    • 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
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/34—Monomer units or repeat units incorporating structural elements in the main chain incorporating partially-aromatic structural elements in the main chain
    • C08G2261/344—Monomer units or repeat units incorporating structural elements in the main chain incorporating partially-aromatic structural elements in the main chain containing heteroatoms
    • 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
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/36—Oligomers, i.e. comprising up to 10 repeat units
    • C08G2261/364—Oligomers, i.e. comprising up to 10 repeat units containing hetero atoms
    • 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
    • C08G2261/40—Polymerisation processes
    • C08G2261/41—Organometallic coupling reactions
    • C08G2261/414—Stille reactions
    • 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
    • C08G2261/90—Applications
    • C08G2261/92—TFT applications
    • 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
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/621—Aromatic anhydride or imide compounds, e.g. perylene tetra-carboxylic dianhydride or perylene tetracarboxylic di-imide

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
JP2017540154A 2015-01-29 2016-01-28 分岐アルキル鎖を有するｄｐｐまたは（および）分岐アルキル鎖を有する縮合チオフェン、並びにそれらの半導体コポリマーの分子量を増加させるための設計戦略 Active JP6875991B2 (ja)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
US201562109176P 2015-01-29 2015-01-29
US62/109,176 2015-01-29
US201562242681P 2015-10-16 2015-10-16
US62/242,681 2015-10-16
US14/968,168 US9580556B2 (en) 2015-01-29 2015-12-14 DPP with branched alkyl-chain or (and) fused thiophene with branched alkyl-chain and the related designing strategy to increase the molecular weight of their semi-conducting copolymers
US14/968,168 2015-12-14
PCT/US2016/015264 WO2016123286A1 (en) 2015-01-29 2016-01-28 Dpp with branched alkyl-chain or (and) fused thiophene with branched alkyl-chain and the related designing strategy to increase the molecular weight of their semi-conducting copolymers

Publications (3)

Publication Number Publication Date
JP2018507289A JP2018507289A (ja) 2018-03-15
JP2018507289A5 JP2018507289A5 (enExample) 2019-05-16
JP6875991B2 true JP6875991B2 (ja) 2021-05-26

Family

ID=55359738

Family Applications (1)

Application Number Title Priority Date Filing Date
JP2017540154A Active JP6875991B2 (ja) 2015-01-29 2016-01-28 分岐アルキル鎖を有するｄｐｐまたは（および）分岐アルキル鎖を有する縮合チオフェン、並びにそれらの半導体コポリマーの分子量を増加させるための設計戦略

Country Status (7)

Country Link
US (1) US9580556B2 (enExample)
EP (1) EP3250624A1 (enExample)
JP (1) JP6875991B2 (enExample)
KR (1) KR102471602B1 (enExample)
CN (1) CN107406585B (enExample)
TW (1) TWI725952B (enExample)
WO (1) WO2016123286A1 (enExample)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102542436B1 (ko) * 2017-06-08 2023-06-13 코닝 인코포레이티드 다른 중합체의 유기 반도체 중합체로의 도핑
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
CN118496480A (zh) * 2018-11-05 2024-08-16 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
CN111244274B (zh) * 2018-11-29 2025-07-11 康宁股份有限公司 具有垂直设计结构及基于给体-受体的有机半导体材料的高电流otft装置
CN111272838A (zh) * 2018-12-05 2020-06-12 康宁股份有限公司 具有大表面积垂直装置设计的基于噻吩基高性能有机半导体材料的气体传感器
CN111752105B (zh) * 2019-03-27 2025-10-21 康宁股份有限公司 用于有机薄膜晶体管的可光图案化的杂型有机半导体聚合物
CN112457328A (zh) * 2019-09-06 2021-03-09 康宁股份有限公司 通过Pd催化的直接(杂)芳基化或直接烯基化的基于FT4的有机半导体小分子的合成
CN114062524B (zh) * 2020-07-31 2026-07-17 康宁股份有限公司 气体传感器

Family Cites Families (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7838623B2 (en) 2004-09-14 2010-11-23 Corning Incorporated Fused thiophenes, methods for making fused thiophenes, and uses thereof
US7893191B2 (en) 2007-02-28 2011-02-22 Corning Incorporated Fused thiophenes, methods for making fused thiophenes, and uses thereof
US7705108B2 (en) 2004-09-14 2010-04-27 Corning Incorporated Fused thiophenes, methods for making fused thiophenes, and uses thereof
US20130085256A1 (en) * 2004-09-14 2013-04-04 Mingqian He Fused thiophenes, methods of making fused thiophenes, and uses thereof
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
US8487114B2 (en) 2008-03-31 2013-07-16 Corning Incorporated Fused thiophenes and methods for making and using same
CN102362314B (zh) 2009-03-23 2014-09-24 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
BRPI1014578A2 (pt) 2009-04-08 2015-08-25 Basf Se Composto, material, camada ou componente semicondutor orgânico, dispositivo, semicondutor, e, uso de um composto.
US7919634B2 (en) * 2009-05-28 2011-04-05 Corning Incorporated Fused thiophenes, articles, and methods thereof
US8624232B2 (en) 2009-08-28 2014-01-07 Prashant Sonar Ambipolar polymeric semiconductor materials and organic electronic devices
US8217183B2 (en) 2010-05-18 2012-07-10 Corning Incorporated Methods of making fused thiophenes
KR101839636B1 (ko) 2010-05-19 2018-03-16 바스프 에스이 유기 반도체 소자에 사용하기 위한 디케토피롤로피롤 중합체
US8278346B2 (en) 2010-08-06 2012-10-02 Corning Incorporated Di-tin fused thiophene compounds and polymers and methods of making
US8394918B2 (en) * 2011-02-28 2013-03-12 Corning Incorporated Five-ring fused heteroaromatic compounds and conjugated polymers thereof
US8642719B2 (en) 2011-02-28 2014-02-04 Corning Incorporated Solvent mixture for molecular weight control
JP6165135B2 (ja) 2011-06-22 2017-07-19 ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ 有機半導体素子内で使用するためのジケトピロロピロールオリゴマー
JP6296980B2 (ja) 2011-09-02 2018-03-20 ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ ジケトピロロピロールオリゴマー、及びジケトピロロピロールオリゴマーを含む組成物
JP5760875B2 (ja) * 2011-09-07 2015-08-12 住友化学株式会社 高分子化合物及びそれを用いた有機トランジスタ
US8846855B2 (en) * 2011-10-31 2014-09-30 Corning Incorporated Conjugated fused thiophenes, methods of making conjugated fused thiophenes, and uses thereof
WO2013066973A1 (en) * 2011-10-31 2013-05-10 Corning Incorporated Fused thiophenes, methods of making fused thiophenes, and uses thereof
EP2789024B1 (en) 2011-12-07 2015-11-18 Basf Se Diketopyrrolopyrrole polymers for use in organic semiconductor devices
KR102079604B1 (ko) 2012-04-04 2020-04-08 바스프 에스이 디케토피롤로피롤 중합체 및 소분자
CN102775273B (zh) * 2012-07-05 2014-09-10 北京大学 一种分叉烷基链及其制备和在有机共轭分子中的应用
JP6127789B2 (ja) * 2012-07-13 2017-05-17 三菱化学株式会社 コポリマー、有機半導体材料、有機電子デバイス及び太陽電池モジュール
US9312044B2 (en) * 2012-08-27 2016-04-12 Corning Incoporated Semiconducting fused thiophene polymer ink formulation
US9070882B2 (en) * 2013-08-22 2015-06-30 Corning Incorporated Boron ester fused thiophene monomers
KR20160091362A (ko) * 2013-11-27 2016-08-02 코닝 인코포레이티드 반전도성 중합체의 향상된 유동 반응기 합성

Also Published As

Publication number Publication date
CN107406585A (zh) 2017-11-28
CN107406585B (zh) 2020-06-19
US20160222167A1 (en) 2016-08-04
KR20170109622A (ko) 2017-09-29
TW201638140A (zh) 2016-11-01
US9580556B2 (en) 2017-02-28
WO2016123286A1 (en) 2016-08-04
KR102471602B1 (ko) 2022-11-28
TWI725952B (zh) 2021-05-01
EP3250624A1 (en) 2017-12-06
JP2018507289A (ja) 2018-03-15

Similar Documents

Publication Publication Date Title
JP5107712B2 (ja) 縮合チオフェン、縮合チオフェンの製造方法、およびその使用方法
US9580556B2 (en) DPP with branched alkyl-chain or (and) fused thiophene with branched alkyl-chain and the related designing strategy to increase the molecular weight of their semi-conducting copolymers
US7838623B2 (en) Fused thiophenes, methods for making fused thiophenes, and uses thereof
US8846855B2 (en) Conjugated fused thiophenes, methods of making conjugated fused thiophenes, and uses thereof
JP2015502921A (ja) 縮合チオフェン、縮合チオフェンの製造方法、およびその使用
JP7159586B2 (ja) 芳香族化合物、有機半導体層、及び有機薄膜トランジスタ
JP5123289B2 (ja) シリルエチニル基を有するアセン−チオフェンコポリマー
US9761803B2 (en) Semiconductor composition
CA2797308C (en) Semiconductor composition
CN101415745B (zh) 并苯-噻吩共聚物
US20160329496A1 (en) Processes for purifying diketopyrrolopyrrole copolymers
KR20120079822A (ko) 유기 반도체 화합물 및 이를 포함하는 트랜지스터와 전자 소자
JP2020057787A (ja) ビフェニレン誘導体、有機半導体層、及び有機薄膜トランジスタ
CN109715696B (zh) 稠合噻吩-芳基噻二唑聚合物、制造所述聚合物的方法及其用途
KR20160023878A (ko) 중합체 및 이를 사용한 태양 전지
JP4017533B2 (ja) ベンゾジイミダゾール化合物およびその製造方法
JP6709275B2 (ja) 有機半導体膜、有機半導体素子、重合体及び有機半導体組成物
Lee et al. Preparation and properties of a novel polythiophene, poly [(3‐hexyliminomethyl) thiophene] with a high regioregularity
JP7508917B2 (ja) 共役ポリマー、有機半導体層形成用溶液、有機半導体層、有機薄膜トランジスタ及びシクロペンタビフェニレン化合物
Tassinari et al. Polymers with alkylsulfanyl side chains for bulk heterojunction solar cells: toward a greener strategy
JP6573840B2 (ja) 有機半導体素子、並びに、これに用いる有機半導体膜、化合物及び有機半導体組成物
JP2007197450A (ja) 高分子化合物およびその合成法と使用法
JP2011084572A (ja) 高分子化合物およびその合成法と使用法

Legal Events

Date Code Title Description
A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20171016

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20190128

A621 Written request for application examination

Free format text: JAPANESE INTERMEDIATE CODE: A621

Effective date: 20190128

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20190403

A977 Report on retrieval

Free format text: JAPANESE INTERMEDIATE CODE: A971007

Effective date: 20200122

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20200205

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20200507

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20200812

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20201109

TRDD Decision of grant or rejection written
A01 Written decision to grant a patent or to grant a registration (utility model)

Free format text: JAPANESE INTERMEDIATE CODE: A01

Effective date: 20210331

A61 First payment of annual fees (during grant procedure)

Free format text: JAPANESE INTERMEDIATE CODE: A61

Effective date: 20210423

R150 Certificate of patent or registration of utility model

Ref document number: 6875991

Country of ref document: JP

Free format text: JAPANESE INTERMEDIATE CODE

Ref document number: 6875991

Country of ref document: JP

Free format text: JAPANESE INTERMEDIATE CODE: R150

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250