CN102482297B - 含氟硅基乙炔基并五苯化合物和组合物以及其制造和使用方法 - Google Patents

含氟硅基乙炔基并五苯化合物和组合物以及其制造和使用方法 Download PDF

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Publication number
CN102482297B
CN102482297B CN201080023410.8A CN201080023410A CN102482297B CN 102482297 B CN102482297 B CN 102482297B CN 201080023410 A CN201080023410 A CN 201080023410A CN 102482297 B CN102482297 B CN 102482297B
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China
Prior art keywords
fluorine
pentacene
branching
substituted
mmol
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Expired - Fee Related
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CN201080023410.8A
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English (en)
Chinese (zh)
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CN102482297A (zh
Inventor
罗伯特·史蒂夫·克拉夫
约翰·E·安东尼
理查德·M·弗林
乔治·G·I·莫尔
马西亚·M·佩恩
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3M Innovative Properties Co
Outrider Technologies Inc
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3M Innovative Properties Co
Outrider Technologies Inc
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Publication of CN102482297A publication Critical patent/CN102482297A/zh
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02Silicon compounds
    • C07F7/08Compounds having one or more C—Si linkages
    • C07F7/0803Compounds with Si-C or Si-Si linkages
    • C07F7/081Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Thin Film Transistor (AREA)
  • Liquid Deposition Of Substances Of Which Semiconductor Devices Are Composed (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
CN201080023410.8A 2009-05-29 2010-05-28 含氟硅基乙炔基并五苯化合物和组合物以及其制造和使用方法 Expired - Fee Related CN102482297B (zh)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US18256109P 2009-05-29 2009-05-29
US61/182,561 2009-05-29
PCT/US2010/036559 WO2010138807A1 (en) 2009-05-29 2010-05-28 Fluorinated silylethynyl pentacene compounds and compositions and methods of making and using the same

Publications (2)

Publication Number Publication Date
CN102482297A CN102482297A (zh) 2012-05-30
CN102482297B true CN102482297B (zh) 2015-12-09

Family

ID=42342513

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Application Number Title Priority Date Filing Date
CN201080023410.8A Expired - Fee Related CN102482297B (zh) 2009-05-29 2010-05-28 含氟硅基乙炔基并五苯化合物和组合物以及其制造和使用方法

Country Status (6)

Country Link
US (1) US8920679B2 (https=)
EP (1) EP2435446B8 (https=)
JP (1) JP5722884B2 (https=)
CN (1) CN102482297B (https=)
SG (1) SG176209A1 (https=)
WO (1) WO2010138807A1 (https=)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8956555B2 (en) 2008-05-30 2015-02-17 3M Innovative Properties Company Silylethynyl pentacene compounds and compositions and methods of making and using the same
WO2009151978A1 (en) 2008-06-11 2009-12-17 3M Innovative Properties Company Mixed solvent systems for deposition of organic semiconductors
US8809568B2 (en) 2010-05-28 2014-08-19 3M Innovative Properties Company Synthesis of silylacetylenes
US8779179B2 (en) 2010-05-28 2014-07-15 3M Innovative Properties Company Synthesis of silyl acetylenes
JP2012212704A (ja) * 2011-03-30 2012-11-01 Sumitomo Chemical Co Ltd 液状組成物及びそれを用いた積層膜の製造方法
JP2016056098A (ja) * 2013-01-28 2016-04-21 旭硝子株式会社 含フッ素芳香族化合物及びその製造方法、ならびに有機半導体材料
EP3001471A4 (en) * 2013-05-23 2016-09-21 Fujifilm Corp ORGANIC SEMICONDUCTOR COMPOSITION, ORGANIC THIN-LAYER TRANSISTOR, ELECTRONIC PAPER AND DISPLAY DEVICE
US10192970B1 (en) * 2013-09-27 2019-01-29 The United States Of America As Represented By The Administrator Of National Aeronautics And Space Administration Simultaneous ohmic contact to silicon carbide
CN107699049A (zh) * 2017-11-10 2018-02-16 上海幂方电子科技有限公司 可喷墨打印的有机半导体材料组合物
JP7061804B2 (ja) * 2018-09-19 2022-05-02 国立大学法人茨城大学 含フッ素多環芳香族化合物とその製造方法、並びに前記含フッ素芳香族化合物を用いる有機薄膜トランジスタ及び太陽電池の製造方法
CN113793901B (zh) * 2021-09-16 2023-11-07 南京大学 一种基于聚合物掺杂n-型有机半导体的并五苯有机场效应晶体管

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20080197325A1 (en) * 2005-05-21 2008-08-21 Stephen William Leeming Oligomeric Polyacene and Semiconductor Formulations
WO2008128618A1 (en) * 2007-04-19 2008-10-30 Merck Patent Gmbh Process for preparing substituted pentacenes
WO2009155106A1 (en) * 2008-05-30 2009-12-23 3M Innovative Properties Company Silylethynyl pentacene compounds and compositions and methods of making and using the same
WO2009158201A1 (en) * 2008-06-27 2009-12-30 3M Innovative Properties Company Methods op fabricating crystalline organic semiconductive layers

Family Cites Families (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1246856B1 (en) 1999-10-27 2009-07-15 3M Innovative Properties Company Fluorochemical sulfonamide surfactants
ATE540913T1 (de) 2000-02-29 2012-01-15 Japan Science & Tech Agency Polyacen-derivate und ihre produktion
CN101108783B (zh) 2001-08-09 2012-04-04 旭化成株式会社 有机半导体元件
US6690029B1 (en) 2001-08-24 2004-02-10 University Of Kentucky Research Foundation Substituted pentacenes and electronic devices made with substituted pentacenes
US6864396B2 (en) 2001-09-27 2005-03-08 3M Innovative Properties Company Substituted pentacene semiconductors
US7098525B2 (en) 2003-05-08 2006-08-29 3M Innovative Properties Company Organic polymers, electronic devices, and methods
EP1687830B1 (en) 2003-11-28 2010-07-28 Merck Patent GmbH Organic semiconducting layer formulations comprising polyacenes and organic binder polymers
US7385221B1 (en) 2005-03-08 2008-06-10 University Of Kentucky Research Foundation Silylethynylated heteroacenes and electronic devices made therewith
US20060220007A1 (en) 2005-04-05 2006-10-05 Bailey David B Acene compounds having a single terminal fused thiophene as semiconductor materials for thin film transistors and methods of making the same
JP5155153B2 (ja) * 2005-05-12 2013-02-27 メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング ポリアセンおよび半導体調製物
CA2547799A1 (en) 2005-05-27 2006-11-27 University Of Ottawa Compounds comprising a linear series of five fused carbon rings, and preparation thereof
US7498662B2 (en) 2005-11-18 2009-03-03 3M Innovative Properties Company Dielectric media including surface-treated metal oxide particles
JP2007158062A (ja) 2005-12-06 2007-06-21 Konica Minolta Holdings Inc 有機半導体材料、有機半導体膜、有機半導体デバイス及び有機薄膜トランジスタ
US20070146426A1 (en) 2005-12-28 2007-06-28 Nelson Brian K All-inkjet printed thin film transistor
KR20080096781A (ko) 2006-01-21 2008-11-03 메르크 파텐트 게엠베하 유기 반도체 조성물을 포함하는 전자 단채널 소자
US7666968B2 (en) 2006-04-21 2010-02-23 3M Innovative Properties Company Acene-thiophene copolymers with silethynly groups
JP2007299852A (ja) * 2006-04-28 2007-11-15 Konica Minolta Holdings Inc 有機半導体材料、有機半導体膜、有機半導体デバイス及び有機薄膜トランジスタ
KR101591101B1 (ko) 2007-03-07 2016-02-03 유니버시티 오브 켄터키 리서치 파운데이션 실릴에티닐화 헤테로아센 및 이로 제조된 전자 장치
US20090001356A1 (en) 2007-06-29 2009-01-01 3M Innovative Properties Company Electronic devices having a solution deposited gate dielectric
US7879688B2 (en) 2007-06-29 2011-02-01 3M Innovative Properties Company Methods for making electronic devices with a solution deposited gate dielectric
WO2009079150A1 (en) 2007-12-17 2009-06-25 3M Innovative Properties Company Solution processable organic semiconductors based on anthracene
JP5745278B2 (ja) * 2008-03-06 2015-07-08 メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングMerck Patent Gesellschaft mit beschraenkter Haftung 有機半導体配合物

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20080197325A1 (en) * 2005-05-21 2008-08-21 Stephen William Leeming Oligomeric Polyacene and Semiconductor Formulations
WO2008128618A1 (en) * 2007-04-19 2008-10-30 Merck Patent Gmbh Process for preparing substituted pentacenes
WO2009155106A1 (en) * 2008-05-30 2009-12-23 3M Innovative Properties Company Silylethynyl pentacene compounds and compositions and methods of making and using the same
WO2009158201A1 (en) * 2008-06-27 2009-12-30 3M Innovative Properties Company Methods op fabricating crystalline organic semiconductive layers

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
Control of the Morphology and Structural Development of Solution-Processed Functionalized Acenes for High-Performance Organic Transistors;Jung Ah Lim等,;《Advanced Functional Materials》;20081230;第19卷(第10期);第1515-1525页 *
Exploiting Substituent Effects for the Synthesis of a Photooxidatively Resistant Heptacene Derivative;Irvinder Kaur等,;《J. AM. CHEM. SOC.》;20090225;第131卷(第10期);第3424-3425页 *
小分子场效应晶体管;汤庆鑫等,;《化学进展》;20061130;第18卷(第11期);第1538-1553页 *

Also Published As

Publication number Publication date
EP2435446B8 (en) 2017-02-22
EP2435446B1 (en) 2016-11-30
SG176209A1 (en) 2012-01-30
JP2012528196A (ja) 2012-11-12
WO2010138807A1 (en) 2010-12-02
US20120061620A1 (en) 2012-03-15
CN102482297A (zh) 2012-05-30
JP5722884B2 (ja) 2015-05-27
EP2435446A1 (en) 2012-04-04
US8920679B2 (en) 2014-12-30

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