JP5658145B2 - シリルメチルペンタセン化合物及び組成物、並びにそれらの製造及び使用方法 - Google Patents

シリルメチルペンタセン化合物及び組成物、並びにそれらの製造及び使用方法 Download PDF

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JP5658145B2
JP5658145B2 JP2011511852A JP2011511852A JP5658145B2 JP 5658145 B2 JP5658145 B2 JP 5658145B2 JP 2011511852 A JP2011511852 A JP 2011511852A JP 2011511852 A JP2011511852 A JP 2011511852A JP 5658145 B2 JP5658145 B2 JP 5658145B2
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JP2011521972A5 (https=
JP2011521972A (ja
Inventor
イー． アンソニー，ジョン
イー． アンソニー，ジョン
エー． カルドウェル，グレッグ
エー． カルドウェル，グレッグ
エス． クロウ，ロバート
エス． クロウ，ロバート
シー． ノバック，ジェイムズ
シー． ノバック，ジェイムズ
エム． ペイン，マルシア
エム． ペイン，マルシア
エイチ． レディンガー，デイビッド
エイチ． レディンガー，デイビッド
ボーゲル，デニス　イー．
イー． ボーゲル，デニス
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3M Innovative Properties Co
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3M Innovative Properties Co
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • 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
    • H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
    • 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
    • H10K85/623—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing five rings, e.g. pentacene
    • 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

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Thin Film Transistor (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Paints Or Removers (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Electroluminescent Light Sources (AREA)
JP2011511852A 2008-05-30 2009-05-29 シリルメチルペンタセン化合物及び組成物、並びにそれらの製造及び使用方法 Expired - Fee Related JP5658145B2 (ja)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US5771508P 2008-05-30 2008-05-30
US61/057,715 2008-05-30
PCT/US2009/045667 WO2009155106A1 (en) 2008-05-30 2009-05-29 Silylethynyl pentacene compounds and compositions and methods of making and using the same

Related Child Applications (1)

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JP2014146824A Division JP2015007049A (ja) 2008-05-30 2014-07-17 シリルエチニルペンタセン化合物及び組成物、並びにそれらの製造及び使用方法

Publications (3)

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JP2011521972A JP2011521972A (ja) 2011-07-28
JP2011521972A5 JP2011521972A5 (https=) 2014-03-20
JP5658145B2 true JP5658145B2 (ja) 2015-01-21

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JP2011511852A Expired - Fee Related JP5658145B2 (ja) 2008-05-30 2009-05-29 シリルメチルペンタセン化合物及び組成物、並びにそれらの製造及び使用方法
JP2014146824A Withdrawn JP2015007049A (ja) 2008-05-30 2014-07-17 シリルエチニルペンタセン化合物及び組成物、並びにそれらの製造及び使用方法

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Country Link
US (1) US8956555B2 (https=)
EP (1) EP2307427B1 (https=)
JP (2) JP5658145B2 (https=)
KR (1) KR101622420B1 (https=)
CN (1) CN102124015B (https=)
WO (1) WO2009155106A1 (https=)

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101622420B1 (ko) 2008-05-30 2016-05-18 쓰리엠 이노베이티브 프로퍼티즈 컴파니 실릴에티닐 펜타센 화합물 및 조성물 및 그의 제조 및 사용 방법
JP5406284B2 (ja) * 2008-06-11 2014-02-05 スリーエム イノベイティブ プロパティズ カンパニー 有機半導体の堆積のための混合溶媒系
SG176209A1 (en) * 2009-05-29 2012-01-30 3M Innovative Properties Co Fluorinated silylethynyl pentacene compounds and compositions and methods of making and using the same
US8779179B2 (en) 2010-05-28 2014-07-15 3M Innovative Properties Company Synthesis of silyl acetylenes
WO2011150020A1 (en) 2010-05-28 2011-12-01 3M Innovative Properties Company Synthesis of silyl acetylenes
EP2614068A1 (en) * 2010-09-10 2013-07-17 Merck Patent GmbH Anthra[2,3-b:7,6b']dithiophene derivatives and their use as organic semiconductors
WO2012071243A2 (en) 2010-11-22 2012-05-31 3M Innovative Properties Company Assembly and electronic devices including the same
US9373801B2 (en) 2011-01-28 2016-06-21 Merck Patent Gmbh Flavanthrene derivatives and their use as organic semiconductors
CN103415526A (zh) 2011-03-11 2013-11-27 默克专利股份有限公司 二萘并[2,3-a:2’,3’-h]吩嗪类和它们作为有机半导体的用途
GB201108864D0 (en) 2011-05-26 2011-07-06 Ct For Process Innovation The Ltd Transistors and methods of making them
GB201108865D0 (en) 2011-05-26 2011-07-06 Ct For Process Innovation The Ltd Semiconductor compounds
GB2491810B (en) * 2011-05-31 2018-03-21 Smartkem Ltd Organic semiconductor compositions
GB201203159D0 (en) 2012-02-23 2012-04-11 Smartkem Ltd Organic semiconductor compositions
US10354049B2 (en) 2012-08-22 2019-07-16 Koninklijke Philips N.V. Automatic detection and retrieval of prior annotations relevant for an imaging study for efficient viewing and reporting
CN105229814B (zh) * 2013-05-23 2017-11-10 富士胶片株式会社 有机半导体组合物、有机薄膜晶体管、以及电子纸及显示装置
KR102091906B1 (ko) 2013-08-28 2020-03-20 스마트켐 리미티드 고분자 유기 반도체 조성물
CN106328812B (zh) * 2015-07-06 2019-10-18 元太科技工业股份有限公司 有源元件及其制作方法
CN106854218B (zh) * 2016-12-30 2019-03-05 上海升翕光电科技有限公司 一种硅蒽类衍生物及其制备方法和有机发光器件
CN107464879A (zh) * 2017-10-17 2017-12-12 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
CN115785141A (zh) * 2022-11-30 2023-03-14 西北师范大学 噻二唑喹喔啉衍生物及其制备方法和应用

Family Cites Families (29)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6026A (en) * 1849-01-09 Cast-iron car-wheel
JP4855616B2 (ja) 1999-10-27 2012-01-18 スリーエム イノベイティブ プロパティズ カンパニー フルオロケミカルスルホンアミド界面活性剤
CA2401487C (en) 2000-02-29 2011-06-21 Japan Science And Technology Agency Polyacene derivatives and process of producing thereof
EP2199437B1 (en) 2001-08-09 2015-07-29 Asahi Kasei Kabushiki Kaisha Use of an organic semiconductor solution to form oriented polyacene crystals on a substrate
US6690029B1 (en) 2001-08-24 2004-02-10 University Of Kentucky Research Foundation Substituted pentacenes and electronic devices made with substituted pentacenes
JP2005504811A (ja) 2001-09-27 2005-02-17 スリーエム イノベイティブ プロパティズ カンパニー 置換ペンタセン半導体
US7098525B2 (en) 2003-05-08 2006-08-29 3M Innovative Properties Company Organic polymers, electronic devices, and methods
EP1783781A3 (en) * 2003-11-28 2007-10-03 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
EP1986247A1 (en) * 2005-05-12 2008-10-29 MERCK PATENT GmbH Polyacene and semiconductor Formulation
JP2008545631A (ja) 2005-05-21 2008-12-18 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 ハフトング オリゴマーポリアセンおよび半導体調製物
US20060267004A1 (en) * 2005-05-27 2006-11-30 Fallis Alexander G 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
EP1974401A1 (en) 2006-01-21 2008-10-01 Merck Patent GmbH Electronic short channel device comprising an organic semiconductor formulation
US7666968B2 (en) 2006-04-21 2010-02-23 3M Innovative Properties Company Acene-thiophene copolymers with silethynly groups
US7495251B2 (en) * 2006-04-21 2009-02-24 3M Innovative Properties Company Electronic devices containing acene-thiophene copolymers with silylethynyl 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
EP2132213B1 (en) 2007-03-07 2013-05-15 University of Kentucky Research Foundation Silylethynylated heteroacenes and electronic devices made therewith
JP5524043B2 (ja) * 2007-04-19 2014-06-18 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 置換されたペンタセン類の調製方法
US7879688B2 (en) 2007-06-29 2011-02-01 3M Innovative Properties Company Methods for making electronic devices with a solution deposited gate dielectric
US20090001356A1 (en) 2007-06-29 2009-01-01 3M Innovative Properties Company Electronic devices having a solution deposited gate dielectric
EP2232606A1 (en) 2007-12-17 2010-09-29 3M Innovative Properties Company Solution processable organic semiconductors based on anthracene
KR101622420B1 (ko) 2008-05-30 2016-05-18 쓰리엠 이노베이티브 프로퍼티즈 컴파니 실릴에티닐 펜타센 화합물 및 조성물 및 그의 제조 및 사용 방법
JP5406284B2 (ja) * 2008-06-11 2014-02-05 スリーエム イノベイティブ プロパティズ カンパニー 有機半導体の堆積のための混合溶媒系
WO2009158201A1 (en) 2008-06-27 2009-12-30 3M Innovative Properties Company Methods op fabricating crystalline organic semiconductive layers
SG176209A1 (en) 2009-05-29 2012-01-30 3M Innovative Properties Co Fluorinated silylethynyl pentacene compounds and compositions and methods of making and using the same

Also Published As

Publication number Publication date
CN102124015B (zh) 2015-03-11
EP2307427A1 (en) 2011-04-13
US8956555B2 (en) 2015-02-17
KR20110026437A (ko) 2011-03-15
JP2011521972A (ja) 2011-07-28
US20110073813A1 (en) 2011-03-31
EP2307427B1 (en) 2015-02-18
JP2015007049A (ja) 2015-01-15
CN102124015A (zh) 2011-07-13
WO2009155106A1 (en) 2009-12-23
KR101622420B1 (ko) 2016-05-18

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