CN102106012B - 用于沉积有机半导体的混合溶剂体系 - Google Patents

用于沉积有机半导体的混合溶剂体系 Download PDF

Info

Publication number
CN102106012B
CN102106012B CN2009801295021A CN200980129502A CN102106012B CN 102106012 B CN102106012 B CN 102106012B CN 2009801295021 A CN2009801295021 A CN 2009801295021A CN 200980129502 A CN200980129502 A CN 200980129502A CN 102106012 B CN102106012 B CN 102106012B
Authority
CN
China
Prior art keywords
substituted
weight
composition
unsubstituted
carbon atoms
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
CN2009801295021A
Other languages
English (en)
Chinese (zh)
Other versions
CN102106012A (zh
Inventor
罗伯特·S·克拉夫
大卫·H·瑞丁格尔
詹姆斯·C·诺瓦克
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.)
3M Innovative Properties Co
Original Assignee
3M Innovative Properties Co
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 3M Innovative Properties Co filed Critical 3M Innovative Properties Co
Publication of CN102106012A publication Critical patent/CN102106012A/zh
Application granted granted Critical
Publication of CN102106012B publication Critical patent/CN102106012B/zh
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Images

Classifications

    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
    • H10K71/10—Deposition of organic active material
    • H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
    • H10K71/15—Deposition of organic active material using liquid deposition, e.g. spin coating characterised by the solvent used
    • 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
    • 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
    • H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
    • H10K71/10—Deposition of organic active material
    • H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
    • H10K71/13—Deposition of organic active material using liquid deposition, e.g. spin coating using printing techniques, e.g. ink-jet printing or screen printing
    • H10K71/135—Deposition of organic active material using liquid deposition, e.g. spin coating using printing techniques, e.g. ink-jet printing or screen printing using ink-jet printing

Landscapes

  • Engineering & Computer Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Materials Engineering (AREA)
  • Manufacturing & Machinery (AREA)
  • Thin Film Transistor (AREA)
  • Liquid Deposition Of Substances Of Which Semiconductor Devices Are Composed (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Paints Or Removers (AREA)
CN2009801295021A 2008-06-11 2009-05-29 用于沉积有机半导体的混合溶剂体系 Expired - Fee Related CN102106012B (zh)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US6059508P 2008-06-11 2008-06-11
US61/060,595 2008-06-11
PCT/US2009/045571 WO2009151978A1 (en) 2008-06-11 2009-05-29 Mixed solvent systems for deposition of organic semiconductors

Publications (2)

Publication Number Publication Date
CN102106012A CN102106012A (zh) 2011-06-22
CN102106012B true CN102106012B (zh) 2013-05-29

Family

ID=40910017

Family Applications (1)

Application Number Title Priority Date Filing Date
CN2009801295021A Expired - Fee Related CN102106012B (zh) 2008-06-11 2009-05-29 用于沉积有机半导体的混合溶剂体系

Country Status (5)

Country Link
US (1) US8232550B2 (cg-RX-API-DMAC7.html)
EP (1) EP2304821B1 (cg-RX-API-DMAC7.html)
JP (1) JP5406284B2 (cg-RX-API-DMAC7.html)
CN (1) CN102106012B (cg-RX-API-DMAC7.html)
WO (1) WO2009151978A1 (cg-RX-API-DMAC7.html)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB0612929D0 (en) 2006-06-29 2006-08-09 Univ Cambridge Tech High-performance organic field-effect transistors based on dilute, crystalline-crystalline polymer blends and block copolymers
PL3981502T3 (pl) 2007-04-26 2025-06-16 Johnson Matthey Public Limited Company Katalizatory scr z metalami przejściowymi/zeolitem
JP5658145B2 (ja) * 2008-05-30 2015-01-21 スリーエム イノベイティブ プロパティズ カンパニー 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
KR20170091788A (ko) * 2009-12-23 2017-08-09 메르크 파텐트 게엠베하 중합체성 결합제를 포함하는 조성물
JP5840621B2 (ja) 2009-12-23 2016-01-06 メルク パテント ゲーエムベーハー 有機半導体化合物を含む組成物
WO2011147523A1 (en) * 2010-05-27 2011-12-01 Merck Patent Gmbh Formulation and method for preparation of organic electronic devices
GB201013820D0 (en) * 2010-08-18 2010-09-29 Cambridge Display Tech Ltd Low contact resistance organic thin film transistors
US8389744B1 (en) * 2011-10-11 2013-03-05 University Of New Hampshire TTPO (5 6,7-trithiapentacene-13-one) and its derivatives: a new class of thermally stable, photooxidatively resistant organic semiconductors
US9293711B2 (en) 2012-08-09 2016-03-22 Polyera Corporation Organic semiconductor formulations
KR102145424B1 (ko) * 2013-11-11 2020-08-18 엘지디스플레이 주식회사 표시장치 제조용 잉크 및 이를 이용한 표시장치의 제조방법
JP6578645B2 (ja) * 2014-10-21 2019-09-25 東ソー株式会社 有機半導体層形成用溶液、有機半導体層、および有機薄膜トランジスタ
JP7019559B2 (ja) * 2015-07-15 2022-02-15 メルク パテント ゲーエムベーハー 有機半導体化合物を含む組成物
US11495744B2 (en) * 2017-03-21 2022-11-08 Nippon Kayaku Kabushiki Kaisha Organic semiconductor composition, organic thin film, and organic thin film transistor
GB2560934A (en) 2017-03-28 2018-10-03 Sumitomo Chemical Co Solvent systems for the preparation of photosensitive organic electronic devices
US11283023B2 (en) 2017-06-08 2022-03-22 Corning Incorporated Doping of other polymers into organic semi-conducting polymers

Family Cites Families (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6265243B1 (en) * 1999-03-29 2001-07-24 Lucent Technologies Inc. Process for fabricating organic circuits
EP1364420B1 (en) * 2001-02-27 2012-10-10 Cambridge Display Technology Limited Formulation for depositing a material on a substrate using ink jet printing
KR100552866B1 (ko) * 2001-08-09 2006-02-20 아사히 가세이 가부시키가이샤 유기 반도체 소자
US6690029B1 (en) * 2001-08-24 2004-02-10 University Of Kentucky Research Foundation Substituted pentacenes and electronic devices made with substituted pentacenes
CN1582506A (zh) * 2001-09-27 2005-02-16 3M创新有限公司 取代并五苯半导体
US7098525B2 (en) * 2003-05-08 2006-08-29 3M Innovative Properties Company Organic polymers, electronic devices, and methods
ATE475971T1 (de) * 2003-11-28 2010-08-15 Merck Patent Gmbh Organische halbleiterschicht-formulierungen mit polyacenen und organischen binderpolymeren
DE102004007777A1 (de) * 2004-02-18 2005-09-08 Covion Organic Semiconductors Gmbh Lösungen organischer Halbleiter
DE102004023276A1 (de) * 2004-05-11 2005-12-01 Covion Organic Semiconductors Gmbh Lösungen organischer Halbleiter
KR20070093075A (ko) 2004-12-28 2007-09-17 이데미쓰 고산 가부시키가이샤 유기 ｅｌ 도포막 형성용 잉크 및 그의 제조 방법
US7264872B2 (en) * 2004-12-30 2007-09-04 3M Innovative Properties Company Durable high index nanocomposites for AR coatings
US7241437B2 (en) 2004-12-30 2007-07-10 3M Innovative Properties Company Zirconia particles
US7211679B2 (en) * 2005-03-09 2007-05-01 3M Innovative Properties Company Perfluoroether acyl oligothiophene compounds
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
US7319153B2 (en) * 2005-07-29 2008-01-15 3M Innovative Properties Company 6,13-Bis(thienyl)pentacene compounds
US7514710B2 (en) 2005-12-28 2009-04-07 3M Innovative Properties Company Bottom gate thin film transistors
US20070146426A1 (en) * 2005-12-28 2007-06-28 Nelson Brian K All-inkjet printed thin film transistor
US7608679B2 (en) * 2006-03-31 2009-10-27 3M Innovative Properties Company Acene-thiophene copolymers
US7495251B2 (en) * 2006-04-21 2009-02-24 3M Innovative Properties Company Electronic devices containing acene-thiophene copolymers with silylethynyl groups
US7666968B2 (en) * 2006-04-21 2010-02-23 3M Innovative Properties Company Acene-thiophene copolymers with silethynly groups
JP2007311677A (ja) * 2006-05-22 2007-11-29 Konica Minolta Holdings Inc 有機薄膜トランジスタの製造方法、有機薄膜トランジスタ
JP5055849B2 (ja) * 2006-06-14 2012-10-24 コニカミノルタホールディングス株式会社 表示装置、有機薄膜トランジスタの製造方法
JP2010512005A (ja) 2006-12-01 2010-04-15 ザ リージェンツ オブ ザ ユニバーシティ オブ カリフォルニア 改善された溶液処理方法による有機半導体膜の性能特性の向上
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
JP5658145B2 (ja) * 2008-05-30 2015-01-21 スリーエム イノベイティブ プロパティズ カンパニー 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
CN102119164A (zh) * 2008-06-19 2011-07-06 3M创新有限公司 可溶液处理的有机半导体
WO2009158201A1 (en) 2008-06-27 2009-12-30 3M Innovative Properties Company Methods op fabricating crystalline organic semiconductive layers
EP2435446B8 (en) 2009-05-29 2017-02-22 3M Innovative Properties Company Fluorinated silylethynyl pentacene compounds and compositions and methods of making and using the same
US7948016B1 (en) * 2009-11-03 2011-05-24 3M Innovative Properties Company Off-center deposition of organic semiconductor in an organic semiconductor device

Also Published As

Publication number Publication date
WO2009151978A1 (en) 2009-12-17
EP2304821B1 (en) 2012-06-27
US8232550B2 (en) 2012-07-31
JP2011525044A (ja) 2011-09-08
US20110092015A1 (en) 2011-04-21
JP5406284B2 (ja) 2014-02-05
EP2304821A1 (en) 2011-04-06
CN102106012A (zh) 2011-06-22

Similar Documents

Publication Publication Date Title
CN102106012B (zh) 用于沉积有机半导体的混合溶剂体系
Lee et al. High-performance thin-film transistor with 6, 13-bis (triisopropylsilylethynyl) pentacene by inkjet printing
Lee et al. Control of droplet morphology for inkjet-printed TIPS-pentacene transistors
JP5470763B2 (ja) カーボンナノチューブ分散溶液、有機半導体コンポジット溶液、有機半導体薄膜ならびに有機電界効果型トランジスタ
US20110180787A1 (en) Ink-Jet Print Ink and Organic Thin Film Transister Using Thereof
CN1812153A (zh) 有机半导体层的形成方法及有机薄膜晶体管
KR20120043009A (ko) 신규한 유기 반도체 재료 및 이것을 이용한 전자 디바이스
KR20080008999A (ko) 전기 전도성 피쳐의 제조방법
KR101069585B1 (ko) 표면처리된 잉크젯 프린트용 기판
US11198698B2 (en) Organic semiconductor composition, organic thin film comprising same, and use thereof
Kim et al. Ink-jet-printed zinc–tin–oxide thin-film transistors and circuits with rapid thermal annealing process
CN101203950A (zh) 有机半导体膜的形成方法、有机半导体膜及有机薄膜晶体管
JP2010219447A (ja) 有機トランジスタ用インク、有機トランジスタの電極及びその形成方法並びに有機トランジスタ
Zhang et al. Brush-controlled oriented growth of TCNQ microwire arrays for field-effect transistors
US10600962B2 (en) Method of manufacturing organic semiconductor thin film using bar-coating process and method of fabricating flexible organic semiconductor transistor comprising the same
Kim et al. Ink-jet printing of organic semiconductor for fabricating organic thin-film transistors: Film uniformity control by ink composition
JP2010093260A (ja) 半導体インク配合物
JP2017098490A (ja) 有機半導体層形成用溶液、有機半導体層、および有機薄膜トランジスタ
Suk et al. Modified polyvinyl alcohol layer with hydrophobic surface for the passivation of pentacene thin-film transistor
EP2356708A1 (en) Off-center deposition of organic semiconductor in an organic semiconductor device
Lim et al. Ink-jet printing of self-aligned soluble-pentacene crystals for high-performance organic field-effect transistors
JP2016162961A (ja) 有機半導体層形成用溶液、有機半導体層、および有機薄膜トランジスタ
JP2017098491A (ja) 有機半導体層形成用溶液、有機半導体層、および有機薄膜トランジスタ
Kim et al. P‐80: WITHDRAWN: P‐81: Printed Organic Single‐crystal TFTs with Bottom‐contact Structure
JP2020167439A (ja) 有機半導体膜及びその製造方法

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
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: 20130529

Termination date: 20180529