JP5155852B2 - アリール−エチレン置換芳香族化合物および有機半導体としてのその使用 - Google Patents

アリール−エチレン置換芳香族化合物および有機半導体としてのその使用 Download PDF

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JP5155852B2
JP5155852B2 JP2008506569A JP2008506569A JP5155852B2 JP 5155852 B2 JP5155852 B2 JP 5155852B2 JP 2008506569 A JP2008506569 A JP 2008506569A JP 2008506569 A JP2008506569 A JP 2008506569A JP 5155852 B2 JP5155852 B2 JP 5155852B2
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JP2008538651A5 (zh
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ホン メン
モーリス スミス エリック
ス チェ−シュン
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Families Citing this family (44)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7838708B2 (en) 2001-06-20 2010-11-23 Grt, Inc. Hydrocarbon conversion process improvements
US20050171393A1 (en) 2003-07-15 2005-08-04 Lorkovic Ivan M. Hydrocarbon synthesis
RU2366642C2 (ru) 2003-07-15 2009-09-10 Джи Ар Ти, Инк. Синтез углеводородов
US20080275284A1 (en) 2004-04-16 2008-11-06 Marathon Oil Company Process for converting gaseous alkanes to liquid hydrocarbons
US20060100469A1 (en) 2004-04-16 2006-05-11 Waycuilis John J Process for converting gaseous alkanes to olefins and liquid hydrocarbons
US7244867B2 (en) 2004-04-16 2007-07-17 Marathon Oil Company Process for converting gaseous alkanes to liquid hydrocarbons
US8642822B2 (en) 2004-04-16 2014-02-04 Marathon Gtf Technology, Ltd. Processes for converting gaseous alkanes to liquid hydrocarbons using microchannel reactor
US8173851B2 (en) 2004-04-16 2012-05-08 Marathon Gtf Technology, Ltd. Processes for converting gaseous alkanes to liquid hydrocarbons
US7674941B2 (en) 2004-04-16 2010-03-09 Marathon Gtf Technology, Ltd. Processes for converting gaseous alkanes to liquid hydrocarbons
WO2006123741A1 (ja) * 2005-05-20 2006-11-23 Sumitomo Chemical Company, Limited 重合体組成物及びそれを用いた高分子発光素子
EA020442B1 (ru) 2006-02-03 2014-11-28 ДжиАрТи, ИНК. Способ превращения углеводородного сырья (варианты) и система для его осуществления
CN101395088B (zh) 2006-02-03 2012-04-04 Grt公司 轻气体与卤素的分离方法
US7528448B2 (en) 2006-07-17 2009-05-05 E.I. Du Pont De Nemours And Company Thin film transistor comprising novel conductor and dielectric compositions
WO2008059817A1 (fr) 2006-11-14 2008-05-22 Idemitsu Kosan Co., Ltd. Transistor mince film organique et transistor électrolumiscent à mince film organique
JP5337490B2 (ja) * 2006-11-14 2013-11-06 出光興産株式会社 有機薄膜トランジスタ及び有機薄膜発光トランジスタ
US8203139B2 (en) * 2006-11-24 2012-06-19 Idemitsu Kosan Co., Ltd Organic thin film transistor and organic thin film light-emitting transistor using an organic semiconductor layer having an aromatic hydrocarbon group or an aromatic heterocyclic group in the center thereof
US8207525B2 (en) 2006-12-04 2012-06-26 Idemitsu Kosan Co., Ltd. Organic thin film transistor and organic thin film light emitting transistor
JP5308164B2 (ja) 2006-12-04 2013-10-09 出光興産株式会社 有機薄膜トランジスタ及び有機薄膜発光トランジスタ
US7718998B2 (en) * 2006-12-14 2010-05-18 Xerox Corporation Thiophene electronic devices
KR101257851B1 (ko) * 2007-03-13 2013-04-24 삼성전자주식회사 디스플레용 박막 트랜지스터 및 그 제조 방법
KR100901885B1 (ko) * 2007-04-11 2009-06-09 경상대학교산학협력단 전자주게 치환기를 갖는 나프탈렌으로 말단 기능화된새로운 올리고머 반도체 화합물과 이를 이용한유기박막트랜지스터
JP2010528054A (ja) 2007-05-24 2010-08-19 ジーアールティー インコーポレイテッド 可逆的なハロゲン化水素の捕捉及び放出を組み込んだ領域反応器
GB0802912D0 (en) * 2008-02-15 2008-03-26 Carben Semicon Ltd Thin-film transistor, carbon-based layer and method of production thereof
US8592805B2 (en) 2008-04-10 2013-11-26 Idemitsu Kosan Co., Ltd. Compound for organic thin-film transistor and organic thin-film transistor using the compound
US8282810B2 (en) 2008-06-13 2012-10-09 Marathon Gtf Technology, Ltd. Bromine-based method and system for converting gaseous alkanes to liquid hydrocarbons using electrolysis for bromine recovery
KR100901856B1 (ko) 2008-06-25 2009-06-09 경상대학교산학협력단 전자주게 치환기를 갖는 나프탈렌으로 말단 기능화된새로운 올리고머 반도체 화합물과 이를 이용한유기박막트랜지스터
US8415517B2 (en) 2008-07-18 2013-04-09 Grt, Inc. Continuous process for converting natural gas to liquid hydrocarbons
KR20100130059A (ko) * 2009-06-02 2010-12-10 다우어드밴스드디스플레이머티리얼 유한회사 신규한 유기 발광 화합물 및 이를 포함하는 유기 발광 소자
CN102781945A (zh) * 2009-12-08 2012-11-14 国立大学法人东京工业大学 噻吩并吡嗪化合物和含有其的场效应晶体管
US8367884B2 (en) 2010-03-02 2013-02-05 Marathon Gtf Technology, Ltd. Processes and systems for the staged synthesis of alkyl bromides
US8198495B2 (en) 2010-03-02 2012-06-12 Marathon Gtf Technology, Ltd. Processes and systems for the staged synthesis of alkyl bromides
US8815050B2 (en) 2011-03-22 2014-08-26 Marathon Gtf Technology, Ltd. Processes and systems for drying liquid bromine
CN102651450A (zh) * 2011-03-29 2012-08-29 京东方科技集团股份有限公司 有机薄膜晶体管及其制造方法
US8436220B2 (en) 2011-06-10 2013-05-07 Marathon Gtf Technology, Ltd. Processes and systems for demethanization of brominated hydrocarbons
US8829256B2 (en) 2011-06-30 2014-09-09 Gtc Technology Us, Llc Processes and systems for fractionation of brominated hydrocarbons in the conversion of natural gas to liquid hydrocarbons
US8802908B2 (en) 2011-10-21 2014-08-12 Marathon Gtf Technology, Ltd. Processes and systems for separate, parallel methane and higher alkanes' bromination
US9193641B2 (en) 2011-12-16 2015-11-24 Gtc Technology Us, Llc Processes and systems for conversion of alkyl bromides to higher molecular weight hydrocarbons in circulating catalyst reactor-regenerator systems
CN105026518B (zh) * 2013-01-04 2017-11-28 日东电工株式会社 用于波长转换的高荧光且光稳定性发色团
JP6415560B2 (ja) 2013-08-23 2018-10-31 ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ 末端ヘテロアリールシアノビニレン基を有する化合物および前記化合物の有機太陽電池における使用
KR102128542B1 (ko) 2014-08-01 2020-06-30 니찌아스 카부시키카이샤 가교제 및 불소 함유 방향족 화합물
CN107305927A (zh) * 2016-04-20 2017-10-31 中国科学院化学研究所 含有不对称电极的微米尺度有机单晶光电器件及其制备方法与应用
US10266325B2 (en) 2016-06-07 2019-04-23 International Business Machines Corporation Polymer with blue light absorbing units chemically bonded to a polymeric backbone of the polymer
US11283023B2 (en) 2017-06-08 2022-03-22 Corning Incorporated Doping of other polymers into organic semi-conducting polymers
CN112608492B (zh) * 2020-12-29 2022-05-27 北京工业大学 基于两头吡唑配体的钴链的金属有机框架材料及制备和苯吸附应用

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4158099A (en) * 1967-07-14 1979-06-12 Ciba-Geigy Ag Production of aromatic compounds containing ethylene double bonds
CH500145A (de) * 1967-07-14 1970-12-15 Ciba Geigy Ag Verfahren zur Herstellung aromatischer, Äthylendoppelbindungen enthaltender Verbindungen
JP3223632B2 (ja) * 1993-03-18 2001-10-29 東洋インキ製造株式会社 有機エレクトロルミネッセンス素子
US5817430A (en) * 1996-11-13 1998-10-06 Xerox Corporation Electroluminescent polymer compositions and processes thereof
KR100806701B1 (ko) * 1997-10-23 2008-02-27 아이시스이노베이션리미티드 발광 덴드리머 및 장치
JP2000012228A (ja) * 1998-06-26 2000-01-14 Sony Corp 有機電界発光素子
JP4061561B2 (ja) * 1998-10-21 2008-03-19 富士電機ホールディングス株式会社 有機分子配向薄膜用材料及び有機分子配向薄膜の製造方法
US6630607B2 (en) * 2001-01-24 2003-10-07 Matsushita Electric Industrial Co., Ltd. Aromatic methylidene compounds, aromatic aldehyde compounds and methylstyryl compounds used to prepare the methylidene compounds, and methods for preparing these compounds
US7002176B2 (en) * 2002-05-31 2006-02-21 Ricoh Company, Ltd. Vertical organic transistor
EP1660450A4 (en) * 2003-08-15 2009-07-29 Univ Laval MONOMERS, OLIGOMERS AND POLYMERS OF 2-FUNCTIONALIZED AND 2.7-DIFUNCTIONALIZED CARBAZOLES
JP2005075868A (ja) * 2003-08-29 2005-03-24 Fujitsu Ltd 蛍光材料、有機エレクトロルミネッセンス素子および有機エレクトロルミネッセンスディスプレイ
WO2005073265A1 (en) * 2004-02-04 2005-08-11 Universite De Montreal Conjugated thiophenes having conducting properties and synthesis of same

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CN102683590A (zh) 2012-09-19
KR20080003883A (ko) 2008-01-08
EP1869720A2 (en) 2007-12-26
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