TWI471328B - 以二噻吩并〔2,3-d:2’,3’-d’〕苯并〔1,2-b:4,5-b’〕二噻吩為主之高效能溶液可加工之半導體 - Google Patents

以二噻吩并〔2,3-d:2’,3’-d’〕苯并〔1,2-b:4,5-b’〕二噻吩為主之高效能溶液可加工之半導體 Download PDF

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TWI471328B
TWI471328B TW98120880A TW98120880A TWI471328B TW I471328 B TWI471328 B TW I471328B TW 98120880 A TW98120880 A TW 98120880A TW 98120880 A TW98120880 A TW 98120880A TW I471328 B TWI471328 B TW I471328B
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alkyl
aryl
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thin film
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TW98120880A
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TW201008948A (en
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荷 尼可 陶
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巴地斯顏料化工廠
馬克斯 普蘭克科學促進公司
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D495/00Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/22Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains four or more hetero rings
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60Organic compounds having low molecular weight
    • H10K85/649Aromatic compounds comprising a hetero atom
    • H10K85/657Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D495/00Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/12Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • HELECTRICITY
    • H05ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05BELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00Electroluminescent light sources
    • H05B33/10Apparatus or processes specially adapted to the manufacture of electroluminescent light sources
    • HELECTRICITY
    • H05ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05BELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00Electroluminescent light sources
    • H05B33/12Light sources with substantially two-dimensional radiating surfaces
    • H05B33/14Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K10/00Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10Non-macromolecular compounds
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    • C09K2211/1011Condensed systems
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    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09K2211/00Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10Non-macromolecular compounds
    • C09K2211/1018Heterocyclic compounds
    • C09K2211/1025Heterocyclic compounds characterised by ligands
    • C09K2211/1092Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
    • GPHYSICS
    • G02OPTICS
    • G02BOPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B6/00Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings
    • G02B6/10Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings of the optical waveguide type
    • G02B6/12Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings of the optical waveguide type of the integrated circuit kind
    • G02B2006/12035Materials
    • G02B2006/12069Organic material
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K10/00Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
    • H10K10/40Organic transistors
    • H10K10/46Field-effect transistors, e.g. organic thin-film transistors [OTFT]
    • H10K10/462Insulated gate field-effect transistors [IGFETs]
    • H10K10/466Lateral bottom-gate IGFETs comprising only a single gate
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00Organic light-emitting devices
    • H10K50/10OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14Carrier transporting layers
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02EREDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00Energy generation through renewable energy sources
    • Y02E10/50Photovoltaic [PV] energy
    • Y02E10/549Organic PV cells

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Manufacturing & Machinery (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Thin Film Transistor (AREA)
TW98120880A 2008-07-02 2009-06-22 以二噻吩并〔2,3-d:2’,3’-d’〕苯并〔1,2-b:4,5-b’〕二噻吩為主之高效能溶液可加工之半導體 TWI471328B (zh)

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EP08159525 2008-07-02

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TW201008948A TW201008948A (en) 2010-03-01
TWI471328B true TWI471328B (zh) 2015-02-01

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US (1) US8367717B2 (enExample)
EP (1) EP2307424B1 (enExample)
JP (1) JP2011526588A (enExample)
KR (2) KR101855051B1 (enExample)
CN (1) CN102083838B (enExample)
CA (1) CA2729334A1 (enExample)
TW (1) TWI471328B (enExample)
WO (1) WO2010000670A1 (enExample)

Families Citing this family (53)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2465626B (en) * 2008-11-28 2013-07-31 Cambridge Display Tech Ltd Organic semiconductors
CN102317345B (zh) 2008-12-18 2013-07-10 巴斯夫欧洲公司 由二噻吩基亚乙烯基共聚物制备的半导体材料
CN102803559A (zh) 2009-04-28 2012-11-28 巴斯夫欧洲公司 生产半导体层的方法
EP2438104B1 (en) 2009-06-05 2014-04-30 Basf Se Fused bithiophene-vinylene polymers
US8653227B2 (en) 2009-06-15 2014-02-18 Basf Se Process for preparing regioregular poly-(3-substituted) thiophenes, selenophenes, thiazoles and selenazoles
JP2011044686A (ja) 2009-07-22 2011-03-03 Ricoh Co Ltd 新規な有機半導体材料とそれを用いた電子デバイス
KR101780083B1 (ko) 2009-12-02 2017-10-10 바스프 에스이 디티에노벤조-티에노[3,2-b]티오펜 공중합체 및 고성능 용액 공정 가능한 반도체 중합체로서 이의 용도
KR101792896B1 (ko) 2010-04-19 2017-11-20 메르크 파텐트 게엠베하 벤조디티오펜의 중합체 및 유기 반도체로서의 이의 용도
JP2011256144A (ja) * 2010-06-10 2011-12-22 Yamamoto Chem Inc チオフェン化合物の製造方法
JP5811542B2 (ja) * 2010-06-15 2015-11-11 株式会社リコー ジチエノベンゾジチオフェン誘導体からなる有機半導体材料前駆体、インク、絶縁部材、電荷輸送性部材の製造方法
JP5728990B2 (ja) * 2011-02-10 2015-06-03 住友化学株式会社 ジカルコゲノベンゾジピロール化合物、該化合物の製造方法、該化合物を含む薄膜及び該薄膜を含む有機半導体デバイス
US8394918B2 (en) * 2011-02-28 2013-03-12 Corning Incorporated Five-ring fused heteroaromatic compounds and conjugated polymers thereof
JP2012188400A (ja) * 2011-03-11 2012-10-04 Tosoh Corp ジチエノベンゾジチオフェンの製造方法
JP5790069B2 (ja) * 2011-03-29 2015-10-07 東ソー株式会社 ジチエノベンゾジチオフェン誘導体の製造方法
JP2012206953A (ja) * 2011-03-29 2012-10-25 Tosoh Corp ジチエノベンゾジチオフェン誘導体及びこれを用いた有機薄膜トランジスタ
JP5990870B2 (ja) * 2011-03-29 2016-09-14 東ソー株式会社 ジチエノベンゾジチオフェン誘導体溶液及び有機半導体層
JP5891646B2 (ja) * 2011-08-11 2016-03-23 株式会社リコー 新規な有機半導体材料およびそれを用いた電子デバイス
JP6108329B2 (ja) * 2011-08-15 2017-04-05 国立大学法人東京工業大学 有機半導体材料
JP5834673B2 (ja) * 2011-09-16 2015-12-24 株式会社リコー ジチエノベンゾジチオフェン誘導体からなる有機発光材料、発光部材、有機発光デバイス
JP5948772B2 (ja) * 2011-09-21 2016-07-06 東ソー株式会社 ジチエノベンゾジチオフェン誘導体組成物及びこれを用いた有機薄膜トランジスタ
CN102585177B (zh) * 2012-03-08 2014-05-07 中国科学院化学研究所 光电活性二噻吩并苯并二噻吩类共轭聚合物及其制备方法与应用
JP2013201363A (ja) * 2012-03-26 2013-10-03 Ricoh Co Ltd 有機薄膜トランジスタ、有機薄膜トランジスタアレイおよび表示装置
JP6047969B2 (ja) * 2012-07-17 2016-12-21 東ソー株式会社 ジチエノベンゾジチオフェン誘導体溶液及びこれを用いた有機半導体層
CN103730581B (zh) * 2012-10-15 2016-05-18 乐金显示有限公司 有机发光装置和使用其的有机发光显示装置
KR101571590B1 (ko) 2012-11-21 2015-11-25 주식회사 두산 유기 화합물 및 이를 이용하는 유기 전계 발광 소자
CN104769002B (zh) * 2012-11-30 2016-10-12 海洋王照明科技股份有限公司 含噻吩并[3,4-b]噻吩单元的苯并二噻吩类共聚物及其制备方法与应用
JP6096313B2 (ja) * 2012-11-30 2017-03-15 オーシャンズ キング ライティング サイエンス アンド テクノロジー シーオー.,エルティーディー ピリジノ[2,1,3]チアジアゾールユニットを含有するベンゾジチオフェン系共重合体、製造方法、及び、その使用方法
JP2014110347A (ja) * 2012-12-03 2014-06-12 Tosoh Corp 有機半導体層形成用材料
JP6056498B2 (ja) * 2013-01-21 2017-01-11 東ソー株式会社 ジチエノベンゾジフラン誘導体及びその製造方法
CN103242343B (zh) * 2013-05-15 2015-12-09 北京博如德工程技术研究有限公司 一种有机小分子半导体材料及其制备方法
CN103289062B (zh) * 2013-06-04 2015-10-28 孟鸿 一种网状低能级p型聚合物半导体材料及其制备方法与应用
JP6252032B2 (ja) * 2013-08-19 2017-12-27 東ソー株式会社 ベンゾジフラン誘導体及び有機薄膜トランジスタ
KR101595919B1 (ko) * 2013-08-30 2016-02-29 한국과학기술연구원 전도성 유기 반도체 화합물 및 이를 포함하는 유기태양전지
JP6016821B2 (ja) * 2014-01-10 2016-10-26 富士フイルム株式会社 有機薄膜トランジスタ、有機半導体薄膜および有機半導体材料
JP6295781B2 (ja) * 2014-03-28 2018-03-20 東ソー株式会社 ヘテロアセン誘導体、有機半導体層、及び有機薄膜トランジスタ
JP6331579B2 (ja) * 2014-03-28 2018-05-30 東ソー株式会社 ヘテロアセン誘導体、有機半導体層、及び有機薄膜トランジスタ
JP6318863B2 (ja) * 2014-05-29 2018-05-09 東ソー株式会社 ジチエノベンゾジチオフェン誘導体の製造方法
JP6344063B2 (ja) * 2014-05-29 2018-06-20 東ソー株式会社 ジチエノベンゾジチオフェン誘導体の製造方法
WO2016009890A1 (ja) 2014-07-18 2016-01-21 富士フイルム株式会社 有機半導体膜形成用組成物、並びに、有機半導体素子及びその製造方法
JP6372290B2 (ja) * 2014-10-07 2018-08-15 東ソー株式会社 1,4−ビス(3−ハロ−2−チエニル)−2,5−ジハロベンゼンの製造方法
CN104393174B (zh) * 2014-10-27 2017-02-15 中国科学院化学研究所 一种有机场效应晶体管及其在紫外光传感中的应用
EP3050887B1 (en) 2015-01-29 2017-06-28 Samsung Electronics Co., Ltd. Fused polycyclic heteroaromatic compound, organic thin film including compound and electronic device including organic thin film
JP6413863B2 (ja) * 2015-03-19 2018-10-31 東ソー株式会社 ヘテロアセン誘導体、有機半導体層、及び有機薄膜トランジスタ
JP6399956B2 (ja) * 2015-03-31 2018-10-03 東ソー株式会社 ヘテロアセン誘導体、その製造方法、有機半導体層、及び有機薄膜トランジスタ
JP6597087B2 (ja) * 2015-09-09 2019-10-30 Dic株式会社 有機化合物、その製造方法、それを含有する有機半導体材料及びそれを含有する有機トランジスタ
JP6484724B2 (ja) 2015-11-20 2019-03-13 富士フイルム株式会社 有機半導体組成物、有機半導体膜、有機薄膜トランジスタおよび有機薄膜トランジスタの製造方法
JP6676181B2 (ja) * 2016-09-29 2020-04-08 富士フイルム株式会社 微結晶有機半導体膜、有機半導体トランジスタ、及び有機半導体トランジスタの製造方法
JP6689393B2 (ja) 2016-09-29 2020-04-28 富士フイルム株式会社 有機半導体膜形成用組成物、有機半導体膜及びその製造方法、並びに、有機半導体素子
JP7078634B2 (ja) * 2016-12-06 2022-05-31 ビーエーエスエフ ソシエタス・ヨーロピア チエノ-インデノ-モノマーおよびポリマー
JP7034541B2 (ja) * 2017-07-18 2022-03-14 株式会社日本触媒 縮合多環式化合物
EP3434679B1 (en) 2017-07-28 2020-04-15 Samsung Electronics Co., Ltd. Organic compound, organic thin film, and electronic device
KR102464890B1 (ko) 2017-10-18 2022-11-07 삼성전자주식회사 축합다환 헤테로방향족 화합물, 유기 박막 및 전자 소자
CN111471055B (zh) * 2020-01-17 2021-07-16 中国长江三峡集团有限公司 苯并三噻吩的二维非富勒烯受体材料与用途

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TW200737559A (en) * 2005-12-12 2007-10-01 Ciba Sc Holding Ag Organic semiconductors, their manufacture and semiconductor devices comprising them

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4423995A (en) 1981-06-17 1984-01-03 Beloit Corporation Arrangement for automatic changeover between ream and skid loading in a continuous sheeter
US5198153A (en) 1989-05-26 1993-03-30 International Business Machines Corporation Electrically conductive polymeric
JP3224829B2 (ja) 1991-08-15 2001-11-05 株式会社東芝 有機電界効果型素子
WO1996021659A1 (en) 1995-01-10 1996-07-18 University Of Technology, Sydney Organic semiconductor
EP1839339A2 (en) 2004-12-23 2007-10-03 Northwestern University Siloxane-polymer dielectric compositions and related organic field-effect transistors
JP2007088016A (ja) * 2005-09-20 2007-04-05 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、有機薄膜トランジスタ及び有機エレクトロルミネッセンス素子
WO2007075748A2 (en) 2005-12-20 2007-07-05 Northwestern University Intercalated superlattice compositions and related methods for modulating dielectric property
JP5499422B2 (ja) 2006-06-28 2014-05-21 コニカミノルタ株式会社 有機半導体材料、有機半導体膜、有機薄膜トランジスタ及び有機薄膜トランジスタの製造方法
JP5272345B2 (ja) * 2006-08-28 2013-08-28 東ソー株式会社 ヘテロアセン誘導体、テトラハロターフェニル誘導体及びそれらの製造方法
EP2067782B2 (en) 2006-08-28 2018-06-27 Tosoh Corporation Heteroacene derivative, tetrahaloterphenyl derivative, and their production methods
WO2009016107A1 (en) 2007-07-30 2009-02-05 Basf Se Method for depositing a semiconducting layer from a liquid
JP5160842B2 (ja) * 2007-08-28 2013-03-13 山本化成株式会社 有機トランジスタ

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TW200737559A (en) * 2005-12-12 2007-10-01 Ciba Sc Holding Ag Organic semiconductors, their manufacture and semiconductor devices comprising them

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US20110155248A1 (en) 2011-06-30
CA2729334A1 (en) 2010-01-07
EP2307424A1 (en) 2011-04-13
TW201008948A (en) 2010-03-01
CN102083838A (zh) 2011-06-01
JP2011526588A (ja) 2011-10-13
KR20170010056A (ko) 2017-01-25
CN102083838B (zh) 2016-05-25
EP2307424B1 (en) 2018-08-15
KR101855051B1 (ko) 2018-05-04
KR20110031364A (ko) 2011-03-25
WO2010000670A1 (en) 2010-01-07
US8367717B2 (en) 2013-02-05

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