JP5787876B2 - ピロロピロール誘導体、その製造方法及び半導体としての使用 - Google Patents

ピロロピロール誘導体、その製造方法及び半導体としての使用 Download PDF

Info

Publication number
JP5787876B2
JP5787876B2 JP2012503967A JP2012503967A JP5787876B2 JP 5787876 B2 JP5787876 B2 JP 5787876B2 JP 2012503967 A JP2012503967 A JP 2012503967A JP 2012503967 A JP2012503967 A JP 2012503967A JP 5787876 B2 JP5787876 B2 JP 5787876B2
Authority
JP
Japan
Prior art keywords
formula
alkyl
group
independently
hydrogen
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
JP2012503967A
Other languages
English (en)
Japanese (ja)
Other versions
JP2012523387A5 (enExample
JP2012523387A (ja
Inventor
アヨ パスカル
アヨ パスカル
フレデリック エビシャー オリヴィエ
フレデリック エビシャー オリヴィエ
デュゲリ マティアス
デュゲリ マティアス
ジェ．エル． トゥルビエ マチュー
ジェ．エル． トゥルビエ マチュー
フォンロドナ トゥロン マルタ
フォンロドナ トゥロン マルタ
チェボタレヴァ ナタリア
チェボタレヴァ ナタリア
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.)
BASF SE
Original Assignee
BASF SE
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 BASF SE filed Critical BASF SE
Publication of JP2012523387A publication Critical patent/JP2012523387A/ja
Publication of JP2012523387A5 publication Critical patent/JP2012523387A5/ja
Application granted granted Critical
Publication of JP5787876B2 publication Critical patent/JP5787876B2/ja
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic 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 two hetero rings
    • C07D495/04—Ortho-condensed systems
    • 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]
    • 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
    • H10K85/621—Aromatic anhydride or imide compounds, e.g. perylene tetra-carboxylic dianhydride or perylene tetracarboxylic di-imide
    • 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
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/655—Aromatic compounds comprising a hetero atom comprising only sulfur as heteroatom
    • 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
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
    • 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
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • 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
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • Y—GENERAL 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
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Photovoltaic Devices (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
JP2012503967A 2009-04-08 2010-03-30 ピロロピロール誘導体、その製造方法及び半導体としての使用 Expired - Fee Related JP5787876B2 (ja)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
EP09157579.5 2009-04-08
EP09157579 2009-04-08
EP09168454 2009-08-24
EP09168454.8 2009-08-24
PCT/EP2010/054152 WO2010115767A1 (en) 2009-04-08 2010-03-30 Pyrrolopyrrole derivatives, their manufacture and use as semiconductors

Publications (3)

Publication Number Publication Date
JP2012523387A JP2012523387A (ja) 2012-10-04
JP2012523387A5 JP2012523387A5 (enExample) 2013-05-16
JP5787876B2 true JP5787876B2 (ja) 2015-09-30

Family

ID=42174107

Family Applications (1)

Application Number Title Priority Date Filing Date
JP2012503967A Expired - Fee Related JP5787876B2 (ja) 2009-04-08 2010-03-30 ピロロピロール誘導体、その製造方法及び半導体としての使用

Country Status (8)

Country Link
US (1) US9067942B2 (enExample)
EP (1) EP2417137A1 (enExample)
JP (1) JP5787876B2 (enExample)
KR (1) KR20120022879A (enExample)
CN (1) CN102388046A (enExample)
BR (1) BRPI1014578A2 (enExample)
TW (1) TW201041891A (enExample)
WO (1) WO2010115767A1 (enExample)

Families Citing this family (52)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2505539C2 (ru) 2008-12-23 2014-01-27 Эбботт Лэборетриз Антивирусные соединения
CN102264737A (zh) 2008-12-23 2011-11-30 雅培制药有限公司 抗病毒化合物
WO2010120935A1 (en) 2009-04-15 2010-10-21 Abbott Laboratories Anti-viral compounds
CN102449030B (zh) 2009-05-27 2014-06-25 巴斯夫欧洲公司 用于有机半导体器件中的二酮基吡咯并吡咯聚合物
US8835579B2 (en) 2009-05-27 2014-09-16 Basf Se Process for polymerising (hetero)aromatic compounds
US8716454B2 (en) 2009-06-11 2014-05-06 Abbvie Inc. Solid compositions
US9394279B2 (en) 2009-06-11 2016-07-19 Abbvie Inc. Anti-viral compounds
US8937150B2 (en) 2009-06-11 2015-01-20 Abbvie Inc. Anti-viral compounds
EP2853531A3 (en) 2009-06-11 2015-08-12 AbbVie Bahamas Ltd. Antiviral compounds
KR101839636B1 (ko) 2010-05-19 2018-03-16 바스프 에스이 유기 반도체 소자에 사용하기 위한 디케토피롤로피롤 중합체
NZ605440A (en) 2010-06-10 2014-05-30 Abbvie Bahamas Ltd Solid compositions comprising an hcv inhibitor
EP2586074B1 (en) 2010-06-24 2016-12-28 Basf Se An organic field effect transistor with improved current on/off ratio and controllable threshold shift
US8946376B2 (en) 2010-09-29 2015-02-03 Basf Se Semiconductors based on diketopyrrolopyrroles
KR101421913B1 (ko) 2010-11-01 2014-07-22 바스프 에스이 유전체로서의 폴리이미드
US9187600B2 (en) 2010-11-01 2015-11-17 Basf Se Polyimides as dielectric
US20130228771A1 (en) 2010-12-22 2013-09-05 Basf Se Semiconductor structure and method for its production
US10201584B1 (en) 2011-05-17 2019-02-12 Abbvie Inc. Compositions and methods for treating HCV
WO2012164479A1 (en) 2011-05-30 2012-12-06 Basf Se Process for the production of polymers by using coupling reactions
JP6165135B2 (ja) 2011-06-22 2017-07-19 ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ 有機半導体素子内で使用するためのジケトピロロピロールオリゴマー
JP6296980B2 (ja) 2011-09-02 2018-03-20 ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ ジケトピロロピロールオリゴマー、及びジケトピロロピロールオリゴマーを含む組成物
CN103044430B (zh) * 2011-10-11 2015-04-29 中国科学院化学研究所 并吡咯二酮-噻吩醌化合物及其制备方法与应用
KR20140101788A (ko) 2011-11-15 2014-08-20 바스프 에스이 유기 반도체 소자 및 이의 제조 방법
KR101990167B1 (ko) 2011-12-07 2019-06-17 바스프 에스이 유기 전계 효과 트랜지스터
EP2789024B1 (en) 2011-12-07 2015-11-18 Basf Se Diketopyrrolopyrrole polymers for use in organic semiconductor devices
US9034832B2 (en) 2011-12-29 2015-05-19 Abbvie Inc. Solid compositions
EP2834284B1 (en) 2012-04-02 2017-05-10 Basf Se Phenanthro[9,10-b]furan polymers and small molecules for electronic applications
KR102079604B1 (ko) 2012-04-04 2020-04-08 바스프 에스이 디케토피롤로피롤 중합체 및 소분자
JP6207606B2 (ja) 2012-07-23 2017-10-04 ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ ジチエノベンゾフランポリマーおよび電子的な応用のための小分子
JP5890366B2 (ja) * 2012-09-26 2016-03-22 富士フイルム株式会社 光電変換素子、撮像素子、光センサ
EP2928940B1 (en) 2012-12-04 2021-03-03 CLAP Co., Ltd. Functionalized benzodithiophene polymers for electronic application
KR102094742B1 (ko) * 2012-12-24 2020-03-30 삼성전자주식회사 유기 반도체 고분자, 유기 박막 트랜지스터 및 전자 소자
CN103087083A (zh) * 2013-01-17 2013-05-08 中国科学院宁波材料技术与工程研究所 一种吡咯并吡咯二酮衍生物及其制备方法和应用
US11484534B2 (en) 2013-03-14 2022-11-01 Abbvie Inc. Methods for treating HCV
WO2014180704A1 (en) 2013-05-06 2014-11-13 Basf Se Soluble cyclic imides containing polymers as dielectrics in organic electronic applications
CN104177364A (zh) * 2013-05-27 2014-12-03 海洋王照明科技股份有限公司 含吡咯并吡咯烷酮单元的有机半导体材料及其制备方法和太阳能电池器件
CN104177374A (zh) * 2013-05-27 2014-12-03 海洋王照明科技股份有限公司 含噻唑并噻唑单元的有机半导体材料及其制备方法和太阳能电池器件
CN104177366A (zh) * 2013-05-27 2014-12-03 海洋王照明科技股份有限公司 含吡咯并吡咯烷酮单元的有机半导体材料及其制备方法和太阳能电池器件
CN104177365A (zh) * 2013-05-27 2014-12-03 海洋王照明科技股份有限公司 含吡咯并吡咯烷酮单元的有机半导体材料及其制备方法和太阳能电池器件
KR101676526B1 (ko) * 2013-06-05 2016-11-16 주식회사 엘지화학 신규한 화합물, 이를 포함하는 광전 변환 소자
EP2818493A1 (en) 2013-06-25 2014-12-31 Basf Se Near infrared absorbing polymers for electronic applications
EP3013885B1 (en) 2013-06-27 2022-08-10 CLAP Co., Ltd. Metathesis polymers as dielectrics
JP6214768B2 (ja) 2013-07-08 2017-10-18 ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ アジド系架橋剤
CN105637009B (zh) * 2013-09-16 2018-06-12 株式会社Lg化学 共聚物和包含其的有机太阳能电池
WO2015103490A1 (en) 2014-01-03 2015-07-09 Abbvie, Inc. Solid antiviral dosage forms
WO2016046659A1 (en) 2014-09-25 2016-03-31 Basf Se Ether-based polymers as photo-crosslinkable dielectrics
JP6590932B2 (ja) * 2014-12-19 2019-10-16 ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ 有機半導体材料として電子デバイスに使用するための６ｈ−ピロロ［３，２−ｂ：４，５−ｂ’］ビス［１，４］ベンゾチアジン−６−カルボン酸エステル
US9580556B2 (en) 2015-01-29 2017-02-28 Corning Incorporated DPP with branched alkyl-chain or (and) fused thiophene with branched alkyl-chain and the related designing strategy to increase the molecular weight of their semi-conducting copolymers
EP3464415B1 (en) 2016-05-25 2020-08-19 Basf Se Semiconductors
WO2018060015A1 (en) 2016-09-27 2018-04-05 Basf Se Star-shaped styrene polymers with enhanced glass transition temperature
TWI764929B (zh) 2016-09-27 2022-05-21 德商巴地斯顏料化工廠 具有經增強的可交聯性之星形及三嵌段聚合物
CN115304610A (zh) * 2022-09-19 2022-11-08 济南大学 一种吡咯并吡咯二酮基红光转光剂材料
CN115385921B (zh) * 2022-09-29 2024-04-16 天津大学 噻唑-5-吡咯并吡咯二酮及其共轭聚合物的制备方法和作为半导体材料的应用

Family Cites Families (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ATE22104T1 (de) 1982-05-17 1986-09-15 Ciba Geigy Ag Herstellung von pyrrolo-(3,4-c)-pyrrolen.
EP0184982B1 (de) 1984-11-07 1991-01-23 Ciba-Geigy Ag Verfahren zur Herstellung von Pyrrolo-[3,4-c]-pyrrolen und neue Pyrrolo-[3,4-c]-pyrrole
US5703436A (en) 1994-12-13 1997-12-30 The Trustees Of Princeton University Transparent contacts for organic devices
US6420031B1 (en) 1997-11-03 2002-07-16 The Trustees Of Princeton University Highly transparent non-metallic cathodes
AT411306B (de) 2000-04-27 2003-11-25 Qsel Quantum Solar Energy Linz Photovoltaische zelle mit einer photoaktiven schicht aus zwei molekularen organischen komponenten
US20030021913A1 (en) 2001-07-03 2003-01-30 O'neill Mary Liquid crystal alignment layer
US20040004433A1 (en) 2002-06-26 2004-01-08 3M Innovative Properties Company Buffer layers for organic electroluminescent devices and methods of manufacture and use
EP1611207B1 (en) 2003-04-10 2016-02-03 Basf Se Fluorescent diketopyrrolopyrroles
DE10326547A1 (de) 2003-06-12 2005-01-05 Siemens Ag Tandemsolarzelle mit einer gemeinsamen organischen Elektrode
CN101747493B (zh) 2003-10-28 2014-07-02 西巴特殊化学品控股有限公司 二酮基吡咯并吡咯聚合物
US7194173B2 (en) 2004-07-16 2007-03-20 The Trustees Of Princeton University Organic devices having a fiber structure
JP2006117591A (ja) 2004-10-22 2006-05-11 Toyo Ink Mfg Co Ltd 蛍光性ジケトピロロピロール化合物
US20070079867A1 (en) 2005-10-12 2007-04-12 Kethinni Chittibabu Photovoltaic fibers
JP2007266285A (ja) * 2006-03-28 2007-10-11 Nippon Kayaku Co Ltd 電界効果トランジスタ
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
US20090302311A1 (en) 2006-06-30 2009-12-10 Turbiez Mathieu G R Diketopyrrolopyrrole polymers as organic semiconductors
JP5431340B2 (ja) 2007-10-09 2014-03-05 ビーエーエスエフ ソシエタス・ヨーロピア ピロロピロール誘導体、その製造及び使用
CN102203160B (zh) 2008-10-31 2013-07-17 巴斯夫欧洲公司 用于有机半导体器件的二酮吡咯并吡咯聚合物
EP2350161B1 (en) 2008-10-31 2018-11-21 Basf Se Diketopyrrolopyrrole polymers for use in organic field effect transistors

Also Published As

Publication number Publication date
CN102388046A (zh) 2012-03-21
US20120095236A1 (en) 2012-04-19
EP2417137A1 (en) 2012-02-15
WO2010115767A1 (en) 2010-10-14
KR20120022879A (ko) 2012-03-12
US9067942B2 (en) 2015-06-30
TW201041891A (en) 2010-12-01
BRPI1014578A2 (pt) 2015-08-25
JP2012523387A (ja) 2012-10-04

Similar Documents

Publication Publication Date Title
US9067942B2 (en) Pyrrolopyrrole derivatives, their manufacture and use as semiconductors
US10177313B2 (en) Diketopyrrolopyrrole polymers for use in organic semiconductor devices
KR101546985B1 (ko) 피롤로피롤 유도체, 그의 제조 및 용도
JP6296980B2 (ja) ジケトピロロピロールオリゴマー、及びジケトピロロピロールオリゴマーを含む組成物
EP2205657B1 (en) Ketopyrroles as organic semiconductors
JP5675787B2 (ja) 有機半導体装置で使用するためのジケトピロロピロールポリマー
JP5921554B2 (ja) ジケトピロロピロール系の半導体
US20110317628A1 (en) Method of performing wireless communication in multi-carrier system

Legal Events

Date Code Title Description
A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20130327

A621 Written request for application examination

Free format text: JAPANESE INTERMEDIATE CODE: A621

Effective date: 20130327

A977 Report on retrieval

Free format text: JAPANESE INTERMEDIATE CODE: A971007

Effective date: 20140508

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20140512

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20140806

A02 Decision of refusal

Free format text: JAPANESE INTERMEDIATE CODE: A02

Effective date: 20150126

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20150515

A911 Transfer to examiner for re-examination before appeal (zenchi)

Free format text: JAPANESE INTERMEDIATE CODE: A911

Effective date: 20150525

TRDD Decision of grant or rejection written
A01 Written decision to grant a patent or to grant a registration (utility model)

Free format text: JAPANESE INTERMEDIATE CODE: A01

Effective date: 20150629

A61 First payment of annual fees (during grant procedure)

Free format text: JAPANESE INTERMEDIATE CODE: A61

Effective date: 20150728

R150 Certificate of patent or registration of utility model

Ref document number: 5787876

Country of ref document: JP

Free format text: JAPANESE INTERMEDIATE CODE: R150

LAPS Cancellation because of no payment of annual fees