TWI480280B - 氯化萘四羧酸衍生物、其製備方法及用於有機電子產品之用途 - Google Patents

氯化萘四羧酸衍生物、其製備方法及用於有機電子產品之用途 Download PDF

Info

Publication number
TWI480280B
TWI480280B TW098118955A TW98118955A TWI480280B TW I480280 B TWI480280 B TW I480280B TW 098118955 A TW098118955 A TW 098118955A TW 98118955 A TW98118955 A TW 98118955A TW I480280 B TWI480280 B TW I480280B
Authority
TW
Taiwan
Prior art keywords
group
formula
compound
alkyl
hydrogen
Prior art date
Application number
TW098118955A
Other languages
English (en)
Chinese (zh)
Other versions
TW201002709A (en
Inventor
Martin Koenemann
Gabriele Mattern
Frank Wuerthner
Cornelia Roeger
Ruediger Schmidt
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 TW201002709A publication Critical patent/TW201002709A/zh
Application granted granted Critical
Publication of TWI480280B publication Critical patent/TWI480280B/zh

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/06—Peri-condensed systems
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/06—Peri-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/06—Peri-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00—Other synthetic dyes of known constitution
    • C09B57/08—Naphthalimide dyes; Phthalimide dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent materials, e.g. electroluminescent or chemiluminescent
    • C09K11/06—Luminescent materials, e.g. electroluminescent or chemiluminescent containing organic luminescent materials
    • 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
    • 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
    • H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
    • H10K30/50—Photovoltaic [PV] devices
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • 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)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Photovoltaic Devices (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
TW098118955A 2008-06-06 2009-06-06 氯化萘四羧酸衍生物、其製備方法及用於有機電子產品之用途 TWI480280B (zh)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102008027214 2008-06-06
US11676008P 2008-11-21 2008-11-21

Publications (2)

Publication Number Publication Date
TW201002709A TW201002709A (en) 2010-01-16
TWI480280B true TWI480280B (zh) 2015-04-11

Family

ID=41009013

Family Applications (1)

Application Number Title Priority Date Filing Date
TW098118955A TWI480280B (zh) 2008-06-06 2009-06-06 氯化萘四羧酸衍生物、其製備方法及用於有機電子產品之用途

Country Status (7)

Country Link
US (2) US9512354B2 (https=)
EP (1) EP2297274B1 (https=)
JP (1) JP5496189B2 (https=)
KR (1) KR101702487B1 (https=)
CN (1) CN102057015B (https=)
TW (1) TWI480280B (https=)
WO (1) WO2009147237A1 (https=)

Families Citing this family (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101689606B (zh) * 2007-07-10 2012-02-08 巴斯夫欧洲公司 用于生产有机太阳能电池和有机光检测器光敏层的混合物
EP2297274B1 (en) 2008-06-06 2014-11-19 Basf Se Chlorinated naphthalenetetracarboxylic acid derivatives, preparation thereof and use thereof in organic electronics
CN102160207A (zh) * 2008-09-19 2011-08-17 巴斯夫欧洲公司 二苯并四苯基二茚并(1,2,3-cd:1’，2’，3’-lm)苝在有机太阳能电池中的用途
TWI422573B (zh) * 2010-02-11 2014-01-11 Nat Univ Tsing Hua 有機薄膜電晶體暨其製備方法
US20110203649A1 (en) * 2010-02-19 2011-08-25 Basf Se Use of indanthrene compounds in organic photovoltaics
US8790426B2 (en) 2010-04-27 2014-07-29 Basf Se Quaternized terpolymer
JP5733612B2 (ja) * 2011-03-08 2015-06-10 国立大学法人信州大学 有機半導体薄膜用材料、該材料を用いた有機半導体薄膜の形成方法および有機薄膜トランジスタ
DE102011013897A1 (de) * 2011-03-11 2012-09-13 Technische Universität Dresden Organische Solarzelle
EP2521195A1 (en) * 2011-03-15 2012-11-07 Basf Se Tetraazaperopyrene compounds and their use as n-type semiconductors
WO2015059647A1 (en) * 2013-10-23 2015-04-30 Basf Se Crystalline form of n,n'-bis-(heptafluorobutyl)-2,6-dichloro-1,4,5,8-naphthalene tetracarboxylic diimide and the use thereof
WO2015193808A1 (en) * 2014-06-17 2015-12-23 Basf Se N-fluoroalkyl-substituted dibromonaphthalene diimides and their use as semiconductor
US10454037B2 (en) * 2014-08-18 2019-10-22 Basf Se Organic semiconductor composition comprising a liquid medium
US10333072B2 (en) * 2014-08-28 2019-06-25 Basf Se Thin film semiconductor comprising a small-molecular semiconducting compound and a non-conductive polymer
JP7114578B2 (ja) 2016-10-06 2022-08-08 ビーエーエスエフ ソシエタス・ヨーロピア ２－フェニルフェノキシ置換ペリレンビスイミド化合物およびそれらの使用
CN108063180A (zh) 2018-01-05 2018-05-22 华南理工大学 一种酰亚胺类化合物阴离子态薄膜及在p型热电器件中的应用
WO2019134360A1 (zh) * 2018-01-05 2019-07-11 华南理工大学 一种具有室温铁磁性的酰亚胺类化合物阴离子态材料及其应用
EP3762979A1 (en) 2018-03-07 2021-01-13 Clap Co., Ltd. Patterning method for preparing top-gate, bottom-contact organic field effect transistors
US20200411781A1 (en) 2018-03-08 2020-12-31 Clap Co., Ltd. Organic field effect transistor comprising semiconducting single-walled carbon nanotubes and organic semiconducting material
EP3735430B1 (en) 2018-06-26 2023-09-13 Clap Co., Ltd. Vinylether-based polymer as dielectric
CN110102345B (zh) * 2019-05-15 2021-09-10 扬州大学 催化烯烃氧化裂解的含硒共聚物催化剂的合成方法
KR102477550B1 (ko) * 2020-07-09 2022-12-15 연세대학교 산학협력단 강유전 형광 자기조립 화합물 및 이를 포함하는 유기 전자 소자
KR102780907B1 (ko) * 2020-08-10 2025-03-12 아주대학교산학협력단 전하 이동 도핑에 의해 전기 전도도가 변화할 수 있는 유기 반도체 소재 및 이를 구비하는 유기 전계 효과 트랜지스터 기반 가스 센서

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007074137A1 (de) * 2005-12-23 2007-07-05 Basf Se Naphthalintetracarbonsäurederivate und deren verwendung als halbleiter
WO2007116001A2 (de) * 2006-04-07 2007-10-18 Basf Se Flüssig-kristalline rylentetracarbonsäurederivate und deren verwendung

Family Cites Families (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3000168A1 (de) 1980-01-04 1981-07-09 Bayer Ag, 5090 Leverkusen Elektrisch leitende cyclische polyimide
US4461922A (en) 1983-02-14 1984-07-24 Atlantic Richfield Company Solar cell module
DE3620332A1 (de) 1986-06-18 1987-12-23 Bayer Ag Verfahren zur herstellung von tetrachlornaphthalintetracarbonsaeuredianhydrid und -diimid, sowie die neue verbindung 2.3.6.7-tetrachlornaphthalin-1.4.5.8.- tetracarbonsaeurediimid
DE3703131A1 (de) 1987-02-03 1988-08-11 Bayer Ag 2.3.6.7-tetrafluornaphthalintetracarbonsaeurebisimide, verfahren zu ihrer herstellung und ihre verwendung
JPH02255789A (ja) 1989-03-29 1990-10-16 Asahi Chem Ind Co Ltd 有機電場発光素子
JPH0527469A (ja) 1991-07-19 1993-02-05 Kao Corp 電子写真感光体
JP3326552B2 (ja) 1997-11-14 2002-09-24 正視 藤井 多段深埋設接地電極
US6451415B1 (en) * 1998-08-19 2002-09-17 The Trustees Of Princeton University Organic photosensitive optoelectronic device with an exciton blocking layer
US6198092B1 (en) 1998-08-19 2001-03-06 The Trustees Of Princeton University Stacked organic photosensitive optoelectronic devices with an electrically parallel configuration
US6198091B1 (en) 1998-08-19 2001-03-06 The Trustees Of Princeton University Stacked organic photosensitive optoelectronic devices with a mixed electrical configuration
CN101312235B (zh) 1999-05-13 2010-06-09 普林斯顿大学理事会 基于电致磷光的极高效有机发光器件
US6864396B2 (en) 2001-09-27 2005-03-08 3M Innovative Properties Company Substituted pentacene semiconductors
US20030097010A1 (en) 2001-09-27 2003-05-22 Vogel Dennis E. Process for preparing pentacene derivatives
DE10148172B4 (de) * 2001-09-28 2007-11-15 Qimonda Ag Fluoreszierende Naphthalin-1,4,5,8-tetracarbonsäurebisimide mit elektronenschiebendem Substituenten am Kern
WO2003035407A1 (en) 2001-10-22 2003-05-01 Mitsui Chemicals, Inc. Imide compounds and optical recording media made by using the same
US6911716B2 (en) * 2002-09-09 2005-06-28 Lucent Technologies, Inc. Bipolar transistors with vertical structures
US6831771B2 (en) * 2003-01-08 2004-12-14 Sipix Imaging Inc. Electronic whiteboard using electrophoretic display
EP1611484B1 (de) 2003-03-19 2021-11-10 Heliatek GmbH Photoaktives bauelement mit organischen schichten
DE10338550A1 (de) 2003-08-19 2005-03-31 Basf Ag Übergangsmetallkomplexe mit Carbenliganden als Emitter für organische Licht-emittierende Dioden (OLEDs)
US7592539B2 (en) 2003-11-07 2009-09-22 The Trustees Of Princeton University Solid state photosensitive devices which employ isolated photosynthetic complexes
WO2005066718A1 (ja) * 2003-12-26 2005-07-21 Canon Kabushiki Kaisha 電子写真感光体、プロセスカートリッジおよび電子写真装置
JP4921982B2 (ja) * 2004-01-26 2012-04-25 ノースウエスタン ユニバーシティ ペリレンｎ型半導体及び関連装置
US20050224905A1 (en) * 2004-04-13 2005-10-13 Forrest Stephen R High efficiency organic photovoltaic cells employing hybridized mixed-planar heterojunctions
US7605394B2 (en) * 2004-12-23 2009-10-20 Northwestern University Siloxane-polymer dielectric compositions and related organic field-effect transistors
US7795145B2 (en) * 2006-02-15 2010-09-14 Basf Aktiengesellschaft Patterning crystalline compounds on surfaces
US8350035B2 (en) * 2006-02-17 2013-01-08 Basf Aktiengesellschaft Fluorinated rylenetetracarboxylic acid derivatives and use thereof
US20080009092A1 (en) * 2006-07-06 2008-01-10 Basf Aktiengesellschaft Use of chlorinated copper phthalocyanines as air-stable n-channel organic semiconductors
US20080035914A1 (en) * 2006-08-11 2008-02-14 Basf Aktiengesellschaft Use of perylene diimide derivatives as air-stable n-channel organic semiconductors
WO2009024512A1 (de) 2007-08-17 2009-02-26 Basf Se Halogenhaltige perylentetracarbonsäurederivate und deren verwendung
WO2009037283A1 (de) * 2007-09-18 2009-03-26 Basf Se Verfahren zur herstellung von mit rylentetracarbonsäurediimiden beschichteten substraten
EP2297274B1 (en) 2008-06-06 2014-11-19 Basf Se Chlorinated naphthalenetetracarboxylic acid derivatives, preparation thereof and use thereof in organic electronics

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007074137A1 (de) * 2005-12-23 2007-07-05 Basf Se Naphthalintetracarbonsäurederivate und deren verwendung als halbleiter
WO2007116001A2 (de) * 2006-04-07 2007-10-18 Basf Se Flüssig-kristalline rylentetracarbonsäurederivate und deren verwendung

Also Published As

Publication number Publication date
WO2009147237A9 (en) 2010-01-28
WO2009147237A1 (en) 2009-12-10
US9512354B2 (en) 2016-12-06
JP2011522097A (ja) 2011-07-28
US10214525B2 (en) 2019-02-26
KR20110015454A (ko) 2011-02-15
EP2297274B1 (en) 2014-11-19
US20090301552A1 (en) 2009-12-10
TW201002709A (en) 2010-01-16
CN102057015A (zh) 2011-05-11
EP2297274A1 (en) 2011-03-23
US20170174676A1 (en) 2017-06-22
JP5496189B2 (ja) 2014-05-21
CN102057015B (zh) 2015-07-22
KR101702487B1 (ko) 2017-02-06

Similar Documents

Publication Publication Date Title
TWI480280B (zh) 氯化萘四羧酸衍生物、其製備方法及用於有機電子產品之用途
JP5627459B2 (ja) ハロゲン含有のペリレンテトラカルボン酸誘導体及びそれらの使用
US8350035B2 (en) Fluorinated rylenetetracarboxylic acid derivatives and use thereof
US8592806B2 (en) Quinone compounds as dopants in organic electronics
JP6861625B2 (ja) 液状媒体を含有する有機半導体組成物
US9583719B2 (en) Carbazolocarbazol-bis(dicarboximides) and their use as semiconductors
EP2583326A1 (en) Use of substituted perylenes in organic solar cells
CN102844886A (zh) 阴丹士林化合物在有机光伏器件中的用途
CN101384655A (zh) 氟化萘嵌苯四甲酸衍生物及其用途
WO2009000831A1 (de) Bromsubstituierte rylentetracarbonsäurederivate und deren verwendung

Legal Events

Date Code Title Description
MM4A Annulment or lapse of patent due to non-payment of fees