JP5624987B2 - 有機半導体のための誘導体化されたフラーレン系ドーパント - Google Patents

有機半導体のための誘導体化されたフラーレン系ドーパント Download PDF

Info

Publication number
JP5624987B2
JP5624987B2 JP2011526631A JP2011526631A JP5624987B2 JP 5624987 B2 JP5624987 B2 JP 5624987B2 JP 2011526631 A JP2011526631 A JP 2011526631A JP 2011526631 A JP2011526631 A JP 2011526631A JP 5624987 B2 JP5624987 B2 JP 5624987B2
Authority
JP
Japan
Prior art keywords
fullerene
fullerene derivative
semiconductor material
osc
halogenated
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
JP2011526631A
Other languages
English (en)
Japanese (ja)
Other versions
JP2012502495A5 (https=
JP2012502495A (ja
Inventor
ニル テスラー,
ニル テスラー,
オルガ ソロメシュチ,
オルガ ソロメシュチ,
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.)
Technion Research and Development Foundation Ltd
Original Assignee
Technion Research and Development Foundation Ltd
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 Technion Research and Development Foundation Ltd filed Critical Technion Research and Development Foundation Ltd
Publication of JP2012502495A publication Critical patent/JP2012502495A/ja
Publication of JP2012502495A5 publication Critical patent/JP2012502495A5/ja
Application granted granted Critical
Publication of JP5624987B2 publication Critical patent/JP5624987B2/ja
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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
    • H10K85/20Carbon compounds, e.g. carbon nanotubes or fullerenes
    • H10K85/211Fullerenes, e.g. C60
    • H10K85/215Fullerenes, e.g. C60 comprising substituents, e.g. PCBM
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B82NANOTECHNOLOGY
    • B82YSPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y10/00Nanotechnology for information processing, storage or transmission, e.g. quantum computing or single electron logic
    • 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]
    • H10K10/484Insulated gate field-effect transistors [IGFETs] characterised by the channel regions
    • H10K10/488Insulated gate field-effect transistors [IGFETs] characterised by the channel regions the channel region comprising a layer of composite material having interpenetrating or embedded materials, e.g. a mixture of donor and acceptor moieties, that form a bulk heterojunction
    • 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]
    • H10K50/18Carrier blocking layers
    • 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
    • H10K85/10Organic polymers or oligomers
    • H10K85/111Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • H10K85/113Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
    • 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
    • H10K85/10Organic polymers or oligomers
    • H10K85/111Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • H10K85/114Poly-phenylenevinylene; Derivatives thereof
    • 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
    • H10K85/10Organic polymers or oligomers
    • H10K85/111Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • H10K85/115Polyfluorene; Derivatives thereof
    • 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
    • H10K85/10Organic polymers or oligomers
    • H10K85/141Organic polymers or oligomers comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/10Definition of the polymer structure
    • C08G2261/14Side-groups
    • C08G2261/141Side-chains having aliphatic units
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/32Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
    • C08G2261/322Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed
    • C08G2261/3223Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed containing one or more sulfur atoms as the only heteroatom, e.g. thiophene
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/90Applications
    • C08G2261/92TFT applications
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L65/00Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Compositions of derivatives of such polymers
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00Properties of the organic materials covered by group H10K85/00
    • H10K2101/30Highest occupied molecular orbital [HOMO], lowest unoccupied molecular orbital [LUMO] or Fermi energy values
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K30/00Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
    • H10K30/50Photovoltaic [PV] devices
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K71/00Manufacture or treatment specially adapted for the organic devices covered by this subclass
    • H10K71/10Deposition of organic active material
    • H10K71/16Deposition of organic active material using physical vapour deposition [PVD], e.g. vacuum deposition or sputtering
    • H10K71/164Deposition of organic active material using physical vapour deposition [PVD], e.g. vacuum deposition or sputtering using vacuum deposition
    • 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
    • H10K85/10Organic polymers or oligomers
    • H10K85/141Organic polymers or oligomers comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE
    • H10K85/146Organic polymers or oligomers comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE poly N-vinylcarbazol; Derivatives thereof
    • 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
    • H10K85/30Coordination compounds
    • H10K85/311Phthalocyanine
    • 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
    • H10K85/615Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • 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
    • H10K85/631Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • 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
    • 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
    • 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
    • Y02PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P70/00Climate change mitigation technologies in the production process for final industrial or consumer products
    • Y02P70/50Manufacturing or production processes characterised by the final manufactured product

Landscapes

  • Engineering & Computer Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Materials Engineering (AREA)
  • Nanotechnology (AREA)
  • Physics & Mathematics (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Theoretical Computer Science (AREA)
  • Mathematical Physics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Electromagnetism (AREA)
  • Optics & Photonics (AREA)
  • Polymers & Plastics (AREA)
  • Medicinal Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Composite Materials (AREA)
  • Photovoltaic Devices (AREA)
  • Electroluminescent Light Sources (AREA)
  • Thin Film Transistor (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Light Receiving Elements (AREA)
JP2011526631A 2008-09-09 2009-09-09 有機半導体のための誘導体化されたフラーレン系ドーパント Expired - Fee Related JP5624987B2 (ja)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US13648608P 2008-09-09 2008-09-09
US61/136,486 2008-09-09
PCT/IL2009/000879 WO2010029542A1 (en) 2008-09-09 2009-09-09 Derivatized fullerene-based dopants for organic semiconductors

Related Child Applications (1)

Application Number Title Priority Date Filing Date
JP2014197706A Division JP2015053489A (ja) 2008-09-09 2014-09-29 有機半導体のための誘導体化されたフラーレン系ドーパント

Publications (3)

Publication Number Publication Date
JP2012502495A JP2012502495A (ja) 2012-01-26
JP2012502495A5 JP2012502495A5 (https=) 2012-10-25
JP5624987B2 true JP5624987B2 (ja) 2014-11-12

Family

ID=41650357

Family Applications (2)

Application Number Title Priority Date Filing Date
JP2011526631A Expired - Fee Related JP5624987B2 (ja) 2008-09-09 2009-09-09 有機半導体のための誘導体化されたフラーレン系ドーパント
JP2014197706A Pending JP2015053489A (ja) 2008-09-09 2014-09-29 有機半導体のための誘導体化されたフラーレン系ドーパント

Family Applications After (1)

Application Number Title Priority Date Filing Date
JP2014197706A Pending JP2015053489A (ja) 2008-09-09 2014-09-29 有機半導体のための誘導体化されたフラーレン系ドーパント

Country Status (6)

Country Link
US (1) US8431434B2 (https=)
EP (1) EP2335299B1 (https=)
JP (2) JP5624987B2 (https=)
KR (1) KR101604102B1 (https=)
CN (1) CN102217110B (https=)
WO (1) WO2010029542A1 (https=)

Families Citing this family (37)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8431434B2 (en) 2008-09-09 2013-04-30 Technion Research & Development Foundation Limited Derivatized fullerene-based dopants for organic semiconductors
EP2439804B1 (en) * 2009-06-01 2021-07-21 Showa Denko Materials Co., Ltd. Organic electronic material, ink composition containing same, and organic thin film, organic electronic element, organic electroluminescent element, lighting device, and display device formed therewith
US20120091449A1 (en) * 2009-06-23 2012-04-19 Sumitomo Chemical Company, Limited Organic electroluminescent element
EP2528855A1 (en) 2010-01-25 2012-12-05 The Board of Regents of the Leland Stanford Junior University Fullerene-doped nanostructures and methods therefor
US8524525B2 (en) 2010-01-25 2013-09-03 The Board Of Trustees Of The Leland Stanford Junior University Joined nanostructures and methods therefor
KR101036213B1 (ko) * 2010-01-26 2011-05-20 광주과학기술원 발광소자와 태양전지 성능을 포함하는 전자소자
JP5933524B2 (ja) * 2010-04-08 2016-06-08 ザ リージェンツ オブ ザ ユニヴァシティ オブ ミシガン 熱および溶媒蒸気アニール工程により製造される、改良されたバルクヘテロジャンクション型デバイス
GB201009718D0 (en) * 2010-06-10 2010-07-21 Univ Manchester Functionalised graphene
DE102010046040B4 (de) * 2010-09-22 2021-11-11 Novaled Gmbh Verfahren zur Herstellung von Fulleren-Derivaten
US9293553B2 (en) 2011-03-10 2016-03-22 The Trustees Of Columbia University In The City Of New York Graphene electrodes for electronic devices
GB201105582D0 (en) * 2011-04-01 2011-05-18 Cambridge Display Tech Ltd Organic light-emitting device and method
US9263524B2 (en) * 2011-04-05 2016-02-16 The Board Of Trustees Of The Leland Stanford Junior University Semiconductor materials, apparatuses and methods
WO2013018251A1 (ja) * 2011-08-03 2013-02-07 パナソニック株式会社 有機発光素子
EP2571072A1 (en) * 2011-09-13 2013-03-20 LANXESS Deutschland GmbH Semiconducting thin [60]fullerene films and their use
GB201118997D0 (en) 2011-11-03 2011-12-14 Cambridge Display Tech Ltd Electronic device and method
CN103427045A (zh) * 2012-05-14 2013-12-04 海洋王照明科技股份有限公司 一种有机电致发光器件及其制备方法
US9881712B2 (en) 2012-07-20 2018-01-30 Rohm And Haas Electronic Materials Llc Highly crystalline electrically conducting polymers, methods of manufacture thereof and articles comprising the same
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
CN102903525B (zh) * 2012-10-19 2015-11-25 中国科学院化学研究所 一种用于全固态电储能器件的正电荷储能材料
GB201309668D0 (en) 2013-05-30 2013-07-17 Isis Innovation Organic semiconductor doping process
US10600964B2 (en) 2013-12-17 2020-03-24 Rohm And Haas Electronic Materials Llc Highly crystalline electrically conducting organic materials, methods of manufacture thereof and articles comprising the same
TWI570982B (zh) * 2013-12-31 2017-02-11 昆山工研院新型平板顯示技術中心有限公司 An organic light emitting display device and a top emission organic light emitting diode device with improved viewing angle characteristics
CN103746075B (zh) * 2014-01-11 2017-03-08 马良 一种改善有机薄膜晶体管稳定性的方法
GB2527606A (en) * 2014-06-27 2015-12-30 Cambridge Display Tech Ltd Charge-transfer salt
WO2016190217A1 (ja) * 2015-05-28 2016-12-01 ソニーセミコンダクタソリューションズ株式会社 光電変換素子および固体撮像装置ならびに電子機器
GB2546523A (en) * 2016-01-21 2017-07-26 Cambridge Display Tech Ltd Organic photodetector with reduced dark current
EP3208862B1 (en) 2016-02-22 2024-10-09 Novaled GmbH Charge transporting semi-conducting material and electronic device comprising it
EP3208863B1 (en) 2016-02-22 2019-10-23 Novaled GmbH Charge transporting semi-conducting material and electronic device comprising it
EP3410510B1 (en) 2017-06-02 2021-10-20 Novaled GmbH Organic electronic device and method for producing the organic electronic device
EP3444662A1 (en) * 2017-08-17 2019-02-20 Université de Strasbourg Liquid crystal spatial light modulator
CN108690602B (zh) * 2018-05-22 2020-12-18 四川大学 一种增强富勒烯荧光性能的方法
CN109205591B (zh) * 2018-07-05 2022-04-26 南京理工大学 一种新型富勒烯衍生物微球的制备方法
DE102018125307A1 (de) * 2018-10-12 2020-04-16 Novaled Gmbh Organische lichtemittierende Vorrichtung
US11527582B1 (en) 2019-09-24 2022-12-13 Apple Inc. Display stack with integrated photodetectors
US11839133B2 (en) * 2021-03-12 2023-12-05 Apple Inc. Organic photodetectors for in-cell optical sensing
US12124002B2 (en) 2021-09-03 2024-10-22 Apple Inc. Beam deflector metasurface
CN113777901A (zh) * 2021-09-08 2021-12-10 上海交通大学 一种掺杂有机小分子供体材料的液晶薄膜器件及显示装置

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1209708B1 (en) 2000-11-24 2007-01-17 Sony Deutschland GmbH Hybrid solar cells with thermal deposited semiconductive oxide layer
US6580027B2 (en) * 2001-06-11 2003-06-17 Trustees Of Princeton University Solar cells using fullerenes
US20070181874A1 (en) * 2004-12-30 2007-08-09 Shiva Prakash Charge transport layers and organic electron devices comprising same
JP4779172B2 (ja) 2005-01-06 2011-09-28 独立行政法人産業技術総合研究所 ドーピングされたカーボンナノチューブ及びその製造方法
US8017863B2 (en) * 2005-11-02 2011-09-13 The Regents Of The University Of Michigan Polymer wrapped carbon nanotube near-infrared photoactive devices
WO2007121252A2 (en) 2006-04-11 2007-10-25 Konarka Technologies, Inc. Tandem photovoltaic cells
US8093580B2 (en) * 2006-11-22 2012-01-10 Nec Corporation Semiconductor device and method of manufacturing the same
KR100846597B1 (ko) * 2007-01-24 2008-07-16 삼성에스디아이 주식회사 함불소 화합물 및 탄소계 화합물을 포함하는 유기 발광소자
US8658290B2 (en) * 2007-10-31 2014-02-25 Basf Se Use of halogenated phthalocyanines
US8431434B2 (en) 2008-09-09 2013-04-30 Technion Research & Development Foundation Limited Derivatized fullerene-based dopants for organic semiconductors

Also Published As

Publication number Publication date
JP2015053489A (ja) 2015-03-19
US20110156019A1 (en) 2011-06-30
US8431434B2 (en) 2013-04-30
KR101604102B1 (ko) 2016-03-25
EP2335299A1 (en) 2011-06-22
KR20110065485A (ko) 2011-06-15
WO2010029542A1 (en) 2010-03-18
CN102217110B (zh) 2014-06-04
JP2012502495A (ja) 2012-01-26
EP2335299B1 (en) 2018-01-10
CN102217110A (zh) 2011-10-12
WO2010029542A8 (en) 2011-03-31

Similar Documents

Publication Publication Date Title
JP5624987B2 (ja) 有機半導体のための誘導体化されたフラーレン系ドーパント
US8828274B2 (en) Polyarylamine ketones
CN101981722B (zh) 有机半导体组合物以及有机薄膜和具有该有机薄膜的有机薄膜元件
US11787965B2 (en) Ink composition for forming an organic layer of a semiconductor
Ohisa et al. Conjugated polyelectrolyte blend with polyethyleneimine ethoxylated for thickness-insensitive electron injection layers in organic light-emitting devices
US12082426B2 (en) Photodetector composition
Suh et al. High-efficiency polymer LEDs with fast response times fabricated via selection of electron-injecting conjugated polyelectrolyte backbone structure
Shin et al. Synthesis and aggregation behavior of a glycolated naphthalene diimide bithiophene copolymer for application in low-level n-doped organic thermoelectrics
Huang et al. Architecture of Conjugated Donor–Acceptor (D–A)‐Type Polymer Films with Cross‐Linked Structures
Porz et al. TIPS‐Tetracene‐and TIPS‐Pentacene‐Annulated Poly (norbornadiene) s: Synthesis and Properties
Lee et al. Molecular stacking effect on small-molecular organic light-emitting diodes prepared with solution process
Zhong et al. Hole‐Trapping Effect of the Aliphatic‐Amine Based Electron Injection Materials in the Operation of OLEDs to Facilitate the Electron Injection
Stolz et al. High-performance electron injection layers with a wide processing window from an amidoamine-functionalized polyfluorene
US7547926B2 (en) Heterojunction with linkages between an electron donor and an electron acceptor in a blend
Lang et al. Pendant perylene polymers with high electron mobility
Tang et al. Aggregation‐Induced Emission by Molecular Design: A Route to High‐Performance Light‐Emitting Electrochemical Cells
Hamilton et al. Optimizing interfacial energetics for conjugated polyelectrolyte electron injection layers in high efficiency and fast responding polymer light emitting diodes
Jaballah et al. New bithiophene-containing electroluminescent polymer: Synthesis, characterization, optical and electrical properties
Zhong et al. An alkane-soluble dendrimer as electron-transport layer in polymer light-emitting diodes
Chandrasekaran et al. Role of molecular and interchain ordering in the formation of a δ-hole-transporting layer in organic solar cells
Fallahi et al. Cationic Water-Soluble Conjugated Polyelectrolytes/Graphene Oxide Nanocomposites as Efficient Green Hole Injection Layers in Organic Light Emitting Diodes
Matsuo et al. Anthracene-based organic small-molecule electron-injecting material for inverted organic light-emitting diodes
Martinez-Ferrero et al. Influence of the molecular weight and size dispersion of the electroluminescent polymer on the performance of air-stable hybrid light-emitting diodes
Tang et al. Electropolymerization of 3-methylthiophene in the presence of a small amount of bithiophene and its usage as hole transport layer in organic light emitting diodes
Solomeshch c12) United States Patent

Legal Events

Date Code Title Description
A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20120904

A621 Written request for application examination

Free format text: JAPANESE INTERMEDIATE CODE: A621

Effective date: 20120904

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20140228

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20140523

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: 20140829

A61 First payment of annual fees (during grant procedure)

Free format text: JAPANESE INTERMEDIATE CODE: A61

Effective date: 20140929

R150 Certificate of patent or registration of utility model

Ref document number: 5624987

Country of ref document: JP

Free format text: JAPANESE INTERMEDIATE CODE: R150

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

LAPS Cancellation because of no payment of annual fees