JP5763632B2 - 少なくとも1つのビチオフェン繰り返し単位を含むポリマー、該ポリマーを合成する方法、およびそれを含む組成物 - Google Patents

少なくとも1つのビチオフェン繰り返し単位を含むポリマー、該ポリマーを合成する方法、およびそれを含む組成物 Download PDF

Info

Publication number
JP5763632B2
JP5763632B2 JP2012518600A JP2012518600A JP5763632B2 JP 5763632 B2 JP5763632 B2 JP 5763632B2 JP 2012518600 A JP2012518600 A JP 2012518600A JP 2012518600 A JP2012518600 A JP 2012518600A JP 5763632 B2 JP5763632 B2 JP 5763632B2
Authority
JP
Japan
Prior art keywords
optionally substituted
copolymer
composition
group
represented
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
JP2012518600A
Other languages
English (en)
Japanese (ja)
Other versions
JP2012532229A5 (enExample
JP2012532229A (ja
Inventor
クリストファー タイラー ブラウン
クリストファー タイラー ブラウン
チャド ランディス
チャド ランディス
エレナ シェイナ
エレナ シェイナ
Original Assignee
ソルベイ ユーエスエイ インコーポレイテッド
ソルベイ ユーエスエイ インコーポレイテッド
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 ソルベイ ユーエスエイ インコーポレイテッド, ソルベイ ユーエスエイ インコーポレイテッド filed Critical ソルベイ ユーエスエイ インコーポレイテッド
Publication of JP2012532229A publication Critical patent/JP2012532229A/ja
Publication of JP2012532229A5 publication Critical patent/JP2012532229A5/ja
Application granted granted Critical
Publication of JP5763632B2 publication Critical patent/JP5763632B2/ja
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L65/00—Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Compositions of derivatives of such polymers
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
    • H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
    • H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
    • H01B1/124—Intrinsically conductive polymers
    • H01B1/127—Intrinsically conductive polymers comprising five-membered aromatic rings in the main chain, e.g. polypyrroles, polythiophenes
    • 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
    • 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
    • C07D495/12—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 three hetero rings
    • C07D495/14—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains three hetero rings
    • C07D513/14—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
    • C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
    • C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
    • C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
    • C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
    • C08G61/124—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one nitrogen atom in the ring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
    • C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
    • C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
    • C08G61/126—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one sulfur atom in the ring
    • 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
    • C09B57/004—Diketopyrrolopyrrole dyes
    • 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
    • C09B57/007—Squaraine dyes
    • 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
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B69/00—Dyes not provided for by a single group of this subclass
    • C09B69/008—Dyes containing a substituent, which contains a silicium atom
    • 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
    • C09B69/00—Dyes not provided for by a single group of this subclass
    • C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
    • C09B69/109—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing other specific dyes
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
    • H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
    • H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
    • 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
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/10—Definition of the polymer structure
    • C08G2261/12—Copolymers
    • C08G2261/124—Copolymers alternating
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/10—Definition of the polymer structure
    • C08G2261/14—Side-groups
    • C08G2261/141—Side-chains having aliphatic units
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/31—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain
    • C08G2261/316—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain bridged by heteroatoms, e.g. N, P, Si or B
    • C08G2261/3162—Arylamines
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
    • C08G2261/324—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed
    • C08G2261/3243—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed containing one or more sulfur atoms as the only heteroatom, e.g. benzothiophene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/33—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain
    • C08G2261/334—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain containing heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/34—Monomer units or repeat units incorporating structural elements in the main chain incorporating partially-aromatic structural elements in the main chain
    • C08G2261/344—Monomer units or repeat units incorporating structural elements in the main chain incorporating partially-aromatic structural elements in the main chain containing heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/36—Oligomers, i.e. comprising up to 10 repeat units
    • C08G2261/364—Oligomers, i.e. comprising up to 10 repeat units containing hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/40—Polymerisation processes
    • C08G2261/41—Organometallic coupling reactions
    • C08G2261/414—Stille reactions
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/90—Applications
    • C08G2261/91—Photovoltaic applications
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
    • H10K71/10—Deposition of organic active material
    • H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
    • H10K71/20—Changing the shape of the active layer in the devices, e.g. patterning
    • H10K71/211—Changing the shape of the active layer in the devices, e.g. patterning by selective transformation of an existing layer
    • 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
    • H10K85/10—Organic polymers or oligomers
    • H10K85/151—Copolymers
    • 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
    • H10K85/611—Charge transfer complexes
    • 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
    • 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
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/582—Recycling of unreacted starting or intermediate materials

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Photovoltaic Devices (AREA)
  • Electroluminescent Light Sources (AREA)
JP2012518600A 2009-06-30 2010-06-30 少なくとも1つのビチオフェン繰り返し単位を含むポリマー、該ポリマーを合成する方法、およびそれを含む組成物 Expired - Fee Related JP5763632B2 (ja)

Applications Claiming Priority (15)

Application Number Priority Date Filing Date Title
US22205309P 2009-06-30 2009-06-30
US61/222,053 2009-06-30
US24013709P 2009-09-04 2009-09-04
US61/240,137 2009-09-04
US24181309P 2009-09-11 2009-09-11
US61/241,813 2009-09-11
US24833509P 2009-10-02 2009-10-02
US61/248,335 2009-10-02
US28931409P 2009-12-22 2009-12-22
US61/289,314 2009-12-22
US29084409P 2009-12-29 2009-12-29
US61/290,844 2009-12-29
US30738710P 2010-02-23 2010-02-23
US61/307,387 2010-02-23
PCT/US2010/040664 WO2011002927A2 (en) 2009-06-30 2010-06-30 Novel compositions, methods and polymers

Publications (3)

Publication Number Publication Date
JP2012532229A JP2012532229A (ja) 2012-12-13
JP2012532229A5 JP2012532229A5 (enExample) 2013-07-25
JP5763632B2 true JP5763632B2 (ja) 2015-08-12

Family

ID=42669008

Family Applications (1)

Application Number Title Priority Date Filing Date
JP2012518600A Expired - Fee Related JP5763632B2 (ja) 2009-06-30 2010-06-30 少なくとも1つのビチオフェン繰り返し単位を含むポリマー、該ポリマーを合成する方法、およびそれを含む組成物

Country Status (5)

Country Link
US (1) US8440785B2 (enExample)
EP (1) EP2449561A2 (enExample)
JP (1) JP5763632B2 (enExample)
KR (1) KR20120061806A (enExample)
WO (1) WO2011002927A2 (enExample)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11283033B2 (en) 2018-03-09 2022-03-22 Lg Chem, Ltd. Composition for organic layer of organic solar cell and organic solar cell

Families Citing this family (48)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8212239B2 (en) * 2007-12-13 2012-07-03 E I Du Pont De Nemours And Company Electroactive materials
US8115200B2 (en) * 2007-12-13 2012-02-14 E.I. Du Pont De Nemours And Company Electroactive materials
US8216753B2 (en) 2007-12-13 2012-07-10 E I Du Pont De Nemours And Company Electroactive materials
US8067764B2 (en) * 2007-12-17 2011-11-29 E. I. Du Pont De Nemours And Company Electroactive materials
US8461291B2 (en) * 2007-12-17 2013-06-11 E I Du Pont De Nemours And Company Organic electroactive materials and an organic electronic device having an electroactive layer utilizing the same material
KR101805203B1 (ko) 2009-05-27 2018-01-10 바스프 에스이 폴리시클릭 디티오펜
US20110006287A1 (en) * 2009-07-10 2011-01-13 Wei You Polymers with tunable band gaps for photonic and electronic applications
WO2011028827A2 (en) * 2009-09-04 2011-03-10 Plextronics, Inc. Organic electronic devices and polymers, including photovoltaic cells and diketone-based polymers
JP5782703B2 (ja) * 2009-10-29 2015-09-24 住友化学株式会社 高分子化合物及びそれを用いた電子素子
KR101839636B1 (ko) 2010-05-19 2018-03-16 바스프 에스이 유기 반도체 소자에 사용하기 위한 디케토피롤로피롤 중합체
EP2578614A4 (en) * 2010-05-24 2014-01-22 Oceans King Lighting Science CHINOXALIN CONJUGATED POLYMER WITH ANELLIED THIOPHONE UNIT, METHOD OF MANUFACTURE AND ITS USE
CN102906151B (zh) * 2010-06-25 2014-05-07 海洋王照明科技股份有限公司 基于苯唑二噻吩和噻吩并吡嗪的共轭聚合物及其制备方法和应用
US9577194B2 (en) 2010-07-02 2017-02-21 Nissan Chemical Industries, Ltd. Hole transport compositions and related devices and methods (I)
JP5692228B2 (ja) * 2010-07-02 2015-04-01 コニカミノルタ株式会社 有機光電変換素子およびそれを用いた太陽電池
JP5964553B2 (ja) * 2011-01-28 2016-08-03 三菱化学株式会社 新規コポリマー、有機半導体材料、及びこれを用いた有機電子デバイス、光電変換素子並びに太陽電池モジュール
US8816040B2 (en) * 2011-06-24 2014-08-26 University Of Tsukuba Polymer dye
KR101830784B1 (ko) * 2011-09-09 2018-02-22 삼성전자주식회사 폴리머 및 상기 폴리머를 포함한 유기 발광 소자
US9949720B2 (en) * 2011-10-21 2018-04-24 C. R. Bard, Inc. Systems and methods for ultrasound-based medical device assessment
JP5884423B2 (ja) * 2011-11-15 2016-03-15 住友化学株式会社 高分子化合物及びそれを用いた有機光電変換素子
EP3718573B1 (en) * 2011-12-30 2026-05-20 University of Washington through its Center for Commercialization Narrowband Chromophore Emitting Polymer Dots
JP5859872B2 (ja) * 2012-02-17 2016-02-16 富士フイルム株式会社 有機光電変換素子組成物、これを含む薄膜、光電池、これに用いられる有機半導体ポリマー、化合物およびポリマーの製造方法
KR102079604B1 (ko) * 2012-04-04 2020-04-08 바스프 에스이 디케토피롤로피롤 중합체 및 소분자
JP6070701B2 (ja) 2012-05-31 2017-02-01 三菱化学株式会社 コポリマー、有機半導体材料、有機電子デバイス及び太陽電池モジュール
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
JP2014051556A (ja) * 2012-09-05 2014-03-20 Kuraray Co Ltd π電子共役ランダム共重合体およびそれを用いた光電変換素子
EP2928940B1 (en) 2012-12-04 2021-03-03 CLAP Co., Ltd. Functionalized benzodithiophene polymers for electronic application
CN103936966B (zh) * 2013-01-17 2016-04-13 海洋王照明科技股份有限公司 含3,6-咔唑-苯并二(苯并噻二唑)共聚物及其制备方法和应用
CN103936964B (zh) * 2013-01-17 2016-02-10 海洋王照明科技股份有限公司 含1,8-咔唑-苯并二(苯并噻二唑)共聚物及其制备方法和应用
CN103965445B (zh) * 2013-01-31 2016-08-17 顾玉奎 含二噻吩苯并噻二唑单元的聚合物
CN105073902B (zh) * 2013-03-06 2018-04-24 巴斯夫欧洲公司 新型杂环荧光染料及其制备方法
WO2014206863A1 (en) 2013-06-24 2014-12-31 Basf Se Polymers based on fused diketopyrrolopyrroles
EP3060622B1 (en) 2013-10-22 2019-06-19 Merck Patent GmbH Conjugated polymers
US9399698B2 (en) 2014-01-31 2016-07-26 Xerox Corporation Processes for purifying diketopyrrolopyrrole copolymers
CN104448253A (zh) * 2014-03-04 2015-03-25 上海大学 基于苯并[1,2-b:4,5-b’]二噻吩的芳香炔共聚物及其制备方法
MY176619A (en) * 2014-04-24 2020-08-18 China Petroleum & Chem Corp Catalyst component for olefin polymerization, and catalyst containing the same
WO2015177763A1 (en) * 2014-05-23 2015-11-26 Universita' Degli Studi Di Milano Electro-active macrocyclic oligoarenes and oligoheteroarenes with stereogenic axes
TWI532821B (zh) * 2014-08-07 2016-05-11 國立清華大學 具有氫鍵的固態有機光電材料及其製備方法
US10875957B2 (en) * 2015-11-11 2020-12-29 The Regents Of The University Of California Fluorine substitution influence on benzo[2,1,3]thiodiazole based polymers for field-effect transistor applications
US20170358766A1 (en) * 2016-06-09 2017-12-14 Solarwindow Technologies, Inc. Organic semiconductor photovoltaic devices and compositions with acceptor-donor-acceptor type polymer electron donors
JP7053010B2 (ja) * 2018-03-05 2022-04-12 公立大学法人大阪 ジアリールエテン化合物、フォトクロミック材料、及び調光部材
CN108727566B (zh) * 2018-04-10 2019-06-14 苏州和颂生化科技有限公司 一类基于咔唑-蒽结构的空穴传输聚合物材料的开发与应用
CN110556482A (zh) * 2018-06-04 2019-12-10 中国科学院青岛生物能源与过程研究所 一种基于苯并二噻唑的非富勒烯有机太阳能电池
FR3091530A1 (fr) * 2019-01-09 2020-07-10 Université De Pau Et Des Pays De L'adour Polymères à très faible bande interdite
CN111647332A (zh) * 2019-03-04 2020-09-11 中核华兴达丰机械工程有限公司 一种塔机用水性漆及其制备方法
CN111333820A (zh) * 2020-03-13 2020-06-26 江西科技师范大学 一种平面刚性单体电聚合制备自支撑薄膜的方法
CN112552489A (zh) * 2020-11-09 2021-03-26 山东师范大学 一种非对称非富勒烯化合物及其制备方法与应用
CN114773580B (zh) * 2022-04-29 2024-04-30 太原理工大学 非规整三元共轭聚合物光催化材料及其制备方法和应用
CN115558412B (zh) * 2022-10-12 2023-06-09 深圳市华之美科技有限公司 一种聚酰亚胺复合材料及其制备方法和应用

Family Cites Families (58)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4356429A (en) 1980-07-17 1982-10-26 Eastman Kodak Company Organic electroluminescent cell
ATE22104T1 (de) 1982-05-17 1986-09-15 Ciba Geigy Ag Herstellung von pyrrolo-(3,4-c)-pyrrolen.
US4539507A (en) 1983-03-25 1985-09-03 Eastman Kodak Company Organic electroluminescent devices having improved power conversion efficiencies
US4585878A (en) 1983-06-29 1986-04-29 Ciba-Geigy Corporation N-substituted 1,4-diketopyrrolo-[3,4-c]-pyrroles
DE3435947A1 (de) 1984-09-29 1986-04-03 Basf Ag, 6700 Ludwigshafen Verfahren zur herstellung von elektrisch leitfaehigen systemen
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
DE3584138D1 (de) 1984-11-07 1991-10-24 Ciba Geigy Ag Pigmentmischungen.
US4931566A (en) 1987-07-31 1990-06-05 Ciba-Geigy Corporation Process for the preparation of pyrrolo[3,4-c]pyrroles
DE3736509A1 (de) 1987-10-28 1989-05-11 Hoechst Ag Vorrichtung zum laminieren und schneiden von fotoresistbahnen
GB8909011D0 (en) 1989-04-20 1989-06-07 Friend Richard H Electroluminescent devices
GB9018698D0 (en) 1990-08-24 1990-10-10 Lynxvale Ltd Semiconductive copolymers for use in electroluminescent devices
JPH07188399A (ja) * 1993-12-27 1995-07-25 Unitika Ltd 光照射部が導電性に変化する成形性またはフィルム形成性組成物
US5723873A (en) 1994-03-03 1998-03-03 Yang; Yang Bilayer composite electrodes for diodes
US5492564A (en) 1994-03-16 1996-02-20 Ciba-Geigy Corporation Diketopyrrolopyrrole pigment with high chroma
CN1280708A (zh) 1997-10-17 2001-01-17 加利福尼亚大学董事会 利用喷墨印刷技术制造有机半导体器件的方法及器件和利用该器件的系统
US6057449A (en) 1998-06-02 2000-05-02 Ciba Specialty Chemicals Corporation Direct preparation of pyrrolo[3,4-c]pyrroles
US6566153B1 (en) 1998-10-14 2003-05-20 The Regents Of The University Of California Process for fabricating organic semiconductor devices using ink-jet printing technology and device and system employing same
US6166172A (en) 1999-02-10 2000-12-26 Carnegie Mellon University Method of forming poly-(3-substituted) thiophenes
US6369089B1 (en) 2000-09-14 2002-04-09 Allergan Sales, Inc. Interheteroaryl 7-oxabicyclic [2.2.1]heptane oxazoles as prostaglandin F2α antagonists
US6631712B2 (en) 2001-07-18 2003-10-14 Lawrence J Koncelik, Jr. Aquatic barbecue ash extinguisher and remover
DE10153450A1 (de) 2001-10-30 2003-05-22 Covion Organic Semiconductors Verfahren zur Herstellung von Arylaminen
US6602974B1 (en) 2001-12-04 2003-08-05 Carnegie Mellon University Polythiophenes, block copolymers made therefrom, and methods of forming the same
US20040004433A1 (en) 2002-06-26 2004-01-08 3M Innovative Properties Company Buffer layers for organic electroluminescent devices and methods of manufacture and use
US6784017B2 (en) 2002-08-12 2004-08-31 Precision Dynamics Corporation Method of creating a high performance organic semiconductor device
US7321012B2 (en) * 2003-02-28 2008-01-22 The University Of Connecticut Method of crosslinking intrinsically conductive polymers or intrinsically conductive polymer precursors and the articles obtained therefrom
US7368624B2 (en) 2004-03-30 2008-05-06 Eastman Kodak Company Synthesis for polycyclic aromatic hydrocarbon compounds
US7554111B2 (en) 2004-05-20 2009-06-30 The Regents Of The University Of California Nanoparticle-polymer bistable devices
US7238883B2 (en) 2004-08-11 2007-07-03 Cardiac Pacemakers, Inc. Lead assembly with flexible portions and method therefor
KR101473220B1 (ko) 2004-09-24 2014-12-22 솔베이 유에스에이 인크. 헤테로 원자를 갖는 위치 규칙적 폴리(3-치환 티오펜)를 포함하는 전기발광 소자
JP2008518446A (ja) 2004-10-25 2008-05-29 ザ リージェンツ オブ ザ ユニバーシティー オブ カリフォルニア 有機電子デバイス用積層電極
KR101314877B1 (ko) 2005-02-10 2013-10-04 플렉스트로닉스, 인크 정공 주입/수송 층 조성물 및 장치
US7781673B2 (en) 2005-07-14 2010-08-24 Konarka Technologies, Inc. Polymers with low band gaps and high charge mobility
CN101415715B (zh) 2006-03-10 2012-10-10 住友化学株式会社 稠环化合物及其制造方法、聚合物、含有它们的有机薄膜,有机薄膜元件及有机薄膜晶体管
JP5004071B2 (ja) 2006-03-10 2012-08-22 住友化学株式会社 縮合環化合物の製造方法
JP5164134B2 (ja) * 2006-03-10 2013-03-13 住友化学株式会社 縮合環化合物及びその製造方法、重合体、これらを含む有機薄膜、並びに、これを備える有機薄膜素子及び有機薄膜トランジスタ
JP5519275B2 (ja) 2006-06-13 2014-06-11 プレックストロニクス インコーポレーティッド フラーレンおよびその誘導体を含む有機光起電装置
US20090302311A1 (en) 2006-06-30 2009-12-10 Turbiez Mathieu G R Diketopyrrolopyrrole polymers as organic semiconductors
KR101559590B1 (ko) 2006-07-21 2015-10-12 솔베이 유에스에이 인크. 전도성 중합체의 술폰화 및 oled 소자, 광기전력 소자 및 esd 소자
JP2008069120A (ja) 2006-09-15 2008-03-27 Idemitsu Kosan Co Ltd 芳香族アミン誘導体及びそれらを用いた有機エレクトロルミネッセンス素子
US8008424B2 (en) 2006-10-11 2011-08-30 Konarka Technologies, Inc. Photovoltaic cell with thiazole-containing polymer
ES2885674T3 (es) 2006-12-01 2021-12-15 Univ California Mejora de las características de rendimiento de películas semiconductoras orgánicas mediante un mejor procesamiento de solución
KR101128943B1 (ko) * 2007-04-13 2012-03-27 주식회사 엘지화학 디옥시피롤기를 포함하는 헤테로고리 화합물 및 이를이용한 유기 전자 소자
US20080299293A1 (en) 2007-05-02 2008-12-04 Plextronics, Inc. Solvent system for conjugated polymers
TW200916498A (en) 2007-05-15 2009-04-16 Plextronics Inc Aryl-substituted conjugated polymers
US8227691B2 (en) 2007-10-31 2012-07-24 The Regents Of The University Of California Processing additives for fabricating organic photovoltaic cells
KR101597373B1 (ko) 2007-12-21 2016-02-24 솔베이 유에스에이 인크. 풀러렌 및 그의 유도체를 포함하는 유기 광기전력 소자 및 풀러렌 유도체의 개선된 제조 방법
US20090221740A1 (en) 2008-02-15 2009-09-03 Plextronics, Inc. Novel compositions, methods, and polymers
US20090229667A1 (en) 2008-03-14 2009-09-17 Solarmer Energy, Inc. Translucent solar cell
EP2254929B1 (en) * 2008-03-17 2018-05-16 Basf Se Substituted oligo- or polythiophenes
CN102056959A (zh) 2008-04-11 2011-05-11 普莱克斯托尼克斯公司 掺杂共轭聚合物、器件及器件的制造方法
WO2010000669A1 (en) 2008-07-02 2010-01-07 Basf Se Poly(5,5'bis(thiophen-2-yl)-benzo[2,1-b;3,4-b']dithiophene) and its use as high performance solution processable semiconducting polymer
US20100018581A1 (en) 2008-07-24 2010-01-28 Solarmer Energy, Inc. Large area solar cell
JP2012500500A (ja) 2008-08-20 2012-01-05 プレックストロニクス インコーポレーティッド 有機太陽電池の製造のための改善された溶媒システム
CN102362314B (zh) * 2009-03-23 2014-09-24 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
EP2503835A1 (en) 2011-03-23 2012-09-26 Panasonic Corporation Resouce assignment for single and multiple cluster transmission
US10055491B2 (en) 2012-12-04 2018-08-21 Sonos, Inc. Media content search based on metadata
EP3800643A1 (en) 2019-10-02 2021-04-07 Imec VZW Magnetic device with a hybrid free layer stack
US11305807B2 (en) 2020-08-25 2022-04-19 Thyssenkrupp Presta Ag Vehicle steering column

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11283033B2 (en) 2018-03-09 2022-03-22 Lg Chem, Ltd. Composition for organic layer of organic solar cell and organic solar cell

Also Published As

Publication number Publication date
WO2011002927A2 (en) 2011-01-06
US8440785B2 (en) 2013-05-14
US20110028644A1 (en) 2011-02-03
KR20120061806A (ko) 2012-06-13
WO2011002927A3 (en) 2011-05-26
JP2012532229A (ja) 2012-12-13
EP2449561A2 (en) 2012-05-09

Similar Documents

Publication Publication Date Title
US8440785B2 (en) Compositions, methods and polymers
JP5685778B2 (ja) 光電池およびジケトンベースのポリマーを含む、有機電子素子およびポリマー
CN105324460B (zh) 共轭聚合物
EP3119776B1 (en) Organic semiconducting compounds
Sharma et al. Improved all-polymer solar cell performance of n-type naphthalene diimide–bithiophene P (NDI2OD-T2) copolymer by incorporation of perylene diimide as coacceptor
US9376529B2 (en) Fluoro monomers, oligomers, and polymers for inks and organic electronic devices
CN104169347A (zh) 共轭聚合物
WO2018036914A1 (en) Organic semiconducting compounds
CN106715519B (zh) 共轭聚合物
JP2017518262A (ja) 縮合ビスアリールフラーレン誘導体
WO2016078744A1 (en) Semiconducting mixtures
US11005043B2 (en) Organic semiconducting polymer
CN112368316A (zh) 有机半导体聚合物
JP7518087B2 (ja) 有機半導体
Ye et al. Conjugated polymers for organic solar cells
Forti Sustainable Donor and Acceptor Components for Organic Photovoltaic Cells

Legal Events

Date Code Title Description
A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20130605

A621 Written request for application examination

Free format text: JAPANESE INTERMEDIATE CODE: A621

Effective date: 20130605

A977 Report on retrieval

Free format text: JAPANESE INTERMEDIATE CODE: A971007

Effective date: 20131118

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20140108

A601 Written request for extension of time

Free format text: JAPANESE INTERMEDIATE CODE: A601

Effective date: 20140408

A602 Written permission of extension of time

Free format text: JAPANESE INTERMEDIATE CODE: A602

Effective date: 20140415

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20140704

A711 Notification of change in applicant

Free format text: JAPANESE INTERMEDIATE CODE: A711

Effective date: 20141208

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20150122

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20150413

RD04 Notification of resignation of power of attorney

Free format text: JAPANESE INTERMEDIATE CODE: A7424

Effective date: 20150514

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: 20150601

A61 First payment of annual fees (during grant procedure)

Free format text: JAPANESE INTERMEDIATE CODE: A61

Effective date: 20150611

R150 Certificate of patent or registration of utility model

Ref document number: 5763632

Country of ref document: JP

Free format text: JAPANESE INTERMEDIATE CODE: R150

LAPS Cancellation because of no payment of annual fees