WO2004003102A3 - Polymerizable, luminescent compounds and mixtures, luminescent polymer materials and their use - Google Patents

Polymerizable, luminescent compounds and mixtures, luminescent polymer materials and their use Download PDF

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Publication number
WO2004003102A3
WO2004003102A3 PCT/EP2003/006450 EP0306450W WO2004003102A3 WO 2004003102 A3 WO2004003102 A3 WO 2004003102A3 EP 0306450 W EP0306450 W EP 0306450W WO 2004003102 A3 WO2004003102 A3 WO 2004003102A3
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WO
WIPO (PCT)
Prior art keywords
polymerizable
mixtures
luminescent
compounds
polymer materials
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.)
Ceased
Application number
PCT/EP2003/006450
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French (fr)
Other versions
WO2004003102A2 (en
Inventor
Eike Poetsch
Thomas Jacob
Jose Serrano
Milagros Pinol
Raquel Gimenez
Joachim Stumpe
Thomas Fischer
Regina Rosenhauer
Burkhard Schulz
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Merck Patent GmbH
Original Assignee
Merck Patent GmbH
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 Merck Patent GmbH filed Critical Merck Patent GmbH
Priority to US10/519,707 priority Critical patent/US20060166033A1/en
Priority to JP2004516620A priority patent/JP2005531618A/en
Priority to EP03761475A priority patent/EP1517975A2/en
Priority to AU2003242731A priority patent/AU2003242731A1/en
Publication of WO2004003102A2 publication Critical patent/WO2004003102A2/en
Publication of WO2004003102A3 publication Critical patent/WO2004003102A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • 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
    • H10K85/141—Organic polymers or oligomers comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
    • C07D271/107—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with two aryl or substituted aryl radicals attached in positions 2 and 5
    • 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
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/0605—Polycondensates containing five-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms
    • C08G73/0616—Polycondensates containing five-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms with only two nitrogen atoms 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
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/08—Polyhydrazides; Polytriazoles; Polyaminotriazoles; Polyoxadiazoles
    • 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
    • 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
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/0403—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit the structure containing one or more specific, optionally substituted ring or ring systems
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional [2D] radiating surfaces
    • H05B33/14—Light sources with substantially two-dimensional [2D] radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
    • 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
    • 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
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K2019/0444—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group
    • 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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
    • 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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • 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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • C09K2211/1048—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with oxygen
    • 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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/14—Macromolecular compounds
    • C09K2211/1408—Carbocyclic compounds
    • 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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/14—Macromolecular compounds
    • C09K2211/1408—Carbocyclic compounds
    • C09K2211/1416—Condensed systems
    • 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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/14—Macromolecular compounds
    • C09K2211/1408—Carbocyclic compounds
    • C09K2211/1425—Non-condensed systems
    • 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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/14—Macromolecular compounds
    • C09K2211/1441—Heterocyclic
    • C09K2211/1466—Heterocyclic containing nitrogen as the only heteroatom
    • 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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/14—Macromolecular compounds
    • C09K2211/1441—Heterocyclic
    • C09K2211/1475—Heterocyclic containing nitrogen and oxygen as heteroatoms
    • 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]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • 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
    • H10K85/114—Poly-phenylenevinylene; Derivatives thereof
    • 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
    • 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
    • H10K85/6565—Oxadiazole compounds

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Materials Engineering (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Polyethers (AREA)
  • Electroluminescent Light Sources (AREA)
  • Epoxy Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

The invention relates to new polymerizable, luminescent compounds of formula I wherein R1, R2, Q and L1 have the meanings given in claim 1. Furthermore the invention relates to polymerizable mixtures containing compounds according to the invention and preferably at least one polymerizable mesogenic compound. Polymer materials obtainable by polymerizing such mixtures are also described. These compounds, mixtures and materials show advantageous photoluminescent and/or electroluminescent properties and may be used in light emitting devices and optical- or electrooptical display elements.
PCT/EP2003/006450 2002-07-01 2003-06-18 Polymerizable, luminescent compounds and mixtures, luminescent polymer materials and their use Ceased WO2004003102A2 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
US10/519,707 US20060166033A1 (en) 2002-07-01 2003-06-18 Polymerizable, luminescent compounds and mixtures, luminescent polymer materials and their use
JP2004516620A JP2005531618A (en) 2002-07-01 2003-06-18 Polymerizable, luminescent compounds and mixtures, luminescent polymer materials and their use
EP03761475A EP1517975A2 (en) 2002-07-01 2003-06-18 Polymerizable, luminescent compounds and mixtures, luminescent polymer materials and their use
AU2003242731A AU2003242731A1 (en) 2002-07-01 2003-06-18 Polymerizable, luminescent compounds and mixtures, luminescent polymer materials and their use

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP02014068 2002-07-01
EP02014068.7 2002-07-01

Publications (2)

Publication Number Publication Date
WO2004003102A2 WO2004003102A2 (en) 2004-01-08
WO2004003102A3 true WO2004003102A3 (en) 2004-08-26

Family

ID=29797139

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2003/006450 Ceased WO2004003102A2 (en) 2002-07-01 2003-06-18 Polymerizable, luminescent compounds and mixtures, luminescent polymer materials and their use

Country Status (5)

Country Link
US (1) US20060166033A1 (en)
EP (1) EP1517975A2 (en)
JP (1) JP2005531618A (en)
AU (1) AU2003242731A1 (en)
WO (1) WO2004003102A2 (en)

Families Citing this family (36)

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GB0715164D0 (en) * 2007-08-06 2007-09-12 Airbus Uk Ltd Method and apparatus for manufacturing a composite material
WO2009086911A1 (en) * 2008-01-11 2009-07-16 Merck Patent Gmbh Reactive mesogenic compounds and mixtures
JP2009239180A (en) * 2008-03-28 2009-10-15 Sumitomo Chemical Co Ltd Organic electroluminescent device
IL196312A (en) 2008-12-31 2014-08-31 Renata Reisfeld Luminescent solar concentrators
US20100326526A1 (en) 2009-06-29 2010-12-30 Nitto Denko Corporation Emissive aryl-heteroaryl compounds
JP5773585B2 (en) * 2009-06-29 2015-09-02 日東電工株式会社 Luminescent triaryl
CN103619803B (en) * 2011-05-31 2016-01-20 Dic株式会社 Cinnamic acid derivative, its polymer, and liquid crystal alignment layer composed of its cured product
WO2015084128A1 (en) 2013-12-06 2015-06-11 주식회사 엘지화학 Block copolymer
WO2015084123A1 (en) 2013-12-06 2015-06-11 주식회사 엘지화학 Block copolymer
CN105960422B (en) 2013-12-06 2019-01-18 株式会社Lg化学 Block copolymer
JP6483694B2 (en) 2013-12-06 2019-03-13 エルジー・ケム・リミテッド Monomers and block copolymers
WO2015084121A1 (en) 2013-12-06 2015-06-11 주식회사 엘지화학 Block copolymer
JP6432847B2 (en) 2013-12-06 2018-12-05 エルジー・ケム・リミテッド Block copolymer
US10150832B2 (en) 2013-12-06 2018-12-11 Lg Chem, Ltd. Block copolymer
WO2015084122A1 (en) 2013-12-06 2015-06-11 주식회사 엘지화학 Block copolymer
JP6361893B2 (en) 2013-12-06 2018-07-25 エルジー・ケム・リミテッド Block copolymer
WO2015084125A1 (en) 2013-12-06 2015-06-11 주식회사 엘지화학 Block copolymer
JP6432846B2 (en) 2013-12-06 2018-12-05 エルジー・ケム・リミテッド Block copolymer
JP6483693B2 (en) 2013-12-06 2019-03-13 エルジー・ケム・リミテッド Block copolymer
WO2015084124A1 (en) 2013-12-06 2015-06-11 주식회사 엘지화학 Block copolymer
JP6419820B2 (en) 2013-12-06 2018-11-07 エルジー・ケム・リミテッド Block copolymer
WO2016053005A1 (en) 2014-09-30 2016-04-07 주식회사 엘지화학 Block copolymer
JP6505212B2 (en) 2014-09-30 2019-04-24 エルジー・ケム・リミテッド Block copolymer
US10633533B2 (en) 2014-09-30 2020-04-28 Lg Chem, Ltd. Block copolymer
EP3214102B1 (en) 2014-09-30 2022-01-05 LG Chem, Ltd. Block copolymer
JP6633062B2 (en) 2014-09-30 2020-01-22 エルジー・ケム・リミテッド Manufacturing method of patterned substrate
WO2016053009A1 (en) 2014-09-30 2016-04-07 주식회사 엘지화학 Block copolymer
US10287430B2 (en) 2014-09-30 2019-05-14 Lg Chem, Ltd. Method of manufacturing patterned substrate
JP6538158B2 (en) 2014-09-30 2019-07-03 エルジー・ケム・リミテッド Block copolymer
EP3202798B1 (en) * 2014-09-30 2022-01-12 LG Chem, Ltd. Block copolymer
US10240035B2 (en) 2014-09-30 2019-03-26 Lg Chem, Ltd. Block copolymer
JP6918352B2 (en) * 2016-07-20 2021-08-11 学校法人立命館 Polymers useful as photoluminescent materials
CA3121202A1 (en) 2018-11-30 2020-06-04 Nuvation Bio Inc. Pyrrole and pyrazole compounds and methods of use thereof
CN109721721B (en) * 2018-12-14 2021-05-14 万华化学集团股份有限公司 Polyether with fluorescence property and synthetic method and application thereof
CN112939715A (en) * 2021-02-01 2021-06-11 惠泽化学科技(濮阳)有限公司 Synthesis method of 4-alkyl biphenyl acetylene
KR20240005069A (en) * 2021-05-07 2024-01-11 메르크 파텐트 게엠베하 reactive mesogen

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Patent Citations (2)

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EP1170273A1 (en) * 2000-07-03 2002-01-09 Korea Research Institute Of Chemical Technology Alkynic compounds, their use as monomers in vacuum deposition polymerisation, thin films formed from these polymers and their use in electroluminescent devices

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ZHAN X; LIU Y; WU X; WANG S; ZHU D: "New Series of Blue-Emitting and Electron-Transporting Copolymers Based on Fluorene", MACROMOLECULES, vol. 35, 2002 - 16 February 2002 (2002-02-16), pages 2529 - 2537, XP002260246 *

Also Published As

Publication number Publication date
AU2003242731A8 (en) 2004-01-19
EP1517975A2 (en) 2005-03-30
US20060166033A1 (en) 2006-07-27
AU2003242731A1 (en) 2004-01-19
JP2005531618A (en) 2005-10-20
WO2004003102A2 (en) 2004-01-08

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