WO2020216801A1 - Composition for preparing a color filter - Google Patents

Composition for preparing a color filter Download PDF

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Publication number
WO2020216801A1
WO2020216801A1 PCT/EP2020/061246 EP2020061246W WO2020216801A1 WO 2020216801 A1 WO2020216801 A1 WO 2020216801A1 EP 2020061246 W EP2020061246 W EP 2020061246W WO 2020216801 A1 WO2020216801 A1 WO 2020216801A1
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WIPO (PCT)
Prior art keywords
block
repeating units
weight
meth
composition according
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/EP2020/061246
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English (en)
French (fr)
Inventor
Hiroshi Yonehara
Andreas OKKEL
Ryo TAKABAYASHI
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.)
BYK Chemie GmbH
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BYK Chemie GmbH
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Priority to CN202080031124.XA priority Critical patent/CN113748171B/zh
Priority to JP2021563616A priority patent/JP7303902B2/ja
Priority to KR1020217038202A priority patent/KR102589005B1/ko
Publication of WO2020216801A1 publication Critical patent/WO2020216801A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004Photosensitive materials
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00Inks
    • C09D11/02Printing inks
    • C09D11/10Printing inks based on artificial resins
    • C09D11/106Printing inks based on artificial resins containing macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C09D11/107Printing inks based on artificial resins containing macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds from unsaturated acids or derivatives thereof
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10Esters
    • C08F220/12Esters of monohydric alcohols or phenols
    • C08F220/14Methyl esters, e.g. methyl (meth)acrylate
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10Esters
    • C08F220/26Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/30Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10Esters
    • C08F220/34Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F265/00Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
    • C08F265/04Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
    • C08F265/06Polymerisation of acrylate or methacrylate esters on to polymers thereof
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F293/00Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/02Homopolymers or copolymers of acids; Metal or ammonium salts thereof
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L51/00Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
    • C08L51/003Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers grafted on to macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L53/00Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00Inks
    • C09D11/02Printing inks
    • C09D11/03Printing inks characterised by features other than the chemical nature of the binder
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00Inks
    • C09D11/02Printing inks
    • C09D11/03Printing inks characterised by features other than the chemical nature of the binder
    • C09D11/037Printing inks characterised by features other than the chemical nature of the binder characterised by the pigment
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00Inks
    • C09D11/30Inkjet printing inks
    • C09D11/32Inkjet printing inks characterised by colouring agents
    • C09D11/322Pigment inks
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00Inks
    • C09D11/30Inkjet printing inks
    • C09D11/32Inkjet printing inks characterised by colouring agents
    • C09D11/324Inkjet printing inks characterised by colouring agents containing carbon black
    • C09D11/326Inkjet printing inks characterised by colouring agents containing carbon black characterised by the pigment dispersant
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00Inks
    • C09D11/30Inkjet printing inks
    • C09D11/32Inkjet printing inks characterised by colouring agents
    • C09D11/328Inkjet printing inks characterised by colouring agents characterised by dyes
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D133/00Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D133/00Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
    • C09D133/02Homopolymers or copolymers of acids; Metal or ammonium salts thereof
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D151/00Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers
    • C09D151/003Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers grafted on to macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D153/00Coating compositions based on block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D17/00Pigment pastes, e.g. for mixing in paints
    • C09D17/001Pigment pastes, e.g. for mixing in paints in aqueous medium
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D5/00Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/02Emulsion paints including aerosols
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40Additives
    • C09D7/45Anti-settling agents
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40Additives
    • C09D7/65Additives macromolecular
    • GPHYSICS
    • G02OPTICS
    • G02BOPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00Optical elements other than lenses
    • G02B5/20Filters
    • G02B5/22Absorbing filters
    • G02B5/223Absorbing filters containing organic substances, e.g. dyes, inks or pigments
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/0005Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
    • G03F7/0007Filters, e.g. additive colour filters; Components for display devices
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004Photosensitive materials
    • G03F7/027Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/032Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
    • G03F7/033Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004Photosensitive materials
    • G03F7/09Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
    • G03F7/105Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images

Definitions

  • the invention relates to a composition comprising a block copolymer, to a process of preparing a color filter, and to a color filter obtainable by the process.
  • US 6413306 relates to pigment dispersions containing ABC triblock polymer dispersants.
  • the pigment dispersions comprise a non-aqueous carrier liquid.
  • the A segment comprises polymerized monomers of alkyl (meth)acrylates, aryl (meth)acrylates, and cycloalkyl
  • the B segment is of polymerized alkyl amino (meth)acrylate monomers.
  • the polymeric C segment is of polymerized monomers of hydroxy alkyl (meth)acrylate having 1 -4 carbon atoms in the alkyl group and monomers selected from the following group: an alkyl (meth)acrylate having 1-12 carbon atoms in the alkyl group, an aryl (meth) acrylate, or a cycloalkyl (meth)acrylate and optionally contains polymerized monomers of glycidyl
  • US 4755563 relates to block copolymer dispersants.
  • This document describes BAB triblock copolymers, wherein the A block comprises ammonium ions, and wherein the B block is polymerized from alkyl (meth)acrylates or alkyl ether (meth)acrylates.
  • compositions for color filters having a low-viscosity, storage-stability, and good developing properties for example in the fields of color filters for liquid crystal displays.
  • a low viscosity of the pigment concentrate and of the coating material is needed for the application of the coating material to the substrate. If the pigment dispersions are not storage-stable and agglomerate, the viscosity of the pigmented composition generally increases and the contrast is impaired.
  • wetting and dispersing agents should have no negative influence on the developing step as for modern color filters the pigment loading is increased and therewith the amount of wetting and dispersing additive which is used in the formulation, too.
  • compositions For use in color filters, a good balance of developing properties and re-solubility in organic solvent, in particular in 1-Methoxy-2-propyl acetate, is desirable for obtaining a high productivity in industrial processes.
  • the compositions should also be suitable for use with a variety of different pigments.
  • the invention provides a composition comprising
  • R 1 represents H or CH 3 ,
  • R 2 represents a hydrocarbyl group
  • R 1 represents H or CH 3 ,
  • R 3 represents a group having at least one non-cyclic ether group, iii) at least one block C comprising at least one of repeating units 3 or 4
  • repeating unit 3 repeating unit 4
  • Z represents O or NH
  • R 1 represents H or CH 3 ,
  • R 4 represents an organic group having 2 to 4 carbon atoms
  • R 5 independently of each other represents an organic group, wherein two R 5 groups are optionally linked to each other to form a cyclic structure
  • R 6 represents an organic group or hydrogen, and X represents a non polymeric anion
  • compositions of the invention have a low-viscosity, storage-stability, and can be used in the manufacture of color filters having good developing properties.
  • the block A of the block co-polymer a) comprises repeating units 1 as described above.
  • the block A comprises one or more different types of repeating units 1.
  • block A comprises 1 to 12 different types of repeating units 1.
  • the repeating units 1 in the block co-polymer are generally derived by polymerization of suitable ethylenically unsaturated polymerizable monomers.
  • the ethylenically unsaturated monomers that form the repeating unit 1 in the block co-polymer are generally selected from acrylic esters, methacrylic esters, acrylamides and/or
  • methacrylamides which preferably carry no primary, secondary, tertiary or quaternized amino group.
  • (meth)acryl refers to both methacryl and acryl.
  • (meth)acrylate refers to both methacrylate and acrylate, likewise.
  • (meth)acrylate isodecyl (meth)acrylate, 2-propylheptyl (meth)acrylate, 3,5,5-trimethyl-1-hexyl (meth)acrylate, nonanyl (meth)acrylate, 2-propylheptyl (meth)acrylate, 2-isopropyl-5-methyl- hexyl (meth)acrylate, tridecyl (meth)acrylate, heptadecyl (meth)acrylate, heneicosanyl
  • aryl (meth)acrylic esters whose aryl ring, without possible additional substituents, contains 5 to 12, preferably 6 to 10, carbon atoms, such as phenyl acrylate; and aralkyl (meth)acrylic esters whose aralkyl radical, without possible additional substituents on the aryl radical, contains 6 to 11 , preferably 7 to 1 1 , carbon atoms, such as benzyl methacrylate, it being possible for the aryl radicals of the aryl (meth)acrylic esters and of the aralkyl (meth)acrylic esters in each case to be unsubstituted or to be substituted up to four times, such as, for example, 4-methylphenyl methacrylate.
  • esters of methacrylic acid rather than esters of acrylic acid.
  • R 2 in repeating unit 1 stands for a branched or unbranched alkyl residue with 1 to 12, preferably 1 to 10 carbon atoms, a cycloalkyl residue with 4 to 8, preferably 6 carbon atoms, an araliphatic residue with 7 to 12 carbon atoms, like benzyl.
  • more than 50 weight-%, more preferably, more than 70 weight-%, the most preferably, more than 90 weight-% of the repeating units of block A are selected from repeating units 1. In some embodiments, all or essentially all repeating units of block A are selected from repeating units 1.
  • the block B of the block co-polymer a) comprises repeating units 2 as described above.
  • Such repeating units are suitably provided by monomers of the following formula (I) wherein
  • R 1 represents H or CH 3 ,
  • R a represents a linear or branched alkylene group with 2 to 6 carbon atoms
  • R b represents aralkyl, preferably benzyl; or alkyl with 1 to 8 carbon atoms, preferably methyl, ethyl, propyl or butyl;
  • n represents an integer from 1 to 150, preferably 1 to 50, more preferably 1 to 25,
  • the [RO] n chain may have a random, block or gradient architecture along the chain.
  • the block B comprises one or more different types of repeating units 2.
  • block B comprises 1 to 12 different types of repeating units 2.
  • the repeating units 2 in the block co-polymer are generally derived by polymerization of suitable ethylenically unsaturated polymerizable monomers.
  • suitable monomers are (meth)acrylic acid esters of monoether monoalcohols or polyether monoalcohols, such as ethers, polyethylene glycols, polypropylene glycols, polybutylene glycols or mixed polyalkylene glycols having 4 to 80 carbon atoms and a statistical, a block or a gradient distribution of the different monomers along the chain, such as, for example, di(ethylene glycol) methyl ether (meth)acrylate, 2-butoxyethyl (meth)acrylate, 2- ethoxyethyl (meth)acrylate, allyloxyethyl (meth)acrylate, 1-ethoxybutyl (meth)acrylate, methyltriglycol (meth)acrylate, ethyltriglycol (meth)acrylate, butyldiglycol (meth)acrylate, polypropylene glycol) methyl ether (meth)acrylate, poly(ethylene glycol) alkyl ether
  • the block B comprises repeating units derived from monomers selected from ethyl triglycol methacrylate, methyl triglycol methacrylate, butyl diglycol methacrylate, methoxy polyethylene glycol) methacrylate and mixtures thereof.
  • repeating units 2 are prepared by a post polymerization modification reaction. Examples of such reactions are ring-opening addition reactions of amine- or hydroxyl functional polyethers with epoxide-functional polymers.
  • Epoxide-functional polymers can be prepared by co-polymerization of epoxide-functional monomers, such as glycidyl (meth)acrylate.
  • Amine-functional polyethers are commercially available under the trade designation Jeffamine® from Huntsman.
  • more than 10 weight-%, more preferably, more than 30 weight-%, the most preferably, more than 50 weight-% of the repeating units of block B are selected from repeating units 2. In some embodiments, all or essentially all repeating units of block B are selected from repeating units 2.
  • the block C of the block co-polymer a) comprises at least one of repeating units 3 or 4 as described above.
  • Repeating units 3 have a tertiary amino group.
  • Repeating units 3 can be generated by polymerization of acrylic esters, methacrylic esters, acrylamides and methacrylamides which have at least one tertiary amino group.
  • the monomers are preferably selected from the group of tert-aminoalkyl (meth)acrylic esters having 2 to 12, preferably 2 to 8 carbon atoms in the tert- aminoalkyl group, including possible additional substituents, like further additional tert-amino groups in residues R 4 and R 5 .
  • repeating unit 3 examples are N,N-dimethylaminoethyl (meth)- acrylate, N,N-diethylaminoethyl (meth)acrylate, N,N-dibutylaminoethyl (meth)acrylate, 2-(2- dimethylaminoethyl(methyl)amino]ethyl (meth)acrylate, 2-(2-dimethylaminoethyloxy)ethyl (meth)acrylate, 2-morpholinoethyl (meth)acrylate, 2-(1-piperidyl)ethyl (meth)acrylate, 2-(N- ethylanilino)ethyl (meth)acrylate, 2-imidazol-1 -ylethyl (meth)acrylate, N,N-dimethylaminopropyl (meth)acrylate, and N,N-dimethylaminoethyl (meth)acrylamide. Most preferred is the use
  • Repeating units 3 containing at least one tertiary amino group can also be produced by reactions after the construction of the polymer chain.
  • oxiran-containing ethylenically unsaturated monomers such as glycidyl methacrylate can be (co)polymerized to form a polymeric block having oxirane groups. They can be reacted with amines after the polymerization. In such case residue R 3 will contain a hydroxyl group. If desired, R 4 and/or R 5 may contain further hydroxyl groups.
  • Suitable for this purpose are primary amines which additionally carry one or more tertiary amino groups or secondary amines, which optionally additionally carry one or more tertiary amino groups.
  • Examples include dimethylaminopropylamine and diethylaminoethylamine; dialkylamines such as diethylamine, dibutylamine and dicyclohexylamine; secondary amines having two different substituents such as, for example, N-(2-hydroxyethyl)aniline; secondary amines which additionally carry one or more tertiary amino groups, such as bis(3-dimethylaminopropyl)amine; dihydroxyalkylamines, such as diethanolamine and diisopropanolamine. Preference is given to secondary amines which, optionally, additionally carry one or more tertiary amino groups.
  • block C further comprises repeating units 4.
  • Repeating units 4 can be described as reaction product of a quaternization reaction of the tertiary amine group of repeating units 3. In one embodiment, quaternization is carried out after formation of the polymer. Alternatively, quaternization may be carried out on the corresponding unsaturated monomers prior to polymerization.
  • repeating units 4 can be introduced by partial quaternization of the amine groups of repeating units 3.
  • Suitable quaternization agents may be selected from alkyl halides and aralkyl halides, or epoxides, for example glycidyl ethers in the presence of acids.
  • alkyl halides and aralkyl halides like benzyl chloride, benzyl bromide, 2- or 4-vinylbenzylchloride, methyl chloride or methyl iodide can be used.
  • tosylates like methyl tosylate can be used.
  • Suitable glycidyl ethers are alkyl glycidyl ethers like 2-ethylhexyl glycidyl ether and Ci 3 /Ci 5 -alkyl glycidyl ether or aryl glycidyl ethers like cresylglycidyl ether as well as glycidyl methacrylate.
  • acids used in this quaternization reaction are carboxylic acids like benzoic acid, acetic acid or lactic acid. Further acids are phosphoric acid ester with one or two ester substituents.
  • Preferred are benzyl chloride, 4-vinylbenzyl chloride and glycidyl methacrylate in combination with a carboxylic acid.
  • quaternization is carried out with a quaternization agent of formula (II)
  • X is a so-called leaving group, like halide, triflate or tosylate that can
  • R 7 is a linear or branched hydrocarbon group with 1 to 8 carbon atoms.
  • Preferred compounds of general formula (II) are monochloroacetic acid, derivatives of lactic acid, such as tosylated lactic acid, monochloropropionic acid, and higher homologous carboxylic acids substituted with a leaving group.
  • One or more types of quaternization agents may be used, either simultaneously or
  • the conversion of repeating units 3 via quaternization can be determined by the amine value of the polymer by DIN 16945.
  • the block co-polymer has an amine value in the range of 1 to 250 mg KOH/g.
  • the amine value of the block copolymer is in the range of 10 to 180 mg KOH/g, more preferred 30 to 160 mg KOH/g, and most preferred 50 to 160 mg KOH/g.
  • repeating units 3 and/or repeating units 4 are selected from repeating units 3 and/or repeating units 4. In some embodiments, all or essentially all repeating units of block C are selected from repeating units 3 and/or repeating units 4.
  • a preferred block co-polymer of the invention is a block co-polymer preferably having a number- average molecular weight M n of 2000 to 20000 g/mol, more preferably of 3000 to 17000 g/mol and most preferably of 4000 to 14000 g/mol.
  • the number-average molecular weight M n and the weight-average molecular weight M w are determined in accordance with DIN 55672-1 :2007-08 by means of gel permeation chromatography using tetrahydrofuran containing 1 % by volume of dibutylamine as eluent and polystyrene as standard. If the number-average molecular weight is too high, the viscosity may deteriorate.
  • the block co-polymer of the invention generally has a low polydispersity.
  • Polydispersity is the weight average molecular weight M w divided by the number average molecular weight M n .
  • the polydispersity of the block co-polymer is in the range of 1.03 to 1.80, more preferably 1.05 to 1.40.
  • the weight ratio of block A to block B to block C in the copolymer is described as follows; block A: 5 to 90 % by weight, preferably, 15 to 70 % by weight, more preferably, 20 to 55 % by weight
  • block B 5 to 90 % by weight, preferably, 15 to 70 % by weight, more preferably, 20 to 55 % by weight
  • block C 2 to 70 % by weight, preferably, 8 to 60 % by weight, more preferably, 13 to 50 % by weight
  • composition of the invention further comprises a colorant b).
  • Suitable colorants include pigments, and dyes, opaqueness providing fillers, and combinations thereof.
  • pigments used as colorant in the composition have an average median particle diameter of 1 pm or less, preferably 0.3 pm or less, further preferably 50 nm or less determined by laser diffraction according ISO 13320:2009.
  • the median primary particle diameter determined by laser diffraction according to ISO 13320:2009 is preferably 0.01 to 0.08 pm and the "nitrogen absorption specific surface area" is preferably 50 to 120 m 2 /g for the black pigments determined via ISO 9277:2010.
  • the relative weight ratio of block-copolymer a) to colorants b) in the compositions of the present invention is preferably 95:5 to 5:95, more preferably 65:35 to 7:93 and in particular preferably 50:50 to 10:90.
  • composition of the invention further comprises compound c) having at least one
  • composition of the invention further comprises an alkali soluble resin d).
  • alkali-soluble resins are described in international patent application
  • Preferred alkali-soluble resins are:
  • Co-polymers of ethylenically unsaturated monomers with (meth)acrylic acid and/or maleic anhydride wherein preferred ethylenically unsaturated co-monomers are selected from the group consisting of styrene, benzyl methacrylate, 2-hydroxyethyl (meth)acrylate, methyl methacrylate, cyclohexyl methacrylate, isobornyl methacrylate, adamantly (meth)acrylate and glycidyl methacrylate.
  • a glycidyl group is incorporated in the polymer a post reaction with acids or acid anhydrides to incorporate functional groups like carboxylic acid or (meth)acrylate moieties can be performed.
  • Reaction products of ethylenically unsaturated monocarboxylic acid or its ester with an epoxy resin and a carboxylic acid anhydride wherein examples of epoxy resins are monomeric and oligomeric bisphenol A, F, S-type epoxy resins, novolak-type epoxy resin, trigylcidyl isocyanurate, fluorene epoxy resin, so called cardo resin, and wherein examples of acid anhydrides are maleic anhydride, succinic anhydride, itaconic anhydride, phthalic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, pyromellitic anhydride and trimellitic anhydride.
  • epoxy resins are monomeric and oligomeric bisphenol A, F, S-type epoxy resins, novolak-type epoxy resin, trigylcidyl isocyanurate, fluorene epoxy resin, so called cardo resin
  • acid anhydrides are maleic anhydride, succ
  • alkali-soluble resins can be used alone or in combination.
  • the alkali-soluble resin has an acid value in the range of 80 to 100 mg KOH/g.
  • Alkali-soluble resins having number average molecular weight in the range of 400 to 8000 g/mol are often used.
  • further components may be included in the composition.
  • further components include film-forming binders, other resins and polymers, reactive diluents and solvents, curing catalysts, as well as further additives.
  • the solvent is suitably an organic solvent.
  • the content of the organic solvent of the inventive composition is preferably 10 to 99% by weight, more preferably 20 to 97 % by weight of the total weight of the inventive composition.
  • Examples of such an organic solvent include glycol monoalkyl ethers such as ethylene glycolmonobutyl ether, propylene glycol monomethyl ether; glycol dialkyl ethers such as ethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether; glycol alkyl ether acetates such as ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, methoxybutyl acetate; dialkyl ethers such as diethyl ether; ketones such as acetone, methyl ethyl ketone,
  • cyclohexanone monohydric or polyhydric alcohols such as ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, and glycerin; aliphatic hydrocarbons such as n-hexane; alicyclic hydrocarbons such as cyclohexane; aromatic hydrocarbons such as toluene, xylene, and cumene; linear or cyclic esters such as ethyl acetate, butyl acetate; nitriles such as acetonitrile, and benzonitrile or mixtures thereof. Also suitable are ethoxy ethyl propionate, and solvent blends containing n-butanol, for example blends of n-butanol and dimethyl sulfoxide.
  • the organic solvent is selected from the group consisting of glycol monoalkyl ethers, glycol dialkyl ethers, glycol alkyl ether acetates and mixtures thereof.
  • Glycol alkyl ether acetates are even more preferred. Most preferred is propylene glycol monomethyl ether acetate.
  • Glycol alkyl ether acetates may be used alone or in combination with other solvents.
  • the composition of the invention is very suitable for preparing a color filter. Therefore, the invention further relates to a process for preparing a color filter, wherein the process comprises the steps of applying the composition of the invention to a substrate and curing selected areas of the composition by exposure to actinic radiation.
  • Actinic radiation is radiation capable of triggering chemical reactions. Examples of actinic radiation are UV radiation and electron beam radiation.
  • the process further comprises the step of treating the color filter with an alkali-containing solution and removing uncured material.
  • the color filter is included in a device such as a liquid crystal display, a liquid crystal screen, a color resolution device or a sensor.
  • ETMA Ethyltriglycol methacrylate (Evonik)
  • MPEG-400MA Methoxy polyglycol (average number of ethyleneoxide unit: 9)
  • MPEG-1000MA Methoxy polyglycol (average number of ethyleneoxide unit: 23) methacrylate (Shin-Nakamura Chemical)
  • DMAEMA N,N-Dimethylaminoethyl methacrylate (Evonik)
  • Grilonit RV 1814 Alkyl (number of carbon: 13 - 15) glycidyl ether (EMS-GRILTECH)
  • GPC Gel Permeation Chromatography
  • the sample (1.0 ⁇ 0.2 g of the tested substance) was weighed accurately into a previously dried aluminum dish and approximately 2 ml of Ethanol was added. After being homogenized, it is dried for 20 minutes at 150°C in the varnish drying cabinet, cooled in a desiccator and then reweighed. The residue corresponds to the solids content in the sample (ISO 3251).
  • 1.5 to 3.0 g of a sample was precisely weighed out into a 80 ml. beaker and is dissolved with 50 ml. of ethanol. Using an automatic titration device provided with a pH electrode, this solution was neutralization-titrated with a 0.1 mol/L ethanolic KOH solution. A flexion point of a titration pH curve was used as a titration endpoint, and an amine value was obtained by the following equation.
  • diblock copolymer DB-1 42.4 g of 1-methoxy-2-propyl acetate (PMA) were placed into a water-free reaction vessel. 46.2 g of monomer mixtures in block A were added dropwise over 60 minutes. Immediately after the start of the metering, the respective amount of MMTP and‘Catalyst’ described above were introduced into the reaction vessel. Throughout the reaction, the reaction temperature was kept at 20°C. After the end of the metering of monomer mixtures in block A, 8.1 g of monomer mixtures in block B were added dropwise over 30 minutes. The subsequent reaction time after the end of the metering of monomer mixtures in block B was 60 minutes. Afterwards 1.6 g of 2-methoxypropanol was added.
  • PMA 1-methoxy-2-propyl acetate
  • Diblock copolymer DB-2 - DB-5 were synthesized using the same procedure as used for block copolymer DB-1 , except using different dosages of MMTP,‘Catalyst’ described above, monomer mixtures in block A and monomer mixtures in block B (Details are described in Table 1).
  • Quaternized triblock copolymer QTB-2 was synthesized using the same procedure as used for quaternized triblock copolymer QTB-1 , except using different type of intermediate polymer (Details are described in Table 4).
  • Quaternized random copolymer QR-1 was synthesized using the same procedure as used for quaternized triblock copolymer QTB-1 , except using different type of intermediate polymer (Details are described in Table 4).
  • PR-254 Irgaphor Red BT-CF (BASF)
  • PB-15:6 Fastogen Blue EP-193 (DIC)
  • Dispersions R-2 - R-5, G-1 - G-10 and B-1 - B-4 were prepared according to the procedure for dispersion R-1 (Details are described in Table 5).
  • VISCOMETER DV-II+ (BROOKFIELD, upper limitation of viscosity: 1000 mPa-s).
  • Particle size (median diameter: D50) of red, green and blue dispersion were measure by using Particle Size Analyzer ELSZ-1000 (Otsuka Electronics).
  • Aronix M305 Pentaerythritol triacrylate (TOA GOSEI)
  • Omnirad 369 Former name: Irgacure 369, 2-benzyl-2-(dimethylamino)-4’- morpholinobutyrophenone (IGM Resins B.V.)
  • Red, Green and Blue resist inks were coated to glass plate by using bar coater No.4 (9.16 pm of thickness at wetting-film), and the coating films were dried at 80°C for 3 minutes.
  • the dried coating films were gradually dipped to 0.05% KOH aqueous solution (interval: 10 - 60 seconds). After washing them by water, the coating films were wiped by using KimWipes (Kimberly Clark Corporation product), and marked appearance of coating film described as follows;
  • Red, Green and Blue resist inks were coated to glass plate by using bar coater No.4 (9.16 pm of thickness at wetting-film), and the coating films were dried at 80°C for 3 minutes.
  • One droplet of PMA was put on the coating film, and wiped immediately by using KimWipes.
  • the appearance of the coating film after wiping was marked as follows;
  • Example 1-12 Viscosity and particle size of red (R), green (G) and blue (B) dispersions, and developing property and re-solubility in PMA of red (R), green (G) and blue (B) resist inks
  • Viscosity (mPa-s at 20 °C, rotation: 60 rpm) and particle size (D50) of red, green and blue dispersions are described in Table 6.
  • developing property and re-solubility in PMA of red, green and blue resist inks are also described in Table 6.
  • Comparison example C-1 to C-7 Viscosity and particle size of red (R), green (G) and blue (B) dispersions, and developing property and re-solubility in PMA of red (R), green (G) and blue (B) resist inks
  • Viscosity (mPa-s at 20 °C, rotation: 60 rpm) and particle size (D50) of red, green and blue dispersions are described in Table 7. Moreover, developing property and re-solubility in PMA of red, green and blue resist inks are also described in Table 7. Table 7
  • red, green and blue dispersions including triblock copolymer showed excellent dispersibility and storage stability. Moreover, red, green and blue resist inks including triblock copolymer also showed excellent balance between developing property and re-solubility in PMA (Example 1 to 12).
  • green and blue dispersions including random copolymer or quaternized random copolymer showed lower dispersibility and/or storage stability (Comparison example C- 5, C-7).
  • Red, green and blue dispersions including diblock copolymer also showed good dispersibility and storage stability.
  • red, green and blue resist inks including diblock copolymer showed poor balance between developing property and/or re-solubility in PMA (Comparison examples C-1 to C-4, C-6).

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TWI831504B (zh) * 2022-06-23 2024-02-01 日商大日精化工業股份有限公司 水性墨水用黏合劑成分及水性墨水

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CN113748171B (zh) 2022-12-13
US12116492B2 (en) 2024-10-15
KR20220005512A (ko) 2022-01-13
EP3959274B1 (en) 2023-06-07
WO2020216800A1 (en) 2020-10-29
JP7253080B2 (ja) 2023-04-05
JP7303902B2 (ja) 2023-07-05
JP2022530230A (ja) 2022-06-28
CN113728061B (zh) 2023-06-02
JP2022530152A (ja) 2022-06-27
KR20220005510A (ko) 2022-01-13
KR102648624B1 (ko) 2024-03-20
CN113748171A (zh) 2021-12-03
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