WO2022168974A1 - Résine soluble dans les alcalis, composition de résine photosensible, produit durci et dispositif d'affichage d'images - Google Patents

Résine soluble dans les alcalis, composition de résine photosensible, produit durci et dispositif d'affichage d'images Download PDF

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Publication number
WO2022168974A1
WO2022168974A1 PCT/JP2022/004685 JP2022004685W WO2022168974A1 WO 2022168974 A1 WO2022168974 A1 WO 2022168974A1 JP 2022004685 W JP2022004685 W JP 2022004685W WO 2022168974 A1 WO2022168974 A1 WO 2022168974A1
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group
carbon atoms
alkali
soluble resin
base
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PCT/JP2022/004685
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English (en)
Japanese (ja)
Inventor
祥穂 伊藤
茂樹 阿波
竜生 森本
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大阪有機化学工業株式会社
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Priority to JP2022579641A priority Critical patent/JPWO2022168974A1/ja
Priority to CN202280013436.7A priority patent/CN116867822A/zh
Priority to KR1020237026699A priority patent/KR20230128119A/ko
Publication of WO2022168974A1 publication Critical patent/WO2022168974A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F120/00—Homopolymers 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
    • C08F120/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F120/10—Esters
    • C08F120/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F120/32—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F120/00—Homopolymers 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
    • C08F120/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F120/10—Esters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/08—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated side groups
    • C08F290/12—Polymers provided for in subclasses C08C or C08F
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/08—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated side groups
    • C08F290/12—Polymers provided for in subclasses C08C or C08F
    • C08F290/126—Polymers of unsaturated carboxylic acids or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/34—Introducing sulfur atoms or sulfur-containing groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/46—Reaction with unsaturated dicarboxylic acids or anhydrides thereof, e.g. maleinisation
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
    • G03F7/033—Non-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
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable

Definitions

  • the present invention relates to alkali-soluble resins, photosensitive resin compositions, cured products, and image display devices.
  • photospacers are used to maintain the thickness of the liquid crystal layer sandwiched between the substrate on the color filter side and the substrate on the thin film transistor (TFT) side.
  • TFT thin film transistor
  • a photospacer is generally formed by applying a photosensitive resin composition to a substrate, drying it, exposing it to light through a photomask having a predetermined fine pattern, and developing it.
  • Patent Literature 1 provides a negative photosensitive resin composition that is excellent in development adhesion and resolution even when processed to a thick film of 10 ⁇ m or more and is capable of forming a fine photospacer with a good shape. with the aim of (A) an alkali-soluble resin, (B) a radical photopolymerization initiator and (C) a photopolymerizable monomer, wherein the (C) photopolymerizable monomer contains (C-1) an isocyanuric acid skeleton.
  • a negative photosensitive resin composition containing a monomer and (C-2) a photopolymerizable monomer having a fluorene skeleton has been proposed.
  • Patent Document 2 aims to provide a photosensitive resin composition that can form a gap of 10 ⁇ m or more, has good adhesion to a substrate, and can ensure transparency after exposure.
  • component binder polymer
  • component photopolymerizable compound
  • C component: photopolymerization initiator
  • D component: mercapto group-containing hydrogen donor
  • the (B) photopolymerizable A photosensitive resin composition has been proposed in which a compound is used as a spacer-forming material containing a photopolymerizable compound having an ethylenically unsaturated group and an isocyanuric ring structure.
  • the present inventors have made intensive studies to solve the above problems, and found that the above objects can be achieved by using the following alkali-soluble resin and a photosensitive resin composition containing the alkali-soluble resin.
  • the present invention has been completed.
  • alkali-soluble resin A containing one or more repeating structural units X represented by the following general formula (1).
  • R 1 is hydrogen or a methyl group
  • R 2 is a linking group having 1 or more carbon atoms
  • R 3 is represented by the following general formula (2) bonded to a carbon atom of the linking group.
  • R 4 is an organic group
  • R 4 is a hydroxy group or an organic group bonded to the carbon atom of the linking group.
  • R 5 is an organic group having a base of 3 to 8 carbon atoms and containing a hetero atom, or an organic group having a base of 2 to 7 carbon atoms and a carboxy group.
  • the present invention includes one or more repeating structural units X' represented by the following general formula (1'), provided that each branched side having 2 to 3 terminals ending in a radically polymerizable substituent
  • the present invention relates to an alkali-soluble resin (hereinafter also referred to as "alkali-soluble resin B") that does not contain a repeating structural unit with a chain.
  • R 1 is hydrogen or a methyl group
  • R 2 is a linking group having 1 or more carbon atoms
  • R 3′ is a carbon atom of the linking group represented by the following general formula (2′) and R 4 is a hydroxy group or an organic group bonded to the carbon atom of the linking group.
  • R 5′ is a hydrocarbon group having a base having 2 to 7 carbon atoms, an organic group having a base having 3 to 8 carbon atoms and containing a hetero atom, or a base having 2 to 7 carbon atoms. and is an organic group having a carboxy group.
  • the linking group of R 2 is a hydrocarbon group having 1 to 10 carbon atoms in the base, or an organic group having 1 to 10 carbon atoms in the base and containing a hetero atom.
  • the linking group of R 2 is a hydrocarbon group having 1 to 10 carbon atoms in the base, or an organic group having 1 to 10 carbon atoms in the base and containing a hetero atom.
  • the organic group for R4 is selected from the group consisting of an acryloyloxy group, a methacryloyloxy group, an acyloxy group, an amidooxy group, an alkoxy group, an aryloxy group, an amino group, and a nitrogen-containing heterocyclic ring. It is preferably an organic group containing one or more selected functional groups.
  • the linking group of R 2 is a hydrocarbon group having a base having 1 to 7 carbon atoms, or an organic group having a base having 1 to 7 carbon atoms and containing a hetero atom.
  • R 4 is preferably a hydroxy group, an acryloyloxy group, or a methacryloyloxy group bonded to the carbon atom of the linking group of R 2 .
  • the linking group of R 2 is a hydrocarbon group having a base having 1 to 7 carbon atoms, or an organic group having a base having 1 to 7 carbon atoms and containing a hetero atom.
  • the R 5 or the R 5' is an organic group represented by the following general formula (3)
  • R 4 is preferably a hydroxy group, an acryloyloxy group, a methacryloyloxy group, or an organic group represented by the following general formula (4), which is bonded to the carbon atom of the linking group of R 2 .
  • each of R 6 and R 7 is independently a hydrocarbon group having 1 to 6 carbon atoms in the base, and the total number of carbon atoms in the base of R 6 and R 7 is 3 to 8.
  • R 8 is hydrogen or a methyl group
  • R 9 is a hydrocarbon group having 1 to 5 carbon atoms as a base, or an organic group having 1 to 5 carbon atoms as a base and containing a hetero atom. be.
  • the content of the repeating structural unit X or X' is preferably 5 to 50 mol% in all repeating structural units.
  • the alkali-soluble resin A or B preferably has an acid value of 20 to 120 mgKOH/g.
  • the alkali-soluble resin A or B preferably has a weight average molecular weight of 5,000 to 40,000.
  • the photosensitive resin composition of the present invention contains at least the alkali-soluble resins A and/or B, a polymerizable monomer, and a photopolymerization initiator.
  • the cured product of the present invention is obtained from the photosensitive resin composition.
  • the cured product is preferably a photospacer, partition wall material, lens material, interlayer insulating film material, protective film material, optical waveguide material, or flattening film material.
  • the present invention also relates to an image display device containing the cured product.
  • the alkali-soluble resin A or B of the present invention contains one or more repeating structural units X or X' represented by the general formula (1) or (1'), and in the repeating structural unit X or X'
  • the main feature is that the length of the side chain is longer than a certain length, and it has a structure having a carboxyl group at the end of the side chain. Due to its characteristic structure, the alkali-soluble resin A or B of the present invention can provide a cured film excellent in development adhesion and resolution even when the film is thickened.
  • the alkali-soluble resin A or B of the present invention since the alkali-soluble resin A or B of the present invention has a hydroxy group or an organic group bonded to the carbon atom of the linking group R2 , it can further have properties derived from these groups.
  • the photosensitive resin composition containing the alkali-soluble resin A and / or B of the present invention can be developed in a short time even when using a weakly alkaline developer, the productivity of cured products such as photospacers is improved. be able to.
  • R 4 is an organic group
  • the alkali-soluble resin A or B of the present invention has a branched structure in the side chain, so that even when the film is thickened, a cured film having even better development adhesion and resolution can be obtained. be able to.
  • the reason for this, although not necessarily bound by theory, is that when R 3 or R 3′ is somewhat long (has a large number of atoms), the terminal carboxy group tends to face the main chain.
  • the number of carboxyl groups that can participate in adhesion to the substrate increases. Furthermore, when the R 4 is an organic group, the side chain of the alkali-soluble resin A or B has a branched structure, so that the terminal carboxy group of the R 3 or R 3′ This is probably because the orientation becomes easier, and the number of carboxyl groups that can participate in adhesion to the substrate increases.
  • the alkali-soluble resin A of the present invention contains one or more repeating structural units X represented by the following general formula (1).
  • R 1 is hydrogen or a methyl group
  • R 2 is a linking group having 1 or more carbon atoms
  • R 3 is represented by the following general formula (2) bonded to a carbon atom of the linking group.
  • R 4 is a hydroxy group or an organic group bonded to the carbon atom of the linking group.
  • R 5 is an organic group having a base of 3 to 8 carbon atoms and containing a hetero atom, or an organic group having a base of 2 to 7 carbon atoms and a carboxy group.
  • the alkali-soluble resin B of the present invention contains one or more repeating structural units X' represented by the following general formula (1'), provided that each has 2 to 3 terminals ending in radically polymerizable substituents. does not contain repeating structural units with branched side chains having (Wherein, R 1 is hydrogen or a methyl group, R 2 is a linking group having 1 or more carbon atoms, and R 3′ is a carbon atom of the linking group represented by the following general formula (2′) and R 4 is a hydroxy group or an organic group bonded to the carbon atom of the linking group.) (Wherein, R 5′ is a hydrocarbon group having a base having 2 to 7 carbon atoms, an organic group having a base having 3 to 8 carbon atoms and containing a hetero atom, or a base having 2 to 7 carbon atoms. and is an organic group having a carboxy group.)
  • (meth)acryl means acrylic or methacrylic
  • (meth)acryloyl means acryloyl or methacryloyl
  • (meth)acrylic acid means acrylic acid or methacrylic acid
  • (meth)acrylate means acrylate or methacrylate, respectively.
  • the number of carbon atoms in the base means the number of carbon atoms in the main skeleton group excluding substituents.
  • R 2 is a linking group having 1 or more carbon atoms
  • R 3 and R 4 , or R 3′ and R 4 are oxygen atoms of an ester bond.
  • the linking group include linear or branched aliphatic saturated or unsaturated hydrocarbon groups, alicyclic saturated or unsaturated hydrocarbon groups (including bridged rings and condensed rings), and aromatic hydrocarbon groups.
  • a hydrogen group an organic group in which some of the carbon atoms constituting the hydrocarbon group are substituted with a hetero atom (e.g., an oxygen atom, a nitrogen atom, a sulfur atom, etc.), and an organic group in which two or more of these are bonded etc.
  • the hydrocarbon group or the organic group includes various substituents (e.g., halogen group, hydroxy group, carboxyl group, amino group, alkyl group, alkenyl group, alkoxy group, aryl group, etc.) and functional groups (e.g., , ester bond, amide bond, ether bond, thioether bond, urethane bond, etc.).
  • the linking group is a hydrocarbon group having 1 to 10 carbon atoms in the base, or an organic is preferably a group.
  • the linking group is a hydrocarbon group having a parent body having 1 to 7 carbon atoms, or a parent body having a carbon number of 1 to 7 and a hetero atom (eg, an oxygen atom, a nitrogen atom, a sulfur atom, etc.). more preferably an organic group containing
  • the hetero atom possessed by the linking group is the portion other than the bonding portion with R 3 or R 3′ in the general formula (1) or (1′), the It is present in the portion other than the bonding portion with R 4 and in the portion other than the bonding portion with the oxygen atom of the ester bond.
  • the linking group may be a linear or branched aliphatic saturated or unsaturated hydrocarbon group having 2 to 7 carbon atoms in the base, or a saturated or unsaturated alicyclic group having 3 to 7 carbon atoms in the base.
  • R 3 is an organic group represented by general formula (2) that bonds to the carbon atom of the linking group of R 2 .
  • R 5 is an organic group having 3 to 8 carbon atoms in the base and containing a hetero atom (e.g., an oxygen atom, a nitrogen atom, a sulfur atom, etc.), or a carbon in the base It is an organic group having a number of 2 to 7 and having a carboxy group.
  • R 5 is preferably an organic group having a matrix of 2 to 7 carbon atoms and a carboxy group.
  • the number of carboxy groups is not particularly limited, but preferably 1-2.
  • the organic groups include various substituents (e.g., halogen groups, hydroxy groups, carboxyl groups, amino groups, alkyl groups, alkenyl groups, alkoxy groups, and aryl groups) and functional groups (e.g., ester bonds, amide bonds, ether bond, thioether bond, urethane bond, etc.).
  • substituents e.g., halogen groups, hydroxy groups, carboxyl groups, amino groups, alkyl groups, alkenyl groups, alkoxy groups, and aryl groups
  • functional groups e.g., ester bonds, amide bonds, ether bond, thioether bond, urethane bond, etc.
  • the organic group represented by the general formula (2) is preferably any one of the following organic groups.
  • R 3′ is an organic group represented by general formula (2′) that bonds to the carbon atom of the linking group of R 2 .
  • R 5′ is a hydrocarbon group having 2 to 7 carbon atoms in the base, a 3 to 8 carbon base in the base, and a hetero atom (e.g., oxygen atom, nitrogen atom, , and a sulfur atom), or an organic group having a base having 2 to 7 carbon atoms and a carboxy group.
  • R 5′ is preferably a hydrocarbon group having a base of 2 to 7 carbon atoms or an organic group having a base of 2 to 7 carbon atoms and a carboxy group.
  • R 5′ has a carboxy group
  • the number of carboxy groups is not particularly limited, but preferably 1-2.
  • the hydrocarbon group include linear or branched aliphatic saturated or unsaturated hydrocarbon groups, alicyclic saturated or unsaturated hydrocarbon groups (including bridged rings and condensed rings), and aromatic hydrocarbons. groups, and hydrocarbon groups in which two or more of these groups are bonded.
  • the hydrocarbon group or the organic group may contain various substituents (e.g., halogen groups, hydroxy groups, carboxyl groups, amino groups, alkyl groups, alkenyl groups, alkoxy groups, and aryl groups) or functional groups (e.g., ester groups). bond, amide bond, ether bond, thioether bond, urethane bond, etc.).
  • the organic group represented by the general formula (2') is preferably any one of the following organic groups.
  • R 5 or R 5' is preferably an organic group represented by the following general formula (3).
  • each of R 6 and R 7 is independently a hydrocarbon group having 1 to 6 carbon atoms in the base, and the total number of carbon atoms in the base of R 6 and R 7 is 3 to 8.
  • hydrocarbon group examples include linear or branched aliphatic saturated or unsaturated hydrocarbon groups, aromatic hydrocarbon groups, and alicyclic saturated or unsaturated hydrocarbon groups.
  • the hydrocarbon group may have various substituents (eg, halogen group, hydroxy group, carboxy group, amino group, alkyl group, alkenyl group, alkoxy group, aryl group, etc.).
  • Examples of the organic group represented by the general formula (3) include the following.
  • R 6 and R 7 are each independently a hydrocarbon group having 1 to 5 carbon atoms as a base, and the total number of carbon atoms in the base of R 6 and R 7 is preferably 3 to 7.
  • the organic group represented by the general formula (2) or (2') is preferably any one of the following organic groups.
  • R 4 is a hydroxy group or an organic group bonded to the carbon atom of the linking group of R 2 .
  • R4 is a hydroxy group
  • the developability can be further improved.
  • R 4 is an organic group
  • properties derived from the organic group eg developability, adhesiveness, solubility, etc.
  • the organic group is not particularly limited, and examples include linear or branched aliphatic saturated or unsaturated hydrocarbon groups, alicyclic saturated or unsaturated hydrocarbon groups (including bridged rings and condensed rings), an aromatic hydrocarbon group, an organic group in which some of the carbon atoms constituting the hydrocarbon group are substituted with heteroatoms (e.g., oxygen atoms, nitrogen atoms, sulfur atoms, etc.), and two or more of these bonded together and the like.
  • heteroatoms e.g., oxygen atoms, nitrogen atoms, sulfur atoms, etc.
  • hydrocarbon group or the organic group includes various substituents (e.g., halogen group, hydroxy group, carboxyl group, amino group, alkyl group, alkenyl group, alkoxy group, aryl group, etc.) and functional groups (e.g., , ester bond, amide bond, ether bond, thioether bond, urethane bond, etc.).
  • substituents e.g., halogen group, hydroxy group, carboxyl group, amino group, alkyl group, alkenyl group, alkoxy group, aryl group, etc.
  • functional groups e.g., ester bond, amide bond, ether bond, thioether bond, urethane bond, etc.
  • the organic group for R4 is one or more functional groups selected from the group consisting of acryloyloxy, methacryloyloxy, acyloxy, amidooxy, alkoxy, aryloxy, amino, and nitrogen-containing heterocycles. and more preferably an acryloyloxy group, a methacryloyloxy group, or an organic group represented by any of the following formulas. (Wherein, R 10 and R 11 are each independently an organic group described in paragraph [0039].)
  • R 4 is preferably a hydroxy group, an acryloyloxy group, a methacryloyloxy group, or an organic group represented by the following general formula (4), which is bonded to the carbon atom of the linking group of R 2 .
  • R 8 is hydrogen or a methyl group
  • R 9 is a hydrocarbon group having 1 to 5 carbon atoms as a base, or an organic group having 1 to 5 carbon atoms as a base and containing a hetero atom. be.
  • R 9 is a hydrocarbon group having 1 to 5 carbon atoms in the base, or a heteroatom (for example, an oxygen atom, a nitrogen atom, and sulfur atoms).
  • a heteroatom for example, an oxygen atom, a nitrogen atom, and sulfur atoms.
  • the heteroatom of the organic group is, in the general formula (4), the portion other than the bonding portion with the nitrogen atom of the urethane bond, and the (meth)acryloyloxy group. It is present in the portion other than the bonding portion with the oxygen atom.
  • the hydrocarbon group includes a linear or branched aliphatic saturated or unsaturated hydrocarbon group.
  • the hydrocarbon group or the organic group may contain various substituents (e.g., halogen groups, hydroxy groups, carboxyl groups, amino groups, alkyl groups, alkenyl groups, alkoxy groups, and aryl groups) or functional groups (e.g., ester groups). bond, amide bond, ether bond, thioether bond, urethane bond, etc.).
  • R 9 is preferably a hydrocarbon group having 1 to 5 carbon atoms as a base, more preferably an ethylene group or a propylene group.
  • Examples of the monomer that is the source of the repeating structural unit other than the repeating structural unit X or X′ constituting the alkali-soluble resin A or B include (meth)acrylic acid, 2-(meth)acryloyloxyethyl succinic acid, Carboxyl group-containing monomers such as maleic acid and itaconic acid; carboxylic anhydride group-containing monomers such as maleic anhydride and itaconic anhydride; methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, butyl Alkyl (meth)acrylates such as (meth)acrylate, benzyl (meth)acrylate, lauryl (meth)acrylate, hydroxyethyl (meth)acrylate, hydroxypropyl (meth)acrylate, ethoxyethyl (meth)acrylate, and glycidyl (meth)acrylate Acrylates; cyclohex
  • styrene, cyclohexylmaleimide, phenylmaleimide, methylmaleimide, ethylmaleimide, n-butylmaleimide, laurylmaleimide, silicone-containing monomers, and the like may be used as copolymerizable monomers. These monomers may be used alone or in combination of two or more.
  • the alkali-soluble resin B contains a repeating structural unit (hereinafter also referred to as "repeating structural unit Y") having a branched side chain having 2 to 3 terminals each ending in a radically polymerizable substituent.
  • the repeating structural unit Y is a monomer unit (1) described in WO 2018/169036.
  • each of the radically polymerizable substituents is, for example, on the hydrocarbon chain (L)
  • Each substituted, the hydrocarbon chain (L) is attached to the main chain of the polymer via, for example, a --COO-- group.
  • the number of carbon atoms constituting the hydrocarbon chain (L) is, for example, 3 to 5, 3 or 4, or 3.
  • the radically polymerizable substituent is, for example, a (meth)acryloyloxy group.
  • the alkali-soluble resin A or B of the present invention is prepared by, for example, reacting a polymer having an epoxy group in a side chain obtained by polymerizing a monomer composition containing an epoxy group-containing (meth)acrylate with a carboxy group-containing compound.
  • a polymer having an ethylenically unsaturated group and a carboxy group is reacted with a compound having an ethylenically unsaturated group and a carboxyl group to convert a side chain having a hydroxy group and an ethylenically unsaturated group, and a hydroxy group such as an isocyanate group is added to the hydroxy group.
  • a compound having a functional group that reacts with the group is reacted, and a compound having a functional group that reacts with an ethylenically unsaturated group such as a hydroxyl group, a thiol group, and an amino group and a carboxy group is added to the ethylenically unsaturated group. It can be synthesized by reaction method (2) or the like.
  • the alkali-soluble resin A or B may be a homopolymer composed of the repeating structural unit X or X', or a random polymer composed of the repeating structural unit X or X' and another repeating structural unit. It may be a copolymer, block copolymer, alternating copolymer, or periodic copolymer.
  • the content of the repeating structural unit X or X' is not particularly limited. From the viewpoint of enabling development in a short time even when a liquid is used, it is preferably 5 to 50 mol %, more preferably 5 to 25 mol % in all repeating structural units.
  • the weight average molecular weight of the alkali-soluble resin A or B is not particularly limited, it is preferably 5,000 to 40,000, more preferably 5,000 to 20,000 from the viewpoint of sensitivity and developability.
  • the weight-average molecular weight is a polystyrene-equivalent value measured using gel permeation chromatography (GPC) and is a value measured according to JIS 7252-4.
  • GPC gel permeation chromatography
  • the acid value of the alkali-soluble resin A or B is not particularly limited, it is preferably 20 to 120 mgKOH/g, more preferably 20, from the viewpoint of enabling development in a short time even when a weakly alkaline developer is used. ⁇ 80 mg KOH/g.
  • the photosensitive resin composition of the present invention contains at least the alkali-soluble resins A and/or B, a polymerizable monomer, and a photopolymerization initiator.
  • the content ratio of the alkali-soluble resin A and / or B to the total solid content in the photosensitive resin composition is not particularly limited, but even when the film is thickened, development From the viewpoint of forming a cured film with excellent adhesion and resolution, and from the viewpoint of enabling development in a short time even when using a weakly alkaline developer, it is usually about 40 to 90% by mass, preferably 40 to 80% by mass. and more preferably 50 to 70% by mass.
  • the polymerizable monomer is not particularly limited, and examples include nonylphenyl carbitol (meth) acrylate, 2-hydroxy-3-phenoxypropyl (meth) acrylate, 2-ethylhexyl carbitol (meth) acrylate, 2-hydroxyethyl (meth) ) Monofunctional monomers such as acrylates and N-vinylpyrrolidone, and polyfunctional aromatic vinyl monomers such as divinylbenzene, diallyl phthalate, and diallylbenzene phosphonate; (di) ethylene glycol di (meth) acrylate, propylene glycol di ( meth)acrylate, trimethylolpropane di(meth)acrylate, trimethylolpropane tri(meth)acrylate, pentaerythritol di(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dip
  • the content of the polymerizable monomer is not particularly limited, but from the viewpoint of sufficiently obtaining the effects of the present invention, the alkali-soluble resin A and / or B 100 parts by mass (when used in combination, the total.) 30 ⁇ It is preferably 100 parts by mass, more preferably 40 to 80 parts by mass, even more preferably 50 to 70 parts by mass.
  • the photopolymerization initiator is not particularly limited, and examples thereof include benzoin and its alkyl ethers such as benzoin, benzoin methyl ether, and benzoin ethyl ether; acetophenones such as; 2-methylanthraquinone, 2-amylanthraquinone, 2-t-butylanthraquinone, 1-chloroanthraquinone and other anthraquinones; 2,4-dimethylthioxanthone, 2,4-diisopropylthioxanthone, 2-chlorothioxanthone, etc.
  • benzoin and its alkyl ethers such as benzoin, benzoin methyl ether, and benzoin ethyl ether
  • acetophenones such as; 2-methylanthraquinone, 2-amylanthraquinone, 2-t-butylanthraquinone, 1-chloroanthraquinone
  • thioxanthones ketals such as acetophenone dimethyl ketal and benzyl dimethyl ketal; benzophenones such as benzophenone; 2-methyl-1-[4-(methylthio)phenyl]-2-morpholino-propan-1-one and 2-benzyl -2-dimethylamino-1-(4-morpholinophenyl)-butanone-1; acylphosphine oxides and xanthones.
  • photopolymerization initiators may be used alone or in combination of two or more.
  • the content of the photopolymerization initiator is not particularly limited, but it is 0.1 to 5 parts by mass with respect to 100 parts by mass of the alkali-soluble resin A and / or B (the total when used in combination). It is preferably 0.2 to 4 parts by mass, and still more preferably 0.5 to 3 parts by mass.
  • a photopolymerization initiation aid may be added to the photosensitive resin composition.
  • photopolymerization initiation aids include 1,3,5-tris(3-mercaptopropionyloxyethyl)-isocyanurate, 1,3,5-tris(3-mercaptobutyloxyethyl)-isocyanurate (Showa Denko manufactured by Karenz MT (registered trademark) NR1), trifunctional thiol compounds such as trimethylolpropane tris (3-mercaptopropionate); butyrate) (manufactured by Showa Denko Co., Ltd., Karenz MT (registered trademark) PEI) and other tetrafunctional thiol compounds; dipentaerythritol hexakis (3-propionate) and other hexafunctional thiol compounds.
  • These photopolymerization initiation aids may be used alone or in combination of two or more.
  • thermal polymerization initiators include, for example, cumene hydroperoxide, diisopropylbenzene peroxide, di-t-butyl peroxide, lauryl peroxide, benzoyl peroxide, t-butylperoxyisopropyl carbonate, t-butylperoxy-2 -organic peroxides such as ethylhexanoate and t-amylperoxy-2-ethylhexanoate; 2,2'-azobis(isobutyronitrile), 1,1'-azobis(cyclohexanecarbonitrile), azo compounds such as 2,2'-azobis(2,4-dimethylvaleronitrile) and dimethyl 2,2'-azobis(2-methylpropionate); These thermal polymerization initiators may be used alone or in combination of two or more.
  • Radically polymerizable oligomers such as unsaturated polyesters, epoxy acrylates, urethane acrylates and polyester acrylates; curable resins such as epoxy resins may be added to the photosensitive resin composition.
  • the photosensitive resin composition may contain a solvent.
  • solvents include ethers such as tetrahydrofuran, dioxane, ethylene glycol dimethyl ether, and diethylene glycol dimethyl ether; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone; ethyl acetate, butyl acetate, propylene glycol monomethyl ether acetate, 3-methoxy esters such as butyl acetate; alcohols such as methanol, ethanol, isopropanol, n-butanol, ethylene glycol monomethyl ether and propylene glycol monomethyl ether; aromatic hydrocarbons such as toluene, xylene and ethylbenzene; mentioned. These solvents may be used alone or in combination of two or more. In addition, the content of the solvent may be appropriately set according to the optimum viscosity when using the composition.
  • the photosensitive resin composition contains fillers such as aluminum hydroxide, talc, clay, barium sulfate, etc., dyes, pigments, antifoaming agents, coupling agents, leveling agents, and sensitizers, as long as the effects of the present invention are not impaired.
  • known additives such as agents, release agents, lubricants, plasticizers, antioxidants, UV absorbers, flame retardants, polymerization inhibitors, thickeners and dispersants.
  • the cured product of the present invention is obtained by curing the photosensitive resin composition.
  • the photosensitive resin composition is injected into a mold (resin mold), or the photosensitive resin composition is placed on a substrate (substrate) or various functional layers.
  • a method of curing the photosensitive resin composition by irradiating it with light (for example, ultraviolet rays) after forming it into a desired shape by coating may be mentioned. Curing conditions are appropriately adjusted according to the photosensitive resin composition to be used.
  • the cured product is suitably used as a photospacer, partition wall material, lens material, interlayer insulating film material, protective film material, optical waveguide material, or flattening film material, and is particularly suitably used as a photospacer.
  • the method for forming the photospacer is not particularly limited, and for example, the photosensitive resin composition may be applied to a substrate such as glass or a transparent plastic film, dried to form a coating film, and then formed by photolithography. can.
  • photolithography for example, a photomask is placed on the coating film, the coating film is photocured by irradiating with ultraviolet rays, and an alkaline aqueous solution is sprayed on the coating film after the ultraviolet irradiation to dissolve and remove the unexposed areas. The remaining exposed portions are washed with water and developed to form photospacers. A post-bake may then be performed.
  • a photospacer having a film thickness of 10 ⁇ m or more, 20 ⁇ m or more, 30 ⁇ m or more, or even 50 ⁇ m or more can be produced with high development adhesion and high resolution.
  • a photospacer having an aspect ratio of 4.0 or more can be produced.
  • the photosensitive resin composition of the present invention can be developed in a short time even when a weakly alkaline developer is used, the photospacer can be produced with high productivity.
  • Alkali-soluble resin 1 containing the following repeating structural units A and X1 was synthesized by the following production method. 100 g of glycidyl methacrylate and 212 g of propylene glycol monomethyl ether acetate were placed in a glass flask equipped with a heating/cooling/stirring device, a reflux condenser, and a nitrogen inlet tube. After the gas phase in the system was replaced with nitrogen, 17 g of 2,2'-azobis(2,4-dimethylvaleronitrile) was added, heated at 80°C, and reacted at the same temperature for 8 hours.
  • the molecular weight was measured by gel permeation chromatography (manufactured by Tosoh Corporation, product number: HLC-8120, column: two connections of G-5000HXL and G-3000HXL, detector: RI, mobile phase: tetrahydrofuran). .
  • the weight average molecular weight was measured by the same method below.
  • the acid value of the alkali-soluble resin 1 was 21 mgKOH/g.
  • Alkali-soluble resin 4 containing the following repeating structural units A and X1 was synthesized by the following production method. 100 g of glycidyl methacrylate and 150 g of propylene glycol monomethyl ether acetate were placed in a glass flask equipped with a heating/cooling/stirring device, a reflux condenser, and a nitrogen inlet tube. After the gas phase in the system was replaced with nitrogen, 5.2 g of 2,2'-azobis(2,4-dimethylvaleronitrile) was added, heated at 80°C, and reacted at the same temperature for 8 hours.
  • Alkali-Soluble Resin 5 containing the following repeating structural units A, B and X2 was synthesized by the following production method. 100 g of glycidyl methacrylate and 160 g of propylene glycol monomethyl ether acetate were placed in a glass flask equipped with a heating/cooling/stirring device, a reflux condenser, and a nitrogen inlet tube. After the gas phase in the system was replaced with nitrogen, 7.5 g of 2,2'-azobis(2,4-dimethylvaleronitrile) was added, heated at 80°C, and reacted at the same temperature for 8 hours.
  • Alkali-soluble resin 6 containing the following repeating structural units A and X3 was synthesized by the following production method. 100 g of glycidyl methacrylate and 212 g of propylene glycol monomethyl ether acetate were placed in a glass flask equipped with a heating/cooling/stirring device, a reflux condenser, and a nitrogen inlet tube. After the gas phase in the system was replaced with nitrogen, 17 g of 2,2'-azobis(2,4-dimethylvaleronitrile) was added, heated at 80°C, and reacted at the same temperature for 8 hours.
  • Examples 1-7 and Comparative Examples 1-3 [Preparation of photosensitive resin composition] 100 parts by mass of the solution containing 45% by mass of the alkali-soluble resin 1, 60 parts by mass of dipentaerythritol hexaacrylate (KAYARAD DPHA manufactured by Nippon Kayaku Co., Ltd.), 1.6 parts by mass of a photopolymerization initiator (SPEEDCURE TPO manufactured by LAMBSON) part, a photopolymerization initiator (BASF Japan Ltd., Irgacure OXE01) 1.0 parts by mass, and a surfactant (manufactured by BYK, BYK-307) 0.2 parts by mass, and the solid content in the composition is A photosensitive resin composition of 50% was prepared (Example 1).
  • each photosensitive resin composition prepared in Examples 1 to 7 and Comparative Examples 1 to 3 using a spin coater After adjusting the rotation speed of the spin coater.
  • Each coating film was formed by coating so that the height of the photospacer was 30 ⁇ m, and each coating film was heated on a hot plate at 100° C. for 2 minutes to completely remove the solvent.
  • each of the obtained coating films was irradiated with 100 mJ/cm 2 of light from an ultra-high pressure mercury lamp through a photospacer forming mask having 100 openings per 1 cm 2 with a diameter of 4 to 30 ⁇ m in increments of 1 ⁇ m ( i-line conversion illuminance 21 mW/cm 2 ).
  • the distance (exposure gap) between the mask and the substrate was set to 100 ⁇ m for exposure.
  • alkali development was performed using a 0.3% Na 2 CO 3 aqueous solution.
  • the development time was set to 1.5 times the shortest development time measured by the method described above.
  • post-baking was performed at 230° C. for 30 minutes to form a photospacer.
  • the photosensitive resin compositions of Examples 1 to 7 have the same photosensitive properties as those of Comparative Examples 1 to 3. It can be seen that development can be completed in a shorter time than with the resin composition, and a cured film having excellent development adhesion can be formed.
  • the alkali-soluble resin of the present invention and the photosensitive resin composition containing the alkali-soluble resin can be used as a photospacer, a partition wall material, a lens material, an interlayer insulating film material, a protective film material, an optical waveguide material, or a flattening film material. It is suitably used as a raw material.

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  • Physics & Mathematics (AREA)
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  • Medicinal Chemistry (AREA)
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Abstract

L'objet de la présente invention est de fournir : une résine soluble dans les alcalis permettant de former un film durci présentant d'excellentes propriétés d'adhérence du développement et de résolution même si le film est épais ; et une composition de résine photosensible qui contient la résine soluble dans les alcalis. Un autre objet de la présente invention est de fournir une composition de résine photosensible qui, en plus des caractéristiques mentionnées ci-dessus, peut être développée en un court laps de temps même si une solution de développement faiblement alcaline est utilisée. Cette résine soluble dans les alcalis contient un ou plusieurs types de motifs de répétition X représentés par la formule générale (1). (Dans la formule, R1 représente un atome d'hydrogène ou un groupe méthyle, R2 représente un groupe de liaison comprenant un ou plusieurs atomes de carbone, R3 représente un groupe organique qui est représenté par la formule générale (2) et se lie à un atome de carbone dans le groupe de liaison, et R4 représente un groupe hydroxyle ou un groupe organique qui se lie à un atome de carbone dans le groupe de liaison). (Dans la formule, R5 représente un groupe organique qui comprend un hétéroatome et qui possède de 3 à 8 atomes de carbone dans la structure principale, ou un groupe organique qui comprend un groupe carboxyle et qui possède de 2 à 7 atomes de carbone dans la structure principale).
PCT/JP2022/004685 2021-02-08 2022-02-07 Résine soluble dans les alcalis, composition de résine photosensible, produit durci et dispositif d'affichage d'images WO2022168974A1 (fr)

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JP2022579641A JPWO2022168974A1 (fr) 2021-02-08 2022-02-07
CN202280013436.7A CN116867822A (zh) 2021-02-08 2022-02-07 碱溶性树脂、感光性树脂组合物、固化物以及图像显示装置
KR1020237026699A KR20230128119A (ko) 2021-02-08 2022-02-07 알칼리 가용성 수지, 감광성 수지 조성물, 경화물,및 화상표시장치

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Publication number Priority date Publication date Assignee Title
WO2023090286A1 (fr) * 2021-11-16 2023-05-25 大阪有機化学工業株式会社 Composition de résine photosensible, produit durci et dispositif d'affichage d'image

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JPS50100128A (fr) * 1973-12-27 1975-08-08
JPS582308A (ja) * 1981-06-19 1983-01-07 チバ−ガイギ−・アクチエンゲゼルシヤフト 重合性組成物
JP2009138156A (ja) * 2007-12-10 2009-06-25 Showa Highpolymer Co Ltd 感光性樹脂および感光性樹脂組成物
JP2009270086A (ja) * 2007-12-28 2009-11-19 Sumitomo Chemical Co Ltd 含フッ素化合物、含フッ素重合体、並びに該重合体を含む組成物および膜
WO2019165425A1 (fr) * 2018-02-26 2019-08-29 The Board Of Supervisors Of Louisiana State University And Agricultural And Mechanical College Composés antimicrobiens à base de gallium et procédés associés
WO2020095774A1 (fr) * 2018-11-08 2020-05-14 昭和電工株式会社 Copolymère, et composition de résine contenant ce copolymère

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JP2013115262A (ja) 2011-11-29 2013-06-10 Sharp Corp 光電変換素子
JP2019124929A (ja) 2018-01-18 2019-07-25 東レ株式会社 ネガ型感光性樹脂組成物、それを用いたフォトスペーサーおよび画像表示装置

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JPS50100128A (fr) * 1973-12-27 1975-08-08
JPS582308A (ja) * 1981-06-19 1983-01-07 チバ−ガイギ−・アクチエンゲゼルシヤフト 重合性組成物
JP2009138156A (ja) * 2007-12-10 2009-06-25 Showa Highpolymer Co Ltd 感光性樹脂および感光性樹脂組成物
JP2009270086A (ja) * 2007-12-28 2009-11-19 Sumitomo Chemical Co Ltd 含フッ素化合物、含フッ素重合体、並びに該重合体を含む組成物および膜
WO2019165425A1 (fr) * 2018-02-26 2019-08-29 The Board Of Supervisors Of Louisiana State University And Agricultural And Mechanical College Composés antimicrobiens à base de gallium et procédés associés
WO2020095774A1 (fr) * 2018-11-08 2020-05-14 昭和電工株式会社 Copolymère, et composition de résine contenant ce copolymère

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023090286A1 (fr) * 2021-11-16 2023-05-25 大阪有機化学工業株式会社 Composition de résine photosensible, produit durci et dispositif d'affichage d'image

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