WO2015137229A1 - Tensioactif à base de fluor, composition de revêtement, composition de matière de protection, et produit durci - Google Patents

Tensioactif à base de fluor, composition de revêtement, composition de matière de protection, et produit durci Download PDF

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Publication number
WO2015137229A1
WO2015137229A1 PCT/JP2015/056489 JP2015056489W WO2015137229A1 WO 2015137229 A1 WO2015137229 A1 WO 2015137229A1 JP 2015056489 W JP2015056489 W JP 2015056489W WO 2015137229 A1 WO2015137229 A1 WO 2015137229A1
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polymerizable monomer
group
polymerizable
fluorine
ring
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PCT/JP2015/056489
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English (en)
Japanese (ja)
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良平 清水
慎 笹本
啓 高野
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Dic株式会社
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Priority to JP2015549879A priority Critical patent/JP5950175B2/ja
Priority to KR1020167023995A priority patent/KR102326845B1/ko
Priority to CN201580013905.5A priority patent/CN106103517B/zh
Publication of WO2015137229A1 publication Critical patent/WO2015137229A1/fr

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    • 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
    • G03F7/0048—Photosensitive materials characterised by the solvents or agents facilitating spreading, e.g. tensio-active agents
    • 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
    • C08F20/00—Homopolymers and 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 a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/10—Esters
    • C08F20/22—Esters containing halogen
    • 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
    • C08F293/00—Macromolecular 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
    • C08F293/005—Macromolecular 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 using free radical "living" or "controlled" polymerisation, e.g. using a complexing agent
    • 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
    • C08F32/00—Homopolymers and copolymers of cyclic compounds having no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system
    • 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
    • C08F8/18—Introducing halogen atoms or halogen-containing groups
    • C08F8/24—Haloalkylation
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING 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
    • C09D201/00—Coating compositions based on unspecified macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING 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
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/65—Additives macromolecular
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • 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
    • G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
    • G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
    • 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
    • G03F7/0046—Photosensitive materials with perfluoro compounds, e.g. for dry lithography
    • 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
    • C08F2/00—Processes of polymerisation
    • C08F2/12—Polymerisation in non-solvents
    • C08F2/16—Aqueous medium
    • C08F2/22—Emulsion polymerisation
    • C08F2/24—Emulsion polymerisation with the aid of emulsifying agents
    • C08F2/30—Emulsion polymerisation with the aid of emulsifying agents non-ionic
    • 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
    • C08F20/00—Homopolymers and 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 a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/10—Esters
    • C08F20/12—Esters of monohydric alcohols or phenols
    • C08F20/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F20/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • 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
    • C08F220/00—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 a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1811—C10or C11-(Meth)acrylate, e.g. isodecyl (meth)acrylate, isobornyl (meth)acrylate or 2-naphthyl (meth)acrylate
    • 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
    • C08F220/00—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 a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1818—C13or longer chain (meth)acrylate, e.g. stearyl (meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING 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
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives

Definitions

  • the present invention relates to a fluorosurfactant capable of obtaining a coating film that is difficult to discolor even when exposed to an alkaline solution or an acidic solution (i.e., less likely to cause blotting), a coating composition using the same, and a resist composition And cured products of these compositions.
  • Color filters used in color liquid crystal display devices and organic EL display devices are generally red (R), green (G), and blue (B) pixels, and a black matrix (BM) for the purpose of improving display contrast therebetween.
  • RGB red
  • G green
  • B blue
  • BM black matrix
  • a resist composition is generally applied on a glass substrate by a coating method such as spin coating or slit coating, and after drying, exposed using a mask and then developed to form a colored pattern.
  • an alkaline developer is used as a developer, and unexposed portions are washed away by rinsing. At that time, there is also a problem that residues such as resin in the unexposed area present in the cleaning liquid adhere to the cured coating surface of the colored pattern in the exposed area, and the resist composition is also required to have characteristics that make it difficult for the residue to adhere to the colored pattern. It is done.
  • composition for forming a color filter pixel in which the residue is less likely to adhere to the colored pattern examples include, for example, a radical polymerizable monomer having a poly (perfluoroalkylene ether) chain and a radical polymerizable monomer having a polyalkylene glycol chain.
  • Fluorine atom-containing surfactant obtained by reacting a copolymer having a reactive functional group obtained by copolymerizing a reactive functional group, a group having reactivity with the reactive functional group, and a compound having a radical polymerizable group
  • a composition for forming a color filter pixel is disclosed (for example, see Patent Document 1).
  • the color pattern obtained using the composition for forming a color filter pixel described in Patent Document 1 changes its color when exposed to an alkaline developer used in the development step.
  • a phenomenon water stain
  • Such water stain disappears after post-baking, so there is no problem as a product, but it is detected as unevenness in the appearance inspection of the patterning surface after development, and it is not possible to distinguish between normal products and abnormal products. It was happening. Therefore, if the inspection sensitivity of the inspection device is lowered in the appearance inspection, the yield of the final color filter product is reduced as a result, which becomes a problem. Accordingly, there is a need for a resist composition that can provide a cured coating film that is less likely to cause water stains in the development process and the washing process.
  • the problem to be solved by the present invention is to use a fluorosurfactant and a fluorosurfactant that can obtain a coating film that is not easily discolored even when exposed to an alkaline solution or an acidic solution (i.e., does not easily cause water stain). It is in providing a coating composition, a resist composition, and the hardened
  • a polymer segment composed of a polymerizable monomer having a fluorinated alkyl group and a polymerizable unsaturated group, a skeleton of a bridged ring hydrocarbon, and a polymerizable unsaturated group A polymerizable monomer having an adamantane ring and a polymerizable unsaturated group, a polymerizable monomer having a dicyclopentane ring and a polymerizable unsaturated group, , A polymerizable monomer having a dicyclopentene ring and a polymerizable unsaturated group, a polymerizable monomer having a norbornane ring and a polymerizable unsaturated group, or a polymerization having a norbornene ring and a polymerizable unsaturated group
  • the present inventors have found that a block copolymer composed of a polymer segment composed of a polymerizable mono
  • the present invention provides a polymerizable monomer containing a polymerizable monomer (a1) having a fluorinated alkyl group having 1 to 6 carbon atoms to which fluorine atoms are directly bonded and a polymerizable unsaturated group.
  • Polymer obtained by using a polymerizable monomer containing a polymer segment (A1) obtained by using the polymerizable monomer (a2) having a skeleton of a bridged ring hydrocarbon and a polymerizable unsaturated group The present invention provides a fluorosurfactant characterized by being a block copolymer containing a segment (A2).
  • the present invention also provides a coating composition comprising the above-mentioned fluorosurfactant.
  • the present invention provides a resist composition containing the fluorine-based surfactant.
  • the present invention provides a cured product obtained by curing the coating composition or the resist composition.
  • the fluorosurfactant of the present invention it is possible to provide a coating composition and a resist composition that hardly cause water stain on a cured product such as a coating film.
  • the fluorosurfactant of the present invention is a polymerizable containing a polymerizable monomer (a1) having a fluorinated alkyl group having 1 to 6 carbon atoms to which fluorine atoms are directly bonded and a polymerizable unsaturated group.
  • a polymerizable monomer including a polymer segment (A1) obtained by using a monomer, and a polymerizable monomer (a2) having a crosslinked cyclic hydrocarbon skeleton and a polymerizable unsaturated group It is a block copolymer containing the polymer segment (A2) obtained.
  • the polymer segment (A1) constituting the block copolymer refers to a segment obtained by polymerizing two or more polymerizable monomers (a1).
  • a polymerizable monomer other than the polymerizable monomer (a1) can be used in combination as long as the effects of the present invention are not impaired.
  • the polymerizable monomer that can be used in combination include a polysynthetic monomer having a polyoxyalkylene chain, a polysynthetic monomer having a linear alkyl group having 1 to 18 carbon atoms, and 1 to 1 carbon atoms. And a polysynthetic monomer having 18 branched alkyl groups.
  • a monomer having a high content of the polymerizable monomer (a1) as the polymerizable monomer containing the polymerizable monomer (a1). ) Is particularly preferable.
  • the polymerizable monomer (a1) having a fluorinated alkyl group having 1 to 6 carbon atoms directly bonded with a fluorine atom and a polymerizable unsaturated group used in the present invention includes the fluorinated alkyl group in the molecule. Any compound having a group and a polymerizable unsaturated group can be used without particular limitation. *
  • the fluorinated alkyl group having 1 to 6 carbon atoms directly bonded with fluorine atoms is a perfluoroalkyl group having 1 to 6 carbon atoms directly bonded with fluorine atoms or a part of hydrogen atoms. It is a partially fluorinated alkyl group having a fluorine atom.
  • a perfluoroalkyl group is preferable because of its high effect as a surfactant.
  • the larger the number of carbon atoms directly bonded with fluorine atoms the better.
  • the number of carbon atoms directly bonded with fluorine atoms is particularly preferably 4-6.
  • Examples of the polymerizable unsaturated group that the polymerizable monomer (a1) has include a (meth) acryloyl group, a vinyl group, and a maleimide group.
  • the (meth) acryloyl group is available because of the availability of raw materials, the ease of controlling the compatibility with the various components in the coating composition and the resist composition, and the good polymerization reactivity. preferable.
  • a monomer represented by the following general formula (1) can be preferably exemplified.
  • the said polymerizable monomer (a1) may use only 1 type, or may use 2 or more types together.
  • R 1 represents a hydrogen atom, a fluorine atom, a methyl group, a cyano group, a phenyl group, a benzyl group, or —C n H 2n —Rf ′ (n represents an integer of 1 to 8, 'Represents any one group of the following formulas (Rf-1) to (Rf-4)), and X represents any one group of the following formulas (X-1) to (X-10) Rf represents any one group of the following formulas (Rf-1) to (Rf-4). ]
  • N in the above formulas (Rf-1) and (Rf-2) represents an integer of 1-6.
  • N in the above formula (Rf-3) represents an integer of 2 to 6.
  • N in the above formula (Rf-4) represents an integer of 4 to 6.
  • (meth) acrylate refers to one or both of methacrylate and acrylate
  • (meth) acrylic acid refers to one or both of methacrylic acid and acrylic acid.
  • the polymerizable monomer (a2) used in the present invention has a bridged cyclic hydrocarbon skeleton and a polymerizable unsaturated group.
  • a layer containing the fluorosurfactant of the present invention (hereinafter sometimes referred to as a block layer) is the surface. Is unevenly distributed.
  • the fluorosurfactant of the present invention has a high glass transition temperature (Tg) due to the presence of the skeleton of the crosslinked ring hydrocarbon, and as a result, the block layer becomes a hard layer.
  • a cured coating film is formed by irradiation with active energy rays, but even when sufficient active energy rays are not irradiated, a sufficiently cured coating film can be obtained due to the presence of a bridged cyclic hydrocarbon skeleton. .
  • the present inventors consider that a coating film obtained by using the fluorosurfactant of the present invention can be a coating film that hardly causes water stain.
  • Examples of the skeleton of the bridged ring hydrocarbon include an adamantane ring, perhydroindene ring, decalin ring, perhydrofluorene ring, perhydroanthracene ring, perhydrophenanthrene ring, dicyclopentane ring, dicyclopentene ring, perhydro Examples include acenaphthene ring, perhydrophenalene ring, norbornane ring, norbornene ring.
  • an adamantane ring, a dicyclopentane ring, a norbornane ring, and a norbornene ring are preferable, because a block layer having a high Tg can be formed on the surface of the coating film, and as a result, a cured coating that is less likely to saturate is obtained.
  • a ring is more preferred.
  • Examples of the polymerizable unsaturated group include a (meth) acryloyl group, a vinyl group, and a maleimide group.
  • the (meth) acryloyl group is available because of the availability of raw materials, the ease of controlling the compatibility with the various components in the coating composition and the resist composition, and the good polymerization reactivity. preferable.
  • Examples of the polymerizable monomer having an adamantane ring and a (meth) acryloyl group include compounds represented by the following formulas (a2-1) and (a2-2).
  • L represents a reactive functional group
  • X and Y represent a divalent organic group or a single bond
  • R represents a hydrogen atom, a methyl group, or CF 3 ).
  • Examples of the reactive functional group include a hydroxyl group, an isocyanate group, an epoxy group, a carboxyl group, a carboxylic acid halide group, and an acid anhydride group.
  • a hydroxyl group is preferable because a fluorosurfactant having good compatibility with the coating composition can be obtained.
  • the organic functional group having the reactive functional group represented by -XL and the bonding position of Y may be bonded to any carbon atom in the adamantane ring.
  • -XL may have two or more.
  • part or all of the hydrogen atoms bonded to the carbon atoms constituting the adamantane ring may be substituted with fluorine atoms, alkyl groups, or the like.
  • X and Y are a divalent organic group or a single bond. Examples of the divalent organic group include carbon atoms such as a methylene group, a propyl group, and an isopropylidene group. Examples thereof include alkylene groups of 1 to 8.
  • the (meth) acryloyl group may be bonded to any carbon atom in the adamantane ring.
  • a part or all of the hydrogen atoms bonded to the carbon atom constituting the adamantane structure in the general formula (a2-1) may be substituted with a fluorine atom, an alkyl group, or the like.
  • polymerizable monomer represented by the general formula (a2-1) include compounds represented by the following.
  • polymerizable monomer represented by the general formula (a2-2) include, for example, compounds represented by the following.
  • a fluorine-based surfactant having good compatibility with other components in the coating composition can be obtained.
  • the compound represented by the formula (a2-1-1), the formula (a2-1-3) and the formula (a2-1-5) are more preferred.
  • the polymerizable monomer having a dicyclopentane ring and a polymerizable unsaturated group that can be preferably used as the polymerizable monomer (a2) in the present invention will be described.
  • Examples of the polymerizable monomer having a dicyclopentane ring and a (meth) acryloyl group include compounds represented by the following formula (a2-3).
  • R represents a hydrogen atom, a methyl group or CF 3.
  • the (meth) acryloyl group may be bonded to any carbon atom in the dicyclopentane ring.
  • the hydrogen atom bonded to the carbon atom constituting the dicyclopentane ring in the general formula (a2-3) may be partially or entirely substituted with a fluorine atom, an alkyl group, or the like. .
  • polymerizable monomer represented by the general formula (a2-3) include, for example, compounds represented by the following.
  • a compound represented by the above formula (a2-3-2) is preferable because the Tg of the coating film is high.
  • Examples of the polymerizable monomer having a dicyclopentene ring and a (meth) acryloyl group include compounds represented by the following formula (a2-4).
  • R represents a hydrogen atom, a methyl group or CF 3.
  • the (meth) acryloyl group may be bonded to any carbon atom in the dicyclopentene ring.
  • a part or all of the hydrogen atoms bonded to the carbon atoms constituting the dicyclopentene ring in the general formula (a2-3) may be substituted with a fluorine atom, an alkyl group, or the like.
  • polymerizable monomer represented by the general formula (a2-4) include, for example, compounds represented by the following.
  • the compound represented by the above formula (a2-4-2) is preferable because the Tg of the coating film is increased.
  • the polymerizable monomer having a norbornane ring and a polymerizable unsaturated group that can be preferably used as the polymerizable monomer (a2) in the present invention will be described.
  • Examples of the polymerizable monomer having a norbornane ring and a (meth) acryloyl group include compounds represented by the following formula (a2-5).
  • R represents a hydrogen atom, a methyl group or CF 3.
  • the (meth) acryloyl group may be bonded to any carbon atom in the norbornane ring.
  • a part or all of the hydrogen atoms bonded to the carbon atom constituting the norbornane ring in the general formula (a2-5) may be substituted with a fluorine atom, an alkyl group, or the like.
  • polymerizable monomer represented by the general formula (a2-5) include, for example, compounds represented by the following.
  • the compound represented by the formula (a2-5-2) is preferable because the Tg of the coating film is increased.
  • the polymerizable monomer having a norbornene ring and a polymerizable unsaturated group that can be preferably used as the polymerizable monomer (a2) in the present invention will be described.
  • Examples of the polymerizable monomer having a norbornene ring and a (meth) acryloyl group include compounds represented by the following formulas (a2-6) and (a2-7).
  • R represents a hydrogen atom, a methyl group or CF 3.
  • the (meth) acryloyl group may be bonded to any carbon atom in the norbornene ring.
  • part or all of the hydrogen atoms bonded to the carbon atoms constituting the norbornene ring may be substituted with fluorine atoms, alkyl groups, or the like.
  • polymerizable monomer represented by the general formula (a2-6) include, for example, compounds represented by the following.
  • a compound represented by the above formula (a2-6-2) is preferable because the Tg of the coating film is increased.
  • the fluorosurfactant of the present invention is a polymerizable monomer (a1) having a fluorinated alkyl group having 1 to 6 carbon atoms to which fluorine atoms are directly bonded and a polymerizable unsaturated group.
  • Polymeric monomer comprising a polymer segment (A1) obtained by using a polymerizable monomer containing, and a polymerizable monomer (a2) having a crosslinked cyclic hydrocarbon skeleton and a polymerizable unsaturated group It is a block copolymer containing the polymer segment (A2) obtained using a body.
  • the polymer segment (A2) is a polymerizable monomer (a2) that is used for obtaining the polymer segment (A2) [constituting the polymer segment (A2)]. What is obtained using 10 to 100% by mass based on the mass is preferable because a fluorosurfactant capable of forming a firmer layer on the coating film surface is obtained, and more preferably obtained using 20 to 90% by mass. preferable.
  • a polymerizable monomer other than the polymerizable monomer (a2) may be used in combination as long as the effects of the present invention are not impaired.
  • the polymerizable monomer that can be used in combination include a polysynthetic monomer having a polyoxyalkylene chain, a polysynthetic monomer having a linear alkyl group having 1 to 18 carbon atoms, and 1 to 1 carbon atoms. And a polysynthetic monomer having 18 branched alkyl groups.
  • the method for producing the fluorosurfactant of the present invention is not particularly limited, but the polymer segment (A1) obtained by using a polymerizable monomer containing the polymerizable monomer (a1), and polymerization Living radical polymerization is preferred from the viewpoint of easy control of the polymerization reaction for obtaining a block copolymer comprising a polymer segment (A2) obtained using a polymerizable monomer containing a polymerizable monomer (a2).
  • a dormant species whose active polymerization end is protected by an atom or an atomic group reversibly generates a radical and reacts with the monomer, whereby the growth reaction proceeds and the first monomer is consumed.
  • the growth terminal can react with the second monomer added sequentially without losing the activity, and the block polymer can be obtained.
  • living radical polymerization include atom transfer radical polymerization (ATRP), reversible addition-cleavage radical polymerization (RAFT), radical polymerization via nitroxide (NMP), radical polymerization using organic tellurium (TERP), etc. Is mentioned.
  • ATRP is polymerized using an organic halide or a sulfonyl halide compound as an initiator, and a metal complex composed of a transition metal compound and a ligand as a catalyst.
  • An organic halogenated compound can be used as the polymerization initiator used in the ATRP.
  • Examples include alkyl esters.
  • alkyl ester having 1 to 6 carbon atoms of the 2-halogenated carboxylic acid having 1 to 6 carbon atoms include, for example, methyl 2-chloropropionate, ethyl 2-chloropropionate, Examples include methyl 2-bromopropionate and ethyl 2-bromoisobutyrate.
  • transition metal compound used in the ATRP is represented by M n + X n .
  • Transition metal M n + is Cu + , Cu 2+ , Fe 2+ , Fe 3+ , Ru 2+ , Ru 3+ , Cr 2+ , Cr 3+ , Mo 0 , Mo + , Mo 2+ , Mo 3+ , W 2+ , W 3+ , Rh 3+ , Rh 4+ , Co + , Co 2+ , Re 2+ , Re 3+ , Ni 0 , Ni + , Mn 3+ , Mn 4+ , V 2+ , V 3+ , Zn + , Zn 2+ , Au + , Au 2+ , Ag + And Ag 2+ .
  • X represents a halogen atom, an alkoxyl group having 1 to 6 carbon atoms, (S0 4 ) 1/2 , (P0 4 ) 1/3 , (HP0 4 ) 1/2 , (H 2 P0 4 ), triflate , Hexafluorophosphate, methane sulfonate, aryl sulfonate (preferably benzene sulfonate or toluene sulfonate), SeR 1 , CN and R 2 COO.
  • R 1 represents aryl, a linear or branched alkyl group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms)
  • R 2 represents 1 to 5 hydrogen atom or halogen.
  • a linear or branched alkyl group having 1 to 6 carbon atoms (preferably a methyl group) which may be substituted once (preferably 1 to 3 times with fluorine or chlorine).
  • n represents a formal charge on the metal and is an integer from 0 to 7.
  • the transition metal complex of 7,8,9,10,11 is still more preferable as zero valent copper, monovalent copper, divalent ruthenium.
  • a complex of divalent iron or divalent nickel may be mentioned.
  • the compound having a ligand capable of coordinating with a transition metal is a ligand containing at least one nitrogen atom, oxygen atom, phosphorus atom or sulfur atom that can be coordinated with the transition metal via a ⁇ bond.
  • a compound having two or more carbon atoms capable of coordinating with a transition metal via a ⁇ bond, a compound having a ligand capable of coordinating with a transition metal via a ⁇ bond or ⁇ bond Is mentioned.
  • the compound having a ligand include, for example, when the central metal is copper, 2,2′-bipyridyl and its derivative, 1,10-phenanthroline and its derivative, tetramethylethylenediamine, pentamethyldiethylenetriamine, hexa And a complex with a ligand such as polyamine such as methyltris (2-aminoethyl) amine.
  • Examples of the divalent ruthenium complex include dichlorotris (triphenylphosphine) ruthenium, dichlorotris (tributylphosphine) ruthenium, dichloro (cyclooctadiene) ruthenium, dichlorobenzeneruthenium, dichlorop-cymenruthenium, dichloro (norbornadiene) ruthenium, Examples thereof include cis-dichlorobis (2,2′-bipyridine) ruthenium, dichlorotris (1,10-phenanthroline) ruthenium, and carbonylchlorohydridotris (triphenylphosphine) ruthenium.
  • examples of the divalent iron complex include a bistriphenylphosphine complex and a triazacyclononane complex.
  • a solvent In the living radical polymerization, it is preferable to use a solvent.
  • the solvent used include ester solvents such as ethyl acetate, butyl acetate, and propylene glycol monomethyl ether acetate; ether solvents such as diisopropyl ether, dimethoxyethane, and diethylene glycol dimethyl ether; halogen solvents such as dichloromethane and dichloroethane; toluene, Aromatic solvents such as xylene; ketone solvents such as methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone; alcohol solvents such as methanol, ethanol and isopropanol; aprotic polar solvents such as dimethylformamide and dimethyl sulfoxide. These solvents can be used alone or in combination of two or more.
  • Method 1 A polymerizable monomer containing a polymerizable monomer (a1) in the presence of a polymerization initiator, a transition metal compound, a compound having a ligand capable of coordinating with the transition metal, and a solvent Living radical polymerization, preferably atom transfer radical polymerization, to obtain a polymer segment (A1), and then a polymerizable monomer containing a polymerizable monomer (a2) is added to further polymerize the polymer segment (A1).
  • Method 2 A polymerizable monomer containing a polymerizable monomer (a2) in the presence of a polymerization initiator, a transition metal compound, a compound having a ligand capable of coordinating with the transition metal, and a solvent
  • living radical polymerization preferably atom transfer radical polymerization
  • a polymerizable monomer containing a polymerizable monomer (a1) is added to the reaction system to form a polymer segment (A2).
  • a method in which a polymerizable monomer containing the polymerizable monomer (a1) is subjected to living radical polymerization, preferably atom transfer radical polymerization.
  • the polymerization temperature in the living radical polymerization is preferably in the range of room temperature to 120 ° C.
  • the fluorosurfactant of the present invention is produced by living radical polymerization
  • the metal resulting from the transition metal compound used in the polymerization may remain in the fluorosurfactant. Therefore, when used in semiconductor applications such as a photoresist composition that causes a problem when the metal remains, it is preferable to remove the residual metal using activated alumina or the like after the polymerization reaction.
  • the weight average molecular weight (Mw) and number average molecular weight (Mn) of the fluorosurfactant of the present invention is preferably from 500 to 200,000, since it becomes a fluorosurfactant that provides a firmer coating surface.
  • the range of 1,000 to 150,000 is more preferable, and the range of 1,500 to 100,000 is more preferable.
  • the dispersity (Mw / Mn) of the fluorosurfactant of the present invention is preferably 1.5 or less, since it becomes a fluorosurfactant that can provide a firmer coating surface.
  • the range of 1.40 is more preferable, and the range of 1.05 to 1.30 is more preferable.
  • the number average molecular weight (Mn) and the weight average molecular weight (Mw) are values converted to polystyrene based on gel permeation chromatography (hereinafter abbreviated as “GPC”) measurement.
  • GPC gel permeation chromatography
  • the fluorine atom content in the fluorosurfactant of the present invention is preferably in the range of 4 to 40% by mass, more preferably in the range of 5 to 35% by mass, since good leveling properties with little coating unevenness can be obtained. A range of 6 to 30% by mass is more preferable.
  • the fluorine atom content can be measured by combustion ion chromatography.
  • the coating composition of the present invention uses the above-described fluorosurfactant of the present invention as an additive.
  • the addition amount of the fluorosurfactant in the coating composition varies depending on the type of coating resin, the coating method, the target film thickness, and the like, but is 0.1% relative to 100 parts by mass of the solid content in the coating composition.
  • the amount is preferably 0001 to 10 parts by mass, more preferably 0.001 to 5 parts by mass, and still more preferably 0.01 to 2 parts by mass. If the amount of the fluorosurfactant added is within this range, the surface tension can be sufficiently lowered, the intended leveling property can be obtained, and the occurrence of problems such as foaming during coating can be suppressed.
  • the fluorosurfactant of the present invention as an additive of the coating composition, it can accumulate to the environment and living organisms compared to conventional fluorosurfactants having a perfluoroalkyl group having 8 or more carbon atoms.
  • a coating composition that exhibits a high leveling property even in a coating method that is low and equivalent to or higher than a conventional fluorosurfactant having a perfluoroalkyl group having 8 or more carbon atoms, that is, high speed and high shearing force. can be provided.
  • Examples of such a coating composition include various coating compositions and photosensitive resin compositions as useful coating compositions.
  • paint composition examples include petroleum resin paints, shellac paints, rosin paints, cellulose paints, rubber paints, rubber paints, lacquer paints, cashew resin paints, oil resin vehicle paints and the like; phenol resins Paints, alkyd resin paints, unsaturated polyester resin paints, amino resin paints, epoxy resin paints, vinyl resin paints, acrylic resin paints, polyurethane resin paints, silicone resin paints, paints using fluororesin paints, etc. It is done.
  • colorants such as pigments, dyes, and carbon
  • inorganic powders such as silica, titanium oxide, zinc oxide, aluminum oxide, zirconium oxide, calcium oxide, and calcium carbonate
  • Organic fine powders such as fatty acids, polyacrylic resins, polyethylene
  • various additives such as light resistance improvers, weather resistance improvers, heat resistance improvers, antioxidants, thickeners, antisettling agents may be added as appropriate Is possible.
  • any method can be used as long as it is a publicly known and publicly used coating method, for example, a roll coater, electrostatic coating, bar coater, gravure coater, knife coater, dipping coating, spray coating, etc. Is mentioned.
  • the above-mentioned photosensitive resin composition changes its physical properties such as resin solubility, viscosity, transparency, refractive index, conductivity, and ion permeability when irradiated with light such as visible light and ultraviolet light.
  • photosensitive resin compositions resist compositions (photoresist compositions, color resist compositions for color filters, etc.) are required to have a high leveling property.
  • a resist composition is applied onto a silicon wafer or a glass substrate on which various metals are vapor-deposited by spin coating with high shearing force so as to have a thickness of about 1 to 2 ⁇ m. Is common.
  • the fluorosurfactant of the present invention is used as an additive for this photosensitive resin composition, particularly a resist composition, thereby exhibiting a high leveling property and forming a uniform coating film (cured product). Therefore, the above problems can be solved.
  • the color resist composition comprises a surfactant and a photoresist agent, and this photoresist agent contains (1) an alkali-soluble resin, (2) a polymerizable compound, and (3) a colorant. What can be illustrated.
  • the alkali-soluble resin (1) used in the present invention is not particularly limited as long as it is soluble in an alkali developer, but at least one acidic group selected from the group of carboxyl group, phenolic hydroxyl group and sulfonic acid group. Or the resin which has the salt is preferable.
  • the (1) alkali-soluble resin may be a polymer obtained by polymerizing a monomer having an acidic group.
  • the monomer having a carboxyl group as an acid group as a raw material for the alkali-soluble resin include, for example, acrylic acid, methacrylic acid, vinyl acetic acid, crotonic acid, itaconic acid, maleic acid, fumaric acid, cinnamic acid or These salts are mentioned.
  • Examples of the monomer having a phenolic hydroxyl group as an acidic group used as a raw material for the alkali-soluble resin include o-hydroxystyrene, m-hydroxystyrene, and p-hydroxystyrene.
  • one or more hydrogen atoms other than the phenolic hydroxyl group and vinyl group bonded to the aromatic ring of these monomers were substituted with an alkyl group, an alkoxyl group, a halogen atom, a nitro group, a cyano group, or an amide group.
  • a compound etc. are also mentioned.
  • Monomers having a sulfonic acid group as an acidic group that is a raw material of the alkali-soluble resin include, for example, vinyl sulfonic acid, styrene sulfonic acid, (meth) allyl sulfonic acid, 2-hydroxy-3- (meth) Allyloxypropanesulfonic acid, (meth) acrylic acid-2-sulfoethyl, (meth) acrylic acid-2-sulfopropyl, 2-hydroxy-3- (meth) acryloxypropanesulfonic acid, 2- (meth) acrylamide-2 -Methylpropanesulfonic acid or a salt thereof.
  • the above-mentioned monomer having an acidic group can be polymerized alone to (1) an alkali-soluble resin, but may be copolymerized with other monomers.
  • Such other monomers include hydrocarbon olefins, vinyl ethers, isopropenyl ethers, allyl ethers, vinyl esters, allyl esters, (meth) acrylic esters, (meth) acrylamides. , Aromatic vinyl compounds, chloroolefins, conjugated dienes and the like. Among these, (meth) acrylic acid esters are preferable.
  • Examples of the (meth) acrylate esters include methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, and n- (meth) acrylate.
  • the monomer having an acidic group that is a raw material for the alkali-soluble resin and the other monomer may be used alone or in combination of two or more.
  • the (2) polymerizable compound is not particularly limited as long as it is a compound having a photopolymerizable functional group that can be polymerized or crosslinked by irradiation with active energy rays such as ultraviolet rays.
  • Specific examples include, for example, trimethylolpropane triacrylate, trimethylolpropane diacrylate, neopentyl glycol di (meth) acrylate, pentaerythritol tetra (meth) acrylate, pentaerythritol tri (meth) acrylate, dipentaerythritol hexa (Meth) acrylate, dipentaerythritol penta (meth) acrylate, hexanediol di (meth) acrylate, trimethylolpropane tri (acryloyloxypropyl) ether, tri (acryloyloxyethyl) isocyanurate, tri (acryloyloxyethy
  • the colorant used in the present invention can be used without particular limitation as long as it can be colored.
  • a pigment is preferred from the viewpoint of high heat resistance and light resistance, and any of organic pigments and inorganic pigments can be used. Can be used.
  • the organic pigment is used according to the color of each pixel of red (R), green (G), and blue (B).
  • red (R) pixels for example, C.I. I. Pigment red 9, C.I. I. Pigment red 97, C.I. I. Pigment red 122, C.I. I. Pigment red 123, C.I. I. Pigment red 149, C.I. I. Pigment red 168, C.I. I. Pigment red 177, C.I. I. Pigment red 180, C.I. I. Pigment red 192, C.I. I. Pigment red 215, C.I. I. Pigment red 216, C.I. I. Pigment red 217, C.I. I.
  • Pigment red 220 C.I. I. Pigment red 223, C.I. I. Pigment red 224, C.I. I. Pigment red 226, C.I. I. Pigment red 227, C.I. I. Pigment red 228, C.I. I. Gment Red 240, C.I. I. Cement red 254, C.I. I. Red pigments such as CI Pigment Red 48: 1 can be used.
  • green (G) pixels for example, C.I. I. Pigment green 7, C.I. I. Green pigments such as CI Pigment Green 36 can be used.
  • blue (B) pixels for example, C.I. I. Pigment blue 15, C.I. I. Pigment blue 15: 6, C.I. I. Pigment blue 22, C.I. I. Pigment blue 60, C.I. I. Blue pigments such as CI Pigment Blue 64 can be used.
  • organic pigments of other colors may be used for hue adjustment.
  • organic pigments for hue adjustment include C.I. I. Pigment violet 19, C.I. I. Pigment violet 23, C.I. I. Pigment violet 29, C.I. I. Pigment violet 30, C.I. I. Pigment violet 37, C.I. I. Pigment violet 40, C.I. I. Violet pigments such as CI Pigment Violet 50; I. Pigment yellow 20, C.I. I. Pigment yellow 24, C.I. I. Pigment yellow 83, C.I. I. Pigment yellow 86, C.I. I. Pigment yellow 93, C.I. I.
  • the (3) colorant used for forming the black matrix (BM) is not particularly limited as long as it is black, but is composed of carbon black, metal oxide, or two or more metal oxides. Pigments such as composite metal compounds are preferred. Further, a combination in which two or more organic pigments selected from pigments having hues of red, blue, green, purple, yellow, cyan, and magenta are mixed and made black by mixing colors may be used.
  • Examples of the carbon black include lamp black, acetylene black, thermal black, channel black, and furnace black.
  • Examples of the metal oxide include titanium black obtained by oxidation of titanium or reduction of titanium dioxide. Usually, titanium black is represented by Ti m O 2m-1 (m is a number of 1 or more).
  • metal oxides such as copper, iron, chromium, manganese, cobalt, are mentioned as a metal oxide.
  • the composite metal compound composed of two or more kinds of metal oxides for example, copper-chromium oxide, copper-chromium-manganese oxide, copper-iron-manganese oxide, or cobalt-iron-manganese An oxide etc. are mentioned.
  • organic pigments examples include quinacridone pigments, perylene pigments, pyrrolo-pyrrole pigments, anthraquinone pigments and the like as pigments having a red hue, and phthalocyanines as pigments having a blue hue.
  • Pigments, indanthrene pigments, etc., pigments having a green hue include halogenated phthalocyanine pigments, and pigments having a purple hue include dioxazine violet, fast violet B, methyl
  • pigments having a hue having a yellow hue include tetrachloroisoindolinone pigments, hansa yellow pigments, benzidine yellow pigments, and azo pigments.
  • a pigment having a cyan hue metal-free phthalo Cyanine, merocyanine, and examples of the pigment having a magenta hue, dimethyl quinacridone, thioindigo, and the like.
  • the colorant used for forming each pixel of red (R), green (G), and blue (B) and the black matrix (BM) may be used alone or in accordance with the required hue. It can also be used in combination.
  • the blending amount of the (3) colorant is preferably in the range of 10 to 80 parts by mass on the basis of 100 parts by mass in total of the (1) alkali-soluble resin and (2) the polymerizable compound. A range of 15 to 65 parts by mass is more preferable.
  • the colorant when (3) the colorant is a pigment, it is preferable to prepare and use a pigment dispersion prepared by dispersing in a organic solvent using a dispersant.
  • the dispersant include surfactants; intermediates or derivatives of pigments; intermediates or derivatives of dyes; resin-type dispersants such as polyamide resins, polyurethane resins, polyester resins, and acrylic resins. It is done.
  • a resin-type dispersant containing an acrylic polymer having an N, N-disubstituted amino group and an acidic group in the main chain or side chain is particularly preferable.
  • resin-type dispersants examples include “BYK-160”, “BYK-161”, “BYK-2001” manufactured by BYK Chemie, “Efka 46” manufactured by Fuka Chemicals, and Ajinomoto Fine. Examples thereof include “Ajisper PB-814” manufactured by Techno Corporation. These dispersants can be used alone or in combination of two or more.
  • organic solvent used in the preparation of the pigment dispersion examples include acetate solvents such as propylene glycol monomethyl ether acetate and propylene glycol monoethyl ether acetate; propionate solvents such as ethoxypropionate; toluene Aromatic solvents such as xylene and methoxybenzene; ether solvents such as butyl cellosolve, propylene glycol monomethyl ether, diethylene glycol ethyl ether and diethylene glycol dimethyl ether; ketone solvents such as methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone; aliphatic carbonization such as hexane Hydrogen solvents; nitrogen compound solvents such as N, N-dimethylformamide, ⁇ -butyrolactam, N-methyl-2-pyrrolidone; ⁇ -butyrolac Lactone solvents such as Ton; carbamates and the like. These solvents can be used
  • Examples of the method for preparing the pigment dispersion include (3) a method of undergoing a kneading and dispersing step and a fine dispersion step of a colorant, and a method of performing only by a fine dispersion step.
  • the colorant, (1) part of the alkali-soluble resin, and, if necessary, the dispersing agent are mixed and kneaded.
  • the machine used for kneading include two rolls, three rolls, ball mills, tron mills, dispersers, kneaders, kneaders, homogenizers, blenders, single-screw or twin-screw extruders, and the like.
  • the colorant can be dispersed by dispersing while applying force.
  • (3) the colorant is preferably refined in particle size by a salt milling method or the like before the kneading.
  • the composition containing the colorant obtained in the kneading and dispersion step is added with a solvent, or (3) the colorant, (1) the alkali-soluble resin, the solvent and necessary
  • the dispersion agent is mixed and dispersed using a disperser together with a dispersion medium for fine particles of glass, zirconia or ceramic, so that (3) the fine particles are close to primary particles. Can be dispersed.
  • the average particle diameter of the primary particles of the colorant is preferably 10 to 100 nm, and more preferably 10 to 60 nm.
  • the average particle size of the colorant (3) is measured with a dynamic light scattering particle size distribution meter.
  • a polymerization initiator is blended in the resist composition of the present invention.
  • the polymerization initiator include benzophenone, acetophenone, benzoin, benzoin ethyl ether, benzoin isobutyl ether, benzyl methyl ketal, azobisisobutyronitrile, 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methyl-1 -Phenyl-1-one, 1- (4'-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one, 1- (4'-dodecylphenyl) -2-hydroxy-2-methylpropane-1 —One, 3,3 ′, 4,4′-tetra (t-butylperoxycarbonyl) benzophenone, 4,4 ′′ -diethylisophthalophen, 2,2-dimethoxy
  • a photosensitizer such as an amine compound or a phosphorus compound can be added to promote photopolymerization.
  • the blending amount of the polymerization initiator is in the range of 0.01 to 15 parts by mass with respect to 100 parts by mass in total of (1) alkali-soluble resin, (2) polymerizable compound and (3) colorant.
  • the range of 0.3 to 7 parts by mass is more preferable.
  • the resist composition of the present invention is an organic solvent, a polymerization inhibitor, an antistatic agent, an antifoaming agent, a viscosity modifier, a light resistance stable, within a range that does not impair the effects of the present invention, depending on purposes such as use and characteristics.
  • Additives such as an agent stabilizer, a heat stabilizer, and an antioxidant can be blended.
  • an organic solvent may be added to adjust the viscosity.
  • the organic solvent that can be used here include acetate solvents such as propylene glycol monomethyl ether acetate and propylene glycol monoethyl ether acetate; propionate solvents such as ethoxypropionate; aromatics such as toluene, xylene, and methoxybenzene.
  • ether solvents such as butyl cellosolve, propylene glycol monomethyl ether, diethylene glycol ethyl ether, diethylene glycol dimethyl ether
  • ketone solvents such as methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone
  • aliphatic hydrocarbon solvents such as hexane
  • N, N- Nitrogen compound solvents such as dimethylformamide, ⁇ -butyrolactam, N-methyl-2-pyrrolidone
  • Lactone solvents such as ⁇ -butyrolactone
  • bamic acid esters examples can be used alone or in combination of two or more.
  • the amount of the organic solvent used varies depending on the purpose of use and the intended film thickness and viscosity, but is 0.5 to 0.5% on a mass basis with respect to the total of (1) the alkali-soluble resin and (2) the polymerizable compound. A range of 6 times the amount is preferable.
  • active energy rays for curing the resist composition of the present invention include active energy rays such as light, electron beam, and radiation.
  • Specific energy sources or curing devices include, for example, germicidal lamps, ultraviolet fluorescent lamps, carbon arcs, xenon lamps, high pressure mercury lamps for copying, medium or high pressure mercury lamps, ultrahigh pressure mercury lamps, electrodeless lamps, metal halide lamps, natural light, etc. Or an electron beam using a scanning type or curtain type electron beam accelerator.
  • germicidal lamps ultraviolet fluorescent lamps, carbon arcs, xenon lamps, high pressure mercury lamps for copying, medium or high pressure mercury lamps, ultrahigh pressure mercury lamps, electrodeless lamps, metal halide lamps, natural light, etc.
  • an electron beam using a scanning type or curtain type electron beam accelerator In addition, when making it harden
  • ultraviolet rays are particularly preferable. Further, it is preferable to irradiate in an inert gas atmosphere such as nitrogen gas since the surface curability of the coating film is improved. Further, if necessary, heat may be used as an energy source and heat treatment may be performed after curing with active energy rays.
  • the application method of the resist composition of the present invention varies depending on the application, for example, gravure coater, roll coater, comma coater, knife coater, curtain coater, shower coater, spin coater, slit coater, dipping, screen printing, spray, applicator, An application method using a bar coater or the like can be mentioned.
  • Example 1 (Synthesis of fluorosurfactant) A flask purged with nitrogen was charged with 47.5 g of 2-propanol and 25.6 g of 3-hydroxy-1-adamantyl methacrylate as solvents, and the temperature was raised to 40 ° C. while stirring under a nitrogen stream. Next, 5.3 g of 2,2′-bipyridyl and 1.9 g of cuprous chloride were charged, and the mixture was stirred for 30 minutes while maintaining the inside of the flask at 40 ° C. Thereafter, 3.3 g of ethyl 2-bromoisobutyrate was added and reacted at 40 ° C.
  • Example 2 (same as above) A flask purged with nitrogen was charged with 81.7 g of 2-propanol and 40.5 g of 3-hydroxy-1-adamantyl methacrylate as solvents, and the temperature was raised to 40 ° C. with stirring under a nitrogen stream. Next, 7.3 g of 2,2′-bipyridyl and 1.5 g of cuprous chloride were charged, and the mixture was stirred for 30 minutes while maintaining the inside of the flask at 40 ° C. Thereafter, 2.5 g of ethyl 2-bromoisobutyrate was added and reacted at 40 ° C. for 2 hours under a nitrogen stream to obtain a polymer segment containing a backbone of a bridged ring hydrocarbon.
  • Example 3 (same as above) A flask purged with nitrogen was charged with 47.5 g of 2-propanol and 25.6 g of dicyclopentanyl methacrylate as solvents, and the temperature was raised to 40 ° C. while stirring under a nitrogen stream. Next, 5.3 g of 2,2′-bipyridyl and 1.9 g of cuprous chloride were charged, and the mixture was stirred for 30 minutes while maintaining the inside of the flask at 40 ° C. Then, 3.3 g of ethyl 2-bromoisobutyrate was added, reacted under nitrogen flow at 40 ° C.
  • Example 4 (same as above) Into a flask purged with nitrogen, 65 g of methyl ethyl ketone and 25.6 g of dicyclopentanyl methacrylate were charged as solvents, and the temperature was raised to 60 ° C. while stirring under a nitrogen stream. Next, 3.1 g of 2,2′-bipyridyl and 1.1 g of cuprous chloride were charged, and the mixture was stirred for 30 minutes while maintaining the inside of the flask at 60 ° C. Thereafter, 2.0 g of ethyl 2-bromoisobutyrate was added and reacted at 40 ° C.
  • Example 5 (same as above) A flask purged with nitrogen was charged with 65 g of methyl ethyl ketone and 31 g of 1-adamantyl methacrylate as solvents, and the temperature was raised to 60 ° C. with stirring under a nitrogen stream. Next, 3.1 g of 2,2′-bipyridyl and 1.1 g of cuprous chloride were charged, and the mixture was stirred for 30 minutes while maintaining the inside of the flask at 60 ° C. Thereafter, 2.0 g of ethyl 2-bromoisobutyrate was added and reacted at 60 ° C. for 3 hours under a nitrogen stream to obtain a polymer segment containing a backbone of a bridged ring hydrocarbon.
  • Example 5 (same as above) To a flask purged with nitrogen, 65 g of methyl ethyl ketone and 31 g of isobornyl methacrylate were charged as solvents, and the temperature was raised to 60 ° C. while stirring under a nitrogen stream. Next, 3.1 g of 2,2′-bipyridyl and 1.1 g of cuprous chloride were charged, and the mixture was stirred for 30 minutes while maintaining the inside of the flask at 60 ° C. Thereafter, 2.0 g of ethyl 2-bromoisobutyrate was added and reacted at 60 ° C. for 3 hours under a nitrogen stream to obtain a polymer segment containing a backbone of a bridged ring hydrocarbon.
  • Comparative Example 1 In a glass flask equipped with a stirrer, a condenser, a dripping device, and a thermometer, 133 parts by mass of methyl isobutyl ketone was placed and heated to 90 ° C. with stirring in a nitrogen stream. Then, 32 parts by mass of 2- (tridecafluorohexyl) ethyl methacrylate, 68 parts by mass of propylene glycol / polybutylene glycol monomethacrylate having an oxypropylene moiety having 1 repeating unit and an oxybutylene moiety having an average repeating unit of 6 are added to methyl isobutyl.
  • Comparative Example 2 A glass flask equipped with a stirrer, a thermometer, a condenser, and a dropping device was charged with 50.4 g of methyl isobutyl ketone as a solvent and heated to 90 ° C. while stirring under a nitrogen stream. Next, a monomer solution in which 44.1 g of 2- (tridecafluorohexyl) ethyl methacrylate and 59.1 g of 3-hydroxy-1-adamantyl methacrylate were dissolved in 167.4 g of methyl isobutyl ketone, and t-butyl as a radical polymerization initiator were used.
  • the molecular weight of the fluorosurfactant (2 ') was measured by GPC (polystyrene equivalent molecular weight). As a result, the number average molecular weight was 3,600 and the weight average molecular weight was 18,000. The fluorine atom content calculated from the raw material charge ratio was 18%, the adamantane content was 24%, and the radical polymerizable unsaturated group equivalent was 550 g / eq. Met.
  • X is a perfluoromethylene group and a perfluoroethylene group, and an average of 7 perfluoromethylene groups and an average of 8 perfluoroethylene groups are present per molecule, and the number of fluorine atoms is (The average is 46.)
  • methyl ethyl ketone solution containing 50% by mass of a fluorosurfactant (3 ') having a polymerizable group.
  • the molecular weight of the fluorosurfactant (3 ') was measured by GPC (polystyrene equivalent molecular weight). As a result, the number average molecular weight was 2,400, the weight average molecular weight was 7,100, and the maximum molecular weight was 200,000.
  • Example 7 (Preparation of resist composition) 42 g of green pigment dispersion using FASTOGEN Green A110 manufactured by DIC Corporation as a colorant, 15 g of Unidic RS20-160 manufactured by DIC Corporation as a binder resin, and NK ester manufactured by Shin-Nakamura Chemical Co., Ltd. as a photopolymerizable monomer 6 g of A-200, 0.5 g of Irgacure # 369 manufactured by BASF Japan Ltd. as a photopolymerization initiator, 0.06 g of the fluorosurfactant (1) of the present invention in terms of solid content, and 37 g of PGMEA were mixed. Thus, a color resist composition (1) was prepared.
  • a cured coating film was obtained using the color resist composition (1).
  • the water stain was evaluated using this cured coating film.
  • a method for creating a cured coating film and a method for evaluating water stain are shown below. The evaluation results are shown in Table 1.
  • the color resist composition (1) was spin-coated on a 7 cm ⁇ 7 cm glass plate at 1000 rpm for 10 seconds, and then exposed to a high-pressure mercury lamp at 200 mJ / cm 2 to form a coating film.
  • Example 8 (same as above) A color resist composition (2) was obtained in the same manner as in Example 7 except that the fluorosurfactant (2) was used in place of the fluorosurfactant (1). The same evaluation as in Example 7 was performed, and the results are shown in Table 1.
  • Example 9 (same as above) A color resist composition (3) was obtained in the same manner as in Example 7 except that the fluorosurfactant (3) was used instead of the fluorosurfactant (1). The same evaluation as in Example 7 was performed, and the results are shown in Table 1.
  • Example 10 (same as above) A color resist composition (4) was obtained in the same manner as in Example 7 except that the fluorosurfactant (4) was used instead of the fluorosurfactant (1). The same evaluation as in Example 7 was performed, and the results are shown in Table 1.
  • Example 11 (same as above) A color resist composition (5) was obtained in the same manner as in Example 7 except that the fluorosurfactant (5) was used instead of the fluorosurfactant (1). The same evaluation as in Example 7 was performed, and the results are shown in Table 1.
  • Example 12 (same as above) A color resist composition (6) was obtained in the same manner as in Example 7 except that the fluorosurfactant (6) was used instead of the fluorosurfactant (1). The same evaluation as in Example 7 was performed, and the results are shown in Table 1.
  • Comparative Example 1 (Preparation of resist composition for comparison) A comparative color resist composition (1 ′) was obtained in the same manner as in Example 7 except that the comparative fluorosurfactant (1 ′) was used instead of the fluorosurfactant (1). The same evaluation as in Example 7 was performed, and the results are shown in Table 1.
  • Comparative Example 2 (same as above) A comparative color resist composition (2 ′) was obtained in the same manner as in Example 7 except that the comparative fluorosurfactant (2 ′) was used instead of the fluorosurfactant (1). The same evaluation as in Example 7 was performed, and the results are shown in Table 1.
  • Comparative Example 3 (same as above) A comparative color resist composition (3 ′) was obtained in the same manner as in Example 7 except that the comparative fluorosurfactant (3 ′) was used instead of the fluorosurfactant (1). The same evaluation as in Example 7 was performed, and the results are shown in Table 1.

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  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
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  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
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Abstract

La présente invention concerne : un tensioactif à base de fluor qui permet d'obtenir une pellicule de revêtement qui ne change pas facilement de couleur (ne forme pas facilement de taches d'eau) même si elle est exposée à des solutions basiques ou des solutions acides. Le tensioactif à base de fluor est caractérisé en ce qu'il est un copolymère bloc contenant : un segment de polymère (A1) obtenu à l'aide de monomères polymérisables incluant un monomère polymérisable (a1) comportant un groupement insaturé polymérisable et un groupement alkyle fluoré comportant 1 à 6 atomes de carbone au(x)quel(s) un atome de fluor est directement lié ; et un segment de polymère (A2) obtenu à l'aide de monomères polymérisables comprenant un monomère polymérisable (a2) comportant un groupement insaturé polymérisable et un squelette hydrocarboné cyclique ponté.
PCT/JP2015/056489 2014-03-13 2015-03-05 Tensioactif à base de fluor, composition de revêtement, composition de matière de protection, et produit durci WO2015137229A1 (fr)

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KR1020167023995A KR102326845B1 (ko) 2014-03-13 2015-03-05 불소계 계면활성제, 코팅 조성물, 레지스트 조성물 및 경화물
CN201580013905.5A CN106103517B (zh) 2014-03-13 2015-03-05 氟系表面活性剂、涂布组合物、保护剂组合物及固化物

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WO2017169951A1 (fr) * 2016-03-31 2017-10-05 株式会社Ｄｎｐファインケミカル Composition de résine, filtre coloré et dispositif d'affichage d'image
JP2018025687A (ja) * 2016-08-10 2018-02-15 東洋インキＳｃホールディングス株式会社 感光性着色組成物およびカラーフィルタ
JP2018081168A (ja) * 2016-11-15 2018-05-24 Dic株式会社 カラーレジスト組成物、カラーフィルター及び液晶表示装置
WO2019065185A1 (fr) * 2017-09-28 2019-04-04 株式会社Ｄｎｐファインケミカル Composition de résine colorante, produit durci, filtre couleur et dispositif d'affichage
JP2021004922A (ja) * 2019-06-25 2021-01-14 東洋インキＳｃホールディングス株式会社 感光性着色組成物、並びにこれを用いたカラーフィルタ、液晶表示装置
JP2021009409A (ja) * 2020-10-16 2021-01-28 東洋インキＳｃホールディングス株式会社 感光性着色組成物およびカラーフィルタ
JP2021051327A (ja) * 2016-03-31 2021-04-01 東友ファインケム株式会社Ｄｏｎｇｗｏｏ Ｆｉｎｅ−Ｃｈｅｍ Ｃｏ．， Ｌｔｄ． 青色感光性樹脂組成物、これを含む青色カラーフィルタおよびディスプレイ素子

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JP7189476B2 (ja) * 2019-09-04 2022-12-14 ダイキン工業株式会社 含フッ素共重合体
CN113552768A (zh) 2020-04-24 2021-10-26 东洋油墨Sc控股株式会社 感光性着色组合物、彩色滤光片及图像显示装置
JP7267532B1 (ja) 2022-04-20 2023-05-02 東洋インキＳｃホールディングス株式会社 感光性組成物、光学フィルタ、画像表示装置、及び固体撮像素子
JP7267533B1 (ja) 2022-04-20 2023-05-02 東洋インキＳｃホールディングス株式会社 感光性組成物、光学フィルタ、画像表示装置、及び固体撮像素子

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JP2004143440A (ja) * 2002-09-27 2004-05-20 Fuji Photo Film Co Ltd インクジェットプリンタ用油性インク組成物及びそれを用いた画像形成方法
JP2009244729A (ja) * 2008-03-31 2009-10-22 Fujifilm Corp 感光性樹脂組成物、遮光性カラーフィルター及びその製造方法、並びに、固体撮像素子
JP2012068374A (ja) * 2010-09-22 2012-04-05 Dic Corp カラーレジスト組成物、カラーフィルター及び液晶表示装置
JP2013006928A (ja) * 2011-06-23 2013-01-10 Dic Corp フッ素系界面活性剤、それを用いたコーティング組成物及びレジスト組成物
JP2013209505A (ja) * 2012-03-30 2013-10-10 Dic Corp フッ素原子含有重合性樹脂、それを用いた活性エネルギー線硬化性組成物、その硬化物及び物品。

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Publication number Priority date Publication date Assignee Title
WO2017169951A1 (fr) * 2016-03-31 2017-10-05 株式会社Ｄｎｐファインケミカル Composition de résine, filtre coloré et dispositif d'affichage d'image
JPWO2017169951A1 (ja) * 2016-03-31 2019-03-22 株式会社Ｄｎｐファインケミカル 樹脂組成物、カラーフィルタ、および画像表示装置
JP2021051327A (ja) * 2016-03-31 2021-04-01 東友ファインケム株式会社Ｄｏｎｇｗｏｏ Ｆｉｎｅ−Ｃｈｅｍ Ｃｏ．， Ｌｔｄ． 青色感光性樹脂組成物、これを含む青色カラーフィルタおよびディスプレイ素子
JP7076209B2 (ja) 2016-03-31 2022-05-27 株式会社Ｄｎｐファインケミカル 樹脂組成物、カラーフィルタ、および画像表示装置
JP2018025687A (ja) * 2016-08-10 2018-02-15 東洋インキＳｃホールディングス株式会社 感光性着色組成物およびカラーフィルタ
JP2018081168A (ja) * 2016-11-15 2018-05-24 Dic株式会社 カラーレジスト組成物、カラーフィルター及び液晶表示装置
WO2019065185A1 (fr) * 2017-09-28 2019-04-04 株式会社Ｄｎｐファインケミカル Composition de résine colorante, produit durci, filtre couleur et dispositif d'affichage
JPWO2019065185A1 (ja) * 2017-09-28 2019-11-14 株式会社Ｄｎｐファインケミカル 着色樹脂組成物、硬化物、カラーフィルタ、及び表示装置
JP2021004922A (ja) * 2019-06-25 2021-01-14 東洋インキＳｃホールディングス株式会社 感光性着色組成物、並びにこれを用いたカラーフィルタ、液晶表示装置
JP2021009409A (ja) * 2020-10-16 2021-01-28 東洋インキＳｃホールディングス株式会社 感光性着色組成物およびカラーフィルタ

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JPWO2015137229A1 (ja) 2017-04-06
JP5950175B2 (ja) 2016-07-13
TW201539128A (zh) 2015-10-16
CN106103517B (zh) 2020-09-11
CN106103517A (zh) 2016-11-09
KR102326845B1 (ko) 2021-11-17

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