WO2014192502A1 - Composition polymérisable, polymère, feuille adhésive optique, dispositif d'affichage d'image et son procédé de production - Google Patents

Composition polymérisable, polymère, feuille adhésive optique, dispositif d'affichage d'image et son procédé de production Download PDF

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WO2014192502A1
WO2014192502A1 PCT/JP2014/062093 JP2014062093W WO2014192502A1 WO 2014192502 A1 WO2014192502 A1 WO 2014192502A1 JP 2014062093 W JP2014062093 W JP 2014062093W WO 2014192502 A1 WO2014192502 A1 WO 2014192502A1
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component
polymerizable composition
image display
polymer
meth
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PCT/JP2014/062093
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English (en)
Japanese (ja)
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一彦 大賀
律子 東
眸 上野
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昭和電工株式会社
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
    • C09J4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00
    • B—PERFORMING OPERATIONS; TRANSPORTING
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    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/30—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers
    • B32B27/308—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers comprising acrylic (co)polymers
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/40—Layered products comprising a layer of synthetic resin comprising polyurethanes
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B3/00—Layered products comprising a layer with external or internal discontinuities or unevennesses, or a layer of non-planar shape; Layered products comprising a layer having particular features of form
    • B32B3/02—Layered products comprising a layer with external or internal discontinuities or unevennesses, or a layer of non-planar shape; Layered products comprising a layer having particular features of form characterised by features of form at particular places, e.g. in edge regions
    • B32B3/08—Layered products comprising a layer with external or internal discontinuities or unevennesses, or a layer of non-planar shape; Layered products comprising a layer having particular features of form characterised by features of form at particular places, e.g. in edge regions characterised by added members at particular parts
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B3/00—Layered products comprising a layer with external or internal discontinuities or unevennesses, or a layer of non-planar shape; Layered products comprising a layer having particular features of form
    • B32B3/10—Layered products comprising a layer with external or internal discontinuities or unevennesses, or a layer of non-planar shape; Layered products comprising a layer having particular features of form characterised by a discontinuous layer, i.e. formed of separate pieces of material
    • B32B3/18—Layered products comprising a layer with external or internal discontinuities or unevennesses, or a layer of non-planar shape; Layered products comprising a layer having particular features of form characterised by a discontinuous layer, i.e. formed of separate pieces of material characterised by an internal layer formed of separate pieces of material which are juxtaposed side-by-side
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    • B32B7/00—Layered products characterised by the relation between layers; Layered products characterised by the relative orientation of features between layers, or by the relative values of a measurable parameter between layers, i.e. products comprising layers having different physical, chemical or physicochemical properties; Layered products characterised by the interconnection of layers
    • B32B7/04—Interconnection of layers
    • B32B7/12—Interconnection of layers using interposed adhesives or interposed materials with bonding properties
    • 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
    • C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
    • C08F299/02—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates
    • C08F299/04—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from polyesters
    • C08F299/0485—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from polyesters from polyesters with side or terminal unsaturations
    • C08F299/0492—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from polyesters from polyesters with side or terminal unsaturations the unsaturation being in acrylic or methacrylic groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
    • C08G18/4236—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups
    • C08G18/4238—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups derived from dicarboxylic acids and dialcohols
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/67—Unsaturated compounds having active hydrogen
    • C08G18/671—Unsaturated compounds having only one group containing active hydrogen
    • C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/73—Polyisocyanates or polyisothiocyanates acyclic
    • C08G18/735—Polyisocyanates or polyisothiocyanates acyclic containing one isocyanate or isothiocyanate group linked to a primary carbon atom and at least one isocyanate or isothiocyanate group linked to a tertiary carbon atom
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/81—Unsaturated isocyanates or isothiocyanates
    • C08G18/8141—Unsaturated isocyanates or isothiocyanates masked
    • C08G18/815—Polyisocyanates or polyisothiocyanates masked with unsaturated compounds having active hydrogen
    • C08G18/8158—Polyisocyanates or polyisothiocyanates masked with unsaturated compounds having active hydrogen with unsaturated compounds having only one group containing active hydrogen
    • C08G18/8175—Polyisocyanates or polyisothiocyanates masked with unsaturated compounds having active hydrogen with unsaturated compounds having only one group containing active hydrogen with esters of acrylic or alkylacrylic acid having only one group containing active hydrogen
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
    • C09J175/04—Polyurethanes
    • C09J175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
    • C09J175/16—Polyurethanes having carbon-to-carbon unsaturated bonds having terminal carbon-to-carbon unsaturated bonds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2307/00—Properties of the layers or laminate
    • B32B2307/40—Properties of the layers or laminate having particular optical properties
    • B32B2307/414—Translucent
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2307/00—Properties of the layers or laminate
    • B32B2307/50—Properties of the layers or laminate having particular mechanical properties
    • B32B2307/54—Yield strength; Tensile strength
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2307/00—Properties of the layers or laminate
    • B32B2307/70—Other properties
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    • B32B2457/00—Electrical equipment
    • B32B2457/20—Displays, e.g. liquid crystal displays, plasma displays
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2551/00—Optical elements
    • 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
    • C08F220/1812—C12-(meth)acrylate, e.g. lauryl (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
    • C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/10—Esters
    • C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
    • C08F222/106—Esters of polycondensation macromers
    • C08F222/1065—Esters of polycondensation macromers of alcohol terminated (poly)urethanes, e.g. urethane(meth)acrylates

Definitions

  • the present invention relates to a polymerizable composition used in an image display device such as a liquid crystal display device used in, for example, smartphones and tablet PCs, a polymer obtained by polymerizing the composition, and an optical having a layer of the polymer
  • the present invention relates to a pressure-sensitive adhesive sheet, a method for producing an image display device using the composition, and an image display device produced by the method.
  • a liquid crystal display device 101 shown in FIG. 6 is known as this type of image display device.
  • the liquid crystal display device 101 has a transparent protective part 103 made of, for example, glass or resin on a liquid crystal display panel 102.
  • a gap 104 is provided between the liquid crystal display panel 102 and the protective part 103 by interposing a spacer 104 between the protective part 103 and the liquid crystal display panel 102. Is provided.
  • the presence of the gap 105 between the liquid crystal display panel 102 and the protection unit 103 causes light scattering, resulting in a decrease in contrast and brightness, and the presence of the gap 105 hinders thinning of the panel. It has become.
  • a resin plate generally has a tendency to have larger distortion and warpage than glass, and there is a demand for the resin that exhibits good adhesion to the resin plate and does not peel off.
  • JP 2012-46658 A discloses a photocurable adhesive composition containing a (meth) acrylate oligomer having an ultraviolet crosslinkable site and a hindered amine, and the composition. Is disclosed for use in bonding an optical display panel and a protective panel.
  • Japanese Patent Application Laid-Open No. 2012-46658 discloses the tensile modulus and adhesion to glass, but does not disclose the storage modulus and durability of peeling, and in particular, resistance to peeling with a resin protective part. Is not disclosed, and there is no disclosure of high dielectric constant.
  • JP 2012-41456 A discloses a (meth) acrylic acid ester monomer having a hydrocarbon group having 1 to 12 carbon atoms, a hydroxyl group-containing (meth) acrylic acid ester monomer, an amide group.
  • An acrylic resin having a weight average molecular weight of 400,000 to 2,000,000 and a dielectric constant of 3 to 6 obtained by copolymerization of a monomer component containing a monomer and a vinyl ester monomer A polymer compound is disclosed, and it is disclosed that the acrylic polymer compound is used for a pressure-sensitive adhesive composition for a touch panel, and that the composition is excellent in adhesion to a glass plate and a resin plate.
  • JP2012-41456A does not disclose the durability of peeling.
  • a curable resin composition is applied to a base having an image display part or a translucent protective part arranged on the image display part, and the base and the protective part are provided.
  • a method for manufacturing an image display device having a process of forming a resin cured material layer between a base portion and a protective portion by being placed in close proximity to each other and cured, and as a curable resin composition, polyurethane acrylate, polyisoprene acrylate Or one or more polymers selected from esterified products thereof, terpene hydrogenated resins and butadiene polymers, and one or more acrylates selected from isobornyl acrylate, dicyclopentenyloxyethyl methacrylate and 2-hydroxybutyl methacrylate.
  • the present invention relates to a polymerizable composition for forming a polymer layer interposed between an image display unit and a translucent protective unit of an image display device, and prevents peeling of the display unit and the protective unit.
  • both the display unit and the protective unit are made of glass, but recently, the protective unit is made of resin (polycarbonate or PMMA), and not only the resistance to peeling from the glass plate but also the resin plate Therefore, an object of the present invention is to provide a polymerizable composition that is excellent not only in peeling resistance with a glass plate but also in peeling resistance with a resin plate. Further, the peeling resistance requires durability and is evaluated under conditions of high temperature and high humidity, and therefore cannot be solved only by improving adhesiveness. An object of the present invention is to provide durable peeling resistance.
  • the present inventors limited the molecular weight of the (meth) acryloyl group-containing polymer compound, which is the main component of the polymerizable composition, to a specific range, and then polymerizable composition.
  • the inventors have found that the above problems can be solved by limiting the storage elastic modulus of the polymer obtained by polymerizing the product to a certain range, and have completed the present invention.
  • the present invention (I) is a polymerizable composition for forming a polymer layer interposed between an image display part and a translucent protective part of an image display device, the polymerizable composition But, (Component 1) containing a (meth) acryloyl group-containing polymer compound having a number average molecular weight in the range of 1000 to 15000, and (Component 2) a photopolymerization initiator, and obtained by polymerizing the polymerizable composition.
  • the present invention relates to a polymerizable composition characterized by having a storage elastic modulus of 1 ⁇ 10 3 to 1 ⁇ 10 5 Pa at 25 ° C. and a frequency of 0.1 Hz.
  • the present invention (II) is a polymerizable composition for forming a polymer layer interposed between the image display part and the translucent protective part of the image display device, the polymerizable composition comprising: (Component 1) (meth) acryloyl group-containing polymer compound having a number average molecular weight in the range of 1000 to 15000, Polymerization obtained by polymerizing the polymerizable composition, comprising (Component 2) a photopolymerization initiator, and (Component 3) a radical polymerizable unsaturated group-containing compound having at least one of an alcoholic hydroxyl group and an amide group.
  • the present invention relates to a polymerizable composition characterized by having a storage elastic modulus of 1 ⁇ 10 3 to 1 ⁇ 10 5 Pa at 25 ° C. and a frequency of 0.1 Hz.
  • the present invention (III) is a polymerizable composition for forming a polymer layer interposed between the image display part of the image display device and the translucent protective part, the polymerizable composition comprising: (Component 1) (meth) acryloyl group-containing polymer compound having a number average molecular weight in the range of 1000 to 15000, (Component 2) Photopolymerization initiator, (Component 3) a radical polymerizable unsaturated group-containing compound having at least one of an alcoholic hydroxyl group and an amide group, and (Component 4) no alcoholic hydroxyl group or amide group, and a viscosity of 25 ° C.
  • a polymer obtained by polymerizing the polymerizable composition containing a (meth) acryloyl group-containing compound that is 500 mPa ⁇ s or less has a storage elastic modulus at 25 ° C. and a frequency of 0.1 Hz of 1 ⁇ 10 3 to
  • the present invention relates to a polymerizable composition characterized by being 1 ⁇ 10 5 Pa.
  • the present invention (IV) is a polymerizable composition for forming a polymer layer interposed between the image display part of the image display device and the translucent protective part, the polymerizable composition comprising: (Component 1) (meth) acryloyl group-containing polymer compound having a number average molecular weight in the range of 1000 to 15000, (Component 2) Photopolymerization initiator, (Component 3) Radical polymerizable unsaturated group-containing compound having at least one of an alcoholic hydroxyl group and an amide group, (Component 4) a (meth) acryloyl group-containing compound which does not have any group of an alcoholic hydroxyl group and an amide group and has a viscosity of 500 mPa ⁇ s or less at 25 ° C.
  • Nonionic surfactant having no (meth) acryloyl group and (Component 6) No (meth) acryloyl group in the molecule, a function for suppressing radical polymerization, a function for inhibiting radical polymerization, light Liquid or solid at 25 ° C., which has neither a polymerization initiation function nor a surface-active function, and is composed of carbon atoms and hydrogen atoms, or is composed of carbon atoms, hydrogen atoms and oxygen atoms
  • the storage modulus of the polymer obtained by polymerizing the polymerizable composition at 25 ° C. and a frequency of 0.1 Hz is 1 ⁇ 10 3 to 1 ⁇ 10 5 Pa.
  • the present invention relates to a polymerizable composition.
  • the present invention (V) relates to a polymer obtained by polymerizing the polymerizable composition of the present invention (I) to the present invention (IV).
  • the present invention (VI) is a polymerizable composition for producing an optical pressure-sensitive adhesive sheet used as a polymer layer interposed between an image display portion and a translucent protective portion of an image display device.
  • the present invention also relates to a polymerizable composition characterized in that the polymerizable composition is the polymerizable composition of the present invention (I) to the present invention (IV).
  • the present invention (VII) has a thickness obtained by applying the polymerizable composition of the present invention (VI), irradiating the polymerizable composition with light capable of being photosensitized by the photopolymerization initiator, and polymerizing the polymerizable composition.
  • the present invention relates to an optical pressure-sensitive adhesive sheet having a polymer layer of 10 to 1000 ⁇ m.
  • the present invention (VIII) is a method for producing an image display device comprising a base having an image display portion, a translucent protective portion, and a polymer layer interposed between the base and the protective portion, The method comprises the step of interposing the polymerizable composition of the present invention (IV) between the base part and the protective part, and irradiating the polymerizable composition with light that can be photosensitized by a photopolymerization initiator.
  • the present invention relates to a method for manufacturing an image display device including a step of forming a polymer layer.
  • This invention (IX) is a manufacturing method of an image display apparatus which has the process of sticking the base which has an image display part, and a translucent protective part using an optical adhesive sheet, Comprising: This optical adhesive sheet is And an optical pressure-sensitive adhesive sheet according to the present invention (VII).
  • the present invention (X) relates to an image display device manufactured by the manufacturing method of the image display device of the present invention (VIII) or the present invention (IX).
  • a polymerizable composition for forming a polymer layer interposed between an image display portion and a translucent protective portion of an image display device comprising: (Component 1) containing a (meth) acryloyl group-containing polymer compound having a number average molecular weight in the range of 1000 to 15000, and (Component 2) a photopolymerization initiator, and obtained by polymerizing the polymerizable composition.
  • a polymerizable composition having a storage elastic modulus of 1 ⁇ 10 3 to 1 ⁇ 10 5 Pa at 25 ° C. and a frequency of 0.1 Hz.
  • the component 5 is a nonionic surfactant having no (meth) acryloyl group, wherein the HLB value of Griffin is 3.0 to 6.0 [7] or [7] 8].
  • a polymerizable composition for producing an optical pressure-sensitive adhesive sheet used as a polymer layer interposed between an image display portion and a translucent protective portion of an image display device, wherein the polymerizable composition A polymerizable composition, wherein the composition is the polymerizable composition according to any one of [1] to [10].
  • a method for manufacturing an image display device comprising: a base having an image display portion; a translucent protective portion; and a polymer layer interposed between the base portion and the protective portion, the method comprising: [7] to [9]
  • the polymerizable composition according to any one of [7] to [9] is interposed between the base portion and the protective portion, and light capable of being photosensitized by a photopolymerization initiator is added to the polymerizable composition.
  • the manufacturing method of the image display apparatus characterized by including the process of irradiating and forming a polymer layer.
  • a method for manufacturing an image display device including a step of attaching a base portion having an image display portion and a translucent protective portion using an optical pressure-sensitive adhesive sheet, the optical pressure-sensitive adhesive sheet according to [12]
  • a method for producing an image display device which is the optical pressure-sensitive adhesive sheet according to claim 1.
  • the polymerizable composition of the present invention can be used to form a polymer layer interposed between an image display portion and a translucent protective portion of an image display device, and is made of a glass display portion or protective portion. It is excellent not only in peeling resistance but also in peeling resistance with a resin-made display part and protective part, and it is possible to impart durable peeling resistance.
  • FIG. 1 is a cross-sectional view showing a main part of an embodiment of a display device according to the present invention.
  • FIG. 2 is a cross-sectional view showing a main part of an embodiment of the display device according to the present invention.
  • FIG. 3 is a cross-sectional view showing a main part of an embodiment of the display device according to the present invention.
  • FIG. 4 is a cross-sectional view showing a main part of an embodiment of the display device according to the present invention.
  • FIG. 5 is a cross-sectional view showing a main part of an embodiment of the display device according to the present invention.
  • FIG. 6 is a cross-sectional view showing a main part of a display device according to the prior art.
  • polyester polyol that can be a raw material of Component 1, which is an essential raw material component of the polymerizable composition of the present invention (I), a polyol (that is, a —COO— bond) that is a raw material of the polyester polyol.
  • this polyol is also defined as being included in the polyester polyol.
  • a polyol which is a raw material component of the polyester polyol to be used is newly added, and the essential component of the polymerizable composition of the present invention (I) When component 1 is produced, the added polyol is included in the polyester polyol even if it has no —COO— bond (carboxylic acid ester bond).
  • a polycarbonate polyol that can be a raw material of Component 1, which is an essential raw material component of the polymerizable composition of the present invention (I)
  • a polyol that is, a carbonate bond
  • this polyol is also included in the polycarbonate polyol.
  • a polyol which is a raw material component of the polycarbonate polyol to be used is newly added, and the essential component of the polymerizable composition of the present invention (I) When component 1 is produced, this added polyol shall be included in the polycarbonate polyol.
  • a polyol that can be a raw material of Component 1, which is an essential raw material component of the polymerizable composition of the present invention (I) when producing a polyether polyol that can be a raw material of Component 1, which is an essential raw material component of the polymerizable composition of the present invention (I), a polyol that is a raw material of the polyether polyol (ie, When a polyol having no ether bond) remains, this polyol is also included in the polyether polyol.
  • a polyol which is a raw material component of the polyether polyol to be used is newly added to the polymerizable composition of the present invention (I).
  • component 1, which is an essential component is produced, the added polyol shall be included in the polyether polyol.
  • the present invention (I) is a polymerizable composition for forming a polymer layer interposed between the image display part of the image display device and the translucent protective part, the polymerizable composition comprising: (Component 1) containing a (meth) acryloyl group-containing polymer compound having a number average molecular weight in the range of 1000 to 15000, and (Component 2) a photopolymerization initiator, and obtained by polymerizing the polymerizable composition.
  • a polymerizable composition having a storage elastic modulus of 1 ⁇ 10 3 to 1 ⁇ 10 5 Pa at 25 ° C. and a frequency of 0.1 Hz.
  • component 1 which is an essential component of the polymerizable composition of the present invention (I) is a (meth) acryloyl group-containing polymer compound having a number average molecular weight in the range of 1000 to 15000.
  • Component 1 is not particularly limited as long as it is a polymer compound having a number average molecular weight in the range of 1000 to 15000 and having a (meth) acryloyl group.
  • the “polymer compound” described in the present specification means a polymer having a molecular weight distribution.
  • the “number average molecular weight” described in the present specification is a number average molecular weight measured in terms of polystyrene by gel permeation chromatography (hereinafter referred to as “GPC”).
  • the number average molecular weight of the polymer compound of component 1 which is an essential component in the present invention (I) is in the range of 1000 to 15000.
  • the range is preferably 1200 to 8000, and more preferably 1500 to 6000.
  • the number average molecular weight is less than 1000, the volume shrinkage during polymerization of the polymer obtained by polymerizing the composition of the present invention (I) may increase, or the polymer may become too hard.
  • the number average molecular weight is 15000 or more, the viscosity may be too high.
  • the (meth) acryloyl group-containing polymer compound having a number average molecular weight in the range of 1000 to 15000 include, for example, polyether (meth) acrylate and polyester (meth) having a number average molecular weight in the range of 1000 to 15000.
  • Acrylate epoxy (meth) acrylate, urethane (meth) acrylate, urethane (meth) acrylamide, polycarbonate (meth) acrylate, and the like.
  • the “(meth) acrylate” in the present specification means at least one group selected from acrylate and methacrylate.
  • “(meth) acrylamide” in the present specification means at least one group selected from acrylamide and methacrylamide.
  • the polyether (meth) acrylate is a (meth) acrylate produced by a dehydration condensation reaction between a polyether polyol and (meth) acrylic acid or a transesterification reaction between the polyether polyol and (meth) acrylic acid ester.
  • (meth) acrylic acid” in the present specification means at least one group selected from acrylic acid and methacrylic acid.
  • the polyester (meth) acrylate is a (meth) acrylate produced by a dehydration condensation reaction between a polyester polyol and (meth) acrylic acid or a transesterification reaction between the polyester polyol and (meth) acrylic acid ester.
  • Epoxy (meth) acrylate has a reaction product of an epoxy group-containing compound having an ether bond, an ester bond or a hydrocarbon chain and (meth) acrylic acid, a polyester polycarboxylic acid, an aliphatic hydrocarbon chain, or an aromatic ring.
  • a reaction product of a polycarboxylic acid such as a polycarboxylic acid or a polycarboxylic acid having a heterocyclic ring and an epoxy group-containing (meth) acryloyl group-containing compound such as glycidyl (meth) acrylate or (meth) acryloyloxybutyl glycidyl ether is there.
  • Urethane (meth) acrylate is a polyaddition reaction using polyol, organic polyisocyanate compound and alcoholic hydroxyl group-containing (meth) acrylate as essential materials, or (meth) acrylate having a polyol and isocyanate group as essential materials.
  • a compound having a urethane bond in the molecule and one or more (meth) acrylate groups by a polyaddition reaction Urethane (meth) acrylamide has a urethane bond in the molecule by a polyaddition reaction using polyol, organic polyisocyanate compound and alcoholic hydroxyl group-containing (meth) acrylamide as essential raw materials, and one or more (meta) ) A compound having an acrylate group.
  • the polycarbonate (meth) acrylate is a (meth) acrylate produced by a condensation reaction between a polycarbonate polyol and (meth) acrylic acid or a transesterification reaction between a polycarbonate polyol and (meth) acrylic acid ester.
  • a (meth) acryloyl group-containing polymer compound having a urethane bond is preferable.
  • urethane (meth) acrylate and urethane (meth) acrylamide are preferable in consideration of the adhesion between the image display unit of the image display device and the translucent protective unit.
  • the “urethane (meth) acrylate” in the present specification is a compound having a urethane bond in the molecule and one or more acrylate groups or methacrylate groups.
  • the “urethane (meth) acrylamide” in the present specification is a compound having a urethane bond in the molecule and having one or more acrylamide groups or methacrylamide groups.
  • urethane (meth) acrylate and urethane (meth) acrylamide are not particularly limited, but can be produced, for example, by the following method.
  • urethane (meth) acrylate is obtained using polyol, organic polyisocyanate compound and alcoholic hydroxyl group-containing (meth) acrylate as essential raw material components.
  • the polyol used in the production of this urethane (meth) acrylate has 2 or more alcoholic hydroxyl groups in one molecule, preferably 2 to 3 alcoholic hydroxyl groups, more preferably 2 Is to have.
  • the preferred structure of the polyol is polyester polyol, polycarbonate polyol, or polyether polyol, more preferably polyester polyol or polycarbonate polyol, and most preferably polyester polyol.
  • the hydroxyl value of this polyol is preferably 10 to 120 mgKOH / g, more preferably 15 to 100 mgKOH / g, and particularly preferably 20 to 80 mgKOH / g.
  • the hydroxyl value of the polyol is less than 10 mgKOH / g, the molecular weight and viscosity of the resulting polyurethane (meth) acrylate are too high, handling properties tend to be poor, and handling tends to be difficult.
  • the hydroxyl value of the polyol is greater than 120 mgKOH / g, the volume shrinkage during polymerization becomes too large, or the cohesive strength of the polymer becomes too high, and the adhesive performance of the polymer is not sufficiently exhibited. There is.
  • the organic polyisocyanate compound is not particularly limited as long as it is an organic compound having two or more isocyanato groups in one molecule.
  • the component 1 which is an essential component of the polymerizable composition of the present invention (I) preferably has a low viscosity in consideration of the degree of freedom of subsequent blending.
  • organic polyisocyanate compounds that meet this purpose include 1,3-bis (isocyanatomethyl) cyclohexane, 1,4-bis (isocyanatomethyl) cyclohexane, 2,4,4-trimethylhexamethylene diisocyanate, 2,2 , 4-trimethylhexanemethylene diisocyanate, 1,6-hexamethylene diisocyanate and norbornane diisocyanate are preferred, more preferably 1,3-bis (isocyanatomethyl) cyclohexane, 2,4,4-trimethylhexamethylene diisocyanate and 2, 2,4-trimethylhexanemethylene diisocyanate, most preferred are 2,4,4-trimethylhexamethylene diisocyanate and 2,2,4-trimethylhexanemethylene diisocyanate It is.
  • the alcoholic hydroxyl group-containing (meth) acrylate is not particularly limited as long as it is a (meth) acrylate having an alcoholic hydroxyl group in one molecule.
  • component 1 which is an essential component of the present invention (I)
  • 2-hydroxyethyl acrylate, 3-hydroxypropyl acrylate and 4-hydroxybutyl acrylate are preferable, and 4-hydroxybutyl acrylate is most preferable.
  • a polyol, an organic polyisocyanate compound, and an alcoholic hydroxyl group-containing (meth) acrylate As a method of reacting a polyol, an organic polyisocyanate compound, and an alcoholic hydroxyl group-containing (meth) acrylate, a polyol, an organic polyisocyanate, in the presence or absence of a known urethanization catalyst such as dibutyltin dilaurate or dioctyltin dilaurate
  • a known urethanization catalyst such as dibutyltin dilaurate or dioctyltin dilaurate
  • the compound can be synthesized by reacting the alcoholic hydroxyl group-containing (meth) acrylate, but the reaction in the presence of a catalyst is preferable in terms of shortening the reaction time.
  • the amount used is polyol, organic polyisocyanate compound, alcoholic hydroxyl group-containing (meth) acrylate.
  • the total amount is preferably 0.001 to 1 part by mass with respect to 100 parts by mass.
  • the order in which the raw materials are charged is not particularly limited.
  • the organic polyisocyanate compound and, if necessary, the urethanization catalyst are charged into the reactor and stirred, and then the temperature in the reactor is set to 40 ° C. to 40 ° C.
  • the temperature in the reactor is set to 40 ° C. to 40 ° C.
  • the temperature in the reactor is 50 ° C. to 160 ° C., preferably 60 ° C. to 140 ° C. React.
  • the temperature in the reactor is 30 ° C. to 120 ° C., preferably 50 ° C.
  • a polymerization inhibitor and a urethanization catalyst are added if necessary, and an alcoholic hydroxyl group-containing (meth) acrylate is added dropwise.
  • the temperature in the reactor is preferably maintained at 30 ° C. to 120 ° C., desirably 50 ° C. to 100 ° C.
  • the temperature in the reactor is maintained at 30 ° C. to 120 ° C., preferably 50 ° C. to 100 ° C., to complete the reaction.
  • an organic polyisocyanate compound, a polymerization inhibitor and / or a urethanization catalyst as necessary are charged into the reactor, and stirred, and then the temperature in the reactor is changed from 30 ° C. to 30 ° C.
  • the alcoholic hydroxyl group-containing (meth) acrylate is added dropwise at 120 ° C., preferably 50 ° C. to 110 ° C.
  • the temperature in the reactor is preferably maintained at 30 ° C. to 120 ° C., desirably 50 ° C. to 110 ° C.
  • the temperature in the reactor is maintained at 30 ° C. to 120 ° C., preferably 50 ° C.
  • reaction product is charged into the reactor containing the polyol while stirring so that the temperature in the reactor can be maintained at 30 ° C. to 120 ° C., preferably 50 ° C. to 100 ° C.
  • the temperature in the reactor is maintained at 30 ° C. to 120 ° C., preferably 50 ° C. to 100 ° C., to complete the reaction.
  • Component 1 which is an essential component of the present invention (I)
  • Component 1 which is an essential component of the present invention (I)
  • only a part of the end of the compound is alcohol. It is desirable that the oligomer be sealed with a compound having one hydroxyl group in the molecule containing a functional hydroxyl group-containing (meth) acrylate.
  • the total number of hydroxyl groups of the polyol used is used. It is necessary to increase the total number of isocyanato groups in the organic polyisocyanate compound. In this case, if the ratio of the total number of hydroxyl groups of the polyol used and the total number of isocyanato groups in the organic polyisocyanate compound is close to 1.0, the average molecular weight of the compound to be produced increases. The average molecular weight decreases as the value decreases.
  • the feed molar ratio of the raw material is not particularly limited, but the ratio of the total number of hydroxyl groups in the polyol used and the number of isocyanate groups in the organic polyisocyanate compound is organic with respect to 1 equivalent of the total number of hydroxyl groups in the polyol.
  • the isocyanate group in the polyisocyanate compound is preferably 1.5 equivalents or more. If the total number of hydroxyl groups in the polyol is less than 1.5 equivalents of the isocyanate group in the organic polyisocyanate compound relative to 1 equivalent, the viscosity may be too high.
  • the polyol used and the alcoholic hydroxyl group-containing (meth) acrylate are used.
  • the total number of hydroxyl groups when a compound having one hydroxyl group in the molecule is added to the total number of isocyanato groups of the organic polyisocyanate compound to be used.
  • the total number of hydroxyl groups and the total number of isocyanato groups in the organic polyisocyanate compound when a compound having one hydroxyl group in the molecule including the polyol and alcoholic hydroxyl group-containing (meth) acrylate is combined.
  • the ratio of the total number of isocyanato groups in the organic polyisocyanate compound is equal to the number of hydroxyl groups when a compound having one hydroxyl group in the molecule including a polyol and an alcoholic hydroxyl group-containing (meth) acrylate is used with respect to 1 equivalent.
  • the total number is preferably 2 equivalents or less. More preferably, it is 1.0 to 1.5 equivalents, and most preferably 1.0 to 1.2 equivalents.
  • the total number of isocyanato groups in the organic polyisocyanate compound is 1 equivalent, and the total number of hydroxyl groups when the compound having one hydroxyl group in the molecule including a polyol and alcoholic hydroxyl group-containing (meth) acrylate is combined is 2
  • the amount is larger than the equivalent amount, the number of molecules having no (meth) acryloyl group increases, and the shape retention of the polymer after polymerization may be deteriorated.
  • the ratio of the total number of hydroxyl groups and the total number of isocyanato groups in the organic polyisocyanate compound when a compound having one hydroxyl group in the molecule including a polyol and an alcoholic hydroxyl group-containing (meth) acrylate is combined is different. Two or more kinds of component 1 may be used in combination in the polymerizable composition.
  • Urethane (meth) acrylamide is an alcoholic hydroxyl group-containing (meth) which is a raw material of the urethane (meth) acrylate produced using a polyol, an organic polyisocyanate compound and an alcoholic hydroxyl group-containing (meth) acrylate as essential raw material components. It can be produced by using alcoholic hydroxyl group-containing (meth) acrylamide instead of acrylate.
  • the production conditions of urethane (meth) acrylamide can be produced under the same conditions as the production conditions of urethane (meth) acrylate.
  • urethane (meth) acrylate is obtained using (meth) acrylate having a polyol and an isocyanato group as essential raw material components.
  • the polyol is as described above.
  • Examples of the (meth) acrylate having an isocyanato group that can be used as the raw material include 2-isocyanatoethyl acrylate and 2-isocyanatoethyl methacrylate.
  • Examples of 2-isocyanatoethyl acrylate include Karenz AOI (registered trademark) manufactured by Showa Denko KK.
  • 2-isocyanatoethyl methacrylate include Karenz MOI (registered trademark) manufactured by Showa Denko KK and the like.
  • a urethane (meth) acrylate obtained by using a polyol and a (meth) acrylate having one isocyanato group in one molecule as an essential raw material component is generally synthesized by the following method. Even if the total amount of hydroxyl groups of the polyol is reacted with the (meth) acrylate having an isocyanato group, only a part of the hydroxyl groups of the polyol are reacted with the (meth) acrylate having an isocyanato group, and some of the hydroxyl groups are converted. It doesn't matter if you leave it.
  • the ratio of the total number of hydroxyl groups of the polyol to the total number of isocyanate groups of the isocyanate group-containing (meth) acrylate used is 1 or less.
  • the isocyanate group-containing (meth) used is determined from the total number of hydroxyl groups of the polyol. It is necessary to charge a small total number of isocyanate groups of acrylate.
  • a polyol, a polymerization inhibitor and, if necessary, a urethanization catalyst and an antioxidant are added, put into the reactor, stirring is started, and the temperature in the reactor is increased.
  • the temperature is raised to 40 ° C to 120 ° C, preferably 50 ° C to 100 ° C.
  • (meth) acrylate having an isocyanato group is dropped.
  • the temperature in the reactor is controlled to 40 ° C to 130 ° C, preferably 50 ° C to 110 ° C.
  • the temperature in the reactor is maintained at 40 ° C. to 120 ° C., preferably 50 ° C. to 100 ° C. while stirring is continued to complete the reaction.
  • Component 1 is a structural unit derived from a diol having 4 to 9 carbon atoms and a component having 4 to 10 carbon atoms.
  • a (meth) acryloyl group-containing polymer compound having a polyester structural unit containing a structural unit derived from dicarboxylic acid is preferred.
  • the “structural unit derived from a diol having 4 to 9 carbon atoms” means a structure in which hydrogen in at least one hydroxyl group of two hydroxyl groups of the diol having 4 to 9 carbon atoms is removed. Means.
  • structural unit derived from a dicarboxylic acid having 4 to 10 carbon atoms means OH in two carboxyl groups (—C ( ⁇ O) OH) of the dicarboxylic acid having 4 to 10 carbon atoms. It means a structure in which a group is removed.
  • diol having 4 to 9 carbon atoms examples include 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, neopentyl glycol, 3-methyl-1,5- Pentanediol, 1,8-octanediol, 1,9-nonanediol, 2-methyl-1,8-octanediol, 2-butyl-2-ethyl-1,3-propanediol, 2,4-diethyl-1 , 5-pentanediol and the like, and these can be used alone or in combination of two or more.
  • 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, neopentyl glycol, and 3-methyl-1,5-pentanediol are more preferable.
  • 1,5-pentanediol, neopentyl glycol, 3-methyl-1,5-pentanediol, and most preferred is 3-methyl-1,5-pentanediol.
  • dicarboxylic acid having 4 to 10 carbon atoms include succinic acid, glutaric acid, methyl succinic acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, terephthalic acid, isophthalic acid, and phthalic acid.
  • glutaric acid methyl succinic acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, 1,1-cyclohexanedicarboxylic acid, 1,3-cyclohexanedicarboxylic acid, 12-cyclohexane- 1,1-dicarboxylic acid, more preferably glutaric acid, methylsuccinic acid, adipic acid, pimelic acid, suberic acid, azelaic acid, and sebacic acid, and most preferably adipic acid.
  • component 2 which is an essential component of the polymerizable composition of the present invention (I) is a photopolymerization initiator.
  • the photopolymerization initiator of component 2 is not particularly limited as long as it is a compound that generates radicals that contribute to the initiation of radical polymerization upon irradiation with light such as near infrared rays, visible rays, and ultraviolet rays.
  • photopolymerization initiator of Component 2 include acetophenone, 2,2-dimethoxy-2-phenylacetophenone, diethoxyacetophenone, 1-hydroxycyclohexyl phenyl ketone, 1,2-hydroxy-2-methyl-1 -Phenylpropan-1-one, ⁇ -hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1- (4-isopropylphenyl) propane- 1-one, 2-hydroxy-2-methyl-1- (4-dodecylphenyl) propan-1-one, and 2-hydroxy-2-methyl-1-[(2-hydroxyethoxy) phenyl] propanone, benzophenone, 2-methylbenzophenone, 3-methylbenzophenone, 4-methyl Benzophenone, 4-methoxybenzophenone, 2-chlorobenzophenone, 4-chlorobenzophenone, 4-bromobenzophenone, 2-carboxybenzone, 2-
  • bisacylphosphine oxides include bis- (2,6-dichlorobenzoyl) phenylphosphine oxide, bis- (2,6-dichlorobenzoyl) -2,5-dimethylphenylphosphine oxide, bis- (2, 6-dichlorobenzoyl) -4-propylphenylphosphine oxide, bis- (2,6-dichlorobenzoyl) -1-naphthylphosphine oxide, bis- (2,6-dimethoxybenzoyl) phenylphosphine oxide, bis- ( 2,6-dimethoxybenzoyl) -2,4,4-trimethylpentylphosphine oxide, bis- (2,6-dimethoxybenzoyl) -2,5-dimethylphenylphosphine oxide, bis- (2,4,6- Trimethylbenzoyl) phenyl phosphite Oxide, (2,5,6-trimethylbenzo
  • a metallocene compound can be used as a photopolymerization initiator.
  • the metallocene compound the transition metal represented by Fe, Ti, V, Cr, Mn, Co, Ni, Mo, Ru, Rh, Lu, Ta, W, Os, Ir, etc. can be used as the metallocene compound,
  • An example is bis ( ⁇ 5-2,4-cyclopentadien-1-yl) -bis [2,6-difluoro-3- (pyrrol-1-yl) phenyl] titanium.
  • photopolymerization initiators can be used alone or in combination of two or more.
  • 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1-hydroxycyclohexyl phenyl ketone, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, 2,4, 6-trimethylbenzoylethoxyphenylphosphine oxide, 2,3,5,6-tetramethylbenzoyldiphenylphosphine oxide particularly preferable examples include 1-hydroxycyclohexyl phenyl ketone, 2,4,6-trimethylbenzoyldiphenylphosphine oxide 2,4,6-trimethylbenzoylethoxyphenylphosphine oxide, most preferably 2,4,6-trimethylbenzoyldiphenylphosphine oxide used alone, 1-hydroxycyclohexyl phenyl ketone and 2,4,6-trimethylbenzoyldiphenylphosphine oxide, 1-hydroxycyclohexyl phenyl ketone
  • 1,4 to 4 may have a function of cutting the ultraviolet region from the viewpoint of protecting the display unit 2 from ultraviolet rays.
  • 2,4,6-trimethylbenzoyldiphenylphosphine oxide, 2,3,5,6-tetramethylbenzoyldiphenylphosphine oxide, 2,4,6-trimethyl which is a photopolymerization initiator that can be sensitized even in the visible light region.
  • Benzoylethoxyphenylphosphine oxide is preferably used, and 2,4,6-trimethylbenzoylethoxyphenylphosphine oxide and 2,4,6-trimethylbenzoyldiphenylphosphine oxide are particularly preferable.
  • the amount of Component 2 used in the present invention (I) is 0.05 to 10.0 parts by weight with respect to 100 parts by weight of the total amount of the polymerizable composition of the present invention (I) excluding Component 2. More preferably, it is 0.1 to 7.0 parts by mass, and particularly preferably 0.2 to 5.0 parts by mass.
  • the amount of component 2 used is less than 0.05 parts by mass relative to 100 parts by mass of component 2 from the total amount of the polymerizable composition of the present invention (I), the polymerization initiator has insufficient polymerization initiation performance. It may become.
  • the polymerizable composition of the present invention the storage modulus at a frequency 0.1Hz is at 25 ° C. of the polymer obtained by polymerizing it was 1 ⁇ 10 3 ⁇ 1 ⁇ 10 5 Pa, 1 ⁇ 10 4 It is preferably ⁇ 1 ⁇ 10 5 Pa.
  • the storage elastic modulus of the polymer at 25 ° C. at a frequency of 0.1 Hz means that a 2.5 mm thick test piece (polymer) is a rheometer manufactured by Auton Pear in an environment of 25 ° C. Is a storage elastic modulus at a frequency of 0.1 Hz measured in vibration mode using MRC301 as a measurement jig and also using a plate PP25 manufactured by Autoon Pear.
  • the storage elastic modulus of the polymer measured under the above conditions is less than 1 ⁇ 10 3 , the polymer may not be able to maintain its shape in a high temperature and high humidity environment or a high temperature environment. Moreover, in the case of 1 ⁇ 10 5 Pa or more, the polymer becomes too hard and sufficient adhesion may not be obtained.
  • the blending amount of the monomer having the alicyclic structure or the aromatic structure among all the raw material monomers constituting Component 1 is 70 mass. % Or less, more preferably 50% by mass or less, and further preferably 5% by mass or more and 40% by mass or less.
  • the storage elastic modulus tends to increase.
  • the number of (meth) acryloyl groups contained in the component 1 compound is preferably 1 to 2 on average per molecule. When the average number exceeds two, the storage elastic modulus increases, and when the average number is less than one, the storage elastic modulus tends to decrease. As described above, the amount of the monomer having an alicyclic structure or an aromatic structure and the number of (meth) acryloyl groups contained in the compound of Component 1 are increased or decreased at a frequency of 0.1 Hz at 25 ° C.
  • the storage elastic modulus can be controlled to be 1 ⁇ 10 3 to 1 ⁇ 10 5 Pa.
  • the present invention (II) is a polymerizable composition for forming a polymer layer interposed between the image display part and the translucent protective part of the image display device, the polymerizable composition comprising: (Component 1) (meth) acryloyl group-containing polymer compound having a number average molecular weight in the range of 1000 to 15000, Polymerization obtained by polymerizing the polymerizable composition, comprising (Component 2) a photopolymerization initiator, and (Component 3) a radical polymerizable unsaturated group-containing compound having at least one of an alcoholic hydroxyl group and an amide group.
  • Component 1 (meth) acryloyl group-containing polymer compound having a number average molecular weight in the range of 1000 to 15000
  • Polymerization obtained by polymerizing the polymerizable composition comprising (Component 2) a photopolymerization initiator, and (Component 3) a radical polymerizable unsaturated group-containing compound having at least one of an alcoholic
  • Component 1 and Component 2 of the present invention (II) are the same as Component 1 and Component 2 of the present invention (I), respectively.
  • the amount of component 2 is the same as the amount of component 2 described above. The reason why the amount used is preferable is also as described above.
  • component 3 which is an essential component of the polymerizable composition of the present invention (II) is a radical polymerizable unsaturated group-containing compound having at least one of an alcoholic hydroxyl group and an amide group.
  • a (meth) acryloyl group-containing polymer compound having at least one of an alcoholic hydroxyl group and an amide group and having a number average molecular weight in the range of 1000 to 15000 is not included in Component 3. Define.
  • a (meth) acryloyl group-containing polymer compound having at least one of an alcoholic hydroxyl group and an amide group and having a number average molecular weight in the range of 1000 to 15000 is not included in Component 3, and the present invention It is included in Component 1 which is an essential component of the polymerizable composition.
  • the “radical polymerizable unsaturated group” means a carbon-carbon double bond capable of addition polymerization by a radical generated by a radical polymerization initiator or the like.
  • radical polymerizable unsaturated group-containing compound having an amide group as Component 3 include, for example, N, N-dimethylacrylamide, N, N-diethylacrylamide, N-acryloylmorpholine, N-isopropylacrylamide, N- tert-butylacrylamide, N-methoxymethylacrylamide, N-ethoxymethylacrylamide, Nn-butoxymethylacrylamide, N-isobutoxymethylacrylamide, N, N-dimethylmethacrylamide, N, N-diethylmethacrylamide, N- Methacryloylmorpholine, N-isopropylmethacrylamide, N-tert-butylmethacrylamide, N-methoxymethylmethacrylamide, N-ethoxymethylmethacrylamide, Nn-butoxymethylmethacrylate And N-isobutoxymethylmethacrylamide, N-vinylpyrrolidone, N-vinylcaprolactam, N-vinylformamide
  • N, N-diethylacrylamide, N-acryloylmorpholine, N-tert-butylacrylamide, N-tert-butylacrylamide, N-ethoxymethylacrylamide, Nn-butoxymethylacrylamide, N -Isobutoxymethylacrylamide and N-vinylpyrrolidone more preferably N, N-diethylacrylamide, N-acryloylmorpholine, N-ethoxymethylacrylamide, Nn-butoxymethylacrylamide, N-isobutoxymethylacrylamide Most preferred is N-acryloylmorpholine.
  • radical polymerizable unsaturated group-containing compound having an alcoholic hydroxyl group as component 3 include, for example, 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, 3-hydroxypropyl acrylate, 2-hydroxybutyl acrylate.
  • 2-hydroxybutyl acrylate, 4-hydroxybutyl acrylate, 2-hydroxypropyl methacrylate, 3-hydroxypropyl methacrylate and 2-hydroxybutyl methacrylate are preferable, and 4-hydroxybutyl acrylate is more preferable.
  • the amount of component 3 used in the present invention (II) is preferably 1 to 30% by mass, more preferably 2 to 20% by mass, particularly based on the total amount of component 1 and component 3 combined. Preferably, it is 3 to 10% by mass.
  • the amount of component 3 used in the present invention (II) is less than 1% by mass relative to the total amount of component 1 and component 3, the polymer of the present invention (V) described later and the optical pressure-sensitive adhesive sheet May whiten in a hot and humid environment.
  • the usage-amount of the component 3 in this invention (II) is more than 30 mass% with respect to the total amount which combined the component 1 and the component 3, at the time of superposition
  • the amount of component 1 used in the present invention (II) is preferably 70 to 99% by mass, more preferably 80 to 98% by mass, based on the total amount of component 1 and component 3 combined. Particularly preferred is 90 to 97% by mass.
  • the usage-amount of the component 3 in this invention (II) is less than 70 mass% with respect to the total amount which combined the component 1 and the component 3, the volume shrinkage at the time of superposition
  • the usage-amount of the component 1 in this invention (II) is 99 mass% or more with respect to the total amount which combined the component 1 and the component 3, the viscosity of polymeric composition may become high too much. is there.
  • the present invention (III) is a polymerizable composition for forming a polymer layer interposed between the image display part of the image display device and the translucent protective part, the polymerizable composition comprising: (Component 1) (meth) acryloyl group-containing polymer compound having a number average molecular weight in the range of 1000 to 15000, (Component 2) Photopolymerization initiator, (Component 3) a radical polymerizable unsaturated group-containing compound having at least one of an alcoholic hydroxyl group and an amide group, and (Component 4) no alcoholic hydroxyl group or amide group, and a viscosity of 25 ° C.
  • a polymer obtained by polymerizing the polymerizable composition containing a (meth) acryloyl group-containing compound that is 500 mPa ⁇ s or less has a storage elastic modulus at 25 ° C. and a frequency of 0.1 Hz of 1 ⁇ 10 3 to The polymerizable composition is 1 ⁇ 10 5 Pa.
  • Component 1 and Component 2 of the present invention (III) are the same as Component 1 and Component 2 of the present invention (I), respectively, and Component 3 of the present invention (III) is a component of the present invention (II). It is the same as 3.
  • the amount of component 2 is the same as the amount of component 2 described above. The reason why the amount used is preferable is also as described above.
  • Component 4 is a (meth) acryloyl group-containing compound which does not have any group of alcoholic hydroxyl group and amide group and has a viscosity of 500 mPa ⁇ s or less at 25 ° C.
  • the group-containing polymer compound is defined as not included in Component 4.
  • the group-containing polymer compound is not included in Component 4, but is included in Component 1 which is an essential component of the polymerizable composition of the present invention.
  • component 4 include, for example, cyclohexyl acrylate, isobornyl acrylate, dicyclopentenyl acrylate, dicyclopentenyloxyethyl acrylate, dicyclopentanyl acrylate, dicyclopentanyl ethyl acrylate, 4-tert-butylcyclohexyl acrylate.
  • the amount of component 4 used in the present invention (III) is preferably 3 to 40% by mass based on the total amount of component 1, component 3 and component 4 as essential components of the present invention (III).
  • the amount is preferably 5 to 35% by mass, particularly preferably 7 to 30% by mass.
  • component 4 used in the present invention (III) is more than 40% by mass with respect to the total amount of component 1, component 3 and component 4 which are essential components of the present invention (III), There is a possibility that the volumetric shrinkage during polymerization of the polymerizable composition of the invention (III) is increased.
  • the amount of component 3 used in the present invention (III) is the same as the preferred amount used for component 3 in the present invention (II) with respect to the total amount of components 1, 3 and 4 combined.
  • the reason why the amount used is preferable is also as described above.
  • the amount of component 1 used in the present invention (III) is preferably 50 to 96% by mass, more preferably 55 to 93% by mass, based on the total amount of component 1, component 3 and component 4 combined. %, Particularly preferably 60 to 90% by mass. The reason why the above range is preferable is the same as in the case of the present invention (II).
  • the present invention (IV) is a polymerizable composition for forming a polymer layer interposed between the image display part of the image display device and the translucent protective part, the polymerizable composition comprising: (Component 1) (meth) acryloyl group-containing polymer compound having a number average molecular weight in the range of 1000 to 15000, (Component 2) Photopolymerization initiator, (Component 3) Radical polymerizable unsaturated group-containing compound having at least one of an alcoholic hydroxyl group and an amide group, (Component 4) a (meth) acryloyl group-containing compound which does not have any group of an alcoholic hydroxyl group and an amide group and has a viscosity of 500 mPa ⁇ s or less at 25 ° C.
  • Nonionic surfactant having no (meth) acryloyl group and (Component 6) No (meth) acryloyl group in the molecule, a function for suppressing radical polymerization, a function for inhibiting radical polymerization, light Liquid or solid at 25 ° C., which has neither a polymerization initiation function nor a surface-active function, and is composed of carbon atoms and hydrogen atoms, or is composed of carbon atoms, hydrogen atoms and oxygen atoms
  • the storage modulus of the polymer obtained by polymerizing the polymerizable composition at 25 ° C. and a frequency of 0.1 Hz is 1 ⁇ 10 3 to 1 ⁇ 10 5 Pa.
  • the present invention relates to a polymerizable composition.
  • Component 1 and Component 2 of the present invention (IV) are respectively the same as Component 1 and Component 2 of the present invention (I), and Component 3 of the present invention (IV) is a component of the present invention (II). 3, component 4 of the present invention (IV) is the same as component 4 of the present invention (III).
  • the amount of component 2 is the same as the amount of component 2 described above. The reason why the blending amount is preferable is also as described above.
  • component 5 which is an essential component of the polymerizable composition of the present invention (IV) will be described.
  • Component 5 is a nonionic surfactant that does not have a (meth) acryloyl group.
  • surfactant in this specification is a generic name for substances having a portion that is familiar with water (hydrophilic group) and a portion that is familiar with oil (lipophilic group / hydrophobic group). And a vesicle, a lamellar structure, and the like, thereby having a property capable of uniformly mixing a polar substance and a nonpolar substance.
  • Griffin's HLB Hydrophilicity-Lipophile Balance
  • HLB value of Griffin is 3.0 to 9.0, more preferably 3. It is 0 to 7.5, and particularly preferably 3.0 to 6.0.
  • component 6 that is an essential component of the polymerizable composition of the present invention (IV) will be described.
  • Component 6 has no (meth) acryloyl group in the molecule, does not have any function of suppressing radical polymerization, function of inhibiting radical polymerization, photopolymerization initiating function, or surface-active function, and carbon atom And a hydrogen atom or a compound composed of a carbon atom, a hydrogen atom and an oxygen atom, which is liquid or solid at 25 ° C.
  • Component 6 is preferably a compound composed of only carbon atoms and hydrogen atoms, or a compound composed of only carbon atoms, hydrogen atoms and oxygen atoms and having no ethylenic double bond.
  • an image display device is manufactured using a manufacturing method including a step of forming a polymer layer by interposing a polymerizable composition between a base portion having an image display portion and a translucent protective portion and polymerizing the polymerizable composition.
  • the polymerizable composition used in this step preferably contains component 6 for the purpose of keeping the volume shrinkage during polymerization low. In addition to suppressing the volume shrinkage during polymerization, it may be used for the purpose of increasing the adhesion of the polymer to an adherend such as glass or acrylic resin.
  • the component 6 a compound that is liquid at 25 ° C. or a compound that is solid at 25 ° C. can be used.
  • Examples of compounds used as component 6 that are liquid at 25 ° C. include poly ( ⁇ -olefin) liquid, ethylene-propylene copolymer liquid, ethylene- ⁇ -olefin copolymer liquid, and propylene- ⁇ -olefin.
  • the poly ( ⁇ -olefin) liquid is a liquid produced by polymerization of ⁇ -olefin, and the ⁇ -olefin is a hydrocarbon compound having one carbon-carbon double bond at the molecular end.
  • the ethylene- ⁇ -olefin copolymer liquid is a liquid polymer produced by copolymerizing ethylene and ⁇ -olefin.
  • An ⁇ -olefin is a hydrocarbon compound having one carbon-carbon double bond at the molecular end, such as 1-butene, 1-pentene, 1-hexene, 1-octene, 1-decene, 1-dodecene, Examples thereof include 1-tetradecene, 1-hexadecene, 1-octadecene and the like.
  • the propylene- ⁇ -olefin copolymer liquid material is a liquid polymer produced by copolymerizing propylene and ⁇ -olefin.
  • An ⁇ -olefin is a hydrocarbon compound having one carbon-carbon double bond at the molecular end, such as 1-butene, 1-pentene, 1-hexene, 1-octene, 1-decene, 1-dodecene, Examples thereof include 1-tetradecene, 1-hexadecene, 1-octadecene and the like.
  • Liquid polybutene is a liquid polymer containing isobutene or n-butene as a (co) polymerization component, such as homopolymerization of isobutene, homopolymerization of n-butene, copolymerization of isobutene and n-butene. It is a compound having a carbon-carbon unsaturated bond.
  • Examples of commercially available liquid polybutene include Nisseki Polybutene LV-7, LV-50, LV-100, HV-15, HV-35, HV-50, HV-100, manufactured by JX Nippon Mining & Energy Corporation. And HV-300.
  • the liquid hydrogenated polybutene is a liquid material having a side chain obtained by hydrogenating the liquid polybutene.
  • palm reel 4 palm reel 6, palm reel 18, palm reel 24 manufactured by NOF Corporation.
  • palm reel EX palm reel EX.
  • Liquid polybutadiene is a butadiene polymer that is liquid at room temperature.
  • POLYVEST110, POLYVEST130 manufactured by Evonik Degussa NISSO-PB B-1000, NISSO-PB B-2000, NISSO-PB B- manufactured by Nippon Soda Co., Ltd. 3000 etc. can be mentioned.
  • the liquid hydrogenated polyptadiene is a liquid material obtained at a normal temperature obtained by reductive hydrogenation of a butadiene polymer.
  • Examples thereof include NISSO-PB BI-2000 and NISSO-PB B-3000 manufactured by Nippon Soda Co., Ltd. Can do.
  • Liquid polyisoprene is a liquid isoprene polymer at room temperature, and examples thereof include Kuraray LIR-30 manufactured by Kuraray Co., Ltd.
  • Liquid hydrogenated polyisoprene is a compound that is liquid at room temperature obtained by reductive hydrogenation of an isoprene polymer, and examples thereof include LIR-200 manufactured by Kuraray Co., Ltd.
  • the liquid polybutadiene polyol is a polymer that is liquid at room temperature and has two or more hydroxyl groups at the molecular terminals and has a polybutadiene structural unit.
  • Examples thereof include G-2000, NISSO-PB G-3000, and Poly bd manufactured by Idemitsu Kosan Co., Ltd.
  • the liquid hydrogenated polybutadiene polyol is a liquid polyol having a structure obtained by reductive hydrogenation of polybutadiene polyol or polybutadiene polycarboxylic acid.
  • NISSO-PB GI-3000 manufactured by Nippon Soda Co., Ltd.
  • the liquid polyisoprene polyol is a polymer that is liquid at room temperature and has two or more hydroxyl groups at the molecular ends and a polyisoprene structural unit, and examples thereof include poly ip manufactured by Idemitsu Kosan Co., Ltd. .
  • the liquid hydrogenated polyisoprene polyol is a liquid polyol having a structure obtained by reductive hydrogenation of polyisoprene polyol or polyisoprene polycarboxylic acid, and examples thereof include Epole manufactured by Idemitsu Kosan Co., Ltd.
  • polyether polyol examples include polypropylene glycol, polytetramethylene glycol, and propylene oxide-tetrahydrofuran copolymer.
  • polyester polyol examples include a polycondensate of a polyol and a polycarboxylic acid, a transesterification product of an ester of a polyol and a polycarboxylic acid, a ring-opening polymer of a cyclic ester into a polyol, and the like.
  • polycarbonate polyol examples include a polycondensate of polyol and phosgene, or a transesterification product of a polyol with an organic carbonate such as dimethyl carbonate, diethyl carbonate, or ethylene carbonate.
  • Polyols used as raw materials for polycarbonate polyols include 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, neopentyl glycol, 3-methyl-1,5-pentanediol, 1,8 -Octanediol, 1,9-nonanediol, 2-methyl-1,8-octanediol, 2-butyl-2-ethyl-1,3-propanediol, 2,4-diethyl-1,5-pentanediol, Examples thereof include trimethylolethane and trimethylolpropane. These can be used alone or in combination of two or more.
  • 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, neopentyl glycol, and 3-methyl-1,5-pentanediol are more preferable.
  • examples thereof include 1,5-pentanediol, neopentyl glycol, 3-methyl-1,5-pentanediol and the like, and most preferred is 3-methyl-1,5-pentanediol.
  • a compound that is solid at 25 ° C. can be used as component 6.
  • the compound used as component 6 that is solid at 25 ° C. is preferably a compound having no carbon-carbon unsaturated bond in the molecule.
  • examples of such compounds include a solid epoxy resin at 25 ° C., a polyester resin solid at 25 ° C., a polyol resin solid at 25 ° C., a hydrogenated petroleum resin solid at 25 ° C., and a terpene hydrogenated resin.
  • Mention may be made of tackifiers such as resins and hydrogenated rosin esters. Among these, preferred are tackifiers such as hydrogenated petroleum resins, terpene hydrogenated resins, and hydrogenated rosin esters.
  • Hydrogenated petroleum resin is a resin obtained by hydrogen reduction of petroleum-based resin.
  • Examples of petroleum resins that are raw materials for hydrogenated petroleum resins include aliphatic petroleum resins, aromatic petroleum resins, aliphatic-aromatic copolymer petroleum resins, alicyclic petroleum resins, dicyclopentadiene resins, and the like.
  • Modified products such as hydrogenated products of The synthetic petroleum resin may be C5 or C9.
  • the terpene-based hydrogenated resin is a resin obtained by reductive hydrogenation of a terpene-based resin.
  • Terpenic resins that are raw materials for terpene hydrogenated resins include ⁇ -pinene resins, ⁇ -pinene resins, ⁇ -limonene resins, ⁇ -limonene resins, pinene-limonene copolymer resins, and pinene-limonene-styrene copolymer resins.
  • the hydrogenated rosin ester is a resin obtained by hydrogenating a rosin ester obtained by esterifying a hydrogenated rosin obtained by hydrogenating a rosin resin or esterifying a rosin.
  • the rosin resin tackifier include modified rosins such as gum rosin, tall oil rosin, wood rosin, disproportionated rosin, polymerized rosin and maleated rosin.
  • a compound in which some alcoholic hydroxyl groups of polyhydric alcohol are esterified with hydrogenated rosin and a compound in which all alcoholic hydroxyl groups of polyhydric alcohol are esterified with hydrogenated rosin Both are defined as being included in the hydrogenated rosin ester.
  • hydrogenated rosin esters and terpene-phenol resins are more preferable, hydrogenated rosin esters are more preferable, and triols such as glycerin, trimethylolpropane, and trimethylolethane are particularly preferable.
  • hydrogenated rosin ester which is esterification of tetraol such as pentaerythritol and hydrogenated rosin, or triol such as glycerin, trimethylolpropane and trimethylolethane or tetraol and rosin ester such as pentaerythritol (rosin ester) ) Hydrogenated rosin ester obtained by hydrogen reduction.
  • the compound of Component 6 includes a compound that is liquid at 25 ° C. and 25 ° C.
  • a solid compound can be used in combination. More preferably, it is a combined use of polyether polyol, polyester polyol or polycarbonate polyol which is liquid at 25 ° C., and a tackifier which is solid at 25 ° C., and particularly preferably polyester polyol or polycarbonate polyol, It is to use together with hydrogenated rosin ester.
  • a preferred combination ratio is 25 by mass ratio with respect to 90 equivalents of the compound that is liquid at 25 ° C. 10 equivalents of the compound that is solid at 25 ° C. to 90 equivalents of the compound that is solid at 25 ° C., more preferably 10 equivalents of the compound that is liquid at 25 ° C. 15 equivalents of the compound that is solid at 25 ° C. with respect to the equivalent amount to 85 equivalents of the compound that is solid at 25 ° C. with respect to 15 equivalents of the compound that is liquid at 25 ° C.
  • the amount of component 5 used in the present invention (IV) is 3 to 40% by mass based on the total amount of component 1, component 3, component 4, component 5 and component 6 as essential components of the present invention (IV). It is preferably 4 to 35% by mass, more preferably 5 to 30% by mass.
  • the amount of component 5 used is less than 3% by mass based on the total amount of component 1, component 3, component 4, component 5 and component 6 as essential components of the present invention (IV)
  • the transparency of the coating film of the polymer obtained by polymerizing the polymerizable composition of IV) may be lost.
  • the usage-amount of the component 5 is contained exceeding 40 mass% with respect to the total amount which combined the component 1, the component 3, the component 4, the component 5, and the component 6 which are essential components of this invention (IV).
  • the film strength of the polymer obtained by polymerizing the polymerizable composition of the present invention (IV) may be too low.
  • the amount of component 6 used in the present invention (IV) is 15 to 85% by mass based on the total amount of component 1, component 3, component 4, component 5 and component 6 as essential components of the present invention (IV). It is preferably 30 to 70% by mass, more preferably 40 to 60% by mass.
  • the usage-amount of the component 6 in this invention (IV) is less than 15 mass% with respect to the total amount which combined the component 1, the component 3, the component 4, the component 5, and the component 6 which are essential components of this invention (IV). In some cases, the effect of adding the component 6 (that is, the effect of reducing the volumetric shrinkage during polymerization) cannot be obtained.
  • the usage-amount of the component 6 in this invention (IV) is 85 mass% with respect to the total amount which combined the component 1, the component 3, the component 4, the component 5, and the component 6 which are essential components of this invention (IV).
  • the coating strength of the polymer obtained by polymerizing the polymerizable composition of the present invention (IV) may become too low.
  • the amount of component 1 used in the present invention (IV) is preferably 10 to 40% by mass, more preferably based on the total amount of component 1, component 3, component 4, component 5 and component 6 combined. Is from 13 to 37% by mass, particularly preferably from 15 to 35% by mass.
  • the amount of component 1 used in the present invention (IV) is less than 10% by mass with respect to the total amount of component 1, component 3, component 4, component 5 and component 6, the image display unit of the image display device There is a possibility that the adhesion strength of the polymer obtained by polymerizing the polymerizable composition of the present invention (IV) to the above material or the material of the translucent protective part is lowered.
  • the usage-amount of the component 1 in this invention (IV) is 40 mass% or more with respect to the total amount which combined the component 1, the component 3, the component 4, the component 5, and the component 6, In some cases, the viscosity becomes too high, or the storage elastic modulus becomes too high.
  • the amount of Component 3 used in the present invention (IV) is preferably 1 to 15% by mass, more preferably, based on the total amount of Component 1, Component 3, Component 4, Component 5 and Component 6. It is 2 to 10% by mass, and particularly preferably 2 to 8% by mass. The reason is the same as in the case of the present invention (II) or the present invention (III).
  • the amount of Component 4 used in the present invention (IV) is 3 to 20% by mass based on the total amount of Component 1, Component 3, Component 4, Component 5 and Component 6 as essential components of the present invention (IV). It is preferably 4 to 19% by mass, more preferably 5 to 18% by mass. The reason is the same as in the case of the present invention (III).
  • the volume shrinkage ratio at the time of polymerization of the polymerizable composition of the present invention (IV). Is preferably 3.5% or less, more preferably 2.7% or less, and most preferably 2.3% or less.
  • the volumetric shrinkage during polymerization of the polymerizable composition of the present invention (IV) is greater than 3.5%, the internal stress accumulated in the polymer increases when the polymerizable composition is polymerized. In some cases, the interface between the polymer layer 5a or 5b and the display unit 2, the protection unit 3 or the touch panel 7 in contact with the polymer layer 5a or 5b may be distorted.
  • the viscosity of the polymerizable composition of the present invention (I) to the present invention (IV) at 25 ° C. is not particularly limited, but is preferably 10000 mPa ⁇ s or less, more preferably 7000 mPa ⁇ s or less in terms of handling. Especially preferably, it is 5000 mPa ⁇ s or less.
  • the viscosity described in this specification is a cone / plate viscometer (manufactured by Brookfield, model: DV-II + Pro, spindle model number: CPE-42) for a composition having a viscosity of 10000 mPa ⁇ s or less at 25 ° C. ) Using a temperature of 25.0 ° C.
  • the viscosity of the polymerizable composition of the present invention (I) to the present invention (IV) is set to 1000 mPa ⁇ s or less at 25 ° C.
  • the polymerizable composition of the present invention (I) to the present invention (IV) is used in a dispenser.
  • the spread of the liquid becomes easy after application, and as a result, it becomes easy to spread the composition with a uniform thickness at the required location, and further, the entrainment of bubbles is suppressed. It becomes easy to be done.
  • a polymerization inhibitor, an inhibitor and an antioxidant can be preferably added.
  • the polymerization inhibitor and the polymerization inhibitor are not particularly limited as long as they have a polymerization inhibition ability or a function to inhibit polymerization.
  • hydroquinone p-methoxyphenol, p-benzoquinone, naphthoquinone, phenanthraquinone, 2,5-diacetoxy-p-benzoquinone, 2,5-dicaproxy-p-benzoquinone, 2,5-acyloxy-p- Benzoquinone, pt-butylcatechol, 2,5-di-t-butylhydroquinone, p-tert-butylcatechol, mono-t-butylhydroquinone, 2,5-di-t-amylhydroquinone, di-t-butyl -Paracresol hydroquinone monomethyl ether and phenothiazine are preferably used.
  • the polymerization inhibitor can be adjusted so as to be added in an amount of 0.01 to 5% by mass based on the total amount of the polymerizable composition of the present invention (I) to the present invention (IV).
  • the amount of the polymerization inhibitor is a value obtained by adding the polymerization inhibitor contained in the component 1, component 2, component 3, component 4 and component 6 when the polymerization inhibitor is contained in advance. It is. That is, generally, a polymerization inhibitor is previously contained in component 1, component 2, component 3, component 4 and component 6, but the total amount of this polymerization inhibitor and the newly added polymerization inhibitor is This means that the added amount is 0.01 to 5% by mass based on the total amount of the polymerizable composition of the present invention (I) to the present invention (IV).
  • the polymerization inhibitor When the polymerization inhibitor is less than 0.01% by mass with respect to the total amount of the polymerizable composition of the present invention (I) to the present invention (IV), the storage stability of the compound is reduced due to insufficient polymerization inhibiting ability. There may be a shortage.
  • the amount of the polymerization inhibitor is more than 5% by mass relative to the total amount of the polymerizable composition of the present invention (I) to the present invention (IV)
  • the color becomes darker due to coloring during heat-resistant storage, The polymerization rate at the time of polymerization may decrease.
  • an antioxidant can be added to the polymerizable compositions of the present invention (I) to the present invention (IV) and is preferable.
  • the antioxidant is not particularly limited.
  • pentaerythritol tetrakis [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate]
  • octadecyl-3- (3,5 -Di-tert-butyl-4-hydroxyphenyl) propionate
  • thiodiethylenebis [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate] 3,5-di-tert-butyl-4 7-C9 alkyl ester of hydroxybenzenepropanoic acid, 4,6-bis (octylthiomethyl) -o-cresol, 3,9-bis [2- [3- (3-tert-butyl-4- Hydroxy-5-methylphenyl) propionyloxy] -1,1-dimethyl
  • Octadecyl-3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate triethylene glycol bis (3-tert-butyl-4-hydroxy-5-methylphenyl) propionate, n-octadecyl 3- (4'-hydroxy-3 ', 5'-di-tert-butylphenyl) propionate, more preferably pentaerythritol tetrakis [3- (3,5-di-tert-butyl-4-hydroxyphenyl) Propionate], triethylene glycol Bis (3-tert-butyl-4-hydroxy-5-methylphenyl) propionate, n-octadecyl 3- (4'-hydroxy-3 ', 5'-di-tert-butylphenyl) propionate, particularly preferred Is triethylene glycol bis (3-tert-butyl-4-hydroxy-5-methylphenyl) propionate, n-octadecyl
  • the antioxidant can be adjusted so as to be added in an amount of 0.01 to 5% by mass relative to the total amount of the polymerizable composition of the present invention (I) to the present invention (IV).
  • the amount of the antioxidant is a value in consideration of the antioxidant contained in the other components such as the component 6 in advance. That is, when an antioxidant is preliminarily contained in the component 6 or the like, the total amount of this antioxidant and the newly added antioxidant is the present invention (I) to the present invention (IV ) To 0.01 to 5% by mass based on the total amount of the polymerizable composition.
  • the antioxidant When the antioxidant is less than 0.01% by mass relative to the total amount of the polymerizable composition of the present invention (I) to the present invention (IV), the addition effect (that is, the antioxidant effect) may not be exhibited. is there. Further, when the amount of the polymerization inhibitor is more than 5% by mass based on the total amount of the polymerizable composition of the present invention (I) to the present invention (IV), the polymer of the present invention (V) described later or the later described From the optical pressure-sensitive adhesive sheet, an antioxidant may precipitate or bleed.
  • the present invention (V) is a polymer obtained by polymerizing the polymerizable composition of the present invention (I) to the present invention (IV).
  • the polymer of the present invention (V) is a low pressure mercury lamp, medium pressure mercury lamp, high pressure mercury lamp, ultra high pressure mercury lamp, xenon lamp, metal halide lamp, electrodeless lamp, LED, etc. It is obtained by polymerizing the polymerizable composition by irradiation through a glass or plastic substrate.
  • the polymer of this invention (V) is a polymer used as a polymer layer interposed between the image display part of an image display apparatus, and a translucent protection part.
  • This polymer must have a storage modulus of 1 ⁇ 10 3 to 1 ⁇ 10 5 Pa at 25 ° C. and a frequency of 0.1 Hz.
  • the “storage modulus of the polymer at 25 ° C. and a frequency of 0.1 Hz” is as defined above.
  • a more preferable value of the storage elastic modulus is 1 ⁇ 10 4 to 1 ⁇ 10 5 Pa.
  • the storage elastic modulus of the polymer is less than 1 ⁇ 10 3 , the polymer cannot maintain its shape in a high-temperature and high-humidity environment or in a high-temperature environment, and sufficient adhesion may not be obtained. . Moreover, in the case of 1 ⁇ 10 5 Pa or more, the polymer becomes too hard and sufficient adhesion may not be obtained.
  • the polymer of the present invention (V) is applied to the polymer (layer) 5b filled between the image display unit 2 and the translucent protection unit 3 in the In-Cell type capacitive touch panel display shown.
  • the dielectric constant of the polymer of the present invention (V) is high.
  • the dielectric constant of the polymer measured at 23 ° C., frequency 1 MHz, and applied voltage 100 mV means that a 2 mm-thick test piece (polymer) is manufactured by Agilent Technologies in an environment of 23 ° C. 4294A Precision Impedance Analyzer 40Hz-110MHz is used as the impedance analyzer, and 16451B dielectric test fixture manufactured by Agilent Technologies is used as the test fixture, and the frequency is 1MHz and the applied voltage is 100mV.
  • a more preferable dielectric constant value is a dielectric constant measured under the above conditions of 5.5 or more, more preferably 6.0 or more, and particularly preferably 6.1 or more.
  • the dielectric constant of the polymer measured under the above conditions is less than 5.0, the sensitivity of the capacitive touch panel may decrease.
  • the upper limit of the dielectric constant is not particularly limited. However, when the dielectric constant is increased, the polarity increases, and as a result, the water resistance tends to decrease. In order to prevent the water resistance from being extremely impaired, the dielectric constant is 40 Or less, more preferably 20 or less, and most preferably 10 or less.
  • a urethane using a polyol and (meth) acrylate having one isocyanato group in one molecule as an essential raw material component
  • (meth) acrylate is obtained, a (meth) acryloyl group-containing polymer having a structural unit derived from a diol having 4 to 9 carbon atoms and a structural unit derived from a dicarboxylic acid having 4 to 10 carbon atoms It is preferable to use molecular compounds.
  • the “structural unit derived from a diol having 4 to 9 carbon atoms” means a structure in which hydrogen in at least one of the two hydroxyl groups of the diol having 4 to 9 carbon atoms is removed. Means. Further, in this specification, “structural unit derived from a dicarboxylic acid having 4 to 10 carbon atoms” means OH in two carboxyl groups (—C ( ⁇ O) OH) of the dicarboxylic acid having 4 to 10 carbon atoms. It means a structure in which a group is removed. When only a diol having 3 or less carbon atoms is used, the hydrophilicity of the polymer obtained by polymerizing component 1 may become too high and the water resistance may be weakened.
  • the dielectric constant of a polymer obtained by polymerizing component 1 may decrease.
  • polymerizing the component 1 of the said polymerization composition may become high too much, and may become weak in water resistance.
  • polymerizing the component 1 of the said polymerization composition may fall.
  • the diol having 4 to 9 carbon atoms are as described above.
  • Specific examples of the dicarboxylic acid having 4 to 10 carbon atoms are as described above.
  • Component 4 is methoxyethyl (meth) acrylate, diethylene glycol monoethyl ether (meth) acrylate, phenoxyethyl (meth) acrylate, 3-methyl-3-oxetanylmethyl (meth) acrylate, 1,4-dioxaspiro [4.5] dec-2-ylmethyl (meth) acrylate, (2-methyl-2-ethyl-1,3-dioxolane-4- (Il) (meth) acryloyl group having a cyclic ester such as (meth) acryloyl group-containing compound having an ether bond in the molecule such as methyl (meth) acrylate, ⁇ -methacryloxy- ⁇ -butyrolactone, ⁇ -acryloxy- ⁇ -butyrolactone
  • it is a contained compound, more preferred Examples include methoxyeth
  • the refractive index of the polymer of the present invention (V) at 25 ° C. is preferably 1.45 to 1.55, and more preferably 1.48 to 1.52.
  • the refractive index at 25 ° C. is less than 1.45 or larger than 1.55, it is too low compared to the refractive index of the optical glass or the like that is the material of the protective part, so the interface between the display part and the protective part.
  • the difference in the refractive index of the image becomes slightly larger, and the scattering and attenuation of the image light from the display portion become slightly larger.
  • the volume shrinkage during polymerization of the polymer of the present invention is preferably 3.5% or less, more preferably 2.7% or less, and most preferably 2.3% or less. become.
  • the internal stress accumulated in the polymer layer when the polymerizable composition is polymerized can be reduced, and the interface between the polymer layer 5a and the touch panel 7 or the protective part 3, or the polymer layer 5b and the touch panel. 7.
  • the polymerizable composition is interposed between the touch panel 7 and the protection unit 3, between the touch panel 7 and the display unit 2, or between the display unit 2 and the protection unit 3, and the polymerizable composition is polymerized.
  • the scattering of light generated at the interface between the polymer layer 5 and the display unit 2, the protection unit 3, and the touch panel 7 can be reduced, and the brightness of the display image can be increased and the visibility can be improved. it can.
  • the volume shrinkage during polymerization is larger than 3.5%, the internal stress accumulated in the polymer when the polymerizable composition is polymerized becomes too large, and the polymer layer 5a or 5b and those May be distorted at the interface with the display unit 2, the protection unit 3, or the touch panel 7 in contact with the touch panel.
  • the component 1 is added to the total amount of the polymerizable composition of the present invention (I) to the present invention (IV).
  • the component 1 is contained in an amount of 10 to 40% by mass based on the total amount of the polymerizable composition of the present invention (I) to the present invention (IV), and the total amount of the component 3 and the component 4 is It is preferable to contain 1 to 25% by mass with respect to the total amount of component 1, component 3, component 4, component 5, and component 6, which are essential components of the present invention (IV).
  • the polymerized product of the present invention (V) was interposed between two glasses at a thickness of 200 ⁇ m to form a laminate, and the polymerization was performed when the laminate was peeled in a direction perpendicular to the glass at 500 mm / min It is desirable that the breaking strength between the object and the glass is 20 N / cm 2 or more.
  • the “laminate” described in the present specification includes a polymerizable composition interposed between two optical glasses having a thickness of 0.7 mm (manufactured by Corning, trade name: Eagle XG (registered trademark)), By irradiating light that can be sensitized by the photopolymerization initiator through the optical glass, using a low pressure mercury lamp, medium pressure mercury lamp, high pressure mercury lamp, ultra high pressure mercury lamp, xenon lamp, metal halide lamp, electrodeless lamp, LED, etc. as a light source It is a laminate composed of any of the polymer layers obtained by preparing a polymer having a thickness of 200 ⁇ m and glass existing outside the polymer layer.
  • the portion sandwiched between the two sheets of glass outside the polymer layer does not contain any spacers, gaskets, or sealants.
  • the breaking strength of the polymer and the glass when the laminate is peeled in the direction perpendicular to the glass at 500 mm / min is 20 N / cm 2 or more” means the outer glass surface (both sides).
  • a plastic jig was affixed using a double-sided tape so that it could be sandwiched between chucks of a tensile tester (manufactured by Shimadzu Corporation, EZ Test / CE). Attach two glass with polymer film with plastic jig attached to Shimadzu EZ Test / CE, and pull the glass on both sides at a speed of 500mm / min.
  • the breaking strength of the polymer and the glass when the property is evaluated is 20 N / cm 2 or more.
  • the breaking strength of the polymer and glass measured under the above conditions is less than 20 N / cm 2 , an image display unit, a translucent protective unit, and an image display device in which a polymer layer is interposed therebetween are produced. Further, peeling may occur between the image display portion and the polymer layer, or between the light-transmitting protective portion and the polymer layer.
  • component 1 is added to the total amount of the polymerizable composition of the present invention (I) to the present invention (IV).
  • the content is preferably 10 to 40% by mass. More preferably, the amount of component 5 used is 5 to 30% by mass based on the total amount of component 1, component 3, component 4, component 5 and component 6 as essential components of the present invention (IV), The amount of component 6 used is preferably 40 to 60% by mass based on the total amount of component 1, component 3, component 4, component 5 and component 6 as essential components of the present invention (IV).
  • a laminate was prepared by interposing the polymer of the present invention (V) with glass, a resin plate and a thickness of 200 ⁇ m between them, and stored in an environment of 60 ° C. and 90% RH for 72 hours, and at 23 ° C. and 50% RH. It is preferable that no peeling occurs between the polymer and the glass and / or between the polymer and the resin plate after storage for 48 hours in an environment of 23 ° C. and 50% RH.
  • a laminate is prepared by interposing the polymer with a glass, a resin plate and a thickness of 200 ⁇ m therebetween” refers to one optical glass having a thickness of 0.7 mm (trade name: manufactured by Corning).
  • the present invention (VI) is a polymerizable composition for producing an optical pressure-sensitive adhesive sheet used as a polymer layer interposed between an image display part and a translucent protective part of an image display device.
  • the polymerizable composition is a polymerizable composition according to the present invention (I) to the present invention (IV). Using the polymerizable composition of the present invention (I) to the present invention (IV) as a raw material, the optical pressure-sensitive adhesive sheet can be produced.
  • the present invention (VII) has a thickness obtained by applying the polymerizable composition of the present invention (VI), irradiating the polymerizable composition with light capable of being photosensitized by the photopolymerization initiator, and polymerizing the polymerizable composition.
  • An optical pressure-sensitive adhesive sheet having a polymer layer of 10 to 1000 ⁇ m.
  • the optical pressure-sensitive adhesive sheet can be obtained by polymerizing a polymerization composition by irradiating light similar to the conditions under which the polymer of the present invention (V) is polymerized.
  • the optical pressure-sensitive adhesive sheet may be a double-sided pressure-sensitive adhesive sheet in which both surfaces of the sheet are pressure-sensitive adhesive surfaces (pressure-sensitive adhesive layer surface), or only one surface of the sheet is a pressure-sensitive adhesive surface (pressure-sensitive adhesive layer surface).
  • a single-sided adhesive sheet may be sufficient. Especially, it is preferable that it is a double-sided adhesive sheet from a viewpoint of bonding two members together.
  • the term “adhesive sheet” includes a tape-shaped material, that is, “adhesive tape”.
  • the optical pressure-sensitive adhesive sheet is a so-called “baseless-less type” optical pressure-sensitive adhesive sheet (hereinafter sometimes referred to as a “baseless-less optical pressure-sensitive adhesive sheet”) that does not have a base material (base material layer). It may also be an optical pressure-sensitive adhesive sheet having a base material.
  • the substrate-less optical pressure-sensitive adhesive sheet include, for example, a double-sided pressure-sensitive adhesive sheet composed only of the polymer layer composed of the polymer of the present invention, and a polymer layer composed of the polymer of the present invention and a pressure-sensitive adhesive other than the polymer layer. Examples thereof include a double-sided pressure-sensitive adhesive sheet composed of layers.
  • a pressure-sensitive adhesive sheet for baseless optics pressure-sensitive adhesive sheet for baseless double-sided optics
  • base material base material layer
  • release liner separator
  • the thickness of the polymer layer of the optical pressure-sensitive adhesive sheet is 10 to 1000 ⁇ m, preferably 20 to 700 ⁇ m, and more preferably 30 to 500 ⁇ m. If the thickness of the polymer layer exceeds 1000 ⁇ m, wrinkles may occur during winding during coating, or white turbidity may be easily caused by humidification. When the thickness of the polymer layer is less than 10 ⁇ m, since the polymer layer is thin, the stress cannot be dispersed and peeling may easily occur.
  • the optical pressure-sensitive adhesive sheet is used as a polymer layer interposed between an image display part of an image display device and a translucent protective part.
  • the optical pressure-sensitive adhesive sheet is used for the polymer (layer) 5b filled between the image display unit 2 and the translucent protection unit 3 in the display device mounted with the In-Cell capacitive touch panel shown in FIG.
  • the optical adhesive sheet has a high dielectric constant. Specifically, it is the same as the physical property values and effects described above for the dielectric constant in the present invention (V).
  • the optical pressure-sensitive adhesive sheet must have a storage elastic modulus of 1 ⁇ 10 3 to 1 ⁇ 10 5 Pa at 25 ° C. and a frequency of 0.1 Hz.
  • the storage elastic modulus of the optical pressure-sensitive adhesive sheet at 25 ° C. and a frequency of 0.1 Hz described in the present specification is as defined above, and the storage elastic modulus was previously described in the present invention (V). The physical property values and effects are the same.
  • the refractive index of the optical pressure-sensitive adhesive sheet at 25 ° C. is the same as the physical properties and effects described above for the refractive index in the present invention (V).
  • the method for forming the polymer layer of the optical pressure-sensitive adhesive sheet may be a known or conventional method for forming a polymer layer, and is not particularly limited, but has an acryloyl group as in the polymerizable composition of the present invention.
  • the polymerizable composition is polymerized to form the polymer layer of the optical pressure-sensitive adhesive sheet, for example, the following methods (1) to (3) can be mentioned.
  • a polymerizable composition having an acryloyl group containing a photopolymerization initiator is coated (coated) with a composition containing additives as necessary on a substrate or a separator (release liner), and a low-pressure mercury lamp , Using a light source such as a medium pressure mercury lamp, a high pressure mercury lamp, an ultra high pressure mercury lamp, a xenon lamp, a metal halide lamp, an electrodeless lamp, and an LED, the photopolymerization initiator irradiates light capable of being polymerized to polymerize the composition. Thus, a polymer layer is formed.
  • a light source such as a medium pressure mercury lamp, a high pressure mercury lamp, an ultra high pressure mercury lamp, a xenon lamp, a metal halide lamp, an electrodeless lamp, and an LED
  • a polymerizable composition having an acryloyl group containing a photopolymerization initiator and a composition (solution) further containing a solvent and, if necessary, an additive are applied (coated) on a substrate or a separator (release liner). And then irradiate the photopolymerization initiator with sensitive light using a light source such as a low-pressure mercury lamp, medium-pressure mercury lamp, high-pressure mercury lamp, ultra-high-pressure mercury lamp, xenon lamp, metal halide lamp, electrodeless lamp, or LED. Then, a polymer layer is formed by polymerizing the composition. (3) The polymer layer formed in (1) above is further dried.
  • a known coating method can be used for coating (coating) in the method for forming the polymer layer, and a conventional coater such as a gravure roll coater, a reverse roll coater, a kiss roll coater, a dip coater can be used.
  • a roll coater, bar coater, knife coater, spray coater, comma coater, direct coater or the like can be used.
  • the substrate is not particularly limited, and examples thereof include various optical films such as a plastic film, an antireflection (AR) film, a polarizing plate and a retardation plate.
  • the material such as the plastic film include, for example, polyester resins such as polyethylene terephthalate (PET), acrylic resins such as polymethyl methacrylate (PMMA), polycarbonate, triacetyl cellulose (TAC), polysulfone, polyarylate, polyimide, Polyvinyl chloride, polyvinyl acetate, polyethylene, polypropylene, ethylene-propylene copolymer, trade name “ARTON (cyclic olefin polymer; manufactured by JSR Corporation)”, trade name “ZEONOR (cycloolefin polymer; ZEON CORPORATION)
  • a plastic material such as a cyclic olefin polymer.
  • a plastic material can be used individually or in combination of 2 or more types.
  • the above-mentioned “base material” is a portion that is attached to the adherend together with the adhesive layer when the optical adhesive sheet is used (attached) to the adherend (optical member or the like).
  • a separator (release liner) that is peeled off when the adhesive sheet is used (attached) is not included in the “base material”.
  • a transparent substrate is preferable as the substrate.
  • the “transparent substrate” means, for example, a substrate having a total light transmittance (according to JIS K7361) of 85% or more in the visible light wavelength region, more preferably 88% or more.
  • the haze of the substrate is, for example, preferably 1.5% or less, and more preferably 1.0% or less.
  • the transparent substrate include PET films and non-oriented films such as trade names “Arton” and trade names “Zeonoa”.
  • the thickness of the substrate is not particularly limited and is preferably 12 to 75 ⁇ m, for example.
  • the said base material may have any form of a single layer and a multilayer.
  • the surface of the substrate may be appropriately subjected to known and conventional surface treatments such as physical treatment such as corona discharge treatment and plasma treatment, and chemical treatment such as undercoating treatment.
  • the pressure-sensitive adhesive sheet of the present invention becomes a pressure-sensitive adhesive functional film having the pressure-sensitive adhesive layer of the present invention on at least one side of the functional film.
  • optical functionality polarizability, photorefractive property, light reflectivity, light transmittance, light absorption property, light diffraction property, optical rotation property, visibility, etc.
  • a hard coat film (a film on which at least one surface of a plastic film such as a PET film is hard-coated), a polarizing film, a wave plate, a retardation film, an optical compensation film, a brightness enhancement film, a light guide plate , Reflective film, antireflection film, transparent conductive film (such as ITO film), design film, decorative film, surface protective film, prism, color filter and the like.
  • said "plate” and “film” shall include forms, such as plate shape, film shape, and sheet shape, respectively, for example, “polarizing film” shall also include “polarizing plate” and “polarizing sheet”.
  • the “functional film” includes “functional plate” and “functional sheet”.
  • the other pressure-sensitive adhesive layer is not particularly limited, and examples thereof include a urethane-based pressure-sensitive adhesive, an acrylic pressure-sensitive adhesive, a rubber-based pressure-sensitive adhesive, and a silicone-based pressure sensitive adhesive layer.
  • examples include known and commonly used pressure-sensitive adhesive layers formed from known pressure-sensitive adhesives such as pressure-sensitive adhesives, polyester-based pressure-sensitive adhesives, polyamide-based pressure-sensitive adhesives, epoxy-based pressure-sensitive adhesives, vinyl alkyl ether-based pressure-sensitive adhesives, and fluorine-based pressure-sensitive adhesives.
  • the above adhesives can be used alone or in combination of two or more.
  • the optical pressure-sensitive adhesive sheet contains neither a base material nor another pressure-sensitive adhesive layer, a polymer layer obtained by polymerizing the polymerizable composition of the present invention (I) to the present invention (IV)
  • a polymer layer obtained by polymerizing the polymerizable composition of the present invention (I) to the present invention (IV) is combined with this other pressure-sensitive adhesive layer.
  • a polymer layer obtained by polymerizing the polymerizable composition of the present invention (I) to the present invention (IV), a layer combining this substrate When both the pressure-sensitive adhesive layer and the substrate are included, the polymer layer obtained by polymerizing the polymerizable composition of the present invention (I) to the present invention (IV), the other pressure-sensitive adhesive layer and the substrate are combined.
  • Layer is defined as “adhesive layer”.
  • the pressure-sensitive adhesive layer surface (adhesive surface) of the optical pressure-sensitive adhesive sheet may be protected by a separator (release liner) until use.
  • a separator release liner
  • each pressure-sensitive adhesive surface may be protected by two separators, respectively, or a single separator whose both surfaces are release surfaces, You may protect in the form wound by the shape.
  • the separator is used as a protective material for the pressure-sensitive adhesive layer, and is peeled off when being applied to an adherend.
  • a separator also plays the role of the support body of an adhesive layer. Note that the separator is not necessarily provided.
  • a conventional release paper or the like can be used, and is not particularly limited.
  • a substrate having a release treatment layer a low adhesive substrate made of a fluoropolymer, a low adhesive substrate made of a nonpolar polymer, etc.
  • a base material which has the said peeling process layer the plastic film, paper, etc. which were surface-treated with peeling processing agents, such as a silicone type, a long-chain alkyl type, a fluorine type, and molybdenum sulfide, are mentioned, for example.
  • fluorine-based polymer in the low-adhesive substrate made of the above-mentioned fluoropolymer examples include polytetrafluoroethylene, polychlorotrifluoroethylene, polyvinyl fluoride, polyvinylidene fluoride, tetrafluoroethylene-hexafluoropropylene copolymer, chloro Examples include fluoroethylene-vinylidene fluoride copolymer.
  • nonpolar polymer olefin resin (for example, polyethylene, a polypropylene, etc.) etc. are mentioned, for example.
  • the separator can be formed by a known or conventional method. Further, the thickness of the separator is not particularly limited.
  • the polymerizable composition of the present invention (I) ⁇ (IV) is storage modulus at frequency 0.1Hz at 25 ° C. as measured by the conditions when polymerizing the polymerizable composition is 1 ⁇ 10 3 ⁇
  • the essential constituents of the present invention (I) to (IV) may be mixed uniformly.
  • the temperature when mixing each component is preferably in the range of 20 to 100 ° C., more preferably in the range of 30 to 95 ° C. And particularly preferably in the range of 40 to 90 ° C.
  • the compound that is solid at 25 ° C. is component 5 alone, a mixture of component 4 and component 5, component 5 and component 6 It is preferable to dissolve in a mixture of compounds that are liquid at 25 ° C. or a mixture of compounds that are component 4, component 5 and component 6 that are liquid at 25 ° C. to obtain a uniform liquid mixture.
  • the temperature at which the compound that is solid at 25 ° C. of the component 6 is desirably higher than the softening point of the component 6 that is solid at 25 ° C. in consideration of the dissolution rate.
  • component 4 is used for dissolution, it is desirable to dissolve at a temperature of 130 ° C.
  • the polymerizable composition of the present invention (I) to (IV) is produced using the uniform liquid mixture in which the compound that is solid at 25 ° C. is dissolved, this mixed liquid is used.
  • the temperature at the time of mixing each of the components is preferably in the range of 20 to 100 ° C., more preferably in the range of 30 to 95 ° C., and particularly preferably in the range of 40 to 90 ° C.
  • the polymer of the image device of the present application and the optical pressure-sensitive adhesive sheet have coloring resistance and high transparency.
  • the color resistance can be evaluated by satisfying the following physical property values.
  • the color coordinate b * value described in JIS Z 8729 after storing the polymer adjusted to a thickness of 200 ⁇ m existing between two glasses at a temperature of 85 ° C. for 500 hours is It is less than 1.6.
  • the polymer obtained by polymerizing the polymerizable composition of the present invention has high transparency. Specifically, the polymer is adjusted to a thickness of 200 ⁇ m existing between two glasses.
  • the haze is preferably 0.4 or less, and more preferably 0.2 or less.
  • polymerized to a thickness of 200 ⁇ m existing between two glasses means two optical glasses having a thickness of 0.7 mm (trade name: Eagle XG, manufactured by Corning). Initiating photopolymerization using a low-pressure mercury lamp, medium-pressure mercury lamp, high-pressure mercury lamp, ultra-high-pressure mercury lamp, xenon lamp, metal halide lamp, electrodeless lamp, LED, etc.
  • the polymer is a polymer having a thickness of 200 ⁇ m obtained by irradiating light capable of being exposed to light, and a spacer, a gasket, a sealant, or the like is provided between the two glass layers outside the polymer layer. Is not included at all.
  • the “color coordinate b * value described in JIS Z 8729 after storage at 85 ° C. for 500 hours” described in the present specification is adjusted to a thickness of 200 ⁇ m existing between the two glasses.
  • the polymer was held at 85 ° C. for 500 hours, and then measured at 23 ° C. in accordance with the method described in JIS Z 8729 using the value of b * of the measured color coordinates (psychometric chroma coordinates). is there.
  • the reference used when measuring the value of b * is one optical glass (manufactured by Corning, trade name: Eagle XG) having a thickness of 0.7 mm.
  • the value of b * measured on the said conditions is 1.6 or less. More preferably, it is 1.2 or less, More preferably, it is 1.0 or less.
  • an appropriate amount of an antioxidant may be added to the polymerizable composition.
  • the amount of the antioxidant used is preferably 0.01 to 5 parts by mass with respect to the total amount of the polymerizable composition of the present invention (I) to the present invention (IV).
  • the amount of the antioxidant is a value in consideration of the antioxidant contained in the other components such as the component 6 in advance. That is, when an antioxidant is preliminarily contained in the component 6 or the like, the total amount of this antioxidant and the newly added antioxidant is the present invention (I) to the present invention (IV ) To 0.01 to 5 parts by mass relative to the total amount of the polymerizable composition.
  • the amount of the antioxidant used is more preferably 0.01 to 4 parts by mass, particularly preferably 0.01 to 3 parts by mass.
  • the addition effect that is, the antioxidant effect
  • the value of b * may exceed 1.6 under the above conditions.
  • the amount of the polymerization inhibitor is more than 5 parts by mass relative to the total amount of the polymerizable composition of the present invention (I) to the present invention (IV)
  • the color coordinate b * value described in JIS Z 8729 after storing the polymer adjusted to a thickness of 200 ⁇ m existing between the two sheets of glass at 95 ° C. for 500 hours is also the above-mentioned 85 ° C. It is preferable to satisfy the physical property values of The measurement method at this time is the same as the method at 85 ° C. described above.
  • the haze described in JIS K 7136 after storing the polymer adjusted to a thickness of 200 ⁇ m existing between two glasses at a temperature of 60 ° C. and 90% for 500 hours is 0.4 or less. It is preferable. More preferably, it is 0.2 or less. In this case as well, the measurement method is the same as that described above. When the haze is 0.4 or more, the light transmittance is reduced.
  • the amount of component 3 used is an essential component of the present invention (IV).
  • the total amount of Component 1, Component 3, Component 4, Component 5 and Component 6 is preferably 1 to 30 parts by mass. More preferably, it is 2 to 20 parts by mass, and particularly preferably 3 to 10 parts by mass.
  • the present invention (VIII) is a method for producing an image display device comprising a base having an image display portion, a translucent protective portion, and a polymer layer interposed between the base and the protective portion, The method comprises the step of interposing the polymerizable composition of the present invention (IV) between the base part and the protective part, and irradiating the polymerizable composition with light that can be photosensitized by a photopolymerization initiator.
  • the present invention relates to a method for manufacturing an image display device including a step of forming a polymer layer.
  • between the base portion having the image display portion and the translucent protective portion means all the portions between the base portion having the image display portion and the translucent protective portion. For example, it means that any of the locations 5a and 5b in FIG. 5 is included in the expression “between the base portion having the image display portion and the translucent protective portion”.
  • FIG. 2, FIG. 3 and FIG. 4 are cross-sectional views showing the main parts of one embodiment of the image display device according to the present invention.
  • the display device 1 of the present embodiment is connected to a drive circuit (not shown) and displays an image display unit 2 that performs a predetermined image display.
  • a translucent protective portion 3 disposed in close proximity to each other at a distance of.
  • the “image display device” described in the present specification is not particularly limited as long as it is a device that displays an image, and can be applied to various devices.
  • a liquid crystal display device or an organic EL display device such as a mobile phone or a mobile game device can be used.
  • the image display unit 2 of the present embodiment is a liquid crystal display panel of a liquid crystal display device.
  • polarizing plates 6a and 6b are provided on the surface thereof as shown in FIG. 2, FIG. 3, or FIG.
  • the spacer 4 and a jetty are provided on the peripheral portion on the image display unit 2, and the region of the present invention (IV) is provided in the inner region thereof.
  • a predetermined amount of the polymerizable composition is dropped.
  • the protective part 3 is arranged on the spacer 4 of the image display part (liquid crystal display panel) 2, and the polymerization of the present invention (IV) is performed in the gap between the image display part (liquid crystal display panel) 2 and the protective part 3.
  • the composition is filled without gaps.
  • the component 2 which is an essential component of the polymerizable composition of the present invention (IV) is irradiated with light capable of being exposed to the polymerizable composition of the present invention (IV) via the protective part 3.
  • the polymerizable composition of the present invention (IV) is polymerized. Thereby, the target image display apparatus 1 is obtained.
  • the refractive index of the polymer layer 5 and the protective part 3 are equal, the brightness and contrast can be increased to improve the visibility.
  • the process of irradiating the component 2 with photosensitive light is a general ultraviolet irradiation device using a low pressure mercury lamp, a medium pressure mercury lamp, a high pressure mercury lamp, an ultrahigh pressure mercury lamp, a xenon lamp, a metal halide lamp, an electrodeless lamp or the like as a light source.
  • a general ultraviolet irradiation device using a low pressure mercury lamp, a medium pressure mercury lamp, a high pressure mercury lamp, an ultrahigh pressure mercury lamp, a xenon lamp, a metal halide lamp, an electrodeless lamp or the like as a light source.
  • UV irradiation dose is generally from about 1000 mJ / cm 2 ⁇ about 8000 mJ / cm 2.
  • the influence of the stress caused by the volume shrinkage during polymerization of the polymerizable composition can be suppressed to the image display unit (liquid crystal display panel) 2 and the protection unit 3, the liquid crystal display panel 2 and the protection unit 3 can be protected. As a result, the image display unit (liquid crystal display panel) 2 is not deformed, so that it is possible to display an image with high brightness and high contrast without display defects.
  • the dielectric constant of the polymer in the polymer layer 5b is maintained high. Even if the thickness of the polymer layer is increased to some extent, it is possible to prevent the sensitivity of the touch sensor from being lowered.
  • This invention (IX) is a manufacturing method of an image display apparatus which has the process of sticking the base which has an image display part, and a translucent protective part using an optical adhesive sheet, Comprising:
  • This optical adhesive sheet is A method for manufacturing an image display device, which is the optical pressure-sensitive adhesive sheet according to the present invention (VII).
  • “attaching a base portion having an image display portion and a translucent protective portion using an optical adhesive sheet” means that the base portion having an image display portion and a translucent portion are used. Meaning that any part between the protective part and the protective part is included in the expression "the base having the image display part and the translucent protective part are attached using an optical adhesive sheet". For example, even if the adhesive sheet is attached to either 5a or 5b in FIG. 5, "the base having the image display part and the translucent protective part are attached using the optical adhesive sheet” It is included in the expression.
  • the first base material is a touch sensor integrated protective portion
  • a manufacturing process in the display device of FIG. 4 in which the base material is a display unit with a polarizing plate will be described as an example.
  • the step of arranging the optical pressure-sensitive adhesive sheet adjacent to one side of the translucent protective part as the first base material, and the surface of the display part with a polarizing plate as the second base material for the optical A step of arranging adjacent to the pressure-sensitive adhesive sheet, a step of heating and / or pressing the optical pressure-sensitive adhesive sheet to follow a step or a ridge, and a photopolymerization initiator on the optical pressure-sensitive adhesive sheet as necessary. It can be manufactured by a method including a step of irradiating photosensitive light. These steps can be performed in various orders.
  • one surface of the optical pressure-sensitive adhesive sheet is disposed adjacent to one side of the translucent protective portion which is the first base material, and the second base material is used.
  • the surface of the display part with a certain polarizing plate is arrange
  • the optical pressure-sensitive adhesive sheet is heated and / or pressurized to cause the pressure-sensitive adhesive sheet to follow a step or a bump.
  • the optical pressure-sensitive adhesive sheet passes through these substrates from the side of the translucent protective part (first base material) and / or the display part (second base material) with a polarizing plate.
  • the photopolymerization initiator is irradiated with light capable of being exposed to light.
  • the translucent protective part (first base material) and the polarizing plate are attached without forming a gap in the vicinity of the step or the bulge of the translucent protective part (first base material).
  • the display portion (second base material) can be adhered.
  • a translucent protective part (first base material) and a display part with a polarizing plate (second base material) are adjacent to the optical pressure-sensitive adhesive sheet, and then the pressure-sensitive adhesive sheet is heated and In order to pressurize, when there is a step or a bulge on the adherend surface of the display unit (second base material) with a polarizing plate (that is, the adhesive sheet is applied on the polarizing plate attached to the image display module)
  • the pressure-sensitive adhesive sheet can be made to follow the steps and bulges of the display portion (second base material) with the polarizing plate, and the formation of voids can be prevented even in the vicinity of the shape.
  • the photopolymerization initiator when the photopolymerization initiator irradiates light capable of being sensitized, at least one of the first base material and the second base material passes through them to the optical pressure-sensitive adhesive sheet, and the photopolymerization initiator is present. It is at least partially transparent so that it can be irradiated with photosensitive light.
  • the step or bulge portion of the first base material does not transmit ultraviolet light
  • the ultraviolet light when the ultraviolet light is irradiated from the first base material side, the ultraviolet light is not irradiated directly below the step or bulge portion, but the irradiated portion
  • the polymerization of the pressure-sensitive adhesive sheet proceeds to some extent even in the non-irradiated part due to the movement of radicals generated in the above.
  • one surface of the optical pressure-sensitive adhesive sheet is a surface side having a step or a bulge in the translucent protective portion (first base material) (that is, a person does not touch during use)
  • the pressure-sensitive adhesive sheet is heated and / or pressurized to cause the pressure-sensitive adhesive sheet to follow a step or a bump.
  • the display unit with the polarizing plate (second base material) is placed on the pressure-sensitive adhesive sheet. It arrange
  • the pressure-sensitive adhesive sheet can be irradiated with ultraviolet rays through the release film, if necessary.
  • the pressure-sensitive adhesive sheet can be polymerized more uniformly.
  • the first base material is at least partially transparent so that the photopolymerization initiator necessary for the polymerization of the pressure-sensitive adhesive sheet can irradiate light capable of being sensitized, from the first base material side, if necessary. Irradiation with ultraviolet rays is also possible. In this way, the first base material and the second base material can be bonded together without forming a gap near the step or bulge of the first base material.
  • the heating step can be performed using a convection oven, a hot plate, a heat laminator, an autoclave, or the like.
  • a convection oven a hot plate
  • a heat laminator a heat laminator
  • an autoclave a heat laminator
  • Pressurization using an autoclave is particularly advantageous for defoaming the optical pressure-sensitive adhesive sheet.
  • the heating temperature of the optical pressure-sensitive adhesive sheet of the present invention may be any temperature as long as the pressure-sensitive adhesive sheet softens or flows and sufficiently follows a step or a bump, and is generally about 30 ° C. or higher, about 40 ° C. or higher, or about 60 ° C.
  • the temperature may be about 150 ° C. or lower, about 120 ° C. or lower, or about 100 ° C. or lower.
  • the applied pressure can be generally about 0.05 MPa or more, or about 0.1 MPa or more, about 2 MPa or less, or about 1 MPa or less.
  • the step of irradiating light that can be photosensitized by the above-described photopolymerization initiator, which is performed as necessary, is the same as the step of irradiating light that can be sensitized by the component 2 described above.
  • the present invention (X) is an image display device manufactured by the manufacturing method of the image display device of the present invention (VIII) or the present invention (IX).
  • the image display device of the present invention (X) generally has a refractive index (n D ) of 1.49 to 1.52 when the main body of the display device is made of optical glass.
  • n D refractive index
  • the protection unit 3 is formed from a plate-like, sheet-like, or film-like translucent member having the same size as the display unit 2.
  • optical glass or plastic acrylic resin such as polymethyl methacrylate
  • An optical layer such as an antireflection film, a light shielding film, or a viewing angle control film may be formed on the front surface or the back surface of the protection unit 3.
  • the protective part 3 is made of an acrylic resin, its refractive index (n D ) is generally 1.49 to 1.51.
  • the protection unit 3 is provided on the display unit 2 via a spacer 4 provided on the peripheral edge of the display unit 2.
  • the spacer 4 has a thickness of about 0.05 to 1.5 mm, whereby the distance between the surfaces of the image display unit 2 and the protection unit 3 is maintained at about 1 mm.
  • a frame-shaped light shielding portion (not shown) is provided at the peripheral portion of the protection portion 3 in order to improve luminance and contrast.
  • the image display device manufactured by the method for manufacturing the image display device of the present invention (VIII) will be described in detail. Between the image display part 2 and the protection part 3, polymer layers 5a and 5b are interposed.
  • the polymer of the present invention (V) is interposed in the polymer layer 5a and the polymer layer 5b.
  • the transmittance in the visible light region is 90% or more.
  • the thickness of the polymer layer 5a or the polymer layer 5b is preferably 10 to 2000 ⁇ m. More preferably, it is 20 to 1700 ⁇ m, and particularly preferably 30 to 1300 ⁇ m.
  • the refractive index (n D ) at 25 ° C. is described in the above-mentioned present invention (V).
  • the physical property values and effects are the same.
  • the polymer composition of the present invention (V) is interposed in the polymer layer 5a and the polymer layer 5b, and therefore the polymerizable composition.
  • the physical properties of the volume shrinkage during polymerization are the same as the physical properties and effects described for the volume shrinkage in the present invention (V).
  • the polymer of this invention (V) for the polymer layer 5b, since the dielectric constant of these polymers is high, the sensitivity when a person touches can be enlarged. Further, when the image display device is produced by the method for producing an image display device of the present invention (IX), the polymer is interposed in the polymer layer 5a and the polymer layer 5b, and therefore the present invention (V) described above. The effects and characteristics obtained when an image display device is manufactured by this method for manufacturing an image display device can be obtained.
  • the image display apparatus manufactured by the image display apparatus manufacturing method of the present invention (IX) will be described in detail.
  • a polymer layer 5a and a polymer layer 5b or a polymer layer 5b are interposed.
  • the optical adhesive sheet is interposed in the polymer layer 5a and the polymer layer 5b, so that the visible light region Of 90% or more.
  • the thickness of the polymer layer 5a and the polymer layer 5b is preferably 10 to 1000 ⁇ m. More preferably, the thickness is 20 to 700 ⁇ m, and particularly preferably 30 to 500 ⁇ m.
  • the refractive index at 25 ° C. (n D ) is the refractive index in the present invention (VIII) first. This is the same as the physical property values and effects described above.
  • the optical pressure-sensitive adhesive sheet has flexibility, even if the protection unit 3, the display unit 2, and the touch panel 7 have an uneven shape, a layer having an uneven surface shape on the display surface of the image display unit. Even if (for example, a polarizing plate) is provided, the internal residual stress of the sheet itself is relaxed, and display unevenness in the image display device can be prevented.
  • the display surface (for example, a polarizing plate) of the image display unit 2 can be used even in a high temperature and high humidity environment.
  • Air bubbles and peeling do not occur at the interface with the optical pressure-sensitive adhesive sheet (that is, the polymer layer 5b) and at the interface between the optical pressure-sensitive adhesive sheet (that is, the polymer layer 5b) and the translucent protective portion 3. No whitening occurs.
  • optical glass plate used in the image display device of the present invention those used as a glass plate for sandwiching the liquid crystal of the liquid crystal cell or a protective plate for the liquid crystal cell can be preferably used.
  • acrylic resin board used what is used as a protective plate of a liquid crystal cell can be used preferably.
  • the average surface roughness of these optical glass plates and acrylic resin plates is usually 1.0 nm or less.
  • the image display device of the present invention (X) includes a polymer layer 5a or a polymer obtained by using the polymer of the present invention (V) or the optical pressure-sensitive adhesive sheet between the image display unit 2 and the protection unit 3. Since the layer 5b is filled, it is strong against impact. In addition, it can be formed thinner than the conventional example in which a gap is provided between the image display unit 2 and the protection unit 3.
  • the image display device of the present invention (X) can take various forms.
  • the image display device 1 may be manufactured by omitting the spacer 4.
  • the photopolymerizable composition of any one of the present invention (I) to the present invention (IV) is applied onto the polarizing plate 6a on the display unit 2, and the above-mentioned Or, for example, as shown in FIG. 5, a laminate composed of the protective portion 3, the polymer layer 5b, the touch panel 7 and the polymer layer 5a (that is, the optical pressure-sensitive adhesive sheet 5a) is formed. It can be obtained by bonding to the display surface on the image display unit 2 (that is, the surface of the polarizing plate 6a).
  • the present invention can be applied not only to the liquid crystal display device described above but also to various panel displays such as an organic EL and a plasma display device.
  • the polymerizable composition of the present invention it is possible to minimize the stress due to volume shrinkage when it is applied between the image display part and the protective part and polymerized, so that the image display part is provided.
  • an image display device is manufactured using a process of forming a polymer layer by interposing a polymerizable composition between a base and a translucent protective part and polymerizing the image display part, The influence on the protection unit can be minimized. Therefore, according to the image display device of the present invention, distortion hardly occurs in the image display unit and the protection unit.
  • the polymerizable composition of the present invention does not contain a volatile solvent (that is, no solvent)
  • the polymer obtained by polymerizing the polymerizable composition of the present invention is divided into an image display part and a protective part.
  • a volatile solvent that is, no solvent
  • the cured product obtained by polymerizing the polymerizable composition of the present invention between the image display part and the protective part has high adhesion to the glass used in the protective part.
  • the polymer and the optical adhesive sheet of the present invention have a refractive index that is a configuration panel of the image display unit or a configuration of the protection unit as compared with a gap that is conventionally provided between the liquid crystal display panel and the protection unit. It is close to the refractive index of the panel, and the light at the interface between the protective part and the polymer, the interface between the polymer and the image display part, the interface between the protective part and the optical adhesive sheet, or the interface between the optical adhesive sheet and the image display part. Reflection is suppressed. As a result, according to the image display device of the present invention, high luminance and high contrast display without display defects becomes possible.
  • the image display unit is a liquid crystal display panel
  • display defects such as disorder of alignment of the liquid crystal material can be reliably prevented and high-quality display can be performed.
  • the image display device of the present invention since the polymer or the optical adhesive sheet is interposed between the image display unit and the protection unit, the image display device is resistant to impact. Furthermore, since the polymer and the optical adhesive sheet of the present invention are not easily colored even when subjected to a thermal history, it is possible to maintain high brightness and high contrast display for a long time. In addition, according to the present invention, it is possible to provide a thin image display device as compared with the conventional example in which a gap is provided between the image display unit and the protection unit.
  • ⁇ Measurement of viscosity> For samples having a viscosity of less than 10 Pa ⁇ s at a temperature of 25.0 ° C., the viscosity was measured by the following method. Using a 1 mL sample, the viscosity was measured at a temperature of 25.0 ° C. and a rotation speed of 5 rpm using a cone / plate viscometer (manufactured by Brookfield, model: DV-II + Pro, spindle model: CPE-42). The value when it became almost constant was measured. For a sample having a viscosity of 10 Pa ⁇ s or more at a temperature of 25.0 ° C., the viscosity was measured by the following method.
  • the number average molecular weight is a value in terms of polystyrene measured by GPC under the following conditions.
  • Device name HPLC unit HSS-2000 manufactured by JASCO Corporation Column: Shodex column LF-804
  • Mobile phase Tetrahydrofuran Flow rate: 1.0 mL / min Detector: RI-2031Plus manufactured by JASCO Corporation Temperature: 40.0 ° C
  • Sample volume Sample loop 100 ⁇ L
  • Sample concentration prepared at around 0.5 wt%
  • Pripol (registered trademark) 2033 (clad hydrogenated dimer diol, hydroxyl value 202 mg KOH / g) 26.2 parts by mass, 1,4-butanediol (Mitsubishi Chemical Corporation) in a 2000 mL reaction vessel equipped with a stirrer and a distillation apparatus 47.2 parts by mass of company), 656.3 parts by mass of 3-methyl-1,5-pentanediol (manufactured by Kuraray Co., Ltd.), 721.4 parts by mass of adipic acid (manufactured by Tokyo Chemical Industry Co., Ltd.), Pripol (registered) Trademark) 1009 (clad hydrogenated dimer acid) 241.5 parts by weight and stannous chloride (manufactured by Tokyo Chemical Industry Co., Ltd.) 0.5 parts by weight were charged, and water was distilled off starting at about 170 ° C.
  • polyester polyol A A polyester polyol having a hydroxyl value of 57.0 mgKOH / g (hereinafter referred to as polyester polyol A) was obtained.
  • Example synthesis example 2-1 In a 100 mL reaction vessel equipped with a stirrer, thermometer, dropping funnel and condenser, a mixture of 2,2,4-trimethylhexamethylene diisocyanate and 2,4,4-trimethylhexamethylene diisocyanate (trade name: VESTANAT®) ) TMDI, manufactured by Evonik Degussa) 15.28 g, dioctyltin dilaurate 15 mg and p-methoxyphenol 24 mg were charged into a reaction vessel, and 10.48 g of 4-hydroxybutyl acrylate was added dropwise using a dropping funnel. During the dropping, the temperature in the reaction vessel was adjusted to 70 ° C. or lower.
  • reaction product ⁇ a reaction product (hereinafter referred to as reaction product ⁇ ).
  • reaction product ⁇ a reaction product (number average molecular weight 2030) was charged, and stirring was started. Thereafter, the total amount of the reaction product ⁇ maintained at 60 ° C. was introduced into the reaction vessel in several portions. Meanwhile, the temperature in the reactor was not allowed to rise above 70 ° C. Thereafter, the temperature in the reactor was maintained at 70 to 75 ° C., and stirring was continued.
  • urethane acrylate 1 having a number average molecular weight of 2380 (hereinafter referred to as “urethane acrylate 1”) was obtained. Since it is considered that 1-fold molar amount of acryloyl group derived from 4-hydroxybutyl acrylate is introduced relative to polyester polyol A, the number of acryloyl groups contained in this urethane acrylate 1 is 1 on average per molecule. It can be assumed that there is.
  • Example synthesis example 2-2 In a 100 mL reaction vessel equipped with a stirrer, thermometer, dropping funnel and condenser, a mixture of 2,2,4-trimethylhexamethylene diisocyanate and 2,4,4-trimethylhexamethylene diisocyanate (trade name: VESTANAT®) ) TMDI, manufactured by Evonik Degussa) 27.83 g, dioctyltin dilaurate 30 mg and p-methoxyphenol 24 mg were charged into a reaction vessel, and 4-hydroxybutyl acrylate 19.08 g was added dropwise using a dropping funnel. During the dropping, the temperature in the reaction vessel was adjusted to 70 ° C. or lower.
  • reaction product ⁇ a reaction product (hereinafter referred to as reaction product ⁇ ).
  • reaction product ⁇ a reaction product (number average molecular weight 2030) was charged, and stirring was started. Thereafter, the total amount of the reaction product ⁇ maintained at a temperature of 60 ° C. was introduced into the reaction vessel in several portions. Meanwhile, the temperature in the reactor was not allowed to rise above 70 ° C. Thereafter, the temperature in the reactor was maintained at 70 to 75 ° C., and stirring was continued.
  • urethane acrylate 2 having a number average molecular weight of 2670 (hereinafter referred to as “urethane acrylate 2”) was obtained. Since it is considered that acryloyl groups derived from 4-hydroxybutyl acrylate in a molar amount of 1.8 times that of polyester polyol A are introduced, the number of acryloyl groups contained in this urethane acrylate 2 is 1 on an average per molecule. .8 can be assumed.
  • urethane acrylate 3 having a number average molecular weight of 2560 (hereinafter referred to as “urethane acrylate 3”) was obtained.
  • urethane acrylate 3 since it is considered that 1.5 times mole amount of acryloyl group derived from 4-hydroxybutyl acrylate with respect to polyester polyol A is introduced, the number of acryloyl groups contained in this urethane acrylate 3 is 1 on an average per molecule. .5 can be assumed.
  • Example synthesis example 2-4 In a 300 mL reaction vessel equipped with a stirrer, a thermometer and a condenser, the above-mentioned polyester polyol A (number average molecular weight 2030) 150 g, 4-hydroxybutyl acrylate 19.08 g, dioctyltin dilaurate 30 mg and p-methoxyphenol 24 mg were reacted. The container was charged and stirring was started.
  • urethane acrylate 4 having a number average molecular weight of 2670. Since it is considered that acryloyl groups derived from 4-hydroxybutyl acrylate in a molar amount of 1.8 times that of polyester polyol A are introduced, the number of acryloyl groups contained in this urethane acrylate 4 is 1 on average per molecule. .8 can be assumed.
  • Example synthesis 2-5 In a 100 mL reaction vessel equipped with a stirrer, thermometer, dropping funnel and condenser, a mixture of 2,2,4-trimethylhexamethylene diisocyanate and 2,4,4-trimethylhexamethylene diisocyanate (trade name: VESTANAT®) ) TMDI, manufactured by Evonik Degussa) 22.94 g, 30 mg of dioctyltin dilaurate and 24 mg of p-methoxyphenol were added to the reaction vessel, and 15.73 g of 4-hydroxybutyl acrylate was added dropwise using a dropping funnel. During the dropping, the temperature in the reaction vessel was adjusted to 70 ° C. or lower.
  • reaction product ⁇ a reaction product (hereinafter referred to as reaction product ⁇ ).
  • polyester polyol trade name: Kuraray polyol P-2050, hydroxyl value 57.0 mg KOH / g, manufactured by Kuraray Co., Ltd., sebacic acid and 3-methyl-1
  • polyester polyol (trade name: Kuraray polyol P-2010, hydroxyl value 57.0 mg KOH / g, manufactured by Kuraray Co., Ltd., adipic acid and A polyester polyol produced using 3-methyl-1,5-pentanediol as a raw material, number average molecular weight 2000) 75 g was added, and stirring was started.
  • urethane acrylate 5 urethane acrylate having a number average molecular weight of 2520
  • Example synthesis 2-6 In a 100 mL reaction vessel equipped with a stirrer, thermometer, dropping funnel and condenser, a mixture of 2,2,4-trimethylhexamethylene diisocyanate and 2,4,4-trimethylhexamethylene diisocyanate (trade name: VESTANAT®) ) TMDI, manufactured by Evonik Degussa) 27.83 g, dioctyltin dilaurate 30 mg and p-methoxyphenol 24 mg were charged into a reaction vessel, and 4-hydroxybutyl acrylate 19.08 g was added dropwise using a dropping funnel. During the dropping, the temperature in the reaction vessel was adjusted to 70 ° C. or lower.
  • reaction product ⁇ a reaction product (hereinafter referred to as reaction product ⁇ ).
  • reaction product ⁇ a reaction product (trade name: Kuraray polyol P-2050, hydroxyl value 57.0 mg KOH / g, manufactured by Kuraray Co., Ltd., number average molecular weight 1980)
  • polyester polyol Product name: Kuraray polyol P-2010, hydroxyl value 57.0 mgKOH / g, manufactured by Kuraray Co., Ltd., number average molecular weight 2000) was added in an amount of 75 g, and stirring was started.
  • Example of formulation 1 Urethane acrylate 5 99.0 parts by mass, 1-hydroxycyclohexyl phenyl ketone (trade name: IRGACURE (registered trademark) 184, manufactured by BASF) 0.8 parts by mass, 2,4,6-trimethylbenzoyldiphenylphosphine oxide (trade name: 0.2 parts by weight of SpeedCure TPO, manufactured by Lambson) and pentaerythritol tetrakis [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate] (trade name: IRGANOX (registered trademark) 1010, manufactured by BASF) 1.0 part by mass was mixed using a rotation / revolution mixer (manufactured by Shinky Co., Ltd., trade name: Rentaro Awatori ARE-310). This blend was designated as a polymerizable composition A1. The viscosity at 25 ° C. of the polymerizable composition A1 was 33,690
  • Example formulation examples 2 to 6 and comparative formulation examples 1 and 2 In the same manner as in Example 1 of blending, blending was performed according to the blending composition shown in Table 1.
  • the formulations prepared in Examples 2 to 6 were designated as polymerizable compositions A2 to A6, respectively, and the formulations prepared in comparative formulation examples 1 and 2 were designated as polymerizable compositions B1 and B2.
  • the unit of the number of each component of the implementation formulation example and the comparative formulation example described in Table 1 is “parts by mass”.
  • a conveyor type ultraviolet irradiation device using a metal halide lamp (GS Yuasa Lighting Co., Ltd.) Manufactured under the trade name: GSN2-40), and ultraviolet rays were irradiated through a silicone-coated PET film under the conditions of irradiation intensity of 190 mW / cm 2 (value of 365 nm) and irradiation amount of 6000 mJ / cm 2 (value of 365 nm).
  • the film thickness is about 2 between the exposed PET film and the release PET film.
  • optical pressure-sensitive adhesive sheet for 0 .mu.m.
  • the optical pressure-sensitive adhesive sheets produced using the polymerizable compositions A1 to A6 and the polymerizable compositions B1 and B2 were referred to as pressure-sensitive adhesive sheets A1 to A6 and pressure-sensitive adhesive sheets B1 and B2, respectively.
  • the adhesive sheets A1 to A6 and the adhesive sheets B1 and B2 each have two glass plates (50 mm ⁇ 50 mm ⁇ 0.7 mm, glass type, product name: EAGLE XG () so that air bubbles do not enter the interface.
  • a test piece was prepared by adhering the adhesive sheet so as to be sandwiched from both sides with a registered trademark and CORNING.
  • Test pieces prepared using the pressure-sensitive adhesive sheets A1 to A6 and the pressure-sensitive adhesive sheets B1 and B2 were referred to as test pieces AS1-1 to AS6-1 and test pieces BS1-1 and BS2-1, respectively. The adhesion of these test pieces to glass was measured by the method described below.
  • the adhesive sheets A1 to A6 and the adhesive sheets B1 and B2 each have two glass plates (50 mm ⁇ 50 mm ⁇ 0.7 mm, glass type, product name: EAGLE XG () so that air bubbles do not enter the interface. (Registered trademark), CORNING) and resin plate (Mitsubishi Gas Chemical Co., Ltd., trade name: MR-85, or Mitsubishi Rayon Co., Ltd., trade name: Acrylite MR-200).
  • a test piece was prepared.
  • a polymer film for an evaluation test which was manufactured using the polymerizable compositions A1 to A6 and the polymerizable compositions B1 and B2 and was sandwiched between the glass plate and the resin plate and having a thickness of about 200 ⁇ m, was tested.
  • the specimens AS1-2 to AS6-2 and specimens BS1-2 and BS2-2 were used.
  • the adhesion of these test pieces to the resin plate was measured by the method described later.
  • the results are shown in Table 4.
  • the below-mentioned peeling resistance test was done using these test pieces.
  • the results are shown in Table 4.
  • “PMMA and glass plate peeling resistance test” described in Table 4 is a test when MR-200 is used for the resin plate.
  • the “Peeling resistance test between PC and glass plate” shown in Table 4 is a test when MR-85 is used for the resin plate.
  • the polymerizable composition A4 to the polymerizable composition A6 and the polymerizable compositions B1 and B2 are each applied to a glass plate so as to have a film thickness of 200 ⁇ m, and sandwiched between glass plates of the same type and shape. Polymerization was performed by irradiating with ultraviolet rays under the same irradiation conditions as the exposure conditions for producing the pressure-sensitive adhesive sheet, and a polymer film for an evaluation test having a thickness of about 200 ⁇ m sandwiched between glass plates was obtained.
  • the polymerizable composition A4 to the polymerizable composition A6 and the polymerizable compositions B1 and B2 are each applied to a glass plate so as to have a film thickness of 200 ⁇ m, and sandwiched between resin plates (the above-mentioned two types).
  • the glass plate is irradiated with ultraviolet rays under the same irradiation conditions as described above to polymerize the glass.
  • a polymer film for an evaluation test having a film thickness of about 200 ⁇ m sandwiched between the plate and the resin plate was obtained.
  • a polymer film for an evaluation test which was manufactured using the polymerizable compositions A4 to A6 and the polymerizable compositions B1 and B2 and was sandwiched between the glass plate and the resin plate and having a thickness of about 200 ⁇ m, was tested.
  • the specimens AL4-2 to AL6-2 and specimens BL1-2 and BL2-2 were used.
  • the adhesion of these test pieces to the resin plate was measured by the method described later.
  • the results are shown in Table 4.
  • the below-mentioned peeling resistance test was done using these test pieces.
  • the results are shown in Table 5.
  • the peeling resistance test means that the above-mentioned test piece is placed in a thermostatic chamber of 60 ° C. and 90% RH and left for 72 hours, and the test piece is taken out in an environment of 23 ° C. and 50% RH and then tested for 48 hours. The piece was allowed to stand in an environment of 23 ° C. and 50% RH. Thereafter, the resin plate and the test pieces AS1-2 to AS6-2 and the test pieces BS1-2 and BS2-2 and the test piece AL4-2 to the test pieces AL6-2 and the test pieces BL1-2 and BL2-2 are visually observed.
  • a polymer film having a thickness of 2 mm obtained by polymerizing the polymerizable composition A1 to the polymerizable composition A6 and the polymerizable compositions B1 and B2 and peeling the PET film coated with silicone was respectively obtained.
  • Polymer film A1 to polymer film A6 and polymer films B1 and B2 are used.
  • Test piece AS1-2 to test piece AS6-2, test piece AL4-2 to test piece AL6-2, test piece BS1-2, BS2-2 and test piece BL1-2, BL2-2, outer glass surface and A plastic jig was affixed to the resin plate surface using a double-sided tape so that each could be sandwiched between chuck portions of a tensile tester. Thereafter, the film was pulled in the direction of peeling perpendicularly to the glass surface in the same manner as in the adhesion test to glass described above. The value obtained by dividing the breaking force by the coating area at that time was evaluated as the adhesion between the resin plate and the glass. The results are shown in Table 4.
  • the polymers obtained by polymerizing the polymerizable compositions of the present invention (I) to the present invention (III) have good adhesion to glass and are used under high temperature conditions or at high temperatures. It was found that even when stored for a long time under humid conditions, appearance changes such as coloring hardly occur, and good light transmittance can be maintained.
  • the polymerizable composition of the present invention (IV) has a low volume shrinkage during polymerization, and the polymer obtained by polymerizing the polymerizable composition of the present invention (IV) has an adhesive property to glass. It was found that good peeling resistance can be maintained even when stored for a long time under high temperature conditions or high temperature and high humidity conditions.
  • the polymer film obtained by polymerizing the polymerizable composition of the present invention (I) to the present invention (III) has good adhesion to glass and is used under high temperature conditions or high temperature and high humidity conditions. Even when stored for a long time, good peeling resistance can be maintained. Also, the dielectric constant is high. Furthermore, the polymerizable composition of the present invention (IV) has a low volume shrinkage during polymerization, and the polymer film obtained by polymerizing the polymerizable composition of the present invention (IV) is adhered to the resin plate. Good peeling resistance can be maintained even when stored for a long time under high temperature conditions or high temperature and high humidity conditions. Therefore, when the polymer film is used as a transparent optical resin layer interposed between the image display portion and the translucent protective portion of the image display device, a good optical adhesive layer can be provided. . Therefore, it is useful to use the polymer in an image display device.

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Abstract

Cette invention concerne une composition polymérisable pour former une couche polymère destinée à être interposée entre une partie d'affichage d'image et une partie protectrice transmettant la lumière, la composition polymérisable manifestant une excellente résistance au pelage par rapport à la partie d'affichage et à la partie protectrice. Cette composition polymérisable comprend un composé polymère contenant un groupe (méth)acryloyle ayant un poids moléculaire moyen en nombre dans la plage de 1000 à 15 000, et un amorceur de photopolymérisation, le polymère obtenu par polymérisation de ladite composition polymérisable ayant un module de conservation de 1×103 à 1×105 Pa à 25°C à une fréquence de 0,1 Hz. La composition polymérisable selon l'invention peut également comprendre, par exemple : un composé contenant un groupe insaturé polymérisable par voie radicalaire comprenant un groupe hydroxyle alcoolisé et/ou un groupe amido ; un composé contenant un groupe (méth)acryloyle ne comprenant ni groupe hydroxyle alcoolisé, ni groupe amido et ayant une viscosité de 500 mPa.s ou moins à 25°C ; et/ou un tensioactif non ionique dépourvu de groupe (méth)acryloyle.
PCT/JP2014/062093 2013-05-31 2014-05-01 Composition polymérisable, polymère, feuille adhésive optique, dispositif d'affichage d'image et son procédé de production WO2014192502A1 (fr)

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