WO2012077806A1 - 光学用粘着材樹脂組成物、光学用粘着材シート、画像表示装置、光学用粘着材シートの製造方法及び画像表示装置の製造方法 - Google Patents

光学用粘着材樹脂組成物、光学用粘着材シート、画像表示装置、光学用粘着材シートの製造方法及び画像表示装置の製造方法 Download PDF

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WO2012077806A1
WO2012077806A1 PCT/JP2011/078616 JP2011078616W WO2012077806A1 WO 2012077806 A1 WO2012077806 A1 WO 2012077806A1 JP 2011078616 W JP2011078616 W JP 2011078616W WO 2012077806 A1 WO2012077806 A1 WO 2012077806A1
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meth
image display
resin composition
acrylate
optical
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PCT/JP2011/078616
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English (en)
French (fr)
Japanese (ja)
Inventor
高橋　亨
高根　信明
和幸 加茂
良典 池内
林　克則
新谷　健一
会津　和郎
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日立化成工業株式会社
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Priority to CN201180059024.9A priority Critical patent/CN103249796B/zh
Priority to JP2012547933A priority patent/JP6166901B2/ja
Publication of WO2012077806A1 publication Critical patent/WO2012077806A1/ja

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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
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29D—PRODUCING PARTICULAR ARTICLES FROM PLASTICS OR FROM SUBSTANCES IN A PLASTIC STATE
    • B29D11/00—Producing optical elements, e.g. lenses or prisms
    • B29D11/0073—Optical laminates
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • 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
    • C08G18/40—High-molecular-weight compounds
    • C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
    • C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
    • C08G18/622—Polymers of esters of alpha-beta ethylenically unsaturated carboxylic acids
    • C08G18/6225—Polymers of esters of acrylic or methacrylic acid
    • C08G18/6229—Polymers of hydroxy groups containing esters of acrylic or methacrylic acid with aliphatic polyalcohols
    • 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
    • C08G18/8108—Unsaturated isocyanates or isothiocyanates having only one isocyanate or isothiocyanate group
    • C08G18/8116—Unsaturated isocyanates or isothiocyanates having only one isocyanate or isothiocyanate group esters of acrylic or alkylacrylic acid having only one isocyanate or isothiocyanate group
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/04—Homopolymers or copolymers of esters
    • C08L33/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
    • 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
    • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/04—Homopolymers or copolymers of esters
    • C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C09J133/062—Copolymers with monomers not covered by C09J133/06
    • C09J133/066—Copolymers with monomers not covered by C09J133/06 containing -OH groups
    • 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
    • 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
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
    • C09J7/38—Pressure-sensitive adhesives [PSA]
    • C09J7/381—Pressure-sensitive adhesives [PSA] based on macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • C09J7/385—Acrylic polymers
    • G—PHYSICS
    • G06—COMPUTING; CALCULATING OR COUNTING
    • G06F—ELECTRIC DIGITAL DATA PROCESSING
    • G06F3/00—Input arrangements for transferring data to be processed into a form capable of being handled by the computer; Output arrangements for transferring data from processing unit to output unit, e.g. interface arrangements
    • G06F3/01—Input arrangements or combined input and output arrangements for interaction between user and computer
    • G06F3/03—Arrangements for converting the position or the displacement of a member into a coded form
    • G06F3/041—Digitisers, e.g. for touch screens or touch pads, characterised by the transducing means
    • 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
    • C08F220/1808—C8-(meth)acrylate, e.g. isooctyl (meth)acrylate or 2-ethylhexyl (meth)acrylate
    • 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
    • C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
    • C09J2203/318—Applications of adhesives in processes or use of adhesives in the form of films or foils for the production of liquid crystal displays
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/133308—Support structures for LCD panels, e.g. frames or bezels
    • G02F1/133331—Cover glasses
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/13338—Input devices, e.g. touch panels
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F2202/00—Materials and properties
    • G02F2202/28—Adhesive materials or arrangements
    • G—PHYSICS
    • G06—COMPUTING; CALCULATING OR COUNTING
    • G06F—ELECTRIC DIGITAL DATA PROCESSING
    • G06F2203/00—Indexing scheme relating to G06F3/00 - G06F3/048
    • G06F2203/041—Indexing scheme relating to G06F3/041 - G06F3/045
    • G06F2203/04103—Manufacturing, i.e. details related to manufacturing processes specially suited for touch sensitive devices

Definitions

  • the present invention relates to an optical pressure-sensitive adhesive resin composition suitable for use in an image display device, a method for producing an optical pressure-sensitive adhesive sheet using the pressure-sensitive adhesive resin composition, an optical pressure-sensitive adhesive sheet, and the optical pressure-sensitive adhesive material.
  • the present invention relates to a method for manufacturing an image display device using a resin composition or an optical pressure-sensitive adhesive sheet and an image display device.
  • a typical image display device is a liquid crystal image display device (liquid crystal display (LCD)).
  • the liquid crystal image display device has a liquid crystal panel composed of a liquid crystal display cell and an optical film such as a polarizing plate attached to both outer surfaces thereof.
  • the liquid crystal display cell has a transparent electrode, a pixel pattern, etc. on the surface in advance.
  • the liquid crystal is filled and sealed through a gap of about several ⁇ m between a pair of glass substrates having a thickness of about 1 mm on which is formed.
  • An image display device typified by the liquid crystal image display device configured as described above is a display component that is thin and easily damaged. Therefore, in particular, in applications such as mobile phones, game machines, digital cameras, and in-vehicle components, a transparent front plate (protective panel) is generally provided on the front surface of the image display device through a certain space.
  • a polarizing plate is provided on the front surface of the liquid crystal panel.
  • the surface of the polarizing plate is antiglare (AG) treated, and visibility is improved by reducing light reflection on the front surface of the image display device.
  • members such as a front plate are not separately provided in order to improve the impact absorption of the device, and they are configured so that the entire liquid crystal panel and the entire set have impact resistance. ing.
  • the problems with such a large liquid crystal image display device are that the image appears blurred due to the AG processing, the liquid crystal panel is bent when touching the surface of the image display device, the image is disturbed, and the stain on the surface is removed due to the AG processing. On the other hand, scratches tend to occur when rubbed strongly.
  • the impact resistance of the liquid crystal panel itself is lowered, and there is a problem in the impact resistance of the image display device.
  • touch panels have been mounted on mobile phones, game machines, digital cameras, in-vehicle parts, notebook computers, desktop computers, personal computer monitors, and the like.
  • a front panel (protective panel), a touch panel, and a liquid crystal panel are stacked in this order, and between the front panel (protective panel) and the touch panel, A certain space exists between the touch panel and the liquid crystal panel.
  • this space causes light scattering, resulting in a decrease in contrast, brightness, and transmittance, and a decrease in image quality due to double projection. obtain.
  • a technique for filling the space with resin or the like is important.
  • a space of about 1 to 5 mm is provided on the front surface (viewing surface side) of the PDP in order to prevent cracking of the panel portion.
  • a front plate such as glass having a thickness of about 3 mm is provided.
  • the area of the front plate is also increased, so that the weight of the entire PDP tends to increase. Therefore, in order to prevent cracking of the image display device (display), a technique of laminating a specific resin on the display surface or a technique of laminating an optical filter on which the specific resin is laminated on the display surface has been proposed (Patent Literature). 7, 8, 9 and 10).
  • JP 05-11239 A Japanese Patent Laid-Open No. 03-204616 Japanese Patent Laid-Open No. 06-59253 JP 2004-125868 A Japanese Patent Laid-Open No. 06-333515 Japanese Patent Laid-Open No. 06-333517 JP 2004-58376 A JP 2005-107199 A JP 2004-263084 A Japanese Patent Laid-Open No. 2007-9115
  • the material that is most excellent in the step following property is a liquid material, but the liquid material has a problem in handling properties such as dripping.
  • thermoplastic resin can be cited as a material that is relatively excellent in level-step following, but when the heat resistance of an image display panel (liquid crystal panel) is not so high as in a liquid crystal image display device (liquid crystal display), the bonding temperature is set to be low. Since the temperature cannot be increased and the temperature difference between the bonding temperature and the use temperature becomes small, reliability cannot be ensured. Even in the above-mentioned references, there is no document describing the step following ability, and there is no pressure-sensitive adhesive sheet having a relatively thin film thickness and excellent step following ability and reliability.
  • a first object is to provide an optical pressure-sensitive adhesive resin composition suitable for the use of an image display device having followability and excellent handleability and adhesion.
  • a second object is to provide an optical pressure-sensitive adhesive sheet using the optical pressure-sensitive adhesive resin composition and a method for producing the same.
  • the present invention solves the above problems by using a resin composition containing a (meth) acrylate polymer and a side chain (meth) acryl-modified (meth) acrylate polymer. Found to get.
  • the present invention has been completed based on such knowledge. That is, the present invention (1) An optical pressure-sensitive adhesive resin composition comprising (A) (meth) acrylate polymer and (B) side chain (meth) acryl-modified (meth) acrylate polymer, (2) An optical pressure-sensitive adhesive material comprising: a step of applying the optical pressure-sensitive adhesive resin composition according to (1) above onto a substrate; and a step of curing the optical pressure-sensitive adhesive resin composition by light or heat.
  • the optical pressure-sensitive adhesive resin composition of the present invention is excellent in transparency because (A) (meth) acrylate polymer and (B) side chain (meth) acryl-modified (meth) acrylate are the same type of polymer. Moreover, since it is a sheet form before bridge
  • Liquid crystal display cells 20 and 22 Polarizing plate 30 Air gap (air layer) 32 Transparent resin layer 40 Front plate (transparent protective substrate) 50 Backlight System 60 Touch Panel 71 Glass Substrate 72 Print Layer 73 Adhesive Layer 74 Floating (Cavity)
  • the optical pressure-sensitive adhesive resin composition of the present invention is characterized by comprising (A) (meth) acrylate polymer and (B) side chain (meth) acryl-modified (meth) acrylate polymer. Then, the amount of modification of (B) side chain (meth) acryl-modified (meth) acrylate polymer and the content ratio of (A) (meth) acrylate polymer and (B) side chain (meth) acryl-modified (meth) acrylate polymer are changed. Thus, the hardness and adhesive strength of the cured product can be arbitrarily adjusted. In addition, by using a high molecular weight acrylic polymer for both (A) and (B), it is possible to maintain the film state even in an uncured state, and therefore, it should be a pressure-sensitive adhesive material with excellent handleability. Can do.
  • the (meth) acrylate polymer used in the present invention is a monomer compound having one (meth) acrylic acid-derived polymerizable unsaturated bond ((meth) acryloyl group) in the molecule. It contains at least a polymer obtained by polymerizing seeds or two or more kinds by a conventionally known method such as bulk polymerization, solution polymerization, suspension polymerization, emulsion polymerization or the like.
  • (meth) acryloyl groups derived from (meth) acrylic acid
  • monomer compounds a polymer obtained by copolymerization of these compounds
  • (A) (meth) acrylate polymer is a polymer obtained by adding another monomer compound having a polymerizable unsaturated bond in addition to the above (meth) acrylic acid monomer compound and copolymerizing them. There may be. However, it is distinguished from the component (B) described later in that it does not have a (meth) acryloyl group in the side chain.
  • the (A) (meth) acrylate polymer molecule has a purpose of improving adhesion to optical members such as a front plate such as glass and a touch panel, and a reactive point when (meth) acryl modification is performed on the side chain.
  • a polar group examples include hydroxyl groups, carboxyl groups, cyano groups, and glycidyl groups.
  • Polar groups that are effective as reaction sites include hydroxyl groups, carboxyl groups, and glycidyl groups. .
  • polar groups are achieved, for example, by copolymerizing a monomer compound having a polar group and a (meth) acrylic acid ester monomer compound such as alkyl (meth) acrylate.
  • a polar group such as a hydroxyl group
  • the resin composition can have an appropriate polarity to prevent white turbidity during moisture absorption.
  • the adhesive sheet or film member can be bonded to the surface of an optical member such as a front plate such as glass, a touch panel, or an image display panel without using an adhesive. Only one type of these polar group-containing monomers can be used, but a plurality of monomers may be used simultaneously.
  • the (meth) acrylate monomer compound constituting the (A) (meth) acrylate polymer includes acrylic acid, methacrylic acid, and derivatives thereof.
  • monomer compounds having one polymerizable unsaturated bond derived from (meth) acrylic acid in the molecule include monomers having a carboxyl group such as acrylic acid and methacrylic acid; methyl (meth) acrylate, n-butyl ( Carbon number of alkyl groups such as (meth) acrylate, isobutyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, isononyl (meth) acrylate, n-octyl (meth) acrylate, lauryl (meth) acrylate, stearyl (meth) acrylate (Meth) acrylates in which 1 to 18 are selected; Aralkyl (meth) acrylates in which aralkyl groups such as benzyl (meth) acrylate have 7
  • (meth) acrylates of polyalkylene glycol aryl ethers having 1 to 10 carbon atoms in the alkylene chain such as (meth) acrylates of hexaethylene glycol phenyl ether and 6 to 20 carbon atoms in the terminal aryl ethers; cyclohexyl (meta ) Acrylate, dicyclopentanyl (meth) acrylate, isobornyl (meth) acrylate, methylene oxide-added cyclodecatriene (meth) acrylate and other (meth) acrylates having a total carbon number of 4 to 30 Fluorinated alkyl (meth) acrylates having a total carbon number of 4 to 30 such as heptadecafluorodecyl (meth) acrylate; 2-hydroxyethyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (Meth) acrylate, mono (meth) acrylates of
  • (meth) acryl means acryl and methacryl, for example, (meth) acrylate means acrylate or methacrylate.
  • the expression of the same kind is meant to include two kinds of expressions.
  • the (meth) acrylate polymer as the component (A) preferably contains a structural unit derived from an alkyl (meth) acrylate having 4 to 18 carbon atoms in the alkyl group.
  • the structural unit derived from the alkyl (meth) acrylate having 4 to 18 carbon atoms in the alkyl group is preferably 40 to 90% by mass, and preferably 50 to 80% by mass, based on the total amount of the (meth) acrylate polymer as the component (A). Is more preferable, and 60 to 75% by mass is particularly preferable. It is more preferable to use a (meth) acrylate and / or acrylamide compound having a hydroxyl group in the molecule. That is, the (meth) acrylate polymer as the component (A) preferably contains a structural unit derived from a (meth) acrylate and / or acrylamide compound having a hydroxyl group in the molecule.
  • 2-ethylhexyl acrylate, 2-hydroxyethyl acrylate ((meth) acrylate having a hydroxyl group in the molecule) and acryloylmorpholine (acrylamide-based compound) are used in combination.
  • the case where a coalescence is used as a (A) (meth) acrylate polymer component is mentioned.
  • the ratio of the monomer compound having a hydroxyl group is not particularly limited, but is preferably 10 to 30% by mass with respect to the total monomer compounds to be used. When the monomer compound having a hydroxyl group is 10% by mass or more, it does not become cloudy at the time of moisture absorption.
  • the proportion of the acrylamide compound is preferably 8 to 15% by mass with respect to the total monomer compounds used. When the content is 8% by mass or more, sufficient adhesive force to the plastic front plate can be obtained, and when it is 15% by mass or less, bonding can be easily performed.
  • alkyl (meth) acrylates having 4 to 18 carbon atoms in the alkyl group, copolymers of (meth) acrylate and glycidyl (meth) acrylate having a hydroxyl group in the molecule.
  • This embodiment is particularly preferable in terms of impact absorption and transparency.
  • the compound When a monomer compound having two or more polymerizable unsaturated bonds derived from (meth) acrylic acid in the molecule is used in combination, the compound has 2 unsaturated bond sites of (meth) acrylic acid contributing to the polymerization reaction in the molecule.
  • monomer compounds include alkylene chains such as 1,4-butanediol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, and 1,9-nonanediol di (meth) acrylate.
  • the ratio shall be 0.3 mass% or less on the basis of the total mass of the monomer compound used as a constituent material of the polymer.
  • the other monomer compound that can be used in combination with the (meth) acrylate monomer compound when preparing the polymer of component (A) may be any compound having a polymerizable unsaturated bond in the molecule.
  • Specific examples include polymerizable compounds such as acrylonitrile, styrene, vinyl acetate, ethylene, and propylene.
  • the weight average molecular weight of the (A) (meth) acrylate polymer obtained by polymerization of the various monomer compounds is preferably 10,000 to 3,000,000 from the viewpoints of adhesive strength and impact absorption.
  • the weight average molecular weight of the (A) (meth) acrylate polymer is preferably 200,000 to 3,000,000, preferably 200,000 to 2 when a volatile solvent (C2) described later is used as a diluent. 1,000,000 are more preferable, and 300,000 to 1,000,000 are more preferable.
  • the weight average molecular weight is 200,000 or more, the resin layer does not tear or deform when subjected to an impact, and excellent high temperature reliability is obtained.
  • tack does not occur in the state of an uncured film, it is easy to handle, and is not deformed when cut into a predetermined dimension.
  • the weight average molecular weight is 3,000,000 or less, the viscosity does not become too high, so that a high pressure is not required when the molten resin is fed.
  • it is not necessary to lower the viscosity it is not necessary to increase the dilution rate with a solvent or the like, and a predetermined film thickness can be easily obtained after solvent drying. Further, the bubbles are easily removed, and the bubbles do not remain in the cured product.
  • the weight average molecular weight of (A) (meth) acrylate polymer is 10 from the point which can improve adhesive force, high temperature reliability, and a handleability, when using the (C1) monomer component mentioned later as a diluent. It is preferably from 30,000 to 700,000, more preferably from 30,000 to 500,000, and particularly preferably from 50,000 to 400,000.
  • the “weight average molecular weight” described in the present specification means a value obtained by measurement using a standard polystyrene calibration curve by gel permeation chromatography.
  • the content of the (A) (meth) acrylate polymer in the optical pressure-sensitive adhesive resin composition of the present invention is 10 to 10% based on the total amount of the optical pressure-sensitive adhesive resin composition when the component (C1) described later is used. It is preferably 70% by mass, more preferably 15 to 60% by mass, and particularly preferably 20 to 50% by mass. When the pressure-sensitive adhesive sheet is within the above range, the viscosity can be improved when the pressure-sensitive adhesive sheet is produced, and the transparency and reliability of the resulting pressure-sensitive adhesive sheet can be further improved.
  • the content of the (A) (meth) acrylate polymer is in the range of 50 to 90% by mass with respect to the total amount of the component (A) and the component (B) when the component (C2) described later is used.
  • the range of 60 to 80% by mass is more preferable.
  • the content of the polymer component (A) is 50% by mass or more, there is no problem in mechanical properties, and the impact absorbability of the optical resin material may be reduced or the adhesive strength may be reduced. Absent.
  • the content is 90% by mass or less, the retention of the cured product is ensured and high reliability is obtained.
  • the (B) side chain (meth) acryl-modified (meth) acrylate polymer used in the present invention may be any (meth) acrylate polymer having a side chain modified with a (meth) acryloyl group. ) And a structural unit represented by the following general formula (2), and the (meth) acrylate polymer before modification is more preferably the component (A).
  • the (A) component side chain is (meth) acryl modified to form the (B) component so that the structures of the (A) component and the (B) component are almost equal, so the compatibility is excellent and the transparency is low. A high cured product can be obtained.
  • a structural unit having a hydroxyl group or a structural unit having a carboxyl group represented by the following general formula (3) in the component (A) is incorporated in the main chain of the polymer.
  • a structural unit having a glycidyl group as represented by the following general formula (5) is provided in the main chain of the polymer and (meth) acrylic acid is added thereto.
  • the hydroxyl group as represented by the following general formula (3) has an isocyanate group such as 2-isocyanatoethyl (meth) acrylate (A method of adding (meth) acrylate or a method of adding (meth) acrylic acid to a glycidyl group as represented by the following general formula (5) is more preferable.
  • a (meth) acrylate having an isocyanate group is added to a hydroxyl group represented by the following general formula (3), the (meth) acrylate having an isocyanate group is added in an amount of 0.01 to 0. It is preferable to add such that the ratio is 9 equivalents.
  • R represents hydrogen or a methyl group
  • R 1 represents an alkyl group having 4 to 18 carbon atoms or an alicyclic alkyl group
  • X represents —CH 2 CH 2 —, — (CH 2 CH 2 O).
  • R represents hydrogen or a methyl group
  • R 2 represents an alkylene group having 1 to 10 carbon atoms or an alicyclic alkylene group.
  • R represents hydrogen or a methyl group
  • R 3 represents an alkylene group having 1 to 10 carbon atoms or an alicyclic alkylene group.
  • R represents hydrogen or a methyl group
  • R 4 represents an alkylene group having 1 to 10 carbon atoms or an alicyclic alkylene group.
  • the weight average molecular weight of the component (B) is preferably about the same as that of the component (A), but it can be used even if the weight average molecular weight is somewhat low because it undergoes side chain modification. Specifically, it is preferably 10,000 to 3,000,000, more preferably 50,000 to 3,000,000, particularly preferably 100,000 to 3,000,000, and 200,000 to 2,000. , 000 is more preferred, and 300,000 to 1,000,000 is even more preferred. In addition, when a monomer component such as a (meth) acrylate monomer described later is used in the optical adhesive material resin composition, the weight average molecular weight of the component (B) is 1,000 to 700, 000 is preferable, and 50,000 to 400,000 is more preferable.
  • the optimal content of the component (B) varies depending on the modification rate of the side chain. However, if the content is too large, the adhesive strength is reduced, and problems such as easy peeling and bubbles are likely to occur. On the other hand, if the amount is too small, the holding force is lowered and the reliability tends to be lowered. From the above points, the content of the component (B) is preferably 20% by mass or less, more preferably 10% by mass or less, and more preferably 7% by mass with respect to the total amount of the optical adhesive resin composition. % Is most preferred. When the content of the component (B) is 20% by mass or less, an adhesive sheet having excellent adhesiveness and having no brittleness even if the elastic modulus is high is obtained.
  • (B) component Although there is no restriction
  • the content is more preferably 0.5% by mass or more, more preferably 1% by mass or more, and particularly preferably 3% by mass or more.
  • the optical adhesive material resin composition of the present invention may contain a diluent as the component (C) as necessary in addition to the components (A) and (B).
  • Diluents include (C1) monomer components and (C2) volatile solvents.
  • the (C1) monomer component is preferably a (meth) acrylate monomer that is liquid at 20 ° C., particularly from the viewpoints of viscosity adjustment, adhesive strength, transparency, high temperature reliability, and pressure-sensitive adhesive sheet formability.
  • Examples of the (meth) acrylate monomer include those similar to the (meth) acrylate monomer compound constituting the (meth) acrylate polymer of the component (A).
  • the content of the monomer component is preferably 5 to 80% by mass, particularly preferably 10 to 70% by mass, and particularly preferably 40 to 70% by mass with respect to the total amount of the optical adhesive resin composition. % Is particularly preferred.
  • the content of the monomer component is within the above range, the adhesiveness and the high temperature reliability can be further improved, and the generation of bubbles can be further suppressed.
  • the (C2) volatile solvent is suitably used for adjusting the viscosity to a desired thickness while applying an appropriate viscosity to prevent the entrainment of bubbles when the optical adhesive resin composition is applied.
  • various general-purpose solvents such as ketone solvents such as acetone and 2-butanone, ether solvents such as tetrahydrofuran (THF), and aromatic solvents such as toluene can be used.
  • Butanone and methyl isobutyl ketone are more preferable.
  • two or more solvents having different boiling points may be used in combination.
  • a small amount of the (C1) monomer component, plasticizer, or the like may be added.
  • a polymerization initiator is further contained in addition to (A) component, (B) component, (C1) monomer component, and (C2) volatile solvent.
  • a polymerization initiator of (D) component is not necessarily essential.
  • the polymerization initiator when the polymerization reaction is carried out, for example, by irradiation with an electron beam, the polymerization reaction may proceed without a polymerization initiator. Therefore, in the present invention, the polymerization initiator is appropriately used when the polymerization reaction does not proceed unless it is used or the polymerization reaction does not proceed easily.
  • the polymerization initiator that can be used in the present invention may be either a photopolymerization initiator or a thermal polymerization initiator, or may be used in combination. Among these, it is more preferable to use a photopolymerization initiator in order to avoid reaction during solvent drying. Moreover, when using a thermal polymerization initiator, it is more preferable to use the polymerization initiator whose 10-hour half-life temperature is higher than the boiling point of a solvent.
  • the polymerization reaction may proceed even without a polymerization initiator. That is, the polymerization reaction for curing the optical pressure-sensitive adhesive resin composition of the present invention can be carried out by a curing method using irradiation with active energy rays, heat, or a combination thereof.
  • active energy ray refers to ultraviolet rays, electron beams, ⁇ rays, ⁇ rays, ⁇ rays and the like.
  • the above-described curing method can also be used for the synthesis of the (meth) acrylate polymer as the component (A) in the optical pressure-sensitive adhesive resin composition.
  • the content of the polymerization initiator is preferably in the range of 0.01 to 5% by mass relative to the total amount of the components (A), (B), (C) and (D).
  • a range of 01 to 3% by mass is more preferable, and a range of 0.03 to 2% by mass is particularly preferable.
  • the range of 0.1 to 5% by mass is preferable with respect to the total amount of the above components (A) to (D), and the range of 0.3 to 3% by mass is preferable.
  • a range of 0.5 to 2% by mass is particularly preferable.
  • the range of 0.01 to 1% by mass is preferable with respect to the total amount of the components (A) to (D), and the range of 0.01 to 0.5% by mass is preferable. More preferred.
  • the photopolymerization initiator used in the present invention can be selected from known compounds such as benzophenone series, anthraquinone series, benzoin series, sulfonium salts, diazonium salts, onium salts and the like. These photopolymerization initiators have high sensitivity to light, particularly ultraviolet rays.
  • compounds that can be used as photopolymerization initiators include benzophenone, N, N′-tetramethyl-4,4′-diaminobenzophenone (Michler ketone), N, N-tetraethyl-4,4′-diaminobenzophenone, 4-methoxy-4'-dimethylaminobenzophenone, ⁇ -hydroxyisobutylphenone, 2-ethylanthraquinone, t-butylanthraquinone, 1,4-dimethylanthraquinone, 1-chloroanthraquinone, 2,3-dichloroanthraquinone, 3-chloro- 2-methylanthraquinone, 1,2-benzoanthraquinone, 2-phenylanthraquinone, 1,4-naphthoquinone, 9,10-phenanthraquinone, thioxanthone, 2-chlorothioxanthone,
  • the compounds exemplified above as the photopolymerization initiator may be used alone or in combination of two or more, and it is preferable to select an appropriate compound according to the purpose.
  • an appropriate compound for example, in order not to color the resin composition, it is preferable to use the following compounds alone or in combination of two or more.
  • acylphosphine oxide compounds such as -trimethyl-pentylphosphine oxide and 2,4,6-trimethylbenzoyl-diphenylphosphine oxide.
  • oligo (2-hydroxy-2-methyl-1- (4- (1-methylvinyl) phenyl) propanone) and oxy-phenyl-acetic acid 2- [2
  • Preference is given to using at least one of a mixture of -oxo-2-phenyl-acetoxy-ethoxy] -ethyl ester and oxy-phenyl-acetic acid 2- [2-hydroxy-ethoxy] -ethyl ester.
  • oxy-phenyl-acetic acid 2- [2-oxo-2-phenyl-acetoxy-ethoxy] -ethyl ester and oxy-phenyl-acetic acid 2- [2 Preference is given to using mixtures with -hydroxy-ethoxy] -ethyl esters.
  • the thermal polymerization initiator is an initiator that generates radicals by heat, and specifically includes benzoyl peroxide, t-butyl perbenzoate, cumene hydroperoxide, diisopropyl peroxydicarbonate, diisopropyl peroxide.
  • the optical adhesive resin composition of the present invention may contain various stabilizers.
  • the stabilizer include polymerization inhibitors such as paramethoxyphenol used for the purpose of enhancing the storage stability of the resin composition, and triphenylphosphine used for enhancing the heat resistance of the cured product of the resin composition.
  • HALS hindered amine light stabilizers
  • a plurality of these stabilizers may be used in combination.
  • other additives may be used as long as the effects of the present invention are obtained.
  • the optical pressure-sensitive adhesive sheet of the present invention preferably uses (C1) a monomer component and / or (C2) a volatile solvent as the (C) diluent.
  • (C2) a volatile solvent used, the manufacturing method in the case of using (C1) monomer component will be described.
  • (C) In the case of using (C2) a volatile solvent as a diluent, the optical adhesive material resin composition is applied to a substrate or the like, and then the volatile solvent is distilled off from the resin composition to adhere. It is characterized by a sheet.
  • the pressure-sensitive adhesive sheet of the present invention is applied to a substrate or the like with the optical pressure-sensitive adhesive resin composition as it is using a general-purpose coating machine, and then a volatile solvent. It is obtained by distilling off.
  • a drying furnace is used to distill off the volatile solvent.
  • a normal blower dryer can be used, but a dryer using infrared rays can also be used.
  • the optical adhesive resin composition of the present invention is applied onto a substrate. And a step of curing the optical pressure-sensitive adhesive resin composition by light or heat. More specifically, the optical adhesive resin composition is applied as it is to a desired thickness on a base material using a general-purpose coating machine, and then irradiated with active energy rays such as ultraviolet rays. Obtained by curing.
  • the optical pressure-sensitive adhesive sheet of the present invention protects the pressure-sensitive adhesive sheet on the surface opposite to the substrate surface side of the optical pressure-sensitive adhesive resin composition layer (pressure-sensitive adhesive sheet) after curing the optical pressure-sensitive adhesive resin composition. In order to do so, another substrate may be laminated.
  • the storage elastic modulus at 25 ° C. of the optical pressure-sensitive adhesive sheet thus obtained is preferably 1.0 ⁇ 10 3 Pa or more and 1.0 ⁇ 10 6 Pa or less, and 1.0 ⁇ 10 4 Pa or more. More preferably, it is 5.0 ⁇ 10 5 Pa or less. Further, from the viewpoint of suppression of bleeding and generation of bubbles, tan ⁇ at 25 to 50 ° C.
  • the glass transition temperature of the optical pressure-sensitive adhesive sheet is preferably in the range of 0 to 30 ° C., and in the range of 10 to 30 ° C. It is more preferable.
  • the peel strength (peel strength) of the optical pressure-sensitive adhesive sheet to the glass (soda lime glass) substrate is preferably 5 N / 10 mm or more and 30 N / 10 mm or less, and preferably 10 N / 10 mm or more and 25 N / 10 mm or less. More preferred.
  • the thickness of the pressure-sensitive adhesive sheet is preferably from 100 ⁇ m to 500 ⁇ m, and more preferably from 150 ⁇ m to 400 ⁇ m.
  • the dielectric constant at 100 kHz of the optical pressure-sensitive adhesive sheet of the present invention is preferably 5 or less, more preferably 4 or less, and particularly preferably 3 or less.
  • a polyester film such as polyethylene terephthalate, a polyolefin such as polypropylene and polyethylene, etc. are preferably used, and among them, a polyethylene terephthalate film (hereinafter referred to as “PET”).
  • PET polyethylene terephthalate film
  • the film is preferably a “film”, and more preferably a PET film whose surface has been release-treated.
  • the thickness of the substrate is preferably 25 ⁇ m or more and 200 ⁇ m or less, and more preferably 30 ⁇ m or more and 150 ⁇ m or less from the viewpoint of handleability.
  • an optical pressure-sensitive adhesive sheet is bonded to the front plate, and the surface opposite to the front plate of the optical pressure-sensitive adhesive sheet is bonded to the image display panel; Then, a method of irradiating with ultraviolet rays, and (2) a method of attaching an optical adhesive sheet to the front plate, irradiating with ultraviolet rays, and then attaching the surface opposite to the front plate of the optical adhesive sheet to the image display panel.
  • the optical pressure-sensitive adhesive sheet is bonded to the front plate before irradiating with ultraviolet rays, the elastic modulus can be lowered by thermal lamination, and high step following ability can be exhibited.
  • the manufacturing method of (1) irradiates ultraviolet rays after bonding two surfaces, it is easy to obtain high adhesion on each surface. Partially insufficient curing may cause problems such as generation of bubbles and coloring.
  • insufficient curing occurs, there are a method of irradiating ultraviolet rays from the side and a method of reacting an uncured part by thermal polymerization using a thermal polymerization initiator in combination, and the insufficient curing can be solved.
  • ultraviolet light is irradiated after one surface is bonded to the front plate, so even if there is a portion that does not allow ultraviolet light to pass through the front plate by irradiating ultraviolet light from the adhesive sheet side.
  • the adhesive force tends to be low.
  • it can be set as the adhesive sheet which shows sufficient adhesive force after ultraviolet irradiation by adjusting the usage-amount of (B) component.
  • the ultraviolet irradiation device used here is not particularly limited, and a known ultraviolet irradiation device such as a single wafer type or a conveyor type can be used.
  • the light source for ultraviolet irradiation may be a low pressure mercury lamp, a medium pressure mercury lamp, a high pressure mercury lamp, a metal halide lamp, an LED lamp or the like, but it is preferable to use a high pressure mercury lamp or a metal halide lamp.
  • the reaction can be carried out in an inert gas atmosphere.
  • a method not subject to oxygen inhibition a method of using a vacuum laminating apparatus for bonding, and irradiating ultraviolet rays under vacuum after bonding is also included.
  • cured material of the optical adhesive material resin composition of this invention is 30 degrees C or less, and it is more preferable that it is 0 degrees C or less.
  • Tg is more preferably ⁇ 20 to ⁇ 60 ° C.
  • the visible light transmittance is in the visible light region (wavelength: 380 to 780 nm) in the film after coating and curing. It is preferably 80% or more, and more preferably 90% or more.
  • the optical pressure-sensitive adhesive resin composition of the present invention can be used as it is in a liquid state by being applied to an image display panel or a front plate and bonded together, or filled in a gap between two members to be bonded together.
  • the optical pressure-sensitive adhesive sheet produced by the above-described method for producing an optical pressure-sensitive adhesive sheet of the present invention may be used.
  • the image display apparatus of this invention using these optical adhesive material resin compositions and optical adhesive material sheets, and its manufacturing method are also provided.
  • a self-supporting sheet or film can be prepared in advance by a curing reaction of the optical pressure-sensitive adhesive resin composition, and these can be used.
  • a method such as a casting method.
  • the curing reaction of the optical adhesive resin composition can be performed by heating, or by irradiating light rays such as ultraviolet rays and radiation such as electron beams.
  • the film thickness is preferably 0.01 mm to 3 mm.
  • the optical pressure-sensitive adhesive sheet formed into the shape of such a sheet or film can be laminated as it is on the surface of an image display panel or image display device or an optical filter, but may also be laminated via an adhesive or an adhesive. it can.
  • the front plate in the present invention is a front plate used in an image display device, and for example, a transparent protective substrate of a liquid crystal display device or the like, and may be a general optical transparent substrate.
  • a transparent protective substrate of a liquid crystal display device or the like may be a general optical transparent substrate.
  • Specific examples include inorganic plates such as glass plates and quartz plates, resin plates such as acrylic plates and polycarbonate plates, and resin sheets such as thick polyester sheets.
  • These front plates (transparent protective substrates) can be used in combination of a plurality of sheets, or can be used by integrally stacking a plurality of sheets.
  • Functional layers such as an antireflection layer, an antifouling layer, a dye layer, and a hard coat layer may be laminated on the surface of these front plates (transparent protective substrate) as necessary.
  • the surface treatment may be performed on one side of the front plate (transparent protective substrate) or on both sides.
  • image display devices examples include plasma displays (PDP), liquid crystal displays (LCD), cathode ray tubes (CRT), field emission.
  • PDP plasma displays
  • LCD liquid crystal displays
  • CRT cathode ray tubes
  • FED field emission
  • organic EL display organic EL display
  • electronic paper etc.
  • a functional layer may be laminated on the surface of such an image display device.
  • the antireflection layer exemplified as the functional layer only needs to have antireflection properties such that the reflectance with respect to visible light is 5% or less, and is processed by a known antireflection method on a transparent substrate such as a transparent plastic film.
  • Layer can be used.
  • the antifouling layer is used for preventing dirt from adhering to the surface, and can be composed of a known material.
  • an antifouling layer is comprised from a fluorine resin, a silicone resin, etc.
  • the dye layer is used to reduce unnecessary light and increase color purity, and is effective when the color purity of light emitted from an image display panel such as a liquid crystal panel is low.
  • a dye that absorbs light in unnecessary areas in a resin By dissolving a dye that absorbs light in unnecessary areas in a resin and forming or laminating it on a base film such as a polyethylene film or a polyester film, or by mixing the dye with an adhesive. It is possible to form.
  • the hard coat layer is used to increase the surface hardness.
  • the hard coat layer can be formed by forming or laminating an acrylic resin such as urethane acrylate or epoxy acrylate, an epoxy resin, or the like on a base film such as a polyethylene film.
  • a vacuum laminator In order to suppress bubbles at the time of bonding, it is preferable to use a vacuum laminator.
  • air bubbles can be reduced by heat and pressure treatment (autoclave treatment) after bonding.
  • the autoclave treatment is performed at 40 to 80 ° C. (preferably 50 to 70 ° C.), 0.3 to 0.8 MPa (preferably 0.4 to 0.7 MPa), 5 to 60 minutes (preferably 10 to 50). Min).
  • the liquid crystal display cell incorporated in a liquid crystal image display apparatus is not specifically limited, You may be comprised from a liquid-crystal material known in this technical field.
  • the liquid crystal material is classified into TN (Twisted Nematic), STN (Super-twisted nematic), VA (Virtual Alignment), IPS (In-Place-Switching), etc. according to the present invention. It may be a liquid crystal display cell using the method.
  • FIG. 1 and 2 are side cross-sectional views schematically showing an example of the structure of a conventional liquid crystal image display device.
  • the liquid crystal image display device shown in FIG. 1 has a liquid crystal display cell 10, polarizing plates 20 and 22 attached to both surfaces thereof, and a gap 30 on the upper surface of the polarizing plate 20 on the viewing side of the liquid crystal image display device.
  • a backlight system 50 provided on the lower surface of the polarizing plate 22.
  • the liquid crystal display cell 10 is a structure in which a liquid crystal material is sealed in two sheets of glass (not shown), and polarizing plates 20 and 22 are attached to the respective glass surfaces (liquid crystal panel).
  • the backlight system 50 typically includes a reflecting unit such as a reflecting plate and an illuminating unit such as a lamp.
  • the liquid crystal image display device shown in FIG. 2 is shown in FIG. 1 except that no front plate (transparent protective substrate) is provided on the upper surface (front surface) of the polarizing plate 20 on the viewing side of the liquid crystal image display device.
  • the configuration is the same as that of a liquid crystal display device.
  • FIG. 3 is a side sectional view schematically showing an example of the structure of the liquid crystal display device according to the present invention.
  • the liquid crystal image display device shown in FIG. 3 corresponds to the conventional liquid crystal image display device shown in FIG. 1, and the gap 30 is a transparent resin layer 32. That is, the liquid crystal image display device shown in FIG. 3 is provided on the upper surface of the liquid crystal display cell 10, the polarizing plates 20 and 22 attached to both surfaces thereof, and the polarizing plate 20 on the viewing side of the liquid crystal image display device.
  • the liquid crystal image display device having such a configuration is hard to break because the impact resistance is improved by the combination of the front plate (transparent protective substrate) and the transparent resin layer.
  • the optical adhesive resin composition of the present invention is filled between the front plate and the plasma display panel (image display panel) and cured, or the optical display of the present invention is used.
  • the image display device includes an image display panel, a touch panel, and a front plate, and the present invention is provided between the image display panel and the touch panel and / or between the touch panel and the front plate. It has a transparent resin layer formed from the optical adhesive material resin composition or optical adhesive material sheet.
  • the polarizing plate in the liquid crystal image display device is attached to the liquid crystal display cell and is a part of the liquid crystal panel (image display panel), it is attached to the touch panel and a part of the touch panel.
  • the polarizing plate is included in the definition as a part of the attached object (that is, defined as a part of their structure).
  • FIG. 4 is a side sectional view schematically showing an example of the structure of a conventional liquid crystal image display device having a touch panel.
  • This is a structure in which a touch panel 60 arranged via a gap is added to the upper surface of the polarizing plate 20 on the viewing side of the image display device in FIG. For this reason, in FIG. 4, there are two voids, and a decrease in display quality due to reflection at the interface is observed.
  • the liquid crystal image display device shown in FIG. 5 corresponds to the conventional liquid crystal image display device shown in FIG. 4, and uses the optical adhesive resin composition or the optical adhesive sheet of the present invention for two voids.
  • the transparent resin layer 32 was used. By adopting such a structure, both the function of the touch panel and the display quality can be achieved.
  • FIG. 6 is a side sectional view schematically showing an example of a structure called an on-cell type.
  • a touch panel 60 and a polarizing plate 20 are provided on the viewing side of the liquid crystal display cell 10, and a transparent resin layer 32 and a front plate (transparent protective substrate) 40 are provided on the viewing side of the polarizing plate.
  • the touch panel 60 may be integrated with the front plate (transparent protective substrate) 40 instead of the liquid crystal display cell.
  • the dielectric constant of the transparent resin layer 32 is lower from the viewpoint of reducing malfunction.
  • the front plate, image display panel or touch panel has a step of 10 to 80 ⁇ m (for example, FIG. 8), the front plate and touch panel, touch panel and image display panel, or front plate and image display panel are optical adhesive sheets. It is preferable to perform the above-mentioned autoclave treatment (heating and pressurizing treatment) from the viewpoint of further removing bubbles in the vicinity of the step after the bonding step.
  • autoclave treatment heating and pressurizing treatment
  • the weight average molecular weight is measured using gel permeation chromatography using tetrahydrofuran (THF) as a solvent, and converted using a standard polystyrene calibration curve using the following apparatus and measurement conditions. It is the determined value.
  • GPC device manufactured by Tosoh (high-speed GPC device HCL-8320GPC)
  • Solvent THF Column: Made by Tosoh (Column TSKge SuperMultipore HZ-H) Column temperature: 40 ° C Flow rate: 0.35 ml / min
  • Each optical pressure-sensitive adhesive sheet obtained in Examples 1 to 5 and Comparative Examples 1 and 2 was evaluated by the following test methods.
  • Step following capability Kapton tape is attached to the surface of a glass plate to prepare a step of 100 ⁇ m, and using an optical adhesive sheet obtained in each example and comparative example, 80 cm, 60 cm at a pressure of 0.2 MPa. Bonding was performed at a speed of / min, and the presence or absence of generation of bubbles at the step portion was visually confirmed. Moreover, it was left to stand at room temperature for 3 days, and the presence or absence of the bubble generation
  • a cured product was prepared by irradiating the optical adhesive sheet obtained in each Example and Comparative Example with 2,000 mJ / cm 2 of ultraviolet light in an inert gas atmosphere, and the following various property confirmation tests Went.
  • (1) Total light transmittance The transparency of the cured product thus prepared was evaluated by measuring the total light transmittance using a color difference / turbidity measuring device COH-300A (manufactured by Nippon Denshoku Industries Co., Ltd.). did.
  • (2) Adhesive strength The prepared cured product was cut into a width of 25 mm, bonded to glass or an acrylic plate, and subjected to a 180 ° peeling test with a peeling tester to measure the adhesive strength.
  • the test was performed at a test temperature of 80 ° C. and a peeling rate of 300 mm / min. (3) Moisture resistance reliability
  • the prepared cured product was placed in a high-temperature and high-humidity test tank at 60 ° C. and 90% RH for 50 hours to conduct a moisture absorption test, and then the appearance change of the sheet was visually observed.
  • the optical adhesive material sheet not irradiated with ultraviolet rays obtained in each of Examples and Comparative Examples was used as a transparent plastic front panel [polycarbonate plate (40 mm ⁇ 50 mm) MR58, thickness: 1 mm, manufactured by Mitsubishi Gas Chemical Co., Ltd.] And a laminator, and this was further laminated to a glass plate by a vacuum laminator. Thereafter, the bubbles generated at the time of bonding were removed by treatment at 0.5 MPa and 60 ° C. for 30 minutes with an autoclave, and ultraviolet rays were irradiated at 2,000 mJ / cm 2 to prepare a cured product. Thereafter, it was placed in a high-temperature test bath at 85 ° C. for 50 hours to conduct a high-temperature test, and then the appearance change was visually observed.
  • Production Example 1 (Preparation of acrylate polymer) Weigh 35.0 g of 2-ethylhexyl acrylate, 15.0 g of 2-hydroxyethyl acrylate, and 50.0 g of 2-butanone as initial monomers in a reaction vessel equipped with a cooling tube, thermometer, stirring device, dropping funnel and nitrogen injection tube. Then, it was heated from room temperature to 75 ° C. over 15 minutes while purging with nitrogen at a flow rate of 100 ml / min.
  • Production Example 2 (Preparation of acrylate polymer) An acrylate polymer was synthesized in the same manner as in Production Example 1 except that the amount of azobisisobutyronitrile was 0.01 g in Production Example 1. The resulting copolymer had a weight average molecular weight of 690,000.
  • Production Example 3 (Preparation of acrylate polymer) A reaction vessel equipped with a cooling tube, a thermometer, a stirring device, a dropping funnel and a nitrogen injection tube was used as an initial monomer, and 35.0 g of 2-ethylhexyl acrylate, 13.22 g of 2-hydroxyethyl acrylate, 1.78 g of 2-glycidyl methacrylate and 2- 50.0 g of butanone was weighed and heated from room temperature to 75 ° C. over 15 minutes while purging with nitrogen at a flow rate of 100 ml / min.
  • Production Example 4 (Preparation of side chain methacryl-modified acrylate polymer)
  • a reaction vessel equipped with a cooling pipe, a thermometer, a stirrer, a dropping funnel and a gas injection pipe 80.0 g of 2-butanone solution of the acrylate polymer obtained in Production Example 1 and 0.07 g of dibutyltin dilaurate were weighed. While flowing dry air at a flow rate of 100 ml / min, heating was performed from room temperature to 50 ° C. over 15 minutes. Thereafter, while maintaining the temperature at 50 ° C., 0.88 g of 2-isocyanatoethyl methacrylate was added dropwise. The reaction was continued for another 6 hours after the addition. After 6 hours, it was confirmed by IR measurement that the isocyanate bond had disappeared, and the reaction was completed.
  • Production Example 5 (Preparation of side chain acrylic modified acrylate polymer) 80.0 g of 2-butanone solution of acrylate polymer obtained in Production Example 3, 0.8 g of acrylic acid, triphenylphosphine,. 08 g and 0.4 g of paramethoxyphenol were weighed and heated from room temperature to 90 ° C. over 15 minutes while flowing dry air at a flow rate of 100 ml / min. Thereafter, the reaction was carried out for 10 hours. After 10 hours, the reaction was completed after confirming that acrylic acid had disappeared by titration.
  • Example 1 (1) Preparation of optical adhesive resin composition for optical use 10.00 g of 2-butanone solution of acrylate polymer prepared in Production Example 1, 4.00 g of 2-butanone solution of side chain methacryl-modified acrylate polymer prepared in Production Example 4, (D) As polymerization initiators, 0.60 g of 1-hydroxy-cyclohexyl-phenyl-ketone (manufactured by BASF Japan Ltd., trade name “Irgacure-184”) was weighed and placed in a reaction vessel, and a three-one motor was used. Then, an optical pressure-sensitive adhesive resin composition was prepared by stirring and mixing at room temperature (25 ° C.) for 30 minutes.
  • optical pressure-sensitive adhesive sheet The optical pressure-sensitive adhesive resin composition obtained in (1) above was coated on an PET film having a surface subjected to a release treatment using an applicator. An optical pressure-sensitive adhesive sheet was prepared by drying at 80 ° C. for 30 minutes. This optical pressure-sensitive adhesive sheet had almost no stickiness at room temperature. The thickness of the optical pressure-sensitive adhesive sheet was 150 ⁇ m. As a result of the evaluation by the above method, no bubble was generated at the step portion with respect to the step following property, and no bubble was observed even after 3 days. The total light transmittance was 91.2%, and the adhesive strength was 30 N / 25 mm. In the moisture resistance reliability test, the sheet after the moisture absorption test showed no cloudiness and the transparency was good. In the high-temperature reliability test, no bubbles were observed after the test, and no positional deviation between MR-58 and the glass plate was observed.
  • Example 2 In Example 1, instead of the 2-butanone solution of the acrylate polymer prepared in Production Example 1, the optical solution was the same as in Example 1 except that the 2-butanone solution of the acrylate polymer prepared in Production Example 2 was used. A pressure-sensitive adhesive resin composition was prepared. Evaluation was performed in the same manner as in Example 1. The optical pressure-sensitive adhesive sheet obtained in Example 2 had almost no stickiness at room temperature and exhibited good step following ability. Further, the total light transmittance was 90.8%, the adhesive strength was 23 N / 25 mm, and both the moisture resistance reliability and the high temperature reliability were good.
  • Example 3 (1) Preparation of optical adhesive resin composition for optical use 10.00 g of 2-butanone solution of acrylate polymer prepared in Production Example 3, 4.00 g of 2-butanone solution of side chain acrylic modified acrylate polymer prepared in Production Example 5, (D) As polymerization initiators, 0.60 g of 1-hydroxy-cyclohexyl-phenyl-ketone (manufactured by BASF Japan Ltd., trade name “Irgacure-184”) was weighed and placed in a reaction vessel, and a three-one motor was used. Then, an optical pressure-sensitive adhesive resin composition was prepared by stirring and mixing at room temperature (25 ° C.) for 30 minutes.
  • Irgacure-184 1-hydroxy-cyclohexyl-phenyl-ketone
  • optical adhesive sheet was produced in the same manner as in Example 1 except that the optical adhesive resin composition obtained in (1) above was used.
  • This optical pressure-sensitive adhesive sheet had almost no stickiness at room temperature.
  • the thickness of the optical pressure-sensitive adhesive sheet was 150 ⁇ m.
  • good step following ability was exhibited as in Example 1, the total light transmittance was 90.3%, and the adhesive strength was 26 N / 25 mm. Moreover, both moisture resistance reliability and high temperature reliability were good.
  • Example 4 The optical pressure-sensitive adhesive sheet of Example 1 was bonded to a glass front plate having black printing on the outer peripheral portion while being heated and pressurized with a roll laminator. No bubbles were observed in the printed part. Next, it was bonded to the liquid crystal panel with a vacuum laminator. After bonding, air bubbles generated at the time of bonding were removed by treatment with an autoclave at 0.5 MPa and 60 ° C. for 30 minutes. Furthermore, it was cured by irradiating with 2,000 mJ / cm 2 of ultraviolet rays using an ultraviolet irradiating device to produce a liquid crystal panel with a front plate.
  • this liquid crystal panel with a front panel was subjected to a high temperature test for 50 hours in a high temperature test tank at 85 ° C. and a high temperature and high humidity test for 50 hours in a high temperature and high humidity tank at 60 ° C. and 90% RH. Observed. Generation of bubbles was not observed in any of the high temperature test and the high temperature and high humidity test. In addition, no change in color or peeling was observed, and good reliability was exhibited. In addition, when it was installed in a housing and checked for operation, it was confirmed that it operated without problems.
  • Example 5 The optical pressure-sensitive adhesive sheet of Example 1 was bonded to a glass front plate having black printing on the outer peripheral portion while being heated and pressurized with a roll laminator. No bubbles were observed in the printed part. Next, it was cured by irradiating an ultraviolet ray of 2,000 mJ / cm 2 with an ultraviolet irradiator, and then bonded to a liquid crystal panel with a vacuum laminator. After bonding, air bubbles generated at the time of bonding were removed by processing at 0.5 MPa and 60 ° C. for 30 minutes with an autoclave, and a liquid crystal panel with a front plate was produced.
  • this liquid crystal panel with a front panel was subjected to a high temperature test for 50 hours in a high temperature test tank at 85 ° C. and a high temperature and high humidity test for 50 hours in a high temperature and high humidity tank at 60 ° C. and 90% RH. Observed. Generation of bubbles was not observed in any of the high temperature test and the high temperature and high humidity test. In addition, no change in color or peeling was observed, and good reliability was exhibited. In addition, when it was installed in a housing and checked for operation, it was confirmed that it operated without problems.
  • Example 4 and 5 it replaced with the optical adhesive material sheet of Example 1, and replaced with the commercially available transparent acrylic adhesive resin sheet (thickness of 175 micrometers) similarly to Example 4 and 5.
  • a liquid crystal panel with a front plate was produced.
  • the liquid crystal panel with a front plate was checked for the step following ability, and bubbles were generated in the vicinity of the step with the Kapton tape on the next day of the test.
  • Example 2 In Examples 4 and 5, in place of the optical pressure-sensitive adhesive sheet in Example 1, an ethylene-vinyl acetate copolymer (EVA) sheet having a softening temperature of 60 ° C. was used. Similarly, a liquid crystal panel with a front plate was produced. The liquid crystal panel with a front plate was checked for the step following property, and no bubbles were generated. However, in the high-temperature reliability test, a positional shift occurred between MR-58 and the glass plate.
  • EVA ethylene-vinyl acetate copolymer
  • the pressure-sensitive adhesive sheets obtained in Examples 6 to 10 and Comparative Examples 3 to 6 were evaluated by the following test methods.
  • the preparation of the optical pressure-sensitive adhesive resin composition and the production of the optical pressure-sensitive adhesive sheet were carried out in the same manner as in Example 1.
  • the thickness of the optical pressure-sensitive adhesive sheet was adjusted by changing the gap of the applicator in the coating process of the optical pressure-sensitive adhesive resin composition. 1.
  • Glass transition temperature, dynamic viscoelasticity evaluation (tan ⁇ , storage elastic modulus, loss elastic modulus measurement) Cut out the produced adhesive sheet to a size of 10mm in width and 5mm in length, and laminate it to a thickness of 1mm, and use a thermal analysis rheological system (EXSTAR6000, manufactured by SII Nanotechnology) to share shear mode
  • the glass transition temperature, storage elastic modulus, and loss elastic modulus were measured at a frequency of 1.0 Hz, a measurement temperature range of ⁇ 40 to 80 ° C., and a heating rate of 5 ° C./min.
  • tan ⁇ was determined from the storage elastic modulus and the loss elastic modulus as follows. Note that tan ⁇ was evaluated by values at 25 ° C. and 50 ° C.
  • the glass transition temperature (Tg) was a temperature at which tan ⁇ showed a peak in the measurement temperature range. When two or more tan ⁇ peaks were observed in this temperature range, the temperature at which the value of tan ⁇ was the largest was taken as the glass transition temperature.
  • Adhesive strength measurement The prepared adhesive sheet was cut into a size of 10 mm in width and 50 mm in length, and the adhesive strength was measured by 180-degree peeling using a tensile testing machine (AG-X / R manufactured by Shimadzu Corporation). The adhesion with the glass substrate was measured under the conditions of a peeling rate of 300 mm / min and a measurement temperature of 25 ° C.
  • the prepared adhesive sheet was cut into a size of 50 mm in width and 100 mm in length, and affixed to a glass substrate having dimensions of 50 mm ⁇ 100 mm ⁇ 0.7 mm (thickness) using a roller. Subsequently, the same glass substrate was bonded together using the roller, and the thing of the structure which pinched
  • the evaluation criteria are C when there are five or more bubbles that can be visually recognized, or B when there are no more than one and less than five bubbles that can be recognized visually without peeling. When there was no exfoliation and generation of bubbles, A was used. Otherwise, it was-when the sheet could not be formed.
  • Step-following capability The produced adhesive sheet having a thickness of 250 mm is cut into a size of 55 mm in width and 85 mm in length, and a glass substrate frame having dimensions of 55 mm (short side) ⁇ 85 mm (long side) ⁇ 0.125 mm (thickness).
  • One side of the pressure-sensitive adhesive sheet is protected on a glass substrate provided with a printed layer (step) having a thickness of 0.06 mm and a width of 9.3 mm on the short side and a width of 9.3 mm on the long side.
  • the film was peeled off and attached using a hand roller (25 ° C., load: 500 g).
  • FIG. 8 is a schematic diagram. C) when occurrence of more than half of the entire frame portion is observed, B when the occurrence of slight lift is recognized with respect to the entire frame portion, and A when almost no lift is observed.
  • Dielectric constant measurement Create an adhesive sheet with a width of 50 mm, a length of 50 mm, and a thickness of 250 ⁇ m, and bond a copper foil of 100 mm x 100 mm on one side of the adhesive sheet so that the adhesive sheet does not protrude On the other surface of the adhesive sheet, a 20 mm ⁇ 20 mm size copper foil was bonded so as not to protrude from the adhesive sheet. A terminal was brought into contact with the center of each of a copper foil having a size of 100 mm ⁇ 100 mm and a copper foil having a size of 20 mm ⁇ 20 mm, and a dielectric constant was measured by a dielectric constant measuring apparatus (manufactured by Agilent Technologies, LCR meter E4980A).
  • Production Example 6 (Preparation of acrylate polymer) Into a reaction vessel equipped with a condenser, a thermometer, a stirrer, a dropping funnel and a nitrogen introducing tube, 84.0 g of 2-ethylhexyl acrylate, 36.0 g of 2-hydroxyethyl acrylate and 150.0 g of methyl ethyl ketone are taken as initial monomers, and 100 ml. Heating was performed from room temperature (25 ° C.) to 80 ° C. in 15 minutes while substituting nitrogen with an air volume of / min.
  • Production Example 7 (Preparation of side chain methacryl-modified acrylate polymer)
  • 100 g of the acrylate polymer of Preparation Example 6 and 1.03 g of 2-isocyanatoethyl methacrylate, and 0.05 g of p-methoxyphenol as a polymerization inhibitor Then, 0.03 g of dibutyltin dilaurate was taken as a catalyst and heated from room temperature (25 ° C.) to 75 ° C. for 15 minutes while replacing oxygen with an air volume of 100 ml / min. Thereafter, the reaction was continued for 120 minutes while maintaining this temperature, and IR measurement was performed.
  • Production Example 8 (Preparation of side chain methacryl-modified acrylate polymer) A side-chain methacryl-modified acrylate polymer having a weight average molecular weight of 180,000 was obtained in the same manner as in Production Example 7, except that 2.06 g of 2-isocyanatoethyl methacrylate was used in Production Example 7.
  • a dissolved solution was prepared, and this solution was added dropwise over 120 minutes. After completion of the addition, the mixture was further reacted for 2 hours. Subsequently, methyl ethyl ketone was distilled off to obtain an acrylate polymer (weight average molecular weight 55,000) of 2-ethylhexyl acrylate and 2-hydroxyethyl acrylate. Next, 100 g of the acrylate polymer (weight average molecular weight 55,000) and 1.03 g of 2-isocyanatoethyl methacrylate were added to a reaction vessel equipped with a cooling pipe, a thermometer, a stirrer, a dropping funnel and an oxygen introduction pipe, and p as a polymerization inhibitor.
  • Production Example 10 (Preparation of side chain methacryl-modified acrylate polymer)
  • a reaction vessel equipped with a condenser, thermometer, stirrer, dropping funnel and nitrogen inlet tube 123.0 g of methyl ethyl ketone was taken as an initial solvent, and the temperature was changed to room temperature (25 ° C.) for 15 minutes while substituting nitrogen with an air volume of 100 ml / min. ) To 80 ° C. Thereafter, while maintaining this temperature, 210.0 g of 2-ethylhexyl acrylate and 90.0 g of 2-hydroxyethyl acrylate were used as dropping monomers, and 0.12 g of 2,2′-azobisisobutyronitrile was dissolved in them.
  • the prepared solution was prepared, and this solution was added dropwise over 120 minutes. After completion of the addition, the reaction was further continued for 2 hours. Subsequently, methyl ethyl ketone was distilled off to obtain an acrylate polymer of 2-ethylhexyl acrylate and 2-hydroxyethyl acrylate (weight average molecular weight 300,000). Subsequently, 100 g of the above acrylate polymer (weight average molecular weight 300,000) and 1.03 g of 2-isocyanatoethyl methacrylate were prohibited in a reaction vessel equipped with a cooling tube, a thermometer, a stirrer, a dropping funnel and an oxygen introduction tube.
  • Production Example 11 (Preparation of side chain methacryl-modified acrylate polymer) Into a reaction vessel equipped with a condenser, thermometer, stirrer, dropping funnel and nitrogen inlet tube, 150.0 g of methyl ethyl ketone was taken as an initial solvent, and nitrogen substitution was performed at an air volume of 100 ml / min. ) To 80 ° C.
  • acrylate polymer weight average molecular weight 200,000
  • 2-ethylhexyl acrylate, 2-ethylhexyl methacrylate and 2-hydroxyethyl acrylate 100 g
  • 100 g of the above acrylate polymer (weight average molecular weight 200,000) and 1.03 g of 2-isocyanatoethyl methacrylate are prohibited in a reaction vessel equipped with a cooling pipe, thermometer, stirring device, dropping funnel and oxygen introducing pipe.
  • Comparative Production Example 2 (Synthesis of polyurethane diacrylate having (meth) acryloyl groups at both ends)
  • polypropylene glycol was used in the same manner as Comparative Production Example 1, except that the amount of unsaturated fatty acid hydroxyalkyl ester-modified ⁇ -caprolactone was 9.80 g and that of isophorone diisocyanate was 34.20 g. And isophorone diisocyanate as repeating units, and a polyurethane diacrylate (weight average molecular weight 80,000) having (meth) acryloyl groups at both ends was obtained.
  • Example 6 34.0 g of the acrylate polymer obtained in Production Example 6, 4.0 g of the side chain methacryl-modified acrylate polymer obtained in Production Example 7, 40.4 g of 2-ethylhexyl acrylate (EHA), 21.1 g of acryloylmorpholine (ACMO) And 0.5 g of 1-hydroxycyclohexyl phenyl ketone (I-184) were weighed and mixed by stirring to obtain an optical pressure-sensitive adhesive resin composition.
  • EHA 2-ethylhexyl acrylate
  • ACMO acryloylmorpholine
  • I-184 1-hydroxycyclohexyl phenyl ketone
  • the optical adhesive material resin composition obtained above was dropped onto a polyethylene terephthalate film (hereinafter sometimes referred to as “base material 1”) whose surface was release-treated, and further the surface of the polyethylene terephthalate ( Hereinafter, the base material 2 may be covered), and the optical pressure-sensitive adhesive resin composition is formed into a sheet with a roller, and is irradiated with 1,200 mJ / cm 2 of ultraviolet light using an ultraviolet irradiation device to be transparent. An adhesive sheet was obtained. The results of evaluating the pressure-sensitive adhesive sheet by the above method are shown in Table 1.
  • Examples 7 to 10 and Comparative Examples 3 to 6 A pressure-sensitive adhesive sheet was obtained in the same manner as in Example 6 except that the composition shown in Tables 1 and 2 was used. Results evaluated in the same manner as in Example 6 are shown in Tables 1 and 2.
  • the optical pressure-sensitive adhesive resin composition of the present invention it is possible to produce an optical pressure-sensitive adhesive sheet that is excellent in transparency, excellent in handleability, and excellent in step following ability. Moreover, by making it bridge
PCT/JP2011/078616 2010-12-10 2011-12-09 光学用粘着材樹脂組成物、光学用粘着材シート、画像表示装置、光学用粘着材シートの製造方法及び画像表示装置の製造方法 WO2012077806A1 (ja)

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