WO2021070635A1 - 光硬化性粘着剤組成物、両面粘着シートおよびその製造方法、ならびに光学デバイスおよびその製造方法 - Google Patents

光硬化性粘着剤組成物、両面粘着シートおよびその製造方法、ならびに光学デバイスおよびその製造方法 Download PDF

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WO2021070635A1
WO2021070635A1 PCT/JP2020/036330 JP2020036330W WO2021070635A1 WO 2021070635 A1 WO2021070635 A1 WO 2021070635A1 JP 2020036330 W JP2020036330 W JP 2020036330W WO 2021070635 A1 WO2021070635 A1 WO 2021070635A1
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Prior art keywords
sensitive adhesive
adhesive sheet
pressure
double
adhesive composition
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English (en)
French (fr)
Japanese (ja)
Inventor
武史 仲野
翔 寳田
千尋 舟木
顕士 渡辺
量子 浅井
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Nitto Denko Corp
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Nitto Denko Corp
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Priority to KR1020227014780A priority Critical patent/KR102702611B1/ko
Priority to CN202080070452.0A priority patent/CN114514299A/zh
Publication of WO2021070635A1 publication Critical patent/WO2021070635A1/ja
Anticipated expiration legal-status Critical
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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
    • 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]
    • 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
    • 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
    • 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
    • B32B27/16—Layered products comprising a layer of synthetic resin specially treated, e.g. irradiated
    • 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
    • B32B27/30—Layered products comprising a layer of synthetic resin comprising vinyl (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
    • 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
    • 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
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • 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
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C09J11/06—Non-macromolecular additives organic
    • 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
    • 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
    • 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
    • C09J201/00—Adhesives based on unspecified macromolecular compounds
    • 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
    • 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
    • C09J2301/00—Additional features of adhesives in the form of films or foils
    • C09J2301/10—Additional features of adhesives in the form of films or foils characterized by the structural features of the adhesive tape or sheet
    • C09J2301/12—Additional features of adhesives in the form of films or foils characterized by the structural features of the adhesive tape or sheet by the arrangement of layers
    • C09J2301/124—Additional features of adhesives in the form of films or foils characterized by the structural features of the adhesive tape or sheet by the arrangement of layers the adhesive layer being present on both sides of the carrier, e.g. double-sided adhesive tape
    • 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
    • C09J2301/00—Additional features of adhesives in the form of films or foils
    • C09J2301/40—Additional features of adhesives in the form of films or foils characterized by the presence of essential components
    • C09J2301/416—Additional features of adhesives in the form of films or foils characterized by the presence of essential components use of irradiation

Definitions

  • the present invention relates to a photocurable pressure-sensitive adhesive composition and a double-sided pressure-sensitive adhesive sheet formed from the photo-curable pressure-sensitive adhesive composition. Furthermore, the present invention relates to an optical device including the double-sided adhesive sheet.
  • adhesive sheets are used for laminating between members.
  • a liquid crystal display device optical films such as a retardation film and a polarizing plate are bonded to both sides of a liquid crystal cell via an adhesive sheet.
  • a circularly polarizing plate is attached to the visible surface of the organic EL cell via an adhesive sheet for the purpose of preventing reflection of external light by the metal electrode of the organic EL cell.
  • optical members such as a touch panel sensor and a cover window are attached to the surface of these image display devices via an adhesive sheet.
  • a photocurable pressure-sensitive adhesive composition that is cured by irradiation with active light rays such as ultraviolet rays as a pressure-sensitive adhesive sheet used for bonding between members of an optical device.
  • a photopolymerization initiator is added to a monomer component and UV polymerization is performed in a solvent-free system, and a polyfunctional monomer and a photopolymerization initiator are added to the obtained polymer (partial polymer) having a low degree of polymerization.
  • Is added to prepare a photocurable pressure-sensitive adhesive composition which is applied onto a substrate and then UV-polymerized again to obtain a transparent pressure-sensitive adhesive sheet.
  • Patent Document 2 a solution containing a monomer component and a thermal polymerization initiator is heated to prepare a polymer solution by solution polymerization, and an isocyanate-based cross-linking agent, a polyfunctional monomer, and a photopolymerization initiator are added to this solution.
  • An example is shown in which a photocurable pressure-sensitive adhesive composition is prepared, applied onto a substrate, and then the solvent is removed by heating to obtain a transparent pressure-sensitive adhesive sheet.
  • the polyfunctional monomer is in an unreacted state, and when the pressure-sensitive adhesive sheet is attached to the adherend and then UV-irradiated, the polyfunctional monomer photopolymerizes and the storage elastic modulus increases. Adhesive reliability to the adherend is improved.
  • a transparent adhesive sheet having a total light transmittance of 90% or more is generally used for bonding between members of an optical device.
  • an adhesive sheet that absorbs visible light is used for an optical device.
  • a pressure-sensitive adhesive composition containing a colorant is used to prepare a pressure-sensitive adhesive sheet that absorbs visible light.
  • An object of the present invention is to provide a pressure-sensitive adhesive composition containing a colorant and capable of photocuring, and a pressure-sensitive adhesive sheet formed by using the pressure-sensitive adhesive composition.
  • the pressure-sensitive adhesive composition of the present invention contains a polymer, a photopolymerizable compound, a photopolymerization initiator, and a colorant, and has photocurability.
  • the colorant contained in the photocurable pressure-sensitive adhesive composition preferably has a maximum transmittance at a wavelength of 330 to 400 nm higher than a maximum transmittance at a wavelength of 400 to 700 nm. Further, it is preferable that the colorant has an average transmittance at a wavelength of 330 to 400 nm higher than the average transmittance at a wavelength of 400 to 700 nm.
  • the colorant pigments, dyes and the like are used.
  • the photopolymerization initiator preferably has at least one absorption maximum in the wavelength range of 330 to 400 nm.
  • the polymer contained in the pressure-sensitive adhesive composition may be an acrylic polymer.
  • the glass transition temperature of the polymer may be 0 ° C. or lower.
  • the pressure-sensitive adhesive composition may contain a cross-linking agent capable of cross-linking with the polymer. Examples of the cross-linking agent include isocyanate-based cross-linking agents and epoxy-based cross-linking agents.
  • a double-sided pressure-sensitive adhesive sheet can be obtained by forming the above pressure-sensitive adhesive composition into a sheet shape.
  • the double-sided adhesive sheet may have a maximum transmittance at a wavelength of 330 to 400 nm higher than a maximum transmittance at a wavelength of 400 to 700 nm, and an average transmittance at a wavelength of 330 to 400 nm is an average transmittance at a wavelength of 400 to 700 nm. It may be greater than the rate.
  • the average transmittance of the double-sided pressure-sensitive adhesive sheet at a wavelength of 400 to 700 nm may be 80% or less.
  • the total light transmittance of the double-sided adhesive sheet may be 80% or less.
  • the thickness of the double-sided adhesive sheet is, for example, about 10 to 500 ⁇ m.
  • the shear storage elastic modulus of the double-sided pressure-sensitive adhesive sheet at a temperature of 25 ° C. may be 10 to 1000 kPa.
  • the shear storage elastic modulus of the double-sided pressure-sensitive adhesive sheet at a temperature of 85 ° C. may be 3 to 300 kPa.
  • the double-sided pressure-sensitive adhesive sheet of the first aspect of the present invention is photopolymerizable by applying the above-mentioned pressure-sensitive adhesive composition in the form of a sheet on a base material and irradiating a sheet-like coating film provided on the base material with ultraviolet rays. It is formed by photocuring a compound. That is, the double-sided pressure-sensitive adhesive sheet of the first form is made of a photo-cured product of a sheet-like molded product of a photo-curable pressure-sensitive adhesive composition.
  • the double-sided pressure-sensitive adhesive sheet of the first form may have a non-volatile content of 90% or more.
  • the double-sided pressure-sensitive adhesive sheet of the second aspect of the present invention is formed by applying the above-mentioned pressure-sensitive adhesive composition on a base material in the form of a sheet and removing the solvent if necessary.
  • the double-sided pressure-sensitive adhesive sheet of the second form is a photocurable pressure-sensitive adhesive sheet containing a photopolymerizable compound in an unreacted state.
  • the double-sided adhesive sheet is used for bonding a plurality of members (adhesive bodies), for example, in forming an optical device such as an image display device.
  • an optical device such as an image display device.
  • the first adherend and the second adherend are attached to the double-sided adhesive sheet. It is pasted together via.
  • the photopolymerizable compound may be photo-cured by irradiating the double-sided pressure-sensitive adhesive sheet with ultraviolet rays after bonding to the adherend.
  • a colored pressure-sensitive adhesive sheet can be obtained by using a pressure-sensitive adhesive composition containing a colorant. Since the colorant contained in the photocurable pressure-sensitive adhesive composition has ultraviolet transparency, even when photocuring is performed by ultraviolet irradiation, curing inhibition is unlikely to occur and the polymerization rate can be increased.
  • FIG. 1 shows an adhesive sheet with a release film in which release films 1 and 2 are temporarily attached to both sides of the double-sided adhesive sheet 5.
  • the double-sided pressure-sensitive adhesive sheet 5 is formed by molding the pressure-sensitive adhesive composition into a sheet shape.
  • the pressure-sensitive adhesive composition is generally a viscous liquid containing a polymer, and a double-sided pressure-sensitive adhesive sheet can be obtained by applying the pressure-sensitive adhesive composition in layers on a substrate and removing the solvent if necessary. ..
  • the double-sided pressure-sensitive adhesive sheet of the present invention is formed by using a photocurable pressure-sensitive adhesive composition.
  • the photocurable pressure-sensitive adhesive composition contains a photopolymerizable compound and a photopolymerization initiator in addition to the polymer.
  • the double-sided pressure-sensitive adhesive sheet of the present invention is a colored pressure-sensitive adhesive sheet that absorbs visible light.
  • a pressure-sensitive adhesive composition containing a colorant is used for forming the colored pressure-sensitive adhesive sheet. That is, the photocurable pressure-sensitive adhesive composition used for forming the double-sided pressure-sensitive adhesive sheet of the present invention contains a colorant in addition to the polymer, the photopolymerizable compound and the photopolymerization initiator.
  • the double-sided adhesive sheet formed by using the photocurable pressure-sensitive adhesive composition is a type that photocures on the base material (first form) and an adherend that does not photocurerate on the base material. It is roughly classified into the type (second form) in which photo-curing is performed after bonding.
  • a photocurable pressure-sensitive adhesive composition containing a polymer, a photopolymerizable compound, a photopolymerization initiator, and a colorant is applied onto a base material, and the base material is coated. It is formed by performing photocuring on the above.
  • Polymers contained in the pressure-sensitive adhesive composition include acrylic polymers, silicone-based polymers, polyesters, polyurethanes, polyamides, polyvinyl ethers, vinyl acetate / vinyl chloride copolymers, modified polyolefins, epoxy-based, fluorine-based, natural rubbers, synthetic rubbers, etc. Examples include rubber-based polymers.
  • an acrylic polymer is preferably used because it exhibits adhesive properties such as appropriate wettability, cohesiveness and adhesiveness, and is also excellent in weather resistance and heat resistance.
  • Acrylic polymer contains (meth) acrylic acid alkyl ester as a main constituent monomer component.
  • (meth) acrylic means acrylic and / or methacryl.
  • the amount of the (meth) acrylic acid alkyl ester with respect to the total amount of the monomer components constituting the acrylic polymer is preferably 50% by weight or more, more preferably 55% by weight or more, still more preferably 60% by weight or more.
  • the (meth) acrylic acid alkyl ester a (meth) acrylic acid alkyl ester having an alkyl group having 1 to 20 carbon atoms is preferably used.
  • the (meth) acrylic acid alkyl ester may have a branched alkyl group or a cyclic alkyl group.
  • (meth) acrylic acid alkyl ester having a chain alkyl group examples include methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, isobutyl (meth) acrylate, and (meth).
  • (meth) acrylate alkyl ester having an alicyclic alkyl group examples include cyclopentyl (meth) acrylate, cyclohexyl (meth) acrylate, cycloheptyl (meth) acrylate, cyclooctyl (meth) acrylate and the like.
  • Examples thereof include (meth) acrylic acid esters having the above aliphatic hydrocarbon rings.
  • the acrylic polymer may contain a polar group-containing monomer such as a hydroxyl group-containing monomer, a carboxy group-containing monomer, and a nitrogen-containing monomer as a constituent monomer component.
  • a polar group-containing monomer such as a hydroxyl group-containing monomer, a carboxy group-containing monomer, and a nitrogen-containing monomer as a constituent monomer component.
  • the amount of the polar group-containing monomer (total of the hydroxy group-containing monomer, the carboxy group-containing monomer, and the nitrogen-containing monomer) with respect to the total amount of the monomer components constituting the acrylic polymer is, for example, about 3 to 50% by weight, and 5 to 40%. It may be% by weight or 10 to 30% by weight.
  • hydroxyl group-containing monomer examples include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 6-hydroxyhexyl (meth) acrylate, and (meth) acrylic.
  • acrylic acid esters such as 8-hydroxyoctyl acid, 10-hydroxydecyl (meth) acrylic acid, 12-hydroxylauryl (meth) acrylic acid and (4-hydroxymethylcyclohexyl) -methyl (meth) acrylate. ..
  • the hydroxyl group can be a reaction point (cross-linking point) with the isocyanate group.
  • carboxy group-containing monomer examples include acrylic monomers such as (meth) acrylic acid, carboxyethyl (meth) acrylate, and carboxypentyl (meth) acrylate, and itaconic acid, maleic acid, fumaric acid, and crotonic acid. ..
  • acrylic monomers such as (meth) acrylic acid, carboxyethyl (meth) acrylate, and carboxypentyl (meth) acrylate
  • itaconic acid maleic acid, fumaric acid, and crotonic acid.
  • the carboxy group can be a reaction point (crosslinking point) with the epoxy group.
  • Nitrogen-containing monomers include N-vinylpyrrolidone, methylvinylpyrrolidone, vinylpyridine, vinylpiperidone, vinylpyrimidine, vinylpiperazine, vinylpyrazine, vinylpyrrole, vinylimidazole, vinyloxazole, vinylmorpholin, (meth) acryloylmorpholin, and N-vinyl.
  • vinyl-based monomers such as carboxylic acid amides and N-vinylcaprolactam
  • cyano group-containing monomers such as acrylonitrile and methacrylonitrile.
  • Acrylic polymers include acid anhydride group-containing monomers, (meth) acrylic acid caprolactone adducts, sulfonic acid group-containing monomers, phosphoric acid group-containing monomers, vinyl acetate, vinyl propionate, styrene, and ⁇ as monomer components other than the above.
  • -Vinyl-based monomers such as methylstyrene; Epoxy group-containing monomers such as glycidyl (meth) acrylate; Polyethylene glycol (meth) acrylate, Polypropylene glycol (meth) acrylate, methoxyethylene glycol (meth) acrylate, (meth) ) Glycol-based acrylic ester monomers such as methoxypolypropylene glycol acrylate; Acrylic acid esters such as tetrahydrofurfuryl (meth) acrylate, fluorine (meth) acrylate, silicone (meth) acrylate and 2-methoxyethyl (meth) acrylate. It may contain a monomer or the like.
  • the glass transition temperature (Tg) of the polymer contained in the pressure-sensitive adhesive composition is preferably 0 ° C. or lower.
  • the glass transition temperature of the polymer may be ⁇ 5 ° C. or lower, ⁇ 10 ° C. or lower, or ⁇ 15 ° C. or lower.
  • the glass transition temperature of the polymer is the peak top temperature of the loss tangent (tan ⁇ ) measured by dynamic viscoelasticity measurement.
  • the glass transition temperature may be calculated from the composition of the polymer based on the theoretical Tg.
  • Tg is the glass transition temperature of the polymer (unit: K)
  • Wi is the weight fraction of the monomer component i constituting the polymer (copolymerization ratio based on the weight)
  • Tg i is the glass transition temperature of the homopolymer of the monomer component i ( Unit: K).
  • the glass transition temperature of the homopolymer the numerical value described in the third edition of the Polymer Handbook (John Wiley & Sons, Inc., 1989) can be adopted.
  • the peak top temperature of tan ⁇ measured by dynamic viscoelasticity measurement may be adopted.
  • a polymer can be obtained by polymerizing the above monomer components by various known methods.
  • the polymerization method is not particularly limited, but in the pressure-sensitive adhesive composition used for producing the first-form double-sided pressure-sensitive adhesive sheet in which the pressure-sensitive adhesive composition is photocured on a substrate, it is preferable to prepare a polymer by photopolymerization. Since the polymer can be prepared without using a solvent in photopolymerization, it is not necessary to dry and remove the solvent when forming the pressure-sensitive adhesive sheet, and a thick pressure-sensitive adhesive sheet can be uniformly formed.
  • the composition used for preparing the prepolymer (composition for forming the prepolymer) preferably contains a photopolymerization initiator in addition to the monomer.
  • the photopolymerization initiator may be appropriately selected depending on the type of monomer. For example, a photoradical polymerization initiator is used for the polymerization of an acrylic polymer.
  • the photopolymerization initiator examples include a benzoin ether-based photopolymerization initiator, an acetophenone-based photopolymerization initiator, an ⁇ -ketol-based photopolymerization initiator, an aromatic sulfonyl chloride-based photopolymerization initiator, and a photoactive oxime-based photopolymerization initiator.
  • Examples thereof include benzoin-based photopolymerization initiators, benzyl-based photopolymerization initiators, benzophenone-based photopolymerization initiators, ketal-based photopolymerization initiators, thioxanthone-based photopolymerization initiators, and acylphosphine oxide-based photopolymerization initiators.
  • a chain transfer agent such as ⁇ -thioglycerol, lauryl mercaptan, glycidyl mercaptan, mercaptoacetic acid, 2-mercaptoethanol, thioglycolic acid, 2-ethylhexyl thioglycolate, and 2,3-dimercapto-1-propanol.
  • thiols such as ⁇ -thioglycerol, lauryl mercaptan, glycidyl mercaptan, mercaptoacetic acid, 2-mercaptoethanol, thioglycolic acid, 2-ethylhexyl thioglycolate, and 2,3-dimercapto-1-propanol.
  • thiols such as ⁇ -thioglycerol, lauryl mercaptan, glycidyl mercaptan, mercaptoacetic acid, 2-mercaptoethanol, thioglycolic acid, 2-
  • the polymerization rate of the prepolymer is not particularly limited, but is preferably 3 to 50% by weight, more preferably 5 to 40% by weight, from the viewpoint of obtaining a viscosity suitable for coating on a substrate.
  • the polymerization rate of the prepolymer can be adjusted to a desired range by adjusting the type and amount of the photopolymerization initiator, the irradiation intensity and irradiation time of active light such as UV light, and the like.
  • the polymerization rate of the prepolymer is a non-volatile component when heated at 130 ° C. for 3 hours, and is calculated by the following formula.
  • the photocurable pressure-sensitive adhesive composition used for forming the colored pressure-sensitive adhesive sheet contains a polymer, a photopolymerizable compound, a photopolymerization initiator, and a colorant.
  • a photocurable pressure-sensitive adhesive composition can be obtained by adding a photopolymerizable compound, a photopolymerization initiator and a colorant to the prepolymer.
  • a prepolymer a low molecular weight polymer (oligomer) may be used, and the low molecular weight polymer may be mixed with a photopolymerizable compound, a photopolymerization initiator and a colorant to prepare a pressure-sensitive adhesive composition. ..
  • the photopolymerizable compound contained in the pressure-sensitive adhesive composition has one or more photopolymerizable functional groups in one molecule.
  • the photopolymerizable functional group may be radically polymerizable, cationically polymerizable or anionically polymerizable, but since it is excellent in reactivity, it is a radically polymerizable functional group having an unsaturated double bond (ethylenically unsaturated group). Is preferable.
  • the prepolymer contains a monomer that has not reacted with the polymer, and the unreacted monomer retains photopolymerizability. Therefore, it is not always necessary to add the photopolymerizable compound in the preparation of the pressure-sensitive adhesive composition.
  • the photopolymerizable compound to be added may be the same as or different from the monomer used for preparing the prepolymer.
  • the compound added as the photopolymerizable compound is preferably a monomer or oligomer having a (meth) acryloyl group as the photopolymerizable functional group because it has high compatibility with the polymer.
  • the photopolymerizable compound may be a polyfunctional compound having two or more photopolymerizable functional groups in one molecule. Examples of the photopolymerizable polyfunctional compound include polyfunctional (meth) acrylate.
  • polyfunctional (meth) acrylate examples include polyethylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate, polytetramethylene glycol di (meth) acrylate, bisphenol A ethylene oxide-modified di (meth) acrylate, and bisphenol A propylene oxide.
  • tetrafunctional (meth) acrylic acid ester such as ditrimethylolpropane tetra (meth) acrylate, ethoxylated pentaeristol tetra (meth) acrylate, pentaeristol tetra (meth) acrylate; dipentaeryristol penta Examples thereof include (meth) acrylates and the like, and pentafunctional or higher functional (meth) acrylic acid esters such as dipentaeryristol hexa (meth) acrylate.
  • the amount of the polyfunctional compound used is 100 parts by weight based on the total amount of the monomers (total of the monomer used for preparing the prepolymer and the photopolymerizable compound added to the prepolymer). , 40 parts by weight or less is preferable, 30 parts by weight or less is more preferable, and 25 parts by weight or less is further preferable. If the amount of the polyfunctional monomer used is excessively large, the viscosity of the pressure-sensitive adhesive sheet after photocuring is low, and the adhesive strength may be poor.
  • the amount of the polyfunctional compound used may be 20 parts by weight or less, 15 parts by weight or less, 10 parts by weight or less, or 5 parts by weight or less.
  • the amount of the polyfunctional monomer used may be 0, and may be 0.1 parts by weight or more, 0.3 parts by weight or more, or 0.5 parts by weight or more.
  • the photocurable pressure-sensitive adhesive composition comprises a photopolymerization initiator.
  • the photopolymerization initiator generates radicals, acids, bases, etc. by irradiation with active rays such as ultraviolet rays, and can be appropriately selected depending on the type of the photopolymerizable compound and the like.
  • the photopolymerizable compound is a compound having a (meth) acryloyl group (for example, a monofunctional or polyfunctional (meth) acrylate)
  • the photopolymerization initiator may be used alone or in combination of two or more.
  • the addition of the photopolymerization initiator may be omitted.
  • the photopolymerization initiator added may be the same as or different from the photopolymerization initiator used in the preparation of the prepolymer.
  • the photopolymerization initiator contained in the pressure-sensitive adhesive composition preferably has an absorption maximum in a wavelength region where light absorption by a colorant described later is small. Specifically, the photopolymerization initiator preferably has an absorption maximum in the wavelength region of 330 to 400 nm. Since the photopolymerization initiator has an absorption maximum in a region where the light absorption by the colorant is small, the curing inhibition by the colorant is suppressed, so that the polymerization rate can be sufficiently increased by the photocuring.
  • Examples of the photoradical polymerization initiator having an absorption maximum in the wavelength region of 330 to 400 nm include hydroxyketones, benzyldimethylketals, aminoketones, acylphosphine oxides, benzophenones, trichloromethyl group-containing triazine derivatives and the like. ..
  • the content of the photopolymerization initiator in the photocurable pressure-sensitive adhesive composition is 0.01 to 100 parts by weight based on 100 parts by weight of the total amount of the monomers (the monomer used for preparing the prepolymer and the photopolymerizable compound added to the prepolymer). It is about 10 parts by weight, preferably about 0.05 to 5 parts by weight.
  • the pressure-sensitive adhesive composition used to form the colored pressure-sensitive adhesive sheet contains a colorant.
  • the colorant may be a dye or a pigment as long as it can be dissolved or dispersed in the pressure-sensitive adhesive composition. Pigments are preferable because they have high color development even when added in a small amount.
  • the colorant preferably absorbs visible light and has ultraviolet transparency is used.
  • the colorant preferably has a maximum transmittance at a wavelength of 330 to 400 nm higher than a maximum transmittance at a wavelength of 400 to 700 nm. Further, the colorant preferably has an average transmittance at a wavelength of 330 to 400 nm higher than the average transmittance at a wavelength of 400 to 700 nm.
  • the transmittance of the colorant is adjusted by using an appropriate solvent such as tetrahydrofuran (THF) or a dispersion medium (an organic solvent having a small absorption in the wavelength range of 330 to 700 nm) so that the transmittance at a wavelength of 400 nm is about 50 to 60%. Measure with a diluted solution or dispersion.
  • Examples of the ultraviolet-transmissive black pigment that absorbs ultraviolet rays less than the absorption of visible light include “9050BLACK” and “UVBK-0001” manufactured by Tokushiki.
  • Examples of the ultraviolet-transparent black dye include “SOC-L-0123” manufactured by Orient Chemical Industries.
  • Carbon black and titanium black which are generally used as black colorants, absorb ultraviolet rays more than they absorb visible light (ultraviolet transmittance is smaller than visible light transmittance). Therefore, when a colorant such as carbon black is added to the photocurable pressure-sensitive adhesive composition having sensitivity to ultraviolet rays, most of the ultraviolet rays irradiated for photocuring are absorbed by the colorant, and the amount of light absorbed by the photopolymerization initiator. Is small, and it takes time to photo-cure (the amount of integrated irradiation light increases).
  • the thickness of the adhesive sheet is large, the amount of ultraviolet rays reaching the surface opposite to the light irradiation surface is small, so that the photocuring tends to be insufficient even if the light irradiation is performed for a long time.
  • a colorant having a higher transmittance of ultraviolet rays than visible light it is possible to suppress curing inhibition caused by the colorant.
  • the content of the colorant in the photocurable pressure-sensitive adhesive composition is, for example, about 0.01 to 20 parts by weight with respect to 100 parts by weight of the total amount of the monomers, and the type of the colorant, the color tone of the pressure-sensitive adhesive sheet, and the light transmittance. It may be set appropriately according to the rate and the like.
  • the colorant may be added to the composition as a solution or dispersion dissolved or dispersed in an appropriate solvent.
  • the photocurable pressure-sensitive adhesive composition may contain components other than the polymer, the photopolymerizable compound, the photopolymerization initiator and the colorant.
  • a chain transfer agent may be contained for the purpose of adjusting the photocuring rate or the like.
  • an oligomer or a tackifier may be contained for the purpose of adjusting the viscosity of the pressure-sensitive adhesive composition, adjusting the adhesive strength of the pressure-sensitive adhesive sheet, and the like.
  • the oligomer for example, one having a weight average molecular weight of about 1000 to 30,000 is used.
  • an acrylic oligomer is preferable because it has excellent compatibility with an acrylic polymer.
  • the pressure-sensitive adhesive composition may contain additives such as a silane coupling agent, a plasticizer, a softening agent, an antioxidant, a filler, an antioxidant, a surfactant, and an antistatic agent.
  • ⁇ Making double-sided adhesive sheet> By applying a photocurable pressure-sensitive adhesive composition containing a colorant on a base material in a sheet form (layered form) and irradiating a coating film of the pressure-sensitive adhesive composition on the base material with ultraviolet rays to perform photo-curing. , A double-sided adhesive sheet can be obtained.
  • photocuring it is preferable to attach a cover sheet to the surface of the coating film and irradiate ultraviolet rays with the pressure-sensitive adhesive composition sandwiched between the two sheets to prevent polymerization inhibition by oxygen. ..
  • the sheet-like coating film may be heated for the purpose of removing the solvent or dispersion medium of the colorant. When removing the solvent or the like by heating, it is preferable to carry out before attaching the cover sheet.
  • the base material and cover sheet used for forming the double-sided adhesive sheet may be any suitable base material.
  • the base material and the cover sheet may be a release film having a release layer on the contact surface with the double-sided adhesive sheet.
  • the film base material of the release film a film made of various resin materials is used.
  • the resin material include polyester resins such as polyethylene terephthalate and polyethylene naphthalate, acetate resins, polyether sulfone resins, polycarbonate resins, polyamide resins, polyimide resins, polyolefin resins, and (meth) acrylic resins.
  • polyester resins such as polyethylene terephthalate and polyethylene naphthalate, acetate resins, polyether sulfone resins, polycarbonate resins, polyamide resins, polyimide resins, polyolefin resins, and (meth) acrylic resins.
  • polyester resins such as polyethylene terephthalate are particularly preferable.
  • the thickness of the film substrate is preferably 10 to 200 ⁇ m, more preferably 25 to 150 ⁇ m.
  • the material of the release layer include a silicone-based release agent, a fluorine-based release agent, a long-chain alkyl-based release agent, and a fatty acid amide-based release agent.
  • the thickness of the release layer is generally about 10 to 2000 nm.
  • the thickness of the double-sided adhesive sheet is not particularly limited, and may be set according to the type and shape of the adherend.
  • the thickness of the double-sided pressure-sensitive adhesive sheet is, for example, about 10 to 500 ⁇ m, and may be 20 ⁇ m or more, 30 ⁇ m or more, 40 ⁇ m or more, or 50 ⁇ m or more.
  • the photocurable composition can be uniformly photocured in the thickness direction even when the thickness of the double-sided pressure-sensitive adhesive sheet is large.
  • the thickness of the double-sided pressure-sensitive adhesive sheet may be 400 ⁇ m or less, 300 ⁇ m or less, 250 ⁇ m or less, or 200 ⁇ m or less.
  • the liquid pressure-sensitive adhesive composition becomes a solid (standard) pressure-sensitive adhesive sheet.
  • the light source for ultraviolet irradiation is not particularly limited as long as the photopolymerization initiator contained in the pressure-sensitive adhesive composition can irradiate light in a sensitive wavelength range, and is an LED light source, a high-pressure mercury lamp, and an ultra-high-pressure mercury. Lamps, metal halide lamps, xenon lamps, etc. are used.
  • the integrated light amount of the irradiation light is, for example, about 100 to 5000 mJ / cm 2.
  • the polymerization rate (nonvolatile content) of the double-sided pressure-sensitive adhesive sheet made of the photocurable product of the photocurable pressure-sensitive adhesive composition is preferably 80% or more, more preferably 85% or more, still more preferably 90% or more.
  • the polymerization rate may be 93% or more or 95% or more.
  • the pressure-sensitive adhesive sheet may be heated to remove volatile components such as residual monomers, unreacted polymerization initiator, and solvent.
  • an adhesive sheet with a release film having the release films temporarily attached to both sides can be obtained.
  • the release film used as the base material or the cover sheet when forming the double-sided adhesive sheet may be used as it is as the release films 1 and 2.
  • the thickness of one release film 1 and the thickness of the other release film 2 may be the same or different.
  • the peeling force when peeling the release film temporarily attached to one surface from the double-sided adhesive sheet 5 and the peeling force when peeling the release film temporarily attached to the other surface from the double-sided adhesive sheet 5 are It may be the same or different. If the peeling forces of the two are different, the release film 2 (light peeling film) having a relatively small peeling force is peeled off from the double-sided adhesive sheet 5 first and bonded to the first adherend, and then relative to each other. Excellent workability when the release film 1 (heavy release film) having a large peeling force is peeled off and bonded to the second adherend.
  • the double-sided pressure-sensitive adhesive sheet containing a colorant has light absorption in visible light.
  • the total light transmittance of the double-sided adhesive sheet is, for example, 80% or less, 70% or less, 60% or less, 50% or less, 40% or less, 30% or less, 20% or less, 10% or less or 5% or less. You may.
  • the double-sided adhesive sheet absorbs ultraviolet rays less than it absorbs visible light.
  • it is preferable maximum transmittance T MUV wavelengths 330 ⁇ 400 nm of the adhesive sheet is larger than the maximum transmittance T MVIS wavelengths 400 ⁇ 700 nm.
  • the average transmittance T AUV wavelengths 330 ⁇ 400 nm of the adhesive sheet is preferably larger than the average transmittance T absorb wavelengths 400 ⁇ 700 nm.
  • the average transmittance TaVIS of the double-sided adhesive sheet at a wavelength of 400 to 700 nm is, for example, 80% or less, 70% or less, 60% or less, 50% or less, 40% or less, 30% or less, 20% or less or 10% or less. It may be.
  • the average transmittance TaUV of the double-sided pressure-sensitive adhesive sheet at a wavelength of 330 to 400 nm is preferably 5% or more, and may be 10% or more, 15% or more, 20% or more, or 25% or more. Difference between TaUV and TaVIS TaUV - TaVIS may be 3% or more, 5% or more, 8% or more, or 10% or more.
  • the maximum transmittance T mVIS in the wavelength range of 400 to 700 nm of the double-sided adhesive sheet is, for example, 85% or less, 80% or less, 70% or less, 60% or less, 50% or less, 40% or less, 30% or less, 20. It may be% or less or 10% or less.
  • the maximum transmittance T mUV in the wavelength range of 330 to 400 nm of the double-sided pressure-sensitive adhesive sheet is preferably 5% or more, and may be 10% or more, 15% or more, 20% or more, or 25% or more. Difference between T mUV and T mVIS T mUV- T mVIS may be 0.1% or more, 0.5% or more, 1% or more, or 1.5% or more.
  • the transmittance of the double-sided adhesive sheet may be adjusted according to the application and purpose.
  • the average transmittance TaVIS of the double-sided pressure-sensitive adhesive sheet at a wavelength of 400 to 700 nm is preferably 10% or less, and may be 7% or less or 5% or less.
  • the TaVIS is preferably 80% or less, and may be 78% or less or 75% or less. In either case, the maximum transmittance TaUV in the wavelength range of 330 to 400 nm of the double-sided adhesive sheet may be higher than that of TaVIS.
  • the shear storage elastic modulus G'25 ° C. at a temperature of the pressure-sensitive adhesive sheet at 25 ° C. is, for example, about 10 to 1000 kPa, may be 30 kPa or more, 50 kPa or more, 70 kPa or more or 100 kPa or more, 700 kPa or less, 500 kPa or less, 300 kPa or less. Alternatively, it may be 200 kPa or less.
  • shear storage elastic modulus of the pressure-sensitive adhesive sheet is, for example, about 3 to 300 kPa, may be 5 kPa or more, 7 kPa or more, or 10 kPa or more, and is 200 kPa or less, 150 kPa or less, or 100 kPa or less. It may be.
  • the shear storage elastic modulus is a value measured by dynamic viscoelasticity measurement at a frequency of 1 Hz.
  • the double-sided pressure-sensitive adhesive sheet of the second aspect of the present invention is a type of pressure-sensitive adhesive sheet that is not photo-cured on a base material, and is formed in the form of a photo-curable pressure-sensitive adhesive composition. Since the double-sided pressure-sensitive adhesive sheet of the second form contains the photopolymerizable compound in an unreacted state, the pressure-sensitive adhesive sheet has photocurability.
  • the pressure-sensitive adhesive composition used for forming the double-sided pressure-sensitive adhesive sheet of the second form contains a polymer, a photopolymerizable compound, a photopolymerization initiator, and a colorant.
  • polymer As the polymer contained in the pressure-sensitive adhesive composition, various polymers can be applied as in the first form, and an acrylic polymer is preferably used.
  • the monomer components constituting the acrylic polymer are the same as those in the first form.
  • the monomer component constituting the polymer contains a hydroxy group-containing monomer and / or a carboxy group-containing monomer.
  • the monomer component constituting the polymer contains a hydroxy group-containing monomer and / or a carboxy group-containing monomer.
  • an isocyanate-based cross-linking agent it is preferable to contain a hydroxy group-containing monomer as a monomer component.
  • an epoxy-based cross-linking agent it is preferable to contain a carboxy group-containing monomer as the monomer.
  • a polymer having a relatively large molecular weight is used as a polymer contained in the photocurable pressure-sensitive adhesive composition in order to form a solid (standard) pressure-sensitive adhesive sheet. Used.
  • the weight average molecular weight of the polymer is, for example, about 100,000 to 2 million.
  • the pressure-sensitive adhesive composition is preferably a solution in which the polymer is dissolved in an organic solvent in order to be applied onto a substrate.
  • a polymer solution can be obtained by solution-polymerizing the monomer components.
  • a polymer solution may be prepared by dissolving a solid polymer in an organic solvent.
  • the polymerization initiator includes an azo-based initiator, a peroxide-based initiator, a redox-based initiator that combines a peroxide and a reducing agent (for example, a combination of a persulfate and sodium hydrogen sulfite, a peroxide and an ascorbin).
  • a thermal polymerization initiator such as (combination of sodium acid acid) is preferably used.
  • the amount of the polymerization initiator used is not particularly limited, but for example, it is preferably about 0.005 to 5 parts by weight, more preferably about 0.02 to 3 parts by weight, based on 100 parts by weight of the total amount of the monomer components forming the polymer. preferable.
  • the photopolymerizable compound contained in the pressure-sensitive adhesive composition in the second form is the same as that described above for the first form, and a compound having one or more photopolymerizable functional groups is used.
  • the photopolymerization initiator contained in the pressure-sensitive adhesive composition in the second form is the same as that described above for the first form, and preferably has an absorption maximum in the wavelength region of 330 to 400 nm.
  • the amount of the photopolymerization initiator is about 0.01 to 10 parts by weight, preferably about 0.05 to 5 parts by weight, based on 100 parts by weight of the polymer.
  • the colorant contained in the pressure-sensitive adhesive composition in the second form is the same as that described above for the first form, and it is preferable that the transmittance at a wavelength of 330 to 400 nm is larger than the transmittance at a wavelength of 400 to 700 nm.
  • the pressure-sensitive adhesive composition of the second form preferably contains a cross-linking agent capable of cross-linking with the above polymer.
  • a cross-linking agent capable of cross-linking with the above polymer.
  • the cross-linking agent for introducing a cross-linked structure into the polymer include an isocyanate-based cross-linking agent, an epoxy-based cross-linking agent, an oxazoline-based cross-linking agent, an aziridine-based cross-linking agent, a carbodiimide-based cross-linking agent, and a metal chelate-based cross-linking agent. Be done.
  • isocyanate-based cross-linking agents and epoxy-based cross-linking agents are preferable because they have high reactivity with the hydroxyl groups and carboxy groups of the polymer and the cross-linked structure can be easily introduced.
  • These cross-linking agents react with functional groups such as hydroxyl groups and carboxy groups introduced into the polymer to form a cross-linked structure.
  • polyisocyanate-based cross-linking agent polyisocyanate having two or more isocyanate groups in one molecule is used.
  • examples of the isocyanate-based cross-linking agent include lower aliphatic polyisocyanates such as butylene diisocyanate and hexamethylene diisocyanate; alicyclic isocyanates such as cyclopentylene diisocyanate, cyclohexylene diisocyanate and isophorone diisocyanate; 2,4-tolylene diisocyanate.
  • Aromatic isocyanates such as isocyanate, 4,4'-diphenylmethane diisocyanate, xylylene diisocyanate; trimethylolpropane / trimylene diisocyanate trimer adduct (eg, "Coronate L” manufactured by Toso), trimethylolpropane / hexamethylene Diisocyanate trimeric adduct (eg, Tosoh's "Coronate HL”), xylylene diisocyanate trimethylolpropane adduct (eg, Mitsui Chemicals' "Takenate D110N", hexamethylene diisocyanate isocyanurate (eg, Tosoh's "Coronate HL”) Examples thereof include isocyanate additives such as "Coronate HX").
  • the epoxy-based cross-linking agent a polyfunctional epoxy compound having two or more epoxy groups in one molecule is used.
  • the epoxy group of the epoxy-based cross-linking agent may be a glycidyl group.
  • Examples of the epoxy-based cross-linking agent include N, N, N', N'-tetraglycidyl-m-xylene diamine, diglycidyl aniline, 1,3-bis (N, N-diglycidyl aminomethyl) cyclohexane, 1, 6-Hexanediol diglycidyl ether, neopentyl glycol diglycidyl ether, ethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether, polypropylene glycol diglycidyl ether, sorbitol polyglycidyl ether, glycerol polyglycidyl ether, penta Ellisritol polyglycid
  • the amount of the cross-linking agent is about 0.01 to 5 parts by weight with respect to 100 parts by weight of the polymer, and may be 0.05 parts by weight or more, 0.1 parts by weight or more, or 0.2 parts by weight or more. It may be 3 parts by weight or less, 2 parts by weight or less, or 1 part by weight or less.
  • the pressure-sensitive adhesive composition of the second form includes oligomers, tackifiers, silane coupling agents, chain transfer agents, plasticizers, softeners, deterioration inhibitors, fillers, antioxidants, and surfactants. It may contain an agent, an antistatic agent and the like.
  • a double-sided pressure-sensitive adhesive sheet is formed on the base material by applying the pressure-sensitive adhesive composition on the base material and, if necessary, drying and removing the solvent.
  • a release film is preferably used as in the first form.
  • the pressure-sensitive adhesive composition contains a solvent
  • the heating and drying temperature is preferably 40 ° C. to 200 ° C., more preferably 50 ° C. to 180 ° C., and particularly preferably 70 ° C. to 170 ° C.
  • the drying time an appropriate time can be adopted as appropriate.
  • the drying time is preferably 5 seconds to 20 minutes, more preferably 5 seconds to 15 minutes, and particularly preferably 10 seconds to 10 minutes.
  • cover sheet After the solvent is dried, it is preferable to attach a cover sheet to protect the surface of the double-sided adhesive sheet.
  • cover sheet it is preferable to use a release film having a release layer on the contact surface with the adhesive sheet, as in the case of the base film.
  • a crosslinked structure is introduced into the polymer by heating as necessary.
  • the heating temperature and heating time may be appropriately set depending on the type of the cross-linking agent used, and are usually in the range of 20 ° C. to 160 ° C. for about 1 minute to 7 days.
  • the heating for drying the solvent may also serve as the heating for crosslinking.
  • the introduction of the crosslinked structure does not necessarily have to be accompanied by heating.
  • the double-sided pressure-sensitive adhesive sheet of the second form preferably has the same thickness, light transmittance, and shear storage elastic modulus as the double-sided pressure-sensitive adhesive sheet of the first form. Since the double-sided pressure-sensitive adhesive sheet of the second form is not photocured on the base material, the photopolymerizable compound is contained in an unreacted state. That is, the double-sided pressure-sensitive adhesive sheet of the second form is a photocurable pressure-sensitive adhesive sheet containing a polymer, a photopolymerizable compound, a photopolymerization initiator, and a colorant.
  • the photocurable adhesive sheet can be photocured by irradiating it with ultraviolet rays after it is attached to the adherend.
  • the adhesive force between the adhesive sheet and the adherend can be changed by photocuring. For example, since the adhesive sheet before photo-curing has high flexibility, it is possible to fill the surface irregularities and steps of the adherend, and after photo-curing, the adhesive strength and adhesive reliability to the adherend can be improved.
  • Ultraviolet rays are used as the active rays for photocuring the adhesive sheet. Similar to the pressure-sensitive adhesive sheet of the first form, since the colorant has a higher transmittance of ultraviolet rays than visible light, it is possible to suppress curing inhibition during photo-curing even when the pressure-sensitive adhesive sheet is thick.
  • the thickness of the double-sided adhesive sheet is not particularly limited, and may be set according to the type and shape of the adherend.
  • the thickness of the double-sided pressure-sensitive adhesive sheet is, for example, about 10 to 500 ⁇ m, and may be 20 ⁇ m or more, 30 ⁇ m or more, 40 ⁇ m or more, or 50 ⁇ m or more. As described above, since the colorant has ultraviolet transparency, curing inhibition is unlikely to occur, and process efficiency can be improved.
  • the double-sided adhesive sheets of the first form and the second form can be used for bonding various transparent members and opaque members.
  • the type of the adherend is not particularly limited, and examples thereof include various resin materials, glass, and metal.
  • the double-sided adhesive sheet is used, for example, for bonding members of an optical device such as an image display device. Since the adhesive sheet is colored, it may have an effect of reducing the emission of scattered light or reflected light in the device to the outside to improve visibility.
  • the double-sided adhesive sheet can be used as an embedding member between members or as a sealing member, and can also be used for sealing an optical semiconductor element.
  • the optical semiconductor element include a light emitting diode (LED).
  • LED light emitting diode
  • the adhesive sheet reduces the scattering and reflection of visible light, it can be expected to have an effect of suppressing the decrease in visibility due to the scattering and reflection of light in the gap between the LEDs.
  • the double-sided adhesive sheet is photocurable, it may be photocured by irradiating it with ultraviolet rays after it is attached to the adherend. Since the adhesive sheet before photo-curing has high flexibility, it has excellent ability to follow irregularities such as gaps between LEDs. By performing photo-curing after making the adhesive sheet follow the unevenness, improvement in adhesive reliability can be expected.
  • the double-sided adhesive sheet can also be put into practical use in a state of being laminated and integrated with other members.
  • an optical film such as a polarizing plate may be attached to one surface of a double-sided adhesive sheet to be put into practical use as an optical film with an adhesive.
  • a laminate in which an adherend is bonded to each of the main surfaces of both side adhesive sheets can also be used as a constituent member of the optical device.
  • the double-sided adhesive sheet may be laminated with a material having ultraviolet absorption.
  • the ultraviolet absorbing layer may be a resin film, an adhesive layer, or the like.
  • the ultraviolet absorbing layer may contain an ultraviolet absorbing agent.
  • the ultraviolet absorber include a benzotriazole-based ultraviolet absorber, a benzophenone-based ultraviolet absorber, a triazine ultraviolet absorber, a salicylate-based ultraviolet absorber, a cyanoacrylate-based ultraviolet absorber, and the like.
  • UV shielding properties may be required for adhesive sheets and the like.
  • An ultraviolet absorber can be added to the photocurable pressure-sensitive adhesive composition for forming the double-sided pressure-sensitive adhesive sheet 5, but the photo-curing is inhibited by the UV-absorbing agent absorbing the ultraviolet rays for photo-curing the pressure-sensitive adhesive. Therefore, the significance of using an ultraviolet-transparent colorant is lost. Therefore, it is preferable to shield the ultraviolet rays by laminating an ultraviolet absorbing layer on the double-sided adhesive sheet.
  • the ultraviolet absorbing layer When the ultraviolet absorbing layer is laminated after the pressure-sensitive adhesive composition is photocured, the ultraviolet absorbing layer may be laminated on one side of the double-sided adhesive sheet, or may be laminated on both sides.
  • the ultraviolet absorbing layer When the ultraviolet absorbing layer is laminated on the pressure-sensitive adhesive composition before photocuring (for example, the double-sided pressure-sensitive adhesive sheet of the second form), the ultraviolet absorbing layer is laminated on one side and the pressure-sensitive adhesive is irradiated with ultraviolet rays from the other side. It may be photo-cured.
  • the release film on one side was peeled off from the adhesive sheet, and non-alkali glass was attached to the exposed side. Then, the release film on the other surface was peeled off from the pressure-sensitive adhesive sheet to obtain a sample in which the pressure-sensitive adhesive sheet was bonded on a non-alkali glass plate. Using this sample, the transmission spectrum of the evaluation sample was measured with a visible ultraviolet spectrophotometer (manufactured by Hitachi High-Technologies Corporation, trade name "U-4100").
  • the ratio of the transmittance (transmitted light amount) of the evaluation sample to the transmittance (transmitted light amount) of the non-alkali glass was defined as the transmittance of the adhesive sheet. From the transmission spectrum of the adhesive sheet, the arithmetic average of the transmittance in the wavelength range of 400 to 700 nm and the arithmetic average of the transmittance in the wavelength range of 330 to 400 nm, and the maximum value of the transmittance in the wavelength range of 400 to 700 nm and the wavelength of 330 to 400 nm. The maximum value of transmittance was calculated.
  • the transmission spectrum of the colorant was measured using a quartz cell having an optical path length of 1 cm using a dispersion liquid diluted to 0.1% by weight with THF as a sample.
  • a PET film having a thickness of 75 ⁇ m (“Diafoil MRE75” manufactured by Mitsubishi Chemical Corporation) having one side treated with silicone peeling as a cover sheet was laminated.
  • This laminate was photocured by irradiating this laminate with ultraviolet rays for 4 minutes from the cover sheet side with a black light whose position was adjusted so that the irradiation intensity on the irradiation surface directly under the lamp was 3.7 mW / cm 2.
  • Amount: 880 mJ / cm 2 ) a transparent double-sided adhesive sheet with a release film attached to both sides was obtained.
  • the non-volatile content of the adhesive sheet was 98.0%.
  • Comparative Example 2 A 20% solution was prepared by dissolving 0.1 parts by weight of a black dye (“VALIFAST BLACK 3810” manufactured by Orient Chemical Industries Co., Ltd.) in 4 parts by weight of 2EHA. This solution was added to 100 parts by weight of the prepolymer composition prepared in the same manner as in the reference example, and an additional photopolymerization initiator was further added, and then defoaming was performed. An attempt was made to prepare a pressure-sensitive adhesive sheet using this composition, but as in Comparative Example 1, the composition was liquid after irradiation with ultraviolet rays for 4 minutes, and a pressure-sensitive adhesive sheet could not be obtained.
  • VALIFAST BLACK 3810 manufactured by Orient Chemical Industries Co., Ltd.
  • Example 1 To 100 parts by weight of the prepolymer composition prepared in the same manner as in the reference example, 0.5 parts by weight of a 20% dispersion of black pigment (“9050BLACK” manufactured by Tokushiki) (0.1 parts by weight as a black pigment), and additional After adding the photopolymerization initiator, defoaming was performed. This composition was applied onto a substrate so as to have a thickness of 100 ⁇ m, and then heated at 80 ° C. for 1 minute in order to remove the dispersion medium. Then, the cover sheets were pasted together to prepare an adhesive sheet in the same manner as in Reference Example 1. The non-volatile content of the adhesive sheet was 97.1%.
  • 9050BLACK manufactured by Tokushiki
  • a pressure-sensitive adhesive sheet was produced in the same manner as in Reference Example 1 except that the irradiation time of ultraviolet rays was changed to 6 minutes and the integrated irradiation amount was changed to 1320 mJ / cm 2.
  • Example 3 and Example 4 A pressure-sensitive adhesive sheet was produced in the same manner as in Example 2 except that the amount of the black pigment added and the thickness of the pressure-sensitive adhesive sheet were changed as shown in Table 1.
  • Example 5 (Polymerization of prepolymer) Lauryl acrylate (LA): 36.5 parts by weight, 2EHA: 60 parts by weight, N-vinylpyrrolidone (NVP): 2.5 parts by weight, and 4HBA: 1 part by weight, and light as monomer components for prepolymer formation.
  • a polymerization initiator BASF's "Irgacure 184": 0.05 parts by weight and BASF's "Irgacure 651”: 0.05 parts by weight
  • BASF's "Irgacure 651" 0.05 parts by weight
  • a pressure-sensitive adhesive sheet was produced in the same manner as in Reference Example 1 except that the irradiation time of ultraviolet rays was changed to 6 minutes and the integrated irradiation amount was changed to 1320 mJ / cm 2.
  • Example 6 and Example 7 A pressure-sensitive adhesive sheet was produced in the same manner as in Example 5 except that the amount of the black pigment added and the thickness of the pressure-sensitive adhesive sheet were changed as shown in Table 1.
  • the irradiation time of ultraviolet rays was 4 minutes for Reference Example 1 and Example 1 (integrated irradiation amount 880 mJ / cm 2 ), 6 minutes for Examples 2 to 7 (integrated irradiation amount 1320 mJ / cm 2 ), and 7 minutes for Comparative Example 1 (integrated irradiation amount 1320 mJ / cm 2).
  • the integrated irradiation dose was 1540 mJ / cm 2 ).
  • the transmission spectrum was measured using a sample irradiated with ultraviolet rays for 7 minutes for Comparative Example 1 and a sample irradiated with ultraviolet rays for 25 minutes for Comparative Example 2.
  • the pressure-sensitive adhesive sheet of Reference Example 1 containing no colorant has an average transmittance of visible light (wavelength 400 to 700 nm) larger than the average transmittance of ultraviolet rays (wavelength 330 to 400 nm), whereas the pressure-sensitive adhesive sheet has a pressure-sensitive adhesive composition.
  • the average transmittance of ultraviolet rays was larger than the average transmittance of visible light.
  • the maximum transmittance in the ultraviolet region was larger than the maximum transmittance in the visible light region.
  • Comparative Example 1 and Comparative Example 2 the average transmittance of ultraviolet rays was smaller than the average transmittance of visible light, and the maximum transmittance in the ultraviolet region was smaller than the maximum average transmittance in the visible light region.
  • Comparative Example 1 since the colorant (dye) was not uniformly dissolved in the pressure-sensitive adhesive composition, the measured value of the transmittance was large.
  • Comparative Example 2 in which a colorant dissolved in a monomer (2EHA) was added in advance, the transmittance of visible light was sufficiently reduced, but the transmittance of ultraviolet rays was also significantly reduced, and it took 25 minutes (25 minutes). Even after irradiation with ultraviolet rays of 5500 mJ / cm 2 ), the adhesive was not sufficiently solidified. From these results, it can be seen that in Comparative Examples 1 and 2, the photocuring rate (photocuring efficiency) of the pressure-sensitive adhesive is significantly reduced due to the colorant absorbing ultraviolet rays.
  • Example 1 has sufficiently high photocurability as compared with Comparative Example 1 and Comparative Example 2. Further, in Examples 2 to 7, as in Example 1, there are few unreacted monomers and high photocuring even when the non-volatile content is large and the content of the colorant is large or the transmittance of visible light is low. It can be seen that it has sex.

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PCT/JP2020/036330 2019-10-07 2020-09-25 光硬化性粘着剤組成物、両面粘着シートおよびその製造方法、ならびに光学デバイスおよびその製造方法 Ceased WO2021070635A1 (ja)

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WO2026053727A1 (ja) * 2024-09-03 2026-03-12 日東電工株式会社 光硬化性粘着剤組成物、粘着剤、粘着剤付き部材、粘着剤の製造方法、硬化体、部材及び硬化体の製造方法

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