WO2021070801A1 - Composition d'adhésif - Google Patents

Composition d'adhésif Download PDF

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Publication number
WO2021070801A1
WO2021070801A1 PCT/JP2020/037825 JP2020037825W WO2021070801A1 WO 2021070801 A1 WO2021070801 A1 WO 2021070801A1 JP 2020037825 W JP2020037825 W JP 2020037825W WO 2021070801 A1 WO2021070801 A1 WO 2021070801A1
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WIPO (PCT)
Prior art keywords
meth
acrylate
sensitive adhesive
pressure
wavelength
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PCT/JP2020/037825
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English (en)
Japanese (ja)
Inventor
悠司 淺津
由紀 西上
浩司 久門
Original Assignee
住友化学株式会社
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Priority to KR1020227014965A priority Critical patent/KR20220082009A/ko
Priority to CN202080070630.XA priority patent/CN114502680B/zh
Publication of WO2021070801A1 publication Critical patent/WO2021070801A1/fr

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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
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
    • C08K5/3472—Five-membered rings
    • C08K5/3475—Five-membered rings condensed with carbocyclic rings
    • 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
    • C09J201/00—Adhesives based on unspecified macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • 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
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/22—Absorbing filters
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/22—Absorbing filters
    • G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements
    • G02B5/3025—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state
    • G02B5/3033—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state in the form of a thin sheet or foil, e.g. Polaroid
    • G02B5/3041—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state in the form of a thin sheet or foil, e.g. Polaroid comprising multiple thin layers, e.g. multilayer stacks
    • G02B5/305—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state in the form of a thin sheet or foil, e.g. Polaroid comprising multiple thin layers, e.g. multilayer stacks including organic materials, e.g. polymeric layers
    • 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
    • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
    • G02F1/133509—Filters, e.g. light shielding masks
    • G02F1/133514—Colour filters
    • 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
    • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
    • G02F1/133528—Polarisers
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/02—Details
    • 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
    • C09J2301/30—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier
    • C09J2301/312—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier parameters being the characterizing feature

Definitions

  • the present invention relates to a pressure-sensitive adhesive composition, a pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition, and an optical laminate in which the pressure-sensitive adhesive layer is laminated.
  • Display devices such as organic electroluminescence displays (organic EL display devices) and liquid crystal display devices include various members such as organic EL elements, display elements such as liquid crystal cells, and optical films such as polarizing plates. It is used.
  • the liquid crystal compound used for the organic EL element or the liquid crystal cell a compound having a relatively weak weather resistance is often used, so that deterioration due to ultraviolet rays (UV) tends to be a problem.
  • Patent Document 1 describes an ultraviolet absorbing (shielding) pressure-sensitive adhesive composition containing an acrylic resin and a triazine-based ultraviolet absorber, and the pressure-sensitive adhesive composition is used.
  • the formed pressure-sensitive adhesive layer with a thickness of 15 ⁇ m is also described.
  • the organic EL display device and the liquid crystal display device are required to be remarkably thinned, and the members used for the organic EL display device and the liquid crystal display device are also required to be remarkably thinned. Therefore, the ultraviolet absorbing (shielding) adhesive layer itself is also required to be thinned. However, if the UV-absorbing (shielding) pressure-sensitive adhesive layer is simply thinned (for example, less than 12 ⁇ m), the UV-absorbing performance of the pressure-sensitive adhesive layer is lowered.
  • the present invention includes the following inventions.
  • Resin (A) A light selective absorption compound (B) that exhibits maximum absorption at a wavelength of 360 nm or more and satisfies the following formulas (1) and (2), and has a polymerizable group in the molecule and has a wavelength of 300 nm or more and a wavelength of less than 360 nm.
  • a pressure-sensitive adhesive composition containing at least one selected from a monomer (C-1) exhibiting maximum absorption and a resin (C-2) exhibiting maximum absorption at a wavelength of 300 nm or more and less than 360 nm.
  • ⁇ (380) ⁇ 25 (1) ⁇ (380) / ⁇ (420) ⁇ 20 (2)
  • ⁇ (380) represents the gram extinction coefficient of the light selective absorption compound (B) at a wavelength of 380 nm
  • ⁇ (420) is the wavelength of the light selective absorption compound (B) of 420 nm.
  • the unit of the gram extinction coefficient is L / (g ⁇ cm).
  • the pressure-sensitive adhesive composition according to [1] which further comprises an initiator (D).
  • the pressure-sensitive adhesive composition according to [11], wherein the resin (A) having a glass transition temperature of 40 ° C. or lower is a (meth) acrylic resin.
  • the present invention has a pressure-sensitive adhesive layer having sufficient ultraviolet absorption performance even if the film thickness is thin (for example, less than 12 ⁇ m), less occurrence of bleed-out, and less absorption of visible light near a wavelength of 420 nm, and the adhesive.
  • a pressure-sensitive adhesive composition for forming an agent layer is provided.
  • An example of the layer structure of the laminated body in which the release film is provided on the pressure-sensitive adhesive layer of the present invention is shown.
  • An example of the layer structure of the optical film with an adhesive layer of the present invention is shown.
  • An example of the layer structure of the optical film with an adhesive layer of the present invention is shown.
  • An example of the layer structure of the optical laminate of the present invention is shown.
  • An example of the layer structure of the optical laminate of the present invention is shown.
  • the pressure-sensitive adhesive composition of the present invention contains the following (Z-1) to (Z-3).
  • Z-1) Resin (A)
  • Z-2) A light selective absorption compound (B) that exhibits maximum absorption at a wavelength of 360 nm or more and satisfies the following formulas (1) and (2) (hereinafter, may be referred to as a light selective absorption compound (B).
  • Z-3) In the case of a monomer (C-1) having a polymerizable group in the molecule and exhibiting maximum absorption at a wavelength of 300 nm or more and less than 360 nm (hereinafter referred to as a light selective absorption compound (C-1)).
  • C-2) exhibiting maximum absorption at a wavelength of 300 nm or more and less than 360 nm
  • the resin (A) of the present invention is not particularly limited as long as it is a resin used in the pressure-sensitive adhesive composition.
  • the resin (A) is preferably a resin having a glass transition temperature (Tg) of 40 ° C. or lower.
  • the glass transition temperature (Tg) of the resin (A) is more preferably 20 ° C. or lower, further preferably 10 ° C. or lower, and particularly preferably 0 ° C. or lower.
  • the glass transition temperature of the resin (A) is usually ⁇ 80 ° C. or higher, preferably ⁇ 70 ° C. or higher, more preferably ⁇ 60 ° C. or higher, and even more preferably ⁇ 55 ° C. or higher.
  • the glass transition temperature of the resin (A) is 40 ° C. or lower, it is advantageous to improve the adhesion of the pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition containing the resin (A) to the adherend. Further, when the glass transition temperature of the resin (A) is ⁇ 80 ° C. or higher, it is advantageous to improve the durability of the pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition containing the resin (A).
  • the glass transition temperature can be measured by a differential scanning calorimeter (DSC). Further, it is preferable that the resin (A) does not show maximum absorption between the wavelength of 300 nm and the wavelength of 780 nm.
  • Examples of the resin (A) include (meth) acrylic resin, silicone resin, rubber resin, urethane resin and the like, and (meth) acrylic resin is preferable.
  • the (meth) acrylic resin is preferably a polymer containing a structural unit derived from the (meth) acrylic acid ester as a main component (preferably containing 50% by mass or more).
  • the structural unit derived from the (meth) acrylic acid ester is a structural unit derived from one or more monomers other than the (meth) acrylic acid ester (for example, a structural unit derived from a monomer having a polar functional group). It may be included.
  • (meth) acrylic acid means that either acrylic acid or methacrylic acid may be used, and "(meth)" in the case of (meth) acrylate or the like has the same meaning. ..
  • Examples of the (meth) acrylic acid ester include (meth) acrylic acid ester represented by the following formula (a).
  • R 1A is represented by a hydrogen atom or a methyl group
  • R 2A is represented by an alkyl group having 1 to 14 carbon atoms or an aromatic hydrocarbon group having 6 to 20 carbon atoms.
  • the hydrogen atom of the aromatic hydrocarbon group may be replaced with an alkoxy group having 1 to 10 carbon atoms.
  • R 2A is preferably an alkyl group having 1 to 14 carbon atoms, and more preferably an alkyl group having 1 to 8 carbon atoms.
  • (meth) acrylic acid ester represented by the formula (a), Methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, n-butyl (meth) acrylate, n-pentyl (meth) acrylate, n-hexyl (meth) acrylate, N-Heptyl (meth) acrylate, n-octyl (meth) acrylate, n-nonyl (meth) acrylate, n-decyl (meth) acrylate, n-dodecyl (meth) acrylate, (meth) acrylate Linear alkyl esters of (meth) acrylic acid, such as lauryl, stearyl (meth) acrylic acid, etc .; (Meta) i-propyl acrylate, (meth) i-butyl acrylate, t-butyl (
  • Alkyl ester Cyclohexyl (meth) acrylate, isobolonyl (meth) acrylate, adamantyl (meth) acrylate, dicyclopentanyl (meth) acrylate, cyclododecyl (meth) acrylate, methylcyclohexyl (meth) acrylate, ( Alicyclic skeleton-containing alkyl ester of (meth) acrylic acid such as trimethylcyclohexyl acrylate, tert-butylcyclohexyl (meth) acrylate, cyclohexyl ⁇ -ethoxyacrylate, etc.; Aromatic ring skeleton-containing ester of (meth) acrylic acid such as phenyl (meth) acrylic acid and benzyl (meth) acrylate; And so on.
  • Examples of the substituent-containing (meth) acrylic acid ester include 2-methoxyethyl (meth) acrylate, ethoxymethyl (meth) acrylate, phenoxyethyl (meth) acrylate, and 2- (2- (2-) (meth) acrylate. Phenoxyethoxy) ethyl and the like can be mentioned.
  • Examples of the (meth) acrylic acid ester include (meth) acrylic acid phenoxydiethylene glycol, (meth) acrylic acid phenoxypoly (ethylene glycol) and the like.
  • Each of these (meth) acrylic acid esters can be used alone, or a plurality of different ones may be used.
  • the resin (A) of the present invention is a structural unit derived from the (meth) acrylic acid alkyl ester (a1) in which the glass transition temperature Tg of the homopolymer is less than 0 ° C. among the (meth) acrylic acid alkyl esters, and the homopolymer. It preferably contains a structural unit derived from the (meth) acrylic acid alkyl ester (a2) having a Tg of 0 ° C. or higher. This is advantageous in increasing the high temperature durability of the pressure-sensitive adhesive layer.
  • Tg of the homopolymer of the (meth) acrylic acid alkyl ester a literature value such as POLYMER HANDBOOK (Wiley-Interscience) can be adopted.
  • (meth) acrylic acid alkyl ester (a1) examples include ethyl acrylate, n- and i-propyl acrylate, n- and i-butyl acrylate, n-pentyl acrylate, n- and i- acrylate. Hexyl, n-heptyl acrylate, n- and i-octyl acrylate, 2-ethylhexyl acrylate, n- and i-nonyl acrylate, n- and i-decyl acrylate, n-dodecyl acrylate, etc. Contains a (meth) acrylic acid alkyl ester having about 2 to 12 carbon atoms in the alkyl group of.
  • (meth) acrylic acid alkyl ester (a1) only one type may be used, or two or more types may be used in combination. Of these, n-butyl acrylate, n-octyl acrylate, 2-ethylhexyl acrylate and the like are preferable from the viewpoint of followability and reworkability when laminated on an optical film.
  • the (meth) acrylic acid alkyl ester (a2) is a (meth) acrylic acid alkyl ester other than the (meth) acrylic acid alkyl ester (a1).
  • Specific examples of the (meth) acrylic acid alkyl ester (a2) include methyl acrylate, cyclohexyl acrylate, isobolonyl acrylate, stearyl acrylate, t-butyl acrylate and the like.
  • the (meth) acrylic acid alkyl ester (a2) only one type may be used, or two or more types may be used in combination. Among them, from the viewpoint of high temperature durability, the (meth) acrylic acid alkyl ester (a2) preferably contains methyl acrylate, cyclohexyl acrylate, isobolonyl acrylate and the like, and more preferably contains methyl acrylate.
  • the structural unit derived from the (meth) acrylic acid ester represented by the formula (a) is preferably 50% by mass or more, preferably 60 to 95% by mass, based on the total structural units contained in the (meth) acrylic resin. It is preferably 65 to 95% by mass or more, and more preferably 65 to 95% by mass or more.
  • a structural unit derived from a monomer other than the (meth) acrylic acid ester a structural unit derived from a monomer having a polar functional group is preferable, and a structure derived from a (meth) acrylic acid ester having a polar functional group is preferable.
  • the unit is more preferred.
  • the polar functional group include a hydroxy group, a carboxyl group, a substituted or unsubstituted amino group, a heterocyclic group such as an epoxy group, and the like.
  • a monomer having a hydroxy group and a monomer having a carboxyl group are preferable, and a monomer having a hydroxy group and a carboxyl group are preferable in terms of the reactivity between the (meth) acrylic acid ester polymer and the cross-linking agent. It is more preferable to contain any of the monomers having.
  • the monomer having a hydroxy group 2-hydroxyethyl acrylate, 3-hydroxypropyl acrylate, 4-hydroxybutyl acrylate, 5-hydroxypentyl acrylate, and 6-hydroxyhexyl acrylate are preferable. In particular, good durability can be obtained by using 2-hydroxyethyl acrylate, 4-hydroxybutyl acrylate and 5-hydroxypentyl acrylate.
  • Acrylic acid is preferably used as the monomer having a carboxyl group.
  • the (meth) acrylic resin should be substantially free of structural units derived from the monomer having an amino group.
  • substantially not contained means that the amount is 0.1 parts by mass or less out of 100 parts by mass of all the structural units constituting the (meth) acrylic resin.
  • the content of the structural unit derived from the monomer having a polar functional group is preferably 20 parts by mass or less, more preferably 0.5 parts by mass, based on 100 parts by mass of all the structural units of the (meth) acrylic resin. More than 15 parts by mass, more preferably 0.5 parts by mass or more and 10 parts by mass or less, and particularly preferably 1 part by mass or more and 7 parts by mass or less.
  • Examples of the structural unit derived from a monomer other than the (meth) acrylic acid ester include a structural unit derived from a monomer having an aromatic group.
  • Examples of the monomer having an aromatic group include (meth) acrylic acid ester having one (meth) acryloyl group and one or more aromatic rings (for example, benzene ring, naphthalene ring, etc.) in the molecule.
  • a (meth) acrylic acid ester having a phenyl group, a phenoxyethyl group, or a benzyl group can be mentioned.
  • the content of the structural unit derived from the monomer having an aromatic group is preferably 20 parts by mass or less, more preferably 4 parts by mass or more and 20 parts by mass with respect to 100 parts by mass of all the structural units of the (meth) acrylic resin. It is less than or equal to parts by mass, more preferably 4 parts by mass or more and 16 parts by mass or less.
  • Structural units derived from monomers other than (meth) acrylic acid esters include structural units derived from styrene-based monomers, structural units derived from vinyl-based monomers, and a plurality of (meth) acryloyl in the molecule.
  • Structural units derived from a monomer having a group, structural units derived from a (meth) acrylamide-based monomer, and the like can also be mentioned.
  • styrene-based monomer examples include styrene; methylstyrene, dimethylstyrene, trimethylstyrene, ethylstyrene, diethylstyrene, triethylstyrene, propylstyrene, butylstyrene, hexylstyrene, heptylstyrene, octylstyrene and other alkylstyrenes; fluorostyrene, Examples thereof include halogenated styrene such as chlorostyrene, bromostyrene, dibromostyrene and iodostyrene; nitrostyrene; acetylstyrene; methoxystyrene; and divinylbenzene.
  • halogenated styrene such as chlorostyrene, bromostyrene, dibromostyren
  • vinyl-based monomer examples include fatty acid vinyl esters such as vinyl acetate, vinyl propionate, vinyl butyrate, vinyl 2-ethylhexanoate, and vinyl laurate; vinyl halides such as vinyl chloride and vinyl bromide; and vinylidene chloride and the like.
  • vinylidene halide nitrogen-containing heteroaromatic vinyl such as vinylpyridine, vinylpyrrolidone and vinylcarbazole; conjugated diene such as butadiene, isoprene and chloroprene; and unsaturated nitriles such as acrylonitrile and methacrylonitrile.
  • Examples of the monomer having a plurality of (meth) acryloyl groups in the molecule include 1,4-butanediol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, and 1,9-nonanediol di ( Two (meth) acryloyl groups in the molecule of meta) acrylate, ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, tetraethylene glycol di (meth) acrylate, tripropylene glycol di (meth) acrylate, etc.
  • Monomer having; Examples thereof include a monomer having three (meth) acryloyl groups in the molecule such as trimethyl propantri (meth) acrylate.
  • Examples of the (meth) acrylamide-based monomer include N-methylol (meth) acrylamide, N- (2-hydroxyethyl) (meth) acrylamide, N- (3-hydroxypropyl) (meth) acrylamide, and N- (4-).
  • N- (methoxymethyl) acrylamide N- (ethoxymethyl) acrylamide, N- (propoxymethyl) acrylamide, N- (butoxymethyl) acrylamide and N- (2-methylpropoxymethyl) acrylamide are preferable.
  • the weight average molecular weight (Mw) of the (meth) acrylic resin is preferably 500,000 to 2.5 million.
  • the weight average molecular weight is 500,000 or more, the durability of the pressure-sensitive adhesive layer is improved, and problems such as floating and peeling between the adherend and the pressure-sensitive adhesive layer and cohesive failure of the pressure-sensitive adhesive layer are caused. Easy to suppress.
  • the weight average molecular weight is 2.5 million or less, it is advantageous from the viewpoint of coatability. From the viewpoint of achieving both the durability of the pressure-sensitive adhesive layer and the coatability of the pressure-sensitive adhesive composition, the weight average molecular weight is preferably 600,000 to 1.8 million, often preferably 700,000 to 1.7 million, and particularly preferably 100. It is 10,000 to 1.6 million.
  • the molecular weight distribution (Mw / Mn) represented by the ratio of the weight average molecular weight (Mw) to the number average molecular weight (Mn) is usually 2 to 10, preferably 3 to 8, and more preferably 3 to 6. ..
  • the weight average molecular weight can be analyzed by gel permeation chromatography and is a value in terms of standard polystyrene.
  • the (meth) acrylic acid resin preferably has a viscosity at 25 ° C. of 20 Pa ⁇ s or less, preferably 0.1 to 15 Pa ⁇ s, when dissolved in ethyl acetate to prepare a solution having a concentration of 20% by mass. Is more preferable.
  • a viscosity in this range is advantageous from the viewpoint of coatability when the pressure-sensitive adhesive composition is applied to the base material.
  • the viscosity can be measured with a Brookfield viscometer.
  • the (meth) acrylic resin can be produced by a known method such as a solution polymerization method, a massive polymerization method, a suspension polymerization method, or an emulsion polymerization method, and the solution polymerization method is particularly preferable.
  • a solution polymerization method for example, a monomer and an organic solvent are mixed, a thermal polymerization initiator is added under a nitrogen atmosphere, and the temperature conditions are 40 to 90 ° C., preferably 50 to 80 ° C., 3 to 15 A method of stirring for about an hour can be mentioned.
  • a monomer or a thermal polymerization initiator may be added continuously or intermittently during the polymerization.
  • the monomer and the thermal polymerization initiator may be in a state of being added to an organic solvent.
  • organic solvent include aromatic hydrocarbons such as toluene and xylene; esters such as ethyl acetate and butyl acetate; aliphatic alcohols such as propyl alcohol and isopropyl alcohol; ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone. And so on.
  • the thermal polymerization initiator a known thermal polymerization initiator can be used. Further, a photopolymerization initiator may be used instead of the thermal polymerization initiator, and a polymerization method using ultraviolet rays or the like may be used.
  • the content of the resin (A) is usually 50% by mass to 99.9% by mass, preferably 60% by mass to 95% by mass, and more preferably 70% by mass, based on 100% by mass of the solid content of the pressure-sensitive adhesive composition. It is from mass% to 90% by mass.
  • the light selective absorption compound (B) exhibits maximum absorption at a wavelength of 360 nm or more.
  • the light selective absorption compound (B) preferably exhibits maximum absorption during a wavelength of 360 nm or more and a wavelength of 420 nm or less, and more preferably exhibits maximum absorption between a wavelength of 370 nm or more and a wavelength of 410 nm or less.
  • the light selective absorption compound (B) satisfies the following formulas (1) and (2).
  • ⁇ (380) ⁇ 25 (1)
  • ⁇ (380) represents the gram absorption coefficient of the light selective absorption compound (B) at a wavelength of 380 nm.
  • the unit of the gram extinction coefficient is L / (g ⁇ cm).
  • ⁇ (380) represents the gram extinction coefficient of the light selective absorption compound (B) at a wavelength of 380 nm
  • ⁇ (420) represents the gram extinction coefficient of the light selective absorption compound (B) at a wavelength of 420 nm. ..
  • the unit of the gram extinction coefficient is L / (g ⁇ cm). ]
  • the value of ⁇ (380) is preferably 30 L / (g ⁇ cm) or more, more preferably 35 L / (g ⁇ cm) or more, and even more preferably 50 L / (g ⁇ cm) or more. , 100 L / (g ⁇ cm) or more, and usually 10000 L / (g ⁇ cm) or less.
  • a compound having a larger value of ⁇ (380) is more likely to absorb light having a wavelength of 380 nm and is more likely to exhibit a function of suppressing deterioration due to ultraviolet rays.
  • the light selective absorption compound (B) preferably has a value of ⁇ (380) / ⁇ (420) of 25 or more, more preferably 35 or more, even more preferably 50 or more, and particularly more 100 or more. preferable.
  • the pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition containing a compound having a large value of ⁇ (380) / ⁇ (420) absorbs ultraviolet rays in the vicinity of 380 nm without disturbing the color expression of the display device. Further, it is possible to suppress photodegradation of display devices such as laminated optical films (phase difference films) and organic EL elements.
  • the light selective absorption compound (B) preferably does not contain a merocyanine structure in the molecule.
  • the light selective absorption compound (B) a commercially available product may be used, and examples thereof include FUV-002B (manufactured by Fuji Film Co., Ltd.).
  • the content of the light selective absorption compound (B) is usually 0.01 to 50 parts by mass, preferably 0.1 to 20 parts by mass, and 0.5 parts by mass with respect to 100 parts by mass of the resin (A). It is more preferably to 10 parts by mass, and particularly preferably 1.0 to 5 parts by mass.
  • the light selective absorption compound (C-1) is a monomer having a polymerizable group in the molecule and exhibiting maximum absorption at a wavelength of 300 nm or more and less than 360 nm.
  • the light selective absorption compound (C-1) preferably exhibits maximum absorption at a wavelength of 320 nm or more and a wavelength of 355 nm or less, and more preferably exhibits maximum absorption at a wavelength of 330 nm or more and a wavelength of 350 nm or less.
  • the polymerizable group of the photoselective absorption compound (C-1) includes a cationically polymerizable group such as an epoxy group, an oxetanyl group, an oxazolino group, an aziridino group and a vinyl ether group; and a radically polymerizable group such as an ethylenically unsaturated group. Radicals can be mentioned.
  • the polymerizable group of the photoselective absorption compound (C-1) is preferably a radical polymerizable group such as an ethylenically unsaturated group.
  • the ethylenically unsaturated group examples include a vinyl group, an ⁇ -methylvinyl group, an acryloyl group, a metaacryloyl group, an allyl group, a styryl group, a (meth) acrylamide group, a vinylsulfone group, a (meth) acryloyloxy group and the like. Can be mentioned.
  • the photoselective absorption compound (C-1) includes, for example, a compound having a polymerizable group and a benzotriazole skeleton in the molecule, a compound having a polymerizable group and a benzoimidazole skeleton in the molecule, and a polymerizable group in the molecule.
  • Examples thereof include a compound having a triazine skeleton, a compound having a polymerizable group and a benzophenone skeleton in the molecule, and a compound having a polymerizable group and a non-polymerizable cyanoacrylate skeleton in the molecule.
  • Examples of the light selective absorption compound (C-1) include the compounds described below. 2- [2- (2,4-dihydroxyphenyl) -2H-benzotriazole-5-yloxy] ethyl methacrylate, 2- [2- (4-ethoxy-2-hydroxyphenyl) -2H-benzotriazole-5-yloxy] ethyl methacrylate, 2- [2- (4-Butoxy-2-hydroxyphenyl) -2H-benzotriazole-5-yloxy] ethyl methacrylate, 2- [2- (4-Benzoyloxy-2-hydroxyphenyl) -2H-benzotriazole-5-yloxy] ethyl methacrylate, 4- [2- (2,4-dihydroxyphenyl) -2H-benzotriazole-5-yloxy] butyl methacrylate, 4- [2- (4-ethoxy-2-hydroxyphenyl) -2H-benzotriazole-5-yloxy] butyl methacrylate, 4-
  • the light selective absorption compound (C-1) may be a compound shown below.
  • the light selective absorption compound (C-1) a commercially available product may be used, and specifically, "RUVA-93” (Otsuka Chemical Co., Ltd.), “CHISORB 5678” (Double bond Chemical Co., Ltd.), “Tinuvin”. R 796 ”(BASF) and the like can be mentioned.
  • the photoselective absorption compound (C-1) includes a compound having a polymerizable group and a benzotriazole skeleton in the molecule, a compound having a polymerizable group and a triazine skeleton in the molecule, or a polymerizable group and a benzophenone skeleton in the molecule. It is preferable that the compound has.
  • the light selective absorption resin (C-2) is a resin that exhibits maximum absorption at a wavelength of 300 nm or more and less than 360 nm.
  • the light selective absorption resin (C-2) preferably exhibits maximum absorption at a wavelength of 320 nm or more and a wavelength of 355 nm or less, and more preferably exhibits maximum absorption at a wavelength of 330 nm or more and a wavelength of 350 nm or less.
  • Examples of the light selective absorption resin (C-2) include a resin containing a structural unit derived from the above-mentioned light selective absorption compound (C-1) (hereinafter, may be referred to as a structural unit (C-1)). Can be mentioned.
  • the light selective absorption resin (C-2) may be a homopolymer containing a structural unit (C-1) or a copolymer.
  • the light selective absorption resin (C-2) is preferably a copolymer containing a structural unit (C-1).
  • the light selective absorption resin (C-2) preferably contains the structural unit (C-1) in an amount of 0.1 to 90% by mass, more preferably 1 to 75% by mass, based on all the structural units. It is more preferably contained in an amount of 5 to 60% by mass, particularly preferably 10 to 50% by mass.
  • the structural unit contained in the light selective absorption resin (C-2) other than the structural unit (C-1) include the structural unit derived from the monomer forming the resin (A) described above. Specifically, the structural unit derived from the (meth) acrylic acid ester represented by the above formula (a), the structural unit derived from the monomer having a polar functional group described above, and the structure derived from the styrene-based monomer described above.
  • Examples thereof include a unit, a structural unit derived from the vinyl-based monomer described above, a structural unit derived from the (meth) acrylamide-based monomer described above, and the like.
  • Examples of the structural unit contained in the light selective absorption resin (C-2) other than the structural unit (C-1) include the structural unit derived from the (meth) acrylate ester represented by the above formula (a) and the above-mentioned polar functional group.
  • a structural unit derived from a monomer having a hydroxy group or the like is preferable, and a structural unit derived from a (meth) acrylic acid ester represented by the above formula (a), a monomer having a hydroxy group, or a (meth) acrylamide-based monomer is derived.
  • Structural units and the like are more preferable.
  • it is preferably a structural unit derived from normal butyl acrylate, methyl acrylate, 2-ethylhexyl acrylate, normal octyl acrylate and the like.
  • the light selective absorption resin (C-2) may be a commercially available product, or may be synthesized by a known method (for example, JP-A-2012-25811). Specific examples of the light selective absorption resin (C-2) include the resins described in JP2012-25811A. Moreover, as a commercial product of a light selective absorption resin (C-2), vana resin UVR series (Shin Nakamura Chemical Industry Co., Ltd.) and the like can be mentioned.
  • the content of the light selective absorption compound (C-1) or the light selective absorption resin (C-2) is usually 0.1 to 70 parts by mass with respect to 100 parts by mass of the resin (A), and is 1.0 to 1.0 parts by mass. It is preferably 50 parts by mass, more preferably 5.0 to 30 parts by mass, further preferably 7.5 to 25 parts by mass, and particularly preferably 10 to 20 parts by mass. When both the light selective absorption compound (C-1) and the light selective absorption resin (C-2) are contained, the total may be within the above range.
  • the pressure-sensitive adhesive composition of the present invention may further contain an initiator (D), a radical curable component (E), and a cross-linking agent (F).
  • the initiator (D) may be any compound that causes a polymerization reaction of the photoselective absorption compound (C-1) or the radical curable component (E) contained if necessary.
  • the initiator (D) is either a compound that causes a polymerization reaction by absorbing heat energy (thermal polymerization initiator) or a compound that causes a polymerization reaction by absorbing light energy (photopolymerization initiator). You may.
  • the light is preferably an active energy ray such as visible light, ultraviolet light, X-ray, or electron beam.
  • thermal polymerization initiator examples include compounds that generate radicals by heating (thermal radical generators), compounds that generate acids by heating (thermal acid generators), and compounds that generate bases by heating (thermal base generators). ) Etc. can be mentioned.
  • Photopolymerization initiators include compounds that generate radicals by absorbing light energy (photoradical generators), compounds that generate acids by absorbing light energy (photoacid generators), and light energy. Examples thereof include a compound (photobase generator) that generates a base by absorbing the above.
  • the radical generator include a thermal radical generator and a photoradical generator.
  • the initiator (D) may contain two or more kinds, and a photoradical generator and a thermal radical generator may be used in combination.
  • the radical generator examples include an alkylphenone compound, a benzoin compound, a benzophenone compound, an oxime ester compound, a phosphine compound and the like.
  • the radical generator is preferably a photoradical generator, and more preferably an oxime ester-based photoradical generator from the viewpoint of reactivity of the polymerization reaction.
  • the reaction rate of the light selective absorption compound (C-1) and the radical curing component (E) can be increased even under curing conditions where the illuminance or the amount of light is weak.
  • alkylphenone compound examples include an ⁇ -aminoalkylphenone compound, an ⁇ -hydroxyalkylphenone compound, and an ⁇ -alkoxyalkylphenone compound.
  • ⁇ -aminoalkylphenone compound examples include 2-methyl-2-morpholino-1- (4-methylsulfanylphenyl) propan-1-one and 2-dimethylamino-1- (4-morpholinophenyl) -2-benzylbutane. Examples thereof include -1-one, 2-dimethylamino-1- (4-morpholinophenyl) -2- (4-methylphenylmethyl) butane-1-one, and preferably 2-methyl-2-morpholino-1-one.
  • Examples thereof include (4-methylsulfanylphenyl) propan-1-one, 2-dimethylamino-1- (4-morpholinophenyl) -2-benzylbutane-1-one and the like.
  • the ⁇ -aminoalkylphenone compounds are Irgacure (registered trademark) 127, 184, 369, 369E, 379EG, 651, 907, 1173, 2959, (above, manufactured by BASF Japan Ltd.), Sequol (registered trademark) BEE (Seiko).
  • Commercially available products such as (manufactured by Kagaku Co., Ltd.) may be used.
  • benzoin compound examples include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether and the like.
  • benzophenone compound examples include benzophenone, methyl o-benzoyl benzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, 3,3', 4,4'-tetra (tert-butylperoxycarbonyl). ) Benzophenone, 2,4,6-trimethylbenzophenone and the like. Commercially available products may be used as the benzophenone compound.
  • Examples of the oxime ester compound include N-benzoyloxy-1- (4-phenylsulfanylphenyl) butane-1-one-2-imine and N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-one-.
  • the oxime compounds are Irgacure OXE-01, OXE-02, OXE-03 (above, manufactured by BASF Japan), N-1919, NCI-730, NCI-831, NCI-930 (manufactured by ADEKA), PBG3057 (TRONLY).
  • a commercially available product such as (manufactured by) may be used.
  • phosphine compound examples include acylphosphine oxides such as phenyl (2,4,6-trimethylbenzoyl) phosphine oxide and diphenyl (2,4,6-trimethylbenzoyl) phosphine oxide.
  • acylphosphine oxides such as phenyl (2,4,6-trimethylbenzoyl) phosphine oxide and diphenyl (2,4,6-trimethylbenzoyl) phosphine oxide.
  • examples of the phosphine compound include Irgacure (registered product) TPO and Irgacure 819 (manufactured by BASF Japan Ltd.).
  • Examples of the acid generator include onium salts such as aromatic iodonium salts and aromatic sulfonium salts; aromatic diazonium salts; and iron-alene complexes.
  • the aromatic iodonium salt is a compound having a diaryliodonium cation, and as the cation, a diphenyliodonium cation can be typically mentioned.
  • the aromatic sulfonium salt is a compound having a triarylsulfonium cation, and examples of the cation include a triphenylsulfonium cation and a 4,4'-bis (diphenylsulfonio) diphenylsulfide cation.
  • the aromatic diazonium salt is a compound having a diazonium cation, and examples of the cation include a benzenediazonium cation.
  • the iron-arene complex is typically a cyclopentadienyl iron (II) arene cationic complex salt.
  • the cations shown above form a photocation generator in pairs with anions (anions).
  • anions which constitute the photo-cation generator special phosphorus based anions [(Rf) n PF 6- n] -, hexafluorophosphate anion PF 6 -, hexafluoroantimonate anion SbF 6 -, pentafluoro-hydroxy antimonate anion SbF 5 (OH) -, hexafluoro ah cell anions AsF 6 -, tetrafluoroborate anion BF 4 -, tetrakis (pentafluorophenyl) borate anion B (C 6 F 5) 4 - and the like.
  • a special phosphate based anionic [(Rf) n PF 6- n] -, hexafluorophosphate anion PF 6 -, tetrakis (pentafluorophenyl phenyl) borate anion B (C 6 F 5) 4 -, hexafluoroantimonate anion SbF 6 - is preferably.
  • Examples of the photobase generator include a carbamate compound, an ⁇ -aminoketone compound, a quaternary ammonium compound, an O-acyloxime compound, and an aminocyclopropenone compound.
  • carbamate compound examples include 1- (2-anthraquinonyl) ethyl 1-piperidin carboxylate, 1- (2-anthraquinonyl) ethyl 1H-2-ethylimidazole-1-carboxylate, and 9-anthrylmethyl 1-piperidincarboxylate.
  • ⁇ -aminoketone compound for example, the following are known. Examples thereof include 1-phenyl-2- (4-morpholinobenzoyl) -2-dimethylaminobutane and 2- (4-methylthiobenzoyl) -2-morpholinopropane.
  • Examples of the quaternary ammonium compound serving as a photobase generator include 1- (4-phenylthiophenacyl) -1-azonia-4-azabicyclo [2,2,2] octanetetraphenylborate and 5- (4- (4-phenylthiophenacil). Phenylthiophenacil) -1-aza-5-azoniabicyclo [4,3,0] -5-nonene tetraphenylborate, 8- (4-phenylthiophenacil) -1-aza-8-azoniabicyclo [5,4 , 0] -7-undecene tetraphenylborate and the like.
  • aminocyclopropenone compound serving as a photobase generator examples include 2-diethylamino-3-phenylcyclopropenone, 2-diethylamino-3- (1-naphthyl) cyclopropenone, and 2-pyrrolidinyl-3-phenylcyclo.
  • examples thereof include propenone, 2-imidazolyl-3-phenylcyclopropenone, 2-isopropylamino-3-phenylcyclopropenone and the like.
  • thermobase generator examples include carbamate derivatives such as 2- (4-biphenyl) -2-propyl carbamate and 1,1-dimethyl-2-cyanoethyl carbamate, and urea such as urea and N, N, N'-trimethylurea.
  • carbamate derivatives such as 2- (4-biphenyl) -2-propyl carbamate and 1,1-dimethyl-2-cyanoethyl carbamate
  • urea such as urea and N, N, N'-trimethylurea.
  • dihydropyridine derivatives such as 1,4-dihydronicotinamide, dicyandiamides
  • salts composed of acids and bases such as organic salts and inorganic salts.
  • the content of the initiator (D) is usually 0.01 to 20 parts by mass, preferably 0.1 to 10 parts by mass, and 0.5 to 5 parts by mass with respect to 100 parts by mass of the resin (A). It is more preferably parts by mass, and even more preferably 1 to 3 parts by mass.
  • radical curable component (E) examples include monomers and oligomers that are cured by a radical polymerization reaction. Examples of the radical curable component (E) include monofunctional or polyfunctional (meth) acrylate compounds, styrene compounds, vinyl compounds and the like.
  • the pressure-sensitive adhesive composition of the present invention may contain two or more radical curable components (E).
  • Examples of the (meth) acrylate-based compound include a (meth) acrylate monomer having at least one (meth) acryloyloxy group in the molecule, a (meth) acrylamide monomer, and at least two (meth) acryloyl groups in the molecule.
  • Examples thereof include (meth) acryloyl group-containing compounds such as (meth) acrylic oligomers having.
  • the (meth) acrylic oligomer is preferably a (meth) acrylate oligomer having at least two (meth) acryloyloxy groups in the molecule.
  • As the (meth) acrylic compound only one kind may be used alone, or two or more kinds may be used in combination.
  • the (meth) acrylate monomer includes a monofunctional (meth) acrylate monomer having one (meth) acryloyloxy group in the molecule and a bifunctional (meth) acrylate having two (meth) acryloyloxy groups in the molecule.
  • Monomers and polyfunctional (meth) acrylate monomers having three or more (meth) acryloyloxy groups in the molecule can be mentioned.
  • Examples of the monofunctional (meth) acrylate monomer include alkyl (meth) acrylate.
  • alkyl (meth) acrylate if the alkyl group has 3 or more carbon atoms, it may be linear, branched, or cyclic.
  • alkyl (meth) acrylate methyl (meth) acrylate, ethyl (meth) acrylate, isopropyl (meth) acrylate, butyl (meth) acrylate, isobutyl (meth) acrylate, t-butyl (meth) acrylate, 2-ethylhexyl ( Meta) acrylate and the like can be mentioned.
  • the monofunctional (meth) acrylate monomer includes aralkyl (meth) acrylate such as benzyl (meth) acrylate; (meth) acrylate of terpenal alcohol such as isobornyl (meth) acrylate; and tetrahydro such as tetrahydrofurfuryl (meth) acrylate.
  • aralkyl (meth) acrylate such as benzyl (meth) acrylate
  • (meth) acrylate of terpenal alcohol such as isobornyl (meth) acrylate
  • tetrahydro such as tetrahydrofurfuryl (meth) acrylate.
  • (Meta) acrylate having a fulfuryl structure having a fulfuryl structure; cyclohexyl at an alkyl group moiety such as cyclohexyl (meth) acrylate, cyclohexylmethylmethacrylate, dicyclopentanyl acrylate, dicyclopentenyl (meth) acrylate, 1,4-cyclohexanedimethanol monoacrylate, etc.
  • (Meta) acrylate having an alkyl group Aminoalkyl (meth) acrylate such as N, N-dimethylaminoethyl (meth) acrylate; 2-phenoxyethyl (meth) acrylate, dicyclopentenyloxyethyl (meth) acrylate, ethyl carbi Examples thereof include (meth) acrylate having an ether bond at the alkyl moiety such as toll (meth) acrylate and phenoxypolyethylene glycol (meth) acrylate.
  • examples of the monofunctional (meth) acrylate monomer include a monofunctional (meth) acrylate having a hydroxyl group at the alkyl moiety; and a monofunctional (meth) acrylate having a carboxyl group at the alkyl moiety.
  • examples of the monofunctional (meth) acrylate having a hydroxyl group at the alkyl moiety include 2-hydroxyethyl (meth) acrylate, 2- or 3-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, and 2-hydroxy-3.
  • -Phenoxypropyl (meth) acrylate trimethylolpropane mono (meth) acrylate, pentaerythritol mono (meth) acrylate can be mentioned.
  • the (meth) acrylamide monomer is preferably (meth) acrylamide having a substituent at the N-position.
  • N-substituted (meth) acrylamide examples include N-methyl (meth) acrylamide, N-ethyl (meth) acrylamide, N-isopropyl (meth) acrylamide, Nn-butyl (meth) acrylamide, and Nt-butyl (N-t-butyl).
  • N-alkyl (meth) acrylamide such as meta) acrylamide, N-hexyl (meth) acrylamide;
  • N, N-dialkyl such as N, N-dimethyl (meth) acrylamide, N, N-diethyl (meth) acrylamide (meth) Meta) Acrylamide and the like.
  • the N-substituted group may be an alkyl group having a hydroxyl group, and examples thereof include N-hydroxymethyl (meth) acrylamide, N- (2-hydroxyethyl) (meth) acrylamide, and N- (2-hydroxy). Examples thereof include propyl) (meth) acrylamide.
  • specific examples of the N-substituted (meth) acrylamide forming the above-mentioned 5-membered ring or 6-membered ring include N-acryloylpyrrolidine, 3-acryloyl-2-oxazolidinone, 4-acryloylmorpholine, and N-acryloyl. Examples thereof include piperidine and N-methacryloyl piperidine.
  • Ethylene glycol di (meth) acrylate As a bifunctional (meth) acrylate monomer, Ethylene glycol di (meth) acrylate, 1,3-butanediol di (meth) acrylate, 1,4-butanediol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, 1,9-nonanediol Alkylene glycol di (meth) acrylates such as di (meth) acrylate and neopentyl glycol di (meth) acrylate; Diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, dipropylene glycol di (meth) acrylate, tripropylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate and Polyoxyalkylene glycol di (meth) acrylate
  • Examples of the trifunctional or higher functional polyfunctional (meth) acrylate monomer include glycerin tri (meth) acrylate, alkoxylated glycerin tri (meth) acrylate, trimethyl propantri (meth) acrylate, ditrimethylol propanthry (meth) acrylate, and ditrimethylol.
  • Propanetetra (meth) acrylate pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, etc.
  • you may use a commercially available product. Examples of commercially available products include A-DPH-12E, A-TMPT, and A-9300 (manufactured by Shin-Nakamura Chemical Industry Co., Ltd.).
  • Examples of the (meth) acrylic oligomer include urethane (meth) acrylic oligomer, polyester (meth) acrylic oligomer, and epoxy (meth) acrylic oligomer.
  • the urethane (meth) acrylic oligomer is a compound having a urethane bond (-NHCOO-) and at least two (meth) acryloyl groups in the molecule.
  • It can be a urethanization reaction product of a terminal isocyanato group-containing urethane compound obtained by reaction and a (meth) acrylic monomer having at least one (meth) acryloyl group and at least one hydroxyl group in the molecule. ..
  • the hydroxyl group-containing (meth) acrylic monomer used in the urethanization reaction can be, for example, a hydroxyl group-containing (meth) acrylate monomer, and specific examples thereof include 2-hydroxyethyl (meth) acrylate and 2-hydroxypropyl (meth).
  • hydroxyl group-containing (meth) acrylate monomer examples include N-hydroxyalkyl (meth) acrylamide monomers such as N-hydroxyethyl (meth) acrylamide and N-methylol (meth) acrylamide.
  • Examples of the polyisocyanate used for the urethanization reaction with the hydroxyl group-containing (meth) acrylic monomer include hexamethylene diisocyanate, lysine diisocyanate, isophorone diisocyanate, dicyclohexylmethane diisocyanate, tolylene diisocyanate, xylylene diisocyanate, and among these diisocyanates, aromatic ones.
  • Diisocyanates obtained by hydrogenating isocyanates for example, hydrogenated tolylene diisocyanates, hydrogenated xylylene diisocyanates, etc.
  • di- or tri-isocyanates such as triphenylmethane triisocyanates, dibenzylbenzene triisocyanates, and the above.
  • examples thereof include polyisocyanate obtained by increasing the amount of diisocyanate.
  • a polyester polyol, a polyether polyol, or the like can be used in addition to an aromatic, aliphatic or alicyclic polyol. it can.
  • Aliphatic and alicyclic polyols include 1,4-butanediol, 1,6-hexanediol, ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, neopentyl glycol, trimethylolethane, trimethylolpropane, and ditri.
  • Examples thereof include methylolpropane, pentaerythritol, dipentaerythritol, dimethylolheptan, dimethylolpropionic acid, dimethylolbutanoic acid, glycerin, and hydrogenated bisphenol A.
  • the polyester polyol is obtained by a dehydration condensation reaction between the above-mentioned polyol and a polybasic carboxylic acid or an anhydride thereof.
  • polybasic carboxylic acids or their anhydrides which may be anhydrous, are represented by adding "(anhydride)" to (anhydrous) succinic acid, adipic acid, (anhydrous) maleic anhydride, (anhydrous).
  • anhydrous trimellitic acid
  • pyromellitic acid (anhydrous) phthalic acid
  • isophthalic acid terephthalic acid
  • the polyether polyol may be a polyoxyalkylene-modified polyol obtained by reacting the above-mentioned polyol or dihydroxybenzenes with an alkylene oxide, in addition to the polyalkylene glycol.
  • the polyester (meth) acrylate oligomer means an oligomer having an ester bond and at least two (meth) acryloyloxy groups in the molecule.
  • the polyester (meth) acrylate oligomer can be obtained, for example, by subjecting (meth) acrylic acid, a polybasic carboxylic acid or an anhydride thereof, and a polyol to a dehydration condensation reaction.
  • the polybasic carboxylic acid or its anhydride include succinic anhydride, adipic acid, maleic anhydride, itaconic anhydride, trimellitic anhydride, pyromellitic anhydride, hexahydrophthalic anhydride, phthalic acid, succinic acid, and maleic acid.
  • Polyols include 1,4-butanediol, 1,6-hexanediol, ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, neopentyl glycol, trimethylolethane, trimethylolpropane, ditrimethylolpropane, pentaerythritol, and di. Examples thereof include pentaerythritol, dimethylolheptan, trimethylolpropionic acid, dimethylolbutanediol, glycerin, hydrogenated bisphenol A and the like.
  • the epoxy (meth) acrylic oligomer can be obtained by an addition reaction between polyglycidyl ether and (meth) acrylic acid.
  • Epoxy (meth) acrylic oligomers have at least two (meth) acryloyloxy groups in the molecule.
  • the polyglycidyl ether include ethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, tripropylene glycol diglycidyl ether, 1,6-hexanediol diglycidyl ether, and bisphenol A diglycidyl ether.
  • styrene compounds include styrene; methyl styrene, dimethyl styrene, trimethyl styrene, ethyl styrene, diethyl styrene, triethyl styrene, propyl styrene, butyl styrene, hexyl styrene, heptyl styrene, octyl styrene and other alkyl styrene; fluorostyrene, chloro styrene.
  • vinyl-based monomer examples include fatty acid vinyl esters such as vinyl acetate, vinyl propionate, vinyl butyrate, vinyl 2-ethylhexanoate, and vinyl laurate; vinyl halides such as vinyl chloride and vinyl bromide; and vinylidene chloride and the like.
  • vinylidene halide nitrogen-containing heteroaromatic vinyl such as vinylpyridine, vinylpyrrolidone and vinylcarbazole; conjugated diene such as butadiene, isoprene and chloroprene; and unsaturated nitriles such as acrylonitrile and methacrylonitrile.
  • the radical curable component (E) is preferably a (meth) acrylate compound, and more preferably a polyfunctional (meth) acrylate compound.
  • the polyfunctional (meth) acrylate compound is preferably trifunctional or higher.
  • the content of the radical curable component (E) is usually 0.5 to 100 parts by mass, preferably 1 to 70 parts by mass, and 3 to 50 parts by mass with respect to 100 parts by mass of the resin (A). It is more preferably 5 to 30 parts by mass, and particularly preferably 7.5 to 20 parts by mass.
  • Cross-linking agent (F) examples include isocyanate-based cross-linking agents, epoxy-based cross-linking agents, aziridine-based cross-linking agents, metal chelate-based cross-linking agents, and the like, and in particular, the pot life of the pressure-sensitive adhesive composition and the durability and cross-linking of the pressure-sensitive adhesive layer. From the viewpoint of speed and the like, an isocyanate-based cross-linking agent is preferable.
  • the isocyanate-based cross-linking agent a compound having at least two isocyanato groups (-NCO) in the molecule is preferable, and for example, an aliphatic isocyanate-based compound (for example, hexamethylene diisocyanate) and an alicyclic isocyanate-based compound (for example, isophorone) are preferable.
  • an aliphatic isocyanate-based compound for example, hexamethylene diisocyanate
  • an alicyclic isocyanate-based compound for example, isophorone
  • diisocyanate hydrogenated diphenylmethane diisocyanate, hydrogenated xylylene diisocyanate
  • aromatic isocyanate-based compounds for example, tolylene diisocyanate, xylylene diisocyanate diphenylmethane diisocyanate, naphthalene diisocyanate, triphenylmethane triisocyanate, etc.
  • the cross-linking agent (F) is an adduct (adduct) of the isocyanate-based compound made of a polyhydric alcohol compound [for example, an adduct made of glycerol, trimethylolpropane, etc.], an isocyanurate compound, a bullet-type compound, a polyether polyol, and the like. It may be a derivative such as a urethane prepolymer type isocyanate compound which has been subjected to an addition reaction with a polyester polyol, an acrylic polyol, a polybutadiene polyol, a polyisoprene polyol or the like.
  • the cross-linking agent (F) can be used alone or in combination of two or more.
  • aromatic isocyanate compounds eg, tolylene diisocyanate, xylylene diisocyanate
  • aliphatic isocyanate compounds eg, hexamethylene diisocyanate
  • their polyhydric alcohol compounds eg, glycerol, trimethylolpropane.
  • isocyanurates e.g., glycerol, trimethylolpropane.
  • the cross-linking agent (F) is an aromatic isocyanate compound and / or an adduct of these polyhydric alcohol compounds or an isocyanurate compound
  • the durability of the adhesive layer can be improved.
  • an adduct made of a tolylene diisocyanate compound and / or a polyhydric alcohol compound thereof can improve durability even when, for example, an adhesive layer is applied to a polarizing plate.
  • the content of the cross-linking agent (F) is usually 0.01 to 25 parts by mass, preferably 0.1 to 15 parts by mass, and more preferably 0.15 parts by mass with respect to 100 parts by mass of the resin (A). It is ⁇ 7 parts by mass, more preferably 0.2 to 5 parts by mass, and particularly preferably 0.25 to 2 parts by mass.
  • the pressure-sensitive adhesive composition of the present invention may further contain a silane compound (G).
  • the silane compound (G) include vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris (2-methoxyethoxy) silane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropyltriethoxysilane, and 3 -Glysidoxypropylmethyldimethoxysilane, 3-Glysidoxypropylethoxydimethylsilane, 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, Examples thereof include 3-methacryloyloxypropyltrimethoxysilane and 3-mercaptopropyltrimethoxysilane.
  • the silane compound (G) may be a silicone oligomer. Specific examples
  • 3-Acryloyloxypropyltriethoxysilane-tetraethoxysilane oligomer 3-acryloyloxypropylmethyldimethoxysilane-tetramethoxysilane oligomer, 3-acryloyloxypropylmethyldimethoxysilane-tetraethoxysilane oligomer, 3-acryloyloxypropylmethyldi Acryloyloxypropyl group-containing oligomers such as ethoxysilane-tetramethoxysilane oligomer, 3-acryloyloxypropylmethyldiethoxysilane-tetraethoxysilane oligomer; vinyltrimethoxysilane-tetramethoxysilane oligomer, vinyltrimethoxysilane-tetraethoxysilane oligomer , Vinyl Triethoxysilane-Tetramethoxysilane oligomer, Vinyltriethoxy
  • the silane compound (G) may be a silane compound represented by the following formula (g1).
  • A represents an alkanediyl group having 1 to 20 carbon atoms or a divalent alicyclic hydrocarbon group having 3 to 20 carbon atoms, and constitutes the alkanediyl group and the alicyclic hydrocarbon group.
  • -CH 2- may be replaced with -O- or -CO-
  • R 41 represents an alkyl group having 1 to 5 carbon atoms
  • R 42 , R 43 , R 44 , R 45 and R 46 are.
  • Examples of the alkanediyl group having 1 to 20 carbon atoms represented by A include a methylene group, a 1,2-ethanediyl group, a 1,3-propanediyl group, a 1,4-butandyl group, a 1,5-pentanediyl group and 1 , 6-Hexanediyl group, 1,7-heptandyl group, 1,8-octanediyl group, 1,9-nonandyl group, 1,10-decandyl group, 1,12-dodecandyl group, 1,14-tetradecandyl group , 1,16-Hexadecandyl group, 1,18-octadecandyl group and 1,20-icosandyl group.
  • Examples of the divalent alicyclic hydrocarbon group having 3 to 20 carbon atoms include a 1,3-cyclopentanediyl group and a 1,4-cyclohexanediyl group.
  • -CH 2- instead of -O- or -CO- constituting the alkanediyl group and the alicyclic hydrocarbon group is replaced with -CH 2 CH 2- O-CH 2 CH 2- , -CH 2 CH 2- O-CH 2 CH 2- O-CH 2 CH 2- , -CH 2 CH 2- O-CH 2 CH 2- O-CH 2 CH 2- O-CH 2 CH 2- , -CH 2 CH 2- CO-O-CH 2 CH 2- , -CH 2 CH 2- O-CH 2 CH 2- CO-O-CH 2 CH 2- , -CH 2 CH 2 CH 2 CH 2- O-CH 2 CH 2- and -CH 2 CH 2 CH 2 CH 2- O-CH 2 CH 2 CH 2- .
  • Examples of the alkyl group having 1 to 5 carbon atoms represented by R 41 to R 46 include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert-butyl group and a pentyl group.
  • the 42-C 1-5 alkoxy group represented by R 46 a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, an isobutoxy group, and a tert- butoxy and pentyloxy groups.
  • silane compound represented by the formula (g1) examples include (trimethoxysilyl) methane, 1,2-bis (trimethoxysilyl) ethane, 1,2-bis (triethoxysilyl) ethane, 1,3-.
  • (Trimethoxysilyl) hexane and 1,8-bis (trimethoxysilyl) octane are preferable.
  • the content of the silane compound (G) is usually 0.01 to 20 parts by mass, preferably 0.1 to 10 parts by mass, and more preferably 0.15 with respect to 100 parts by mass of the resin (A). It is ⁇ 7 parts by mass, more preferably 0.2 to 5 parts by mass, and particularly preferably 0.25 to 2 parts by mass.
  • the pressure-sensitive adhesive composition further comprises one or more additives such as an antistatic agent, a solvent, a cross-linking catalyst, a tack fire, a plasticizer, a softening agent, a pigment, a rust preventive, an inorganic filler, and light-scattering fine particles. Can be contained.
  • additives such as an antistatic agent, a solvent, a cross-linking catalyst, a tack fire, a plasticizer, a softening agent, a pigment, a rust preventive, an inorganic filler, and light-scattering fine particles. Can be contained.
  • the pressure-sensitive adhesive composition of the present invention is dissolved or dispersed in a solvent to obtain a solvent-containing pressure-sensitive adhesive composition, which is then applied to the surface of a substrate and dried. After that, it can be formed by irradiating with active energy rays. It can be said that the pressure-sensitive adhesive layer of the present invention is a photocurable product of the pressure-sensitive adhesive composition.
  • a plastic film is suitable as the base material, and specific examples thereof include a release film that has been subjected to a mold release treatment.
  • the release film include those in which one surface of a film made of a resin such as polyethylene terephthalate, polybutylene terephthalate, polycarbonate, or polyarylate is subjected to a mold release treatment such as silicone treatment.
  • the conditions (drying temperature, drying time) for drying the coating film formed from the solvent-containing pressure-sensitive adhesive composition can be appropriately set depending on the composition and concentration, but are preferably 60 to 150 ° C. for 1 to 60 minutes. ..
  • the activation energy ray irradiation after the coating film is dried is preferably ultraviolet irradiation.
  • Illuminance of the irradiated ultraviolet ray is preferably 10mW / cm 2 ⁇ 3000mW / cm 2. Further, it is preferable that the integrated quantity of ultraviolet light is 10mJ / cm 2 ⁇ 5000mJ / cm 2.
  • the ultraviolet lamp that irradiates ultraviolet rays may be a mercury lamp, a metal halide lamp, or an LED lamp.
  • the pressure-sensitive adhesive layer of the present invention is preferably a pressure-sensitive adhesive layer that satisfies the following formula (3), and more preferably a pressure-sensitive adhesive layer that satisfies the formula (4).
  • a (380) ⁇ 0.6 (3) [In formula (3), A (380) represents the absorbance at a wavelength of 380 nm. ]
  • a (380) / A (420) ⁇ 5 (4) [In the formula (4), A (380) represents the absorbance at a wavelength of 380 nm, and A (420) represents the absorbance at a wavelength of 420 nm. ]
  • the value of A (380) is less than 0.6, the absorption at a wavelength of 380 nm is low, and the deterioration of members (for example, display devices such as organic EL elements and liquid crystal retardation films) that are easily deteriorated by light near ultraviolet rays is deteriorated. It is easy to happen.
  • the value of A (380) is preferably 0.75 or more, more preferably 0.85 or more, and particularly preferably 1.0 or more. There is no particular upper limit, but it is usually 10 or less.
  • the value of A (380) / A (420) represents the magnitude of absorption at a wavelength of 380 nm with respect to the magnitude of absorption at a wavelength of 420 nm, and the larger this value is, the more specific absorption is in the wavelength region near ultraviolet rays. Represent.
  • the value of A (380) / A (420) is preferably 5 or more, more preferably 20 or more, further preferably 50 or more, and particularly preferably 100 or more.
  • the thickness of the pressure-sensitive adhesive layer of the present invention is usually less than 200 ⁇ m, preferably 100 ⁇ m or less, more preferably 20 ⁇ m or less, still more preferably 12 ⁇ m or less or less than 12 ⁇ m, still more preferably 10 ⁇ m or less. , Especially preferably 7 ⁇ m or less. Further, it is usually 0.1 ⁇ m or more, preferably 0.5 ⁇ m or more, more preferably 1 ⁇ m or more, still more preferably 2 ⁇ m or more. According to the present invention, for example, even a thin film adhesive layer having a thickness of less than 12 ⁇ m can sufficiently absorb ultraviolet rays, which is advantageous from the viewpoint of thinning the display device.
  • the gel fraction of the pressure-sensitive adhesive layer of the present invention is usually 50 to 99.9% by mass, preferably 60 to 99% by mass, more preferably 70 to 95% by mass, and further preferably 75 to 90% by mass. %
  • the pressure-sensitive adhesive composition of the present invention and the pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition can be used, for example, for bonding optical films.
  • the present invention also includes an optical film with an adhesive layer in which an optical film is laminated on at least one surface of the pressure-sensitive adhesive layer of the present invention.
  • the pressure-sensitive adhesive composition was dissolved or dispersed in a solvent to obtain a solvent-containing pressure-sensitive adhesive composition, which was then applied to the surface of the optical film and dried. It can be formed later by irradiating with active energy rays. It can also be obtained by forming an adhesive layer on the release film in the same manner and laminating (transferring) the adhesive layer on the surface of the optical film.
  • An optical film is a film having optical functions such as transmitting, reflecting, and absorbing light rays.
  • the optical film may be a single-layer film or a multi-layer film.
  • Examples of the optical film include a polarizing film, a retardation film, a brightness improving film, an antiglare film, an antireflection film, a diffusion film, a condenser film, and the like, and the optical film is a polarizing film, a retardation film, or a laminated film thereof. Is preferable.
  • the condensing film is used for the purpose of controlling the optical path, and can be a prism array sheet, a lens array sheet, a sheet with dots, or the like.
  • the brightness improving film is used for the purpose of improving the brightness in a liquid crystal display device to which a polarizing plate is applied.
  • a reflective polarizing separation sheet designed to generate anisotropy in reflectance by laminating a plurality of thin films having different refractive index anisotropy, an alignment film of cholesteric liquid crystal polymer, and its orientation. Examples thereof include a circularly polarized light separation sheet in which a liquid crystal layer is supported on a base film.
  • the polarizing film is a film having a property of absorbing linearly polarized light having a vibrating surface parallel to the absorption axis and transmitting linearly polarized light having a vibrating surface orthogonal to the absorption axis (parallel to the transmission axis), for example.
  • a film in which a dichroic dye is adsorbed and oriented on a polyvinyl alcohol-based resin film can be used.
  • the dichroic dye include iodine and a dichroic organic dye.
  • the saponification degree of the polyvinyl alcohol-based resin is usually 85 mol% to 100 mol%, preferably 98 mol% or more.
  • the polyvinyl alcohol-based resin may be modified, for example, polyvinyl formal or polyvinyl acetal modified with aldehyde.
  • the degree of polymerization of the polyvinyl alcohol-based resin is usually 1,000 to 10,000, preferably 1,500 to 5,000.
  • a film made of a polyvinyl alcohol-based resin is used as the raw film of the polarizing film.
  • the polyvinyl alcohol-based resin can be formed into a film by a known method.
  • the thickness of the raw film is usually 1 to 150 ⁇ m, and is preferably 10 ⁇ m or more in consideration of ease of stretching and the like.
  • the polarizing film is, for example, a step of uniaxially stretching the raw film, a step of dyeing the film with a dichroic dye and adsorbing the dichroic dye, a step of treating the film with a boric acid aqueous solution, and a step of treating the film with a boric acid aqueous solution.
  • the film is washed with water and finally dried to produce.
  • the thickness of the polarizing film is usually 1 to 30 ⁇ m, and is preferably 20 ⁇ m or less, more preferably 15 ⁇ m or less, and particularly preferably 10 ⁇ m or less, from the viewpoint of thinning the optical film with an adhesive layer.
  • At least one surface of the polarizing film is preferably a polarizing plate provided with a protective film via an adhesive.
  • an adhesive a known adhesive may be used, and it may be a water-based adhesive or an active energy ray-curable adhesive.
  • water-based adhesive examples include conventional water-based adhesives (for example, an adhesive composed of an aqueous polyvinyl alcohol-based resin solution, a water-based two-component urethane-based emulsion adhesive, an aldehyde compound, an epoxy compound, a melamine-based compound, a methylol compound, and an isocyanate compound. (Amine compounds, cross-linking agents such as polyvalent metal salts, etc.) can be mentioned. Of these, an aqueous adhesive composed of an aqueous solution of a polyvinyl alcohol-based resin can be preferably used.
  • a water-based adhesive When a water-based adhesive is used, it is preferable to carry out a step of adhering the polarizing film and the protective film and then drying them in order to remove water contained in the water-based adhesive. After the drying step, a curing step of curing at a temperature of, for example, about 20 to 45 ° C. may be provided.
  • the adhesive layer formed from the water-based adhesive is usually 0.001 to 5 ⁇ m.
  • the active energy ray-curable adhesive means an adhesive that cures by irradiating an active energy ray such as an ultraviolet ray or an electron beam.
  • an active energy ray such as an ultraviolet ray or an electron beam.
  • a curable composition containing a polymerizable compound and a photopolymerization initiator, a photoreaction examples thereof include a curable composition containing a sex resin, a curable composition containing a binder resin and a photoreactive cross-linking agent, and an ultraviolet curable adhesive is preferable.
  • Examples of the method of laminating the polarizing film and the protective film include a method of subjecting at least one of these laminating surfaces to a surface activation treatment such as saponification treatment, corona treatment, and plasma treatment.
  • a surface activation treatment such as saponification treatment, corona treatment, and plasma treatment.
  • the adhesive for bonding these resin films may be the same type of adhesive or different types of adhesives.
  • the protective film is preferably a film formed of a translucent thermoplastic resin. Specific examples thereof include a film composed of a polyolefin resin; a cellulosic resin; a polyester resin; a (meth) acrylic resin; or a mixture thereof, a copolymer, or the like.
  • the protective film used may be a film made of different thermoplastic resins or a film made of the same thermoplastic resin.
  • the protective film is preferably a protective film made of a polyolefin resin or a cellulosic resin. By using these films, it is possible to effectively suppress the shrinkage of the polarizing film in a high temperature environment without impairing the optical characteristics of the polarizing film.
  • the protective film may also be an oxygen shielding layer.
  • a preferred configuration of the polarizing plate is a polarizing plate in which a protective film is laminated on at least one surface of the polarizing film via an adhesive layer.
  • a protective film is laminated on only one surface of the polarizing film, it is more preferable that the protective film is laminated on the visual side.
  • the protective film laminated on the visual side is preferably a protective film made of a triacetyl cellulose-based resin or a cycloolefin-based resin.
  • the protective film may be an unstretched film, or may be stretched in any direction and have a phase difference.
  • a surface treatment layer such as a hard coat layer or an anti-glare layer may be provided on the surface of the protective film laminated on the visual side.
  • the protective film on the panel side is a protective film or retardation film made of a triacetyl cellulose-based resin, a cycloolefin-based resin, or an acrylic resin. It is preferable to have.
  • the retardation film may be a zero retardation film described later.
  • the retardation film is an optical film exhibiting optical anisotropy, for example, polyvinyl alcohol, polycarbonate, polyester, polyarylate, polyimide, polyolefin, polycycloolefin, polystyrene, polysulfone, polyether sulfone, polyvinylidene fluor.
  • optical anisotropy for example, polyvinyl alcohol, polycarbonate, polyester, polyarylate, polyimide, polyolefin, polycycloolefin, polystyrene, polysulfone, polyether sulfone, polyvinylidene fluor.
  • Examples thereof include a stretched film obtained by stretching a polymer film composed of ride / polymethylmethacrylate, acetylcellulose, ethylene-vinyl acetate copolymer saponified product, polyvinyl chloride and the like about 1.01 to 6 times.
  • the retardation film may be a retardation film in which a liquid crystal compound is applied to a base material and optical anisotropy is exhibited by coating and orientation.
  • the retardation film includes a zero retardation film, and also includes a film called a uniaxial retardation film, a low photoelasticity retardation film, a wide viewing angle retardation film, and the like.
  • the zero retardation film is an optically isotropic film in which both the front retardation R e and the thickness direction retardation R th are -15 to 15 nm.
  • the zero retardation film include a resin film made of a cellulose resin, a polyolefin resin (chain polyolefin resin, polycycloolefin resin, etc.) or a polyethylene terephthalate resin, and the retardation value can be easily controlled and can be obtained.
  • a cellulose-based resin or a polyolefin-based resin is preferable because it is easy.
  • the zero retardation film can also be used as a protective film.
  • Zero retardation films include "Z-TAC” (trade name) sold by FUJIFILM Corporation, "Zero Tuck (registered trademark)” sold by Konica Minolta Opto Co., Ltd., and Zeon Corporation.
  • ZF-14 trade name
  • the retardation film is preferably a retardation film in which optical anisotropy is exhibited by coating and orientation of a liquid crystal compound.
  • Examples of the film in which optical anisotropy is exhibited by coating and orientation of the liquid crystal compound include the following first to fifth forms.
  • Second form retardation film in which the rod-shaped liquid crystal compound is oriented in the direction perpendicular to the supporting base material
  • Third form A retardation film in which the rod-shaped liquid crystal compound is spirally oriented in the plane
  • Fourth form A retardation film in which the disk-shaped liquid crystal compound is obliquely oriented
  • the first form, the second form, and the fifth form are preferably used.
  • the retardation films of these forms may be laminated and used.
  • the retardation film When the retardation film is a layer made of a polymer in the oriented state of the polymerizable liquid crystal compound (hereinafter, may be referred to as an "opticallyotropic layer"), the retardation film may have anti-wavelength dispersibility. preferable.
  • the inverse wavelength dispersibility is an optical characteristic in which the in-plane retardation value of the liquid crystal alignment at a short wavelength is smaller than the in-plane retardation value of the liquid crystal alignment at a long wavelength. (7) and equation (8) are satisfied.
  • Re ( ⁇ ) represents an in-plane retardation value with respect to light having a wavelength of ⁇ nm.
  • the coloring at the time of black display on the display device is reduced, and 0.82 ⁇ in the above formula (7). More preferably, Re (450) / Re (550) ⁇ 0.93. Further, 120 ⁇ Re (550) ⁇ 150 is preferable.
  • the polymerizable liquid crystal compound is described in "3" of the Liquid Crystal Handbook (edited by the Liquid Crystal Handbook Editorial Committee, published on October 30, 2000 by Maruzen Co., Ltd.).
  • the compounds described in ".8.6 Network (completely crosslinked type)" and "6.5.1 Liquid crystal material b. Polymerizable nematic liquid crystal material” compounds having a polymerizable group, and Japanese Patent Application Laid-Open No. 2010-31223 Japanese Patent Application Laid-Open No. 2010-270108, Japanese Patent Application Laid-Open No. 2011-6360, Japanese Patent Application Laid-Open No.
  • Examples of the method for producing a retardation film from the polymer in the oriented state of the polymerizable liquid crystal compound include the methods described in JP-A-2010-31223.
  • the front retardation value Re (550) may be adjusted in the range of 0 to 10 nm, preferably in the range of 0 to 5 nm, and the phase difference value R th in the thickness direction is ⁇ 10 to ⁇ . It may be adjusted in the range of 300 nm, preferably in the range of ⁇ 20 to ⁇ 200 nm.
  • the phase difference value R th in the thickness direction which means the refractive index anisotropy in the thickness direction, is the phase difference between the phase difference value R 50 and the in-plane phase difference measured by inclining 50 degrees with the in-plane phase advance axis as the inclination axis. It can be calculated from the value R 0.
  • the retardation value R th in the thickness direction is the in-plane retardation value R 0 , the retardation value R 50 measured by inclining 50 degrees with the phase advance axis as the tilt axis, the thickness d of the retardation film, and the position.
  • n x , ny and n z From the average refractive index n 0 of the retardation film, n x , ny and n z can be obtained by the following equations (10) to (12), and these can be substituted into the equation (9) for calculation.
  • R th [(n x + ny ) / 2- nz ] x d (9)
  • R 0 (n x ⁇ n y ) ⁇ d (10)
  • n y ' n y x n z / [ ny 2 x sin 2 ( ⁇ ) + n z 2 x cos 2 ( ⁇ )] 1/2
  • a film that expresses optical anisotropy by coating and orientation of a liquid crystal compound and a film that expresses optical anisotropy by coating an inorganic layered compound a film called a temperature-compensated retardation film, JX "NH film” (trade name; film in which rod-shaped liquid crystal is inclined oriented) sold by Nikko Nisseki Energy Co., Ltd., "WV film” (trade name; disk-shaped liquid crystal) sold by Fujifilm Co., Ltd. Inclined oriented film), "VAC film” (trade name; completely biaxially oriented film) sold by Sumitomo Chemical Co., Ltd., "new VAC film” sold by Sumitomo Chemical Co., Ltd. ( Product name; biaxially oriented film) and the like.
  • the retardation film may be a multilayer film having two or more layers.
  • a protective film is laminated on one side or both sides of a retardation film, and two or more retardation films are laminated via an adhesive or an adhesive.
  • FIG. 1 to 5 show examples of a laminate in which a release film is provided on the pressure-sensitive adhesive layer of the present invention, an optical film with a pressure-sensitive adhesive layer of the present invention, and a layer structure of the optical laminate.
  • the laminate 10 provided with the release film on the pressure-sensitive adhesive layer shown in FIG. 1 is provided on one surface of the pressure-sensitive adhesive layer for temporary protection of one surface of the pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition of the present invention. It is in a state where the release film (separate film) 2 is attached.
  • the 2 is a pressure-sensitive adhesive containing a protective film 3, an adhesive layer 4, a polarizing film 5, a pressure-sensitive adhesive layer 1 formed from the pressure-sensitive adhesive composition of the present invention, and a release film 2. It is an optical film with a layer.
  • the protective film 3, the adhesive layer 4, and the polarizing film 5 constitute a polarizing plate 100 (optical film 40).
  • the protective film 3 may have a phase difference. Further, a hard coat layer or the like may be further laminated on the protective film 3.
  • the optical film 10B with an adhesive layer shown in FIG. 3 is an adhesive layer formed from a protective film 3, an adhesive layer 4, a polarizing film 5, an adhesive layer 7, a protective film 6, and the adhesive composition of the present invention. 1.
  • the protective film 3, the adhesive layer 4, the polarizing film 5, the adhesive layer 7, and the protective film 6 constitute a polarizing plate 100 (optical film 40).
  • the optical laminate 10C shown in FIG. 4 and the optical laminate 10D shown in FIG. 5 include a protective film 3, an adhesive layer 4, a polarizing film 5, and an adhesive layer 1 formed from the adhesive composition of the present invention. It is an optical laminate including a retardation film 110 (optical film 40), an adhesive layer 1a, and a light emitting element 30 (liquid crystal cell, organic EL cell).
  • the protective film 3, the adhesive layer 4, and the polarizing film 5 constitute a polarizing plate 100 (optical film 40).
  • the pressure-sensitive adhesive layer 1a may be a pressure-sensitive adhesive layer formed from a known pressure-sensitive adhesive composition, or may be a pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition of the present invention.
  • the retardation film is a multilayer film as shown in FIGS. 4 and 5, as shown in FIG. 4, with the 1/4 wavelength retardation layer 70 that imparts a retardation of 1/4 wavelength to the transmitted light.
  • the retardation film 110 (optical film 40) in which the 1/4 wavelength retardation layer 50a and the positive C layer 80 are laminated via the adhesive layer or the pressure-sensitive adhesive layer 60 is included.
  • the configuration is also mentioned.
  • the 1/4 wavelength retardation layer 70 that imparts a phase difference of 1/4 wavelength in FIG. 4 and the 1/2 wavelength retardation layer 50 that imparts a phase difference of 1/2 wavelength to transmitted light are the first. It may be the optical film of the fifth form or the optical film of the fifth form. In the case of the configuration of FIG. 4, it is more preferable that at least one of them is the fifth form. In the case of the configuration of FIG. 5, the 1/4 wavelength retardation layer 50a is preferably the optical film of the first form, and more preferably satisfies the formulas (7) and (8).
  • the pressure-sensitive adhesive composition of the present invention and an optical film with a pressure-sensitive adhesive layer containing a pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition can be used as an optical laminate laminated on a display element such as an organic EL element or a liquid crystal cell. It can be used for display devices such as organic EL display devices and liquid crystal display devices.
  • ⁇ Maximum absorption wavelength and gram absorption coefficient ⁇ measurement> A 2-butanone solution (0.006 g / L) of "FUV002B" (manufactured by Fuji Film Co., Ltd.) was placed in a 1 cm quartz cell, and the quartz cell was set in a spectrophotometer UV-2450 (manufactured by Shimadzu Corporation). The absorbance in the wavelength range of 300 to 800 nm was measured every 1 nm step by the double beam method. The gram extinction coefficient for each wavelength was calculated from the obtained absorbance value, the concentration of "FUV002B" in the solution, and the optical path length of the quartz cell.
  • ⁇ ( ⁇ ) A ( ⁇ ) / CL
  • ⁇ ( ⁇ ) represents the gram extinction coefficient (L / (g ⁇ cm)) of “FUV002B” at wavelength ⁇ nm
  • a ( ⁇ ) represents the absorbance at wavelength ⁇ nm
  • C represents “FUV002B” in solution.
  • L represents the optical path length (cm) of the quartz cell.
  • the maximum absorption wavelength of "FUV002B" was 370 nm.
  • the ⁇ (380) of "FUV002B" is 108.9 L / (g ⁇ cm), the ⁇ (420) is 0.2 L / (g ⁇ cm), and the ⁇ (380) / ⁇ (420) is 544.5. It was.
  • Polymerization Example 1 Preparation of acrylic resin (A1) 81.8 parts of ethyl acetate, 96 parts of butyl acrylate, 2 acrylic acid as solvents in a reaction vessel equipped with a cooling tube, a nitrogen introduction tube, a thermometer and a stirrer. A mixed solution of 3 parts of hydroxyethyl methyl and 1 part of acrylic acid was charged, and the internal temperature was raised to 55 ° C. while replacing the air in the apparatus with nitrogen gas to make it oxygen-free. Then, a total amount of a solution prepared by dissolving 0.14 parts of azobisisobutyronitrile (polymerization initiator) in 10 parts of ethyl acetate was added.
  • ethyl acetate was continuously added into the reaction vessel at an addition rate of 17.3 parts / hr while maintaining the internal temperature at 54 to 56 ° C. to concentrate the acrylic resin.
  • the addition of ethyl acetate was stopped when the temperature reached 35%, and the temperature was kept at this temperature until 12 hours had passed from the start of addition of ethyl acetate.
  • ethyl acetate was added to adjust the concentration of the acrylic resin to 20%, and an ethyl acetate solution of the acrylic resin was prepared.
  • the obtained acrylic resin had a polystyrene-equivalent weight average molecular weight Mw of 1.47 million and Mw / Mn of 5.5 by GPC. This is referred to as acrylic resin (A1).
  • the obtained acrylic resin (A1) did not show maximum absorption in the wavelength range of 300 nm to 780 nm.
  • Example 1 Preparation of pressure-sensitive adhesive composition (1) A cross-linking agent (F) was applied to 100 parts of a solid content of an ethyl acetate solution (resin concentration: 20%) of an acrylic resin (A1) as a resin (A).
  • silane compound (G) (Shinetsu Chemical Industry Co., Ltd .: trade name "KBM3066") 0.28 Part, radical curable component (E) (manufactured by Shin-Nakamura Chemical Industry Co., Ltd .: trade name "A-DPH-12E", hexafunctional (meth) acrylate compound) 10 parts, initiator (D) (ADEKA Co., Ltd.) Manufactured by: Trade name "NCI-730", 1.5 parts of photoradical generator which is an oxime ester compound), 2.5 parts of light selective absorption compound (B) (manufactured by Fuji Film Co., Ltd .; "FUV002B"), light 10 parts of the selective absorption compound (C-1) (manufactured by Otsuka Chemical Co., Ltd .: trade name "RUVA-93", 2- [2'-hydroxy-5'
  • Examples 2 to 5 and Comparative Examples 1 to 11 The pressure-sensitive adhesive composition (2) to the pressure-sensitive adhesive composition (16) were prepared in the same manner as in Example 1 except that each component and the content of each component were changed as shown in Table 1 or Table 2.
  • the amount of the cross-linking agent blended is the number of parts by mass as the active ingredient, and the acrylic resin (A1) is the number of parts by mass of the solid content.
  • the absorption wavelength ( ⁇ max) is 337 nm.
  • ⁇ Initiator (D)> NCI-730: ADEKA Corporation, trade name: NCI-730, oxime ester-based photoradical generator PBG3057: TRONLY (Joshu Strong Electronics New Materials Co., Ltd.
  • ⁇ Measurement of absorbance of adhesive layer> The obtained pressure-sensitive adhesive layers are respectively bonded to glass, the separate film is peeled off, and then a cycloolefin polymer (COP) film (ZF-14 manufactured by Nippon Zeon Co., Ltd.) is bonded to the pressure-sensitive adhesive layer.
  • COP cycloolefin polymer
  • a laminate having a structure of an adhesive layer / glass was prepared. The prepared laminate was set in a spectrophotometer UV-2450 (manufactured by Shimadzu Corporation), and the absorbance was measured in the wavelength range of 300 to 800 nm in 1 nm steps by the double beam method.
  • the pressure-sensitive adhesive composition of the example showed an absorbance of 0.6 or more at any of a wavelength of 300 nm, a wavelength of 330 nm, a wavelength of 350 nm, and a wavelength of 380 nm, and showed good ultraviolet absorber performance.
  • the absorbance at a wavelength of 420 nm was less than 0.10 (more preferably less than 0.01), showing a high transmittance.
  • the pressure-sensitive adhesive composition of the present invention showed good bleed resistance without crystal precipitation.
  • the pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition of the present invention exhibits high absorbance in the vicinity of a wavelength of 300 nm to 380 nm, while transmitting light having a wavelength of 420 nm, so that the color expression of the display device is not impaired. Has good UV absorption performance. It also has good bleed resistance. The pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition of the present invention has sufficient ultraviolet absorption performance and good bleed resistance even if it is a thin layer having a thickness of less than 12 ⁇ m.
  • the pressure-sensitive adhesive composition of the present invention and an optical film with a pressure-sensitive adhesive layer containing a pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition are suitably used for liquid crystal panels and liquid crystal display devices.
  • Adhesive layer formed from the adhesive composition of the present invention 1a Adhesive layer 2 Release film 10 Laminated body 10A, 10B Optical film with adhesive layer 10C, 10D Optical laminated body 3, 6 Protective film 4, 7 Adhesive Layer 5 Polarizing film 8 Phase difference film 30 Light emitting element 40 Optical film 70, 50a 1/4 wavelength phase difference layer 60 Adhesive layer or adhesive layer 50 1/2 wavelength phase difference layer 80 Positive C layer 100 Plate plate 110 Phase difference the film.

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  • Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Nonlinear Science (AREA)
  • Mathematical Physics (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Adhesive Tapes (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Laminated Bodies (AREA)

Abstract

L'invention fournit une couche d'adhésif possédant des performances d'absorption des rayons ultraviolets suffisantes, y compris dans le cas d'un amincissement d'épaisseur, présentant des risques d'exsudation réduits, et n'absorbant que faiblement une lumière visible proche de ４２０ｎｍ de longueur d'onde, et fournit également une composition d'adhésif destinée à la formation de cette couche d'adhésif. Plus précisément, l'invention concerne une composition d'adhésif qui contient : une résine (A) ; un composé d'absorption sélective de lumière (B) présentant une absorption maximale supérieure ou égale à 360nm de longueur d'onde, et satisfaisant les formules (1) et (2) ; et au moins un composant choisi parmi un monomère (C-1) possédant un groupe polymérisable à l'intérieur de chaque molécule, et présentant une absorption maximale supérieure ou égale à 300nm de longueur d'onde et inférieure à 360nm de longueur d'onde, et une résine (C-2) présentant une absorption maximale supérieure ou égale à 300nm de longueur d'onde et inférieure à 360nm de longueur d'onde.　ε（３８０）≧　２５　（１）　ε（３８０）／ε（４２０）≧　２０　（２） [Dans les formules (1) et (2), ε（３８０） représente l'indice de pouvoir d'absorption par gramme à une longueur d'onde de 380nm du composé d'absorption sélective de lumière (B), et ε（４２０）représente l'indice de pouvoir d'absorption par gramme à une longueur d'onde de 420nm du composé d'absorption sélective de lumière (B). L'unité de l'indice de pouvoir d'absorption par gramme est Ｌ／（ｇ・ｃｍ）.
PCT/JP2020/037825 2019-10-11 2020-10-06 Composition d'adhésif WO2021070801A1 (fr)

Priority Applications (2)

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KR1020227014965A KR20220082009A (ko) 2019-10-11 2020-10-06 점착제 조성물
CN202080070630.XA CN114502680B (zh) 2019-10-11 2020-10-06 粘合剂组合物

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JP2019187461 2019-10-11
JP2019-187461 2019-10-11

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WO2021070801A1 true WO2021070801A1 (fr) 2021-04-15

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WO2024162053A1 (fr) * 2023-01-31 2024-08-08 デンカ株式会社 Composition pour fixation temporaire, adhésif pour fixation temporaire et procédé de production de tranche mince

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WO2015029940A1 (fr) * 2013-08-30 2015-03-05 三洋化成工業株式会社 Composition photosensible, substance durcie et dispositif d'affichage d'image
JP2017095658A (ja) * 2015-11-27 2017-06-01 三星エスディアイ株式会社Samsung SDI Co., Ltd. 粘着剤組成物、光学部材および粘着シート
WO2019004047A1 (fr) * 2017-06-27 2019-01-03 住友化学株式会社 Composition d'adhésif, et film avec couche d'adhésif

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JP2007284516A (ja) * 2006-04-14 2007-11-01 Toyo Ink Mfg Co Ltd 紫外線遮断性樹脂組成物及びその利用
WO2015029940A1 (fr) * 2013-08-30 2015-03-05 三洋化成工業株式会社 Composition photosensible, substance durcie et dispositif d'affichage d'image
JP2017095658A (ja) * 2015-11-27 2017-06-01 三星エスディアイ株式会社Samsung SDI Co., Ltd. 粘着剤組成物、光学部材および粘着シート
WO2019004047A1 (fr) * 2017-06-27 2019-01-03 住友化学株式会社 Composition d'adhésif, et film avec couche d'adhésif

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Publication number Priority date Publication date Assignee Title
WO2024162053A1 (fr) * 2023-01-31 2024-08-08 デンカ株式会社 Composition pour fixation temporaire, adhésif pour fixation temporaire et procédé de production de tranche mince

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CN114502680B (zh) 2023-12-01
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KR20220082009A (ko) 2022-06-16
CN114502680A (zh) 2022-05-13

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