WO2020196282A1 - Composition adhésive - Google Patents

Composition adhésive Download PDF

Info

Publication number
WO2020196282A1
WO2020196282A1 PCT/JP2020/012336 JP2020012336W WO2020196282A1 WO 2020196282 A1 WO2020196282 A1 WO 2020196282A1 JP 2020012336 W JP2020012336 W JP 2020012336W WO 2020196282 A1 WO2020196282 A1 WO 2020196282A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
meth
acrylate
sensitive adhesive
pressure
Prior art date
Application number
PCT/JP2020/012336
Other languages
English (en)
Japanese (ja)
Inventor
悠司 淺津
昭一 小澤
Original Assignee
住友化学株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 住友化学株式会社 filed Critical 住友化学株式会社
Priority to CN202080036527.3A priority Critical patent/CN113825811B/zh
Priority to KR1020217034662A priority patent/KR20210145205A/ko
Publication of WO2020196282A1 publication Critical patent/WO2020196282A1/fr

Links

Images

Classifications

    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/46—Polymerisation initiated by wave energy or particle radiation
    • C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
    • C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
    • C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
    • C08F265/06—Polymerisation of acrylate or methacrylate esters on to polymers thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F36/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
    • C08F36/22—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having three or more carbon-to-carbon double bonds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C09J11/06—Non-macromolecular additives organic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/04—Homopolymers or copolymers of esters
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
    • C09J175/04—Polyurethanes
    • 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
    • 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]
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
    • C09J2203/318—Applications of adhesives in processes or use of adhesives in the form of films or foils for the production of liquid crystal displays
    • 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 film in which the pressure-sensitive adhesive layer is laminated.
  • Various members such as organic EL elements, display elements such as liquid crystal cells, and optical films such as polarizing plates are used in display devices (FPDs: flat panel displays) such as organic EL display devices and liquid crystal display devices. Since organic EL compounds and liquid crystal compounds used for these members are often compounds having weak weather resistance among organic substances, deterioration due to not only ultraviolet rays (UV) but also short wavelength visible light of 420 nm or less is a problem. It is easy to become.
  • UV ultraviolet rays
  • Patent Document 1 a (meth) acrylic resin and a light selective absorption compound having an indole structure and selectively absorbing a wavelength near 400 nm (BONASORB UA manufactured by Orient Chemical Industry Co., Ltd.) A pressure-sensitive adhesive composition containing ⁇ 3911) and an optical film in which the pressure-sensitive adhesive layer is laminated are described.
  • the above-mentioned compound that selectively absorbs a specific wavelength has compatibility with the pressure-sensitive adhesive composition containing the light-selective absorption compound and the pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition. It was not sufficient, and there was a problem that the light selective absorption compound was precipitated during long-term storage, and the bleed resistance was not sufficient.
  • a pressure-sensitive adhesive composition containing a resin (A), a photoselective absorption compound (B) having a merocyanine structure and a polymerizable group in the molecule, and a photoinitiator (D).
  • a pressure-sensitive adhesive composition containing a resin (A), a photoselective absorption compound (B) having a merocyanine structure and a polymerizable group in the molecule, and a photoinitiator (D).
  • the pressure-sensitive adhesive composition according to any one of [1] to [11], wherein the photoselective absorption compound (B) having a merocyanine structure and a polymerizable group in the molecule satisfies the following formula (1).
  • ⁇ (405) represents the gram extinction coefficient of the photoselective absorption compound (B) having a merocyanine structure and a polymerizable group in the molecule at a wavelength of 405 nm.
  • the unit of the gram extinction coefficient is L / (g ⁇ cm).
  • the pressure-sensitive adhesive composition according to any one of [1] to [12], wherein the photoselective absorption compound (B) having a merocyanine structure and a polymerizable group in the molecule satisfies the following formula (2).
  • ⁇ (405) represents the gram extinction coefficient of the photoselective absorption compound (B) having a merocyanine structure and a polymerizable group in the molecule at a wavelength of 405 nm
  • ⁇ (440) represents merocyanin in the molecule. It represents the gram extinction coefficient of the light selective absorption compound (B) having a structure and a polymerizable group at a wavelength of 440 nm.
  • R 6 and R 7 independently represent a hydrogen atom, an alkyl group having 1 to 25 carbon atoms, an electron-withdrawing group, or an ethylenically unsaturated group.
  • R 1A and R 1B each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
  • R 1 and R 2 may be connected to each other to form a ring structure,
  • R 2 and R 3 may be connected to each other to form a ring structure, and
  • R 2 and R 4 may be connected to each other to form a ring structure.
  • R 3 and R 6 may be connected to each other to form a ring structure
  • R 5 and R 7 may be connected to each other to form a ring structure
  • R 6 and R 7 may be formed. May be connected to each other to form a ring structure.
  • any one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 is an ethylenically unsaturated group.
  • R 11 , R 12 , R 13 , R 14 and R 15 are independently hydrocarbon hydrocarbons having 1 to 25 carbon atoms which may have a hydrogen atom and a substituent. Represents an aromatic hydrocarbon group or a heterocyclic group having 6 to 15 carbon atoms which may have a group or a substituent, and —CH 2 ⁇ contained in the aliphatic hydrocarbon group or aromatic hydrocarbon group is It may be substituted with -NR 11A- , -SO 2- , -CO-, -O- or -S-.
  • R 16 and R 17 each independently represent a hydrogen atom, an alkyl group having 1 to 25 carbon atoms, an electron-withdrawing group, or an ethylenically unsaturated group.
  • R 11A and R 11B each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
  • R 11 and R 12 may be connected to each other to form a ring structure
  • R 12 and R 13 may be connected to each other to form a ring structure
  • R 12 and R 14 may be connected to each other to form a ring structure. May be formed.
  • One of R 16 or R 17 is an ethylenically unsaturated group.
  • a (405) ⁇ 0.5 (3) [In formula (3), A (405) represents the absorbance at a wavelength of 405 nm. ] [18] Further, the pressure-sensitive adhesive layer according to [17], which satisfies the following formula (4).
  • a (405) / A (440) ⁇ 5 (4) [In the formula (4), A (405) represents the absorbance at a wavelength of 405 nm, and A (440) represents the absorbance at a wavelength of 440 nm.
  • the pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition of the present invention has good bleed resistance without precipitation of photoselective absorbing compounds even after a long period of time after production.
  • An example of the layer structure of 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 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.
  • the pressure-sensitive adhesive composition of the present invention includes a resin (A), a photoselective absorption compound (B) having a merocyanine structure and a polymerizable group in the molecule (hereinafter, may be referred to as a light selective absorption compound (B)) and Contains the photoinitiator (D).
  • the pressure-sensitive adhesive composition of the present invention may further contain a photocurable component (C), a cross-linking agent (E), a silane compound and the like.
  • the resin (A) 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 of 40 ° C. or lower.
  • the glass transition temperature (Tg) of the resin (A) is more preferably 20 ° C. or lower, more preferably 10 ° C. or lower, and further preferably 0 ° C. or lower.
  • the glass transition temperature of the resin (A) is usually ⁇ 80 ° C. or higher, preferably ⁇ 60 ° C. or higher, more preferably ⁇ 50 ° C. or higher, and even more preferably ⁇ 45 ° C. or higher. , -30 ° C or higher is particularly preferable.
  • the glass transition temperature of the resin (A) is 40 ° C. or lower, it is advantageous to improve the adhesion between the pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition containing the resin (A) and the optical film. Further, when the glass transition temperature of the resin (A) is ⁇ 80 ° C. or higher, the durability of the pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition containing the resin (A) (appearance defects during a high-temperature test: aggregation failure, etc.) ) Is advantageous.
  • the glass transition temperature can be measured by a differential scanning calorimeter (DSC).
  • Examples of the resin having a glass transition temperature of 40 ° C. or lower 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 constituent 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 alkoxy group having 7 to 20 carbon atoms
  • hydrogen of the alkyl group or the aralkyl group The atom 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 (I)
  • 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 so on.
  • a substituent-containing (meth) acrylic acid alkyl ester in which a substituent is introduced into the alkyl group in the (meth) acrylic acid alkyl ester can also be mentioned.
  • the substituent of the substituent-containing (meth) acrylic acid alkyl ester is a group that substitutes the hydrogen atom of the alkyl group, and specific examples thereof include a phenyl group, an alkoxy group, and a phenoxy group.
  • Specific examples of the substituent-containing (meth) acrylic acid alkyl ester include (meth) acrylic acid 2-methoxyethyl, (meth) acrylic acid ethoxymethyl, (meth) acrylic acid phenoxyethyl, and (meth) acrylic acid 2-. Examples thereof include (2-phenoxyethoxy) ethyl, phenoxydiethylene glycol (meth) acrylate, and phenoxypoly (ethylene glycol) (meth) acrylate.
  • Each of these (meth) acrylic acid esters can be used alone, or a plurality of different ones may be used.
  • the (meth) acrylic resin (A) is a structural unit derived from an acrylic acid alkyl ester (a1) having a homopolymer glass transition temperature Tg of less than 0 ° C., and an alkyl acrylate having a homopolymer Tg of 0 ° C. or higher. It preferably contains a structural unit derived from the ester (a2). It is advantageous to contain a structural unit derived from the acrylic acid alkyl ester (a1) and a structural unit derived from the acrylic acid alkyl ester (a2) in order to enhance 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.
  • 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-hexyl acrylate. , N-heptyl acrylate, n- and i-octyl acrylate, 2-ethylhexyl acrylate, n- and i-nonyl acrylate, n- and i-decyl acrylate, n-dodecyl acrylate and the like
  • acrylic acid alkyl esters having a group having about 2 to 12 carbon atoms examples include acrylic acid alkyl esters having a group having about 2 to 12 carbon atoms.
  • Acrylic acid alkyl ester (a1) may be used alone or in combination of two or more. Among them, n-butyl acrylate, n-octyl acrylate, 2-ethylhexyl acrylate and the like are preferable from the viewpoint of followability and reworkability when the pressure-sensitive adhesive layer of the present invention is laminated on an optical film.
  • the acrylic acid alkyl ester (a2) is an acrylic acid alkyl ester other than the acrylic acid alkyl ester (a1).
  • Specific examples of the acrylic acid alkyl ester (a2) include methyl acrylate, cyclohexyl acrylate, and isobolonyl acrylate. Includes stearyl acrylate, t-butyl acrylate and the like.
  • Acrylic acid alkyl ester (a2) may be used alone or in combination of two or more. Above all, from the viewpoint of high temperature durability, the 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 or a monomer having a carboxyl group is 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 a group.
  • 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 (A) substantially contains a structural unit derived from a monomer having an amino group. It is preferable that there is no such thing.
  • substantially not contained means that the amount is 0.1 parts by mass or less out of 100 parts by mass of all the constituent units constituting the (meth) acrylic resin (a).
  • 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, with respect to 100 parts by mass of all the structural units of the (meth) acrylic resin (A). It is 5.5 parts by mass or more and 15 parts by mass or less, 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.
  • 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, based on 100 parts by mass of all the structural units of the (meth) acrylic resin (A). More than 20 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) acrylates include structural units derived from styrene-based monomers, structural units derived from vinyl-based monomers, and a plurality of (meth) acryloyls 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; 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 a molecule such as meta) acrylate, ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, tetraethylene glycol di (meth) acrylate, and tripropylene glycol di (meth) acrylate.
  • Monomer having; Examples thereof include a monomer having three (meth) acryloyl groups in the molecule such as trimethylolpropane tri (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 (A) is preferably 500,000 to 2.5 million.
  • the weight average molecular weight is 500,000 or more, the durability of the adhesive layer in a high temperature environment is improved, and problems such as floating and peeling between the adherend and the adhesive sheet and cohesive failure of the adhesive sheet are caused. Easy to suppress.
  • the weight average molecular weight is 2.5 million or less, it is advantageous from the viewpoint of coatability.
  • 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 viscosity at 25 ° C. is preferably 20 Pa ⁇ s or less, and 0.1 to 15 Pa ⁇ s. 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 substrate.
  • the viscosity can be measured with a Brookfield viscometer.
  • the (meth) acrylic resin (A) 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 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.
  • 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 photoselective absorption compound (B) is a compound containing a merocyanine structure and a polymerizable group in the molecule.
  • the merocyanine structure of the present invention does not include an indole ring.
  • polymerizable group examples include an epoxy group, an oxetanyl group, an oxazolino group, an aziridino group, an ethylenically unsaturated group and the like.
  • the polymerizable group of the light selective absorption compound (B) is preferably an ethylenically unsaturated group.
  • Specific examples of the ethylenically unsaturated group include a vinyl group, an ⁇ -methylvinyl group, an acryloyl group, a metaacryloyl group, an allyl group, a styryl group and a group represented by the formula (I-2) described later.
  • the photoselective absorption compound (B) having a merocyanine structure and a polymerizable group in the molecule preferably satisfies the following formula (1), and more preferably satisfies the formula (2).
  • ⁇ (405) ⁇ 5 (1) [In the formula (1), ⁇ (405) represents the gram extinction coefficient of the photoselective absorption compound (B) having a merocyanine structure and a polymerizable group in the molecule at a wavelength of 405 nm. The unit of the gram extinction coefficient is L / (g ⁇ cm).
  • ⁇ (405) represents the gram extinction coefficient of the photoselective absorption compound (B) having a merocyanine structure and a polymerizable group in the molecule at a wavelength of 405 nm.
  • ⁇ (440) represents the gram extinction coefficient of the light selective absorption compound (B) having a merocyanine structure and a polymerizable group in the molecule at a wavelength of 440 nm.
  • the photoselective absorption compound (B) having a merocyanine structure and a polymerizable group in the molecule preferably has a value of ⁇ (405) of 5 L / (g ⁇ cm) or more, preferably 10 L / (g ⁇ cm) or more. It is more preferably 20 L / (g ⁇ cm) or more, further preferably 30 L / (g ⁇ cm) or more, and usually 500 L / (g ⁇ cm) or less.
  • a compound having a larger value of ⁇ (405) is more likely to absorb light having a wavelength of 405 nm, and is more likely to exhibit a function of suppressing deterioration due to ultraviolet rays or visible light having a short wavelength.
  • the photoselective absorption compound (B) having a merocyanine structure and a polymerizable group in the molecule preferably has a value of ⁇ (405) / ⁇ (440) of 20 or more, more preferably 40 or more. 70 or more is even more preferable, and 80 or more is particularly more preferable.
  • the pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition containing a compound having a large value of ⁇ (405) / ⁇ (440) absorbs light having a wavelength of around 405 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.
  • Examples of the photoselective absorption compound (B) having a merocyanine structure and a polymerizable group in the molecule include a compound represented by the formula (I).
  • R 1 , R 2 , R 3 , R 4 and R 5 are independently hydrocarbon hydrocarbons having 1 to 25 carbon atoms which may have hydrogen atoms and substituents. It represents an aromatic hydrocarbon group having 6 to 15 carbon atoms, a heterocyclic group or an ethylenically unsaturated group which may have a group or a substituent, and is contained in the aliphatic hydrocarbon group or the aromatic hydrocarbon group.
  • -CH 2- may be replaced with -NR 1A- , -SO 2- , -CO-, -O- or -S-.
  • R 6 and R 7 independently represent a hydrogen atom, an alkyl group having 1 to 25 carbon atoms, an electron-attracting group, or an ethylenically unsaturated group.
  • R 1A represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
  • R 1 and R 2 may be connected to each other to form a ring structure
  • R 2 and R 3 may be connected to each other to form a ring structure
  • R 2 and R 4 may be connected to each other to form a ring structure.
  • R 3 and R 6 may be connected to each other to form a ring structure
  • R 5 and R 7 may be connected to each other to form a ring structure
  • R 6 and R 7 may be formed. May be connected to each other to form a ring structure.
  • at least one of R 1 to R 7 is an ethylenically unsaturated group
  • Examples of the aliphatic hydrocarbon group having 1 to 25 carbon atoms represented by R 1 to R 5 include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a tert-butyl group and a sec-butyl group.
  • n-pentyl group isopentyl group, n-hexyl group, isohexyl group, n-octyl group, isooctyl group, n-nonyl group, isononyl group, n-decyl group, isodecyl group, n-dodecyl group, isododecyl group, Linear or branched alkyl group having 1 to 25 carbon atoms such as undecyl group, lauryl group, myristyl group, cetyl group and stearyl group: 3 to 25 carbon atoms such as cyclopropyl group, cyclobutyl group, cyclopentyl group and cyclohexyl group.
  • Cycloalkyl group A cycloalkylalkyl group having 4 to 25 carbon atoms such as a cyclohexylmethyl group, and an alkyl group having 4 to 25 carbon atoms is preferable.
  • substituent that the aliphatic hydrocarbon group having 1 to 25 carbon atoms represented by R 1 to R 5 may have include a hydroxy group, a cyano group, a halogen atom, a mercapto group, an amino group, a nitro group and the like.
  • the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
  • Examples of the aromatic hydrocarbon group having 6 to 15 carbon atoms represented by R 1 to R 5 include an aryl group having 6 to 15 carbon atoms such as a phenyl group, a naphthyl group, an anthracenyl group and a biphenyl group; a benzyl group and a phenylethyl group. Examples thereof include an aralkyl group having 7 to 15 carbon atoms such as a group, a naphthylmethyl group and phenyl.
  • Examples of the substituent that the aromatic hydrocarbon group having 6 to 15 carbon atoms represented by R 1 to R 5 may have include a hydroxy group, a cyano group, a halogen atom, a mercapto group, an amino group and a nitro group.
  • it represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms
  • R 4A represents an alkyl group having 1 to 6 carbon atoms.
  • halogen atom examples include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
  • alkoxy group examples include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, an octyloxy group, a 2-ethylhexyloxy group, a nonyloxy group, a decyloxy group, an undecyloxy group and a dodecyloxy group.
  • Alkoxy groups having 1 to 12 carbon atoms can be mentioned.
  • alkylthio group examples include an alkylthio group having 1 to 12 carbon atoms such as a methylthio group, an ethylthio group, a propylthio group and a butylthio group.
  • acyl group examples include an acyl group having 2 to 13 carbon atoms such as an acetyl group, a propionyl group and a butyryl group.
  • acyloxy group examples include methylcarbonyloxy group, ethylcarbonyloxy group, n-propylcarbonyloxy group, isopropylcarbonyloxy group, n-butylcarbonyloxy group, sec-butylcarbonyloxy group, tert-butylcarbonyloxy group and pentylcarbonyl.
  • examples thereof include an acyloxy group having 2 to 13 carbon atoms such as an oxy group, a hexylcarbonyloxy group, an octylcarbonyloxy group and a 2-ethylhexylcarbonyloxy group.
  • alkoxycarbonyl group examples include a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, a butoxycarbonyl group, a pentyloxycarbonyl group, a hexyloxycarbonyl group, an octyloxycarbonyl group, a 2-ethylhexyloxycarbonyl group, a nonyloxycarbonyl group, and a decyl.
  • alkoxycarbonyl groups having 2 to 13 carbon atoms such as an oxycarbonyl group, an undecyloxycarbonyl group, and a dodecyloxycarbonyl group.
  • the -CONR 3A R 3B aminocarbonyl group, methylaminocarbonyl group, dimethylaminocarbonyl group, ethylaminocarbonyl group, and the like methyl aminocarbonyl group.
  • Examples of -C (NR 2A ) R 2B include a methylimino group, a dimethylimino group, a methylethylimino group and the like.
  • Examples of -SO 2 R 4A include a methyl sulfonyl group and an ethyl sulfonyl group.
  • Examples of the alkyl group having 1 to 6 carbon atoms represented by R 1A and R 1B include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a tert-butyl group, a sec-butyl group and the like. Can be mentioned.
  • the heterocyclic groups represented by R 1 to R 5 include a pyrrolidine ring group, a pyrolin ring group, an imidazolidine ring group, an imidazoline ring group, an oxazoline ring group, a thiazolin ring group, a piperidine ring group, a morpholine ring group, and a piperazin ring.
  • An aliphatic heterocyclic group having 4 to 20 carbon atoms or an aliphatic heterocyclic group having 3 to 20 carbon atoms such as a group, an indole ring group, an isoindole ring group, a quinoline ring group, a thiophene ring group, a pyrrol ring group, a thiazolin ring group and a furan ring group.
  • Examples include aromatic heterocyclic groups.
  • Alkyl groups having 1 to 25 carbon atoms represented by R 6 and R 7 include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, tert-butyl group, sec-butyl group and n.
  • -Pentyl group isopentyl group, n-hexyl group, isohexyl group, n-octyl group, isooctyl group, n-nonyl group, isononyl group, n-decyl group, isodecil group, n-dodecyl group, isododecyl group, undecyl group, Examples thereof include linear or branched alkyl groups having 1 to 25 carbon atoms such as lauryl group, myristyl group, cetyl group and stearyl group.
  • Examples of the electron-attracting group represented by R 6 and R 7 include a cyano group, a nitro group, a halogen atom, an alkyl group substituted with a halogen atom, and a group represented by the formula (I-1). Be done.
  • R 111 represents a hydrocarbon group having 1 to 25 carbon atoms which may have a hydrogen atom or a halogen atom, and at least one of the methylene groups contained in the hydrocarbon group is replaced with an oxygen atom. It may have been.
  • X 1 is, -CO- * 1, -COO- * 1 , -CS- * 1, -CSS- * 1, -CSNR 112 - * 1, -CONR 113 - * 1, -CNR 114 - * 1 or - Represents SO 2- * 1 .
  • R 112 , R 113 and R 114 each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms or a phenyl group.
  • * 1 represents a bond with R 111 .
  • halogen atom examples include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
  • Alkyl groups substituted with halogen atoms include, for example, trifluoromethyl group, perfluoroethyl group, perfluoropropyl group, perfluoroisopropyl group, perfluorobutyl group, perfluorosec-butyl group, perfluorotert-butyl group, perfluoropentyl group and Examples thereof include perfluoroalkyl groups such as perfluorohexyl groups.
  • the number of carbon atoms of the alkyl group substituted with the halogen atom is usually 1 to 25, preferably 1 to 12 carbon atoms.
  • the hydrocarbon group having 1 to 25 carbon atoms which may have a halogen atom represented by R 111 includes a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group and a tert-butyl group.
  • Alkylated group monoiodomethyl group, diiodomethyl group, triiodomethyl group, 2,2,2-triiodoethyl group, periodoethyl group, periodopropyl group, periodobutyl group, periodopentyl group, periode
  • An alkyl iodide group having 1 to 25 carbon atoms such as a hexyl group; can be mentioned.
  • Examples of the alkyl group having 1 to 6 carbon atoms represented by R 112 , R 113 and R 114 include the same alkyl group having 1 to 6 carbon atoms represented by R 1A .
  • R 111 is preferably an alkyl group having 4 to 25 carbon atoms which may have a halogen atom, and more preferably an alkyl group having 4 to 12 carbon atoms which may have a halogen atom. .. X 1 is preferably -CO- * 1 and -COO- * 1 .
  • the electron-attracting groups represented by R 6 and R 7 are independently cyano groups, nitro groups, fluoro groups, trifluoromethyl groups, and groups represented by the formula (I-1). Is preferable. Particularly preferably, it is a cyano group.
  • the ring structure formed by bonding R 1 and R 2 to each other is a nitrogen-containing ring structure containing a nitrogen atom to which R 1 and R 2 are bonded, and is, for example, a 4-membered ring to a 10-membered ring.
  • a nitrogen-containing heterocycle can be mentioned.
  • the ring structure formed by connecting R 1 and R 2 to each other may be a monocyclic ring, a polycyclic ring, or a condensed ring.
  • a pyrrolidine ring examples thereof include a pyrrolidine ring, a pyrroline ring, an imidazolidine ring, an imidazoline ring, an oxazoline ring, a thiazolin ring, a piperazine ring, a morpholine ring, a piperazine ring, an indole ring, and an isoindole ring.
  • the ring formed by bonding R 1 and R 2 to each other may have a substituent, and the substituent may have 1 carbon number such as a methyl group, an ethyl group, a propyl group, a butyl group and an isobutyl group.
  • Alkyl groups to 12 examples thereof include alkoxy groups having 1 to 12 carbon atoms such as methoxy group, ethoxy group, propoxy group and butoxy group.
  • the ring structure formed by bonding R 2 and R 3 to each other is a nitrogen-containing ring structure containing a nitrogen atom to which R 2 is bonded, and is, for example, a nitrogen-containing heterocycle having a 4-membered ring to a 10-membered ring. Ring is mentioned.
  • the ring structure formed by connecting R 2 and R 3 to each other may be a monocyclic ring, a polycyclic ring, or a condensed ring.
  • a pyrrolidine ring a pyrroline ring, an imidazolidine ring, an imidazoline ring, an oxazoline ring, a thiazolin ring, a piperazine ring, a morpholine ring, a piperazine ring, an indole ring, an isoindole ring, and the following formula (I-3).
  • Ring structure can be mentioned.
  • X represents a nitrogen atom, an oxygen atom, and a sulfur atom.
  • Ring W 1 represents a ring having a nitrogen atom and X as components.
  • the ring W 1 is preferably a 5-membered ring or a 6-membered ring having a nitrogen atom and X as components.
  • Specific examples of the ring structure represented by the formula (I-3) include the following rings.
  • the ring structure formed by bonding R 2 and R 3 to each other may have a substituent, and the substituent may be a carbon such as a methyl group, an ethyl group, a propyl group, a butyl group or an isobutyl group.
  • Alkyl group of number 1 to 12; alkoxy group having 1 to 12 carbon atoms such as methoxy group, ethoxy group, propoxy group, butoxy group and the like can be mentioned.
  • the ring structure formed by bonding R 2 and R 3 to each other is preferably a ring structure represented by the following formula (I-4).
  • R 1 has the same meaning as above.
  • m2 represents an integer from 1 to 7.
  • R 11a , R 11b , R 11c and R 11d each independently represent a hydrogen atom or an alkyl group having 1 to 12 carbon atoms. * Represents a bond with a carbon atom.
  • m2 is preferably 2 or 3, and more preferably 2.
  • Examples of the ring structure formed by bonding R 2 and R 4 to each other include a nitrogen-containing ring structure having a 4-membered ring to a 10-membered ring, and a nitrogen-containing ring structure having a 5-membered ring to a 9-membered ring is preferable.
  • the ring structure formed by bonding R 2 and R 4 to each other may be monocyclic or polycyclic. These rings may have substituents. Examples of such a ring structure include a pyrrole ring, an indole ring, a pyrimidine ring, and the rings described below.
  • the ring structure formed by bonding R 2 and R 4 to each other may have a substituent, and the substituent may have a number of carbon atoms such as a methyl group, an ethyl group, a propyl group, a butyl group and an isobutyl group.
  • R 22A and R 22B each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms); 1 to 12 carbon atoms such as a methylthio group, an ethylthio group, a propylthio group, a butylthio group, a pentylthio group, etc.
  • Alkylthio group of: Pyrrolidinyl group, piperidinyl group, morpholinyl group and other heterocyclic groups having 4 to 9 carbon atoms can be mentioned.
  • a phenyl group and the like can be mentioned.
  • Examples of the ring structure formed by connecting R 5 and R 7 to each other include the ring structure described below.
  • the ring structure formed by bonding R 5 and R 7 to each other may have a substituent, and the substituent may have a number of carbon atoms such as a methyl group, an ethyl group, a propyl group, a butyl group and an isobutyl group.
  • Alkyl groups of 1 to 12; alkoxy groups having 1 to 12 carbon atoms such as methoxy group, ethoxy group, propoxy group and butoxy group can be mentioned.
  • Examples of the ring structure formed by connecting R 6 and R 7 to each other include the ring structure described below.
  • the ring structure formed by bonding R 6 and R 7 to each other may have substituents (R 1 to R 16 in the following formula), and the substituents include a methyl group, an ethyl group and a propyl group.
  • Alkyl groups having 1 to 12 carbon atoms such as groups, butyl groups and isobutyl groups; alkoxy groups having 1 to 12 carbon atoms such as methoxy groups, ethoxy groups, propoxy groups and butoxy groups; and ethylenically unsaturated groups described below. Be done. [In the formula, * represents a bond with a carbon atom. ]
  • Examples of the ethylenically unsaturated group represented by R 1 to R 7 include a vinyl group, an ⁇ -methyl vinyl group, an acryloyl group, a metaacryloyl group, an allyl group, a styryl group and a group represented by the formula (I-2). Can be mentioned.
  • X 2 represents a vinyl group, an acryloyl group or a meta-acryloyl group.
  • R 115 represents a divalent aliphatic hydrocarbon group having 1 to 18 carbon atoms, and -CH 2- contained in the aliphatic hydrocarbon group is -O-, -CO-, -CS- or -NR. It may be replaced with 116-.
  • R 116 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. * Represents a bond with a carbon atom or a nitrogen atom.
  • Examples of the divalent aliphatic hydrocarbon group having 1 to 18 carbon atoms represented by R 115 include a methylene group, an ethylene group, a propane-1,3-diyl group, a propane-1,2-diyl group and butane-1.
  • the ethylenically unsaturated groups represented by R 1 to R 7 are preferably vinyl groups, acryloyl groups, metaacryloyl groups, and groups represented by the formula (I-2), respectively.
  • any one of R 6 and R 7 is an electron attracting group. It is preferable that either one of R 6 and R 7 is an ethylenically unsaturated group.
  • the compound represented by the formula (I) is preferably a compound represented by the formula (II).
  • R 11 , R 12 , R 13 , R 14 and R 15 are independently hydrocarbon hydrocarbons having 1 to 25 carbon atoms which may have a hydrogen atom and a substituent. Represents an aromatic hydrocarbon group or a heterocyclic group having 6 to 15 carbon atoms which may have a group or a substituent, and —CH 2 ⁇ contained in the aliphatic hydrocarbon group or aromatic hydrocarbon group is It may be substituted with -NR 11A- , -SO 2- , -CO-, -O- or -S-.
  • R 16 and R 17 each independently represent a hydrogen atom, an alkyl group having 1 to 25 carbon atoms, an electron-attracting group, or an ethylenically unsaturated group.
  • R 11A represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
  • R 12 and R 13 may be connected to each other to form a ring structure, and R 12 and R 14 may be connected to each other to form a ring structure.
  • either one of R 16 or R 17 is an ethylenically unsaturated group.
  • R 11 ⁇ The substituent may have a number of 1 to 25 aliphatic carbon hydrocarbon groups represented by R 15, carbon atoms 1 may have a substituent represented by R 1 ⁇ The same as the 25 aliphatic hydrocarbon groups can be mentioned.
  • the aromatic hydrocarbon group having 6 to 15 carbon atoms which may have a substituent represented by R 11 to R 15 may have a substituent represented by R 1 and has 6 carbon atoms.
  • the same as the aromatic hydrocarbon groups of ⁇ 15 can be mentioned.
  • Examples of the heterocycle represented by R 11 to R 15 include the same heterocycle represented by R 1 .
  • Examples of the alkyl group having 1 to 25 carbon atoms represented by R 16 and R 17 include the same alkyl group having 1 to 25 carbon atoms represented by R 6 .
  • Examples of the electron-attracting group represented by R 16 and R 17 include the same electron-attracting group represented by R 6 .
  • Examples of the alkyl group having 1 to 6 carbon atoms represented by R 11A and R 11B include the same alkyl group having 1 to 6 carbon atoms represented by R 1A .
  • Examples of the ring structure in which R 12 and R 13 can be formed by connecting with each other include the same ring structure in which R 2 and R 3 can be formed by connecting with each other.
  • the ring structure that can be formed by connecting R 12 and R 13 to each other is preferably a monocyclic structure.
  • Examples of the ring structure in which R 12 and R 14 can be formed by connecting with each other include the same ring structure in which R 2 and R 4 can be formed by connecting with each other.
  • the ring structure that can be formed by connecting R 12 and R 14 to each other is preferably a monocyclic structure.
  • the ring structure that can be formed by connecting R 12 and R 14 to each other is preferably an aromatic ring, and more preferably a pyrimidine ring structure.
  • Each of R 11 , R 13 and R 15 is preferably an aliphatic hydrocarbon group having 1 to 25 carbon atoms, which may independently have a substituent, and may have a substituent. It is more preferably an alkyl group having 1 to 25 carbon atoms, and further preferably an alkyl group having 1 to 12 carbon atoms which may have a substituent.
  • R 11 is preferably an aliphatic hydrocarbon group having 1 to 10 carbon atoms, more preferably an alkyl group having 1 to 10 carbon atoms, and even more preferably a methyl group.
  • R 12 and R 14 are each independently an aliphatic hydrocarbon group having 1 to 25 carbon atoms which may have a substituent, or R 12 and R 14 are linked to each other to form a ring structure. It is preferable to do so.
  • R 12 and R 13 are preferably connected to each other to form a ring structure, and more preferably a ring structure represented by the above-mentioned formula (I-4).
  • the ring structure represented by the formula (I-4) is particularly preferable. It is preferably a ring structure represented by the formula (I-4-1).
  • the ring structure represented by the formula (I-4), the formula (I-4-1) or the formula (I-4-2) may further have a substituent. It is preferable that one of R 16 and R 17 is an ethylenically unsaturated group and the other is an electron-attracting group.
  • the electron-attracting groups represented by R 16 and R 17 are independently cyano groups, nitro groups, fluoro groups, trifluoromethyl groups, and groups represented by the formula (I-1). Is preferable. Particularly preferably, it is a cyano group.
  • the ethylenically unsaturated groups represented by R 16 and R 17 are preferably vinyl groups, acryloyl groups, metaacryloyl groups, and groups represented by the formula (I-2), respectively.
  • the compound represented by the formula (II) in which R 12 and R 13 are connected to each other to form a ring structure is a compound represented by the formula (II-A-1) or a compound represented by the formula (II-A-2). ) Is preferable.
  • the compound represented by the formula (II) in which R 12 and R 14 are linked to each other to form a ring structure is preferably a compound represented by the formula (II-B-1). [In the formula (II-A-1), the formula (II-A-2) and the formula (II-B-1), R 11 , R 14 , R 15 , R 16 and R 17 have the same meanings as described above, respectively. Represents.
  • R 11e , R 11f , R 11g , R 11h , R 11k , R 11m , and R 11n each independently represent a hydrogen atom or an alkyl group having 1 to 12 carbon atoms.
  • R 11q and R 11p are independent hydrogen atoms, an alkyl group having 1 to 12 carbon atoms, and a group represented by -NR 22A R 22B (R 22A and R 22B are independent hydrogen atoms or, respectively. Represents an alkyl group having 1 to 6 carbon atoms) or a heterocycle.
  • the compound represented by the formula (II) in which the electron-attracting group is a cyano group is obtained by reacting the compound represented by the following formula (I') with the compound represented by the formula (L).
  • R222 represents a divalent linking group and X 2 represents a polymerizable group.
  • the reaction between the compound represented by the formula (I') and the compound represented by the formula (L) can be carried out under any conditions used for general Knephener gel condensation. For example, it is preferably carried out in the presence of a base or a carboxylic acid anhydride.
  • Examples of the base include triethylamine, N, N-diisopropylethylamine, pyridine, piperidine, pyrrolidine, proline, N, N-dimethylaminopyridine, imidazole, sodium hydroxide, potassium hydroxide, potassium carbonate, sodium carbonate, sodium hydrogencarbonate. , Potassium hydrogen carbonate, potassium hydroxide butoxide, sodium hydroxide, sodium hydrogen and the like.
  • Examples of the carboxylic acid anhydride include acetic anhydride, succinic anhydride, phthalic anhydride, maleic anhydride, benzoic anhydride and the like.
  • the amount of the base used is preferably 0.1 to 10 mol with respect to 1 mol of the compound represented by the formula (I').
  • the amount of the carboxylic acid anhydride used is preferably 0.2 to 5 mol with respect to 1 mol of the compound represented by the formula (I').
  • the reaction between the compound represented by the formula (I') and the compound represented by the formula (L) is preferably carried out in an organic solvent.
  • the organic solvent include toluene, acetonitrile, dichloromethane, trichloromethane and the like.
  • the reaction between the compound represented by the formula (I') and the compound represented by the formula (L) is to mix the compound represented by the formula (I') and the compound represented by the formula (L). It will be carried out at.
  • the reaction temperature of the compound represented by the formula (I') and the compound represented by the formula (L) is preferably ⁇ 40 to 130 ° C., and the reaction time is usually preferably 1 to 24 hours.
  • the compound represented by the formula (I') can be synthesized, for example, according to the method described in JP-A-2014-194508.
  • the compound represented by the formula (L) can be obtained, for example, by reacting cyanoacetic acid with a hydroxyalkyl acrylate.
  • the amount of cyanoacetic acid used is preferably 0.5 to 3 mol with respect to 1 mol of the hydroxyalkyl acrylate.
  • the reaction between cyanoacetic acid and hydroxyalkyl acrylate can be carried out using any esterification catalyst used in general esterification reactions, but is preferably carried out in the presence of a base and a carbodiimide condensing agent.
  • Examples of the base include triethylamine, diisopropylethylamine, pyridine, piperidine, pyrrolidine, proline, N, N-dimethylaminopyridine, imidazole, sodium hydroxide, potassium hydroxide, potassium carbonate, sodium carbonate, sodium hydrogencarbonate, potassium hydrogencarbonate. , Potassium hydroxide, sodium hydroxide, sodium hydrogen, and the like.
  • Examples of the carbodiimide condensing agent include N, N-dicyclohexylcarbodiimide, N, N-diisopropylcarbodiimide, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride and the like.
  • the amount of the base used is preferably 0.5 to 5 mol with respect to 1 mol of cyanoacetic acid.
  • the reaction between cyanoacetic acid and hydroxyalkyl acrylate is preferably carried out in an organic solvent.
  • the organic solvent include acetonitrile, isopropanol, toluene, trichloromethane, dichloromethane and the like.
  • the reaction between cyanoacetic acid and hydroxyalkyl acrylate is carried out by mixing cyanoacetic acid and hydroxyalkyl acrylate.
  • the reaction temperature of cyanoacetic acid and hydroxyalkyl acrylate is preferably ⁇ 40 to 130 ° C., and the reaction time is usually preferably 1 to 24 hours.
  • Examples of the photoselective absorption compound (B) having a merocyanine structure and a polymerizable group in the molecule include the compounds described below.
  • the content of the photoselective absorption compound (B) having a merocyanine structure and a polymerizable group in the molecule is usually 0.1 to 50 parts by mass with respect to 100 parts by mass of the resin (A), and is 0.5. It is preferably about 20 parts by mass, more preferably 1 to 10 parts by mass, and even more preferably 2 to 7 parts by mass. Two or more kinds of photoselective absorption compounds (B) having a merocyanine structure and a polymerizable group in the molecule may be contained.
  • the photoinitiator (D) is a compound (polymerization initiator) that causes a polymerization reaction by absorbing light energy.
  • the light is preferably an active energy ray such as visible light, ultraviolet light, X-ray, or electron beam.
  • the photoinitiator (D) is a compound that generates radicals by absorbing light energy (photoradical generator) and a compound that generates cations (acids) by absorbing light energy (acid).
  • Photocation generator a compound that generates an anion (base) by absorbing light energy (photobase generator), and examples thereof.
  • the photoinitiator (D) may be appropriately selected to react with the polymerizable group of the photoselective absorption compound (B) having a merocyanine structure and a polymerizable group in the molecule.
  • the photoinitiator (D) may be a photoradical generator. preferable.
  • the photoinitiator (D) is a photocationic generator. Is preferable. Further, from the viewpoint of the reactivity of the light selective absorption compound (B), the photoinitiator (D) is preferably a photoradical generator.
  • Two or more types of photoinitiator (D) may be contained.
  • the polymerizable group of the photoselective absorption compound (B) having a merocyanine structure and a polymerizable group in the molecule is radically polymerizable
  • the photocurable component (C) described later is a photocationic curable component.
  • a photoradical generator and a photocation generator may be used in combination.
  • Examples of the photoradical generator include alkylphenone compounds, benzoin compounds, benzophenone compounds, oxime ester compounds, phosphine compounds and the like.
  • alkylphenon compound examples include an ⁇ -aminoalkylphenon compound, an ⁇ -hydroxyalkylphenon compound, and an ⁇ -alkoxyalkylphenon 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 and 2-dimethylamino-1- (4-morpholinophenyl) -2-benzylbutane-1-one.
  • 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 Chemical Company) 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 Ltd.), 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.).
  • the photoradical generator is preferably an oxime ester compound from the viewpoint of the reactivity of the light selective absorption compound (B).
  • photocation generator examples include onium salts such as aromatic iodonium salt and aromatic sulfonium salt; aromatic diazonium salt; and iron-arene complex.
  • the aromatic iodonium salt is a compound having a diaryl iodonium cation, and as the cation, a diphenyl iodonium 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 typical examples of the cation include a benzenediazonium cation.
  • the iron-arene complex is typically a cyclopentadienyl iron (II) arene cationic complex salt.
  • anions which constitute the photo-cation generator
  • 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
  • a special phosphate based anionic [(Rf) n PF 6- n] -, hexafluorophosphate anion PF 6 -, tetrakis (penta fluorophenyl) borate anion B (C 6 F 5) 4 - is preferably.
  • the content of the photoinitiator (D) is usually 0.01 to 20 parts by mass, preferably 0.05 to 10 parts by mass, and 0.1 to 0.1 parts by mass with respect to 100 parts by mass of the resin (A). It is more preferably 5 parts by mass, and further preferably 0.2 to 3 parts by mass.
  • the pressure-sensitive adhesive composition of the present invention can contain a photocurable component (C).
  • the photocurable component (C) may be a photoradical curable component such as a compound or an oligomer that is cured by a radical polymerization reaction by irradiation with light. Further, it may be a photocurable component such as a compound or an oligomer that is cured by a cationic polymerization reaction by irradiation with light.
  • the light is preferably an active energy ray such as visible light, ultraviolet light, X-ray, or electron beam.
  • the photocurable component (C) preferably reacts with the polymerizable group of the photoselective absorption compound (B) having a merocyanine structure and a polymerizable group in the molecule.
  • the photocurable component (C) is a photoradical curable component. It is preferable to have. Two or more kinds of photocurable components (C) may be contained.
  • Examples of the photoradical polymerizable component include radically polymerizable (meth) acrylic compounds.
  • Examples of the (meth) acrylic 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.
  • (Meta) acryloyl group-containing compounds such as (meth) acrylic oligomers having the above can be mentioned.
  • 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.
  • Examples include monomers and polyfunctional (meth) acrylate monomers having three or more (meth) acryloyloxy groups in the molecule.
  • 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.
  • 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) acrylamides 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.
  • 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.
  • an aromatic, aliphatic or alicyclic polyol a polyester polyol, a polyether polyol or the like may be used. 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 its anhydride.
  • 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
  • (anhydrous) pyromellitic acid (anhydrous) phthalic acid
  • isophthalic acid terephthalic acid
  • hexahydro (anhydrous) phthalic acid and the like.
  • the polyether polyol may be the above-mentioned polyol or a polyoxyalkylene-modified polyol obtained by reacting dihydroxybenzenes with alkylene oxide.
  • 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 dehydrating and condensing (meth) acrylic acid, a polybasic carboxylic acid or an anhydride thereof, and a polyol.
  • the polybasic carboxylic acid or its anhydride include succinic anhydride, adipic acid, maleic anhydride, itaconic anhydride, trimellitic anhydride, pyromellitic anhydride, phthalic 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, trimethylolbutanoic acid, 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.
  • the photoradical curable component preferably contains a (meth) acrylate compound, and more preferably contains a polyfunctional (meth) acrylate compound.
  • Photocationic curable component examples include epoxy compounds, oxetane compounds, vinyl compounds and the like.
  • the epoxy compound examples include an alicyclic epoxy compound, an aromatic epoxy compound, a hydride epoxy compound, and an aliphatic epoxy compound.
  • the alicyclic epoxy compound is a compound having one or more epoxy groups bonded to the alicyclic ring in the molecule.
  • Examples of the epoxy group bonded to the alicyclic ring include an oxabicyclohexyl group and an oxabicycloheptyl group.
  • the alicyclic epoxy compound may be a compound containing one alicyclic epoxy group, or may contain two or more alicyclic epoxy groups.
  • Examples of the alicyclic epoxy compound include 3,4-epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate, 3,4-epoxy-6-methylcyclohexylmethyl 3,4-epoxy-6-methylcyclohexanecarboxylate, and ethylenebis.
  • Aromatic epoxy compounds are compounds that have an aromatic ring and an epoxy group in the molecule.
  • the aromatic epoxy compound include bisphenol-type epoxy compounds such as bisphenol A diglycidyl ether, bisphenol F diglycidyl ether, and bisphenol S diglycidyl ether or oligomers thereof; phenol novolac epoxy resin, cresol novolac epoxy resin, and hydroxybenzaldehyde.
  • Novolak type epoxy resin such as phenol novolac epoxy resin; polyfunctional type such as 2,2', 4,4'-tetrahydroxydiphenylmethane glycidyl ether, 2,2', 4,4'-tetrahydroxybenzophenone glycidyl ether, etc.
  • the hydrogenated epoxy compound is a glycidyl ether of a polyol having an alicyclic ring, and is a nuclear hydrogenated poly obtained by selectively hydrogenating an aromatic polyol on an aromatic ring under pressure in the presence of a catalyst. It can be a glycidyl etherified hydroxy compound.
  • aromatic polyols include bisphenol-type compounds such as bisphenol A, bisphenol F, and bisphenol S; novolak-type resins such as phenol novolac resin, cresol novolac resin, and hydroxybenzaldehyde phenol novolac resin; tetrahydroxydiphenylmethane and tetrahydroxy. Contains polyfunctional compounds such as benzophenone and polyvinylphenol.
  • Glycidyl ether can be obtained by reacting epichlorohydrin with an alicyclic polyol obtained by hydrogenating the aromatic ring of an aromatic polyol.
  • the hydrogenated epoxy compounds the diglycidyl ether of hydrogenated bisphenol A can be mentioned.
  • the aliphatic epoxy compound is a compound having at least one oxylan ring (three-membered cyclic ether) bonded to an aliphatic carbon atom in the molecule.
  • monofunctional epoxy compounds such as butyl glycidyl ether and 2-ethylhexyl glycidyl ether; bifunctional such as 1,4-butanediol diglycidyl ether, 1,6-hexanediol diglycidyl ether and neopentyl glycol diglycidyl ether.
  • Epoxide compounds Trifunctional or higher functional epoxy compounds such as trimethylolpropan triglycidyl ether and pentaerythritol tetraglycidyl ether; with one epoxy group directly bonded to the alicyclic ring such as 4-vinylcyclohexendioxide and limonendioxide. , Epoxide compounds having an oxylane ring bonded to an aliphatic carbon atom and the like.
  • An oxetane compound is a compound containing one or more oxetane rings (oxetanyl groups) in the molecule.
  • examples of the oxetane compound include 3-ethyl-3-hydroxymethyloxetane, 2-ethylhexyloxetane, 1,4-bis [ ⁇ (3-ethyloxetane-3-yl) methoxy ⁇ methyl] benzene, and 3-ethyl-3 [ ⁇ .
  • Examples of the vinyl compound include an aliphatic or alicyclic vinyl ether compound.
  • Examples of the vinyl compound include alkyl having 5 to 20 carbon atoms such as n-amyl vinyl ether, i-amyl vinyl ether, n-hexyl vinyl ether, n-octyl vinyl ether, 2-ethylhexyl vinyl ether, n-dodecyl vinyl ether, stearyl vinyl ether and oleyl vinyl ether.
  • Vinyl ether of alkenyl alcohol hydroxyl group-containing vinyl ether such as 2-hydroxyethyl vinyl ether, 3-hydroxypropyl vinyl ether, 4-hydroxybutyl vinyl ether; aliphatic ring or fragrance such as cyclohexyl vinyl ether, 2-methylcyclohexylvinyl ether, cyclohexylmethylvinyl ether, benzylvinyl ether Monoalcohol vinyl ether having a group ring; glycerol monovinyl ether, 1,4-butanediol monovinyl ether, 1,4-butanediol divinyl ether, 1,6-hexanediol divinyl ether, neopentyl glycol divinyl ether, pentaerythritol divinyl ether , Pentaerytritor tetravinyl ether, trimethylolpropandivinyl ether, trimethylolpropanetrivinyl
  • the content of the photocurable component (C) is usually 0.1 to 300 parts by mass, preferably 0.5 to 100 parts by mass, and 1 to 50 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 5 to 30 parts by mass.
  • the pressure-sensitive adhesive composition of the present invention can contain a cross-linking agent (E).
  • a cross-linking agent (E) examples include an isocyanate-based cross-linking agent, an epoxy-based cross-linking agent, an aziridine-based cross-linking agent, a metal chelate-based cross-linking agent, and the like. 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 compounds for example, tolylene diisocyanate, xylylene diisocyanate diphenylmethane diisocyanate, naphthalenedi isocyanate, triphenylmethane triisocyanate, etc.
  • the cross-linking agent (E) is an adduct (adduct) of the isocyanate compound made of a polyhydric alcohol compound [for example, an adduct made of glycerol, trimethylolpropane, etc.], an isocyanurate, a burette-type compound, a polyether polyol, or a polyester. It may be a derivative such as a urethane prepolymer type isocyanate compound which has been subjected to an addition reaction with a polyol, an acrylic polyol, a polybutadiene polyol, a polyisoprene polyol or the like.
  • the cross-linking agent (B) can be used alone or in combination of two or more.
  • the cross-linking agent (B) is an aromatic isocyanate compound and / or an adduct of these polyhydric alcohol compounds or isocyanurates, it is advantageous for forming an optimum cross-linking density (or cross-linking structure).
  • the durability of the adhesive layer can be improved. In particular, when it is an adduct made of a tolylene diisocyanate compound and / or these polyhydric alcohol compounds, durability can be improved even when a pressure-sensitive adhesive layer is applied to a polarizing plate, for example.
  • the content of the cross-linking agent (E) is usually 0.01 to 15 parts by mass, preferably 0.05 to 10 parts by mass, and more preferably 0.1 parts by mass with respect to 100 parts by mass of the resin (A). ⁇ 5 parts by mass.
  • the pressure-sensitive adhesive composition of the present invention may further contain a silane compound (F).
  • the silane compound (F) include vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris (2-methoxyethoxy) silane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropyltriethoxysilane, and 3 -Glysidoxypropylmethyldimethoxysilane, 3-glycidoxypropylethoxydimethylsilane, 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, Examples thereof include 3-methacryloyloxypropyltrimethoxysilane and 3-mercaptopropyltrimethoxysilane.
  • the silane compound (D) may be a silicone oligomer. Specific examples of the
  • 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 , Vinyltriethoxysilane-tetramethoxysilane oligomer, vinyltriethoxy
  • the silane compound (F) may be a silane compound represented by the following formula (f1).
  • 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.
  • the alkanediyl group having 1 to 20 carbon atoms represented by A includes 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-heptanediyl group, 1,8-octanediyl group, 1,9-nonandyl group, 1,10-decandyl group, 1,12-dodecandyl group, 1,14-tetradecandyl group , 1,16-Hexadecanediyl group, 1,18-octadecanediyl 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.
  • the groups in which -CH 2-, which constitutes the alkanediyl group and the alicyclic hydrocarbon group, are replaced with -O- or -CO- include -CH 2 CH 2- O-CH 2 CH 2- , -CH.
  • Examples of the alkyl group having 1 to 5 carbon atoms represented by R 41 to R 45 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 45 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 (f1) examples include (trimethoxysilyl) methane, 1,2-bis (trimethoxysilyl) ethane, 1,2-bis (triethoxysilyl) ethane, and 1,3-.
  • (Trimethoxysilyl) hexane and 1,8-bis (trimethoxysilyl) octane are preferable.
  • the content of the silane compound (F) is usually 0.01 to 10 parts by mass, preferably 0.03 to 5 parts by mass, and more preferably 0.05 with respect to 100 parts by mass of the resin (A). It is about 2 parts by mass, more preferably 0.1 to 1 part by mass.
  • the pressure-sensitive adhesive composition may further contain an antistatic agent.
  • the antistatic agent include a surfactant, a siloxane compound, a conductive polymer, an ionic compound and the like, and an ionic compound is preferable.
  • the ionic compound include conventional ones.
  • the cation component constituting the ionic compound include organic cations and inorganic cations.
  • the organic cation include pyridinium cation, pyrrolidinium cation, piperidinium cation, imidazolium cation, ammonium cation, sulfonium cation, phosphonium cation and the like.
  • Examples of the inorganic cation include alkali metal cations such as lithium cation, potassium cation, sodium cation and cesium cation, and alkaline earth metal cations such as magnesium cation and calcium cation.
  • alkali metal cations such as lithium cation, potassium cation, sodium cation and cesium cation
  • alkaline earth metal cations such as magnesium cation and calcium cation.
  • alkali metal cations such as lithium cation, potassium cation, sodium cation and cesium cation
  • alkaline earth metal cations such as magnesium cation and calcium cation.
  • pyridinium cation, imidazolium cation, pyrrolidinium cation, lithium cation and potassium cation are preferable.
  • the anion component constituting the ionic compound may be either an inorganic anion or an organic anion, but an anion component containing a fluorine atom is prefer
  • anion component containing a fluorine atom examples include hexafluoroborate anion (PF 6- ), bis (trifluoromethanesulfonyl) imide anion [(CF 3 SO 2 ) 2 N-], and bis (fluorosulfonyl) imide anion [(FSO). 2 ) 2 N-], tetra (pentafluorophenyl) borate anion [(C 6 F 5 ) 4 B-] and the like.
  • PF 6- hexafluoroborate anion
  • bis (fluorosulfonyl) imide anion [(FSO). 2 ) 2 N-] examples of the anion component containing a fluorine atom.
  • bis (trifluoromethanesulfonyl) imide anion [(CF 3 SO 2 ) 2 N-], bis (fluorosulfonyl) imide anion [(FSO 2 ) 2 N-], tetra (pentafluorophenyl) borate anion [(C) 6 F 5 ) 4 B-] is preferable.
  • An ionic compound that is solid at room temperature is preferable in terms of the stability of the antistatic performance of the pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition over time.
  • the content of the antistatic agent is, for example, 0.01 to 20 parts by mass, preferably 0.1 to 10 parts by mass, and more preferably 1 to 7 parts by mass with respect to 100 parts by mass of the resin (A).
  • the pressure-sensitive adhesive composition may further contain one or more additives such as 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. it can.
  • additives such as 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.
  • 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 a specific example thereof is a release film that has undergone 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 satisfying the following formula (3), and more preferably a pressure-sensitive adhesive layer satisfying the formula (4).
  • a (405) ⁇ 0.5 (3) [In formula (3), A (405) represents the absorbance at a wavelength of 405 nm. ]
  • a (405) / A (440) ⁇ 5 (4) [In the formula (4), A (405) represents the absorbance at a wavelength of 405 nm, and A (440) represents the absorbance at a wavelength of 440 nm. ]
  • the value of A (405) is less than 0.5, the absorption at a wavelength of 405 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 400 nm is deteriorated. It is easy to happen.
  • the value of A (405) is preferably 0.6 or more, more preferably 0.8 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 (405) / A (440) represents the magnitude of absorption at a wavelength of 405 nm with respect to the magnitude of absorption at a wavelength of 440 nm, and the larger this value is, the more specific absorption is in the wavelength region near 405 nm.
  • the value of A (405) / A (440) is preferably 10 or more, more preferably 30 or more, further preferably 75 or more, and particularly preferably 100 or more.
  • the thickness of the pressure-sensitive adhesive layer of the present invention is usually 0.1 to 30 ⁇ m, preferably 0.5 to 25 ⁇ m, more preferably 1 to 15 ⁇ m, and particularly preferably 2.5 to 10 ⁇ m.
  • the thinner the pressure-sensitive adhesive layer the thinner the total thickness of the optical film and the optical laminate, which is particularly suitable for smartphones and tablets that require thinning.
  • 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 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 that has 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 degree of saponification 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 an aqueous boric acid solution, and 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 laminate 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, a water-based 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 with active energy rays such as ultraviolet rays and electron beams.
  • active energy rays such as ultraviolet rays and electron beams.
  • 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 bonding the polarizing film and the protective film include a method of subjecting at least one of these bonding surfaces to a surface activation treatment such as a saponification treatment, a corona treatment, or a plasma treatment.
  • a surface activation treatment such as a saponification treatment, a corona treatment, or a 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. Specifically, a film made of a polyolefin resin; a cellulosic resin; a polyester resin; a (meth) acrylic resin; or a mixture thereof, a copolymer, or the like is fried.
  • 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, the shrinkage of the polarizing film in a high temperature environment can be effectively suppressed 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 at least one surface of the polarizing film via an adhesive layer.
  • 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 photoelastic modulus 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 Co., Ltd., "Zero Tuck (registered trademark)” sold by Konica Minolta Opto Co., Ltd., and Zeon Japan Co., Ltd. Examples include “ZF-14” (trade name) sold by.
  • the retardation film is preferably a retardation film in which a liquid crystal compound is applied and oriented to develop optical anisotropy.
  • 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 liquid crystal alignment in-plane retardation value at a short wavelength is smaller than the liquid crystal alignment in-plane retardation value at a long wavelength, and the retardation film is preferably expressed by the following formula. (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). It is more preferable that 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.).
  • 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 retardation 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 the phase advance axis by 50 degrees, 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 + n y ) / 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 with tilted rod-shaped liquid crystal) sold by Nikko Nisseki Energy Co., Ltd., "WV film” (trade name; disc-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.
  • the optical film 10 with an adhesive layer shown in FIG. 1 has a release film (separate film) 2 on the adhesive layer surface 1 for temporary protection of the adhesive layer 1 surface formed from the adhesive composition of the present invention. Is in a state of being pasted.
  • the optical film 10A with an adhesive layer shown in FIG. 2 is an adhesive containing a protective film 3, an adhesive layer 4, a polarizing film 5, an adhesive layer 1 formed from the adhesive composition of the present invention, and a release film 2. It is a layered optical film.
  • 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 has an adhesive layer formed from a protective form 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 optical laminate 10C shown in FIG. 4 and the optical laminate 10D shown in FIG. 5 have a protective form 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 an adhesive layer 7, a retardation film 110, an adhesive layer 1a, and a light emitting element 30 (liquid crystal cell, organic EL cell).
  • 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 1/4 wavelength retardation layer 50 that imparts a retardation of 1/4 wavelength to the transmitted light An example includes a configuration including a retardation film 110 in which a 1/2 wavelength retardation layer 70 that imparts a phase difference of 1/2 wavelength to transmitted light is laminated via an adhesive layer or an adhesive layer 60.
  • a configuration including an optical film 40 in which a 1/4 wavelength retardation layer 50a and a positive C layer 80 are laminated via an adhesive layer or an adhesive layer 60 can be mentioned.
  • the 1/4 wavelength retardation layer 50 that imparts a phase difference of 1/4 wavelength in FIG. 4 and the 1/2 wavelength retardation layer 70 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 resin of the present invention, the pressure-sensitive adhesive composition containing the resin, and the optical laminate containing the pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition are laminated on a display element such as an organic EL element or a liquid crystal cell to be organic. It can be used for display devices (FPD: flat panel display) such as EL display devices and liquid crystal display devices.
  • FPD flat panel display
  • Synthesis Example 1 Synthesis of a photoselective absorbing compound (1) having a merocyanine structure and a polymerizable group in the molecule After replacing the inside of the 2000 mL four-necked flask equipped with a thermometer with a nitrogen atmosphere, 100 parts of 4-hydroxybutyl acrylate, 65 parts of cyanoacetic acid, 8.5 parts of 4-dimethylaminopyridine, 2,6-di-t- 7.7 parts of butyl-4-methylphenol and 500 parts of acetonitrile were charged and cooled to 0 ° C. to 10 ° C. with stirring. While maintaining the same temperature, 96 parts of N, N'-diisopropylcarbodiimide was added dropwise over 2 hours. After completion of the dropping, the obtained mixture was filtered to obtain 725 parts of an acetonitrile solution containing the compound represented by the formula (UVA-M-03).
  • UVA-M-01 the compound represented by the formula (UVA-M-01) synthesized with reference to JP-A-2014-194508, 71 parts of acetic anhydride, And 837 parts of acetonitrile were charged, and then 725 parts of an acetonitrile solution containing a compound represented by the formula (UVA-M-03) was charged. While stirring the obtained mixture, 90 parts of diisopropylethylamine was added dropwise to the obtained mixture over 2 hours.
  • ⁇ Gram absorption coefficient ⁇ measurement> A 2-butanone solution (0.006 g / L) of the compound represented by the formula (UVA-1) is placed in a 1 cm quartz cell, and the quartz cell is set in a spectrophotometer UV-2450 (manufactured by Shimadzu Corporation). The absorbance was measured in the wavelength range of 300 to 800 nm in 1 nm steps by the double beam method. The gram extinction coefficient for each wavelength was calculated from the obtained absorbance value, the concentration of the compound represented by the formula (UVA-1) in the solution, and the optical path length of the quartz cell.
  • ⁇ ( ⁇ ) A ( ⁇ ) / CL
  • ⁇ ( ⁇ ) represents the gram extinction coefficient (L / (g ⁇ cm)) of the resin (A) at the wavelength ⁇ nm
  • a ( ⁇ ) represents the absorbance at the wavelength ⁇ nm
  • C represents the concentration (g / cm). It represents L)
  • L represents the optical path length (cm) of the quartz cell.
  • the obtained compound represented by the formula (UVA-1) had ⁇ (405) of 45 L / (g ⁇ cm) and ⁇ (440) of 0 L / (g ⁇ cm).
  • the resulting mixture was held at 60 ° C. for 1 hour, then ethyl acetate was continuously added into the reaction vessel at an addition rate of 17.3 parts / hr while maintaining the internal temperature at 50-70 ° C. to increase the concentration of acrylic resin.
  • concentration reached 35%
  • the addition of ethyl acetate was stopped, and the temperature was kept at this temperature until 12 hours had passed from the start of the 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 1.48 million and Mw / Mn of 3.45 by GPC. This is referred to as resin (A-1).
  • the glass transition temperature by DSC was ⁇ 45 ° C.
  • the monomer composition of the obtained acrylic resin was 96% by mass of butyl acrylate, 3% by mass of 2-hydroxyethyl acrylate, and 1% by mass of acrylic acid.
  • Example 1 Preparation of the pressure-sensitive adhesive composition (1) In an ethyl acetate solution (resin concentration: 20%) of the resin (A-1) obtained above, with respect to 100 parts of the solid content of the solution.
  • Example 2 Preparation of pressure-sensitive adhesive composition (2)
  • the pressure-sensitive adhesive composition (2) was prepared in the same manner as in Example 1 except that the content of the photoradical generator was changed to the amount shown in Table 1. Prepared.
  • Example 3 Preparation of pressure-sensitive adhesive composition (3) A photocurable component (Shin Nakamura Chemical Industry Co., Ltd.) with respect to 100 parts of a solid content of an ethyl acetate solution (resin concentration: 20%) of the resin (A-1). Manufacture; The pressure-sensitive adhesive composition (3) was prepared in the same manner as in Example 1 except that 10 parts (trade name "A-DPH-12E") was added.
  • Examples 4 to 31 and Comparative Examples 1 and 2 Preparation of the pressure-sensitive adhesive composition (4) to the pressure-sensitive adhesive composition (33)
  • the resin (A) has a melanin structure and a polymerizable group in the molecule.
  • Tables 1 and 2 show the types and contents of the photoselective absorption compound (B), the photoinitiator (D), the photocurable component (C), the cross-linking agent (E), and the silane compound (F).
  • the pressure-sensitive adhesive composition (4) to the pressure-sensitive adhesive composition (33) were prepared in the same manner as in Example 1 except as described above.
  • BONASORB UA-3911 manufactured by Kagaku Kogyo Co., Ltd. 0.3 parts of cross-linking agent (manufactured by Toso; trade name “Coronate L", isocyanate-based compound, solid content 75%) and silane compound (manufactured by Shin-Etsu Chemical Industry: trade name KBM-3066 ”) 0.28 parts were mixed, and 2-butanone was further added so that the solid content concentration became 14% to obtain a pressure-sensitive adhesive composition (1).
  • the amount of the cross-linking agent (Coronate L) blended is the number of parts by mass as the active ingredient.
  • Resin (A-1) Acrylic resin (A-1) obtained in Polymerization Example 1.
  • Formula (UVA-1) Compound represented by the formula (UVA-1) obtained in Synthesis Example 1
  • NCI730 Manufactured by ADEKA Co., Ltd., trade name "NCI-730”
  • photoradical generator IrgTPO which is an oxime ester compound : BASF Japan Co., Ltd., trade name "Irgacure (registered trademark) TPO”
  • phosphine compound photoradical generator Irg184 BASF Japan Co., Ltd., trade name "Irgacure (registered trademark) TPO”
  • Photoradical generator NCI-831E manufactured by ADEKA Co., Ltd., trade name "NCI-831E", photoradical generator PBG3057, which is an oxime ester compound, manufactured by TRONLY Co., Ltd., trade name "PBG3057”, an oxime ester compound.
  • Photoradical generator A-DPH-12E Shin-Nakamura Chemical Industry Co., Ltd., trade name "A-DPH-12E", ethoxy or dipentaerythritol polyacrylate, hexafunctional (meth) acrylate compound
  • A-TMPT Shin-Nakamura Chemical Industry Co., Ltd.
  • the gel fraction in the pressure-sensitive adhesive layer of the present invention is a value measured according to the following (a) to (d).
  • the measurements were made according to the following (a) to (d), and the results are shown in Tables 3 and 4.
  • (A) An adhesive sheet having an area of about 8 cm ⁇ about 8 cm and a metal mesh (whose weight is Wm) made of SUS304 having an area of about 10 cm ⁇ about 10 cm are bonded together.
  • the higher the conversion rate value of the photoinitiator the less the unreacted photoinitiator remaining in the pressure-sensitive adhesive layer, which is advantageous in durability such as heat resistance and weather resistance.
  • the higher the conversion rate value of the light selective absorption compound the smaller the number of unreacted light selective absorption compounds, and the bleed resistance is further improved.
  • the bleed resistance is improved, there is no transferability of the light selective absorption compound to another layer, which is advantageous in suppressing the phase difference change.
  • ⁇ Measurement of absorbance of adhesive layer> Each of the obtained pressure-sensitive adhesive layers is bonded to glass, the separator 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 to obtain a COP film / adhesive.
  • a laminate having an agent layer / glass structure 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 absorbance of the prepared pressure-sensitive adhesive layer is shown in Tables 3 and 4. The absorbance of the glass and the absorbance of the COP film at a wavelength of 405 nm and a wavelength of 440 nm are both 0.
  • composition for forming a photo-alignment film Light by mixing 5 parts of a photo-alignment material having the following structure and 95 parts of cyclopentanone as components and stirring the obtained mixture at 80 ° C. for 1 hour. A composition for forming an alignment film was obtained.
  • the following photo-oriented materials were synthesized by the method described in JP2013-33248.
  • composition A Containing Polymerizable Liquid Liquid Compound A 12 parts of the polymerizable liquid crystal compound A having the following structure, a polyacrylate compound (leveling agent; BYK-361N manufactured by BYK-Chemie) 0.12 part, a polymerization initiator ( 0.72 parts of Irgacure 369 manufactured by Ciba Specialty Chemicals Co., Ltd. and 100 parts of cyclopentanone were mixed to obtain a composition containing a polymerizable liquid crystal compound.
  • a polyacrylate compound leveling agent; BYK-361N manufactured by BYK-Chemie
  • a polymerization initiator 0.72 parts of Irgacure 369 manufactured by Ciba Specialty Chemicals Co., Ltd.
  • 100 parts of cyclopentanone were mixed to obtain a composition containing a polymerizable liquid crystal compound.
  • the polymerizable liquid crystal compound A was synthesized by the method described in JP-A-2010-31223.
  • the maximum absorption wavelength ⁇ max (LC) of the polymerizable liquid crystal compound A was 350 nm.
  • a cycloolefin polymer film (ZF-14 manufactured by Nippon Zeon Co., Ltd.) has an output of 0.3 kW and a processing speed using a corona treatment device (AGF-B10, manufactured by Kasuga Electric Co., Ltd.). The treatment was performed once under the condition of 3 m / min.
  • the composition for forming a photoalignment film obtained in (iii) was coated on the corona-treated surface with a bar coater, dried at 80 ° C. for 1 minute, and subjected to a polarized UV irradiation device (SPOT CURE SP-7; Ushio Denki Co., Ltd.).
  • SPOT CURE SP-7 Ushio Denki Co., Ltd.
  • a polarized UV exposure was carried out with an integrated light intensity of 100 mJ / cm 2 .
  • the film thickness of the obtained alignment film was measured with an ellipsometer and found to be 100 nm.
  • a coating liquid composed of the composition A containing the polymerizable liquid crystal compound obtained in (iv) was applied onto the alignment film using a bar coater, dried at 120 ° C. for 1 minute, and then a high-pressure mercury lamp.
  • a bar coater dried at 120 ° C. for 1 minute, and then a high-pressure mercury lamp.
  • Ushio Denki Co., Ltd. is used to irradiate ultraviolet rays from the surface side coated with the composition containing the polymerizable liquid crystal compound (in a nitrogen atmosphere, integrated light amount at a wavelength of 313 nm: 500 mJ / cm 2).
  • the film thickness of the obtained optically anisotropic layer 1 was measured with a laser microscope and found to be 2 ⁇ m.
  • the pressure-sensitive adhesive layer (3) formed from the pressure-sensitive adhesive composition (3) obtained in Example 3 was attached to the cycloolefin resin film surface of the polarizing plate prepared in (ii) above, and the separator was peeled off. Further, the surface of the pressure-sensitive adhesive layer (3) from which the separator was peeled off and the surface of the optically anisotropic layer prepared in (V) opposite to the COP surface were bonded together to peel off the COP. An adhesive layer (A) with a separator was attached to the surface of the optically anisotropic layer from which the COP was peeled off to obtain an optical film (3).
  • the obtained evaluation optical film was cut into a size of 30 mm ⁇ 30 mm, the separator laminated on the adhesive layer (A) was peeled off, and this was made of non-alkali glass [trade name “EAGLE XG” manufactured by Corning Inc. ] And pasted together.
  • the phase difference value of the obtained optical film with glass at a wavelength of 450 nm was measured by a birefringence measuring device (KOBRA-WR; manufactured by Oji Measuring Instruments Co., Ltd.). Then, the optical laminate with glass was put into an oven at a temperature of 85 ° C. for 120 hours, taken out, left to stand in an environment of 23 ° C. and 50% for 24 hours, and then the phase difference value having a wavelength of 450 nm was measured again. The change value of the phase difference value before and after the durability test was calculated.
  • Phase difference change amount Phase difference change value before and after the durability test of the optical film (3) -Phase difference change value before and after the durability test of the evaluation optical film
  • the pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition of the present invention has good bleed resistance because the light-selective absorbing compound does not precipitate over time even after long-term storage. Further, the optical film containing the pressure-sensitive adhesive layer and the retardation film formed from the pressure-sensitive adhesive composition of the present invention has little phase difference change even after a heat resistance test (85 ° C. for 120 hours) and has good durability. Is shown. Since the pressure-sensitive adhesive layer of the present invention has good bleed resistance, the effect of the light selective absorption compound on the retardation film is small, so that the optical film of the present invention is expected to have good durability.
  • the retardation film is a retardation film containing an optically anisotropic layer (a film containing a cured film in the orientation state of the polymerizable liquid crystal compound)
  • the light selective absorption compound is precipitated, so that the polymerizable liquid crystal compound is formed. Since the orientation of the liquid crystal is disturbed and the amount of change in phase difference tends to be large, bleed resistance in the pressure-sensitive adhesive layer tends to be required. Therefore, the pressure-sensitive adhesive composition of the present invention having high bleed resistance performance is particularly useful for organic EL display devices, which often use a retardation film having an optically anisotropic layer.
  • the resin of the present invention, the pressure-sensitive adhesive composition containing the resin, and the optical laminate containing the pressure-sensitive adhesive layer formed from the initial 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, 10A, 10B, 10C, 10D Optical film with adhesive layer 3, 6 Protective film 4, 7 Adhesive layer 5 Polarized Film 8 Phase difference film 30 Light emitting element 40 Optical film 50, 50a 1/4 wavelength phase difference layer 60 Adhesive layer or adhesive layer 70 1/2 wavelength retardation layer 80 Positive C layer 100 Plate plate 110 Phase difference film

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Adhesive Tapes (AREA)
  • Polarising Elements (AREA)
  • Polymerisation Methods In General (AREA)
  • Graft Or Block Polymers (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

La présente invention concerne un film optique ayant une couche adhésive qui est obtenu par superposition d'une couche adhésive sur un film optique et qui présente une bonne résistance au saignement s'il est stocké pendant une longue période de temps. La présente invention concerne également une couche adhésive ayant une bonne résistance au saignement ; et une composition adhésive capable de former la couche adhésive.　La présente invention concerne une composition adhésive qui contient (A) une résine, (B) un composé d'absorption de lumière sélective ayant une structure de mérocyanine et un groupe polymérisable dans chaque molécule ainsi qu'un (D) photoinitiateur. La composition adhésive peut en outre contenir (C) un composant photodurcissable.
PCT/JP2020/012336 2019-03-28 2020-03-19 Composition adhésive WO2020196282A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
CN202080036527.3A CN113825811B (zh) 2019-03-28 2020-03-19 粘合剂组合物
KR1020217034662A KR20210145205A (ko) 2019-03-28 2020-03-19 점착제 조성물

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2019062574 2019-03-28
JP2019-062574 2019-03-28

Publications (1)

Publication Number Publication Date
WO2020196282A1 true WO2020196282A1 (fr) 2020-10-01

Family

ID=72608682

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2020/012336 WO2020196282A1 (fr) 2019-03-28 2020-03-19 Composition adhésive

Country Status (5)

Country Link
JP (1) JP7456224B2 (fr)
KR (1) KR20210145205A (fr)
CN (1) CN113825811B (fr)
TW (1) TWI826672B (fr)
WO (1) WO2020196282A1 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPWO2022149585A1 (fr) * 2021-01-08 2022-07-14
JPWO2022181725A1 (fr) * 2021-02-25 2022-09-01

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS61169831A (ja) * 1985-01-19 1986-07-31 アグフア‐ゲヴエルト・アクチエンゲゼルシヤフト 感光性安定化写真記録材料
JP2002053824A (ja) * 2000-06-02 2002-02-19 Fuji Photo Film Co Ltd 紫外線吸収粘着フイルム
JP2006002069A (ja) * 2004-06-18 2006-01-05 Hayashibara Biochem Lab Inc メロシアニン色素共重合体及びその用途
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
WO2019004043A1 (fr) * 2017-06-27 2019-01-03 住友化学株式会社 Feuille adhésive et film ayant une couche adhésive

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2011068780A (ja) 2009-09-25 2011-04-07 Nippon Shokubai Co Ltd 近赤外線吸収粘着剤組成物
JP2016204406A (ja) * 2015-04-15 2016-12-08 藤森工業株式会社 粘着剤層及び粘着フィルム
JP2017165941A (ja) 2015-12-25 2017-09-21 日東電工株式会社 有機ｅｌ表示装置用粘着剤組成物、有機ｅｌ表示装置用粘着剤層、有機ｅｌ表示装置用粘着剤層付き偏光フィルム、及び有機ｅｌ表示装置
WO2019004042A1 (fr) * 2017-06-27 2019-01-03 住友化学株式会社 Film optique
CN111201252A (zh) 2017-10-13 2020-05-26 住友化学株式会社 树脂和粘合剂组合物

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS61169831A (ja) * 1985-01-19 1986-07-31 アグフア‐ゲヴエルト・アクチエンゲゼルシヤフト 感光性安定化写真記録材料
JP2002053824A (ja) * 2000-06-02 2002-02-19 Fuji Photo Film Co Ltd 紫外線吸収粘着フイルム
JP2006002069A (ja) * 2004-06-18 2006-01-05 Hayashibara Biochem Lab Inc メロシアニン色素共重合体及びその用途
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
WO2019004043A1 (fr) * 2017-06-27 2019-01-03 住友化学株式会社 Feuille adhésive et film ayant une couche adhésive

Also Published As

Publication number Publication date
CN113825811A (zh) 2021-12-21
JP7456224B2 (ja) 2024-03-27
JP2020164835A (ja) 2020-10-08
KR20210145205A (ko) 2021-12-01
CN113825811B (zh) 2024-01-05
TWI826672B (zh) 2023-12-21
TW202102635A (zh) 2021-01-16

Similar Documents

Publication Publication Date Title
WO2019073869A1 (fr) Résine et composition adhésive
JP7182913B2 (ja) 粘着剤シート及び粘着剤層付フィルム
WO2020196282A1 (fr) Composition adhésive
CN112566949B (zh) 树脂及粘合剂组合物
JP2021006891A (ja) 光学層及び該光学層を含む積層体
WO2021070800A1 (fr) Composition d'adhésif
WO2021070799A1 (fr) Composition d'adhésif
WO2020196284A1 (fr) Composition adhésive
WO2021132235A1 (fr) Composition adhésive
WO2021070801A1 (fr) Composition d'adhésif
KR102603487B1 (ko) 광학 필름
TWI844515B (zh) 光學膜

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 20778074

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

ENP Entry into the national phase

Ref document number: 20217034662

Country of ref document: KR

Kind code of ref document: A

122 Ep: pct application non-entry in european phase

Ref document number: 20778074

Country of ref document: EP

Kind code of ref document: A1