WO2022209476A1 - Adhésif pour dispositif d'affichage et feuille adhésive l'utilisant - Google Patents

Adhésif pour dispositif d'affichage et feuille adhésive l'utilisant Download PDF

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Publication number
WO2022209476A1
WO2022209476A1 PCT/JP2022/007748 JP2022007748W WO2022209476A1 WO 2022209476 A1 WO2022209476 A1 WO 2022209476A1 JP 2022007748 W JP2022007748 W JP 2022007748W WO 2022209476 A1 WO2022209476 A1 WO 2022209476A1
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Prior art keywords
group
adhesive
ultraviolet absorber
pressure
sensitive adhesive
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PCT/JP2022/007748
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English (en)
Japanese (ja)
Inventor
敦史 山井
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株式会社巴川製紙所
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Application filed by 株式会社巴川製紙所 filed Critical 株式会社巴川製紙所
Priority to JP2023510669A priority Critical patent/JPWO2022209476A1/ja
Priority to KR1020237036696A priority patent/KR20230163480A/ko
Priority to CN202280011521.XA priority patent/CN116888232A/zh
Publication of WO2022209476A1 publication Critical patent/WO2022209476A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C09J11/06—Non-macromolecular additives organic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
    • C09J7/38—Pressure-sensitive adhesives [PSA]
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • 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 an adhesive for display devices and an adhesive sheet using the same.
  • Display devices such as liquid crystal displays and organic EL displays are constructed by laminating various functional films. In recent years, these display devices have been used for various purposes, and films having various functions are attached on the surface of the liquid crystal cell, the surface of the organic EL panel, or the outermost surface of the display screen according to the purpose. is used in
  • a retardation plate on the surface of the liquid crystal display and in an organic EL display, various functional films such as a polarizing plate on the surface of the organic EL panel are laminated and used.
  • These films are laminated and attached using an adhesive, and when used outdoors, they are used in high temperature or high temperature and high humidity environments. In particular, light resistance against ultraviolet rays) is required.
  • Patent Document 1 discloses a resin member using an ultraviolet absorber that efficiently absorbs light in the wavelength range of 350 to 390 nm.
  • Patent Document 1 may cause precipitation and peeling of the ultraviolet absorber in a high temperature environment or a high temperature and high humidity environment, and the resin member is used for absorption on the long wavelength side. was difficult to do.
  • the present invention has been made in view of the above-described problems, and has an electromagnetic wave absorbing power on the longer wavelength side of about 405 nm, thereby suppressing deterioration of the display device due to electromagnetic waves.
  • An object of the present invention is to provide a pressure-sensitive adhesive sheet using an agent.
  • a certain aspect of the present invention is an adhesive for a display device.
  • the adhesive for a display device contains an acrylic copolymer, an ultraviolet absorber (A), and an ultraviolet absorber (B), and the ultraviolet absorber (A) is 2-phenylbenzo It is a triazole derivative, the ultraviolet absorber (B) is liquid at room temperature, and the content (parts by mass) of the ultraviolet absorber (B) is the content (parts by mass) of the ultraviolet absorber (A). 1 to 10 times.
  • the pressure-sensitive adhesive for a display device of the above-described aspect may have a 405 nm transmittance of 1% or less measured under the following conditions.
  • a pressure-sensitive adhesive layer having a thickness of 100 ⁇ m is produced using the pressure-sensitive adhesive for display device according to any one of the aspects described above.
  • the transmittance at 405 nm of the pressure-sensitive adhesive layer is measured using a spectrophotometer.
  • the pressure-sensitive adhesive for display device of the above-described aspect may have a haze increase value ⁇ H of 3% or less calculated under the following conditions.
  • a pressure-sensitive adhesive layer having a thickness of 100 ⁇ m is produced using the pressure-sensitive adhesive for display device according to any one of the aspects described above.
  • (2) Laminating a PET film with a thickness of 100 ⁇ m on one main surface of the adhesive layer, laminating soda glass with a thickness of 1.8 mm on the other main surface of the adhesive layer, and forming the adhesive layer A laminate comprising: (3) Measure the haze value H0 (%) of the laminate immediately after the laminate is produced. (4) Measure the haze value H1 (%) of the laminate after 1000 hours at 85° C. and 85% RH. (5) Haze increase value ⁇ H (%) is calculated using the following formula. ⁇ H H1 - H0
  • the pressure-sensitive adhesive sheet includes a substrate and the display device pressure-sensitive adhesive according to any one of the aspects described above laminated on at least one main surface of the substrate.
  • a pressure-sensitive adhesive for a display device and a pressure-sensitive adhesive sheet using the pressure-sensitive adhesive for a display device can suppress deterioration of a display device due to electromagnetic waves by having an electromagnetic wave absorption power up to a longer wavelength side of about 405 nm.
  • the notation “a to b" in the description of numerical ranges means from a to b, unless otherwise specified.
  • the term “acryl” includes “methacrylic”
  • the term “acrylate” includes “methacrylate”.
  • the expression that the composition does not contain a certain component means that the content of a certain component in the composition is the amount that is unavoidably present or less.
  • the display device adhesive according to this embodiment contains an acrylic copolymer, an ultraviolet absorber (A), and an ultraviolet absorber (B).
  • A an ultraviolet absorber
  • B an ultraviolet absorber
  • acrylic copolymer An acrylic copolymer can be obtained by copolymerizing a monomer composition containing an acrylic monomer.
  • the monomer composition according to this embodiment is not particularly limited, but more preferably contains ethyl acrylate and 2-ethylhexyl acrylate.
  • acrylic monomers contained in the monomer composition are not particularly limited as long as they do not impair the effects of the present invention, and may include known monomers.
  • monomers include methyl acrylate, n-butyl acrylate, i-butyl acrylate, n-octyl acrylate, i-octyl acrylate, n-nonyl acrylate, i-nonyl acrylate, n-decyl acrylate, n-dodecyl acrylate, stearyl linear or branched alkyl esters of acrylic acid such as acrylates; Linear or branched alkyl acrylic monomers of methacrylic acid such as methyl methacrylate, ethyl methacrylate, n-butyl methacrylate, n-dodecyl methacrylate, stearyl methacrylate; 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, 3-hydroxypropyl
  • monomers other than acrylic monomers copolymerizable with acrylic monomers can also be included.
  • Monomers other than acrylic monomers are not particularly limited as long as they do not inhibit the effects of the present invention, and examples include N-vinylpyrrolidone, N-vinylcaprolactam, N-vinylacetamide, acrylonitrile, styrene, and vinyl acetate. can. These can be used singly or in combination.
  • An acrylic copolymer can be obtained by radically reacting a monomer composition in the presence of a polymerization initiator.
  • the method of the radical reaction is not particularly limited, and examples thereof include living radical polymerization and free radical polymerization. According to living radical polymerization, a copolymer having a more uniform molecular weight and composition can be obtained as compared with free radical polymerization, the generation of low molecular weight components can be suppressed, and the cohesive force of the pressure-sensitive adhesive layer can be increased. can do.
  • the polymerization method is not particularly limited, and conventionally known methods can be used. Examples thereof include solution polymerization (boiling point polymerization or constant temperature polymerization), emulsion polymerization, suspension polymerization, bulk polymerization and the like. Among them, solution polymerization is preferable because of its simple synthesis.
  • ethyl acetate, toluene, methyl ethyl ketone, methyl sulfoxide, ethanol, acetone, diethyl ether, etc. can be used as the reaction solvent. These can be used singly or in combination.
  • the polymerization initiator is not particularly limited as long as it does not impair the effects of the present invention, and for example, organic peroxides, azo compounds and the like can be used.
  • Organic peroxides include 1,1-bis(t-hexylperoxy)-3,3,5-trimethylcyclohexane, t-hexylperoxypivalate, t-butylperoxypivalate, 2,5-dimethyl -2,5-bis(2-ethylhexanoylperoxy)hexane, t-hexylperoxy-2-ethylhexanoate, t-butylperoxy-2-ethylhexanoate, t-butylperoxyisobutyl rate, t-butylperoxy-3,5,5-trimethylhexanoate, t-butylperoxylaurate and the like.
  • azo compounds include azobisisobutyronitrile and azobiscyclohex
  • examples of polymerization initiators include organic tellurium polymerization initiators.
  • the organic tellurium polymerization initiator is not particularly limited as long as it does not impair the effects of the present invention, and those generally used for living radical polymerization can be used. Examples include organic tellurium compounds and organic telluride compounds. be able to.
  • an azo compound can be used as a polymerization initiator in addition to the organic tellurium polymerization initiator for the purpose of accelerating the polymerization rate.
  • the acrylic copolymer can be further crosslinked using a crosslinking agent for the purpose of moderately adjusting the gel fraction.
  • the cross-linking agent is not particularly limited as long as it does not impair the effects of the present invention. These can be used singly or in combination. Among these, the isocyanate-based cross-linking agent has suitable reactivity and is preferable from the viewpoint of productivity.
  • the isocyanate-based cross-linking agent is not particularly limited as long as it does not impede the effects of the present invention.
  • Aromatic polyisocyanates such as; hexamethylene diisocyanate, isophorone diisocyanate, aliphatic polyisocyanates such as dicyclohexamethane diisocyanate; cyclohexane 1,4-diisocyanate, isophorone diisocyanate (IPDI), hydrogenated xylylene diisocyanate, hydrogenated bis(isocyanate alicyclic polyisocyanates such as natophenyl)methane and bicycloheptane triisocyanate; isocyanurate compounds; buret type compounds; These can be used singly or in combination. It is preferable to contain an isocyanurate compound in terms of making the pressure-sensitive adhesive higher in hardness and imparting further excellent heat resistance and heat and humidity resistance. This makes it possible to obtain a pressure-sensitive adhesive that is
  • the weight average molecular weight of the acrylic copolymer is not particularly limited as long as it does not impair the effects of the present invention, but is, for example, 300,000 to 2,000,000, preferably 400,000 to 1,500,000.
  • the weight-average molecular weight is in the range, the hardness, heat resistance, and heat and humidity resistance of the pressure-sensitive adhesive are good. This makes it possible to obtain a pressure-sensitive adhesive that is less likely to swell or peel off.
  • a known measurement method can be used, for example, a method in accordance with JIS K7252-1:2008 "Plastics - Determining the average molecular weight and molecular weight distribution of a polymer by size exclusion chromatography". can be measured by
  • the glass transition temperature (hereinafter referred to as Tg) of the acrylic copolymer can be -50°C to -10°C, preferably -40°C to -15°C, and more preferably -35°C to -20°C.
  • Tg glass transition temperature
  • the pressure-sensitive adhesive can be made to have higher hardness, and the adhesiveness to the outermost surface of the display device can be increased. This makes it possible to obtain a pressure-sensitive adhesive that is less likely to swell or peel off.
  • a known measuring method can be used for measuring Tg, for example, it can be measured by a method conforming to JIS K7121-1987 "Method for measuring transition temperature of plastics".
  • a monomer solution is prepared by mixing raw material monomers and an organic solvent such as toluene or ethyl acetate. Place the monomer solution in a sealed container and heat to a predetermined temperature (eg, 40° C. to 90° C.) with nitrogen sparge and stirring. A predetermined polymerization initiator is added dropwise to a predetermined monomer solution, and heating and stirring are continued until the reaction is completed to obtain an acrylic copolymer (solution). At this time, the weight average molecular weight can be adjusted by adjusting the type of solvent, heating temperature, and the like.
  • the blending amount of ethyl acrylate in the raw material monomer composition can be 25% by mass to 60% by mass when the total monomer components in the monomer solution are 100% by mass.
  • the blending amount of 2-ethylhexyl acrylate in the raw material monomer composition can be 10% by mass to 40% by mass when the total monomer components in the monomer solution are 100% by mass.
  • the amount of monomers other than ethyl acrylate and 2-ethylhexyl acrylate in the raw material monomer composition can be 40% by mass to 90% by mass when the total monomer components in the monomer solution are 100% by mass.
  • the amount of the monomer to be blended can be freely adjusted according to the desired glass transition temperature, hardness, etc. of the hard acrylic copolymer (or adhesive).
  • the ultraviolet absorber (A) contained in the adhesive for display device of the present embodiment is a 2-phenylbenzotriazole derivative having a thioaryl ring group (hereinafter simply referred to as "2-phenylbenzotriazole derivative”), It is represented by the following formula (1).
  • the 2-phenylbenzotriazole derivative is a powdery solid at normal temperature (25° C.).
  • R 1 to R 9 are each independently selected from a hydrogen atom, a halogen atom, a hydrocarbon group, an aromatic group, an unsaturated group, an oxygen atom-containing group, a phosphorus atom-containing group and a sulfur atom-containing group. It is an atom or group corresponding to at least one selected, and at least one of R 1 to R 9 is a thioaryl ring group.
  • halogen atoms include fluorine, chlorine, bromine and iodine atoms.
  • a hydrocarbon group is a group composed of carbon atoms and hydrogen atoms.
  • the hydrocarbon groups may be aliphatic or aromatic groups and may have unsaturated groups such as carbon-carbon double bonds. Since the aromatic group, which is a hydrocarbon group, will be described later, the aliphatic group will be described here.
  • Aliphatic groups may be acyclic or cyclic and are, for example, straight-chain or branched alkyl, alkenyl or alkynyl groups and, for example, hydrogen atoms substituted by alkyl groups. cycloalkyl or cycloalkenyl groups.
  • cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl groups.
  • the number of carbon atoms in the hydrocarbon group is preferably 1-20, more preferably 1-18, even more preferably 1-10, and particularly preferably 4-9.
  • Preferred examples of hydrocarbon groups include linear or branched alkyl groups having 1 to 20, 1 to 9, further 4 to 9 or 1 to 3 carbon atoms, especially branched having 4 to 9 carbon atoms.
  • Alkyl groups and cyclic alkyl groups having 3 to 10 carbon atoms, further 3 to 8 carbon atoms are included.
  • the linear or branched alkyl group is not particularly limited, and examples thereof include methyl group, benzyl group, ⁇ , ⁇ -dimethylbenzyl group, ethane-1-yl group, propan-1-yl group, 1-methylethane- 1-yl group, butan-1-yl group, butan-2-yl group, 2-methylpropan-1-yl group, 2-methylpropan-2-yl group, pentane-1-yl group, pentane-2- yl group, hexan-1-yl group, heptane-1-yl group, octan-1-yl group, 1,1,3,3-tetramethylbutan-1-yl group, nonan-1-yl group, decane- 1-yl group, undecane-1-yl group, dodecane-1-yl group, tridecane-1-yl group, tetradecane-1-yl group, pentadecane-1-yl group, hexadecane
  • Linear or branched alkenyl groups include, for example, vinyl group, prop-1-en-1-yl group, allyl group, isopropenyl group, but-1-en-1-yl group, but-2-en- 1-yl group, but-3-en-1-yl group, 2-methylprop-2-en-1-yl group, 1-methylprop-2-en-1-yl group, pent-1-en-1- yl group, pent-2-en-1-yl group, pent-3-en-1-yl group, pent-4-en-1-yl group, 3-methylbut-2-en-1-yl group, 3 -methylbut-3-en-1-yl group, hex-1-en-1-yl group, hex-2-en-1-yl group, hex-3-en-1-yl group, hex-4-ene -1-yl group, hex-5-en-1-yl group, 4-methylpent-3-en-1-yl group, 4-methylpent-3-en-1-yl group
  • Linear or branched alkynyl groups include, for example, ethynyl, prop-1-yn-1-yl group, prop-2-yn-1-yl group, but-1-yn-1-yl group, but-3 -yn-1-yl group, 1-methylprop-2-yn-1-yl group, pent-1-yn-1-yl group, pent-4-yn-1-yl group, hex-1-yn-1 -yl group, hex-5-yn-1-yl group, hept-1-yn-1-yl group, hept-6-yn-1-yl group, octa-1-yn-1-yl group, octa- 7-yn-1-yl group, non-1-yn-1-yl group, non-8-yn-1-yl group, deca-1-yn-1-yl group, deca-9-yn-1- yl group, undec-1-yn-1-yl group, undec-10-
  • Examples of preferred cyclic alkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl groups.
  • the aromatic group is a monocyclic aromatic group or polycyclic aromatic group containing an aromatic ring such as a benzene ring, naphthalene ring, or anthracene ring.
  • the aromatic group may contain a heteroatom and may have a substituent.
  • the number of carbon atoms in the aromatic group is preferably 6-18, more preferably 6-14.
  • aromatic groups include phenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 3,4-dimethyl phenyl group, 3,5-dimethylphenyl group, 2,4,5-trimethylphenyl group, 2,4,6-trimethylphenyl group, 4-biphenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthracenyl group , 2-anthracenyl group, 9-anthracenyl group, 2-methoxyphenyl group, 3-methoxyphenyl group, 4-methoxyphenyl group, 2-ethoxyphenyl group, 3-ethoxyphenyl group, 4-ethoxyphenyl group, 2-chlorophenyl groups, 2-fluorophenyl groups and 4-fluorophenyl groups.
  • An unsaturated group is a group containing an unsaturated bond.
  • Unsaturated bonds are carbon-carbon unsaturated bonds or carbon-heteroatoms such as carbon-carbon double bonds, carbon-carbon triple bonds, carbon-oxygen double bonds, carbon-nitrogen double bonds, carbon-nitrogen triple bonds. It is an unsaturated bond.
  • the carbon-oxygen double bond may be contained in a carbonyl group, an aldehyde group, a carboxyl group or the like
  • the carbon-nitrogen double bond may be contained in an isocyanate group or the like
  • the carbon-nitrogen triple bond may be included in a cyano group, a cyanato group, or the like.
  • the total number of carbon atoms and heteroatoms contained in the unsaturated group is preferably 1-10, more preferably 1-8.
  • unsaturated groups include acryloyl, methacryloyl, maleic monoester, styryl, allyl, vinyl, amide, carbamoyl, cyano and isocyanate groups.
  • An oxygen atom-containing group is a group containing an oxygen atom.
  • Oxygen atom-containing groups usually contain carbon atoms and/or hydrogen atoms along with oxygen atoms.
  • the number of carbon atoms contained in the oxygen atom-containing group is 6 to 20, especially 6 to 12 when it contains an aromatic ring group and/or an alicyclic group, and when it does not contain an aromatic ring group and an alicyclic group 0 to 20, more preferably 0 to 12, especially 0 to 6.
  • oxygen-containing groups include hydroxy, alkoxy, acetoxy, acetyl, aldehyde, carboxy, carbamoyl, urethane, amide, imide, urea, ether, carbonyl, and ester groups.
  • alkoxy groups include methoxy, ethoxy, propoxy, butoxy, phenoxy, methylphenoxy, dimethylphenoxy, naphthoxy, phenylmethoxy and phenylethoxy groups.
  • preferred oxygen atom-containing groups include a hydroxy group, an alkoxy group having 1 to 18 carbon atoms, an ether group having 1 to 18 carbon atoms, an ester group having 1 to 18 carbon atoms, and a polyoxyethylene group having 1 to 20 carbon atoms. is included.
  • a phosphorus atom-containing group is a group containing a phosphorus atom.
  • Phosphorus atom-containing groups typically contain carbon and/or hydrogen atoms along with the phosphorus atom.
  • the number of carbon atoms contained in the phosphorus atom-containing group is 6 to 20, particularly 6 to 12 when it contains an aromatic ring group and/or an alicyclic group, and when it does not contain an aromatic ring group and an alicyclic group 0 to 20, more preferably 0 to 12, especially 0 to 6.
  • Examples of phosphorus atom-containing groups include phosphine groups, phosphite groups, phosphonic acid groups, phosphinic acid groups, trimethylphosphine groups, tributylphosphine groups, tricyclohexylphosphine groups, triphenylphosphine groups, tritolylphosphine groups, methylphosphite groups. groups, ethylphosphite groups, phenylphosphite groups, phosphonic acid groups, phosphinic acid groups, phosphate groups and phosphate ester groups.
  • a sulfur atom-containing group is a group containing a sulfur atom.
  • Sulfur-containing groups generally contain carbon and/or hydrogen atoms along with sulfur atoms.
  • the number of carbon atoms contained in the sulfur atom-containing group is 6 to 20, further 6 to 12, particularly 6 to 10 when it contains an aromatic ring group and/or an alicyclic group, and an aromatic ring group and/or an alicyclic group.
  • sulfur atom-containing groups include 0 to 20, more preferably 0 to 12, particularly 0 to 10, particularly preferably 0 to 6 when not containing a group, thiol group, sulfide group, disulfide group, sulfonyl group, sulfo thiocarbonyl, thiocarbamoyl, thiourea, thioalkoxy, thiocarboxy, thiophene and thiazole groups.
  • the thioaryl ring group may have a hydrogen atom substituent, and the substituent includes an alkyl group having 4 to 9 carbon atoms.
  • the alkyl group may be a linear alkyl group or a branched chain alkyl group.
  • Aryl rings contained in the thioaryl ring group include a benzene ring and/or a naphthalene ring.
  • examples of the ultraviolet absorber (A) include 2-phenylbenzotriazole derivatives represented by the following chemical formulas.
  • 2-phenylbenzotriazole derivatives represented by the following chemical formulas are preferable in order to enhance the long-wavelength (405 nm) electromagnetic wave absorption effect.
  • the lower limit of the content of the ultraviolet absorber (A) is preferably 0.5 parts by mass or more, more preferably 1 part by mass or more, and still more preferably 2 parts by mass with respect to 100 parts by mass of the acrylic copolymer. Part by mass or more.
  • the upper limit of the content of the ultraviolet absorber (A) is preferably 10 parts by mass or less, more preferably 8 parts by mass or less, and still more preferably 5 parts by mass with respect to 100 parts by mass of the acrylic copolymer. Part by mass or less.
  • the long wavelength (405 nm) The electromagnetic wave absorption power of the can be made sufficient.
  • the ultraviolet absorber (B) contained in the pressure-sensitive adhesive for a display device of the present embodiment is liquid at room temperature (25° C.), and the above-mentioned ultraviolet absorber (A) (2-phenylbenzotriazole derivative having a thioaryl ring group ). Benzotriazole derivatives and/or triazine derivatives are preferable as the ultraviolet absorber (B).
  • Benzotriazole derivatives include 2-(5-methyl-2-hydroxyphenyl)benzotriazole, 2-(2-hydroxy-5-t-butylphenyl)-2H-benzotriazole, octyl-3[3-tert-butyl- 4-hydroxy-5-(5-chloro-2H-benzotriazol-2-yl)phenyl]propionate and 2-ethylhexyl-3-[3-tert-butyl-4-hydroxy-5-(5-chloro-2H- A mixture of benzotriazol-2-yl)phenyl]propionates, 2-[2-hydroxy-3,5-bis( ⁇ , ⁇ -dimethylbenzyl)phenyl]-2H-benzotriazole, 2-(3-tbutyl-5 -methyl-2-hydroxyphenyl)-5-chlorobenzotriazole, 2-(3,5-di-t-amyl-2-hydroxyphenyl)benzotriazole, 2-(2'-hydroxy-5'-
  • Triazine derivatives include 2-[4,6-di(2,4-xylyl)-1,3,5-triazin-2-yl]-5-octyloxyphenol, 2-[4,6-bis(2 ,4-dimethylphenyl)-1,3,5-triazin-2-yl]-5-[3-(dodecyloxy)-2-hydroxypropoxy]phenol, 2-(2,4-dihydroxyphenyl)-4, Reaction product of 6-bis(2,4-dimethylphenyl)-1,3,5-triazine and (2-ethylhexyl-glycidate ester, 2,4-bis "2-hydroxy-4-butoxyphenyl"-6 -(2,4-dibutoxyphenyl)-1,3-5-triazine and the like.
  • KEMISORB 102 manufactured by Chemipro Kasei Co., Ltd., "TINUVIN 400", “TINUVIN 405", “TINUVIN 460”, “TINUVIN 477”, “TINUVIN 479”, "TINUVIN 1577” manufactured by BASF, and "TINUVIN 1577” manufactured by ADEKA “ADEKA STAB LA-46", “ADEKA STAB LA-F70”, “CYASORBUV-1164” manufactured by Sun Chemical Co., Ltd., and the like.
  • Tinuvin109 and Tinuvin477 are preferable in terms of enhancing the long-wavelength (405 nm) electromagnetic wave absorption effect.
  • the pressure-sensitive adhesive for display device of the present embodiment can enhance the compatibility with the acrylic copolymer by using both the ultraviolet absorber (A) and the ultraviolet absorber (B). As a result, it is possible to prevent precipitation of the ultraviolet absorber, improve durability and light resistance in a high-temperature environment or a high-temperature and high-humidity environment, and exhibit long-wavelength (405 nm) electromagnetic wave absorption.
  • the lower limit of the content of the ultraviolet absorber (B) is 1 time or more, preferably 2 times or more, more preferably 3 times or more, and 4 times or more with respect to the content of the ultraviolet absorber (A). More preferred.
  • the upper limit of the ultraviolet absorber (B) is 10 times or less, preferably 8 times or less, more preferably 6 times or less, with respect to the content of the ultraviolet absorber (A).
  • crosslinking agent When producing a pressure-sensitive adhesive from the obtained acrylic copolymer, it is preferable to add a cross-linking agent as necessary for the formation of the pressure-sensitive adhesive.
  • the type of cross-linking agent is not particularly limited as long as it does not impair the effects of the present invention, and conventionally known agents can be used in a conventional manner.
  • the amount of the cross-linking agent added is preferably 0.1 to 10 parts by mass, more preferably 0.3 to 5 parts by mass, and 0.5 parts by mass when the acrylic copolymer is 100 parts by mass. parts to 3 parts by mass are more preferable.
  • the pressure-sensitive adhesive for display devices of the present embodiment can contain other components.
  • Other components are not particularly limited as long as they do not inhibit the effects of the present invention.
  • Various additives commonly used in the field of pressure-sensitive adhesive compositions such as ultraviolet absorbers, antioxidants, light stabilizers, and surfactants, may be contained.
  • ultraviolet absorbers such as ultraviolet absorbers, antioxidants, light stabilizers, and surfactants
  • conventionally known ones can be used in a conventional manner, and since they do not particularly characterize the present invention, detailed description thereof will be omitted.
  • the pressure-sensitive adhesive for display device of the present embodiment preferably has a 405 nm transmittance of 1% or less measured under the following conditions.
  • An adhesive layer having a thickness of 100 ⁇ m is produced using the adhesive for a display device of the present embodiment.
  • the transmittance at 405 nm of the pressure-sensitive adhesive layer is measured using a spectrophotometer. When the 405 nm transmittance is 1% or less, the long wavelength (405 nm) electromagnetic wave absorbing power can be made more sufficient.
  • the pressure-sensitive adhesive for display device of the present embodiment preferably has a haze increase value ⁇ H of 3% or less calculated under the following conditions.
  • An adhesive layer having a thickness of 100 ⁇ m is produced using the adhesive for a display device of the present embodiment.
  • a PET film having a thickness of 100 ⁇ m is laminated on one main surface of the pressure-sensitive adhesive for a display device of the present embodiment, and a soda glass having a thickness of 1.8 mm is laminated on the other main surface of the pressure-sensitive adhesive layer, A laminate including the pressure-sensitive adhesive layer is produced.
  • Measure the haze value H0 of the laminate immediately after the laminate is produced.
  • the pressure-sensitive adhesive for display devices can be used for lamination of a polarizing plate and a retardation plate on the surface of a liquid crystal cell in a liquid crystal display, and a polarizing plate on the surface of an organic EL panel in an organic EL display. It can also be used as an adhesive for anti-scattering films and anti-reflection films used on the outermost surface of the display screen of a display device.
  • the pressure-sensitive adhesive sheet of the present embodiment includes a substrate and the above-described display device pressure-sensitive adhesive laminated on at least one main surface of the substrate. More specifically, the pressure-sensitive adhesive sheet of the present embodiment includes a single-sided pressure-sensitive adhesive sheet in which an adhesive for display devices is laminated on one main surface of a substrate, and a double-sided pressure-sensitive adhesive sheet in which pressure-sensitive adhesives for display devices are laminated on both main surfaces of a substrate. It includes a pressure-sensitive adhesive sheet and a double-sided pressure-sensitive adhesive sheet obtained by laminating a pressure-sensitive adhesive for display devices on one main surface of a substrate and a known pressure-sensitive adhesive (for example, an acrylic pressure-sensitive adhesive) on the other main surface of the substrate.
  • the adhesive sheet of the present embodiment may be in the form of strip-shaped adhesive tape.
  • the adhesive for display devices When the adhesive for display devices is used as an adhesive sheet, the adhesive for display devices can be applied onto a base material and laminated. By heating the laminated sheet to evaporate the organic solvent, the adhesive sheet can be formed. When a cross-linking agent is added, a mixture of the acrylic copolymer and the cross-linking agent is applied before coating and heated to complete the cross-linking reaction.
  • the heating conditions can be freely selected according to the type of cross-linking agent and the type and concentration of the organic solvent used.
  • Examples of methods for forming the adhesive into a sheet include comma coaters, blade coaters, lip coaters, rod coaters, squeeze coaters, reverse coaters, transfer roll coaters, gravure coaters, spray coaters, screen printing methods, curtain coating methods, Spray coating method, roll coating method, etc. may be mentioned, and the surface of the layer to be laminated may be directly coated, or the surface of a release sheet or the like may be coated in a sheet form, and then transferred to the surface of the layer to be laminated.
  • a method of lamination can be mentioned.
  • the base material is not particularly limited as long as it does not interfere with the effects of the present invention.
  • a polarizing plate, a film containing a hard code layer (anti-scattering film), an antireflection film, etc. can be used.
  • the thickness of the substrate is not particularly limited, it can be, for example, 10 ⁇ m to 200 ⁇ m, more preferably 25 ⁇ m to 100 ⁇ m.
  • the thickness of the display device adhesive is not particularly limited, but can be, for example, 1 ⁇ m to 250 ⁇ m, preferably 20 ⁇ m to 200 ⁇ m, more preferably 50 ⁇ m to 150 ⁇ m.
  • 2EHA 2-ethylhexyl acrylate
  • EA ethyl acrylate
  • DMAA N,N-dimethylacrylamide
  • acrylic copolymer solution Ethyl acetate was added to this acrylic copolymer solution so that the solid content was 30% to obtain acrylic copolymer 1 (solution) having a glass transition temperature of ⁇ 33.2° C. and a weight average molecular weight (Mw) of 950,000. rice field. Specific formulations are shown in Table 1.
  • Example 1 As an ultraviolet absorber (A) for 100 parts by mass of acrylic copolymer 1, 3 parts by mass of the 2-phenylbenzotriazole derivative represented by the above chemical formula (powder at 25 ° C.), 15 parts by mass of Tinuvin 109 (liquid at 25 ° C.) manufactured by BASF as an ultraviolet absorber (B), and A paint 1 was prepared by blending 2 parts by mass of Coronate HX manufactured by Tosoh Corporation. Subsequently, the paint 1 is applied to the release surface side of the release PET so that the film thickness after drying is 100 ⁇ m, and dried at 80 ° C. for 5 minutes to obtain composition 1. was cured at room temperature (about 25° C.) for 1 week to obtain a pressure-sensitive adhesive sheet 1 having a layer of pressure-sensitive adhesive 1 on the release PET.
  • a paint 1 was prepared by blending 2 parts by mass of Coronate HX manufactured by Tosoh Corporation. Subsequently, the paint 1 is applied to the release surface side of the release PET so that the film
  • Examples 2 to 7, Comparative Examples 1 to 4 The pressure-sensitive adhesive sheets 2 to 7 of Examples 2 to 7, which have layers of the pressure-sensitive adhesives 2 to 7 on the release PET, and the release PET Adhesive sheets ae of Comparative Examples 1-5 were obtained, having layers of adhesives ae thereon.
  • Tinuvin477 (liquid at 25°C) listed in Table 2 is an ultraviolet absorber manufactured by BASF.
  • the pressure-sensitive adhesive sheets obtained in Examples and Comparative Examples were subjected to 405 nm transmittance measurement, initial deposition evaluation, light resistance test, and haze rise measurement, and the results are summarized in Table 3. A specific evaluation method is shown below.
  • a 100 ⁇ m thick PET film (manufactured by Toyobo Co., Ltd., A4360) is laminated on one main surface (exposed surface) of the adhesive layer of the adhesive sheets obtained in Examples and Comparative Examples, and the PET of the adhesive layer is laminated. After peeling off the release PET on the side opposite to the film, soda glass with a thickness of 1.8 mm was laminated on the exposed side to prepare a laminate including an adhesive layer.
  • the laminate is placed in a light resistance tester (manufactured by Suga Test Instruments Co., Ltd., ultraviolet fade meter U48, light source: carbon arc lamp), and ultraviolet rays from the PET film side (illuminance: 500 W / m2, BP temperature 63 °C ⁇ 3 °C) for 500 hours.
  • a light resistance tester manufactured by Suga Test Instruments Co., Ltd., ultraviolet fade meter U48, light source: carbon arc lamp
  • ultraviolet rays from the PET film side luminance: 500 W / m2, BP temperature 63 °C ⁇ 3 °C
  • the precipitation state was evaluated according to the following criteria.
  • ⁇ Precipitation to the extent that the appearance is impaired cannot be confirmed over the entire test piece.
  • x Precipitation to the extent that the appearance is impaired can be confirmed in a part or the whole of the test piece.
  • the adhesives 1 to 7 of Examples 1 to 7 and the adhesive sheets 1 to 7 formed by the layers of the adhesive have excellent durability under high temperature and high humidity. low rise. Moreover, it was confirmed that the light resistance is good and the electromagnetic wave absorption power at a wavelength of 405 nm is excellent. Moreover, precipitation of the ultraviolet absorber at the initial stage could be suppressed.
  • the pressure-sensitive adhesives a to e of Comparative Examples 1 to 5 and the pressure-sensitive adhesive sheets a to e formed from the layers of the pressure-sensitive adhesives did not satisfy all of these evaluation items, unlike the examples.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

L'invention concerne : un adhésif de dispositif d'affichage, qui est en mesure d'absorber des ondes électromagnétiques jusqu'à des longueurs d'onde plus longues allant jusqu'à environ 405 nm ; et une feuille adhésive obtenue à l'aide de l'adhésif pour un dispositif d'affichage. Un mode de réalisation de cet adhésif pour un dispositif d'affichage contient un copolymère acrylique, un absorbeur de rayonnement ultraviolet (A) et un absorbeur de rayonnement ultraviolet (B). L'absorbeur de rayonnement ultraviolet (A) est un dérivé de 2-phénylbenzotriazole présentant un groupe cyclique thioaryle. L'absorbeur de rayonnement ultraviolet (B) est un liquide à température normale. La teneur (parties en masse) en absorbeur de rayonnement ultraviolet (B) représente 1-10 fois la teneur (parties en masse) en absorbeur de rayonnement ultraviolet (A).
PCT/JP2022/007748 2021-03-31 2022-02-24 Adhésif pour dispositif d'affichage et feuille adhésive l'utilisant WO2022209476A1 (fr)

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JP2023510669A JPWO2022209476A1 (fr) 2021-03-31 2022-02-24
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CN202280011521.XA CN116888232A (zh) 2021-03-31 2022-02-24 显示装置用粘着剂和使用其的粘着片

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Cited By (1)

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Publication number Priority date Publication date Assignee Title
WO2023190124A1 (fr) * 2022-04-01 2023-10-05 株式会社ダイセル Feuille adhésive et dispositif de régulation de lumière utilisant celle-ci

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Publication number Priority date Publication date Assignee Title
JP2002543266A (ja) * 1999-05-03 2002-12-17 チバ スペシャルティ ケミカルズ ホールディング インコーポレーテッド 高度に溶解性で、レッド−シフトされた、光安定なベンゾトリアゾール紫外線吸収剤を含む安定化された接着剤組成物及びそれから誘導された積層物品
CN103224758A (zh) * 2013-01-29 2013-07-31 中科院广州化学有限公司 一种太阳能电池封装用eva胶膜及其制备方法
WO2016021664A1 (fr) * 2014-08-05 2016-02-11 ミヨシ油脂株式会社 Additif pour conférer une capacité d'absorption des ultraviolets et/ou un indice de réfraction élevé à la matrice, et élément en résine l'utilisant
WO2020137819A1 (fr) * 2018-12-26 2020-07-02 ミヨシ油脂株式会社 Absorbant d'uv résistant à la lumière, résistant à la chaleur et durable

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002543266A (ja) * 1999-05-03 2002-12-17 チバ スペシャルティ ケミカルズ ホールディング インコーポレーテッド 高度に溶解性で、レッド−シフトされた、光安定なベンゾトリアゾール紫外線吸収剤を含む安定化された接着剤組成物及びそれから誘導された積層物品
CN103224758A (zh) * 2013-01-29 2013-07-31 中科院广州化学有限公司 一种太阳能电池封装用eva胶膜及其制备方法
WO2016021664A1 (fr) * 2014-08-05 2016-02-11 ミヨシ油脂株式会社 Additif pour conférer une capacité d'absorption des ultraviolets et/ou un indice de réfraction élevé à la matrice, et élément en résine l'utilisant
WO2020137819A1 (fr) * 2018-12-26 2020-07-02 ミヨシ油脂株式会社 Absorbant d'uv résistant à la lumière, résistant à la chaleur et durable

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023190124A1 (fr) * 2022-04-01 2023-10-05 株式会社ダイセル Feuille adhésive et dispositif de régulation de lumière utilisant celle-ci

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