WO2017073584A1 - タッチパネル用紫外線硬化型樹脂組成物、それを用いた硬化物及びタッチパネル - Google Patents

タッチパネル用紫外線硬化型樹脂組成物、それを用いた硬化物及びタッチパネル Download PDF

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WO2017073584A1
WO2017073584A1 PCT/JP2016/081646 JP2016081646W WO2017073584A1 WO 2017073584 A1 WO2017073584 A1 WO 2017073584A1 JP 2016081646 W JP2016081646 W JP 2016081646W WO 2017073584 A1 WO2017073584 A1 WO 2017073584A1
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resin composition
curable resin
meth
ultraviolet curable
acrylate
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PCT/JP2016/081646
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English (en)
French (fr)
Japanese (ja)
Inventor
高橋　真二郎
貴文 水口
隼 本橋
麻衣 鍔本
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日本化薬株式会社
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Priority to KR1020187010312A priority Critical patent/KR20180075494A/ko
Priority to JP2017547811A priority patent/JPWO2017073584A1/ja
Priority to CN201680060820.7A priority patent/CN108137993A/zh
Publication of WO2017073584A1 publication Critical patent/WO2017073584A1/ja

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • 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
    • 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
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
    • C08F220/343—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate in the form of urethane links
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
    • C08L23/10—Homopolymers or copolymers of propene
    • C08L23/12—Polypropene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/04—Homopolymers or copolymers of esters
    • C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
    • C08L33/08—Homopolymers or copolymers of acrylic acid esters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L57/00—Compositions of unspecified polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C08L57/02—Copolymers of mineral oil hydrocarbons
    • G—PHYSICS
    • G06—COMPUTING; CALCULATING OR COUNTING
    • G06F—ELECTRIC DIGITAL DATA PROCESSING
    • G06F3/00—Input arrangements for transferring data to be processed into a form capable of being handled by the computer; Output arrangements for transferring data from processing unit to output unit, e.g. interface arrangements
    • G06F3/01—Input arrangements or combined input and output arrangements for interaction between user and computer
    • G06F3/03—Arrangements for converting the position or the displacement of a member into a coded form
    • G06F3/041—Digitisers, e.g. for touch screens or touch pads, characterised by the transducing means

Definitions

  • the present invention relates to an ultraviolet curable resin composition for bonding at least two optical substrates, a cured product using the same, and a touch panel.
  • a touch panel In recent years, display devices that allow screen input by attaching a touch panel to a display screen of a display device such as a liquid crystal display, a plasma display, or an organic EL display have been widely used.
  • a glass plate or a resin film on which a transparent electrode is formed is bonded with a slight gap facing each other. If necessary, a transparent protection made of glass or resin is provided on the touch surface. It has a structure in which plates are bonded together.
  • the touch panel and the display unit are bonded with an ultraviolet curable adhesive
  • the cured film of the resin composition is too hard at the time of bonding, the cured resin is less likely to follow the substrate when the substrate is distorted.
  • a problem occurs.
  • a gap is generated between the substrate and the cured resin layer when cured after bonding, and the substrate and the cured product layer are peeled off, resulting in a decrease in yield.
  • peeling occurs due to biting air or the like.
  • Patent Document 1 discloses a technique for preventing this problem by a method of moving the pressing means on the substrate and spreading it out as a bonding method.
  • a method of moving the pressing means on the substrate and spreading it out as a bonding method.
  • a gap is generated between the substrate and the cured resin layer during curing after bonding, or due to the impact or environmental change described above. The problem of generating gaps will remain.
  • Patent Document 2 discloses a technique for preventing the above problem of peeling by using a resin composition having a high elongation rate and high adhesion.
  • the components in the resin composition must be operated, and in order to satisfy the physical properties, the range in which the resin composition material and the component ratio in the composition can be adjusted is limited, It becomes difficult to ensure other physical properties such as elasticity.
  • a resin having only a high elongation has a limited ability to follow the substrate, and it is difficult to sufficiently follow the substrate and prevent the generation of a gap during curing after bonding.
  • the present invention provides a cured resin layer having a low shrinkage rate, high adhesive strength, and high flexibility, whereby an optical member such as a display unit having good curability and adhesion can be obtained. It aims at providing the ultraviolet curable resin composition for touchscreens which a hardened
  • the present inventors have completed the present invention as a result of intensive studies in order to solve the above problems. That is, the present invention relates to the following (1) to (11).
  • R 1 represents a hydrogen atom, a hydroxyl group, a methylol group, or an organic group not containing a (meth) acryloyl group having a condensed polycyclic hydrocarbon group.
  • R 2 has a condensed polycyclic hydrocarbon group (meta ) Represents an organic group not containing an acryloyl group, n represents 0 or 1.
  • n represents 0 or 1.
  • Each of a plurality of R 1 may be present independently and may be the same or different.
  • the organic group not containing the (meth) acryloyl group having the condensed polycyclic hydrocarbon group of R 1 is any one of the following formulas (2A) to (2C):
  • R 3 is R 3 are each independently of.
  • Plurality of represents a hydrogen atom or a hydrocarbon group having 1 to 6 carbon atoms And may be the same or different.
  • the organic group not containing the (meth) acryloyl group having the condensed polycyclic hydrocarbon group represented by R 2 is any one of the following (3A) to (3C):
  • R 3 represents a hydrogen atom or a hydrocarbon group having 1 to 6 carbon atoms. A plurality of R 3 are each independently selected. And may be the same or different.
  • the ultraviolet curable resin composition as described in (1) represented by these.
  • the photopolymerizable oligomer (C) is selected from the group consisting of urethane (meth) acrylate, polyisoprene or (meth) acrylate having a hydrogenated polyisoprene skeleton, polybutadiene or (meth) acrylate having a hydrogenated polybutadiene skeleton.
  • the photopolymerizable oligomer (C) is a urethane (meth) acrylate having at least one skeleton selected from the group consisting of polypropylene / polybutadiene / hydrogenated polybutadiene / polyisoprene / hydrogenated polyisoprene (4 ) UV curable resin composition.
  • the photopolymerizable monomer (D) the following formula (10)
  • R 5 represents a hydrogen atom or CH 3 , and n represents an integer of 1 to 3)
  • the liquid softening component (B1) is contained, and the liquid softening component (B1) includes any one of hydroxyl group-containing polymer and liquid terpene resin, or both of them (1) to (7)
  • the ultraviolet curable resin composition of this invention is demonstrated.
  • the phrase “can be added to an ultraviolet curable resin composition used for optics” means that an additive that lowers the transparency of the cured product to an extent that it cannot be used for optics is not included.
  • (meth) acrylate means either one or both of methacrylate and acrylate. The same applies to “(meth) acrylic acid” and the like.
  • “Acrylate” represents only acrylate, and methacrylate is excluded.
  • the ultraviolet curable resin composition of the present invention contains a compound (A) represented by the following formula (1).
  • R 1 s each independently represent a hydrogen atom, a hydroxyl group, a methylol group, or an organic group that does not contain a (meth) acryloyl group having a condensed polycyclic hydrocarbon group.
  • R 2 represents a condensed polycyclic ring.
  • An organic group not containing a (meth) acryloyl group having a hydrocarbon group, n represents 0 or 1.
  • a plurality of R 1 s exist independently and may be the same or different. .
  • R 1 is any one of the following formulas (2A) to (2C) as an organic group not containing a (meth) acryloyl group having a condensed polycyclic hydrocarbon group.
  • R 3 is R 3 are each independently of. Plurality of represents a hydrogen atom or a hydrocarbon group having 1 to 6 carbon atoms And may be the same or different.
  • light resistance is excellent in the order of (2C), (2A), and (2B).
  • R 3 is preferably a hydrogen atom or an organic group having 1 to 3 carbon atoms.
  • R 1 is preferably any one of the following formulas (4A) to (4C).
  • R 2 is an organic group not containing a (meth) acryloyl group having a condensed polycyclic hydrocarbon group, and any one of the following formulas (3A) to (3C):
  • R 3 represents a hydrogen atom or a hydrocarbon group having 1 to 6 carbon atoms.
  • a plurality of R 3 are each independently selected. And may be the same or different.
  • R 3 is preferably a hydrogen atom or an organic group having 1 to 3 carbon atoms.
  • R 2 is preferably any one of the following formulas (5A) to (5C).
  • specific examples of the compound represented by the above formula (1) include esterified products of glycerin and ester compounds of pentaerythritol.
  • the esterified product of glycerin is represented by the following formula (6).
  • R 4 is the above formulas (7A) to (7C) and two are hydrogen atoms is a 1-substituent
  • two R 4 are the above formulas (7A) to (7C)
  • An atom is a disubstituted product
  • three of R 4 are the above formulas (7A) to (7C).
  • R 4 is a hydrogen atom or the following formula (7A) ⁇ (7C)
  • R 3 and * are the same as described above.
  • a plurality of R 3 and R 4 are present independently and may be the same or different.
  • light resistance is excellent in the order of (7C), (7A), and (7B).
  • R 4 in the formula (6) is preferably any one of the following formulas (8A) to (8C).
  • the ultraviolet curable resin composition of the present invention may contain a mixture of 1-substituted to 3-substituted products.
  • the mixture it is preferable that three of R 4 are compounds represented by any one of the above formulas (7A) to (7C). Particularly preferred are compounds.
  • each of R 4 in (7A) - the formula the substituent represented by (7C) are different (6) A mixture of compounds is preferred.
  • the esterified product of pentaerythritol is represented by the following formula (9).
  • R 4 is represented by the above formulas (7A) to (7C) and three are hydrogen atoms is a single substituent, and two of R 4 are the above formulas (7A) to (7C), and two are hydrogen.
  • An atom is a disubstituted product, three of R 4 are the above formulas (7A) to (7C), and one is a hydrogen atom, a three substituent, and four of R 4 are the above formulas (7A) to (7C). ) Is a 4-substitution.
  • R 4 is the same as described above.
  • a plurality of R 4 may be present independently and may be the same or different.
  • R 4 is the formulas (7A) to (7C)
  • it is preferably any one of the formulas (8A) to (8C).
  • two or more of R 4 in the formula (9) are any one of the formulas (7A) to (7C).
  • the ultraviolet curable resin composition of the present invention contains a mixture of a plurality of compounds having different numbers in which R 4 is substituted by any one of the above formulas (7A) to (7C) in the above formula (9). Can be made.
  • it is set as the said mixture, it is preferable that it is a 2 substituted body or a 3 substituted body.
  • each of R 4 in (7A) - the formula the substituent represented by (7C) are different (9)
  • a mixture of compounds is preferred.
  • it is preferably a mixture of compounds of the above formula (9), which are disubstituted and trisubstituted, each having a different substituent represented by (7A) to (7C) of R 4 .
  • the esterified product of pentaerythritol has more ester bond sites than the esterified product of glycerin and compatibility is improved, it is suitable for mixing with other raw materials.
  • Particularly preferred compounds include the following compounds.
  • the softening point of the compound represented by the above formula (1) is preferably 80 to 150 ° C, more preferably 90 to 105 ° C. By being in such a softening point, it can contribute to improving the elasticity of a resin cured material layer. Further, it is possible to immediately follow the substrate according to the pressure / temperature change and restore it.
  • the acid value is preferably 2 to 10.
  • the hydroxyl value is preferably 38 to 47. By being in such a range, generation
  • APHA is preferably 150 or less, and more preferably 50 or less. By being in such a suitable range, the visibility of the touch panel can be remarkably improved.
  • the ultraviolet curable resin composition for a touch panel of the present invention is a resin composition used for bonding at least two optical substrates, and contains a liquid softening component (B1) as a softening component (B). be able to.
  • the liquid softening component (B1) can be used without particular limitation as long as it is liquid at room temperature (25 ° C.).
  • the liquid softening component (B1) is not cross-linked by ultraviolet rays, and is present between the cross-links of the photopolymerizable oligomer or photopolymerizable monomer, thereby providing flexibility and reducing the shrinkage rate. have.
  • liquid softening component (B1) examples include polymers, oligomers, phthalates, phosphates, glycols, citrates, and aliphatic dibasic esters that are compatible in the composition. , Fatty acid esters, epoxy plasticizers, castor oils, terpene resins, hydrogenated terpene resins, liquid terpenes, and the like.
  • oligomer and polymer examples include polyisoprene skeleton, hydrogenated polyisoprene skeleton, polybutadiene skeleton, oligomer or polymer having hydrogenated polybutadiene skeleton or xylene skeleton and esterified product thereof, adipic acid ester oligomer, polybutene, and the like. be able to. From the viewpoint of transparency, hydrogenated terpene resins, hydrogenated polyisoprene, hydrogenated polybutadiene, polybutene, and liquid terpenes are preferable.
  • the liquid softening component (B1) the specific gravity of the liquid at 20 ° C. is preferably 0.93 or less, the dielectric constant at 1 Hz is preferably 3.5 or less, and the iodine value is 400. The following is preferable.
  • the liquid softening component (B1) preferably has a viscosity of 0.01 to 100 Pa ⁇ s with a cone plate rheometer at 25 ° C. under atmospheric pressure.
  • the ultraviolet curable resin composition for touch panels of this invention can contain a solid softening component (B2) as a softening component (B).
  • the solid softening component (B2) can be used without particular limitation as long as it is solid at room temperature (25 ° C.).
  • the solid softening component (B2) is not cross-linked by ultraviolet rays, is present between the cross-links of the photopolymerizable oligomer or photopolymerizable monomer, and sticks to the hardened product surface by arranging on the hardened product layer surface. Can be provided, and the effect of improving the adhesion improving function is exhibited.
  • Examples of such a solid softening component (B2) include polymers, oligomers, phthalates, phosphate esters, glycol esters, citrate esters, and aliphatic dibasic esters that are compatible in the composition. , Fatty acid esters, epoxy plasticizers, castor oils, terpene resins, hydrogenated terpene resins, liquid terpenes, and the like.
  • oligomer and polymer examples include polyisoprene skeleton, hydrogenated polyisoprene skeleton, polybutadiene skeleton, oligomer or polymer having hydrogenated polybutadiene skeleton or xylene skeleton and esterified product thereof, adipic acid ester oligomer, polybutene, and the like. be able to. From the viewpoint of transparency, hydrogenated terpene resins, hydrogenated polyisoprene, hydrogenated polybutadiene, polybutene, and liquid terpenes are preferable.
  • hydroxyl group-containing polymers such as hydrogenated polybutadiene contained in the side chain, and liquid terpene resins are particularly preferable.
  • a softening point is 60 degreeC or more, and it is more preferable that it is 70 degreeC or more.
  • the said liquid softening component (B1) and said (solid softening component (B2) and the total amount of the compound of the said Formula (1)) are constant mass ratios.
  • the ratio is usually 50.5: 49.5 to 99.9: 0.1.
  • the softening point of the solid softening component (B2) is generally correlated with the molecular weight of the solid softening component, and the softening point of the solid softening component (B2) showing a softening point of 60 ° C or higher is 60 to 115 ° C.
  • the mass ratio of the liquid softening component (B1) and (the total amount of the compound described in the formula (1) and the solid softening component (B2)) is preferably Is in the range of 94.9 to 50.5: 49.5 to 5.1, more preferably 89.9 to 50.5: 49.5 to 10.1.
  • the solid softening component (B2) having a softening point of 115 ° C. to 150 ° C. is used, the liquid softening component (B1) and (the solid softening component (B2) and the compound of the formula (1) are used.
  • the mass ratio of the total amount is preferably in the range of 99.9 to 55.5: 44.5 to 0.1, more preferably 99.9 to 60.5: 39.5 to 0.1.
  • the liquid softening component (B1) has a larger mass ratio than the solid softening component (B2), so that the elasticity of the cured resin layer in temporary curing or main curing can be remarkably improved. it can. And since it has high elasticity in this way, even when stress generated by pressure / temperature change or contraction rate difference between the substrate and the resin composition is applied to the substrate, it can immediately follow and restore to the substrate Can do. In addition, since the cured resin layer follows the substrate even after curing after bonding, it is difficult for separation to occur, so that the yield can be improved.
  • the weight ratio of the softening component in the ultraviolet curable resin composition (the total amount of the solid softening component (B2) and the compound represented by the formula (1)) is usually 5 to 40% by weight, preferably 10 to 35%. % By weight.
  • the liquid softening component (B1) is usually 10 to 70% by weight, preferably 20 to 60% by weight.
  • the ultraviolet curable resin composition of the present invention can contain a photopolymerizable oligomer (C).
  • a photopolymerizable oligomer (C) in the ultraviolet curable resin composition of this invention,
  • skeleton It is preferable to use one selected from the group consisting of (meth) acrylates having a polybutadiene skeleton.
  • urethane (meth) acrylate is preferable from the viewpoint of adhesive strength, and has at least one skeleton selected from the group consisting of polybutadiene / hydrogenated polybutadiene / polyisoprene / hydrogenated polyisoprene from the viewpoint of moisture resistance. Urethane (meth) acrylate is more preferable.
  • the urethane (meth) acrylate is obtained by reacting polyhydric alcohol, polyisocyanate and hydroxyl group-containing (meth) acrylate.
  • polyhydric alcohol examples include polybutadiene glycol, hydrogenated polybutadiene glycol, polyisoprene glycol, hydrogenated polyisoprene glycol, neopentyl glycol, 3-methyl-1,5-pentanediol, ethylene glycol, propylene glycol, 1,4 A cyclic skeleton such as butanediol, alkylene glycol having 1 to 10 carbon atoms such as 1,6-hexanediol, triol such as trimethylolpropane and pentaerythritol, tricyclodecane dimethylol, bis- [hydroxymethyl] -cyclohexane, etc.
  • polycarbonate polyol for example, polycarbonate diol obtained by reaction of 1,6-hexanediol and diphenyl carbonate, etc.
  • polyether polyol for example, polyethylene glycol, polypropylene glycol, polytetramethylene glycol, ethylene oxide-modified bisphenol A, etc.
  • the polyhydric alcohol is preferably propylene glycol, polybutadiene glycol, hydrogenated polybutadiene glycol, polyisoprene glycol, or hydrogenated polyisoprene glycol, and weight average molecular weight from the viewpoint of transparency and flexibility.
  • Hydrogenated polybutadiene glycol is preferred from the viewpoints of discoloration such as heat-resistant coloring and compatibility.
  • the upper limit of the weight average molecular weight at this time is not particularly limited, but is preferably 10,000 or less, and more preferably 5000 or less. Moreover, you may use together 2 or more types of polyhydric alcohol as needed.
  • organic polyisocyanate examples include isophorone diisocyanate, hexamethylene diisocyanate, tolylene diisocyanate, xylene diisocyanate, diphenylmethane-4,4'-diisocyanate, and dicyclopentanyl isocyanate.
  • isophorone diisocyanate is preferable from the viewpoint of toughness.
  • hydroxyl group-containing (meth) acrylates include hydroxy C2-C4 alkyl (meth) acrylates such as hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate, hydroxybutyl (meth) acrylate, dimethylol cyclohexyl mono ( A (meth) acrylate, a hydroxycaprolactone (meth) acrylate, a hydroxyl group terminal polyalkylene glycol (meth) acrylate, etc. can be used.
  • hydroxy C2-C4 alkyl (meth) acrylates such as hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate, hydroxybutyl (meth) acrylate, dimethylol cyclohexyl mono ( A (meth) acrylate, a hydroxycaprolactone (meth) acrylate, a hydroxyl group terminal polyalkylene glycol (meth) acryl
  • the reaction for obtaining the urethane (meth) acrylate is performed, for example, as follows. That is, the polyhydric alcohol is mixed with an organic polyisocyanate per equivalent of the hydroxyl group so that the isocyanate group is preferably 1.1 to 2.0 equivalent, more preferably 1.1 to 1.5 equivalent. Is preferably reacted at 70 to 90 ° C. to synthesize a urethane oligomer. Next, the hydroxy (meth) acrylate compound is mixed so that the hydroxyl group is preferably 1 to 1.5 equivalents per equivalent of the isocyanate group of the urethane oligomer, and reacted at 70 to 90 ° C. to react with the target urethane (meth). ) Acrylate can be obtained.
  • the weight average molecular weight of the urethane (meth) acrylate is preferably about 7,000 to 100,000, and more preferably 10,000 to 60,000. When the weight average molecular weight is 7000 or more, the shrinkage becomes smaller, and when the weight average molecular weight is 100,000 or less, the curability is further improved.
  • urethane (meth) acrylates can be used alone or in admixture of two or more.
  • the weight ratio of urethane (meth) acrylate in the ultraviolet curable resin composition of the present invention is usually 5 to 90% by weight, preferably 10 to 50% by weight.
  • the (meth) acrylate having the polyisoprene skeleton has a (meth) acryloyl group at the terminal or side chain of the polyisoprene molecule.
  • (Meth) acrylates having a polyisoprene skeleton are available as UC-203, UC102, and UC-1 (manufactured by Kuraray Co., Ltd.).
  • the (meth) acrylate having a polyisoprene skeleton preferably has a polystyrene-equivalent number average molecular weight of 1,000 to 50,000, more preferably about 25,000 to 45,000.
  • the weight ratio of the (meth) acrylate having a polyisoprene skeleton in the ultraviolet curable resin composition of the present invention is usually 5 to 90% by weight, preferably 10 to 50% by weight.
  • the ultraviolet curable resin composition of the present invention contains a photopolymerizable monomer (D).
  • a photopolymerizable monomer (D) a (meth) acrylate having one (meth) acryloyl group in the molecule can be preferably used.
  • the photopolymerizable monomer (D) excludes (meth) acrylate having urethane (meth) acrylate, polyisoprene or hydrogenated polyisoprene skeleton, (meth) acrylate having polybutadiene or hydrogenated polybutadiene skeleton ( (Meth) acrylate is shown.
  • R 5 represents a hydrogen atom or CH 3 , and n represents an integer of 1 to 3
  • the monofunctional acrylate represented by these can be used conveniently.
  • the composition ratio of the ultraviolet curable resin composition is preferably 1 to 20% by weight of the monofunctional acrylate represented by the above formula (10), 5 to 90% by weight of the photopolymerizable oligomer (C),
  • the photopolymerizable monomer (D) other than (10) is 5 to 90% by weight
  • the photopolymerization initiator (E) is 0.1 to 5% by weight
  • the other components are the balance.
  • Examples of the monofunctional acrylate represented by the formula (10) in the ultraviolet curable resin composition of the present invention include 4-hydroxybutyl acrylate, 2-hydroxypropyl acrylate, 3-hydroxypropyl acrylate, 2-hydroxyethyl acrylate, and the like. 2 or more may be used in combination as required.
  • R 5 when n is 2 or less (particularly when n is 1 or less), R 5 is preferably a methyl group. When n is 3 or more, R 5 is preferably a hydrogen atom.
  • a total carbon number of 2 or more is preferable because a resin composition with low volatility and low cloudiness can be obtained.
  • the following formula (11) is preferable because a resin composition with low volatility and low cloudiness can be obtained.
  • n represents an integer of 2 to 4.
  • the monofunctional acrylate represented by these is preferable.
  • Examples of the monofunctional acrylate represented by the formula (11) include 4-hydroxybutyl acrylate, 3-hydroxypropyl acrylate, 2-hydroxyethyl acrylate and the like.
  • 4-hydroxybutyl acrylate is particularly preferable from the viewpoint of low volatility. When a methacrylate resin is used, the curing rate tends to be slow, and when the resin composition is actually used, it may take time to cure.
  • the MOH / (MC + MB) is preferably 0.3 or less, particularly preferably 0.28 or less, and particularly preferably 0.25 or less.
  • the monofunctional acrylate represented by the formula (10) that satisfies the condition is referred to as a low volatility / whitening-resistant acrylate.
  • the content of the photopolymerizable monomer represented by the formula (10) is preferably 1 to 20% by weight, more preferably 2 to 10% by weight, and particularly preferably 5.5 to 8% by weight.
  • the content of the formula (10) component is 1% or more, the whitening resistance is further improved.
  • it is 20% by weight or less bubbles do not easily enter during bonding, and compatibility with other components is improved and the liquid does not become cloudy.
  • containing a methacrylate having a hydroxyl group in the ultraviolet curable resin composition may adversely affect physical properties such as a decrease in the curing rate and whitening resistance.
  • the content is preferably 10% by weight or less, particularly preferably 5% by weight or less.
  • Specific examples of the (meth) acrylate having one (meth) acryloyl group in the molecule other than the photopolymerizable monomer represented by the formula (10) include isooctyl (meth) acrylate and isoamyl (meth) acrylate. , Lauryl (meth) acrylate, isodecyl (meth) acrylate, stearyl (meth) acrylate, cetyl (meth) acrylate, isomyristyl (meth) acrylate, isostearyl (meth) acrylate, tridecyl (meth) acrylate, etc.
  • alkyl (meth) acrylates benzyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, acryloylmorpholine, phenylglycidyl (meth) acrylate, tricyclodecane (meth) acrylate, dicyclopentenyl Acrylate, dicyclopentenyloxyethyl (meth) acrylate, isobornyl (meth) acrylate, dicyclopentanyl (meth) acrylate, 1-adamantyl acrylate, 2-methyl-2-adamantyl acrylate, 2-ethyl-2-adamantyl acrylate, 1-adamantyl methacrylate, polypropylene oxide modified nonylphenyl (meth) acrylate, (meth) acrylate having a cyclic skeleton such as dicyclopentadieneoxyethyl (meth) acrylate, alkyl (meth) acrylate
  • X represents an acryloyl group
  • R 6 represents an alkyl group having 8 to 20 carbon atoms (preferably 10 to 20 carbon atoms)
  • a monofunctional acrylate represented by the following formula (13) is preferred from the viewpoint of adhesive strength:
  • the monofunctional acrylate represented by these is more preferable.
  • isostearyl acrylate is more preferable from the viewpoints of low volatility, reactivity, and flexibility.
  • the number of R 6 alkyl groups in the above formula (12) is defined as MR, and the formula (10).
  • the resin composition preferably a resin composition containing both compounds such that MR / (MC + MB) (hereinafter referred to as a special ratio) is 5.5 or less, and particularly preferably 5 or less. preferable. Further, from the viewpoint of making the whitening resistance particularly excellent, the resin composition contains both compounds having the low volatility / whitening resistance acrylate and the special ratio of 5.5 or less. It is preferably 5 or less.
  • composition of the present invention can contain (a (meth) acrylate other than a (meth) acrylate having one (meth) acryloyl group in the molecule) as long as the characteristics of the present invention are not impaired.
  • a (meth) acrylate other than a (meth) acrylate having one (meth) acryloyl group in the molecule for example, tricyclodecane dimethylol di (meth) acrylate, dioxane glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate, polytetramethylene glycol di (meth) acrylate, alkylene oxide modified bisphenol A type di (meth) acrylate Trimethylol C2-C10 alkanes such as caprolactone-modified hydroxypivalic acid neopentyl glycol di (meth) acrylate, ethylene oxide-modified phosphoric acid di (meth) acrylate, trimethylolpropane tri
  • trimethylol C2-C10 alkane polyalkoxy tri (meth) acrylate tris [(meth) acryloyloxyethyl] isocyanurate
  • pentaerythritol tri (meth) Alkylene oxide modified trimethylolpropane tri (meth) acrylate such as acrylate, ethylene oxide modified trimethylolpropane tri (meth) acrylate, propylene oxide modified trimethylolpropane tri (meth) acrylate
  • pentaerythritol polyethoxytetra (meth) acrylate penta Erythritol polypropoxytetra (meth) acrylate
  • pentaerythritol tetra (meth) acrylate ditrime Trimethylolpropane tetra (meth) acrylate, dipentaerythritol tetra (meth) acrylate, dipentaerythritol penta (
  • these (meth) acrylate monomer components can be used alone or in admixture of two or more at any ratio.
  • the weight ratio of the photopolymerizable monomer (D) other than the above formula (1) in the photocurable transparent resin composition of the present invention is usually 5 to 90% by weight, preferably 10 to 50% by weight. If it is less than 5% by weight, the curability may be poor, and if it is more than 90% by weight, shrinkage may increase.
  • the ratio (weight ratio) of the component of formula (10): component of formula (12) is preferably in the range of 1: 2 to 1:25, particularly in the range of 1: 3 to 1:15. preferable.
  • epoxy (meth) acrylate can be used as long as the characteristics of the present invention are not impaired.
  • Epoxy (meth) acrylate has a function of improving curability and improving the hardness and curing speed of a cured product. Any epoxy (meth) acrylate can be used as long as it is obtained by reacting a glycidyl ether type epoxy compound with (meth) acrylic acid, and preferably used epoxy (meth) acrylate.
  • Examples of the glycidyl ether type epoxy compound to be obtained include diglycidyl ether of bisphenol A or its alkylene oxide adduct, diglycidyl ether of bisphenol F or its alkylene oxide adduct, diglycidyl of hydrogenated bisphenol A or its alkylene oxide adduct.
  • Diglycidyl ether ethylene glycol diglycidyl ether, propylene glycol diglycidyl ether of ether, hydrogenated bisphenol F or its alkylene oxide adduct Neopentyl glycol diglycidyl ether, butanediol diglycidyl ether hexanediol diglycidyl ether to, cyclohexanedimethanol diglycidyl ether, and polypropylene glycol diglycidyl ether.
  • Epoxy (meth) acrylate is obtained by reacting these glycidyl ether type epoxy compounds with (meth) acrylic acid under the following conditions.
  • (Meth) acrylic acid is preferably reacted at a ratio of 0.9 to 1.5 mol, more preferably 0.95 to 1.1 mol, per 1 equivalent of epoxy group of the glycidyl ether type epoxy compound.
  • the reaction temperature is preferably 80 to 120 ° C., and the reaction time is about 10 to 35 hours.
  • a catalyst such as triphenylphosphine, TAP, triethanolamine, or tetraethylammonium chloride.
  • paramethoxyphenol, methylhydroquinone or the like can be used as a polymerization inhibitor.
  • An epoxy (meth) acrylate that can be suitably used in the present invention is a bisphenol A type epoxy (meth) acrylate obtained from a bisphenol A type epoxy compound.
  • the weight average molecular weight of the epoxy (meth) acrylate is preferably 500 to 10,000.
  • the weight ratio of the epoxy (meth) acrylate in the ultraviolet curable resin composition of the present invention is usually 1 to 80% by weight, preferably 5 to 30% by weight.
  • the photopolymerization initiator (E) contained in the composition of the present invention is not particularly limited, and examples thereof include 2,4,6-trimethylbenzoyldiphenylphosphine oxide and 2,4,6-trimethylbenzoylphenylethoxyphosphine.
  • Fin oxide bis (2,4,6-trimethylbenzoyl) -phenylphosphine oxide, bis (2,6-dimethoxybenzoyl) -2,4,4-trimethyl-pentylphosphine oxide, 1-hydroxycyclohexyl phenyl ketone ( Irgacure 184; manufactured by BASF), 2-hydroxy-2-methyl- [4- (1-methylvinyl) phenyl] propanol oligomer (Esacure ONE; manufactured by Lamberti), 1- [4- (2-hydroxyethoxy) -phenyl ] -2-Hydroxy-2-methyl -1-propan-1-one (Irgacure 2959; manufactured by BASF), 2-hydroxy-1- ⁇ 4- [4- (2-hydroxy-2-methyl-propionyl) -benzyl] -phenyl ⁇ -2-methyl -Propan-1-one (Irgacure 127; manufactured by BASF), 2,2-dimethoxy-2-phen
  • the molar extinction coefficient at 302 nm or 313 nm measured in acetonitrile or methanol is 300 ml / (g ⁇ cm) or more, and the molar extinction coefficient at 365 nm is 100 ml. It is preferable to use a photopolymerization initiator that is not more than / (g ⁇ cm). By using such a photopolymerization initiator, it is possible to contribute to an improvement in adhesive strength.
  • the molar extinction coefficient at 302 nm or 313 nm is 300 ml / (g ⁇ cm) or more, curing at the time of curing in the following step 3 is sufficient.
  • photopolymerization initiator (E) examples include 1-hydroxycyclohexyl phenyl ketone (Irgacure 184; manufactured by BASF), 2-hydroxy-2-methyl-1-phenyl-propan-1-one (Darocur 1173).
  • these photopolymerization initiators (E) can be used alone or in admixture of two or more at any ratio.
  • the weight ratio of the photopolymerization initiator (E) in the ultraviolet curable resin composition of the present invention is usually 0.2 to 5% by weight, preferably 0.3 to 3% by weight. If it is 5% by weight or less, when obtaining a cured product layer having a cured portion and an uncured portion on the side opposite to the optical substrate side, the uncured portion is reliably formed, and the transparency of the cured resin layer is obtained. Will improve.
  • the ultraviolet curable resin composition of the present invention can contain additives, which will be described later, as other components.
  • amines that can serve as photopolymerization initiation assistants can be used in combination with the above photopolymerization initiator.
  • examples of amines that can be used include benzoic acid 2-dimethylaminoethyl ester, dimethylaminoacetophenone, p-dimethylaminobenzoic acid ethyl ester, and p-dimethylaminobenzoic acid isoamyl ester.
  • the content in the ultraviolet curable resin composition of the present invention is usually 0.005 to 5% by weight, preferably 0.01 to 3% by weight.
  • an antioxidant In the ultraviolet curable resin composition of the present invention, an antioxidant, an organic solvent, a silane coupling agent, a polymerization inhibitor, a leveling agent, an antistatic agent, a surface lubricant, a fluorescent whitening agent, and a light stabilizer are optionally added. You may add additives, such as an agent (for example, hindered amine compound etc.) and a filler.
  • an agent for example, hindered amine compound etc.
  • antioxidants include, for example, BHT, 2,4-bis- (n-octylthio) -6- (4-hydroxy-3,5-di-t-butylanilino) -1,3,5-triazine Pentaerythrityl tetrakis [3- (3,5-di-t-butyl-4-hydroxyphenyl) propionate], 2,2-thio-diethylenebis [3- (3,5-di-t-butyl- 4-hydroxyphenyl) propionate], triethylene glycol-bis [3- (3-tert-butyl-5-methyl-4-hydroxyphenyl) propionate], 1,6-hexanediol-bis [3- (3-t -Butyl-5-methyl-4-hydroxyphenyl) propionate], octadecyl-3- (3,5-di-t-butyl-4-hydroxyphenyl) propionate, , N-hexamethylenebis (3,5-di-di
  • organic solvent examples include alcohols such as methanol, ethanol and isopropyl alcohol, dimethyl sulfone, dimethyl sulfoxide, tetrahydrofuran, dioxane, toluene, xylene and the like.
  • silane coupling agent examples include, for example, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 2- (3,4-epoxy) (Cyclohexyl) ethyltrimethoxysilane, N- (2-aminoethyl) 3-aminopropylmethyldimethoxysilane, ⁇ -mercapropropyltrimethoxysilane, N- (2-aminoethyl) 3-aminopropylmethyltrimethoxysilane, 3 -Aminopropyltriethoxysilane, 3-mercaptopropyltrimethoxysilane, vinyltrimethoxysilane, N- (2- (vinylbenzylamino) ethyl) 3-aminopropyltrimethoxysilane hydrochloride, 3-methacryloxypropyltri
  • polymerization inhibitor examples include paramethoxyphenol and methylhydroquinone.
  • the light stabilizer include, for example, 1,2,2,6,6-pentamethyl-4-piperidyl alcohol, 2,2,6,6-tetramethyl-4-piperidyl alcohol, 1,2,2, 6,6-pentamethyl-4-piperidyl (meth) acrylate (LA-82, manufactured by ADEKA Corporation), tetrakis (1,2,2,6,6-pentamethyl-4-piperidyl) -1,2,3 4-butanetetracarboxylate, tetrakis (2,2,6,6-tetramethyl-4-piperidyl) -1,2,3,4-butanetetracarboxylate, 1,2,3,4-butanetetracarboxylic acid And 1,2,2,6,6-pentamethyl-4-piperidinol and 3,9-bis (2-hydroxy-1,1-dimethylethyl) -2,4,8,10-tetraoxaspiro [5.5 Unde Mixed ester with decanoic acid bis (2,2,6,6-tetramethyl)
  • the filler include, for example, crystalline silica, fused silica, alumina, zircon, calcium silicate, calcium carbonate, silicon carbide, silicon nitride, boron nitride, zirconia, fosterite, steatite, spinel, titania, talc and the like.
  • examples thereof include powder or beads obtained by spheroidizing these.
  • the weight ratio of the various additives in the photocurable transparent resin composition is 0.01 to 3% by weight, preferably 0.01 to 1% by weight, more preferably 0.02 to 0.5% by weight.
  • the ultraviolet curable resin composition of the present invention can be obtained by mixing and dissolving the aforementioned components at room temperature to 80 ° C., and if necessary, impurities may be removed by an operation such as filtration.
  • impurities may be removed by an operation such as filtration.
  • Step 1 By applying the ultraviolet curable resin composition to at least one optical substrate to form a coating layer, and irradiating the coating layer with ultraviolet rays, an optical group in the coating layer is formed.
  • a cured portion (hereinafter referred to as “cured portion of the cured product layer” or simply “cured portion”) present on the material side (lower side of the coating layer) and the side opposite to the optical substrate side (upper side of the coating layer) Step of obtaining an optical substrate having a cured product layer having an uncured portion (hereinafter, referred to as “uncured portion of the cured product layer” or simply “uncured portion”) present on the atmosphere side.
  • Step 1 there is no particular limitation on the curing rate of the coating layer after ultraviolet irradiation, and there is an uncured portion on the surface opposite to the optical substrate side (the upper side of the coating layer, usually the air side).
  • Step 2 Another optical substrate is bonded to the uncured portion of the cured product layer of the optical substrate obtained in Step 1, or the other optical substrate obtained in Step 1 is cured. The process of bonding the uncured part of the material layer.
  • FIG. 1 is a process diagram showing a first embodiment of a production process of an optical member using the ultraviolet curable resin composition of the present invention.
  • This method is a method of obtaining an optical member by bonding the liquid crystal display unit 1 and the transparent substrate 2 together.
  • the liquid crystal display unit 1 is a liquid crystal display unit in which a liquid crystal material is sealed between a pair of substrates on which electrodes are formed, and a polarizing plate, a driving circuit, a signal input cable, and a backlight unit are provided.
  • the transparent substrate 2 is a transparent substrate such as a glass plate, a polymethyl methacrylate (PMMA) plate, a polycarbonate (PC) plate, an alicyclic polyolefin polymer (COP) plate, an acrylic resin, or polyethylene terephthalate.
  • the transparent substrate may be subjected to hard coat treatment or antireflection treatment on one side or both sides.
  • the transparent substrate 2 having a black frame-shaped light-shielding portion 4 on the surface of the transparent substrate can be preferably used, and the light-shielding portion 4 is formed by applying a tape, applying a paint, printing, or the like. In the present invention, the present invention can also be applied to a device that does not have the light shielding portion 4.
  • transparent substrate having a light-shielding portion can be read as “transparent substrate”, and can be considered as an example in which the light-shielding portion is not provided as it is.
  • an ultraviolet curable resin composition is apply
  • the coating method include a slit coater, a roll coater, a spin coater, and a screen printing method.
  • the ultraviolet curable resin composition applied to the surface of the liquid crystal display unit 1 and the transparent substrate 2 having the light shielding portion may be the same, or different ultraviolet curable resin compositions may be used. Usually, it is preferable that both are the same ultraviolet curable resin composition.
  • the resin composition reaches the light shielding layer by filling the difference in height between the substrate and the light shielding layer.
  • the film thickness of the cured product of each ultraviolet curable resin is adjusted so that the cured resin layer 7 after bonding has a thickness of 50 to 500 ⁇ m, preferably 50 to 350 ⁇ m, and more preferably 100 to 350 ⁇ m.
  • the film thickness of the cured layer of the ultraviolet curable resin existing on the surface of the transparent substrate 2 having the light-shielding portion depends on the film thickness, the ultraviolet curable resin usually existing on the surface of the liquid crystal display unit 1 is used.
  • the thickness is equal to or thicker than the thickness of the cured product layer of the mold resin. This is to minimize the portion that remains uncured even after irradiation with ultraviolet rays in Step 3 described later, thereby eliminating the risk of curing failure.
  • the ultraviolet curable resin composition layer 5 after application is irradiated with ultraviolet rays 8 and a cured portion (in the drawing, the liquid crystal display unit side or the transparent substrate side as viewed from the ultraviolet curable resin composition) is present (in the figure). Curing with uncured parts (not shown in the figure) present on the upper side of the coating layer (on the opposite side of the liquid crystal display unit side or on the opposite side of the transparent substrate side) (on the atmospheric side when performed in the atmosphere) A physical layer 6 is obtained.
  • the irradiation amount is preferably 5 to 2000 mJ / cm 2 , particularly preferably 10 to 1000 mJ / cm 2 .
  • uncured refers to a fluid state in a 25 ° C. environment.
  • the resin composition layer is touched with a finger after ultraviolet irradiation and a liquid component adheres to the finger, it is determined to have an uncured portion.
  • any light source may be used as long as it is a lamp that irradiates ultraviolet to near ultraviolet rays.
  • a low-pressure, high-pressure or ultrahigh-pressure mercury lamp, metal halide lamp, (pulse) xenon lamp, or electrodeless lamp can be used.
  • the wavelength of the ultraviolet ray irradiated to the ultraviolet curable resin composition is not particularly limited, but when the maximum illuminance in the range of 320 nm to 450 nm is 100, the ratio of the maximum illuminance at 200 to 320 nm.
  • the (illuminance ratio) is preferably 30 or less, and particularly preferably the illuminance at 200 to 320 nm is 10 or less.
  • the maximum illuminance in the range of 320 nm to 450 nm is 100
  • the ratio of the maximum illuminance (illuminance ratio) at 200 to 320 nm is higher than 30, the adhesive strength of the optical member finally obtained may be inferior. is there. This is because if the illuminance at a low wavelength is high, the curing of the ultraviolet curable resin composition proceeds excessively at the time of curing in the step 1, and the contribution to the adhesion at the time of curing in the ultraviolet irradiation in the step 3 is reduced. This is thought to be due to this.
  • the method of irradiating ultraviolet rays so as to achieve the above illuminance ratio includes, for example, a method of applying a lamp that satisfies the illuminance ratio as a lamp that irradiates ultraviolet to near ultraviolet rays, Even if the above condition is not satisfied, such illuminance can be obtained by using a base material (for example, a short wave ultraviolet cut filter, a glass plate, a film, etc.) that cuts short wavelength ultraviolet rays at the time of irradiation in step 1. Irradiation at a ratio is possible. Although it does not specifically limit as a base material which adjusts the illumination intensity ratio of an ultraviolet-ray, For example, the glass plate, soda-lime glass, PET film etc.
  • irradiation with ultraviolet rays is usually carried out in the air at the upper surface on the coating side (on the opposite side of the liquid crystal display unit side or on the transparent substrate side as seen from the ultraviolet curable resin composition) (normal atmospheric surface) ). Further, ultraviolet irradiation may be performed while spraying a curing-inhibiting gas on the upper surface of the coating layer after evacuation.
  • the side opposite to the liquid crystal display unit side or the side opposite to the transparent substrate side is the atmosphere side.
  • ultraviolet rays may be irradiated in a vacuum environment or in a gas environment that does not cause hardening inhibition such as nitrogen.
  • step 3 when step 3 is omitted, curing can be suitably performed in a vacuum or while spraying a gas (for example, nitrogen) that promotes curing. Thereby, even if the step 3 is omitted, sufficient adhesion can be performed.
  • the state of the uncured portion and the film thickness of the uncured portion can be adjusted by spraying oxygen or ozone onto the surface of the ultraviolet curable resin layer (coating layer) during the ultraviolet irradiation. That is, when oxygen or ozone is sprayed on the surface of the coating layer, oxygen inhibition of curing of the ultraviolet curable resin composition occurs on the surface, so that the uncured portion of the surface can be ensured or the uncured portion
  • the film thickness can be increased.
  • the optical member obtained by bonding the transparent substrate 2 and the liquid crystal display unit 1 is irradiated with the ultraviolet-ray 8 from the transparent substrate 2 side which has a light-shielding part, and ultraviolet curable type
  • the resin composition (coating layer) is cured.
  • the dose of ultraviolet rays is preferably about 100 ⁇ 4000mJ / cm 2 in accumulated light quantity, particularly preferably 200 ⁇ 3000mJ / cm 2 approximately.
  • the light source used for curing by irradiation with ultraviolet to near ultraviolet light may be any lamp as long as it is a lamp that emits ultraviolet to near ultraviolet light.
  • a low-pressure, high-pressure or ultrahigh-pressure mercury lamp, metal halide lamp, (pulse) xenon lamp, or electrodeless lamp can be used. In this way, an optical member as shown in FIG. 5 can be obtained.
  • the optical member of the present invention may be manufactured by the second modified embodiment described below. Note that the details in each step are the same as those in the first embodiment, and therefore, the description of the same parts is omitted.
  • the resin composition reaches the light shielding layer by filling the difference in height between the substrate and the light shielding layer.
  • the wavelength of the ultraviolet ray irradiated to the ultraviolet curable resin composition is not particularly limited, but when the maximum illuminance in the range of 320 nm to 450 nm is 100, the ratio of the maximum illuminance at 200 to 320 nm is preferably 30 or less. Particularly preferably, the illuminance at 200 to 320 nm is 10 or less.
  • the adhesive strength of the final optical member is further improved.
  • a transparent substrate 2 having a liquid crystal display unit 1 and a light shielding portion in a form in which the uncured portion of the obtained cured product layer 6 and the display surface of the liquid crystal display unit 1 face each other.
  • Bonding can be performed either in air or in vacuum.
  • FIG. 3 is a process diagram showing a third embodiment of a method for producing an optical member using the ultraviolet curable resin composition of the present invention. Note that the details in each step are the same as those in the first embodiment, and therefore, the description of the same parts is omitted. In addition, the same code
  • the ultraviolet curable composition was applied to the surface of the liquid crystal display unit 1. Thereafter, the ultraviolet curable resin composition layer 5 is irradiated with ultraviolet rays 8, and a cured portion existing on the lower side of the coating layer (on the transparent substrate side as viewed from the ultraviolet curable resin composition) and the upper side of the coating layer ( A cured product layer 6 having an uncured portion present on the side opposite to the transparent substrate side is obtained.
  • the wavelength of ultraviolet rays irradiated to the ultraviolet curable resin composition is not particularly limited, but when the maximum illuminance in the range of 320 nm to 450 nm is 100, the maximum illuminance at 200 to 320 nm is preferably 30 or less. The illuminance at 200 to 320 nm is preferably 10 or less. When the maximum illuminance in the range of 320 nm to 450 nm is 100, if the maximum illuminance at 200 to 320 nm is 30 or less, the adhesive strength of the optical member finally obtained is further improved.
  • the liquid crystal display unit 1 is formed such that the uncured portion of the obtained cured product layer 6 and the surface on which the light shielding portion on the transparent substrate 2 having the light shielding portion is formed face each other. And a transparent substrate 2 having a light shielding portion are bonded together. Bonding can be performed either in air or in vacuum.
  • the optical member of the present invention may be manufactured according to the following modified fourth embodiment. Note that the details in each step are the same as those in the first embodiment, and therefore, the description of the same parts is omitted.
  • the fourth embodiment is described based on the second embodiment in which the step 3 is omitted, but the omission can be performed in the first to third embodiments.
  • the resin composition reaches the light shielding layer by filling the difference in height between the substrate and the light shielding layer.
  • the wavelength of the ultraviolet ray irradiated to the ultraviolet curable resin composition is not particularly limited, but when the maximum illuminance in the range of 320 nm to 450 nm is 100, the ratio of the maximum illuminance at 200 to 320 nm is preferably 30 or less. Particularly preferably, the illuminance at 200 to 320 nm is 10 or less.
  • the adhesive strength of the final optical member is further improved.
  • any method for adjusting the film thickness of the uncured portion by spraying nitrogen or ozone is not applied only to the above-described embodiment, but can be applied to any manufacturing method included in the present invention.
  • optical base material is an optical base material
  • the optical base material bonded thereto is at least one display unit selected from the group consisting of a liquid crystal display unit, a plasma display unit, and an organic EL unit.
  • One optical base material is a protective base material having a light-shielding part, and another optical base material bonded to it is a touch panel or a display unit having a touch panel, and at least two optical base materials are bonded.
  • a mode in which the optical member is a touch panel having a protective base material having a light-shielding portion or a display unit having the same.
  • the ultraviolet curable resin composition is applied to either the surface of the protective base material having the light shielding portion, the touch surface of the touch panel, or both of them. It is preferable to apply.
  • One optical substrate is an optical substrate having a light-shielding portion, the other optical substrate bonded to it is a display unit, and an optical member having at least two optical substrates bonded thereto
  • the aspect which is a display body unit which has an optical base material which has a light-shielding part.
  • the ultraviolet curable resin is applied to either the surface of the optical substrate having the light shielding portion on the side where the light shielding portion is provided, the display surface of the display unit, or both of them. It is preferable to apply the composition.
  • the optical substrate having a light shielding part include a display screen protective plate having a light shielding part, or a touch panel provided with a protective substrate having a light shielding part.
  • the optical substrate having the light-shielding portion is a protective plate for a display screen having the light-shielding portion
  • the surface of the optical substrate having the light-shielding portion is provided on the side on which the light-shielding portion is provided. It is the surface on the side where the part is provided.
  • the optical substrate having the light shielding portion is a touch panel having a protective substrate having the light shielding portion
  • the surface having the light shielding portion of the protective substrate having the light shielding portion is bonded to the touch surface of the touch panel.
  • the surface of the optical substrate having the light shielding portion on the side where the light shielding portion is provided means the substrate surface of the touch panel opposite to the touch surface of the touch panel.
  • the light-shielding part of the optical base material having the light-shielding part may be at any position of the optical base material, but is usually created in a frame shape around the optical base material in the form of a transparent plate or sheet, and its width is The thickness is about 0.5 mm to 10 mm, preferably about 1 to 8 mm, and more preferably about 2 to 8 mm.
  • the ultraviolet curable resin composition of the present invention is produced by bonding at least two optical substrates by the above (Step 1) to (Step 2) and, if necessary, further (Step 3). Can be used in the way.
  • the curing shrinkage of the cured product of the ultraviolet curable resin composition of the present invention is preferably 4.0% or less, and particularly preferably 3.0% or less.
  • the transmittance at 400 nm to 800 nm of the cured product of the ultraviolet curable resin composition of the present invention is preferably 90% or more. If the transmittance is 90% or less, light is easily transmitted, and visibility is improved when used in a display device. Further, when the cured product has a high transmittance at 400 to 450 nm, the visibility can be further improved. Therefore, the transmittance at 400 to 450 nm is preferably 90% or more.
  • the ultraviolet curable resin composition of the present invention can be suitably used as an adhesive for producing an optical member by laminating a plurality of optical substrates by the above (Step 1) to (Step 3).
  • an optical base material used in the manufacturing method of the optical member using the resin composition of this invention a transparent plate, a sheet
  • the “optical substrate” means both an optical substrate having no light shielding part on the surface and an optical substrate having a light shielding part on the surface.
  • at least one of a plurality of optical substrates used is an optical substrate having a light shielding part.
  • the position of the light shielding part in the optical substrate having the light shielding part is not particularly limited.
  • a band-shaped light shielding portion having a width of 0.05 to 20 mm, preferably about 0.05 to 10 mm, more preferably about 0.1 to 6 mm is formed in the peripheral portion of the optical substrate.
  • the light-shielding portion on the optical substrate can be formed by attaching a tape, applying a coating or printing.
  • Various materials can be used as the material of the optical substrate used in the present invention. Specifically, resins such as PET, PC, PMMA, a composite of PC and PMMA, glass, COC, COP, plastic (such as acrylic resin), and the like can be given.
  • an optical substrate used in the present invention for example, a transparent plate or sheet, a sheet or transparent plate obtained by laminating a plurality of films or sheets such as polarizing plates, a non-laminated sheet or transparent plate, and a transparent made from inorganic glass Plates (inorganic glass plates and processed products thereof, such as lenses, prisms, ITO glass) and the like can be used.
  • the optical substrate used in the present invention is a laminate composed of a plurality of functional plates or sheets (hereinafter referred to as “functional laminate”) such as a touch panel (touch panel input sensor) or the following display unit in addition to the polarizing plate described above. Also called “body”).
  • Examples of the sheet that can be used as an optical substrate used in the method for producing an optical member using the resin composition of the present invention include an icon sheet, a decorative sheet, and a protective sheet.
  • Examples of the plate (transparent plate) that can be used in the method for producing an optical member using the resin composition of the present invention include a decorative plate and a protective plate.
  • materials for these sheets or plates those listed as materials for transparent plates can be applied.
  • Examples of the material of the touch panel surface that can be used as an optical substrate used in the method for producing an optical member using the resin composition of the present invention include glass, PET, PC, PMMA, a composite of PC and PMMA, COC, and COP. Is mentioned.
  • the thickness of a plate-like or sheet-like optical substrate such as a transparent plate or a sheet is not particularly limited, and is usually about 5 ⁇ m to 5 cm, preferably about 10 ⁇ m to 10 mm, more preferably about 50 ⁇ m to 3 mm. Is the thickness.
  • a plate-like or sheet-like transparent optical base material having a light-shielding portion and the functional laminate described above are used.
  • cured material of the ultraviolet curable resin composition can be mentioned.
  • a display unit such as a liquid crystal display device, as one of the optical base materials, and using an optical functional material as another optical base material.
  • a display unit with an optical functional material (hereinafter also referred to as a display panel) can be manufactured.
  • Examples of the display unit include display devices such as LCD, EL display, EL illumination, electronic paper, and plasma display in which a polarizing plate is attached to glass.
  • Examples of the optical functional material include transparent plastic plates such as acrylic plates, PC plates, PET plates, and PEN plates, tempered glass, and touch panel input sensors.
  • the refractive index of the cured product is 1.45 to 1.55 in order to improve the visibility because the visibility of the display image is further improved.
  • the difference in refractive index from the base material used as the optical base material can be reduced, and the light loss can be reduced by suppressing the irregular reflection of light.
  • Preferred embodiments of the optical member obtained by the production method of the present invention include the following (i) to (vii).
  • An optical base selected from the group consisting of a transparent glass substrate having a light shielding part, a transparent resin substrate having a light shielding part, and a glass substrate on which a light shielding material and a transparent electrode are formed, as the optical base material having the light shielding part.
  • the optical member according to (i), which is a material and the functional laminate is a display unit or a touch panel.
  • a touch panel or touch panel input sensor in which a plate-shaped or sheet-shaped optical substrate having a light-shielding portion is bonded to the surface on the touch surface side of the touch panel using the cured product of the ultraviolet curable resin composition of the present invention.
  • a display panel in which a plate-like or sheet-like optical substrate having a light-shielding part is bonded to the display screen of the display unit using the cured product of the ultraviolet curable resin composition of the present invention.
  • the ultraviolet curable resin composition of the present invention By using the ultraviolet curable resin composition of the present invention and bonding a plurality of optical substrates selected from the above optical substrates by the method described in (Step 1) to (Step 3), The optical member of the invention is obtained.
  • the ultraviolet curable resin composition may be applied to only one of the surfaces facing each other through the cured product layer in the two optical substrates to be bonded, or may be applied to both surfaces. good.
  • the functional laminate is a touch panel or a display unit
  • any one surface of the protective base material having a light shielding part, preferably the light shielding part is provided.
  • the resin composition may be applied to only one of the provided surface and the touch surface of the touch panel or the display surface of the display unit, or may be applied to both of them.
  • a light shielding portion of the protective base material is provided in Step 1, in which a protective base material or a touch panel for protecting the display screen of the display body unit is bonded to the display body unit.
  • the resin composition may be applied to only one of the substrate surface opposite to the surface or the touch surface of the touch panel and the display surface of the display unit, or to both of them.
  • the optical member including the display unit knit obtained by the manufacturing method of the present invention and the optical base material having the light shielding portion can be incorporated into an electronic device such as a television, a small game machine, a mobile phone, and a personal computer.
  • Synthesis example 1 To a reactor equipped with a reflux condenser, a stirrer, a thermometer, and a temperature control device, GI-2000 manufactured by Nippon Soda Co., Ltd. (iodine value: 12.2, hydroxyl value: 46.8 mg ⁇ KOH) as a hydrogenated polybutadiene polyol compound / G) is 545.99 g (0.23 mol), 7.19 g (0.0023 mol) of Exenol 3020 (polypropylene glycol, hydroxyl value: 35.9 mg ⁇ KOH / g) manufactured by Asahi Glass Co., Ltd. as a diol compound is polymerizable.
  • GI-2000 manufactured by Nippon Soda Co., Ltd.
  • Example 1 15 parts by mass of the polyurethane compound (E-1) of Synthesis Example 1, 9.3 parts by mass of S-1800A (isostearyl acrylate) manufactured by Shin-Nakamura Chemical Co., Ltd., Arakawa Chemical Co., which is a compound represented by the formula (1) 33.7 parts by mass of a pine crystal KE-311 and S-1800A manufactured by Kogyo Co., Ltd.
  • Example 2 15 parts by mass of the polyurethane compound (E-1) of Synthesis Example 1, 9.3 parts by mass of S-1800A (isostearyl acrylate) manufactured by Shin-Nakamura Chemical Co., Ltd., Arakawa Chemical Co., which is a compound represented by the formula (1) 33.7 parts by mass of pine crystal KE-359 and S-1800A manufactured by Kogyo Co., Ltd.
  • Example 3 15 parts by mass of the polyurethane compound (E-1) of Synthesis Example 1, 9.3 parts by mass of S-1800A (isostearyl acrylate) manufactured by Shin-Nakamura Chemical Co., Ltd., Arakawa Chemical Co., which is a compound represented by the formula (1) 33.7 parts by mass of Pine Crystal PE-590 manufactured by Kogyo Co., Ltd., 13 parts by mass of LV-100 (polybutene) manufactured by JX Nippon Mining & Energy, GI-2000 manufactured by Nippon Soda Co., Ltd.
  • LAMBSON speed cure TPO (2,4,6-trimethylbenzoyldiphenylphosphine oxide) 0.5 parts by mass
  • BASF IRGACURE184 (1-hydroxycyclohexyl phenyl ketone) 0.5 parts by mass Part
  • PBD (2- (4-biphenyl) -5- (4-t-butylphenyl) -1,3 manufactured by Wako Pure Chemical Industries, Ltd. 4-oxadiazole 0.1 parts by mass, Nippon Kasei Co., Ltd.
  • Examples 1 to 3 are shown in Table 1 and evaluated as follows.
  • the refractive index (25 ° C.) of the resin was measured with an Abbe refractometer (DR-M2: manufactured by Atago Co., Ltd.).
  • Each resin composition of Examples 1 to 3 was applied to a slide glass having a thickness of 1 mm so that the film thickness became 200 ⁇ m, and a release PET film was bonded to the coated surface. Thereafter, the composition was irradiated with ultraviolet rays having an integrated light amount of 4000 mJ / cm 2 through a peeled PET film with a high-pressure mercury lamp (80 W / cm, with ozone-less / IR cut filter). The obtained joined body was put in an environment of 80 ° C. and 85% RH for 48 hours, and then the state of the film 15 minutes after being taken out in the environment of 25 ° C. and 45% RH, and the state of the cured film 3 hours after being taken out. It was confirmed visually. As a result of the evaluation, the compositions of Examples 1 to 3 were all good. ⁇ : No whitening of the film ⁇ : Whitening after 15 minutes but no whitening after 3 hours ⁇ : Whitening after 15 minutes and also whitening after 3 hours
  • a glass joined body was obtained according to the following experimental example. Two glass plates having a size of width 2 cm ⁇ length 3.5 cm ⁇ thickness 1 mm were prepared, and each resin composition was applied to the center of one glass plate so as to form a circle having a thickness of 200 ⁇ m and a diameter of 1 cm. . Thereafter, an electrodeless ultraviolet lamp (D-bulb manufactured by Heraeus Noblelight Fusion Ubuy Co., Ltd.) is used for the obtained coating layer, and the accumulated light quantity is 100 mJ from the atmosphere through an ultraviolet cut filter that blocks a wavelength of 320 nm or less.
  • D-bulb manufactured by Heraeus Noblelight Fusion Ubuy Co., Ltd.
  • the cured product layer having a cured portion present on the lower side (glass plate side) of the coating layer and an uncured portion present on the upper side (atmosphere side) of the coating layer.
  • the ratio of the maximum illuminance in the range of 200 to 320 nm was 3 when the maximum illuminance in the range of 320 to 450 nm was 100.
  • the uncured portion existing on the upper side (atmosphere side) of the coating layer and the other glass plate are bonded in a cross shape (direction crossing 90 ° C.), and the accumulated light amount is 2000 mJ / over through the bonded glass.
  • the cured resin layer was cured by irradiating cm 2 ultraviolet rays to obtain a joined body.
  • the ultraviolet curable resin composition of the present invention has good curability, high whitening resistance, strong adhesion to the base material, and further, after being directly applied to the base material to be bonded, It can be seen that even when cured by irradiating with ultraviolet rays and the other substrate is bonded, it has a high adhesive force.
  • compositions of Examples 1 to 3 were applied to the display surface of the liquid crystal display unit having an area of 3.5 inches and the surface on which the light-shielding portion on the transparent substrate having the light-shielding portion (width 5 mm) was formed on the outer periphery. It apply
  • an electrodeless ultraviolet lamp (D bulb, manufactured by Heraeus Noblelight Fusion Ubuy Co., Ltd.) was used for the obtained coating layer, and the accumulated light quantity from the atmosphere side was 100 mJ / A cured product layer having a cured portion and an uncured portion existing on the atmosphere side was formed by performing ultraviolet irradiation of cm 2 . At this time, the ratio of the maximum illuminance in the range of 200 to 320 nm was 3 when the maximum illuminance in the range of 320 to 450 nm was 100. Thereafter, a liquid crystal display unit and a transparent substrate having a light-shielding portion were bonded together with the uncured portions facing each other.
  • D bulb manufactured by Heraeus Noblelight Fusion Ubuy Co., Ltd.
  • the resin cured product layer is cured by irradiating UV light with an integrated light amount of 2000 mJ / cm 2 from the glass substrate side having the light shielding portion with an ultra-high pressure mercury lamp (TOSCURE752, manufactured by Harrison Toshiba Lighting Co., Ltd.). Produced.
  • the transparent substrate was removed from the obtained optical member, and the cured resin layer of the light shielding part was washed away with heptane, and then the cured state was confirmed. There was no evidence that the uncured resin composition was removed, and the resin in the light shielding portion was sufficiently cured.
  • 1 liquid crystal display unit 2 transparent substrate having light-shielding part, 3 transparent substrate, 4 light-shielding part, 5 ultraviolet curable resin composition (ultraviolet curable resin composition layer), 6 cured material layer having uncured part, 7 resin Hardened material layer, 8 UV

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PCT/JP2016/081646 2015-10-27 2016-10-25 タッチパネル用紫外線硬化型樹脂組成物、それを用いた硬化物及びタッチパネル WO2017073584A1 (ja)

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WO2015111584A1 (ja) * 2014-01-22 2015-07-30 旭硝子株式会社 硬化性樹脂組成物、ならびに、硬化性樹脂組成物を用いた積層体および画像表示装置

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JP2014189758A (ja) * 2013-03-28 2014-10-06 Nippon Shokubai Co Ltd 不飽和カルボニル変性共役ジエン系ポリマーを用いたエネルギー線硬化型樹脂組成物
JP2015007191A (ja) * 2013-06-25 2015-01-15 株式会社日本触媒 不飽和カルボニル変性共役ジエン系水添ポリマーを用いたエネルギー線硬化型樹脂組成物
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WO2019244959A1 (ja) * 2018-06-20 2019-12-26 日本化薬株式会社 接着剤、その硬化物及び光学部材

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