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WO2014092095A1 - Composition durcissable par rayonnement d'énergie actif pour formation de film optique, film optique, et plaque de polarisation - Google Patents

Composition durcissable par rayonnement d'énergie actif pour formation de film optique, film optique, et plaque de polarisation Download PDF

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Publication number
WO2014092095A1
WO2014092095A1 PCT/JP2013/083122 JP2013083122W WO2014092095A1 WO 2014092095 A1 WO2014092095 A1 WO 2014092095A1 JP 2013083122 W JP2013083122 W JP 2013083122W WO 2014092095 A1 WO2014092095 A1 WO 2014092095A1
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Prior art keywords
meth
compound
optical film
composition
group
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English (en)
Japanese (ja)
Inventor
望月　克信
貴之 竹本
谷内　健太郎
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Toagosei Co Ltd
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Toagosei Co Ltd
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Priority claimed from JP2012270790A external-priority patent/JP6127490B2/ja
Priority claimed from JP2012270711A external-priority patent/JP6094193B2/ja
Application filed by Toagosei Co Ltd filed Critical Toagosei Co Ltd
Priority to KR1020157017641A priority Critical patent/KR20150094664A/ko
Publication of WO2014092095A1 publication Critical patent/WO2014092095A1/fr
Anticipated expiration legal-status Critical
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes
    • C09D175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
    • 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
    • C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
    • C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
    • C08G18/622—Polymers of esters of alpha-beta ethylenically unsaturated carboxylic acids
    • C08G18/6237—Polymers of esters containing glycidyl groups of alpha-beta ethylenically unsaturated carboxylic acids; reaction products thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/67—Unsaturated compounds having active hydrogen
    • C08G18/68—Unsaturated polyesters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/81—Unsaturated isocyanates or isothiocyanates
    • C08G18/8108—Unsaturated isocyanates or isothiocyanates having only one isocyanate or isothiocyanate group
    • C08G18/8116—Unsaturated isocyanates or isothiocyanates having only one isocyanate or isothiocyanate group esters of acrylic or alkylacrylic acid having only one isocyanate or isothiocyanate group
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements
    • G02B5/3025—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state
    • G02B5/3033—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state in the form of a thin sheet or foil, e.g. Polaroid
    • G02B5/3041—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state in the form of a thin sheet or foil, e.g. Polaroid comprising multiple thin layers, e.g. multilayer stacks
    • G02B5/305—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state in the form of a thin sheet or foil, e.g. Polaroid comprising multiple thin layers, e.g. multilayer stacks including organic materials, e.g. polymeric layers

Definitions

  • the present invention relates to an active energy ray-curable composition used for forming an optical film and an optical film obtained by curing the composition, and belongs to these technical fields.
  • the “optical film” in the present invention means “optical film or sheet”, and the thickness is not particularly limited. Further, acrylate or methacrylate is represented as (meth) acrylate.
  • Patent Document 1 discloses that photoelasticity is reduced by blending an acrylic resin having negative photoelasticity with a cellulose ester resin having positive photoelasticity.
  • Patent Document 2 achieves both a low photoelastic coefficient and a low retardation by blending polyvinylpyrrolidone with a cellulose ester resin.
  • Patent Document 3 discloses that an optical film made of urethane (meth) acrylate has a small photoelastic coefficient.
  • the TAC film has a retardation in the thickness direction, although the retardation with respect to the incident light in the front direction is small. Such retardation significantly affects viewing angle characteristics as the size of liquid crystal displays increases. Therefore, a material that can achieve both a low photoelastic coefficient and a low retardation is required.
  • the composition described in Patent Document 1 has a large retardation and cannot achieve both a low photoelastic coefficient and a low retardation.
  • the heat and moisture resistance is not sufficient, and when a polarizing plate using the film as a polarizer protective film is used at high temperature or high humidity, the polarizing plate may be deformed, There is a drawback that the performance of the polarizing plate such as the degree of polarization and the hue deteriorates.
  • the composition described in Patent Document 2 is a combination of a cellulose ester resin and polyvinylpyrrolidone, there is a problem that the heat and humidity resistance is worse than that of the composition described in Patent Document 1.
  • the optical film described in Patent Document 3 has an absolute value of the photoelastic coefficient as large as TAC (13 ⁇ 10 ⁇ 12 Pa ⁇ 1 ), which is not satisfactory. Further, the retardation is large, and a low photoelastic coefficient and a low retardation cannot be achieved at the same time.
  • the optical film that has been studied as a material for the polarizer protective film in place of the conventional TAC is not compatible with the low photoelastic coefficient and the low retardation, or even if it is compatible, the heat and moisture resistance is not sufficient,
  • a polarizing plate using the film as a polarizer protective film is used at high temperature or high humidity, there are disadvantages that the polarizing plate is deformed and polarizing plate performance such as degree of polarization and hue is lowered.
  • An object of the present invention is to provide an active energy ray-curable composition for forming an optical film that has both a low photoelastic coefficient and a low retardation, good heat-and-moisture resistance, and excellent flexibility, and an optical obtained from the composition. It aims at providing a film, a polarizer protective film, and a polarizing plate.
  • the inventors of the present invention have a specific active energy ray-curable composition containing a (meth) acrylate-based polymer having a (meth) acryloyl group in the side chain.
  • the present inventors have found that the above problems can be solved and have completed the present invention.
  • the cured product has a photoelastic coefficient of 10 ⁇ 10 ⁇ 12 Pa ⁇ 1 or less, and when measured at a thickness of 40 ⁇ m, the cured product has an in-plane retardation and a thickness direction of 40 ° obliquely.
  • the retardation is 5 nm or less, which makes the cured product less susceptible to birefringence change due to external force.
  • the obtained cured product is excellent in flexibility, and particularly excellent in cutting property and bending resistance. Therefore, the active energy ray-curable optical film of the present invention can be suitably used for a polarizer protective film, and can provide a liquid crystal display excellent in viewing angle characteristics and free from light leakage and white spots.
  • FIG. 1 shows an example of production of an optical film using the composition of the present invention.
  • FIG. 2 shows an example of production of an optical film using the composition of the present invention.
  • the present invention relates to an active energy ray-curable composition for forming an optical film comprising the following component (A) or / and component (B).
  • compound (a2) Acrylate polymer (B) component: (meth) acrylate polymer (b1) having a carboxyl group or a hydroxyl group in the side chain obtained by copolymerizing compound (a2) and a monomer copoly
  • the component (A) is a (meth) acrylate polymer having a (meth) acryloyl group in the side chain which is a reaction product of the polymer (a1) and the compound (a2).
  • the “(meth) acrylate polymer” means a polymer having (meth) acrylate as a main component as a constituent monomer unit.
  • Polymer (a1) The polymer (a1) is a (meth) acrylate polymer having a functional group capable of reacting with a carboxyl group or a hydroxyl group in the side chain.
  • the functional group capable of reacting with a carboxyl group include an epoxy group and an isocyanate group.
  • Examples of the functional group capable of reacting with a hydroxyl group include an isocyanate group.
  • a (meth) acrylate polymer having an epoxy group in the side chain and a (meth) acrylate polymer having an isocyanate group in the side chain are preferable.
  • the polymer (a1) a compound having a functional group capable of reacting with a carboxyl group or a hydroxyl group and an ethylenically unsaturated group [hereinafter referred to as “monomer (a11)”], the monomer (a11), A copolymer with a copolymerizable ethylenically unsaturated group-containing compound (hereinafter referred to as “monomer (a12)”) is preferred.
  • epoxy unsaturated compound a compound having an epoxy group and an ethylenically unsaturated group
  • isocyanate a compound having an isocyanate group and an ethylenically unsaturated group
  • examples of the epoxy unsaturated compound include glycidyl (meth) acrylate, 3,4-epoxycyclohexyl (meth) acrylate, and 4-hydroxybutyl (meth) acrylate glycidyl ether.
  • isocyanate-based unsaturated compound examples include 2-isocyanate ethyl (meth) acrylate, a monoadduct of isophorone diisocyanate and 2-hydroxyethyl acrylate, and the like.
  • the monomer (a11) an epoxy-based unsaturated group compound is preferable from the viewpoint that the cured composition is excellent in optical characteristics.
  • the monomer (a12) is not particularly limited as long as it is a compound that can be copolymerized with the monomer (a11) and has an ethylenically unsaturated group, but can be copolymerized with the monomer (a11).
  • a compound having a (meth) acryloyl group is preferred because of its superiority.
  • Examples of the compound having a (meth) acryloyl group include methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, butyl (meth) acrylate, t-butyl (meth) acrylate, isobornyl (meth) acrylate, cyclohexyl ( (Meth) acrylates such as (meth) acrylate, dicyclopentanyl (meth) acrylate, dicyclopentenyl (meth) acrylate, glycidyl (meth) acrylate; N- (meth) acryloylmorpholine; Acrylamides such as (meth) acrylamide, N-methylolacrylamide, N, N-dimethyl (meth) acrylamide, N, N-diethyl (meth) acrylamide and N, N-dimethylaminopropyl (meth) acrylamide; and (meth) Examples include
  • the monomer (a12) is preferably methyl (meth) acrylate, more preferably methyl methacrylate from the viewpoint of excellent optical properties of the obtained component (A).
  • the proportion of methyl methacrylate is preferably 80% by weight or more.
  • the composition containing the component (A) obtained from the copolymer (a1) having this copolymerization ratio has excellent mechanical properties, particularly elongation at break, of the cured product.
  • the method for producing the copolymer of the monomer (a11) and the monomer (a12) is not particularly limited, and using the above-described compounds, suspension polymerization, emulsion polymerization, bulk polymerization, solution polymerization, etc. These known methods can be used. Among these, the solution polymerization method is preferable because the polymer can be easily produced and does not contain extra impurities such as an emulsifier.
  • the raw material monomer to be used is dissolved in an organic solvent, a thermal polymerization initiator is added, and the mixture is heated and stirred.
  • a thermal radical polymerization initiator is added, and the mixture is heated and stirred.
  • a chain transfer agent can be used to adjust the molecular weight of the polymer, if necessary.
  • Organic solvents used in the solution polymerization method include ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone; esters such as ethyl acetate and butyl acetate; ethers such as propylene glycol monomethyl ether; aromatic carbonization such as toluene and xylene. Hydrogen; and aliphatic hydrocarbons such as hexane, heptane and mineral spirit.
  • thermal polymerization initiators such as azobisisobutyronitrile, azobisisovaleronitrile, azobiscyclohexanecarbonitrile, and azobiscyanovaleric acid; Organic peroxides such as t-butyl peroxypivalate, t-hexyl peroxypivalate, dilauroyl peroxide, di (2-ethylhexyl) peroxydicarbonate, di-t-butyl peroxide and dicumyl peroxide And hydrogen peroxide-iron (II) salt, peroxodisulfate-sodium hydrogen sulfite, cumene hydroperoxide-iron (II) salt, and the like.
  • azo initiators such as azobisisobutyronitrile, azobisisovaleronitrile, azobiscyclohexanecarbonitrile, and azobiscyanovaleric acid
  • Organic peroxides such as t-butyl peroxypivalate,
  • the proportion of the thermal polymerization initiator used is preferably 0.1 to 10 parts by weight with respect to 100 parts by weight of the total amount of all monomers used.
  • Mw weight average molecular weight
  • GPC gel permeation chromatography
  • the compound (a2) is a compound having a carboxyl group or a hydroxyl group and a (meth) acryloyl group and having a number average molecular weight of 180 or more.
  • the number average molecular weight of the compound (a2) (hereinafter referred to as “P-Mn”) means the number average molecular weight based on the acid value or hydroxyl value.
  • P-Mn means the number average molecular weight based on the acid value or hydroxyl value.
  • a compound having a carboxyl group and a (meth) acryloyl group it means a value determined according to the following formula.
  • the cured product of the composition containing the resulting polymer becomes brittle.
  • the P—Mn of the compound (a2) is preferably 180 to 1,000.
  • carboxyl group-containing (meth) acrylic compound examples include caprolactone adduct of (meth) acrylic acid and hydroxyalkyl (meth) acrylate. Examples include acid anhydride adducts.
  • the caprolactone adduct of (meth) acrylic acid is a compound represented by the following formula (1).
  • R 1 represents a hydrogen atom or a methyl group
  • n represents a number of 1 to 10.
  • examples of hydroxyalkyl (meth) acrylate include hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate, hydroxybutyl (meth) acrylate, and the like.
  • examples of the anhydride include phthalic anhydride, hexahydrophthalic anhydride, and succinic anhydride.
  • Specific examples of the hydroxyalkyl (meth) acrylate acid anhydride adduct include hydroxyethyl (meth) acrylate phthalic anhydride adduct and hydroxyethyl (meth) acrylate succinic anhydride adduct.
  • Carboxy group-containing (meth) acrylic compounds are commercially available, and ⁇ -carboxypolycaprolactone monoacrylate [Aronix M-5300 manufactured by Toagosei Co., Ltd.] and hydroxyethyl acrylate phthalic anhydride adduct [manufactured by Toagosei Co., Ltd.] Aronix M-5400] and the like.
  • the carboxyl group-containing (meth) acrylic compound is preferably a caprolactone adduct of (meth) acrylic acid in that the cured product of the composition has excellent mechanical properties, particularly bending resistance.
  • n showing the preferable average addition number of the caprolactone in the said Formula (1), 1 or more and 3 or less are preferable. When the value of n is 1 or more, excellent mechanical properties are exhibited, and when the value of n is 3 or less, excellent optical properties (low photoelasticity) are exhibited.
  • hydroxyl group-containing (meth) acrylic compound examples include caprolactone adduct of hydroxyalkyl (meth) acrylate and polyalkylene glycol mono (meth) acrylate, etc. Is mentioned.
  • the caprolactone adduct of hydroxyalkyl (meth) acrylate is a compound represented by the following formula (2).
  • CH 2 C (R 1 ) COOR 2 O [CO (CH 2 ) 5 O] n H (2)
  • R 1 represents a hydrogen atom or a methyl group
  • R 2 represents a divalent hydrocarbon group
  • n represents a number of 1 to 10.
  • Examples of the divalent hydrocarbon group for R 2 include an ethylene group, a propylene group, and a tetramethylene group.
  • Preferable specific examples of the hydroxyalkyl (meth) acrylate caprolactone adduct include hydroxyethyl (meth) acrylate caprolactone adduct.
  • polyalkylene glycol mono (meth) acrylate examples include polyethylene glycol mono (meth) acrylate and polypropylene glycol mono (meth) acrylate.
  • a caprolactone adduct of hydroxyalkyl (meth) acrylate is preferable in that the cured product of the composition has excellent optical properties.
  • N representing the average number of caprolactone additions in the above formula (2) is preferably 1 or more and 3 or less. When the value of n is 1 or more, excellent mechanical properties are exhibited, and when the value of n is 3 or less, excellent optical properties (low photoelasticity) are exhibited.
  • the compound is commercially available, and a caprolactone adduct of hydroxyethyl acrylate [Placcel FA1DDM manufactured by Daicel Corporation], polyethylene glycol mono (meth) acrylate [Blemmer AE-90, Blemmer PE-90 (both NOF Corporation) And polypropylene glycol mono (meth) acrylate (Blenmer AP-150, Blenmer PP-1000 [both manufactured by NOF Corporation]].
  • the reaction (A) component of the polymer (a1) and the compound (a2) is a reaction product of the polymer (a1) and the compound (a2).
  • the polymer (a1) is a polymer having an epoxy group
  • the reaction between the polymer having an epoxy group and the carboxyl group-containing (meth) acrylic compound may be carried out in accordance with a conventional method.
  • the polymer having an epoxy group and the carboxyl group-containing (meth) acrylic compound are preferably present in the presence of an addition catalyst. Examples of the method include heating and stirring.
  • Catalysts for the addition reaction between epoxy groups and carboxyl groups include tertiary amines such as triethylamine, tripropylamine, tributylamine, dimethyllaurylamine, triethylenediamine and tetramethylethylenediamine; triethylbenzylammonium chloride, trimethylcetylammonium bromide, tetra Quaternary ammonium salts such as butylammonium bromide, quaternary phosphonium salts such as triphenylbutylphosphonium bromide and tetrabutylphosphonium bromide; and phosphine compounds such as triphenylphosphine and tributylphosphine.
  • tertiary amines such as triethylamine, tripropylamine, tributylamine, dimethyllaurylamine, triethylenediamine and tetramethylethylenediamine
  • the carboxyl group-containing (meth) acrylic compound As a reaction ratio of the carboxyl group-containing (meth) acrylic compound with respect to the polymer having an epoxy group, the carboxyl group-containing (meth) acrylic compound is 0.8 with respect to a total of 1 mol of epoxy groups in the polymer having an epoxy group. ⁇ 1.2 mol is preferred.
  • the polymer (a1) is a polymer having an isocyanate group
  • the reaction between the polymer having an isocyanate group and the carboxyl group-containing (meth) acrylic compound may be carried out in accordance with a conventional method, and the polymer having an isocyanate group and the carboxyl group-containing (meth) acrylic compound are preferably present in the presence of an addition catalyst.
  • the method include heating and stirring.
  • the catalyst for the urethanization reaction between an isocyanate group and a carboxyl group include an organometallic compound.
  • organometallic compounds include di-n-butyltin oxide, di-n-butyltin dilaurate, di-n-butyltin, di-n-butyltin diacetate, di-n-octyltin oxide, di-n-octyltin dilaurate, Organic tin compounds such as monobutyltin trichloride, di-n-butyltin dialkyl mercaptan, di-n-octyltin dialkyl mercaptan; organic lead compounds such as lead oleate, lead 2-ethylhexanoate, lead naphthenate, lead octenoate An organic bismuth compound such as bismuth octylate; As the reaction ratio of the carboxyl group-containing (meth) acrylic compound to the polymer having an isocyanate group, the carboxyl group-containing (meth) acrylic compound 1.0 is used with respect to a total of 1
  • the reaction between the polymer having an isocyanate group and the hydroxyl group-containing (meth) acrylic compound may be carried out according to a conventional method.
  • the polymer having an isocyanate group and the hydroxyl group-containing (meth) acrylic compound are preferably heated in the presence of an addition catalyst. Examples include a method of stirring.
  • an addition catalyst include a method of stirring.
  • the same catalyst as in the urethanization reaction described above can be used.
  • the reaction ratio of the hydroxyl group-containing (meth) acrylic compound to the polymer having an isocyanate group is 1.0 to 1 with respect to a total of 1 mol of isocyanate groups in the polymer having an isocyanate group. .2 moles are preferred.
  • the component (B) is a (meth) acrylate polymer having a (meth) acryloyl group in the side chain which is a reaction product of the polymer (b1) and the compound (b2).
  • the reaction of the polymer (b1), the compound (b2) and the polymer (b1) with the compound (b2) will be described.
  • Polymer (b1) The polymer (b1) has in its side chain a carboxyl group or a hydroxyl group obtained by copolymerizing the compound (a2) and a monomer copolymerizable therewith [hereinafter referred to as “monomer (b12)”]. It is a (meth) acrylate polymer.
  • Compound (a2) includes the same compounds as described above, and preferred embodiments are also the same.
  • the monomer (b12) is not particularly limited as long as it is a compound that can be copolymerized with the compound (a2) and has an ethylenically unsaturated group, but is excellent in copolymerizability with the compound (a2) ( A compound having a (meth) acryloyl group is preferred.
  • Specific examples of the monomer (b12) include the same compounds as the monomer (a12).
  • the monomer (b12) is preferably methyl (meth) acrylate, more preferably methyl methacrylate from the viewpoint of excellent optical properties of the obtained component (B).
  • the proportion of methyl methacrylate is preferably 80% by weight or more.
  • the Mw of the polymer (b1) is preferably 2,000 to 100,000, more preferably 3,000 to 80,000, and still more preferably 4,000 to 50,000.
  • the compound (b2) is a compound having a functional group capable of reacting with a carboxyl group or a hydroxyl group and a (meth) acryloyl group.
  • Examples of the functional group capable of reacting with a carboxyl group include an epoxy group and an isocyanate group.
  • Examples of the functional group capable of reacting with a hydroxyl group include an isocyanate group.
  • Examples of the compound (b2) include an epoxy unsaturated compound and an isocyanate unsaturated compound. Specific examples of these compounds include the same compounds as those mentioned for the monomer (a11).
  • the reaction (B) component of the polymer (b1) and the compound (b2) is a reaction product of the polymer (b1) and the compound (b2).
  • the polymer (b1) is a polymer having a carboxyl group
  • the reaction between the polymer having a carboxyl group and the epoxy group-containing (meth) acrylic compound, and the reaction between the polymer having a carboxyl group and the isocyanate group-containing (meth) acrylic compound may be carried out in accordance with conventional methods, and the same method as described above. Is mentioned.
  • an isocyanate group-containing (meth) acrylic compound is preferably used as the compound (b2).
  • the reaction between the polymer having a hydroxyl group and the isocyanate group-containing (meth) acrylic compound may be carried out in accordance with a conventional method, and examples thereof include the same method as described above.
  • the components (A) and (B) (A) and (B) each have a (meth) acryloyl group in the side chain, and the (meth) acryloyl group is not less than a certain amount from the main chain. It is a (meth) acrylate polymer at a position where the distance is maintained.
  • the component Mw is preferably 2,000 to 100,000 in any case. By setting it to 2,000 or more and 100,000 or less, the mechanical properties of the cured product of the composition become excellent.
  • Component Mw is more preferably 3,000 to 80,000, and still more preferably 4,000 to 50,000.
  • the average number of (meth) acryloyl groups in the components (A) and (B) is preferably 1.2 to 5.0 on average per molecule, more preferably 1.2 to 4.0.
  • the proportion of the polymer in which (meth) acryloyl groups are not introduced increases, and the (A) component and (B) component are sufficiently incorporated into the matrix. Therefore, heat resistance, moist heat resistance and brittleness may be insufficient.
  • the average number (f) of (meth) acryloyl groups in the component (A) can be represented by the following formula (1).
  • XA number average molecular weight Mn of polymer (a1) measured by GPC YA: molecular weight of compound unit having reactive group in polymer (a1) ZA: part by weight of compound unit having reactive group in polymer (a1)
  • the reactive group in polymer (a1) is The compound unit has a monomer unit derived from an epoxy unsaturated compound if it is a polymer having an epoxy group, and a monomer unit derived from an isocyanate unsaturated compound if it is a polymer having an isocyanate group. To do.
  • the average number (f) of (meth) acryloyl groups in the component (B) can be expressed by the following formula (2).
  • XB number average molecular weight Mn of polymer (b1) measured by GPC
  • YB Molecular weight of the compound unit having a reactive group in the polymer (b1)
  • ZB Weight part of the compound unit having a reactive group in the polymer (b1)
  • the reactive group in the polymer (b1) is The compound unit having means a monomer unit derived from the compound (a2).
  • the components (A) and (B) preferably have a photoelastic coefficient of the cured product of 5 ⁇ 10 ⁇ 12 Pa ⁇ 1 or less, more preferably ⁇ 5 ⁇ 10 ⁇ 12 to 5 ⁇ 10 ⁇ 12 Pa ⁇ 1. It is preferably ⁇ 5 ⁇ 10 ⁇ 12 to 4 ⁇ 10 ⁇ 12 Pa ⁇ 1 .
  • the photoelastic coefficient is a coefficient representing the ease of occurrence of a change in birefringence due to an external force, and means that the change in birefringence due to an external force is smaller as the value of the photoelastic coefficient is closer to zero.
  • the photoelastic coefficient (C) is a value defined by the following equation (3), where ⁇ is an extensional stress and ⁇ n is a birefringence when stress is applied.
  • C [Pa ⁇ 1 ] ⁇ n / ⁇ (3)
  • ⁇ n is defined by the following equation (4), where n 1 is the refractive index in the direction parallel to the stretching direction and n 2 is the refractive index in the direction perpendicular to the stretching direction.
  • ⁇ n n 1 ⁇ n 2 (4)
  • the photoelastic coefficient in this invention means the value measured at the temperature of 23 degreeC.
  • the active energy ray-curable composition for forming an optical film is an active energy ray-curable composition for forming an optical film comprising the component (A) or / and the component (B) as an essential component.
  • This composition what is necessary is just to follow a conventional method, and only obtaining (A) and / or (B), or using other components further as needed, and these can be obtained by stirring and mixing. it can.
  • the composition of the present invention preferably has a cured product having a photoelastic coefficient of 10 ⁇ 10 ⁇ 12 Pa ⁇ 1 or less.
  • cured material becomes a thing which does not produce birefringence change by external force easily, and when used as a polarizer protective film, light leakage and white spot can be prevented.
  • the composition of the present invention preferably has a cured product having a photoelastic coefficient of ⁇ 10 ⁇ 10 ⁇ 12 Pa ⁇ 1 or more.
  • the composition of the present invention preferably has a front surface of the cured product, an in-plane retardation of 40 ° oblique and a retardation in the thickness direction of 5 nm or less when measured at a thickness of 40 ⁇ m.
  • the in-plane retardation of the cured product when measured at a thickness of 40 ⁇ m is 1 nm or less
  • the in-plane retardation at an oblique angle of 40 ° is 5 nm or less
  • the retardation in the thickness direction is 5 nm or less.
  • the lower limit of each retardation is preferably ⁇ 5 nm.
  • the retardation means a phase difference caused by birefringence when the transmitted light is considered to be decomposed into two linearly polarized lights orthogonal to each other when the linearly polarized light enters the optical film.
  • the in-plane retardation (Re) and the thickness direction retardation (Rth) are nx, ny (where nx ⁇ ny), and nz is the refractive index in the thickness direction.
  • the film thickness is a value defined by the following formulas (5) and (6).
  • the in-plane retardation at an angle of 40 ° means an in-plane retardation when linearly polarized light is incident on the optical film at an angle of 40 °.
  • the ratio when the component (A) and the component (B) are used together may be appropriately set depending on the purpose, but the total amount of the component (A) and the component (B) is a standard.
  • the component (A) is preferably 10 to 90% by weight and the component (B) is 10 to 90% by weight, more preferably 10 to 80% by weight of the component (A) and 20 to 90% by weight of the component (B).
  • the composition of the present invention essentially comprises the component (A) and the component (B), but various components can be blended depending on the purpose. Specifically, an ethylenically unsaturated compound other than the components (A) and (B) [hereinafter referred to as (C) component], a photopolymerization initiator [hereinafter referred to as (D) component], an organic solvent [hereinafter referred to as ( E) component], a compound having an isocyanate group [hereinafter referred to as component (F)], a polymerization inhibitor or / and an antioxidant, a light resistance improver, and a polymer having a negative photoelastic coefficient other than component (B) Etc.
  • C ethylenically unsaturated compound other than the components (A) and (B)
  • D photopolymerization initiator
  • E organic solvent
  • component (F) component a compound having an isocyanate group
  • component (F) a polymerization inhibitor or / and an antioxidant
  • Component (C) is an ethylenically unsaturated compound other than the components (A) and (B).
  • a component is a component mix
  • component (C) examples include (meth) acrylates other than the components (A) and (B) (hereinafter referred to as “other (meth) acrylates”), N-vinyl-2-pyrrolidone, and the like.
  • (meth) acrylates include a compound having one (meth) acryloyl group (hereinafter referred to as “monofunctional (meth) acrylate”) and a compound having two or more (meth) acryloyl groups [hereinafter referred to as “multiple”. Functional (meth) acrylate ”and the like.
  • monofunctional (meth) acrylates include isobornyl (meth) acrylate, dicyclopentenyl (meth) acrylate, dicyclopentanyl (meth) acrylate, cyclohexyl (meth) acrylate, trimethylcyclohexyl (meth) acrylate, 1- Adamantyl (meth) acrylate, methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, n-butyl (meth) acrylate, i-butyl (meth) acrylate, t-butyl (meth) acrylate, hexyl ( (Meth) acrylate, 2-ethylhexyl (meth) acrylate, lauryl (meth) acrylate, stearyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, glycidyl (meth)
  • component (C) only one kind of the above-described compounds may be used, or two or more kinds may be used in combination.
  • urethane (meth) acrylate is preferable in that the mechanical properties of the cured product of the composition, particularly the bending resistance, is excellent.
  • the urethane (meth) acrylate include a reaction product of a polyol, an organic polyisocyanate, and a hydroxyl group-containing (meth) acrylate.
  • Urethane (meth) acrylates include diols having P-Mn of 500 or more (hereinafter collectively referred to as “diol a”), diols having P-Mn of less than 500 (hereinafter collectively referred to as “diol b”). ), Urethane (meth) acrylate which is a reaction product of non-yellowing organic diisocyanate and hydroxyl group-containing (meth) acrylate is preferable.
  • urethane (meth) acrylate which is a reaction product of caprolactone adduct of diol b (diol having P—Mn of less than 500), non-yellowing organic diisocyanate and hydroxyl group-containing (meth) acrylate is used. Particularly preferred.
  • urethane (meth) acrylate a compound (urethane adduct) obtained by an addition reaction between a hydroxyl group-containing (meth) acrylate and a non-yellowing organic polyisocyanate may be used.
  • hydroxyl group-containing (meth) acrylate various compounds can be used. Specifically, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, hydroxybutyl (meth) acrylate, hydroxyhexyl (meta) ) Acrylate, Examples include trimethylolpropane di (meth) acrylate, di or tri (meth) acrylate of pentaerythritol, di or tri (meth) acrylate of ditrimethylolpropane, and di, tri, tetra or penta (meth) acrylate of dipentaerythritol. It is done.
  • a compound having three or less (meth) acryloyl groups and one hydroxyl group is preferable in view of excellent mechanical strength and adhesiveness of the cured product.
  • 2-hydroxyethyl Preference is given to meth) acrylate, 2-hydroxypropyl (meth) acrylate, trimethylolpropane di (meth) acrylate, pentaerythritol tri (meth) acrylate and ditrimethylolpropane tri (meth) acrylate.
  • non-yellowing organic polyisocyanate non-yellowing organic diisocyanate is preferable.
  • Non-yellowing organic diisocyanates include hexamethylene diisocyanate, lysine methyl ester diisocyanate, 2,4,4-trimethylhexamethylene diisocyanate, dimer acid diisocyanate and other aliphatic diisocyanates, isophorone diisocyanate (hereinafter referred to as “IPDI”), 4, Examples thereof include alicyclic diisocyanates such as 4′-methylenebis (cyclohexyl isocyanate), norbornane diisocyanate and ⁇ , ⁇ ′-diisocyanate dimethylcyclohexane, and nurate type trimers thereof.
  • IPDI isophorone diisocyanate
  • organic polyisocyanates may be used alone or in combination of two or more.
  • IPDI is preferable because it is excellent in mechanical strength and optical properties of the cured product.
  • tricyclodecane dimethanol di (meth) acrylate from the viewpoint of the balance between optical properties and mechanical properties.
  • the proportion of the component (C) may be appropriately set according to the purpose, and may be an amount that does not reduce the flexibility of the resulting cured product, but the total amount of the component (A) and / or the component (B).
  • the amount is preferably 1 to 70 parts by weight, more preferably 1 to 50 parts by weight with respect to 100 parts by weight.
  • the blending ratio when urethane (meth) acrylate is used as the component (C) is preferably 2 to 33 parts by weight, more preferably 100 parts by weight of the total amount of (A) and / or (B). 4 to 19 parts by weight.
  • the proportion of urethane (meth) acrylate is 2 parts by weight or more, the mechanical properties are excellent, and when it is 25 parts by weight or less, excellent optical properties are exhibited.
  • a component is a photoinitiator.
  • a component is a component mix
  • Component (D) includes benzyl dimethyl ketal, benzyl, benzoin, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methyl-1-phenylpropan-1-one 1- [4- (2-hydroxyethoxy) phenyl] -2-hydroxy-2-methyl-1-propan-1-one, oligo [2-hydroxy-2-methyl-1- [4-1- (methylvinyl)] Phenyl] propanone, 2-hydroxy-1- ⁇ 4- [4- (2-hydroxy-2-methylpropionyl) benzyl] phenyl ⁇ -2-methylpropan-1-one, 2-methyl-1- [4- ( Methylthio)] phenyl] -2-morpholinopropan-1-one, 2-benzene Dil-2-dimethylamino-1- (4-morpholinophenyl) butan-1
  • the component (D) when the component (C) is included with respect to a total of 100 parts by weight of the component (A) and the component (B), the component (A), the component (B), and ( C) 0.01 to 10% by weight is preferable with respect to 100 parts by weight of the total amount of components, and more preferably 0.1 to 5% by weight.
  • the blending ratio of the component (D) By setting the blending ratio of the component (D) to 0.01% by weight or more, the composition can be cured with an appropriate amount of ultraviolet rays or visible light, and the productivity can be improved. By doing, it can be made the thing excellent in the weather resistance and transparency of hardened
  • composition of the present invention preferably contains an organic solvent as the component (E) for the purpose of improving the coating property to the substrate.
  • component (E) examples include hydrocarbon solvents such as n-hexane, benzene, toluene, xylene, ethylbenzene and cyclohexane; Methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 2-butanol, isobutyl alcohol, 2-methoxyethanol, 2-ethoxyethanol, 2- (methoxymethoxy) ethanol, 2-isopropoxyethanol, 2-butoxy Ethanol, 2-isopentyloxyethanol, 2-hexyloxyethanol, 2-phenoxyethanol, 2-benzyloxyethanol, furfuryl alcohol, tetrahydrofurfuryl alcohol, diethylene glycol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, 1 -Methoxy-2-propanol, 1-ethoxy-2-propanol and propylene glycol monomethyl Alcohol solvents such as ether;
  • Ketone solvents Ester solvents such as ethyl acetate, butyl acetate, isobutyl acetate, methyl glycol acetate, propylene glycol monomethyl ether acetate, cellosolve acetate;
  • Examples include aprotic polar solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, dimethyl sulfoxide, N-methyl-2-pyrrolidone, and ⁇ -butyrolactone.
  • component (E) one or more of the aforementioned compounds can be used.
  • an organic solvent you may add separately and you may use as it is, without isolate
  • the proportion of the component (E) may be appropriately set in consideration of the viscosity of the composition, the purpose of use, etc., but is preferably 10 to 90% by weight, more preferably 40 to 80% by weight in the composition. It is.
  • the component (F) is a compound having an isocyanate group.
  • the component (F) is preferably blended for the purpose of further improving the adhesion between the polarizer and the cured product, particularly in applications where the protective film is directly formed on the polarizer, when the cured product of the composition is used as a polarizer protective film. It is an ingredient to do.
  • the component (F) includes a compound having an ethylenically unsaturated group [hereinafter simply referred to as “(F-1) component”] or a compound having no ethylenically unsaturated group [hereinafter referred to simply as “(F-2) component”. Can be used.
  • the component (F-1) and the component (F-2) will be described.
  • the ethylenically unsaturated group in component (F-1) includes vinyl group, vinyl ether group, (meth) acryloyl group and (meth) acrylamide group, and is easy to produce. And a (meth) acryloyl group is preferred.
  • component (F-1) there are compounds having one isocyanate group and compounds having two or more, and one isocyanate group is used because the storage stability of the viscosity of the composition is excellent.
  • examples of the skeleton connecting the ethylenically unsaturated group and the isocyanate group include various skeletons as long as they can bond the ethylenically unsaturated group and the isocyanate group.
  • examples thereof include a saturated hydrocarbon skeleton (an alkylene skeleton, an oxyalkylene skeleton, etc.) and an aromatic hydrocarbon skeleton which may be included.
  • any of a low molecular weight compound and a high molecular weight compound can be used.
  • specific examples of the low molecular weight compound include the following compounds.
  • examples of the compound in which these two groups are linked by an alkylene skeleton include (meth) (meth) acrylic acid such as 2- (meth) acryloyloxyethyl isocyanate.
  • Acryloyloxyalkyl isocyanate examples include (meth) acryloyloxyalkoxyalkyl isocyanate such as 2- (meth) acryloyloxyethoxyethyl isocyanate, and Examples of the compound in which these two groups are linked by an aromatic hydrocarbon skeleton include 2- (meth) acryloyloxyphenyl isocyanate.
  • examples of compounds in which these two groups are linked by a branched saturated hydrocarbon skeleton include 1,1-bis [(meta ) Acrylyloxymethyl] ethyl isocyanate.
  • Examples of the component (F-1) include a reaction product of polyisocyanate and a hydroxyl group-containing (meth) acrylate.
  • Examples of the polyisocyanate include diisocyanate and triisocyanate.
  • Examples of the diisocyanate include aliphatic diisocyanates such as hexamethylene diisocyanate and trimethylhexamethylene diisocyanate; aromatic diisocyanates such as tolylene diisocyanate, 4,4′-diphenylmethane diisocyanate, xylene diisocyanate and naphthalene diisocyanate; isophorone diisocyanate, 4,4 ′.
  • -Alicyclic diisocyanates such as dicyclohexylmethane diisocyanate, norbornene diisocyanate and hydrogenated xylene diisocyanate.
  • the triisocyanate include 1,6,11-undecane triisocyanate, 1,3,6-hexamethylene triisocyanate, and bicycloheptane triisocyanate.
  • Examples of the high molecular weight compound in the component (F-1) include polymers of hydroxyalkyl (meth) acrylate and diisocyanate. Such a compound is commercially available, and examples thereof include Laromar LR9000 manufactured by BASF, which is a polymer of 2-hydroxyethyl acrylate and hexamethylene diisocyanate.
  • the molecular weight of the component (F-1) can be from low to high, but the composition can have a low viscosity, and the composition has excellent curability.
  • low molecular weight compounds are preferred. That is, in a compound having one ethylenically unsaturated group and one isocyanate group, a compound in which these two groups are linked by an alkylene skeleton, a compound in which these two groups are linked by an oxyalkylene skeleton, and , A compound in which these two groups are linked by an aromatic hydrocarbon skeleton, and more specifically, 2- (meth) acryloyloxyethyl isocyanate, 2- (meth) acryloyloxyethoxyethyl isocyanate and 2- ( (Meth) acryloyloxyphenyl isocyanate is preferred.
  • the (meth) acryloyloxy is used because the composition is in a liquid form without crystallizing and there is no deformation of the substrate due to heat generation during curing.
  • Alkyl isocyanate is preferred.
  • (F-1) Component may be used alone or in combination of two or more.
  • ⁇ (F-2) component (F-2) components include tolylene diisocyanate, phenylene diisocyanate, chlorophenylene diisocyanate, xylylene diisocyanate, cyclohexane diisocyanate, hexamethylene diisocyanate, tetramethylene diisocyanate, norbornene diisocyanate , Isophorone diisocyanate, xylylene diisocyanate, 4,4′-diphenylmethane diisocyanate, dicyclohexylmethane diisocyanate, phthalene diisocyanate, dimethyldiphenyl diisocyanate, dianiline diisocyanate, tetramethylxylylene isocyanate, trimethylhexamethylene diisocyanate, lysine diisocyanate, etc.
  • isocyanate compounds are examples include adduct isocyanate compounds added to polyfunctional alcohols such as limethylol propane, isocyanurate compounds, biuret type compounds, allophanate type compounds of these isocyanate compounds, and further known polyether polyols, polyester polyols, acrylic polyols. , Urethane prepolymer type isocyanate compounds obtained by addition reaction of polybutadiene polyol, polyisoprene polyol and the like.
  • (F-2) Component may be used alone or in combination of two or more. Further, the component (F-1) and the component (F-2) can be used in combination.
  • the ratio of the component (F) is preferably 1 to 20 parts by weight, more preferably 1 to 10 parts by weight with respect to 100 parts by weight of the component (A).
  • the ratio of a component into 1 weight part or more adhesiveness with a polyvinyl alcohol-type polarizer can be improved, and the storage stability of a composition is ensured by setting it as 20 weight part or less on the other hand. can do.
  • polymerization inhibitor or / and antioxidant It is preferable to add a polymerization inhibitor or / and an antioxidant to the composition of the present invention because the storage stability of the composition of the present invention can be improved.
  • a polymerization inhibitor hydroquinone, hydroquinone monomethyl ether, 2,6-di-tert-butyl-4-methylphenol, and various phenolic antioxidants are preferable, but sulfur secondary antioxidants, phosphorus secondary antioxidants are preferable. A secondary antioxidant or the like can also be added.
  • the total blending ratio of these polymerization inhibitors or / and antioxidants includes the component (C) with respect to a total of 100 parts by weight of the component (A) and the component (B), the component (A),
  • the content is preferably 0.001 to 3% by weight, more preferably 0.01 to 0.5% by weight, based on 100 parts by weight of the total amount of the component (B) and the component (C).
  • the composition of the light resistance improver present invention the light resistance improving agent such as an ultraviolet absorber or a light stabilizer may be added.
  • ultraviolet absorbers include 2- (2′-hydroxy-5-methylphenyl) benzotriazole, 2- (2′-hydroxy-3 ′, 5′-di-t-butylphenyl) benzotriazole, 2- (2 Benzotriazole compounds such as'-hydroxy-3'-t-butyl-5'-methylphenyl)benzotriazole; Triazine compounds such as 2,4-bis (2,4-dimethylphenyl) -6- (2-hydroxy-4-isooctyloxyphenyl) -s-triazine; 2,4-dihydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxy-4'-methylbenzophenone, 2,2'-dihydroxy-4-methoxybenzophenone, 2,4,4'-tri Hydroxybenzophenone, 2,2 ', 4,4'-t
  • Examples of the light stabilizer include N, N′-bis (2,2,6,6-tetramethyl-4-piperidyl) -N, N′-diformylhexamethylenediamine, bis (1,2,2,6). , 6-Pentamethyl-4-piperidyl) -2- (3,5-ditertiarybutyl-4-hydroxybenzyl) -2-n-butylmalonate, bis (1,2,2,6,6-pentamethyl-4 -Piperidinyl) sebacate, etc., low molecular weight hindered amine compounds; N, N′-bis (2,2,6,6-tetramethyl-4-piperidyl) -N, N′-diformylhexamethylenediamine, bis (1, And hindered amine light stabilizers such as high molecular weight hindered amine compounds such as 2,2,6,6-pentamethyl-4-piperidinyl) sebacate.
  • the blending ratio of the light fastness improver includes the component (A), the component (B) and the component (C) when the component (C) is included with respect to 100 parts by weight of the component (A) and the component (B). ) It is preferably 0 to 5% by weight, more preferably 0 to 1% by weight, based on 100 parts by weight of the total amount of the components.
  • the composition of the present invention can employ various methods of use depending on the purpose of forming the optical film. Specifically, a method of applying a composition to a substrate and irradiating it with an active energy ray to cure, applying a composition to a substrate and bonding it to another substrate, and then irradiating with an active energy ray. And a curing method, a method of pouring the composition into a mold having a recess, and curing by irradiation with active energy rays.
  • any of a peelable substrate and a substrate having no releasability can be used.
  • the peelable substrate include a release-treated film, a surface untreated film having peelability, and a metal (hereinafter collectively referred to as “release material”).
  • release material include silicone-treated polyethylene terephthalate film, surface untreated polyethylene terephthalate film, surface untreated cycloolefin polymer film, and surface untreated OPP film (polypropylene).
  • silicone-treated polyethylene terephthalate film surface untreated polyethylene terephthalate film, surface untreated cycloolefin polymer film, and surface untreated OPP film (polypropylene).
  • the surface roughness (centerline average roughness) Ra is 150 nm or less as a peelable substrate.
  • a material is preferably used, and a substrate of 1 to 100 nm is more preferable.
  • the haze is preferably 3.0% or less.
  • Specific examples of the substrate include a surface untreated polyethylene terephthalate film and a surface untreated OPP film (polypropylene).
  • the surface roughness Ra means a value obtained by measuring the surface roughness of the film and calculating an average roughness.
  • non-releasable substrate examples include various plastics other than those described above, such as cellulose acetate resins such as polyvinyl alcohol, triacetyl cellulose and diacetyl cellulose, acrylic resin, polyester, polycarbonate, polyarylate, polyethersulfone, norbornene and the like. And cyclic polyolefin resins having a cyclic olefin as a monomer.
  • plastics other than those described above such as cellulose acetate resins such as polyvinyl alcohol, triacetyl cellulose and diacetyl cellulose, acrylic resin, polyester, polycarbonate, polyarylate, polyethersulfone, norbornene and the like.
  • cyclic polyolefin resins having a cyclic olefin as a monomer.
  • the raw material components are used. It is preferable to use a purified product after stirring and mixing.
  • a method for purifying the composition a method of filtering the composition is simple and preferable. Examples of the filtration method include pressure filtration. The filtration accuracy is preferably 10 ⁇ m or less, more preferably 5 ⁇ m or less. The lower the filtration accuracy, the better. However, if the filter accuracy is too small, the filter is likely to be clogged, and the filter replacement frequency increases and the productivity is lowered. Therefore, the lower limit is preferably 0.1 ⁇ m.
  • a coating method it may be appropriately set according to the purpose, and conventionally known bar coat, applicator, doctor blade, knife coater, comma coater, reverse roll coater, die coater, lip coater, gravure coater, micro gravure coater, etc. The method of coating with is mentioned.
  • Examples of active energy rays include electron beams, ultraviolet rays and visible rays.
  • an electron beam is more preferable in that it is not always necessary to add a photopolymerization initiator and the cured product is excellent in heat resistance and light resistance.
  • the irradiation conditions such as dose and irradiation intensity in the active energy ray irradiation may be appropriately set according to the composition to be used, the substrate, the purpose and the like.
  • composition of the present invention can be preferably used for the production of an optical film.
  • optical film will be described. In the following, a part of the description will be given with reference to FIGS.
  • Manufacturing method of optical film As a manufacturing method of an optical film, what is necessary is just to follow a conventional method, for example, after apply
  • FIG. 1 shows an example of a preferable method for producing an optical film composed of a release material / cured product.
  • (1) means a release material.
  • the composition is a solventless type (FIG. 1: F1)
  • the composition is applied to a release material [FIG. 1: (1)].
  • the composition contains an organic solvent or the like (FIG. 1: F2)
  • the composition is applied to a release material [FIG. 1: (1)] and then dried to evaporate the organic solvent or the like (FIG. 1: 1). -1).
  • an optical film composed of the release material / cured product is obtained.
  • the active energy ray is usually irradiated from the composition layer side, but can also be irradiated from the release material side.
  • a release material is used as the substrate (1), an optical film composed of the release material / cured product can be produced.
  • the coating amount of the composition of the present invention may be appropriately selected according to the application to be used, but it is preferable that the coating is performed so that the film thickness after drying the organic solvent or the like is 5 to 200 ⁇ m.
  • the thickness is preferably 10 to 100 ⁇ m.
  • the composition When the composition contains an organic solvent or the like, it is heated and dried after coating to evaporate the organic solvent or the like.
  • a heating / drying method a method of passing through a furnace equipped with a heating device, or it can be carried out by blowing air,
  • the heating / drying conditions may be appropriately set according to the organic solvent used, and examples thereof include a method of heating to a temperature of 40 to 150 ° C.
  • the proportion of the organic solvent is preferably 1% by weight or less.
  • the irradiation conditions such as dose and irradiation intensity in the active energy ray irradiation may be appropriately set according to the composition to be used, the substrate, the purpose and the like.
  • FIG. 2 shows an example of a preferable method for producing an optical film composed of a release material / cured product / release material.
  • (1), (3), and (4) mean release materials.
  • the composition is a solventless type (FIG. 2: F1)
  • the composition is applied to a release material [FIG. 2: (1)].
  • the composition contains an organic solvent or the like (FIG. 2: F2)
  • the composition is applied to a release material [FIG. 2: (1)] and then dried to evaporate the organic solvent (FIG. 2: 2). -1).
  • the composition layer (2) is laminated with the release material (3) and then irradiated with active energy rays, or after being irradiated with active energy rays, the release material (4) is laminated to obtain a release material, a cured product and a release material. An optical film formed in this order is obtained.
  • an optical film can also be manufactured using a non-mold release base material.
  • a non-releasable base material is used in place of the release material of (1) and is cured by irradiation with active energy rays in the same manner as described above, and is composed of a non-releasable base material / cured product.
  • An optical film can also be manufactured.
  • a non-releasing substrate is used as the release material of any of (1), (3) and (4), and cured by irradiation with active energy rays in the same manner as described above.
  • An optical film composed of a release material / cured product / non-releasing substrate or an optical film composed of a non-releasing substrate / cured material / non-releasing substrate can also be produced.
  • Specific examples of the embodiment include a method in which a polarizer is used as a non-releasing substrate, a composition is applied, an active energy ray is irradiated, and a protective film is directly formed on the polarizer. .
  • This embodiment will be described in more detail in later section 6-2-2.
  • a transparent plastic film is used as a non-releasing substrate, and after coating the composition, a metal mold is bonded to the coating film as a release material, and the transparent plastic film is used. Examples include a method of irradiating active energy rays from the side. This embodiment will be described in more detail later in 6-2-3.
  • the optical film is produced by applying the composition to a substrate.
  • the composition is formed on a mold having a specific recess.
  • An optical film can also be produced by pouring an object and irradiating active energy rays in the same manner as described above to cure the composition.
  • optical film formed from the composition of the present invention can be used for various optical uses, more specifically, a polarizer protective film for polarizing plates used for liquid crystal display devices, etc.
  • a polarizer protective film for polarizing plates used for liquid crystal display devices etc.
  • Examples include a support film for a prism sheet, a light guide film, and a base film of a transparent conductive film.
  • Other applications include lens sheet lenses such as Fresnel lenses and lenticular lenses, support films, and the like, and lenticular lenses can be used for naked-eye 3D displays.
  • a polarizing plate using a polarizer protective film (hereinafter simply referred to as “protective film”) formed from the composition of the present invention, a polarizing plate having a protective film directly formed on the polarizer, and a lens sheet will be described.
  • the polarizing plate is a structure in which a protective film is laminated on at least one surface of a polarizer.
  • the polarizing plate may be manufactured by directly coating and curing the composition of the present invention on at least one surface of a polarizer to form a protective film, or may be manufactured by bonding a polarizer and a protective film. .
  • polarizer various materials can be used as long as they have a function of selectively transmitting linearly polarized light in one direction from natural light.
  • an iodine polarizing film in which iodine is adsorbed and oriented on a polyvinyl alcohol film a dye polarizing film in which a dichroic dye is adsorbed and oriented on a polyvinyl alcohol film, and a dichroic dye is coated.
  • examples include a fixed coating type polarizer.
  • These iodine-based polarizing films, dye-based polarizing films, and coating-type polarizers have a function of selectively transmitting linearly polarized light in one direction from natural light and absorbing linearly polarized light in the other direction.
  • the polarizing plate of the present invention is a polarizing plate in which the optical film of the present invention is laminated as a protective film on at least one surface of a polarizer, and is bonded by an adhesive.
  • any adhesive can be used for the adhesive between the polarizer and the protective film in consideration of the respective adhesiveness.
  • the adhesive include polyvinyl alcohol-based water-based adhesives, solvent-based adhesives, hot-melt-based adhesives, and solvent-free adhesives, and solvent-free active energy ray-curable adhesives. It can be used suitably.
  • the active energy ray curable adhesive include a photo cation curable adhesive, a photo radical curable adhesive, and a hybrid adhesive that uses both photo cation curing and photo radical curing.
  • the photo cation curable adhesive include photo cation curable compounds such as epoxy compounds and oxetane compounds, and adhesives including a photo cation polymerization initiator.
  • photo-radical curable adhesive examples include photo-radical curable compounds such as (meth) acrylates, vinyl ethers and vinyl compounds, and adhesives containing a photo-radical polymerization initiator.
  • the hybrid adhesive examples include an adhesive containing the above-described photocationic curable compound, photoradical curable compound, photocationic polymerization initiator, and photoradical polymerization initiator.
  • the protective film of the present invention can be used on one side and a protective film other than the protective film of the present invention (hereinafter referred to as “other protective film”) can be used on the other side.
  • other protective films include cellulose acetate resin films such as triacetyl cellulose and diacetyl cellulose, acrylic resin films, polyester resin films, and cyclic polyolefin resin films containing cyclic olefins such as norbornene as monomers.
  • the film which has phase difference may be sufficient.
  • Polarizing plate in which a protective film is directly formed on a polarizer In the above description, a polarizing plate in which a polarizer and a protective film are bonded using an adhesive has been described.
  • the composition of the present invention can be applied directly to a polarizer and then cured by irradiation with an active energy ray to produce a protective film. That is, the present invention is also a polarizing plate in which a film-like cured product of the active energy ray-curable composition described above is directly formed as a protective film on at least one surface of a polarizer.
  • the cured product of the composition is directly formed on at least one surface of the polarizer, it is possible to reduce the amount of foreign matter mixed in and to reduce the thickness of the polarizing plate as compared with bonding using an adhesive or the like.
  • the composition used in this application is preferably a composition containing the component (F) (isocyanate-containing compound) in addition to the component (A) or / and the component (B).
  • the polarizer since the polarizer can be prevented from being deteriorated, an ultraviolet curable composition is preferable, and a composition containing a component (D) (photopolymerization initiator) is more preferable.
  • a component containing urethane (meth) acrylate as the component (C) is preferable.
  • the composition containing (E) component organic solvent
  • These components can be used in the preferred proportions described above.
  • the polarizing plate various forms can be adopted as long as a cured product of the composition is formed on at least one surface of the polarizer.
  • the polarizing plate of the following structure etc. which formed one layer of the hardened
  • cured material / polarizer In addition to this, the polarizing plate of the following structure etc. which formed two layers of the hardened
  • a polarizing plate having the following constitution having one layer of a cured product laminated on one side of a polarizer and having a base material that can be peeled off from the cured product.
  • Polarizer / cured product / peelable substrate In addition to this, two layers of the cured product of the composition are formed on both sides of the polarizer, and each cured product has a peelable substrate as described below.
  • a polarizing plate etc. are mentioned. Peelable substrate / cured product / polarizer / cured product / peelable substrate
  • the detachable substrate examples include the above-described release material, and specific examples similar to those described above can be given.
  • a substrate having a surface roughness Ra of 150 nm or less should be used as a peelable substrate. Is preferred.
  • Specific examples of the substrate include a surface untreated polyethylene terephthalate film and a surface untreated OPP film (polypropylene).
  • the surface roughness Ra means a value obtained by measuring the surface roughness of the film and calculating an average roughness.
  • the composition is directly applied to the polarizer and irradiated with an active energy ray to cure, and the active energy ray is further applied after the composition is applied to a peelable substrate and bonded to the polarizer.
  • the method of irradiating and hardening and peeling a base material etc. is mentioned.
  • the composition of the resulting optical film is stirred and mixed in order to prevent the introduction of foreign substances, the occurrence of defects such as voids, and the excellent optical properties. Then, it is preferable to use a purified one, and the same method as described above can be used. What is necessary is just to set suitably as a coating method according to the objective, The method similar to the above is mentioned.
  • Examples of the active energy rays include ultraviolet rays, visible rays, and electron beams.
  • the active energy ray since the active energy ray is directly irradiated to the polarizer, deterioration of the polarizer becomes a problem. Since these problems can be prevented, ultraviolet rays and visible rays are preferable among these, and ultraviolet rays are more preferable. What is necessary is just to set suitably irradiation conditions, such as irradiation intensity
  • FIG. 1 means a polarizer.
  • F1 solventless type
  • F2 organic solvent or the like
  • FIG. 1: F2 polarizer [FIG. 1: (1)] and then dried to evaporate the organic solvent
  • a polarizing plate composed of a polarizer / cured product is obtained by irradiating active energy rays to a sheet having the composition layer (2) formed on the polarizer.
  • the active energy ray is usually irradiated from the composition layer side, but can also be irradiated from the polarizer side.
  • the coating amount of the composition of the present invention may be appropriately selected depending on the application to be used, but it is preferable that the coating is performed so that the film thickness after drying the organic solvent or the like is 5 to 100 ⁇ m.
  • the thickness is preferably 10 to 40 ⁇ m.
  • the composition contains an organic solvent or the like, it is heated and dried after coating to evaporate the organic solvent or the like.
  • the heating / drying method include the same methods and conditions as described above.
  • the method of heating to the temperature of 80 degrees C or less at which a polarizer does not heat-shrink is preferable.
  • the proportion of the organic solvent is preferably 1% by weight or less.
  • Irradiation conditions such as irradiation intensity and dose in active energy ray irradiation may be appropriately set according to the composition to be used, the substrate, and the like.
  • a part of the “release material” in FIG. 2 is replaced with a “polarizer”.
  • a polarizer an example of the preferable manufacturing method of the polarizing plate comprised from polarizer / hardened
  • (1) means a release material
  • (3) means a polarizer.
  • the composition is a solventless type (FIG. 2: F1)
  • the composition is applied to a release material [FIG. 2: (1)].
  • the composition contains an organic solvent or the like (FIG. 2: F2)
  • the composition is applied to a release material [FIG. 2: (1)] and then dried to evaporate the organic solvent (FIG. 2: 2). -1).
  • active energy rays After laminating the polarizer (3) on the sheet having the composition layer (2) formed on the release material, the release material, the cured product, and the polarizer are formed in this order. A polarizing plate is obtained, and the release material is peeled off in use.
  • the composition of the present invention can be preferably used for producing a lens sheet.
  • the lens sheet include a lens sheet lens such as a Fresnel lens and a lenticular lens, a support film, and the like.
  • the lenticular lens can also be used for a naked-eye 3D display.
  • the composition is applied or poured onto a base material, and a mold having a range shape on the coated surface is bonded (hereinafter referred to as “case 1”), Or after coating or pouring the composition into a mold having a lens shape, and pasting a sheet-like substrate on the coated surface (hereinafter referred to as “Case 2”), Examples include a method of irradiating active energy rays from the substrate side and curing.
  • the substrate examples include non-releasable substrates, and conventional materials known as lens sheet support films can be used. Specifically, it is a transparent plastic film, and in addition to the lens sheet support film produced from the composition of the present invention, sheet-like materials such as methacrylic resin, polycarbonate resin, methyl methacrylate-styrene resin and styrene resin. Can be used.
  • the composition is applied onto a substrate.
  • a purified product after stirring and mixing the raw material components and examples thereof include the same method as described above. What is necessary is just to set suitably as a coating method according to the composition to be used and the objective, and the method similar to the above is mentioned.
  • the coating amount of the composition of the present invention may be appropriately selected according to the application to be used, but it is preferable that the coating is performed so that the film thickness after drying the organic solvent or the like is 5 to 200 ⁇ m. The thickness is preferably 10 to 100 ⁇ m.
  • the same method as described above may be used by heating and drying after coating to evaporate the organic solvent or the like.
  • the material of the mold having a lens shape is not particularly limited, and examples thereof include metals such as brass and nickel, and resins such as epoxy resins. It is preferable that the mold is made of metal in view of the long life of the mold.
  • Case 2 the composition is applied or poured into a mold having a lens shape, and a sheet-like substrate is bonded to the coated surface.
  • the mold having a lens shape include the same as described above.
  • the method for applying the composition include the same methods as described above.
  • the composition of the present invention can be poured (injected) between a mold having a target lens shape and a substrate.
  • the same method as described above may be used by heating and drying after application to evaporate the organic solvent or the like.
  • An active energy ray is irradiated from the base material side with respect to the laminated body comprised from the base material / composition film / molding die obtained in Case 1 or Case 2.
  • the same one as described above can be used.
  • a lens sheet is obtained by removing the mold from the cured product.
  • parts means parts by weight.
  • MMA methyl methacrylate
  • GMA glycidyl methacrylate
  • MIBK methyl isobutyl ketone
  • V-65 manufactured by Kogyo Co., Ltd.
  • MEK methyl ethyl ketone
  • BHT 2,6-di-t-butyl-4-methylphenol
  • TBAB tetrabutylammonium bromide
  • Production Examples A2 to A6 [Production of component (A)] A component (A) was produced in the same manner as in Production Example A1, except that the type and amount of raw materials were changed as shown in Table 1.
  • GMA Glycidyl methacrylate MOI: 2-isocyanate ethyl methacrylate [Karenz MOI, Showa Denko KK]
  • -MMA methyl methacrylate-MA: methyl acrylate-PV: t-hexyl peroxypivalate, perhexyl PV manufactured by NOF Corporation
  • M5300 caprolactone adduct of acrylic acid [Aronix M5300, manufactured by Toagosei Co., Ltd., average degree of polymerization of caprolactone: 2, P-Mn; 300]
  • FA2D Caprolactone adduct of 2-hydroxyethyl acrylate [Placcel FA2D, manufactured by Daicel Corporation, average polymerization degree of caprolactone: 2, P-Mn; 344]
  • FM5 Caprolactone adduct of 2-hydroxyethyl methacryl
  • BHT 2,6-di-t-butyl-4-methylphenol as a polymerization inhibitor
  • the MEK solution containing urethane acrylate (hereinafter referred to as “UA-1”) (solid content 80%) )
  • the polystyrene-equivalent weight average molecular weight (hereinafter referred to as Mw) of UA-1 was 2,400 as measured by GPC (solvent: tetrahydrofuran, column: HSPgel HR MB-L manufactured by Waters).
  • Examples F1 to F19 and Comparative Examples F1 to F5 (Production of optical film by electron beam curing)
  • Examples 1 to 10 and Comparative Examples 1 to 6 were applied to a film “Lumirror 50-T60” (surface untreated polyethylene terephthalate film, thickness 50 ⁇ m, hereinafter referred to as “Lumirror”) manufactured by Toray Industries, Inc. having a width of 300 mm and a length of 300 mm.
  • the composition obtained in (1) was coated with an applicator so that the film thickness after drying at 120 ° C. for 10 minutes was 40 ⁇ m.
  • Examples F1 to F19 are optical films obtained from the compositions of Examples 1 to 19 which are the compositions of the present invention, and the photoelastic coefficient is the photoelasticity of a TAC conventionally used as a polarizer protective film. The coefficient was smaller than 13 ⁇ 10 ⁇ 12 Pa ⁇ 1 , and there was no concern about light leakage or white spots.
  • Comparative Example F1 is an optical film produced from the composition of Comparative Example 1 containing an acrylic polymer having an acryloyl group different from the component (A), but was fragile and low in mechanical properties.
  • Comparative Examples F2 and F3 are optical films obtained from the compositions of Comparative Examples 2 and 3 from which the ratio of the acrylic polymer having an acryloyl group was reduced and the ratio of the component (C) was increased.
  • Comparative Example F4 is an optical film produced from the composition of Comparative Example 4 using an acrylic polymer having an acryloyl group different from component (B), and was fragile and low in mechanical properties.
  • Comparative Example F5 is an optical film obtained from the composition of Comparative Example 4 in which the ratio of the acrylic polymer having an acryloyl group is reduced and the ratio of the component (C) is increased, but the mechanical properties are improved. However, the photoelastic coefficient was high and a decrease in optical properties was observed.
  • the 30-micrometer-thick polarizer (henceforth polarizer P).
  • the obtained polarizer P was measured for polarization degree and single transmittance using a spectrophotometer with a polarizing prism (UV-2200, manufactured by Shimadzu Corporation), it was 99.99% and 43.1%, respectively. there were.
  • Examples P1 to P19 (Production of polarizing plate)
  • the optical film obtained in Examples F1 to F19 was used as the polarizer protective film, and the adhesive UVX was applied to both sides of the polarizer P with a film thickness of 5 ⁇ m, and the optical film was bonded together.
  • the conveyor speed is adjusted by a conveyor type ultraviolet irradiation device (high pressure mercury lamp, lamp height 15 cm, 365 nm irradiation intensity 370 mW / cm 2 (measured value of UV POWER PUCK manufactured by Fusion UV Systems Japan Co., Ltd.)
  • An ultraviolet ray with an integrated light quantity of 220 mJ / cm 2 was applied to obtain a polarizing plate (width 100 mm ⁇ length 100 mm).
  • no corona treatment was performed on any of the polarizer protective films.
  • Examples D1 to D10 Production of compositions
  • the components shown in Table 9 below were charged into a stainless steel container at the ratio shown in Table 9, and stirred with a magnetic stirrer while heating the components other than the component (F). Then, (F) component was thrown in at room temperature, it stirred until it became uniform, and the composition was obtained.
  • the solution of the component (A) obtained in Production Example A6 and the solution of the component (C) obtained in Production Examples C1 to C2 are used.
  • the ratio contained in the component (A), component (C) and component (E) [the sum of the component (A) and the component (E) brought in from the solution (C)] is described separately. ing.
  • SUCCX-001 Urethane adduct compound obtained by addition reaction of IPDI and 2-hydroxypropyl acrylate, Art Resin SUCCX-001 manufactured by Negami Kogyo Co., Ltd.
  • Irg184 1-hydroxycyclohexyl phenyl ketone, IRGACURE 184 manufactured by BASF Japan MEK: methyl ethyl ketone AOI: 2-acryloyloxyethyl isocyanate, Karenz AOI manufactured by Showa Denko KK TPA-100: Isocyanate compound mainly composed of 1,6-hexamethylene diisocyanate nurate-type trimer, Duranate TPA-100 manufactured by Asahi Kasei Chemicals Corporation
  • Examples D1 to D10 (measurement of photoelastic coefficient) UV curing obtained in Examples D1 to D10 on a film “Lumirror 50-T60” (surface untreated polyethylene terephthalate film, thickness 50 ⁇ m, hereinafter referred to as “Lumirror”) manufactured by Toray Industries, Inc. having a width of 300 mm and a length of 300 mm
  • the mold composition was applied with an applicator so that the film thickness after drying at 80 ° C. for 10 minutes was 20 ⁇ m.
  • composition layer was coated with a conveyor-type ultraviolet irradiation device (high pressure mercury lamp, lamp height 17 cm, 365 nm irradiation intensity 200 mW / cm 2 (Fusion UV Systems Japan Co., Ltd. UV POWER).
  • the conveyor speed was adjusted according to the measurement value of PUCK)), and an ultraviolet ray was irradiated with an integrated light amount of 400 mJ / cm 2 to obtain an optical film. After curing, it was peeled off from Lumirror and used for measurement of photoelastic coefficient.
  • the obtained optical film was cut into 15 mm ⁇ 60 mm, the in-plane retardation value was measured by the same method as described above, and the photoelastic coefficient was obtained from the slope of the approximate straight line prepared according to the above formula. The results are shown in Table 10.
  • Examples PD1 to 10 Manufacture of polarizing plates
  • an applicator was used so that the film thickness after drying at 80 ° C. for 10 minutes on one side of the polarizer P was 20 ⁇ m.
  • a conveyor type ultraviolet irradiation device manufactured by Eye Graphics Co., Ltd.
  • Examples PD1 to 8 were polarizing plates obtained by using the compositions of Examples D1 to 8, and the performance of the polarizer P was maintained, and the heat and moisture resistance and adhesiveness were good.
  • Example PD9 and 10 are the polarizing plates obtained using the composition of Example D9 and 10 which does not contain (F) component, the performance of polarizer P is maintained. The wet heat resistance was good, but the adhesiveness in polarizing plate applications was not sufficient.
  • the active energy ray-curable composition for forming an optical film of the present invention can be suitably used for the production of an optical film. Furthermore, as described in detail above, the optical film of the present invention is suitably used in a polarizer protective film application.

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Abstract

La présente invention vise à fournir une composition durcissable par rayonnement d'énergie actif pour former un film optique, ayant une bonne résistance à l'humidité et à la chaleur et une excellente flexibilité, et par lequel un faible coefficient photoélastique et un faible retard peuvent être tous deux obtenus, et vise à fournir un film optique obtenu à partir de la composition, un film protecteur de polariseur, et une plaque de polarisation. A cet effet, l'invention concerne une composition durcissable par rayonnement d'énergie actif pour former un film optique, contenant un composant (A) et/ou un composant (B). Composant (A) : un réactif d'un polymère à base de (méth)acrylate (a1) ayant dans une chaîne latérale de celui-ci un groupement fonctionnel apte à réagir avec un groupement carboxyle ou un groupement hydroxyle, et un composé (a2) ayant un groupement (méth)acryloyle et un groupement carboxyle ou un groupement hydroxyle ayant un poids moléculaire moyen en nombre de 180 ou supérieur. Composant (B) : un réactif d'un polymère à base de (méth)acrylate (b1) ayant dans une chaîne latérale de celui-ci un groupement hydroxyle ou un groupement carboxyle ayant le composé (a2) en tant que monomère de constitution, et un composé (b2) ayant un groupement (méth)acryloyle et un groupement fonctionnel apte à réagir avec un groupement carboxyle ou un groupement hydroxyle.
PCT/JP2013/083122 2012-12-11 2013-12-10 Composition durcissable par rayonnement d'énergie actif pour formation de film optique, film optique, et plaque de polarisation Ceased WO2014092095A1 (fr)

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JP2022075274A (ja) * 2020-11-06 2022-05-18 東亞合成株式会社 活性エネルギー線硬化性組成物

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KR20160093885A (ko) * 2015-01-30 2016-08-09 동우 화인켐 주식회사 편광판 및 이를 포함하는 화상 표시 장치
KR102143606B1 (ko) * 2016-09-19 2020-08-11 동우 화인켐 주식회사 광학 투명 점착제 조성물, 그를 포함하는 광학 투명 점착 필름 및 평판표시장치
KR101903906B1 (ko) * 2017-09-22 2018-10-02 주식회사 엘지화학 편광판 보호층용 무용제형 광경화성 수지 조성물, 이의 경화물을 포함하는 편광판 및 화상표시장치
JP7240090B2 (ja) * 2017-10-03 2023-03-15 日東電工株式会社 偏光板、画像表示装置、および偏光板の製造方法
KR102087506B1 (ko) * 2018-07-10 2020-03-10 주식회사 엘지화학 편광판 보호층용 무용제형 광경화성 수지 조성물, 이의 경화물을 포함하는 편광판 및 화상표시장치

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