WO2015046818A1 - 편광판 및 이를 포함하는 화상표시장치 - Google Patents
편광판 및 이를 포함하는 화상표시장치 Download PDFInfo
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- WO2015046818A1 WO2015046818A1 PCT/KR2014/008732 KR2014008732W WO2015046818A1 WO 2015046818 A1 WO2015046818 A1 WO 2015046818A1 KR 2014008732 W KR2014008732 W KR 2014008732W WO 2015046818 A1 WO2015046818 A1 WO 2015046818A1
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/10—Optical coatings produced by application to, or surface treatment of, optical elements
- G02B1/14—Protective coatings, e.g. hard coatings
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- 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
Definitions
- the present invention relates to a polarizing plate and an image display device including the same, and more particularly, to a polarizing plate capable of securing adhesive strength of a polarizer and a protective layer through a covalent bond, not a hydrogen bond, and an image display device including the same.
- the polarizing plate has been commonly used in a structure in which a protective film is laminated on both sides of a polarizer made of a polyvinyl alcohol (hereinafter referred to as 'PVA')-based resin dyed with a dichroic dye or iodine.
- 'PVA' polyvinyl alcohol
- the triacetyl cellulose (TAC, triacetyl cellulose) -based film has been used a lot of films in terms of excellent optical transparency and moisture permeability.
- the transparent thin film layer proposed so far has secured adhesive strength through hydrogen bonding between the hydroxy group of the polarizer made of mostly PVA resin and the hydrophilic functional group of the transparent thin film layer.
- water molecules can also be hydrogen-bonded with a hydroxy group of a polarizer made of the PVA-based resin or a hydrophilic functional group of the transparent thin film layer. Since the number of hydrogen bonds between the hydrophilic functional groups is reduced, there is a disadvantage that the adhesive strength is lowered.
- active energy ray-curable compositions including epoxy compounds is particularly active.
- an active energy ray-curable composition containing an epoxy compound a ring-opening reaction occurs between a hydroxyl group and an epoxy compound of a polarizer made of a PVA-based resin during curing by ultraviolet irradiation, and covalent bonds occur by the ring-opening reaction.
- Excellent adhesion can be ensured even in a high humidity atmosphere.
- the active energy ray-curable composition containing such an epoxy compound has a number of disadvantages in the manufacturing process because the curing rate is slow because the curing proceeds in a cationic manner, not in a radical manner, and the curing degree is low.
- a new polarizing plate capable of securing adhesive strength through covalent bonding rather than hydrogen bonding, having excellent adhesion between the polarizer and the protective layer, excellent water resistance and heat resistance, and which can be manufactured in a thin shape is required.
- the present invention is to provide an adhesive force through a covalent bond rather than a hydrogen bond, excellent adhesion of the polarizer and the protective layer, excellent water resistance and heat resistance, to provide a polarizing plate that can be manufactured in a thin shape and an image display device including the same do.
- the present invention is a polarizing plate comprising a polarizer, and a protective layer formed on at least one surface of the polarizer, the protective layer is (A) an acid anhydride compound having at least one unsaturated carbon bond between carbons; (B) a vinyl compound having at least one electron donor group; (C) a radical initiator; And (D) a polarizing plate which is a cured product of a radical curable composition comprising a cation generator.
- the polarizer and the protective layer is preferably secured through the covalent bond generated as a result of the esterification reaction between the hydroxyl group of the polarizer and the acid anhydride group of the protective layer.
- content of the said acid anhydride type compound and the said vinyl type compound is 0.8-1.0 by the compounding equivalence ratio represented by following formula (1).
- M is the number of carbon-to-carbon unsaturated double bonds that can participate in polymerization in a molecule containing an acid anhydride group contained in the acid anhydride compound
- N is the number of carbon-to-carbon unsaturated double bonds that can participate in the polymerization in the molecule contained in the vinyl compound.
- the acid anhydride compound may be at least one compound selected from the group consisting of compounds represented by the following [Formula I] to [Formula IV].
- R 1 is a (meth) acryloyl group, a (meth) acryloylalkyl group, or a (meth) acryloyloxyalkyl group
- R 2 is a halogen atom or a C 1-10 alkyl group
- a is an integer of 1 to 2
- b is an integer of 0 to 2
- X 1 is a single bond, -O-, -CO-, -COO-, or -OCO-.
- R 3 to R 5 are each independently hydrogen or a halogen atom; C 1-10 alkyl group, C 4-14 cycloalkyl group, C 6-14 aryl group or a combination thereof.
- R 6 and R 7 are each independently hydrogen or a halogen atom; C 1-10 alkyl group, C 4-14 cycloalkyl group, C 6-14 aryl group or a combination thereof.
- R 8 to R 11 are each independently hydrogen or a halogen atom; C 1-10 alkyl group, C 4-14 cycloalkyl group, C 6-14 aryl group or a combination thereof.
- the electron donor group of the vinyl compound is preferably a functional group represented by the following [formula A] or [formula B].
- R 12 is hydrogen or a C 1-10 alkyl group.
- R 13 is hydrogen or a C 1-10 alkyl group.
- the vinyl compound may be a compound represented by the following [Formula V].
- R 14 is hydrogen or a C 1-10 alkyl group
- R 15 is a c-valent C 1 ⁇ 10 aliphatic chain, C 4 ⁇ 14 alicyclic, C 6 ⁇ 14 aromatic ring, or a combination thereof, and; c is an integer from 1 to 4
- X 2 is -O- or -OCO-.
- radical curable composition of the present invention may further include a radical polymerizable compound represented by the following [Formula VI].
- R 16 is an ester group (-COO-), an amide group (-CON-), or a thioate group (-COS-);
- R 17 is a C 1-10 alkyl group, a C 4-10 cycloalkyl group, or a combination thereof, wherein R 17 has at least one hydroxy substituent in the molecule;
- R 18 is hydrogen or a C 1-10 alkyl group.
- the glass transition temperature after curing of the radical curable composition is preferably at least 60 °C.
- the radical curable composition preferably has a viscosity of 10 to 200 cP.
- the protective layer preferably has a thickness of 0.5 to 20 ⁇ m.
- the polarizing plate of the present invention may be further attached to the protective film via the adhesive layer on the opposite side of the surface on which the protective layer of the polarizer is formed.
- the polarizing plate of the present invention may further include an adhesive layer on the protective layer.
- the polarizer is preferably a polyvinyl alcohol-based film containing iodine or dichroic dye.
- the present invention provides an image display device including the polarizing plate.
- the polarizing plate of the present invention can secure the adhesive strength of the polarizer and the protective layer through a covalent bond rather than a hydrogen bond, it is excellent in the adhesion between the polarizer and the protective layer, and excellent in water resistance.
- the polarizing plate of the present invention can sufficiently protect the polarizer even in a high temperature environment, and thus has excellent heat resistance of the polarizing plate.
- the polarizing plate of the present invention has a thin protective layer compared to the polarizing plate having a conventional transparent protective film, it can be manufactured in a thin shape.
- the present inventors have conducted a study, vinyl-based compound having at least one electron donor group, a radical initiator having an acid anhydride compound having at least one unsaturated carbon bond between carbon atoms in a radically curable composition for forming a protective layer And when used in combination with the cation generator, it is possible to secure the adhesive force through covalent bonds, not hydrogen bonds, it is excellent in the adhesion between the polarizer and the protective layer, excellent in water resistance and heat resistance, it can be manufactured thin The present invention was completed.
- the polarizing plate of the present invention is a polarizing plate comprising a polarizer and a protective layer formed on at least one surface of the polarizer, wherein the protective layer (A) an acid anhydride compound having at least one unsaturated carbon bond between carbons; (B) a vinyl compound having at least one electron donor group; (C) a radical initiator; And (D) hardened
- the polarizer and the protective layer is preferably secured through the covalent bond generated as a result of the esterification reaction between the hydroxyl group of the polarizer and the acid anhydride group of the protective layer.
- adhesion between the polarizer and the protective layer is secured through covalent bonding, so that adhesion between the polarizer and the protective layer may be stably maintained even in a high humidity environment.
- the polarizer of the present invention may use a film made of polyvinyl alcohol (PVA) containing a polarizer well known in the art, for example, iodine or dichroic dye.
- PVA polyvinyl alcohol
- the polarizer may be prepared by dyeing iodine or dichroic dye on a polyvinyl alcohol film, but a method of manufacturing the same is not particularly limited.
- the polarizer means a state not including a protective layer (or protective film), and the polarizing plate means a state including a polarizer and a protective layer (or protective film).
- the polyvinyl alcohol-based film can be used without particular limitation as long as it contains a polyvinyl alcohol resin or a derivative thereof.
- examples of the derivative of the polyvinyl alcohol resin include, but are not limited to, polyvinyl formal resin, polyvinyl acetal resin, and the like.
- the polyvinyl alcohol-based film may be a commercially available polyvinyl alcohol-based film generally used in the manufacture of polarizers in the art, such as P30, PE30, PE60 from Kureray, M2000, M3000 M6000, etc. It may be.
- the polyvinyl alcohol-based film is not limited to this, but the degree of polymerization is preferably about 1,000 to 10,000, preferably 1,500 to 5,000. This is because when the degree of polymerization satisfies the above range, the molecular motion is free and can be mixed flexibly with iodine or dichroic dye.
- the protective layer of the present invention is formed using the radical curable composition to support and protect the polarizer, it may be formed by a method well known in the art.
- the radical curable composition is applied to one surface of the polarizer by a coating method well known in the art such as spin coating, bar coating, roll coating, gravure coating, blade coating, and the like to form a protective layer. It may be carried out by a method of curing through active energy ray irradiation.
- the irradiation method is not particularly limited, for example, it may be carried out by a method of irradiating ultraviolet light of about 10 to 2500mJ / cm 2 using an ultraviolet irradiation device (fusion lamp, D bulb).
- the acid anhydride-based compound included in the radical curable composition of the present invention enables curing of the composition through radical curing, and furthermore, secures adhesion through covalent bonding by esterification with a hydroxyl group of the polarizer.
- various acid anhydride compounds capable of radical curing by including at least one unsaturated carbon-to-carbon double bond in the molecule can be used.
- At least one of the carbon-unsaturated double bonds of the acid anhydride-based compound is preferably conjugated with at least one carbonyl group of the acid anhydride group for better radical curing.
- the acid anhydride compound may be, but is not limited to, at least one compound selected from the group consisting of compounds represented by the following [Formula I] to [Formula IV].
- R 1 is a (meth) acryloyl group, a (meth) acryloylalkyl group, or a (meth) acryloyloxyalkyl group
- R 2 is a halogen atom or a C 1-10 alkyl group
- a is an integer of 1 to 2
- b is an integer of 0 to 2
- X 1 is a single bond, -O-, -CO-, -COO-, or -OCO-.
- the alkyl group of the (meth) acryloylalkyl group refers to a linear or branched hydrocarbon site of 1 to 10, or 1 to 8, or 1 to 4 carbon atoms,
- the alkyl group may include at least one unsaturated bond in the molecule.
- the (meth) acryloyl group of the (meth) acryloylalkyl group may be positioned at any position of the alkyl group. That is, the said (meth) acryloyl group may come to the terminal of an alkyl group, and may come in the middle of an alkyl group.
- the remaining hydrogen atoms included in the alkyl group may be substituted with any substituent.
- the alkyl group of the (meth) acryloyloxyalkyl group means a straight or branched chain hydrocarbon site of 1 to 10, or 1 to 8, or 1 to 4 carbon atoms
- the alkyl group may include at least one unsaturated bond in the molecule.
- the (meth) acryloyloxy group of the (meth) acryloyloxyalkyl group may be positioned at any position of the alkyl group. That is, the said (meth) acryloyloxy group may come to the terminal of an alkyl group, and may come in the middle of an alkyl group.
- the remaining hydrogen atoms included in the alkyl group may be substituted with any substituent.
- the alkyl group refers to a straight or branched chain hydrocarbon site of 1 to 10, or 1 to 8, or 1 to 4 carbon atoms, wherein the alkyl group in the molecule It may also contain one unsaturated bond.
- the alkyl group may be, but is not limited to, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decanyl, and the like.
- R 3 to R 5 are each independently hydrogen or a halogen atom; C 1-10 alkyl group, C 4-14 cycloalkyl group, C 6-14 aryl group, or a combination thereof.
- the alkyl group refers to a straight or branched chain hydrocarbon site of 1 to 10, or 1 to 8, or 1 to 4 carbon atoms, wherein the alkyl group It may also contain at least one unsaturated bond in the molecule.
- the alkyl group may be, but is not limited to, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decanyl, and the like.
- the cycloalkyl group means 4 to 14, or 4 to 10, or 4 to 6 non-aromatic monocyclic, bicyclic or tricyclic hydrocarbon moieties.
- the cycloalkyl group may include at least one unsaturated bond in the molecule.
- the cycloalkyl group is not limited thereto, and examples thereof include a cyclopentane ring, a cyclopentene ring, a cyclohexane ring, a cyclohexene ring, and the like.
- the aryl group means a monocyclic, bicyclic or tricyclic aromatic hydrocarbon moiety having 6 to 14, or 6 to 12 ring atoms, but is not limited thereto.
- the R 3 to R 5 is, whereby but are not limited to, inter alia, each independently, preferably a hydrogen, a halogen atom, or C 1 ⁇ 10 alkyl group, a hydrogen, a halogen atom, or C 1 ⁇ 6 alkyl group more preferred, and still more preferably a hydrogen, a halogen atom, or C 1 ⁇ 4 alkyl group;
- R 6 and R 7 are each independently hydrogen or a halogen atom; C 1-10 alkyl group, C 4-14 cycloalkyl group, C 6-14 aryl group, or a combination thereof.
- the alkyl group refers to a straight or branched chain hydrocarbon site of 1 to 10, or 1 to 8, or 1 to 4 carbon atoms, wherein the alkyl group It may also contain at least one unsaturated bond in the molecule.
- the alkyl group may be, but is not limited to, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decanyl, and the like.
- the cycloalkyl group refers to a non-aromatic monocyclic, bicyclic or tricyclic hydrocarbon moiety of 4 to 14, or 4 to 10, or 4 to 6 ring carbons.
- the cycloalkyl group may include at least one unsaturated bond in the molecule.
- the cycloalkyl group is not limited thereto, and examples thereof include a cyclopentane ring, a cyclopentene ring, a cyclohexane ring, a cyclohexene ring, and the like.
- the aryl group means a monocyclic, bicyclic or tricyclic aromatic hydrocarbon moiety having 6 to 14, or 6 to 12 ring atoms, but is not limited thereto.
- the R 6 and R 7 are, thereby but are not limited to, inter alia, each independently, preferably a hydrogen, a halogen atom, or C 1 ⁇ 10 alkyl group, a hydrogen, a halogen atom, or C 1 ⁇ 6 alkyl group more preferred, and still more preferably a hydrogen, a halogen atom, or C 1 ⁇ 4 alkyl group;
- R 8 to R 11 are each independently hydrogen or a halogen atom; C 1-10 alkyl group, C 4-14 cycloalkyl group, C 6-14 aryl group, or a combination thereof.
- the alkyl group refers to a straight or branched chain hydrocarbon site of 1 to 10, or 1 to 8, or 1 to 4 carbon atoms, wherein the alkyl group It may also contain at least one unsaturated bond in the molecule.
- the alkyl group may be, but is not limited to, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decanyl, and the like.
- the cycloalkyl group means a non-aromatic monocyclic, bicyclic or tricyclic hydrocarbon moiety of 4 to 14, or 4 to 10, or 4 to 6 ring carbons.
- the cycloalkyl group may include at least one unsaturated bond in the molecule.
- the cycloalkyl group is not limited thereto, and examples thereof include a cyclopentane ring, a cyclopentene ring, a cyclohexane ring, a cyclohexene ring, and the like.
- the aryl group means a monocyclic, bicyclic or tricyclic aromatic hydrocarbon moiety having 6 to 14, or 6 to 12 ring atoms, but is not limited thereto.
- the R 8 to R 11 are, thereby but are not limited to, inter alia, each independently, preferably a hydrogen, a halogen atom, or C 1 ⁇ 10 alkyl group, a hydrogen, a halogen atom, or C 1 ⁇ 6 alkyl group more preferred, and still more preferably a hydrogen, a halogen atom, or C 1 ⁇ 4 alkyl group;
- the compound represented by [Formula I] to [Formula IV] is not limited thereto, and may be, for example, a compound represented by the following [Formula 1] to [Formula 6]. These can be used individually or in mixture.
- the vinyl compound included in the radical curable composition of the present invention forms a charge complex with the acid anhydride compound by an electron donor group when the radical curable composition is cured. Copolymerization with acid anhydride compounds allows radical curing to occur very effectively.
- the vinyl compound may be used without particular limitation as long as it has an electron donor group, and may form a charge complex with the acid anhydride compound when the radical curable composition is cured.
- the vinyl-based compound is meant to exclude compounds overlapping with the radically polymerizable compound to be described later, except for the examples listed below.
- the electron donor group of the vinyl compound is preferably a functional group represented by the following [Formula A] or [Formula B]. This is because it is possible to form a charge complex with the acid anhydride compound more excellent in this case.
- R 12 is hydrogen or a C 1-10 alkyl group.
- the alkyl group refers to a straight or branched chain hydrocarbon site of 1 to 10, or 1 to 8, or 1 to 4 carbon atoms, wherein the alkyl group is at least in the molecule It may also contain one unsaturated bond.
- the alkyl group may be, but is not limited to, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decanyl, and the like.
- R 13 is hydrogen or a C 1-10 alkyl group.
- the alkyl group refers to a straight or branched chain hydrocarbon site of 1 to 10, or 1 to 8, or 1 to 4 carbon atoms, wherein the alkyl group is at least in the molecule It may also contain one unsaturated bond.
- the alkyl group may be, but is not limited to, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decanyl, and the like.
- the vinyl compound is not limited thereto, but may be a compound represented by the following [Formula V].
- R 14 is hydrogen or a C 1-10 alkyl group
- R 15 is a c-valent C 1 ⁇ 10 aliphatic chain, C 4 ⁇ 14 alicyclic, C 6 ⁇ 14 aromatic ring, or a combination thereof, and; c is an integer from 1 to 4
- X 2 is -O- or -OCO-.
- the alkyl group means a straight or branched chain hydrocarbon site of 1 to 10, or 1 to 8, or 1 to 4 carbon atoms, wherein the alkyl group is at least in the molecule It may also contain one unsaturated bond.
- the alkyl group may be, but is not limited to, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decanyl, and the like.
- the aliphatic chain means a straight or branched chain saturated or unsaturated trivalent hydrocarbon moiety of 1 to 10, or 1 to 8, or 1 to 4 carbon atoms, and examples thereof include, but are not limited to, trivalent, methane chains, ethane chains, propane chains, butane chains, alkane chains such as pentane chains, hexane chains, heptane chains, octane chains, nonane chains and decane chains. have. do.
- One or more hydrogen atoms included in the aliphatic hydrocarbon chain may be substituted with any substituent.
- the aliphatic ring is 4 to 14, or 4 to 10, or saturated or unsaturated non-aromatic trivalent monocyclic, bicyclic or tricyclic of 4 to 6 ring carbons.
- Cycloalkane ring such as a trivalent, cyclopentane ring, a cyclohexane ring, or a trivalent, cyclopentene ring, a cyclopentene ring, a cyclohexene ring, a cyclooctene ring, etc.
- Alkene (cycloalkene) ring etc. are mentioned.
- One or more hydrogen atoms included in the aliphatic hydrocarbon ring may be substituted with any substituent.
- the aromatic ring means a trivalent monocyclic, bicyclic or tricyclic aromatic hydrocarbon moiety having 6 to 14, or 6 to 12 ring atoms, but is not limited thereto. And trivalent, benzene ring, naphthalene ring, anthracene ring, biphenyl ring and the like.
- One or more hydrogen atoms included in the aromatic hydrocarbon ring may be substituted with any substituent.
- the compound represented by [Formula V] is not limited thereto, and may be, for example, a compound represented by the following [Formula 7] to [Formula 17]. These can be used individually or in mixture.
- M is the number of carbon-to-carbon unsaturated double bonds that can participate in the polymerization in the molecule containing the acid anhydride group contained in the acid anhydride-based compound
- N is the carbon-to-carbon unsaturated double that can participate in the polymerization in the molecule included in the vinyl-based compound Number of bonds
- the number M of carbon-to-carbon unsaturated double bonds that can participate in the polymerization contained in the acid anhydride-based compound is (the carbon-to-carbon unsaturated double bond that can participate in the polymerization of each acid anhydride-based compound).
- the number N of the carbon-containing unsaturated double bonds which can participate in the polymerization contained in the vinyl compound and the number N of X (mole fraction of the acid anhydride compound) can also participate in the polymerization of each vinyl compound.
- the total amount of the number of carbon-containing unsaturated double bonds) X) (mole fraction of the vinyl compound) is present.
- the acid anhydride compound and the vinyl compound are included to satisfy the range of such a compounding equivalence ratio, the acid anhydride compound and the vinyl compound are charged complexes (Charge complexes), resulting in excellent radical curing by copolymerization.
- the radical initiator included in the radical curable composition according to the present invention is for promoting the radical polymerization property to improve the curing rate, and as the radical initiator, radical initiators generally used in the art are not limited. Can be used.
- the radical initiator is, for example, 1-Hydroxy-cyclohexyl-phenyl-ketone, 2-hydroxy-2-methyl-1-phenyl-1 -Propanone (2-Hydroxy-2-methyl-1-phenyl-1-propanone), 2-hydroxy-1- [4- (2-hydroxyethoxy) phenyl] -2-methyl-1-propanone (2-Hydroxy-1- [4- (2-hydroxyethoxy) phenyl] -2-methyl-1-propanone), Methylbenzoylformate, Oxy-phenyl-acetic acid-2- [2-oxo-2- Phenyl-acetoxy-ethoxy] -ethyl ester (oxy-phenyl-acetic acid-2- [2 oxo-2phenyl-acetoxy-ethoxy] -ethyl ester), oxy-phenyl-acetic acid-2- [2-hydroxy- Oxy-phenyl-acetic acid-2- [2-hydroxy- Oxy
- the content of the radical initiator is preferably about 1 to 10 parts by weight, 1 to 5 parts by weight or about 2 to 4 parts by weight based on 100 parts by weight of the radical curable composition. This is because when the content of the radical initiator satisfies the numerical range, the radical curable composition may be smoothly cured.
- the cation generator included in the radical curable composition according to the present invention transfers a cation (H +) to the acid anhydride compound during curing of the radical curable composition to effect esterification with a hydroxyl group of a polarizer.
- a cation generator since the present invention uses a cation generator, it is possible to secure excellent adhesion to the polarizer through covalent bonds, which are formed by the esterification reaction even under low temperature conditions.
- the cation generator usable in the present invention includes, for example, sulfonium salt or iodonium salt.
- Specific examples of the cation generator including sulfonium salt or iodonium salt include, for example, diphenyl (4-phenylthio) phenylsulfonium hexafluoroantimonate (Diphenyl (4- phenylthio) phenylsulfonium hexafluoroantimonate), diphenyl (4-phenylthio) phenylsulfonium hexafluorophosphate (Diphenyl (4-phenylthio) phenylsulfonium hexafluorophosphate), (phenyl) [4- (2-methylpropyl) phenyl] -iodium hexa Fluorophosphate ((phenyl) [4- (2-methylpropyl) phenyl] -I
- the content of the cation generator may be, for example, 10 parts by weight or less, preferably 1 to 10 parts by weight, 2 to 8 parts by weight, or 2 to 6 parts by weight based on 100 parts by weight of the radical curable composition. This is because when the cation generator is included in the content of the numerical range in the radical curable composition according to the present invention, the esterification reaction is performed well.
- the radical curable composition of the present invention further comprises a radically polymerizable compound represented by the following [Formula VI] in order to enable the protective layer film to be more rigid through the reaction of the hydroxyl group with the acid anhydride while maintaining excellent adhesion. can do.
- R 16 is an ester group (-COO-), an amide group (-CON-), or a thioate group (-COS-);
- R 17 is a C 1-10 alkyl group, a C 4-10 cycloalkyl group, or a combination thereof, wherein R 17 has at least one hydroxy substituent in the molecule;
- R 18 is hydrogen or a C 1-10 alkyl group.
- the alkyl group refers to a straight or branched chain hydrocarbon site of 1 to 10, or 1 to 8, or 1 to 4 carbon atoms, wherein the alkyl group is at least in the molecule It may also contain one unsaturated bond.
- the alkyl group may be, but is not limited to, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decanyl, and the like.
- the cycloalkyl group means 4 to 14, or 4 to 10, or 4 to 6 non-aromatic monocyclic, bicyclic or tricyclic hydrocarbon sites.
- the cycloalkyl group may include at least one unsaturated bond in the molecule.
- the cycloalkyl group is not limited thereto, and examples thereof include a cyclopentane ring, a cyclohexane ring, and the like.
- the hydroxy group may be substituted at any position in the alkyl group or the cycloalkyl group.
- the hydroxy group may be at the end of the alkyl group or may be in the middle of the alkyl group.
- the remaining hydrogen atoms contained in the alkyl group or cycloalkyl group may be substituted with any substituent.
- the alkyl group means a straight or branched chain hydrocarbon site of 1 to 10, or 1 to 8, or 1 to 4 carbon atoms, wherein the alkyl group is at least in the molecule It may also contain one unsaturated bond.
- the alkyl group may be, but is not limited to, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decanyl, and the like.
- One or more hydrogen atoms included in the alkyl group may be substituted with any substituent.
- the radically polymerizable compound is not limited thereto, and may be, for example, a compound represented by the following [Formula 18] to [Formula 28]. These can be used individually or in mixture.
- the radically curable composition of the present invention comprises 100 parts by weight of the total composition, 1 to 50 parts by weight of the acid anhydride compound and the vinyl compound; 40 to 97 parts by weight of the radical polymerizable compound; 1 to 10 parts by weight of radical initiator; And 1 to 10 parts by weight of the cation generator.
- the content of the acid anhydride compound and the vinyl compound means the total content of the two compounds added in the equivalent ratio as described above.
- the content of the acid anhydride compound and the vinyl compound is about 1 to 50 parts by weight, preferably about 5 to 45 parts by weight, and more preferably 10 to 40 parts by weight based on 100 parts by weight of the total composition. May be enough.
- adhesion is particularly excellent, and problems such as viscosity increase do not occur.
- the content of the radically polymerizable compound may be about 40 to 97 parts by weight, preferably about 45 to 90 parts by weight, and more preferably about 50 to 80 parts by weight based on 100 parts by weight of the total composition.
- the content of the radically polymerizable compound is included in the content of the numerical range, it is possible to ensure more excellent adhesion.
- the content of the radical initiator may be about 1 to 10 parts by weight, preferably about 1 to 5 parts by weight, and more preferably about 2 to 4 parts by weight based on 100 parts by weight of the total composition.
- the content of the radical initiator is included in the content of the numerical range, the curing can be made smoothly.
- the content of the cation generator may be about 1 to 10 parts by weight, preferably about 2 to 8 parts by weight, and more preferably about 2 to 6 parts by weight based on 100 parts by weight of the total composition.
- the esterification reaction may occur effectively well.
- the radical curable composition is preferably a glass transition temperature of 60 °C or more after curing, for example, may be about 60 to 200 °C, 65 to 150 °C or 70 to 120 °C.
- the protective layer formed is thermally very stable, because the heat resistance of the polarizing plate including the same is excellent.
- the radical curable composition preferably has a viscosity of about 10 to 200 cP or about 20 to 100 cP.
- the thickness of the protective layer may be thinly formed, and since the composition has a low viscosity, there is an excellent workability.
- the thickness of the protective layer formed using the radical curable composition is preferably 0.5 to 20 ⁇ m, for example, may be 0.5 to 15 ⁇ m or 0.5 to 10 ⁇ m. This is because when the thickness of the protective layer satisfies the above range, the thickness of the polarizing plate produced can be reduced. If it is less than 0.5 ⁇ m, the thermal shock stability and curl characteristics of the polarizer are weak, and if it is 20 ⁇ m or more, the thickness of the polarizing plate is difficult.
- the polarizing plate of the present invention may further include a protective film on one surface of the polarizer as needed. More specifically, in the polarizing plate of the present invention, when the protective layer is formed on one surface of the polarizer, a separate protective film may be attached through the adhesive layer to support and protect the polarizer on the opposite side of the surface on which the protective layer is formed. have.
- the protective film is for supporting and protecting the polarizer
- protective films of various materials generally known in the art for example, cellulose-based film, polyethylene terephthalate (PET) film, cyclo An olefin polymer (COP, cycloolefin polymer) film, acrylic film, or the like can be used without limitation.
- PET polyethylene terephthalate
- COP cycloolefin polymer
- acrylic film or the like
- the acrylic film usable in the present invention can be obtained by molding a molding material containing (meth) acrylate-based resin as a main component by extrusion molding.
- the (meth) acrylate-based resin is a resin containing a (meth) acrylate-based unit as a main component, as well as a homopolymer resin consisting of (meth) acrylate-based units, as well as (meth) acrylate-based units
- the concept also includes a blend resin blended with other resin.
- the (meth) acrylate-based unit may be, for example, an alkyl (meth) acrylate-based unit.
- the alkyl (meth) acrylate-based unit means both an alkyl acrylate-based unit and an alkyl methacrylate-based unit
- the alkyl group of the alkyl (meth) acrylate-based unit is preferably 1 to 10 carbon atoms, It is more preferable that it is C1-C4.
- a styrene type unit, a maleic anhydride type unit, a maleimide type unit, etc. are mentioned as a monomeric unit copolymerizable with the said (meth) acrylate type unit.
- the styrene-based unit is not limited thereto, and examples thereof include styrene, ⁇ -methylstyrene, and the like;
- the maleic anhydride monomer include, but are not limited to, maleic anhydride, methyl maleic anhydride, cyclohexyl maleic anhydride, phenyl maleic anhydride, and the like;
- the maleimide monomers include, but are not limited to, maleimide, N-methyl maleimide, N-cyclohexyl maleimide, N-phenyl maleimide, and the like. These may be used alone or in combination.
- the acrylic film may be a film containing a (meth) acrylate resin having a lactone ring structure.
- (meth) acrylate type resin which has a lactone ring structure it is the lactone described, for example in Unexamined-Japanese-Patent No. 2000-230016, Unexamined-Japanese-Patent No. 2001-151814, 2002-120326, etc.
- (Meth) acrylate type resin which has a ring structure is mentioned.
- the method for producing the acrylic film is not particularly limited, and for example, (meth) acrylate-based resin and other polymers, additives, and the like are sufficiently mixed by any suitable mixing method to prepare a thermoplastic resin composition, which is then film-molded. Or (meth) acrylate-based resin and other polymers, additives and the like may be prepared in a separate solution and then mixed to form a uniform mixed solution and then film-molded.
- the acrylic film may be any of an unstretched film or a stretched film. In the case of a stretched film, it may be a uniaxial stretched film or a biaxially stretched film, and in the case of a biaxially stretched film, it may be either a simultaneous biaxially stretched film or a successive biaxially stretched film.
- the polarizing plate of the present invention may further include a primer layer between the adhesive layer and the protective film in order to further improve the adhesive force.
- the primer layer may be formed by coating and drying a coating solution containing a water dispersible polymer resin, water dispersible fine particles and water on a protective film using a bar coating method, a gravure coating method, or the like.
- the water-dispersible polymer resin may be, for example, a water-based polyurethane resin, a water-based acrylic resin, a water-based polyester resin, or a combination thereof, and the water-dispersible microparticles may be inorganic fine particles such as silica, titania, alumina, zirconia, or the like.
- organic fine particles made of silicone resin, fluorine resin, (meth) acrylic resin, crosslinked polyvinyl alcohol and melamine resin, or a combination thereof may be used, but are not limited thereto.
- the polarizer and the protective film is attached to the surface of the polarizer or the protective film using a roll coater, gravure coater, bar coater, knife coater or capillary coater, etc., and then heat lamination with a lamination roll, It may be carried out by a method of pressing at room temperature and laminating or a method of UV irradiation after lamination.
- the adhesive various polarizing plate adhesives used in the art, for example, polyvinyl alcohol-based adhesives, polyurethane-based adhesives, acrylic adhesives, cationic or radical-based adhesives and the like can be used without limitation.
- the polarizing plate of the present invention may include an adhesive layer on an upper portion of the protective layer, if necessary, for attachment to an optical film such as a display panel or a retardation film.
- the pressure-sensitive adhesive layer may be formed using various pressure-sensitive adhesives well known in the art, and the kind thereof is not particularly limited.
- the pressure-sensitive adhesive layer may be a rubber pressure sensitive adhesive, an acrylic pressure sensitive adhesive, a silicone pressure sensitive adhesive, a urethane pressure sensitive adhesive, a polyvinyl alcohol pressure sensitive adhesive, a polyvinylpyrrolidone pressure sensitive adhesive, a polyacrylamide pressure sensitive adhesive, a cellulose pressure sensitive adhesive, a vinyl alkyl ether pressure sensitive adhesive, or the like. It can be formed using. Among these, in consideration of transparency, heat resistance and the like, it is particularly preferable to use an acrylic pressure-sensitive adhesive.
- the pressure-sensitive adhesive layer may be formed by applying a pressure-sensitive adhesive on the protective layer, or may be formed by a method of attaching the pressure-sensitive adhesive sheet prepared by applying the pressure-sensitive adhesive on the release sheet and dried on the protective layer.
- the polarizing plate of the present invention as described above can be usefully applied to an image display device such as a liquid crystal display device.
- the image display apparatus may be, for example, a liquid crystal display including a liquid crystal panel and polarizing plates provided on both surfaces of the liquid crystal panel, wherein at least one of the polarizing plates may be a polarizing plate according to the present invention.
- the type of liquid crystal panel included in the liquid crystal display device is not particularly limited.
- a panel of a passive matrix type such as, but not limited to, a twisted nematic (TN) type, a super twisted nematic (STN) type, a ferrolectic (F) type, or a polymer dispersed (PD) type; Active matrix panels such as two-terminal or three-terminal; All known panels, such as an In Plane Switching (IPS) panel and a Vertical Alignment (VA) panel, can be applied.
- IPS In Plane Switching
- VA Vertical Alignment
- other configurations constituting the liquid crystal display device for example, types of upper and lower substrates (eg, color filter substrates or array substrates) are not particularly limited, and configurations known in the art may be employed without limitation. Can be.
- the raw material hopper is a resin composition obtained by uniformly mixing poly (N-cyclohexylmaleimide-co-methylmethacrylate), styrene-maleic anhydride copolymer resin and phenoxy resin in a weight ratio of 100: 2.5: 5. From the extruder to a nitrogen-substituted 24 ⁇ extruder and melted at 250 ° C. to prepare a raw material pellet.
- the poly (N-cyclohexylmaleimide-co-methylmethacrylate) resin was used in which the content of N-cyclohexylmaleimide was 6.5% by weight as a result of NMR analysis.
- the obtained raw material pellets were vacuum-dried and melted with an extruder at 260 degreeC, passed through the T-die of a coat hanger type, and the film of 150 micrometers in thickness was produced through the chrome plating casting roll, a drying roll, etc.
- the film was stretched at a rate of 170% using a speed difference of the roll in the MD direction at 125 ° C. using a pilot stretching equipment to produce an acrylic film.
- Radical curable composition A 20 parts by weight of itaconic anhydride, 15 parts by weight of 2-hydroxyethyl vinyl ether, 57 parts by weight of 2-hydroxyethyl acrylate, 3 parts by weight of radical initiator (Igarcure 819), diphenyl (4-phenylthio) as a cation generator Radical curable composition A was prepared by mixing 5 parts by weight of phenylsulfonium hexafluoroantimonate.
- Radical curable composition B 20 parts by weight of maleic anhydride, 15.7 parts by weight of 2-hydroxyethyl vinyl ether, 56.3 parts by weight of 2-hydroxyethyl acrylate, 3 parts by weight of radical initiator (Igacure 819), diphenyl (4-phenylthio) as a cation generator Radical curable composition B was prepared by mixing 5 parts by weight of phenylsulfonium hexafluoroantimonate.
- a radical curable composition D was prepared by mixing 20 parts by weight of acrylomorpholine, 40 parts by weight of hydroxyethylacrylamide, 37 parts by weight of hydroxyethyl acrylate, and 3 parts by weight of a radical initiator (Igacure 819).
- Radical curable composition A was applied to the primer layer of the acrylic film-based protective film prepared in Preparation Example 1 with a dropper, laminated on one surface of a polarizer (PVA device), and then the conditions were such that the thickness of the final adhesive layer was 1 to 2 ⁇ m. After setting, passed the laminator (5m / min). Then, using a UV irradiation device (fusion lamp, D bulb) on the surface of the acrylic film is laminated, a polarizing plate having a protective film on one surface of the polarizer was prepared by irradiating ultraviolet light of 900mJ / cm 2 .
- a polarizer fusion lamp, D bulb
- the radical curable composition A is applied to the other surface of the surface on which the protective film of the PVA device of the prepared polarizer is laminated, the PET film having a releasing force is laminated, and then the final protective layer thickness is 5 to 6 ⁇ m. After setting conditions, it passed the laminator (5 m / min). Then, by using an ultraviolet irradiation device (fusion lamp, D bulb) to the surface on which the release PET film is laminated, the ultraviolet ray of 900mJ / cm 2 is irradiated, the PET film is removed, one side of the polarizer is provided with a protective film On the other side, the polarizing plate provided with a protective layer was manufactured. The polarizing plate was manufactured in a constant temperature and humidity environment with a temperature of 20 ° C. and a humidity of 50%.
- Example 1 a polarizing plate was manufactured by the same method except that the radical curable composition B was used instead of the radical curable composition A.
- Example 1 a polarizing plate was manufactured by the same method except that the radical curable composition C was used instead of the radical curable composition A.
- Example 1 a polarizing plate was manufactured by the same method except that the radical curable composition D was used instead of the radical curable composition A.
- the compounding equivalent ratio represented by said Formula (1) of the acid anhydride type compound and the vinyl type compound of the radical curable composition used in the said Examples 1-3 was calculated, and is shown in following [Table 1].
- the number M of carbon-containing unsaturated double bonds that can participate in the polymerization included in the acid anhydride compound is (the number of carbon-containing unsaturated double bonds that can participate in the polymerization of each acid anhydride compound)
- X the corresponding acid anhydride system
- N the number of inter-carbon unsaturated double bonds that can participate in polymerization included in the vinyl-based compound
- N the number of inter-carbon unsaturated double bonds that can participate in polymerization of each vinyl-based compound
- Adhesion evaluation The radical curable composition used in Examples 1 to 3 and Comparative Examples was applied on the polarizer (PVA device), the polarizer (PVA device) was laminated thereon, and passed through the laminator, followed by an ultraviolet irradiation device (fusion). lamp, D bulb) was used to irradiate 900mJ / cm 2 of ultraviolet light to prepare a peel force sample consisting of a polarizer / protective layer / polarizer. The prepared sample was cut to a width of 20 mm and a length of 100 mm, and then measured using a Texture Analyzer (TA-XT Plus, Stable Micro Systems), and the peeling force was measured at a peeling rate of 300 mm / min and 90 degrees.
- a Texture Analyzer TA-XT Plus, Stable Micro Systems
- the adhesiveness As can be seen in Table 1, in Examples 1 to 3 of the present invention, the adhesiveness. It is excellent in thermal shock stability, water resistance, and it can be seen that the glass transition temperature is high. However, in the case of the comparative example to secure the adhesive strength through hydrogen bonding, it can be seen that although the adhesion is excellent, it is very vulnerable to the water resistance.
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Abstract
Description
구분 | 조성물 | 배합 당량비 | 보호층 두께[㎛] | 밀착성 | 내수성 | 유리전이온도[℃] | 열충격안정성 |
실시예 1 | A | 1 (M:N=1:1) | 5 | 우수 | 우수 | 67 | 우수 |
실시예 2 | B | 1 (M:N=1:1) | 5 | 양호 | 우수 | 63 | 양호 |
실시예 3 | C | 1 (M:N=1:1) | 5 | 우수 | 우수 | 74 | 우수 |
비교예 | D | - | 5 | 우수 | 나쁨 | 76 | 우수 |
Claims (15)
- 편광자; 및상기 편광자의 적어도 일면에 형성되는 보호층을 포함하는 편광판이며,상기 보호층은 (A) 적어도 하나의 탄소간 불포화 이중 결합을 갖는 산 무수물계 화합물; (B) 적어도 하나의 전자 도너(Donor)기를 갖는 비닐계 화합물; (C) 라디칼 개시제; 및 (D) 양이온 발생제를 포함하는 라디칼 경화형 조성물의 경화물인 편광판.
- 제 1 항에 있어서,상기 편광자와 보호층은 상기 편광자의 히드록시기와 상기 보호층의 산 무수물기 간의 에스테르화 반응 결과 발생되는 공유 결합을 통해 접착력이 확보되는 것인 편광판.
- 제 1 항에 있어서,상기 산 무수물계 화합물과 상기 비닐계 화합물의 함유량이 하기 식 (1)로 표시되는 배합 당량비로 0.8 내지 1.0 인 편광판.식 (1): 배합 당량비 = M/N상기 식 (1)에서, M은 상기 산 무수물계 화합물 중에 포함되는 산 무수물기를 포함한 분자에서 중합에 참여할 수 있는 탄소간 불포화 이중 결합의 수이고; N은 상기 비닐계 화합물 중에 포함되는 분자에서 중합에 참여할 수 있는 탄소간 불포화 이중 결합의 수임.
- 제 1 항에 있어서,상기 산 무수물계 화합물은 하기 [화학식 I] 내지 [화학식 Ⅳ]로 표시되는 화합물로 이루어진 군으로부터 선택된 1종 이상의 화합물인 편광판.[화학식 I]상기 [화학식 I]에 있어서, R1은 (메트)아크릴로일기, (메트)아크릴로일알킬기, 또는 (메트)아크릴로일옥시알킬기이고; R2는 할로겐원자 또는 C1~10 알킬기이고; a는 1~2의 정수이고; b는 0~2의 정수이며; X1은 단일결합, -O-, -CO-, -COO-, 또는 -OCO-임.[화학식 Ⅱ]상기 [화학식 Ⅱ]에 있어서, R3 내지 R5는 각각 독립적으로 수소 또는 할로겐원자이거나; C1~10 알킬기, C4~14 사이클로알킬기, C6~14 아릴기 또는 이들의 조합임.[화학식 Ⅲ]상기 [화학식 Ⅲ]에 있어서, R6 및 R7은 각각 독립적으로 수소 또는 할로겐원자이거나; C1~10 알킬기, C4~14 사이클로알킬기, C6~14 아릴기 또는 이들의 조합임.[화학식 Ⅳ]상기 [화학식 Ⅳ]에 있어서, R8 내지 R11은 각각 독립적으로 수소 또는 할로겐원자이거나; C1~10 알킬기, C4~14 사이클로알킬기, C6~14 아릴기 또는 이들의 조합임.
- 제 7 항에 있어서,상기 라디칼 경화형 조성물은 전체 조성물 100 중량부에 대하여, 상기 산 무수물계 화합물 및 비닐계 화합물 1 내지 50 중량부; 상기 라디칼 중합성 화합물 40 내지 97 중량부; 상기 라디칼 개시제 1 내지 10 중량부; 및 상기 양이온 발생제 1 내지 10 중량부를 포함하는 편광판.
- 제 1 항에 있어서,상기 라디칼 경화형 조성물의 경화 후 유리전이온도는 60℃ 이상인 편광판.
- 제 1 항에 있어서,상기 라디칼 경화형 조성물의 점도는 10 내지 200cP 인 편광판.
- 제 1 항에 있어서,상기 보호층은 두께가 0.5 내지 20㎛인 편광판.
- 제 1 항에 있어서,상기 편광자의 보호층이 형성된 면의 반대면에 접착제층을 매개로 보호 필름을 더 부착된 편광판.
- 제 1 항에 있어서,상기 보호층 상부에 점착층을 더 포함하는 편광판.
- 제 1 항에 있어서,상기 편광자는 요오드 또는 이색성 염료를 포함하는 폴리비닐알코올계 필름인 편광판,
- 제 1 항 내지 제 14 항 중 어느 한 항의 편광판을 포함하는 화상표시장치.
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US15/024,706 US9971067B2 (en) | 2013-09-30 | 2014-09-19 | Polarizing plate and image display apparatus comprising same |
JP2016545676A JP6297705B2 (ja) | 2013-09-30 | 2014-09-19 | 偏光板およびこれを含む画像表示装置 |
CN201480054155.1A CN105593720B (zh) | 2013-09-30 | 2014-09-19 | 偏光板及包含该偏光板的图像显示装置 |
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KR20130040725A (ko) * | 2011-10-14 | 2013-04-24 | 주식회사 엘지화학 | 편광판용 접착제 및 이를 포함하는 편광판 |
KR20130103290A (ko) * | 2012-03-09 | 2013-09-23 | 제일모직주식회사 | 편광판용 접착제 조성물 및 이를 이용한 편광판 |
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JP2006163082A (ja) * | 2004-12-08 | 2006-06-22 | Nippon Paper Chemicals Co Ltd | 光学部材及びその製造方法、並びに液晶表示装置 |
JP2009008860A (ja) * | 2007-06-27 | 2009-01-15 | Nitto Denko Corp | 偏光板の製造方法、偏光板、光学フィルムおよび画像表示装置 |
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