KR20160084094A - Curable composition with active energy ray, polarizing plate comprising thereof and liquid crystal display device - Google Patents

Abstract

The present invention relates to an active energy ray-curable resin composition, a polarizing plate including the same, and a liquid crystal display device. More specifically, the present invention relates to an active energy ray-curable resin composition including an epoxy-based compound along with an ionic compound which has a functional group capable of forming a strong ionic bond with an epoxy group on the epoxy compound. The present invention further relates to a polarizing plate including the same and a liquid crystal display device. The active energy ray-curable resin composition prevents reduction in the optical properties of polarizers due to an anti-static agent fixed onto a polymer, and increases adhesiveness to the polarizers. In addition, the active energy ray-curable resin composition can be an alternative to an anti-static layer and transparent protective films such as conventional triacetyl cellulose (TAC) without an additional adhesive layer or a cohesive layer, and also enables thinning and weight lightening of the polarizing plate.

Description

TECHNICAL FIELD [0001] The present invention relates to an active energy ray-curable resin composition, a polarizing plate including the same, and a liquid crystal display device using the same. BACKGROUND ART < RTI ID = 0.0 >

The present invention relates to an active energy ray-curable resin composition capable of preventing the deterioration of the optical properties of a polarizer by fixing an antistatic agent on a polymer and enhancing adhesion with a polarizer, a polarizing plate containing the same, and a liquid crystal display device.

BACKGROUND ART A liquid crystal display device (LCD) basically includes a liquid crystal cell containing a liquid crystal and a polarizing plate.

The polarizing plate includes a polyvinyl alcohol (PVA) polarizer (or 'polarizing film') which is stretched in a predetermined direction and in which an iodine compound or a dichroic polarizing material is adsorbed and oriented, and a polarizer And a transparent protective film is formed.

As the transparent protective film, triacetyl cellulose (TAC), polyethylene terephthalate (PET), cycloolefin polymer (COP), acrylic film and the like are used.

The transparent protective film and the adhesive for attaching the polarizer may be selected from the group consisting of an acrylic adhesive, a dry laminate adhesive obtained by mixing a polyurethane resin solution and a polyisocyanate resin solution, a styrene butadiene rubber adhesive, an epoxy adhesive, a polyvinyl alcohol adhesive, , An adhesive containing a polyester-based ionomer-type urethane resin and a compound having a glycidyloxy group, and a thermosetting adhesive.

Considering that the polarizer and the transparent protective film are attached to the polarizer by an adhesive layer, the thickness of the polarizer is usually at least 135 탆 considering that the polarizer is 25 탆, the thickness of the transparent protective film is at least 40 탆 and the thickness of the adhesive layer is at least 15 탆. , And various functional films such as a retardation film, an overcoat film, a diffusion film, a prism sheet, and a brightness enhancement film are introduced thereinto can not satisfy the thin and light weight required for a polarizing plate in recent years.

On the other hand, when the release film is peeled off from the pressure-sensitive adhesive layer in the process of attaching the polarizing plate to the liquid crystal cell, static electricity is generated, and the static electricity generated thereby affects the orientation of the liquid crystal, thereby causing defects or causing electrostatic attraction between the liquid crystal cell and the pressure- Thereby causing contamination.

In order to solve the problems caused by the generation of static electricity, methods have been proposed in which an antistatic layer containing an antistatic agent is formed on the layer constituting the polarizing plate or an antistatic agent is added to the composition of the existing layer.

Usually, an antistatic agent is an ionic substance such as a conductive polymer, a metal oxide particle, a method of adding a substance having a conductive component such as carbon particles, a metal salt organic salt or a surfactant. These antistatic agents have been applied not only in antistatic function but also in various ways within a range that does not hinder the physical properties of the polarizing plate.

For example, Japanese Patent Laying-Open No. 2005-27796 discloses an antistatic pressure-sensitive adhesive optical film, and specifically relates to a coating composition in which a conductive polymer such as polyaniline, polypyrrole, or polythiophene is dispersed in an organic solvent And an adhesive layer based on an acrylic polymer is formed on the antistatic layer made of the acrylic polymer.

In this patent, the generation of static electricity in the optical film can be suppressed, but the adhesion between the polarizer and the antistatic layer is insufficient and migration of the antistatic agent to the polarizer occurs, and the protective film of the polarizer of the polarizer is deformed by the organic solvent, .

Furthermore, this method does not meet the demand for a thin and lightweight polarizing plate which is required recently, which leads to an increase in the overall thickness of the polarizing plate as a new layer of an antistatic layer is stacked.

Regarding material change, Japanese Patent Laid-Open Publication No. 2006-011365 and Korean Patent Publication No. 2010-0122885 disclose a pressure-sensitive adhesive composition containing an ionic liquid in a liquid state at room temperature as an antistatic agent. However, the pressure-sensitive adhesive layer made of such a pressure-sensitive adhesive composition has insufficient adhesiveness to the polarizer, and thus the antistatic agent migrates to the polarizer, resulting in deterioration of optical characteristics.

Furthermore, the low adhesion force causes problems such as lifting of the adhesive layer, bubbling and peeling, and this problem has been more seriously caused in a high temperature or high temperature-high humidity environment.

Japanese Patent Application Laid-Open No. 2005-27796 Japanese Patent Application Laid-Open No. 2006-011365 Korean Patent Publication No. 2010-0122885

As a result of various studies by the present inventors in order to solve the above problems, it has been found that when the antistatic agent is fixed with another material, the migration of the antistatic agent to the polarizer can be suppressed, A composition prepared by adding an ionic compound having an epoxy-reactive functional group capable of ionic bonding as an antistatic agent was prepared and introduced into an adhesive layer in contact with the polarizer. As a result, the antistatic effect and the adhesion to the polarizer were increased, It is possible to replace the functions of the conventional transparent protective film and the antistatic layer in addition to the excellent optical durability of the polarizing plate.

Accordingly, an object of the present invention is to provide an active energy ray-curable resin composition capable of immobilizing an antistatic agent in an epoxy compound.

Another object of the present invention is to provide the above-mentioned active energy ray-curable resin composition at the upper and lower portions of the polarizer, thereby making the polarizer thin and light.

It is still another object of the present invention to provide a liquid crystal display device including the polarizer.

In order to accomplish the above object, the present invention provides an epoxy resin composition comprising an epoxy compound, a cationic polymerization initiator, and an antistatic agent,

The antistatic agent includes one kind of compound selected from the group consisting of carboxylic acid group-containing ionic compounds represented by the following Chemical Formulas 1 to 3, thiol group-containing ionic compounds represented by Chemical Formulas 4 to 6, and combinations thereof Wherein the active energy ray-curable resin composition comprises:

[Chemical Formula 1]

(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(In the above Chemical Formulas 1 to 6, R _1, To R < ₁₀ >, X, Y, L and n are as described in the specification)

At this time, the active energy ray-curable resin composition further includes an oxetane compound, an acrylate compound, and a photo radical initiator.

The present invention also provides a polarizer comprising a polarizer, a first adhesive layer formed on one surface of the polarizer, and a second adhesive layer formed on the other surface of the polarizer,

Wherein the first adhesive layer and the second adhesive layer comprise the active energy ray-curable resin composition.

In addition, the present invention provides a liquid crystal display device including the polarizing plate.

The active energy ray curable resin composition of the present invention has an adhesive layer in contact with a polarizer and has an effect of providing excellent adhesion strength with a polarizer when introduced and preventing movement of an antistatic agent to a polarizer to prevent a decrease in optical durability.

In addition, it has an excellent antistatic effect, water resistance and dimensional stability even under the conditions of high temperature or high temperature and high humidity, so that the stability and quality of the polarizing plate can be enhanced.

In addition, since this adhesive layer can replace the role of a transparent protective film such as a conventional TAC and an antistatic layer, it is possible to exclude the adhesive layer and the TAC, and a separate adhesive layer required for attachment to the polarizer is not required A thin and lightweight polarizer can be achieved.

In particular, even in the manufacturing process, the adhesive layer can be easily cured on both sides of the polarizer by only one irradiation of light, thereby simplifying the manufacturing process compared to the conventional steps of manufacturing the adhesive layer, the transparent protective film, the antistatic layer and the adhesive layer As a result, there is an advantage that the manufacturing cost of the entire polarizing plate and the liquid crystal display device can be reduced.

The active energy ray curable resin composition according to the present invention is an epoxy resin composition comprising an epoxy compound and a cationic polymerization initiator, wherein the antistatic agent contains a functional group capable of forming a strong ionic bond with the epoxy group of the epoxy compound Ionic compounds are used.

The functional group may be a carboxylic acid group (COOH) and a thiol group (SH), preferably a carboxylic acid group-containing ionic compound and a thiol group-containing ionic compound. As the antistatic agent is immobilized on the epoxy resin itself due to strong ionic bonding by the carboxylic acid group and the thiol group, the conventional antistatic agent component is transferred to the polarizer, thereby effectively preventing the degradation of the optical characteristics of the polarizer. In addition to the above-mentioned antistatic function, strong adhesion to an epoxy compound can provide excellent adhesion when a cured film is formed.

Preferably, the ionic compound comprising a functional group capable of forming an ionic bond is represented by the following formulas (1) to (6):

(In the above Chemical Formulas 1 to 6,

X is nitrogen, phosphorus or sulfur,

R ₁ and R ₂ are the same or different and are each independently a C ₁ to C ₁₀ alkyl group, a C ₆ to C ₁₅ aryl group or a C ₃ to C ₁₂ heteroaryl group,

R ₃ is a C ₁ to C ₁₀ alkyl group, a C ₆ to C ₁₅ aryl group, or a C ₃ to C ₁₂ heteroaryl group when X is nitrogen or phosphorous, wherein R ₃ does not exist when X is sulfur,

R ₄ is C ₁ To C < ₁₀ >

R ₅ is C ₁ To C ₆ alkylene groups, C ₆ To C ₁₅ arylene groups or C ₃ To C ₁₂ heteroarylene group,

R ₆ to R ₁₀ are the same or different and each independently represents a C ₁ to C ₆ alkyl group, C ₆ To C ₁₅ arylene groups or C ₃ To C ₁₂ heteroarylene group,

Y is a substituted or unsubstituted C ₁ To C ₆ alkylene groups, substituted or unsubstituted C ₆ To C ₁₅ arylene groups or substituted or unsubstituted C ₃ To C ₁₂ heteroarylene group,

L is an anion,

and n is an integer of 1 to 5)

The alkyl group referred to in the present invention includes straight or branched and includes methyl, ethyl, n-propyl, i-propyl, n-butyl, isobutyl, , n-decyl, and the like.

The aryl groups mentioned in the present invention include phenyl, biphenyl, terphenyl, stilbene, naphthyl, anthracenyl, phenanthryl, pyrenyl and the like.

The heteroaryl group referred to in the present invention is a saturated or unsaturated ring structure containing at least one hetero atom (N, O or S) in the ring and is a furyl, thienyl, pyridyl, quinolinyl, isoquinolinyl, indole A thiazolyl, a thiazolyl, a benzofuranyl, a benzothiophenyl, a carbazolyl, a benzoxazolyl, a pyrimidinyl, a benzimidazolyl, a thiazolyl, a thiazolyl, a thiazolyl, Wherein R is selected from the group consisting of pyridyl, quinoxalinyl, benzothiazolyl, naphthyridinyl, isoxazolyl, isothiazolyl, furunyl, quinazolinyl, pyrazinyl, 1-oxydopyridyl, pyridazinyl, triazinyl, Oxadiazolyl, thiadiazole, tetrahydronaphthyl, and the like.

Unless otherwise specified, "alkylene" is a bivalent form of "alkyl", "arylene" is a bivalent form of "aryl" and "heteroarylene" is a divalent form of "heteroaryl".

The alkylene group, arylene group or heteroarylene group of Y referred to in the present invention is a group in which at least one hydrogen is substituted with a C ₁ to C ₆ alkyl group, a C ₂ to C ₆ alkenyl group, a C ₂ to C ₆ alkynyl group , A C ₃ to C ₁₀ cycloalkyl group, a C ₃ to C ₁₀ heterocycloalkyl group, a C ₃ to C ₁₀ heterocycloalkyloxy group, a C ₁ to C ₆ haloalkyl group, a C ₁ to C ₆ alkoxy group, A C ₁ to C ₆ thioalkoxy group, a C ₆ to C ₁₅ An aryl group, an acyl group, a hydroxy group, a thiol group, a halogen group, an amino group, an alkoxycarbonyl group, a carboxyl group, a carbamoyl group, a cyano group or a nitro group.

Wherein the cycloalkyl group includes cyclopropyl, cyclopropylmethyl, cyclopentyl, cyclohexyl, adamantyl, and substituted and unsubstituted boronyl, norbornyl, and norbornenyl.

Further, the heterocycloalkyl group means a cycloalkyl group in which at least one hydrogen is substituted with a hetero atom (N, O or S).

The heterocycloalkyloxy group is substituted by at least one hydrogen atom with a heteroatom (N, O or S) and includes oxygen (O) in the molecular structure.

The haloalkyl group means an alkyl group in which at least one hydrogen is substituted with a halogen atom.

The alkoxy includes methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.

The thioalkoxy group means a methylthio group, an ethylthio group, a propylthio group, an isopropylthio group, a butylthio group, an isobutylthio group or a t-butylthio group

Preferably, in the above Chemical Formulas 1 to 6 R ₁ and R ₂ are different from or equal to each other, a C ₁ to the aryl group of the C ₄ alkyl group or a C ₆ to C ₁₂ a, R ₃ is X is nitrogen or-ynyl when C ₁ To C ₄ alkyl group or C ₆ to C ₁₂ aryl group, and when X is sulfur, R ₄ is not C ₁ To an alkyl group of C _4, R ₅ is C ₁ To C ₄ alkylene groups, C ₆ To C ₁₂ arylene group or C ₆ To C ₁₂ heteroarylene groups, R ₆ to R ₁₀ are the same or different and each independently represents a C ₁ to C ₆ alkyl group or C ₆ To C ₁₂ arylene group, Y is C ₁ To C ₄ alkylene groups, C ₆ To C ₁₂ arylene group or C ₆ To C ₁₂ heteroarylene group, and L is a sulfonate, a halogen, an antimonate, a nitrile, a carboxyl, a borate, or a phosphate.

To preferably L is (methanesulfonate trifluoroacetate) OTf, OTs (toluene-4-sulfonate), OMs (methanesulfonate), Cl, Br, I, AlCl 4, Al 2 Cl 7, BF 4, PF _{6, ClO 4, NO 3,} CH 3 COO, CF 3 COO, CH 3 SO 3, CF 3 SO 3, (CF 3 SO 2) 2 N, (CF 3 SO 2) 3 C, AsF 6, SbF 6, _{NbF 6, TaF 6, F (} HF) n, (CN) 2 N, C 4 F 9 SO 3, (C 2 F 5 SO 2) 2 N, C 3 F 7 COO or (CF ₃ SO ₂₎ (CF ₃ CO) N (TFSI), more preferably PF ₆ or (CF ₃ SO ₂ ) (CF ₃ CO) N.

Most preferably, the carboxylic acid group-containing ionic compound is represented by the following formulas (7) to (17):

Preferably, the thiol group-containing ionic compound is represented by the following general formulas (18) to (22):

The ionic compound containing a functional group capable of forming an ionic bond in the present invention is contained in an amount of 1 to 40 parts by weight, preferably 2 to 30 parts by weight, based on 100 parts by weight of the epoxy compound. If the content is less than the above range, a sufficient charging effect can not be obtained, the effect of improving the compatibility of the antistatic agent is insufficient and it is difficult to secure durability. On the other hand, if the content exceeds the above range, Therefore, it is used properly within the above range.

The kind of the epoxy compound and cationic polymerization initiator constituting the active energy ray-curable resin composition together with the above ionic compound is not particularly limited in the present invention, and may include materials known in this field.

The epoxy compound is used for increasing the adhesion and adhesion of the cured film, and preferably a hydrogenated epoxy compound, an alicyclic epoxy compound, an aliphatic epoxy compound, or a mixture thereof.

The hydrogenated epoxy compound means a resin obtained by selectively hydrogenating an aromatic epoxy resin under a pressure in the presence of a catalyst. Examples of the aromatic epoxy resin include bisphenol-type epoxy resins such as diglycidyl ether of bisphenol A, diglycidyl ether of bisphenol F, and diglycidyl ether of bisphenol S; Novolak type epoxy resins such as phenol novolac epoxy resin, cresol novolac epoxy resin, and hydroxybenzaldehyde phenol novolac epoxy resin; A glycidyl ether of tetrahydroxyphenylmethane, a glycidyl ether of tetrahydroxybenzophenone, and an epoxy-modified polyvinyl phenol. Although the hydrogenated epoxy resin of the aromatic epoxy resin becomes a hydrogenated epoxy resin, it is preferable to use hydrogenated bisphenol A glycidyl ether.

The alicyclic epoxy-based compound means an alicyclic cyclic compound containing at least one epoxy group in the molecule, as shown in Formula 23 below.

(In the above formula (23), m represents an integer of 2 to 15)

Specifically, the alicyclic epoxy compound represented by Formula 23 is obtained by reacting 7-oxabicyclo [4.1.0] heptane-3-carboxylic acid with (7-oxabicyclo [4.1.0] hepto- Ester compound with 4-methyl-7-oxabicyclo [4.1.0] heptane-3-carboxylic acid and (4-methyl-7-oxabicyclo [4.1.0] hept- Esters, esters of 7-oxabicyclo [4.1.0] heptane-3-carboxylic acid with 1,2-ethanediol, (7-oxabicyclo [4.1.0] hept- (4-methyl-7-oxabicyclo [4.1.0] hept-3-yl) methanol and adipic acid, an ester of (7-oxabicyclo [4.1.0] hept- 3-yl) methanol and 1,2-ethanediol.

More specifically, the alicyclic epoxy compound may be an alicyclic diepoxycarboxylate. For example, 3,4-epoxycyclohexylmethyl-3 ', 4'-epoxycyclohexanecarboxylate, 2- (3,4-epoxycyclohexyl-5,5-spiro-3,4- Bis ((3,4-epoxy-6-methylcyclohexyl) methyl) adipate, 3,4-epoxy-6-methyl Cyclohexyl-3 ', 4'-epoxy-6'-methylcyclohexanecarboxylate, ε-caprolactone-modified 3,4-epoxycyclohexylmethyl-3', 4'-epoxycyclohexanecarboxylate, Epoxy-cyclohexylmethyl-3 ', 4'-epoxycyclohexanecarboxylate, 3,4-epoxycyclohexylmethyl-3', 4'-epoxy Cyclohexanecarboxylate, methylenebis (3,4-epoxycyclohexane), di (3,4-epoxycyclohexylmethyl) ether of ethylene glycol, ethylenebis (3,4-epoxycyclohexyl Epoxycyclohexylhydrophthalic acid dioctyl and epoxycyclohexahydrophthalic acid di-2-ethylhexyl. In the examples of the present invention, 3,4-epoxycyclohexylmethyl-3 ', 4' -Epoxy cyclohexanecarboxylate was used.

The aliphatic epoxy compound may be an aliphatic polyhydric alcohol or a polyglycidyl ether of an alkylene oxide adduct thereof. Specific examples thereof include diglycidyl ether of 1,4-butanediol, diglycidyl ether of 1,6-hexanediol, triglycidyl ether of glycerin, triglycidyl ether of trimethylol propane, diglycidyl ether of polyethylene glycol (Ethylene oxide, propylene oxide or the like) to aliphatic polyhydric alcohols such as ethylene glycol, propylene glycol, and glycerin and the like, which are obtainable by adding one or more alkylene oxides (ethylene oxide, propylene oxide, etc.) And polyglycidyl ether of ether polyol.

The hydrogenated epoxy compound, alicyclic epoxy compound and aliphatic epoxy compound may be used alone or in admixture of two or more.

The epoxy equivalent of the epoxy compound used in the present invention is usually 30 to 3000 g / equivalent, preferably 50 to 1500 g / equivalent. At this time, if the epoxy equivalent is less than 30 g / equivalent, the flexibility of the coated film after curing may deteriorate or the adhesive strength may decrease. On the other hand, if it exceeds 3,000 g / equivalent, there is a possibility that the compatibility with other components may deteriorate.

The cationic polymerization initiator is used for curing the epoxy compound, and initiates the polymerization reaction of the epoxy compound with a compound that produces a cation or a Lewis acid by irradiation with an active energy ray or heating.

The cationic polymerization initiator that can be used is not particularly limited in the present invention, and representative examples thereof include onium salts such as aromatic diazonium salts, aromatic iodo aluminum salts, and aromatic sulfonium salts, and teth-allene complexes, but are not limited thereto .

Examples of the aromatic diazonium salt include benzene diazonium hexafluoroantimonate, benzene diazonium hexafluorophosphate, and benzene diazonium hexafluoroborate.

Examples of the aromatic iodo aluminum salt include diphenyl iodonium tetrakis (pentafluorophenyl) borate, diphenyl iodonium hexafluorophosphate, diphenyl iodonium hexafluoroantimonate, di (4-nonylphenyl) Iodonium hexafluorophosphate, and the like.

Examples of the aromatic sulfonium salt include triphenylsulfonium hexafluorophosphate, triphenylsulfonium hexafluoroantimonate, triphenylsulfonium tetrakis (pentafluorophenyl) borate, 4,4'-bis [diphenyl sulfide Bis [di (? - hydroxyethoxy) phenylsulfonio] diphenyl sulfide bishexafluoroantimonate, 4,4'-bis [Di (? - hydroxyethoxy) phenylsulfonio] diphenyl sulfide bishexafluorophosphate, 7- [di (p-toluyl) sulfonio] -2-isopropylthioxanthone hexafluoroanti (Pentafluorophenyl) borate, 4-phenylcarbonyl-4 ' -diphenylsulfonio- < / RTI > Diphenyl sulfide hexafluorophosphate, 4- (p-tert-butylphenylcarbonyl) -4'-diphenylsulfonio- Diphenylsulfide tetrakis (pentafluorophenyl) borate, and the like can be used in place of the compound represented by the following general formula (1): < EMI ID = .

Examples of the teth-allene complexes include xylene-cyclopentadienyl iron (II) hexafluoroantimonate, cumene-cyclopentadienyl iron (II) hexafluorophosphate, xylene-cyclopentadiene (II) -tris (trifluoromethylsulfonyl) methanide, and the like.

These cationic polymerization initiators may be used singly or in combination of two or more of the above-mentioned compositions. Among them, especially when an aromatic sulfonium salt is used, the curability is excellent and the mechanical properties and adhesive strength of the cured film can be further improved.

The cationic polymerization initiator may be used directly or may be purchased commercially. For example, commercially available products include Kayalad PCI-220, Kayalad PCI-620, UVI-6990 manufactured by Union Carbide, Adekaoftama SP-150, Adekahopma SP-170, manufactured by Nippon Kayaku Co., DPI-101, DPI-102, DPI-103 and CIP-2064 manufactured by Nihon Soda Co., Ltd., CI-5102, CIT-1370, CIT-1682, CIP-1866 S, 101, TPS-102, TPS-103, TPS-105, MDS-103, MDS-103, BBI- 105, DTS-102, and DTS-103, and PI-2074 of Rhodia Japan Co., Ltd.

The cationic polymerization initiator performs sufficient curing of the epoxy compound to limit its content so as not to affect the physical properties of the coating film. It is preferably used in an amount of 0.01 to 10 parts by weight, more preferably 1 to 6 parts by weight, based on 100 parts by weight of the epoxy compound. If the content is less than the above range, the curing of the epoxy compound becomes insufficient and the mechanical strength and the adhesive strength of the cured film deteriorate. On the other hand, if the content exceeds the above range, The moisture absorption of the film is increased and the optical durability performance may be lowered. Therefore, the film is suitably adjusted within the above range.

The above-mentioned active energy ray-curable resin composition comprising an ionic compound having a carboxylic acid or thiol group, an epoxy compound, and a cationic polymerization initiator may further include other compositions.

Preferably, the active energy-curable resin composition of the present invention further comprises an oxetane compound, an acrylate-based compound and a photo radical initiator.

The oxetane compound lowers the viscosity of the active energy ray-curable resin composition, thereby facilitating the film production process as well as increasing the curing rate and improving the optical performance by suppressing the yellowing of the finally obtained cured film.

The oxetane compound is preferably used when an epoxy compound is applied to the active energy ray curable resin composition, and a compound having at least one oxetane ring (quaternary ring ether) in the molecular structure may be used.

The oxetane compound that can be used is not particularly limited in the present invention, but typically includes 3-ethyl-3-hydroxymethyloxetane, 1,4-bis [(3-ethyl- , 3-ethyl-3- (2-ethylhexyloxymethyl) oxetane, phenol novolac, (3-ethyl-3-oxycetanylmethyl) ether is used in the examples of the present invention.

These oxetane-based compounds can be used either directly or by purchasing commercially available materials. Specific examples of the oxetane-based compounds include Aronoxetane OXT-101, Aronoxetane OXT-121, Aronoxetane OXT-211, Cetane OXT-221, and alon oxetane OXT-212.

In the present invention, oxetane is used in an amount of 10 to 50 parts by weight, preferably 20 to 40 parts by weight, based on 100 parts by weight of the epoxy compound, to control the content of the oxetane compound in order to maximize adhesiveness, do. If the content is less than the above range, the viscosity decreases due to addition of the oxetane-based compound or the effect such as improvement of the optical performance is not sufficient. On the other hand, if the content exceeds the above range, the adhesion to the polarizer may be deteriorated , It is preferable to use them appropriately within the above range.

Acrylate compound is a polymerizable substance which can be polymerized by irradiation with an active energy ray (for example, ultraviolet rays, visible light, electron beam, X-ray or the like), and a (meth) acrylate compound having at least one (meth) acryloyloxy group in the molecular structure, Acrylic compound.

Examples of the (meth) acrylic compound having at least one (meth) acryloyloxy group in the molecule include (meth) acrylate monomers having at least one (meth) acryloyloxy group in the molecule, (Meth) acryloyloxy group-containing compounds such as (meth) acrylate oligomers having an acryloyloxy group.

(Meth) acryloyloxy group means acryloyloxy group and methacryloyloxy group, and (meth) acrylic compound means acrylate ester derivative and methacrylate ester derivative, and (meth) acryloyloxy group and Means an acrylate monomer and a methacrylate monomer, and (meth) acrylate oligomer means an acrylate oligomer or a methacrylate oligomer, respectively.

(Meth) acrylate monomers include monofunctional (meth) acrylate monomers having one (meth) acryloyloxy group in the molecule, bifunctional (meth) acrylate monomers having two (meth) acryloyloxy groups in the molecule (Meth) acryloyloxy monomer having at least three (meth) acryloyloxy groups in the molecule. These (meth) acrylate monomers may be used alone or in combination of two or more.

More specifically, the monofunctional (meth) acrylate monomer is selected from the group consisting of tetrahydrofurfuryl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) (Meth) acrylate, 2-hydroxybutyl (meth) acrylate, 2-hydroxy-3-phenoxypropyl (meth) acrylate, isobutyl (meth) (Meth) acrylate, cyclohexyl (meth) acrylate, dicyclopentenyl (meth) acrylate, benzyl (meth) acrylate, isobonyl Acrylate, trimethylolpropane (meth) acrylate, pentaerythritol (meth) acrylate, phenoxypolyethylene glycol (meth) acrylate, (Meth) acrylate monomers such as 2- (meth) acryloyloxyethylphthalic acid, 2- (meth) acryloyloxyethylhexahydrophthalic acid, carboxyethyl (meth) acrylate, (Meth) acryloyloxyethyl succinic acid, N- (meth) acryloyloxy-N ', N'-dicarboxy-p-phenylenediamine, 4- (meth) acryloyloxyethyltri And mellitic acid. The monofunctional (meth) acrylate monomer also includes a (meth) acryloylamino group-containing monomer such as 4- (meth) acryloylamino-1-carboxymethylpiperidine.

Examples of bifunctional (meth) acrylate monomers include alkylene glycol di (meth) acrylates, polyoxyalkylene glycol di (meth) acrylates, halogen-substituted alkylene glycol di (meth) acrylates, Di (meth) acrylates of di (meth) acrylates, hydrogenated dicyclopentadiene or tricyclodecanedialanol, di (meth) acrylates of dioxane glycol or dioxanedialanol, bisphenol A or bisphenol A Di (meth) acrylates of alkylene oxide adducts of bisphenol A and bisphenol A, epoxy di (meth) acrylates of bisphenol A or bisphenol F, and the like.

Specific examples of the bifunctional (meth) acrylate monomers include ethylene glycol di (meth) acrylate, 1,3-butanediol di (meth) acrylate, 1,4-butanediol di (meth) (Meth) acrylate such as hexanediol di (meth) acrylate, 1,9-nonanediol di (meth) acrylate, neopentyl glycol di (meth) acrylate, trimethylolpropane di (Meth) acrylate, diethylene glycol di (meth) acrylate, dipropylene glycol di (meth) acrylate, tripropylene glycol di Acrylate, poly (ethylene glycol) di (meth) acrylate, polypropylene glycol di (meth) acrylate, polytetramethylene glycol di (Meth) acrylate, 2,2-bis [4- (meth) acryloyloxyethoxyethoxyphenyl] propane, 2,2- (Meth) acrylate, tricyclodecane dimethanol di (meth) acrylate, 1,3-dioxane-2,5-diyl (meth) acrylate, Di (meth) acrylate (trade name: DIOXAN LIKOR), acetal compound of hydroxypivalic aldehyde and trimethylol propane (chemical name: 2- (2-hydroxy-1,1-dimethylethyl) Di (meth) acrylate of 1,3,5-tris (hydroxymethyl-1,3-dioxane) and di (meth) acrylate of 1,3,5-tris (2-hydroxyethyl) isocyanurate.

Examples of the polyfunctional (meth) acrylate monomer include glycerin tri (meth) acrylate, trimethylol propane tri (meth) acrylate, ditrimethylol propane tri (meth) acrylate, ditrimethylol propane tetra (meth) (Meth) acrylate, dipentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, Poly (meth) acrylates of tri- or higher aliphatic polyols such as acrylate and the like, and poly (meth) acrylates of tri- or higher halogen substituted polyols, tri (meth) acrylates of alkylene oxide adducts of glycerin, Tri (meth) acrylates of alkylene oxide adducts of trimethylolpropane, 1,1,1-tris [(meth) acryloyl Tri (meth) acrylate of cyclohexyl (methoxy) ethoxy] propane, 1,3,5-tris (2-hydroxyethyl) isocyanurate and silicone hexa (meth) acrylate.

These acrylate compounds are used in an amount of 50 to 90 parts by weight, more preferably 60 to 80 parts by weight, based on 100 parts by weight of the epoxy compound, in order to sufficiently secure the adhesion and adhesion of the cured film . If the content is less than the above range, the adhesive strength and adhesion to the polarizer may be deteriorated. On the contrary, when the content exceeds the above range, yellowing may occur in the cured film, resulting in deterioration of optical performance. do.

The photo-radical initiator is used for curing the acrylate-based compound and the ionic compound.

The photo-radical initiator that can be used is not particularly limited in the present invention, and any photo-initiator that can initiate photo-curing by irradiation of a known active energy ray can be used. The active energy ray includes visible rays, ultraviolet rays, X rays, electron rays, and the like.

Typically, the photoradical initiator is selected from the group consisting of acetophenone, 3-methylacetophenone, benzyldimethylketal, 1- (4-isopropylphenyl) -2-hydroxy- 2-methyl-1-phenylpropan-1-one, benzophenone, 4 (methylthio) A benzophenone-based initiator including chlorobenzophenone, 4,4'-diaminobenzophenone, a benzoin ether-based initiator including benzoin propyl ether, benzoin ethyl ether, Thiazane-based initiators, other quinones, fluorenone, cordierite-quinone, benzaldehyde, anthraquinone, and the like.

These photo radical initiators control the content thereof so that physical properties of the coating film can be secured through sufficient curing. Preferably, the photo-radical initiator is used in an amount of 0.5 to 20 parts by weight, preferably 1 to 6 parts by weight, based on 100 parts by weight of the epoxy compound. If the content is less than the above range, the curing tends to be insufficient and the mechanical strength and the adhesive strength tend to decrease. On the other hand, if the content exceeds the above range, the ionic substances in the cured product increase, , It is preferably adjusted within the above range.

In addition to the above-mentioned components, the active energy ray-curable resin composition according to the present invention may further contain an antioxidant, a leveling agent, a surface-treating agent, an antioxidant, Lubricants, dyes, pigments, defoamers, fillers, light stabilizers, and the like.

The method for producing the active energy ray-curable resin composition containing the above-mentioned composition is not particularly limited in the present invention, but follows the well-known method.

The active energy ray-curable resin composition according to the present invention can be preferably used as a polarizing plate of a liquid crystal display, in particular, as an adhesive layer directly contacting a polarizer of a polarizing plate.

Specifically, a polarizing plate according to the present invention includes a first adhesive layer formed on one surface of a polarizer, and a second adhesive layer formed on the other surface of the polarizer, wherein the first adhesive layer and the second adhesive layer are formed by a tact And one active energy ray-curable resin composition.

Since the ionic compound having a carboxylic acid or thiol group as an antistatic agent is fixed to the epoxy-based polymer, the migration of the antistatic agent to the polarizer is suppressed, and the deterioration of the optical characteristics of the polarizer is originally blocked by the antistatic agent . In addition, it is possible to secure an effect of excellent antistatic properties, water resistance, dimensional stability, and excellent adhesion by a polarizer.

At this time, the adhesive layer has a thickness of 1 to 20 탆, preferably 2 to 10 탆.

The adhesive layer has physical properties such as transparency, mechanical strength, thermal stability and moisture barrier property required for a transparent protective film such as TAC and can be used in place of a protective film. The adhesive layer has an antistatic effect, And can be easily attached to the polarizer without the need for a separate adhesive layer or adhesive layer or the like for attachment of these layers.

As a result, the conventional polarizer has a structure of a protective film / adhesive layer / polarizer / adhesive layer / protective film so as to have a thickness of at least 115 μm. In the present invention, since it can be formed of an adhesive layer / polarizer / adhesive layer It can be manufactured at a level of 65 μm or less (the thickness of the polarizer is 25 μm), so that the thin and light weight of the polarizing plate can be achieved. The production of the polarizing plate is not particularly limited in the present invention, but follows the well-known method.

For example, the active energy ray-curable resin composition is directly applied to a polarizer to form a coating film, or after forming a coating film on the other substrate, photo-curing is performed by irradiation of active energy rays.

Preferably, the adhesive layer can be formed by irradiating the active energy ray-curable resin composition with a polarizer after forming the coating film, and irradiating the active energy ray with only one active energy ray. This method is a very simplified process as compared with the lamination and laminating process of the conventional adhesive layer and the transparent protective film (for example, TAC), and can reduce the overall process cost.

The application to the coating or substrate may be performed according to a conventionally known method and may be carried out by a known method such as a natural coater, knife belt coater, floating knife, knife over roll, knife on blanket, spray, dip, kiss roll, squeeze roll, A curtain float coater, a comma coater, a gravure coater, a micro gravure coater, a die coater and a curtain coater.

The substrate is not particularly limited in the present invention and may be any known polymer material, paper or metal foil.

As mentioned above, the active energy ray includes visible rays, ultraviolet rays, X-rays and electron rays. Ultraviolet rays are preferred because they can be used at low cost. As a light source for curing by ultraviolet rays, various materials can be used, and examples thereof include pressurized or high-pressure mercury lamps, metal halide lamps, xenon lamps, electrodeless discharge lamps, carbon arc lamps, and LEDs.

In the case of curing by electron beam, various devices can be used as the EB irradiating device that can be used. Examples of the EB irradiating device include a COCROW WALTON type, a Bandegraph type, and a resonant transformer type device. Preferably has an energy of 50 to 1000 eV, more preferably 100 to 300 eV.

A polarizing plate having a structure in which an adhesive layer / polarizer / adhesive layer is laminated is manufactured through the above-described method.

At this time, the upper and lower portions of the polarizing plate may further include a known optical functional film used in this field.

Examples of the optically functional film include an optical compensation film in which a liquid crystal compound or a polymer compound thereof is oriented on the surface of a base material, a reflection type film that transmits polarized light of any kind, A polarizing separating film, a retardation film containing a polycarbonate resin, a retardation film containing a cyclic polyolefin resin, an antireflection functional film having a concavo-convex shape on its surface, an additional film having antireflection treatment on its surface, , And a transflective film having both a reflecting function and a transmitting function. One or two or more of these optical functional films can be laminated and used. Such an optically functional film may be introduced in a film state as described above, and in some cases, a treatment for hard coat treatment, antireflection treatment, anti-sticking, diffusion or anti-glare may be performed.

Further, the surface treatment can be performed for the purpose of improving the adhesion and the like. Examples of the surface treatment include a dry treatment such as a primer treatment, a plasma treatment and a corona treatment, a chemical treatment such as an alkali treatment (saponification treatment), and a coating treatment for forming an easy adhesive layer.

Such a polarizing plate can be applied to all ordinary liquid crystal display devices.

The polarizing plate of the present invention can be applied to both the upper plate and the lower plate polarizing plate of a liquid crystal display device. In particular, when applied to a lower plate polarizing plate, since light is transmitted to the liquid crystal cell after resolving the distortion of light, desirable.

In this case, the liquid crystal display device is not particularly limited, and liquid crystal display devices of various driving methods such as reflective type, transmissive type and transflective type liquid crystal display (LCD) and TN type, STN type, OCB type, HAN type, VA type, Device (LCD) can be preferably used.

In the present invention, since the liquid crystal display device is well known to those skilled in the art, detailed description of each configuration will be omitted.

It will be apparent to those skilled in the art that various modifications and variations can be made in the present invention without departing from the spirit or scope of the present invention. Such variations and modifications are intended to be within the scope of the appended claims. The content of each composition is based on the weight of the solid content, unless otherwise specified.

Example  One: Active energy ray  Preparation of Curable Resin Composition

)로 표시되는 에폭시 반응성 관능기 함유 이온성 화합물 2 중량부를 첨가하고, 균일하게 혼합하여 활성에너지선 경화성 수지 조성물을 제조하였다.
100 parts by weight of an epoxy compound (3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, Daicel Chemical Industries, Ltd., Serokissite 2021P), a cationic polymerization initiator (4,4'-bis [Diphenylsulfonio] diphenyl sulfide bishexafluorophosphate), and 5 parts by weight of an antistatic agent represented by the following formula (7)

) And 2 parts by weight of an epoxy reactive functional group-containing ionic compound represented by the following formula (1) were added and uniformly mixed to prepare an active energy ray curable resin composition.

Example  2: Active energy ray  Preparation of Curable Resin Composition

)을 사용한 것을 제외하고는 상기 실시예 1과 동일하게 수행하여 활성에너지선 경화성 수지 조성물을 제조하였다.
As an antistatic agent, the compound of formula (8) (

) Was used in place of the compound (1) to prepare an active energy ray-curable resin composition.

Example  3: Active energy ray  Preparation of Curable Resin Composition

)을 사용한 것을 제외하고는 상기 실시예 1과 동일하게 수행하여 활성에너지선 경화성 수지 조성물을 제조하였다.
As an antistatic agent, the compound of formula (9) (

) Was used in place of the compound (1) to prepare an active energy ray-curable resin composition.

Example  4: Active energy ray  Preparation of Curable Resin Composition

)을 사용한 것을 제외하고는 상기 실시예 1과 동일하게 수행하여 활성에너지선 경화성 수지 조성물을 제조하였다.
As an antistatic agent, the compound of formula (10) (

) Was used in place of the compound (1) to prepare an active energy ray-curable resin composition.

Example  5: Active energy ray  Preparation of Curable Resin Composition

)을 사용한 것을 제외하고는 상기 실시예 1과 동일하게 수행하여 활성에너지선 경화성 수지 조성물을 제조하였다.
As the antistatic agent, the compound of the formula (11) (

) Was used in place of the compound (1) to prepare an active energy ray-curable resin composition.

Example  6: Active energy ray  Preparation of Curable Resin Composition

)을 사용한 것을 제외하고는 상기 실시예 1과 동일하게 수행하여 활성에너지선 경화성 수지 조성물을 제조하였다.
As an antistatic agent, the compound of the formula (12) (

) Was used in place of the compound (1) to prepare an active energy ray-curable resin composition.

Example  7: Active energy ray  Preparation of Curable Resin Composition

)을 사용한 것을 제외하고는 상기 실시예 1과 동일하게 수행하여 활성에너지선 경화성 수지 조성물을 제조하였다.
Instead of the compound of the formula (7) as the antistatic agent, the compound of the formula (13

) Was used in place of the compound (1) to prepare an active energy ray-curable resin composition.

Example  8: Active energy ray  Preparation of Curable Resin Composition

)을 사용한 것을 제외하고는 상기 실시예 1과 동일하게 수행하여 활성에너지선 경화성 수지 조성물을 제조하였다.Instead of the compound of the formula (7) as the antistatic agent, the compound of the formula (14

) Was used in place of the compound (1) to prepare an active energy ray-curable resin composition.

Example  9: Active energy ray  Preparation of Curable Resin Composition

)을 사용한 것을 제외하고는 상기 실시예 1과 동일하게 수행하여 활성에너지선 경화성 수지 조성물을 제조하였다.Instead of the compound of the formula (7) as the antistatic agent, the compound of the formula (15)

) Was used in place of the compound (1) to prepare an active energy ray-curable resin composition.

Example  10: Active energy ray  Preparation of Curable Resin Composition

)을 사용한 것을 제외하고는 상기 실시예 1과 동일하게 수행하여 활성에너지선 경화성 수지 조성물을 제조하였다.Instead of the compound of the formula (7) as the antistatic agent, the compound of the formula (16)

) Was used in place of the compound (1) to prepare an active energy ray-curable resin composition.

Example  11: Active energy ray  Preparation of Curable Resin Composition

)을 사용한 것을 제외하고는 상기 실시예 1과 동일하게 수행하여 활성에너지선 경화성 수지 조성물을 제조하였다.
Instead of the compound of the formula (7) as the antistatic agent, the compound of the formula (17

) Was used in place of the compound (1) to prepare an active energy ray-curable resin composition.

Example  12: Active energy ray  Preparation of Curable Resin Composition

)을 사용한 것을 제외하고는 상기 실시예 1과 동일하게 수행하여 활성에너지선 경화성 수지 조성물을 제조하였다.
As the antistatic agent, the compound of formula (18) (

) Was used in place of the compound (1) to prepare an active energy ray-curable resin composition.

Example  13: Active energy ray  Preparation of Curable Resin Composition

)을 사용한 것을 제외하고는 상기 실시예 1과 동일하게 수행하여 활성에너지선 경화성 수지 조성물을 제조하였다.
As an antistatic agent, the compound of formula (19) (

) Was used in place of the compound (1) to prepare an active energy ray-curable resin composition.

Example  14: Active energy ray  Preparation of Curable Resin Composition

)을 사용한 것을 제외하고는 상기 실시예 1과 동일하게 수행하여 활성에너지선 경화성 수지 조성물을 제조하였다.
As an antistatic agent, the compound of formula (20) (

) Was used in place of the compound (1) to prepare an active energy ray-curable resin composition.

Example  15: Active energy ray  Preparation of Curable Resin Composition

)을 사용한 것을 제외하고는 상기 실시예 1과 동일하게 수행하여 활성에너지선 경화성 수지 조성물을 제조하였다.
As an antistatic agent, the compound of the formula (21) (

) Was used in place of the compound (1) to prepare an active energy ray-curable resin composition.

Example  16: Active energy ray  Preparation of Curable Resin Composition

)을 사용한 것을 제외하고는 상기 실시예 1과 동일하게 수행하여 활성에너지선 경화성 수지 조성물을 제조하였다.
As an antistatic agent, the compound of the formula (22) (

) Was used in place of the compound (1) to prepare an active energy ray-curable resin composition.

Example  17: Active energy ray  Preparation of Curable Resin Composition

) 2 중량부, 및 옥세탄 화합물(비스(3-에틸-3-옥세타닐메틸)에테르, 동아합성제, 알론옥세탄 OXT-221) 30 중량부를 첨가하고, 균일하게 혼합하여 활성에너지선 경화성 수지 조성물을 제조하였다
100 parts by weight of an epoxy compound (3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, Daicel Chemical Industries, Ltd., Serokissite 2021P), a cationic polymerization initiator (4,4'-bis [Diphenylsulfonio] diphenyl sulfide bishexafluorophosphate), 5 parts by weight of the compound of the formula (11) as an antistatic agent

) And 30 parts by weight of an oxetane compound (bis (3-ethyl-3-oxetanylmethyl) ether, Donga Synthetic Agent, Alonoxetane OXT-221) were added and uniformly mixed to obtain an active energy ray- A resin composition was prepared

Example  18: Active energy ray  Preparation of Curable Resin Composition

75 parts by weight of an acrylate compound (tricyclodecane dimethanol diacrylate, A-DCP, manufactured by Shin-Nakamura Chemical Co., Ltd.), and 75 parts by weight of a photo radical initiator (2-hydroxy- 1-one (DAROCURE 1173, manufactured by Ciba Specialty Chemicals, Inc.) was further added to prepare an active energy ray-curable resin composition.

Comparative Example 1: Active energy ray  Preparation of Curable Resin Composition

An active energy ray-curable resin composition was prepared in the same manner as in Example 1 except that no antistatic agent was used.

Comparative Example 2: Active energy ray  Preparation of Curable Resin Composition

An active energy ray curable resin composition was prepared in the same manner as in Example 18 except that no antistatic agent was used.

Comparative Example 3: Active energy ray  Preparation of Curable Resin Composition

An active energy ray curable resin composition was prepared in the same manner as in Example 1 except that NaPF ₆ was used as an antistatic agent.

Comparative Example 4: Active energy ray  Preparation of Curable Resin Composition

An active energy ray curable resin composition was prepared in the same manner as in Example 18 except that NaPF ₆ was used as an antistatic agent.

Experimental Example  1: active Energy line  Polarizing plate production using curable composition

(1) Production of Polarizer

A polyvinyl alcohol film having an average degree of polymerization of about 2400 and a degree of saponification of 99.9 mol% and a thickness of 75 탆 was immersed in pure water at 30 캜.

Subsequently, the substrate was immersed in an aqueous solution of oxo / potassium iodide / water in an aqueous solution having a weight ratio of 0.02 / 2/100 at 30 ° C, and then immersed in an aqueous solution having a weight ratio of potassium iodide / boric acid / water of 12/5/100 at 56.5 ° C.

Subsequently, the substrate was washed with pure water at 8 占 폚, dried at 65 占 폚, and a polarizer (or polarizing film, 30 占 퐉) in which oxo was adsorbed and oriented in polyvinyl alcohol was obtained. At this time, the elongation was made to be 5.3 times.

(2) active Energy line  A composition comprising a curable composition Curing membrane  Produce

The active energy ray-curable resin composition prepared in the above Examples and Comparative Examples was applied on a polyethylene terephthalate (PET) film (Ester Film E5100, manufactured by Toyobo Co., Ltd.) using Barcoater # 7.

Two PET films coated with a coating film were placed on both sides of the polarizer produced in the above (1) so that the coating film side became an adhesive surface.

Subsequently, ultraviolet rays were irradiated with an integrated dose of 1,500 mJ / cm ² by a D-valve manufactured by Fusion UV System to form a cured film.

Subsequently, the PET film on both sides was peeled off to obtain a polarizing plate having an adhesive layer with a thickness of 12 탆.

Test Example  1: Property test and analysis

The properties of the polarizer prepared in Experimental Example 1 were examined in the following manner.

(1) Thickness

(ZC-101, manufactured by Nikon Corporation).

(2) Adhesion

On the surface of the adhesive layer, a checkerboard pattern of 1 mm square was cut with a cutter knife, and a cellophane tape was laid out thereon, and a stripping test was carried out to count the number of checkerboard patterns that were not peeled out of 100 checkerboard patterns.

(3) Daejeon Preventiveness

(Hirest-up MCP-HT450, manufactured by Mitsubishi Chemical Corporation) at 23 캜 and 55% RH.

(4) Optical durability

60 DEG C and 90% RH, and the change in optical performance with time was measured.

First, the polarizing plate was cut into a size of 3 cm x 3 cm, and then a pressure-sensitive adhesive was used to adhere to glass to prepare a measurement sample. The sample was allowed to stand for 24 hours under 50 ℃, after the pressure treatment the autoclave for 1 hour at 5kg / cm ² (490.3kPa), again 23 ℃, 55% RH environment.

The transmittance spectrum of the obtained sample in the transmission axis direction and the absorption axis direction of the polarizer in a wavelength range of 380 to 700 nm of FT-IR (UV2450, manufactured by Shimadzu Corporation) was measured, ) And a unit transmissibility Ty (unit:%) were calculated.

The optical performance in this state was measured at the initial stage after standing for 120 hours under the environment of 60 占 폚 and 90% RH.

[Equation 1]

Percent change in polarization degree (ΔPy,%) = Py after initial test - Initial Py

 [Evaluation standard]

&Amp; cir &: Variation of polarization degree is less than 1

?: Variation of polarization degree is less than 1 to 5

X: Change amount of polarization degree is 5 or more

 &Quot; (2) "

(%) ≪ tb > < tb > Ty-initial Ty

[Evaluation standard]

⊚: Change in transmittance is less than 1

DELTA: Change in transmittance is less than 3 to 5

X: Change amount of transmittance is 5 or more

The physical properties measured in the above (1) to (4) are shown in Table 1 below.

division Thickness (㎛) Adhesiveness
(100/100) Surface resistance
(Ω / □) Optical durability ΔPy,% ΔTy,% Example 1 55 100 2.1 X 10 ¹⁰ ◎ ◎ Example 2 54 100 2.3 X 10 ¹⁰ ◎ ◎ Example 3 55 100 3.0 X 10 ¹⁰ ◎ ◎ Example 4 54 100 2.5 X 10 ¹⁰ ◎ ◎ Example 5 54 100 3.6 X 10 ¹⁰ ◎ ◎ Example 6 56 100 1.9 X 10 ¹⁰ ◎ ◎ Example 7 54 100 4.7 X 10 ¹⁰ ◎ ◎ Example 8 55 100 1.6 X 10 ¹⁰ ◎ ◎ Example 9 53 100 2.5 X 10 ¹⁰ ◎ ◎ Example 10 55 100 3.4 X 10 ¹⁰ ◎ ◎ Example 11 57 100 2.7 X 10 ¹⁰ ◎ ◎ Example 12 55 100 3.8 X 10 ¹⁰ ◎ ◎ Example 13 54 100 2.0 X 10 ¹⁰ ◎ ◎ Example 14 57 100 5.2 X 10 ¹⁰ ◎ ◎ Example 15 55 100 4.0 X 10 ¹⁰ ◎ ◎ Example 16 54 100 3.1 X 10 ¹⁰ ◎ ◎ Example 17 56 100 2.6 X 10 ¹⁰ ◎ ◎ Example 18 54 100 5.0 X 10 ¹⁰ ◎ ◎ Comparative Example 1 55 100 9.9 X 10 ¹³ OVER ◎ ◎ Comparative Example 2 53 100 9.9 X 10 ¹³ OVER ◎ ◎ Comparative Example 3 55 90 6.2 X 10 ¹¹ X X Comparative Example 4 54 92 3.8 X 10 ¹¹ X X

Referring to Table 1, it can be seen that the films of Examples 1 to 18 according to the present invention are excellent in adhesion of the adhesive layer to the polarizer, and excellent in optical durability even under high temperature and humid conditions while maintaining high chargeability.

In contrast, in Comparative Examples 1 and 2 in which no antistatic agent was used, the antistatic effect could not be expected because of the high resistance.

In addition, in Comparative Examples 3 and 4 using other antistatic agents, the adhesiveness was low and the optical characteristics were poor. This result was attributable to the fact that the antistatic agent was transferred to the polarizer.

Claims (9)

An epoxy-based compound, a cationic polymerization initiator, and an antistatic agent,
Wherein the antistatic agent is at least one functional group-containing ion selected from the group consisting of carboxylic acid group-containing ionic compounds represented by the following Chemical Formulas 1 to 3, thiol group-containing ionic compounds represented by Chemical Formulas 4 to 6, Wherein the active energy ray-curable resin composition comprises:
[Chemical Formula 1]

(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(In the above Chemical Formulas 1 to 6,
X is nitrogen, phosphorus or sulfur,
R ₁ and R ₂ are the same or different and are each independently a C ₁ to C ₁₀ alkyl group, a C ₆ to C ₁₅ aryl group or a C ₃ to C ₁₂ heteroaryl group,
R ₃ is a C ₁ to C ₁₀ alkyl group, a C ₆ to C ₁₅ aryl group, or a C ₃ to C ₁₂ heteroaryl group when X is nitrogen or phosphorous, wherein R ₃ does not exist when X is sulfur,
R ₄ is C ₁ To C < ₁₀ >
R ₅ is C ₁ To C ₆ alkylene groups, C ₆ To C ₁₅ arylene groups or C ₃ To C ₁₂ heteroarylene group,
R ₆ to R ₁₀ are the same or different and each independently represents a C ₁ to C ₆ alkyl group, C ₆ To C ₁₅ arylene groups or C ₃ To C ₁₂ heteroarylene group,
Y is a substituted or unsubstituted C ₁ To C ₆ alkylene groups, substituted or unsubstituted C ₆ To C ₁₅ arylene groups or substituted or unsubstituted C ₃ To C ₁₂ heteroarylene group,
L is an anion,
and n is an integer of 1 to 5) [6] The compound according to claim 1,
R_One And R₂Are the same or different, and C_One To C₄Alkyl group or C₆ To C₁₂Lt; / RTI >
R₃When X is nitrogen or phosphorous, C_One To C₄Or an alkyl group of C₆ To C₁₂Lt; / RTI > is not present when X is sulfur,
R₄C_One To C₄Lt; / RTI >
R₅C_One To C₄An alkylene group of C₆ To C₁₂Or an arylene group of C₆ To C₁₂Lt; / RTI >
R₆ To R₁₀Are each independently of the other C_One To C₆Alkyl group or C₆ To C₁₂Lt; / RTI >
Y is C_One To C₄An alkylene group of C₆ To C₁₂Or an arylene group of C₆ To C₁₂Lt; / RTI >
L is a sulfonate, a halogen, an antimonate, a nitrile, a carboxyl, a borate, or a phosphate,
and n is an integer of 1 to 5. The active energy ray-curable resin composition according to claim 1, wherein the carboxylic acid group-containing ionic compound is represented by the following formulas (7) to (17):
(7)

[Chemical Formula 8]

[Chemical Formula 9]

[Chemical formula 10]

(11)

[Chemical Formula 12]

[Chemical Formula 13]

[Chemical Formula 14]

[Chemical Formula 15]

[Chemical Formula 16]

[Chemical Formula 17]

The active energy ray-curable resin composition according to claim 1, wherein the carboxylic acid group-containing ionic compound is represented by the following formulas (18) to (22):
[Chemical Formula 18]

[Chemical Formula 19]

[Chemical Formula 20]

[Chemical Formula 21]

[Chemical Formula 22]

The active energy ray-curable resin composition according to claim 1, wherein the active energy ray-curable resin composition comprises 0.01 to 10 parts by weight of a cationic polymerization initiator and 1 to 40 parts by weight of a functional group-containing ionic compound per 100 parts by weight of the epoxy- Curable resin composition. The active energy ray-curable resin composition according to claim 1, wherein the active energy ray-curable resin composition further comprises an oxetane compound, an acrylate-based compound, and a photo radical initiator [Claim 7] The active energy ray-curable resin composition according to claim 6,
Wherein the composition comprises 10 to 50 parts by weight of an oxetane compound, 50 to 90 parts by weight of an acrylate compound, and 0.5 to 20 parts by weight of a photo radical initiator per 100 parts by weight of the epoxy compound. A polarizer comprising a first adhesive layer formed on one surface of a polarizer, and a second adhesive layer formed on the other surface of the polarizer,
Wherein the first adhesive layer and the second adhesive layer comprise the active energy ray-curable resin composition according to any one of claims 1 to 7. A liquid crystal display device comprising the polarizing plate of claim 8.