KR102051173B1 - Adhesive composition and polarizing plate comprising adhesive layer formed by using the same - Google Patents
Adhesive composition and polarizing plate comprising adhesive layer formed by using the same Download PDFInfo
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- KR102051173B1 KR102051173B1 KR1020150151640A KR20150151640A KR102051173B1 KR 102051173 B1 KR102051173 B1 KR 102051173B1 KR 1020150151640 A KR1020150151640 A KR 1020150151640A KR 20150151640 A KR20150151640 A KR 20150151640A KR 102051173 B1 KR102051173 B1 KR 102051173B1
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J7/00—Adhesives in the form of films or foils
- C09J7/20—Adhesives in the form of films or foils characterised by their carriers
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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
- G02B5/3033—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state in the form of a thin sheet or foil, e.g. Polaroid
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- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
- G02F1/133528—Polarisers
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
- C09J2203/318—Applications of adhesives in processes or use of adhesives in the form of films or foils for the production of liquid crystal displays
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- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nonlinear Science (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Mathematical Physics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Polarising Elements (AREA)
Abstract
The present specification relates to an adhesive composition and a polarizing plate including an adhesive layer formed using the same.
Description
The present specification relates to an adhesive composition and a polarizing plate including an adhesive layer formed using the same.
The polarizing plate has been commonly used as a structure in which a protective film is laminated using one or both sides of a polarizer made of a polyvinyl alcohol (hereinafter referred to as 'PVA')-based resin dyed with dichroic dye or iodine. Conventionally, a triacetyl cellulose (TAC) film has been mainly used as a polarizer protective film, but such a TAC film has a problem in that it is easily deformed in a high temperature and high humidity environment. Accordingly, recently, protective films of various materials that can replace TAC films have been developed. For example, polyethylene terephthalate (PET), cycloolefin polymer (COP, cycloolefin polymer), and acrylic films may be used alone. Or a mixed use has been proposed.
At this time, an aqueous adhesive composed mainly of an aqueous solution of polyvinyl alcohol-based resin is used as the adhesive used to attach the polarizer and the protective film. However, in the case of the water-based adhesive, when using an acrylic film or a COP film other than TAC as a protective film, there is a problem that its use is limited depending on the film material because the adhesive strength is weak. In addition, in the case of the water-based adhesive, in addition to the problem of poor adhesion to the material, if the material of the protective film applied to both sides of the PVA device is different, the problem of curl generation of the polarizing plate by the drying process of the water-based adhesive and initial optical Problems such as deterioration of physical properties occur. In addition, when using the water-based adhesive, a drying step is necessary, and there is a problem in that a difference in moisture permeability, thermal expansion, etc. occurs in such a drying step, thereby increasing the defective rate. As an alternative to solve the above problems, a method of using a non-aqueous adhesive instead of an aqueous adhesive has been proposed.
The non-aqueous adhesive for polarizing plates proposed to date can be divided into radical curable adhesives and cationic curable adhesives according to the curing method. Cationic curable adhesives have the advantage of having excellent adhesion to films of various materials, but have a number of disadvantages in the manufacturing process due to the slow curing rate and low curing degree. In order to solve the problem of such a cationic curable adhesive, a radical curable adhesive having an acrylamide compound as a main component has been proposed. However, in the case of a radically curable adhesive containing an acrylamide compound as a main component, although the curing speed is faster than that of the cationic curable adhesive, there is a problem in that the curing speed is lowered and the adhesive strength is lowered in a high humidity atmosphere. On the other hand, since the polarizing plate manufacturing process includes a wet process in which the swelling, dyeing, and stretching of the polyvinyl alcohol film is performed in an aqueous solution, the moisture content is high. Therefore, in order to apply the acrylamide-based adhesive to the polarizing plate, the polarizer may be used before applying the adhesive. It is a situation that additional processes such as hot air drying or surface treatment such as plasma should be performed.
Therefore, the development of an adhesive that does not lower the curing rate and adhesive strength even in a high humidity environment so that it can be applied to the polarizing plate without a separate treatment is required.
The present specification provides an adhesive composition, a polarizing plate including an adhesive layer formed using the same.
According to an exemplary embodiment of the present specification, the first epoxy compound; Acrylic compounds; And a radical initiator, wherein the first epoxy-based compound includes at least one alkoxy silyl group in a molecule.
According to an exemplary embodiment of the present specification, the polarizer; An adhesive layer provided on at least one surface of the polarizer and formed of the adhesive composition described above; And it provides a polarizing plate comprising a protective film provided on at least one surface on the adhesive layer.
Further, according to one embodiment of the present specification, a display panel; And it provides an image display device comprising the above-described polarizing plate provided on one side or both sides of the display panel.
The adhesive composition according to an exemplary embodiment of the present specification not only has excellent adhesion to films of various materials, for example, TAC film, acrylic film, COP film, PET film, etc., but also has excellent water resistance and stable adhesion even at high humidity. Can be maintained.
Hereinafter, this specification is demonstrated in detail.
In the present specification, when a part "includes" a certain component, this means that it may further include other components, without excluding other components unless specifically stated otherwise.
In this specification, when a member is located "on" another member, this includes not only when a member is in contact with another member but also when another member exists between the two members.
According to an exemplary embodiment of the present specification, the first epoxy compound; A second epoxy compound different from the first epoxy compound; Acrylic compounds; And a radical initiator, wherein the first epoxy-based compound includes at least one alkoxy silyl group in a molecule.
Since the first epoxy compound according to one embodiment of the present specification includes at least one alkoxy silyl group in a molecule, an effect of increasing adhesion to a specific film (TAC film, etc.) is increased as compared with an epoxy compound not containing an alkoxy silyl group. In addition, since the epoxy and alkoxy silyl groups exist in one structure, the alkoxy reaction and the epoxy reaction can be induced at the same time, and thus have excellent curability and excellent water resistance and adhesion after curing.
According to an exemplary embodiment of the present specification, the first epoxy compound is represented by the following formula (1).
[Formula 1]
In Chemical Formula 1,
L1 to L3 are the same as or different from each other, and each independently a direct bond; -O-; -S-; Substituted or unsubstituted alkylene group; Or a substituted or unsubstituted arylene group,
R1 to R3 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group,
n and p are each an integer of 1 or more,
m is an integer from 1 to 10,
When n, m and p are two or more, the structures in two or more parentheses are the same as or different from each other.
In the present specification, the term "substituted" means that a hydrogen atom bonded to a carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited to a position where the hydrogen atom is substituted, that is, a position where the substituent can be substituted, 2 or more When substituted, two or more substituents may be the same or different from one another.
As used herein, an alkylene group refers to a straight or branched chain divalent hydrocarbon moiety of 1 to 20, 1 to 10, or 1 to 8, or 1 to 6 carbon atoms, wherein the alkylene group It may also contain at least one unsaturated bond in the molecule. On the other hand, the alkylene group, but is not limited thereto, methylene group, ethylene group, n-propylene group, isopropylene group, n-butylene group, t-butylene group, isobutylene group, pentylene group, hexylene group, Heptylene group, octylene group, nonylene group, tecanylene group, trimethylene group, tetramethylene group, pentamethylene group, hexamethylene group, heptamethylene group, nonamethylene group, decamethylene group, etc. are mentioned.
As used herein, an arylene group means a divalent monocyclic, bicyclic or tricyclic aromatic hydrocarbon moiety having 6 to 20, or 6 to 14 ring atoms, but is not limited to phenylene group, biphenyl Examples thereof include a reylene group, a naphthylene group, an anthracenylene group and the like. One or more hydrogen atoms included in the arylene group may be substituted with any substituent.
An alkyl group herein refers to a straight or branched chain hydrocarbon site of 1 to 20, 1 to 10, or 1 to 8, or 1 to 6 carbon atoms, wherein the alkyl group herein refers to at least 1 It may also include three unsaturated bonds. Meanwhile, the alkyl group is not limited thereto, but may be a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, t-butyl group, isobutyl group, pentyl group, hexyl group, heptyl group or jade. A til group, a nonyl group, a tecanyl group, etc. are mentioned as an example.
According to an exemplary embodiment of the present specification, in the general formula 1, L1 is a direct bond; -O-; An alkylene group having 1 to 20 carbon atoms unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms; An alkylene group having 2 to 20 carbon atoms unsubstituted or substituted with an alkenyl group having 1 to 20 carbon atoms; An arylene group having 6 to 20 carbon atoms unsubstituted or substituted with an alkenyl group having 2 to 20 carbon atoms; Or an arylene group having 6 to 20 carbon atoms unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms.
According to an exemplary embodiment of the present specification, in the general formula 1, L1 is a direct bond; -O-; A methylene group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms; Or a phenylene group unsubstituted or substituted with an alkenyl group having 2 to 20 carbon atoms.
According to an exemplary embodiment of the present specification, in the general formula 1, L1 is a direct bond; -O-; A methylene group unsubstituted or substituted with a methyl group; Or a phenylene group unsubstituted or substituted with a 2-propenyl group.
According to an exemplary embodiment of the present specification, in the general formula 1, L3 is an alkylene group having 1 to 10 carbon atoms.
According to an exemplary embodiment of the present specification, in the general formula 1, L3 is a methylene group.
According to an exemplary embodiment of the present specification, Chemical Formula 1 is represented by the following Chemical Formula 2 or 3.
[Formula 2]
[Formula 3]
In Chemical Formulas 2 and 3,
L2 and L12 are the same as or different from each other, and are each independently -O-; -S-; Substituted or unsubstituted alkylene group; Or a substituted or unsubstituted arylene group,
R1 to R6 and R11 to R13 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted alkenyl group.
As used herein, an alkenyl group refers to a straight or branched chain unsaturated hydrocarbon moiety of 2 to 20, 2 to 10 or 2 to 8, or 2 to 4 carbon atoms, and the alkenyl group is limited thereto. Vinyl, 1-propenyl, 2-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3 -Methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2- Examples thereof include phenyl-2- (naphthyl-1-yl) vinyl-1-yl, 2,2-bis (diphenyl-1-yl) vinyl-1-yl, stilbenyl group and styrenyl group. have.
According to an exemplary embodiment of the present specification, in the general formulas 2 and 3, L2 and L12 are the same as or different from each other, and each independently, an alkylene group having 1 to 10 carbon atoms.
According to an exemplary embodiment of the present specification, in the general formulas 2 and 3, L2 and L12 are n-propylene groups.
According to an exemplary embodiment of the present specification, in the general formulas 2 and 3, R1 to R3 are the same as or different from each other, and each independently an alkyl group having 1 to 10 carbon atoms.
According to an exemplary embodiment of the present specification, in the formula 2 and 3, R1 to R3 is an ethyl group.
According to an exemplary embodiment of the present specification, in the general formulas 2 and 3, R4 and R5 are the same as or different from each other, and each independently, an alkyl group having 1 to 10 carbon atoms.
According to an exemplary embodiment of the present specification, in the general formulas 2 and 3, R4 and R5 is a methyl group.
According to an exemplary embodiment of the present specification, in the general formula 3, R6 is a 2-propenyl group (2-propenyl).
According to an exemplary embodiment of the present specification, in the general formula 2, R11 to R13 are the same as or different from each other, and each independently an alkyl group having 1 to 10 carbon atoms.
According to an exemplary embodiment of the present specification, in the general formula 2 and 3, R11 to R13 is an ethyl group.
According to an exemplary embodiment of the present specification, Formula 1 is represented by the following formula (4) or formula (5).
[Formula 4]
[Formula 5]
According to an exemplary embodiment of the present specification, the adhesive composition further includes a second epoxy-based compound.
According to an exemplary embodiment of the present specification, the second epoxy compound is different from the first epoxy compound.
According to one embodiment of the present specification, the second epoxy compound is not particularly limited as long as it is different from the first epoxy compound, and examples thereof include an aromatic epoxy compound, a hydrogenated epoxy compound, an epoxy group-containing (meth) acrylic compound, Aliphatic epoxy compound etc. are mentioned. These can be used individually or in mixture of 2 or more.
In this case, the aromatic epoxy compound means an epoxy compound including at least one aromatic hydrocarbon ring in a molecule, but is not limited thereto, for example, diglycidyl ether of bisphenol A, 4,4'-methylene Bisphenol type epoxy resins such as diphenol diglycidyl ether, diglycidyl ether of bisphenol F, and diglycidyl ether of bisphenol S; Novolak-type epoxy resins, such as a phenol novolak epoxy resin, a cresol novolak epoxy resin, and a hydroxy benzaldehyde phenol novolak epoxy resin; And polyfunctional epoxy resins such as glycidyl ether of tetrahydroxyphenyl methane, glycidyl ether of tetrahydroxybenzophenone, and epoxidized polyvinylphenol.
In addition, the hydrogenated epoxy compound means an epoxy compound obtained by selectively hydrogenating the aromatic epoxy compound in the presence of a catalyst under pressure, but is not limited thereto, and particularly among the hydrogenated bisphenol A Preference is given to using diglycidyl ether.
In addition, the said epoxy group containing (meth) acrylic-type compound means the compound containing both an epoxy group and a (meth) acryloyloxy group in a molecule | numerator, It is not limited to this, For example, glycidyl acrylate, 2-methyl Glycidyl acrylate, 3,4-epoxybutyl acrylate, 6,7-epoxyheptyl acrylate, 3,4-epoxycyclohexyl acrylate, glycidyl methacrylate, 2-methylglycidyl methacrylate And 3,4-epoxybutyl methacrylate, 6,7-epoxyheptyl methacrylate, 3,4-epoxycyclohexyl methacrylate, 4-hydroxybutyl acrylate glycidyl ether and the like.
In addition, the aliphatic epoxy compound means an epoxy compound including an aliphatic chain or an aliphatic ring in a molecule, but is not limited thereto. For example, 1,4-cyclohexanedimethanol diglycidyl ether, 1 , 4-butanediol diglycidyl ether, 1,6-hexanediol diglycidyl ether, neopentyl diglycidyl ether, resorcinol diglycidyl ether, diethylene glycol diglycidyl ether, ethylene glycol di Glycidyl ether, trimethylol propane triglycidyl ether, n-butyl glycidyl ether, 2-ethylhexyl glycidyl ether, etc. are mentioned.
Specifically, the second epoxy compound does not include an alkoxy silyl group in the molecule.
According to an exemplary embodiment of the present specification, the second epoxy compound includes at least one epoxy group in a molecule.
According to an exemplary embodiment of the present specification, the second epoxy compound includes at least two epoxy groups in a molecule.
According to an exemplary embodiment of the present specification, the second epoxy compound includes two epoxy groups in a molecule.
According to an exemplary embodiment of the present specification, the acrylic compound includes at least one selected from the group consisting of a monofunctional acrylic compound, and a polyfunctional acrylic compound. Here, the acryl-based compound includes not only a compound containing an acrylate group, but also a compound containing a methacrylate group.
According to an exemplary embodiment of the present specification, the acrylic compound includes an acrylic compound having a hydrophilic group.
The monofunctional acrylic compound includes one intramolecular acrylate or (meth) acrylate.
The multifunctional acrylic compound may include two or more, specifically 2 to 6, acrylate or (meth) acrylate in the molecule.
The monofunctional acrylic compound and the polyfunctional acrylic compound may include one or more hydrophilic groups in a molecule, and the hydrophilic group may be a hydroxyl group, a phosphate group, or a carboxyl group, preferably a hydroxyl group.
The monofunctional acrylic compound may be phenoxy ethyl (meth) acrylate, benzyl (meth) acrylate, 2-phenylthio-1-ethyl (meth) acrylate, 6- (4,6-dibromo-2-iso) Propyl phenoxy) -1-hexyl (meth) acrylate, 6- (4,6-dibromo-2-sec-butyl phenoxy) -1-hexyl (meth) acrylate, 2,6-dibromo -4-nonylphenyl (meth) acrylate, 2,6-dibromo-4-dodecyl phenyl (meth) acrylate, 2- (1-naphthyloxy) -1-ethyl (meth) acrylate, 2 -(2-naphthyloxy) -1-ethyl (meth) acrylate, 6- (1-naphthyloxy) -1-hexyl (meth) acrylate, 6- (2-naphthyloxy) -1-hexyl (Meth) acrylate, 8- (1-naphthyloxy) -1-octyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, 4-tert-butylcyclohexyl (meth) acrylate, 8- (2-naphthyloxy) -1-octyl (meth) acrylate, isobornyl (meth) acrylate (isobornyl (meth) acrylate ), Cyclohexyl (meth) acrylate, norbornanyl (meth) acrylate, norbornenyl (meth) acrylate, dicyclopentadienyl (meth) acrylate, ethynylcyclohexane ( Meth) acrylate, ethynylcyclohexene (meth) acrylate, ethynyl decahydronaphthalene (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 2- Hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 6-hydroxyhexyl (meth) acrylate, 1,4-cyclohexanedimethanol mono (meth) acrylate, 1-chloro- 2-hydroxypropyl (meth) acrylate, diethylene glycol mono (meth) acrylate, 1,6-hexanediol mono (meth) acrylate, 2-hydroxy-3-phenyloxypropyl (meth) acrylate, 4-hydroxycyclopentyl (meth) acrylic , 2-hydroxy-3-phenyloxybutyl (meth) acrylate, 4-hydroxycyclohexyl (meth) acrylate, 4-hydroxymethylcyclohexyl (meth) acrylate, and 2,3-dihydroxy It may include one or more of propyl (meth) acrylate, but is not limited thereto.
The polyfunctional acrylic diethylene glycol di (meth) acrylate, dipropylene glycol di (meth) acrylate, tripropylene glycol di (meth) acrylate, decanediol di (meth) acrylate, nonanediol di (meth) krill Rate, 1,4-butanediol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, neopentyl glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, neopentyl glycoladi Pate (neopentylglycol adipate) di (meth) acrylate, hydroxyl puivalic acid neopentylglycol di (meth) acrylate, dicyclopentanyl di (meth) acrylate, caprolactone modified dicyclophene Tenyl di (meth) acrylate, ethylene oxide modified di (meth) acrylate, di (meth) acryloxy ethyl isocyanurate, allylated cyclohexyl di (meth) acrylate , Tricyclodecane dimethanol (meth) acrylate, dimethylol dicyclopentane di (meth) acrylate, ethylene oxide modified hexahydrophthalic acid di (meth) acrylate, tricyclodecane dimethanol (meth) acrylate, neo Pentyl glycol modified trimethylpropane di (meth) acrylate, adamantane di (meth) acrylate, 9,9-bis [4- (2-acryloyloxyethoxy) phenyl] fluorene Or 2- (5-((buta-1,3-dien-2-yloxy) methyl-5-ethyl-1,3-dioxan-2-yl) 2-methylpropyl (meth) acrylate, 3, 3 '-(4,4'-(propane-2,2-diyl) bis (4,1-phenylene)) bis (oxy) bis (2-hydroxypropane-3,1-diyl) di (meth) acrylate, 3 , 3 '-(4,4'-(propane-2,2-diyl) bis (4,1-phenylene)) bis (oxy) bis (2-hydroxypropane-3,1-diyl) di (meth) acrylate and Bifunctional acrylic compounds such as 3,3 '-(2,2-dimethylpropane-1,3-diyl) bis (oxy) bis (2-hydroxypropane-3,1-diyl) di (meth) acrylate; Trimethylolpropane tri (meth) acrylate, dipentaerythritol tri (meth) acrylate, propionic acid modified dipentaerythritol tri (meth) acrylate, pentaerythritol tri (meth) acrylate, propylene oxide Trifunctional acrylic compounds such as modified trimethylolpropane tri (meth) acrylate, trifunctional urethane (meth) acrylate, or tris (meth) acryloxyethyl isocyanurate; Tetrafunctional acryl-based compounds such as diglycerin tetra (meth) acrylate or pentaerythritol tetra (meth) acrylate; 5-functional acrylic compounds, such as propionic acid modified dipentaerythritol penta (meth) acrylate; And dipentaerythritol hexa (meth) acrylate, caprolactone modified dipentaerythritol hexa (meth) acrylate, or urethane (meth) acrylate (eg, isocyanate monomer and trimethylolpropane tri (meth) acrylate 6 functional acryl-type compounds, such as reactants), but is not limited thereto.
According to one embodiment of the present specification, the radical initiator is intended to improve the curing rate by promoting radical polymerizability, and as the radical initiator, radical initiators generally used in the art may be used without limitation.
More specifically, 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-ethoxy] -ethyl ester, alpha-dimethoxy-alpha-phenylacetophenone, 2- Benzyl-2- (dimethylamino) 1- [4- (4-morpholinyl) phenyl] -1-butanone (2-Benzyl-2- (dimethylamino) -1- [4- (4-morpholinyl) phenyl] -1-butanone), 2-methyl-1- [4- ( Methylthio) phenyl] -2- (4-morpholinyl) -1-propanone (2-Methyl-1- [4- (methylthio) phenyl] -2- (4-morpholinyl) -1-propanone), di Phenyl (2,4,6-trimethylbenzoyl) -phosphine oxide (Diphenyl (2,4,6-trimethylbenzoyl) -phosphine oxide), phosphine oxide, phenylbis (2,4,6-trimethylbenzoyl ) -Phosphine oxide (phenylbis (2,4,6-trimethylbenzoyl) -phosphineoxide) may be one or more selected from the group consisting of. In particular, in the present invention, phenylbis (2,4,6-trimethylbenzoyl) -phosphineoxide may be preferably used.
According to the exemplary embodiment of the present specification, with respect to 100 parts by weight of the adhesive composition, 5 to 70 parts by weight of the first epoxy compound, 10 to 85 parts by weight of the acrylic compound, and 0.1 to 20 of the radical initiator. Contains by weight.
According to another exemplary embodiment of the present specification, the first epoxy compound includes 5 to 70 parts by weight, more preferably 10 to 60 parts by weight.
When the adhesive composition comprises 5 parts by weight to 70 parts by weight of the first epoxy compound, the adhesive force and the water resistance improvement effect is excellent.
According to another exemplary embodiment of the present specification, the acrylic compound includes 10 to 60 parts by weight, preferably 10 to 55 parts by weight, more preferably 15 to 50 parts by weight.
When the adhesive composition comprises 10 to 85 parts by weight of the acrylic compound, it is excellent in the effect of improving the physical properties of the adhesive composition, the cross-linking role between the epoxy groups and the ring opening of the epoxy group sufficiently to speed up the curing rate of the epoxy. In addition, in the case of the acrylate, since the curing rate is relatively faster than the epoxy group, there is an excellent effect on the curing rate and degree of curing of the entire adhesive.
According to yet an embodiment of the present disclosure, the radical initiator comprises 0.1 to 10 parts by weight, preferably 1 to 8 parts by weight, more preferably 1 to 5 parts by weight.
In the adhesive composition, when the radical initiator is 0.1 parts by weight, the curing rate and the degree of curing are poor, and the adhesive force and physical properties are insufficient. When the ratio is more than 20 parts by weight, the curing rate of the adhesive composition is dropped at a too fast curing rate to cause the slow curing. The adhesion is lowered by interfering with other reactions with velocity.
According to the exemplary embodiment of the present specification, the second epoxy compound may further include 10 to 60 parts by weight based on 100 parts by weight of the adhesive composition.
According to another exemplary embodiment of the present specification, the second epoxy compound includes 10 to 60 parts by weight, more preferably 20 to 60 parts by weight.
When the adhesive composition comprises 10 to 60 parts by weight of the second epoxy-based compound, the adhesive force and the water resistance improvement effect is excellent.
According to one embodiment of the present specification, the adhesive composition may further include a photoacid generator (PAG).
The photoacid generator means a compound that generates an acid (H +) by an active energy ray. As the photoacid generator usable in the present invention, for example, a sulfonium salt or an iodonium salt is preferably included. Specific examples of photoacid generators that include sulfonium salts or iodonium salts include, for example, diphenyl (4-phenylthio) phenylsulfonium hexafluoroantimonate (Diphenyl (4- phenylthio) phenylsulfonium hexafluoroantimonate), diphenyl (4-phenylthio) phenylsulfonium hexafluorophosphate, (phenyl) [4- (2-methylpropyl) phenyl] -iodine hexa Fluorophosphate ((phenyl) [4- (2-methylpropyl) phenyl] -Iodonium hexafluorophosphate), (thiodi-4,1-phenylene) bis (diphenylsulfonium) dihexafluoroantimonate ((Thiodi- 4,1-phenylene) bis (diphenylsulfonium) dihexafluoroantimonate) and (thiodi-4,1-phenylene) bis (diphenylsulfonium) dihexafluorophosphate ((Thiodi-4,1-phenylene) bis (diphenylsulfonium) dihexafluorophosphate) and one or more selected from the group consisting of, but not limited thereto. is.
The photoacid generator may be about 0.1 to 15 parts by weight, preferably about 1 to 10 parts by weight, and more preferably about 2 to 8 parts by weight based on 100 parts by weight of the adhesive composition. When the photoacid generator satisfies the content range, not only the curing of the adhesive can be made smoothly, but also it is advantageous to impart excellent water resistance.
According to one embodiment of the present specification, the adhesive composition may further include a photosensitizer.
The photosensitizers include, for example, carbonyl compounds, organic sulfur compounds, persulfides, redox compounds, azo and diazo compounds, anthracene compounds, halogen compounds, photoreducing dyes, and the like, but are not limited thereto. no.
According to an exemplary embodiment of the present specification, the polarizer; An adhesive layer provided on at least one surface of the polarizer and formed of the adhesive composition described above; And it provides a polarizing plate comprising a protective film provided on at least one surface on the adhesive layer.
The polarizer is not particularly limited, and a film made of polyvinyl alcohol (PVA) including a polarizer well known in the art, for example, iodine or dichroic dye, may be used. The polarizer may be prepared by dyeing iodine or dichroic dye on the PVA film, but a method of manufacturing the same is not particularly limited. In the present specification, the polarizer means a state not including a protective film, and the polarizing plate means a state including a polarizer and a protective film.
Next, the adhesive layer is formed by using the adhesive composition according to the above-described embodiments of the present specification, and may be formed by a method well known in the art. For example, the adhesive composition may be applied to one surface of a polarizer or a protective film to form an adhesive layer, and then laminated with a polarizer and a protective film, followed by curing. In this case, the coating may be performed by coating methods well known in the art, for example, spin coating, bar coating, roll coating, gravure coating, blade coating, and the like.
On the other hand, the curing may be carried out by irradiating active energy rays, such as light curing, more specifically ultraviolet light, visible light, electron beam X-rays. For example, it can be carried out by a method of irradiating ultraviolet light of about 10 to 2500mJ / cm 2 using a ultraviolet halide lamp (Metal halide lamp).
Alternatively, the curing may be carried out by thermal curing, more specifically thermal curing at a curing temperature of 60 or more. In this case, a known amine initiator may be further added to the composition in order to increase the curing rate upon thermal curing.
Alternatively, the curing may be to additionally perform the thermal curing after the photo-curing, may be to perform the additional photo-cure after the thermal curing.
On the other hand, the thickness of the adhesive layer is more than 0 to 20㎛ or less, more than 0 to about 10㎛ or less, preferably 0.1 to 10㎛ or 0.1 to 5㎛ or so. If the thickness of the adhesive layer is too thin, the uniformity and adhesion of the adhesive layer may be lowered, and if the thickness of the adhesive layer is too thick, the appearance of wrinkles in the polarizer may occur.
The protective film is for supporting and protecting the polarizer, and protective films of various materials generally known in the art, for example, cellulose-based films, polyethylene terephthalate (PET) films, and cycloolefin polymers. (COP, cycloolefin polymer) film, acrylic film and the like can be used without limitation. Among them, it is particularly preferable to use an acrylic film in view of optical properties, durability, economy and the like.
On the other hand, the acrylic film usable in the present specification can be obtained by molding a molding material containing (meth) acrylate-based resin as a main component by extrusion molding. In this case, 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 In addition to the copolymer resin copolymerized with other monomer units and the (meth) acrylate-based resin as described above, the concept also includes a blend resin blended with other resin.
Meanwhile, the (meth) acrylate-based unit may be, for example, an alkyl (meth) acrylate-based unit. Here, 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.
Moreover, 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. In this case, the styrene-based unit is not limited thereto, and examples thereof include styrene, α-methylstyrene, and the like; Examples of the maleic anhydride monomer include, but are not limited to, maleic anhydride, methyl maleic anhydride, cyclohexyl maleic anhydride, phenyl maleic anhydride, and the like; Examples of 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.
On the other hand, the acrylic film may be a film containing a (meth) acrylate resin having a lactone ring structure. As a specific example of (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. In addition, 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.
On the other hand, the polarizing plate of the present specification may further include a primer layer between the adhesive layer and the protective film in order to further improve the adhesive force. In this case, 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. B, 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.
According to an exemplary embodiment of the present specification, a display panel; And a polarizing plate according to the above-described embodiment provided on one or both surfaces of the display panel.
The display panel may be a liquid crystal panel, a plasma panel, and an organic light emitting panel.
Accordingly, the image display device may be a liquid crystal display (LCD), a plasma display device (PDP), and an organic light emitting display device (OLED).
More specifically, the image display apparatus is provided on both sides of the liquid crystal panel and the liquid crystal panel.
Each of the polarizing plates may include a liquid crystal display device, wherein at least one of the polarizing plates may be a polarizing plate including a polarizer according to one embodiment of the present specification. That is, the polarizing plate comprises a polyvinyl alcohol polarizer in which iodine and / or dichroic dye is dyed and a protective film provided on at least one surface of the polyvinyl alcohol polarizer, in a wavelength range of 400 nm to 800 nm. Has a polarization cancellation area having a single transmittance of 80% or more, the arithmetic mean roughness Ra of the polarization removal area is 200 nm or less, a polarization degree of 10% or less, and sagging is 10 µm or less.
In this case, the type of liquid crystal panel included in the liquid crystal display device is not particularly limited. For example, 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. In addition, the type of other components constituting the liquid crystal display device, for example, the upper and lower substrates (for example, color filter substrates or array substrates) is not particularly limited, and the configurations known in the art are not limited. Can be employed.
Hereinafter, the present invention will be described in more detail. However, the following examples are only intended to illustrate the present invention, but are not intended to limit the scope of the present invention.
Example 1-1
30 wt% of 4,4'-methylenediphenol diglycidyl ether, 20 wt% of SY-DP-A21 (manufactured by Samyang Corp.), a compound of Formula 4, (4-((buta-1,3-diene- 2-yloxy) methyl) cyclohexyl) methanol ((4-((buta-1,3-dien-2-yloxy) methyl) cyclohexyl) methanol) 12 wt%, 2,3-dihydroxypropyl methacrylate 6 parts by weight of (2,3-dihydroxypropyl methacrylate), 10% by weight of dicyclopentanyl diacrylate, and 22% by weight of dipropylglycol diacrylate were added to 100 parts by weight of the resin composition. Diphenyl (4-phenylthio) phenylsulfonium hexafluorophosphate: 3 parts by weight of San Apro Co., Ltd., 2 parts by weight of 200K (manufactured by San Afro Co., Ltd.), radical initiator Irgacure 819 (manufactured by BASF) 0.5 Part by weight and 0.5 parts by weight of the photosensitizer Isopropylthioxanthone (ITX) were added to prepare an adhesive composition.
Comparative Example 1-1
In Example 1-1, 4,4'-methylenediphenol diglycidyl ether and 4,4'-methylenediphenol diglyci instead of SY-DP-A21 (manufactured by Samyang), a compound of Formula 4 An adhesive composition was prepared in the same manner as in Example 1-1, except that 50% by weight of diethyl ether was used.
Adhesion Evaluation 1
The adhesive force of the adhesive composition prepared by Example 1-1 and Comparative Example 1-1 was evaluated. Evaluation methods and results are shown in Table 1 below, and the adhesive strength of the COP (cycloolefin polymer) film and the TAC (tri-acetyl-cellulose) film was evaluated. Specifically, the polarizing plates prepared in Example 1-1 and Comparative Example 1-1 were cut to a width of 20 mm and a length of 100 mm, and then the texture analyzer (TA-XT Plus by Stable Micro Systems), speed 300 mm / min, Peel force between the polarizer and the film was measured at 90 degrees. At this time, when peeling force is 2.0 N / cm <2> or more, it was represented by ( double- circle), peeling force 1N / cm <2> or more as (circle) and peeling force less than 1.0 N / cm <2> .
In Table 1, Example 1-1, which is an adhesive composition according to an exemplary embodiment of the present specification, compared to the adhesive composition of Comparative Example 1-1 using only an epoxy compound containing no alkoxy silyl group, in a COP film and a TAC film It was found that the adhesive strength is excellent.
As a result of the evaluation, it was found that the adhesive composition according to the present specification has excellent adhesion to various films as compared with the adhesive composition using only an epoxy-based compound containing no alkoxy silyl group.
Example 2-1
40 wt% of 4,4'-methylenediphenol diglycidyl ether, 10 wt% of SY-DP-A21 (manufactured by Samyang), a compound of Formula 4, (4-((buta-1,3-diene- 2-yloxy) methyl) cyclohexyl) methanol ((4-((buta-1,3-dien-2-yloxy) methyl) cyclohexyl) methanol) 12 wt%, 2,3-dihydroxypropyl methacrylate 6 parts by weight of 200K (manufactured by San Apro Co., Ltd.) in 100 parts by weight of (2,3-dihydroxypropyl methacrylate), 100% by weight of dicyclopentanyl diacrylate, and 22% by weight of dipropylglycol diacrylate. Part, 0.5 parts by weight of the radical initiator Irgacure 819 (manufactured by BASF) and 0.5 parts by weight of the photosensitizer Isopropylthioxanthone (ITX) were prepared to prepare an adhesive composition.
Example 2-2
Except that in Example 2-1 30 wt% of 4,4'-methylenediphenol diglycidyl ether and 20 wt% of SY-DP-A21 (manufactured by Samyang), a compound of Formula 4, were used. An adhesive composition was prepared in the same manner as in Example 2-1.
Example 2-3
Except that 20 wt% of 4,4'-methylenediphenol diglycidyl ether and 30 wt% of SY-DP-A21 (manufactured by Samyang Co., Ltd.), a compound of Formula 4, were used in Example 2-1. An adhesive composition was prepared in the same manner as in Example 2-1.
Comparative Example 2-1
In Example 2-1 to 4,4'-methylenedi instead of 4,4'-methylenediphenol diglycidyl ether and SY-DP-A21 (manufactured by Samyang Co., Ltd.) An adhesive composition was prepared in the same manner as in Example 2-1, except that 50 wt% of phenol diglycidyl ether was used.
Adhesion Evaluation 2
The adhesive force of the adhesive composition manufactured by Example 2-1, 2-2, Comparative Example 2-1, and Comparative Example 2-2 was evaluated. Evaluation methods and results are shown in Table 2 below, and the adhesive strength of the COP (cycloolefin polymer) film and the TAC (tri-acetyl-cellulose) film was evaluated. Specifically, the polarizing plates prepared in Examples 2-1 to 2-3 and Comparative Example 2-1 were cut to a width of 20 mm and a length of 100 mm as in the evaluation of adhesive strength 1, followed by Texture Analyzer (Stable Micro Systems, Inc. TA-XT). Plus), the peel force between the polarizer and the film at a speed of 300 mm / min and 90 degrees was measured. At this time, when peeling force is 2.0 N / cm <2> or more, it was represented by ( double- circle), peeling force 1N / cm <2> or more as (circle) and peeling force less than 1.0 N / cm <2> .
In Table 1, Examples 2-1 to 2-3, which is an adhesive composition according to an exemplary embodiment of the present specification, are compared to the adhesive composition of Comparative Example 2-1 using only an epoxy-based compound that does not contain an alkoxy silyl group, and a COP film. And it was found that the adhesion in the TAC film is excellent.
In particular, Examples 2-1 to 2-3 can be seen that the adhesive strength in the COP film is superior to Comparative Example 2-1, and in the adhesive composition of Example 2-2 the adhesive strength of the COP film is superior to other adhesive compositions Could know.
As a result of the evaluation, it was found that the adhesive composition according to the present specification has excellent adhesion to various films as compared with the adhesive composition using only an epoxy-based compound containing no alkoxy silyl group.
Claims (12)
A first epoxy compound; Acrylic compounds; And radical initiators,
The first epoxy compound includes at least one alkoxy silyl group in the molecule,
Adhesive composition comprising 5 to 70 parts by weight of the first epoxy compound based on 100 parts by weight of the total adhesive composition.
[Formula 1]
In Chemical Formula 1,
L1 to L3 are the same as or different from each other, and each independently a direct bond; -O-; -S-; Substituted or unsubstituted alkylene group; Or a substituted or unsubstituted arylene group,
R1 to R3 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group,
n and p are each an integer of 1 or more,
m is an integer from 1 to 10,
When n, m and p are two or more, the structures in two or more parentheses are the same as or different from each other.
[Formula 2]
[Formula 3]
In Chemical Formulas 2 and 3,
L2 and L12 are the same as or different from each other, and each independently a direct bond; -O-; -S-; Substituted or unsubstituted alkylene group; Or a substituted or unsubstituted arylene group,
R1 to R6 and R11 to R13 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted alkenylene group.
5 to 70 parts by weight of the first epoxy compound,
10 to 85 parts by weight of the acrylic compound, and
Adhesive composition comprising 0.1 to 20 parts by weight of the radical initiator.
An adhesive layer provided on at least one surface of the polarizer and formed of an adhesive composition according to any one of claims 1 to 9; And
Polarizing plate comprising a protective film provided on at least one surface on the adhesive layer.
An image display device comprising the polarizing plate of claim 10 provided on one side or both sides of the display panel.
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| KR101072371B1 (en) * | 2010-09-20 | 2011-10-11 | 주식회사 엘지화학 | Adhesive for polarizing plate and polarizing plate comprising the same |
| KR20140105162A (en) * | 2013-02-22 | 2014-09-01 | 한국생산기술연구원 | Composition and cured product comprising epoxy compound having alkoxysilyl group and use thereof |
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