KR102762128B1 - Compound, adhesive composition, polarizer and display apparatus - Google Patents

Abstract

The present specification relates to a compound represented by chemical formula 1, an adhesive composition comprising the same, a polarizing plate, and an image display device.

Description

COMPOUND, ADHESIVE COMPOSITION, POLARIZER AND DISPLAY APPARATUS

The present specification relates to a compound, an adhesive composition, a polarizing plate, and an image display device.

Polarizing plates used in various image display devices such as liquid crystal displays, plasma displays, and electroluminescent devices are structured with a polarizer made of a polyvinyl alcohol film and a protective film formed on at least one surface of the polarizer. Meanwhile, polyvinyl alcohol adhesives are mainly used as adhesives for polarizing plates used to bond the polarizer and the protective film.

However, since the polyvinyl alcohol-based resin adhesive is a water-soluble polymer, there was a problem that the adhesive dissolved under high humidity conditions, causing the polarizer and protective film to peel off.

To improve these problems, methods have been proposed, such as modifying a polyvinyl alcohol-based resin by adding an acetoacetyl group to it, copolymerizing it with hydrophobic vinyl monomers such as ethyl acrylate, methyl acrylate, acrylic acid, or methacrylic acid, or mixing a crosslinking agent such as glyoxalate or an amine metal salt into the polyvinyl alcohol-based resin.

In the case of polyvinyl alcohol-based adhesives manufactured by the above methods, the water resistance tends to be somewhat improved compared to when polyvinyl alcohol is used alone, but there is still a problem that the water resistance and adhesive strength are insufficient when applied to a high-speed production line. In addition, in the case of modified polyvinyl alcohol-based resin adhesives, there was a problem that stains occurred under alkaline pH conditions, and in the case of methods of mixing a crosslinking agent, there were also problems such as the optical properties of the polarizing plate deteriorating depending on the amount of the crosslinking agent.

Therefore, an adhesive for bonding a polarizer and a protective film that has excellent adhesion and water resistance to the polarizer and the protective film while maintaining the optical properties of the polarizing plate is required.

Japanese Public Notice 2003-121644

The present specification provides a compound, an adhesive composition, a polarizing plate, and an image display device.

According to one embodiment of the present specification, a compound represented by the following chemical formula 1 is provided.

[Chemical Formula 1]

In the above chemical formula 1,

R1 and R2 are the same or different from each other, and each independently represents a substituted or unsubstituted alkyl group; or a substituted or unsubstituted cycloalkyl group, or are combined with each other to form a substituted or unsubstituted ring,

R3 is hydrogen; -CO ₂ R; -SO ₂ R';-COR'';-CONR'''R''''; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,

R4 and R5 are the same or different, and each independently hydrogen; -CN; -CO ₂ R; -SO ₂ R';-COR'';-CONR'''R''''; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,

R, R', R'', R''' and R'''' are the same or different and each independently represents hydrogen; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group,

R6 to R8 are the same or different, and each independently represents hydrogen; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted alkoxy group.

According to another embodiment of the present specification, an adhesive composition comprising the compound is provided.

According to another embodiment of the present specification, a polarizing plate comprising the adhesive composition or a cured product thereof is provided.

According to another embodiment of the present specification, an image display device including the polarizing plate is provided.

By using the compound described in this specification as an adhesive composition for a polarizing plate, it is possible to provide an adhesive composition having excellent performance in blocking ultraviolet rays and exhibiting excellent durability without deteriorating the optical properties of the polarizing plate when applied to the polarizing plate.

FIG. 1 is a cross-sectional view of a polarizing plate according to one embodiment of the present specification.
FIG. 2 is a cross-sectional view of an image display device including a polarizing plate according to one embodiment of the present specification.

Below, the present specification is described in more detail.

According to one embodiment of the present specification, a compound represented by the chemical formula 1 is provided.

The compound represented by the above chemical formula 1 can be used by mixing it into an adhesive composition. The compound of the above chemical formula 1 has a substituted amine group as a donor with pyridine as a core and an acceptor group containing a nitrile group, so that it has an excellent molar absorption coefficient and effectively absorbs an ultraviolet region including a blue region of 380 nm or more. When a film is manufactured using the adhesive composition containing the compound represented by the above chemical formula 1 or a cured product thereof and applied to a polarizing plate, the durability of the polarizing plate can be improved without deteriorating the optical properties thereof.

In this specification, when a part is said to "include" a certain component, this does not mean that other components are excluded, but rather that other components may be included, unless otherwise specifically stated.

In this specification, when it is said that a member is located "on" another member, this includes not only cases where a member is in contact with the other member, but also cases where another member exists between the two members.

Examples of substituents in this specification are described below, but are not limited thereto.

The term "substitution" above means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position of the substitution is not limited to the position at which the hydrogen atom is replaced, i.e., a position at which the substituent can be replaced, and when two or more are substituted, the two or more substituents may be the same or different from each other.

The term "substituted or unsubstituted" as used herein means substituted with one or more substituents selected from the group consisting of deuterium; a halogen group; a cyano group; a nitrile group; a nitro group; a carboxyl group (-COOH); an ester group; a hydroxyl group; an alkyl group; a cycloalkyl group; an alkoxy group; an aryl group; and a heterocyclic group, or substituted with a substituent in which two or more substituents are connected among the above-mentioned substituents, or has no substituents. For example, "a substituent having two or more substituents connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent having two phenyl groups connected. Another example of a "substituent having two or more substituents connected" may be an ethenylphenyl group. It is interpreted as a substituent having an ethenyl group and a phenyl group connected.

In one embodiment of the present specification, the term "substituted or unsubstituted" means substituted with 1 or 2 or more substituents selected from the group consisting of deuterium; a halogen group; a cyano group; a nitrile group; a nitro group; a carboxyl group (-COOH); an ester group having 1 to 10 carbon atoms; a hydroxyl group; an alkyl group having 1 to 10 carbon atoms; a cycloalkyl group having 3 to 30 carbon atoms; an alkoxy group having 1 to 10 carbon atoms; an aryl group having 6 to 30 carbon atoms; and a heterocyclic group having 2 to 30 carbon atoms, or substituted with a substituent in which two or more of the substituents exemplified above are connected, or having no substituents.

In this specification, the halogen group can be fluorine, chlorine, bromine or iodine.

In the present specification, the ester group can be -C(=O)OR ₁₀₅ , or -OC(=O)R ₁₀₆ , wherein R ₁₀₅ and R ₁₀₆ are the same as or different from each other, and are each independently hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted aryl group, but are not limited thereto. Specifically, the oxygen of the ester group can be substituted with an alkyl group having 1 to 25 carbon atoms; an alkenyl group having 2 to 25 carbon atoms; an aryl group having 6 to 30 carbon atoms; or a heterocyclic group having 2 to 30 carbon atoms. In one embodiment of the present specification, the oxygen is substituted with an alkyl group having 1 to 10 carbon atoms; an alkenyl group having 1 to 10 carbon atoms; an aryl group having 6 to 20 carbon atoms; or a heterocyclic group having 2 to 20 carbon atoms.

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30; 1 to 20; 1 to 10; or 1 to 5. Specific examples include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1-dimethylpropyl, isohexyl, 4-methylhexyl, 5-methylhexyl, and the like.

In the present specification, the cycloalkyl group is not particularly limited, but is preferably one having 3 to 30 carbon atoms; 3 to 20 carbon atoms; 3 to 10 carbon atoms; or 3 to 6 carbon atoms, and specifically includes, but is not limited to, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like.

In the present specification, the alkoxy group is an alkyl group connected to an oxygen atom, and may be a straight chain, branched chain, or cyclic chain. The number of carbon atoms in the alkoxy group is not particularly limited, but is preferably 1 to 30; 1 to 20; 1 to 10; or 1 to 5. Specifically, the alkoxy group may be, but is not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, and the like.

In the present specification, an aryl group means a monovalent group of a monovalent aromatic hydrocarbon or an aromatic hydrocarbon derivative. In the present specification, an aromatic hydrocarbon means a compound including a ring in which pi electrons are completely conjugated and are planar, and a group derived from an aromatic hydrocarbon means a structure in which an aromatic hydrocarbon or a cyclic aliphatic hydrocarbon is condensed with an aromatic hydrocarbon. In addition, in the present specification, an aryl group is intended to include a monovalent group in which two or more aromatic hydrocarbons or aromatic hydrocarbon derivatives are linked to each other. The aryl group is not particularly limited, but is preferably one having 6 to 50; 6 to 30; 6 to 25; 6 to 20; 6 to 18; or 6 to 13 carbon atoms, and the aryl group may be monocyclic or polycyclic. Specifically, the monocyclic aryl group may include, but is not limited to, a phenyl group, a biphenyl group, a terphenyl group, etc. Specifically, the polycyclic aryl group may include, but is not limited to, a naphthyl group, anthracenyl group, a phenanthryl group, a triphenyl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, etc.

In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be combined with each other to form a substituted or unsubstituted ring.

In the present specification, when it is said that a fluorenyl group can be substituted, the substituted fluorenyl group includes all compounds in which substituents of the five-membered ring of fluorene are spiro-bonded to each other to form an aromatic hydrocarbon ring. The substituted fluorenyl group includes, but is not limited to, 9,9'-spirobifluorene, spiro[cyclopentane-1,9'-fluorene], spiro[benzo[c]fluorene-7,9-fluorene], and the like.

In this specification, an aryloxy group is an aryl group connected to an oxygen atom, and the aryl group of the aryloxy group is the same as the example of the aryl group described above. Specifically, examples of the aryloxy group include a phenoxy group, a p-toryloxy group, a m-toryloxy group, a 3,5-dimethyl-phenoxy group, a 2,4,6-trimethylphenoxy group, a p-tert-butylphenoxy group, a 3-biphenyloxy group, a 4-biphenyloxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, a 4-methyl-1-naphthyloxy group, a 5-methyl-2-naphthyloxy group, a 1-anthryloxy group, a 2-anthryloxy group, a 9-anthryloxy group, a 1-phenanthryloxy group, a 3-phenanthryloxy group, a 9-phenanthryloxy group, and the like, and examples of the arylthioxy group include a phenylthioxy group, a 2-methylphenylthioxy group, a 4-tert-butylphenylthioxy group, and the like, but are not limited thereto.

In this specification, the “ring” that forms a substituted or unsubstituted ring by combining may be applied to the description of a heterocyclic group or hydrocarbon ring described below.

In the present specification, a heterocyclic group includes one or more non-carbon atoms or heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, and S, etc. The number of carbon atoms is not particularly limited, but is preferably 2 to 50; 2 to 30; 2 to 25; 2 to 20; 2 to 18; or 2 to 13, and the heterocyclic group may be monocyclic or polycyclic. Examples of heterocyclic groups include thiophene group, furanyl group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, pyridine group, bipyridine group, pyrimidine group, triazine group, triazole group, acridine group, pyridazine group, pyrazine group, quinoline group, quinazoline group, quinoxaline group, phthalazine group, pyridopyrimidine group, pyridopyrazine group, pyrazino pyrazine group, isoquinoline group, indole group, carbazole group, benzoxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuran group, phenanthroline, thiazole group, isoxazole group, oxadiazole group, thiadiazole group, Examples thereof include, but are not limited to, benzothiazole groups, phenothiazine groups, dibenzofuran groups, dihydrophenothiazine groups, dihydrobenzoisoquinoline groups, chromene groups, and chromenone groups.

In the present specification, the heterocyclic group may be monocyclic or polycyclic, and may be an aromatic, aliphatic, or a condensed ring of aromatic and aliphatic groups, and may be selected from the examples of the heterocyclic group.

In the present specification, a heteroaryl group means a monovalent aromatic heterocycle. Here, the aromatic heterocycle means a monovalent group of an aromatic ring or a derivative of an aromatic ring, which includes at least one of N, O, and S as a heteroatom in the ring. The derivative of the aromatic ring includes all structures in which an aromatic ring or an aliphatic ring is condensed with an aromatic ring. In addition, in the present specification, the heteroaryl group is intended to include a monovalent group in which an aromatic ring including two or more heteroatoms or a derivative of an aromatic ring including a heteroatom are connected to each other. It is preferable that the heteroaryl group has 2 to 50; 2 to 30; 2 to 20; 2 to 18; or 2 to 13 carbon atoms.

In the present specification, the ring may be an aromatic, aliphatic or a condensed ring of an aromatic and an aliphatic group, and may be selected from examples of the cycloalkyl group or the aryl group, except for the non-monovalent ones, and examples of the condensed ring of an aromatic and an aliphatic group include, but are not limited to, a 1,2,3,4-tetrahydronaphthalene group and a 2,3-dihydro-1H-indene group.

In this specification, the term "adjacent" may refer to a substituent substituted on an atom directly connected to the atom substituted by the substituent, a substituent stereostructurally closest to the substituent, or another substituent substituted on the atom substituted by the substituent. For example, two substituents substituted at the ortho position in a benzene ring and two substituents substituted on the same carbon in an aliphatic ring may be interpreted as "adjacent" groups to each other.

In this specification, the term “adjacent groups combine with each other to form a substituted or unsubstituted ring” among the substituents means that adjacent groups combine with each other to form a substituted or unsubstituted hydrocarbon ring; or a substituted or unsubstituted heterocycle.

In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently represents a substituted or unsubstituted alkyl group; or a substituted or unsubstituted cycloalkyl group, or are combined with each other to form a substituted or unsubstituted ring.

In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; or a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; or are combined with each other to form a substituted or unsubstituted ring.

In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; or a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; or are combined with each other to form a substituted or unsubstituted ring.

In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; or a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms; or are combined with each other to form a substituted or unsubstituted ring.

In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently represents a substituted or unsubstituted alkyl group.

In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently represents a substituted or unsubstituted ethyl group; or a substituted or unsubstituted methyl group.

In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently represent an ethyl group substituted with a nitrile group, -CO ₂ CH ₂ CH ₃ or a phenyl group; or an ethyl group substituted or unsubstituted with a nitrile group.

In one embodiment of the present specification, R3 is hydrogen; -CO ₂ R; -SO ₂ R';-COR'';-CONR'''R''''; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, R3 is CO ₂ R; -SO ₂ R';-COR''; or -CONR'''R''''.

In one embodiment of the present specification, R, R', R'', R''' and R'''' are the same as or different from each other, and each independently represents hydrogen; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group.

In one embodiment of the present specification, R, R', R'', R''' and R'''' are the same as or different from each other, and each independently represents hydrogen; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In one embodiment of the present specification, R, R', R'', R''' and R'''' are the same as or different from each other, and each independently represents hydrogen; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, R, R', R'', R''' and R'''' are the same as or different from each other, and each independently represents hydrogen; a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms.

In one embodiment of the present specification, R, R', R'', R''' and R'''' are the same as or different from each other, and each independently represents hydrogen; a substituted or unsubstituted methyl group; a substituted or unsubstituted ethyl group; a substituted or unsubstituted tert-butyl group; or a substituted or unsubstituted phenyl group.

In one embodiment of the present specification, R, R', R'', R''' and R'''' are the same as or different from each other, and are each independently hydrogen; a methyl group; an ethyl group; a tert-butyl group; or a phenyl group.

In one embodiment of the present specification, R3 is -CO ₂ R, and R is hydrogen; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group.

In one embodiment of the present specification, R is hydrogen; or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

In one embodiment of the present specification, R is hydrogen; or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

In one embodiment of the present specification, R is hydrogen; or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

In one embodiment of the present specification, R is hydrogen; a substituted or unsubstituted methyl group; or a substituted or unsubstituted ethyl group.

In one embodiment of the present specification, R4 and R5 are the same as or different from each other, and each independently represent hydrogen; -CN; -CO ₂ R; -SO ₂ R';-COR'';-CONR'''; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, R4 and R5 are the same as or different from each other, and each independently represent hydrogen; -CN; -CO ₂ R; -SO ₂ R';-COR'';-CONR'''; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 3 to 30 carbon atoms.

In one embodiment of the present specification, R4 and R5 are the same as or different from each other, and each independently represent hydrogen; -CN; -CO ₂ R; -SO ₂ R';-COR'';-CONR'''; a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heterocyclic group having 3 to 20 carbon atoms.

In one embodiment of the present specification, R4 and R5 are the same as or different from each other, and each independently represent hydrogen; -CN; -CO ₂ R; -SO ₂ R';-COR'';-CONR'''; a substituted or unsubstituted aryl group having 6 to 12 carbon atoms; or a substituted or unsubstituted heterocyclic group having 3 to 12 carbon atoms.

In one embodiment of the present specification, R4 is -CN.

In one embodiment of the present specification, R6 to R8 are the same as or different from each other, and are each independently hydrogen; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted alkoxy group.

In one embodiment of the present specification, R5 to R8 are hydrogen.

In one embodiment of the present specification, the compound represented by the chemical formula 1 is represented by any one of the following compounds.

The compound according to one embodiment of the present specification can be manufactured by the manufacturing method described below. In the manufacturing examples described below, representative examples are described, but, if necessary, substituents can be added or excluded, and the positions of the substituents can be changed. In addition, starting materials, reactants, reaction conditions, etc. can be changed based on techniques known in the art.

For example, a compound represented by the above chemical formula 1 can be produced with a core structure as shown in the following general formula 1. The substituents can be combined by a method known in the art, and the type, position, or number of the substituents can be changed according to a technique known in the art. The substituents can be combined as shown in the following general formula 1, but are not limited thereto.

[General formula 1]

In the above general formula 1, the description of the substituents is as described above.

According to one embodiment of the present specification, an adhesive composition comprising the compound is provided.

The above adhesive composition further comprises a polymer polymerized with an acrylic monomer.

The compound represented by the chemical formula 1 included in the adhesive composition may be included in an amount of 0.01 to 10 parts by weight based on 100 parts by weight of a polymer polymerized with an acrylic monomer.

When the content of the compound represented by the above chemical formula 1 satisfies the above range, it can be more advantageous in providing an adhesive composition having excellent performance in blocking ultraviolet rays including the blue region, optical properties of a polarizing plate, and durability. When the content of the above compound is excessively high, the adhesive properties may be affected or a crystallization phenomenon may occur.

The polymer polymerized with the above acrylic monomer is subject to the following description.

Specifically, the polymer polymerized with the acrylic monomer may be a polymer polymerized with the first to third acrylic monomers.

In one embodiment of the present specification, the first acrylic monomer is 1 or 2 selected from the group consisting of isobornyl acrylate (IBOA) and isobornyl methacrylate (IBOMA).

In one embodiment of the present specification, the second acrylic monomer is 1 or 2 selected from the group consisting of hydroxyethyl acrylate (HEA) and hydroxyethyl methacrylate (HEMA).

In one embodiment of the present specification, the adhesive composition may further include one or two or more third acrylic monomers selected from the group consisting of hydroxybutyl acrylate (HBA), hydroxybutyl metaacrylate (HBMA), hydroxypropyl acrylate (HPA), and hydroxypropyl metaacrylate (HPMA).

In one embodiment, the polymer made of the acrylic monomer may be an alkyl (meth)acrylate. Specifically, the alkyl (meth)acrylate may be n-butyl methacrylate, but is not limited thereto.

The polymer polymerized with the above acrylic monomer can be produced by a known polymerization method. For example, a monomer mixture in which a (meth)acrylic acid ester monomer and a polar group-containing copolymerizable monomer and/or other comonomers are appropriately mixed according to the desired weight ratio can be applied to a conventional polymerization method such as solution polymerization, photo polymerization, bulk polymerization, suspension polymerization, or emulsion polymerization to produce an acrylic polymer. If necessary, a polymerization initiator or chain transfer agent may be used together during the polymerization process.

In one embodiment of the present specification, the adhesive composition includes an epoxy compound. Examples of the above epoxy compounds include 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, bis(3,4-epoxycyclohexylmethyl)adipate, a caprolactone modified product of 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, an ester or caprolactone modified product of a polyhydric carboxylic acid and 3,4-epoxycyclohexylmethyl alcohol, a silicone compound having an alicyclic epoxy group at the terminal, a diglycidyl ether of bisphenol A, a diglycidyl ether of bisphenol F, a diglycidyl ether of brominated bisphenol A, a phenol novolac-type epoxy resin, a cresol novolac-type epoxy resin, a biphenyl-type epoxy resin, a terephthalic acid diglycidyl ester, a phthalic acid diglycidyl ester, a terminal carboxylic acid polybutadiene, and Addition products of bisphenol A type epoxy resin, dicyclopentadiene dioxide, limonene dioxide, 4-vinylcyclohexene dioxide, polyethylene glycol (repeated number 3 or more) diglycidyl ether, polypropylene glycol (repeated number 3 or more) diglycidyl ether, polytetramethylene glycol (repeated number 3 or more) diglycidyl ether, hydrogenated bisphenol A diglycidyl ether, epoxidized vegetable oil, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltriethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, polybutadiene diglycidyl ether of both terminal hydroxyl groups, internal epoxidation of polybutadiene, compounds in which double bonds of styrene-butadiene copolymers are partially epoxidized [for example, Examples thereof include “Epofriend” manufactured by Daicel Chemical Industry Co., Ltd., and compounds in which the isoprene unit of a block copolymer of ethylene-butylene copolymer and polyisoprene is partially epoxidized (e.g., “L-207” manufactured by KRATON).

According to one embodiment of the present specification, the adhesive composition may contain additives such as an antioxidant, a stabilizer, and a coupling agent. By adding the additives, an adhesive having desired performance can be obtained.

The above antioxidants and stabilizers may be appropriately employed as materials used in the art, and are not limited thereto.

The above coupling agent may be a silane coupling agent. The silane coupling agent is one or two or more selected from the group consisting of ν-glycidoxypropyltrimethoxysilane, ν-glycidoxypropyltriethoxysilane, ν-glycidoxypropylmethyldimethoxysilane, ν-glycidoxypropylmethyldiethoxysilane, β-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, β-(3,4-epoxycyclohexyl)ethyltriethoxysilane, β-(3,4-epoxycyclohexyl)ethylmethyldiethoxysilane, ν-glycidoxypropyltriisopropenyloxysilane, and ν-glycidoxypropyltriiminooxysilane.

According to one embodiment of the present specification, a polarizing plate including the adhesive composition or a cured product thereof is provided.

The above adhesive composition or its cured product forms an adhesive layer.

Specifically, the polarizing plate comprises a polarizer; an adhesive layer provided on at least one surface of the polarizer and including the aforementioned adhesive composition or a cured product thereof; and a protective film provided on at least one surface of the adhesive layer.

The polarizer is not particularly limited, and a polarizer well known in the art, for example, a film made of polyvinyl alcohol (PVA) containing iodine or a dichroic dye, can be used. The polarizer can be manufactured by dyeing a PVA film with iodine or a dichroic dye, but the manufacturing method thereof is not particularly limited. In the present specification, a polarizer means a state in which it does not include a protective film, and a polarizing plate means a state in which it includes a polarizer and a protective film.

Next, the adhesive layer may be formed by a method well known in the art, including an adhesive composition according to the embodiments of the present disclosure described above. For example, the adhesive layer may be formed by applying an adhesive composition to one surface of a polarizer or a protective film, and then the polarizer and the protective film may be laminated and then cured. At this time, the coating may be performed by a coating method well known in the art, such as spin coating, bar coating, roll coating, gravure coating, or blade coating. The curing may be performed by a thermal curing method, and a thermal curing method used in the art may be appropriately applied.

Meanwhile, the thickness of the adhesive layer is preferably in the range of 0 to 30 ㎛, more than 0 to 10 ㎛, and preferably in the range of 0.1 ㎛ to 10 ㎛ or 1 ㎛ to 7 ㎛. If the thickness of the adhesive layer is too thin, the uniformity and adhesive strength of the adhesive layer may deteriorate, and if the thickness of the adhesive layer is too thick, the problem of wrinkles on the appearance of the polarizing plate may occur.

The above protective film is intended to support and protect the polarizer, and various protective films made of materials generally known in the art, such as a cellulose-based film, a polyethylene terephthalate (PET) film, a cycloolefin polymer (COP) film, an acrylic film, etc., can be used without limitation. Among these, considering optical properties, durability, cost-effectiveness, etc., it is particularly preferable to use an acrylic film.

Meanwhile, 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 adhesive strength. At this time, the primer layer may be formed by a method of applying a coating solution containing a water-dispersible polymer resin, water-dispersible fine particles, and water onto the protective film using a bar coating method, a gravure coating method, or the like, and drying it. The water-dispersible polymer resin may be, for example, a water-dispersible polyurethane-based resin, a water-dispersible acrylic resin, a water-dispersible polyester-based resin, or a combination thereof, and the water-dispersible fine particles may be, but are not limited to, inorganic fine particles such as silica, titania, alumina, and zirconia, or organic fine particles composed of a silicone-based resin, a fluorine-based resin, a (meth)acrylic-based resin, cross-linked polyvinyl alcohol, and a melamine-based resin, or a combination thereof.

One embodiment of the present specification provides an image display device including the polarizing plate.

Specifically, the above image display device is an image display device including a display panel; and a polarizing plate according to the above-described embodiment provided on one or both sides of the display panel.

The above display panel can be a liquid crystal panel, a plasma panel, and an organic light-emitting panel.

Accordingly, the display device may be a liquid crystal display (LCD), a plasma display device (PDP), and an organic light emitting display (OLED).

More specifically, the image display device may be a liquid crystal display device including a liquid crystal panel and polarizing plates provided on each of both sides of the liquid crystal panel, wherein at least one of the polarizing plates may be a polarizing plate including a polarizer according to one embodiment of the present specification described above. That is, the polarizing plate is characterized in that the polarizing plate includes a polyvinyl alcohol-based polarizer dyed with iodine and/or a dichroic dye and a protective film provided on at least one side of the polyvinyl alcohol-based polarizer, and has a depolarization region having a group transmittance of 80% or more in a local wavelength band of 400 nm to 800 nm, and an arithmetic average roughness (Ra) of the depolarization region is 200 nm or less, a polarization degree is 10% or less, and a sagging is 10 μm or less.

At this time, the type of the liquid crystal panel included in the liquid crystal display device is not particularly limited. For example, without limitation to the type, all known panels such as a passive matrix type panel such as a TN (twisted nematic) type, an STN (super twisted nematic) type, an F (ferroelectic) type or a PD (polymer dispersed) type; an active matrix type panel such as a two-terminal type or a three-terminal type; an IPS (In Plane Switching) panel and a VA (Vertical Alignment) panel can be applied. In addition, the types of other components constituting the liquid crystal display device, such as upper and lower substrates (for example, a color filter substrate or an array substrate), are also not particularly limited, and components known in this field can be employed without limitation.

Hereinafter, in order to specifically explain this specification, examples will be given and described in detail. However, the examples according to this specification may be modified in various different forms, and the scope of this application is not construed as being limited to the examples described below. The examples of this application are provided to more completely explain this specification to a person having average knowledge in the art.

<Manufacturing Example>

Preparation of compound 1

Preparation of compound 1-1

6-Chloronicotinaldehyde (20 g, 142 mmol) and dimethylamine (10 g, 213 mmol) (95 g) were added to 100 mL of N,N-dimethylformamide, and then heated to 80°C. After completion of the reaction, the mixture was cooled to room temperature, diluted with ethyl acetate, washed three times with water, and the combined organic layer was treated with anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. Compound 1-1 (14.5 g (68% yield)) was prepared by separation through silica gel column chromatography.

Preparation of compound 1

Compound 1-1 (20 g, 133 mmol) and ethyl 2-cyanoacetate (16.6 g, 147 mmol) were dissolved in 100 mL of 1,4-dioxane, 10 mL of 2N NaOH was added, and the mixture was heated to 80°C. After the reaction was completed, the mixture was cooled to room temperature, 100 mL of water was slowly added, and the precipitated solid was filtered. The filtered solid was slurried again with EtOH to obtain 26.8 g (82% yield) of the target compound 1. MS: [M+H] ⁺ = 246

Preparation of compound 2

Preparation of compound 2-1

Using dibenzylamine (30.1 g, 156 mmol) instead of dimethylamine, the same experiment as in the preparation example of compound 1-1 was performed to prepare 26.1 g (75% yield) of compound 2-1.

Preparation of compound 2

Compound 2-1 (15 g, 61.2 mmol) and 2-cyanoacetic acid (5.72 g, 67.3 mmol) were added to 100 mL of 1,4-dioxane, 10 mL of 2N NaOH was added, and the mixture was heated to 80°C. After the reaction was completed, the mixture was cooled to room temperature, 2N HCl was added to adjust the pH to neutral, and the precipitated solid was filtered. The filtered solid was slurried with hexane and isopropyl alcohol solvents to produce 17.2 g (76%) of the target compound 2. MS: [M+H] ⁺ = 370

Preparation of compound 3

Preparation of compound 3-1

Using 3-(methylamino)propanenitrile (20 g, 142 mmol) instead of dimethylamine, the same experiment as in the preparation example of compound 1-1 was performed to prepare 19.3 g (72% yield) of compound 3-1.

Preparation of compound 3

Compound 3-1 (20 g, 106 mmol) and 2-(phenylsulfonyl)acetonitrile (20.1 g, 111 mmol) were added to 150 mL of ethanol, and 0.1 mL of piperidine was added and heated. After the reaction was completed, it was cooled to room temperature, concentrated under reduced pressure, and the concentrated compound was dissolved in ethyl acetate and washed three times with water to separate the organic layer. Anhydrous magnesium sulfate was added to the organic layer thus obtained to remove water, filtered, and concentrated under reduced pressure. The concentrated compound was separated through silica gel column chromatography to produce 12.4 g (49% yield) of the target compound 3. MS: [M+H] ⁺ = 353

Preparation of compound 4

Preparation of compound 4

Compound 1-1 (20 g, 133 mmol) and 3-oxo-3-phenylpropanenitrile (21.3 g, 146.6 mmol) were used in the same manner as in the preparation of compound 3 to prepare 29.5 g (80% yield) of the target compound 4. MS: [M+H] ⁺ = 278

Preparation of compound 5

Preparation of compound 5

Compound 2-1 (20 g, 66 mmol) and N-(tert-butyl)-2-cyanoacetamide (10.2 g, 72.8 mmol) were used in the same manner as in the preparation of compound 3 to prepare 19.9 g (71% yield) of the target compound 5. MS: [M+H] ⁺ = 425

<Example>

Example 1

[Preparation of adhesive composition]

In a 1 L reactor equipped with a cooling device for refluxing nitrogen gas and easy temperature control, 99 parts by weight of n-butyl acrylate (n-BA) and 1 part by weight of 2-hydroxybutyl acrylate (2-HBA) were charged, and nitrogen gas was purged for 60 minutes to remove oxygen. Thereafter, the temperature was maintained at 67°C, and 0.05 parts by weight of AIBN (azobisisobutyronitrile), a reaction initiator, was charged, and the reaction was performed for 8 hours. After the reaction, the mixture was diluted with ethyl acetate to produce an acrylic polymer having a solid concentration of 30 wt% and a weight average molecular weight of 1,000,000 g/mol.

An adhesive composition was prepared by mixing 1.5 parts by weight of a compound represented by the compound 1 as an ultraviolet absorber with respect to 100 parts by weight of the acrylic polymer manufactured above, a crosslinking agent (XDI isocyanate, T-39M manufactured by Mitsui Chemicals), and a silane coupling agent (T-78J manufactured by Shinetsu) in a solvent so that the solid concentration became 30% by weight.

[Manufacturing of adhesive layer]

The adhesive composition manufactured above was coated on the release-treated surface of a release-treated PET (poly(ethyl eneterephthalate)) film (thickness: 38 ㎛, MRF-39, manufactured by Mitsubishi Corporation) to a thickness of 7 ㎛ after drying, and heat-cured in an oven at 80° C. for 3 minutes to manufacture an adhesive layer.

[Manufacturing of polarizing plates]

A polarizer was manufactured by stretching a polyvinyl alcohol-based resin film, dyeing it with iodine, and then treating it with a boric acid aqueous solution. Then, a 60 ㎛ thick TAC (triacetyl cellulose) film was attached to one side of the polarizer using an aqueous polyvinyl alcohol-based adhesive. Then, a surface of the manufactured adhesive layer was laminated using the same aqueous polyvinyl alcohol-based adhesive as above to a surface of the polyvinyl alcohol-based polarizer to which the TAC film was not attached, to manufacture a polarizing plate.

Example 2

An adhesive composition, an adhesive layer, and a polarizing plate were manufactured in the same manner as in Example 1, except that the material of compound 2 was used instead of compound 1 in Example 1.

Example 3

An adhesive composition, an adhesive layer, and a polarizing plate were manufactured in the same manner as in Example 1, except that the material of compound 3 was used instead of compound 1 in Example 1.

Example 4

An adhesive composition, an adhesive layer, and a polarizing plate were prepared in the same manner as in Example 1, except that the material of compound 4 was used instead of compound 1 in Example 1.

Example 5

An adhesive composition, an adhesive layer, and a polarizing plate were manufactured in the same manner as in Example 1, except that the material of compound 5 was used instead of compound 1 in Example 1.

<Comparative Example>

Comparative Example 1

An adhesive composition, an adhesive layer, and a polarizing plate were manufactured in the same manner as in Example 1, except that the ultraviolet absorbent was not used.

Comparative Example 2

An adhesive composition, an adhesive layer, and a polarizing plate were manufactured in the same manner as in Example 1, except that a compound of the following chemical formula A was used instead of the compound represented by the chemical formula 1 used as the ultraviolet absorbent in Example 1.

[Chemical Formula A]

Evaluation Example 1 Evaluation of optical properties of polarizing plate

The polarizing plates manufactured in the examples and comparative examples were cut to a size of 25 mm × 25 mm (width × height) to manufacture specimens. By measuring the transmittance of the polarizing plates using an ultraviolet-visible spectrometer (V-7100, manufactured by JASCO), the ultraviolet ray blocking performance including the blue region was evaluated, and the results are shown in Table 1. The light transmittance in Table 1 below is expressed as a % ratio when the total light transmittance is set to 100.

Evaluation Example 2 Evaluation of color characteristics of polarizing plate

The polarizing plates manufactured in the examples and comparative examples were cut to a size of 25 mm × 25 mm (width × height) to manufacture specimens. The ab color values of the polarizing plates were measured using an ultraviolet-visible spectrometer (V-7100, manufactured by JASCO) to evaluate the visual characteristics of the polarizing plates, and the results are shown in Table 1. In the ab color values of the polarizing plates in Table 1 below, it can be confirmed that the visual characteristics are excellent because the change in the b value in particular is not large.

Evaluation Example 3 Durability Evaluation under Reliability Conditions

The polarizing plates manufactured in the Examples and Comparative Examples were cut to a size of 90 mm × 170 mm (width × height), and two specimens were prepared for each of the Examples and Comparative Examples. Then, the two prepared specimens were attached to both sides of a glass substrate (110 mm × 190 mm × 0.7 mm = width × height × thickness) so that the optical absorption axes of each polarizing plate crossed each other, thereby manufacturing a sample. The pressure applied during the attachment was approximately 5 kg/cm2, and the work was performed in a clean room so that no air bubbles or foreign substances were generated at the interface. The manufactured samples were placed in a reliability chamber and left for 1,000 hours under conditions of a temperature of 60°C and a relative humidity of 90%, and then the occurrence of lifting at the adhesive layer interface was observed. The durability evaluation criteria are as follows.

<Durability Evaluation Criteria>

◎: No lifting

○: Minor swelling occurs

△: Occurrence of a lift

×: A lot of lifting occurs

Optical properties of polarizing plates Color values of polarizing plates durability 380nm 410nm a b Example 1 0.00964 0.86813 -3.47596 6.81665 ◎ Example 2 0.0077 0.36083 -4.08728 7.92232 ◎ Example 3 0.00009 1.93391 -2.11241 4.49116 ◎ Example 4 0.02052 2.95266 -2.89452 5.79614 ◎ Example 5 0.1105 2.63084 -2.74404 5.56437 ◎ Comparative Example 1 0.24822 32.7043 -1.02422 2.37472 ◎ Comparative Example 2 0.0411 0.15561 -12.8472 23.49686 ◎

According to Table 1 above, it can be confirmed that Examples 1 to 5 have excellent UV blocking properties and excellent visual characteristics while exhibiting low transmittance for light with a wavelength of 380 nm to 410 nm.

10: Polarizing plate
20: Video display device
100: Polarizer
101: Protective layer
102: Adhesive layer
103: Protective film
201: Liquid crystal display panel
202: 1st polarizing plate
203: Second polarizing plate
204: Light source section

Claims (10)

A compound represented by the following chemical formula 1:
[Chemical Formula 1]

In the above chemical formula 1,
R1 and R2 are the same or different from each other, and each independently represents a substituted or unsubstituted alkyl group; or a substituted or unsubstituted cycloalkyl group, or are combined with each other to form a substituted or unsubstituted ring,
R3 is -CO ₂ R; -SO ₂ R';-COR''; or -CONR'''R'''',
R4 is -CN,
R5 are the same or different, and each independently hydrogen; -CN; -CO ₂ R; -SO ₂ R';-COR'';-CONR'''R''''; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,
R, R', R'', R''' and R'''' are the same or different and each independently represents hydrogen; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group,
R6 to R8 are the same or different, and each independently represents hydrogen; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted alkoxy group. delete delete A compound according to claim 1, wherein R5 to R8 are hydrogen. A compound according to claim 1, wherein R1 and R2 are the same as or different from each other, and each independently represents a substituted or unsubstituted alkyl group. A compound according to claim 1, wherein R1 and R2 are the same as or different from each other, and each independently represents a substituted or unsubstituted methyl group; or a substituted or unsubstituted ethyl group. In claim 1, the compound represented by the chemical formula 1 is a compound represented by any one of the following compounds:


. An adhesive composition comprising a compound according to any one of claims 1 and 4 to 7. A polarizing plate comprising an adhesive composition according to claim 8 or a cured product thereof. An image display device comprising a polarizing plate according to claim 9.