KR20160146319A - Crosslinkable composition - Google Patents

Crosslinkable composition Download PDF

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KR20160146319A
KR20160146319A KR1020150083422A KR20150083422A KR20160146319A KR 20160146319 A KR20160146319 A KR 20160146319A KR 1020150083422 A KR1020150083422 A KR 1020150083422A KR 20150083422 A KR20150083422 A KR 20150083422A KR 20160146319 A KR20160146319 A KR 20160146319A
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formula
crosslinkable composition
compound
ionic compound
composition according
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KR1020150083422A
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Korean (ko)
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박형숙
이지영
양세우
손현희
윤소라
한슬기
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주식회사 엘지화학
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Publication of KR20160146319A publication Critical patent/KR20160146319A/en

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    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F222/00Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/36Amides or imides
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00Processes of polymerisation
    • C08F2/44Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/24Homopolymers or copolymers of amides or imides
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J133/00Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/24Homopolymers or copolymers of amides or imides

Abstract

The present application relates to a crosslinkable composition, an optical member and a display device. In the present application, a pressure-sensitive adhesive layer having excellent workability and reworkability and exhibiting excellent durability after application can be formed, and a pressure-sensitive adhesive layer capable of stably maintaining antistatic properties under moisture- and moisture- May be provided.

Description

CROSSLINKABLE COMPOSITION [0002]

The present application relates to a crosslinkable composition, a sticky optical member and a display device.

The crosslinkable composition can be utilized in various fields. For example, a protective film or an optical element may be attached to an LCD (Liquid Crystal Display) panel (not shown) in order to prevent dirt such as dust or the like from adhering to the optical element such as a polarizing plate, Or the like, may be applied to the element or the like, and such a pressure-sensitive adhesive or adhesive may be formed of a crosslinkable composition.

The present application relates to a crosslinkable composition, a sticky optical member and a display device.

The term crosslinkable composition in the present application may mean a composition that can be crosslinked or cured. Such a crosslinkable composition may be crosslinked or cured to form a pressure-sensitive adhesive or an adhesive.

Exemplary crosslinkable compositions of the present application may comprise a compound represented by the following formula (1).

[Chemical Formula 1]

Figure pat00001

In the general formula (1), A is a core containing a polyalkylene oxide unit, B is a chain connected to the core, a chain containing a polyalkylene oxide unit, and m is a number of 2 or more.

In one example, the compound of Formula 1 may act as a crosslinking retarder to delay the reaction with the acrylic resin and the crosslinking agent among the components of the crosslinking composition described below, but the present invention is not limited thereto.

The compound of formula (1) may have a radial structure in which two or more chains (B) are connected to the core A. As described later, the terminal of the chain (B) of the formula (1) may be a hydroxy group or an alkyl group, and may be a hydroxy group, as appropriate.

The core and chain of the compound of formula (1) each contain at least one polyalkylene oxide unit.

The term polyalkylene oxide unit in the present application may be represented by the following formula (2).

(2)

Figure pat00002

In formula (2), A is an alkylene group.

The alkylene group of formula (2) may be, for example, a straight chain or branched chain alkylene group having 2 to 12 carbon atoms, 2 to 8 carbon atoms, and 2 to 4 carbon atoms.

For example, when A in the formula (2) is an alkyl group having 2 carbon atoms, the formula (2) may be represented by the following formula (A) In the present specification, the unit represented by the following formula (A) can be simply referred to as a PEG unit, and the unit represented by the following formula (B) can be simply referred to as a PPG unit.

(A)

Figure pat00003

[Chemical Formula B]

Figure pat00004

In one example, the core (A) of Formula (1) may include a unit of 2 or 3 carbon atoms in Formula (2), and may include, for example, the PEG or PPG unit.

The core (A) of the compound of formula (1) as described above may be a unit derived from a polyol. That is, as described later, the compound of formula (1) is a polyol having two or more hydroxyl groups, and a polyol containing the unit of formula (2) is reacted with a straight chain polymer compound having an isocyanate group at the terminal Lt; / RTI >

As the polyol forming the core (A) of the formula (1), for example, a polyol having a weight average molecular weight in the range of 1000 to 10,000, including the repeating unit of the above formula (2) no.

Examples of such polyols include polyols known under the names KPX PP-2000, KPX PP-2600, KPX GP-4000, KPX-GP-5000, KPX GP-4000 or KPX-HP3753 But is not limited thereto.

In the formula (1), the number of chains connected to the core (A) is represented by m, and the range of m is not particularly limited. For example, the range of m may be 2 or more or 3 or more. In another example, m may be less than 30, less than 25, less than 20, less than 15, less than 10, or less than 5.

In one example of the formula (1), B may be represented by the following formula (3). In the following formula (3), the left side of L 1 may be connected to the core (A).

(3)

Figure pat00005

In formula 3 A 1 to A 3 are each independently an alkylene group, Q 1 and Q 2 is an alicyclic or aromatic divalent residue, and L 1 to L 4 is a linker, x is a number greater than or equal to 1, y is 0, And z is a number of 1 or more.

The alkylene group in the formula (3) may be, for example, a straight chain or branched chain alkylene group having 2 to 12 carbon atoms, 2 to 8 carbon atoms, and 2 to 4 carbon atoms. The alkylene group may be optionally substituted by one or more substituents.

In formula (3), A 1 or A 2 and an oxygen atom (a repeating unit defined by x or z) connected thereto may form a repeating unit of the above-mentioned formula (2).

In the formula (3), the kind of the linker represented by L 1 to L 4 is not particularly limited and includes, for example, an oxygen atom, a sulfur atom, an alkylene group, an alkenylene group or an alkynylene group, have. The alkylene group may be a linear or branched alkylene group having 1 to 20 carbon atoms, 1 to 16 carbon atoms, 1 to 12 carbon atoms, 1 to 8 carbon atoms, or 1 to 4 carbon atoms, and the alkenylene group or alkynylene group may have, A straight chain or branched alkenylene group or an alkynylene group having 2 to 20 carbon atoms, 2 to 16 carbon atoms, 2 to 12 carbon atoms, 2 to 8 carbon atoms, or 2 to 4 carbon atoms.

≪ RTI ID = 0.0 &

Figure pat00006

[Chemical Formula D]

Figure pat00007

In the formulas C and D, R 1 and R 2 are each independently a hydrogen atom or an alkyl group.

The alicyclic or aromatic divalent residue in general formula (3) may be a divalent residue derived from an alicyclic compound or an aromatic compound.

The above aromatic compound means a compound or a derivative thereof having a structure in which one benzene ring structure, two or more benzene rings are linked together by sharing one or two carbon atoms, or is linked by any linker can do. The aromatic compound may be, for example, a compound having 6 to 30 carbon atoms, 6 to 25 carbon atoms, 6 to 21 carbon atoms, 6 to 18 carbon atoms, or 6 to 13 carbon atoms.

In the above, the alicyclic compound means a compound containing a cyclic hydrocarbon structure which is not an aromatic cyclic structure. The alicyclic compound may be, for example, a compound having 3 to 30 carbon atoms, 3 to 25 carbon atoms, 3 to 21 carbon atoms, 3 to 18 carbon atoms, or 3 to 13 carbon atoms unless otherwise specified.

The structure of -L 1 -Q 1 -L 2 - in formula (3) or the structure of -L 3 -Q 2 -L 4 - may be a structure derived from a diisocyanate compound as described later.

In one example, the chain (B) of the compound of formula (1) may be represented by the following formula (4).

[Chemical Formula 4]

Figure pat00008

In formula (4), A 1 to A 3 are each independently an alkylene group, Q 1 and Q 2 are alicyclic or aromatic divalent residues, R 1 to R 4 are each independently a hydrogen atom or an alkyl group, and x is 1 or more Y is a number equal to or greater than 0, and z is a number equal to or greater than 1.

The structure of the formula (4) is a structure in which L 1 to L 4, which are linking groups in the formula (3), are embodied in the above formula (C) or (D).

Therefore, in the formula (4), the contents of the formula (3) can be similarly applied to the details of the alkylene group, the divalent residue or the linker.

The compound of the formula (1) can be produced, for example, by reacting a polyol compound with a chain prepared by reacting a polyalkylene glycol with a diisocyanate compound.

For example, when polyethylene glycol is reacted with isobornyl diisocyanate in the production of the above chain, a chain as shown in the leftmost column in the following reaction formula A is formed, and a polyol (in the reaction formula A, triol, P A compound having three chains (m is 3) can be prepared upon reaction with the core (ex. Formula A)). The following Scheme B shows the same mechanism as Scheme A except that polypropylene glycol is applied during chain formation.

[Reaction Scheme A]

Figure pat00009

[Scheme B]

Figure pat00010

The range of x, y, and z in the general formula (3) or (4) is not particularly limited, and may be set within a range satisfying the following weight average molecular weight, for example.

The compound of formula (1) may have a weight average molecular weight of 10,000 or more, 15,000 or more, 20,000 or more, or 21,000 or more. The upper limit of the weight average molecular weight is not particularly limited and may be, for example, 100,000 or less.

The crosslinkable composition may further comprise an acrylic resin and a crosslinking agent together with the compound of the formula (1).

The acrylic resin may be, for example, an adhesive polymer. The term adhesive polymer may refer to a polymer which may exhibit stickiness before or after crosslinking.

As the adhesive polymer, for example, an acrylic resin having a carboxyl group can be used. By using such an adhesive polymer, a crosslinkable composition to be formed together with an ionic compound, which will be described later, can form a pressure-sensitive adhesive which exhibits stable durability under the conditions of humidity resistance and wet heat resistance, while showing little change in surface resistance with time. In addition, through the use of the adhesive polymer, a particularly effective effect can be obtained in the so-called VA mode.

As such an adhesive polymer, for example, a polymer comprising a polymerization unit of a (meth) acrylic acid ester monomer and a polymerization unit of an acidic monomer can be used. As used herein, the term " polymerized unit " may mean a state in which a corresponding monomer forms a polymer skeleton of a polymer by a polymerization reaction.

As the (meth) acrylic acid ester compound, for example, alkyl (meth) acrylate can be used. In consideration of the control of the cohesion, the glass transition temperature and the tackiness, the alkyl (meth) acrylate having an alkyl group having 2 to 12 carbon atoms (Meth) acrylate can be used. Examples of such monomers include methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, (Meth) acrylate, n-butyl (meth) acrylate, sec-butyl (meth) acrylate, pentyl (Meth) acrylate, isooctyl (meth) acrylate, isononyl (meth) acrylate and lauryl (meth) acrylate. Of these, one kind or more than two kinds may be included in the polymer.

The pressure-sensitive adhesive polymer may also contain, for example, an acidic monomer as a polymerization unit. The term acidic monomer means a copolymerizable monomer having an acidic group, for example, a monomer having a carboxyl group can be used. Examples of the monomer having a carboxyl group as mentioned above include (meth) acrylic acid, 2- (meth) acryloyloxyacetic acid, 3- (meth) acryloyloxypropyl acid, 4- (meth) acryloyloxybutyric acid, Dicarboxylic acid, itaconic acid, maleic acid or maleic anhydride, but the present invention is not limited thereto.

The adhesive polymer may contain at least about 5 parts by weight, at least about 5.5 parts by weight, or at least about 6 parts by weight, based on 100 parts by weight of the (meth) acrylic acid ester compound, of an acidic monomer as a polymerization unit. As used herein, the term " weight portion " may mean a ratio of weight between components, unless otherwise specified. The acidic monomer may be included in a ratio of up to about 20 parts by weight, up to about 15 parts by weight, or up to about 10 parts by weight in another example.

The pressure-sensitive adhesive polymer may further contain, if necessary, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 6-hydroxyhexyl (Meth) acrylate such as 2-hydroxyethyl (meth) acrylate or 2-hydroxypropyl (meth) acrylate, or hydroxyalkyl Hydroxy group-containing monomers such as phenol (meth) acrylate; Containing monomers such as (meth) acrylonitrile, (meth) acrylamide, N-methyl (meth) acrylamide, N-butoxymethyl (meth) acrylamide, N-vinylpyrrolidone or N-vinylcaprolactam ; (Meth) acrylic acid esters, alkoxy alkylene glycol (meth) acrylic acid esters, alkoxy alkylene glycol (meth) acrylic acid esters, alkoxy alkylene glycol (Meth) acrylic acid esters, phenoxy alkylene glycol (meth) acrylic acid esters, phenoxy alkylene glycol (meth) acrylic acid esters, phenoxy trialkylene glycol Alkylene oxide group-containing monomers such as polyalkylene glycol (meth) acrylic acid esters and the like; Styrene-based monomers such as styrene or methylstyrene; Glycidyl group-containing monomers such as glycidyl (meth) acrylate; Or vinyl acetate esters such as vinyl acetate. ≪ RTI ID = 0.0 > [0040] < / RTI >

The above-mentioned pressure-sensitive adhesive polymer can be produced through a conventional polymerization method. For example, a monomer mixture prepared by compounding the required monomers according to the desired monomer composition can be prepared by solution polymerization. If necessary in this process, suitable polymerization initiators or molecular weight regulators, chain transfer agents and the like may be used together.

The crosslinkable composition may further comprise a crosslinking agent, specifically, a crosslinking agent capable of crosslinking the adhesive polymer. As the crosslinking agent, a compound having two or more functional groups capable of reacting with a carboxyl group contained in the adhesive polymer may be used. As such a cross-linking agent, those usual in this field can be used, and examples thereof include an epoxy cross-linking agent or an aziridine cross-linking agent. Specific examples include ethylene glycol diglycidyl ether, triglycidyl ether, trimethylol propane triglycidyl ether, N, N, N ', N'-tetraglycidylethylenediamine, glycerin diglycidyl ether, Bis (1-aziridine carboxamide), N, N'-diphenylmethane-4,4'-bis (1-aziridine carboxamide), triethylene melamine, bis (2-methylaziridine) or tri-1-aziridinylphosphine oxide, but the present invention is not limited thereto. The crosslinking agent may be included in the crosslinkable composition in an amount of 0.01 to 15 parts by weight based on 100 parts by weight of the adhesive polymer, but is not limited thereto.

The crosslinkable composition may further comprise an isocyanate compound. Such a compound can serve, for example, to improve the adhesion with the optical member when the crosslinkable composition is applied to the optical member described later. Specific examples of such isocyanate compounds include tolylene diisocyanate, xylene diisocyanate, diphenylmethane diisocyanate, hexamethylene diisocyanate, isoform diisocyanate, tetramethyl xylene diisocyanate, naphthalene diisocyanate, and any one of the above polyols (eg, trimethylolpropane), and the like, but is not limited thereto. Such an isocyanate compound may be contained in an amount of 0.01 to 10 parts by weight based on 100 parts by weight of the adhesive polymer, but is not limited thereto.

The pressure-sensitive adhesive composition may further comprise an ionic compound. As the ionic compound, an ionic compound having an octanol-water partition coefficient (Log P) of 4 or more may be selected. The octanol partition coefficient is a measure of the distribution of solutes in the two unmixed phases, octanol and water. When the ionic compound having an octanol water partition coefficient of 4 or more is mixed with the crosslinkable composition, a crosslinkable composition capable of stably maintaining the antistatic property without changing the surface resistance over time under high humidity or high temperature and high humidity conditions can be provided . The octanol distribution coefficient may be at least 4.5, at least 5, or at least 5.5 in other examples. The higher the octanol distribution coefficient of water is, the higher the stability of the ionic compound in a high-humidity or high-humidity high-temperature condition is ensured, and the upper limit thereof is not particularly limited. In one example, the octanol distribution coefficient may be less than 30, less than 25, less than 20, or less than 15.

The ionic compound may also contain cations having a cation water binding energy in the range of 0 to 0.6 Kcal / mol. The higher the value of the binding energy, the more favorable the cation is in contact with water, and the binding energy in the above range can be advantageous in ensuring stability of the ionic compound in high humidity and high temperature and high humidity conditions. The binding energy with the water may be from 0 Kcal / mol to 0.55 Kcal / mol, from 0.1 Kcal / mol to 0.55 Kcal / mol, from 0.2 Kcal / mol to 0.55 Kcal / mol or from 0.3 Kcal / .

As the ionic compound, a known compound can be used without particular limitation that it exhibits the octanol water partition coefficient in the above range and, if necessary, exhibits binding energy with water in the above range.

As an ionic compound in one example, an ionic compound containing a cation of the following formula (5) can be used.

[Chemical Formula 5]

Figure pat00011

In Formula (5), R 1 is an alkyl group having 1 to 3 carbon atoms, and R 2 to R 4 are each independently an alkyl group having 4 to 20 carbon atoms.

In formula (5), the alkyl group of R 1 to R 4 may be linear, branched or cyclic, and may be suitably straight-chain. The alkyl group may be optionally substituted by a substituent such as another alkyl group.

In the formula (5), R 2 to R 4 in each of the other examples may independently be an alkyl group having 4 to 16 carbon atoms, 4 to 12 carbon atoms, or 4 to 8 carbon atoms.

The cation of the above structure is a structure in which a nitrogen atom is bonded to four alkyl groups and three of the alkyl groups are a long chain alkyl group having a carbon number of 4 or more. The cation of such a structure has an octanol distribution coefficient in the above- It is advantageous in securing the bonding energy of the antenna.

As the cation of the formula (5), N-methyl-N, N, N-tributylammonium, N-ethyl- N, N, N-trioctylammonium, N-methyl-N, N, N-trioctylammonium or N- It is not.

Examples of the anion included in the ionic compound include, without limitation, PF 6 - , AsF - , NO 2 - , fluoride (F - ), chloride (Cl - ), bromide (Br - ), iodide (I -), perchlorate (ClO 4 -), hydroxide (OH -), carbonate (CO 3 2 -), nitrate (NO 3 -), trifluoromethane sulfonate (CF 3 SO 3 -), (CH 3 C 6 H 4 SO 3 - ), p-toluenesulfonate (CH 3 C 6 H 4 SO 3 - ), sulfonic acid (SO 4 - ), hexafluorophosphate (PF 6 - ), methylbenzene sulfonate -), tetraborate (B 4 O 7 2-), carboxymethyl sulfonate (COOH (C 6 H 4) SO 3 -), sulfonate as a triple (CF 3 SO 2 -), benzo carbonate (C 6 H 5 COO -), acetate (CH 3 COO -), a triple acetate (CF 3 COO -), tetrafluoroborate (BF 4 -), tetra-benzyl borate (B (C 6 H 5) 4 -) or with ethyl trifluoroacetate in tris-pentafluoro-phosphate (P (C 2 F 5) 3 F 3 -) , etc. It can be used.

In one example, the ionic compound may include an anionic or bifluorosulfonylimide represented by the following formula (6), and the like.

[Chemical Formula 6]

[X (YO m R f ) n ] -

X is a nitrogen atom or a carbon atom, Y is a carbon atom or a sulfur atom, R f is a perfluoroalkyl group, m is 1 or 2, and n is 2 or 3.

In formula (6), when Y is carbon, m is 1, and when Y is sulfur, m is 2, n is 2 when X is nitrogen, and n is 3 when X is carbon.

The anion or bis (fluorosulfonyl) imide of formula (6) exhibits high electronegativity due to the perfluoroalkyl group (R f ) or the fluorine group and also forms a weak bond with the cation, including a unique resonance structure And at the same time has hydrophobicity. Therefore, the ionic compound exhibits excellent compatibility with other components of the composition such as a polymer, and can give a high antistatic property even in a small amount.

R f in formula (6) may be a perfluoroalkyl group having 1 to 20 carbon atoms, 1 to 12 carbon atoms, 1 to 8 carbon atoms or 1 to 4 carbon atoms, wherein the perfluoroalkyl group may be a linear, branched or cyclic Type structure. The anion of the formula (6) may be a sulfonylimide-based, sulfonylimide-based, carbonylimide-based or carbonylimide-based anion, and specifically may be a tris trifluoromethanesulfonylmethide, a bistrifluoromethane- A perfluorobutanesulfonylimide, bispentafluoroethanesulfonylimide, tris trifluoromethanecarbonylmide, bis perfluorobutanecarbonylimide or bispentafluoroethanecarbonyl, bispentafluoroethanesulfonylimide, bis Imide, etc., or a mixture of two or more species.

The ratio of the ionic compound in the crosslinkable composition is not particularly limited and may be adjusted to an appropriate range in consideration of the desired antistatic property.

In the crosslinkable composition, the ionic compound may not substantially form a chelate with the compound of formula (1). Further, in the crosslinkable composition, the compound of formula (I) may exhibit a higher affinity for an acrylic resin than an ionic compound.

The crosslinkable composition may contain, besides the above-mentioned components, one selected from the group consisting of a silane coupling agent, a tackifier, an epoxy resin, a crosslinking agent, an ultraviolet stabilizer, an antioxidant, a colorant, a reinforcing agent, a filler, a defoamer, a surfactant and a plasticizer The above additives may further be included.

The present application also relates to an optical element comprising: an optical element; And a pressure-sensitive optical member formed on one surface of the optical element and including a pressure-sensitive adhesive layer of the crosslinkable composition. The term pressure-sensitive adhesive layer of the crosslinkable composition as used herein refers to a pressure-sensitive adhesive layer formed using the above-mentioned crosslinkable composition. For example, the pressure-sensitive adhesive layer may be formed by volatilizing an organic solvent in the above-mentioned crosslinkable composition, Can be formed. In addition, in the above, the adhesive optical member may mean an optical member formed such that the optical member can be attached to the adherend by the adhesive layer.

As the optical element, for example, a polarizing film, a brightness enhancement film, a retardation film, or the like can be applied without particular limitation, and a polarizing film can be typically used.

The kind of the polarizing film is not particularly limited, and for example, general types known in this field such as a polyvinyl alcohol polarizing film and the like can be employed without limitation.

A polarizing film is a functional film capable of extracting only light vibrating in one direction from incident light while vibrating in various directions. Such a polarizing film may be, for example, a form in which a dichroic dye is adsorbed and oriented on a polyvinyl alcohol-based resin film. The polyvinyl alcohol-based resin constituting the polarizing film can be obtained by, for example, gelling a polyvinyl acetate-based resin. In this case, the polyvinyl acetate-based resin that can be used may include not only homopolymers of vinyl acetate but also copolymers of vinyl acetate and other monomers copolymerizable therewith. Examples of the monomer copolymerizable with vinyl acetate include monomers such as unsaturated carboxylic acids, olefins, vinyl ethers, unsaturated sulfonic acids, and acrylamides having an ammonium group, or a mixture of two or more thereof. no. The degree of gelation of the polyvinyl alcohol-based resin may be generally from 85 mol% to 100 mol% or 98 mol% or more. The polyvinyl alcohol resin may be further modified. For example, polyvinyl formal or polyvinyl acetal modified with aldehydes may be used. The degree of polymerization of the polyvinyl alcohol-based resin may be about 1,000 to 10,000 or about 1,500 to 5,000.

The polarizing film is formed by a process of stretching a polyvinyl alcohol resin film as described above (e.g., uniaxially stretching), a process of dyeing a polyvinyl alcohol resin film with a dichroic dye and adsorbing the dichroic dye, A step of treating the adsorbed polyvinyl alcohol based resin film with an aqueous solution of boric acid and a step of water washing after treatment with an aqueous solution of boric acid. As the dichroic dye, iodine or dichroic organic dyes may be used.

In the case where the optical element is a polarizing film, the optical member may further include a protective film attached to one side or both sides of the polarizing film. In this case, the pressure sensitive adhesive layer may be formed on one side of the protective film have. The kind of the protective film is not particularly limited and includes, for example, a cellulose-based film such as TAC (triacetyl cellulose); Polycarbonate film or PET (poly (ethylene terephthalate)); Polyethersulfone-based films; Or a polyolefin film produced by using a polyethylene film, a polypropylene film, a resin having a cyclo or norbornene structure, or an ethylene-propylene copolymer, or the like, or a film having a laminate structure of two or more layers.

The method of forming the pressure-sensitive adhesive layer on the optical element as described above in the present application is not particularly limited. For example, a method of directly coating and curing the crosslinkable composition on the polarizing plate may be used, A method in which the release-treated surface of the release film is coated and cured and then transferred to a polarizing plate.

On the surface of the optical element on which the pressure-sensitive adhesive layer is adhered, a treatment layer such as a corona treatment layer or a plasma treatment layer may further be present. A hydroxy group exists in the treatment layer, and the hydroxy group reacts with the isocyanate compound or the like to increase the interfacial adhesion.

The present application also relates to a display device to which the above-mentioned adhesive optical member is attached. The apparatus may include, for example, a liquid crystal panel and the optical member attached to one or both surfaces of the liquid crystal panel.

Examples of the liquid crystal panel include passive matrix type panels such as TN (twisted nematic) type, STN (super twisted nematic) type, F (ferroelectic) type or PD (polymer dispersed) type; An active matrix type panel such as a two terminal or a three terminal; A known panel such as an in-plane switching (IPS) panel and a vertical alignment (VA) panel may be used. Particularly, when the above-mentioned pressure sensitive adhesive is applied, the liquid crystal panel of the VA mode can be effectively used as the liquid crystal panel.

Other types of liquid crystal display devices, such as a color filter substrate or an array substrate, are not particularly limited, and configurations known in the art can be employed without limitation.

In the present application, a pressure-sensitive adhesive layer having excellent workability and reworkability and exhibiting excellent durability after application can be formed, and a pressure-sensitive adhesive layer capable of stably maintaining antistatic properties under moisture- and moisture- May be provided.

Claims (20)

A crosslinkable composition comprising a compound of the formula
[Chemical Formula 1]
Figure pat00012

In the general formula (1), A is a core containing a polyalkylene oxide unit, B is a chain connected to the core, a chain containing a polyalkylene oxide unit, and m is a number of 2 or more.
2. The crosslinkable composition according to claim 1, wherein the polyalkylene oxide unit represented by the formula (1)
(2)
Figure pat00013

In formula (2), A is a straight or branched alkylene group having 2 to 12 carbon atoms.
The crosslinkable composition according to claim 1, wherein the weight average molecular weight of the core is in the range of 1000 to 10,000. 2. The crosslinkable composition according to claim 1, wherein B in the formula (1)
(3)
Figure pat00014

In formula (3), A 1 to A 3 are each independently an alkylene group, Q 1 and Q 2 are aliphatic or aromatic divalent moieties, L 1 to L 4 are linkers, x is a number of 1 or more, y is 0 or more And z is a number of 1 or more.
2. The crosslinkable composition according to claim 1, wherein B in the formula (1)
[Chemical Formula 4]
Figure pat00015

In Formula 4, A 1 to A 3 are each independently an alkylene group, Q 1 and Q 2 are aliphatic or aromatic divalent moieties, x is a number of 1 or more, y is a number of 0 or more, and z is a number of 1 or more .
The crosslinkable composition according to claim 1, further comprising an acrylic resin having a carboxyl group and a crosslinking agent capable of crosslinking the acrylic polymer. 7. The crosslinkable composition of claim 6, further comprising an isocyanate compound. 7. The crosslinkable composition of claim 6, further comprising an ionic compound. The crosslinkable composition of claim 8, wherein the ionic compound has a water partition coefficient of octanol of 4 or more. 9. The crosslinkable composition of claim 8, wherein the ionic compound has an octanol water partition coefficient of 5 or greater. 9. The crosslinkable composition according to claim 8, wherein the ionic compound comprises a cation having a binding energy with water in the range of 0 to 0.6 Kcal / mol. 9. The crosslinkable composition according to claim 8, wherein the ionic compound comprises a cation of the following formula (5):
[Chemical Formula 5]
Figure pat00016

In Formula (5), R 1 is an alkyl group having 1 to 3 carbon atoms, and R 2 to R 4 are each independently an alkyl group having 4 to 20 carbon atoms.
9. The crosslinkable composition according to claim 8, wherein the ionic compound comprises an anion of the following formula (6):
[Chemical Formula 6]
[X (YO m R f ) n ] -
X is a nitrogen atom or a carbon atom, Y is a carbon atom or a sulfur atom, R f is a perfluoroalkyl group, m is 1 or 2, and n is 2 or 3.
The crosslinkable composition of claim 8, wherein the ionic compound does not substantially form a chelate with the compound of formula (I). The crosslinkable composition according to claim 8, wherein the compound of formula (1) exhibits a higher affinity for an acrylic resin than an ionic compound. The crosslinkable composition of claim 1, wherein the acrylic resin comprises at least 5 parts by weight of carboxyl group functional monomer units relative to 100 parts by weight of alkyl (meth) acrylate units and the alkyl (meth) acrylate units. An optical element; And a pressure-sensitive adhesive layer formed on one surface of the optical element, the pressure-sensitive adhesive layer comprising a crosslinked product of the crosslinkable composition of claim 1. The adhesive optical member according to claim 17, further comprising a corona treatment layer or a plasma treatment layer on a surface to which the pressure-sensitive adhesive layer of the optical element is adhered. A display device to which the adhesive optical member of claim 17 is attached. A VA-mode liquid crystal panel and a display device having the adhesive optical member according to claim 17 adhered to the liquid crystal panel.
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