KR101631380B1 - Pressure sensitive adhesive composition - Google Patents

Abstract

The present invention relates to a pressure-sensitive adhesive composition, a protective film, an optical laminate, a polarizing plate and a display device. The pressure-sensitive adhesive composition according to the present application exhibits a stable antistatic property, and the antistatic property is stably maintained even when it is left for a long time under a severe condition or in a severe condition such as a change in environment, and the pressure-sensitive adhesive composition has various physical properties such as adhesiveness, durability, An excellent pressure-sensitive adhesive can be provided. Incidentally, when the pressure-sensitive adhesive composition is used additionally, the coating process can be efficiently performed even when the solid content of the coating is kept high, so that the pressure-sensitive adhesive excellent in productivity and excellent in thickness uniformity can be formed. Further, the pressure-sensitive adhesive composition can be used for an optical film such as a protective film or a polarizing plate.

Description

[0001] PRESSURE SENSITIVE ADHESIVE COMPOSITION [0002]

The present invention relates to a pressure-sensitive adhesive composition, a protective film, an optical laminate, a polarizing plate and a display device.

The generation of static electricity causes various problems throughout the electronics industry. Fine dust entering electronic components due to static electricity causes problems such as temporary or permanent damage, malfunction or process delay of components as well as mechanical damage. In order to solve these problems, the development of the electronic industry and the improvement of antistatic technology are continuously required. For example, Patent Documents 1 and 2 disclose a pressure-sensitive adhesive to which conductivity is imparted as one solution for preventing electrification.

Patent Document 1: Korean Patent Publication No. 2009-0101761 Patent Document 2: JP-A-2005-031282

The present application provides a pressure-sensitive adhesive composition, a protective film, an optical laminate, a polarizing plate and a display device.

Exemplary pressure sensitive adhesive compositions may include block copolymers. As used herein, the term block copolymer may refer to a copolymer comprising blocks of differently polymerized monomers.

In one example, the block copolymer may include a first block having a glass transition temperature of 50 ° C or higher and a second block having a glass transition temperature of -10 ° C or lower. In the present specification, the "glass transition temperature of a given block" of the block copolymer means the glass transition temperature of the numerical value calculated based on the monomers forming the block. In one example, the glass transition temperature of the first block may be at least 60 ° C, at least 65 ° C, at least 70 ° C, at least 75 ° C, at least 80 ° C, or at least 90 ° C. The upper limit of the glass transition temperature of the first block is not particularly limited and may be, for example, about 150 캜, 140 캜, 130 캜 or 120 캜.

In another example, the glass transition temperature of the second block may be -20 占 폚 or lower, -30 占 폚 or lower, -35 占 폚 or lower, or -40 占 폚 or lower. The lower limit of the glass transition temperature of the second block is not particularly limited and may be, for example, about -80 캜, -70 캜, -60 캜 or -55 캜.

The block copolymer including the first and second blocks forms an appropriate fine-phase-separated structure in the pressure-sensitive adhesive, and accordingly, the cohesive force and the stress relaxation property are ensured at an appropriate level, and the endurance reliability, the light- The antistatic property can be ensured by realizing this excellent pressure-sensitive adhesive and by excellent interaction with the antistatic agent.

The first block may have a Number Average Molecular Weight (M _n ) of, for example, from 2,500 to 150,000. The number average molecular weight of the first block may mean, for example, the number average molecular weight of the polymer produced by polymerizing only the monomer forming the first block. The number average molecular weight referred to in the present specification can be measured by a conventional method using, for example, GPC (Gel Permeation Chromatograph). The number average molecular weight of the first block may be about 5,000 to 100,000 or 10,000 to 50,000 in another example.

The block copolymer may have a number average molecular weight of from 50,000 to 300,000. The number average molecular weight of the block copolymer may be in the range of 90,000 to 275,000, 90,000 to 250,000, or 100,000 to 250,000 in another example.

The block copolymer may have a molecular weight distribution (PDI; Mw / Mn), that is, a ratio (Mw / Mn) of a weight average molecular weight (Mw) to a number average molecular weight (Mn) of 1.0 to 2.5 or 1.4 to 2.5 .

A pressure-sensitive adhesive composition or pressure-sensitive adhesive having excellent physical properties can be provided by the block copolymer having the molecular weight characteristics as described above.

The block copolymer may be a crosslinkable copolymer having a crosslinkable functional group. Examples of the crosslinkable functional group include a hydroxyl group, a carboxyl group, an isocyanate group and a glycidyl group, and for example, a hydroxy group can be used.

When the functional group includes a crosslinkable functional group, for example, the functional group may be contained in, for example, a block having a relatively low glass transition temperature, that is, a second block. In one example, the crosslinkable functional group is not included in the first block, but may be included only in the second block. When the crosslinkable functional group is included in the second block, a pressure-sensitive adhesive exhibiting an appropriate cohesive force and stress relaxation property and having excellent physical properties such as durability, light-shielding properties and reworkability can be formed.

The kind of the monomer forming the first block and the second block in the block copolymer is not particularly limited as long as the glass transition temperature as described above can be ensured by the combination of the respective monomers.

The first block may comprise polymerized units derived, for example, from (meth) acrylic acid ester monomers. In the present specification, the fact that a monomer is contained in a polymer or a block in a polymerized unit may mean that the monomer undergoes a polymerization reaction to form the skeleton of the polymer or block, for example, a main chain or a side chain. As the (meth) acrylic acid ester monomer, for example, alkyl (meth) acrylate may be used. (Meth) acrylate having an alkyl group of 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 in consideration of control of cohesion, glass transition temperature and tackiness, Can be used. The alkyl group in the above may be straight-chain, branched-chain or cyclic. 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 or lauryl (meth) acrylate. Of these, Can be selected and used.

As the monomer forming the first block in consideration of the ease of controlling the glass transition temperature and the like, methacrylic acid ester monomers such as alkyl methacrylate and the like in the above monomers, for example, monomers having 1 to 20 carbon atoms, 1 to 16 carbon atoms, Alkyl methacrylates having 1 to 12 carbon atoms, 1 to 8 carbon atoms, or 1 to 4 carbon atoms can be used.

The second block may comprise, for example, 60 to 99.9 parts by weight of a (meth) acrylic acid ester monomer and 0.1 to 10 parts by weight of a copolymerizable monomer having a crosslinkable functional group. In the present specification, the unit weight portion may mean the ratio of the weight between each component. For example, the fact that the second block contains polymerized units derived from 60 to 99.9 parts by weight of the (meth) acrylic acid ester monomer and 0.1 to 10 parts by weight of the copolymerizable monomer having a crosslinkable functional group, (A: B) based on the weight of the (meth) acrylic ester monomer (A) forming the polymerized unit of the block and the copolymerizable monomer (B) having the crosslinkable functional group is 60 to 99.9: 0.1 to 10 It can mean the case. In this range of weight ratios, the physical properties of the pressure-sensitive adhesive, for example, the adhesive strength and the durability are maintained to be excellent, and the antistatic characteristics can be stably maintained even if the pressure-sensitive adhesive is exposed to high temperature or high humidity for a long period of time.

As the (meth) acrylic acid ester monomer forming the second block, it is preferable that the glass transition temperature in the range described above can be finally secured through copolymerization with the copolymerizable monomer among the monomers that may be contained in the first block Type monomers can be selected and used. As the (meth) acrylic acid ester monomer forming the second block in consideration of the ease of controlling the glass transition temperature and the like, an acrylic acid ester monomer such as an alkyl acrylate, for example, Alkyl acrylates having from 1 to 20 carbon atoms, from 1 to 16 carbon atoms, from 1 to 12 carbon atoms, from 1 to 8 carbon atoms, or from 1 to 4 carbon atoms.

Examples of the copolymerizable monomer having a crosslinkable functional group forming the second block include a copolymerizable monomer having a moiety copolymerizable with other monomers contained in the block copolymer such as an acrylic acid ester monomer and having a crosslinkable functional group , For example, a monomer having a hydroxyl group or the like can be used. In the production of pressure-sensitive adhesives, a variety of copolymerizable monomers having the above-mentioned crosslinkable functional groups are known, and all of these monomers can be used in the polymer. Examples of the copolymerizable monomer having a hydroxyl group include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) Hydroxyalkyl (meth) acrylate or 2-hydroxypropyleneglycol (meth) acrylate such as hydroxyalkyl (meth) acrylate or 8-hydroxyoctyl (Meth) acrylate, and the like can be used, but the present invention is not limited thereto.

For example, the first block or the second block may also include a polymerized unit derived from a monomer having an alkylene oxide unit in consideration of interaction with an antistatic agent and the like. The polymerization unit derived from the monomer having an alkylene oxide unit may be contained in only one of the first and second blocks or may be included in both of the two types of blocks.

As the monomer having an alkylene oxide unit, for example, a compound represented by the following formula (1) can be used.

[Chemical Formula 1]

Q is hydrogen or an alkyl group, U is an alkylene group or an alkylidene group, Z is hydrogen, an alkyl group or an aryl group, and m is an arbitrary number, for example, a number of 1 to 20. [

When two or more [-U-O-] units are present in the formula (1), the number of carbon atoms of the U in the unit may be the same or different.

In formula (1), m may be, for example, 1 to 16, 1 to 12, 4 to 16, 4 to 12, 4 to 10 or 4 to 8. Within this range, it is possible to maintain the polymerization efficiency and the crystallinity of the polymer in an appropriate range during the production of the polymer, and to provide the pressure-sensitive adhesive with antistatic properties appropriate.

The term "alkyl group" as used herein may mean an alkyl 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, unless otherwise specified. The alkyl group may be straight-chain, branched or cyclic. The alkyl group may be substituted by one or more substituents, or may be unsubstituted.

The term "alkylene group or alkylidene group" as used herein means an alkylene group or an 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, It may be the redeeming period. The alkylene group or alkylidene group may be linear, branched or cyclic. The alkylene or alkylidene group may be optionally substituted by one or more substituents.

In another embodiment, Q in formula (1) may be an alkyl group, for example, an alkyl group having 1 to 8 carbon atoms or 1 to 4 carbon atoms. When Q is an alkyl group, for example, it may be advantageous that the protective film is easily removed without residue or unevenness on the adherend when the pressure-sensitive adhesive composition is applied to a protective film or the like.

The term " aryl group " as used herein, unless otherwise specified, includes a benzene ring, or two or more benzene rings are linked, or two or more benzene rings share one or more carbon atoms Condensed or bonded to each other or a derivative thereof. The aryl group may be, for example, an aryl group having 6 to 25 carbon atoms, 6 to 22 carbon atoms, 6 to 16 carbon atoms, or 6 to 13 carbon atoms. Examples of the aryl group include a phenyl group, a phenylethyl group, a phenylpropyl group, a benzyl group, a tolyl group, a xylyl group and a naphthyl group.

Examples of the substituent which may be substituted in the specific functional group, for example, the alkyl group, the alkylidene group or the alkylene group in the present specification include an alkyl group, an alkoxy group, an alkenyl group, an epoxy group, a cyano group, a carboxyl group, An acryloyloxy group, a methacryloyloxy group or an aryl group, but the present invention is not limited thereto.

Examples of the compound represented by the general formula (1) include ethoxyethoxyethyl acrylate, alkoxy dialkylene glycol (meth) acrylate ester, alkoxytrialkylene glycol (meth) acrylate ester, alkoxy tetraalkylene glycol (Meth) acrylic acid esters such as dialkyleneglycol (meth) acrylate, aryloxytrialkylene glycol (meth) acrylate, aryloxytetraalkylene glycol (meth) acrylate and polyalkylene glycol monoalkyl ether But is not limited thereto.

When the monomer having an alkylene oxide unit is included, it is contained in a proportion of about 0.1 to 30 parts by weight, about 0.5 to 30 parts by weight, or about 1 to 30 parts by weight, for example, relative to 100 parts by weight of the block Block. For example, if the first block comprises a monomer having an alkylene oxide unit, the first block comprises 65 to 85 parts by weight of the (meth) acrylic acid ester monomer and 1 to 30 parts by weight of a monomer having an alkylene oxide unit And may include a polymerization unit derived from a weight portion. If the second block contains a monomer having an alkylene oxide unit, the second block preferably comprises 60 to 99.9 parts by weight of the (meth) acrylic acid ester monomer, 0.1 to 50 parts by weight of a copolymerizable monomer having a crosslinkable functional group, And 0.1 to 30 parts by weight of a monomer having an alkylene oxide unit. However, the above ratios are illustrative, and the proportion of the monomer having an alkylene oxide unit can be changed when necessary in consideration of the interaction with the antistatic agent.

The first block and / or the second block may further comprise any other comonomer, if necessary, for example, for controlling the glass transition temperature and the like, and the monomer may be included as polymerized units have. Examples of the comonomer include (meth) acrylonitrile, (meth) acrylamide, N-methyl (meth) acrylamide, N-butoxymethyl (meth) acrylamide, N-vinylpyrrolidone, Nitrogen-containing monomers such as lactam and the like; Glycidyl group-containing monomers such as glycidyl (meth) acrylate; And carboxylic acid vinyl esters such as vinyl acetate, but are not limited thereto. These comonomers may be included in the polymer by selecting one kind or more than two types as appropriate according to need. Such comonomers may be included in the block copolymer at a ratio of, for example, 20 parts by weight or less, or 0.1 parts by weight to 15 parts by weight, based on the weight of the other monomers, in each block copolymer.

The block copolymer may comprise 5 parts by weight to 50 parts by weight of the first block and 50 parts by weight to 95 parts by weight of the second block. The ratio of the weight between the first block and the second block is not particularly limited, but it is possible to provide the pressure-sensitive adhesive composition and the pressure-sensitive adhesive of excellent physical properties by controlling the ratio of the weight between blocks to the above ratio. In another example, the block copolymer comprises 5 to 45 parts by weight of the first block and 55 to 95 parts by weight of the second block, or 5 to 40 parts by weight of the first block and 60 to 60 parts by weight of the second block, 95 parts by weight.

In one example, the block copolymer may be a diblock copolymer comprising the first and second blocks, i.e. a block copolymer comprising only two blocks of the first and second blocks. By using the diblock copolymer, the durability of the pressure-sensitive adhesive, the stress relaxation property, and the reworkability can be maintained more excellent.

The method for producing the block copolymer is not particularly limited and can be produced by a conventional method. The block polymer is polymerized by, for example, an LRP (Living Radical Polymerization) method, and examples thereof include an organic rare earth metal complex as a polymerization initiator or an alkali metal or alkaline earth metal salt using an organic alkali metal compound as a polymerization initiator , An anion polymerization method in which an organic alkali metal compound is used as a polymerization initiator and synthesized in the presence of an organoaluminum compound, an atomic transfer radical polymerization method using an atom transfer radical polymerization agent as a polymerization initiator (ATRP), an activator regenerated by electron transfer (ARGET) atom transfer radical polymerization (ATRP), and an initiator for ICAR (polymerization initiator) for performing polymerization under an organic or inorganic reducing agent that generates electrons using an atom transfer radical polymerization agent as a polymerization initiator continuous activator regeneration) Atom Transfer Radical Polymerization (ATRP), weapon (RAFT) using a reversible addition-cleavage chain transfer agent using a reducing agent addition-cleavage chain transfer agent, or a method using an organic tellurium compound as an initiator. Among these methods, an appropriate method can be selected and applied.

The pressure-sensitive adhesive composition may further comprise an antistatic agent. As the antistatic agent, for example, an ionic compound may be used. As the ionic compound, an organic salt or an inorganic salt can be exemplified.

As the inorganic salt, for example, a metal salt containing a metal ion as a cation may be used. The metal salt may include, for example, an alkali metal cation or an alkaline earth metal cation. Examples of the cation include lithium ion (Li ⁺ ), sodium ion (Na ⁺ ), potassium ion (K ⁺ ), rubidium ion (Rb ⁺ ), cesium ion (Cs ⁺ ), beryllium ion (Be ²⁺ ) ⁺⁾ and calcium ions (Ca ^{2 +),} strontium ion (Sr ^{2 +)} and barium ion (Ba ^{2 +),} there is iljong or two kinds or more of the like can be illustrated, for example, a lithium ion, a sodium ion, a potassium ion , A lithium ion can be used in consideration of one or more kinds of magnesium ion, calcium ion and barium ion, or ion stability and mobility.

As the organic salt, for example, an ionic compound containing an organic cation can be used. As the organic cation, an onium cation can be exemplified. The term onium cation as used herein refers to a positive charged ion comprising a structure in which at least some of the charge is localized to atoms such as nitrogen (N), phosphorus (P) and / or sulfur (S) can do. The onium cation may be a cyclic or non-cyclic compound, and when cyclic, it may be an aromatic or non-aromatic compound. The onium cation may further comprise other atoms such as oxygen or carbon atoms in addition to the nitrogen, phosphorus and / or sulfur. The onium cation may optionally be substituted by a substituent such as a halogen, an alkyl group or an aryl group. For example, the acyclic compound may include one or more substituents, which may be cyclic or acyclic substituents, aromatic or nonaromatic substituents.

As the organic salt, a substance which is liquid at room temperature can be used. As used herein, the term " normal temperature " refers to a temperature that is not a heating or cooling state but is a natural temperature, for example, a temperature of about 10 캜 to about 30 캜, about 15 캜 to about 30 캜, about 23 캜, It can mean. By using a substance present in a liquid state at room temperature, it is possible to maintain the optical property, adhesive property and workability of the pressure-sensitive adhesive excellent, while ensuring adequate antistatic property. Further, even when the pressure-sensitive adhesive is allowed to stand or be stored for a long period of time, precipitation of the ionic compound from the pressure-sensitive adhesive and change or deterioration with time of the optical transparency or adhesive property of the pressure-sensitive adhesive can be prevented.

Examples of the onium cation include quaternary ammonium ion, phosphonium, pyridinium, imidazolium, pyrolidinium or piperidinium, and the like. And quaternary ammonium ions can usually be applied.

As the quaternary ammonium ion, a compound represented by the following general formula (2) can be exemplified.

(2)

In the formula (2), each of R ₂ to R ₅ independently represents hydrogen, alkyl, alkoxy, alkenyl or alkynyl.

In the definition of formula (2), alkyl or alkoxy may be alkyl or alkoxy having 1 to 20 carbon atoms, 1 to 12 carbon atoms, 1 to 8 carbon atoms or 1 to 4 carbon atoms. Alkyl or alkoxy may be linear, branched or cyclic and may optionally be substituted by one or more substituents.

In the definition of formula (2), alkenyl or alkynyl may be an alkenyl or alkynyl having 2 to 20 carbon atoms, 2 to 12 carbon atoms, 2 to 8 carbon atoms or 2 to 4 carbon atoms. In addition, the alkenyl or alkynyl may be linear, branched or cyclic alkenyl or alkynyl, and may optionally be substituted by one or more substituents.

In the definition of formula 2, when alkyl, alkoxy, alkenyl or alkynyl is substituted with one or more substituents, examples of substituents include hydroxy, alkyl, alkoxy, alkenyl, alkynyl, cyano, thiol, amino, Heteroaryl, and the like, but are not limited thereto.

In one example, R ₂ to R ₅ in the above formula (2) may each independently be alkyl, for example, a straight or branched chain having 1 to 12 carbon atoms, or R ₂ to R ₅ each independently represent a straight or branched And R < ₂ > to R < ₅ > may not be simultaneously alkyl of the same carbon number. That is, in the above example, it is preferable that R ₁ to R ₄ are all alkyl of the same carbon number. When R ₂ to R ₅ are both alkyl of the same carbon number, there is a high probability that the organic salt exists in a solid phase at room temperature.

Specific examples of the cation of the formula (2) include N, N-dimethyl N-propylammonium, N, N, N-trimethyl-N-propylammonium, , N-ethyl-N, N, N-tributylammonium, N-methyl-N, N, N-trihexylammonium, , N-trioctylammonium or N-ethyl-N, N, N-trioctylammonium, and the like.

In one example, R ₂ in the general formula (2) is alkyl having 1 to 3 carbon atoms, and R ₃ to R ₅ each independently represent an alkyl group having 4 to 20 carbon atoms, preferably 4 to 15 carbon atoms, more preferably 4 to 10 carbon atoms Cations which are alkyl can be used. By using such a cation, it is possible to provide a pressure-sensitive adhesive excellent in optical property, adhesive property, workability and antistatic property.

Examples of anions included in the ionic compounds such as inorganic salts and organic salts include PF ₆ ^- , AsF ^- , NO 2 ^- , fluoride (F ^- ), chloride (Cl ^- ), bromide (Br ^- ), iodide ^- ), perchlorate (ClO ₄ ^- ), hydroxide (OH ^- ), carbonate (CO ₃ ^{2 -} ), nitrate (NO ₃ ^- ), trifluoromethanesulfonate (CF ₃ SO ₃ ^- (SO ₄ ^-), phosphate (PF ₆ ^-) hexafluoropropane, methyl benzene sulfonate _{(CH 3 (C 6 H 4} ) SO 3 -), p- toluenesulfonate _{(CH 3 C 6 H 4 SO} 3 -) , tetraborate (B ₄ O ₇ ^2-), carboxymethyl sulfonate _{(COOH (C 6 H 4)} SO 3 -), sulfonate to flow (CF ₃ SO ₂ ^-), benzo carbonate (C ₆ H ₅ COO ^-), acetate (CH ₃ COO ^-), a triple acetate (CF ₃ COO ^-), borates (BF ₄ ^{tetrafluoro-),} tetra-benzyl borate _{(B (C 6 H 5)} 4 -) or tris-pentafluoropropane (P (C ₂ F ₅ ) ₃ F ₃ ^- ) and the like can be exemplified have.

In another example, the anion may be an anion or bifluorosulfonylimide represented by the following formula (3), or the like.

(3)

[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 (3), 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 (3) 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 (3) 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 linear, branched or cyclic Structure. The anion of formula (3) may be a sulfonylimide-based, sulfonylimide-based, carbonylimide-based or carbonylimide-based anion, and specifically includes tris trifluoromethanesulfonylmethide, bistrifluoromethanesulfonyl 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 antistatic agent may be adjusted in consideration of the desired antistatic property. In one example, 0.1 part by weight to 10 parts by weight, 0.1 part by weight to 9 parts by weight, and 0.1 part by weight To 8 parts by weight, from 0.5 part by weight to 7 parts by weight, from 0.5 part by weight to 6 parts by weight, from 0.5 part by weight to 5 parts by weight, or from 1 part by weight to 4 parts by weight. The pressure-sensitive adhesive composition according to the present application can have excellent antistatic property even if the content of the antistatic agent contained in the pressure-sensitive adhesive composition is included in a small proportion by including a monomer capable of improving the antistatic property as a polymerization unit.

The pressure-sensitive adhesive composition of the present application may satisfy the following conditions (1) to (3).

[Equation 1]

X ₁ ≤ 10 × 10 ¹¹ Ω / □

[Formula 2]

X ₂ ≤ 10 × 10 ¹¹ Ω / □

[Formula 3]

X ₃ ≤ 10 × 10 ¹¹ Ω / □

In the formulas 1 to 3 X ₁ denotes the initial surface resistance measured on a foundation sample so that a polarizing plate was prepared by using the pressure-sensitive adhesive of the pressure-sensitive adhesive composition of the present application 5cm × 5cm (horizontal × vertical), X ₂ is the X ₃ represents the resistance to heat and humidity measured after leaving the sample polarizing plate at 60 ° C and 90% relative humidity for 7 days, .

In the above formulas 1 to 3, the lower limit of X ₁ to X ₃ is not particularly limited because the lower the measured value is, the better the antistatic performance is. However, for example, X ₁ may be 10 10 ¹¹ ? /? ¹¹ Ω / □ or less, 8 × 10 ¹¹ Ω / □ or less, 7 × 10 ¹¹ Ω / □ or less, 6 × 10 ¹¹ Ω / □ or less, or 5 × 10 ¹¹ Ω / □ can be equal to or less than, the X ₂ is 10 × 10 ¹¹ Ω / □ or less, 9.0 × 10 ¹¹ Ω / □ or less, 8.0 × 10 ¹¹ Ω / □ or less, 7.0 × 10 ¹¹ Ω / □ or less, or 6.0 × 10 ¹¹ Ω / □ can be less than, X ₃ is 10 × 10 ¹¹ Ω / □ or less, 9.0 × 10 ¹¹ Ω / □ or less, or 8.0 × 10 ¹¹ Ω / □ or less.

In the present application, by including a monomer capable of improving the antistatic performance as described above in the pressure-sensitive adhesive composition as a polymerization unit, the heat resistance or anti-wet heat surface resistance value of the pressure-sensitive adhesive or optical member containing the pressure- It can be suitably applied to an optical member requiring an antistatic function.

The pressure-sensitive adhesive composition may further comprise a crosslinking agent capable of crosslinking the block copolymer. As the crosslinking agent, a crosslinking agent having at least two functional groups capable of reacting with the crosslinkable functional group contained in the block copolymer may be used. Examples of such a crosslinking agent include an isocyanate crosslinking agent, an epoxy crosslinking agent, an aziridine crosslinking agent or a metal chelate crosslinking agent, and for example, an isocyanate crosslinking agent may be used.

Examples of the isocyanate crosslinking agent include diisocyanate compounds such as tolylene diisocyanate, xylene diisocyanate, diphenylmethane diisocyanate, hexamethylene diisocyanate, isoboron diisocyanate, tetramethylxylene diisocyanate and naphthalene diisocyanate, A compound obtained by reacting a diisocyanate compound with a polyol can be used. As the polyol, for example, trimethylolpropane and the like can be used.

The pressure-sensitive adhesive composition may contain one or more of the above-mentioned crosslinking agents, but the crosslinking agents that can be used are not limited thereto.

The multifunctional crosslinking agent may be contained in the adhesive composition in an amount of, for example, 0.01 to 10 parts by weight and 0.01 to 5 parts by weight based on 100 parts by weight of the block copolymer, and the gel fraction, cohesive strength, Durability and the like can be excellently maintained.

The pressure-sensitive adhesive composition may further include a silane coupling agent. As the silane coupling agent, for example, a silane coupling agent having a beta-cyano group or an acetoacetyl group can be used. Such a silane coupling agent can be used, for example, so that a pressure-sensitive adhesive formed by a copolymer having a low molecular weight can exhibit excellent adhesion and adhesion stability, and can maintain excellent durability reliability under heat and moisture and heat have.

As the silane coupling agent having a beta-cyano group or an acetoacetyl group, for example, a compound represented by the following formula (4) or (5) can be used.

[Chemical Formula 4]

(R ₁ ) _n Si (R ₂ ) _(4-n)

[Chemical Formula 5]

(R ₃ ) _n Si (R ₂ ) _(4-n)

In formula 4, or 5, R ₁ is a beta-cyano-acetyl or beta-and cyano-acetyl group, R ₃ is acetonitrile, and an acetyl group or an acetoacetyl group, R ₂ is an alkoxy group, n is from 1 to 3 Number.

In Formula 4 or 5, the alkyl group may be an alkyl 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 alkyl group may be linear, branched or cyclic have. In the general formula (2) or (3), the alkoxy group may be an alkoxy 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 alkoxy group may be a straight chain, Can be.

In formula (4) or (5), n may be, for example, 1 to 3, 1 to 2 or 1.

Examples of the compound of formula (4) or (5) include, for example, acetoacetylpropyltrimethoxysilane, acetoacetylpropyltriethoxysilane, beta-cyanoacetylpropyltrimethoxysilane or beta-cyanoacetylpropyltriethoxysilane , But are not limited thereto.

In the pressure-sensitive adhesive composition, the silane coupling agent may be contained in an amount of 0.01 to 5 parts by weight or 0.01 to 1 part by weight based on 100 parts by weight of the block copolymer, and the desired physical properties may be effectively imparted to the pressure-sensitive adhesive within this range.

The pressure-sensitive adhesive composition may further include a tackifier as necessary. Examples of the tackifier include a hydrocarbon resin or hydrogenated product thereof, a rosin resin or hydrogenated product thereof, a rosin ester resin or hydrogenated product thereof, a terpene resin or hydrogenated product thereof, a terpene phenol resin or hydrogenated product thereof, Polymerized rosin ester resin, and the like, or a mixture of two or more of them may be used, but the present invention is not limited thereto. The tackifier may be contained in the pressure-sensitive adhesive composition in an amount of 100 parts by weight or less based on 100 parts by weight of the block copolymer.

The pressure-sensitive adhesive composition may further include, if necessary, further at least one additive selected from the group consisting of an epoxy resin, a curing agent, a UV stabilizer, an antioxidant, a colorant, a reinforcing agent, a filler, a defoamer, a surfactant and a plasticizer.

The pressure-sensitive adhesive composition may have a gel fraction of 80% by weight or less after implementing the crosslinked structure. The gel fraction can be calculated by the following general formula (1).

[Formula 1]

Gel fraction (%) = B / A x 100

In the general formula (1), A represents the mass of the pressure-sensitive adhesive composition which implements the crosslinked structure, and B represents the mass of the pressure-sensitive adhesive composition of mass A in a net of 200 mesh, This indicates the dry weight of the insoluble fraction collected after immersion.

By maintaining the gel fraction at 80 wt% or less, workability, durability and reworkability can be maintained. The lower limit of the gel fraction is not particularly limited, and may be, for example, 0% by weight. However, when the gel fraction is 0% by weight, it does not mean that no crosslinking has proceeded to the pressure-sensitive adhesive composition at all. For example, a pressure-sensitive adhesive composition having a gel fraction of 0 wt% has some degree of crosslinking or crosslinking, but the degree of crosslinking is low, so that the gel can not be retained in the mesh having a size of 200 mesh Leakage may also be included.

The pressure-sensitive adhesive composition can be used in various applications. Typical applications include, but are not limited to, application to a protective film or optical film described below.

The present application is also directed to a protective film. The protective film can be used, for example, for protecting the surface of various optical films.

Examples of the optical film include a polarizing plate, a polarizer, a polarizer protective film, a retardation film, a viewing angle compensation film, and a brightness enhancement film, but the present invention is not limited thereto. As used herein, the term polarizer and polarizer refers to objects that are distinguished from each other. That is, the polarizer refers to a film, sheet or device itself exhibiting a polarization function, and the polarizer refers to an optical element including other elements together with the polarizer. Other elements that can be included in the optical element together with the polarizer include, but are not limited to, a polarizer protective film or a retardation layer.

The protective film may include, for example, a protective substrate layer and a pressure-sensitive adhesive layer on one or both surfaces of the substrate layer. The pressure-sensitive adhesive layer may include, for example, the pressure-sensitive adhesive composition described above. The pressure-sensitive adhesive composition may be contained in the pressure-sensitive adhesive layer, for example, in a crosslinked state, that is, a state in which a crosslinked structure is realized.

As the protective substrate layer, a general film or sheet known in this field can be used. For example, a polyester film such as polyethylene terephthalate or polybutylene terephthalate, a polytetrafluoroethylene film, a polyethylene film, a polypropylene film, a polybutene film, a polybutadiene film, a poly (vinyl chloride) film or a polyimide film And the like. Such a film may be composed of a single layer, or two or more layers may be laminated, and in some cases, a functional layer such as an antifouling layer may be further included. From the viewpoint of improving the adhesion of the substrate, a surface treatment such as a primer treatment may be performed on one surface or both surfaces of the substrate.

The thickness of the base layer is not particularly limited and may be suitably selected according to the application, and it may be usually formed to a thickness of 5 to 500 탆 or 10 to 100 탆.

The thickness of the pressure-sensitive adhesive layer included in the protective film is not particularly limited, and may be, for example, 2 占 퐉 to 100 占 퐉 or 5 占 퐉 to 50 占 퐉.

The pressure-sensitive adhesive composition may be used for an optical film. For the optical film, for example, a polarizing plate, a polarizer, a retardation film, an anti-glare film, a wide viewing angle compensation film, or a brightness enhancement film are laminated to each other, or the optical film or its laminate is adhered to an adherend such as a liquid crystal panel For example.

That is, the present application is also directed to a pressure-sensitive adhesive optical laminate. Exemplary optical stacks include optical films; And a pressure-sensitive adhesive layer formed on one side or both sides of the optical film. The pressure-sensitive adhesive layer may be, for example, for adhering the optical film to a liquid crystal panel or other optical film of an LCD device, or for laminating another optical film to the laminate. The pressure-sensitive adhesive layer may comprise the above pressure-sensitive adhesive composition. The pressure-sensitive adhesive composition may, for example, be contained in the pressure-sensitive adhesive layer in a state of realizing a crosslinked structure. Examples of the optical film include a polarizer, a retardation film, a brightness enhancement film, and a laminate in which two or more of the above are laminated.

The present application also relates to an adhesive polarizing plate. The polarizing plate may have, for example, a structure in which the optical film is a polarizer in the adhesive optical laminate.

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

A polarizer is a functional film capable of extracting only light vibrating in one direction from incident light while vibrating in various directions. Such a polarizer 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 polarizer 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%, preferably 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 polarizer is formed by a process of stretching a polyvinyl alcohol-based resin film as described above (e.g., uniaxial stretching), dyeing a polyvinyl alcohol-based resin film with a dichroic dye and adsorbing the dichroic dye, A process of treating a polyvinyl alcohol resin film with a boric acid aqueous solution and a process of washing with a boric acid aqueous solution after washing. As the dichroic dye, iodine or dichroic organic dyes may be used.

The polarizing plate may further include a protective film attached to one side or both sides of the polarizer. In this case, the pressure sensitive adhesive layer may be formed on one side of the protective film. 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 polarizing plate may further include at least one functional layer selected from the group consisting of a protective layer, a reflective layer, an antiglare layer, a retardation film, a wide view angle compensation film, and a brightness enhancement film.

The method for forming the pressure-sensitive adhesive layer on the protective film, the polarizing plate or the optical film in the present application is not particularly limited. For example, the pressure-sensitive adhesive composition may be directly coated and cured to form a crosslinked structure, And a method of forming a crosslinked structure by coating and curing the pressure-sensitive adhesive composition on the release-treated surface of the pressure-sensitive adhesive composition, followed by transferring the crosslinked structure.

The method of coating the pressure-sensitive adhesive composition is not particularly limited. For example, a method of applying the pressure-sensitive adhesive composition by a common means such as a bar coater may be used.

The multifunctional crosslinking agent contained in the pressure-sensitive adhesive composition during the coating process is preferably controlled in such a manner that the crosslinking reaction of the functional groups does not proceed from the viewpoint of performing a uniform coating process. Thus, the crosslinking agent can be crosslinked Structure to improve the cohesive force of the pressure-sensitive adhesive, and improve the adhesive property and cuttability.

The coating process is also preferably performed after sufficiently removing the bubble-inducing component such as volatile components or reaction residues in the pressure-sensitive adhesive composition, and thus the crosslinking density or the molecular weight of the pressure-sensitive adhesive is too low to lower the elastic modulus, It is possible to prevent the problem that the bubbles existing between the glass plate and the adhesive layer become large and scatterers are formed inside.

The method of curing the pressure-sensitive adhesive composition to realize a crosslinked structure is not particularly limited. For example, a method of maintaining the coating layer at a proper temperature so that a crosslinking reaction between the block copolymer contained in the coating layer and the multi- And the like.

The present application is also directed to a display device, for example, an LCD device. Mentioned exemplary optical laminate or polarizing plate. When the display device is an LCD, the device may include a liquid crystal panel and the polarizing plate or optical laminate attached to one or both sides of the liquid crystal panel. The polarizing plate or the optical laminate may be attached to the liquid crystal panel by the above-described pressure-sensitive adhesive. Examples of the liquid crystal panel to be applied to the LCD 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 type; A known panel such as an in-plane switching (IPS) panel and a vertical alignment (VA) panel may be used.

Other configurations of the display device, for example, types of upper and lower substrates such as a color filter substrate or an array substrate in an LCD are not particularly limited, and configurations known in this field can be employed without limitation.

The pressure-sensitive adhesive composition according to the present application exhibits a stable antistatic property, and the antistatic property is stably maintained even when it is left for a long time under a severe condition or in a severe condition such as a change in environment, and the pressure-sensitive adhesive composition has various physical properties such as adhesiveness, durability, An excellent pressure-sensitive adhesive can be provided. Incidentally, when the pressure-sensitive adhesive composition is used additionally, the coating process can be efficiently performed even when the solid content of the coating is kept high, so that the pressure-sensitive adhesive excellent in productivity and excellent in thickness uniformity can be formed. Further, the pressure-sensitive adhesive composition can be used for an optical film such as a protective film or a polarizing plate.

Hereinafter, the pressure-sensitive adhesive composition will be described in detail with reference to examples and comparative examples, but the scope of the pressure-sensitive adhesive composition is not limited to the examples shown below.

1. Evaluation of molecular weight

The number average molecular weight (Mn) and the molecular weight distribution (PDI) were measured using GPC under the following conditions, and the measurement results were converted using a standard polystyrene of Agilent system for the calibration curve.

<Measurement Conditions>

Measuring instrument: Agilent GPC (Agilent 1200 series, U.S.)

Column: Two PL Mixed B connections

Column temperature: 40 ° C

Eluent: THF (Tetrahydrofuran)

Flow rate: 1.0 mL / min

Concentration: ~ 1 mg / mL (100 μL injection)

2. Surface resistance evaluation (initial, heat and Wet heat  Surface resistance)

<Measurement Conditions>

Measuring instrument: Hiresta-UP (MCP-HT 450, Mitsubishi chemical)

Probe: URS

Voltage: 500V

<Measurement procedure>

1) The polarizing plates prepared in Examples and Comparative Examples were cut to a length of 5 cm and a length of 5 cm.

2) Measure the initial surface resistance for the cut sample.

3) The polarizing plate having the surface resistance measured in the step 2) is allowed to stand at 80 DEG C for 7 days, and the heat resistance surface resistance is measured.

4) The polarizing plate having the surface resistance measured in the above step 2) is allowed to stand at 60 ° C and 90% relative humidity for 7 days, and the surface resistance of wet heat resistance is measured.

3. Evaluation of durability (heat resistance and Wet heat  durability)

The polarizing plates prepared in Examples and Comparative Examples were cut to a width of about 180 mm and a length of about 320 mm to prepare specimens, which were then attached to 19-inch commercial panels. Thereafter, the panel is stored in an autoclave (50 DEG C, 5 atmospheres) for about 20 minutes to prepare a sample. (1) Heat resistance durability was evaluated by observing the occurrence of bubbles and peeling after maintaining the sample at 80 DEG C for 500 hours, and (2) After standing for 500 hours under relative humidity conditions, the occurrence of bubbles and peeling at the adhesive interface was observed and evaluated according to the following criteria.

<Evaluation Criteria>

A: No bubbles and peeling occurred

B: Bubbles and / or slight peeling occurred

C: large amount of bubbles and / or peeling occurred

Manufacturing example  1. Preparation of block copolymer (A1)

0.08 g of EBiB (ethyl 2-bromoisobutyrate), 11.2 g of methyl methacrylate (MMA) and 2.8 g of butyl methacrylate (BMA) were mixed in 6.1 g of ethyl acetate (EAc). The flask containing the mixture was sealed with a rubber membrane, purged with nitrogen at about 25 캜 for about 30 minutes and stirred, and dissolved oxygen was removed through bubbling. Then 0.002 g of CuBr ₂ , 0.005 g of TPMA (tris (2-pyridylmethyl) amine) and 0.016 g of 2,2'-azobis (2,4-dimethyl valeronitrile) were added to the oxygen- And the reaction was initiated by immersing in a reaction tank at about 67 ° C (polymerization of the first block). , 140 g of butyl acrylate (BA) previously bubbled with nitrogen, 4.7 g of hydroxybutyl acrylate (HBA), 4 g of ethoxyethoxyethyl acrylate (EOEOEA ) And 250 g of ethyl acetate (EAc) were added in the presence of nitrogen. Then, 0.006 g of CuBr ₂ , 0.012 g of TPMA and 0.05 g of V-65 were added to the reaction flask, and a chain extension reaction was carried out (polymerization of the second block). When the conversion of the monomer (BA) reaches 80% or more, the reaction mixture is exposed to oxygen, diluted with an appropriate solvent, and the reaction is terminated to prepare a block copolymer (in the above process, V- The reaction mixture was appropriately divided and added until the end of the reaction).

Manufacturing example  2 to 5. Block copolymers (A2, B1, C1  And D1 )

A block copolymer was prepared in the same manner as in Preparation Example 1, except that the raw materials used in the polymerization of the first block and the second block were adjusted in the ratio shown in Table 1 below.

division Block copolymer A1 A2 B1 C1 D1 The first block MMA  ratio 80 70 80 80 70 BMA  ratio 20 30 15 30 EOEOEA  ratio - - 5 20 - Mn (x10000) 2.3 2.7 2.5 2.3 2.7 PDI 1.34 1.41 1.36 1.34 1.41 The second block BA  ratio 90.0 92.0 92.0 97.0 95.0 HBA  ratio 3.0 5.0 3.0 3.0 5.0 EOEOEA  ratio 7.0 3.0 5.0 - - block
Copolymer Mn (× 10000) 14.5 19.8 19.8 17.0 18.8 PDI 2.1 1.9 1.7 1.8 2.0 Content Unit: g
MMA : methyl 메록acrylate  (Homopolymer Tg : About 110 ° C)
BMA : butyl 메록acrylate  (Homopolymer Tg : About 27 ° C)
EOEOEA : ethoxy ethoxy ethyl acrylate  (Homopolymer Tg : About -70 ° C)
BA : butyl acrylate (Homopolymer Tg : About -45 ° C)
HBA : 4- hydroxybutyl acrylate (Homopolymer Tg : About -80 ° C)
Tg : Glass transition temperature
Mn : Number average molecular weight
PDI : Molecular weight distribution

Manufacturing example  6. Random copolymers ( E1 )

8 parts by weight of methyl methacrylate (MMA), 89.3 parts by weight of n-butyl acrylate, and 2.7 parts by weight of 4-hydroxybutyl acrylate were charged into a 1 L reactor equipped with a cooling device to easily regulate the temperature and nitrogen gas was refluxed 100 parts by weight of n-dodecylmercaptan was added as a molecular weight regulator, and 120 parts by weight of ethyl acetate was added as a solvent. Next, nitrogen gas was purged for about 60 minutes to remove oxygen, 0.05 parts by weight of AIBN (azobisisobutyronitrile) as a reaction initiator was added while maintaining the temperature at 60 占 폚, and the reaction was carried out for about 8 hours to prepare a random copolymer. The number average molecular weight (Mn) of the prepared random copolymer (B3) was about 162,000, and the molecular weight distribution (PDI) was about 4.7.

Example  One

Preparation of coating liquid (pressure-sensitive adhesive composition)

0.04 parts by weight of a cross-linking agent (Coronate L, manufactured by NPU, Japan), 0.1 part by weight of DBTDL (Dibutyltin dilaurate) and 0.2 part by weight of a silane coupling agent having a? -Cyano acetyl group were added to 100 parts by weight of the block copolymer (A1) And ethyl acetate as a solvent were mixed to prepare a coating solution (pressure-sensitive adhesive composition) by adjusting the coating solid content to about 30% by weight.

Production of adhesive polarizer

The prepared coating solution was coated on a release-treated surface of a poly (ethylene terephthalate) (MRF-38, manufactured by Mitsubishi) having a thickness of 38 탆 and subjected to release treatment so that the thickness after drying was about 23 탆, For about 3 minutes. After drying, a WV liquid crystal layer of a polarizing plate (TAC / PVA / TAC laminated structure: TAC = triacetyl cellulose, PVA = polyvinyl alcohol polarizing film) coated with a WV (Wide View) The formed coating layer was laminated to prepare a pressure-sensitive polarizer.

Example  2 to 6, Comparative Example  1 to 3

A pressure-sensitive adhesive composition (coating solution) and a pressure-sensitive polarizer were prepared in the same manner as in Example 1, except that components and ratios thereof were controlled as shown in Table 2 in the preparation of the pressure-sensitive adhesive composition (coating solution).

division Example Comparative Example One 2 3 4 5 6 One 2 3 acryl
polymer Kinds A1 A1 A2 A2 B1 C1 D1 D1 E1 content 100 100 100 100 100 100 100 100 100 Cross-linking agent  content 0.04 0.04 0.04 0.04 0.04 0.04 0.04 0.04 0.04 DBTDL  content 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 SCA  content 0.2 0.2 0.2 0.2 0.2 0.2 0.2 0.2 0.2 Antistatic agent
( Inorganic salt ) content 2.0 1.0 2.0 - 2.0 2.0 2.0 - 5.0 Antistatic agent
( Organic salt ) content - - - 2.0 - - - 2.0 - Content Unit: Weight portion
Cross-linking agent : Coronate  L, Japan NPU My)
DBTDL : Dibutyltin dilaurate
SCA : β- Cyano acetyl group  Branch Silane Coupling agent  ( M812 , LG  Chemical)
Antistatic agent ( Inorganic salt ): LiTFSi  ( Lithium trifluorosulfonylimide )
Antistatic agent ( Organic salt ): 트리티틸 메메 Ammonium Bis ( trifluoromethanesulfone imide

The results of the physical properties evaluation of each of the above Examples and Comparative Examples are shown in Table 3 below.

division Example Comparative Example One 2 3 4 5 6 One 2 3 Initial surface resistance 1.17 2.33 2.24 2.35 1.89 4.15 4.78 4.42 1.19 Heat Resistance Surface Resistance 1.35 2.56 2.58 2.72 1.97 5.67 9.88 12.34 11.97 Wet heat  Surface resistance 1.62 2.65 2.79 2.91 2.11 7.73 48.35 37.79 34.85 Heat resistance durability A A A A A A B A B Wet heat  durability A A A A A A A A C Heat resistance: 80 ℃
Wet heat : 60 &lt; 0 &gt; C, 90% R.H.
Surface Resistance Unit: × 10 ¹¹  Ω / □

Claims (19)

A block copolymer having a first block having a glass transition temperature of 50 DEG C or higher and a second block having a glass transition temperature of -10 DEG C or lower and a crosslinking agent,
Wherein the first block or the second block is a pressure-sensitive adhesive composition comprising a polymerization unit derived from a monomer having an alkylene oxide unit,
Wherein the monomer having the alkylene oxide unit is represented by the following general formula (1), the second block includes a crosslinkable functional group, the crosslinkable functional group is not included in the first block, And a second block, wherein the pressure-sensitive adhesive composition comprises:
[Chemical Formula 1]

Wherein Q is hydrogen or an alkyl group, U is an alkylene group or an alkylidene group, Z is hydrogen, an alkyl group or an aryl group, and m is a number of 1 to 20. [ delete delete The pressure-sensitive adhesive composition according to claim 1, wherein the first block comprises a polymerization unit derived from a methacrylic acid ester monomer. The pressure-sensitive adhesive composition according to claim 1, wherein the second block comprises polymerized units derived from 60 to 99.9 parts by weight of an acrylic acid ester monomer and 0.1 to 10 parts by weight of a copolymerizable monomer having a crosslinkable functional group. delete The pressure-sensitive adhesive composition according to claim 1, wherein the first block and the second block each comprise a polymerization unit derived from a monomer having an alkylene oxide unit. delete The pressure-sensitive adhesive composition according to claim 1, further comprising an antistatic agent. The pressure-sensitive adhesive composition according to claim 9, wherein the antistatic agent is an organic salt or an inorganic salt. 11. The adhesive composition of claim 10, wherein the inorganic salt comprises an alkali metal cation or an alkaline earth metal cation. The pressure-sensitive adhesive composition according to claim 10, wherein the organic salt comprises a cation of the following formula (2):
(2)

In the general formula (2), R ₂ to R ₅ each independently represent hydrogen, an alkyl group, an alkoxy group, an alkenyl group or an alkynyl group. The pressure-sensitive adhesive composition according to claim 10, wherein the inorganic salt or organic salt comprises an anion represented by the following formula (3):
(3)
[X (YO _m R _f ) _n ] ^-
In the above formula (3), X represents nitrogen or carbon, Y represents carbon or sulfur, R _f represents a perfluoroalkyl group, m represents 1 or 2, and n represents 2 or 3. The pressure-sensitive adhesive composition according to claim 9, wherein the antistatic agent is contained in an amount of 0.1 to 10 parts by weight based on 100 parts by weight of the block copolymer. The pressure-sensitive adhesive composition according to claim 1, wherein the crosslinking agent is a crosslinking agent having two or more functional groups capable of reacting with a crosslinkable functional group. A protective substrate layer; And a pressure-sensitive adhesive layer comprising the pressure-sensitive adhesive composition of claim 1, which is formed on one side or both sides of the protective substrate layer. Optical film; And a pressure-sensitive adhesive layer comprising the pressure-sensitive adhesive composition according to claim 1, which is formed on one side or both sides of the optical film. A polarizer; And a pressure-sensitive adhesive layer comprising the pressure-sensitive adhesive composition according to claim 1, which is present on one side or both sides of the polarizer. A display device comprising the optical laminate of claim 17 or the polarizer of claim 18.