JP2009132909A - Pressure-sensitive adhesive for optical member and optical member - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a pressure-sensitive adhesive for an optical member, which has excellent antistatic properties and further, even under high-temperature and high-humidity conditions, has excellent durability, for example, further can realize excellent adhesion between an optical laminate, especially a polarizing plate, and a glass substrate, is free from foaming or separation between a pressure-sensitive adhesive layer and the glass substrate, and further can suppress the occurrence of a light leakage phenomenon caused by shrinkage of a polarizing film, and an optical member with the pressure-sensitive adhesive layer. <P>SOLUTION: The pressure-sensitive adhesive for the optical member is produced by cross-linking a resin composition [I] composed mainly of an acrylic resin (A) produced by polymerizing a polymerizable component containing ≥15 wt.% hydroxyl group-containing monomer. <P>COPYRIGHT: (C)2009,JPO&INPIT

Description

The present invention relates to an adhesive for optical members and an optical member with an adhesive layer containing the same.
Specifically, an optical film (polarizing film, retardation film, optical compensation film, brightness enhancement film, etc.) suitably used for an image display device such as a liquid crystal display device, an organic EL display device, and a PDP, for example, a polarizing film, An optical member pressure-sensitive adhesive used for adhesion between an optical laminate coated with a protective film such as a cellulose triacetate film and a glass substrate of a liquid crystal cell, and a pressure-sensitive adhesive layer made of this optical member pressure-sensitive adhesive were formed. The present invention relates to an optical member with an adhesive layer, particularly a polarizing plate with an adhesive layer.

  Conventionally, a polarizing film, for example, a polarizing plate coated with a cellulose film, for example, a cellulose triacetate film, on both sides of a polarizing film, for example, a polyvinyl alcohol film having a polarizing property, is a liquid crystal component that is aligned between two glass plates. Lamination is carried out on the surface of the sandwiched liquid crystal cell to form a liquid crystal display panel. This lamination to the liquid crystal cell surface is performed by bringing the pressure-sensitive adhesive layer provided on the polarizing plate surface into contact with the liquid crystal cell surface. This is usually done by pressing.

  The pressure-sensitive adhesive layer provided on the surface of the optical member such as the polarizing plate is provided with a separator for the purpose of preventing scratches or dirt, or the surface for the purpose of preventing scratches or dirt generated during processing and transporting processes. Although a protective film or the like is provided, these separators and the surface protective film are not necessary and are peeled and removed when they are bonded to a liquid crystal cell or the like. Static electricity is generated when the separator or the surface protection film is peeled off from such an optical member, and this static electricity causes dust to adhere to the optical member, causes an abnormal display due to disorder of the liquid crystal alignment, and peripheral circuit elements. There is a problem that problems such as electrostatic breakdown occur.

In addition, when an optical member provided with the above-mentioned pressure-sensitive adhesive layer is bonded to a liquid crystal cell, if foreign matter is mixed, damaged, or an adhesion error occurs, it will be peeled off and re-bonded. As described above, static electricity is generated and a problem occurs.
As such a countermeasure, for example, in an adhesive composition used for an optical member, it has been proposed to add an ionic liquid to a base polymer (see, for example, Patent Document 1).
JP 2006-11365 A

  However, in the disclosed technique of Patent Document 1, although the effect of antistatic performance is recognized, since it depends on the antistatic performance of only the ionic liquid, the antistatic performance is insufficient. Further, since the base polymer itself is a general polymer having no antistatic ability, the compatibility with the blended ionic liquid is low, and the ionic liquid may bleed over time. Further, durability and light leakage prevention performance, which are important for optical members, particularly polarizing plates, are not considered at all.

  Liquid crystal display panels using polarizing plates are widely used as display devices for personal computers, liquid crystal televisions, car navigation systems, etc., and as a result, the usage environment has become very harsh. It is required to be excellent in durability even in use, for example, there is no phenomenon such as foaming or peeling that occurs between the pressure-sensitive adhesive layer and the glass plate even under harsh environments such as high temperature and high humidity. In a high-temperature, high-humidity environment, the polarizing film contracts, whereas the adhesive layer cannot follow the contraction of the polarizing film, and light leaks from the peripheral edge of the liquid crystal display panel. It is required that there is no so-called light leakage phenomenon.

  Therefore, in the present invention, under such a background, the antistatic performance is excellent, and further, even under high temperature and high humidity conditions, the optical laminate, particularly, the adhesive property between the polarizing plate and the glass substrate is excellent, and the pressure-sensitive adhesive. The pressure-sensitive adhesive for optical members is excellent in durability, such as no foaming or peeling between the layer and the glass substrate, and preventing light leakage caused by contraction of the polarizing film, and the like. An object of the present invention is to provide an attached optical member.

  However, as a result of intensive studies in view of such circumstances, the present inventor uses a hydroxyl group-containing monomer as a polymerization component in the main component acrylic resin constituting the pressure-sensitive adhesive in a larger amount than the conventional substantial use amount. Thus, the present inventors have found that an adhesive for an optical member excellent in antistatic performance with improved antistatic performance of the acrylic resin itself can be obtained, and the present invention has been completed.

That is, the gist of the present invention is that the resin composition [I] obtained by polymerizing an acrylic resin (A) obtained by polymerizing a polymerization component containing 15% by weight or more of a hydroxyl group-containing monomer is crosslinked. It is related with the adhesive for optical members characterized by these.
In this invention, the optical member with an adhesive layer formed by laminating | stacking the said adhesive for optical members on an optical member is also provided.

  The pressure-sensitive adhesive for optical members of the present invention has an excellent effect on antistatic performance, and is excellent in adhesion between the optical laminate and the glass substrate even under high temperature and high humidity conditions. There is an effect that a liquid crystal display panel can be obtained in which foaming or peeling does not occur between the glass substrate and the glass substrate, and a light leakage phenomenon caused by contraction of the optical film can be suppressed.

The present invention is described in detail below.
In the present invention, (meth) acryl means acryl or methacryl, (meth) acryloyl means acryloyl or methacryloyl, and (meth) acrylate means acrylate or methacrylate.

  The acrylic resin (A) used in the present invention contains a hydroxyl group-containing monomer as an essential component as a polymerization component, and is obtained by homopolymerization or copolymerization with other copolymerization components.

Examples of the hydroxyl group-containing monomer (a1) in the present invention include 2-hydroxyethyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 5-hydroxypentyl (meth) acrylate, 6-hydroxyhexyl (meth) acrylate, (Meth) acrylic acid hydroxyalkyl esters such as 8-hydroxyoctyl (meth) acrylate, 10-hydroxydecyl (meth) acrylate, (4-hydroxymethylcyclohexyl) methyl (meth) acrylate, caprolactone-modified 2-hydroxyethyl ( 1) caprolactone-modified monomers such as (meth) acrylate, 2-acryloyloxyethyl-2-hydroxyethylphthalic acid, N-methylol (meth) acrylamide, N-hydroxyethyl (meth) acrylamide, etc. Hydroxyl group-containing monomer: 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 2-hydroxy-3-phenoxypropyl (meth) acrylate, 3-chloro-2-hydroxypropyl (meth) acrylate, 2- Secondary hydroxyl group-containing monomers such as hydroxy-3-phenoxypropyl (meth) acrylate; tertiary hydroxyl group-containing monomers such as 2,2-dimethyl-2-hydroxyethyl (meth) acrylate.
In addition, polyethylene glycol derivatives such as diethylene glycol (meth) acrylate and polyethylene glycol mono (meth) acrylate, polypropylene glycol derivatives such as propylene glycol mono (meth) acrylate, polyethylene glycol-polypropylene glycol-mono (meth) acrylate, poly (ethylene Oxyalkylene-modified monomers such as glycol-tetramethylene glycol) mono (meth) acrylate and poly (propylene glycol-tetramethylene glycol) mono (meth) acrylate may be used.

  Among the hydroxyl group-containing monomers (a1), a primary hydroxyl group-containing monomer is preferable in terms of excellent reactivity with a crosslinking agent, and it is more preferable to use 2-hydroxyethyl (meth) acrylate. It is particularly preferable in that it is easy to manufacture because of few impurities such as.

  As the hydroxyl group-containing monomer (a1) used in the present invention, it is also preferable to use a monomer having a content of di (meth) acrylate as an impurity of 0.5% or less, more preferably 0.2% or less. It is preferable to use 0.1% or less.

  As other copolymerization components other than the hydroxyl group-containing monomer (a1), a (meth) acrylic acid ester monomer (a2), if necessary, a functional group-containing monomer (a3) other than the hydroxyl group-containing monomer (a1) (hereinafter, And simply referred to as “functional group-containing monomer (a3)”) and other copolymerizable monomers (a4).

  Examples of the (meth) acrylic acid ester monomer (a2) include (meth) acrylic acid alkyl esters and (meth) acrylic acid phenyl esters.

  About this (meth) acrylic acid alkyl ester, it is preferable that carbon number of an alkyl group is 1-12 normally, especially 1-8, Furthermore, it is preferable that it is 4-8, Specifically, methyl (meth) acrylate , Ethyl (meth) acrylate, n-butyl (meth) acrylate, iso-butyl (meth) acrylate, tert-butyl (meth) acrylate, n-propyl (meth) acrylate, n-hexyl (meth) acrylate, 2-ethylhexyl (Meth) acrylate, n-octyl (meth) acrylate, isodecyl (meth) acrylate, lauryl (meth) acrylate, cetyl (meth) acrylate, stearyl (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, etc. Can be mentioned. Examples of (meth) acrylic acid phenyl ester include benzyl (meth) acrylate and phenoxyethyl (meth) acrylate.

  Other (meth) acrylic acid ester monomers include 2-methoxyethyl (meth) acrylate, 2-ethoxyethyl (meth) acrylate, 3-methoxybutyl (meth) acrylate, 2-butoxyethyl (meth) acrylate, 2- Butoxydiethylene glycol (meth) acrylate, methoxydiethylene glycol (meth) acrylate, methoxytriethylene glycol (meth) acrylate, ethoxydiethylene glycol (meth) acrylate, methoxydipropylene glycol (meth) acrylate, methoxypolyethylene glycol (meth) acrylate, octoxypolyethylene Glycol-polypropylene glycol-mono (meth) acrylate, lauroxypolyethylene glycol mono (meth) acrylate, Allo carboxymethyl (meth) acrylic acid esters of aliphatic such as polyethylene glycol mono (meth) acrylate, tetrahydrofurfuryl Lil (meth) acrylate. These can be used alone or in combination of two or more.

  Among such (meth) acrylic acid ester monomers (a2), n-butyl (meth) acrylate and 2-ethylhexyl (meth) acrylate are preferable in terms of copolymerizability, adhesive properties, ease of handling, and availability of raw materials. N-butyl (meth) acrylate is preferably used from the viewpoint of excellent antistatic performance.

  Examples of the functional group-containing monomer (a3) include a carboxyl group-containing monomer, a glycidyl group-containing monomer, an amide group-containing monomer, an amino group-containing monomer, a nitrogen-containing monomer, a phosphate group-containing monomer, and a sulfonic acid group-containing monomer. These may be used alone or in combination of two or more.

  Examples of the carboxyl group-containing monomer include Michael addition of acrylic acid, methacrylic acid, crotonic acid, maleic acid, maleic anhydride, itaconic acid, fumaric acid, acrylamide N-glycolic acid, cinnamic acid, and (meth) acrylic acid. (Eg, acrylic acid dimer, methacrylic acid dimer, acrylic acid trimer, methacrylic acid trimer, acrylic acid tetramer, methacrylic acid tetramer, etc.), 2- (meth) acryloyloxyethyl dicarboxylic acid monoester (eg, 2-acryloyloxyethyl) Succinic acid monoester, 2-methacryloyloxyethyl succinic acid monoester, 2-acryloyloxyethyl phthalic acid monoester, 2-methacryloyloxyethyl phthalic acid monoester, 2-acryloyloxyethyl hexahi Rofutaru acid monoester, 2-methacryloyloxyethyl hexahydrophthalic acid mono ester) and the like.

  Examples of the glycidyl group-containing monomer include glycidyl (meth) acrylate and allyl glycidyl ether.

  Examples of the amide group-containing monomer include acrylamide, methacrylamide, N- (n-butoxyalkyl) acrylamide, N- (n-butoxyalkyl) methacrylamide, N, N-dimethyl (meth) acrylamide, N, N- Examples include diethyl (meth) acrylamide, N, N-dimethylaminopropyl (meth) acrylamide, acrylamide-3-methylbutylmethylamine, dimethylaminoalkylacrylamide, and dimethylaminoalkylmethacrylamide.

  Examples of the amino group-containing monomer include dimethylaminoethyl (meth) acrylate and diethylaminoethyl (meth) acrylate.

  Examples of the nitrogen-containing monomer include acryloylmorpholine.

  Examples of the phosphoric acid group-containing monomer include 2- (meth) acryloyloxyethyl acid phosphate, bis (2- (meth) acryloyloxyethyl) acid phosphate, and the like.

  Examples of the sulfonic acid group-containing monomer include olefin sulfonic acids such as ethylene sulfonic acid, allyl sulfonic acid, and methallyl sulfonic acid, 2-acrylamido-2-methylpropane sulfonic acid, styrene sulfonic acid, and salts thereof. .

  Among such functional group-containing monomers (a3), carboxyl group-containing monomers, glycidyl group-containing monomers, amide group-containing monomers, and nitrogen-containing monomers are preferably used. Furthermore, the carboxyl group-containing monomers have excellent release properties and are durable. It is particularly preferably used because it contributes to the properties.

  Examples of other copolymerizable monomers (a4) include acrylonitrile, methacrylonitrile, styrene, α-methylstyrene, vinyl acetate, vinyl propionate, vinyl stearate, vinyl chloride, vinylidene chloride, alkyl vinyl ether, vinyl toluene, Examples include vinyl pyridine, vinyl pyrrolidone, itaconic acid dialkyl ester, fumaric acid dialkyl ester, allyl alcohol, acrylic chloride, methyl vinyl ketone, N-acrylamidomethyltrimethylammonium chloride, allyltrimethylammonium chloride, and dimethylallyl vinylketone.

  For the purpose of increasing the molecular weight, ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate A compound having two or more ethylenically unsaturated groups such as divinylbenzene can also be used in combination.

  In the present invention, it is also preferable to copolymerize a compound having antistatic performance as a copolymerizable monomer in order to further improve the antistatic performance of the acrylic resin (A). .

  The compound having such antistatic performance may be any compound having a hydrophilic structural portion, and examples of the hydrophilic group include a compound having an ionic group. Compounds having an ionic group include quaternized products such as dimethylaminoethyl (meth) acrylate, ionic liquids and ionic solids having a polymerizable group such as (meth) acrylate of an imidazolium salt, and quaternary ammonium bases. Examples include ionic group-containing polymerizable compounds such as urethane (meth) acrylate compounds.

  Among these, polyethylene glycol (meth) acrylate, imidazolium salt-based ionic liquid containing a (meth) acryloyl group, urethane (meth) acrylate containing a quaternary ammonium salt, polyethylene having 5 to 50 ethylene glycol repeating units Urethane (meth) acrylate using glycol or one terminal methyl, ethyl, allyl or the like as a raw material can be particularly preferably used.

  It is also possible to introduce a compound having antistatic performance into the side chain of the acrylic resin (A) once produced by copolymerization by grafting reaction. In this case, for example, a compound containing a hydroxyl group is selected from the compounds having the above hydrophilic structure sites, reacted with a polyisocyanate compound to form a urethane prepolymer, and then reacted with the hydroxyl group of the acrylic resin (A). May be introduced.

  In the present invention, the acrylic resin (A) is produced by polymerizing the monomer components (a1) to (a4). In the polymerization, solution radical polymerization, suspension polymerization, bulk polymerization, It can be performed by a conventionally known method such as emulsion polymerization. For example, polymerization monomers such as the above hydroxyl group-containing monomer (a1), (meth) acrylic acid ester monomer (a2), other functional group-containing monomer (a3), and other copolymerizable monomer (a4) in an organic solvent Then, a polymerization initiator (azobisisobutyronitrile, azobisisovaleronitrile, benzoyl peroxide, etc.) is mixed or dropped and polymerized at reflux or at 50 to 90 ° C. for 2 to 20 hours.

  Such a hydroxyl group-containing monomer (a1) must be contained as a copolymerization component of the acrylic resin (A) in an amount of 15% by weight or more based on the entire copolymerization component, and if it is too small, sufficient antistatic performance can be obtained. It becomes impossible. The preferable range of the content of the hydroxyl group-containing monomer (a1) is 15 to 90% by weight, more preferably 20 to 70% by weight, and particularly preferably 25 to 50% by weight. If the content of the hydroxyl group-containing monomer (a1) is too large, the storage stability of the acrylic resin tends to decrease, and if it is too small, the antistatic performance tends to be insufficient.

  Moreover, as a content rate of superposition | polymerization components other than a hydroxyl-containing monomer (a1), (meth) acrylic acid ester monomer (a2) is 0 to 85 weight%, Especially 10 to 85 weight%, Furthermore, 30 to 80 weight% It is preferable that the functional group-containing monomer (a3) other than the hydroxyl group-containing monomer (a1) is 0 to 40% by weight, particularly 0 to 30% by weight, more preferably 0 to 20% by weight, The other copolymerizable monomer (a4) is preferably 0 to 50% by weight, particularly 0 to 40% by weight, and more preferably 0 to 30% by weight.

  The weight average molecular weight of the acrylic resin (A) thus obtained is usually 100,000 to 3,000,000, preferably 300,000 to 2,500,000, particularly preferably 600,000 to 2,000,000. If the weight average molecular weight is too small, there is a tendency that sufficient agglomeration force cannot be obtained even by at least one crosslinking treatment of active energy ray irradiation and heat, which will be described later. And the cost tends to be unfavorable.

  The degree of dispersion (weight average molecular weight / number average molecular weight) of the acrylic resin (A) is not particularly limited, but is preferably 7 or less, particularly preferably 5.5 or less, and further 4.5 or less. Is particularly preferable, 3.5 or less is preferable. When the degree of dispersion is too high, the pressure-sensitive adhesive layer tends to be inferior in durability performance such as heat and moisture resistance and light leakage. The lower limit of the degree of dispersion is usually 1.1 from the viewpoint of production limit.

  Further, the glass transition temperature of the acrylic resin (A) is not generally specified, but is preferably −80 to −20 ° C., particularly preferably −75 to −25 ° C., more preferably −60 to −30 ° C., and the glass transition temperature. If it is too high, tack tends to be insufficient, and if it is too low, heat resistance tends to be poor.

In addition, said weight average molecular weight is a weight average molecular weight by standard polystyrene molecular weight conversion, and it is a column in high performance liquid chromatography (The Japan Waters company "Waters 2695 (main body)" and "Waters 2414 (detector)"). : Shodex GPC KF-806L (exclusion limit molecular weight: 2 × 10 ⁷ , separation range: 100 to 2 × 10 ⁷ , theoretical plate number: 10,000 plates / piece, filler material: styrene-divinylbenzene copolymer, filler The particle size is 10 μm), and the degree of dispersion is determined from the weight average molecular weight and the number average molecular weight. The glass transition temperature is calculated from the Fox equation.

  In the present invention, the resin composition [I] contains the acrylic resin (A) as a main component. Here, “containing as a main component” means that the acrylic resin (A) is usually 50% by weight or more, preferably 60% by weight or more, more preferably 70% by weight based on the total amount of the resin composition [I]. % Or more content. The upper limit is usually 99.9% by weight.

  In the present invention, the resin composition [I] containing the acrylic resin (A) as a main component is crosslinked to become an adhesive.

  As a method of crosslinking the resin composition [I], [α] a method of containing an unsaturated group-containing compound (B) and a polymerization initiator (C) and crosslinking with at least one of active energy rays and heat, [Β] A method of crosslinking using a crosslinking agent (D) is mentioned. As for the degree of crosslinking, only the method [α] or the method [β] alone can be sufficient, but if possible, the pressure-sensitive adhesive is more closely cross-linked and light leakage occurs. It is particularly preferable to use the above [α] and [β] in combination from the viewpoint of improving prevention.

  First, an unsaturated group-containing compound (B) and a polymerization initiator (C), which are the methods of [α], are contained, and the resin composition [I] is treated with at least one of active energy rays and heat (active energy rays). A method of crosslinking by at least one of irradiation and heating will be described.

  In the case of crosslinking by at least one of the active energy rays and heat (at least one of the active energy ray irradiation and heating), in addition to the acrylic resin (A) described above as the resin composition [I], The resin composition [I] containing the unsaturated group-containing compound (B) and the polymerization initiator (C) is used. Thus, by containing an unsaturated group containing compound (B), hardening can be adjusted and it becomes possible to implement | achieve the adhesive physical property suitable for an optical member use. Moreover, the reaction at the time of irradiation of active energy rays and / or heating can be stabilized by containing the said polymerization initiator (C).

  In the case of the cross-linking, the unsaturated group-containing compound (B) is polymerized (polymerized) by active energy rays and / or heat to perform cross-linking (physical cross-linking) with the acrylic resin (A). When the acrylic resin (A) contains an unsaturated group in the side chain, the unsaturated group-containing acrylic is not limited to polymerization of the unsaturated group-containing compound (B) by active energy rays and / or heat. Cross-linking accompanying polymerization of the resin (A) and the unsaturated group-containing compound (B) will also occur.

  The unsaturated group-containing compound (B) used in the present invention may be a monofunctional unsaturated group-containing compound having one unsaturated group in one molecule, or two or more in one molecule. A polyfunctional unsaturated group-containing compound having an unsaturated group may be used, but preferably an unsaturated group-containing compound having two or more unsaturated groups, more preferably an unsaturated group-containing compound having three or more unsaturated groups. A saturated group-containing compound is preferred from the viewpoint of curability during irradiation with active energy rays.

Examples of the structure of the unsaturated group-containing compound (B) include urethane (meth) acrylate compounds, epoxy (meth) acrylate compounds, polyester (meth) acrylate compounds, and one or more ethylene in one molecule. An ethylenically unsaturated monomer containing a polymerizable unsaturated group, for example, a monofunctional monomer, a bifunctional monomer, a trifunctional or higher functional monomer, and the like can be used. Among these, it is preferable to use the urethane (meth) acrylate compound (b1) and the ethylenically unsaturated monomer (b2) from the viewpoint of excellent curing speed and ultimate physical properties.
In addition, the unsaturated group-containing compound (B) may be a compound containing a oxyalkylene chain, a hydroxyl group, or an acid-base ion pair and / or a hydrophilic site such as a betaine structure. Is more preferable.

  The urethane (meth) acrylate compound (b1) is a (meth) acrylate compound having a urethane bond in the molecule, and can be produced by reacting a (meth) acrylic compound containing a hydroxyl group with a polyvalent isocyanate compound. .

  The (meth) acrylic compound containing the hydroxyl group is not particularly limited, and examples thereof include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 4- Hydroxybutyl (meth) acrylate, 6-hydroxyhexyl (meth) acrylate, 2- (meth) acryloyloxyethyl-2-hydroxypropyl phthalate, 2-hydroxy-3- (meth) acryloyloxypropyl (meth) acrylate, Caprolactone-modified 2-hydroxyethyl (meth) acrylate, pentaerythritol tri (meth) acrylate, dipentaerythritol penta (meth) acrylate, caprolactone-modified dipentaerythritol penta (meth) acrylate, capro Examples include kuton-modified pentaerythritol tri (meth) acrylate, ethylene oxide-modified dipentaerythritol penta (meth) acrylate, and ethylene oxide-modified pentaerythritol tri (meth) acrylate. Among them, hydroxyl group-containing (meta) having three or more acryloyl groups ) Acrylic compounds are preferably used. Moreover, these can be used 1 type or in combination of 2 or more types.

  The polyvalent isocyanate compound is not particularly limited, and examples thereof include aromatic, aliphatic, and alicyclic polyisocyanates. Among them, tolylene diisocyanate, diphenylmethane diisocyanate, hydrogenated diphenylmethane diisocyanate, Polyphenylmethane polyisocyanate, modified diphenylmethane diisocyanate, hydrogenated xylylene diisocyanate, xylylene diisocyanate, hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, tetramethylxylylene diisocyanate, isophorone diisocyanate, norbornene diisocyanate, 1,3-bis (isocyanato) Methyl) cyclohexane, phenylene diisocyanate, lysine diisocyanate, lysine triisocyanate And polyisocyanates such as naphthalene diisocyanate, trimer compounds or multimeric compounds of these polyisocyanates, burette-type polyisocyanates, water-dispersed polyisocyanates (for example, “Aquanate 100”, “Aqua Nate 110 ”,“ Aquanate 200 ”,“ Aquanate 210 ”, etc.), or the reaction products of these polyisocyanates and polyols. Among these, isophorone diisocyanate, tolylene diisocyanate, hexamethylene diisocyanate, and their trimer compounds or multimeric compounds are preferably used.

  Examples of the polyol include, but are not limited to, alkylene glycols such as ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, polyethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, butylene glycol, and polybutylene glycol. Compounds, 1,6-hexanediol, neopentyl glycol, cyclohexanedimethanol, hydrogenated bisphenol A, polycaprolactone, trimethylolethane, trimethylolpropane, polytrimethylolpropane, pentaerythritol, polypentaerythritol, sorbitol, mannitol, Multivalent alcohols such as glycerin, polyglycerin, polytetramethylene glycol A polyether polyol having at least one structure of polyethylene oxide, polypropylene oxide, ethylene oxide / propylene oxide block or random copolymerization; the polyhydric alcohol or polyether polyol and maleic anhydride, maleic acid, fumaric acid, anhydrous Polyester polyols that are condensates with polybasic acids such as itaconic acid, itaconic acid, adipic acid, and isophthalic acid; caprolactone-modified polyols such as caprolactone-modified polytetramethylene polyol; polyolefin-based polyols; polybutadiene-based polyols such as hydrogenated polybutadiene polyols Etc. Among these, polyethylene glycol derivatives are preferably used, and polyethylene glycol and polyethylene glycol monomethyl ether are particularly preferably used.

  Furthermore, as the polyol, for example, 2,2-bis (hydroxymethyl) butyric acid, tartaric acid, 2,4-dihydroxybenzoic acid, 3,5-dihydroxybenzoic acid, 2,2-bis (hydroxymethyl) propionic acid, 2,2-bis (hydroxyethyl) propionic acid, 2,2-bis (hydroxypropyl) propionic acid, dihydroxymethylacetic acid, bis (4-hydroxyphenyl) acetic acid, 4,4-bis (4-hydroxyphenyl) pentanoic acid Also included are carboxyl group-containing polyols such as homogentisic acid, sulfonic acid group or sulfonate group-containing polyols such as sodium 1,4-butanediolsulfonate.

  When using the reaction product of polyisocyanate and polyol, for example, it may be used as a terminal isocyanate group-containing polyisocyanate obtained by reacting the polyol with the polyisocyanate. In the reaction between the polyisocyanate and the polyol, a metal catalyst such as dibutyltin dilaurate or an amine catalyst such as 1,8-diazabicyclo [5.4.0] undecene-7 is used for the purpose of promoting the reaction. Is also preferable.

  In addition, it is preferable to use an oxyalkylene chain-containing urethane (meth) acrylate compound as the urethane (meth) acrylate compound (b1) in view of excellent antistatic performance.

  The oxyalkylene chain-containing urethane (meth) acrylate compound is obtained by using an alkylene glycol compound among the polyols, and the structure of the oxyalkylene chain-containing urethane (meth) acrylate compound is as follows. One of the hydroxyl groups at both ends of the alkylene glycol compound reacts with an isocyanate group, and the other is a urethane (meth) acrylate having an oxyalkylene chain structure that remains as a hydroxyl group. Even after the treatment, the oxyalkylene chain has a high degree of freedom and is easy to transport ions, which is preferable in that it exhibits excellent antistatic performance.

  The oxyalkylene chain-containing urethane (meth) acrylate compound is obtained by using an alkylene glycol compound having only one hydroxyl group in place of the polyol alkylene glycol compound having a plurality of hydroxyl groups. It may be a thing. Examples of the alkylene glycol compounds having only one hydroxyl group include polyethylene glycol monomethyl ether, polyethylene glycol monoallyl ether, polyethylene glycol lauryl ether, polyethylene glycol cetyl ether, polyethylene glycol stearyl ether, polyethylene glycol nonyl phenyl ether, polyethylene glycol Examples include alkyl group-containing polyalkylene glycol derivatives such as polyethylene glycol derivatives such as tridecyl ether, polyethylene glycol oleyl ether, polyethylene glycol octyl phenyl ether, polyoxyethylene oleyl cetyl ether, and polypropylene glycol derivatives such as polypropylene glycol monomethyl ether.

  The method for producing the urethane (meth) acrylate compound is not particularly limited. For example, a method of mixing a hydroxyl group-containing (meth) acrylic compound and a polyvalent isocyanate compound and reacting at 30 to 80 ° C. for 2 to 10 hours. Is given. In this reaction, it is preferable to use a urethanization catalyst such as tin octenoate, di-n-butyltin dilaurate, lead octylate, potassium octylate, potassium acetate, stannous octoate, or triethylenediamine.

  The weight average molecular weight of the urethane (meth) acrylate compound is preferably 300 to 4000, more preferably 400 to 3000, and particularly preferably 500 to 2000. That is, if the weight average molecular weight is too small, the cohesive force tends to be insufficient after curing, and if it is too large, the viscosity becomes too high and production tends to be difficult.

  In addition, as the urethane (meth) acrylate compound in the present invention, it is also preferable to use a urethane (meth) acrylate compound having a quaternary ammonium salt structure or an imidazolium salt in the molecule. In addition, it is preferable that the urethane (meth) acrylate compound has a structure in which an isocyanate group is intentionally left, from the viewpoint of improving the durability by making the network of the unsaturated group-containing compound and the acrylic resin dense.

  As the ethylenically unsaturated monomer (b2) used in the present invention, a monofunctional monomer, a bifunctional monomer, a trifunctional or higher monomer, and the like can be used.

  As said monofunctional monomer, what is necessary is just a monomer containing one ethylenically unsaturated group, for example, styrene, vinyl toluene, chlorostyrene, (alpha) -methylstyrene, methyl (meth) acrylate, ethyl (meth) acrylate, Acrylonitrile, vinyl acetate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, phenoxyethyl (meth) acrylate, 2-phenoxy-2-hydroxypropyl (meth) Acrylate, 2-hydroxy-3-phenoxypropyl (meth) acrylate, 3-chloro-2-hydroxypropyl (meth) acrylate, glycerin mono (meth) acrylate, glycidyl (meth) acrylate, lauryl (meth) acrylate Lilate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, tricyclodecanyl (meth) acrylate, dicyclopentenyl (meth) acrylate, n-butyl (meth) acrylate, hexyl (meth) acrylate, heptyl (meth) acrylate , Octyl (meth) acrylate, nonyl (meth) acrylate, decyl (meth) acrylate, isodecyl (meth) acrylate, dodecyl (meth) acrylate, n-stearyl (meth) acrylate, benzyl (meth) acrylate, phenol ethylene oxide modified ( Of phthalic acid derivatives such as (meth) acrylate, nonylphenol propylene oxide modified (meth) acrylate, 2- (meth) acryloyloxy-2-hydroxypropyl phthalate Half ester (meth) acrylate, furfuryl (meth) acrylate, carbitol (meth) acrylate, benzyl (meth) acrylate, butoxyethyl (meth) acrylate, allyl (meth) acrylate, acryloylmorpholine, 2-hydroxyethylacrylamide, N -Methylol (meth) acrylamide, N-vinylpyrrolidone, 2-vinylpyridine, 2- (meth) acryloyloxyethyl acid phosphate monoester and the like.

  Examples of the ethylenically unsaturated monomer include, in addition to the above, a Michael adduct of acrylic acid or 2-acryloyloxyethyl dicarboxylic acid monoester, and examples of the Michael adduct of acrylic acid include acrylic acid dimer, methacrylic acid dimer, Examples include acrylic acid trimer, methacrylic acid trimer, acrylic acid tetramer, and methacrylic acid tetramer. Examples of the 2-acryloyloxyethyl dicarboxylic acid monoester that is a carboxylic acid having a specific substituent include 2-acryloyloxyethyl succinic acid monoester, 2-methacryloyloxyethyl succinic acid monoester, and 2-acryloyloxy. Examples thereof include ethylphthalic acid monoester, 2-methacryloyloxyethylphthalic acid monoester, 2-acryloyloxyethyl hexahydrophthalic acid monoester, and 2-methacryloyloxyethyl hexahydrophthalic acid monoester. Furthermore, oligoester acrylate is also mentioned.

  The bifunctional monomer may be any monomer containing two ethylenically unsaturated groups. For example, ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, tetraethylene glycol di (meth) acrylate, polyethylene Glycol di (meth) acrylate, propylene glycol di (meth) acrylate, dipropylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate, butylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, ethylene Oxide modified bisphenol A type di (meth) acrylate, propylene oxide modified bisphenol A type di (meth) acrylate, 1,6-hexanediol di (meth) acrylate 1,6-hexanediol ethylene oxide modified di (meth) acrylate, glycerin di (meth) acrylate, pentaerythritol di (meth) acrylate, ethylene glycol diglycidyl ether di (meth) acrylate, diethylene glycol diglycidyl ether di ( (Meth) acrylate, phthalic acid diglycidyl ester di (meth) acrylate, hydroxypivalic acid modified neopentyl glycol di (meth) acrylate, isocyanuric acid ethylene oxide modified diacrylate, 2- (meth) acryloyloxyethyl acid phosphate diester, etc. It is done.

  The tri- or higher functional monomer may be any monomer containing three or more ethylenically unsaturated groups. For example, trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) ) Acrylate, dipentaerythritol tri (meth) acrylate, dipentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, tri (meth) acryloyloxyethoxytrimethylolpropane, Glycerin polyglycidyl ether poly (meth) acrylate, isocyanuric acid ethylene oxide modified tri (meth) acrylate, ethylene oxide modified dipentaerythritol (Meth) acrylate, ethylene oxide modified dipentaerythritol hexa (meth) acrylate, ethylene oxide modified pentaerythritol tri (meth) acrylate, ethylene oxide modified pentaerythritol tetra (meth) acrylate, succinic acid modified pentaerythritol tri (meth) acrylate Etc.

Among the ethylenically unsaturated monomers (b2), it is preferable to use a compound containing an oxyalkylene chain. Such an oxyalkylene chain-containing ethylenically unsaturated monomer is not particularly limited, and for example, And a monofunctional ethylenically unsaturated monomer, a bifunctional ethylenically unsaturated monomer, a trifunctional or higher functional ethylenically unsaturated monomer.

  Examples of the monofunctional ethylenically unsaturated monomer containing the oxyalkylene chain include a monofunctional ethylenically unsaturated monomer containing an oxyalkylene chain represented by the following general formula (1).

（式中、Ｘはアルキレン基、ｎは１以上の整数であり、Ａは（メタ）アクリロイル基又はアルケニル基、Ｂは水素原子、アルキル基、フェニル基又はアシル基である。）

(In the formula, X is an alkylene group, n is an integer of 1 or more, A is a (meth) acryloyl group or alkenyl group, and B is a hydrogen atom, an alkyl group, a phenyl group, or an acyl group.)

  X in the general formula (1) is an alkylene group, among which an alkylene group having 1 to 10 carbon atoms is preferable, and in particular, an alkylene group having 1 to 4 carbon atoms such as an ethylene group, a propylene group, or a tetramethylene group. Is preferred. Further, when n is a polyoxyalkylene chain moiety having 2 or more, a homopolymer of the same oxyalkylene chain may be used, or different oxyalkylene chains may be copolymerized randomly or in a block form.

  A in the general formula (1) is a (meth) acryloyl group or an alkenyl group. As the alkenyl group, those having 2 to 6 carbon atoms, for example, a vinyl group or an allyl group are usually used. Among these, a methacryloyl group, an acryloyl group, and an allyl group are preferable, and a methacryloyl group and an acryloyl group are particularly preferable.

  B in the general formula (1) is a hydrogen atom, an alkyl group, a phenyl group, or an acyl group. As the alkyl group, those having 1 to 20 carbon atoms, preferably 1 to 10 carbon atoms are usually used. Among these, a hydrogen atom, a methyl group, and an ethyl group are preferable.

  N in the general formula (1) is an integer of 1 or more, preferably 1 to 500, particularly preferably 2 to 100, and more preferably 3 to 50. If the value of n is too small, the antistatic ability tends to be insufficient, and if it is too large, the durability tends to be insufficient.

As a specific example of the monofunctional monomer containing the oxyalkylene chain, [A: In the case of (meth) acryloyl group]
For example, polyethylene glycol derivatives such as polyethylene glycol mono (meth) acrylate, polypropylene glycol derivatives such as polypropylene glycol mono (meth) acrylate, polyethylene glycol-polypropylene glycol-mono (meth) acrylate, poly (ethylene glycol-tetramethylene glycol) mono (Meth) acrylate, poly (propylene glycol-tetramethylene glycol) mono (meth) acrylate, alkoxy polyethylene glycol (meth) acrylate and the like.

[A: In the case of an alkenyl group]
Examples thereof include polyethylene glycol derivatives such as polyethylene glycol monoallyl ether, polypropylene glycol derivatives such as polypropylene glycol monoallyl ether, and polyethylene glycol-polypropylene glycol-monoallyl ether.

  Among these, polyethylene glycol derivatives are preferable, and the number of moles of added ethylene oxide n is preferably 5 to 500, particularly 5 to 100, and more preferably 6 to 30 in terms of the balance between antistatic ability and durability. If the ethylene oxide addition mole number n is too small, the antistatic ability tends to be inferior, and if it is too large, the durability tends to deteriorate. Furthermore, A is preferably a (meth) acryloyl group from the viewpoint of influence on curability.

  Moreover, as a weight average molecular weight of the monofunctional ethylenically unsaturated monomer containing the oxyalkylene chain shown by the said General formula (1), 100-20000 are preferable normally, Especially it is 200-10000, Furthermore, 300-1000. Is preferred. If the weight average molecular weight is too small, the antistatic ability tends to be inferior, and if it is too large, the heat-and-moisture resistance tends to decrease.

  Examples of the bifunctional ethylenically unsaturated monomer containing the oxyalkylene chain include ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, tetraethylene glycol di (meth) acrylate, and polyethylene glycol di (meta). ) Acrylate, propylene glycol di (meth) acrylate, dipropylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate, butylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, ethylene oxide modified bisphenol A Type di (meth) acrylate, propylene oxide modified bisphenol A type di (meth) acrylate, 1,6-hexanediol ethylene oxide modified (Meth) acrylate, glycerin di (meth) acrylate, pentaerythritol di (meth) acrylate, ethylene glycol diglycidyl ether di (meth) acrylate, diethylene glycol diglycidyl ether di (meth) acrylate, diglycidyl phthalate di (meth) Examples thereof include acrylate, hydroxypivalic acid-modified neopentyl glycol di (meth) acrylate, isocyanuric acid ethylene oxide-modified diacrylate, and the like.

  Examples of the trifunctional or higher functional ethylenically unsaturated monomer containing an oxyalkylene chain include, for example, isocyanuric acid ethylene oxide modified triacrylate, ethylene oxide modified dipentaerythritol penta (meth) acrylate, ethylene oxide modified dipentaerythritol hexa ( And (meth) acrylate, ethylene oxide-modified pentaerythritol tri (meth) acrylate, ethylene oxide-modified pentaerythritol tetra (meth) acrylate, and the like.

  Among the unsaturated group-containing compounds (B), an ethylenically unsaturated monomer having an oxyalkylene chain and a urethane (meth) acrylate compound (b1) having an oxyalkylene chain in that it exhibits excellent antistatic performance. It is also preferable to use (b2). Moreover, the compound containing 3 or more of unsaturated groups is preferable from a viewpoint of durability improvement. It is also preferable to have a cyclic structure in the molecule.

  In addition, it is also preferable to use a (meth) acrylate compound containing an acid-base ion pair and / or a betaine structure in the molecule as the unsaturated group-containing compound (B) from the viewpoint of further improving the antistatic ability. .

  As a method for producing a (meth) acrylate compound containing an acid-base ion pair and / or a betaine structure in the molecule, for example, potassium hydroxide is added to a polyfunctional (meth) acrylate monomer containing a carboxyl group. Although the method of making it react is mention | raise | lifted, it is not limited to this. Specifically, a neutralized product of (meth) acrylic acid such as potassium (meth) acrylate, a neutralized potassium hydroxide of M-510 manufactured by Toagosei Co., Ltd., and the like are preferably used.

Further, as the unsaturated group-containing compound (B), an ionic liquid containing a polymerizable unsaturated group can be used, for example, 1- (2- (meth) acryloyloxyethyl) -3-octylimidazolium bromide. And halogen salts of (meth) acryloyloxyalkyl-3-alkylimidazolium such as 1- (2- (meth) acryloyloxyethyl) -3-octylimidazolium chloride, 1- (2- (meth) acryloyl (Methoxy) acryloyloxyalkyl-3-alkylimidazoles such as loxyethyl) -3-octylimidazolium trifluoromethanesulfonimide and 1- (2- (meth) acryloyloxyethyl) -3-octylimidazolium tetrafluoroborate Fluorine-containing salt of lithium, 1- (2- (meth) acryloyloxyethyl) -3-ethyl Cyano groups of (meth) acryloyloxyalkyl-alkylimidazoliums such as 2-methylimidazolium dicyanamide and 1- (2- (meth) acryloyloxyethyl) -3-ethyl-2-methylimidazolium thiocyanate Vinyl imidazoliums such as (meth) acryl imidazolium compounds such as salt containing, 1-butyl-3-vinylimidazolium tetrafluoroborate (1B3VIBF4), 1-butyl-3-vinylimidazolium trifluoromethanesulfonimide (1B3VITFSI) And ionic liquids composed of quaternary ammonium salt compounds such as trimethylaminoethyl (meth) acrylate dicyanamide.
In addition, the ionic liquid in this invention represents the ionic substance which consists of a cation component and an anion component which hold | maintain a liquid at the fixed temperature of the range of 0-100 degreeC.

  These unsaturated group containing compounds (B) may be used independently and may use 2 or more types together.

  As content of the said unsaturated group containing compound (B), 5-99 weight part is preferable with respect to 100 weight part of acrylic resin (A), More preferably, it is 7-50 weight part, More preferably, it is 10-30. Parts by weight. If the content of the unsaturated group-containing compound (B) is too large, the compatibility with the resin is deteriorated and the coating tends to be whitened. If the content is too small, the crosslinking density of the pressure-sensitive adhesive is insufficient. Leakage prevention and durability tend to decrease.

  In the present invention, the unsaturated group content as a whole of the resin composition [I] is usually preferably 10 to 360 mmol / 100 g from the viewpoint of balancing durability and light leakage prevention performance. Especially preferably, it is 30-240 mmol / 100g, More preferably, it is 50-180 mmol / 100g. If the unsaturated group content is too small, the cohesive strength will be insufficient, which tends to make it difficult to balance the durability and light leakage prevention performance.If the content is too large, the adhesive strength will be too low and the durability will be adversely affected. There is a tendency to affect.

  As the polymerization initiator (C), for example, various polymerization initiators such as a photopolymerization initiator (c1) and a thermal polymerization initiator (c2) can be used, and in particular, a photopolymerization initiator ( Use of c1) is preferable in that it can be crosslinked (cured) by irradiation with active energy rays such as ultraviolet rays for a very short time.

  When the photopolymerization initiator (c1) is used, the resin composition [I] is crosslinked by irradiation with active energy rays, and when the thermal polymerization initiator (c2) is used, the resin composition [I] is heated. It is also preferable to use both in combination, if necessary.

  The photopolymerization initiator (c1) is not particularly limited, and examples thereof include diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, benzyldimethyl ketal, 4- (2 -Hydroxyethoxy) phenyl- (2-hydroxy-2-propyl) ketone, 1-hydroxycyclohexylphenylketone, 2-methyl-2-morpholino (4-thiomethylphenyl) propan-1-one, 2-benzyl-2- Acetophenones such as dimethylamino-1- (4-morpholinophenyl) butanone and 2-hydroxy-2-methyl-1- [4- (1-methylvinyl) phenyl] propanone oligomer; benzoin, benzoin methyl ether, benzoin ethyl Ether, benzoin isopropyl ether, benzoy Benzoins such as isobutyl ether; benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyl-diphenyl sulfide, 3,3 ', 4,4'-tetra (t-butylperoxy Carbonyl) benzophenone, 2,4,6-trimethylbenzophenone, 4-benzoyl-N, N-dimethyl-N- [2- (1-oxo-2-propenyloxy) ethyl] benzenemethananium bromide, (4-benzoyl) Benzophenones such as (benzyl) trimethylammonium chloride; 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, 1-chloro-4-propoxythioxanthone, 2- (3-dimethyl Thioxanthones such as mino-2-hydroxy) -3,4-dimethyl-9H-thioxanthone-9-one mesochloride; 2,4,6-trimethylbenzoyl-diphenylphosphine oxide, bis (2,6-dimethoxybenzoyl) Acylphosphones such as -2,4,4-trimethyl-pentylphosphine oxide and bis (2,4,6-trimethylbenzoyl) -phenylphosphine oxide; In addition, as for these photoinitiators (c1), only 1 type may be used independently and 2 or more types may be used together.

  These auxiliary agents include triethanolamine, triisopropanolamine, 4,4′-dimethylaminobenzophenone (Michler ketone), 4,4′-diethylaminobenzophenone, 2-dimethylaminoethylbenzoic acid, 4-dimethylaminobenzoic acid. Ethyl, 4-dimethylaminobenzoic acid (n-butoxy) ethyl, isoamyl 4-dimethylaminobenzoate, 2-ethylhexyl 4-dimethylaminobenzoate, 2,4-diethylthioxanthone, 2,4-diisopropylthioxanthone Etc. can be used in combination.

  Among these, benzyl dimethyl ketal, 1-hydroxycyclohexyl phenyl ketone, benzoyl isopropyl ether, 4- (2-hydroxyethoxy) -phenyl (2-hydroxy-2-propyl) ketone, 2-hydroxy-2-methyl-1- It is preferable to use phenylpropan-1-one.

  Examples of the thermal polymerization initiator (c2) include methyl ethyl ketone peroxide, cyclohexanone peroxide, methyl cyclohexanone peroxide, methyl acetoacetate peroxide, acetyl acetate peroxide, 1,1-bis (t-hexyl peroxide). ) -3,3,5-trimethylcyclohexane, 1,1-bis (t-hexylperoxy) -cyclohexane, 1,1-bis (t-butylperoxy) -3,3,5-trimethylcyclohexane, 1, 1-bis (t-butylperoxy) -2-methylcyclohexane, 1,1-bis (t-butylperoxy) -cyclohexane, 1,1-bis (t-butylperoxy) cyclododecane, 1,1- Bis (t-butylperoxy) butane, 2,2-bis (4 -Di-t-butylperoxycyclohexyl) propane, p-menthane hydroperoxide, diisopropylbenzene hydroperoxide, 1,1,3,3-tetramethylbutyl hydroperoxide, cumene hydroperoxide, t-hexyl hydroper Oxide, t-butyl hydroperoxide, α, α′-bis (t-butylperoxy) diisopropylbenzene, dicumyl peroxide, 2,5-dimethyl-2,5-bis (t-butylperoxy) hexane, t-Butyl cumyl peroxide, di-t-butyl peroxide, 2,5-dimethyl-2,5-bis (t-butylperoxy) hexyne-3, isobutyryl peroxide, 3,5,5-trimethylhexa Noyl peroxide, octanoyl per Oxide, lauroyl peroxide, stearoyl peroxide, succinic acid peroxide, m-toluoyl benzoyl peroxide, benzoyl peroxide, di-n-propyl peroxydicarbonate, diisopropyl peroxydicarbonate, bis (4-t-butyl) (Cyclohexyl) peroxydicarbonate, di-2-ethoxyethyl peroxydicarbonate, di-2-ethoxyhexyl peroxydicarbonate, di-3-methoxybutyl peroxydicarbonate, di-s-butyl peroxydicarbonate, Di (3-methyl-3-methoxybutyl) peroxydicarbonate, α, α'-bis (neodecanoylperoxy) diisopropylbenzene, cumylperoxyneodecanoate, 1,1,3,3-te Lamethylbutyl peroxyneodecanoate, 1-cyclohexyl-1-methylethylperoxyneodecanoate, t-hexylperoxyneodecanoate, t-butylperoxyneodecanoate, t-hexylperoxy Pivalate, t-butylperoxypivalate, 1,1,3,3-tetramethylbutylperoxy-2-ethylhexanoate, 2,5-dimethyl-2,5-bis (2-ethylhexanoylper) Oxy) hexanoate, 1-cyclohexyl-1-methylethylperoxy-2-ethylhexanoate, t-hexylperoxy-2-ethylhexanoate, t-butylperoxy-2-ethylhexanoate, t- Hexyl peroxyisopropyl monocarbonate, t-butyl peroxyisobutyrate t-butyl peroxymalate, t-butyl peroxy-3,5,5-trimethylhexanoate, t-butyl peroxylaurate, t-butyl peroxyisopropyl monocarbonate, t-butyl peroxy-2 -Ethylhexyl monocarbonate, t-butyl peroxyacetate, t-butyl peroxy-m-toluylbenzoate, t-butyl peroxybenzoate, bis (t-butylperoxy) isophthalate, 2,5-dimethyl-2,5 -Bis (m-toluylperoxy) hexane, t-hexylperoxybenzoate, 2,5-dimethyl-2,5-bis (benzoylperoxy) hexane, t-butylperoxyallyl monocarbonate, t-butyltrimethylsilylper Oxide, 3,3 ', 4,4'-tetra Organic peroxide initiators such as (t-butylperoxycarbonyl) benzophenone and 2,3-dimethyl-2,3-diphenylbutane; 2-phenylazo-4-methoxy-2,4-dimethylvaleronitrile, 1- [(1-cyano-1-methylethyl) azo] formamide, 1,1′-azobis (cyclohexane-1-carbonitrile), 2,2′-azobis (2-methylbutyronitrile), 2,2′- Azobisisobutyronitrile, 2,2'-azobis (2,4-dimethylvaleronitrile), 2,2'-azobis (2-methylpropionamidine) dihydrochloride, 2,2'-azobis (2-methyl- N-phenylpropionamidine) dihydrochloride, 2,2'-azobis [N- (4-chlorophenyl) -2-methylpropionamidine] Hydride chloride, 2,2'-azobis [N- (4-hydrophenyl) -2-methylpropionamidine] dihydrochloride, 2,2'-azobis [2-methyl-N- (phenylmethyl) propionamidine] dihydrochloride 2,2'-azobis [2-methyl-N- (2-propenyl) propionamidine] dihydrochloride, 2,2'-azobis [N- (2-hydroxyethyl) -2-methylpropionamidine] dihydrochloride, 2,2'-azobis [2- (5-methyl-2-imidazolin-2-yl) propane] dihydrochloride, 2,2'-azobis [2- (2-imidazolin-2-yl) propane] dihydrochloride, 2,2'-azobis [2- (4,5,6,7-tetrahydro-1H-1,3-diazepin-2-yl) Lopan] dihydrochloride, 2,2'-azobis [2- (3,4,5,6-tetrahydropyrimidin-2-yl) propane] dihydrochloride, 2,2'-azobis [2- (5-hydroxy-3 , 4,5,6-tetrahydropyrimidin-2-yl) propane] dihydrochloride, 2,2'-azobis [2- [1- (2-hydroxyethyl) -2-imidazolin-2-yl] propane] dihydrochloride 2,2'-azobis [2- (2-imidazolin-2-yl) propane], 2,2'-azobis [2-methyl-N- [1,1-bis (hydroxymethyl) -2-hydroxyethyl] ] Propionamide], 2,2'-azobis [2-methyl-N- [1,1-bis (hydroxymethyl) ethyl] propionamide], 2,2'-azobis [2-me Til-N- (2-hydroxyethyl) propionamide], 2,2'-azobis (2-methylpropionamide), 2,2'-azobis (2,4,4-trimethylpentane), 2,2'- Azobis (2-methylpropane), dimethyl-2,2-azobis (2-methylpropionate), 4,4'-azobis (4-cyanopentanoic acid), 2,2'-azobis [2- (hydroxymethyl ) Propionitrile] and the like; and the like. In addition, only 1 type may be used independently for these thermal polymerization initiators, and 2 or more types may be used together.

  About content of the said polymerization initiator (C), 0.01-10 weight part with respect to 100 weight part of said acrylic resin (A), Especially 0.1-7 weight part, Furthermore, 0.3 It is preferably ~ 3 parts by weight. If the content of the polymerization initiator (C) is too small, the curability tends to be poor and the physical properties tend not to be stable, and if it is too much, no further effect can be obtained.

  In the active energy ray irradiation, far ultraviolet rays, ultraviolet rays, near ultraviolet rays, infrared rays and other electromagnetic waves, X rays, γ rays and other electromagnetic waves, as well as electron beams, proton rays, neutron rays, etc. can be used. Curing by ultraviolet irradiation is advantageous from the standpoint of availability of the device and price. In addition, when performing electron beam irradiation, it can harden | cure without using the said photoinitiator (c1).

As a light source for the ultraviolet irradiation, a high pressure mercury lamp, an electrodeless lamp, an ultrahigh pressure mercury lamp, a carbon arc lamp, a xenon lamp, a metal halide lamp, a chemical lamp, a black light, or the like is used. In the case of the high-pressure mercury lamp, for example, it is performed under conditions of 5 to 3000 mJ / cm ² , preferably 10 to 1000 mJ / cm ² . Moreover, in the case of the said electrodeless lamp, it is performed on the conditions of 2-1500 mJ / cm < ² >, for example, Preferably it is 5-500 mJ / cm < ² >. The irradiation time varies depending on the type of the light source, the distance between the light source and the coating surface, the coating thickness, and other conditions, but may be usually from several seconds to several tens of seconds, and in some cases, may be a fraction of a second. On the other hand, in the case of the electron beam irradiation, for example, an electron beam having an energy in the range of 50 to 1000 Kev is used, and the irradiation amount is preferably 2 to 50 Mrad.

  Moreover, when using a thermal-polymerization initiator (c2) as said polymerization initiator (C), a polymerization reaction is started and advanced by heating. The treatment temperature and treatment time during crosslinking by heating vary depending on the type of thermal polymerization initiator (c2) used, and are usually calculated from the half-life of the initiator, but the treatment temperature is usually The temperature is preferably 70 ° C to 170 ° C, and the treatment time is usually preferably 0.2 to 20 minutes, and particularly preferably 0.5 to 10 minutes.

Next, a method of crosslinking using the [β] crosslinking agent (D) will be described.
In the case of crosslinking using the crosslinking agent (D), as the resin composition [I], in addition to the acrylic resin (A), a resin composition [I] further containing a crosslinking agent (D) is used.

  When the crosslinking agent (D) is used, the acrylic resin (A) preferably has a functional group, and crosslinking (chemical crosslinking) is performed by reacting the functional group with the crosslinking agent.

  As said crosslinking agent (D), what is necessary is just a compound which has a functional group which reacts with the functional group contained in the said acrylic resin (A), for example, an isocyanate type compound, an epoxy-type compound, an aziridine type compound, a melamine type Examples include compounds, aldehyde compounds, amine compounds, and metal chelate compounds. Among these, an isocyanate compound is preferably used from the viewpoint of improving the adhesion with the base material and the reactivity with the base polymer.

  Examples of the isocyanate compound include 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, hydrogenated tolylene diisocyanate, 1,3-xylylene diisocyanate, 1,4-xylylene diisocyanate, and hexamethylene diisocyanate. , Diphenylmethane-4,4-diisocyanate, isophorone diisocyanate, 1,3-bis (isocyanatomethyl) cyclohexane, tetramethylxylylene diisocyanate, 1,5-naphthalene diisocyanate, triphenylmethane triisocyanate, and polyisocyanate compounds thereof Examples include adducts with polyol compounds such as trimethylolpropane, burettes and isocyanurates of these polyisocyanate compounds.

  Examples of the epoxy compound include bisphenol A / epichlorohydrin type epoxy resin, ethylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether, glycerin diglycidyl ether, glycerin triglycidyl ether, 1,6-hexanediol diglycidyl ether, Examples include trimethylolpropane triglycidyl ether, sorbitol polyglycidyl ether, polyglycerol polyglycidyl ether, pentaerythritol polyglycidyl erythritol, diglycerol polyglycidyl ether, and the like.

  Examples of the aziridine compound include tetramethylolmethane-tri-β-aziridinylpropionate, trimethylolpropane-tri-β-aziridinylpropionate, N, N′-diphenylmethane-4,4 ′. -Bis (1-aziridinecarboxamide), N, N'-hexamethylene-1,6-bis (1-aziridinecarboxyamide) and the like.

  Examples of the melamine compound include hexamethoxymethyl melamine, hexaethoxymethyl melamine, hexapropoxymethyl melamine, hexaptoxymethyl melamine, hexapentyloxymethyl melamine, hexahexyloxymethyl melamine, and melamine resin.

  Examples of the aldehyde compounds include glyoxal, malondialdehyde, succindialdehyde, maleindialdehyde, glutardialdehyde, formaldehyde, acetaldehyde, benzaldehyde and the like.

  Examples of the amine compound include hexamethylenediamine, triethyldiamine, polyethyleneimine, hexamethylenetetraamine, diethylenetriamine, triethyltetraamine, isophoronediamine, amino resin, polyamide, and the like.

  Examples of the metal chelate compound include multimetallic acetylacetone and acetoacetyl ester coordination compounds such as aluminum, iron, copper, zinc, tin, titanium, nickel, antimony, magnesium, panadium, chromium, and zirconium.

  Moreover, these crosslinking agents (D) may be used independently and may be used together 2 or more types.

  The content of the crosslinking agent (D) can be appropriately selected depending on the amount of the functional group contained in the acrylic resin (A), the molecular weight of the acrylic resin (A), and the purpose of use. (A) It is preferable that it is 0.1-15 weight part with respect to 100 weight part, Furthermore, it is preferable that it is 0.2-12 weight part, especially 1.5-10 weight part. If the amount of the crosslinking agent (D) is too small, there is a tendency that the cohesive force is insufficient and sufficient durability cannot be obtained. If the amount is too large, the flexibility and adhesive strength are lowered, the durability is deteriorated, and peeling is caused. Therefore, it tends to be difficult to bond the optical member to the optical member.

  In the present invention, in order to further improve the antistatic performance of the pressure-sensitive adhesive obtained by crosslinking the resin composition [I], a part of the crosslinking agent (D) has an antistatic performance. It is also preferable to use a cross-linking agent into which is introduced.

  For example, when a polyisocyanate compound is used as a crosslinking agent, a compound having a hydroxyl group in the structure is used as a method for introducing a structural site having antistatic performance into such a crosslinking agent. What is necessary is just to use it, and the crosslinking agent by which the structure site | part which has antistatic performance was introduce | transduced in part can be manufactured by the said hydroxyl group reacting with an isocyanate group.

  In addition, regarding the introduction of the structural part having antistatic performance into the crosslinking agent, the structural part having antistatic performance may be introduced into the crosslinking agent in advance and mixed with the acrylic resin (A), or acrylic. At the time of mixing with the system resin (A) and the crosslinking agent (D), a compound having antistatic performance may be blended at the same time and reacted with the crosslinking agent (D).

  In the present invention, sufficient crosslinking can be obtained only by the above-mentioned [α] active energy rays and / or heat (irradiation and / or heating of active energy rays). It is preferable to use in combination, and the cross-linking density of the pressure-sensitive adhesive is increased and the cohesive force is increased, so that a further superior one in terms of prevention of light leakage and durability can be obtained.

  In the present invention, it is preferable that the resin composition [I], which is a pressure-sensitive adhesive forming material, further contains a silane coupling agent (E) from the viewpoint of improving the adhesion to the optical member. As content of the said silane coupling agent (E), it is 0.001-10 weight part normally with respect to 100 weight part of acrylic resin (A), More preferably, 0.01-1 weight part, Particularly preferred is 0.03 to 0.8 parts by weight. If the content of the silane coupling agent (E) is too small, the blending effect tends not to be obtained. If the content is too large, the compatibility with the acrylic resin (A) is deteriorated and adhesive strength and cohesive strength are obtained. There is a tendency to disappear.

  Examples of the silane coupling agent (E) include an epoxy silane coupling agent, an acrylic silane coupling agent, a mercapto silane coupling agent, a hydroxyl group silane coupling agent, a carboxyl group silane coupling agent, and amino. Examples thereof include a base silane coupling agent, an amide group silane coupling agent, and an isocyanate group silane coupling agent. These may be used alone or in combination of two or more. Among these, an epoxy silane coupling agent and a mercapto silane coupling agent are preferably used, and the combined use of an epoxy silane coupling agent and a mercapto silane coupling agent also improves wet heat durability and has adhesive strength. It is preferable in that it does not rise too much.

  Specific examples of the epoxy-based silane coupling agent include, for example, γ-glycidoxypropyltrimethoxysilane, γ-glycidoxypropyltriethoxysilane, γ-glycidoxypropylmethyldiethoxysilane, and γ-glycid. Examples include xylpropylmethyldimethoxysilane, methyltri (glycidyl) silane, β- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, β- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, and the like. -Glycidoxypropyltrimethoxysilane, [gamma] -glycidoxypropyltriethoxysilane, [gamma] -glycidoxypropylmethyldiethoxysilane, [beta]-(3,4-epoxycyclohexyl) ethyltrimethoxysilane.

  Specific examples of the mercapto silane coupling agent include γ-mercaptopropyltrimethoxysilane, γ-mercaptopropyltriethoxysilane, and γ-mercaptopropyldimethoxymethylsilane.

The resin composition [I] of the present invention preferably further contains an antistatic agent (F). As such an antistatic agent, conventionally known antistatic agents (compounds having an ionic group) can be used. For example, alkali metal salts, alkaline earth metal salts, quaternary ammonium salts, imidazolium salts, cyano group-containing salts , Aliphatic sulfonate, higher alcohol sulfate ester salt, higher alcohol alkylene oxide adduct sulfate ester salt, higher alcohol phosphate ester salt, higher alcohol alcohol alkylene oxide adduct phosphate ester salt, alkylbetaine compound, alkylimidazoline compound, An alkylalanine compound, a polyvinyl benzyl type cation compound, a polyacrylic acid type cation compound, or the like can be used.
Among these, alkali metal salts, alkaline earth metal salts, quaternary ammonium salts, imidazolium salts, and cyano group-containing salts are preferably used, and alkali metal salts and imidazolium salts are particularly preferably used.

Examples of the alkali metal salt include a cation selected from Li ⁺ , Na ⁺ and K ⁺ and Cl ⁻ , Br ⁻ , I ⁻ , BF ₄ ⁻ , PF ₆ ⁻ , SCN ⁻ , ClO ₄ ⁻ and CF ₃ SO _{3. ^{-, (CF 3 sO 2)}} 2 N -, (CF 3 sO 2) 3 C - metal salt composed of anions selected from is suitably used. Among these, lithium salts are preferable in that they have excellent ion conductivity and excellent antistatic function. Specifically, LiBr, LiI, LiBF ₄ , LiPF ₆ , LiSCN, LiClO ₄ , LiCF ₃ SO ₃ , Li (CF ₃ Lithium salts such as SO ₂ ) ₂ N and Li (CF ₃ SO ₂ ) ₃ C are preferably used, and LiCF ₃ SO ₃ , Li (CF ₃ SO ₂ ) ₂ N, LiI, and LiClO ₄ are particularly preferably used, and LiCF ₃ SO ₃ and Li (CF ₃ SO ₂ ) ₂ N are more preferably used, and LiCF ₃ SO ₃ is particularly preferably used. Moreover, you may use this alkali metal salt, making it dissolve in polyether polyol.

  Examples of the alkaline earth metal salts include calcium salts, magnesium salts, and halides thereof.

  Preferred examples of the quaternary ammonium salt include tetraalkylammonium salts such as alkyltrimethylammonium salts and dialkyldimethylammonium salts, trialkylbenzylammonium salts, alkylpyridinium salts, and (poly) oxyalkylene trialkylammonium salts.

  Examples of the imidazolium salt include imidazolium salts having an alkyl imidazolium cation such as a monoalkyl imidazolium cation, a dialkyl imidazolium cation, and a trialkyl imidazolium cation. Specifically, 1,3-dimethyl Imidazolium cation, 1,3-diethylimidazolium cation, 1-ethyl-3-methylimidazolium cation, 1-butyl-3-methylimidazolium cation, 1-hexyl-3-methylimidazolium cation, 1-octyl -3-methylimidazolium cation, 1-decyl-3-methylimidazolium cation, 1-dodecyl-3-methylimidazolium cation, 1-tetradecyl-3-methylimidazolium cation, 1,2-dimethyl-3-propiyl An imidazolium salt having an imidazolium cation, 1-ethyl-2,3-dimethylimidazolium cation, 1-butyl-2,3-dimethylimidazolium cation, 1-hexyl-2,3-dimethylimidazolium cation, etc. Can be mentioned.

  As the cyano group-containing salt, an ionic compound having a known general cyano group-containing anion can be used. In particular, an ionic compound having a cyano group-containing anion represented by the following general formula (2) is used. Is preferred.

（式中、Ｘは、ホウ素、炭素、窒素、アルミニウム、ケイ素、リン、砒素及びセレンからなる群より選ばれるいずれか１種の元素を表す。Ｙは、水素原子、アルキル基、またはトリフルオロメチル基を表す。Ｌ₁およびＬ₂ は、同一または異なっていてもよい有機連結基を表す。ａは、１以上の整数であり、ｂ、ｃ及びｄは、０以上の整数である。）

(In the formula, X represents any one element selected from the group consisting of boron, carbon, nitrogen, aluminum, silicon, phosphorus, arsenic, and selenium. Y represents a hydrogen atom, an alkyl group, or trifluoromethyl. L ₁ and L ₂ represent the same or different organic linking groups, a is an integer of 1 or more, and b, c, and d are integers of 0 or more.

  X in the general formula (2) is at least one element selected from the group consisting of boron, carbon, nitrogen, sulfur, aluminum, silicon, phosphorus, arsenic, and selenium. Among these, boron, carbon, nitrogen Sulfur is preferred.

  Y in the general formula (2) represents a hydrogen atom, an alkyl group, or a trifluoromethyl group, and the alkyl group preferably has 1 to 10 carbon atoms, more preferably 1 to 4 carbon atoms. Yes, specific examples of the alkyl group include a methyl group and an ethyl group. Y is preferably a hydrogen atom, a methyl group, or a trifluoromethyl group.

L ₁ and L ₂ in the general formula (2) is an organic linking group, preferably -S -, - O -, - SO 2 -, - a CO-, especially -SO ₂ -, - CO -Is preferred. Such L ₁ and L ₂ may be the same or different.

  In the general formula (2), a is an integer of 1 or more, and b, c, and d are integers of 0 or more, but since the valence of the anion is −1, when the valence of the element X is x , X−1 = (a + d) so that the values of a and c are determined.

Specific examples of the cyano group-containing anion represented by the general formula (2) include S ⁻ (CN), N ⁻ (CN) ₂ , N ⁻ (—SO ₂ —CN) ₂ , C ⁻ (CN) ₃ , B ^- (CN) ₄ and the like. among ^{them, S - (CN), N} - (CN) 2 are preferably used.

  Moreover, as molecular weight of a cyano group containing anion, it is 30-300 normally, Preferably it is 50-250.

The cation component of the cyano group-containing ionic compound is not particularly limited, and examples thereof include metal cations such as alkali metals, alkaline earth metals, transition metals, rare earth metals, and cations of heterocyclic compounds. And quaternary ammonium cations, quaternary phosphonium cations, and the like. Among these, it is preferable to use a cation of a heterocyclic compound and a quaternary ammonium cation.
Further, as the cation of the heterocyclic compound, a cation of a 1-6 membered heterocyclic compound containing 1 to 5 heteroatoms is preferable, and in particular, 1 to 5 containing a nitrogen atom as a heteroatom. Cations of 1- to 5-membered heterocyclic compounds containing 1 heteroatom are preferred, especially imidazolium salts.

  Specific examples of the ionic compound having a cyano group-containing anion represented by the general formula (2) include 1,3-dimethylimidazolium dicyanamide, 1-ethyl-3-methylimidazolium dicyanamide, 1 -Methyl-3-propylimidazolium dicyanamide, 1-butyl-3-methylimidazolium dicyanamide, 1-methyl-3-pentylimidazolium dicyanamide, 1-hexyl-3-methylimidazolium dicyanamide 1-heptyl-3-methylimidazolium dicyanamide, 1-methyl-3-octylimidazolium dicyanamide, 1-decyl-3-methylimidazolium dicyanamide, 1-dodecyl-3-methylimidazolium di Cyanamide, 1-ethyl-3-propylimidazolium dicyanamide Dialkylimidazolium dicyanamide such as 1-butyl-3-ethylimidazolium dicyanamide, 3-ethyl-1,2-dimethyl-imidazolium dicyanamide, 1,2-dimethyl-3-propylimidazolium dicyanamide Amide, 1-butyl-2,3-dimethylimidazolium dicyanamide, 1,2-dimethyl-3-hexylimidazolium dicyanamide, 1,2-dimethyl-3-octylimidazolium dicyanamide, 1-ethyl -3,4-dimethylimidazolium dicyanamide, trialkylimidazolium dicyanamide such as 1-isopropyl-2,3-dimethylimidazolium dicyanamide, 1,3-dimethylimidazolium thiocyanate, 1-ethyl-3 -Methylimidazolium thiocyanate, 1-methyl -3-propylimidazolium thiocyanate, 1-butyl-3-methylimidazolium thiocyanate, 1-methyl-3-pentylimidazolium thiocyanate, 1-hexyl-3-methylimidazolium thiocyanate, 1-heptyl-3-methylimidazolium Thiocyanate, 1-methyl-3-octylimidazolium thiocyanate, 1-decyl-3-methylimidazolium thiocyanate, 1-dodecyl-3-methylimidazolium thiocyanate, 1-ethyl-3-propylimidazolium thiocyanate, 1-butyl- Dialkyl imidazolium thiocyanate such as 3-ethyl imidazolium thiocyanate, 3-ethyl-1,2-dimethyl-imidazolium thiocyanate, 1,2-dimethyl-3-propyl imidazoli Umthiocyanate, 1-butyl-2,3-dimethylimidazolium thiocyanate, 1,2-dimethyl-3-hexylimidazolium thiocyanate, 1,2-dimethyl-3-octylimidazolium thiocyanate, 1-ethyl-3,4- Examples thereof include trialkylimidazolium thiocyanates such as dimethylimidazolium thiocyanate and 1-isopropyl-2,3-dimethylimidazolium thiocyanate.

  Among these, the use of a solid imidazolium salt is preferable because it can be easily recrystallized by purification, and thus it is easy to prepare a high-purity ionic compound, and 1-ethyl-2,3-dimethylimidazolium disulfide is particularly preferable. Cyanamide and 1-ethyl-2,3 dimethylimidazolium thiocyanate are used because they are easy to prepare high-purity ionic compounds.

    As the antistatic agent (F), it is also preferable to use a so-called ionic liquid among ionic compounds. The ionic liquid in this invention represents the ionic substance which consists of a cation component and an anion component which hold | maintain a liquid at the fixed temperature of the range of 0-100 degreeC.

  The cation component is not particularly limited, and a cation used in a general ionic liquid is used. Examples of such cations include, for example, cations of heterocyclic compounds, particularly cations of 1 to 5 membered heterocyclic compounds containing 1 to 5 heteroatoms, particularly nitrogen atoms as heteroatoms. Examples thereof include cations of 1 to 5 membered heterocyclic compounds containing 1 to 5 heteroatoms, and among them, imidazolium cation, pyrrolidinium cation, piperidinium cation, pyridinium cation and the like are preferable. It is also preferable to use a chain-like quaternary ammonium cation or quaternary phosphonium cation. Among these, imidazolium cation, pyridinium cation, quaternary ammonium cation, and quaternary phosphonium cation are preferable, and imidazolium cation is particularly preferable in terms of low viscosity.

On the other hand, the anion component is not particularly limited. For example, Cl ⁻ , Br ⁻ , AlCl ₄ ⁻ , Al ₂ Cl ₇ ⁻ , BF ₄ ⁻ , PF ₆ ⁻ , ClO ₄ ⁻ , NO ₃ ⁻ , _{^{CH 3 COO -, CF 3 COO}} -, CH 3 SO 3 - CF 3 SO 3 -, (CF 3 SO 2) 2 N -, (CF 3 SO 2) 3 C -, AsF 6 -, SbF 6 -, NbF ₆ ⁻ , TaF ₆ ⁻ , F (HF) n ⁻ , (CN) ₂ N ⁻ , SCN ⁻ , C ₄ F ₉ SO ₃ ⁻ , (C ₂ F ₅ SO ₂ ) ₂ N ⁻ , C ₃ F ₇ COO ⁻ , (CF ₃ SO ₂ ) (CF ₃ CO) N- ^{and the} like can be used with anions used in general ionic liquids.

  The content of the antistatic agent (F) is usually set to 0.001 to 20 parts by weight, more preferably 0.01 to 10 parts by weight, with respect to 100 parts by weight of the acrylic resin (A). Particularly preferred is 0.02 to 5 parts by weight. If the content of the antistatic agent (F) is too small, there is a tendency that the blending effect cannot be obtained. If the content is too large, the durability may deteriorate or the antistatic agent may bleed out.

In the present invention, the resin composition [I], which is a pressure-sensitive adhesive-forming material, further includes other acrylic pressure-sensitive adhesives, other pressure-sensitive adhesives, urethane resins, rosins, and rosin esters as long as the effects of the present invention are not impaired. , Hydrogenated rosin esters, phenolic resins, aromatic modified terpene resins, aliphatic petroleum resins, alicyclic petroleum resins, styrene resins, xylene resins, polyols and other tackifiers, colorants, fillers, aging Conventionally known additives such as inhibitors, ultraviolet absorbers and functional dyes, and compounds that cause coloration or discoloration upon irradiation with ultraviolet rays or radiation can be blended.
In addition to the above additives, a small amount of impurities contained in the raw materials for producing the constituent components of the resin composition [I] may be contained.

Thus, in the present invention, an adhesive for optical members obtained by crosslinking the above resin composition [I] is obtained. By providing such an adhesive on the optical member (optical laminate), the adhesive is provided. A layered optical member can be obtained.
The optical member with the pressure-sensitive adhesive layer is preferably further provided with a release sheet on the surface opposite to the optical member of the pressure-sensitive adhesive layer.

The method for producing the optical member with the pressure-sensitive adhesive layer is not particularly limited. (1) A method of further bonding a release sheet after applying and drying the resin composition [I] on the optical member. Or (2) The resin composition [I] is applied on the release sheet, dried, and then manufactured by a method of laminating the optical member. The resin composition on the release sheet of (2) The production method of applying [I] is preferable in that the possibility that the substrate is deteriorated by the diluting solvent is low.
In practical use, the release sheet is peeled off and used, and the release sheet is preferably a silicon-based release sheet.

  Further, when the resin composition [I] is crosslinked by at least one of active energy ray irradiation and heating, [1] the resin composition [I] is coated on the optical member, dried, and then released. A method of pasting sheets and performing treatment by at least one of active energy ray irradiation and heating, [2] On the release sheet, after applying and drying the resin composition [I], the optical members are pasted, Method of performing treatment by at least one of active energy ray irradiation and heating, [3] After applying and drying resin composition [I] on the optical member, and further performing treatment by at least one of active energy ray irradiation and heating , A method of laminating a release sheet, [4] coating and drying the resin composition [I] on the release sheet, and further performing a treatment with at least one of irradiation with active energy rays and heating After, it possible to produce a method by which bonding an optical member. Among these, the method [2] and only the active energy ray irradiation are preferable from the viewpoint of not damaging the substrate, workability and stable production.

  In the above application, it is preferably applied after diluting with a solvent, and the dilution concentration is preferably 10 to 50% by weight, particularly preferably 11 to 25% by weight. Such a solvent is not particularly limited as long as it dissolves the resin composition [I]. For example, ester solvents such as methyl acetate, ethyl acetate, methyl acetoacetate, and ethyl acetoacetate, acetone, methyl ethyl ketone, A ketone solvent such as methyl isobutyl ketone and an aromatic solvent such as toluene and xylene can be used. Among these, ethyl acetate and methyl ethyl ketone are preferably used from the viewpoints of solubility, drying property, price, and the like.

  The gel fraction of the pressure-sensitive adhesive layer produced by the above method is preferably 80% or more from the viewpoint of durability performance and light leakage prevention performance, and particularly preferably 90% or more. If the gel fraction is too low, the durability and light leakage phenomenon due to insufficient cohesive force tend to be deteriorated. The upper limit of the normal gel fraction is 100%.

  In adjusting the gel fraction of the optical member pressure-sensitive adhesive to the above range, for example, adjusting the irradiation amount and irradiation intensity of the active energy ray, adjusting the type and amount of the unsaturated group-containing compound, This is achieved by adjusting the type of polymerization initiator and the combination ratio thereof, adjusting the blending amount of the polymerization initiator, adjusting the type and amount of the crosslinking agent, and the like. Moreover, since the gel fraction changes by each interaction, the irradiation amount and irradiation intensity | strength of the said active energy ray, the composition ratio of a polymerization initiator, and a compounding quantity need to balance each.

In addition, the said gel fraction becomes a standard of a crosslinking degree, and is computed with the following method.
That is, an adhesive sheet (not provided with a separator) obtained as described below is wrapped in a 200 mesh SUS wire mesh, immersed in toluene at 23 ° C. for 24 hours, and the insoluble adhesive component remaining in the wire mesh The weight percentage is taken as the gel fraction. However, the weight of the substrate is subtracted.

  Moreover, the thickness of the pressure-sensitive adhesive layer in the obtained optical member with the pressure-sensitive adhesive layer is not particularly limited, but is preferably 5 to 300 μm, particularly preferably 10 to 50 μm, and more preferably 12 to 30 μm. If the thickness of the pressure-sensitive adhesive layer is too thin, the adhesive physical properties tend to be difficult to stabilize, and if it is too thick, the thickness of the entire optical part tends to increase too much.

  The optical member with the pressure-sensitive adhesive layer obtained in the present invention is directly or has a release sheet, and after peeling off the release sheet, the surface of the pressure-sensitive adhesive layer is bonded to a glass substrate and used for, for example, a liquid crystal display board. It is.

  The initial adhesive strength of the pressure-sensitive adhesive layer of the present invention is appropriately determined according to the material of the adherend. For example, when sticking to a non-alkali glass plate, it is preferable to have an adhesive strength of 0.01 N / 25 mm to 50 N / 25 mm. Even in the case of permanent bonding, if static electricity is generated during rework (re-sticking), dust is trapped, and thus antistatic properties are required.

  The initial adhesive strength is calculated as follows. About the prepared optical member with an adhesive layer, it cut | judged to width 25mm width, peels a release film, presses the adhesive layer side to a non-alkali glass board (Corning company make, "Corning 1737"), optical The member and the glass plate were bonded together. Then, an autoclave process (50 degreeC, 0.5 Mpa, 20 minutes) is performed, and a 180 degreeC peeling test is done 24 hours later.

  The optical member in the present invention is not particularly limited, and an optical film suitably used for an image display device such as a liquid crystal display device, an organic EL display device, or a PDP, such as a polarizing plate, a retardation plate, or an elliptical polarizing plate. , An optical compensation film, a brightness enhancement film, and those in which these are laminated, and the like. Among them, a polarizing plate is particularly effective in the present invention.

  The polarizing plate used in the present invention is usually obtained by laminating a cellulose triacetate film as a protective film on both sides of a polarizing film, and the polarizing film has an average polymerization degree of 1,500 to 10,000, saponification. A uniaxially stretched film dyed with an aqueous solution of iodine-potassium iodide or a dichroic dye (2 to 10 times, preferably 3 A draw ratio of about 7 times) is used.

  Polyvinyl alcohol resins are usually produced by saponifying polyvinyl acetate obtained by polymerizing vinyl acetate, but small amounts of unsaturated carboxylic acids (including salts, esters, amides, nitriles, etc.), olefins, vinyl ethers, A component copolymerizable with vinyl acetate, such as a saturated sulfonate, may be contained. Moreover, what is called polyvinyl acetal resin and polyvinyl alcohol derivatives, such as polybutyral resin, polyvinyl formal resin, etc. which reacted polyvinyl alcohol with aldehydes in presence of an acid is mentioned.

EXAMPLES Hereinafter, although an Example is given and this invention is demonstrated further more concretely, this invention is not limited to a following example, unless the summary is exceeded.
In the examples, “parts” and “%” mean weight basis unless otherwise specified.

[Preparation of hydroxyl group-containing acrylic resin (A)] (See Table 1)

[Acrylic resin (A-1)]
A 4-neck round bottom flask equipped with a reflux condenser, stirrer, nitrogen gas inlet and thermometer was charged with 100 parts of ethyl acetate, and 0.05 parts of azobisisobutyronitrile (AIBN) as a polymerization initiator. The mixture was heated while stirring, and a mixture of 20 parts of 2-hydroxyethyl acrylate (a1), 79 parts of butyl acrylate (a2) and 1 part of acrylic acid (a3) was added dropwise at reflux temperature over 2 hours. During polymerization, while sequentially adding a polymerization initiator solution in which 0.05 part of AIBN was dissolved in 10 parts of ethyl acetate, the mixture was polymerized at the ethyl acetate reflux temperature for 3.5 hours, and then diluted with an acrylic resin (A-1 ) Solution (weight average molecular weight (Mw) 870,000, dispersity (Mw / Mn) 4.9, glass transition temperature -47 ° C., solid content 35%, viscosity 7,000 mPa · s (25 ° C.)).

[Acrylic resin (A-2)]
A 4-neck round bottom flask equipped with a reflux condenser, stirrer, nitrogen gas inlet and thermometer was charged with 100 parts of ethyl acetate, and 0.05 parts of azobisisobutyronitrile (AIBN) as a polymerization initiator. The mixture was heated while stirring, and a mixture of 30 parts of 2-hydroxyethyl acrylate (a1), 69 parts of butyl acrylate (a2) and 1 part of acrylic acid (a3) was added dropwise at reflux temperature over 2 hours. In the course of polymerization, a polymerization initiator solution in which 0.05 part of AIBN was dissolved in 10 parts of ethyl acetate was sequentially added, and the mixture was polymerized at the ethyl acetate reflux temperature for 3.5 hours, and then diluted with an acrylic resin (A-2 ) Solution (weight average molecular weight (Mw) 850,000, dispersity (Mw / Mn) 4.5, glass transition temperature -43 ° C., solid content 35%, viscosity 7,000 mPa · s (25 ° C.)).

[Acrylic resin (A-3)]
A 4-neck round bottom flask equipped with a reflux condenser, stirrer, nitrogen gas inlet and thermometer was charged with 120 parts of ethyl acetate, and 0.05 parts of azobisisobutyronitrile (AIBN) as a polymerization initiator. The mixture was heated with stirring, and a mixture of 50 parts of 2-hydroxyethyl acrylate (a1), 49 parts of butyl acrylate (a2) and 1 part of acrylic acid (a3) was added dropwise at reflux temperature over 2 hours. In the course of polymerization, a polymerization initiator solution in which 0.05 part of AIBN was dissolved in 10 parts of ethyl acetate was successively added, and the mixture was polymerized at the ethyl acetate reflux temperature for 3.5 hours, and then diluted with an acrylic resin (A-3 ) Solution (weight average molecular weight (Mw) 760,000, dispersity (Mw / Mn) 4.4, glass transition temperature -35 ° C., solid content 27%, viscosity 3,000 mPa · s (25 ° C.)).

[Acrylic resin (A-4)]
A 4-neck round bottom flask equipped with a reflux condenser, stirrer, nitrogen gas inlet and thermometer was charged with 100 parts of ethyl acetate, and 0.05 parts of azobisisobutyronitrile (AIBN) as a polymerization initiator. The mixture was heated while stirring, and at reflux temperature, 30 parts of 2-hydroxyethyl acrylate (a1), 30 parts of 2-methoxyethyl acrylate (a2), 39 parts of butyl acrylate (a2), acrylic acid (a3) 1 Part of the mixture was added dropwise over 2 hours. In the course of polymerization, a polymerization initiator solution in which 0.05 part of AIBN was dissolved in 10 parts of ethyl acetate was successively added, and the mixture was polymerized at the ethyl acetate reflux temperature for 3.5 hours, and then diluted with an acrylic resin (A-4 ) Solution (weight average molecular weight (Mw) 980,000, dispersity (Mw / Mn) 4.3, glass transition temperature -42 ° C., solid content 32%, viscosity 7,000 mPa · s (25 ° C.)).

[Acrylic resin (A-5)]
A 4-neck round bottom flask equipped with a reflux condenser, stirrer, nitrogen gas inlet and thermometer was charged with 100 parts of ethyl acetate, and 0.05 parts of azobisisobutyronitrile (AIBN) as a polymerization initiator. The mixture was heated while stirring, and a mixture of 30 parts of 2-hydroxyethyl acrylate (a1) and 70 parts of butyl acrylate (a2) was added dropwise at reflux temperature over 2 hours. In the middle of the polymerization, while sequentially adding a polymerization initiator solution in which 0.05 part of AIBN was dissolved in 10 parts of ethyl acetate, the mixture was polymerized for 3.5 hours at the reflux temperature of ethyl acetate, and then diluted with an acrylic resin (A-5 ) Solution (weight average molecular weight (Mw) 850,000, dispersity (Mw / Mn) 4.4, glass transition temperature -43 ° C., solid content 35%, viscosity 5,500 mPa · s (25 ° C.)).

[Acrylic resin (A-6)]
A 4-neck round bottom flask equipped with a reflux condenser, stirrer, nitrogen gas inlet and thermometer was charged with 100 parts of ethyl acetate, and 0.05 parts of azobisisobutyronitrile (AIBN) as a polymerization initiator. The mixture was heated while stirring, and a mixture of 30 parts of 4-hydroxybutyl acrylate (a1), 69 parts of butyl acrylate (a2) and 1 part of acrylic acid (a3) was added dropwise at reflux temperature over 2 hours. During polymerization, while sequentially adding a polymerization initiator solution in which 0.05 part of AIBN was dissolved in 10 parts of ethyl acetate, polymerization was performed at the ethyl acetate reflux temperature for 3.5 hours, and then diluted with an acrylic resin (A-6 ) Solution (weight average molecular weight (Mw) 680,000, dispersity (Mw / Mn) 4.9, glass transition temperature -44 ° C., solid content 29%, viscosity 1,900 mPa · s (25 ° C.)).

[Acrylic resin (A-7)]
A 4-neck round bottom flask equipped with a reflux condenser, stirrer, nitrogen gas inlet and thermometer was charged with 70 parts of ethyl acetate, and 0.05 parts of azobisisobutyronitrile (AIBN) as a polymerization initiator. The mixture was heated while stirring, and a mixture of 30 parts of 2-hydroxyethyl acrylate (a1), 69 parts of 2-ethylhexyl acrylate (a2) and 1 part of acrylic acid (a3) was added dropwise over 2 hours at the reflux temperature. . During polymerization, while sequentially adding a polymerization initiator solution in which 0.05 part of AIBN was dissolved in 10 parts of ethyl acetate, the mixture was polymerized at the ethyl acetate reflux temperature for 3.5 hours and then diluted with an acrylic resin (A-7 ) Solution (weight average molecular weight (Mw) 940,000, dispersity (Mw / Mn) 5.4, glass transition temperature -56 ° C., solid content 28%, viscosity 9,200 mPa · s (25 ° C.)).

[Acrylic resin (A-8)]
In a 4-neck round bottom flask equipped with a reflux condenser, a stirrer, a nitrogen gas inlet and a thermometer, 1.5 parts of 2-hydroxyethyl acrylate (a1), 98 parts of butyl acrylate (a2), acrylic acid ( a3) 0.5 parts, 75 parts of ethyl acetate and 45 parts of acetone were added, and after heating to reflux, 0.03 part of azobisisobutyronitrile (AIBN) was added as a polymerization initiator, and the mixture was refluxed at ethyl acetate for 3 hours. After the reaction, the mixture was diluted with ethyl acetate, and the acrylic resin (A-8) solution (weight average molecular weight (Mw) 2 million, dispersity (Mw / Mn) 3.1, glass transition temperature -54 ° C., solid content 16 %, Viscosity 8,000 mPa · s (25 ° C.)).

[Acrylic resin (A-9)]
In a 4-neck round bottom flask equipped with a reflux condenser, a stirrer, a nitrogen gas inlet and a thermometer, 12 parts of 2-hydroxyethyl acrylate (a1), 87.5 parts of butyl acrylate (a2), acrylic acid ( a3) 0.5 part, 100 parts of ethyl acetate and 45 parts of acetone were added, and after heating to reflux, 0.03 part of azobisisobutyronitrile (AIBN) was added as a polymerization initiator, and the mixture was refluxed at ethyl acetate for 3 hours. After the reaction, the reaction mixture was diluted with 100 parts of ethyl acetate and 100 parts of toluene, and further reacted at 80 ° C. for 3 hours. Then, it is diluted with ethyl acetate, and an acrylic resin (A-9) solution (weight average molecular weight (Mw) 1.35 million, dispersity (Mw / Mn) 11, glass transition temperature −50 ° C., solid content 20%, viscosity. 4800 mPa · s (25 ° C.)) was obtained.

（注）ＢＡ：ブチルアクリレート
２ＥＨＡ：２−エチルヘキシルアクリレート
２ＨＥＡ：２−ヒドロキシエチルアクリレート
４ＨＢＡ：４−ヒドロキシブチルアクリレート
ＭＥＡ：２−メトキシエチルアクリレート
ＡＡｃ：アクリル酸

(Note) BA: butyl acrylate 2EHA: 2-ethylhexyl acrylate 2HEA: 2-hydroxyethyl acrylate 4HBA: 4-hydroxybutyl acrylate MEA: 2-methoxyethyl acrylate AAc: acrylic acid

[Production of unsaturated group-containing compound (B-1)]
In a 4-neck round bottom flask equipped with a reflux condenser, a stirrer, a nitrogen gas inlet and a thermometer, 19.2 parts of isophorone diisocyanate, 0.05 part of di-t-butylhydroxyphenol, 0.02 of dibutyltin dilaurate The reaction was continued at 70 ° C. at a temperature of 50 ° C. or less and 80.8 parts of a mixture of pentaerythritol triacrylate and pentaerythritol tetraacrylate (Kyoeisha Chemical Co., Ltd., light acrylate PE-3A, hydroxyl value 120 mg KOH / g). Then, an unsaturated group-containing compound (B-1) was obtained.

[Photopolymerization initiator (C-1)]
The following were prepared as the photopolymerization initiator (C-1).
A mixture of benzophenone and 1-hydroxycyclohexyl phenyl ketone in a mass ratio of 1: 1 (Ciba Specialty Chemicals, “Irgacure 500”)

[Crosslinking agent (D-1)]
The following were prepared as a crosslinking agent (D-1).
-55% ethyl acetate solution of trimethylolpropane tolylene diisocyanate adduct (manufactured by Nippon Polyurethane Co., Ltd., "Coronate L-55E")

[Silane compound (E-1)]
The following were prepared as the silane compound (E-1).
γ-glycidoxypropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., “KBM403”)

[Antistatic agent (F)]
The following were prepared as the antistatic agent (F-1).
1-ethyl-2,3-dimethylimidazolium dicyanamide The following were prepared as an antistatic agent (F-2).
-1-ethyl-3-methylimidazolium bis (trifluoromethylsulfonyl) imide antistatic agent (F-3) was prepared as follows.
・ Lithium perchlorate (Nippon Carlit)
The following were prepared as an antistatic agent (F-4).
Trifluoromethanesulfonyl lithium (LiCF ₃ SO ₃ ) (Sankonol EAc-30T manufactured by Sanko Chemical)

Examples 1 to 7, Comparative Examples 1 and 2
In the obtained acrylic resins (A-1 to A-9), 2.5 parts of the crosslinking agent (D-1) is blended with 100 parts of the acrylic resin, and the viscosity (which can be applied with ethyl acetate) A resin composition diluted to 1000-5000 mPa · s / 25 ° C.) was prepared. The resin composition was applied to a polyester release sheet so that the thickness after drying was 25 μm, dried at 90 ° C. for 3 minutes, and then the resin composition layer side was placed on a polyethylene terephthalate film (thickness 38 μm). Transferred, 23 ° C., 65% R.D. H. The sample with an adhesive was obtained by aging under the conditions of 14 days.

(Surface resistivity)
After the obtained sample with adhesive was cut into 40 × 40 mm, the sample was conditioned at 23 ° C. and 65% RH for 3 hours, and then the release sheet was peeled off, and the adhesive layer after 10 to 20 seconds was manufactured by Mitsubishi Chemical Corporation The surface resistivity was measured using a resistivity meter “High Lester UP”. In addition, it means that antistatic ability is so good that the value of surface resistance is small.

  Acrylic resin containing only 1.5 or 12% by weight of a hydroxyl group-containing monomer (A) compared to the surface resistance of an adhesive using an acrylic resin (A-1 to 7) containing at least 15% by weight of a hydroxyl group-containing monomer The surface resistivity of the adhesive using -8) or (A-9) is a large value, and the antistatic performance of the adhesive using acrylic resin (A-8) or (A-9) is high. It turns out that it is inferior.

Example 8
A composition [I] solution (diluted to a viscosity (1000-10000 mPa · s / 25 ° C.) with ethyl acetate) was prepared with the composition shown in Table 3. The obtained composition [I] solution was applied to a polyester release sheet so that the thickness after drying was 25 μm, dried at 90 ° C. for 3 minutes, and then the composition [I] layer side was coated with a polarizing plate. The film was transferred onto (thickness 190 μm), and irradiated with ultraviolet light at a peak illuminance of 600 mW / cm ² and an integrated exposure amount of 240 mJ / cm ² with an electrodeless lamp [H bulb of LH6UV lamp] manufactured by Fusion, at 23 ° C. and 65 % R. H. The film was aged for 14 days to obtain a polarizing plate with an adhesive layer.

  The polarizing plate was laminated with a cellulose triacetate film having a thickness of 80 μm on both sides of a 30 μm-thick polyvinyl alcohol polarizing film (average polymerization degree 1700, average saponification degree 99 mol%, iodine staining, 4-fold stretching). A polarizing plate (inclined in the direction of the stretching axis of the polyvinyl alcohol polarizing film by 45 degrees and cut into 100 mm × 100 mm) was used.

Examples 9-13 and Comparative Examples 3 and 4
The same operation as in Example 8 was performed with the blending composition shown in Table 3 to obtain a polarizing plate with an adhesive layer.

  Further, in the same manner as described above, a gel for measuring the gel fraction and the surface resistance was obtained using a polyethylene terephthalate film (thickness 38 μm) instead of the polarizing plate.

(Gel fraction)
After cutting the obtained sample to 40 × 40 mm, the release sheet is peeled off and the pressure-sensitive adhesive layer side is bonded to a 50 × 100 mm SUS mesh sheet (200 mesh), and then to the longitudinal direction of the SUS mesh sheet. After wrapping the sample from the center and wrapping the sample, the gel fraction (%) was measured by weight change when immersed in a sealed container containing 250 g of toluene.

(durability)
The release sheet of the obtained polarizing plate with the pressure-sensitive adhesive layer was peeled off, and the pressure-sensitive adhesive layer side was pressed against a non-alkali glass plate (Corning 1737, manufactured by Corning) to bond the polarizing plate and the glass plate. Thereafter, autoclaving (50 ° C., 0.5 MPa, 20 minutes) was performed, and thereafter, foaming, peeling, and light leakage phenomenon were evaluated in the following durability tests (heat resistance test, moist heat resistance test, heat cycle test). The evaluation criteria are as follows. The evaluation results are shown in Table 4.

For the heat resistance test only, the same sample was bonded to both the front and back surfaces so that the polarizing plate was crossed Nicol, and was used for light leakage observation.

The test piece size used is 10cm x 10cm in the heat and moisture resistance heat cycle,
A 20 cm × 15 cm test was used in the heat resistance test.

〔An endurance test〕
(1) Heat resistance test 80 ° C., 100 hour durability test (2) Moist heat resistance test 60 ° C., 90% RH, 100 hour durability test (3) Heat cycle test After standing at −40 ° C. for 30 minutes, at 85 ° C. Endurance test for 100 cycles, with 30 minutes of operation as one cycle

〔Evaluation criteria〕
(Foam)
○ ... No foaming △ ... Slight foaming is observed × ... Many foaming is observed (peeling)
○ ・ ・ ・ No peeling or peeling less than 0.5mm, or generation of ukiato △ ・ ・ ・ Peeling less than 1mm or generation of ukiato × ・ ・ ・ Peeling of 1mm or more, or generation of ukiato (light leakage)
○ ・ ・ ・ No or almost no light leakage △ ・ ・ ・ Slight leakage occurred × ・ ・ ・ Large light leakage on 4 sides

〔Adhesive force〕
About the prepared polarizing plate with an adhesive layer, it cuts to width 25mm width, peels off a release film, presses the adhesive layer side to a non-alkali glass board (Corning company make, "Corning 1737"), and polarized light The plate and the glass plate were bonded together. Thereafter, autoclaving (50 ° C., 0.5
MPa, 20 minutes), and a 180 ° C. peel test was conducted 24 hours later. In the peelability, it is desired that the adhesive strength is small, and the target is 10 N / 25 mm or less after one day.

※湿熱試験で剥離が生じたため発泡については評価しなかった

* Foaming was not evaluated because peeling occurred in the wet heat test.

From the above results, in Examples 8 and 9 and Comparative Example 3 in which no antistatic agent (F) was blended, Comparative Example 3 using an acrylic resin (A-9) with a small content of hydroxyl group-containing monomer was used. It can be seen that the adhesives of Examples 8 and 9 have higher antistatic performance than the adhesive.
Further, when focusing attention on Examples 10 to 13 and Comparative Example 4 in which the antistatic agent (F) was blended, the antistatic agent was blended so that the antistatic performance of both the pressure-sensitive adhesives was lower than that in the case of not blending both. Although improvement is observed, Examples 10 to 13 using the acrylic resin (A-2) containing 30 parts by weight of the OH group-containing monomer have better antistatic performance than Comparative Example 4. .
In addition, the acrylic resin (A) using a large amount of the hydroxyl group-containing monomer is excellent in antistatic performance, and further has excellent durability as a pressure-sensitive adhesive for optical members from the results shown in Table 4. I understand that.

  The pressure-sensitive adhesive for optical members of the present invention is less likely to be charged with static electricity generated in each step, and has excellent adhesion between the optical laminate and the glass substrate even under high temperature and high humidity conditions. Since foaming and peeling do not occur between the glass substrate and the light leakage phenomenon caused by the contraction of the optical film can be suppressed, a liquid crystal display panel with excellent durability can be obtained, which is very useful. is there.

Claims (8)

  A pressure-sensitive adhesive for optical members, wherein the resin composition [I] containing as a main component an acrylic resin (A) obtained by polymerizing a polymerization component containing 15% by weight or more of a hydroxyl group-containing monomer is crosslinked. .   2. The optical member according to claim 1, wherein the resin composition [I] contains an unsaturated group-containing compound (B) and a polymerization initiator (C) and is crosslinked by active energy rays and / or heat. Adhesive.   The pressure-sensitive adhesive for optical members according to claim 1 or 2, wherein the resin composition [I] contains a crosslinking agent (D) and is crosslinked by the crosslinking agent.   Resin composition [I] contains a silane coupling agent (E) further, The adhesive for optical members in any one of Claims 1-3 characterized by the above-mentioned. The resin composition [I] further contains an antistatic agent (F).
4. The adhesive for optical members according to any one of 4 above.   The pressure-sensitive adhesive for optical members according to any one of claims 1 to 5, wherein the pressure-sensitive adhesive has a gel fraction of 80% or more.   The pressure-sensitive adhesive for optical members according to any one of claims 1 to 6, wherein the optical member is a polarizing plate.   It has an adhesive layer containing the adhesive for optical members in any one of Claims 1-7, The optical member with an adhesive layer characterized by the above-mentioned.