JP6781818B2 - Optical member with optical functional layer - Google Patents

Description

The present invention relates to an optical member with an optical functional layer. Further, the optical member with an optical functional layer of the present invention can be applied to an image display device such as a liquid crystal panel, a liquid crystal display device having the liquid crystal panel, or an organic EL display device.

In an image display device or the like, it is indispensable to arrange polarizing elements on both sides of a liquid crystal cell due to the image forming method, and generally, a polarizing film is attached. When the polarizing film is attached to the liquid crystal cell, an adhesive is usually used. Further, in order to reduce the loss of light, the polarizing film and the liquid crystal cell are usually adhered to each other by using an adhesive. In such a case, the pressure-sensitive adhesive has an advantage that a drying step is not required to fix the polarizing film. Therefore, the pressure-sensitive adhesive is polarized light with a pressure-sensitive adhesive layer previously provided as a pressure-sensitive adhesive layer on one side of the polarizing film. Films are commonly used.

Further, it has been proposed to give an arbitrary hue to a polarizing film by adding a dye or a pigment to the pressure-sensitive adhesive layer to obtain a high-contrast liquid crystal display (Patent Document 1). In recent years, image display devices are required to have brightness and vividness (that is, wide color gamut), and organic EL display devices (OLEDs) are attracting attention, but liquid crystal display devices are also widened in color gamut. Is required. For example, as a method for widening the color gamut of a liquid crystal display device, a polarizing film is applied to one or both sides of the liquid crystal cell via an adhesive layer containing a dye that exhibits a maximum absorption wavelength in a specific wavelength (560 to 610 nm) range. It has been proposed to stack (Patent Documents 2 and 3).

Jitsuto No. 3052812 specification Japanese Unexamined Patent Publication No. 2011-039093 Japanese Unexamined Patent Publication No. 2014-092611

As described above, the dye can be contained in the pressure-sensitive adhesive layer, and can also be contained in the film layer applied to the optical member. By incorporating the dye in a resin layer such as a film layer or an adhesive layer in this way, an optical functional layer containing the dye can be formed. However, since the optical functional layer contains a dye, the dye in the optical functional layer deteriorates with time from the viewpoint of moisture permeability of the resin layer that is the base of the optical functional layer, and the optical functional layer deteriorates with time. Gradually fades. In particular, when the optical functional layer is a pressure-sensitive adhesive layer containing a dye, the durability of the pressure-sensitive adhesive layer is not sufficient from the viewpoint of moisture permeability, and the pressure-sensitive adhesive layer initially colored by the dye is used. Even if there is, it will gradually fade. As described above, when the dye in the optical functional layer (particularly, the pressure-sensitive adhesive layer) deteriorates with time, it is difficult to maintain the wide color gamut by the dye.

An object of the present invention is to provide an optical functional layer containing a dye, which has good stability over time and can maintain a wide color gamut due to the dye.

As a result of diligent studies to solve the above problems, the present inventors have found the following optical member with an optical functional layer, and have completed the present invention.

That is, the present invention is an optical functional layer containing a dye, and an optical member with an optical functional layer having a first optical member and a second optical member on both sides of the optical functional layer.
At least the first optical member, an oxygen permeability of ^{1 [cm 3 / (m 2} · 24h · atm)] The optical member with an optical functional layer, characterized in that at most, about.

In the optical member with an optical functional layer, a separator can be used as the first optical member. Further, in the optical member with an optical functional layer, a member containing a polyvinyl alcohol-based polarizer can be used as the first optical member.

In the optically-attached optical functional layer, the second optical member is preferably oxygen permeability is less than ^{1 [cm 3 / (m 2} · 24h · atm)]. A separator can be used as the second optical member.

In the optical member with an optical functional layer, a dye having a maximum absorption wavelength in at least one of a wavelength range of 470 to 510 nm and a wavelength range of 570 to 610 nm can be used.

In the optical member with an optical functional layer, a porphyrin-based dye can be used as the dye.

In the optical member with an optical functional layer, it is preferable that the dye is contained in an amount of 0.01 to 5 parts by weight with respect to 100 parts by weight of the base polymer forming the resin layer of the optical functional layer.

The optical member with an optical functional layer of the present invention has an optical functional layer containing a dye. The optical functional layer can adjust the overall hue of the liquid crystal display device by absorbing light having a part of wavelengths by the dye, and can improve the vividness by widening the color gamut. In particular, a dye having a maximum absorption wavelength in at least one of 470 to 510 nm and 570 to 610 nm in the wavelength range is used for color expression in a wavelength range other than RGB (wavelength range 470 to 510 nm and / or wavelength range 570 to 610 nm). It is possible to absorb unnecessary light emission and suppress the unnecessary light emission, which is effective for widening the color range.

Further, the optical member with an optical functional layer of the present invention has optical members on both sides of the optical functional layer containing the dye. Even in such a configuration of an optical member with an optical functional layer having optical members on both sides of the optical functional layer, the dye in the optical functional layer has faded. It was found that the fading was caused by oxygen passing through the optical member, entering the optical functional layer, and being activated by heat to attack the dye. The optical member with an optical functional layer of the present invention, on at least one surface of the optical function layer containing a dye, oxygen permeability is ^{1 [cm 3 / (m 2} · 24h · atm)] or less of the optical member is laminated .. By using such an optical member having low oxygen transmittance, it is possible to prevent oxygen from entering the optical functional layer in the optical member with an optical functional layer, thereby suppressing fading (decomposition) of the dye and stabilizing it over time. The optical functional layer can be provided to maintain a wide color gamut.

It is sectional drawing which shows schematic outline of the optical member with an optical functional layer of this invention. It is sectional drawing which shows typically one Embodiment of the optical member with an optical functional layer of this invention. It is sectional drawing which shows typically one Embodiment of the optical member with an optical functional layer of this invention.

Hereinafter, embodiments of the optical member with an optical functional layer of the present invention will be described in detail with reference to the drawings. However, the present invention is not limited to the embodiments of the drawings.

As shown in FIG. 1, the optical member with an optical functional layer of the present invention has a dye-containing optical functional layer A and a first optical member B1 and a second optical member B2 on both sides of the optical functional layer A. The first optical member B1 is laminated on the first single surface of the optical functional layer A, and the second optical member B2 is laminated on the second single surface of the optical functional layer A. Wherein the first optical member B1 are those oxygen permeability ^{1 [cm 3 / (m 2} · 24h · atm)] in the following is used. As the first optical member B1, for example, a separator, a laminate containing a polyvinyl alcohol-based polarizer, a polyvinyl alcohol-based polarizer, or the like is used. On the other hand, various materials can be used for the first optical member B2, but a separator or the like is used. Wherein for the second optical member B2, those oxygen permeability ^{1 [cm 3 / (m 2} · 24h · atm)] in the following is preferred. The optical member with an optical functional layer of the present invention is used in combination with the first optical member B1 and the second optical member B2.

For example, FIG. 2 shows a base material-less adhesive sheet with a double-sided separator in which a separator (s) as a first optical member B1 and a separator (s) as a second optical member B2 are laminated on both sides of the optical functional layer A. ..

For example, FIG. 3 shows a polarizing film (p) containing a polyvinyl alcohol-based polarizer as the first optical member B1 on the first surface of the optical functional layer A, and a separator as the second optical member B2 on the other second surface. The polarizing film with an optical functional layer with a separator which (s) was laminated is shown.

The optical member with an optical functional layer of the present invention has an optical functional layer containing a dye, and has a first optical member and a second optical member on both sides of the optical functional layer. Hereinafter, each member will be described.

<Optical functional layer>
The optical functional layer of the present invention is not particularly limited as long as it is a resin layer containing a dye. Examples of the resin layer include a film layer and an adhesive layer. The optical functional layer can be formed from a composition containing a base polymer and a dye.

<Dye>
Various dyes can be used as the dye contained in the optical functional layer of the present invention. Examples of the dye include various compounds such as tetraazaporphyrin type, porphyrin type, cyanine type, azo type, pyrromethene type, squarylium type, xanthene type, oxonor type, and skualine type. From the viewpoint of widening the color gamut, the dye is preferably a tetraazaporphyrin-based dye, a porphyrin-based dye, a cyanine-based dye, a squalium-based dye, or a squaline-based dye, and particularly preferably a tetraazaporphyrin-based dye. Specifically, the dye is disclosed in Japanese Patent Application Laid-Open No. 2011-116818 and the like. Only one type of the dye may be used, or two or more types may be used in combination.

The dye preferably has a maximum absorption wavelength in at least one of a wavelength range of 470 to 500 nm and a wavelength range of 580 to 610 nm. The dye having the maximum absorption wavelength in the wavelength range can absorb light emission unnecessary for color expression and suppress the light emission, which is effective for widening the color gamut. A porphyrin-based dye can be preferably used as the dye having the maximum absorption wavelength in the wavelength range. For example, as dyes showing a maximum absorption wavelength in the wavelength range of 580 to 610 nm, tetraazaporphyrin compounds manufactured by Yamamoto Chemicals, Inc. (trade names: PD-320, PD311) and tetraazaporphyrin compounds manufactured by Yamada Chemicals, Inc. (trade names: PD-320, PD311) Product name: FDG-007) and the like. The maximum absorption wavelength of the dye was measured by a spectrophotometer (V-570 manufactured by JASCO Corporation).

The content of the dye in the optical functional layer of the present invention is adjusted by the absorption wavelength range of the dye, the extinction coefficient and the type of the base polymer, but is usually 0.01 to 5 parts by weight with respect to 100 parts by weight of the base polymer. It is preferably 0.05 to 3 parts by weight, and more preferably 0.1 to 1 part by weight. In particular, the above range is preferable when a tetraazaporphyrin dye is used.

<Adhesive layer>
Examples of the optical functional layer of the present invention include a pressure-sensitive adhesive layer containing a dye, and the pressure-sensitive adhesive layer can be formed from a pressure-sensitive base polymer and a pressure-sensitive adhesive composition containing a dye. The type of adhesive base polymer is not particularly limited, but for example, rubber-based polymer, (meth) acrylic-based polymer, silicone-based polymer, urethane-based polymer, vinyl alkyl ether-based polymer, polyvinyl alcohol-based polymer, polyvinylpyrrolidone-based polymer. Various polymers such as polymers, polyacrylamide-based polymers, and cellulose-based polymers can be mentioned.

The pressure-sensitive adhesive composition of the present invention contains a sticky base polymer as a main component. The main component refers to the component having the highest content ratio in the total solid content contained in the pressure-sensitive adhesive composition, for example, a component accounting for more than 50% by weight of the total solid content contained in the pressure-sensitive adhesive composition. In addition, it refers to a component that accounts for more than 70% by weight.

Among these adhesive base polymers, those having excellent optical transparency, exhibiting appropriate wettability, cohesiveness, and adhesive adhesive properties, and having excellent weather resistance and heat resistance are preferably used. A (meth) acrylic polymer is preferably used to exhibit such characteristics. Hereinafter, an acrylic pressure-sensitive adhesive using a (meth) acrylic polymer containing alkyl (meth) acrylate as a monomer unit as a base polymer as a material for forming the pressure-sensitive adhesive layer will be described.

<(Meta) acrylic polymer>
The (meth) acrylic polymer usually contains an alkyl (meth) acrylate as a main component as a monomer unit. In addition, (meth) acrylate means acrylate and / or methacrylate, and has the same meaning as (meth) of the present invention.

Examples of the alkyl (meth) acrylate constituting the main skeleton of the (meth) acrylic polymer include those having a linear or branched alkyl group having 1 to 18 carbon atoms. These can be used alone or in combination. The average number of carbon atoms of these alkyl groups is preferably 3 to 9.

Further, from the viewpoints of adhesive properties, durability, adjustment of phase difference, adjustment of refractive index, etc., alkyl (meth) acrylate containing an aromatic ring such as phenoxyethyl (meth) acrylate and benzyl (meth) acrylate is used. be able to.

One or more of the (meth) acrylic polymers having a polymerizable functional group having an unsaturated double bond such as a (meth) acryloyl group or a vinyl group for the purpose of improving adhesiveness and heat resistance. The copolymerization monomer of can be introduced by copolymerization. Specific examples of such a copolymerization monomer include 2-hydroxyethyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, and 6 (meth) acrylate. Hydroxyl group-containing monomers such as −hydroxyhexyl, 8-hydroxyoctyl (meth) acrylate, 10-hydroxydecyl (meth) acrylate, 12-hydroxylauryl (meth) acrylate and (4-hydroxymethylcyclohexyl) -methylacrylate. Carboxyl group-containing monomers such as (meth) acrylic acid, carboxyethyl (meth) acrylate, carboxypentyl (meth) acrylate, itaconic acid, maleic acid, fumaric acid, and crotonic acid; acid anhydrides such as maleic anhydride and itaconic anhydride. Material group-containing monomer; Acrylic acid caprolactone adduct; styrene sulfonic acid, allyl sulfonic acid, 2- (meth) acrylamide-2-methylpropane sulfonic acid, (meth) acrylamide propane sulfonic acid, sulfopropyl (meth) acrylate, ( Meta) Examples thereof include sulfonic acid group-containing monomers such as acrylicoyloxynaphthalene sulfonic acid; and phosphoric acid group-containing monomers such as 2-hydroxyethylacryloyl phosphate.

In addition, (N-substituted) amides such as (meth) acrylamide, N, N-dimethyl (meth) acrylamide, N-butyl (meth) acrylamide, N-methylol (meth) acrylamide, and N-methylolpropane (meth) acrylamide. Monomer; (meth) alkylaminoalkyl-acrylate monomer such as aminoethyl (meth) acrylate, N, N-dimethylaminoethyl (meth) acrylate, t-butylaminoethyl (meth) acrylate; (meth) acrylic (Meta) alkoxyalkyl-based monomers such as methoxyethyl acid and ethoxyethyl (meth) acrylate; N- (meth) acryloyloxymethylene succinimide, N- (meth) acryloyl-6-oxyhexamethylene succinimide, N-( Meta) Succimimide-based monomers such as acryloyl-8-oxyoctamethylene succinimide and N-acryloylmorpholin; maleimide-based monomers such as N-cyclohexyl maleimide, N-isopropyl maleimide, N-lauryl maleimide and N-phenylmaleimide; N-methylitacon Italonimide-based monomers such as imide, N-ethylitaconimide, N-butylitaconimide, N-octylitaconimide, N-2-ethylhexylitaconimide, N-cyclohexylitaconimide, and N-laurylitaconimide, etc. As an example of the monomer of.

Further, as modified monomers, vinyl acetate, vinyl propionate, N-vinylpyrrolidone, methylvinylpyrrolidone, vinylpyridine, vinylpiperidone, vinylpyrimidine, vinylpiperazin, vinylpyrazine, vinylpyrrole, vinylimidazole, vinyloxazole, vinylmorpholin, N- Vinyl-based monomers such as vinylcarboxylic acid amides, styrene, α-methylstyrene, N-vinylcaprolactam; cyanoacrylate-based monomers such as acrylonitrile and methacrylonitrile; epoxy group-containing acrylic monomers such as glycidyl (meth) acrylate; Glycol-based acrylic ester monomers such as (meth) polyethylene glycol acrylate, (meth) polypropylene glycol acrylate, (meth) methoxyethylene glycol acrylate, (meth) methoxypolypropylene glycol acrylate; (meth) tetrahydrofurfuryl acrylate, Acrylic acid ester-based monomers such as fluorine (meth) acrylate, silicone (meth) acrylate and 2-methoxyethyl acrylate can also be used. Further, isoprene, butadiene, isobutylene, vinyl ether and the like can be mentioned.

Further, examples of the copolymerizable monomer other than the above include a silane-based monomer containing a silicon atom. Examples of the silane-based monomer include 3-acryloxypropyltriethoxysilane, vinyltrimethoxysilane, vinyltriethoxysilane, 4-vinylbutyltrimethoxysilane, 4-vinylbutyltriethoxysilane, and 8-vinyloctyltrimethoxysilane. , 8-vinyloctyloxydecyltriethoxysilane, 10-methacryloyloxydecyltrimethoxysilane, 10-acryloyloxydecyltrimethoxysilane, 10-methacryloyloxydecyltriethoxysilane, 10-acryloyloxydecyltriethoxysilane and the like.

Examples of the copolymerization monomer include tripropylene glycol di (meth) acrylate, tetraethylene glycol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, bisphenol A diglycidyl ether di (meth) acrylate, and neo. Pentyl glycol di (meth) acrylate, trimethyl propantri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate , Caprolactone-modified dipentaerythritol Hexa (meth) Acrylate and other (meth) acrylic acids and polyhydric alcohols such as esterified products such as (meth) acryloyl groups and vinyl groups and other unsaturated double bonds having two or more unsaturated double bonds. Polyester (meth) acrylates and epoxys (meth) acrylates and epoxys in which two or more unsaturated double bonds such as (meth) acryloyl groups and vinyl groups are added as functional groups similar to the monomer components to the skeleton of sex monomers, polyesters, epoxys, urethanes, etc. Meta) acrylate, urethane (meth) acrylate and the like can also be used.

The (meth) acrylic polymer contains alkyl (meth) acrylate as a main component in the weight ratio of all the constituent monomers, and the ratio of the copolymerized monomer in the (meth) acrylic polymer is not particularly limited, but the same. The proportion of the polymerized monomer is preferably about 0 to 20%, about 0.1 to 15%, and more preferably about 0.1 to 10% in terms of the weight ratio of all the constituent monomers.

Among these copolymerizable monomers, a hydroxyl group-containing monomer and a carboxyl group-containing monomer are preferably used from the viewpoint of adhesiveness and durability. A hydroxyl group-containing monomer and a carboxyl group-containing monomer can be used in combination. These copolymerizable monomers serve as reaction points with the cross-linking agent when the pressure-sensitive adhesive composition contains the cross-linking agent. Since the hydroxyl group-containing monomer and the carboxyl group-containing monomer are highly reactive with the intermolecular cross-linking agent, they are preferably used for improving the cohesiveness and heat resistance of the obtained pressure-sensitive adhesive layer. The hydroxyl group-containing monomer is preferable in terms of reworkability, and the carboxyl group-containing monomer is preferable in terms of achieving both durability and reworkability.

When a hydroxyl group-containing monomer is contained as the copolymerization monomer, the proportion thereof is preferably 0.01 to 15% by weight, more preferably 0.03 to 10% by weight, and further preferably 0.05 to 7% by weight. preferable. When the carboxyl group-containing monomer is contained as the copolymerization monomer, the proportion thereof is preferably 0.05 to 10% by weight, more preferably 0.1 to 8% by weight, and further preferably 0.2 to 6% by weight. preferable.

As the (meth) acrylic polymer of the present invention, those having a weight average molecular weight in the range of 500,000 to 3,000,000 are usually used. Considering durability, particularly heat resistance, it is preferable to use one having a weight average molecular weight of 700,000 to 2.7 million. Further, it is preferably 800,000 to 2.5 million. If the weight average molecular weight is less than 500,000, it is not preferable in terms of heat resistance. Further, when the weight average molecular weight is larger than 3 million, a large amount of diluting solvent is required to adjust the viscosity for coating, which is not preferable because it increases the cost. The weight average molecular weight is a value measured by GPC (gel permeation chromatography) and calculated in terms of polystyrene.

For the production of such a (meth) acrylic polymer, known production methods such as solution polymerization, radiation polymerization such as UV polymerization, bulk polymerization, emulsion polymerization, and various radical polymerizations can be appropriately selected. Further, the obtained (meth) acrylic polymer may be any of a random copolymer, a block copolymer, a graft copolymer and the like.

In solution polymerization, for example, ethyl acetate, toluene and the like are used as the polymerization solvent. As a specific example of solution polymerization, the reaction is carried out under an inert gas stream such as nitrogen, a polymerization initiator is added, and usually at about 50 to 70 ° C. under reaction conditions of about 5 to 30 hours.

The polymerization initiator, chain transfer agent, emulsifier and the like used for radical polymerization are not particularly limited and can be appropriately selected and used. The weight average molecular weight of the (meth) acrylic polymer can be controlled by the amount of the polymerization initiator and the chain transfer agent used, and the reaction conditions, and the amount of the (meth) acrylic polymer used is appropriately adjusted according to these types.

Examples of the radical polymerization initiator include 2,2'-azobisisobutyronitrile, 2,2'-azobis (2-amidinopropane) dihydrochloride, and 2,2'-azobis [2- (5-methyl-). 2-Imidazolin-2-yl) propane] dihydrochloride, 2,2'-azobis (2-methylpropionamidine) disulfate, 2,2'-azobis (N, N'-dimethyleneisobutyramidine), 2, Azo-based initiators such as 2'-azobis [N- (2-carboxyethyl) -2-methylpropionamidine] hydrate (manufactured by Wako Pure Chemical Industries, Ltd., VA-057), persulfates such as potassium persulfate and ammonium persulfate. Salt, di (2-ethylhexyl) peroxydicarbonate, di (4-t-butylcyclohexyl) peroxydicarbonate, di-sec-butylperoxydicarbonate, t-butylperoxyneodecanoate, t-hexyl Peroxypivalate, t-butylperoxypivalate, dilauroyl peroxide, di-n-octanoyl peroxide, 1,1,3,3-tetramethylbutylperoxy-2-ethylhexanoate, di ( Peroxides such as 4-methylbenzoyl) peroxide, dibenzoyl peroxide, t-butylperoxyisobutyrate, 1,1-di (t-hexylperoxy) cyclohexane, t-butylhydroperoxide, hydrogen peroxide, etc. Examples include system initiators, redox-based initiators that combine peroxides and reducing agents, such as a combination of persulfate and sodium hydrogen sulfite, and a combination of peroxide and sodium ascorbate, but are limited to these. It is not something that is done.

The radical polymerization initiator may be used alone or in combination of two or more, but the total content is 0.005 to 1% by weight based on 100 parts by weight of the monomer. The amount is preferably about 0.02 to 0.5 parts by weight, more preferably about 0.02 to 0.5 parts by weight.

Examples of the chain transfer agent include lauryl mercaptan, glycidyl mercaptan, mercaptoacetic acid, 2-mercaptoethanol, thioglycolic acid, 2-ethylhexyl thioglucolate, 2,3-dimercapto-1-propanol and the like. The chain transfer agent may be used alone or in combination of two or more, but the total content is 0.1 part by weight with respect to 100 parts by weight of the total amount of the monomer components. It is below the degree.

Examples of the emulsifier used in the case of emulsion polymerization include anionic emulsifiers such as sodium lauryl sulfate, ammonium lauryl sulfate, sodium dodecylbenzene sulfonate, ammonium polyoxyethylene alkyl ether sulfate, and sodium polyoxyethylene alkyl phenyl ether sulfate, and polyoxy. Examples thereof include nonionic emulsifiers such as ethylene alkyl ether, polyoxyethylene alkyl phenyl ether, polyoxyethylene fatty acid ester, and polyoxyethylene-polyoxypropylene block polymer. These emulsifiers may be used alone or in combination of two or more.

Further, as an emulsifier into which a radically polymerizable functional group such as a propenyl group or an allyl ether group has been introduced as a reactive emulsifier, specifically, for example, Aqualon HS-10, HS-20, KH-10, BC-05. , BC-10, BC-20 (all manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd.), Adecaria Soap SE10N (manufactured by Asahi Denko Co., Ltd.) and the like. Since the reactive emulsifier is incorporated into the polymer chain after polymerization, it has good water resistance and is preferable. The amount of the emulsifier used is more preferably 0.3 to 5 parts by weight and 0.5 to 1 part by weight from the viewpoint of polymerization stability and mechanical stability with respect to 100 parts by weight of the total amount of the monomer components.

<Crosslinking agent>
Further, in the present invention, a cross-linking agent can be contained in the pressure-sensitive adhesive composition forming the pressure-sensitive adhesive layer having a pigment. As the cross-linking agent, an organic cross-linking agent or a polyfunctional metal chelate can be used. Examples of the organic cross-linking agent include isocyanate-based cross-linking agents, peroxide-based cross-linking agents, epoxy-based cross-linking agents, and imine-based cross-linking agents. A polyfunctional metal chelate is one in which a polyvalent metal is covalently or coordinated to an organic compound. Examples of the polyvalent metal atom include Al, Cr, Zr, Co, Cu, Fe, Ni, V, Zn, In, Ca, Mg, Mn, Y, Ce, Sr, Ba, Mo, La, Sn, Ti and the like. Can be mentioned. Examples of the atom in the organic compound having a covalent bond or a coordination bond include an oxygen atom and the like, and examples of the organic compound include an alkyl ester, an alcohol compound, a carboxylic acid compound, an ether compound and a ketone compound.

Examples of the compound related to the isocyanate-based cross-linking agent include isocyanate monomers such as tolylene diisocyanate, chlorphenylene diisocyanate, tetramethylene diisocyanate, xylylene diisocyanate, diphenylmethane diisocyanate, and hydrogenated diphenylmethane diisocyanate, and these isocyanate monomers. Examples include isocyanate compounds added with trimetylolpropane and the like, isocyanurates, bullet-type compounds, and urethane prepolymer-type isocyanates which have been subjected to an addition reaction such as polyether polyols, polyester polyols, acrylic polyols, polybutadiene polyols, and polyisoprene polyols. be able to. Particularly preferred is a polyisocyanate compound, which is one selected from the group consisting of hexamethylene diisocyanate, hydrogenated xylylene diisocyanate, and isophorone diisocyanate, or a polyisocyanate compound derived thereto. Here, one selected from the group consisting of hexamethylene diisocyanate, hydrogenated xylylene diisocyanate, and isophorone diisocyanate or a polyisocyanate compound derived thereto includes hexamethylene diisocyanate, hydrogenated xylylene diisocyanate, isophorone diisocyanate, and polyol modification. Hexamethylene diisocyanate, polyol-modified hydrogenated xylylene diisocyanate, trimmer-type hydrogenated xylylene diisocyanate, polyol-modified isophorone diisocyanate and the like are included. The exemplified polyisocyanate compound is particularly preferable because the reaction with the hydroxyl group proceeds rapidly by using the acid and the base contained in the polymer as a catalyst, which contributes to the speed of cross-linking.

As the peroxide, any peroxide that generates radically active species by heating or light irradiation to promote cross-linking of the base polymer of the pressure-sensitive adhesive composition can be appropriately used, but in consideration of workability and stability. It is preferable to use a peroxide having a half-life temperature of 80 ° C. to 160 ° C. for 1 minute, and more preferably to use a peroxide having a half-life temperature of 90 ° C. to 140 ° C.

Examples of the peroxide include di (4-t-butylcyclohexyl) peroxydicarbonate (1 minute half-life temperature: 92.1 ° C.) and di-sec-butylperoxydicarbonate (1 minute half-life temperature). : 92.4 ° C.), t-Butylperoxyneodecanoate (1 minute half-life temperature: 103.5 ° C.), t-hexylperoxypivalate (1 minute half-life temperature: 109.1 ° C.), t -Butyl peroxypivalate (1 minute half-life temperature: 110.3 ° C), dilauroyl peroxide (1 minute half-life temperature: 116.4 ° C), di-n-octanoyl peroxide (1 minute half-life temperature) 117.4 ° C.), 1,1,3,3-tetramethylbutylperoxy-2-ethylhexanoate (1 minute half-life temperature: 124.3 ° C.), di (4-methylbenzoyl) peroxide (1) Minute half-life temperature: 128.2 ° C.), Dibenzoyl peroxide (1 minute half-life temperature: 130.0 ° C.), t-Butyl peroxyisobutyrate (1 minute half-life temperature: 136.1 ° C.), 1 , 1-di (t-hexylperoxy) cyclohexane (1 minute half-life temperature: 149.2 ° C.) and the like. Among them, di (4-t-butylcyclohexyl) peroxydicarbonate (1 minute half-life temperature: 92.1 ° C.) and dilauroyl peroxide (1 minute half-life temperature: 116.) Since the cross-linking reaction efficiency is particularly excellent. 4 ° C.), dibenzoylperoxide (1 minute half-life temperature: 130.0 ° C.) and the like are preferably used.

The half-life of peroxide is an index showing the decomposition rate of peroxide, and means the time until the residual amount of peroxide is halved. The decomposition temperature for obtaining a half-life at an arbitrary temperature and the half-life time at an arbitrary temperature are described in the manufacturer's catalog, etc. For example, "Organic peroxide catalog 9th edition" of Nippon Oil & Fats Co., Ltd. (May 2003) ”etc.

The amount of the cross-linking agent used is preferably 20 parts by weight or less, more preferably 0.01 to 20 parts by weight, based on 100 parts by weight of the base polymer such as the (meth) acrylic polymer in the pressure-sensitive adhesive composition. Further, 0.03 to 10 parts by weight is preferable. If the amount of the cross-linking agent is more than 20 parts by weight, the moisture resistance is not sufficient and peeling is likely to occur in a reliability test or the like.

Further, the pressure-sensitive adhesive composition forming the pressure-sensitive adhesive layer having the dye of the present invention may contain a silane coupling agent. Durability can be improved by using a silane coupling agent. Specific examples of the silane coupling agent include 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropyltriethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 2- (3,). Epoxy group-containing silane coupling agent such as 4-epoxycyclohexyl) ethyltrimethoxysilane, 3-aminopropyltrimethoxysilane, N-2- (aminoethyl) -3-aminopropylmethyldimethoxysilane, 3-triethoxysilyl- Amino group-containing silane coupling agents such as N- (1,3-dimethylbutylidene) propylamine and N-phenyl-γ-aminopropyltrimethoxysilane, 3-acryloxypropyltrimethoxysilane, 3-methacryloxypropyltri. Examples thereof include a (meth) acrylic group-containing silane coupling agent such as ethoxysilane, and an isocyanate group-containing silane coupling agent such as 3-isocyanatepropyltriethoxysilane.

The silane coupling agent may be used alone or in combination of two or more, but the total content is 100 parts by weight of the base polymer such as the (meth) acrylic polymer. On the other hand, the silane coupling agent is preferably 0.001 to 5 parts by weight, more preferably 0.01 to 1 part by weight, further preferably 0.02 to 1 part by weight, and further preferably 0.05 to 0 parts by weight. 6.6 parts by weight is preferred. It is an amount that improves durability and appropriately retains adhesive force to optical members such as liquid crystal cells.

Further, in the present invention, a polyether-modified silicone can be blended in the pressure-sensitive adhesive composition forming the pressure-sensitive adhesive layer having a pigment. As the polyether-modified silicone, for example, those disclosed in JP-A-2010-275522 can be used.

Further, in the present invention, other known additives may be contained in the pressure-sensitive adhesive composition forming the pressure-sensitive adhesive layer having a pigment, for example, powders such as colorants and pigments, dyes, and surfactants. Agents, plasticizers, tackifiers, surfactants, leveling agents, softeners, anti-aging agents, antioxidants, light stabilizers, UV absorbers, polymerization inhibitors, inorganic or organic fillers, metal powders, It can be appropriately added depending on the intended use of particles, foils and the like. Further, a redox system to which a reducing agent is added may be adopted within a controllable range.

A pressure-sensitive adhesive layer having a pigment is formed by the pressure-sensitive adhesive composition. In forming the pressure-sensitive adhesive layer, the amount of the cross-linking agent added is adjusted, and the influences of the cross-linking treatment temperature and the cross-linking treatment time are fully considered. Is preferable.

The cross-linking treatment temperature and the cross-linking treatment time can be adjusted depending on the cross-linking agent used. The crosslinking treatment temperature is preferably 170 ° C. or lower.

Further, the cross-linking treatment may be performed at the temperature at the time of the drying step of the pressure-sensitive adhesive layer, or a separate cross-linking treatment step may be provided after the drying step.

The crosslinking treatment time can be set in consideration of productivity and workability, but is usually about 0.2 to 20 minutes, preferably about 0.5 to 10 minutes.

As a method for forming the pressure-sensitive adhesive layer having a dye, for example, the pressure-sensitive adhesive composition is applied to a peeled separator or the like, and a polymerization solvent or the like is dried and removed to form the pressure-sensitive adhesive layer, and then the first or second pressure-sensitive adhesive layer is formed. By a method of transferring to an optical member, or a method of applying the pressure-sensitive adhesive composition to the first or second optical member and drying and removing a polymerization solvent or the like to form a pressure-sensitive adhesive layer on the first or second optical member. It is made. When applying the pressure-sensitive adhesive, one or more solvents other than the polymerization solvent may be newly added as appropriate.

A silicone release liner is preferably used as the release-treated separator. In the step of applying the adhesive composition of the present invention on such a liner and drying it to form an adhesive layer, an appropriate method is appropriately adopted as a method of drying the adhesive, depending on the purpose. obtain. Preferably, a method of overheating and drying the coating film is used. The heating and drying temperature is preferably 40 ° C. to 200 ° C., more preferably 50 ° C. to 180 ° C., and particularly preferably 70 ° C. to 170 ° C. By setting the heating temperature in the above range, a pressure-sensitive adhesive having excellent adhesive properties can be obtained.

As the drying time, an appropriate time can be adopted as appropriate. The drying time is preferably 5 seconds to 20 minutes, more preferably 5 seconds to 10 minutes, and particularly preferably 10 seconds to 5 minutes.

Further, an anchor layer can be formed on the surface of the first or second optical member, or an adhesive layer can be formed after various easy-adhesion treatments such as corona treatment and plasma treatment are performed. Further, the surface of the pressure-sensitive adhesive layer may be subjected to an easy-adhesion treatment.

Various methods are used as the method for forming the pressure-sensitive adhesive layer. Specifically, for example, roll coat, kiss roll coat, gravure coat, reverse coat, roll brush, spray coat, dip roll coat, bar coat, knife coat, air knife coat, curtain coat, lip coat, die coater, etc. Examples include a method such as an extrusion coating method.

The thickness of the pressure-sensitive adhesive layer is not particularly limited, and is, for example, about 1 to 100 μm. It is preferably 2 to 50 μm, more preferably 2 to 40 μm, and even more preferably 5 to 35 μm.

When the pressure-sensitive adhesive layer is exposed, the pressure-sensitive adhesive layer may be protected by a sheet (separator) that has been peeled off until it is put into practical use.

<Film layer>
Further, examples of the optical functional layer of the present invention include a film layer containing a dye, and the film layer can be formed from a base polymer for film formation and a composition containing a dye. As the material of the base polymer forming the film layer, the same materials as those constituting the transparent protective film described later can be exemplified. In particular, as the material, a cellulose resin such as triacetyl cellulose, a polyester resin, a (meth) acrylic resin, a cyclic polyolefin resin (norbornen-based resin) and the like are preferably used. The film layer can be applied to the first optical member and the second optical member by appropriately using an adhesive, an adhesive or the like.

As a method for forming the film layer containing the dye, various methods can be adopted. For example, when the pellets of the resin material are dissolved in a solvent, a dye is mixed to prepare a composition, and the composition is cast or extruded to produce a film layer. At that time, the film layer can be formed to an appropriate thickness. When preparing the composition, additives can be appropriately added.

The thickness of the film layer is not particularly limited and is the same as that of the pressure-sensitive adhesive layer, for example, about 1 to 100 μm. It is preferably 2 to 50 μm, more preferably 2 to 40 μm, and even more preferably 5 to 35 μm.

<Optical member>
In the present invention, various optical members can be used. Examples of the optical member include a separator, a polarizing film, a retardation film, a brightness improving film, a glass plate and the like.

Examples of the constituent material of the separator include plastic films such as polyethylene, polypropylene, polyethylene terephthalate and polyester film, porous materials such as paper, cloth and non-woven fabric, nets, foam sheets, metal foils, and laminates thereof. An appropriate thin leaf body can be mentioned, but a plastic film is preferably used because of its excellent surface smoothness.

The plastic film is not particularly limited as long as it can protect the optical functional layer (particularly, the pressure-sensitive adhesive layer), and is, for example, a polyvinyl alcohol film, a polyethylene film, a polypropylene film, a polybutene film, a polybutadiene film, or a polymethyl. Examples thereof include a penten film, a polyvinyl chloride film, a vinyl chloride copolymer film, a polyethylene terephthalate film, a polybutylene terephthalate film, a polyurethane film, and an ethylene-vinyl acetate copolymer film.

The thickness of the separator is usually 1 to 500 μm, preferably 5 to 200 μm, preferably about 5 to 100 μm. If necessary, the separator may be used for mold release and antifouling treatment with a silicone-based, fluorine-based, long-chain alkyl-based or fatty acid amide-based mold release agent, silica powder, etc., as well as a coating type, a kneading type, and a vapor deposition type. It is also possible to perform antistatic treatment such as. In particular, the peelability from the optical functional layer (particularly, the pressure-sensitive adhesive layer) can be further enhanced by appropriately performing a peeling treatment such as a silicone treatment, a long-chain alkyl treatment, or a fluorine treatment on the surface of the separator.

As the polarizing film, one having a transparent protective film on one side or both sides of the polarizing element is generally used.

The polarizer is not particularly limited, and various polarizers can be used. As the polarizer, for example, a hydrophilic polymer film such as a polyvinyl alcohol-based film, a partially formalized polyvinyl alcohol-based film, an ethylene-vinyl acetate copolymerization system partially saponified film, and a bicolor property of iodine or a bicolor dye are used. Examples thereof include a uniaxially stretched film by adsorbing a substance, a polyene-based oriented film such as a dehydrated product of polyvinyl alcohol and a dehydrogenated product of polyvinyl chloride. Among these, a polarizer made of a polyvinyl alcohol-based film and a dichroic substance such as iodine is preferable. The thickness of these polarizers is not particularly limited, but is generally about 80 μm or less.

A polarizer obtained by dyeing a polyvinyl alcohol-based film with iodine and uniaxially stretching it can be prepared, for example, by dyeing the polyvinyl alcohol-based film by immersing it in an aqueous solution of iodine and stretching it to 3 to 7 times the original length. it can. If necessary, it can be immersed in an aqueous solution of potassium iodide or the like, which may contain boric acid, zinc sulfate, zinc chloride or the like. Further, if necessary, the polyvinyl alcohol-based film may be immersed in water and washed with water before dyeing. In addition to being able to clean the surface of the polyvinyl alcohol film and blocking inhibitors by washing the polyvinyl alcohol film with water, it also has the effect of preventing non-uniformity such as uneven dyeing by swelling the polyvinyl alcohol film. is there. Stretching may be performed after dyeing with iodine, stretching while dyeing, or stretching and then dyeing with iodine. It can be stretched even in an aqueous solution such as boric acid or potassium iodide or in a water bath.

Further, as the polarizer, a thin polarizer having a thickness of 10 μm or less can be used. From the viewpoint of thinning, the thickness is preferably 1 to 7 μm. It is preferable that such a thin polarizing element has less unevenness in thickness, is excellent in visibility, is excellent in durability because there is little dimensional change, and can be made thinner as a polarizing film.

Typical examples of the thin polarizing element include JP-A-51-069644, JP-A-2000-338329, WO2010 / 100917 pamphlet, PCT / JP2010 / 00146, or Japanese Patent Application No. 2010-. Examples thereof include the thin polarizing film described in the specification of No. 269002 and the specification of Japanese Patent Application No. 2010-263692. These thin polarizing films can be obtained by a manufacturing method including a step of stretching a polyvinyl alcohol-based resin (hereinafter, also referred to as PVA-based resin) layer and a resin base material for stretching in a laminated state and a step of dyeing. With this manufacturing method, even if the PVA-based resin layer is thin, it can be stretched without any trouble such as breakage due to stretching because it is supported by the stretching resin base material.

The thin polarizing film can be stretched at a high magnification and the polarization performance can be improved even in a manufacturing method including a step of stretching in a laminated state and a step of dyeing, and the WO2010 / 100917 pamphlet, PCT / It is preferably obtained by a production method including a step of stretching in an aqueous boric acid solution as described in JP2010 / 00460, or in Japanese Patent Application No. 2010-269002 and Japanese Patent Application No. 2010-263692, particularly preferably. It is preferably obtained by a production method including a step of auxiliary stretching in the air before stretching in an aqueous boric acid solution described in Japanese Patent Application No. 2010-269002 and Japanese Patent Application No. 2010-263692.

As a material constituting the transparent protective film, for example, a thermoplastic resin having excellent transparency, mechanical strength, thermal stability, moisture blocking property, isotropic property and the like is used. Specific examples of such thermoplastic resins include cellulose resins such as triacetyl cellulose, polyester resins, polyether sulfone resins, polysulfone resins, polycarbonate resins, polyamide resins, polyimide resins, polyolefin resins, (meth) acrylic resins, and cyclic resins. Examples thereof include polyolefin resins (norbornene-based resins), polyarylate resins, polystyrene resins, polyvinyl alcohol resins, and mixtures thereof. A transparent protective film is attached to one side of the polarizer by an adhesive layer, but as a transparent protective film on the other side, (meth) acrylic, urethane, acrylic urethane, epoxy, silicone. A thermosetting resin such as a system or an ultraviolet curable resin can be used. The transparent protective film may contain one or more of any suitable additives. Examples of the additive include an ultraviolet absorber, an antioxidant, a lubricant, a plasticizer, a mold release agent, a color inhibitor, a flame retardant, a nucleating agent, an antistatic agent, a pigment, a colorant and the like. The content of the thermoplastic resin in the transparent protective film is preferably 50 to 100% by weight, more preferably 50 to 99% by weight, still more preferably 60 to 98% by weight, and particularly preferably 70 to 97% by weight. .. When the content of the thermoplastic resin in the transparent protective film is 50% by weight or less, the high transparency inherent in the thermoplastic resin may not be sufficiently exhibited.

A functional layer (surface layer) such as a hard coat layer, an antireflection layer, an antisticking layer, a diffusion layer or an antiglare layer can be provided on the surface of the transparent protective film to which the polarizer is not adhered.

The thickness of the transparent protective film is not particularly limited as long as the total thickness of the polarizing film is 100 μm or less, and is, for example, about 10 to 90 μm. It is preferably 15 to 60 μm, more preferably 20 to 50 μm.

The adhesive used for bonding the polarizer and the transparent protective film is not particularly limited as long as it is optically transparent, and various forms such as water-based, solvent-based, hot-melt-based, radical-curing type, and cation-curing type are used. However, water-based adhesives or radical curable adhesives are suitable.

As the glass plate, various types applied to the optical member can be used. The glass plate includes a flexible glass plate. The thickness of the glass is preferably about 15 to 150 μm. The constituent material of the glass is not particularly limited, and examples thereof include SiO ₂ , Al ₂ O ₃ , B ₂ O ₃ , MgO, CaO, SrO, BaO, Na ₂ O, and Li ₂ O. These materials may be used alone, in combination of two or more, and may further contain other components.

The first optical member of the present invention, the Among the optical member, the oxygen permeability of ^{1 [cm 3 / (m 2} · 24h · atm)] using the following things. Oxygen permeability of the first optical ^member, is ^{0.8 [cm 3 / (m 2} · 24h · atm)] or less, and further ^{0.6 [cm 3 / (m 2} · 24h · atm)] or less preferably, more preferably ^{0.5 [cm 3 / (m 2} · 24h · atm)] or less. As for the second optical member, the oxygen permeability in the same manner as the first optical ^member 1 is preferably ^{[cm 3 / (m 2 ·} 24h · atm)] or less.

The oxygen permeability of the optical member is determined by the material, thickness and the like. The oxygen permeability of the optical member is specifically measured according to the description of Examples.

Oxygen ^{permeability,} 1 as the ^{[cm 3 / (m 2 ·} 24h · atm)] separator capable of satisfying the following, among the polyvinyl alcohol film, polyethylene terephthalate film and the like are preferable. The thickness of the film is not particularly limited as long as it can satisfy the oxygen permeability, and from the viewpoint of handling, a film having a thickness of 1 to 500 μm, preferably 1 to 200 μm is usually used. ..

The oxygen ^{permeability,} 1 as the polarizing film ^{[cm 3 / (m 2 ·} 24h · atm)] can be satisfied or less, for example, those using a polyvinyl alcohol-based polarizer can be mentioned. The thickness of the polyvinyl alcohol-based polarizer is not particularly limited as long as it can satisfy the oxygen permeability, and the thickness can be used. From the viewpoint of thinning, usually 1 Those having a thickness of 10 μm can be used.

<LCD panel>
The optical member with an optical functional layer of the present invention can be suitably used when forming a liquid crystal panel. For example, in the case of an optical member with an adhesive layer in which the optical functional layer of the optical member with an optical functional layer of the present invention is an adhesive layer, the optical member with an adhesive layer (for example, no base material with a double-sided separator) The pressure-sensitive adhesive layer in the pressure-sensitive adhesive sheet) can be suitably used when a polarizing film is attached to a liquid crystal cell to form a liquid crystal panel. Further, when a polarizing film is used as the optical member, the polarizing film with an adhesive layer can be bonded to at least one surface of the liquid crystal cell to form a liquid crystal panel. The pressure-sensitive adhesive layer or the polarizing film with a pressure-sensitive adhesive layer in the optical member with a pressure-sensitive adhesive layer of the present invention is preferably used on the visual side of the liquid crystal cell.

As the liquid crystal cell, any type such as TN type, STN type, π type, VA type, and IPS type can be used, but the liquid crystal cell of the IPS mode is preferably used for the liquid crystal panel of the present invention.

In addition to the polarizing film, another optical layer can be applied to form the liquid crystal panel. The optical layer is not particularly limited, but for example, a liquid crystal panel such as a reflector, a transflective plate, a retardation plate (including a wave plate such as 1/2 or 1/4), a viewing angle compensation film, or a brightness improving film. One or two or more optical layers that may be used for formation can be used on the visual side and / or the back side of the liquid crystal cell.

<Liquid crystal display device>
The liquid crystal panel is used in the liquid crystal display device, and is formed by appropriately assembling components such as a lighting system and incorporating a drive circuit as needed. Further, when forming the liquid crystal display device, for example, an appropriate component such as a diffuser plate, an anti-glare layer, an antireflection film, a protective plate, a prism array, a lens array sheet, a light diffuser plate, and a backlight is placed in one layer or at an appropriate position. Two or more layers can be arranged. Further, an appropriate liquid crystal display device such as a lighting system using a backlight or a reflector can be formed.

Hereinafter, the present invention will be specifically described with reference to Examples, but the present invention is not limited to these Examples. In addition, each part and% in each example is based on weight. All the conditions for leaving at room temperature, which are not specified below, are 23 ° C. and 65% RH.

<Measurement of weight average molecular weight of (meth) acrylic polymer>
The weight average molecular weight (Mw) of the (meth) acrylic polymer was measured by GPC (gel permeation chromatography). Mw / Mn was also measured in the same manner.
-Analyzer: HLC-8120GPC manufactured by Tosoh Corporation
-Column: Made by Tosoh, G7000H _XL + GMH _XL + GMH _XL
-Column size: 7.8 mm φ x 30 cm each, 90 cm in total
-Column temperature: 40 ° C
・ Flow rate: 0.8 mL / min
・ Injection amount: 100 μL
-Eluent: Tetrahydrofuran-Detector: Differential Refractometer (RI)
・ Standard sample: Polystyrene

<Measurement of oxygen permeability>
It was determined according to JISK 7126-2 under the conditions of 23 ° C. and 0% RH using an oxygen permeability measuring device OX-TRAN manufactured by Mocon.

<Optical member>
PVA: A polyvinyl alcohol film (trade name PE4500 manufactured by Kuraray Co., Ltd.) was used. Oxygen permeability was less than ^{0.02 [cm 3 / (m 2} · 24h · atm)].
PET: A polyethylene terephthalate film (trade name MRF38CK manufactured by Mitsubishi Plastics) was used. Oxygen permeability was ^{0.29 [cm 3 / (m 2} · 24h · atm)].
PMMA: A polymethyl methacrylate film was used. Oxygen permeability was ^{5 [cm 3 / (m 2} · 24h · atm)].
COP: A cyclic olefin film (trade name: Zeonoa ZF16 manufactured by Zeon Corporation) was used. Oxygen permeability was ^{652 [cm 3 / (m 2} · 24h · atm)].
Glass: A glass plate having a thickness of 1000 μm (soda glass manufactured by Matsunami Glass Industry Co., Ltd.) was used. Oxygen permeability was ^{0.02 [cm 3 / (m 2} · 24h · atm)] less (less than detection limit).

The PMMA (polymethylmethacrylate film) was formed by putting a trade name of Delpet manufactured by Asahi Kasei Chemical Co., Ltd. into a single-screw extruder, melt-mixing the film, and passing it through a T-die. The obtained extruded film was simultaneously biaxially stretched twice in the length direction and the width direction (surface magnification 4.0) at a stretching temperature of 240 ° C. to obtain a film having a thickness of 40 μm. The stretching speed was 10% / sec in both the length direction and the width direction. In this way, the above PMMA was obtained.

<Preparation of (meth) acrylic polymer>
A monomer mixture containing 100 parts of butyl acrylate, 0.01 part of 2-hydroxyethyl acrylate, and 5 parts of acrylic acid was charged into a reaction vessel equipped with a cooling tube, a nitrogen introduction tube, a thermometer and a stirrer. Further, with respect to 100 parts of the monomer mixture, 0.1 part of 2,2'-azobisisobutyronitrile as a polymerization initiator was charged together with 100 parts of ethyl acetate, and nitrogen gas was introduced with gentle stirring to introduce nitrogen. After the substitution, the liquid temperature in the flask was maintained at around 55 ° C. and the polymerization reaction was carried out for 8 hours to carry out a polymerization reaction (solid content concentration) of an acrylic polymer having a weight average molecular weight (Mw) of 1.8 million and Mw / Mn = 4.1. 30% by weight) was prepared.

Example 1
(Preparation of adhesive composition)
With respect to 100 parts of the solid content of the acrylic polymer solution produced above
0.3 copies of benzoyl peroxide (trade name NOF BMT manufactured by NOF CORPORATION),
0.6 part of isocyanate-based cross-linking agent (trade name Coronate L manufactured by Tosoh Corporation) and tetraazaporphyrin-based dye (trade name PD-320 manufactured by Yamamoto Kasei Co., Ltd .: having a maximum absorption wavelength at a wavelength of 595 nm). Part 1,
Was blended to obtain an adhesive composition.

(Manufacturing of optical member with adhesive layer)
The pressure-sensitive adhesive composition is uniformly applied to the surface of a release base material (MRF38CK manufactured by Mitsubishi Resin Co., Ltd.) of a polyethylene terephthalate film treated with a silicone-based release agent with an applicator, and in an air circulation type constant temperature oven at 155 ° C. After drying for 2 minutes, a 20 μm-thick pressure-sensitive adhesive layer was formed on the surface of the base material. The release base material was also bonded to the other surface of the obtained pressure-sensitive adhesive layer to obtain a pressure-sensitive adhesive sheet having the release base material on both sides.

Next, the peeling base material was peeled off from one side of the pressure-sensitive adhesive sheet, and the glass was bonded to the exposed pressure-sensitive adhesive layer surface as a second optical member. The peeled base material was also peeled off from the other side, and the PVA was bonded to the exposed pressure-sensitive adhesive layer surface as a first optical member as a sample.

(Evaluation of fading)
After measuring the transmittance (initial) of the sample, the sample was left in a constant temperature bath at 85 ° C. for 24 hours, returned to room temperature (23 ° C.), and then the transmittance (after 24 hours) was measured again.
From the transmittance, the rate of change in transmittance = transmittance (after 24 hours) / transmittance (initial) × 100 (%) was determined.
It can be said that the smaller the rate of change in transmittance, the less fading.

<Measurement of transmittance>
The transmittance was measured using a spectral transmittance measuring device with an integrating sphere (Dot-3c of Murakami Color Technology Research Institute). The transmittance was measured when the sample was at 23 ° C.

Examples 2-3, Comparative Examples 1-2
An optical member with an adhesive layer was produced in the same manner as in Example 1 except that the first and second optical members used in the preparation of the sample were changed as shown in Table 1.

In the examples, the rate of change in transmittance was small, and fading could not be confirmed.
On the other hand, in the comparative example, the rate of change in the transmittance was large, and fading was confirmed.

A Optical functional layer B1 First optical member B2 Second optical member

Claims (8)

An optical functional layer containing a dye, and an optical member with an optical functional layer having a first optical member and a second optical member on both sides of the optical functional layer.
The first optical member is a polarizing film having a thickness of 100 μm or less containing a polyvinyl alcohol-based polarizer, a separator having a thickness of 5 to 200 μm, or a glass plate having a thickness of 15 to 150 μm.
The second optical member is a polarizing film having a thickness of 100 μm or less containing a polyvinyl alcohol-based polarizer, a separator having a thickness of 5 to 200 μm, or a glass plate having a thickness of 15 to 150 μm.
At least the first optical member, an oxygen permeability of ^{1 [cm 3 / (m 2} · 24h · atm)] The optical member with an optical functional layer of equal to or less than. The optical member with an optical functional layer according to claim 1, wherein the first optical member is a separator having a thickness of 5 to 200 μm. The optical member with an optical functional layer according to claim 1, wherein the first optical member is a polarizing film having a thickness of 100 μm or less containing a polyvinyl alcohol-based polarizing element. The second optical member, an oxygen permeability of ^{1 [cm 3 / (m 2} · 24h · atm)] optical functional layer according to any one of claims 1 to 3, wherein, wherein the less is Attached optical member. The optical member with an optical functional layer according to claim 3, wherein the second optical member is a separator having a thickness of 5 to 200 μm. The optical member with an optical functional layer according to any one of claims 1 to 5, wherein the dye has a maximum absorption wavelength in at least one of a wavelength range of 470 to 510 nm and a wavelength range of 570 to 610 nm. The optical functional layer optical member according to any one of claims 1 to 6, wherein the dye is a tetraazaporphyrin-based dye. The optical functional layer according to any one of claims 1 to 7, wherein the dye is contained in an amount of 0.01 to 5 parts by weight with respect to 100 parts by weight of the base polymer forming the resin layer of the optical functional layer. Attached optical member.

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