TW201943818A - Polarizing plate provided with phase difference layer, and organic el display device - Google Patents

Abstract

The invention provides a polarizing plate with a retardation layer which suppresses cracking of a retardation layer in a high-temperature environment. The polarizing plate with a retardation layer of the present invention has a polarizing plate, a first retardation layer, an adhesive layer, and a second retardation layer in this order. The first retardation layer and the second retardation layer include a liquid crystal compound to form adhesion The adhesive of the agent layer contains 0.05 parts by weight or more of an isocyanate crosslinking agent with respect to 100 parts by weight of the base polymer.

Description

Polarizing plate with retardation layer and organic EL display device

The invention relates to a polarizing plate with a retardation layer and an organic EL (Electroluminescence) display device.

In recent years, with the popularity of thin displays, image display devices (organic EL display devices) equipped with organic EL panels have been proposed. The organic EL panel has a highly reflective metal layer, which is prone to problems such as external light reflection and background reflection. For this reason, it is known to prevent such problems by providing a polarizing plate (circular polarizing plate) with a retardation layer on the viewing side. However, when a laminated body formed by bonding two retardation layers containing a liquid crystal compound by an adhesive is used as the retardation layer of such a polarizing plate with a retardation layer, the retardation layer exists in a high temperature environment. A crack occurs.
[Prior technical literature]
[Patent Literature]

[Patent Document 1] Japanese Patent No. 3325560

[Problems to be solved by the invention]

The present invention was made in order to solve the above-mentioned previous problems, and its main object is to provide a polarizing plate with a retardation layer that suppresses cracking of a retardation layer in a high-temperature environment, and a polarizing plate using such a retardation layer with a retardation layer. Organic EL display device.
[Technical means to solve the problem]

The polarizing plate with a retardation layer of the present invention has a polarizing plate, a first retardation layer, an adhesive layer, and a second retardation layer in this order. The first retardation layer and the second retardation layer include a liquid crystal compound. In addition, the adhesive constituting the above-mentioned adhesive layer contains 0.05 parts by weight or more of an isocyanate crosslinking agent with respect to 100 parts by weight of the base polymer.
In one embodiment, the base polymer-based (meth) acrylic polymer is described above.
In one embodiment, the base polymer contains a carboxyl group-containing monomer as a monomer component.
In one embodiment, the adhesive constituting the adhesive layer further includes an ultraviolet absorber.
In one embodiment, the ultraviolet absorbent has 0 to 3 hydroxyl groups in a molecular structure.
In one embodiment, the adhesive constituting the adhesive layer further includes a pigment compound having a maximum absorption wavelength in an absorption spectrum in a wavelength range of 380 nm to 430 nm.
According to another aspect of the present invention, an organic EL display device is provided. This organic EL display device includes the above-mentioned polarizing plate with a retardation layer.
[Effect of the invention]

According to the present invention, by making the adhesive constituting the adhesive layer disposed between the two retardation layers contain 0.05 parts by weight or more of an isocyanate cross-linking agent with respect to 100 parts by weight of the base polymer, suppression of a high temperature environment can be achieved. The retardation layer generates a cracked polarizing plate with a retardation layer.

Hereinafter, embodiments of the present invention will be described. However, the present invention is not limited to these embodiments.

A. Polarizing plate with retardation layer FIG. 1 is a schematic cross-sectional view of a polarizing plate with retardation layer according to an embodiment of the present invention. As shown in FIG. 1, the polarizing plate 100 with a retardation layer includes a polarizing plate 10, a first retardation layer 20, an adhesive layer 30, and a second retardation layer 40 in this order. That is, the first retardation layer 20 and the second retardation layer 40 are laminated via the adhesive layer 30. The first retardation layer 20 and the second retardation layer 40 are composed of a liquid crystal compound. The adhesive constituting the adhesive layer 30 contains 0.05 parts by weight or more of an isocyanate crosslinking agent with respect to 100 parts by weight of the base polymer. This can prevent the first retardation layer 20 and / or the second retardation layer 30 from cracking in a high-temperature environment. Another adhesive layer 50 may be laminated on the opposite side of the second retardation layer 40 from the adhesive layer 30. This makes it easy to adhere to, for example, an organic EL panel.

The base polymer of the adhesive is preferably a (meth) acrylic polymer. The base polymer of the above-mentioned adhesive preferably contains a carboxyl group-containing monomer as a monomer component. In one embodiment, the adhesive constituting the adhesive layer 30 further includes an ultraviolet absorber. In this case, the ultraviolet absorber preferably has 0 to 3 hydroxyl groups in the molecular structure. Furthermore, in one embodiment, the adhesive constituting the adhesive layer 30 further includes a pigment compound having a maximum absorption wavelength in an absorption spectrum in a wavelength range of 380 nm to 430 nm. With the above-described configuration, the adhesive layer 30 can be provided with an ultraviolet absorbing function, whereby the deterioration of the organic EL element can be suppressed when the polarizing plate with a retardation layer is used in an organic EL display device.

Hereinafter, each layer constituting the polarizing plate 100 with a retardation layer will be described in detail.

B. Polarizing Plate The polarizing plate 10 typically includes a polarizing element, a first protective layer disposed on one side of the polarizing element, and a second protective layer disposed on the other side of the polarizing element. Typically, the polarizing element is an absorption-type polarizing element. One of the first protective layer and the second protective layer may be omitted.

B-1. Polarizer As the polarizer, any appropriate polarizer can be used. For example, the resin film forming the polarizing element may be a single-layer resin film or a laminated body of two or more layers.

Specific examples of the polarizing element including a single-layer resin film include hydrophilic polymers such as polyvinyl alcohol (PVA) -based films, partially formalized PVA-based films, and ethylene-vinyl acetate copolymer-based partially saponified films. The film is made of a dichroic substance such as iodine or a dichroic dye and subjected to a dyeing treatment and an extension treatment, a polyene-based alignment film such as a dehydrated product of PVA or a dehydrochlorinated product of polyvinyl chloride. From the standpoint of excellent optical characteristics, it is preferred to use a polarizing element obtained by dyeing a PVA film with iodine and uniaxially stretching it.

The above-mentioned dyeing with iodine can be performed, for example, by immersing a PVA-based film in an iodine aqueous solution. The stretching ratio of the uniaxial stretching is preferably 3 to 7 times. Stretching can be performed after the dyeing treatment, or it can be performed while dyeing. It can also be stretched and dyed. The PVA-based film is subjected to a swelling treatment, a crosslinking treatment, a washing treatment, a drying treatment, and the like, as necessary. For example, by immersing the PVA-based film in water and washing with water before dyeing, not only the stains on the surface of the PVA-based film or anti-blocking agent can be cleaned, but also the PVA-based film can be swelled to prevent uneven dyeing.

Specific examples of the polarizing element obtained by using a laminate include a laminate using a resin substrate and a PVA-based resin layer (PVA-based resin film) laminated on the resin substrate, or a resin substrate and coating formed on A polarizing element obtained by laminating a PVA-based resin layer of the resin substrate. A polarizing element obtained by using a laminate of a resin substrate and a PVA-based resin layer formed on the resin substrate can be produced, for example, by applying a PVA-based resin solution to the resin substrate and drying it. Then, a PVA-based resin layer is formed on the resin substrate to obtain a laminated body of the resin substrate and the PVA-based resin layer; the laminated body is extended and dyed, and the PVA-based resin layer is made into a polarizing element. In this embodiment, typically, stretching includes immersing a laminated body in a boric acid aqueous solution for stretching. Furthermore, if necessary, the stretching may further include stretching the laminate in the air at a high temperature (for example, above 95 ° C.) before the stretching in the boric acid aqueous solution. The obtained laminate of the resin substrate / polarizing element can be used directly (that is, the resin substrate can be used as a protective layer of the polarizing element), or the resin substrate can be peeled from the laminate of the resin substrate / polarizing element. This peeled area layer is used after using any appropriate protective layer. The details of the method of manufacturing such a polarizing element are described in, for example, Japanese Patent Laid-Open No. 2012-73580. The entire description of this publication is incorporated herein by reference.

The thickness of the polarizing element is, for example, 1 μm to 35 μm. In one embodiment, the thickness of the polarizing element is preferably 1 μm to 15 μm, further preferably 3 μm to 10 μm, and particularly preferably 3 μm to 8 μm. When the thickness of the polarizing element is within such a range, curling during heating can be satisfactorily suppressed, and good appearance durability during heating can be obtained.

B-2. Protective layer The first and second protective layers are formed of any appropriate protective film that can be used as a film for protecting a polarizing element. Specific examples of the material of the main component of the protective film include cellulose-based resins such as triacetyl cellulose (TAC), or polyester-based, polyvinyl alcohol-based, polycarbonate-based, polyamide-based, and poly- Transparent resins such as fluorene imide, polyether fluorene, polyfluorene, polystyrene, polynorbornene, polyolefin, (meth) acrylic, and acetate. In addition, thermosetting resins such as (meth) acrylic, urethane, urethane, (meth) acrylic, epoxy, and silicone, or ultraviolet curable resins can also be mentioned. Other examples include glassy polymers such as siloxane polymers. In addition, a polymer film described in Japanese Patent Laid-Open No. 2001-343529 (WO01 / 37007) may be used. As the material of the film, for example, a resin combination containing a thermoplastic resin having a substituted or unsubstituted imine group in a side chain and a thermoplastic resin having a substituted or unsubstituted phenyl group and a nitrile group in a side chain can be used. Examples of the resin include a resin composition having an alternating copolymer containing isobutylene and N-methylcis butylene diimide, and an acrylonitrile-styrene copolymer. The polymer film may be, for example, an extruded product of the resin composition.

The thickness of the protective film is preferably 10 μm to 100 μm. The protective film may be laminated on the polarizing element via an adhesive layer (specifically, an adhesive layer and an adhesive layer), or may be laminated on the polarizing element in close contact (without the adhesive layer). The adhesive layer is formed of any appropriate adhesive. Examples of the adhesive include a water-soluble adhesive containing a polyvinyl alcohol resin as a main component. The water-soluble adhesive containing a polyvinyl alcohol-based resin as a main component preferably further contains a metal compound colloid. The metal compound colloid may be one obtained by dispersing fine particles of the metal compound in a dispersion medium, and may be statically stable due to mutual repulsion of the same kind of charges of the fine particles, thereby having permanent stability. The average particle diameter of the fine particles forming the metal compound colloid may be any appropriate value as long as it does not adversely affect optical characteristics such as polarizing characteristics. It is preferably 1 nm to 100 nm, and further preferably 1 nm to 50 nm. The reason is that the fine particles can be uniformly dispersed in the adhesive layer, the adhesiveness is ensured, and the crack point can be suppressed. The "crack point" refers to a local unevenness defect generated at the interface between the polarizing element and the protective film. The adhesive layer contains any suitable adhesive.

C. Phase difference layer As described above, the first and second phase difference layers are composed of a liquid crystal compound. Typically, the first and second retardation layers may include an alignment cured layer of a liquid crystal composition containing a liquid crystal compound. In this specification, the "alignment-cured layer" refers to a layer in which a liquid crystal compound is aligned in a specific direction in a layer, and its alignment state is fixed. The alignment curing layer of the liquid crystal compound can be formed by performing an alignment treatment on the surface of a specific substrate, and applying a coating liquid containing a liquid crystal compound on the surface, so that the liquid crystal compound is aligned and fixed in a direction corresponding to the above-mentioned alignment treatment. The alignment state. In one embodiment, the substrate is any appropriate resin film, and the alignment cured layer formed on the substrate can be transferred to the surface of other layers constituting the polarizing plate with a retardation layer. Specific examples of the liquid crystal compound and a method for forming the alignment cured layer are described in Japanese Patent Laid-Open No. 2006-163343. The description of this publication is incorporated by reference in this specification.

In one embodiment, the in-plane retardation Re (550) of the first retardation layer is preferably 200 nm to 300 nm, and the in-plane retardation Re (550) of the second retardation layer is preferably 100 nm ~ 150 nm. Therefore, in this case, the first retardation layer can function as a λ / 2 plate, and the second retardation layer can function as a λ / 4 plate. The angle formed by the absorption axis of the polarizing element and the late phase axis of the first retardation layer is preferably 5 ° to 25 °, and particularly preferably about 15 °. The angle formed by the absorption axis of the polarizing element and the late phase axis of the second retardation layer is preferably 65 ° to 85 °, and particularly preferably about 75 °. In another embodiment, the in-plane retardation Re (550) of the first retardation layer is preferably 120 nm ~ 160 nm, and the second retardation layer satisfies the relationship of the refractive index ellipsoid nz> nx = ny. Therefore, in this case, the first retardation layer can function as a λ / 4 plate, and the second retardation layer can function as a so-called positive C plate. The angle formed by the absorption axis of the polarizing element and the late phase axis of the first retardation layer is preferably 39 ° to 51 °, and particularly preferably about 45 °.

C-1. First Phase Difference Layer In one embodiment, the first phase difference layer may include an alignment cured layer of a liquid crystal composition containing a disc type liquid crystal compound that is substantially vertically aligned. In this specification, "disk-type liquid crystal compound" refers to a liquid crystal primordium having a disc-like shape in the molecular structure, and 2 to 8 side chains are bonded to the liquid crystalline radical by ether bonds or ester bonds. By. The thickness of the first retardation layer can be set in a manner to obtain a desired in-plane retardation, and is preferably 1 μm to 20 μm, and more preferably 1 μm to 12 μm. The liquid crystal composition containing a disc-type liquid crystal compound is not particularly limited as long as it includes a disc-type liquid crystal compound and exhibits liquid crystallinity. The content of the disc-type liquid crystal compound in the liquid crystal composition is preferably 100 parts by weight or more and less than 100 parts by weight based on 100 parts by weight of the total solid content of the liquid crystal composition. The retardation film as the alignment cured layer of the liquid crystal composition containing the disc-type liquid crystal compound having substantially vertical alignment can be obtained by a method described in Japanese Patent Laid-Open No. 2001-56411.

In another embodiment, the first retardation layer may include an alignment curing layer that is aligned (horizontal alignment) in a state where the rod-like liquid crystal compounds are aligned in the retardation axis direction of the retardation layer. As a liquid crystal compound, the liquid crystal compound whose liquid crystal phase is a nematic phase (nematic liquid crystal) is mentioned, for example. As such a liquid crystal compound, for example, a liquid crystal polymer or a liquid crystal monomer can be used. The liquid crystal properties of the liquid crystal compound can be expressed by liquid or heat. When the liquid crystal compound is a liquid crystal monomer, the liquid crystal monomer is preferably a polymerizable monomer and a crosslinkable monomer. The reason is that the alignment state of the liquid crystal monomer can be fixed by polymerizing or crosslinking the liquid crystal monomer. As the liquid crystal monomer, any appropriate liquid crystal monomer can be used. For example, the polymerizable liquid crystal primitive compounds described in Japanese Patent Publication No. 2002-533742 (WO00 / 37585), EP358208 (US5211877), EP66137 (US4388453), WO93 / 22397, EP0261712, DE19504224, DE4408171, and GB2280445 can be used. Wait. Specific examples of such a polymerizable liquid crystal priming compound include, for example, the trade name LC242 of BASF, the trade name E7 of Merck, and the trade name LC-Sillicon-CC3767 of Wacker-Chem. The thickness of the first retardation layer can be set in a manner to obtain a desired in-plane retardation, and is preferably 1 μm to 10 μm, and more preferably 1 μm to 6 μm.

C-2. The second retardation layer that can function as a λ / 4 plate can be formed by using the materials and methods described in the above C-1 for the first retardation layer.

The second retardation layer that can function as a positive C plate may include any appropriate liquid crystal compound as long as the refractive index ellipsoid satisfies the relationship of nz> nx = ny. The details of such a liquid crystal compound are described in Japanese Patent No. 4186980 and Japanese Patent No. 6055569. The description of this publication is incorporated by reference in this specification. In one embodiment, the second retardation layer may include the following chemical formula (I) (the numbers 65 and 35 in the formula represent the mole percentage of the monomer unit, and for convenience, the block polymer is expressed: weight average molecular weight 5000), a side chain liquid crystal polymer, and a polymerizable liquid crystal exhibiting a nematic liquid crystal phase.

[Chemical 1]

D. Adhesive layer As described above, the adhesive contains 0.05 parts by weight or more of an isocyanate crosslinking agent with respect to 100 parts by weight of the base polymer, and preferably further contains an ultraviolet absorber and / or a pigment compound.

The thickness of the adhesive layer is, for example, 2 μm to 50 μm, and preferably 5 μm to 30 μm. The gel fraction of the adhesive layer is preferably 40% to 95%, more preferably 50% to 95%, even more preferably 65% to 93%, particularly preferably 80% to 93%, and most preferably 85%. ~ 93%. In the case where the gel fraction of the adhesive layer is small, there are cases where the cohesive force is poor, and there are problems with workability or handling. From the viewpoint of preventing appearance defects such as paste dents, the gel fraction immediately after the formation of the adhesive layer is preferably 60% or more, more preferably 63% or more, and still more preferably 66% or more. It is preferably at least 70%.

D-1. Base polymer As the base polymer, any appropriate polymer can be used as long as it exhibits the required adhesiveness and adhesion. Specific examples of the base polymer include (meth) acrylic polymers and rubber-based polymers. A base polymer-based (meth) acrylic polymer is preferred.

The (meth) acrylic polymer contains, as a monomer unit, an alkyl (meth) acrylate as a main component. Examples of the (meth) acrylic acid alkyl ester include a linear or branched ester terminal having an alkyl group having 1 to 24 carbon atoms. The (meth) acrylic acid alkyl ester may be used singly or in combination of two or more kinds. The "alkyl (meth) acrylate" refers to an alkyl acrylate and / or an alkyl methacrylate.

The (meth) acrylic acid alkyl ester having an alkyl group having 1 to 24 carbon atoms at the ester end is preferably 40% by weight or more with respect to the total amount of the monofunctional monomer component forming the (meth) acrylic polymer. It is more preferably 50% by weight or more, and still more preferably 60% by weight or more.

The monomer component may include a comonomer other than the alkyl (meth) acrylate as the monofunctional monomer component. Comonomers can be used as the remainder of the alkyl (meth) acrylate in the monomer component. Examples of the comonomer include a cyclic nitrogen-containing monomer. As the cyclic nitrogen-containing monomer, those having a polymerizable functional group having an unsaturated double bond such as a (meth) acrylfluorenyl group or a vinyl group and having a cyclic nitrogen structure can be used without particular limitation. The cyclic nitrogen structure is preferably one having a nitrogen atom in the cyclic structure. The content of the cyclic nitrogen-containing monomer relative to the total amount of the monofunctional monomer component forming the (meth) acrylic polymer is preferably 0.5 to 50% by weight, and more preferably 0.5 to 40% by weight. More preferably, it is 0.5 to 30% by weight.

The monomer component forming the (meth) acrylic polymer may include other functional group-containing monomers. Examples of such a monomer include a carboxyl group-containing monomer and a monomer having a cyclic ether group. When a carboxyl group-containing monomer is contained, the content is preferably 0.05 to 10% by weight, more preferably 0.1 to 8% by weight, and still more preferably 0.2 to 6% by weight. By containing a carboxyl group-containing monomer, the gel fraction of the adhesive layer can be set to a value within a preferable range. As a result, cracks in the retardation layer can be suppressed.

The monomer component may contain a hydroxyl-containing monomer. As the hydroxyl group-containing monomer, those having a polymerizable functional group having an unsaturated double bond such as a (meth) acrylfluorenyl group or a vinyl group, and having a hydroxyl group can be used without particular limitation. From the viewpoint of improving the adhesion and the cohesion, the content of the above-mentioned hydroxyl-containing monomer is preferably 0.08% by weight or more relative to the total amount of the monofunctional monomer component forming the (meth) acrylic polymer. It is more preferably 0.3% by weight or more, and even more preferably 1% by weight or more. On the other hand, the upper limit of the content of the hydroxyl-containing monomer is preferably 30% by weight, more preferably 27% by weight, relative to the total amount of the monofunctional monomer component forming the (meth) acrylic polymer. It is preferably 25% by weight. When there are too many hydroxyl-containing monomers, there may be a case where the adhesive layer becomes hard, and the adhesive force may decrease, and there may be a case where the viscosity of the adhesive becomes too high.

In order to adjust the cohesive force of the adhesive, the monomer component forming the (meth) acrylic polymer may contain any appropriate polyfunctional monomer in addition to the above-mentioned monofunctional monomer as necessary.

The (meth) acrylic polymer generally uses a weight average molecular weight in a range of 500,000 to 3 million. In consideration of durability, particularly heat resistance, it is preferable to use a weight average molecular weight of 700,000 to 2.7 million. Furthermore, it is preferably 800,000 to 2.5 million. When the weight average molecular weight is less than 500,000, the heat resistance is not good. In addition, if the weight average molecular weight becomes more than 3 million, a large amount of a diluent solvent is required in order to adjust the viscosity suitable for coating, and the cost is increased, which is unfavorable. The weight average molecular weight refers to a value measured by GPC (Gel Permeation Chromatography) and calculated by polystyrene conversion.

As a method for producing the (meth) acrylic polymer, any appropriate method such as radiation polymerization such as solution polymerization, ultraviolet (UV) polymerization, block polymerization, and emulsion polymerization can be adopted. The obtained (meth) acrylic polymer may be any of a random copolymer, a block copolymer, and a graft copolymer.

When a (meth) acrylic polymer is produced by radical polymerization, a polymerization initiator, a chain transfer agent, an emulsifier, and the like used in the radical polymerization may be appropriately added to the monomer component to perform polymerization. The polymerization initiator, chain transfer agent, emulsifier, and the like used in the radical polymerization are not particularly limited, and may be appropriately selected and used. In addition, the weight average molecular weight of the (meth) acrylic polymer can be controlled by the amount of polymerization initiator, chain transfer agent used, and reaction conditions, and the amount used can be appropriately adjusted according to the type of these.

When a (meth) acrylic polymer is produced by radiation polymerization, it can be produced by irradiating a monomer component with radiation such as an electron beam and ultraviolet (UV) to polymerize it. Among these, ultraviolet polymerization is preferable. In the case of performing ultraviolet polymerization, it is preferred that the monomer component contains a photopolymerization initiator from the advantages of shortening the polymerization time.

The photopolymerization initiator is not particularly limited, and a photopolymerization initiator having an absorption band at a wavelength of 400 nm or more is preferred. Examples of such a photopolymerization initiator include bis (2,4,6-trimethylbenzylidene) -phenylphosphine oxide (manufactured by BASF, product name "Irgacure 819"), 2,4,6 -Trimethylbenzyl-diphenyl-phosphine oxide ("LUCIRIN TPO", manufactured by BASF) and the like.

The photopolymerization initiator may contain a photopolymerization initiator having an absorption band at a wavelength of less than 400 nm. The photopolymerization initiator is not particularly limited as long as it starts photopolymerization by generating free radicals with ultraviolet rays and has an absorption band at a wavelength of less than 400 nm. Generally, the photopolymerization initiators used are all Can be used better. For example, benzoin ether-based photopolymerization initiator, acetophenone-based photopolymerization initiator, α-keto alcohol-based photopolymerization initiator, photoactive oxime-based photopolymerization initiator, and benzoin-based photopolymerization initiator can be used. Agent, benzophenone-based photopolymerization initiator, benzophenone-based photopolymerization initiator, ketal-based photopolymerization initiator, 9-oxysulfur Based photopolymerization initiator, fluorenyl phosphine oxide based photopolymerization initiator, and the like.

D-2. Isocyanate crosslinking agent In the adhesive, the content of the isocyanate crosslinking agent relative to 100 parts by weight of the base polymer is preferably from 0.1 to 12 parts by weight. The lower limit of the content of the isocyanate crosslinking agent with respect to 100 parts by weight of the base polymer is preferably 0.5 parts by weight, more preferably 1 part by weight, and particularly preferably 2 parts by weight. This can effectively suppress cracks in the retardation layer in a high-temperature environment. The upper limit of the content of the isocyanate crosslinking agent with respect to 100 parts by weight of the base polymer is preferably 8 parts by weight, and more preferably 5 parts by weight. This can suppress whitening of the adhesive layer.

An isocyanate crosslinking agent refers to a compound having two or more isocyanate groups (including isocyanate-regenerating functional groups that temporarily protect the isocyanate group by a blocking agent or polyploidization) in one molecule. Examples of the isocyanate crosslinking agent include aromatic isocyanates such as toluene diisocyanate and xylene diisocyanate; alicyclic isocyanates such as isophorone diisocyanate; and aliphatic isocyanates such as hexamethylene diisocyanate. Toluene diisocyanate is preferred. The reason is that the gel fraction of the adhesive layer can be increased.

More specifically, examples include lower aliphatic polyisocyanates such as butylene diisocyanate and hexamethylene diisocyanate; and cycloaliphatic groups such as cyclopentyl diisocyanate, cyclohexane diisocyanate, and isophorone diisocyanate. Isocyanates; 2,4-toluene diisocyanate, 4,4'-diphenylmethane diisocyanate, xylene diisocyanate, polymethylene polyphenyl isocyanate and other aromatic diisocyanates; trimethylolpropane / toluene Diisocyanate trimer adduct (manufactured by Nippon Polyurethane Industry Co., Ltd., product name "Coronate L"), trimethylolpropane / hexamethylene diisocyanate trimer adduct (Nippon Polyurethane Industry Co., Ltd. Product, product name "Coronate HL"), isocyanurate of hexamethylene diisocyanate (product of "Nippon Polyurethane Industry Co., Ltd. product name" Coronate HX ") and other isocyanate adducts; xylene diisocyanate Trimethylolpropane adduct (manufactured by Mitsui Chemicals, Inc., product name "D110N"), trimethylolpropane of hexamethylene diisocyanate Adducts (manufactured by Mitsui Chemicals Co., Ltd., product name "D160N"); polyether polyisocyanates, polyester polyisocyanates, and these adducts with various polyols; through isocyanurate bonds, condensation Polyfunctional polyisocyanates, such as diurea bonds and urethane bonds.

D-3. Ultraviolet absorbent As the ultraviolet absorbent, any appropriate ultraviolet absorbent can be used. The ultraviolet absorber preferably has 0 to 3 hydroxyl groups in its molecular structure. Specific examples thereof include a tri-based ultraviolet absorber, a benzotriazole-based ultraviolet absorber, a benzophenone-based ultraviolet absorber, an oxybenzophenone-based ultraviolet absorber, a salicylate-based ultraviolet absorber, A cyanoacrylate-based ultraviolet absorber and the like may be used singly or in combination of two or more kinds. Among these, a three-series ultraviolet absorber and a benzotriazole-based ultraviolet absorber are preferred, because of good solubility in the monomers used to form the acrylic adhesive composition, and ultraviolet rays near a wavelength of 380 nm The absorption capacity is high, so it is preferably selected from the group consisting of a three-series ultraviolet absorbent having one or less hydroxyl groups in one molecule and a benzotriazole ultraviolet absorbent having one benzotriazole skeleton in one molecule. At least one ultraviolet absorber in the group. The ultraviolet absorber may be used alone or as a mixture of two or more kinds.

The content of the ultraviolet absorber is preferably 0.1 to 20 parts by weight, more preferably 0.1 to 10 parts by weight, still more preferably 0.1 to 5 parts by weight, and particularly preferably 0.5 to 3 parts relative to 100 parts by weight of the base polymer. Parts by weight.

The maximum absorption wavelength of the absorption spectrum of the ultraviolet absorber is preferably in a wavelength region of 300 nm to 400 nm, and more preferably in a wavelength region of 320 nm to 380 nm. The maximum absorption wavelength can be measured using a UV-visible spectrophotometer.

As the ultraviolet absorbent, a commercially available one can be preferably used, and examples thereof include Tinosorb S (manufactured by BASF), SeeSorb 106 (manufactured by Shipro Kasei Co., Ltd.), and the like.

D-4. Pigment compound As described above, the maximum absorption wavelength of the absorption spectrum of the pigment compound exists in a wavelength range of 380 nm to 430 nm. The maximum absorption wavelength of the absorption spectrum of the pigment compound is preferably present in a wavelength range of 380 nm to 420 nm. By using such a pigment compound in combination with an ultraviolet absorber, light in a region (wavelength 380 nm to 430 nm) that does not affect the light emission of the organic EL element can be sufficiently absorbed, and the light emission region (longer than 430 nm) of the organic EL element can be sufficiently absorbed. (Wavelength side) can be fully transmitted.

The half-value width of the pigment compound is preferably 80 nm or less, more preferably 5 nm to 70 nm, and still more preferably 10 nm to 60 nm. Thereby, light in a region that does not affect the light emission of the organic EL element can be sufficiently absorbed, and light having a wavelength side longer than 430 nm can be sufficiently transmitted. The half-value width of the pigment compound can be measured using a UV-visible spectrophotometer (manufactured by Hitachi High-Tech Science Co., Ltd., product name "U-4100") from the transmission spectrum of the pigment compound solution under the following measurement conditions. Representatively, the spectroscopic spectrum measured by adjusting the concentration so that the absorbance at the maximum absorption wavelength is 1.0, and the wavelength interval (full amplitude at half maximum) between 2 points which is 50% of the peak value is set as the pigment compound. Half the width.
(Measurement conditions)
Solvent: toluene or chloroform Cell: quartz cell Optical path length: 10 mm

The pigment compound may be any compound whose maximum absorption wavelength exists in the above-mentioned wavelength region, and its structure and the like are not particularly limited. Examples of the pigment compound include an organic pigment compound and an inorganic pigment compound. Among these, an organic pigment compound is preferred from the viewpoint of maintaining the dispersibility and transparency of the resin component with respect to the resin component.

Examples of the organic pigment compound include a methylimine compound, an indole compound, a cinnamic acid compound, a pyrimidine compound, a porphyrin compound, and a polymethine compound.

As the organic pigment compound, a commercially available one can be preferably used. Specifically, as the indole-based compound, BONASORB UA3911 (manufactured by Orient Chemical Industries Co., Ltd., the maximum absorption wavelength of the absorption spectrum: 398 nm, half-value width : 48 nm), BONASORB UA3912 (manufactured by Orient Chemical Industries Co., Ltd., the maximum absorption wavelength of the absorption spectrum: 386 nm, half-value width: 53 nm). As a cinnamic acid compound, SOM-5-0106 (Orient Chemical Industries Co., Ltd., the maximum absorption wavelength of the absorption spectrum: 416 nm, half-value width: 50 nm). As the pyrimidine-based compound, FDB-009 (manufactured by Yamada Chemical Industry Co., Ltd., the maximum absorption wavelength of the absorption spectrum: 394 nm, half-value width: 43 nm). As a porphyrin-based compound, FDB-001 (manufactured by Yamada Chemical Industry Co., Ltd., maximum absorption wavelength of absorption spectrum: 420 nm, half-value width: 14 nm) is used. Examples of polymethine compounds include DAA247 (manufactured by Yamada Chemical Industry Co., Ltd., the maximum absorption wavelength of the absorption spectrum: 389 nm, the half-value width: 49.5 nm) and many more.

D-5. Other components The adhesive composition may include other components such as a silane coupling agent, an antioxidant, an anti-aging agent, and a plasticizer, as necessary. Examples of the antioxidant include phenol-based, phosphorus-based, sulfur-based, and amine-based antioxidants. Examples of the silane coupling agent include epoxy-containing silane coupling agents such as 3-glycidyloxypropyltrimethoxysilane, amine-containing silane coupling agents such as 3-aminopropyltrimethoxysilane, and 3 -(Meth) acrylic group-containing silane coupling agents such as propylene methoxypropyltrimethoxysilane, isocyanate-containing silane coupling agents such as 3-isocyanopropyltriethoxysilane, and ethyl acetate Acetyl ethyl silane coupling agent.

E. Organic EL display device The polarizing plate with a retardation layer described in the above items A to D can be used for an image display device. Therefore, the present invention also includes an image display device using such an optical laminate. Typical examples of the image display device include a liquid crystal display device and an organic electroluminescence (EL) display device. An image display device (organic EL display device) according to an embodiment of the present invention includes the optical multilayer body described in the above items A to D.
[Example]

Hereinafter, the present invention will be specifically described by examples, but the present invention is not limited to these examples. In addition, the measurement method of each characteristic is as follows.
(1) Thickness An interference film thickness meter (manufactured by Otsuka Electronics Co., Ltd., MCPD2000) was used to measure the thickness of the retardation layer. The thickness of layers other than the retardation layer was measured using a digital micrometer (KC-351C, manufactured by Anritsu Co., Ltd.).
(2) Phase difference value The refractive index nx, ny, and nz of the phase difference layer are measured by an automatic birefringence measuring device (manufactured by Oji Measurement Co., Ltd., automatic birefringence meter KOBRA-WPR), and the in-plane phase difference Re and The thickness direction retardation Rth.
(3) Penetration of the adhesive layer. The release films of each adhesive layer obtained in the examples and comparative examples were peeled off. The adhesive layer was mounted on a measuring jig, and a spectrophotometer (manufactured by Hitachi High-Technologies Co., Ltd.) was used. , Product name "U4100"). The transmittance is the transmittance in the range of 300 nm to 450 nm.
(4) Gel fraction of the adhesive layer: 0.2 g of each adhesive layer (adhesive composition) obtained in the examples and comparative examples was wrapped in a fluororesin (made by Nitto Denko Corporation, The product name is "TEMISH NTF-1122", weight: Wa). After tightening to prevent the adhesive from leaking, measure the weight (Wb) and place it in a sample bottle. 40 cc of ethyl acetate was added and left for 7 days. After that, the fluororesin was taken out and dried on an aluminum cup at 130 ° C. for 2 hours. The weight (Wc) of the fluororesin containing the sample was measured, and the gel fraction was determined by the following formula (I).
Formula (I): Gel fraction = (Wc-Wa) / (Wb-Wa) × 100 (% by weight)
The measurement of the gel fraction was performed after the adhesive layer was formed and then left at room temperature (23 ° C) for one week.

＜ Manufacture example 1 ＞
(Production of polarizing plate)
For a long roll of 30 μm thick polyvinyl alcohol film (manufactured by Kuraray, product name "PE3000"), it was uniaxially extended in the lengthwise direction by a roll stretcher so that the lengthwise direction became 5.9 times, while swelling and dyeing were performed simultaneously. , Cross-linking, washing treatment, and finally drying treatment to produce a polarizing element with a thickness of 12 μm.
Specifically, the swelling treatment is 2.2 times as long as it is treated with pure water at 20 ° C. Next, the dyeing treatment was carried out in a 30 ° C aqueous solution with a weight ratio of iodine and potassium iodide of 1: 7 adjusted so that the transmittance of the polarizing film was 45.0%, and the extension was 1.4 times. . Furthermore, the cross-linking treatment is performed in two stages. The first-stage cross-linking treatment is performed in an aqueous solution in which boric acid and potassium iodide are dissolved at 40 ° C, and is extended to 1.2 times. The boric acid content of the cross-linked aqueous solution in the first stage was 5.0% by weight, and the potassium iodide content was 3.0% by weight. The cross-linking treatment in the second stage was treated at 65 ° C in an aqueous solution in which boric acid and potassium iodide were dissolved, and extended to 1.6 times. The boric acid content of the cross-linked aqueous solution in the second stage was set to 4.3% by weight, and the potassium iodide content was set to 5.0% by weight. The washing treatment was performed with a potassium iodide aqueous solution at 20 ° C. The potassium iodide content of the rinsed aqueous solution was set to 2.6% by weight. Finally, the drying process was performed at 70 ° C for 5 minutes to obtain a polarizing element.
A TAC film (product name: KC2UA, thickness: 25 μm) manufactured by Konica Minolta Co., Ltd. was attached to both sides of the obtained polarizing element through a polyvinyl alcohol-based adhesive, and HC (Hard) was provided on one side of the TAC film. Coating (hard coating) layer of HC-TAC film (thickness: 32 μm) to obtain a polarizing plate 1 with a protective film laminated on both sides of the polarizing element.

＜ Manufacture example 2 ＞
(Production of phase difference layer A)
10 g of a polymerizable liquid crystal (manufactured by BASF Corporation, product name "PaliocolorLC242", represented by the following formula) and 3 g of a photopolymerization initiator (Ciba) for the polymerizable liquid crystal compound Specialty Chemicals (product name: "Irgacure 907") was dissolved in 40 g of toluene to prepare a liquid crystal composition (coating liquid).
[Chemical 2]

The surface of a polyethylene terephthalate (PET) film (thickness: 38 μm) was rubbed with a rubbing cloth, and an alignment treatment was performed. The conditions of the alignment treatment are the number of rubbings (the number of rubbing rollers) is 1, the radius of the rubbing roller is 76.89 mm, the speed of the rubbing roller nr is 1500 rpm, the film conveying speed v is 83 mm / sec, the friction strength RS and the pressing amount M The tests were performed under the five conditions (a) to (e) shown in Table 1.

[Table 1]

The direction of the alignment treatment was set to a direction of -75 ° when viewed from the side of the polarizing element when it was attached to the polarizing plate with respect to the absorption axis of the polarizing element. The above-mentioned coating liquid was applied to the alignment treatment surface by a bar coater, and heated and dried at 90 ° C. for 2 minutes to align the liquid crystal compound. Under the conditions (a) to (c), the alignment state of the liquid crystal compound is very good. Under the conditions (d) and (e), the alignment of the liquid crystal compound causes a small amount of confusion, but it is a level where there is no problem in practical use. The liquid crystal layer thus formed was irradiated with 1 mJ / cm ² of light using a metal halide lamp to harden the liquid crystal layer, thereby forming a retardation layer A on the PET film. The thickness of the retardation layer A is 2 μm, and the in-plane retardation Re is 270 nm. Furthermore, the retardation layer A has a refractive index distribution of nx> ny = nz.

＜ Manufacture example 3 ＞
(Production of Phase Difference Layer B)
The surface of a polyethylene terephthalate (PET) film (thickness: 38 μm) was rubbed with a rubbing cloth, and an alignment treatment was performed. The direction of the alignment treatment was set to a direction of -15 ° when viewed from the recognition side when the direction with respect to the absorption axis of the polarizing element was attached to the polarizing plate. On this alignment treatment surface, the same liquid crystal coating liquid as described above was applied, and the liquid crystal was aligned and hardened in the same manner as described above to form a retardation layer B on the PET film. The thickness of the retardation layer B is 1.2 μm, and the in-plane retardation Re is 140 nm. Further, the retardation layer B has a refractive index distribution of nx> ny = nz.

[Example 1]
1. Preparation of Adhesive Layer <Preparation of (meth) acrylic polymer (1)>
In a reaction vessel equipped with a cooling tube, a nitrogen introduction tube, a thermometer and a stirring device, 99 parts of butyl acrylate, 1.0 part of 4-hydroxybutyl acrylate, and 0.3 part of 2,2'-azobisisobutyronitrile were added with ethyl acetate. After reacting at 60 ° C. for 4 hours under a stream of nitrogen, ethyl acetate was added to the reaction solution to obtain a solution (solid content concentration 30%) containing an acrylic polymer having a weight average molecular weight of 1.6 million.
＜ Preparation of adhesive composition ＞
Using the above-mentioned acrylic polymer as a base polymer, 0.3 part of benzamidine peroxide (manufactured by Nippon Oil & Fat Co., Ltd., product name "Nyper BMT") per 100 parts of solid content of the acrylic polymer solution, 0.1 part of trimethylolpropane xylene diisocyanate (manufactured by Mitsui Chemicals Co., Ltd., product name "Takenate D110N") and 0.2 part of silane coupling agent (manufactured by Soken Chemical Co., Ltd., product name "A-100" , Silane coupling agent containing ethyl acetoacetate) to obtain adhesive composition A (solution).
＜ Production of adhesive layer ＞
The above-mentioned adhesive composition A was applied to a release film including a polyester film surface-treated with a silicone-based release agent, and heat-treated at 155 ° C for 3 minutes, thereby obtaining an adhesive layer having a thickness of 20 μm. .
2. Production of a polarizing plate with a retardation layer The above-mentioned TAC film surface of the polarizing plate and the retardation layer A are cured by ultraviolet rays so that the angle between the absorption axis of the polarizing plate and the retardation axis of the retardation layer A becomes 75 °. Type adhesive is bonded. Next, the retardation layer A and the retardation layer B are bonded through the above-mentioned adhesive layer so that the angle between the absorption axis of the polarizing plate and the retardation axis of the retardation layer B becomes 15 °, thereby obtaining the retardation layer with the retardation layer. Polarizer.

[Example 2]
Add 2 parts by weight (weight of solid content) of 2,4-bis-[[4- (4-ethylhexyloxy) -4-hydroxy} -phenyl] -6- (4-methoxyphenyl ) -1,3,5-tri (BASF Japan, product name "Tinosorb S", "a1" in Table 1) was used as an ultraviolet absorbent, and an adhesive composition was obtained in the same manner as in Example 1. B.
A polarizing plate with an adhesive layer and a retardation layer was obtained in the same manner as in Example 1 except that the above-mentioned adhesive composition B was used.

[Example 3]
An adhesive composition C was obtained in the same manner as in Example 2 except that the addition amount of trimethylolpropane xylene diisocyanate was 0.5 parts with respect to 100 parts of the solid content of the acrylic polymer solution.
A polarizing plate with an adhesive layer and a retardation layer was obtained in the same manner as in Example 1 except that the above-mentioned adhesive composition C was used.

[Example 4]
Add 2 parts by weight (weight of solid content) of 2,2 ', 4,4'-tetrahydroxybenzophenone (made by Shipro Kasei Co., Ltd., product name "SeeSorb106", "a2" in Table 1) instead An adhesive composition D was obtained in the same manner as in Example 3 except that the ultraviolet absorbent a1 was used as an ultraviolet absorbent.
A polarizing plate with an adhesive layer and a retardation layer was obtained in the same manner as in Example 1 except that the above-mentioned adhesive composition D was used.

[Example 5]
The addition amount of the ultraviolet absorber a1 was set to 3 parts by weight, and 3 parts by weight (solid content weight) of a pyrimidine-based compound (manufactured by Yamada Chemical Industry Co., Ltd., product name "FDB-009", shown in Table 1 "B1") was obtained in the same manner as in Example 3, except that a pigment compound was used as a pigment compound, and an adhesive composition E was obtained.
A polarizing plate with an adhesive layer and a retardation layer was obtained in the same manner as in Example 1 except that the above-mentioned adhesive composition E was used.

[Example 6]
The addition amount of the ultraviolet absorber a2 was set to 3 parts by weight, and 2 parts by weight (weight of solid content) of an indole-based compound (manufactured by Orient Chemical Industries Co., Ltd., product name "BONASORB UA3912", as shown in Table 1 "B3") was obtained in the same manner as in Example 4 except that the pigment compound was a pigment compound, and an adhesive composition F was obtained.
A polarizing plate with an adhesive layer and a retardation layer was obtained in the same manner as in Example 1 except that the above-mentioned adhesive composition F was used.

[Example 7]
95 parts of butyl acrylate, 4.9 parts of acrylic acid, and 2-hydroxyethyl acrylate were added to a reaction vessel equipped with a cooling pipe, a nitrogen introduction pipe, a thermometer, and a stirring device with 100 parts of ethyl acetate (solid content) of ethyl acetate. 0.1 part and 0.3 part of benzamidine diperoxide were reacted at 60 ° C for 7 hours under a nitrogen gas stream, and ethyl acetate was added to the reaction solution to obtain an acrylic polymer having a weight average molecular weight of 2.2 million. Solution (solid content 30% by weight).
Using the above acrylic polymer as a base polymer, 0.5 part of trimethylolpropane toluene diisocyanate (manufactured by Nippon Polyurethane Co., Ltd., product name "Coronate L" was prepared per 100 parts of solid content of the acrylic polymer solution. "), 0.075 parts of γ-glycidyloxypropylmethoxysilane (manufactured by Shin-Etsu Chemical Industry Co., Ltd., product name" KBM-403 "), and 3 parts by weight of ultraviolet absorbent a1 to obtain an adhesive agent combination物 G。 Object G.
Except having used the said adhesive composition G, it carried out similarly to Example 1, and obtained the adhesive layer and the polarizing plate with a retardation layer.

[Example 8]
An adhesive composition H was obtained in the same manner as in Example 7 except that the pigment compound b1 was added in an amount of 3 parts by weight (the weight of the solid component).
Except having used the said adhesive composition H, it carried out similarly to Example 1, and obtained the adhesive layer and the polarizing plate with a retardation layer.

[Example 9]
An adhesive composition I was obtained in the same manner as in Example 7 except that the pigment compound b3 was added in an amount of 3 parts by weight (the weight of the solid component).
A polarizing plate with an adhesive layer and a retardation layer was obtained in the same manner as in Example 1 except that the above-mentioned adhesive composition I was used.

[Example 10]
3 parts by weight (weight of solid content) of a polymethine compound (manufactured by Yamada Chemical Industry Co., Ltd., product name "DAA247", "b2" in Table 1) was added as a pigment compound. 7 Similarly, the adhesive composition J was obtained.
A polarizing plate with an adhesive layer and a retardation layer was obtained in the same manner as in Example 1 except that the above-mentioned adhesive composition J was used.

[Example 11]
An adhesive composition K was obtained in the same manner as in Example 10 except that the addition amount of trimethylolpropane toluene diisocyanate was 0.8 parts based on 100 parts of the solid content of the acrylic polymer solution.
A polarizing plate with an adhesive layer and a retardation layer was obtained in the same manner as in Example 1 except that the above-mentioned adhesive composition K was used.

[Example 12]
An adhesive composition L was obtained in the same manner as in Example 10 except that the amount of trimethylolpropane toluene diisocyanate added was 2.5 parts based on 100 parts of the solid content of the acrylic polymer solution.
A polarizing plate with an adhesive layer and a retardation layer was obtained in the same manner as in Example 1 except that the above-mentioned adhesive composition L was used.

[Example 13]
An adhesive composition M was obtained in the same manner as in Example 10 except that the addition amount of trimethylolpropane toluene diisocyanate was set to 10 parts with respect to 100 parts of the solid content of the acrylic polymer solution.
A polarizing plate with an adhesive layer and a retardation layer was obtained in the same manner as in Example 1 except that the above-mentioned adhesive composition M was used.

[Comparative Example 1]
An adhesive composition N was obtained in the same manner as in Example 2 except that the addition amount of trimethylolpropane xylene diisocyanate was 0.02 parts with respect to 100 parts of the solid content of the acrylic polymer solution.
A polarizing plate with an adhesive layer and a retardation layer was obtained in the same manner as in Example 1 except that the above-mentioned adhesive composition N was used.

(Evaluation)
The polarizing plates with retardation layers obtained in the examples and comparative examples were evaluated as follows. The results are shown in Table 2.
＜ Heat resistance ＞
The polarizing plate with a retardation layer was cut into a size of 120 mm × 60 mm, and the surface on the side of the retardation layer B was bonded to the glass through the adhesive used in Example 1 to prepare a test sample. After putting this test sample in an 85 ° C oven for 500 hours, the presence or absence of cracks in the retardation layer was confirmed with an optical microscope.
The heat resistance was evaluated based on the following criteria.
◎ ...... No cracks occurred in the retardation layer.
◎ ・ ・ A crack occurs from a portion of the retardation layer starting from the adhesion of foreign matter.
○ ・ ・ ・ A crack occurs in a part of the retardation layer, but it is a level that cannot be seen visually.
Δ ・ ・ ・ A crack occurs in a part of the retardation layer, and it is a level that can be confirmed visually.
× ... A large number of cracks occurred on the entire surface of the retardation layer.

[Table 2]

It is apparent from Table 2 that cracks in the retardation layer of the polarizing plate with a retardation layer in the embodiment are suppressed. In addition, Examples 2 to 13 containing an ultraviolet absorber as an adhesive composition were excellent in ultraviolet absorption characteristics, and Examples 5 to 6 and 8 to 13 further containing a pigment compound were particularly excellent in ultraviolet absorption characteristics.
[Industrial availability]

The optical laminated body of the present invention can be preferably used for an image display device such as an organic EL display device.

10‧‧‧ polarizing plate

20‧‧‧ the first phase difference layer

30‧‧‧ Adhesive layer

40‧‧‧ 2nd phase difference layer

50‧‧‧ Adhesive layer

100‧‧‧ polarizing plate with retardation layer

FIG. 1 is a schematic cross-sectional view of a polarizing plate with a retardation layer according to an embodiment of the present invention.

Claims (10)

A polarizing plate with a retardation layer includes a polarizing plate, a first retardation layer, an adhesive layer, and a second retardation layer in this order. The first retardation layer and the second retardation layer include a liquid crystal compound, and The adhesive constituting the above-mentioned adhesive layer contains 0.05 parts by weight or more of an isocyanate crosslinking agent with respect to 100 parts by weight of the base polymer. For example, the polarizing plate with a retardation layer according to claim 1, wherein the base polymer is a (meth) acrylic polymer. For example, the polarizing plate with a retardation layer in claim 1, wherein the base polymer contains a carboxyl group-containing monomer as a monomer component. For example, the polarizing plate with a retardation layer in claim 2, wherein the base polymer contains a carboxyl group-containing monomer as a monomer component. The polarizing plate with a retardation layer according to any one of claims 1 to 4, wherein the adhesive constituting the adhesive layer further includes an ultraviolet absorber. For example, the polarizing plate with a retardation layer in claim 5, wherein the ultraviolet absorber has 0 to 3 hydroxyl groups in a molecular structure. The polarizing plate with a retardation layer according to any one of claims 1 to 4, wherein the adhesive constituting the adhesive layer further includes a pigment compound having an absorption spectrum whose maximum absorption wavelength exists in a wavelength range of 380 nm to 430 nm. For example, the polarizing plate with a retardation layer in claim 5, wherein the adhesive constituting the adhesive layer further includes a pigment compound having an absorption spectrum whose maximum absorption wavelength exists in a wavelength region of 380 nm to 430 nm. For example, the polarizing plate with a retardation layer in claim 6, wherein the adhesive constituting the adhesive layer further includes a pigment compound having an absorption spectrum whose maximum absorption wavelength exists in a wavelength range of 380 nm to 430 nm. An organic EL display device having a polarizing plate with a retardation layer as in any one of claims 1 to 9.