WO2021131505A1

WO2021131505A1 - Optical laminate and image display device

Info

Publication number: WO2021131505A1
Application number: PCT/JP2020/044453
Authority: WO
Inventors: 亨神野; 悠司淺津; 白石　貴志
Original assignee: 住友化学株式会社
Priority date: 2019-12-23
Filing date: 2020-11-30
Publication date: 2021-07-01
Also published as: KR20220116272A; CN114846375A; JP2021099477A; TW202129322A

Abstract

[Problem] To provide a novel optical laminate in which color defects are suppressed in end sections of a polarizer at high temperature and high humidity. [Solution] An optical laminate having a polarizer and a selectively light-absorbing pressure-sensitive adhesive layer that is laminated in contact with the polarizer, the optical laminate being such that: iodine in the polarizer is oriented in an adsorption orientation, and the boron content of the polarizer is 5.0 mass% or less; and a pressure-sensitive adhesive composition for forming the selectively light-absorbing pressure-sensitive adhesive layer contains a selectively light-absorbing polymer.

Description

Optical laminate and image display device

The present invention relates to an optical laminate and a display device.

Polarizing plates made by laminating and laminating a protective film on one or both sides of a polarizer are used for image display devices such as liquid crystal display devices such as mobile televisions and organic electroluminescence (organic EL) display devices, especially in recent years. It is an optical member widely used in various mobile devices such as telephones, smartphones, and tablet terminals.
The polarizing plate is often used by being bonded to an image display element (liquid crystal cell, organic EL display element, etc.) via an adhesive layer (for example, Japanese Patent Application Laid-Open No. 2010-229321 (Patent Document 1)). Therefore, the polarizing plate may be marketed in the form of a polarizing plate with an adhesive layer in which an adhesive layer is previously provided on one surface of the polarizing plate.

In addition, mobile devices are often used in harsh environments of high temperature and high humidity, and high durability is required as a polarizer. The JP 2013-105036 (Patent Document 2), by increasing the boric acid content in the polarizer, by generating many borate crosslinked, present in high stability I ₃ complex is highly oriented It is described that the occurrence of blue leak is suppressed and a polarizer having excellent low-temperature and high-humidity durability can be obtained.

Japanese Unexamined Patent Publication No. 2010-229321 Japanese Unexamined Patent Publication No. 2013-105036

In the polarizing plate, there was a problem that color loss was likely to occur at the end of the polarizer in a high temperature and high humidity environment. Such a problem was remarkable in the configuration in which the protective film was laminated and laminated on only one side of the polarizer. Although a method of suppressing color loss of the polarizer by increasing the boron content in the polarizer is known, there is a problem that the method tends to shrink due to heating.

An object of the present invention is to provide a novel optical laminate in which color loss is suppressed at the end of a polarizer under high temperature and high humidity.

The present invention provides an optical laminate illustrated below and an image display device using the same.
[1] An optical laminate having a polarizer and a light selective absorbing pressure-sensitive adhesive layer laminated in contact with the polarizer.
Iodine is adsorbed and oriented in the polarizer, and the boron content is 5.0% by mass or less.
The pressure-sensitive adhesive composition forming the light-selective-absorbing pressure-sensitive adhesive layer is an optical laminate containing a light-selective-absorbing polymer.
[2] The optical laminate according to [1], further comprising a protective film laminated on the side of the polarizer opposite to the light selective absorption pressure-sensitive adhesive layer side.
[3] The photoselective absorbent polymer has the following chemical formula (1):
> NC = CC = C <(1)
[However, not all of one N atom and four C atoms constituting the chemical formula (1) form a part or all of the aromatic heterocycle. ]
The optical laminate according to [1] or [2], which is a resin containing a structural unit having the structure shown by and having a glass transition temperature of 40 ° C. or lower.
[4] In the photoselective absorbent polymer, the content of the structural unit having the structure represented by the chemical formula (1) is 0.01 part by mass or more and 50 parts by mass or less with respect to 100 parts by mass of all the structural units. , [3].
[5] The optical laminate according to any one of claims [1] to [4], wherein the photoselective absorbent polymer has a weight average molecular weight of 300,000 or more.
[6] The pressure-sensitive adhesive composition does not contain a light selective absorber, or the content of the light selective absorber is 0.1 parts by mass or less with respect to 100 parts by mass of all resin components, [1] to [ 5] The optical laminate according to any one of the items.
[7] The optical lamination according to any one of [1] to [6], further comprising a λ / 4 retardation layer laminated on the side of the light selective absorbing pressure-sensitive adhesive layer opposite to the polarizer. body.
[8] The optical laminate according to any one of [1] to [7], which is an antireflection polarizing plate.
[9] An image display device including an image display panel and the optical laminate according to [8] arranged in front of the image display panel.
[10] The image display device according to [9], which is an organic EL display device.

According to the present invention, it is possible to provide an optical laminate in which color loss is suppressed at an end portion of a polarizer in a high temperature and high humidity environment, and an image display device including the same.

It is the schematic sectional drawing which shows an example of the optical laminated body of this invention. It is the schematic sectional drawing which shows another example of the optical laminated body of this invention. It is a figure which shows an example of the observation image with an optical microscope. It is a figure which shows an example of the data which converted the observation image into black-and-white 256 gradations.

Hereinafter, embodiments of the present invention will be described with reference to the drawings, but the present invention is not limited to the following embodiments. In all the drawings below, the scale is appropriately adjusted to make it easier to understand each component, and the scale of each component shown in the drawings does not necessarily match the scale of the actual component.

<Optical laminate>
The optical laminate of the present invention has a polarizer and a light selective absorbing pressure-sensitive adhesive layer laminated in contact with the polarizer. An example of the layer structure of the optical laminate of the present invention is shown in FIGS. 1 and 2.
FIG. 1 is a schematic cross-sectional view of an example of the optical laminate of the present invention. The optical laminate 100 shown in FIG. 1 has a protective film 11, a polarizer 10, and a light selective absorbing pressure-sensitive adhesive layer 20 in this order.

FIG. 2 is a schematic cross-sectional view of an example of the optical laminate of the present invention. The optical laminate 200 shown in FIG. 2 has an optical laminate 100 shown in FIG. 1 and a retardation laminate 300 laminated on the light selective absorption adhesive layer 20 side of the optical laminate 100. The retardation laminate 300 includes a first retardation layer 30, an adhesive layer 33, a second retardation layer 31, and a second adhesive in order from the light selective absorption pressure-sensitive adhesive layer 20 side of the optical laminate 100. It has a layer 32 and.

The thicknesses of the

optical laminates

100 and 200 are not particularly limited because they differ depending on the functions required of the optical laminate and the application of the optical laminate, but for example, they may be 5 μm or more and 200 μm or less, and 10 μm or more and 150 μm or less. It may be 120 μm or less.

The light selective absorption pressure-sensitive adhesive layer contains a light selective absorption polymer. In the optical laminate of the present invention, at least the light selective absorption pressure-sensitive adhesive layer has light selective absorption performance, so that the optical laminate as a whole also has light selective absorption performance. The light selective absorption performance refers to a property of easily absorbing light having a specific wavelength, and has at least one absorption maximum in the ultraviolet wavelength region to the visible light region. For example, when the light selective absorption pressure-sensitive adhesive layer has an ultraviolet absorbing ability, the optical laminate arranged on the image display element has a function of protecting the image display element from ultraviolet rays.

The optical laminate of the present invention may have a structure including a layer having light selective absorption performance in addition to the light selective absorption pressure-sensitive adhesive layer. Examples of the other layer include the protective film 11. In the present invention, the light selective absorption adhesive layer has the light selective absorption performance and contributes to the development of the light selective absorption performance of the entire optical laminate, so that the light selective absorption performance of the other layers can be improved. The degree of design freedom can be improved. For example, the protective film 11 may need to be designed to be thicker in order to improve the light selective absorption performance, but the protective film 11 has a high degree of freedom in designing the light selective absorption performance. It becomes easy to make a thin film.

The light selective absorption pressure-sensitive adhesive layer has a structure in which the light selective absorption polymer has light selective absorption performance and contributes to the development of the light selective absorption performance of the light selective absorption pressure-sensitive adhesive layer. The adhesive layer can be configured not to contain a light selective absorber or to reduce the content of the light selective absorber to suppress color loss at the ends of the polarizer under high temperature and high humidity. Can be done.

The present inventors have found that there is a correlation between the content of the light selective absorber contained in the pressure-sensitive adhesive layer and the degree of color loss at the end of the polarizer under high temperature and high humidity. .. Based on this finding, when a light selective absorber having a relatively low molecular weight is used, the light selective absorber in the pressure-sensitive adhesive layer tends to migrate to the polarizer side under high temperature and high humidity, and such migration tends to occur in color. It is considered to be one of the factors that cause omission. The present inventors have conducted further diligent studies, and imparted the light selective absorption performance to the pressure-sensitive adhesive layer by a method of containing a light selective absorption polymer instead of a method of adding a light selective absorption agent. The present invention has been made by finding that color loss at the end of a polarizer under high temperature and high humidity can be suppressed. Since the photoselective absorptive polymer has a relatively large molecular weight, it is considered that the transfer to the polarizer is suppressed and the color loss at the end of the polarizer is suppressed.

[Polarizer]
The polarizer has a property of absorbing linearly polarized light having a vibration plane parallel to its absorption axis and transmitting linearly polarized light having a vibration plane orthogonal to the absorption axis (parallel to the transmission axis). The polarizer 10 in the optical laminate of the present invention has iodine adsorbed and oriented, and has a boron content of 5.0% by mass or less.
With a structure in which the boron content is 5.0% by mass or less, preferably 4.5% by mass or less, shrinkage caused by heating can be suppressed. The content of boron is preferably 0.5% by mass or more, and more preferably 1% by mass or more. In the polarizer 10, the smaller the boron content, the more likely it is that color loss will occur at the ends of the polarizer under high temperature and high humidity. Boron in the polarizer 10 improves the degree of cross-linking of the polarizer 10 and contributes to stably retaining iodine in the polarizer 10. Therefore, when the boron content is low, iodine is stably retained. It is considered that it cannot be held and color loss occurs. In the present invention, even if the boron content of the polarizer 10 is 5.0% by mass or less, color loss under high temperature and high humidity can be suppressed.

Examples of the polarizer 10 include a stretched film or a stretched layer on which a dichroic dye having absorption anisotropy is adsorbed, a cured product of a polymerizable liquid crystal compound, and a liquid crystal cured layer containing a dichroic dye. The dichroic dye refers to a dye having a property in which the absorbance in the major axis direction and the absorbance in the minor axis direction of the molecule are different, and iodine is preferably used as the dye.

The polarizer, which is a stretched film on which a dye having absorption anisotropy is adsorbed, is usually obtained by uniaxially stretching a polyvinyl alcohol-based resin film or dyeing the polyvinyl alcohol-based resin film with a dichroic dye such as iodine. , The step of adsorbing the dichroic dye, the step of treating the polyvinyl alcohol-based resin film on which the dichroic dye is adsorbed with an aqueous boric acid solution, and the step of washing with water after the treatment with the aqueous boric acid solution can be produced. ..

The thickness of the polarizer is usually 30 μm or less, preferably 15 μm or less, more preferably 13 μm or less, further preferably 10 μm or less, and particularly preferably 8 μm or less. The thickness of the polarizer is usually 2 μm or more, preferably 3 μm or more, and may be, for example, 5 μm or more.

The polyvinyl alcohol-based resin is obtained by saponifying the polyvinyl acetate-based resin. As the polyvinyl acetate-based resin, in addition to polyvinyl acetate which is a homopolymer of vinyl acetate, a copolymer of vinyl acetate and another monomer copolymerizable therewith is used. Examples of other monomers copolymerizable with vinyl acetate include unsaturated carboxylic acid compounds, olefin compounds, vinyl ether compounds, unsaturated sulfone compounds, and (meth) acrylamide compounds having an ammonium group. ..

The saponification degree of the polyvinyl alcohol-based resin is usually about 85 mol% or more and 100 mol% or less, preferably 98 mol% or more. The polyvinyl alcohol-based resin may be modified, and polyvinyl formal, polyvinyl acetal, and the like modified with aldehydes can also be used. The degree of polymerization of the polyvinyl alcohol-based resin is usually 1000 or more and 10000 or less, preferably 1500 or more and 5000 or less.

The polarizer, which is a stretched layer on which a dye having absorption anisotropy is adsorbed, is usually a step of applying a coating liquid containing the polyvinyl alcohol-based resin on a base film, and a step of uniaxially stretching the obtained laminated film. , A step of adsorbing a dichroic dye to form a polarizer by dyeing a polyvinyl alcohol-based resin layer of a uniaxially stretched laminated film with a dichroic dye such as iodine, a film on which the dichroic dye is adsorbed. Can be produced through a step of treating with an aqueous boric acid solution and a step of washing with water after the treatment with the aqueous boric acid solution. The base film used for forming the polarizer may be used as the protective film 11. If necessary, the base film may be peeled off from the polarizer. The material and thickness of the base film may be the same as the material and thickness of the protective film 11 described later.

[Protective film]
The protective film 11 is made of an optically transparent thermoplastic resin such as a cyclic polyolefin resin; a cellulose acetate resin composed of a resin such as triacetyl cellulose or diacetyl cellulose; a resin such as polyethylene terephthalate, polyethylene naphthalate, or polybutylene terephthalate. Polyester resin; Polycarbonate resin; (meth) acrylic resin; Polypropylene resin, a coating layer or film composed of one or a mixture of two or more of these. The protective film 11 may contain a light selective absorber described later. Since the light selective absorber contained in the protective film 11 is held in the protective film 11, it is unlikely that the light selective absorber will be transferred to the polarizer.

A hard coat layer may be formed on the protective film 11. The hard coat layer may be formed on one surface of the protective film 11 or may be formed on both sides. By providing the hard coat layer, the protective film 11 having improved hardness and scratchability can be obtained. The hard coat layer may be, for example, a cured layer such as an acrylic resin, a silicone resin, a polyester resin, a urethane resin, an amide resin, or an epoxy resin. The hard coat layer may contain additives to improve strength. Additives are not limited and include inorganic fine particles, organic fine particles, or mixtures thereof. The hard coat layer is, for example, a cured layer of an ultraviolet curable resin. Examples of the ultraviolet curable resin include acrylic resin, silicone resin, polyester resin, urethane resin, amide resin, epoxy resin and the like.

The thickness of the protective film 11 is usually 1 μm or more and 100 μm or less, preferably 5 μm or more and 80 μm or less, more preferably 8 μm or more and 60 μm or less, and 12 μm or more and 45 μm or less from the viewpoint of strength and handleability. Is more preferable.

The resin film, which is the protective film 11, is attached to the polarizer 10 via, for example, an adhesive layer. Examples of the adhesive forming the adhesive layer include a water-based adhesive, an active energy ray-curable adhesive, and a thermosetting adhesive, and a water-based adhesive and an active energy ray-curable adhesive can be used. preferable. The two opposing surfaces bonded via the adhesive layer may be subjected to corona treatment, plasma treatment, flame treatment or the like in advance, or may have a primer layer or the like.

[Light selective absorption adhesive layer]
The photoselective absorbent pressure-sensitive adhesive layer 20 can be formed by applying a diluent in which a pressure-sensitive adhesive composition containing a light-selective absorbent polymer is dissolved or dispersed in an organic solvent onto a substrate and drying it. A plastic film is preferable as the base material, and specific examples thereof include a release film that has been subjected to a mold release treatment. Examples of the release film include those in which one surface of a film made of a resin such as polyethylene terephthalate, polybutylene terephthalate, polycarbonate, or polyarylate is subjected to a mold release treatment such as silicone treatment.

The thickness of the light selective absorption pressure-sensitive adhesive layer is, for example, 0.1 μm or more and 150 μm or less. When laminated with an image display panel, the thickness of the light selective absorption adhesive layer is usually 8 μm or more and 60 μm or less, and in terms of thinning, it is 30 μm or less, further 25 μm or less, and particularly 20 μm or less. Is preferable. When laminated with another optical film, for example, a λ / 4 retardation layer, the thickness of the light selective absorption pressure-sensitive adhesive layer is usually 2 μm or more and 30 μm or less, preferably 25 μm or less, more preferably 20 μm or less, particularly. It is preferably 18 μm or less, preferably 3 μm or more, for example, 10 μm or more, but in terms of further thinning, 10 μm or less, particularly 7 μm or less is preferable.

The light selective absorbing pressure-sensitive adhesive layer 20 preferably has an absorbance of 0.1 or more and 1.6 or less at a wavelength of 410 nm. This is because the light selective absorption pressure-sensitive adhesive layer 20 having such an absorbance makes it easy to form the entire optical laminate in a thin shape while exhibiting desired light selective absorption performance as the entire optical laminate.

The light selective absorbing pressure-sensitive adhesive layer usually has an absorbance at a wavelength of 390 nm of 5.0 or less, and may be 4.5 or less.
The light selective absorbing pressure-sensitive adhesive layer usually has an absorbance at a wavelength of 400 nm of 5.0 or less, and may be 4.5 or less.
The light selective absorbing pressure-sensitive adhesive layer has an absorbance at a wavelength of 420 nm of usually 1.00 or less, preferably 0.60 or less, more preferably 0.40 or less, and 0.00 or more.
The light selective absorbing pressure-sensitive adhesive layer has an absorbance at a wavelength of 430 nm, usually less than 0.20, preferably 0.18 or less, more preferably 0.10 or less, particularly preferably 0.05 or less, and 0.00 or more. is there.
The light selective absorbing pressure-sensitive adhesive layer has an absorbance at a wavelength of 440 nm, usually less than 0.10, preferably 0.05 or less, and 0.00 or more. When the absorbance at each wavelength is in the above range, the light in the visible light region can be transmitted as it is while sufficiently absorbing the light in the ultraviolet region.

The light selective absorption pressure-sensitive adhesive layer is preferably a pressure-sensitive adhesive layer satisfying the following formula (3), and more preferably a pressure-sensitive adhesive layer satisfying the formula (4).
A (405) ≥ 0.5 (3)
[In formula (3), A (405) represents the absorbance at a wavelength of 405 nm. ]
A (405) / A (440) ≧ 5 (4)
[In the formula (4), A (405) represents the absorbance at a wavelength of 405 nm, and A (440) represents the absorbance at a wavelength of 440 nm. ]

The larger the value of A (405), the higher the absorption at the wavelength of 405 nm. When the value of A (405) is less than 0.5, the absorption at a wavelength of 405 nm is low, and the deterioration of members (for example, display devices such as organic EL elements and liquid crystal retardation films) that are easily deteriorated by light near 400 nm is deteriorated. It is easy to happen. The value of A (405) is preferably 0.6 or more, more preferably 0.8 or more, and particularly preferably 1.0 or more. There is no particular upper limit, but it is usually 10 or less.

The value of A (405) / A (440) represents the magnitude of absorption at a wavelength of 405 nm with respect to the magnitude of absorption at a wavelength of 440 nm, and the larger this value is, the more specific absorption is in the wavelength region near 405 nm. Represent. The value of A (405) / A (440) is preferably 10 or more, more preferably 30 or more, further preferably 75 or more, and particularly preferably 100 or more.

[Adhesive composition]
(Light selective absorbent polymer)
The pressure-sensitive adhesive composition comprises a light-selective absorbent polymer. The light selective absorption polymer is a polymer having light selective absorption performance. The light selective absorption polymer can preferably absorb light having a wavelength in the region of 360 nm to 420 nm. The photoselective absorptive polymer contains a photoselective absorptive structural unit having a moiety having a light selective absorption performance. The light selective absorption structural unit preferably has a portion having a light selective absorption performance in the side chain. Examples of the site having the light selective absorption performance include a benzophenone group, a benzotriazole group, and a structure represented by the following chemical formula (1).

The photoselective absorptive polymer is preferably composed of the following chemical formula (1):
> NC = CC = C <(1)
[However, not all of one N atom and four C atoms constituting the chemical formula (1) form a part or all of the aromatic heterocycle. ]
A resin (A) containing a structural unit having a structure represented by (hereinafter referred to as “merocyanine structure”) as a photoselective absorbing structural unit and having a glass transition temperature of 40 ° C. or lower.
The resin (A) may have a merocyanine structure in the main chain or a side chain. The resin (A) more preferably contains a structural unit having a merocyanine structure in the side chain.

The glass transition temperature (Tg) of the resin (A) is 40 ° C. or lower, preferably 20 ° C. or lower, more preferably 10 ° C. or lower, and even more preferably 0 ° C. or lower. The glass transition temperature of the resin (A) is usually −80 ° C. or higher, preferably −60 ° C. or higher, more preferably −50 ° C. or higher, and even more preferably −45 ° C. or higher. , -30 ° C or higher is particularly preferable. When the glass transition temperature of the resin (A) is 40 ° C. or lower, it is advantageous to improve the adhesion of the light selective absorption pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition containing the resin (A) to the adherend. .. Further, when the glass transition temperature of the resin (A) is −80 ° C. or higher, the durability of the light selective absorbing pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition containing the resin (A) (appearance defects during a high temperature test). : Advantageous in improving coagulation failure, etc.). The glass transition temperature can be measured by a differential scanning calorimeter (DSC).

The structural unit having a merocyanine structure in the side chain is not particularly limited, but is preferably a structural unit derived from a compound having a polymerizable group and a merocyanine structure.

The compound having a polymerizable group and a merocyanine structure preferably satisfies the following formula (1-a), and more preferably satisfies the formula (2-a).
ε (405) ≧ 5 (1-a)
[In formula (1-a), ε (405) represents the gram absorption coefficient of a compound having a polymerizable group and a merocyanine structure at a wavelength of 405 nm. The unit of the gram extinction coefficient is L / (g · cm). ]
ε (405) / ε (440) ≧ 20 (2-a)
[In formula (2-a), ε (405) represents the gram extinction coefficient of a compound having a polymerizable group and a merocyanine structure at a wavelength of 405 nm, and ε (440) represents a polymerizable group and a merocyanine structure at a wavelength of 440 nm. Represents the gram extinction coefficient of the compound. ]

The compound having a polymerizable group and a merocyanine structure preferably has a value of ε (405) of 5 L / (g · cm) or more, more preferably 10 L / (g · cm) or more, and 20 L / (g · cm) or more. It is more preferably (g · cm) or more, further preferably 30 L / (g · cm) or more, and usually 500 L / (g · cm) or less. A compound having a larger value of ε (405) is more likely to absorb light having a wavelength of 405 nm, and is more likely to exhibit a function of suppressing deterioration due to ultraviolet rays or visible light having a short wavelength.
The compound having a polymerizable group and a merocyanine structure preferably has a value of ε (405) / ε (440) of 20 or more, more preferably 40 or more, further preferably 70 or more, and even more preferably 80 or more. Is particularly preferable. The resin containing a compound having a large value of ε (405) / ε (440) absorbs light in the vicinity of 405 nm without disturbing the color expression of the display device, and the light of a display device such as a retardation film or an organic EL element. Deterioration can be suppressed.

Examples of the structural unit having a merocyanine structure in the side chain include a structural unit derived from the compound represented by the formula (I).

[In formula (I), R ¹ , R ² , R ³ , R ⁴ and R ⁵ are aliphatic hydrocarbons having 1 to 25 carbon atoms which may independently have a hydrogen atom and a substituent. It represents an aromatic hydrocarbon group having 6 to 15 carbon atoms, a heterocyclic group or an ethylenically unsaturated group which may have a group or a substituent, and is contained in the aliphatic hydrocarbon group or the aromatic hydrocarbon group. -CH _2- may be replaced with -NR ^1A- , -SO _2- , -CO-, -O- or S-.
R ⁶ and R ⁷ independently represent a hydrogen atom, an alkyl group having 1 to 25 carbon atoms, an electron-withdrawing group, or an ethylenically unsaturated group.
R ^1A represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
R ¹ and R ² may be connected to each other to form a ring structure, R ² and R ³ may be connected to each other to form a ring structure, and R ² and R ⁴ may be connected to each other to form a ring structure. R ³ and R ⁶ may be connected to each other to form a ring structure, R ⁵ and R ⁷ may be connected to each other to form a ring structure, and R ⁶ and R ^{7 may be formed.} May be connected to each other to form a ring structure.
However, ^one of R 1 to R ⁷ is an ethylenically unsaturated group]

Examples of the aliphatic hydrocarbon group having 1 to 25 carbon atoms represented by R ¹ to R ⁵ include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a tert-butyl group and a sec-butyl group. Group, n-pentyl group, isopentyl group, n-hexyl group, isohexyl group, n-octyl group, isooctyl group, n-nonyl group, isononyl group, n-decyl group, isodecyl group, n-dodecyl group, isododecyl group, Linear or branched alkyl group having 1 to 25 carbon atoms such as undecyl group, lauryl group, myristyl group, cetyl group and stearyl group: 3 to 25 carbon atoms such as cyclopropyl group, cyclobutyl group, cyclopentyl group and cyclohexyl group. Cycloalkyl group: A cycloalkylalkyl group having 4 to 25 carbon atoms such as a cyclohexylmethyl group, and an alkyl group having 4 to 25 carbon atoms is preferable.
Examples of the substituent that the aliphatic hydrocarbon group having 1 to 25 carbon atoms represented by R ¹ to R ⁵ may have include a hydroxy group, a cyano group, a halogen atom, a mercapto group, an amino group, a nitro group and the like. Can be mentioned.
Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

Examples of the aromatic hydrocarbon group having 6 to 15 carbon atoms represented by R ¹ to R ⁵ include an aryl group having 6 to 15 carbon atoms such as a phenyl group, a naphthyl group, an anthracenyl group and a biphenyl group; a benzyl group and a phenylethyl group. Examples thereof include an aralkyl group having 7 to 15 carbon atoms such as a group, a naphthylmethyl group and phenyl.
Examples of the substituent that the aromatic hydrocarbon group having 6 to 15 carbon atoms represented by R ¹ to R ⁵ may have include a hydroxy group, a cyano group, a halogen atom, a mercapto group, an amino group and a nitro group. Alkoxy group, alkylthio group, alkoxycarbonyl group, acyl group, acyloxy group, -C (NR ^2A ) R ^2B , -CONR ^3A R ^3B , -SO ₂ R ^4A (R ^2A , R ^2B , R ^3A and R ^3B , respectively. Independently, it represents a hydrogen atom or an alkyl group ^{having 1 to 6 carbon atoms, and R 4A} represents an alkyl group having 1 to 6 carbon atoms.)

Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
Examples of the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, an octyloxy group, a 2-ethylhexyloxy group, a nonyloxy group, a decyloxy group, an undecyloxy group and a dodecyloxy group. Alkoxy groups having 1 to 12 carbon atoms can be mentioned.
Examples of the alkylthio group include an alkylthio group having 1 to 12 carbon atoms such as a methylthio group, an ethylthio group, a propylthio group and a butylthio group.
Examples of the acyl group include an acyl group having 2 to 13 carbon atoms such as an acetyl group, a propionyl group and a butyryl group.
Examples of the acyloxy group include a methylcarbonyloxy group, an ethylcarbonyloxy group, an n-propylcarbonyloxy group, an isopropylcarbonyloxy group, an n-butylcarbonyloxy group, a sec-butylcarbonyloxy group, a tert-butylcarbonyloxy group, and a pentylcarbonyl. Examples thereof include acyloxy groups having 2 to 13 carbon atoms such as an oxy group, a hexylcarbonyloxy group, an octylcarbonyloxy group and a 2-ethylhexylcarbonyloxy group.
Examples of the alkoxycarbonyl group include a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, a butoxycarbonyl group, a pentyloxycarbonyl group, a hexyloxycarbonyl group, an octyloxycarbonyl group, a 2-ethylhexyloxycarbonyl group, a nonyloxycarbonyl group, and a decyl. Examples thereof include alkoxycarbonyl groups having 2 to 13 carbon atoms such as an oxycarbonyl group, an undecyloxycarbonyl group, and a dodecyloxycarbonyl group.
The -CONR ^3A R ^3B, aminocarbonyl group, methylaminocarbonyl group, dimethylaminocarbonyl group, ethylaminocarbonyl group, and the like methyl aminocarbonyl group.
Examples of -C (NR ^2A ) R ^2B include a methylimino group, a dimethylimino group, a methylethylimino group and the like.
Examples of -SO ₂ R ^4A include a methyl sulfonyl group and an ethyl sulfonyl group.

^Examples of the alkyl group having 1 to 6 carbon atoms represented by R 1A and R ^1B include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a tert-butyl group, a sec-butyl group and the like. Can be mentioned.

Examples of the heterocyclic group represented by R ¹ to R ⁵ include a pyrrolidine ring group, a pyrolin ring group, an imidazolidine ring group, an imidazoline ring group, an oxazoline ring group, a thiazolin ring group, a piperidine ring group, a morpholine ring group, and a piperazine ring. An aliphatic heterocyclic group having 4 to 20 carbon atoms or an aliphatic heterocyclic group having 3 to 20 carbon atoms such as a group, an indole ring group, an isoindole ring group, a quinoline ring group, a thiophene ring group, a pyrrol ring group, a thiazolin ring group and a furan ring group. Examples include aromatic heterocyclic groups.

Alkyl groups having 1 to 25 carbon atoms represented by R ⁶ and R ⁷ include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, tert-butyl group, sec-butyl group and n. -Pentyl group, isopentyl group, n-hexyl group, isohexyl group, n-octyl group, isooctyl group, n-nonyl group, isononyl group, n-decyl group, isodecil group, n-dodecyl group, isododecyl group, undecyl group, Examples thereof include linear or branched alkyl groups having 1 to 25 carbon atoms such as lauryl group, myristyl group, cetyl group and stearyl group.

Examples of the electron-withdrawing group represented by R ⁶ and R ⁷ include a cyano group, a nitro group, a halogen atom, an alkyl group substituted with a halogen atom, and a group represented by the formula (I-1). ..

[In the formula, R ¹¹¹ represents a hydrogen atom or a hydrocarbon group having 1 to 25 carbon atoms, and at least one of the methylene groups contained in the alkyl group may be substituted with an oxygen atom.
X ¹ ^{^{^{^{is, -CO- * 1, -COO- * 1}}}} , -CS- * 1, -CSS- * 1, -CSNR 112 - * 1, -CONR 113 - * 1, -CNR 114 - * 1 or SO Represents _2- * ^1.
R ¹¹² , R ¹¹³ and R ¹¹⁴ independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms or a phenyl group.
* ¹ represents a bond with R ^111.
* Represents a bond with a carbon atom. ]

Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
Alkyl groups substituted with halogen atoms include, for example, trifluoromethyl group, perfluoroethyl group, perfluoropropyl group, perfluoroisopropyl group, perfluorobutyl group, perfluorosec-butyl group, perfluorotert-butyl group, perfluoropentyl group and Examples thereof include a perfluoroalkyl group such as a perfluorohexyl group. The number of carbon atoms of the alkyl group substituted with the halogen atom is usually 1 to 25.

Examples of the hydrocarbon group having 1 to 25 carbon atoms represented by R ¹¹¹ include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a tert-butyl group, a sec-butyl group and an n-pentyl group. Group, isopentyl group, n-hexyl group, isohexyl group, n-octyl group, isooctyl group, n-nonyl group, isononyl group, n-decyl group, isodecyl group, n-dodecyl group, isododecyl group, undecyl group, lauryl group , A linear or branched alkyl group having 1 to 25 carbon atoms such as a myristyl group, a cetyl group and a stearyl group: a cycloalkyl group having 3 to 25 carbon atoms such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group and a cyclohexyl group; Cycloalkylalkyl group having 4 to 25 carbon atoms such as cyclopropylmethyl group and cyclohexylmethyl group; aryl group having 6 to 25 carbon atoms such as phenyl group, naphthyl group, anthracenyl group and biphenyl group; benzyl group, phenylethyl group, etc. Examples thereof include an aralkyl group having 7 to 25 carbon atoms such as a naphthylmethyl group and phenyl.
^Examples of the alkyl group having 1 to 6 carbon atoms represented by R 112, R ¹¹³ and R ¹¹⁴ include the same alkyl group having 1 to 6 carbon atoms represented by ^{R 1A.}

R ¹¹¹ is preferably an alkyl group having 4 to 25 carbon atoms, and more preferably an alkyl group having 4 to 12 carbon atoms.
X ¹ is preferably −CO− * ¹ and COO− * ^1.

The ^{electron-withdrawing groups represented by R 6} and R ⁷ are preferably cyano groups and groups represented by the formula (I-1), respectively.

The ring structure formed by bonding ^{R 1} and R ² ^{to each other is a nitrogen-containing ring structure containing a nitrogen atom to which R 1} and R ² are bonded, and is, for example, a 4-membered ring to a 10-membered ring. A nitrogen-containing heterocycle can be mentioned. The ^{ring structure formed by connecting R 1} and R ² to each other may be monocyclic or polycyclic. Specific examples thereof include a pyrrolidine ring, a pyrroline ring, an imidazolidine ring, an imidazoline ring, an oxazoline ring, a thiazolin ring, a piperidine ring, a morpholine ring, a piperazine ring, an indole ring, and an isoindole ring. The ^{ring formed by bonding R 1} and R ² to each other may have a substituent, and the substituent may have a carbon number of 1 such as a methyl group, an ethyl group, a propyl group, a butyl group, and an isobutyl group. Alkyl groups of to 12; alkoxy groups having 1 to 12 carbon atoms such as methoxy group, ethoxy group, propoxy group, butoxy group and the like can be mentioned.

The ring structure formed by bonding ^{R 2} and R ³ ^{to each other is a nitrogen-containing ring structure containing a nitrogen atom to which R 2} is bonded, and is, for example, a nitrogen-containing heterocycle having a 4-membered ring to a 10-membered ring. Ring is mentioned. The ^{ring structure formed by connecting R 2} and R ³ to each other may be monocyclic or polycyclic. Specifically, it is represented by a pyrrolidine ring, a pyrroline ring, an imidazolidine ring, an imidazoline ring, an oxazoline ring, a thiazolin ring, a piperidine ring, a morpholine ring, a piperazine ring, an indol ring, an isoindole ring and the following formula (I-3). Ring structure can be mentioned.

[In formula (I-3), X represents a nitrogen atom, an oxygen atom, and a sulfur atom.
Ring W ¹ represents a ring having a nitrogen atom and X as constituent elements. ]

Ring W ¹ is preferably a 5-membered ring or a 6-membered ring having a nitrogen atom and X as constituent elements.
Specific examples of the ring structure represented by the formula (I-3) include the following rings.

The ^{ring structure formed by bonding R 2} and R ³ to each other may have a substituent, and the substituent may be a carbon such as a methyl group, an ethyl group, a propyl group, a butyl group or an isobutyl group. Alkyl group of number 1 to 12; alkoxy group having 1 to 12 carbon atoms such as methoxy group, ethoxy group, propoxy group, butoxy group and the like can be mentioned.

The ^{ring structure formed by bonding R 2} and R ³ to each other is preferably a ring structure represented by the following formula (I-4).

[In formula (I-4), R ¹¹ has the same meaning as above. m2 represents an integer from 1 to 7.
R ^11a , R ^11b , R ^11c and R ^11d each independently represent a hydrogen atom or an alkyl group having 1 to 12 carbon atoms.
* Represents a bond with a carbon atom. ]
m2 is preferably 2 or 3, more preferably 2.

Examples of the ^{ring structure formed by bonding R 2} and R ⁴ to each other include a nitrogen-containing ring structure having a 4-membered ring to a 10-membered ring, and a nitrogen-containing ring structure having a 5-membered ring to a 9-membered ring is preferable. The ^{ring structure formed by bonding R 2} and R ⁴ to each other may be monocyclic or polycyclic. These rings may have substituents. Examples of such a ring structure include a pyrrole ring, an indole ring, a pyrimidine ring, and the rings described below.

The ^{ring structure formed by bonding R 2} and R ⁴ to each other may have a substituent, and the substituent may have a number of carbon atoms such as a methyl group, an ethyl group, a propyl group, a butyl group and an isobutyl group. Alkyl group of 1 to 12; alkoxy group having 1 to 12 carbon atoms such as methoxy group, ethoxy group, propoxy group and butoxy group; -NR ^22AR ^{22B such as amino group, methylamino group and dimethylamino group.} Groups (R ^22A and R ^22B each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms); 1 to 12 carbon atoms such as a methyl thio group, an ethyl thio group, a propyl thio group, a butyl thio group, a pentyl thio group, etc. Alkylthio group; Examples thereof include a heterocyclic group having 4 to 9 carbon atoms such as a pyrrolidinyl group, a piperidinyl group and a morpholinyl group.

As a ring structure formed by connecting ^{R 3} and R ⁶ ^{to each other, R 3} -C = CC = C-R ⁶ is a ring structure forming a ring skeleton. For example, a phenyl group and the like can be mentioned.

Examples of the ^{ring structure formed by connecting R 5} and R ⁷ to each other include the ring structures described below. The ^{ring structure formed by bonding R 5} and R ⁷ to each other may have a substituent, and the substituent may have a number of carbon atoms such as a methyl group, an ethyl group, a propyl group, a butyl group and an isobutyl group. Alkyl groups of 1 to 12; alkoxy groups having 1 to 12 carbon atoms such as methoxy group, ethoxy group, propoxy group, butoxy group and the like can be mentioned.

Examples of the ^{ring structure formed by connecting R 6} and R ⁷ to each other include the ring structure described below. The ^{ring structure formed by bonding R 6} and R ⁷ to each other may have substituents (R ₁ to R ₁₆ in the following formula), and the substituents include a methyl group, an ethyl group and a propyl group. An alkyl group having 1 to 12 carbon atoms such as a group, a butyl group and an isobutyl group; an alkoxy group having 1 to 12 carbon atoms such as a methoxy group, an ethoxy group, a propoxy group and a butoxy group; Be done.

[In the formula, * represents a bond with a carbon atom. ]

Examples of the ethylenically unsaturated group represented by R ¹ to R ⁷ include a vinyl group, an α-methyl vinyl group, an acryloyl group, a metaacryloyl group, an allyl group, a styryl group and a group represented by the formula (I-2). Can be mentioned.

[In formula (I-2), X ² represents a vinyl group, an acryloyl group or a meta-acryloyl group.
R ¹¹⁵ represents a divalent aliphatic hydrocarbon group having 1 to 18 carbon atoms, and -CH _2- contained in the aliphatic hydrocarbon group is -O-, -CO-, -CS- or NR ^116. It may be replaced with-.
R ¹¹⁶ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
* Represents a bond with a carbon atom or a nitrogen atom. ]

Examples of the divalent aliphatic hydrocarbon group having 1 to 18 carbon atoms represented by R ¹¹⁵ include a methylene group, an ethylene group, a propane-1,3-diyl group, a propane-1,2-diyl group and butane-1. , 4-diyl group, pentane-1,5-diyl group, hexane-1,6-diyl group, butane-1,3-diyl group, 2-methylpropane-1,3-diyl group, 2-methylpropane- Alcandiyl groups having 1 to 18 carbon atoms such as 1,2-diyl group, pentane-1,4-diyl group and 2-methylbutane-1,4-diyl group: cyclopropanediyl group, cyclobutanediyl group, cyclopentanediyl Examples thereof include a cycloalkandyl group having 3 to 18 carbon atoms such as a group and a cyclohexanediyl group, and a divalent aliphatic hydrocarbon group having 1 to 12 carbon atoms is preferable.
^Examples of the alkyl group having 1 to 6 carbon atoms represented by R 116 include the same alkyl groups having 1 to 6 carbon atoms represented by ^{R 1A.}

The ^{ethylenically unsaturated groups represented by R 1} to R ⁷ are preferably vinyl groups, acryloyl groups, metaacryloyl groups, and groups represented by the formula (I-2), respectively.

It is preferable that any one of R ⁶ and R ^{7 is an electron-withdrawing group.}
It is preferable that either one of R ⁶ and R ^{7 is an ethylenically unsaturated group.}

The structural unit derived from the compound represented by the formula (I) is preferably a structural unit derived from the compound represented by the formula (II).

[In formula (II), R ¹¹ , R ¹² , R ¹³ , R ¹⁴ and R ¹⁵ are aliphatic hydrocarbons having 1 to 25 carbon atoms which may independently have a hydrogen atom and a substituent. Represents an aromatic hydrocarbon group or a heterocyclic group having 6 to 15 carbon atoms which may have a group or a substituent, and —CH ₂ − contained in the aliphatic hydrocarbon group or the aromatic hydrocarbon group is It ^{may be substituted with -NR 11A-} , -SO _2- , -CO-, -O- or S-.
R ¹⁶ and R ¹⁷ independently represent a hydrogen atom, an alkyl group having 1 to 25 carbon atoms, an electron-withdrawing group, or an ethylenically unsaturated group.
R ^11A represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
R ¹² and R ¹³ may be connected to each other to form a ring structure, and R ¹² and R ¹⁴ may be connected to each other to form a ring structure.
However, ^{either one of R 16} or R ¹⁷ is an ethylenically unsaturated group. ]

R ^{11 ~} The substituent may have a number of 1 to 25 aliphatic carbon hydrocarbon groups represented by R ^15, carbon atoms 1 may have a substituent represented by R ¹ ~ The same as the 25 aliphatic hydrocarbon groups can be mentioned.
The aromatic hydrocarbon group having 6 to 15 carbon atoms which may have a substituent represented by R ¹¹ to R ¹⁵ ^{may have a substituent represented by R 1} and has 6 carbon atoms. The same as the aromatic hydrocarbon groups of ~ 15 can be mentioned.
Examples of the heterocycle represented by R ¹¹ to R ¹⁵ include the same heterocycle represented by ^{R 1.}

Examples of the alkyl group having 1 to 25 carbon atoms represented by ^{R 16} and R ¹⁷ include the same alkyl group having 1 to 25 carbon atoms represented by ^{R 6.}
Examples of the electron-withdrawing group represented by R ¹⁶ and R ¹⁷ include the same as the electron-withdrawing group represented by ^{R 6.}
^Examples of the alkyl group having 1 to 6 carbon atoms represented by R 11A and R ^11B include the same alkyl group having 1 to 6 carbon atoms represented by ^{R 1A.}

Examples of the ^{ring structure in which R 12} and R ¹³ can be formed by connecting with each other include the ^{same ring structure in which R 2} and R ³ can be formed by connecting with each other. The ^{ring structure that can be formed by connecting R 12} and R ¹³ to each other is preferably a monocyclic structure.

Examples of the ^{ring structure in which R 12} and R ¹⁴ can be formed by connecting with each other include the ^{same ring structure in which R 2} and R ⁴ can be formed by connecting with each other. The ^{ring structure that can be formed by connecting R 12} and R ¹⁴ to each other is preferably a monocyclic structure. The ^{ring structure formed by connecting R 12} and R ¹⁴ to each other is preferably an aromatic ring, and more preferably a pyrimidine ring structure.

R ¹¹ , R ¹³ and R ¹⁵ are preferably aliphatic hydrocarbon groups having 1 to 25 carbon atoms, which may independently have a substituent, and may have a substituent. It is more preferably an alkyl group having 1 to 25 carbon atoms, and further preferably an alkyl group having 1 to 12 carbon atoms which may have a substituent.
In particular, R ¹¹ is preferably an aliphatic hydrocarbon group having 1 to 10 carbon atoms, more preferably an alkyl group having 1 to 10 carbon atoms, and even more preferably a methyl group.
R ¹² and R ¹⁴ are independently aliphatic hydrocarbon groups having 1 to 25 carbon atoms which may have substituents, or R ¹² and R ¹⁴ are linked to each other to form a ring structure. It is preferable to do so.
R ¹² and R ¹³ are preferably connected to each other to form a ring structure, and more preferably a ring structure represented by the above formula (I-4). Among the ring structures represented by the formula (I-4), the ring structure represented by the formula (I-4-1) or the ring structure represented by the formula (I-4-2) is particularly preferable. It is preferably a ring structure represented by the formula (I-4-1).

It is preferable that one of R ¹⁶ and R ¹⁷ is an ethylenically unsaturated group and the other is an electron-withdrawing group.
The ^{electron-withdrawing groups represented by R 16} and R ¹⁷ may be independently represented by a cyano group, a nitro group, a fluoro group, a trifluoromethyl group, and a group represented by the formula (I-1). preferable. Particularly preferably, it is a cyano group.
The ^{ethylenically unsaturated groups represented by R 16} and R ¹⁷ are preferably vinyl groups, acryloyl groups, metaacryloyl groups, and groups represented by the formula (I-2), respectively. More preferably, * -CO-O- (CH ₂ ) n-X ² , (X ² represents a vinyl group, an acryloyl group or a meta-acryloyl group, and is an integer of n = 1 to 10 (preferably n = 2 to 6). It represents an integer).

The ^{compound represented by the formula (II) in which R 12} and R ¹³ are connected to each other to form a ring structure is a compound represented by the formula (II-A-1) or a compound represented by the formula (II-A-2). ) Is preferable. The ^{compound represented by the formula (II) in which R 12} and R ¹⁴ are linked to each other to form a ring structure is preferably a compound represented by the formula (II-B-1).

[In formula (II-A-1), formula (II-A-2) and formula (II-B-1), R ¹¹ , R ¹⁴ , R ¹⁵ , R ¹⁶ and R ¹⁷ , respectively have the same meaning as above. Represents.
R ^11e , R ^11f , R ^11g , R ^11h , R ^11k , R ^11m , and R ¹¹ⁿ each independently represent a hydrogen atom or an alkyl group having 1 to 12 carbon atoms.
R ^11q and R ^11p are each independently a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, and a group represented by ^{-NR 22A} R ^22B ^{(R 22A} and R ^22B are each independently a hydrogen atom or a hydrogen atom or a group. Represents an alkyl group having 1 to 6 carbon atoms) or a heterocycle. ]

For example, the compound represented by the formula (II) in which the electron-withdrawing group is a cyano group is obtained by reacting the compound represented by the following formula (I') with the compound represented by the formula (L). be able to.

[In the formula, R ²²² represents a divalent linking group and X ² represents a polymerizable group. ]
The reaction between the compound represented by the formula (I') and the compound represented by the formula (L) can be carried out under any conditions used for general Knephener gel condensation. For example, it is preferable to carry out in the presence of a base or a carboxylic acid anhydride. Examples of the base include triethylamine, N, N-diisopropylethylamine, pyridine, piperidine, pyrrolidine, proline, N, N-dimethylaminopyridine, imidazole, sodium hydroxide, potassium hydroxide, potassium carbonate, sodium carbonate, sodium hydrogen carbonate. , Potassium hydrogen carbonate, potassium hydroxide butoxide, sodium hydroxide, sodium hydrogen and the like. Examples of the carboxylic acid anhydride include acetic anhydride, succinic anhydride, phthalic anhydride, maleic anhydride, benzoic anhydride and the like. The amount of the base used is preferably 0.1 to 10 mol with respect to 1 mol of the compound represented by the formula (I'). The amount of acetic anhydride used is preferably 0.2 to 5 mol with respect to 1 mol of the compound represented by the formula (I').
The reaction between the compound represented by the formula (I') and the compound represented by the formula (L) is preferably carried out in an organic solvent. Examples of the organic solvent include toluene, acetonitrile, dichloromethane, trichloromethane and the like.

The reaction between the compound represented by the formula (I') and the compound represented by the formula (L) is to mix the compound represented by the formula (I') and the compound represented by the formula (L). It will be carried out at.
The reaction temperature of the compound represented by the formula (I') and the compound represented by the formula (L) is preferably −40 to 130 ° C., and the reaction time is usually preferably 1 to 24 hours.

The compound represented by the formula (I') can be synthesized, for example, according to the method described in JP-A-2014-194508.

The compound represented by the formula (L) can be obtained, for example, by reacting cyanoacetic acid with a hydroxyalkyl acrylate.
The amount of cyanoacetic acid used is preferably 0.5 to 3 mol with respect to 1 mol of the hydroxyalkyl acrylate.
The reaction between cyanoacetic acid and hydroxyalkyl acrylate can be carried out using any esterification catalyst used in general esterification reactions, but is preferably carried out in the presence of a base and a carbodiimide condensing agent. Examples of the base include triethylamine, diisopropylethylamine, pyridine, piperidine, pyrrolidine, proline, N, N-dimethylaminopyridine, imidazole, sodium hydroxide, potassium hydroxide, potassium carbonate, sodium carbonate, sodium hydrogencarbonate, potassium hydrogencarbonate. , Potassium hydroxide, sodium hydroxide, sodium hydrogen and the like. Examples of the carbodiimide condensing agent include N, N-dicyclohexylcarbodiimide, N, N-diisopropylcarbodiimide, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride and the like. The amount of the base used is preferably 0.5 to 5 mol with respect to 1 mol of cyanoacetic acid.
The reaction between cyanoacetic acid and hydroxyalkyl acrylate is preferably carried out in an organic solvent. Examples of the organic solvent include acetonitrile, isopropanol, toluene, trichloromethane, dichloromethane and the like.

The reaction between cyanoacetic acid and hydroxyalkyl acrylate is carried out by mixing cyanoacetic acid and hydroxyalkyl acrylate.
The reaction temperature of cyanoacetic acid and hydroxyalkyl acrylate is preferably −40 to 130 ° C., and the reaction time is usually preferably 1 to 24 hours.

Examples of the compound having a polymerizable group and a merocyanine structure include the compounds described below.

The resin (A) may be a homopolymer of a structural unit having a merocyanine structure in the side chain, or a copolymer containing a structural unit having a merocyanine structure in the side chain and other structural units. The resin (A) is preferably a copolymer.
Examples of the structural unit that the resin (A) may contain in addition to the structural unit having a merocyanine structure in the side chain include the structural units described in the following group A.
Group A: Structural unit derived from (meth) acrylic acid ester, structural unit derived from styrene-based monomer, structural unit derived from vinyl-based monomer, structural unit represented by the formula (a), formula ( The structural unit represented by b) and the structural unit represented by the formula (c).

[In the formula, ^Ra1 represents a divalent hydrocarbon group.
R ^b1 and R ^b2 independently represent a hydrogen atom or a hydrocarbon group.
R ^c1 and R ^c2 each independently represent a divalent hydrocarbon group. ]

Examples of the (meth) acrylic acid ester include methyl (meth) acrylic acid, ethyl (meth) acrylic acid, n-propyl (meth) acrylic acid, n-butyl (meth) acrylic acid, n-pentyl (meth) acrylic acid, and the like. N-hexyl (meth) acrylic acid, n-heptyl (meth) acrylic acid, n-octyl (meth) acrylic acid, n-nonyl (meth) acrylic acid, n-decyl (meth) acrylic acid, (meth) acrylic acid Linear alkyl esters of (meth) acrylic acids such as n-dodecyl, lauryl (meth) acrylate, stearyl (meth) acrylate; i-propyl (meth) acrylate, i-butyl (meth) acrylate, T-butyl (meth) acrylic acid, i-pentyl (meth) acrylic acid, i-hexyl (meth) acrylic acid, 2-ethylhexyl (meth) acrylic acid, i-octyl (meth) acrylic acid, (meth) acrylic acid Branched alkyl esters of (meth) acrylic acids such as i-nonyl, i-stearyl (meth) acrylic acid, i-amyl (meth) acrylic acid; cyclohexyl (meth) acrylic acid, (meth) acrylic acid Isobolonyl, adamantyl (meth) acrylate, dicyclopentanyl (meth) acrylate, cyclododecyl (meth) acrylate, methylcyclohexyl (meth) acrylate, trimethylcyclohexyl (meth) acrylate, tert- (meth) acrylate Examples thereof include alicyclic skeleton-containing alkyl esters of (meth) acrylic acid such as butylcyclohexyl and α-ethoxyacrylic acid cyclohexyl; and aromatic ring skeleton-containing esters of (meth) acrylic acid such as phenyl (meth) acrylic acid.

As the structural unit derived from the (meth) acrylic acid ester, a substituent-containing (meth) acrylic acid alkyl ester in which a substituent is introduced into the alkyl group in the (meth) acrylic acid alkyl ester can also be mentioned. The substituent of the substituent-containing (meth) acrylic acid alkyl ester is a group that substitutes a hydrogen atom of the alkyl group, and specific examples thereof include a phenyl group, an alkoxy group, and a phenoxy group. Specific examples of the substituent-containing (meth) acrylic acid alkyl ester include (meth) acrylic acid 2-methoxyethyl, (meth) acrylic acid ethoxymethyl, (meth) acrylic acid phenoxyethyl, and (meth) acrylic acid 2-. Examples thereof include (2-phenoxyethoxy) ethyl, phenoxydiethylene glycol (meth) acrylate, and phenoxypoly (ethylene glycol) (meth) acrylate.

Each of these (meth) acrylic acid esters can be used alone, or a plurality of different ones may be used.

The resin (A) of the present invention is a structural unit derived from the (meth) acrylic acid alkyl ester (a1) in which the glass transition temperature Tg of the homopolymer is less than 0 ° C. among the (meth) acrylic acid alkyl esters, and the homopolymer. It preferably contains a structural unit derived from the (meth) acrylic acid alkyl ester (a2) having a Tg of 0 ° C. or higher. This is advantageous in increasing the high temperature durability of the pressure-sensitive adhesive layer. As the Tg of the homopolymer of the (meth) acrylic acid alkyl ester, a literature value such as POLYMER HANDBOOK (Wiley-Interscience) can be adopted.

Specific examples of the (meth) acrylic acid alkyl ester (a1) include ethyl acrylate, n- and i-propyl acrylate, n- and i-butyl acrylate, n-pentyl acrylate, n- and i- acrylate. Hexyl, n-heptyl acrylate, n- and i-octyl acrylate, 2-ethylhexyl acrylate, n- and i-nonyl acrylate, n- and i-decyl acrylate, n-dodecyl acrylate, etc. Contains a (meth) acrylic acid alkyl ester having about 2 to 12 carbon atoms in the alkyl group of.

As the (meth) acrylic acid alkyl ester (a1), only one type may be used, or two or more types may be used in combination. Of these, n-butyl acrylate, n-octyl acrylate, 2-ethylhexyl acrylate and the like are preferable from the viewpoint of followability and reworkability when laminated on an optical film.

The (meth) acrylic acid alkyl ester (a2) is a (meth) acrylic acid alkyl ester other than the (meth) acrylic acid alkyl ester (a1). Specific examples of the (meth) acrylic acid alkyl ester (a2) include methyl acrylate, cyclohexyl acrylate, isobolonyl acrylate, stearyl acrylate, t-butyl acrylate and the like.

As the (meth) acrylic acid alkyl ester (a2), only one type may be used, or two or more types may be used in combination. Among them, from the viewpoint of high temperature durability, the (meth) acrylic acid alkyl ester (a2) preferably contains methyl acrylate, cyclohexyl acrylate, isobolonyl acrylate and the like, and more preferably contains methyl acrylate.

Further, as the structural unit derived from the (meth) acrylic acid ester, a structural unit derived from the (meth) acrylic acid ester having a polar functional group can also be mentioned.
Examples of the (meth) acrylic acid ester monomer having a polar functional group include (meth) acrylic acid 1-hydroxymethyl, (meth) acrylic acid 1-hydroxyethyl, (meth) acrylic acid 1-hydroxyheptyl, and (meth). 1-Hydroxybutyl acrylate, 1-hydroxypentyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, (meth) 2-Hydroxypentyl acrylate, 2-hydroxyhexyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, 3-hydroxybutyl (meth) acrylate, 3-hydroxypentyl (meth) acrylate, (meth) 3-Hydroxyhexyl acrylate, 3-hydroxyheptyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 4-hydroxypentyl (meth) acrylate, 4-hydroxyhexyl (meth) acrylate, (meth) 4-Hydroxyheptyl acrylate, 4-hydroxyoctyl (meth) acrylate, 2-chloro-2-hydroxypropyl (meth) acrylate, 3-chloro-2-hydroxypropyl (meth) acrylate, (meth) acrylate 2-Hydroxy-3-phenoxypropyl, 5-hydroxypentyl (meth) acrylate, 5-hydroxyhexyl (meth) acrylate, 5-hydroxyheptyl (meth) acrylate, 5-hydroxyoctyl (meth) acrylate, (meth) ) 5-Hydroxyhexyl acrylate, 6-hydroxyhexyl (meth) acrylate, 6-hydroxyheptyl (meth) acrylate, 6-hydroxyoctyl (meth) acrylate, 6-hydroxynonyl (meth) acrylate, (meth) ) 6-Hydroxydecyl acrylate, 7-hydroxyheptyl (meth) acrylate, 7-hydroxyoctyl (meth) acrylate, 7-hydroxynonyl (meth) acrylate, 7-hydroxydecyl (meth) acrylate, (meth) ) 7-Hydroxyundesyl acrylate, 8-hydroxyoctyl (meth) acrylate, 8-hydroxynonyl (meth) acrylate, 8-hydroxydecyl (meth) acrylate, 8-hydroxyundecyl (meth) acrylate, 8-Hydroxydodecyl (meth) acrylate, 9-hydroxynonyl (meth) acrylate, 9-hydroxydecyl (meth) acrylate, 9-hydroxyunde (meth) acrylate Syl, 9-hydroxydodecyl (meth) acrylate, 9-hydroxytridecyl (meth) acrylate, 10-hydroxydecyl (meth) acrylate, 10-hydroxyundecyl (meth) acrylate, 10 (meth) acrylate -Hydroxydodecyl, 10-hydroxytridecyl acrylate, 10-hydroxytetradecyl (meth) acrylate, 11-hydroxyundecyl (meth) acrylate, 11-hydroxydodecyl (meth) acrylate, 11 (meth) acrylate -Hydroxytridecyl, 11-hydroxytetradecyl (meth) acrylate, 11-hydroxypentadecyl (meth) acrylate, 12-hydroxydodecyl (meth) acrylate, 12-hydroxytridecyl (meth) acrylate, (meth) ) 12-Hydroxytetradecyl acrylate, 13-hydroxypentadecyl (meth) acrylate, 13-hydroxytetradecyl (meth) acrylate, 13-hydroxypentadecyl (meth) acrylate, 14-hydroxy (meth) acrylate (Meta) acrylic acid alkyl esters having a hydroxy group such as tetradecyl, (meth) acrylic acid 14-hydroxypentadecyl, (meth) acrylic acid 15-hydroxypentadecyl, (meth) acrylic acid 15-hydroxyheptadecyl, etc. Can be mentioned.

Examples of the styrene-based monomer include styrene; methylstyrene, dimethylstyrene, trimethylstyrene, ethylstyrene, diethylstyrene, triethylstyrene, propylstyrene, butylstyrene, hexylstyrene, heptylstyrene, octylstyrene and other alkylstyrenes; fluorostyrene, Examples thereof include halogenated styrenes such as chlorostyrene, bromostyrene, dibromostyrene and iodostyrene; nitrostyrene; acetylstyrene; methoxystyrene; and divinylbenzene.

Examples of the vinyl-based monomer include fatty acid vinyl esters such as vinyl acetate, vinyl propionate, vinyl butyrate, vinyl 2-ethylhexanoate and vinyl laurate; vinyl halides such as vinyl chloride and vinyl bromide; vinylidene chloride and the like. Examples thereof include vinylidene halide; nitrogen-containing heteroaromatic vinyl such as vinylpyridine, vinylpyrrolidone and vinylcarbazole; conjugated diene such as butadiene, isoprene and chloroprene; and unsaturated nitriles such as acrylonitrile and methacrylonitrile.

The compound that derives the structural unit represented by the formula (a) can be synthesized, for example, by reacting a diisocyanate compound with a polyol.
The compound that derives the structural unit represented by the formula (b) can be synthesized, for example, by reacting a silane halide or a silane having a hydroxy group.
The compound that derives the structural unit represented by the formula (c) can be synthesized, for example, by reacting a polycarboxylic acid with a polyol.

The structural unit selected from the structural units described in group A is preferably a structural unit derived from (meth) acrylic acid ester. The structural unit derived from the (meth) acrylic acid ester is preferably a (meth) acrylic acid alkyl ester and a (meth) acrylic acid alkyl ester having a hydroxy group.

The resin (A) of the present invention may contain yet another structural unit (sometimes referred to as a structural unit (aa)). Specifically, a structural unit derived from a (meth) acrylamide-based monomer, a structural unit derived from a monomer having a carboxyl group, a structural unit derived from a monomer having a heterocyclic group, substituted or unsubstituted. Examples thereof include structural units derived from monomers having an amino group.

Examples of the (meth) acrylamide-based monomer include N-methylol (meth) acrylamide, N- (2-hydroxyethyl) (meth) acrylamide, N- (3-hydroxypropyl) (meth) acrylamide, and N- (4-). Hydroxybutyl) (meth) acrylamide, N- (5-hydroxypentyl) (meth) acrylamide, N- (6-hydroxyhexyl) (meth) acrylamide, N, N-dimethyl (meth) acrylamide, N, N-diethyl ( Meta) acrylamide, N-isopropyl (meth) acrylamide, N- (3-dimethylaminopropyl) (meth) acrylamide, N- (1,1-dimethyl-3-oxobutyl) (meth) acrylamide, N- [2-( 2-Oxo-1-imidazolidinyl) ethyl] (meth) acrylamide, 2-acrylloylamino-2-methyl-1-propanesulfonic acid, N- (methoxymethyl) acrylamide, N- (ethoxymethyl) (meth) acrylamide, N -(Prooxymethyl) (meth) acrylamide, N- (1-methylethoxymethyl) (meth) acrylamide, N- (1-methylpropoxymethyl) (meth) acrylamide, N- (2-methylpropoxymethyl) (meth) Acrylamide, N- (butoxymethyl) (meth) acrylamide, N- (1,1-dimethylethoxymethyl) (meth) acrylamide, N- (2-methoxyethyl) (meth) acrylamide, N- (2-ethoxyethyl) (Meta) acrylamide, N- (2-propoxyethyl) (meth) acrylamide, N- [2- (1-methylethoxy) ethyl] (meth) acrylamide, N- [2- (1-methylpropoxy) ethyl] ( Meta) acrylamide, N- [2- (2-methylpropoxy) ethyl] (meth) acrylamide, N- (2-butoxyethyl) (meth) acrylamide, N- [2- (1,1-dimethylethoxy) ethyl] Examples include (meth) acrylamide. Of these, N- (methoxymethyl) acrylamide, N- (ethoxymethyl) acrylamide, N- (propoxymethyl) acrylamide, N- (butoxymethyl) acrylamide and N- (2-methylpropoxymethyl) acrylamide are preferable.

Examples of the monomer having a carboxyl group include (meth) acrylic acid, carboxyalkyl (meth) acrylate (for example, carboxyethyl (meth) acrylate, carboxypentyl (meth) acrylate), maleic acid, maleic anhydride, fumaric acid, and the like. Examples thereof include crotonic acid, and acrylic acid is preferable.

Examples of the monomer having a heterocyclic group include acryloyl morpholine, vinyl caprolactam, N-vinyl-2-pyrrolidone, vinyl pyridine, tetrahydrofurfuryl (meth) acrylate, caprolactone-modified tetrahydrofurfuryl acrylate, and 3,4-epoxycyclohexylmethyl. Examples thereof include (meth) acrylate, glycidyl (meth) acrylate, and 2,5-dihydrofuran.

Examples of the monomer having a substituted or unsubstituted amino group include aminoethyl (meth) acrylate, N, N-dimethylaminoethyl (meth) acrylate, and dimethylaminopropyl (meth) acrylate.

The structural unit (aa) other than the structural unit having a merocyanine structure and the structural unit selected from group A is preferably a monomer having a carboxyl group.

The content of the structural unit having a merocyanine structure in the side chain is preferably 0.01 to 50 parts by mass, preferably 0.1 to 20 parts by mass, based on 100 parts by mass of all the structural units contained in the resin (A). The amount is more preferably 0.5 to 10 parts by mass.
The content of at least one structural unit selected from the structural units described in group A is preferably 50 parts by mass or more, preferably 60 to 99.99 parts by mass, based on 100 parts by mass of all structural units of the resin (A). More preferably, it is by mass.

When the resin (A) contains the structural unit (aa), it is preferably 20 parts by mass or less, more preferably 0.5 parts by mass or more and 15 parts by mass with respect to 100 parts by mass of all the structural units of the resin (A). Hereinafter, it is more preferably 0.5 parts by mass or more and 10 parts by mass or less, and particularly preferably 1 part by mass or more and 7 parts by mass or less.

When the resin (A) contains a structural unit derived from a (meth) acrylic acid alkyl ester having a hydroxy group, the content of the structural unit is preferably based on 100 parts by mass of the total structural unit of the resin (A). Is 20 parts by mass or less, more preferably 0.5 parts by mass or more and 15 parts by mass or less, further preferably 0.5 parts by mass or more and 10 parts by mass or less, and particularly preferably 1 part by mass or more and 7 parts by mass or less.
From the viewpoint of preventing the peeling power of the separate film that can be laminated on the outer surface of the pressure-sensitive adhesive layer from being enhanced, it is preferable that the monomer having an amino group is substantially not contained. Here, substantially not contained means that the amount is 0.1 parts by mass or less out of 100 parts by mass of all the constituent units constituting the resin (A).

In terms of reactivity between the resin (A) and the cross-linking agent (B) described later, the resin (A) is a structural unit derived from a (meth) acrylic acid alkyl ester having a hydroxy group or a monomer having a carboxyl group. It is preferable to include a structural unit derived from the structural unit, and it is more preferable to include both a structural unit derived from a (meth) acrylic acid alkyl ester having a hydroxy group and a structural unit derived from a monomer having a carboxyl group. As the (meth) acrylic acid alkyl ester having a hydroxy group, 2-hydroxyethyl acrylate, 3-hydroxypropyl acrylate, 4-hydroxybutyl acrylate, 5-hydroxypentyl acrylate, and 6-hydroxyhexyl acrylate are preferable. .. In particular, good durability can be obtained by using 2-hydroxyethyl acrylate, 4-hydroxybutyl acrylate and 5-hydroxypentyl acrylate. Acrylic acid is preferably used as the monomer having a carboxyl group.

The weight average molecular weight (Mw) of the resin (A) is preferably 300,000 to 2.5 million, and more preferably 500,000 to 2.5 million. When the weight average molecular weight is 300,000 or more, the durability of the pressure-sensitive adhesive layer in a high temperature environment is improved, and the floating and peeling between the adherend and the light-selective absorbing pressure-sensitive adhesive layer and the light-selective absorbing pressure-sensitive adhesive are observed. It is easy to suppress defects such as cohesive failure of layers. When the weight average molecular weight is 2.5 million or less, it is advantageous from the viewpoint of coatability when the pressure-sensitive adhesive composition is processed into, for example, a sheet (coating on a base material). From the viewpoint of achieving both the durability of the light selective absorption pressure-sensitive adhesive layer and the coatability of the pressure-sensitive adhesive composition, the weight average molecular weight is preferably 600,000 to 1.8 million, more preferably 700,000 to 1.7 million. Particularly preferably, it is 1 million to 1.6 million. The molecular weight distribution (Mw / Mn) represented by the ratio of the weight average molecular weight (Mw) to the number average molecular weight (Mn) is usually 2 to 10, preferably 3 to 8. The weight average molecular weight can be analyzed by gel permeation chromatography and is a value in terms of standard polystyrene.

When the resin (A) is dissolved in ethyl acetate to prepare a solution having a concentration of 20% by mass, the viscosity at 25 ° C. is preferably 20 Pa · s or less, and more preferably 0.1 to 15 Pa · s. preferable. A viscosity in this range is advantageous from the viewpoint of coatability when the pressure-sensitive adhesive composition is applied to the substrate. The viscosity can be measured with a Brookfield viscometer.

The resin (A) of the present invention can be produced by a known method such as a solution polymerization method, a bulk polymerization method, a suspension polymerization method, or an emulsion polymerization method, and the solution polymerization method is particularly preferable. As a solution polymerization method, for example, a monomer and an organic solvent are mixed, a thermal polymerization initiator is added under a nitrogen atmosphere, and the temperature conditions are 40 to 90 ° C., preferably 50 to 80 ° C., 3 to 15 A method of stirring for about an hour can be mentioned. For reaction control, monomers and thermal polymerization initiators may be added continuously or intermittently during the polymerization. The monomer and the heat initiator may be in a state of being added to an organic solvent.

As the polymerization initiator, a thermal polymerization initiator, a photopolymerization initiator, or the like is used. Examples of the photopolymerization initiator include 4- (2-hydroxyethoxy) phenyl (2-hydroxy-2-propyl) ketone. Examples of the thermal polymerization initiator include 2,2'-azobisisobutyronitrile, 2,2'-azobis (2-methylbutyronitrile), 1,1'-azobis (cyclohexane-1-carbonitrile), and 2 , 2'-azobis (2,4-dimethylvaleronitrile), 2,2'-azobis (2,4-dimethyl-4-methoxyvaleronitrile), dimethyl-2,2'-azobis (2-methylpropionate) ), 2,2'-Azobis (2-hydroxymethylpropionitrile) and other azo compounds; lauryl peroxide, t-butyl hydroperoxide, benzoyl peroxide, t-butyl peroxybenzoate, cumene hydroperoxide, Organic peroxides such as diisopropylperoxydicarbonate, dipropylperoxydicarbonate, t-butylperoxyneodecanoate, t-butylperoxypivalate, (3,5,5-trimethylhexanoyl) peroxide ; Examples include inorganic peroxides such as potassium persulfate, ammonium persulfate, and hydrogen peroxide. In addition, a redox-based initiator in which a peroxide and a reducing agent are used in combination can also be used.

The ratio of the polymerization initiator is about 0.001 to 5 parts by mass with respect to 100 parts by mass of the total amount of the monomers constituting the resin (A). For the polymerization of the resin (A), a polymerization method using active energy rays (for example, ultraviolet rays) may be used.

Organic solvents include aromatic hydrocarbons such as toluene and xylene; esters such as ethyl acetate and butyl acetate; fatty alcohols such as propyl alcohol and isopropyl alcohol; ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone. Can be mentioned.

The resin (A) is preferably a resin satisfying the following formula (1), and more preferably a resin satisfying the following formula (2).
ε (405) ≧ 0.02 (1)
[In formula (1), ε (405) represents the gram extinction coefficient of the resin at a wavelength of 405 nm. The unit of the gram extinction coefficient is L / (g · cm). ]
ε (405) / ε (440) ≧ 5 (2)
[In formula (2), ε (405) represents the gram extinction coefficient of the resin at a wavelength of 405 nm, and ε (440) represents the gram extinction coefficient of the resin at a wavelength of 440 nm. ]
The gram absorbance coefficient of the resin (A) can be measured by the method described in Examples.

The larger the value of ε (405), the easier it is for the resin (A) to absorb light having a wavelength of 405 nm, and the value of ε (405) is preferably 0.02 L / (g · cm) or more, preferably 0.1 L. It is more preferably / (g · cm) or more, further preferably 0.2 L / (g · cm) or more, and usually 10 L / (g · cm) or less.
When the pressure-sensitive adhesive composition containing the resin (A) is applied to a display device (FPD: flat panel display) such as an organic electroluminescence display (organic EL display device) or a liquid crystal display device, the resin (A) ε (405) ) Is 0.02 L / (g · cm) or more, the absorption performance of visible light in the vicinity of 400 nm is good. Deterioration of the organic EL light emitting element due to visible light can be suppressed.

The resin (A) can selectively absorb light having a wavelength near 400 nm as the value of ε (405) / ε (440) increases. The value of ε (405) / ε (440) is preferably 5 or more, more preferably 50 or more, further preferably 75 or more, and particularly preferably 100 or more.
When ε (405) / ε (440) of the resin (A) is 5 or more, the pressure-sensitive adhesive composition containing the resin (A) is displayed on a display device (FPD: flat panel) such as an organic EL display device or a liquid crystal display device. When applied to a display), it can absorb light in the vicinity of 405 nm and suppress photodeterioration of a retardation film, an organic EL element, or the like without disturbing the color expression of the display device.

(Other ingredients contained in the pressure-sensitive adhesive composition)
The pressure-sensitive adhesive composition may further contain a cross-linking agent (B), a silane compound (D), an antistatic agent, a light selective absorber, a resin other than the resin (A), and the like.
The content of the resin (A) is usually 60% by mass to 99.99% by mass, preferably 70% by mass to 99.9% by mass, more preferably 70% by mass, based on 100% by mass of the solid content of the pressure-sensitive adhesive composition. Is 80% by mass to 99.7% by mass.

The pressure-sensitive adhesive composition can contain a cross-linking agent (B).
Examples of the cross-linking agent (B) include an isocyanate-based cross-linking agent, an epoxy-based cross-linking agent, an aziridine-based cross-linking agent, a metal chelate-based cross-linking agent, and the like. From the viewpoint of speed and the like, an isocyanate-based cross-linking agent is preferable.

As the isocyanate-based compound, a compound having at least two isocyanato groups (-NCO) in the molecule is preferable, and for example, an aliphatic isocyanate-based compound (for example, hexamethylene diisocyanate) and an alicyclic isocyanate-based compound (for example, isophorone diisocyanate) are preferable. , Hydrogenated diphenylmethane diisocyanate, hydrogenated xylylene diisocyanate), aromatic isocyanate-based compounds (for example, tolylene diisocyanate, xylylene diisocyanate diphenylmethane diisocyanate, naphthalene diisocyanate, triphenylmethane triisocyanate, etc.) and the like. The cross-linking agent (B) is an adduct (adduct) of the isocyanate compound made of a polyhydric alcohol compound [for example, an adduct made of glycerol, trimethylolpropane, etc.], an isocyanurate, a burette-type compound, a polyether polyol, or a polyester. It may be a derivative such as a urethane prepolymer type isocyanate compound which has been subjected to an addition reaction with a polyol, an acrylic polyol, a polybutadiene polyol, a polyisoprene polyol or the like. The cross-linking agent (B) can be used alone or in combination of two or more. Of these, typically aromatic isocyanate compounds (eg, tolylene diisocyanate, xylylene diisocyanate), aliphatic isocyanate compounds (eg, hexamethylene diisocyanate) or their polyhydric alcohol compounds (eg, glycerol, trimethylolpropane). ), Or isocyanurates. Is it because the cross-linking agent (B) is an adduct of an aromatic isocyanate compound and / or a polyhydric alcohol compound thereof, or an isocyanurate compound, which is advantageous for forming an optimum cross-linking density (or cross-linking structure)? The durability of the adhesive layer can be improved. In particular, an adduct made of a tolylene diisocyanate compound and / or a polyhydric alcohol compound thereof can improve durability even when, for example, an adhesive layer is applied to a polarizing plate.

The content of the cross-linking agent (B) is usually 0.01 to 15 parts by weight, preferably 0.05 to 10 parts by weight, and more preferably 0.1 parts by weight with respect to 100 parts by weight of the resin (A). ~ 5 parts by weight.

The pressure-sensitive adhesive composition may further contain the silane compound (D).
Examples of the silane compound (D) include vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris (2-methoxyethoxy) silane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropyltriethoxysilane, and 3 -Glysidoxypropylmethyldimethoxysilane, 3-glycidoxypropylethoxydimethylsilane, 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, Examples thereof include 3-methacryloyloxypropyltrimethoxysilane and 3-mercaptopropyltrimethoxysilane.
The silane compound (D) may be a silicone oligomer. Specific examples of the silicone oligomer are as follows in the form of a combination of the monomers.

3-Mercaptopropyltrimethoxysilane-tetramethoxysilane oligomer, 3-mercaptopropyltrimethoxysilane-tetraethoxysilane oligomer, 3-mercaptopropyltriethoxysilane-tetramethoxysilane oligomer, 3-mercaptopropyltriethoxysilane-tetraethoxysilane Mercaptopropyl group-containing oligomers such as oligomers; mercaptomethyltrimethoxysilane-tetramethoxysilane oligomer, mercaptomethyltrimethoxysilane-tetraethoxysilane oligomer, mercaptomethyltriethoxysilane-tetramethoxysilane oligomer, mercaptomethyltriethoxysilane-tetraethoxy Mercaptomethyl group-containing oligomers such as silane oligomers; 3-glycidoxypropyltrimethoxysilane-tetramethoxysilane copolymer, 3-glycidoxypropyltrimethoxysilane-tetraethoxysilane copolymer, 3-glycidoxypropyltriethoxysilane- Tetramethoxysilane copolymer, 3-Glydoxypropyltriethoxysilane-Tetraethoxysilane copolymer, 3-Glydoxypropylmethyldimethoxysilane-Tetramethoxysilane copolymer, 3-Glydoxypropylmethyldimethoxysilane-Tetraethoxysilane copolymer, 3-Glydoxypropyl group-containing copolymers such as 3-glycidoxypropylmethyldiethoxysilane-tetramethoxysilane copolymer, 3-glycidoxypropylmethyldiethoxysilane-tetraethoxysilane copolymer; 3-methacryloyloxypropyltri Methoxysilane-tetramethoxysilane oligomer, 3-methacryloyloxypropyltrimethoxysilane-tetraethoxysilane oligomer, 3-methacryloyloxypropyltriethoxysilane-tetramethoxysilane oligomer, 3-methacryloyloxypropyltriethoxysilane-tetraethoxysilane oligomer, 3-methacryloyloxypropylmethyldimethoxysilane-tetramethoxysilane oligomer, 3-methacryloyloxypropylmethyldimethoxysilane-tetraethoxysilane oligomer, 3-methacryloyloxypropylmethyldiethoxysilane-tetramethoxysilane oligomer, 3-methacryloyloxypropylmethyldi Ethoxysilane-tetraethoxysilane oligomer And other methacryloyloxypropyl group-containing oligomers; 3-acryloyloxypropyltrimethoxysilane-tetramethoxysilane oligomer, 3-acryloyloxypropyltrimethoxysilane-tetraethoxysilane oligomer, 3-acryloyloxypropyltriethoxysilane-tetramethoxysilane oligomer. , 3-Acryloyloxypropyltriethoxysilane-tetraethoxysilane oligomer, 3-acryloyloxypropylmethyldimethoxysilane-tetramethoxysilane oligomer, 3-acryloyloxypropylmethyldimethoxysilane-tetraethoxysilane oligomer, 3-acryloyloxypropylmethyldi Acryloyloxypropyl group-containing oligomers such as ethoxysilane-tetramethoxysilane oligomer, 3-acryloyloxypropylmethyldiethoxysilane-tetraethoxysilane oligomer; vinyltrimethoxysilane-tetramethoxysilane oligomer, vinyltrimethoxysilane-tetraethoxysilane oligomer , Vinyl Triethoxysilane-Tetramethoxysilane oligomer, Vinyltriethoxysilane-Tetraethoxysilane oligomer, Vinylmethyldimethoxysilane-Tetramethoxysilane oligomer, Vinylmethyldimethoxysilane-Tetraethoxysilane oligomer, Vinylmethyldiethoxysilane-Tetramethoxysilane Vinyl group-containing oligomers such as oligomers and vinylmethyldiethoxysilane-tetraethoxysilane oligomers; 3-aminopropyltrimethoxysilane-tetramethoxysilane copolymer, 3-aminopropyltrimethoxysilane-tetraethoxysilane copolymer, 3-aminopropyltri Ethoxysilane-tetramethoxysilane copolymer, 3-aminopropyltriethoxysilane-tetraethoxysilane copolymer, 3-aminopropylmethyldimethoxysilane-tetramethoxysilane copolymer, 3-aminopropylmethyldimethoxysilane-tetraethoxysilane copolymer, 3-amino Amino group-containing copolymers such as propylmethyldiethoxysilane-tetramethoxysilane copolymer and 3-aminopropylmethyldiethoxysilane-tetraethoxysilane copolymer.

The silane compound (D) may be a silane compound represented by the following formula (d1).

(In the formula, A represents an alkanediyl group having 1 to 20 carbon atoms or a divalent alicyclic hydrocarbon group having 3 to 20 carbon atoms, and constitutes the alkanediyl group and the alicyclic hydrocarbon group. -CH _2- may be replaced with -O- or -CO-, R ⁴¹ represents an alkyl group having 1 to 5 carbon atoms, and R ⁴² , R ⁴³ , R ⁴⁴ , R ⁴⁵ and R ⁴⁶ are. , Each independently represents an alkyl group having 1 to 5 carbon atoms or an alkoxy group having 1 to 5 carbon atoms.)

Examples of the alkanediyl group having 1 to 20 carbon atoms represented by A include a methylene group, a 1,2-ethanediyl group, a 1,3-propanediyl group, a 1,4-butandyl group, a 1,5-pentanediyl group and 1 , 6-Hexanediyl group, 1,7-heptandyl group, 1,8-octanediyl group, 1,9-nonandyl group, 1,10-decandyl group, 1,12-dodecandyl group, 1,14-tetradecandyl group , 1,16-Hexadecandyl group, 1,18-octadecandyl group and 1,20-icosandyl group. Examples of the divalent alicyclic hydrocarbon group having 3 to 20 carbon atoms include a 1,3-cyclopentanediyl group and a 1,4-cyclohexanediyl group. _{As the group in which -CH 2-} instead of -O- or -CO- constituting the alcandiyl group and the alicyclic hydrocarbon group is _{replaced with -CH 2} CH _2- O-CH ₂ CH _2- , -CH ₂ CH _2- O-CH ₂ CH _2- O-CH ₂ CH _2- , -CH ₂ CH _2- O-CH ₂ CH _2- O-CH ₂ CH _2- O-CH ₂ CH _2- , -CH ₂ CH _2- CO-O-CH ₂ CH _2- , -CH ₂ CH _2- O-CH ₂ CH _2- CO-O-CH ₂ CH _2- , -CH ₂ CH ₂ CH ₂ CH _2- O-CH ₂ CH _2- and CH ₂ CH ₂ CH ₂ CH _2- O-CH ₂ CH ₂ CH ₂ CH _2- .

Examples ^{of the alkyl group having 1 to 5 carbon atoms represented by R 41} to R ⁴⁵ include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert-butyl group and a pentyl group. the ^42-C 1-5 alkoxy group represented by ^{R 45,} a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, an isobutoxy group, and a tert- butoxy and pentyloxy groups.

Examples of the silane compound represented by the formula (d1) include (trimethoxysilyl) methane, 1,2-bis (trimethoxysilyl) ethane, 1,2-bis (triethoxysilyl) ethane, and 1,3-. Bis (trimethoxysilyl) propane, 1,3-bis (triethoxysilyl) propane, 1,4-bis (trimethoxysilyl) butane, 1,4-bis (triethoxysilyl) butane, 1,5-bis ( Trimethoxysilyl) pentane, 1,5-bis (triethoxysilyl) pentane, 1,6-bis (trimethoxysilyl) hexane, 1,6-bis (triethoxysilyl) hexane, 1,6-bis (tripropoxy) Bis (tri-C1-5 alkoxysilyl) such as silyl) hexane, 1,8-bis (trimethoxysilyl) octane, 1,8-bis (triethoxysilyl) octane, 1,8-bis (tripropoxysilyl) octane. C1-10 alkanes; bis (dimethoxymethylsilyl) methane, 1,2-bis (dimethoxymethylsilyl) ethane, 1,2-bis (dimethoxyethylsilyl) ethane, 1,4-bis (dimethoxymethylsilyl) butane, 1 , 4-bis (dimethoxyethylsilyl) butane, 1,6-bis (dimethoxymethylsilyl) hexane, 1,6-bis (dimethoxyethylsilyl) hexane, 1,8-bis (dimethoxymethylsilyl) octane, 1,8 -Bis (dimethoxyethylsilyl) octane and other bis (diC1-5 alkoxy C1-5 alkylsilyl) C1-10 alkanes; 1,6-bis (methoxydimethylsilyl) hexane, 1,8-bis (methoxydimethylsilyl) Examples thereof include bis (mono C1-5 alkoxy-di C1-5 alkylsilyl) C1-10 alkane such as octane. Of these, 1,2-bis (trimethoxysilyl) ethane, 1,3-bis (trimethoxysilyl) propane, 1,4-bis (trimethoxysilyl) butane, 1,5-bis (trimethoxysilyl) Bis (tri-C1-3 alkoxysilyl) C1-10 alkanes such as pentane, 1,6-bis (trimethoxysilyl) hexane, and 1,8-bis (trimethoxysilyl) octane are preferable, and 1,6-bis is particularly preferable. (Trimethoxysilyl) hexane and 1,8-bis (trimethoxysilyl) octane are preferable.

The content of the silane compound (D) is usually 0.01 to 10 parts by mass, preferably 0.03 to 5 parts by mass, and more preferably 0.05 with respect to 100 parts by mass of the resin (A). It is about 2 parts by mass, more preferably 0.1 to 1 part by mass.

The pressure-sensitive adhesive composition may further contain an antistatic agent.
Examples of the antistatic agent include a surfactant, a siloxane compound, a conductive polymer, an ionic compound and the like, and an ionic compound is preferable. Examples of the ionic compound include conventional ones. Examples of the cation component constituting the ionic compound include organic cations and inorganic cations. Examples of the organic cation include pyridinium cation, pyrrolidinium cation, piperidinium cation, imidazolium cation, ammonium cation, sulfonium cation, phosphonium cation and the like. Examples of the inorganic cation include alkali metal cations such as lithium cation, potassium cation, sodium cation and cesium cation, and alkaline earth metal cations such as magnesium cation and calcium cation. In particular, pyridinium cations, imidazolium cations, pyrrolidinium cations, lithium cations, and potassium cations are preferable from the viewpoint of compatibility with (meth) acrylic resins. The anion component constituting the ionic compound may be either an inorganic anion or an organic anion, but an anion component containing a fluorine atom is preferable from the viewpoint of antistatic performance. Examples of the anion component containing a fluorine atom include hexafluorophosphate anion (PF _6- ), bis (trifluoromethanesulfonyl) imide anion [(CF ₃ SO ₂ ) ₂ N-], and bis (fluorosulfonyl) imide anion [(FSO). ₂ ) ₂ N-], tetra (pentafluorophenyl) borate anion [(C ₆ F ₅ ) ₄ B-] and the like. These ionic compounds can be used alone or in combination of two or more. In particular, bis (trifluoromethanesulfonyl) imide anion [(CF ₃ SO ₂ ) ₂ N-], bis (fluorosulfonyl) imide anion [(FSO ₂ ) ₂ N-], tetra (pentafluorophenyl) borate anion [(C) ₆ F ₅ ) ₄ B-] is preferable.
An ionic compound that is solid at room temperature is preferable in terms of the stability over time of the antistatic performance of the light selective absorbing pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition.

The content of the antistatic agent is, for example, 0.01 to 20 parts by mass, preferably 0.1 to 10 parts by mass, and more preferably 1 to 7 parts by mass with respect to 100 parts by mass of the resin (A).

The pressure-sensitive adhesive composition contains the resin (A) which is a light-selective absorbent polymer, and may or may not contain a light-selective absorbent. The pressure-sensitive adhesive composition preferably does not contain a light selective absorber. The light selective absorber selectively absorbs light having a specific wavelength, and preferably contains a compound having at least one absorption maximum at a wavelength of 360 nm to 420 nm, and preferably contains a compound having an absorption maximum at 380 nm to 410 nm. It is more preferable to include it. When the light selective absorber is contained, the content of the light selective absorber is preferably 0.1 part by mass or less with respect to 100 parts by mass of all the resin components. Since there is a correlation between the content of the light selective absorber and the degree of color loss at the ends of the polarizer under high temperature and high humidity, the content of the light selective absorber is 0 from the viewpoint of suppressing color loss. It is preferably 1 part by mass or less.

The photoselective absorber is not particularly limited, but for example, an oxybenzophenone-based photoselective absorber, a benzotriazole-based photoselective absorber, a salicylate ester-based photoselective absorber, a benzophenone-based photoselective absorber, and a cyanoacrylate-based light selective absorber. , Organic light selective absorbers such as triazine light selective absorbers. More specifically, for example, 5-chloro-2- (3,5-di-sec-butyl-2-hydroxylphenyl) -2H-benzotriazole, (2-2H-benzotriazole-2-yl) -6- (Linear and side chain dodecyl) -4-methylphenol, 2-hydroxy-4-benzyloxybenzophenone, 2,4-benzyloxybenzophenone and the like can be mentioned. These organic light selective absorbers may be used alone or in combination of two or more.

As the light selective absorber, a commercially available product may be used. For example, as a triazine-based light selective absorber, "Kemisorb 102" manufactured by Chemipro Kasei Co., Ltd., "ADEKA STAB LA46", "ADEKA STAB LAF70" manufactured by ADEKA Corporation, etc. BASF Japan's "Chinubin 109", "Chinubin 171", "Chinubin 234", "Chinubin 326", "Chinubin 327", "Chinubin 328", "Chinubin 928", "Chinubin 400", "Chinubin 460", Examples thereof include "Chinubin 405" and "Chinubin 477". Benzotriazole-based photoselective absorbers include "ADEKA STAB LA31" and "ADEKA STAB LA36" manufactured by ADEKA Corporation, and "Sumisorb 200", "Sumisorb 250", "Sumisorb 300", and "Sumisorb 340" manufactured by Sumika Chemtex Co., Ltd. And "Sumisorb 350", "Kemisorb 74", "Kemisorb 79" and "Kemisorb 279" made by Chemipro Kasei Co., Ltd., "TINUVIN 99-2", "TINUVIN 900" and "TINUVIN 928" made by BASF, etc. Be done.

The light selective absorber may be an inorganic light selective absorber. Examples of the inorganic light selective absorber include titanium oxide, zinc oxide, indium oxide, tin oxide, talc, kaolin, calcium carbonate, titanium oxide-based composite oxide, zinc oxide-based composite oxide, ITO (tin-doped indium oxide), and the like. ATO (antimonated tin oxide) and the like can be mentioned. Examples of the titanium oxide-based composite oxide include silica and zinc oxide doped with alumina. These inorganic light selective absorbers can be used alone or in combination of two or more. An organic light selective absorber and an inorganic light selective absorber may be used in combination.

The pressure-sensitive adhesive composition can contain one or more additives such as a solvent, a cross-linking catalyst, a tack fire, a plasticizer, a softening agent, a pigment, a rust preventive, an inorganic filler, and light-scattering fine particles.

[Phase difference layer]
The optical laminate of the present invention may further include a retardation layer laminated on the opposite side of the light selective absorbing pressure-sensitive adhesive layer to the polarizer. The retardation layer may be one layer or two or more layers. The optical laminate 200 shown in FIG. 2 includes a first retardation layer 30 and a second retardation layer 31.

The retardation layer is an optical film that exhibits optical anisotropy. Examples of the optical film exhibiting optical anisotropy include polyvinyl alcohol, polycarbonate, polyester, polyarylate, polyimide, polyolefin, polycycloolefin, polystyrene, polysulfone, polyether sulfone, polyvinylidene fluoride / polymethylmethacrylate, and acetyl. Examples thereof include a stretched film obtained by stretching a polymer film made of cellulose, an ethylene-vinyl acetate copolymer saponified product, polyvinyl chloride, etc. about 1.01 to 6 times. Among the stretched films, a polymer film obtained by uniaxially stretching or biaxially stretching an acetyl cellulose, polyester, polycarbonate film or cycloolefin resin film is preferable. Further, the retardation layer may be a retardation layer made of a cured product of the polymerizable liquid crystal compound, which exhibits optical anisotropy by coating and orienting the polymerizable liquid crystal compound on a base material.

In the present specification, the retardation layer includes a retardation layer having zero retardation, and also includes a film called a uniaxial retardation film, a low photoelastic modulus retardation film, a wide viewing angle retardation film, and the like. ..
The zero retardation retardation layer is an optically isotropic film in which both the front retardation Re and the thickness direction retardation Rth are -15 to 15 nm.
Examples of the zero retardation film include a resin film made of a cellulose resin, a polyolefin resin (chain polyolefin resin, polycycloolefin resin, etc.) or a polyethylene terephthalate resin, and the retardation value can be easily controlled and can be obtained. A cellulose-based resin or a polyolefin-based resin is preferable because it is easy. The zero retardation film can also be used as a protective film. Zero retardation films include "Z-TAC" (trade name) sold by FUJIFILM Corporation, "Zero Tuck (registered trademark)" sold by Konica Minolta Opto Co., Ltd., and Zeon Corporation. Examples include "ZF-14" (trade name) sold by.

In the optical laminate of the present invention, the retardation layer is preferably a retardation layer which is a cured product of a polymerizable liquid crystal compound.
Examples of the retardation layer, which is a cured product of the polymerizable liquid crystal compound, include the first form to the fifth form.
First form: a retardation layer in which the rod-shaped liquid crystal compound is oriented horizontally with respect to the supporting base material Second form: a retardation layer in which the rod-shaped liquid crystal compound is oriented in the direction perpendicular to the supporting base material Third form : A retardation layer in which the direction of orientation of the rod-shaped liquid crystal compound changes spirally in the plane Fourth form: A retardation layer in which the disk-shaped liquid crystal compound is obliquely oriented Fifth form: The disk-shaped liquid crystal compound Biaxial retardation layer oriented perpendicular to the supporting substrate For example, as an optical film used for an organic electroluminescence display, the first form, the second form, and the fifth form are preferably used. Be done. Alternatively, the retardation layers of these forms may be laminated and used.

When the retardation layer is a layer made of a polymer in the oriented state of the polymerizable liquid crystal compound (hereinafter, may be referred to as an “optical anisotropic layer”), the retardation layer may have anti-wavelength dispersibility. preferable. The inverse wavelength dispersibility is an optical characteristic in which the in-plane retardation value of the liquid crystal alignment at a short wavelength is smaller than the in-plane retardation value of the liquid crystal alignment at a long wavelength. (7) and equation (8) are satisfied. Re (λ) represents an in-plane retardation value with respect to light having a wavelength of λ nm.
Re (450) / Re (550) ≤ 1 (7)
1 ≦ Re (630) / Re (550) (8)
In the optical laminate of the present invention, when the retardation layer has the first form and anti-wavelength dispersibility, it is preferable because coloring at the time of black display on the display device is reduced, and 0.82 in the above formula (7). More preferably, ≤Re (450) / Re (550) ≤0.93. Further, 120 ≦ Re (550) ≦ 150 is preferable.

As a polymerizable liquid crystal compound used for forming a retardation layer, "3.8.6 network (completely crosslinked type)" of the Liquid Crystal Handbook (edited by the Liquid Crystal Handbook Editorial Committee, published on October 30, 2000 by Maruzen Co., Ltd.) ) ”,“ 6.5.1 Liquid crystal material b. Polymerizable nematic liquid crystal material ”, compounds having a polymerizable group, and JP-A-2010-31223, JP-A-2010-270108. In Japanese Patent Application Laid-Open No. 2011-6360, Japanese Patent Application Laid-Open No. 2011-207765, Japanese Patent Application Laid-Open No. 2011-162678, Japanese Patent Application Laid-Open No. 2016-81035, International Publication No. 2017/043438, and Japanese Patent Application Laid-Open No. 2011-207765. Examples thereof include the above-mentioned polymerizable liquid crystal compounds.
Examples of the method for producing the retardation layer from the polymer in the oriented state of the polymerizable liquid crystal compound include the methods described in JP-A-2010-31223.

The thickness of the retardation layer, which is a liquid crystal cured layer obtained by curing a polymerizable liquid crystal compound, is, for example, 0.1 μm or more and 10 μm or less, preferably 0.5 μm or more and 8 μm or less, and more preferably 1 μm or more and 6 μm or less. is there.

A retardation layer that develops optical anisotropy by coating and orientation of a liquid crystal compound and a retardation layer that develops optical anisotropy by coating an inorganic layered compound are called temperature-compensated retardation films. Film, "NH film" (trade name; film with tilted rod-shaped liquid crystal) sold by JX Nikko Nisseki Energy Co., Ltd., "WV film" (trade name) sold by FUJIFILM Corporation. ; "VAC film" (trade name; completely biaxially oriented film) sold by Sumitomo Chemical Co., Ltd., "new" sold by Sumitomo Chemical Co., Ltd. VAC film "(trade name; biaxially oriented film) and the like can be mentioned.

The retardation layer is a λ / 4 retardation layer that imparts a phase difference of 1/4 wavelength to transmitted light, a λ / 2 retardation layer that imparts a phase difference of 1/2 wavelength to transmitted light, and a positive A plate. , And can be a positive C plate. When the first retardation layer 30 and the second retardation layer 31 are included as in the optical laminate 200 shown in FIG. 2, the combination of the first retardation layer 30 and the second retardation layer 31 is the λ / 2 position. Examples thereof include a combination of a retardation layer and a λ / 4 retardation layer, a combination of a λ / 4 retardation layer and a positive C layer, and the like.

The optical laminate of the present invention may be configured as a circularly polarizing plate having a λ / 4 retardation layer. The circular polarizing plate can be used as an antireflection polarizing plate.

[Lated layer]
The optical laminate of the present invention can include a laminating layer for joining the two layers. Examples of the bonding layer include an adhesive layer and a pressure-sensitive adhesive layer (hereinafter, also referred to as “second pressure-sensitive adhesive layer”). The optical laminate 200 shown in FIG. 2 has an adhesive layer 33 that is interposed between the first retardation layer 30 and the second retardation layer 31 and joins them, and an adhesive layer of the second retardation layer 31. It includes a second pressure-sensitive adhesive layer 32 laminated on the surface opposite to 33.

For the adhesive layer, a water-based adhesive, an active energy ray-curable adhesive, a thermosetting adhesive, or the like is used. The thickness of the adhesive layer is, for example, 10 nm or more and 20 μm or less, preferably 100 nm or more and 10 μm or less, and more preferably 500 nm or more and 5 μm or less.

The second pressure-sensitive adhesive layer may be composed of the same pressure-sensitive adhesive composition as the pressure-sensitive adhesive composition forming the above-mentioned light-selective absorbing pressure-sensitive adhesive layer, and may be composed of (meth) acrylic-based, rubber-based, urethane-based, or the like. It may be composed of a pressure-sensitive adhesive composition (hereinafter, also referred to as “second pressure-sensitive adhesive composition”) containing a resin as a main component, such as an ester-based, a silicone-based, or a polyvinyl ether-based resin. As the second pressure-sensitive adhesive composition, a pressure-sensitive adhesive composition using a (meth) acrylic resin having excellent transparency, weather resistance, heat resistance and the like as a base polymer is suitable. The second pressure-sensitive adhesive composition may be an active energy ray-curable type or a thermosetting type. The thickness of the second pressure-sensitive adhesive layer is usually 0.1 μm or more and 150 μm or less, for example, 8 μm or more and 60 μm or less, preferably 30 μm or less, and more preferably 20 μm or less from the viewpoint of thinning.

<Manufacturing method of optical laminate>
The

optical laminates

100 and 200 can be manufactured by a method including a step of laminating layers constituting the laminate 100 via a laminating layer. When the layers are bonded to each other via the bonding layer, it is preferable to perform a surface activation treatment such as a corona treatment on one or both of the bonding surfaces in order to improve the adhesion.

<Optical laminate>
The optical laminate of the present invention has a planar shape, and its area is, for example, 30 mm × 30 mm to 180 mm × 90 mm.
The optical laminate of the present invention may be a rectangle such as a rectangle or a square, a shape having a notch portion in which a part of the side constituting the rectangle is cut out, a semicircular shape, or a through hole in the plane. It may be a so-called irregular shape such as a shape having.
When the outer shape of the optical laminate has a straight side, the absorption axis of the polarizer constituting the optical laminate may be parallel to the side, orthogonal to the side, or diagonally, for example. They may intersect at an angle of 45 °.
When the optical laminate has a retardation layer and the retardation layer has an in-plane slow-phase axis, the slow-phase axis and the absorption axis of the polarizer constituting the optical laminate intersect at 45 °. It may intersect at 15 °, or at 75 °.

<Image display device>
The

optical laminates

100 and 200 are arranged on the front surface (visual side) of the image display panel and can be used as a component of the image display device. The optical laminate, which is a circularly polarizing plate, can also be used as an antireflection polarizing plate that imparts an antireflection function in an image display device. The image display device is not particularly limited, and examples thereof include an image display device such as an organic electroluminescence (organic EL) display device, an inorganic electroluminescence (inorganic EL) display device, a liquid crystal display device, and an electric field emission display device.

Hereinafter, the present invention will be described in more detail with reference to examples, but the present invention is not limited thereto. Unless otherwise specified, "%" and "parts" in Examples and Comparative Examples are "% by mass" and "parts by mass".

[Manufacturing of single-sided protective polarizing plate]
(Making a polarizer)
A polyvinyl alcohol film having a thickness of 20 μm, a degree of polymerization of 2400, and a degree of saponification of 99% or more was uniaxially stretched on a thermal roll at a stretching ratio of 4.1 times, and while maintaining a tense state, iodine was 0.05 per 100 parts by weight of water. It was immersed in a dyeing bath containing 5 parts by weight of potassium iodide and 5 parts by weight at 28 ° C. for 60 seconds.

Next, it was immersed in an aqueous boric acid solution 1 containing 5.5 parts by weight of boric acid and 15 parts by weight of potassium iodide per 100 parts by weight of water at 64 ° C. for 110 seconds. Then, it was immersed in boric acid aqueous solution 2 containing 5.5 parts by weight of boric acid and 15 parts by weight of potassium iodide per 100 parts by weight of water at 67 ° C. for 30 seconds. Then, it was washed with pure water at 10 ° C. and dried to obtain a polarizer. The thickness of the obtained polarizer was 8 μm, and the boron content was 4.3% by weight.

(Adjustment of water-based adhesive)
In 100 parts by weight of water, 3 parts by mass of carboxyl group-modified polyvinyl alcohol (Kurare Co., Ltd., trade name "KL-318") is dissolved, and a polyamide epoxy additive (Taoka Chemical Industry Co., Ltd.), which is a water-soluble epoxy resin, is dissolved in the aqueous solution. A water-based adhesive was prepared by adding 1.5 parts by mass of a trade name "Smiley's Resin (registered trademark) 650 (30), an aqueous solution having a solid content concentration of 30% by weight).

(Protective film A and release film B)
As the protective film A, a film having a hard coat layer having a thickness of 3 μm formed on a stretched film made of a norbornene resin having a thickness of 25 μm (manufactured by Nippon Paper Industries, Ltd., trade name “COP25ST-HC”) was used.
As the release film B, a triacetyl cellulose film (manufactured by FUJIFILM Corporation, "TD80UL") was used. The thickness of the release film is 80 [mu] m, the moisture permeability was 502g ^/ m 2 · 24hr.

(Manufacturing of single-sided protective polarizing plate)
The produced polarizer was continuously conveyed, the protective film A was continuously unwound from the roll of the protective film A, and the release film B was continuously unwound from the roll of the release film B. A water-based adhesive is injected between the polarizer and the corona-treated protective film A, and pure water is injected between the polarizer and the release film B, and the film is passed through a bonding roll to adhere the protective film A / water-based adhesive. A laminated film composed of an agent / polarizer / pure water / release film B was obtained. The laminated film is transported and heat-treated at 80 ° C. for 300 seconds in a drying furnace to dry the water-based adhesive and volatilize and remove the pure water interposed between the polarizer and the release film B. A single-sided protective polarizing plate with a release film was obtained. The release film B was peeled from the single-sided protective polarizing plate with a release film to obtain a single-sided protective polarizing plate.

[Manufacturing of retardation laminate]
(First liquid crystal cured layer)
As the first liquid crystal cured layer (first retardation layer), a layer formed by curing a nematic liquid crystal compound, an alignment film, and a transparent substrate, which gives a phase difference of λ / 4, was used. The total thickness of the cured layer and the oriented layer of the nematic liquid crystal compound was 2 μm.

(Preparation of second liquid crystal cured layer)
As a composition for forming an oriented layer, 10.0 parts by mass of polyethylene glycol di (meth) acrylate (manufactured by Shin-Nakamura Chemical Industry Co., Ltd., A-600) and trimethylolpropan triacrylate (manufactured by Shin-Nakamura Chemical Industry Co., Ltd.) 10.0 parts by mass of A-TMPT) and 10.0 parts by mass of 1,6-hexanediol di (meth) acrylate (manufactured by Shin-Nakamura Chemical Co., Ltd., A-HD-N), and Irgacure as a photopolymerization initiator. 1.50 parts by mass of 907 (Irg-907, manufactured by BASF) was dissolved in 70.0 parts by mass of the solvent methyl ethyl ketone to prepare a coating liquid for forming an orientation layer.

A long cyclic olefin resin (COP) film (manufactured by Nippon Zeon Corporation) with a thickness of 20 μm is prepared as a base film, and a coating liquid for forming an alignment layer is applied to one side of the base film with a bar coater. did.

After the coating layer after coating is heat-treated at a temperature of 80 ° C. for 60 seconds, it is ^{irradiated with ultraviolet rays (UVB) at 220 mJ / cm 2} to polymerize and cure the composition for forming an orientation layer to form a base film. An oriented layer having a thickness of 2.3 μm was formed on the top.

20.0 parts by mass of a photopolymerizable nematic liquid crystal compound (RMM28B, manufactured by Merck) as a composition for forming a retardation layer, and 1.0 mass by Irgacure 907 (Irg-907, manufactured by BASF) as a photopolymerization initiator. The parts were dissolved in 80.0 parts by mass of the solvent propylene glycol monomethyl ether acetate to prepare a coating liquid for forming a retardation layer.

A coating liquid for forming a retardation layer was applied onto the previously obtained alignment layer, and the coating layer was heat-treated at a temperature of 80 ° C. for 60 seconds. Then, it was irradiated with ultraviolet rays (UVB) at 220 mJ / cm ² to polymerize and cure the composition for forming a retardation layer to form a retardation layer having a thickness of 0.7 μm on the alignment layer. In this way, a second liquid crystal cured layer (second retardation layer) having a thickness of 3 μm composed of an alignment layer and a retardation layer was obtained on the base film.

(Manufacturing of retardation laminate)
The first liquid crystal layer and the second liquid crystal layer were bonded to each other with an ultraviolet curable adhesive (thickness 1 μm) so that the respective liquid crystal layer surfaces (the surface opposite to the base film) were bonded surfaces. Next, the ultraviolet curable adhesive was cured by irradiating with ultraviolet rays to prepare a retardation laminate including two retardation layers, a first liquid crystal curing layer and a second liquid crystal curing layer. The thickness of the retardation laminate including the first liquid crystal cured layer, the ultraviolet curable adhesive layer, and the second liquid crystal cured layer was 6 μm.

[Preparation of light-selective absorbent adhesive layer]
<Adhesive layer (1) used for the optical laminate of Example 1>
(Synthesis of light selective absorption monomer)
The inside of a 300 mL-four-necked flask equipped with a Dimroth condenser and a thermometer is set to a nitrogen atmosphere, and 10 parts of 2-hydroxyethyl acrylate, 8.1 parts of cyanoacetic acid, and 1.1 parts of N, N-dimethyl-4-aminopyridine are used. , 0.95 part of dibutylhydroxytoluene and 50 parts of toluene were charged and stirred with a magnetic stirrer. After cooling in an ice bath and confirming that the internal temperature reached 10 ° C., 12 parts of N, N-diisopropylcarbodiimide was added dropwise over 1 hour, and after the addition was completed, the internal temperature was kept at 0 to 10 ° C. for another 2 hours. .. Then, the insoluble component was removed by filtration under reduced pressure to obtain 70 parts of a filtrate containing a compound represented by UVA-M-02.

2. 20 parts of the compound represented by UVA-M-01 synthesized with reference to JP-A-2014-194508, with the inside of a 300 mL-four-necked flask equipped with a Dimroth condenser and a thermometer as a nitrogen atmosphere, acetic anhydride 7. 1 part, 70 parts of a flask containing UVA-M-02 and 40 parts of acetonitrile were charged and stirred with a magnetic stirrer. At an internal temperature of 25 ° C., 9 parts of N, N-diisopropylethylamine was added dropwise to the obtained mixture over 1 hour. The obtained mixture was kept warm at an internal temperature of 25 ° C. for 2 hours. 200 g of ice water was added to the obtained mixture, and the mixture was stirred, and the precipitated composition organisms were taken out by vacuum filtration. The obtained crude product was recrystallized from isopropanol to obtain 10 parts of the compound represented by UVA-01. The obtained compound represented by UVA-01 was ^{identified by LC-MS and 1} H-NMR.

(Adjustment of light selective absorption polymer (A-1))
In a reaction vessel equipped with a cooling tube, a nitrogen introduction tube, a thermometer and a stirrer, 96 parts by mass of butyl acrylate (referred to as "BA" in Table 1) and 2-hydroxyethyl acrylate (referred to as "HEA" in Table 1). ) 3 parts by mass, 1 part by mass of the light selective absorption monomer represented by UVA-01 (total solid content 100 parts by mass), and 135 parts by mass of ethyl acetate as a container are mixed and mixed with nitrogen gas. The internal temperature was raised to 60 ° C. while replacing the air in the apparatus to make it oxygen-free.
To the obtained mixture, a total amount of a solution prepared by dissolving 0.4 part of azobisisobutyronitrile (polymerization initiator) in 10 parts of ethyl acetate was added. The obtained mixture was held at 60 ° C. for 1 hour, and then ethyl acetate was continuously added into the reaction vessel at an addition rate of 17.3 parts / hr while maintaining the internal temperature at 50 to 70 ° C. to increase the concentration of the acrylic resin. When the concentration reached 35%, the addition of ethyl acetate was stopped, and the internal temperature was kept at 50 to 70 ° C. until 12 hours had passed from the start of the addition of ethyl acetate. Ethyl acetate was added to the obtained mixture of the photoselective absorbent polymer (A-1) to adjust the concentration of the resin component to 20%, and the ethyl acetate of the photoselective absorbent polymer (A-1) was adjusted. The solution was prepared. The photoselective absorbent polymer (A-1) had a polystyrene-equivalent weight average molecular weight Mw of 500,000 and Mw / Mn of 7.5 by GPC. The glass transition temperature by DSC was −48.4 ° C.

(Preparation of Adhesive Composition and Adhesive Layer)
(A) Preparation of Adhesive Composition A cross-linking agent (Coronate L,) was added to an ethyl acetate solution (resin concentration: 20%) of the photoselective absorbent polymer (A-1) with respect to 100 parts of the solid content of the solution. Mix 0.5 parts of solid content 75% (manufactured by Toso) and 0.5 part of silane compound (manufactured by Shinetsu Chemical Industry: KBM-403), and add 2-butanone so that the solid content concentration becomes 14%. The pressure-sensitive adhesive composition (1) was obtained. The blending amount of the cross-linking agent (Coronate L) is the number of parts by mass as the active ingredient.

(B) Preparation of Adhesive Layer Adhesive prepared in (a) above on the release-treated surface of a polyethylene terephthalate film (SP-PLR382050 manufactured by Lintec Corporation, hereinafter abbreviated as "separator") that has been subjected to a release treatment. The agent composition was applied using an applicator so that the thickness of the pressure-sensitive adhesive layer after drying was 5 μm, and dried at 100 ° C. for 1 minute to prepare a pressure-sensitive adhesive layer. The obtained pressure-sensitive adhesive layer was designated as a pressure-sensitive adhesive layer (1).

<Adhesive layer (2) used for the optical laminate of Example 2>
Using the photoselective absorbent polymer (A-2), the pressure-sensitive adhesive layer (2) was prepared in the same manner as the pressure-sensitive adhesive layer (1) of Example 1. The photoselective absorbent polymer (A-2) contains 95 parts by mass of BA and the amount of the photoselective absorbent monomer represented by UVA-01 in the preparation of the photoselective absorbent polymer (A-1). The only difference is that it is 2 parts by mass. The photoselective absorbent polymer (A-2) had a polystyrene-equivalent weight average molecular weight Mw of 500,000 and Mw / Mn of 6.3 according to GPC.

<Adhesive layer (3) used for the optical laminate of Example 3>
Using the photoselective absorbent polymer (A-3), the pressure-sensitive adhesive layer (3) was prepared in the same manner as the pressure-sensitive adhesive layer (1) of Example 1. The photoselective absorbent polymer (A-3) contains 93 parts by mass of BA and the amount of the photoselective absorbent monomer represented by UVA-01 in the preparation of the photoselective absorbent polymer (A-1). The only difference is that it is 4 parts by mass. The photoselective absorbent polymer (A-3) had a polystyrene-equivalent weight average molecular weight Mw of 600,000 and Mw / Mn of 7.0 according to GPC.

<Adhesive layer (4) used in the optical laminate of Comparative Example 1>
(Adjustment of acrylic resin (A-4))
In a reaction vessel equipped with a cooling tube, a nitrogen introduction tube, a thermometer and a stirrer, 61.9 parts of butyl acrylate and 1.9 parts of 2-hydroxyethyl acrylate and 86.4 parts of ethyl acetate as a solvent were added. The mixed solution was charged, and the internal temperature was raised to 60 ° C. while replacing the air in the apparatus with nitrogen gas to make it oxygen-free. Then, a total amount of a solution prepared by dissolving 0.4 part of azobisisobutyronitrile (polymerization initiator) in 10 parts of ethyl acetate was added. The obtained mixture was held at 60 ° C. for 1 hour, and then ethyl acetate was continuously added into the reaction vessel at an addition rate of 17.3 parts / hr while maintaining the internal temperature at 50 to 70 ° C. to increase the concentration of the acrylic resin. When the concentration reached 35%, the addition of ethyl acetate was stopped, and the temperature was kept at this temperature until 12 hours had passed from the start of the addition of ethyl acetate. Finally, ethyl acetate was added to adjust the concentration of the acrylic resin to 20%, and an ethyl acetate solution of the acrylic resin was prepared. The obtained acrylic resin had a polystyrene-equivalent weight average molecular weight Mw of 600,000 and Mw / Mn of 7.0 by GPC. This is referred to as acrylic resin (A-4). The glass transition temperature by DSC was −52.9 ° C.

(Preparation of Adhesive Composition and Adhesive Layer)
(A) Preparation of Adhesive Composition In an ethyl acetate solution (resin concentration: 20%) of acrylic resin (A-4), a cross-linking agent (coronate L, solid content 75%) was added to 100 parts of the solid content of the solution. : 0.5 parts of Toso Co., Ltd., 0.5 parts of silane compound (manufactured by Shinetsu Chemical Industry Co., Ltd .: KBM-403) and the light selective absorption compound (Synthesis Example 2) described in paragraph [0142] of JP-A-2019-007001 2.5 parts of the compound (photoselective absorber) represented by the following formula (aa2) described as 2) is mixed, and 2-butanone is further added so that the solid content concentration becomes 14%, and the adhesive is adhered. The agent composition (4) was obtained. The blending amount of the cross-linking agent (Coronate L) is the number of parts by mass as the active ingredient.

(B) Preparation of Adhesive Layer A pressure-sensitive adhesive layer (4) was prepared from the pressure-sensitive adhesive composition by the same method as in Example 1.

<Adhesive layer (5) used in the optical laminate of Comparative Example 2>
In the preparation of the pressure-sensitive adhesive composition, the pressure-sensitive adhesive layer (5) was prepared by the same method as the preparation of the pressure-sensitive adhesive layer (4) except that the blending amount of the light selective absorber was 3.7 parts.

<Adhesive layer (6) used in the optical laminate of Comparative Example 3>
In the preparation of the pressure-sensitive adhesive composition, the pressure-sensitive adhesive layer was prepared by the same method as in the preparation of the pressure-sensitive adhesive layer (4) except that the blending amount of the light selective absorber was 2.5 parts and the thickness of the pressure-sensitive adhesive layer was 17 μm. (6) was prepared.

[Preparation of second adhesive layer]
In an ethyl acetate solution (resin concentration: 20%) of the above acrylic resin (A-4), 0.5 part of a cross-linking agent (coronate L, solid content 75%: manufactured by Tosoh) and a silane compound (manufactured by Shin-Etsu Chemical Industry: KBM-) 403) 0.5 parts were mixed, and 2-butanone was further added so that the solid content concentration became 14% to obtain a pressure-sensitive adhesive composition (7). The blending amount of the above-mentioned cross-linking agent (Coronate L) is the number of parts by mass as an active ingredient.

The pressure-sensitive adhesive composition (7) is applied to the release-treated surface of the separator used for producing the light-selective absorbing pressure-sensitive adhesive layer using an applicator so that the thickness of the pressure-sensitive adhesive layer after drying is 15 μm or 25 μm. Then, it was dried at 100 ° C. for 1 minute to prepare a second pressure-sensitive adhesive layer.

[Preparation of optical laminate]
(Example 1)
The pressure-sensitive adhesive layer (1) was attached to the polarizer side of the prepared single-sided protective polarizing plate, and the separator was peeled off. The surface from which the separator of the pressure-sensitive adhesive layer (1) was peeled off was bonded to the first liquid crystal cured layer side of the produced retardation laminate, and the base film of the second liquid crystal cured layer was peeled off. A second pressure-sensitive adhesive layer with a separator having the thickness shown in Table 1 was attached to the surface from which the base film was peeled off. The optical laminate of Example 1 had a configuration as shown in FIG.

(Examples 2 and 3, Comparative Examples 1 to 3)
By the same method as the optical laminate of Example 1, the adhesive layer (2) was used instead of the adhesive layer (1) of Example 1, and the optical laminate of Example 2 was subjected to the adhesive layer (3). The optical laminate of Example 3 was used, the optical laminate of Comparative Example 1 was used with the pressure-sensitive adhesive layer (4), and the optical laminate of Comparative Example 2 was used with the pressure-sensitive adhesive layer (5). The optical laminate of Comparative Example 3 was prepared using the layer (6).

[Measurement of absorbance of adhesive layer]
The pressure-sensitive adhesive layer (6) is bonded to the glass from the pressure-sensitive adhesive layer (1), the separator is peeled off, and then a cycloolefin polymer (COP) film (ZF-14 manufactured by Nippon Zeon Corporation) is attached to the pressure-sensitive adhesive layer. Then, a laminate for evaluating the pressure-sensitive adhesive layer was prepared. The laminate for evaluating the pressure-sensitive adhesive layer was set on a spectrophotometer UV-2450 (manufactured by Shimadzu Corporation), and the absorbance was measured in the wavelength range of 300 to 800 nm in 1 nm steps by the double beam method. Table 1 shows the absorbance of the prepared pressure-sensitive adhesive layer at a wavelength of 410 nm. The absorbance of the glass and the absorbance of the COP film at a wavelength of 410 nm are both 0.

[Measurement of weight average molecular weight (Mw)]
The weight average molecular weight (Mw) of the photoselective absorbent polymers (A-1), (A-2), (A-3) and the acrylic resin (A-4) is defined as the polystyrene-equivalent number average molecular weight (Mn). , Tetrahydrofuran was used as the mobile phase, and it was determined by the following size exclusion chromatography (SEC). The (meth) acrylic polymer to be measured was dissolved in tetrahydrofuran at a concentration of about 0.05% by mass, and 10 μL was injected into SEC. The mobile phase was flowed at a flow rate of 1.0 mL / min. PLgel MIXED-B (manufactured by Polymer Laboratories) was used as a column. A UV-VIS detector (trade name: Agilent GPC) was used as the detector.

[Measurement of boron content]
0.2 g of the polarizer was dissolved in 200 g of a 1.9 wt% mannitol aqueous solution. The obtained aqueous solution was titrated with a 1 mol / L NaOH aqueous solution, and the boron content of the polarizer was calculated by comparing the amount of the NaOH solution required for neutralization with the calibration curve.

[Moisture resistance test and observation of color loss]
The separators of the optical laminates obtained in Examples 1 to 3 and Comparative Examples 1 to 3 were peeled off, bonded to a non-alkali glass plate, and then left to stand in an environment of a temperature of 65 ° C. and a humidity of 90% RH for 500 hours. .. Then, a polarizing plate having a cross-nicol relationship was attached to a non-alkali glass surface opposite to the tested optical laminate, observed with an optical microscope, and the observed image was stored. As the optical microscope, "VHX-500" manufactured by KEYENCE CORPORATION was used. FIG. 3 shows an example of an observation image with an optical microscope. In FIG. 3, when observed along the straight line indicated by the arrow inward from the end 50 of the optical laminate (the straight line extending vertically from the end 50), the color loss region 51 and the region where no color loss occurs. It can be seen that there is (non-color loss region) 52.

[Measurement of color loss by image processing]
The image observed with a microscope was converted into black-and-white 256 gradations (0 to 255) using image analysis software "ImageJ (free software)". As a method of converting to black and white 256 gradations (0 to 255), a method of averaging RGB values was used. FIG. 4 shows an example of the converted data. The midpoint between the color loss region 51 and the non-color loss region 52 (middle of the color loss gradation) in the gradation profile in the direction perpendicular to the end 50 of the optical laminate (arrow in FIG. 3) is the color loss of the optical laminate. As the end portion (FIG. 4), the distance (μm) from the end portion 50 of the optical laminate to the color loss end portion was measured as the color loss distance. Table 1 shows the color loss distance of the optical laminate. The smaller the color loss distance, the narrower the color loss range and the better the moisture resistance and heat resistance.

The color loss distances of the optical laminates using the pressure-sensitive adhesive layers showing the same absorbance (Example 1 and Comparative Example 1, Example 2 and Comparative Example 2, and Example 3 and Comparative Example 3) were compared, and the difference and the difference. Table 1 shows the improvement rate of the color loss distance ((absolute value of difference / color loss distance of Comparative Examples 1 to 3) × 100).

10 Polarizer, 11 Protective film, 20 Light selective absorption adhesive layer, 30 First retardation layer, 31 Second retardation layer, 32 Second adhesive layer, 33 Adhesive layer, 50 Edge of optical laminate , 51 color loss area, 52 non-color loss area, 100, 200 optical laminate, 300 retardation laminate.

Claims

An optical laminate having a polarizer and a light selective absorbing pressure-sensitive adhesive layer laminated in contact with the polarizer.
Iodine is adsorbed and oriented in the polarizer, and the boron content is 5.0% by mass or less.
The pressure-sensitive adhesive composition forming the light-selective-absorbing pressure-sensitive adhesive layer is an optical laminate containing a light-selective-absorbing polymer.
The optical laminate according to claim 1, further comprising a protective film laminated on the side of the polarizer opposite to the light selective absorbing pressure-sensitive adhesive layer side.
The photoselective absorbent polymer has the following chemical formula (1):
> NC = CC = C <(1)
[However, not all of one N atom and four C atoms constituting the chemical formula (1) form a part or all of the aromatic heterocycle. ]
The optical laminate according to claim 1 or 2, which is a resin containing a structural unit having the structure shown by and having a glass transition temperature of 40 ° C. or lower.
The claim that the light selective absorption polymer has a content of a structural unit having a structure represented by the chemical formula (1) of 0.01 parts by mass or more and 50 parts by mass or less with respect to 100 parts by mass of all structural units. The optical laminate according to 3.
The optical laminate according to any one of claims 1 to 4, wherein the light selective absorption polymer has a weight average molecular weight of 300,000 or more.
Any of claims 1 to 5, wherein the pressure-sensitive adhesive composition does not contain a light selective absorber, or the content of the light selective absorber is 0.1 parts by mass or less with respect to 100 parts by mass of all resin components. The optical laminate according to item 1.
The optical laminate according to any one of claims 1 to 6, further comprising a λ / 4 retardation layer laminated on the opposite side of the light selective absorbing pressure-sensitive adhesive layer to the polarizer.
The optical laminate according to any one of claims 1 to 7, which is an antireflection polarizing plate.
An image display device including the image display panel and the optical laminate according to claim 8 arranged in front of the image display panel.
The image display device according to claim 9, which is an organic EL display device.