WO2020031830A1

WO2020031830A1 - Resin and pressure-sensitive adhesive composition

Info

Publication number: WO2020031830A1
Application number: PCT/JP2019/030177
Authority: WO
Inventors: 悠司淺津; 昭一小澤; 国見　信孝
Original assignee: 住友化学株式会社
Priority date: 2018-08-09
Filing date: 2019-08-01
Publication date: 2020-02-13
Also published as: JP2020026528A; KR20210041568A; TWI819053B; CN112566949A; CN112566949B; TW202017953A

Abstract

A resin (A) which includes a structural unit having an indole structure. It is preferable that the resin (A) be a resin which includes a structural unit having a side chain including an indole structure and have a glass transition temperature of 40°C or lower. The resin (A) preferably satisfies relationship (1). (1): ɛ(405)≥0.02 [In relationship (1), ɛ(405) indicates the gram absorptivity coefficient of the resin (A) at wavelength 405 nm. The unit of the gram absorptivity coefficient is L/(g·cm).]

Description

Resin and adhesive composition

The present invention relates to an optical laminate in which a resin, a pressure-sensitive adhesive composition containing the resin, and a pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition are laminated.

2. Description of the Related Art Various members such as organic EL elements, display elements such as liquid crystal cells, and optical films such as polarizing plates, etc., are used in display devices (FPDs: flat panel displays) such as organic electroluminescence displays (organic EL display devices) and liquid crystal display devices. Used. Among these members, the organic EL light emitting element, the liquid crystal compound, and the like are organic substances, and thus are liable to be deteriorated by ultraviolet rays (UV). Furthermore, it has been clarified that a liquid crystal phase difference film and an organic EL light-emitting element obtained by aligning and photo-curing a polymerizable liquid crystal compound tend to deteriorate not only by ultraviolet rays but also by short-wavelength visible light. Have been. In order to solve the above-mentioned problem, it is known to provide a layer containing a compound that absorbs short-wavelength visible light. For example, Patent Document 1 discloses an adhesive formed from an adhesive composition containing a copolymer composed of n-butyl acrylate, 2-hydroxyethyl acrylate and N, N-dimethylacrylamide, and an indole ultraviolet absorber. A polarizing plate with an agent layer is described.

JP-A-2017-48340

However, when the pressure-sensitive adhesive layer containing an ultraviolet absorber described in Patent Document 1 is used as an optical laminate, it is possible to suppress deterioration due to ultraviolet light or short-wave visible light, but it is difficult to prevent the ultraviolet absorber from being applied to another layer. It has been found that migration creates another problem of impairing optical properties. Above all, it was found that in the laminate with the liquid crystal phase difference film, the deterioration of the optical characteristics (change in the phase difference value) due to the transfer of the ultraviolet absorber to another layer became remarkable.

The present invention includes the following inventions.
[1] A resin (A) containing a structural unit having an indole structure.
[2] The resin according to [1], wherein the resin (A) has a glass transition temperature of 40 ° C or lower.
[3] The resin according to [1] or [2], wherein the resin (A) satisfies the following formula (1).
ε (405) ≧ 0.02 (1)
[In the formula (1), ε (405) represents a gram extinction coefficient of the resin (A) at a wavelength of 405 nm. The unit of the gram extinction coefficient is L / (g · cm). ]
[4] The resin according to any one of [1] to [3], wherein the resin (A) satisfies the following formula (2).
ε (405) / ε (440) ≧ 5 (2)
[In the formula (2), ε (405) represents the gram absorption coefficient of the resin (A) at a wavelength of 405 nm, and ε (440) represents the gram absorption coefficient of the resin at a wavelength of 440 nm. ]
[5] The resin according to any one of [1] to [4], wherein the resin (A) is a resin containing a structural unit having an indole structure in a side chain.
[6] The resin according to [5], wherein the structural unit having an indole structure in the side chain is a structural unit derived from a photoselective absorption compound having a polymerizable group and an indole structure.
[7] The resin according to [6], wherein the light selective absorption compound having a polymerizable group and an indole structure is a compound satisfying the following formula (1-a).
ε (405) ≧ 5 (1-a)
[In the formula (1-a), ε (405) represents a gram extinction coefficient of a compound having a polymerizable group and an indole structure at a wavelength of 405 nm. The unit of the gram extinction coefficient is L / (g · cm). ]
[8] The resin according to [7], wherein the light selective absorption compound having a polymerizable group and an indole structure is a compound satisfying the following formula (2-a).
ε (405) / ε (440) ≧ 10 (2-a)
[In the formula (2-a), ε (405) represents a gram extinction coefficient of a compound having a polymerizable group and an indole structure at a wavelength of 405 nm, and ε (440) represents a polymerizable group and an indole structure at a wavelength of 440 nm. It represents the gram extinction coefficient of the compound having.
[9] The structural unit according to [5], wherein the structural unit having an indole structure in the side chain is a structural unit derived from the compound represented by the formula (I) or a structural unit derived from the compound represented by the formula (II). Resin.

[In the formula (I), R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ each independently represent a hydrogen atom, a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxy group, A carboxy group, an aliphatic hydrocarbon group having 1 to 25 carbon atoms which may have a substituent or an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent; —CH ₂ — contained in the hydrocarbon group or the aromatic hydrocarbon group may be substituted with —NR ^1A —, —SO ₂ —, —CO—, —O—, —S—, or —CF ₂ —. Good.
R ^1A represents a hydrogen atom, an alkyl group having 1 to 25 carbon atoms or an aromatic hydrocarbon group having 6 to 18 carbon atoms.
E ¹ represents an electron-withdrawing group.
Z represents a linking group.
A represents a polymerizable group.
In the formula (II), R ¹² and R ¹⁷ each independently represent a hydrogen atom, a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxy group, a carboxy group, or an optionally substituted carbon atom. Represents an aliphatic hydrocarbon group having a number of 1 to 25 or an aromatic hydrocarbon group having a carbon number of 6 to 18 which may have a substituent, and is included in the aliphatic hydrocarbon group or the aromatic hydrocarbon group; CH ₂ — may be substituted by —NR ^11A —, —SO ₂ —, —CO—, —O—, —S— or —CF ₂ —.
R ¹¹ , R ¹³ , R ¹⁴ , R ¹⁵ and R ¹⁶ are each independently a hydrogen atom, a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxy group, a carboxy group, a group containing a polymerizable group, Represents an aliphatic hydrocarbon group having 1 to 25 carbon atoms which may have a substituent or an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent; Alternatively, —CH ₂ — included in the aromatic hydrocarbon group may be substituted with —NR ^12A —, —SO ₂ —, —CO—, —O—, —S—, or —CF ₂ —.
However, at least one of R ¹¹ , R ¹³ , R ¹⁴ , R ¹⁵ and R ¹⁶ represents a group containing a polymerizable group.
R ^11A and R ^12A each independently represent an elementary atom, an alkyl group having 1 to 25 carbon atoms, or an aromatic hydrocarbon group having 6 to 18 carbon atoms.
E ¹¹ represents an electron-withdrawing group. ]
[10] The resin according to [9], wherein R ² is a phenyl group.
[11] The resin according to [9], wherein the compound represented by the formula (I) is a compound represented by the formula (III).

[R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ and E ¹ represent the same meaning as described above.
R ⁷ represents a hydrogen atom, a methyl group or a phenyl group.
Z ¹ is an alkanediyl group having 1 to 12 carbon atoms, a divalent aromatic hydrocarbon group having 6 to 18 carbon atoms, —OR ^2A — * 1, —SR ^2B — * 1, or —NR ^1D Represents -R ^2C- * 1.
Z ² is a single bond, * 2-CO-O-, * 2-O-CO-, * 2-S (= O) _2- , * 2-O-SO _2- , * 2-CO-NR ^1B -, * 2-NR ^1C -CO-, * 2-R ^2D OP (= O) -OR ^2E- , * 2-NR ^1E -CO-O-, * 2-O-CO-NR ^1F- , * 2- (OR ^2F ) _s1- , * 2-CO-S-, * 2-S-CO- or a perfluoroalkanediyl group having 1 to 4 carbon atoms.
R ^1B , R ^1C, R ^1D , R ^1E and R ^1F each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
R ^2A , R ^2B , R ^2C , R ^2D , R ^2E and R ^2F each independently represent a divalent hydrocarbon group having 1 to 18 carbon atoms.
* 1 represents a binding position to ^{Z 2.}
* 2 represents a bond to ^{Z 1.} ]
[12] The resin according to any one of [1] to [11], wherein the resin (A) further has at least one structural unit selected from the structural units described in Group A below.
Group A: a structural unit derived from a (meth) acrylate, a structural unit derived from a styrene-based monomer, a structural unit derived from a vinyl-based monomer, a structural unit derived from an epoxy compound, and a compound represented by the formula (a) The structural unit represented by the structural unit represented by the formula (b) and the structural unit represented by the formula (c)

[In the formula, R ^a1 represents a divalent hydrocarbon group.
R ^b1 and R ^b2 each independently represent a hydrogen atom or a hydrocarbon group.
R ^c1 and R ^c2 each independently represent a divalent hydrocarbon group. ]
[13] The resin according to [12], wherein the content of at least one structural unit selected from the structural units described in Group A is 50% by mass or more based on all structural units of the resin (A).
[14] An adhesive composition containing the resin according to any one of [1] to [13].
[15] The pressure-sensitive adhesive composition according to [14], further comprising a crosslinking agent (B).
[16] An adhesive layer formed from the adhesive composition according to [14] or [15].
[17] The pressure-sensitive adhesive layer according to [16], which satisfies the following formula (3).
A (405) ≧ 0.5 (3)
[In the formula (3), A (405) represents the absorbance at a wavelength of 405 nm. ]
[18] The pressure-sensitive adhesive layer according to [17], further satisfying the following formula (4).
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. ]
[19] An optical laminate in which an optical film is laminated on at least one surface of the pressure-sensitive adhesive layer according to any one of [16] to [18].
[20] The optical laminate according to [19], wherein the optical film is a polarizing plate.
[21] An image display device including the optical laminate according to [20].
[22] A compound represented by the formula (I) or the formula (IV).

[In the formula (I), R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ each independently represent a hydrogen atom, a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxy group, A carboxy group, an aliphatic hydrocarbon group having 1 to 25 carbon atoms which may have a substituent or an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent; —CH ₂ — contained in the hydrocarbon group or the aromatic hydrocarbon group may be substituted with —NR ^1A —, —SO ₂ —, —CO—, —O—, —S—, or —CF ₂ —. Good.
R ^1A represents a hydrogen atom, an alkyl group having 1 to 25 carbon atoms or an aromatic hydrocarbon group having 6 to 18 carbon atoms.
E ¹ represents an electron-withdrawing group.
Z represents a linking group.
A represents a polymerizable group.
In the formula (IV), R ¹² and R ¹⁷ each independently represent a hydrogen atom, a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxy group, a carboxy group, or a carbon which may have a substituent. Represents an aliphatic hydrocarbon group having a number of 1 to 25 or an aromatic hydrocarbon group having a carbon number of 6 to 18 which may have a substituent, and is included in the aliphatic hydrocarbon group or the aromatic hydrocarbon group; CH ₂ — may be substituted by —NR ^11A —, —SO ₂ —, —CO—, —O—, —S— or —CF ₂ —.
R ¹¹ , R ¹³ , R ¹⁴ , R ¹⁵ and R ¹⁶ are each independently a hydrogen atom, a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxy group, a carboxy group, a group containing a polymerizable group, Represents an aliphatic hydrocarbon group having 1 to 25 carbon atoms which may have a substituent or an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent; Alternatively, —CH ₂ — included in the aromatic hydrocarbon group may be substituted with —NR ^12A —, —SO ₂ —, —CO—, —O—, —S—, or —CF ₂ —.
However, at least one of R ¹³ , R ¹⁴ , R ¹⁵ and R ¹⁶ represents a group containing a polymerizable group.
R ^11A and R ^12A each independently represent an elementary atom, an alkyl group having 1 to 25 carbon atoms, or an aromatic hydrocarbon group having 6 to 18 carbon atoms.
E ¹¹ represents an electron-withdrawing group. ]
[23] The compound according to [22], wherein R ² is a phenyl group.
[24] The compound according to [22], wherein the compound represented by the formula (I) is a compound represented by the formula (III).

[R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ and E ¹ represent the same meaning as described above.
R ⁷ represents a hydrogen atom, a cyano group, a methyl group or a phenyl group.
Z ¹ is an alkanediyl group having 1 to 12 carbon atoms, a divalent aromatic hydrocarbon group having 6 to 18 carbon atoms, —OR ^2A — * 1, —SR ^2B — * 1, or —NR ^1D Represents -R ^2C- * 1.
Z ² is a single bond, * 2-CO-O-, * 2-O-CO-, * 2-S (= O) _2- , * 2-O-SO _2- , * 2-CO-NR ^1B -, * 2-NR ^1C -CO-, * 2-R ^2D OP (= O) -OR ^2E- , * 2-NR ^1E -CO-O-, * 2-O-CO-NR ^1F- , * 2- (OR ^2F ) _s1- , * 2-CO-S-, * 2-S-CO- or a perfluoroalkanediyl group having 1 to 4 carbon atoms.
R ^1B , R ^1C, R ^1D , R ^1E and R ^1F each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
R ^2A , R ^2B , R ^2C , R ^2D , R ^2E and R ^2F each independently represent a divalent hydrocarbon group having 1 to 18 carbon atoms.
* 1 represents a binding position to ^{Z 2.}
* 2 represents a bond to ^{Z 1.} ]
[25] The compound according to any one of [22] to [24], wherein E ¹ is a cyano group.

The present invention provides a pressure-sensitive adhesive layer capable of suppressing deterioration of an organic EL light-emitting device and a liquid crystal phase difference film, and a pressure-sensitive adhesive composition forming the pressure-sensitive adhesive layer. Further, there is provided a resin capable of forming a pressure-sensitive adhesive composition capable of favorably suppressing deterioration of an organic EL light emitting element and a retardation film.

1 shows an example of a layer configuration of a pressure-sensitive adhesive layer of the present invention. 1 shows an example of a layer configuration of the optical laminate of the present invention. 1 shows an example of a layer configuration of the optical laminate of the present invention. 1 shows an example of a layer configuration of the optical laminate of the present invention. 1 shows an example of a layer configuration of the optical laminate of the present invention.

<Adhesive composition>
The pressure-sensitive adhesive composition of the present invention contains a resin (A) containing a structural unit having an indole structure. The pressure-sensitive adhesive composition of the present invention may further contain a crosslinking agent (B), a silane compound (D), an antistatic agent and the like.

<Resin (A)>
The resin (A) of the present invention is a resin containing a structural unit having an indole structure, and is preferably a resin containing a structural unit derived from a light selective absorption compound having an indole structure.

The glass transition temperature (Tg) of the resin (A) is preferably 40 ° C. or lower, more preferably 20 ° C. or lower, further preferably 10 ° C. or lower, and particularly preferably 0 ° C. or lower. preferable. Further, 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. When the glass transition temperature of the resin (A) is 40 ° C. or lower, it is advantageous for improving the adhesion of the pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition containing the resin (A) to an adherend. Further, when the glass transition temperature of the resin (A) is -80 ° C or more, it is advantageous for improving the durability of the pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition containing the resin (A). The glass transition temperature can be measured by a differential scanning calorimeter (DSC).

The resin (A) is preferably a resin satisfying the following formula (1).
ε (405) ≧ 0.02 (1)
[In equation (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). ]
The gram absorbance coefficient of the resin (A) can be measured by the method described in Examples.

The larger the value of ε (405) in the resin (A), the more easily light having a wavelength of 405 nm is absorbed. The value of ε (405) is preferably 0.02 L / (g · cm) or more, more preferably 0.1 L / (g · cm) or more, and 0.2 L / (g · cm) or more. Is still more preferable, and is usually 10 L / (g · cm) or less.
When the pressure-sensitive adhesive composition containing the resin (A) is applied to a display device such as an organic EL display device or a liquid crystal display device, when the ε (405) of the resin (A) is 0.02 L / (g · cm) or more, In some cases, since the absorption performance of visible light near 400 nm is good, the deterioration of the retardation film or the organic EL light-emitting element used in a display device such as an organic EL display device or a liquid crystal display device due to visible light is suppressed. Can be.

The resin (A) is preferably a resin satisfying the following formula (2).
ε (405) / ε (440) ≧ 5 (2)
[In equation (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 larger the value of ε (405) / ε (440), the resin (A) can selectively absorb light having a wavelength near 400 nm. The value of ε (405) / ε (440) is preferably 5 or more, more preferably 10 or more, and even more preferably 30 or more.
When ε (405) / ε (440) of the resin (A) is 5 or more, when the pressure-sensitive adhesive composition containing the resin (A) is applied to a display device such as an organic EL display device or a liquid crystal display device. In addition, light near 400 nm can be absorbed and light deterioration of the retardation film can be suppressed without hindering the color expression of the display device.

(4) The resin (A) may contain a structural unit having an indole structure in the main chain, or may contain a structural unit having an indole structure in a side chain. The resin (A) preferably contains a structural unit having an indole structure in a side chain.

構造 The structural unit having an indole structure in the side chain is not particularly limited, but is preferably a structural unit derived from a compound having a polymerizable group and an indole structure. The structural unit derived from a compound having a polymerizable group and an indole structure is preferably a structural unit derived from a light selective absorption compound having a polymerizable group and an indole structure.

The light selective absorption compound having a polymerizable group and an indole structure preferably satisfies the following formula (1-a), and more preferably satisfies the following formula (2-a).
ε (405) ≧ 5 (1-a)
[In the formula (1-a), ε (405) represents a gram extinction coefficient of a compound having a polymerizable group and an indole structure at a wavelength of 405 nm. The unit of the gram extinction coefficient is L / (g · cm). ]
ε (405) / ε (440) ≧ 10 (2-a)
[In the formula (2-a), ε (405) represents a gram extinction coefficient of a compound having a polymerizable group and an indole structure at a wavelength of 405 nm, and ε (440) represents a polymerizable group and an indole structure at a wavelength of 440 nm. It represents the gram extinction coefficient of the compound having. ]

The compound having a polymerizable group and an indole structure has a value of ε (405) of preferably 5 L / (g · cm) or more, more preferably 10 L / (g · cm) or more, and more preferably 20 L / (g · cm). (G · cm) or more, more 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 caused by ultraviolet light or visible light having a short wavelength.
The compound having a polymerizable group and an indole structure preferably has a value of ε (405) / ε (440) of 10 or more, more preferably 15 or more. A compound having a larger value of ε (405) / ε (440) absorbs light near 405 nm and suppresses light deterioration of a display device such as a retardation film or an organic EL element without hindering color expression of the display device. can do.

The structural unit having an indole structure in the side chain is preferably a structural unit derived from the compound represented by the formula (I) or a structural unit derived from the compound represented by the formula (II). More preferably, it is a structural unit derived from the compound represented by the formula:

[In the formula (I), R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ each independently represent a hydrogen atom, a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxy group, A carboxy group, an aliphatic hydrocarbon group having 1 to 25 carbon atoms which may have a substituent or an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent; —CH ₂ — contained in the hydrocarbon group or the aromatic hydrocarbon group may be substituted with —NR ^1A —, —SO ₂ —, —CO—, —O—, —S—, or —CF ₂ —. Good.
R ^1A represents a hydrogen atom, an alkyl group having 1 to 25 carbon atoms or an aromatic hydrocarbon group having 6 to 18 carbon atoms.
E ¹ represents an electron-withdrawing group.
Z represents a linking group.
A represents a polymerizable group.
In the formula (II), R ¹² and R ¹⁷ each independently represent a hydrogen atom, a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxy group, a carboxy group, or an optionally substituted carbon atom. Represents an aliphatic hydrocarbon group having a number of 1 to 25 or an aromatic hydrocarbon group having a carbon number of 6 to 18 which may have a substituent, and is included in the aliphatic hydrocarbon group or the aromatic hydrocarbon group; CH ₂ — may be substituted by —NR ^11A —, —SO ₂ —, —CO—, —O—, —S— or —CF ₂ —.
R ¹¹ , R ¹³ , R ¹⁴ , R ¹⁵ and R ¹⁶ are each independently a hydrogen atom, a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxy group, a carboxy group, a group containing a polymerizable group, Represents an aliphatic hydrocarbon group having 1 to 25 carbon atoms which may have a substituent or an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent; Alternatively, —CH ₂ — included in the aromatic hydrocarbon group may be substituted with —NR ^12A —, —SO ₂ —, —CO—, —O—, —S—, or —CF ₂ —.
However, at least one of R ¹¹ , R ¹³ , R ¹⁴ , R ¹⁵ and R ¹⁶ represents a group containing a polymerizable group.
R ^11A and R ^12A each independently represent an elementary atom, an alkyl group having 1 to 25 carbon atoms, or an aromatic hydrocarbon group having 6 to 18 carbon atoms.
E ¹¹ represents an electron-withdrawing group. ]

Examples of the electron withdrawing group represented by E ¹ and E ¹¹ 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). No.

[Wherein, 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- * 3, -COO- * 3} , -CS- * 3, -CSS- * 3, -CSNR 112 - * 3, -CONR 113 - * 3, -CNR 114 - * 3 or - Represents SO _2- * 3.
R ¹¹² , R ¹¹³ and R ¹¹⁴ each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms or a phenyl group.
* 3 represents a bond to ^{R 111.}
* Represents a bond to a carbon atom. ]

Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
Examples of the alkyl group substituted with a halogen atom include a monofluoromethyl group, a monofluoroethyl group, a monochloromethyl group, a monochloroethyl group, a monobromomethyl group, a monobromoethyl group, a monoiodomethyl group, and a monoiodoethyl group. , Difluoromethyl group, difluoroethyl group, dichloromethyl group, dichloroethyl group, dibromomethyl group, dibromoethyl group, diiodomethyl group, diiodoethyl group, trifluoromethyl group, trichloromethyl group, tribromomethyl group, triiodomethyl group And a halogenated alkyl group. The carbon number of the alkyl group substituted by a halogen atom is usually 1 to 25.

Examples of the hydrocarbon group having 1 to 25 carbon atoms represented by R ¹¹¹ 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, isodecyl group, n-dodecyl group, isododecyl group, undecyl group, myristyl group Linear or branched alkyl group having 1 to 25 carbon atoms such as cetyl group, stearyl group and the like: cycloalkyl group having 3 to 25 carbon atoms such as cyclopropyl group, cyclobutyl group, cyclopentyl group and cyclohexyl group; cyclopropylmethyl A cycloalkylalkyl group having 4 to 25 carbon atoms, such as a cyclohexylmethyl group; a phenyl group, a naphthyl group, An aryl group having 6 to 25 carbon atoms such as a tracenyl group and a biphenyl group; and an aralkyl group having 7 to 25 carbon atoms such as a benzyl group, a phenylethyl group, 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 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.

The linking group represented by Z is not particularly limited as long as it is a divalent linking group.

The polymerizable group represented by A is not particularly limited. For example, it may be a cationic polymerizable group, an anionic polymerizable group, or a radical polymerizable group. More specifically, alkynyl groups such as ethynyl group; epoxy group; oxetanyl group; vinyl ether group; acrylonitrile group; methacrylonitrile group; vinyl group, α-methylvinyl group, acryloyl group, methacryloyl group, allyl group, styryl group. And ethylenically unsaturated groups such as acrylamide group and methacrylamide group.

Examples of the halogen atom represented by R ¹ to R ⁶ and R ¹¹ to R ¹⁷ include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
Examples of the heterocyclic groups represented by R ¹ to R ⁶ and R ¹¹ to R ¹⁷ include groups obtained by removing one hydrogen atom from a heterocyclic ring. Specifically, a pyrrolidine ring group, a pyrroline ring group, an imidazoline ring group, an imidazoline ring group, an oxazoline ring group, a thiazoline ring group, a piperidine ring group, a morpholine ring group, a piperazine ring group, an indole ring group, and an isoindole ring group , Quinoline ring group, thiophene ring group, pyrrole ring group, thiazoline ring group and furan ring group, pyridine ring group, dioxane ring group, morpholine ring group, thiazine ring group, triazole ring group, tetrazole ring group, dioxofuran ring group, pyrazine An aliphatic heterocyclic group having 4 to 30 carbon atoms, an aromatic heterocyclic group having 3 to 20 carbon atoms, such as a ring group, a purine ring group, and the like, are exemplified. These heterocyclic groups may have a structure in which an unsaturated bond is hydrogenated, a structure in which a cyclic skeleton is condensed (for example, a benzimidal ring or a benzimidazole ring), and a hydrogen atom in the heterocycle is further heterocyclic. It may be substituted with a group, a halogen atom, a nitro group, a cyano group, a hydroxy group, a carboxy group or the like.

Examples of the aliphatic hydrocarbon group having 1 to 25 carbon atoms represented by R ¹ to R ⁶ and R ¹¹ to R ¹⁷ include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, and a tert- group. Butyl, sec-butyl, n-pentyl, isopentyl, n-hexyl, isohexyl, n-octyl, isooctyl, n-nonyl, isononyl, n-decyl, isodecyl, n- A linear or branched alkyl group having 1 to 25 carbon atoms, such as a dodecyl group, an isododecyl group, an undecyl group, a myristyl group, a cetyl group, a stearyl group; A cycloalkyl group having 3 to 25 carbon atoms; a cycloalkylalkyl group having 4 to 25 carbon atoms such as a cyclopropylmethyl group and a cyclohexylmethyl group; From the viewpoint of solubility, a branched alkyl group having 3 to 25 carbon atoms such as a 2-ethylhexyl group and a 2-butyloctyl group is preferable.
Examples of the substituent which the aliphatic hydrocarbon group having 1 to 25 carbon atoms represented by R ¹ to R ⁶ and R ¹¹ to R ¹⁷ may have include a heterocyclic group, a halogen atom, a nitro group and a cyano group. , A hydroxy group, a carboxy group, an acetamido group, an amino group, and an alkylamino group having 1 to 12 carbon atoms. As the heterocyclic group, those similar to the heterocyclic group represented by R ¹ can be mentioned.

The aromatic hydrocarbon group having 6 to 18 carbon atoms represented by R ¹ to R ⁶ and R ¹¹ to R ^{17 includes} 6 to 18 carbon atoms such as a phenyl group, a naphthyl group, an anthracenyl group, a biphenyl group and a methylphenyl group. And an aryl group having 18; an aralkyl group having 7 to 18 carbon atoms such as a benzyl group, a phenylethyl group, a naphthylmethyl group, and a phenoxy group. -CH _2- contained in the aromatic hydrocarbon group having 6 to 18 carbon atoms represented by R ¹ to R ⁶ and R ¹¹ to R ¹⁷ is -SO _2- , -CO-, -O-, -S- Alternatively, examples of the group replaced with —CF ₂ — include an aroxy group such as a phenoxy group and a naphthyloxy group. From the viewpoint of wavelength selectivity, the aromatic hydrocarbon group having 6 to 18 carbon atoms represented by R ¹ to R ⁶ and R ¹¹ to R ¹⁷ is an aralkyl group having 7 to 18 carbon atoms or 6 to 18 carbon atoms. And more preferably a benzyl group or an aryloxy group having 6 to 18 carbon atoms.
Examples of the substituent which the aromatic hydrocarbon group having 6 to 18 carbon atoms represented by R ¹ to R ⁶ and R ¹¹ to R ¹⁷ may have include a heterocyclic group, a halogen atom, a nitro group and a cyano group. , A hydroxy group, a carboxy group, an acetamido group, an amino group, and an alkylamino group having 1 to 12 carbon atoms. As the heterocyclic group, those similar to the heterocyclic group represented by R ¹ can be mentioned.

The group containing a polymerizable group represented by R ¹¹ , R ¹³ , R ¹⁴ , R ¹⁵ and R ¹⁶ is not particularly limited as long as it is a group having a polymerizable group at a terminal, and specifically, a compound represented by the formula ( And groups represented by I-2).

[In the formula (I-2), X ² represents a polymerizable group.
R ¹¹⁵ represents an alkanediyl group having 1 to 12 carbon atoms, and —CH ₂ — contained in the alkanediyl group may be replaced by —O—, —CO—, —CS— or —NR ¹¹⁶ —. Good.
R ¹¹⁶ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
* Represents a bond to a carbon atom or a nitrogen atom. ]

Examples of the polymerizable group represented by X ² include the same as the polymerizable group represented by A, and preferably include a vinyl group, an α-methylvinyl group, an acryloyl group, a methacryloyl group, an allyl group, and styryl. And ethylenically unsaturated groups such as a acrylamide group and a methacrylamide group.
The alkanediyl group having 1 to 12 carbon atoms represented by R ¹¹⁵ includes a methylene group, an ethylene group, a propane-1,3-diyl group, a butane-1,4-diyl group, a pentane-1,5-diyl group And hexane-1,6-diyl, ethane-1,1-diyl, propane-1,2-diyl, butane-1,3-diyl, 2-methylpropane-1,3-diyl, 2 -Methylpropane-1,2-diyl group, pentane-1,4-diyl group and 2-methylbutane-1,4-diyl group.
^Examples of the alkyl group having 1 to 6 carbon atoms represented by R ¹¹⁶ include the same as the alkyl group having 1 to 6 carbon atoms represented by R ¹¹² .

At least one of R ¹¹ , R ¹³ , R ¹⁴ , R ¹⁵ and R ¹⁶ represents a group containing a polymerizable group.
At least one of R ¹³ , R ¹⁴ , R ¹⁵ and R ¹⁶ is preferably a group containing a polymerizable group, and any one of R ¹³ , R ¹⁴ , R ¹⁵ or R ¹⁶ is a group containing a polymerizable group. Is more preferable.

R ² is preferably an aromatic hydrocarbon group having 6 to 18 carbon atoms or a heterocyclic group, and is an aromatic hydrocarbon group having 6 to 18 carbon atoms or an aromatic heterocyclic group having 3 to 20 carbon atoms. Is more preferable.
The polymerizable group represented by A is preferably an ethylenically unsaturated group.
Preferably, E ¹ and E ¹¹ are each independently a cyano group.

The compound represented by the formula (I) is preferably a compound represented by the formula (III).

[R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ and E ¹ represent the same meaning as described above.
R ⁷ represents a hydrogen atom, a cyano group, a methyl group or a phenyl group.
Z ¹ is an alkanediyl group having 1 to 12 carbon atoms, a divalent aromatic hydrocarbon group having 6 to 18 carbon atoms, —OR ^2A — * 1, —SR ^2B — * 1, or —NR ^1D Represents -R ^2C- * 1.
Z ² is a single bond, * 2-CO-O-, * 2-O-CO-, * 2-S (= O) _2- , * 2-O-SO _2- , * 2-CO-NR ^1B -, * 2-NR ^1C -CO-, * 2-R ^2D OP (= O) -OR ^2E- , * 2-NR ^1E -CO-O-, * 2-O-CO-NR ^1F- , * 2- (OR ^2F ) _s1- , * 2-CO-S-, * 2-S-CO- or a perfluoroalkanediyl group having 1 to 4 carbon atoms.
R ^1B , R ^1C, R ^1D , R ^1E and R ^1F each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
R ^2A , R ^2B , R ^2C , R ^2D , R ^2E and R ^2F each independently represent a divalent hydrocarbon group having 1 to 18 carbon atoms.
* 1 represents a binding position to ^{Z 2.}
* 2 represents a bond to ^{Z 1.} ]

As the alkanediyl group having 1 to 12 carbon atoms represented by Z ¹ , the same alkanediyl group having 1 to 12 carbon atoms represented by R ¹¹⁵ can be mentioned.
Examples of the divalent aromatic hydrocarbon group having 6 to 18 carbon atoms represented by Z ¹ include a phenylene group and a naphthylene group.

^Examples of the alkyl group having 1 to 6 carbon atoms represented by R ^1B , R ^1C, R ^1D , R ^1E and R ^1F include the same alkyl groups having 1 to 6 carbon atoms represented by R ¹¹² .
Examples of the divalent hydrocarbon group having 1 to 18 carbon atoms represented by R ^2A , R ^2B , R ^2C , R ^2D , R ^2E and R ^2F include a methylene group, an ethylene group and a propane-1,3-diyl group. , Butane-1,4-diyl, pentane-1,5-diyl, hexane-1,6-diyl, ethane-1,1-diyl, propane-1,2-diyl, butane-1, 3-diyl group, 2-methylpropane-1,3-diyl group, 2-methylpropane-1,2-diyl group, pentane-1,4-diyl group and 2-methylbutane-1,4-diyl group An alkanediyl group having 1 to 18 carbon atoms; a divalent aromatic hydrocarbon group having 6 to 18 carbon atoms such as a phenylene group and a naphthylene group.

Z ¹ is preferably —OR ^2A — * 1 (more preferably, R ^2A is an alkanediyl group having 1 to 8 carbon atoms, further preferably alkanediyl group having 4 to 8 carbon atoms).
Z ² is preferably * 2-O-CO-, * 2-O-SO _2- , * 2-NR ^1C -CO- (more preferably, R ^1C is a hydrogen atom).

The compound represented by the formula (II) is preferably a compound represented by the formula (IV).

[R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R ¹⁷ and E ¹¹ represent the same meaning as described above. However, at least one of R ¹³ , R ¹⁴ , R ¹⁵ and R ¹⁶ represents a group containing a polymerizable group. ]

Examples of the compound represented by the formula (I) include the compounds described below.

Examples of the compound represented by the formula (II) include the compounds described below.

The compound represented by the formula (I) wherein A is an ethylenically unsaturated group can be obtained, for example, by reacting a compound represented by the formula (Ia) with a compound represented by the formula (c1). it can.

[In the formula (Ia), R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ and E ¹ represent the same meaning as described above. Z ³ in the formula (c) represents a divalent linking group, and A ¹ represents an ethylenic polymerizable group. ]

The amount of the compound represented by the formula (c1) is preferably 0.5 to 5 mol based on 1 mol of the compound represented by the formula (Ia).
The reaction between the compound represented by the formula (Ia) and the compound represented by the formula (c1) can use a known esterification reaction, but is preferably performed 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, 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 to be used is preferably 0.001 to 0.5 mol per 1 mol of the compound represented by the formula (Ia). The amount of the carbodiimide condensing agent to be used is preferably 0.5 to 5 mol per 1 mol of the compound represented by the formula (Ia).
The reaction between the compound represented by the formula (Ia) and the compound represented by the formula (c1) is preferably performed in an organic solvent. Examples of the organic solvent include toluene, acetonitrile, dichloromethane, trichloromethane and the like.

重合 A polymerization inhibitor may be added to inhibit the reaction between ethylenically unsaturated groups contained in the compound represented by the formula (c1). Examples of the polymerization inhibitor include 2,6-di-t-butyl-4-methylphenol (BHT), 4-methoxyphenol and the like.

The reaction between the compound represented by the formula (Ia) and the compound represented by the formula (c1) is carried out by mixing the compound represented by the formula (Ia) and the compound represented by the formula (c1). .
The reaction temperature of the compound represented by the formula (Ia) with the compound represented by the formula (c1) is preferably -20 to 120 ° C., and the reaction time is usually preferably 1 to 50 hours.

Examples of the compound represented by the formula (Ia) include the compounds described below.

化合物 Examples of the compound represented by the formula (c1) include 4-hydroxybutyl acrylate, 2-hydroxyethyl acrylate and the like.

The compound represented by the formula (Ia) can be obtained by reacting a compound represented by the formula (Ib) with a compound represented by the formula (c2).

[Wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ and E ¹ represent the same meaning as described above. ]

The amount of the compound represented by the formula (c2) is preferably 0.5 to 5 mol based on 1 mol of the compound represented by the formula (Ib).
The reaction between the compound represented by the formula (Ib) and the compound represented by the formula (c2) is preferably performed in the presence of a base. Examples of the base include pyridine, pyrrolidine, piperidine, triethylamine, diisopropylethylamine and the like. The amount of the base to be used is preferably 0.5 to 5 mol per 1 mol of the compound represented by the formula (Ib).
The reaction between the compound represented by the formula (Ib) and the compound represented by the formula (c2) is preferably performed in an organic solvent. Examples of the organic solvent include acetonitrile, isopropanol, toluene, trichloromethane, dichloromethane and the like.
The reaction between the compound represented by the formula (Ib) and the compound represented by the formula (c2) is carried out by mixing the compound represented by the formula (Ia) and the compound represented by the formula (c1). .
The reaction temperature between the compound represented by the formula (Ia) and the compound represented by the formula (c1) is preferably 0 to 120 ° C., and the reaction time is usually preferably 1 to 50 hours.

The resin (A) may be a homopolymer of a structural unit having an indole structure, or a copolymer containing a structural unit having an indole structure and another structural unit. The resin (A) is preferably a copolymer.
Examples of the structural unit that the resin (A) may include in addition to the structural unit having an indole structure include the structural units described in Group A below.
Group A: a structural unit derived from a (meth) acrylate, a structural unit derived from a styrene-based monomer, a structural unit derived from a vinyl-based monomer, a structural unit derived from an epoxy compound, and a compound represented by the formula (a) The structural unit represented by the structural unit represented by the formula (b) and the structural unit represented by the formula (c)

[In the formula, R ^a1 represents a divalent hydrocarbon group.
R ^b1 and R ^b2 each 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) acrylate include methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, n-butyl (meth) acrylate, n-pentyl (meth) acrylate, N-hexyl (meth) acrylate, n-heptyl (meth) acrylate, n-octyl (meth) acrylate, n-nonyl (meth) acrylate, n-decyl (meth) acrylate, (meth) acrylic acid linear alkyl esters of (meth) acrylic acid such as n-dodecyl, lauryl (meth) acrylate, stearyl (meth) acrylate;
I-propyl (meth) acrylate, i-butyl (meth) acrylate, t-butyl (meth) acrylate, i-pentyl (meth) acrylate, i-hexyl (meth) acrylate, (meth) acrylic acid Branching of (meth) acrylic acid such as 2-ethylhexyl, i-octyl (meth) acrylate, i-nonyl (meth) acrylate, i-stearyl (meth) acrylate, i-amyl (meth) acrylate Alkyl esters;
Cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, adamantyl (meth) acrylate, dicyclopentanyl (meth) acrylate, cyclododecyl (meth) acrylate, methylcyclohexyl (meth) acrylate, ( Alicyclic skeleton-containing alkyl esters of (meth) acrylic acid, such as trimethylcyclohexyl (meth) acrylate, tert-butylcyclohexyl (meth) acrylate, and cyclohexyl α-ethoxyacrylate;
Aromatic skeleton-containing esters of (meth) acrylic acid such as phenyl (meth) acrylate;
And the like.

構造 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 alkyl (meth) acrylate 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 alkyl (meth) acrylate include 2-methoxyethyl (meth) acrylate, ethoxymethyl (meth) acrylate, phenoxyethyl (meth) acrylate, and 2- (meth) acrylate. (2-phenoxyethoxy) ethyl, phenoxydiethylene glycol (meth) acrylate, phenoxy poly (meth) acrylate (ethylene glycol) and the like.

These (meth) acrylates can be used alone or in different pluralities.

The resin (A) of the present invention includes, among the alkyl (meth) acrylates, a homopolymer having a glass transition temperature Tg of less than 0 ° C., a structural unit derived from the alkyl (meth) acrylate (a1), and a homopolymer. It preferably contains a structural unit derived from an alkyl (meth) acrylate (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 alkyl (meth) acrylate, literature values such as POLYMER @ HANDBOOK (Wiley-Interscience) can be adopted.

Specific examples of the alkyl (meth) acrylate (a1) include ethyl acrylate, n- and i-propyl acrylate, n- and i-butyl acrylate, n-pentyl acrylate, and 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. (Meth) acrylic acid alkyl esters having about 2 to 12 carbon atoms in the alkyl group.

アルキル As the alkyl (meth) acrylate (a1), one type may be used alone, or two or more types may be used in combination. Among them, 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.

アルキル The alkyl (meth) acrylate (a2) is an alkyl (meth) acrylate other than the alkyl (meth) acrylate (a1). Specific examples of the alkyl (meth) acrylate (a2) include methyl acrylate, cyclohexyl acrylate, isobornyl acrylate, stearyl acrylate, t-butyl acrylate, and the like.

アルキル As the alkyl (meth) acrylate (a2), one type may be used alone, or two or more types may be used in combination. Among them, from the viewpoint of high-temperature durability, the alkyl (meth) acrylate (a2) preferably contains methyl acrylate, cyclohexyl acrylate, isobornyl acrylate, and the like, and more preferably contains methyl acrylate.

Examples of the structural unit derived from the (meth) acrylate include a structural unit derived from the (meth) acrylate having a polar functional group.
As the (meth) acrylate monomer having a polar functional group,
1-hydroxymethyl (meth) acrylate, 1-hydroxyethyl (meth) acrylate, 1-hydroxyheptyl (meth) acrylate, 1-hydroxybutyl (meth) acrylate, 1-hydroxypentyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 2-hydroxypentyl (meth) acrylate, 2-hydroxyhexyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, 3-hydroxybutyl (meth) acrylate, 3-hydroxypentyl (meth) acrylate, 3-hydroxyhexyl (meth) acrylate, 3-hydroxyheptyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, (meth) 4-hydroxypentyl acrylate, 4-hydroxyhexyl (meth) acrylate, 4-hydroxyheptyl (meth) acrylate, 4-hydroxyoctyl (meth) acrylate, 2-chloro-2-hydroxypropyl (meth) acrylate 3-chloro-2-hydroxypropyl (meth) acrylate, 2-hydroxy-3-phenoxypropyl (meth) acrylate, 5-hydroxypentyl (meth) acrylate, 5-hydroxyhexyl (meth) acrylate, (meth) ) 5-hydroxyheptyl acrylate, 5-hydroxyoctyl (meth) acrylate, 5-hydroxynonyl (meth) acrylate, 6-hydroxyhexyl (meth) acrylate, 6-hydroxyheptyl (meth) acrylate, (meth) ) 6-hydroxyoctyl acrylate, (meth) 6-hydroxynonyl acrylate, 6-hydroxydecyl (meth) acrylate, 7-hydroxyheptyl (meth) acrylate, 7-hydroxyoctyl (meth) acrylate, 7-hydroxynonyl (meth) acrylate, (meth) 7-hydroxydecyl acrylate, 7-hydroxyundecyl (meth) acrylate, 8-hydroxyoctyl (meth) acrylate, 8-hydroxynonyl (meth) acrylate, 8-hydroxydecyl (meth) acrylate, (meth) ) 8-hydroxyundecyl acrylate, 8-hydroxydodecyl (meth) acrylate, 9-hydroxynonyl (meth) acrylate, 9-hydroxydecyl (meth) acrylate, 9-hydroxyundecyl (meth) acrylate, 9-hydroxydodecyl (meth) acrylate, (meth) 9-hydroxytridecyl acrylate, 10-hydroxydecyl (meth) acrylate, 10-hydroxyundecyl (meth) acrylate, 10-hydroxydodecyl (meth) acrylate, 10-hydroxytridecyl acrylate, (meth) 10-hydroxytetradecyl acrylate, 11-hydroxyundecyl (meth) acrylate, 11-hydroxydodecyl (meth) acrylate, 11-hydroxytridecyl (meth) acrylate, 11-hydroxytetradecyl (meth) acrylate 11-hydroxypentadecyl (meth) acrylate, 12-hydroxydodecyl (meth) acrylate, 12-hydroxytridecyl (meth) acrylate, 12-hydroxytetradecyl (meth) acrylate, 13 (meth) acrylic acid -Hydroxypentadecyl 13-hydroxytetradecyl (meth) acrylate, 13-hydroxypentadecyl (meth) acrylate, 14-hydroxytetradecyl (meth) acrylate, 14-hydroxypentadecyl (meth) acrylate, 15 (meth) acrylic acid And (meth) acrylic acid alkyl esters having a hydroxy group such as -hydroxypentadecyl and 15-hydroxyheptadecyl (meth) acrylate.

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

Vinyl monomers 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 include vinylidene halides; nitrogen-containing heteroaromatic vinyls such as vinylpyridine, vinylpyrrolidone and vinylcarbazole; conjugated dienes such as butadiene, isoprene and chloroprene; and unsaturated nitriles such as acrylonitrile and methacrylonitrile.

An epoxy compound is a compound having an epoxy group in a molecule. The epoxy group may be an epoxy group bonded to an alicyclic ring such as an epoxycyclopentane structure and an epoxycyclohexane structure.
Examples of the epoxy compound include 3,4-epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate, 3,4-epoxy-6-methylcyclohexylmethyl 3,4-epoxy-6-methylcyclohexanecarboxylate, ethylenebis (3, 4-epoxycyclohexanecarboxylate), bis (3,4-epoxycyclohexylmethyl) adipate, bis (3,4-epoxy-6-methylcyclohexylmethyl) adipate, diethylene glycol bis (3,4-epoxycyclohexylmethyl ether), ethylene Glycol bis (3,4-epoxycyclohexyl methyl ether), 2,3,14,15-diepoxy-7,11,18,21-tetraoxatrispiro [5.2.2.5.2.2] hemicosan, 3- 3,4-epoxycyclohexyl) -8,9-epoxy-1,5-dioxaspiro [5.5] undecane, 4-vinylcyclohexenedionoxide, limonenedoxide, bis (2,3-epoxycyclopentyl) ether, dicyclo Examples include pentadienedioxide, 1,4-butanediol diglycidyl ether, 1,6-hexanediol diglycidyl ether, neopentyl glycol diglycidyl ether, trimethylolpropane triglycidyl ether, and pentaerythritol tetraglycidyl ether.

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

{Structural units selected from the structural units described in Group A are preferably structural units derived from (meth) acrylates. The structural units derived from the (meth) acrylic acid ester are preferably an alkyl (meth) acrylate and an alkyl (meth) acrylate having a hydroxy group.

樹脂 The resin (A) of the present invention may further contain 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 carboxy group, a structural unit derived from a monomer having a heterocyclic group, substituted or unsubstituted Examples include a structural unit derived from a monomer having an amino group.

(Meth) acrylamide monomers include N-methylol (meth) acrylamide, N- (2-hydroxyethyl) (meth) acrylamide, N- (3-hydroxypropyl) (meth) acrylamide, N- (4- (Hydroxybutyl) (meth) acrylamide, N- (5-hydroxypentyl) (meth) acrylamide, N- (6-hydroxyhexyl) (meth) acrylamide, N, N-dimethyl (meth) acrylamide, N, N-diethyl ( (Meth) 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-acryloylamino-2-methyl-1-propanesulfonic acid, N- (methoxymethyl) acrylamide, N- (ethoxymethyl) (meth) acrylamide, N- (propoxymethyl) (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) (meth) acrylamide, N- (2-propoxyethyl) (meth ) Acrylamide, N- [2- (1-methylethoxy) ethyl] (Meth) acrylamide, N- [2- (1-methylpropoxy) ethyl] (meth) acrylamide, N- [2- (2-methylpropoxy) ethyl] (meth) acrylamide, N- (2-butoxyethyl) (meth) ) Acrylamide, N- [2- (1,1-dimethylethoxy) ethyl] (meth) acrylamide and the like. Among them, N- (methoxymethyl) acrylamide, N- (ethoxymethyl) acrylamide, N- (propoxymethyl) acrylamide, N- (butoxymethyl) acrylamide and N- (2-methylpropoxymethyl) acrylamide are preferred.

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

Examples of the monomer having a heterocyclic group include acryloylmorpholine, vinylcaprolactam, N-vinyl-2-pyrrolidone, vinylpyridine, tetrahydrofurfuryl (meth) acrylate, caprolactone-modified tetrahydrofurfuryl acrylate, and 3,4-epoxycyclohexylmethyl (Meth) acrylate, glycidyl (meth) acrylate, 2,5-dihydrofuran and the like.

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

The structural unit (aa) other than the structural unit having an indole structure and the structural unit selected from Group A is preferably a monomer having a carboxy group.

The content of the structural unit having an indole structure is preferably from 0.01 to 50 parts by mass, and more preferably from 0.1 to 20 parts by mass, based on 100 parts by mass of all the structural units contained in the resin (A). More preferably, it is more preferably 0.5 to 15 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, and more preferably 55 to 99.99 parts by mass, based on 100 parts by mass of all the structural units of the resin (A). It is more preferable that the amount be from 50 to 85 parts by mass.
When the resin (A) contains the structural unit (aa), it is preferably 20 parts by mass or less, more preferably 0.5 part 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). The content is more preferably from 0.5 to 10 parts by mass, particularly preferably from 1 to 7 parts by mass.

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 all the structural units 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, still more preferably 0.5 parts by mass or more and 10 parts by mass or less, particularly preferably 1 part by mass or more and 7 parts by mass or less.
From the viewpoint of preventing an increase in the peeling force of the separate film that can be laminated on the outer surface of the pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition, it is preferable that the film does not substantially include a monomer having an amino group. Here, the term "substantially free of a monomer having an amino group" means that the content of the structural unit derived from the monomer having an amino group is 0.1% in 100 parts by mass of all the constituent units constituting the resin (A). It means that it is 1 part by mass or less.

In view of the reactivity between the resin (A) and a crosslinking agent (B) described below, the resin (A) is a monomer having a carboxy group or a structural unit derived from an alkyl (meth) acrylate having a hydroxy group. It preferably contains a structural unit derived from an alkyl (meth) acrylate having a hydroxy group and more preferably contains a structural unit derived from a monomer having a carboxy group. As the alkyl (meth) acrylate 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 carboxy group.

樹脂 The weight average molecular weight (Mw) of the resin (A) of the present invention is preferably 300,000 to 2,500,000, more preferably 500,000 to 2,000,000. 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 problems such as floating between the adherend and the pressure-sensitive adhesive layer and cohesive failure of the pressure-sensitive adhesive layer are reduced. Easy to control. 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 a sheet shape (coated on a substrate). The weight average molecular weight is preferably from 600,000 to 1,800,000, more preferably from 700,000 to 1,700,000, further preferably from 100,000 to 1,700,000, from the viewpoint of compatibility between the durability of the pressure-sensitive adhesive layer and the coating property of the pressure-sensitive adhesive composition. 10,000 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) of the present invention is dissolved in ethyl acetate to form a solution having a concentration of 20% by mass, the viscosity at 25 ° C. is preferably 20 Pa · s or less, and is 0.1 to 15 Pa · s. Is more preferable. When the viscosity is in this range, it is advantageous from the viewpoint of coatability when applying the pressure-sensitive adhesive composition to a substrate. The viscosity can be measured with a Brookfield viscometer.

樹脂 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, and an emulsion polymerization method, and a solution polymerization method is particularly preferable. As a solution polymerization method, for example, a monomer having an indole structure, a monomer for leading a structural unit described in Group A and an organic solvent are mixed as needed, and a thermal polymerization initiator is added under a nitrogen atmosphere. And stirring at a temperature of about 40 to 90 ° C., preferably about 50 to 80 ° C. for about 3 to 15 hours. In order to control the reaction, a monomer or a thermal polymerization initiator may be added continuously or intermittently during the polymerization. The monomer and the thermal initiator may be added to an organic solvent.

熱 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), , 2'-azobis (2,4-dimethylvaleronitrile), 2,2'-azobis (2,4-dimethyl-4-methoxyvaleronitrile), dimethyl-2,2'-azobis (2-methylpropionate) ), Azo compounds such as 2,2'-azobis (2-hydroxymethylpropionitrile); lauryl peroxide, t-butyl hydroperoxide, benzoyl peroxide, t-butylperoxybenzoate, cumene hydroperoxide; Diisopropylperoxydicarbonate, dipropylperoxydicarbonate, t-butylperoxyneode Organic peroxides such as noate, t-butylperoxypivalate and (3,5,5-trimethylhexanoyl) peroxide; and inorganic peroxides such as potassium persulfate, ammonium persulfate and hydrogen peroxide. . Further, a redox initiator using a peroxide and a reducing agent in combination can also be used.

割合 The ratio of the polymerization initiator is about 0.001 to 5 parts by mass based on 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 an active energy ray (for example, ultraviolet light) may be used.

Examples of the organic solvent include aromatic hydrocarbons such as toluene and xylene; esters such as ethyl acetate and butyl acetate; aliphatic alcohols such as propyl alcohol and isopropyl alcohol; ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone. Is mentioned.

The content of the resin (A) is usually from 60% by mass to 99.99% by mass, preferably from 70% by mass to 99.9% by mass, more preferably from 100% by mass, based on 100% by mass of the solid content of the pressure-sensitive adhesive composition. Is from 80% by mass to 99.7% by mass.

<Crosslinking agent (B)>
The pressure-sensitive adhesive composition of the present invention can contain a crosslinking agent (B).
Examples of the crosslinking agent (B) include an isocyanate-based crosslinking agent, an epoxy-based crosslinking agent, an aziridine-based crosslinking agent, and a metal chelate-based crosslinking agent. From the viewpoint of speed and the like, an isocyanate-based crosslinking agent is preferred.

As the isocyanate compound, a compound having at least two isocyanato groups (—NCO) in a molecule is preferable. For example, an aliphatic isocyanate compound (eg, hexamethylene diisocyanate), an alicyclic isocyanate compound (eg, isophorone diisocyanate) Hydrogenated diphenylmethane diisocyanate, hydrogenated xylylene diisocyanate) and aromatic isocyanate compounds (for example, tolylene diisocyanate, xylylene diisocyanate diphenyl methane diisocyanate, naphthalene diisocyanate, triphenyl methane triisocyanate, etc.). The crosslinking agent (B) may be an adduct (adduct) of the isocyanate compound with a polyhydric alcohol compound (for example, an adduct of glycerol, trimethylolpropane, or the like), an isocyanurate, a buret-type compound, a polyether polyol, or a polyester. A derivative such as a urethane prepolymer-type isocyanate compound obtained by an addition reaction with a polyol, an acrylic polyol, a polybutadiene polyol, a polyisoprene polyol, or the like may be used. The crosslinking agents (B) can be used alone or in combination of two or more. Of these, typically, aromatic isocyanate compounds (for example, tolylene diisocyanate, xylylene diisocyanate), aliphatic isocyanate compounds (for example, hexamethylene diisocyanate) or polyhydric alcohol compounds thereof (for example, glycerol, trimethylolpropane )) Or isocyanurate. If the cross-linking agent (B) is an aromatic isocyanate compound and / or an adduct of these polyhydric alcohol compounds or isocyanurates, it is advantageous for forming an optimum cross-link density (or cross-link structure), The durability of the pressure-sensitive adhesive layer can be improved. In particular, when it is an adduct of a tolylene diisocyanate compound and / or a polyhydric alcohol compound thereof, the durability can be improved even when, for example, an adhesive layer is applied to a polarizing plate.

The content of the crosslinking agent (B) is generally 0.01 to 15 parts by mass, preferably 0.05 to 10 parts by mass, more preferably 0.1 to 100 parts by mass with respect to 100 parts by mass of the resin (A). To 5 parts by mass.

The pressure-sensitive adhesive composition of the present invention may further contain a silane compound (D).
Examples of the silane compound (D) include vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris (2-methoxyethoxy) silane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropyltriethoxysilane, and -Glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropylethoxydimethylsilane, 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, Examples include 3-methacryloyloxypropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, and the like.
The silane compound (D) may be a silicone oligomer. Specific examples of the silicone oligomer are described below in the form of a combination of 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 Oligomers containing mercaptomethyl groups such as silane oligomers; 3-glycidoxypropyl Trimethoxysilane-tetramethoxysilane copolymer, 3-glycidoxypropyltrimethoxysilane-tetraethoxysilane copolymer, 3-glycidoxypropyltriethoxysilane-tetramethoxysilane copolymer, 3-glycidoxypropyltriethoxysilane-tetra An ethoxysilane copolymer, a 3-glycidoxypropylmethyldimethoxysilane-tetramethoxysilane copolymer, a 3-glycidoxypropylmethyldimethoxysilane-tetraethoxysilane copolymer, a 3-glycidoxypropylmethyldiethoxysilane-tetramethoxysilane copolymer, Copolymers containing 3-glycidoxypropyl groups, such as 3-glycidoxypropylmethyldiethoxysilane-tetraethoxysilane copolymer; 3-methacryloyl Oxypropyltrimethoxysilane-tetramethoxysilane oligomer, 3-methacryloyloxypropyltrimethoxysilane-tetraethoxysilane oligomer, 3-methacryloyloxypropyltriethoxysilane-tetramethoxysilane oligomer, 3-methacryloyloxypropyltriethoxysilane-tetraethoxy Silane oligomer, 3-methacryloyloxypropylmethyldimethoxysilane-tetramethoxysilane oligomer, 3-methacryloyloxypropylmethyldimethoxysilane-tetraethoxysilane oligomer, 3-methacryloyloxypropylmethyldiethoxysilane-tetramethoxysilane oligomer, 3-methacryloyloxy Propylmethyldiethoxysilane-tetraethoxysilane oligomer Oligomers containing a methacryloyloxypropyl group such as 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 Ethoxysilane-tetramethoxysilane oligomer, 3-acryloyloxypropyl Acryloyloxypropyl group-containing oligomers such as tildiethoxysilane-tetraethoxysilane oligomer; vinyltrimethoxysilane-tetramethoxysilane oligomer, vinyltrimethoxysilane-tetraethoxysilane oligomer, vinyltriethoxysilane-tetramethoxysilane oligomer, vinyltriol Ethoxysilane-tetraethoxysilane oligomer, vinylmethyldimethoxysilane-tetramethoxysilane oligomer, vinylmethyldimethoxysilane-tetraethoxysilane oligomer, vinylmethyldiethoxysilane-tetramethoxysilane oligomer, vinylmethyldiethoxysilane-tetraethoxysilane oligomer, etc. Vinyl group-containing oligomer of 3-aminopropyltrimethoxysilane-tetramethoxysilane Polymer, 3-aminopropyltrimethoxysilane-tetraethoxysilane copolymer, 3-aminopropyltriethoxysilane-tetramethoxysilane copolymer, 3-aminopropyltriethoxysilane-tetraethoxysilane copolymer, 3-aminopropylmethyldimethoxysilane-tetra Amino group-containing methoxysilane copolymer, 3-aminopropylmethyldimethoxysilane-tetraethoxysilane copolymer, 3-aminopropylmethyldiethoxysilane-tetramethoxysilane copolymer, 3-aminopropylmethyldiethoxysilane-tetraethoxysilane copolymer, etc. Copolymers and the like.

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

(In the formula, A ¹ represents an alkanediyl group having 1 to 20 carbon atoms or a divalent alicyclic hydrocarbon group having 3 to 20 carbon atoms, and is a constituent of the alkanediyl group and the alicyclic hydrocarbon group. —CH ₂ — may be replaced by —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 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 ¹ include a methylene group, a 1,2-ethanediyl group, a 1,3-propanediyl group, a 1,4-butanediyl group, a 1,5-pentanediyl group, 1,6-hexanediyl group, 1,7-heptanediyl group, 1,8-octanediyl group, 1,9-nonanediyl group, 1,10-decanediyl group, 1,12-dodecanediyl group, 1,14-tetradecanediyl And 1,16-hexadecanediyl, 1,18-octadecanediyl and 1,20-icosandiyl. 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. Examples of the group in which -CH _2- constituting the alkanediyl group and the alicyclic hydrocarbon group is replaced by -O- or -CO- include -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. ^Examples of the alkoxy group having 1 to 5 carbon atoms represented by ⁴² to R ⁴⁵ include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, an isobutoxy group, a tert-butoxy group, and a pentyloxy group.

Examples of the silane compound represented by the formula (d1) include (trimethoxysilyl) methane, 1,2-bis (trimethoxysilyl) ethane, 1,2-bis (triethoxysilyl) ethane, 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) Silyl) hexane, 1,8-bis (trimethoxysilyl) octane, 1,8-bis (triethoxysilyl) octane, 1,8-bis (tri Bis (tri-C1-5alkoxysilyl) C1-10alkanes such as ropoxysilyl) octane; 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 1,6-bis (dimethoxymethylsilyl) octane, 1,8-bis (dimethoxyethylsilyl) octane and other bis (diC1-5alkoxyC1-5alkylsilyl) C1-10 alkanes; 1,6-bis (methoxydimethyl) Silyl) hexane, 1,8-bis (methoxydimethylsilyl) octane Bis such emissions (mono C1-5 alkoxy - di C1-5 alkylsilyl) such as C1-10 alkanes. Of these, 1,2-bis (trimethoxysilyl) ethane, 1,3-bis (trimethoxysilyl) propane, 1,4-bis (trimethoxysilyl) butane, 1,5-bis (trimethoxysilyl) Bis (tri-C1-3alkoxysilyl) C1-10alkanes 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 preferred.

The content of the silane compound (D) is usually 0.01 to 10 parts by mass, preferably 0.03 to 5 parts by mass, more preferably 0.05 to 100 parts by mass for the resin (A). To 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, and an ionic compound, and an ionic compound is preferable. Conventional ionic compounds can be used. Examples of the cation component constituting the ionic compound include an organic cation and an inorganic cation. Examples of the organic cation include a pyridinium cation, a pyrrolidinium cation, a piperidinium cation, an imidazolium cation, an ammonium cation, a sulfonium cation, and a phosphonium cation. Examples of the inorganic cation include an alkali metal cation such as a lithium cation, a potassium cation, a sodium cation, and a cesium cation, and an alkaline earth metal cation such as a magnesium cation and a calcium cation. In particular, a pyridinium cation, an imidazolium cation, a pyrrolidinium cation, a lithium cation, and a potassium cation are preferable from the viewpoint of compatibility with the (meth) acrylic resin. The anion component constituting the ionic compound may be either an inorganic anion or an organic anion, but is preferably an anion component containing a fluorine atom 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-] and a tetra (pentafluorophenyl) borate anion [(C ₆ F ₅ ) ₄ B-]. 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 preferred.
An ionic compound that is solid at room temperature is preferable in terms of the stability over time of the antistatic performance of the 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 may contain one or more kinds of additives such as a solvent, a crosslinking catalyst, a tackifier, a plasticizer, a softener, a pigment, a rust inhibitor, an inorganic filler, and light scattering fine particles.

<Adhesive layer>
The pressure-sensitive adhesive layer of the present invention is, for example, by dissolving or dispersing the pressure-sensitive adhesive composition in a solvent to form a solvent-containing pressure-sensitive adhesive composition, and then applying it to the surface of a substrate and drying it. Can be formed.
As the substrate, a plastic film is suitable, and specifically, a release film subjected to a release treatment is exemplified. Examples of the release film include a film obtained by subjecting one surface of a film made of a resin such as polyethylene terephthalate, polybutylene terephthalate, polycarbonate, and polyarylate to a release treatment such as a silicone treatment.

The pressure-sensitive adhesive layer of the present invention 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 the 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 a wavelength of 405 nm. If the value of A (405) is less than 0.5, the absorption at a wavelength of 405 nm is low, and light near 400 nm tends to cause deterioration of the organic EL light emitting element and the liquid crystal phase difference film. The value of A (405) is preferably 0.6 or more, more preferably 0.8 or more, and particularly preferably 1.0 or more. Although there is no particular upper limit, 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. The larger the value of A (405) / A (440), the more specific absorption is in the wavelength region around 405 nm, and the pressure-sensitive adhesive layer of the present invention is used for a display device such as an organic EL display device or a liquid crystal display device. When applied, light near 400 nm is absorbed without impairing the color expression of the display device, and light degradation of the organic EL light emitting element and the liquid crystal phase difference film can be suppressed. The value of A (405) / A (440) is preferably 10 or more, more preferably 30 or more, and even more preferably 60 or more.

(4) The thickness of the pressure-sensitive adhesive layer of the present invention is usually 0.1 to 100 μm, preferably 3 to 50 μm, and more preferably 4 to 25 μm.

<Optical laminate>
The pressure-sensitive adhesive composition of the present invention and the pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition can be used, for example, for bonding optical films.
An optical laminate in which an optical film is laminated on at least one surface of the pressure-sensitive adhesive layer of the present invention is also included in the present invention.
The optical laminate of the present invention can be formed by dissolving or dispersing the pressure-sensitive adhesive composition in a solvent to form a solvent-containing pressure-sensitive adhesive composition, and then applying this to the surface of an optical film and drying. . Alternatively, it can also be obtained by forming a pressure-sensitive adhesive layer on a release film in the same manner and laminating (transferring) this pressure-sensitive adhesive layer onto the surface of the optical film.

The optical laminate including the pressure-sensitive adhesive layer of the present invention will be described with reference to the drawings.
Examples of the layer constitution of the pressure-sensitive adhesive layer of the present invention and the optical laminate of the present invention are shown in FIGS.
The pressure-sensitive adhesive layer 1 shown in FIG. 1 is in a state where a release film 2 is adhered to the pressure-sensitive adhesive layer surface 1 for temporary protection of the pressure-sensitive adhesive layer surface.
The optical laminate 10A shown in FIG. 2 is an optical laminate including the optical film 40, the pressure-sensitive adhesive layer 1 of the present invention, and the release film 2.
The optical laminate 10B shown in FIG. 3 is an optical laminate including a protective film 8, an adhesive layer 7, a polarizing film 9, an adhesive layer 7, a protective film 8, the pressure-sensitive adhesive layer 1 of the present invention, and a release film 2. is there.
The optical laminated body 10C shown in FIG. 4 and the optical laminated body 10D shown in FIG. , An optical laminate including the retardation film 110, the pressure-sensitive adhesive layer 7a, and the light emitting element 30 (liquid crystal cell, organic EL cell).

The optical film 40 is a film having an optical function of transmitting, reflecting and absorbing light rays. The optical film 40 may be a single-layer film or a multilayer film. The optical film 40 includes, for example, a polarizing film, a retardation film, a brightness enhancement film, an antiglare film, an antireflection film, a diffusion film, a light-condensing film, a window film, and the like. It is preferable to use these laminated films.

The light-condensing film is used for the purpose of controlling an optical path and may be a prism array sheet, a lens array sheet, a dot-attached sheet, or the like.

The brightness enhancement film is used for the purpose of improving brightness in a liquid crystal display device to which a polarizing plate is applied. Specifically, a plurality of thin film films having different refractive index anisotropies are laminated to each other, and a reflective polarization separation sheet designed to have anisotropy in reflectance, an alignment film of cholesteric liquid crystal polymer and its alignment. Circularly polarized light separating sheets in which a liquid crystal layer is supported on a base film are exemplified.

(4) A wind film means a front plate of a flexible display device such as a flexible display, and is generally disposed on the outermost surface of the display device. Examples of the window film include a resin film made of a polyimide resin. The window film may be a hybrid film of an organic material and an inorganic material, such as a resin film containing polyimide and silica. In addition, a hard coat layer for imparting surface hardness, stain resistance and fingerprint resistance to the surface of the window film may be provided. Examples of the window film include a film described in JP-A-2017-94488.

A polarizing film is a film having 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 perpendicular to the absorption axis (parallel to the transmission axis). A film in which a dichroic dye is adsorbed and oriented on a polyvinyl alcohol-based resin film can be used.
Examples of the dichroic dye include iodine and a dichroic organic dye.
The saponification degree of the polyvinyl alcohol-based resin is usually 85 mol% to 100 mol%, preferably 98 mol% or more. The polyvinyl alcohol-based resin may be modified, for example, polyvinyl formal or polyvinyl acetal modified with aldehyde. The polymerization degree of the polyvinyl alcohol-based resin is usually from 1,000 to 10,000, preferably from 1,500 to 5,000.

Usually, a film obtained by forming a polyvinyl alcohol-based resin is used as a raw film of a polarizing film. The polyvinyl alcohol-based resin can be formed into a film by a known method. The thickness of the raw film is usually 1 to 150 μm, and preferably 10 μm or more in consideration of ease of stretching.

Polarizing film, for example, for the raw film, a step of uniaxially stretching, a step of dyeing the film with a dichroic dye and adsorbing the dichroic dye, a step of treating the film with a boric acid aqueous solution, and The film is washed with water, and finally dried and manufactured. The thickness of the polarizing film is usually 1 to 30 μm, and preferably 20 μm or less, more preferably 15 μm or less, and particularly preferably 10 μm or less, from the viewpoint of reducing the thickness of the optical laminate with an adhesive layer.

At least one surface of the polarizing film is preferably a polarizing plate provided with a protective film via an adhesive.
A known adhesive is used as the adhesive, and may be a water-based adhesive or an active energy ray-curable adhesive.

Examples of the water-based adhesive include a conventional water-based adhesive (for example, an adhesive composed of an aqueous solution of a polyvinyl alcohol-based resin, an aqueous two-part urethane-based emulsion adhesive, an aldehyde compound, an epoxy compound, a melamine-based compound, a methylol compound, an isocyanate compound, Amine compounds, crosslinking agents such as polyvalent metal salts, etc.). Among these, a water-based adhesive composed of an aqueous solution of a polyvinyl alcohol-based resin can be suitably used. When an aqueous adhesive is used, it is preferable to perform a step of bonding the polarizing film and the protective film and then drying the laminated adhesive to remove water contained in the aqueous adhesive. After the drying step, a curing step of curing at a temperature of, for example, about 20 to 45 ° C. may be provided. The thickness of the adhesive layer formed from the aqueous adhesive is usually 0.001 to 5 μm.

The active energy ray-curable adhesive refers to an adhesive that cures when irradiated with an active energy ray such as an ultraviolet ray or an electron beam, for example, a curable composition containing a polymerizable compound and a photopolymerization initiator, a photoreaction. Curable compositions containing a curable resin, curable compositions containing a binder resin and a photoreactive crosslinking agent, and the like, and are preferably ultraviolet curable adhesives.

方法 Examples of a method of bonding the polarizing film and the protective film include a method of subjecting at least one of these surfaces to a surface activation treatment such as a saponification treatment, a corona treatment, or a plasma treatment. When protective films are bonded on both sides of the polarizing film, the adhesive for bonding these resin films may be the same type of adhesive or different types of adhesives.

The protective film is preferably a film formed of a translucent thermoplastic resin. Specifically, a film comprising a polyolefin-based resin; a cellulose-based resin; a polyester-based resin; a (meth) acryl-based resin; or a mixture or copolymer thereof, is fried. When protective films are provided on both surfaces of the polarizing film, the protective films used may be films made of different thermoplastic resins or films made of the same thermoplastic resin.
When the protective film is laminated on at least one surface of the polarizing film, the protective film is preferably a protective film made of a polyolefin resin or a cellulose resin. By using these films, shrinkage of the polarizing film in a high-temperature environment can be effectively suppressed without impairing the optical characteristics of the polarizing film. Note that the protective film may also be an oxygen shielding layer.

A preferred configuration of the polarizing plate is a polarizing plate in which a protective film is laminated on at least one surface of a polarizing film via an adhesive layer. When the protective film is laminated only on one surface of the polarizing film, it is more preferable that the protective film is laminated on the viewing side. The protective film laminated on the viewing side is preferably a protective film made of a triacetyl cellulose resin or a cycloolefin resin. The protective film may be an unstretched film, or may be stretched in an arbitrary direction and have a phase difference. A surface treatment layer such as a hard coat layer or an anti-glare layer may be provided on the surface of the protective film laminated on the viewing side.
When the protective film is laminated on both sides of the polarizing film, the protective film on the panel side (the side opposite to the viewing side) is a protective film or a retardation film made of a triacetyl cellulose resin, a cycloolefin resin or an acrylic resin. Preferably, there is. The retardation film may be a zero retardation film described later.

The retardation film is an optical film exhibiting optical anisotropy, for example, polyvinyl alcohol, polycarbonate, polyester, polyarylate, polyimide, polyolefin, polycycloolefin, polystyrene, polysulfone, polyethersulfone, polyvinylidene fluoride. Stretched films obtained by stretching a polymer film composed of ride / polymethyl methacrylate, acetylcellulose, saponified ethylene-vinyl acetate copolymer, polyvinyl chloride, etc. to about 1.01 to 6 times are exemplified. Among the stretched films, a polymer film obtained by uniaxially or biaxially stretching an acetylcellulose, polyester, polycarbonate film or cycloolefin resin film is preferable. Further, the retardation film may be a retardation film in which a liquid crystal compound is applied to a substrate and has optical anisotropy developed by orientation.
In this specification, the retardation film includes a zero retardation film, and also includes a film called a uniaxial retardation film, a low photoelastic modulus retardation film, a wide viewing angle retardation film, or the like.

The zero Letters retardation film, and the retardation R _th for the front retardation R _e and the thickness direction, are both -15 ~ 15 nm, refers to the isotropic film optically. Examples of the zero retardation film include a resin film made of a cellulose resin, a polyolefin resin (a chain polyolefin resin, a polycycloolefin resin, etc.) or a polyethylene terephthalate resin. In terms of ease, a cellulose resin or a polyolefin resin is preferred. The zero retardation film can also be used as a protective film. Examples of the zero retardation film include “Z-TAC” (trade name) sold by FUJIFILM Corporation, “Zero Tac (registered trademark)” sold by Konica Minolta Opto, Ltd., and Zeon Corporation And "ZF-14" (trade name) sold by the company.

において In the optical film of the present invention, the retardation film is preferably a retardation film in which a liquid crystal compound is applied and oriented to develop optical anisotropy.

Examples of the film in which optical anisotropy is developed by coating and orientation of the liquid crystal compound include the following first to fifth embodiments.
First form: a retardation film in which a rod-shaped liquid crystal compound is oriented in a horizontal direction with respect to a supporting substrate. Second form: a retardation film in which a rod-shaped liquid crystal compound is oriented in a direction perpendicular to a supporting substrate. : Retardation film in which rod-shaped liquid crystal compound is spirally changed in plane in the plane. Fourth form: Retardation film in which discotic liquid crystal compound is tilted. Fifth form: Discotic liquid crystal compound is Biaxial retardation film oriented perpendicular to supporting substrate

For example, as an optical film used for an organic electroluminescence display, the first mode, the second mode, and the fifth mode are suitably used. Alternatively, a retardation film of these forms may be laminated and used.

When the retardation film is a layer made of a polymer in an alignment state of the polymerizable liquid crystal compound (hereinafter, sometimes referred to as an “optically anisotropic layer”), the retardation film may have reverse wavelength dispersion. preferable. The reverse wavelength dispersibility is an optical property 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. Preferably, the retardation film has the following formula: (7) and Expression (8) must be satisfied. Note that Re (λ) represents an in-plane retardation value for light having a wavelength of λ nm.
Re (450) / Re (550) ≦ 1 (7)
1 ≦ Re (630) / Re (550) (8)
In the optical film of the present invention, when the retardation film is in the first form and has reverse wavelength dispersion, it is preferable because coloring during black display on a display device is reduced, and 0.82 ≦ in the formula (7). More preferably, Re (450) / Re (550) ≦ 0.93. Further, it is preferable that 120 ≦ Re (550) ≦ 150.

When the retardation film is a film having an optically anisotropic layer, examples of the polymerizable liquid crystal compound include “3” in Liquid Crystal Handbook (edited by Liquid Crystal Handbook Editing Committee, published by Maruzen Co., Ltd. on October 30, 2000). Compounds having a polymerizable group among compounds described in “8.8.6 {Network (completely cross-linked type)” and “6.5.1 {Liquid crystal material} b. Polymerizable nematic liquid crystal material” ”, and JP-A-2010-31223. JP, JP-A-2010-270108, JP-A-2011-6360, JP-A-2011-207765, JP-A-2011-162678, JP-A-2016-81035, and WO2017 / 043438. And polymerizable liquid crystal compounds described in JP-T-2011-207765.

(4) A method for producing a retardation film from a polymer in an alignment state of a polymerizable liquid crystal compound includes, for example, a method described in JP-A-2010-31223.

In the case of the second embodiment, the front retardation value Re (550) may be adjusted in the range of 0 to 10 nm, preferably in the range of 0 to 5 nm, and the retardation value _{Rth in the} thickness direction is -10 to- It may be adjusted to a range of 300 nm, preferably to a range of -20 to -200 nm. The retardation value R _th in the thickness direction, which means the refractive index anisotropy in the thickness direction, is the retardation value R ₅₀ measured at an angle of 50 degrees with the in-plane fast axis being the inclined axis, and the in-plane retardation value R _50. It can be calculated from the value R ₀ . That is, the retardation value R _th in the thickness direction is the in-plane retardation value R ₀ , the retardation value R ₅₀ measured by inclining the fast axis by 50 degrees with the fast axis as the inclination axis, the thickness d of the retardation film, and the position. the average refractive index n ₀ of the retardation film, obtains the n _x, n _y and n _z by the following equation (10) to (12), these are substituted into equation (9) can be calculated.

R _th = [( _nx + _ny ) / 2− _nz ] × d (9)
_{_{_{R 0 = (n x -n y}}} ) × d (10)
_{_{_{R 50 = (n x -n y}}} ') × d / cos (φ) (11)
_{_{_{(n x + n y + n}}} z) / 3 = n 0 (12)
here,
φ = sin ^-1 [sin (40 °) / n ₀ ]
_{_{_{n y '= n y × n}}} z / _{^{^{[n y 2 × sin 2 (φ}}} ) + n z 2 × cos 2 (φ) ] ^1/2

Films that exhibit optical anisotropy by application and orientation of liquid crystal compounds and films that exhibit optical anisotropy by application of inorganic layered compounds include films referred to as temperature-compensated retardation films and JX. "NH film" (trade name; a film in which rod-shaped liquid crystals are tilted) sold by Nippon Mining & Energy Co., Ltd., and "WV film" (trade name: disc-shaped liquid crystal) sold by Fuji Film Co., Ltd. Is a film with tilted orientation), “VAC film” (trade name; fully biaxially-oriented film) sold by Sumitomo Chemical Co., Ltd., and “new @ VAC film” (trade name) sold by Sumitomo Chemical Co., Ltd. Trade name; biaxially oriented film).

The retardation film may be a multilayer film having two or more layers. For example, there are a retardation film in which a protective film is laminated on one or both sides, and a retardation film in which two or more retardation films are laminated via an adhesive or an adhesive.

When the retardation film is a multilayer film, the structure of the optical laminate including the optical film of the present invention is, as shown in FIG. Includes a retardation film 110 in which a wavelength retardation layer 50 and a 波長 wavelength retardation layer 70 that imparts a phase difference of 波長 wavelength to transmitted light are laminated via an adhesive layer or an adhesive layer 60. Configuration. Further, as shown in FIG. 5, a configuration including the optical film 40 in which the quarter-wave retardation layer 50a and the positive C layer 80 are laminated via the adhesive layer or the pressure-sensitive adhesive layer 60 is also included.

The 図 wavelength retardation layer 50 for imparting a 差 wavelength phase difference and the 波長 wavelength retardation layer 70 for imparting a 波長 wavelength phase difference to transmitted light in FIG. The optical film of the fifth embodiment or the optical film of the fifth embodiment may be used. In the case of the configuration shown in FIG. 4, it is more preferable that at least one of them has the fifth mode.

In the case of the configuration of FIG. 5, the quarter-wave retardation layer 50a is preferably the optical film of the first embodiment, and more preferably satisfies the expressions (7) and (8).
The pressure-sensitive adhesive layer 7a in FIGS. 4 and 5 is a layer formed from the pressure-sensitive adhesive composition. For the pressure-sensitive adhesive layer 7a, a known pressure-sensitive adhesive composition may be used, or the pressure-sensitive adhesive composition of the present invention may be used.

<Liquid crystal display device>
The resin of the present invention, a pressure-sensitive adhesive composition containing the resin, and an optical laminate including a pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition are laminated on a display element such as an organic EL element or a liquid crystal cell to form an organic layer. It can be used for a display device (FPD: flat panel display) such as an EL display device or a liquid crystal display device.

Hereinafter, the present invention will be described in more detail with reference to Examples and Comparative Examples. “%” And “parts” in Examples, Comparative Examples and Polymerization Examples are “% by mass” and “parts by mass” unless otherwise specified.

[Example 1]: Synthesis of light selective absorption compound having indole structure and polymerizable group

After replacing the inside of a 1000 mL four-necked flask equipped with a Dimroth condenser and a thermometer with a nitrogen atmosphere, a compound represented by the formula (1) (1-methyl-2-phenyl-1H-indole-3-carboxaldehyde) is obtained. 100 parts, 40 parts of cyanoacetic acid, 76 parts of piperidine and 300 parts of acetonitrile were charged and kept at 80 ° C. for 4 hours while stirring. From the resulting mixture, the precipitated crystals were separated by filtration and taken out. The obtained crystals and 500 parts of 5% sulfuric acid were mixed and kept at 80 ° C. for 1 hour with stirring. The obtained mixture was filtered to obtain a solid. The obtained solid is washed with 300 parts of water and dried, and the compound represented by the formula (2) (2-cyano-3- (1-methyl-2-phenyl-1H-indol-3-yl)- 116 parts of 2-propenoic acid) were obtained.

Identification of the compound represented by the formula (2)
¹ H-NMR (CDCl ₃ ) δ: 3.70 (s, 3H), 7.30-7.42 (dt, 2H), 7.50-7.55 (m, 2H), 7.60-7 .64 (m, 3H), 7.68 (d, 1H), 7.93 (s, 1H), 8.26 (d, 1H)

After replacing the inside of a 100 mL four-necked flask equipped with a thermometer with a nitrogen atmosphere, 5 parts of the compound represented by the formula (2), 2.3 parts of 4-hydroxybutyl acrylate, N, N-dimethyl-4 -Aminopyridine 0.4 part, 2,6-di-t-butyl-4-methylphenol 0.2 part and trichloromethane 50 part were charged and cooled to 0 ° C. 2.2 parts of N, N'-diisopropylcarbodiimide was added dropwise to the obtained mixture while maintaining the temperature at 0 to 5 ° C. After the dropwise addition, the resulting mixture was kept at 10 ° C. for 4 hours. The obtained mixture was filtered to obtain a filtrate. The obtained filtrate was concentrated to obtain an oil. To the obtained oil, 50 parts of toluene and 50 parts of water were mixed and separated to obtain a toluene layer. The obtained toluene layer was concentrated to obtain yellow crude crystals. The crude crystals were recrystallized from isopropyl alcohol to give a compound of the formula (3) (2-cyano-3- (1-methyl-2-phenyl-1H-indol-3-yl) -2-propenoic acid- 4-Acryloyloxybutyl) 4.9 parts were obtained. The maximum absorption wavelength of the compound represented by the formula (3) was 386 nm.

Identification of the compound represented by the formula (3)
¹ H-NMR (CDCl ₃ ) δ: 1.75-1.80 (m, 4H), 3.70 (s, 3H), 4.15-4.20 (t, 2H), 4.23-4 .27 (t, 2H), 5.78-5.82 (dd, 1H), 6.06-6.14 (dd, 1H), 6.36-6.41 (dd, 1H) 7.35- 7.43 (m, 5H), 7.54-7.57 (m, 3H), 8.12 (s, 1H), 8.42-8.45 (m, 1H)

The obtained methyl ethyl ketone solution (0.006 g / L) of the compound represented by the formula (3) is placed in a 1 cm quartz cell, and the quartz cell is set on a spectrophotometer UV-2450 (manufactured by Shimadzu Corporation). The absorbance was measured in a wavelength range of 300 to 800 nm in 1 nm steps by the double beam method. The gram extinction coefficient for each wavelength was calculated from the obtained absorbance value, the concentration of the compound in the solution, and the optical path length of the quartz cell. As a result, ε (405) = 34.9 L / (g · cm), ε (440) = 2.0 L / (g · cm), and ε (405) / ε (440) = 17.5. Met.
ε (λ) = A (λ) / CL
[Where ε (λ) represents the gram extinction coefficient L / (g · cm) of the compound represented by the formula (3) at the wavelength λnm, A (λ) represents the absorbance at the wavelength λnm, and C represents the concentration. g / L, where L is the optical path length cm of the quartz cell. ]

[Example 2]: Synthesis of light selective absorption compound having indole structure and polymerizable group

A compound represented by the formula (4) (2-cyanoethyl) was prepared in the same manner as in Example 1 except that 2.3 parts of 4-hydroxybutyl acrylate was used instead of 2.3 parts of 2-hydroxyethyl acrylate. 4.3 parts of -2- (1-methyl-2-phenyl-1H-indol-3-yl) -2-propenoic acid-2-acryloyloxyethyl) were obtained. The maximum absorption wavelength of the compound represented by the formula (4) was 388 nm. When the gram extinction coefficient was determined in the same manner as in Example 1, ε (405) = 45.4 L / (g · cm), ε (440) = 1.0 L / (g · cm), and ε (405) / ε (440) = 45.4.

Identification of the compound represented by the formula (4)
¹ H-NMR (CDCl ₃ ) δ: 3.70 (s, 3H), 4.38-4.43 (dt, 2H), 4.43-4.48 (dt, 2H), 5.83-5 .86 (dd, 1H), 6.09-6.17 (dd, 1H), 6.4-6.45 (dd, 1H) 7.35-7.45 (m, 5H), 7.52- 7.58 (m, 3H), 8.12 (s, 1H), 8.42-8.45 (m, 1H)

[Example 3]: Synthesis of resin (A-1) containing structural unit having an indole structure In a reaction vessel equipped with a cooling pipe, a nitrogen introduction pipe, a thermometer, and a stirrer, 141 parts of ethyl acetate as a solvent, acrylic acid A mixed solution of 94 parts of butyl, 3 parts of 2-hydroxyethyl acrylate, and 3 parts of the compound represented by the formula (3) was charged, and the inside temperature of the apparatus was reduced to 60 while replacing the air in the apparatus with nitrogen gas to eliminate oxygen. ° C. To the obtained mixture, a solution prepared by dissolving 0.63 parts of azobisisobutyronitrile (polymerization initiator) in 10 parts of ethyl acetate was added in total. The obtained mixture was kept at 60 ° C. for 7 hours, and then a solution prepared by dissolving 0.0012 parts of 4-methoxyphenol (polymerization inhibitor) in 5 parts of ethyl acetate was added to the obtained mixture. Ethyl acetate was added to the obtained mixture to adjust the concentration of the resin (A-1) having an indole structure to 20%, thereby preparing an ethyl acetate solution of the resin (A-1) having an indole structure. The obtained resin (A-1) having an indole structure had a weight average molecular weight Mw of 740,000 in terms of polystyrene by GPC and Mw / Mn of 5.2. The glass transition temperature by DSC was -51 ° C.

<Gram extinction coefficient ε measurement>
A solution of the obtained resin (A-1) in methyl ethyl ketone (0.011 g / L) was placed in a 1 cm quartz cell, and the quartz cell was set on a spectrophotometer UV-2450 (manufactured by Shimadzu Corporation), followed by a double beam method. The absorbance was measured in a wavelength range of 300 to 800 nm in steps of 1 nm. The gram extinction coefficient for each wavelength was calculated from the obtained absorbance value, the concentration of the resin (A) in the solution, and the optical path length of the quartz cell. As a result, ε (405) of resin (A-1) = 0.442 L / (g · cm), ε (440) = 0.008 L / (g · cm), ε (405) / ε (440) = 53.3.
ε (λ) = A (λ) / CL
[Where ε (λ) represents the gram extinction coefficient L / (g · cm) of the resin (A) at a wavelength λnm, A (λ) represents the absorbance at a wavelength λnm, and C represents the concentration g / L. , L represent the optical path length cm of the quartz cell. ]

Example 4 Synthesis of Resin (A-2) Containing Structural Unit Having Indole Structure In a reaction vessel equipped with a cooling pipe, a nitrogen introduction pipe, a thermometer, and a stirrer, 141 parts of ethyl acetate as a solvent, acrylic acid A mixed solution of 94 parts of butyl, 3 parts of 2-hydroxyethyl acrylate, and 3 parts of the compound represented by the formula (4) was charged, and the inside temperature of the apparatus was adjusted to 60 while replacing the air in the apparatus with nitrogen gas to eliminate oxygen. ° C. To the obtained mixture, a solution prepared by dissolving 0.63 parts of azobisisobutyronitrile (polymerization initiator) in 10 parts of ethyl acetate was added in total. The obtained mixture was kept at 60 ° C. for 7 hours, and then a solution prepared by dissolving 0.0012 parts of 4-methoxyphenol (polymerization inhibitor) in 5 parts of ethyl acetate was added to the obtained mixture. Ethyl acetate was added to the obtained mixture to adjust the concentration of the resin (A-2) having an indole structure to 20%, thereby preparing an ethyl acetate solution of the resin (A-2) having an indole structure. The obtained resin (A-2) having an indole structure had a weight average molecular weight Mw of 670,000 in terms of polystyrene measured by GPC and Mw / Mn of 4.9. The glass transition temperature by DSC was -50 ° C. The gram extinction coefficient of the resin (A-2) was measured in the same manner as in Example 3. As a result, ε (405) = 0.336 L / (g · cm) and ε (440) = 0.035 L / ( g · cm), and ε (405) / ε (440) = 9.5.

[Polymerization Example 1]: Preparation of acrylic resin (A-3) 141 parts of ethyl acetate, 94 parts of butyl acrylate, and 3 parts of 2-hydroxyethyl acrylate were charged, and air in the apparatus was replaced with nitrogen gas to remove oxygen. The internal temperature was set to 60 ° C. To the obtained mixture, a solution prepared by dissolving 0.63 parts of azobisisobutyronitrile (polymerization initiator) in 10 parts of ethyl acetate was added in total. The obtained mixture was kept at 60 ° C. for 7 hours, and then a solution prepared by dissolving 0.0012 parts of 4-methoxyphenol (polymerization inhibitor) in 5 parts of ethyl acetate was added to the obtained mixture. Ethyl acetate was added to the obtained mixture to adjust the concentration of the acrylic resin (A-3) to 20%, thereby preparing an ethyl acetate solution of the acrylic resin (A-3). The obtained acrylic resin (A-3) had a weight average molecular weight Mw in terms of polystyrene measured by GPC of 600,000 and Mw / Mn of 6.0. The glass transition temperature by DSC was -49 ° C. The gram extinction coefficient was measured in the same manner as in Example 3. As a result, there was no absorption at the wavelengths of 405 nm and 440 nm, and both the absorbances were 0.

<Preparation of pressure-sensitive adhesive composition and pressure-sensitive adhesive layer>
(A) Preparation of pressure-sensitive adhesive composition [Example 5]: Preparation of pressure-sensitive adhesive composition (1) Ethyl acetate solution (resin concentration: 20%) of the obtained resin (A-1) having an indole structure, To 100 parts of the solid content of the solution, 0.5 part of a crosslinking agent (Coronate L, 75% of solid content: manufactured by Tosoh) and 0.5 part of a silane compound (manufactured by Shin-Etsu Chemical: KBM-403) were mixed. Further, 2-butanone was added so that the solid content concentration became 14%, to obtain a pressure-sensitive adhesive composition (1). In addition, the compounding quantity of the said crosslinking agent (Coronate L) is a mass part as an active ingredient.

[Example 6]: Preparation of pressure-sensitive adhesive composition (2) To an ethyl acetate solution (resin concentration: 20%) of the obtained resin (A-2) having an indole structure, based on 100 parts of solid content of the solution Then, 0.5 parts of a cross-linking agent (Coronate L, solid content 75%: manufactured by Tosoh) and 0.5 part of a silane compound (manufactured by Shin-Etsu Chemical: KBM-403) are mixed, and the solid content concentration becomes 14%. Thus, 2-butanone was added to obtain a pressure-sensitive adhesive composition (2). In addition, the compounding quantity of the said crosslinking agent (Coronate L) is a mass part as an active ingredient.

[Comparative Example 1]: Preparation of pressure-sensitive adhesive composition (3) In an ethyl acetate solution of acrylic resin (A-3) (resin concentration: 20%), a crosslinking agent (coronate) was added to 100 parts of solid content of the solution. L, 75% solid content: 0.5 part by Tosoh Corporation, 0.5 part of a silane compound (KBM-403 by Shin-Etsu Chemical Co., Ltd.) and a light-absorbing compound (ultraviolet absorber; BONASORB UA-3911 by Orient Chemical Co., Ltd.) 3) were mixed, and 2-butanone was added so that the solid content concentration became 14%, to obtain a pressure-sensitive adhesive composition (3). In addition, the compounding quantity of the said crosslinking agent (Coronate L) is a mass part as an active ingredient.

[Preparation Example 1]: Preparation of pressure-sensitive adhesive composition (4) In an ethyl acetate solution (resin concentration: 20%) of acrylic resin (A-3), a crosslinking agent (coronate) was added to 100 parts of solid content of the solution. L, 75% solids: 0.5 part of Tosoh) and 0.5 part of a silane compound (KBM-403 manufactured by Shin-Etsu Chemical Co., Ltd.) are mixed, and 2-butanone is further added so that the solid concentration becomes 14%. Was added to obtain a pressure-sensitive adhesive composition (4).

(B) Preparation of Pressure-Sensitive Adhesive Layer A release-treated polyethylene terephthalate film (SP-PLR382050, manufactured by Lintec Co., Ltd .; hereinafter, abbreviated as “separator”) was prepared on the release-treated surface in (a) above. Each pressure-sensitive adhesive composition was applied using an applicator and dried at 100 ° C. for 1 minute to prepare a pressure-sensitive adhesive layer. The thickness of the obtained pressure-sensitive adhesive layer was 15 μm.
The pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition obtained in Example 5 was referred to as a pressure-sensitive adhesive layer (1), and the pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition obtained in Example 6 was referred to as a pressure-sensitive adhesive layer. (2) The pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition obtained in Comparative Example 1 was bonded to the pressure-sensitive adhesive layer (3), and the pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition obtained in Preparation Example 1 was bonded to the pressure-sensitive adhesive layer. This was the agent layer (4).

<Absorbance measurement of adhesive layer>
The obtained pressure-sensitive adhesive layer (1) was bonded to an alkali-free glass (trade name “EAGLE XG” manufactured by Corning Incorporated), and the separator was peeled off. ZF-14) manufactured by ZEON CORPORATION was laminated to prepare a laminate for evaluating an adhesive layer. The prepared laminate for evaluating an adhesive layer was set on a spectrophotometer UV-2450 (manufactured by Shimadzu Corporation), and the absorbance was measured by a double beam method in a wavelength range of 300 to 800 nm in 1 nm steps. The absorbance of the alkali-free glass alone and the cycloolefin-based resin film alone was 0 at wavelengths of 405 nm and 440 nm.
Similarly, the absorbances of the pressure-sensitive adhesive layers (2) and (3) were measured. Table 1 shows the absorbance of the pressure-sensitive adhesive layers (1) to (3).

<Preparation of optical laminate>
(I) Production of Polarizing Film A polyvinyl alcohol film (“Kuraray Poval Film VF-PE # 3000”, manufactured by Kuraray Co., Ltd.) having an average degree of polymerization of about 2400, a degree of saponification of 99.9 mol%, and a thickness of 30 μm was obtained by using 37 After being immersed in pure water at 30 ° C., it was immersed at 30 ° C. in an aqueous solution containing iodine and potassium iodide (iodine / potassium iodide / water (weight ratio) = 0.04 / 1.5 / 100). Then, it was immersed in an aqueous solution containing potassium iodide and boric acid (potassium iodide / boric acid / water (weight ratio) = 12 / 3.6 / 100) at 56.5 ° C. Next, the film was washed with pure water at 10 ° C. and then dried at 85 ° C. to obtain a polarizing film A having a thickness of about 12 μm in which iodine was adsorbed and oriented in polyvinyl alcohol. Stretching was mainly performed in the steps of iodine dyeing and boric acid treatment, and the total stretching ratio was 5.3 times.

(Ii) Preparation of Polarizing Plate A transparent protective film ("25KCHCN-TC") obtained by applying a 7 μm hard coat layer to a 25 μm thick triacetyl cellulose film on one side of the polarizing film obtained in (i) , Toppan Printing Co., Ltd.) via an adhesive made of an aqueous solution of a polyvinyl alcohol-based resin, and a 23 μm-thick cycloolefin-based resin film (Nippon Zeon Co., Ltd.) on the surface opposite to the transparent protective film. "ZF14-023") was laminated to produce an optical film A (polarizing plate, thickness 67 μm).

(Iii) Preparation of a composition for forming a photo-alignment film A compound having the following structure was synthesized by the method described in JP-A-2013-33248. 5 parts of the following compound and 95 parts of cyclopentanone were mixed as components, and the obtained mixture was stirred at 80 ° C. for 1 hour to obtain a composition for forming a photo-alignment film.

(Iv) Preparation of Composition Containing Polymerizable Liquid Crystal Compound Polymerizable liquid crystal compound A having the following structure was synthesized by the method described in JP-A-2010-31223. The maximum absorption wavelength λmax (LC) of the polymerizable liquid crystal compound A was 350 nm.
12 parts of a polymerizable liquid crystal compound A having the following structure, 0.12 parts of a polyacrylate compound (leveling agent; BYK-361N manufactured by BYK-Chemie), 0.72 parts of a polymerization initiator (Irgacure 369 manufactured by Ciba Specialty Chemicals) and cyclo 100 parts of pentanone were mixed to obtain a composition containing a polymerizable liquid crystal compound.

(V) Production of Optically Anisotropic Layer A cycloolefin resin film (ZF-14, manufactured by Zeon Corporation) was treated with a corona treatment device (AGF-B10, manufactured by Kasuga Electric Co., Ltd.) at an output of 0.3 kW. Processing was performed once at a speed of 3 m / min. The composition for forming a photo-alignment film obtained in (iii) is coated on the surface subjected to the corona treatment with a bar coater, dried at 80 ° C. for 1 minute, and polarized UV irradiation apparatus (SPOT CURE SP-7; USHIO Inc.) Was used to perform polarized UV exposure with an integrated light amount of 100 mJ / cm ² . It was 100 nm when the film thickness of the obtained alignment film was measured with an ellipsometer.
Subsequently, a coating liquid comprising the composition A containing the polymerizable liquid crystal compound obtained in (iv) was applied on the alignment film using a bar coater, dried at 120 ° C. for 1 minute, and then subjected to a high-pressure mercury lamp. UV light was applied from the side coated with the composition containing the polymerizable liquid crystal compound (Unicur VB-15201BY-A, manufactured by Ushio Inc.) (in a nitrogen atmosphere, the integrated light amount at a wavelength of 313 nm: 500 mJ / cm ^2). ) To form an optical film including the optically anisotropic layer 1. When the thickness of the obtained optically anisotropic layer 1 was measured with a laser microscope, it was 2 μm.

Example 7 Production of Optical Laminate (1) The pressure-sensitive adhesive layer (1) was bonded to the surface of the cycloolefin resin film of the polarizing plate produced in (ii) above, and the separator was peeled off. Further, the surface of the pressure-sensitive adhesive layer (1) from which the separator was peeled off was bonded to the surface of the optically anisotropic layer prepared in (v) opposite to the surface of the cycloolefin-based resin film, and the cycloolefin-based resin film was peeled off. The pressure-sensitive adhesive layer (4) with a separator was attached to the surface of the optically anisotropic layer from which the cycloolefin-based resin film was peeled off, to obtain an optical laminate (1).

[Example 8]: Production of optical laminate (2) An optical laminate (2) was obtained in the same manner as in Example 7, except that the pressure-sensitive adhesive layer (1) was replaced with the pressure-sensitive adhesive layer (2).

Comparative Example 2 Production of Optical Laminate (3) An optical laminate (3) was obtained in the same manner as in Example 7, except that the pressure-sensitive adhesive layer (1) was replaced with the pressure-sensitive adhesive layer (3).

[Production Example 2]: Production of Optical Laminate (4) An optical laminate (4) was obtained in the same manner as in Example 5, except that the pressure-sensitive adhesive layer (1) was replaced with the pressure-sensitive adhesive layer (4).

<Evaluation of bleed resistance of pressure-sensitive adhesive layer>
The obtained optical laminated body (1) is cut into a size of 40 mm × 40 mm, the separator laminated on the pressure-sensitive adhesive layer (4) is peeled off, and this is alkali-free glass [trade name “EAGLE” manufactured by Corning Incorporated). XG "]. In the obtained optical laminated body with glass, precipitation of in-plane compound crystals was confirmed using a microscope. Thereafter, the obtained optical laminated body with glass is put into an oven at a temperature of 23 ° C. and 60% for 500 hours, and precipitation of compound crystals in the plane is confirmed using a microscope. confirmed. Table 2 shows the evaluation results.

粘着 The bleed resistance of the pressure-sensitive adhesive layer was evaluated in the same manner as described above, except that the optical laminate (1) was replaced with the optical laminate (2). Table 2 shows the evaluation results.

粘着 The bleed resistance of the pressure-sensitive adhesive layer was evaluated in the same manner as described above except that the optical laminate (1) was replaced with the optical laminate (3). Table 2 shows the evaluation results.

<Confirmation of phase difference change effect on optically anisotropic layer by adhesive layer>
The obtained optical laminated body (1) is cut into a size of 40 mm × 40 mm, the separator laminated on the pressure-sensitive adhesive layer (4) is peeled off, and this is alkali-free glass [trade name “EAGLE” manufactured by Corning Incorporated). XG "]. The retardation value at a wavelength of 450 nm of the obtained optical laminated body with glass was measured by a birefringence measuring device (KOBRA-WR; manufactured by Oji Scientific Instruments). Thereafter, the optical laminate with glass was put into an oven at a temperature of 80 ° C. for 120 hours, taken out and left in an environment of 23 ° C. and 50% for 24 hours, and then a phase difference value at a wavelength of 450 nm was measured again.
In the same manner as above, the measurement was performed by replacing the optical laminate (1) with the optical laminate (4).
The change in the retardation value of the optical laminate (1) is calculated from the amount of change in the retardation value of the optical laminate (1) at a wavelength of 450 nm before and after the endurance of the optical laminate (1). The change was subtracted. Table 2 shows the phase difference value change values.

影響 The effect of the phase difference change on the optically anisotropic layer due to the pressure-sensitive adhesive layer was confirmed in the same manner as described above except that the optical laminate (1) was replaced with the optical laminate (2). Table 2 shows the phase difference change values before and after endurance.

(4) The effect of a phase difference change on the optically anisotropic layer due to the pressure-sensitive adhesive layer was confirmed in the same manner as described above except that the optical laminate (1) was replaced with the optical laminate (3). Table 2 shows the phase difference change values before and after endurance.

<Absorbance measurement of optical film>
The obtained optical laminated body (1) is cut into a size of 40 mm × 40 mm, the separator laminated on the pressure-sensitive adhesive layer (4) is peeled off, and this is alkali-free glass [trade name “EAGLE” manufactured by Corning Incorporated). XG "]. About the obtained measurement sample, the transmission axis direction and the absorption axis of the optical laminated body (1) in the wavelength range of 380 to 780 nm were measured using a spectrophotometer with an integrating sphere [product name “V7100” manufactured by JASCO Corporation]. The transmission spectrum in the direction was measured, and the absorbance at a wavelength of 405 nm of the optical laminate (1) was calculated from the transmission spectrum in the transmission axis direction of the optical laminate (1). In addition, the absorbance at a wavelength of 350 nm, a wavelength of 405 nm, and a wavelength of 440 nm was 0 for each of the TAC film alone, the COP film alone, and the alkali-free glass alone.

<Evaluation of weather resistance>
The optical laminate (1) was put into a sunshine weather meter (manufactured by Suga Test Instruments Co., Ltd .: model number SUNSHINE WEATHER METER S80) at 63 ° C. and 50% humidity for 24 hours, and a 24-hour weather resistance test was performed. The absorbance of the sample taken out was measured in the same manner as in the above <Measurement of absorbance of optical film>. From the measured absorbance, the absorbance retention of the sample at a wavelength of 405 nm was determined based on the following equation. Table 1 shows the results. The higher the absorbance retention, the better the weather resistance without deterioration of the light selective absorption function.
Absorbance retention = (A (405) after endurance test / A (405) before endurance test) × 100

When a pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition containing the resin (A) of the present invention was laminated on an optical film, a change in retardation was suppressed. This is because, by incorporating a light selective absorption compound having a polymerizable group and an indole structure into a resin, a light selective absorption compound having an indole structure is compared with a pressure-sensitive adhesive composition containing only a light selective absorption compound having an indole structure. This is probably because the transfer of the absorbing compound was suppressed.
Further, the pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition containing the resin (A) of the present invention does not increase the precipitation of the compound even after subjected to a heat test at 85 ° C. for 120 hours, and has good bleed resistance. Have. Further, the pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition containing the resin (A) of the present invention has a good value of A (405) / A (440).

The resin of the present invention, a pressure-sensitive adhesive composition containing the resin, a pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition, and an optical laminate including the pressure-sensitive adhesive layer are suitably used for a liquid crystal panel and a liquid crystal display device. .

DESCRIPTION OF SYMBOLS 1 Adhesive layer 2

Release film

10A, 10B, 10C, 10D Optical laminated body 8 Protective film 7 Adhesive layer 7a Adhesive layer 9 Polarizing film 30 Light emitting element 40

Optical film

50, 50a Quarter-wave retardation layer 60 Adhesive Layer or pressure-sensitive adhesive layer 70 1/2 wavelength retardation layer 80 positive C layer 100 polarizing plate 110 retardation film

Claims

樹脂 Resin (A) containing a structural unit having an indole structure.
樹脂 The resin according to claim 1, wherein the resin (A) has a glass transition temperature of 40 ° C or lower.
The resin according to claim 1, wherein the resin (A) satisfies the following formula (1).
ε (405) ≧ 0.02 (1)
[In the formula (1), ε (405) represents a gram extinction coefficient of the resin (A) at a wavelength of 405 nm. The unit of the gram extinction coefficient is L / (g · cm). ]
4. The resin according to claim 1, wherein the resin (A) satisfies the following formula (2).
ε (405) / ε (440) ≧ 5 (2)
[In the formula (2), ε (405) represents the gram absorption coefficient of the resin (A) at a wavelength of 405 nm, and ε (440) represents the gram absorption coefficient of the resin at a wavelength of 440 nm. ]
(5) The resin according to any one of (1) to (4), wherein the resin (A) is a resin containing a structural unit having an indole structure in a side chain.
The resin according to claim 5, wherein the structural unit having an indole structure in the side chain is a structural unit derived from a photoselective absorption compound having a polymerizable group and an indole structure.
The resin according to claim 6, wherein the light selective absorption compound having a polymerizable group and an indole structure is a compound satisfying the following formula (1-a).
ε (405) ≧ 5 (1-a)
[In the formula (1-a), ε (405) represents a gram extinction coefficient of a compound having a polymerizable group and an indole structure at a wavelength of 405 nm. The unit of the gram extinction coefficient is L / (g · cm). ]
The resin according to claim 7, wherein the light selective absorption compound having a polymerizable group and an indole structure is a compound satisfying the following formula (2-a).
ε (405) / ε (440) ≧ 10 (2-a)
[In the formula (2-a), ε (405) represents a gram extinction coefficient of a compound having a polymerizable group and an indole structure at a wavelength of 405 nm, and ε (440) represents a polymerizable group and an indole structure at a wavelength of 440 nm. It represents the gram extinction coefficient of the compound having.
The resin according to claim 5, wherein the structural unit having an indole structure in a side chain is a structural unit derived from a compound represented by the formula (I) or a structural unit derived from a compound represented by the formula (II).

[In the formula (I), R 1 , R 2 , R 3 , R 4 , R 5 and R 6 each independently represent a hydrogen atom, a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxy group, A carboxy group, an aliphatic hydrocarbon group having 1 to 25 carbon atoms which may have a substituent or an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent; —CH 2 — contained in the hydrocarbon group or the aromatic hydrocarbon group may be substituted with —NR 1A —, —SO 2 —, —CO—, —O—, —S—, or —CF 2 —. Good.
R 1A represents a hydrogen atom, an alkyl group having 1 to 25 carbon atoms or an aromatic hydrocarbon group having 6 to 18 carbon atoms.
E 1 represents an electron-withdrawing group.
Z represents a linking group.
A represents a polymerizable group.
In the formula (II), R 12 and R 17 each independently represent a hydrogen atom, a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxy group, a carboxy group, or an optionally substituted carbon atom. Represents an aliphatic hydrocarbon group having a number of 1 to 25 or an aromatic hydrocarbon group having a carbon number of 6 to 18 which may have a substituent, and is included in the aliphatic hydrocarbon group or the aromatic hydrocarbon group; CH 2 — may be substituted by —NR 11A —, —SO 2 —, —CO—, —O—, —S— or —CF 2 —.
R 11 , R 13 , R 14 , R 15 and R 16 are each independently a hydrogen atom, a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxy group, a carboxy group, a group containing a polymerizable group, Represents an aliphatic hydrocarbon group having 1 to 25 carbon atoms which may have a substituent or an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent; Alternatively, —CH 2 — included in the aromatic hydrocarbon group may be substituted with —NR 12A —, —SO 2 —, —CO—, —O—, —S—, or —CF 2 —.
However, at least one of R 11 , R 13 , R 14 , R 15 and R 16 represents a group containing a polymerizable group.
R 11A and R 12A each independently represent an elementary atom, an alkyl group having 1 to 25 carbon atoms, or an aromatic hydrocarbon group having 6 to 18 carbon atoms.
E 11 represents an electron-withdrawing group. ]
Resin according to claim 9 R 2 is a phenyl group.
The resin according to claim 9, wherein the compound represented by the formula (I) is a compound represented by the formula (III).

[R 1 , R 3 , R 4 , R 5 , R 6 and E 1 represent the same meaning as described above.
R 7 represents a hydrogen atom, a cyano group, a methyl group or a phenyl group.
Z 1 is an alkanediyl group having 1 to 12 carbon atoms, a divalent aromatic hydrocarbon group having 6 to 18 carbon atoms, —OR 2A — * 1, —SR 2B — * 1, or —NR 1D Represents -R 2C- * 1.
Z 2 is a single bond, * 2-CO-O-, * 2-O-CO-, * 2-S (= O) 2- , * 2-O-SO 2- , * 2-CO-NR 1B -, * 2-NR 1C -CO-, * 2-R 2D OP (= O) -OR 2E- , * 2-NR 1E -CO-O-, * 2-O-CO-NR 1F- , * 2- (OR 2F ) s1- , * 2-CO-S-, * 2-S-CO- or a perfluoroalkanediyl group having 1 to 4 carbon atoms.
R 1B , R 1C, R 1D , R 1E and R 1F each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
R 2A , R 2B , R 2C , R 2D , R 2E and R 2F each independently represent a divalent hydrocarbon group having 1 to 18 carbon atoms.
* 1 represents a binding position to Z 2.
* 2 represents a bond to Z 1. ]
The resin according to any one of claims 1 to 11, wherein the resin (A) further has at least one structural unit selected from the structural units described in Group A below.
Group A: a structural unit derived from a (meth) acrylate, a structural unit derived from a styrene-based monomer, a structural unit derived from a vinyl-based monomer, a structural unit derived from an epoxy compound, and a compound represented by the formula (a) The structural unit represented by the structural unit represented by the formula (b) and the structural unit represented by the formula (c)

[In the formula, R a1 represents a divalent hydrocarbon group.
R b1 and R b2 each independently represent a hydrogen atom or a hydrocarbon group.
R c1 and R c2 each independently represent a divalent hydrocarbon group. ]
The resin according to claim 12, wherein the content of at least one structural unit selected from the structural units described in Group A is 50% by mass or more based on all structural units of the resin (A).
A pressure-sensitive adhesive composition containing the resin according to any one of claims 1 to 13.
粘着 The pressure-sensitive adhesive composition according to claim 14, further comprising a crosslinking agent (B).
An adhesive layer formed from the adhesive composition according to claim 14 or 15.
The pressure-sensitive adhesive layer according to claim 16, wherein the following formula (3) is satisfied.
A (405) ≧ 0.5 (3)
[In the formula (3), A (405) represents the absorbance at a wavelength of 405 nm. ]
The pressure-sensitive adhesive layer according to claim 17, further satisfying the following formula (4).
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. ]
An optical laminate in which an optical film is laminated on at least one surface of the pressure-sensitive adhesive layer according to any one of claims 16 to 18.
20. The optical laminate according to claim 19, wherein the optical film is a polarizing plate.
An image display device comprising the optical laminate according to claim 20.
A compound represented by the formula (I) or the formula (IV).

[In the formula (I), R 1 , R 2 , R 3 , R 4 , R 5 and R 6 each independently represent a hydrogen atom, a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxy group, A carboxy group, an aliphatic hydrocarbon group having 1 to 25 carbon atoms which may have a substituent or an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent; —CH 2 — contained in the hydrocarbon group or the aromatic hydrocarbon group may be substituted with —NR 1A —, —SO 2 —, —CO—, —O—, —S—, or —CF 2 —. Good.
R 1A represents a hydrogen atom, an alkyl group having 1 to 25 carbon atoms or an aromatic hydrocarbon group having 6 to 18 carbon atoms.
E 1 represents an electron-withdrawing group.
Z represents a linking group.
A represents a polymerizable group.
In the formula (IV), R 12 and R 17 each independently represent a hydrogen atom, a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxy group, a carboxy group, or a carbon which may have a substituent. Represents an aliphatic hydrocarbon group having a number of 1 to 25 or an aromatic hydrocarbon group having a carbon number of 6 to 18 which may have a substituent, and is included in the aliphatic hydrocarbon group or the aromatic hydrocarbon group; CH 2 — may be substituted by —NR 11A —, —SO 2 —, —CO—, —O—, —S— or —CF 2 —.
R 11 , R 13 , R 14 , R 15 and R 16 are each independently a hydrogen atom, a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxy group, a carboxy group, a group containing a polymerizable group, Represents an aliphatic hydrocarbon group having 1 to 25 carbon atoms which may have a substituent or an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent; Alternatively, —CH 2 — included in the aromatic hydrocarbon group may be substituted with —NR 12A —, —SO 2 —, —CO—, —O—, —S—, or —CF 2 —.
However, at least one of R 13 , R 14 , R 15 and R 16 represents a group containing a polymerizable group.
R 11A and R 12A each independently represent an elementary atom, an alkyl group having 1 to 25 carbon atoms, or an aromatic hydrocarbon group having 6 to 18 carbon atoms.
E 11 represents an electron-withdrawing group. ]
A compound according to claim 22 R 2 is a phenyl group.
The compound according to claim 22, wherein the compound represented by the formula (I) is a compound represented by the formula (III).

[R 1 , R 3 , R 4 , R 5 , R 6 and E 1 represent the same meaning as described above.
R 7 represents a hydrogen atom, a cyano group, a methyl group or a phenyl group.
Z 1 is an alkanediyl group having 1 to 12 carbon atoms, a divalent aromatic hydrocarbon group having 6 to 18 carbon atoms, —OR 2A — * 1, —SR 2B — * 1, or —NR 1D Represents -R 2C- * 1.
Z 2 is a single bond, * 2-CO-O-, * 2-O-CO-, * 2-S (= O) 2- , * 2-O-SO 2- , * 2-CO-NR 1B -, * 2-NR 1C -CO-, * 2-R 2D OP (= O) -OR 2E- , * 2-NR 1E -CO-O-, * 2-O-CO-NR 1F- , * 2- (OR 2F ) s1- , * 2-CO-S-, * 2-S-CO- or a perfluoroalkanediyl group having 1 to 4 carbon atoms.
R 1B , R 1C, R 1D , R 1E and R 1F each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
R 2A , R 2B , R 2C , R 2D , R 2E and R 2F each independently represent a divalent hydrocarbon group having 1 to 18 carbon atoms.
* 1 represents a binding position to Z 2.
* 2 represents a bond to Z 1. ]
25. The compound according to claim 22, wherein E 1 is a cyano group.