KR20220081987A - adhesive composition - Google Patents

Abstract

[Problem] Provided are a pressure-sensitive adhesive layer having sufficient ultraviolet absorption performance even when the film thickness is made thin and less occurrence of bleed-out, and a pressure-sensitive adhesive composition for forming the pressure-sensitive adhesive layer.
[Solutions] Resin (A), a light-selective absorption compound (B) containing a merocyanine structure in a molecule and exhibiting maximum absorption at a wavelength of 360 nm or more, and a light-selective absorption compound showing maximum absorption at a wavelength of 300 nm or more and less than 360 nm A pressure-sensitive adhesive composition comprising an absorbent resin (C). Moreover, the adhesive layer formed from this adhesive composition.

Description

adhesive composition

The present invention relates to a pressure-sensitive adhesive composition, a pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition, and an optical laminate on which the pressure-sensitive adhesive layer is laminated.

In display devices (FPD: flat panel display) such as organic electroluminescent displays (organic EL display devices) and liquid crystal displays, various members such as organic EL elements, display elements such as liquid crystal cells, and optical films such as polarizing plates are used. have. Among these members, a compound having relatively weak weather resistance is often used for the liquid crystal compound used for an organic EL device or a liquid crystal cell, and deterioration by ultraviolet (UV) tends to become a problem. In order to solve this problem, Patent Document 1 discloses an ultraviolet absorbing (shielding) pressure-sensitive adhesive composition containing an acrylic resin and a triazine-based ultraviolet absorber, and a pressure-sensitive adhesive layer having a thickness of 15 µm formed from this pressure-sensitive adhesive composition is also described.

Patent Document 1: Japanese Patent Laid-Open No. 2008-248131

In recent years, remarkable thin film formation is calculated|required for an organic electroluminescent display device and a liquid crystal display device, and remarkable thin film formation is calculated|required also for the member used for an organic electroluminescent display device or a liquid crystal display device. Therefore, thin film formation is calculated|required also for the ultraviolet-absorbing (shielding property) adhesive layer itself. However, when the ultraviolet-absorbing (shielding) pressure-sensitive adhesive layer is simply thinned (for example, less than 12 µm), the ultraviolet-absorbing performance of the pressure-sensitive adhesive layer is lowered. On the other hand, if the addition amount of the ultraviolet absorber is increased to thin the pressure-sensitive adhesive layer while maintaining the ultraviolet absorption performance, problems such as bleed-out of the ultraviolet absorber will occur.

The present invention includes the following inventions.

[1] Resin (A),

A photoselective absorption compound (B) containing a merocyanine structure in a molecule and exhibiting maximum absorption at a wavelength of 360 nm or more, and

A pressure-sensitive adhesive composition comprising a light-selective absorption resin (C) having a maximum absorption at a wavelength of 300 nm or more and less than 360 nm.

[2] The pressure-sensitive adhesive composition according to [1], further comprising a radical curable component (E).

[3] The pressure-sensitive adhesive composition according to [2], wherein the radical curable component (E) is a (meth)acrylate-based compound.

[4] The pressure-sensitive adhesive composition according to [2] or [3], wherein the radical curable component (E) is a polyfunctional (meth)acrylate-based compound.

[5] The pressure-sensitive adhesive composition according to any one of [1] to [4], further comprising a radical initiator (D).

[6] The pressure-sensitive adhesive composition according to [5], wherein the radical initiator (D) is an optical radical generator.

[7] The pressure-sensitive adhesive composition according to [5] or [6], wherein the radical initiator (D) is an oxime ester-based photo-radical generator.

[8] The pressure-sensitive adhesive composition according to any one of [1] to [7], further comprising a crosslinking agent (F).

[9] The pressure-sensitive adhesive composition according to [8], wherein the crosslinking agent (F) is an isocyanate-based crosslinking agent.

[10] The pressure-sensitive adhesive composition according to any one of [1] to [9], wherein the resin (A) has a glass transition temperature of 40°C or less.

[11] The pressure-sensitive adhesive composition according to [10], wherein the resin (A) having a glass transition temperature of 40°C or less is a (meth)acrylic resin.

[12] The light-selective absorption compound (B) containing a merocyanine structure in a molecule and exhibiting maximum absorption at a wavelength of 360 nm or more is described in any one of [1] to [11], satisfying the following formula (1) A pressure-sensitive adhesive composition.

ε(380)≥25 (1)

[In formula (1), ε(380) represents the gram extinction coefficient at a wavelength of 380 nm of the light-selective absorption compound (B) having a merocyanine structure in the molecule and exhibiting maximum absorption at a wavelength of 360 nm or more. The unit of the gram extinction coefficient is L/(g·cm)]

[13] The light-selective absorption compound (B) containing a merocyanine structure in a molecule and exhibiting maximum absorption at a wavelength of 360 nm or more is described in any one of [1] to [12], satisfying the following formula (2) A pressure-sensitive adhesive composition.

ε(380)/ε(420)≥20 (2)

[In formula (2), ε(380) is the gram extinction coefficient of the resin at a wavelength of 380 nm of the photoselective absorption compound (B) that contains a merocyanine structure in the molecule and exhibits maximum absorption at a wavelength of 360 nm or more. indicate,

ε (420) represents the gram extinction coefficient of the light-selective absorption compound (B) at a wavelength of 420 nm of the light-selective absorption compound (B) having a merocyanine structure in the molecule and exhibiting maximum absorption at a wavelength of 360 nm or more .]

[14] The pressure-sensitive adhesive according to [1] to [13], wherein the light-selective absorption compound (B) containing a merocyanine structure in a molecule and exhibiting maximum absorption at a wavelength of 360 nm or more is a compound represented by the formula (Y). composition.

[In formula (Y),

R ^Y3 , R ^Y4 and R ^Y5 each independently represent an electron withdrawing group.

R ^Y1 , R ^Y2 , R ^Y6 and R ^Y7 are each independently a hydrogen atom, a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxy group, a thiol group, a carboxy group, -SCF ₃ , -SF ₅ , -SF ₃ , - SO ₃ H, —SO ₂ H, 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, and —CH contained in the aliphatic hydrocarbon group or aromatic hydrocarbon group ₂ - or -CH= is -NR ^1A -, -SO ₂ -, -CO-, -O-, -COO-, -OCO-, -CONR ^2A -, -NR ^3A -CO-, -S-, -SO-, -SO ₂ -, -CF ₂ -, or -CHF- may be substituted.

R ^1A , R ^2A and R ^3A each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.

R ^Y1 and R ^Y2 may be linked to each other to form a ring.

R ^Y1 and R ^Y6 may be linked to each other to form a ring.

R ^Y4 and R ^Y5 may be linked to each other to form a ring.]

[15] The light-selective absorption compound (B) containing a merocyanine structure in a molecule and exhibiting maximum absorption at a wavelength of 360 nm or more is a compound having a molecular weight of 3000 or less and having a partial structure represented by formula (X) [ The pressure-sensitive adhesive composition according to any one of 1] to [13].

[In formula (X), ring W ¹ represents a ring structure having at least one double bond as a component of the ring and not having aromaticity.

R ³ is a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a thiol group, a carboxy group, -SF ₅ , -SF ₃ , -SO ₃ H, -SO ₂ H, optionally having 1 to 25 carbon atoms represents an aliphatic hydrocarbon group or an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent, and -CH ₂ - or -CH= contained in the aliphatic hydrocarbon group or aromatic hydrocarbon group is -O-, -S-, -NR ^1xA -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -CONR ^2xA -, -NR ^3xA -CO-, -O-CO-NR ^4xA -, -NR ^5xA -CO-O-, -NR ^6xA -CO-NR ^7xA -, -CO-S-, -S-CO-S-, -S-CO-NR ^8xA -, -NR ^9xA -CO-S-, -CS -, -O-CS-, -CS-O-, -NR ^10xA -CS-, -NR ^11xA -CS-S-, -S-CS-, -CS-S-, -S-CS-S-, -SO- or -SO ₂ - may be substituted.

R ^1xA , R ^2xA , R ^3xA , R 4xA , R ^5xA , R ^6xA , R ^7xA , R ^8xA , R ^9xA , R ^10xA and R ^11xA each independently ^represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.]

[16] As described in [15], wherein the compound having a molecular weight of 3000 or less and having a partial structure represented by the formula (X) is any one of the compound represented by the formula (I) to the compound represented by the formula (VIII). adhesive composition.

[In formulas (I) to (VIII),

Rings W ¹ and R ³ have the same meanings as above.

Ring W ² , Ring W ³ , Ring W ⁴ , Ring W ⁵ , Ring W ⁶ , Ring W ⁷ , Ring W ⁸ , Ring W ⁹ , Ring W ¹⁰ , Ring W ¹¹ and Ring W ¹² are each independently a constituent of a ring It represents a ring structure having at least one double bond as an element.

Ring W ¹¹¹ represents a ring having at least two nitrogen atoms as a component.

Ring W ¹¹² and ring W ¹¹³ each independently represent a ring having at least one nitrogen atom as a constituent element.

R ¹ , R ⁴¹ , R ⁵¹ , R ⁶¹ , R ⁹¹ , R ¹⁰¹ , R ¹¹¹ , R ² , R ¹² , R ⁴² , R ⁵² , R ⁶² , R ⁷² , R ⁸² , R ⁹² , R ¹⁰² and R ¹¹² . are each independently a hydrogen atom, a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a thiol group, a carboxy group, -SF ₅ , -SF ₃ , -SO ₃ H, -SO ₂ H, the number of carbon atoms which may have a substituent represents an aliphatic hydrocarbon group having 1 to 25 or an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent, and -CH ₂ - or -CH= contained in the aliphatic hydrocarbon group or aromatic hydrocarbon group is -NR ^12A -, -SO ₂ -, -CO-, -O-, -COO-, -OCO-, -CONR ^13A -, -NR ^14A -CO-, -S-, -SO-, -CF ₂ - or -CHF- good to be

R ¹³ , R ²³ , R ³³ , R ⁴³ , R ⁵³ , R ⁶³ , R ⁷³ , R ⁸³ , R ⁹³ , R ¹⁰³ and R ¹¹³ are each independently a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxy group; A thiol group, a carboxyl group, -SF ₅ , -SF ₃ , -SO ₃ H, -SO ₂ H, an optionally substituted aliphatic hydrocarbon group having 1 to 25 carbon atoms or an optionally substituted aromatic hydrocarbon group having 6 to 18 carbon atoms and -CH ₂ - or -CH= contained in this aliphatic hydrocarbon group or aromatic hydrocarbon group is -O-, -S-, -NR ^1A -, -CO-, -CO-O-, -O-CO- , -O-CO-O-, -CONR ^2A -, -NR ^3A -CO-, -O-CO-NR ^4A -, -NR ^5A -CO-O-, -NR ^6A -CO-NR ^7A -, - CO-S-, -S-CO-S-, -S-CO-NR ^8A -, -NR ^9A -CO-S-, -CS-, -O-CS-, -CS-O-, -NR ^10A -CS-, -NR ^11A -CS-S-, -S-CS-, -CS-S-, -S-CS-S-, -SO- or -SO ₂ - may be substituted.

R ^1A , R ^2A , R ^3A , R ^4A , R ^5A , R ^6A , R ^7A , R ^8A , R ^9A , R ^10A , R ^11A , R ^12A , R ^13A and R ^14A are each independently a hydrogen atom or 1 carbon atom It represents the alkyl group of -6.

R ⁴ , R ¹⁴ , R ²⁴ , R ³⁴ , R ⁴⁴ , R ⁵⁴ , R ⁶⁴ , R ⁷⁴ , R ⁸⁴ , R ⁹⁴ , R ¹⁰⁴ , R ¹¹⁴ , R ⁵ , R ¹⁵ , R ²⁵ , R ³⁵ , R ⁷⁵ and R ⁸⁵ each independently represents an electron withdrawing group.

R ¹ and R ² may be bonded to each other to form a ring.

R ⁴¹ and R ⁴² may be bonded to each other to form a ring.

R ⁵¹ and R ⁵² may be bonded to each other to form a ring.

R ⁶¹ and R ⁶² may be bonded to each other to form a ring.

R ⁹¹ and R ⁹² may be bonded to each other to form a ring.

R ¹⁰¹ and R ¹⁰² may combine with each other to form a ring.

R ¹¹¹ and R ¹¹² may be bonded to each other to form a ring.

R ² and R ³ may be bonded to each other to form a ring.

R ¹² and R ¹³ may be bonded to each other to form a ring.

R ⁴² and R ⁴³ may be bonded to each other to form a ring.

R ⁵² and R ⁵³ may be bonded to each other to form a ring.

R ⁶² and R ⁶³ may be bonded to each other to form a ring.

R ⁷² and R ⁷³ may be bonded to each other to form a ring.

R ⁸² and R ⁸³ may be bonded to each other to form a ring.

R ⁹² and R ⁹³ may be bonded to each other to form a ring.

R ¹⁰² and R ¹⁰³ may be bonded to each other to form a ring.

R ¹¹² and R ¹¹³ may be bonded to each other to form a ring.

R ⁴ and R ⁵ may be bonded to each other to form a ring.

R ¹⁴ and R ¹⁵ may be bonded to each other to form a ring.

R ²⁴ and R ²⁵ may be bonded to each other to form a ring.

R ³⁴ and R ³⁵ may combine with each other to form a ring.

R ⁷⁴ and R ⁷⁵ may be bonded to each other to form a ring.

R ⁸⁴ and R ⁸⁵ may be bonded to each other to form a ring.

R ⁶ and R ⁸ each independently represent a divalent linking group.

R ⁷ represents a single bond or a divalent linking group.

R ⁹ and R ¹⁰ each independently represent a trivalent linking group.

R ¹¹ represents a tetravalent linking group.]

[17] A pressure-sensitive adhesive layer formed of the pressure-sensitive adhesive composition according to any one of [1] to [16].

[18] The pressure-sensitive adhesive layer according to [17], which satisfies the following formula (3).

A(380)≥0.60 (3)

[In formula (3), A (380) represents the absorbance at a wavelength of 380 nm.]

[19] The pressure-sensitive adhesive layer according to [17] or [18], which further satisfies the following formula (4).

A(380)/A(420)≥5 (4)

[In formula (4), A (380) represents the absorbance at a wavelength of 380 nm, and A (420) represents the absorbance at a wavelength of 420 nm.]

[20] The pressure-sensitive adhesive layer according to any one of [17] to [19], wherein the pressure-sensitive adhesive layer has a thickness of 10 µm or less.

[21] An optical film with a pressure-sensitive adhesive layer in which an optical film is laminated on at least one surface of the pressure-sensitive adhesive layer according to any one of [17] to [20].

[22] The optical film with an adhesive layer according to [21], wherein the optical film is a polarizing plate.

[23] An image display device comprising the optical film with an adhesive layer according to [21] or [22].

The present invention provides a good pressure-sensitive adhesive layer having sufficient ultraviolet absorption performance even when the film thickness is made thin (for example, less than 12 µm) and less occurrence of bleed-out, and a pressure-sensitive adhesive composition for forming the pressure-sensitive adhesive layer.

1 : shows an example of the layer structure of the laminated body in which the peeling film was provided in the adhesive layer of this invention.
2 : shows an example of the laminated constitution of the optical film with an adhesive layer of this invention.
3 : shows an example of the laminated constitution of the optical film with an adhesive layer of this invention.
4 : shows an example of the layer structure of the optical laminated body of this invention.
5 : shows an example of the layer structure of the optical laminated body of this invention.

<Adhesive composition>

The adhesive composition of this invention contains the following (Z-1)-(Z-3).

(Z-1): Resin (A)

(Z-2): A light-selective absorption compound (B) containing a merocyanine structure in a molecule and having a maximum absorption wavelength of 360 nm or more (hereinafter sometimes referred to as a light-selective absorption compound (B).)

(Z-3): Light-selective absorption resin (C) showing maximum absorption at a wavelength of 300 nm or more and less than 360 nm (hereinafter sometimes referred to as light-selective absorption resin (C).)

<Resin (A)>

Resin (A) of this invention will not be specifically limited if it is resin used for an adhesive composition. It is preferable that the resin (A) does not show a maximum absorption in a wavelength range of 300 nm to 780 nm.

It is preferable that resin (A) is resin whose glass transition temperature (Tg) is 40 degrees C or less. As for the glass transition temperature (Tg) of resin (A), it is more preferable that it is 20 degrees C or less, It is still more preferable that it is 10 degrees C or less, It is especially preferable that it is 0 degrees C or less. The glass transition temperature of the resin (A) is usually -80°C or higher, preferably -70°C or higher, more preferably -60°C or higher, still more preferably -55°C or higher, and particularly preferably -50°C or higher. desirable. It is advantageous for the improvement of the adhesiveness with respect to the to-be-adhered body of the adhesive layer formed from the adhesive composition containing resin (A) as the glass transition temperature of resin (A) is 40 degrees C or less. Moreover, it is advantageous for the durability improvement of the adhesive layer formed from the adhesive composition containing resin (A) as the glass transition temperature of resin (A) is -80 degreeC or more. In addition, the glass transition temperature can be measured by differential scanning calorimetry (DSC).

As resin (A), (meth)acrylic-type resin, silicone resin, rubber-type resin, urethane-type resin, etc. are mentioned, It is preferable that it is (meth)acrylic-type resin.

As (meth)acrylic resin, it is preferable that it is a polymer which has the structural unit derived from (meth)acrylic acid ester as a main component (preferably 50 mass % or more is included.). The structural unit derived from (meth)acrylic acid ester may include a structural unit derived from a monomer other than one or more types of (meth)acrylic acid ester (for example, a structural unit derived from a monomer having a polar functional group). In addition, in this specification, (meth)acrylic acid means that either acrylic acid or methacrylic acid may be sufficient, and "(meth)" at the time of calling (meth)acrylate etc. has the same meaning.

As (meth)acrylic acid ester, the (meth)acrylic acid ester represented by a following formula (a) is mentioned.

[In formula (a), R _1A represents a hydrogen atom or a methyl group, R _2A represents an alkyl group having 1 to 14 carbon atoms or an aromatic hydrocarbon group having 6 to 20 carbon atoms, and the hydrogen atom of the alkyl group and the aromatic hydrocarbon group is 1 carbon atom It may be substituted with the alkoxy group of -10.]

In the formula (a), R _2A is preferably an alkyl group having 1 to 14 carbon atoms, more preferably an alkyl group having 1 to 8 carbon atoms.

As (meth)acrylic acid ester represented by Formula (a),

(meth) methyl acrylate, (meth) ethyl acrylate, (meth) acrylate n-propyl, (meth) acrylate n-butyl, (meth) acrylate n-pentyl, (meth) acrylate n-hexyl, (meth) acrylic acid n- Heptyl, (meth)acrylic acid n-octyl, (meth)acrylic acid n-nonyl, (meth)acrylic acid n-decyl, (meth)acrylic acid n-dodecyl, (meth)acrylic acid lauryl, (meth)acrylic acid stearyl, etc. linear alkyl esters of (meth)acrylic acid;

(meth)acrylic acid i-propyl, (meth)acrylic acid i-butyl, (meth)acrylic acid t-butyl, (meth)acrylic acid i-pentyl, (meth)acrylic acid i-hexyl, (meth)acrylic acid 2-ethylhexyl, ( Branched alkyl esters of (meth)acrylic acid, such as meth)acrylic acid i-octyl, (meth)acrylic acid i-nonyl, (meth)acrylic acid i-stearyl, and (meth)acrylic acid i-amyl;

(meth)acrylic acid cyclohexyl, (meth)acrylic acid isoboronyl, (meth)acrylic acid adamantyl, (meth)acrylic acid dicyclopentanyl, (meth)acrylic acid cyclododecyl, (meth)acrylic acid methylcyclohexyl, (meth) alicyclic skeleton-containing alkyl esters of (meth)acrylic acid such as trimethylcyclohexyl acrylate, (meth)acrylic acid tert-butylcyclohexyl, and α-ethoxyacrylic acid cyclohexyl;

Aromatic ring skeleton containing ester of (meth)acrylic acid, such as (meth)acrylic-acid phenyl and (meth)acrylic-acid benzyl;

and the like.

In addition, as the substituent-containing (meth)acrylic acid ester, (meth)acrylic acid 2-methoxyethyl, (meth)acrylic acid ethoxymethyl, (meth)acrylic acid phenoxyethyl, (meth)acrylic acid 2-(2-phenoxyethoxy) Ethyl etc. are mentioned.

As (meth)acrylic acid ester, (meth)acrylic acid phenoxydiethylene glycol, (meth)acrylic acid phenoxypoly(ethylene glycol), etc. are mentioned.

These (meth)acrylic acid esters can be used independently, respectively, and other plurality may be used.

The resin (A) of the present invention has a structural unit derived from the (meth)acrylic acid alkylester (a1) whose glass transition temperature (Tg) of the homopolymer is less than 0°C among the (meth)acrylic acid alkylesters, and the Tg of the homopolymer is 0°C It is preferable to contain the structural unit derived from the above (meth)acrylic-acid alkylester (a2). This is advantageous in improving the high temperature durability of the pressure-sensitive adhesive layer. For the Tg of the homopolymer of the (meth)acrylic acid alkyl ester, a literature value such as POLYMER HANDBOOK (Wiley-Interscience) can be adopted.

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

(meth)acrylic acid alkylester (a1) may use only 1 type, and may use 2 or more types together. 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.

(meth)acrylic acid alkylesters (a2) are (meth)acrylic acid alkylesters other than (meth)acrylic acid alkylesters (a1). Specific examples of the (meth)acrylic acid alkyl ester (a2) include methyl acrylate, cyclohexyl acrylate, isoboronyl acrylate, stearyl acrylate, and t-butyl acrylate.

(meth)acrylic acid alkylester (a2) may use only 1 type and may use 2 or more types together. Among them, from the viewpoint of high temperature durability, the (meth)acrylic acid alkylester (a2) preferably contains methyl acrylate, cyclohexyl acrylate, isoboronyl acrylate, and the like, and more preferably contains methyl acrylate.

The structural unit derived from the (meth)acrylic acid ester represented by the formula (a) is preferably 50% by mass or more, preferably 60 to 95% by mass, among all the structural units contained in the (meth)acrylic resin, It is more preferable that it is 65-95 mass % or more.

As the structural unit derived from a monomer other than (meth)acrylic acid ester, a structural unit derived from a monomer having a polar functional group is preferable, and a structural unit derived from a (meth)acrylic acid ester having a polar functional group is more preferable. Examples of the polar functional group include a hydroxy group, a carboxyl group, a substituted or unsubstituted amino group, and a heterocyclic group such as an epoxy group.

As a monomer having a polar functional group,

(meth)acrylic acid 1-hydroxymethyl, (meth)acrylic acid 1-hydroxyethyl, (meth)acrylic acid 1-hydroxyheptyl, (meth)acrylic acid 1-hydroxybutyl, (meth)acrylic acid 1-hydroxypentyl; (meth)acrylic acid 2-hydroxyethyl, (meth)acrylic acid 2-hydroxypropyl, (meth)acrylic acid 2-hydroxybutyl, (meth)acrylic acid 2-hydroxypentyl, (meth)acrylic acid 2-hydroxyhexyl; (meth)acrylic acid 3-hydroxypropyl, (meth)acrylic acid 3-hydroxybutyl, (meth)acrylic acid 3-hydroxypentyl, (meth)acrylic acid 3-hydroxyhexyl, (meth)acrylic acid 3-hydroxyheptyl; (meth)acrylic acid 4-hydroxybutyl, (meth)acrylic acid 4-hydroxypentyl, (meth)acrylic acid 4-hydroxyhexyl, (meth)acrylic acid 4-hydroxyheptyl, (meth)acrylic acid 4-hydroxyoctyl; (meth)acrylic acid 2-chloro-2-hydroxypropyl, (meth)acrylic acid 3-chloro-2-hydroxypropyl, (meth)acrylic acid 2-hydroxy-3-phenoxypropyl, (meth)acrylic acid 5-hydroxy Roxypentyl, (meth)acrylic acid 5-hydroxyhexyl, (meth)acrylic acid 5-hydroxyheptyl, (meth)acrylic acid 5-hydroxyoctyl, (meth)acrylic acid 5-hydroxynonyl, (meth)acrylic acid 6-hydroxy Hydroxyhexyl, (meth)acrylic acid 6-hydroxyheptyl, (meth)acrylic acid 6-hydroxyoctyl, (meth)acrylic acid 6-hydroxynonyl, (meth)acrylic acid 6-hydroxydecyl, (meth)acrylic acid 7-hydroxy Hydroxyheptyl, (meth)acrylic acid 7-hydroxyoctyl, (meth)acrylic acid 7-hydroxynonyl, (meth)acrylic acid 7-hydroxydecyl, (meth)acrylic acid 7-hydroxyundecyl, (meth)acrylic acid 8- Hydroxyoctyl, (meth)acrylic acid 8-hydroxynonyl, (meth)acrylic acid 8-hydroxydecyl, (meth)acrylic acid 8-hydroxyundecyl, (meth)acrylic acid 8-hydroxydodecyl, (meth)acrylic acid 9-hydroxynonyl, (meth)acrylic acid 9-hydroxydecyl, (meth)acrylic acid 9-hydroxyundecyl, (meth)acrylic acid 9-hydroxydodecyl, (meth)acrylic acid 9-hydroxytridecyl, ( 10-hydroxydecyl (meth)acrylic acid, 10-hydroxyundecyl (meth)acrylic acid, 10-hydroxydodecyl (meth)acrylic acid, 10-hydroxytridecyl acrylic acid, 10-hydroxytetradecyl (meth)acrylic acid, (meth)acrylic acid 11-hydroxyundecyl, (meth)acrylic acid 11-hydroxydodecyl, (meth)acrylic acid 11-hydroxytridecyl, (meth)acrylic acid 11-hydroxytetradecyl, (meth)acrylic acid 11-hydroxypentadecyl , (meth)acrylic acid 12-hydroxydodecyl, (meth)acrylic acid 12-hydroxytridecyl, (meth)acrylic acid 12-hydroxytetradecyl, (meth)acrylic acid 13-hydroxypentadecyl, (meth)acrylic acid 13 -Hydroxytetradecyl, (meth)acrylic acid 13-hydroxypentadecyl, (meth)acrylic acid 14-hydroxytetradecyl, (meth)acrylic acid 14-hydroxypentadecyl, (meth)acrylic acid 15-hydroxypentadecyl, monomers having a hydroxyl group such as (meth)acrylic acid 15-hydroxyheptadecyl;

Monomers having a carboxyl group, such as (meth)acrylic acid, carboxyalkyl (meth)acrylate (eg, carboxyethyl (meth)acrylate, carboxypentyl (meth)acrylate), maleic acid, maleic anhydride, fumaric acid, and crotonic acid;

Acryloylmorpholine, vinylcaprolactam, N-vinyl-2-pyrrolidone, vinylpyridine, tetrahydrofurfuryl (meth)acrylate, caprolactone-modified tetrahydrofurfuryl acrylate, 3,4-epoxycyclohexyl monomers having a heterocyclic group such as methyl (meth)acrylate, glycidyl (meth)acrylate, and 2,5-dihydrofuran;

and monomers having a substituted or unsubstituted amino group, such as aminoethyl (meth)acrylate, N,N-dimethylaminoethyl (meth)acrylate, and dimethylaminopropyl (meth)acrylate.

Among them, from the viewpoint of reactivity between the (meth)acrylic acid ester polymer and the crosslinking agent, a monomer having a hydroxyl group and a monomer having a carboxyl group are preferable, and it is more preferable to include both a monomer having a hydroxyl group and a monomer having a carboxyl group.

As the monomer having a hydroxyl 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.

It is preferable to use acrylic acid as a monomer which has a carboxyl group.

From the viewpoint of preventing the improvement of the peeling force of the separate film that can be laminated on the outer surface of the pressure-sensitive adhesive layer, the (meth)acrylic resin preferably does not substantially contain a structural unit derived from a monomer having an amino group. Here, "not included" means that it is 0.1 mass part or less among 100 mass parts of all structural units which comprise (meth)acrylic-type resin.

The content of the structural unit derived from the monomer having a polar functional group is preferably 20 parts by mass or less, more preferably 0.5 parts by mass or more and 15 parts by mass or less, with respect to 100 parts by mass of all structural units of the (meth)acrylic resin, More preferably, they are 0.5 mass part or more and 10 mass parts or less, Especially preferably, they are 1 mass part or more and 7 mass parts or less.

As a structural unit derived from monomers other than (meth)acrylic acid ester, the structural unit derived from the monomer which has an aromatic group is also mentioned. Examples of the monomer having an aromatic group include (meth)acrylic acid esters having one (meth)acryloyl group and one or more aromatic rings (eg, a benzene ring, a naphthalene ring, etc.) in a molecule, for example, a phenyl group, a phenoxyethyl group, or (meth)acrylic acid ester which has a benzyl group is mentioned. The content of the structural unit derived from the monomer having an aromatic group is preferably 20 parts by mass or less, more preferably 4 parts by mass or more and 20 parts by mass or less, with respect to 100 parts by mass of all the structural units of the (meth)acrylic resin. Preferably they are 4 mass parts or more and 16 mass parts or less.

As a structural unit derived from monomers other than (meth)acrylic acid ester, a structural unit derived from a styrene-type monomer, a structural unit derived from a vinyl-type monomer, and a structure derived from a monomer having a plurality of (meth)acryloyl groups in the molecule A unit, a structural unit derived from a (meth)acrylamide type monomer, etc. are mentioned.

Examples of the styrene-based monomer include styrene; alkyl styrenes such as methyl styrene, dimethyl styrene, trimethyl styrene, ethyl styrene, diethyl styrene, triethyl styrene, propyl styrene, butyl styrene, hexyl styrene, heptyl styrene, and octyl styrene; halogenated styrenes such as fluorostyrene, chlorostyrene, bromostyrene, dibromostyrene, and iodostyrene; nitrostyrene; acetyl styrene; methoxystyrene; and divinylbenzene.

Examples of the vinyl-based monomer include fatty acid vinyl esters such as vinyl acetate, vinyl propionate, vinyl butyrate, vinyl 2-ethylhexanoate, and vinyl laurate; vinyl halides such as vinyl chloride and vinyl bromide; vinylidene halides such as vinylidene chloride; 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.

Examples of the monomer having a plurality of (meth)acryloyl groups in the molecule include 1,4-butanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,9-nonanedioldi(meth) Two (meth) in a molecule such as acrylate, ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate a monomer having an acryloyl group; The monomer which has three (meth)acryloyl groups in molecules, such as trimethylol propane tri(meth)acrylate, is mentioned.

As a (meth)acrylamide type monomer, 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-dimethyl toxy)ethyl](meth)acrylamide etc. are mentioned. Among them, N-(methoxymethyl)acrylamide, N-(ethoxymethyl)acrylamide, N-(propoxymethyl)acrylamide, N-(butoxymethyl)acrylamide and N-(2-methylpropoxy) Methyl)acrylamide is preferred.

The weight average molecular weight (Mw) of (meth)acrylic-type resin becomes like this. Preferably it is 500,000-2.5 million. When the weight average molecular weight is 500,000 or more, the pressure-sensitive adhesive layer durability 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 easily suppressed. It is advantageous from a viewpoint of coatability that a weight average molecular weight is 2.5 million or less. From a viewpoint of the durability of an adhesive layer, and coatability coexistence of an adhesive composition, a weight average molecular weight becomes like this. Preferably it is 600,000-1.8 million, More preferably, it is 700,000-1.7 million, Especially preferably, it is 1 million-1.6 million. . The molecular weight distribution (Mw/Mn) expressed 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, and more preferably 3 to 6. The weight average molecular weight can be analyzed by gel permeation chromatography and is a value in terms of standard polystyrene.

When the (meth)acrylic acid resin is dissolved in ethyl acetate to obtain a solution having a concentration of 20% by mass, the viscosity at 25°C is preferably 20 Pa·s or less, more preferably 0.1 to 15 Pa·s. It is advantageous from a viewpoint of the coatability at the time of coating an adhesive composition to a base material as it is a viscosity of the said range. Here, the viscosity can be measured with a Brookfield viscometer.

The (meth)acrylic resin can be produced by known methods such as solution polymerization, bulk polymerization, suspension polymerization, and emulsion polymerization, and solution polymerization is particularly preferred. As the solution polymerization method, for example, a method in which a monomer and an organic solvent are mixed, a thermal polymerization initiator is added under a nitrogen atmosphere, and stirred for about 3 to 15 hours under a temperature condition of about 40 to 90°C, preferably about 50 to 80°C. can be heard For reaction control, a monomer or a thermal polymerization initiator may be added continuously or intermittently during polymerization. The above-mentioned monomer and thermal polymerization initiator may be added to the organic solvent. 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, etc. are mentioned. As the thermal polymerization initiator, a known thermal polymerization initiator can be used. In addition, a photoinitiator may be used instead of a thermal polymerization initiator, and the polymerization method by an ultraviolet-ray etc. may be used.

Content of resin (A) is 50 mass % - 99.9 mass % normally in 100 mass % of solid content of an adhesive composition, Preferably they are 60 mass % - 95 mass %, More preferably, they are 70 mass % - 90 mass % to be.

<Light Selective Absorption Compound (B)>

The light-selective absorption compound (B) is a compound having a merocyanine structure in the molecule.

In the present invention, the merocyanine structure means a partial structure represented by N-C=C-C=C. However, the merocyanine structure in this invention does not contain an indole ring. In addition, the merocyanine structure in the present invention is an aromatic condensed ring (for example, a benzotriazole ring, a benzimidazole ring, It is preferable not to contain an isoindole ring, a quinoline ring, etc.).

The light-selective absorption compound (B) shows maximum absorption at a wavelength of 360 nm or more. The light-selective absorption compound (B) preferably exhibits maximum absorption at a wavelength of 360 nm or more and 420 nm or less, and more preferably exhibits maximum absorption at a wavelength of 370 nm or more and 410 nm or less. By exhibiting maximum absorption at a wavelength of 360 nm or more, even a small amount of addition can efficiently absorb light in the vicinity of 380 nm.

The light-selective absorption compound (B) preferably satisfies the following formula (1), and more preferably satisfies the formula (2).

ε(380)≥25 (1)

[In formula (1), ε(380) represents the gram extinction coefficient at a wavelength of 380 nm of the light-selective absorption compound (B) having a merocyanine structure in the molecule and exhibiting maximum absorption at a wavelength of 360 nm or more. The unit of the gram extinction coefficient is L/(g·cm)]

ε(380)/ε(420)≥20 (2)

[In formula (2), ε(380) represents the gram extinction coefficient at a wavelength of 380 nm of the light-selective absorption compound (B) having a merocyanine structure in the molecule and exhibiting maximum absorption at a wavelength of 360 nm or more.

ε (420) represents the gram extinction coefficient at a wavelength of 420 nm of the light-selective absorption compound (B) having a merocyanine structure in the molecule and exhibiting maximum absorption at a wavelength of 360 nm or more. The unit of the gram extinction coefficient is L/(g·cm)]

The value of ε (380) is preferably 30 L/(g cm) or more, more preferably 35 L/(g cm) or more, still more preferably 50 L/(g cm) or more, and 100 L It is still more preferable that it is /(g*cm) or more, and it is 10000 L/(g*cm) or less normally. The larger the value of ε(380), the easier it is to absorb light having a wavelength of 380 nm, and the more likely it is to exhibit a function of suppressing deterioration due to ultraviolet rays.

The light selective absorption compound (B) preferably has a value of ε(380)/ε(420) of 25 or more, more preferably 35 or more, still more preferably 50 or more, and particularly more preferably 100 or more. The pressure-sensitive adhesive layer formed of the pressure-sensitive adhesive composition including a compound having a large value of ε(380)/ε(420) absorbs ultraviolet rays in the vicinity of 380 nm without inhibiting color expression of a display device. Moreover, photodegradation of display apparatuses, such as a laminated|stacked optical film (retardation film) and organic electroluminescent element, can be suppressed.

Examples of the light-selective absorption compound (B) include compounds having a merocyanine structure described in International Publication Nos. 2019/073869 and International Publication No. 2019/004046.

Moreover, it is preferable that the light-selective absorption compound (B) has a structure in which the carbon atom contained in a merocyanine structure couple|bonds with an electron withdrawing group. Specifically, the light-selective absorption compound (B) preferably has a partial structure represented by NC=C(R ^Y3 )-C=C (where R ^Y3 represents an electron withdrawing group).

The light-selective absorption compound (B) having a partial structure represented by NC=C(R ^Y3 )-C=C includes, for example, a compound represented by the following formula (Y).

[In formula (Y), R ^Y3 , R ^Y4 and R ^Y5 each independently represent an electron withdrawing group.

R ^Y1 , R ^Y2 , R ^Y6 and R ^Y7 are each independently a hydrogen atom, a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxy group, a thiol group, a carboxy group, -SCF ₃ , -SF ₅ , -SF ₃ , - SO ₃ H, —SO ₂ H, 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, and —CH contained in the aliphatic hydrocarbon group or aromatic hydrocarbon group ₂ - or -CH= is -NR ^1A -, -SO ₂ -, -CO-, -O-, -COO-, -OCO-, -CONR ^2A -, -NR ^3A -CO-, -S-, -SO-, -SO ₂ -, -CF ₂ -, or -CHF- may be substituted.

R ^1A , R ^2A and R ^3A each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.

R ^Y1 and R ^Y2 may be linked to each other to form a ring.

R ^Y1 and R ^Y6 may be linked to each other to form a ring.

R ^Y4 and R ^Y5 may be linked to each other to form a ring.]

Examples of the electron withdrawing group represented by R ^Y3 , R ^Y4 and R ^Y5 include a halogen atom, a nitro group, a cyano group, a carboxy group, a halogenated alkyl group, a halogenated aryl group, -OCF ₃ , -SCF ₃ , -SF ₅ , -SF ₃ , -SO ₃ H, -SO ₂ H, a group represented by a formula (Y-1) is mentioned.

[In formula (Y-1),

X ¹ represents -CO-, -COO-, -OCO-, -CS-, -CSS-, -COS-, -CSO-, -SO ₂ -, -NR ²²³ CO- or -CONR ²²⁴ -.

R ²²² represents a hydrogen atom, an optionally substituted alkyl group having 1 to 25 carbon atoms, or an optionally substituted aromatic hydrocarbon group having 6 to 18 carbon atoms.

R ²²³ and R ²²⁴ each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group.

* indicates the number of bonds.]

A fluorine atom, a chlorine atom, a bromine atom, and an iodine atom are mentioned as a halogen atom.

Examples of the halogenated alkyl group include trifluoromethyl group, perfluoroethyl group, perfluoropropyl group, perfluoroisopropyl group, perfluorobutyl group, perfluorosec-butyl group, perfluorotert-butyl group, Fluoroalkyl groups, such as a perfluoropentyl group and a perfluorohexyl group, etc. are mentioned, It is preferable that it is a perfluoroalkyl group. The number of carbon atoms in the halogenated alkyl group is usually 1 to 25, preferably 1 to 12 carbon atoms. The halogenated alkyl group may be linear or branched.

A fluorophenyl group, a chlorophenyl group, a bromophenyl group etc. are mentioned as a halogenated aryl group, It is preferable that it is a fluoroaryl group, and it is more preferable that it is a perfluoroaryl group. The number of carbon atoms in the halogenated aryl group is usually 6 to 18, preferably 6 to 12 carbon atoms.

X ¹ is preferably -COO- or -SO ₂ -.

Examples of the alkyl group having 1 to 25 carbon atoms represented by R ²²² include a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, tert-butyl group, sec-butyl group, n-pentyl group, n-hexyl group and linear or branched C1-C25 alkyl groups, such as 1-methylbutyl group, 3-methylbutyl group, n-octyl group, n-decyl, 2-hexyl-octyl group. R ²²² is preferably an alkyl group having 1 to 12 carbon atoms.

Examples of the substituent that the C1-C25 alkyl group represented by R ²²² may have include a halogen atom and a hydroxyl group.

Examples of the aromatic hydrocarbon group having 6 to 18 carbon atoms represented by R ²²² include aryl groups having 6 to 18 carbon atoms, such as a phenyl group, a naphthyl group, an anthracenyl group, and a biphenyl group; and an aralkyl group having 7 to 18 carbon atoms, such as a benzyl group, a phenylethyl group, and a naphthylmethyl group.

Examples of the substituent which the aromatic hydrocarbon group having 6 to 18 carbon atoms represented by R ²²² may have include a halogen atom and a hydroxyl group.

Examples of the alkyl group having 1 to 6 carbon atoms represented by R ²²³ and R ²²⁴ include a methyl group, an ethyl group, n-propyl group, isopropyl group, n-butyl group, tert-butyl group, sec-butyl group, n-pentyl group, n -hexyl group, 1-methylbutyl group, 3-methylbutyl, etc. are mentioned.

R ^Y3 is a nitro group, a cyano group, -F, -OCF ₃ , -SCF ₃ , -SF ₅ , -SF ₃ , -SO ₂ -R ²²² (R ²²² is a hydrogen atom, optionally having 1 to 25 carbon atoms) represents an alkyl group or an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent), a fluoroalkyl group (preferably a fluoroalkyl group having 1 to 25 carbon atoms) or a fluoroaryl group (preferably a C6-C18 aromatic hydrocarbon group) fluoroaryl group), more preferably a cyano group, -F, -OCF ₃ , -SCF ₃ , or a fluoroalkyl group (preferably a C1-C25 fluoroalkyl group), and a cyano group more preferably.

At least one selected from R ^Y4 and R ^Y5 is a cyano group, a nitro group, -OCF ₃ , -SCF ₃ , -SF ₅ , -CO-OR ²²² , -SO ₂ -R ²²² (R ²²² is a hydrogen atom, a substituent represents an alkyl group having 1 to 25 carbon atoms which may have or an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent), a fluoroalkyl group (preferably a fluoroalkyl group having 1 to 25 carbon atoms) or a fluoroaryl group ( Preferably, it is a C6-C18 fluoroaryl group). More preferably, it is a cyano group, a nitro group, -CO-OR ²²² or -SO ₂ -R ²²² , More preferably, it is a cyano group.

It is preferable that R ^Y4 and R ^Y5 have the same structure.

R ^Y4 and R ^Y5 may combine with each other to form a ring. The ring formed by combining R ^Y4 and R ^Y5 with each other may be monocyclic or condensed, but is preferably monocyclic. Further, the ring formed by bonding R ^Y4 and R ^Y5 to each other may contain a hetero atom (nitrogen atom, oxygen atom, sulfur atom) or the like as a constituent element of the ring.

The ring formed by combining R ^Y4 and R ^Y5 with each other is usually a 3- to 10-membered ring, preferably a 5- to 7-membered ring, and more preferably a 5-membered or 6-membered ring.

Examples of the ring formed by bonding R ^Y4 and R ^Y5 to each other include the structures described below.

[In the formula, * represents the number of bonds with a carbon atom. R ^1E to R ^16E each independently represent a hydrogen atom or a substituent.]

The ring formed by combining R ^Y4 and R ^Y5 with each other may have a substituent (R ^1E to R ^16E in the above formula).

Examples of the substituent represented by R ^1E to R ^16E include a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom and an iodine atom; an alkyl group having 1 to 12 carbon atoms, such as a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, and a nonyl group; Fluoromethyl group, difluoromethyl group, trifluoromethyl group, 2-fluoroethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group, 1,1,2,2-tetrafluoro halogenated alkyl groups having 1 to 12 carbon atoms, such as a roethyl group and a 1,1,2,2,2-pentafluoroethyl group; an alkoxy group having 1 to 12 carbon atoms, such as a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, and a hexyloxy group; an alkylthio group having 1 to 12 carbon atoms, such as a methylthio group, an ethylthio group, a propylthio group, a butylthio group, a pentylthio group, and a hexylthio group; Fluorination of 1 to 12 carbon atoms, such as monofluoromethoxy group, difluoromethoxy group, trifluoromethoxy group, 2-fluoroethoxy group, 1,1,2,2,2-pentafluoroethoxy group alkoxy group; an amino group which may be substituted with an alkyl group having 1 to 6 carbon atoms, such as an amino group, a methylamino group, an ethylamino group, a dimethylamino group, a diethylamino group, and methylethyl; an alkylcarbonyloxy group having 2 to 12 carbon atoms, such as a methylcarbonyloxy group and an ethylcarbonyloxy group; an alkylsulfonyl group having 1 to 12 carbon atoms, such as a methylsulfonyl group and an ethylsulfonyl group; an arylsulfonyl group having 6 to 12 carbon atoms, such as a phenylsulfonyl group; cyano group; nitro group; hydroxyl group; thiol group; carboxyl group; -SF ₃ ; -SF ₅ etc. are mentioned.

R ^1E to R ^16E are each independently preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, and still more preferably a methyl group.

Examples of the aliphatic hydrocarbon group having 1 to 25 carbon atoms represented by R ^Y1 , R ^Y2 , R ^Y6 and R ^Y7 include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a tert-butyl group, and a sec-butyl group. group, n-pentyl group, isopentyl group, n-hexyl group, isohexyl group, n-octyl group, isooctyl group, n-nonyl group, isononyl group, n-decyl group, isodecyl group, n-dodecyl group , isododecyl group, undecyl group, lauryl group, myristyl group, cetyl group, stearyl group, etc. linear or branched alkyl groups having 1 to 25 carbon atoms: cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclo C3-C25 cycloalkyl groups, such as a hexyl group; C4-C25 cycloalkylalkyl groups, such as a cyclohexylmethyl group, etc. are mentioned.

The aliphatic hydrocarbon group having 1 to 25 carbon atoms represented by R ^Y1 , R ^Y2 , R ^Y6 and R ^Y7 is each independently preferably an alkyl group having 1 to 15 carbon atoms, more preferably an alkyl group having 1 to 12 carbon atoms.

Examples of the substituent which the aliphatic hydrocarbon group having 1 to 25 carbon atoms represented by R ^Y1 , R ^Y2 , R ^Y6 and R ^Y7 may have include a halogen atom, a hydroxyl group, a nitro group, a cyano group, -SO ₃ H, a thiol group, and an amino group. can

-CH ₂ - or -CH= contained in the C1-C25 aliphatic hydrocarbon group represented by R ^Y1 , R ^Y2 , R ^Y6 and R ^Y7 is -NR ^1A -, -SO ₂ -, -CO-, -O -, -COO-, -OCO-, -CONR ^2A -, -NR ^3A -CO-, -S-, -SO-, -CF ₂ - or -CHF- may be substituted.

When -CH ₂ - or -CH= included in the aliphatic hydrocarbon group having 1 to 25 carbon atoms is substituted, it is preferably substituted with -O-, -S-, -COO- or -SO ₂ -.

When -CH ₂ - or -CH= contained in the C1-C25 aliphatic hydrocarbon group is substituted with -O-, the aliphatic hydrocarbon group is -OR ¹¹¹ (R ¹¹¹ is a C1-C24 aliphatic hydrocarbon group which may have a halogen atom It is preferable that it is an alkoxy group represented by an alkyl group). Moreover, polyalkyleneoxy groups, such as a polyethyleneoxy group and a polypropyleneoxy group, may be sufficient.

When -CH ₂ - or -CH= contained in the C1-C25 aliphatic hydrocarbon group is substituted with -S-, the aliphatic hydrocarbon group is -SR ¹¹¹ (R ¹¹¹ is a C1-C24 aliphatic hydrocarbon group which may have a halogen atom It is preferably an alkylthio group represented by an alkyl group).

When -CH ₂ - or -CH= contained in the aliphatic hydrocarbon group having 1 to 25 carbon atoms is substituted with -COO-, the aliphatic hydrocarbon group is -COO-R ¹¹¹ (R ¹¹¹ represents 1 to carbon atoms which may have a halogen atom) It is preferable that it is group represented by the alkyl group of 24).

When -CH ₂ - or -CH= contained in the aliphatic hydrocarbon group having 1 to 25 carbon atoms is substituted with -SO ₂ -, the aliphatic hydrocarbon group is -SO ₂ -R ¹¹¹ (R ¹¹¹ is the number of carbon atoms which may have a halogen atom) It is preferable that it is group represented by the alkyl group of 1-24), -SO ₂ CHF ₂ , -SO ₂ CH ₂ F, etc. may be sufficient.

Examples of the aromatic hydrocarbon group having 6 to 18 carbon atoms represented by R ^Y1 , R ^Y2 , R ^Y6 and R ^Y7 include a phenyl group, a naphthyl group, an anthracenyl group, a tetracenyl group, a pentacenyl group, a phenanthryl group, a chrysenyl group, and a tri an aryl group having 6 to 18 carbon atoms, such as a phenylenyl group, a tetraphenyl group, a pyrenyl group, a perylenyl group, a coronenyl group, and a biphenyl group; and an aralkyl group having 7 to 18 carbon atoms, such as a benzyl group, a phenylethyl group, and a naphthylmethyl group. An aryl group having 6 to 18 carbon atoms is preferable, and a phenyl group or a benzyl group is more preferable.

Examples of the substituent which the aromatic hydrocarbon group having 6 to 18 carbon atoms represented by R ^Y1 , R ^Y2 , R ^Y6 and R ^Y7 may have include a halogen atom; hydroxyl group; thiol group; amino group; nitro group; cyano group; -SO ₃ H group, and the like.

-CH ₂ - or -CH= contained in the aromatic hydrocarbon group having 6 to 18 carbon atoms represented by R ^Y1 , R ^Y2 , R ^Y6 and R ^Y7 is -NR ^1A -, -SO ₂ -, -CO-, -O -, -COO-, -OCO-, -CONR ^2A -, -NR ^3A -CO-, -S-, -SO-, -CF ₂ - or -CHF- may be substituted.

When -CH ₂ - or -CH= included in the aromatic hydrocarbon group having 6 to 18 carbon atoms is substituted, it is preferably substituted with -O- or -SO ₂ -.

When -CH ₂ - or -CH= contained in the aromatic hydrocarbon group having 6 to 18 carbon atoms is substituted with -O-, the aromatic hydrocarbon group may include an aryloxy group having 6 to 17 carbon atoms such as a phenoxy group; It is preferable that they are an aryl alkoxy group of a phenoxyethyl group, a phenoxydiethylene glycol group, a phenoxy polyalkylene glycol group, etc.

When -CH ₂ - or -CH= included in the aromatic hydrocarbon group having 6 to 17 carbon atoms is substituted with -SO ₂ -, the aromatic hydrocarbon group is -SO ₂ -R ¹¹² (R ¹¹² is an aryl group having 6 to 17 carbon atoms) or an aralkyl group having 7 to 17 carbon atoms).

Examples of the alkyl group having 1 to 6 carbon atoms represented by R ^1A , R ^2A and R ^3A include the same groups as the alkyl group having 1 to 6 carbon atoms represented by R ²²³ .

Examples of the halogen atom represented by R ^Y1 , R ^Y2 , R ^Y6 and R ^Y7 include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

Examples of the heterocyclic group represented by R ^Y1 , R ^Y2 , R ^Y6 and R ^Y7 include a pyridyl group, a pyrrolidyl group, a tetrahydrofurfuryl group, a tetrahydrothiophene group, a pyrrole group, a furyl group, a thiopheno group, and a piperidine group. , tetrahydropyranyl group, tetrahydrothiopyranyl group, thiapyranyl group, imidazolino group, pyrazole group, oxazole group, thiazolyl group, dioxanyl group, morpholino group, thiadinyl group, triazole group, tetrazole group, diox Soranyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, indolyl group, isoindolyl group, benzoimidazolyl group, furinyl group, benzotriazolyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group , quinoxalinyl group, cinnolinyl group, pteridinyl group, benzopyranyl group, anthryl group, acridinyl group, xanthenyl group, carbazolyl group, tetracenyl group, porphinyl group, chlorinyl group, corinyl group, Aliphatic heterocyclic groups having 3 to 16 carbon atoms, such as adenyl group, guanyl group, cytosyl group, thyminyl group, uracil group, quinolyl group, thiophenyl group, imidazolyl group, oxazolyl group, and thiazolyl group, and 3 to 16 carbon atoms of aromatic heterocyclic groups. The heterocyclic groups represented by R ¹ , R ² , R ⁶ and R ⁷ are each independently a pyrrolidyl group, a piperidyl group, a tetrahydrofurfuryl group, a tetrahydropyranyl group, a tetrahydrothiopheno group, and a tetrahydrothiopyra group. It is preferable that it is a nyl group or a pyridyl group.

The ring formed by combining R ^Y1 and R ^Y2 with each other includes one nitrogen atom as a component of the ring. The ring formed by combining R ^Y1 and R ^Y2 with each other may be monocyclic or condensed, but is preferably monocyclic. The ring formed by bonding R ^Y1 and R ^Y2 to each other may further contain a hetero atom (oxygen atom, sulfur atom, nitrogen atom, etc.) as a component of the ring. The ring formed by combining R ^Y1 and R ^Y2 with each other is preferably a ring having no unsaturated bond.

The ring formed by combining R ^Y1 and R ^Y2 with each other is usually a 3- to 10-membered ring, preferably a 5- to 7-membered ring, and more preferably a 5-membered or 6-membered ring.

The ring formed by combining R ^Y1 and R ^Y2 with each other may have a substituent. Examples of the substituent include the same substituents as those represented by R ^1E .

Examples of the ring formed by bonding R ^Y1 and R ^Y2 to each other include the rings described below.

R ^Y1 and R ^Y2 are each independently preferably an alkyl group having 1 to 25 carbon atoms, more preferably an alkyl group having 1 to 12 carbon atoms, still more preferably a linear alkyl group having 1 to 6 carbon atoms, a methyl group or an ethyl group , n-propyl group or n-butyl group is particularly preferred.

R ^Y6 and R ^Y7 are each independently preferably an alkyl group having 1 to 25 carbon atoms, more preferably an alkyl group having 1 to 12 carbon atoms, still more preferably a branched alkyl group having 1 to 6 carbon atoms, and isopropyl group , an isobutyl group and a t-butyl group are particularly preferable.

Examples of the compound represented by the formula (Y) include the compound represented by the formula (Y-1) to the compound represented by the formula (Y-136) described below.

The compound (Y) is, for example, a compound represented by the formula (Y-A) (hereinafter sometimes referred to as compound (Y-A)) and a compound represented by the formula (Y-B) (hereinafter sometimes referred to as compound (Y-B). ) can be obtained by reacting

[Wherein, R ^Y1 to R ^Y7 have the same meaning as above.]

The reaction of compound (Y-A) and compound (Y-B) is usually carried out by mixing compound (Y-A) and compound (Y-B), and it is preferable to add compound (Y-B) to compound (Y-A).

In addition, in the reaction of compound (Y-A) and compound (Y-B), it is preferable to mix compound (Y-A) and compound (Y-B) in the presence of a base and a methylating agent,

It is preferred to mix compound (Y-A), compound (Y-B), a base and a methylating agent,

It is more preferable to mix the compound (Y-B) and the base with the mixture of the compound (Y-A) and the methylating agent,

It is more preferred to add the mixture of compound (Y-B) and the base to the mixture of compound (Y-A) and the methylating agent.

Examples of the base include metal hydroxides (preferably alkali metal hydroxides) such as sodium hydroxide, lithium hydroxide, potassium hydroxide, cesium hydroxide, rubidium hydroxide, calcium hydroxide, barium hydroxide, and magnesium hydroxide; Metal alkoxides (preferably alkali metal alkoxides), such as sodium methoxide, potassium methoxide, lithium methoxide, sodium ethoxide, sodium isopropoxide, sodium-t-butoxide, potassium-t-butoxide ; metal hydrides such as lithium hydride, sodium hydride, potassium hydride, lithium aluminum hydride, sodium borohydride, aluminum hydride, and sodium aluminum hydride; metal oxides such as calcium oxide and magnesium oxide; metal carbonates such as sodium hydrogencarbonate, sodium carbonate and potassium carbonate (preferably alkaline earth metal carbonates); organoalkyl metal compounds such as normal butyl lithium, tert-butyl lithium, methyl lithium, and Grignard reagent; Ammonia, triethylamine, diisopropylethylamine, ethanolamine, pyrrolidine, piperidine, diazabicycloundecene, diazabicyclononene, guanidine, tetramethylammonium hydroxide, tetraethylammonium hydroxide, pyridine, aniline, amine compounds such as dimethoxyaniline, ammonium acetate and β-alanine (preferably tertiary amines such as triethylamine and diisopropylethylamine); metal amide compounds (preferably alkali metal amides) such as lithium diisopropylamide, sodium amide and potassium hexamethyldisilazide; sulfonium compounds such as trimethylsulfonium hydroxide; iodonium compounds such as diphenyliodonium hydroxide; and a phosphazene base.

The amount of the base used is usually 0.1 to 5 moles, preferably 0.5 to 2 moles, per 1 mole of compound (Y-A).

Examples of the methylating agent include iodomethane, dimethyl sulfate, methyl methanesulfonate, methyl fluorosulfonate, methyl paratoluenesulfonate, methyl trifluoromethanesulfonate, and trimethyloxonium tetrafluoroborate.

The amount of the methylating agent to be used is usually 0.1 to 5.0 moles, preferably 0.5 to 2.0 moles, per 1 mole of compound (Y-A).

The reaction time between compound (Y-A) and compound (Y-B) is usually 0.1 to 10 hours, preferably 0.2 to 3 hours.

The reaction temperature of the compound (Y-A) and the compound (Y-B) is usually -50 to 150°C, preferably -20 to 100°C.

The usage-amount of compound (Y-B) is 0.1-10 mol normally with respect to 1 mol of compound (Y-A), and it is preferable that it is 0.5-5 mol.

Examples of the compound (Y-A) include the compounds described below.

A commercial item may be used as a compound (Y-B), The compound etc. which were described below are mentioned.

The compound (Y-A) is, for example, a compound represented by the formula (Y-C) (hereinafter sometimes referred to as compound (Y-C)) and a compound represented by the formula (Y-D) (hereinafter sometimes referred to as compound (Y-D). ) can be obtained by reacting

[In formula (YC), R ^Y1 , R ^Y2 , R ^Y3 , R ^Y6 and R ^Y7 have the same meaning as above. E ₁ represents a leaving group.]

Examples of the leaving group represented by E ₁ include a halogen atom, a p-toluenesulfonyl group, and a trifluoromethylsulfonyl group.

The reaction of the compound (Y-C) and the compound (Y-D) is carried out by mixing the compound (Y-C) and the compound (Y-D).

The usage-amount of compound (Y-D) is 0.1-5 mol normally with respect to 1 mol of compound (Y-C), and it is preferable that it is 0.5-2 mol.

The reaction between compound (Y-C) and compound (Y-D) may be carried out in the presence of a solvent. Examples of the solvent include acetonitrile, benzene, toluene, acetone, ethyl acetate, chloroform, dichloroethane, monochlorobenzene, methanol, ethanol, isopropanol, tert-butanol, 2-butanone, tetrahydrofuran, diethyl ether, dimethyl sulfoxide. , N,N-dimethylacetamide, N,N-dimethylformamide, and water. Preferably, they are acetonitrile, tetrahydrofuran, chloroform, dichloromethane, and diethyl ether, More preferably, they are acetonitrile, tetrahydrofuran, and chloroform, More preferably, they are methanol, ethanol, isopropanol, and acetonitrile.

The reaction time between compound (Y-C) and compound (Y-D) is usually 0.1 to 10 hours.

The reaction temperature of compound (Y-C) and compound (Y-D) is usually -50 to 150°C.

Examples of the compound (Y-C) include the compounds described below.

As the compound (Y-D), a commercially available product may be used. For example, chlorocyanide, bromocyanide, paratoluenesulfonylcyanide, trifluoromethanesulfonylcyanide, 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis( Tetrafluoroborate (also called Selectfluoro (registered trademark of Air Products and Chemicals)), benzoyl (phenyliodonio) (trifluoromethanesulfonyl) methanide, 2,8-difluoro-5- (trifluoromethyl)-5H-dibenzo[b, d]thiophene-5-ium trifluoromethanesulfonate, N-bromosuccinimide, N-chlorosuccinimide, N-iodosuccin Mead etc. are mentioned.

Compound (Y-C) is a compound represented by formula (Y-E) (hereinafter sometimes referred to as compound (Y-E)) and a compound represented by formula (Y-F) (hereinafter sometimes referred to as compound (Y-F).) can be obtained by reacting

[Wherein, R ^Y1 , R ^Y2 , R ^Y6 and R ^Y7 have the same meaning as above.]

The reaction of the compound (Y-E) and the compound (Y-F) is carried out by mixing the compound (Y-E) and the compound (Y-F).

The usage-amount of compound (Y-F) is 0.1-5 mol normally with respect to 1 mol of compound (Y-E), and it is preferable that it is 0.5-2 mol.

The reaction between compound (Y-E) and compound (Y-F) may be carried out in the presence of a solvent. Acetonitrile, benzene, toluene, acetone, ethyl acetate, chloroform, dichloroethane, monochlorobenzene, methanol, ethanol, isopropanol, tert-butanol, 2-butanone, tetrahydrofuran, diethyl ether, dimethyl sulfoxide, N, N-dimethylacetamide, N,N-dimethylformamide, water, etc. are mentioned. Preferably, they are benzene, toluene, ethanol, and acetonitrile.

The reaction time between compound (Y-E) and compound (Y-F) is usually 0.1 to 10 hours.

The reaction temperature between compound (Y-E) and compound (Y-F) is usually -50 to 150°C.

As compound (Y-E), the compound etc. which were described below are mentioned.

Examples of the compound (Y-F) include primary amines such as methylamine, ethylamine, ethanolamine and 4-hydroxybutylamine; and secondary amines such as dimethylamine, diethylamine, dibutylamine, pyrrolidine, piperidine, 3-hydroxypyrrolidine and 4-hydroxypiperidine.

Further, the light-selective absorption compound (B) is also preferably a compound having a part of the merocyanine structure as a component of the ring. Examples of the compound having a part of the merocyanine structure as a component of the ring include compounds in which the carbon-carbon bond structural moiety in the merocyanine structure becomes a component of the ring.

The light-selective absorption compound (B) having a part of the merocyanine structure as a component of the ring is, for example, a compound having a partial structure represented by the following formula (X) (hereinafter sometimes referred to as compound (X)). can be heard

[In formula (X), ring W ¹ represents a ring structure having at least one double bond as a component of the ring and not having aromaticity.

R ³ is a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a thiol group, a carboxy group, -SF ₅ , -SF ₃ , -SO ₃ H, -SO ₂ H, optionally having 1 to 25 carbon atoms represents an aliphatic hydrocarbon group or an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent, and -CH ₂ -, -CH= contained in the aliphatic hydrocarbon group or aromatic hydrocarbon group is -O-, -S-, -NR ^1xA - , -CO-, -CO-O-, -O-CO-, -O-CO-O-, -CONR ^2xA -, -NR ^3xA -CO-, -O-CO-NR ^4xA -, -NR ^5xA - CO-O-, -NR ^6xA -CO-NR ^7xA -, -CO-S-, -S-CO-S-, -S-CO-NR ^8xA -, -NR ^9xA -CO-S-, -CS- , -O-CS-, -CS-O-, -NR ^10xA -CS-, -NR ^11xA -CS-S-, -S-CS-, -CS-S-, -S-CS-S-, - SO- or -SO ₂ - may be substituted.

R ^1xA , R ^2xA , R ^3xA , R 4xA , R ^5xA , R ^6xA , R ^7xA , R ^8xA , R ^9xA , R ^10xA and R ^11xA each independently ^represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.]

Ring W ¹ is not particularly limited as long as it is a ring having at least one double bond as a component of the ring and is a ring having no aromaticity. Ring W ¹ may be a monocyclic ring or a condensed ring may be sufficient as it.

The ring W ¹ may be a heterocyclic ring containing a hetero atom (eg, an oxygen atom, a sulfur atom, a nitrogen atom, etc.) as a component of the ring, or an aliphatic hydrocarbon ring containing a carbon atom and a hydrogen atom.

Ring W ¹ has at least one double bond as a component of the ring, but the number of double bonds contained in ring W ¹ is usually 1 to 4, preferably 1 to 3, more preferably 1 or 2, and one It is more preferable that

Ring W ¹ is usually a ring having 5 to 18 carbon atoms, preferably a 5 to 7 membered ring structure, and more preferably a 6 membered ring structure.

Ring W ¹ is preferably monocyclic.

Ring W ¹ may have a substituent. As said substituent, Halogen atoms, such as a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom; an alkyl group having 1 to 12 carbon atoms, such as a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, and a nonyl group; Fluoromethyl group, difluoromethyl group, trifluoromethyl group, 2-fluoroethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group, 1,1,2,2-tetrafluoro halogenated alkyl groups having 1 to 12 carbon atoms, such as a roethyl group and a 1,1,2,2,2-pentafluoroethyl group; an alkoxy group having 1 to 12 carbon atoms, such as a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, and a hexyloxy group; an alkylthio group having 1 to 12 carbon atoms, such as a methylthio group, an ethylthio group, a propylthio group, a butylthio group, a pentylthio group, and a hexylthio group; Fluorination of 1 to 12 carbon atoms, such as monofluoromethoxy group, difluoromethoxy group, trifluoromethoxy group, 2-fluoroethoxy group, 1,1,2,2,2-pentafluoroethoxy group alkoxy group; an amino group which may be substituted with an alkyl group having 1 to 6 carbon atoms, such as an amino group, a methylamino group, an ethylamino group, a dimethylamino group, a diethylamino group, and methylethyl; an alkylcarbonyloxy group having 2 to 12 carbon atoms, such as a methylcarbonyloxy group and an ethylcarbonyloxy group; an alkylsulfonyl group having 1 to 12 carbon atoms, such as a methylsulfonyl group and an ethylsulfonyl group; an arylsulfonyl group having 6 to 12 carbon atoms, such as a phenylsulfonyl group; cyano group; nitro group; hydroxyl group; thiol group; carboxyl group; -SF ₃ ; -SF ₅ etc. are mentioned.

The substituent which the ring W ¹ may have is preferably an amino group which may be substituted with an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkylthio group having 1 to 12 carbon atoms, or an alkyl group having 1 to 6 carbon atoms. .

Examples of the ring W ¹ include the groups described below.

[In the formula, *1 represents the number of bonds with a nitrogen atom, and *2 represents the number of bonds with a carbon atom.]

Examples of the heterocyclic group represented by R ³ include the same heterocyclic group represented by R ^Y1 in the formula (Y).

The heterocyclic group represented by R ³ is preferably a pyrrolidyl group, a piperidyl group, a tetrahydrofurfuryl group, a tetrahydropyranyl group, a tetrahydrothiopheno group, a tetrahydrothiopyranyl group, or a pyridyl group.

Examples of the aliphatic hydrocarbon group having 1 to 25 carbon atoms represented by R ³ include the same groups as the aliphatic hydrocarbon group having 1 to 25 carbon atoms represented by R ^Y1 in the formula (Y).

It is preferable that it is a C1-C15 alkyl group, and, as for the C1-C25 aliphatic hydrocarbon group represented by R< ³ >, it is more preferable that it is a C1-C12 alkyl group.

As a substituent which the aliphatic hydrocarbon group represented by R< ³ > may have, a halogen atom, a hydroxyl group, a nitro group, a cyano group, _-SO3H , etc. are mentioned.

-CH ₂ - or -CH= contained in the aliphatic hydrocarbon group having 1 to 25 carbon atoms represented by R ³ is -O-, -S-, -NR ^1xA -, -CO-, -CO-O-, -O -CO-, -O-CO-O-, -CONR ^2xA -, -NR ^3xA -CO-, -O-CO-NR ^4xA -, -NR ^5xA -CO-O-, -NR ^6xA -CO-NR ^7xA -, -CO-S-, -S-CO-S-, -S-CO-NR ^8xA -, -NR ^9xA -CO-S-, -CS-, -O-CS-, -CS-O-, -NR ^10xA -CS-, -NR ^11xA -CS-S-, -S-CS-, -CS-S-, -S-CS-S-, -SO- or -SO ₂ - may be substituted.

When -CH ₂ - or -CH= included in the C1-C25 aliphatic hydrocarbon group is substituted, it is preferably substituted with -O-, -S-, -CO-O- or -SO ₂ -.

Alkoxy represented by -OR (R is an alkyl group having 1 to 24 carbon atoms which may have a halogen atom) when -CH ₂ - or -CH= contained in the aliphatic hydrocarbon group having 1 to 25 carbon atoms is substituted with -O- It is preferably a group, polyethylene glycol or polypropylene glycol.

When -CH ₂ - or -CH= contained in the aliphatic hydrocarbon group having 1 to 25 carbon atoms is substituted with -S-, alkyl represented by -SR (R is an alkyl group having 1 to 24 carbon atoms which may have a halogen atom) It is preferable that it is a thio group.

When -CH ₂ - or -CH= contained in the above-mentioned aliphatic hydrocarbon group having 1 to 25 carbon atoms is substituted with -COO-, -COO-R ¹¹¹ (R ¹¹¹ is an alkyl group having 1 to 24 carbon atoms which may have a halogen atom) It is preferably a group represented by .

When -CH ₂ - or -CH= contained in the C1-C25 aliphatic hydrocarbon group is substituted with -SO ₂ -, -SO ₂ -R ¹¹² (R ¹¹² represents a C1-C24 halogen atom) It is preferable that it is a group represented by the alkyl group).

^{As an alkyl group having 1 to 6 carbon atoms represented by R 1xA , R 2xA , R 3xA , R 4xA , R 5xA , R 6xA , R 7xA , R 8xA , R 9xA , R 10xA and R 11xA , R in formula ( Y )} The same thing as the C1-C6 alkyl group represented by ^1A is mentioned.

Examples of the aromatic hydrocarbon group having 6 to 18 carbon atoms represented by R ³ include the same ones as the aromatic hydrocarbon group having 6 to 18 carbon atoms represented by R ^Y1 in the formula (Y).

It is preferable that it is a C6-C18 aryl group, and, as for the C6-C18 aromatic hydrocarbon group represented by R< ³ >, it is more preferable that it is a phenyl group or a benzyl group.

Examples of the substituent which the aromatic hydrocarbon group having 6 to 25 carbon atoms represented by R ³ may have include a halogen atom; hydroxyl group; thiol group; amino group; nitro group; cyano group; -SO ₃ H group, and the like.

-CH ₂ - or -CH= contained in the aromatic hydrocarbon group having 6 to 18 carbon atoms represented by R ³ is -O-, -S-, -NR ^1xA -, -CO-, -CO-O-, -O -CO-, -O-CO-O-, -CONR ^2xA -, -NR ^3xA -CO-, -O-CO-NR ^4xA -, -NR ^5xA -CO-O-, -NR ^6xA -CO-NR ^7xA -, -CO-S-, -S-CO-S-, -S-CO-NR ^8xA -, -NR ^9xA -CO-S-, -CS-, -O-CS-, -CS-O-, -NR ^10xA -CS-, -NR ^11xA -CS-S-, -S-CS-, -CS-S-, -S-CS-S-, -SO- or -SO ₂ - may be substituted.

When -CH ₂ - or -CH= included in the aromatic hydrocarbon group having 6 to 18 carbon atoms is substituted, it is preferably substituted with -O- or -SO ₂ -.

When -CH ₂ - or -CH= contained in the aromatic hydrocarbon group having 6 to 18 carbon atoms is substituted with -O-, it is preferably an aryloxy group having 6 to 26 carbon atoms, such as a phenoxy group.

When -CH ₂ - or -CH= included in the aromatic hydrocarbon group having 6 to 18 carbon atoms is substituted with -SO ₂ -, -SO ₂ -R (R is an aryl group having 6 to 18 carbon atoms or an aryl group having 7 to 18 carbon atoms It is preferable that it is a group represented by the aralkyl group.).

R ³ is a nitro group; cyano group; halogen atom; -OCF ₃ ; -SCF ₃ ; -SF ₅ ; -SF ₃ ; a fluoroalkyl group having 1 to 25 carbon atoms; a fluoroaryl group having 6 to 18 carbon atoms; -CO-OR ^111xA or -SO ₂ -R ^112xA (R ^111xA and R ^112xA each independently represent an alkyl group having 1 to 24 carbon atoms which may have a halogen atom.)

cyano group; fluorine atom; chlorine atom; -OCF ₃ ; -SCF ₃ ; a fluoroalkyl group having 1 to 12 carbon atoms; -CO-OR ^111xA or -SO ₂ -R ^112xA (R ^111xA and R ^112xA each independently represent an alkyl group having 1 to 24 carbon atoms which may have a halogen atom.)

It is especially preferable that it is a cyano group.

The molecular weight of compound (X) becomes like this. Preferably it is 2500 or less, More preferably, it is 2000 or less, More preferably, it is 1500 or less, Especially preferably, it is 1000 or less. Moreover, Preferably it is 100 or more, 150 or more, and 200 or more.

The compound (X) may be a homopolymer or a copolymer as long as the molecular weight is 3000 or less, but is preferably a monomer.

As compound (X), it is preferable that it is any one of the compound represented by Formula (I) - the compound represented by Formula (VIII), It is more preferable that it is a compound represented by Formula (I).

[In formulas (I) to (VIII), rings W ¹ and R ³ have the same meanings as above.

Ring W ² , Ring W ³ , Ring W ⁴ , Ring W ⁵ , Ring W ⁶ , Ring W ⁷ , Ring W ⁸ , Ring W ⁹ , Ring W ¹⁰ , Ring W ¹¹ and Ring W ¹² are each independently a constituent of a ring It represents a ring structure having at least one double bond as an element.

Ring W ¹¹¹ represents a ring having at least two nitrogen atoms as a component.

Ring W ¹¹² and ring W ¹¹³ each independently represent a ring having at least one nitrogen atom as a constituent element.

R ¹ , R ⁴¹ , R ⁵¹ , R ⁶¹ , R ⁹¹ , R ¹⁰¹ , R ¹¹¹ , R ² , R ¹² , R ⁴² , R ⁵² , R ⁶² , R ⁷² , R ⁸² , R ⁹² , R ¹⁰² and R ¹¹² . are each independently a hydrogen atom, a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a thiol group, a carboxy group, -SF ₅ , -SF ₃ , -SO ₃ H, -SO ₂ H, the number of carbon atoms which may have a substituent represents an aliphatic hydrocarbon group having 1 to 25 or an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent, and -CH ₂ - or -CH= contained in the aliphatic hydrocarbon group or aromatic hydrocarbon group is -NR ^12A -, -SO ₂ -, -CO-, -O-, -COO-, -OCO-, -CONR ^13A -, -NR ^14A -CO-, -S-, -SO-, -CF ₂ - or -CHF- good to be

R ¹³ , R ²³ , R ³³ , R ⁴³ , R ⁵³ , R ⁶³ , R ⁷³ , R ⁸³ , R ⁹³ , R ¹⁰³ and R ¹¹³ are each independently a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxy group; A thiol group, a carboxyl group, -SF ₅ , -SF ₃ , -SO ₃ H, -SO ₂ H, an optionally substituted aliphatic hydrocarbon group having 1 to 25 carbon atoms or an optionally substituted aromatic hydrocarbon group having 6 to 18 carbon atoms indicate,

-CH ₂ - or -CH= included in the aliphatic hydrocarbon group or aromatic hydrocarbon group is -O-, -S-, -NR ^1A -, -CO-, -CO-O-, -O-CO-, - O-CO-O-, -CONR ^2A -, -NR ^3A -CO-, -O-CO-NR ^4A -, -NR ^5A -CO-O-, -NR ^6A -CO-NR ^7A -, -CO- S-, -S-CO-S-, -S-CO-NR ^8A -, -NR ^9A -CO-S-, -CS-, -O-CS-, -CS-O-, -NR ^10A -CS -, -NR ^11A -CS-S-, -S-CS-, -CS-S-, -S-CS-S-, -SO- or -SO ₂ - may be substituted.

R ^1A , R ^2A , R ^3A , R ^4A , R ^5A , R ^6A , R ^7A , R ^8A , R ^9A , R ^10A , R ^11A , R ^12A , R ^13A and R ^14A are each independently a hydrogen atom or 1 carbon atom It represents the alkyl group of -6.

R ⁴ , R ¹⁴ , R ²⁴ , R ³⁴ , R ⁴⁴ , R ⁵⁴ , R ⁶⁴ , R ⁷⁴ , R ⁸⁴ , R ⁹⁴ , R ¹⁰⁴ , R ¹¹⁴ , R ⁵ , R ¹⁵ , R ²⁵ , R ³⁵ , R ⁷⁵ and R ⁸⁵ each independently represents an electron withdrawing group.

R ¹ and R ² may be bonded to each other to form a ring.

R ⁴¹ and R ⁴² may be bonded to each other to form a ring.

R ⁵¹ and R ⁵² may be bonded to each other to form a ring.

R ⁶¹ and R ⁶² may be bonded to each other to form a ring.

R ⁹¹ and R ⁹² may be bonded to each other to form a ring.

R ¹⁰¹ and R ¹⁰² may combine with each other to form a ring.

R ¹¹¹ and R ¹¹² may be bonded to each other to form a ring.

R ² and R ³ may be bonded to each other to form a ring.

R ¹² and R ¹³ may be bonded to each other to form a ring.

R ⁴² and R ⁴³ may be bonded to each other to form a ring.

R ⁵² and R ⁵³ may be bonded to each other to form a ring.

R ⁶² and R ⁶³ may be bonded to each other to form a ring.

R ⁷² and R ⁷³ may be bonded to each other to form a ring.

R ⁸² and R ⁸³ may be bonded to each other to form a ring.

R ⁹² and R ⁹³ may be bonded to each other to form a ring.

R ¹⁰² and R ¹⁰³ may be bonded to each other to form a ring.

R ¹¹² and R ¹¹³ may be bonded to each other to form a ring.

R ⁴ and R ⁵ may be bonded to each other to form a ring.

R ¹⁴ and R ¹⁵ may be bonded to each other to form a ring.

R ²⁴ and R ²⁵ may be bonded to each other to form a ring.

R ³⁴ and R ³⁵ may combine with each other to form a ring.

R ⁷⁴ and R ⁷⁵ may be bonded to each other to form a ring.

R ⁸⁴ and R ⁸⁵ may be bonded to each other to form a ring.

R ⁶ and R ⁸ each independently represent a divalent linking group.

R ⁷ represents a single bond or a divalent linking group.

R ⁹ and R ¹⁰ each independently represent a trivalent linking group.

R ¹¹ represents a tetravalent linking group.]

Ring W ² , Ring W ³ , Ring W ⁴ , Ring W ⁵ , Ring W ⁶ , Ring W ⁷ , Ring W ⁸ , Ring W ⁹ , Ring W ¹⁰ , Ring W ¹¹ and Ring W ¹² are each independently a constituent of a ring It is not particularly limited as long as it is a ring having at least one double bond as an element. Each of the rings W ² to W ¹² may be a monocyclic ring or a condensed ring. ^In addition, an aliphatic ring may be sufficient as the ring W2 ^- ring W12, and an aromatic ring may be sufficient as it.

The ring W ² to the ring W ¹² may be a heterocyclic ring containing a hetero atom (eg, an oxygen atom, a sulfur atom, a nitrogen atom, etc.) as a component of the ring.

Ring W ² - Ring W ¹² has at least one double bond as a component of the ring, but the double bonds contained in Ring W ² - Ring W ¹² are each independently usually 1 to 4, preferably 1 to 3 And, it is more preferable that it is 1 or 2, and it is still more preferable that it is one.

Each of the rings W ² to W ¹² is independently a ring having 5 to 18 carbon atoms, preferably a 5 to 7 membered ring structure, and more preferably a 6 membered ring structure.

It is preferable that the ring W ² - the ring W ¹² are each independently monocyclic. Moreover, it is preferable that the ring W ² - the ring W ¹² are each independently a ring which does not have aromaticity.

Ring W ² - Ring W ¹² may have a substituent. Examples of the substituent include the same substituents that the ring W ¹ may have.

Examples of the substituent which the ring W ² to the ring W ¹² may have include an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkylthio group having 1 to 12 carbon atoms, or an amino group which may be substituted with an alkyl group having 1 to 6 carbon atoms. It is preferable to be

Specific examples of the ring W ² to the ring W ¹² include the same as the specific examples of the ring W ¹ .

Ring W ¹¹¹ is a ring containing two nitrogen atoms as a component of the ring. The ring W ¹¹¹ may be a monocyclic ring or a condensed ring, but is preferably a monocyclic ring.

Ring W ¹¹¹ is usually a 5- to 10-membered ring, preferably a 5- to 7-membered ring, and more preferably a 5-membered or 6-membered ring.

Ring W ¹¹¹ may have a substituent. Examples of the substituent that the ring W ¹¹¹ may have include a hydroxyl group; thiol group; aldehyde group; C1-C6 alkyl groups, such as a methyl group and an ethyl group; C1-C6 alkoxy groups, such as a methoxy group and an ethoxy group; C1-C6 alkylthio groups, such as a methylthio group and an ethylthio group; an amino group which may be substituted with an alkyl group having 1 to 6 carbon atoms, such as an amino group, a methylamino group, a dimethylamino group, and methylethyl; -CONR ^1f R ^2f (R ^1f and R ^2f each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms); -COSR ^3f (R ^3f represents an alkyl group having 1 to 6 carbon atoms); -CSSR ^4f (R ^4f represents an alkyl group having 1 to 6 carbon atoms); -CSOR ^5f (R ^5f represents an alkyl group having 1 to 6 carbon atoms); _-SO2R6f ( ^R5f represents a C6- ^C12 aryl group or a C1-C6 alkyl group which may have a fluorine atom.) etc. are mentioned.

Examples of the ring W ¹¹¹ include the rings described below.

Ring W ¹¹² and ring W ¹¹³ are each independently a ring including one nitrogen atom as a component of the ring. The ring W ¹¹² and the ring W ¹¹³ each independently may be a monocyclic ring or a condensed ring, but is preferably a monocyclic ring.

Ring W ¹¹² and ring W ¹¹³ each independently represent a 5- to 10-membered ring, preferably a 5- to 7-membered ring, and more preferably a 5- or 6-membered ring.

Ring W ¹¹² and ring W ¹¹³ may have a substituent. Examples of the substituent that the ring W ¹¹² and the ring W ¹¹³ may have include the same substituents as the substituent of the ring W ¹ .

Examples of the ring W ¹¹² and the ring W ¹¹³ include the rings described below.

R ⁴ , R ¹⁴ , R ²⁴ , R ³⁴ , R ⁴⁴ , R ⁵⁴ , R ⁶⁴ , R ⁷⁴ , R ⁸⁴ , R ⁹⁴ , R ¹⁰⁴ , R ¹¹⁴ , R ⁵ , R ¹⁵ , R ²⁵ , R ³⁵ , R ⁷⁵ And as an electron withdrawing group represented by R ⁸⁵ , the same thing as R ^Y3 in Formula (Y) is mentioned.

R ⁴ , R ¹⁴ , R ²⁴ , R ³⁴ , R ⁴⁴ , R ⁵⁴ , R ⁶⁴ , R ⁷⁴ , R ⁸⁴ , R ⁹⁴ , R ¹⁰⁴ , R ¹¹⁴ , R ⁵ , R ¹⁵ , R ²⁵ , R ³⁵ , R ⁷⁵ and as the electron withdrawing group represented by R ⁸⁵ , each independently a nitro group, a cyano group, a halogen atom, -OCF ₃ , -SCF ₃ , -SF ₅ , -SF ₃ , a fluoroalkyl group (preferably having 1 to carbon atoms) 25), a fluoroaryl group (preferably having 6 to 18 carbon atoms), -CO-OR ²²² , -SO ₂ -R ²²² or -CO-R ²²² (R ²²² is a hydrogen atom, optionally having 1 to carbon atoms having a substituent) It is preferably an alkyl group of 25 or an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent.)

Nitro group, cyano group, fluorine atom, chlorine atom, -OCF ₃ , -SCF ₃ , fluoroalkyl group, -CO-OR ²²² or -SO ₂ -R ²²² (R ²²² is a hydrogen atom, optionally having 1 carbon atom) It represents a -25 alkyl group or a C6-C18 aromatic hydrocarbon group which may have a substituent.) is more preferable, and it is still more preferable that it is a cyano group.

It is preferable that at least one of R ⁴ and R ⁵ is a cyano group, R ⁴ is a cyano group, and R ⁵ is a cyano group, -CO-OR ²²² or -SO ₂ -R ²²² (R ²²² is each independently a hydrogen atom , an alkyl group having 1 to 25 carbon atoms which may have a halogen atom or an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a halogen atom) is more preferable.

Examples of the ring formed by bonding R ⁴ and R ⁵ to each other are the same as the ring formed by bonding R ^Y4 and R ^Y5 in the formula (Y) to each other.

The ring formed by combining R ⁴ and R ⁵ with each other is usually a 3- to 10-membered ring, preferably a 5- to 7-membered ring, and more preferably a 5-membered or 6-membered ring.

Examples of the ring formed by bonding R ⁴ and R ⁵ to each other include the structures described below.

[In the formula, * represents the number of bonds with a carbon atom. R ^1E to R ^16E each independently represent a hydrogen atom or a substituent.]

The ring formed by combining R ⁴ and R ⁵ with each other may have a substituent (R ^1E to R ^16E in the above formula). Examples of the substituent include the same substituents that the ring W ¹ may have. R ^1E to R ^16E are each independently preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, and still more preferably a methyl group.

Examples of the ring formed by bonding R ¹⁴ and R ¹⁵ to each other include the same ring formed by bonding of R ⁴ and R ⁵ to each other.

Examples of the ring formed by bonding R ²⁴ and R ²⁵ to each other include the same ring formed by bonding of R ⁴ and R ⁵ to each other.

Examples of the ring formed by bonding R ³⁴ and R ³⁵ to each other include the same ring formed by bonding of R ⁴ and R ⁵ to each other.

Examples of the ring formed by bonding R ⁷⁴ and R ⁷⁵ to each other include the same ring formed by bonding of R ⁴ and R ⁵ to each other.

Examples of the ring formed by bonding R ⁸⁴ and R ⁸⁵ to each other include the same ring formed by bonding of R ⁴ and R ⁵ to each other.

R ¹ , R ⁴¹ , R ⁵¹ , R ⁶¹ , R ⁹¹ , R ¹⁰¹ , R ¹¹¹ , R ² , R ¹² , R ⁴² , R ⁵² , R ⁶² , R ⁷² , R ⁸² , R ⁹² , R ¹⁰² , R ¹¹² , R ¹³ , R ²³ , R ³³ , R ⁴³ , R ⁵³ , R ⁶³ , R ⁷³ , R ⁸³ , R ⁹³ , R ¹⁰³ and R ¹¹³ as a heterocyclic group represented by R ^Y1 in formula (Y) such as the heterocyclic group that becomes

R ¹ , R ⁴¹ , R ⁵¹ , R ⁶¹ , R ⁹¹ , R ¹⁰¹ , R ¹¹¹ , R ² , R ¹² , R ⁴² , R ⁵² , R ⁶² , R ⁷² , R ⁸² , R ⁹² , R ¹⁰² , R ¹¹² The heterocyclic groups represented by , R ¹³ , R ²³ , R ³³ , R ⁴³ , R ⁵³ , R ⁶³ , R ⁷³ , R ⁸³ , R ⁹³ , R ¹⁰³ and R ¹¹³ are each independently a pyrrolidyl group, a piperidyl group, A tetrahydrofurfuryl group, a tetrahydropyranyl group, a tetrahydrothiopheno group, a tetrahydrothiopyranyl group or a pyridyl group is preferable.

R ¹ , R ⁴¹ , R ⁵¹ , R ⁶¹ , R ⁹¹ , R ¹⁰¹ , R ¹¹¹ , R ² , R ¹² , R ⁴² , R ⁵² , R ⁶² , R ⁷² , R ⁸² , R ⁹² , R ¹⁰² , R ¹¹² , R ¹³ , R ²³ , R ³³ , R ⁴³ , R ⁵³ , R ⁶³ , R ⁷³ , R ⁸³ , R ⁹³ , R ¹⁰³ and R ¹¹³ As an aliphatic hydrocarbon group having 1 to 25 carbon atoms, The same thing as the C1-C25 aliphatic hydrocarbon group represented by R ^Y1 in this is mentioned.

It is preferable that it is a C1-C15 alkyl group, and, as for the said C1-C25 aliphatic hydrocarbon group, it is more preferable that it is a C1-C12 alkyl group.

R ¹ , R ⁴¹ , R ⁵¹ , R ⁶¹ , R ⁹¹ , R ¹⁰¹ , R ¹¹¹ , R ² , R ¹² , R ⁴² , R ⁵² , R ⁶² , R ⁷² , R ⁸² , R ⁹² , R ¹⁰² , R ¹¹² The aliphatic hydrocarbon group represented by , R ¹³ , R ²³ , R ³³ , R ⁴³ , R ⁵³ , R ⁶³ , R ⁷³ , R ⁸³ , R ⁹³ , R ¹⁰³ and R ¹¹³ may have as a substituent a halogen atom, a hydroxyl group, a nitro group, a cyano group, -SO ₃ H, and the like.

Also, R ¹ , R ⁴¹ , R ⁵¹ , R ⁶¹ , R ⁹¹ , R ¹⁰¹ , R ¹¹¹ , R ² , R ¹² , R ⁴² , R ⁵² , R ⁶² , R ⁷² , R ⁸² , R ⁹² , R ¹⁰² , -CH ₂ - or -CH= contained in the aliphatic hydrocarbon group having 1 to 25 carbon atoms represented by R ¹¹² is -NR ^12A -, -SO ₂ -, -CO-, -O-, -COO-, -OCO- , -CONR ^13A -, -NR ^14A -CO-, -S-, -SO-, -CF ₂ - or -CHF- may be substituted.

^{-CH 2 -} _or ^{_ _ _ _ _ _ _ _} -CH= is, -O-, -S-, -NR ^1A -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -CONR ^2A -, -NR ^3A -CO-, -O-CO-NR ^4A -, -NR ^5A -CO-O-, -NR ^6A -CO-NR ^7xA -, -CO-S-, -S-CO-S-, -S-CO -NR ^8A -, -NR ^9A -CO-S-, -CS-, -O-CS-, -CS-O-, -NR ^10A -CS-, -NR ^11A -CS-S-, -S-CS -, -CS-S-, -S-CS-S-, -SO-, or -SO ₂ - may be substituted.

When -CH ₂ - or -CH= included in the C1-C25 aliphatic hydrocarbon group is substituted, it is preferably substituted with -O-, -S-, -CO-O- or -SO ₂ -.

When -CH ₂ - or -CH= contained in the aliphatic hydrocarbon group having 1 to 25 carbon atoms is substituted with -O-, the aliphatic hydrocarbon group is -O-R'(R' is a carbon number 1 to which may have a halogen atom. It is preferable that it is an alkoxy group represented by the alkyl group of 24).

Moreover, polyalkyleneoxy groups, such as a polyethyleneoxy group and a polypropyleneoxy group, may be sufficient. Examples of the alkoxy group represented by -O-R' include a methoxy group, an ethoxy group, and a -OCF ₃ group.

When -CH ₂ - or -CH= contained in the aliphatic hydrocarbon group having 1 to 25 carbon atoms is substituted with -S-, the aliphatic hydrocarbon group is -S-R'(R' is a group having 1 to carbon atoms which may have a halogen atom. It is preferable that it is an alkylthio group represented by the alkyl group of 24). Moreover, polyalkylenethio groups, such as a polyethylenethio group and a polypropylenethio group, may be sufficient. Examples of the alkylthio group represented by -S-R' include a methylthio group, an ethylthio group, a -SCF ₃ group, a polyethylenethio group, and a polypropylenethio group.

When -CH ₂ - or -CH= contained in the aliphatic hydrocarbon group having 1 to 25 carbon atoms is substituted with -COO-, the aliphatic hydrocarbon group is -COO-R'(R' is a C 1 to carbon atom which may have a halogen atom. It is preferable that it is group represented by the alkyl group of 24).

When -CH ₂ - or -CH= contained in the C1-C25 aliphatic hydrocarbon group is substituted with -SO ₂ -, the aliphatic hydrocarbon group is -SO ₂ -R'(R' is the number of carbon atoms which may have a halogen atom. 1-24 alkyl group) is preferable, and -SO ₂ CHF ₂ group, -SO ₂ CH ₂ F group, etc. may be sufficient.

R ^1A , R ^2A and R ^3A are the same as those described in the formula (Y).

As an alkyl group having 1 to 6 carbon atoms represented by R ^4A , R ^5A , R ^6A , R ^7A , R ^8A , R ^9A , R ^10A , R ^11A , R ^12A , R ^13A and R ^14A , R in formula (Y) The same thing as the C1-C6 alkyl group represented by ^1A is mentioned.

R ¹ , R ⁴¹ , R ⁵¹ , R ⁶¹ , R ⁹¹ , R ¹⁰¹ , R ¹¹¹ , R ² , R ¹² , R ⁴² , R ⁵² , R ⁶² , R ⁷² , R ⁸² , R ⁹² , R ¹⁰² , R ¹¹² , R ¹³ , R ²³ , R ³³ , R ⁴³ , R ⁵³ , R ⁶³ , R ⁷³ , R ⁸³ , R ⁹³ , R ¹⁰³ and R ¹¹³ as an aromatic hydrocarbon group having 6 to 18 carbon atoms represented by the formula (Y) Examples of the aromatic hydrocarbon group represented by 6 to 18 carbon atoms represented by R ^Y1 in R Y1 are preferably an aryl group having 6 to 18 carbon atoms, and more preferably a phenyl group or a benzyl group.

Examples of the substituent which the aromatic hydrocarbon group having 6 to 18 carbon atoms may have include a halogen atom; hydroxyl group; thiol group; amino group; nitro group; cyano group; -SO ₃ H group, and the like.

R ¹ , R ⁴¹ , R ⁵¹ , R ⁶¹ , R ⁹¹ , R ¹⁰¹ , R ¹¹¹ , R ² , R ¹² , R ⁴² , R ⁵² , R ⁶² , R ⁷² , R ⁸² , R ⁹² , R ¹⁰² , R ¹¹² -CH ₂ - or -CH= contained in the aromatic hydrocarbon group having 6 to 18 carbon atoms represented by is, -NR ^12A -, -SO ₂ -, -CO-, -O-, -COO-, -OCO-, - It may be substituted with CONR ^13A -, -NR ^14A -CO-, -S-, -SO-, -CF ₂ - or -CHF-.

^{-CH 2 -} _or ^{_ _ _ _ _ _ _ _} -CH= is, -O-, -S-, -NR ^1A -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -CONR ^2A -, -NR ^3A -CO-, -O-CO-NR ^4A -, -NR ^5A -CO-O-, -NR ^6A -CO-NR ^7A -, -CO-S-, -S-CO-S-, -S-CO -NR ^8A -, -NR ^9A -CO-S-, -CS-, -O-CS-, -CS-O-, -NR ^10A -CS-, -NR ^11A -CS-S-, -S-CS -, -CS-S-, -S-CS-S-, -SO-, or -SO ₂ - may be substituted.

When -CH ₂ - or -CH= included in the aromatic hydrocarbon group having 6 to 18 carbon atoms is substituted, it is preferably substituted with -O- or -SO ₂ -.

When -CH ₂ - or -CH= included in the aromatic hydrocarbon group having 6 to 18 carbon atoms is substituted with -O-, the aromatic hydrocarbon group may include an aryloxy group having 6 to 17 carbon atoms such as a phenoxy group; It is preferable that they are an aryl alkoxy group of a phenoxyethyl group, a phenoxydiethylene glycol group, a phenoxy polyalkylene glycol group, etc.

When -CH ₂ - or -CH= included in the aromatic hydrocarbon group having 6 to 18 carbon atoms is substituted with -SO ₂ -, the aromatic hydrocarbon group is -SO ₂ -R"(R" is an aryl group having 6 to 17 carbon atoms) or an aralkyl group having 7 to 17 carbon atoms).

R ² and R ³ may be linked to each other to form a ring. A component of a ring formed by connecting R ² and R ³ , and includes a double bond constituting the ring W ¹ . That is, the ring formed by connecting R ² and R ³ and the ring W ¹ form a condensed ring. Specific examples of the ring formed by connecting R ² and R ³ and the condensed ring formed by the ring W ¹ include the ring structures described below.

Examples of the ring formed by bonding of R ¹² and R ¹³ to each other are the same as the ring formed by bonding of R ² and R ³ to each other.

Examples of the ring formed by bonding of R ⁴² and R ⁴³ to each other are the same as the ring formed by bonding of R ² and R ³ to each other.

Examples of the ring formed by bonding of R ⁵² and R ⁵³ to each other are the same as the ring formed by bonding of R ² and R ³ to each other.

Examples of the ring formed by bonding R ⁶² and R ⁶³ to each other include the same ring formed by bonding of R ² and R ³ to each other.

Examples of the ring formed by bonding of R ⁷² and R ⁷³ to each other are the same as the ring formed by bonding of R ² and R ³ to each other.

Examples of the ring formed by bonding of R ⁸² and R ⁸³ to each other include the same ring formed by bonding of R ² and R ³ to each other.

Examples of the ring formed by bonding of R ⁹² and R ⁹³ to each other include the same ring formed by bonding of R ² and R ³ to each other.

Examples of the ring formed by bonding R ¹⁰² and R ¹⁰³ to each other include the same ring formed by bonding of R ² and R ³ to each other.

Examples of the ring formed by bonding of R ¹¹² and R ¹¹³ to each other include the same ring formed by bonding of R ² and R ³ to each other.

Examples of the ring formed by bonding of R ¹ and R ² to each other are the same as the ring formed by bonding of R ^Y1 and R ^Y2 in the formula (Y) to each other.

The ring formed by combining R ¹ and R ² with each other is usually a 3- to 10-membered ring, preferably a 5- to 7-membered ring, and more preferably a 5-membered or 6-membered ring.

The ring formed by combining R ¹ and R ² with each other may have a substituent, and examples thereof include the same substituents that the ring W ² to W ¹² may have.

Examples of the ring formed by bonding R ⁴¹ and R ⁴² to each other include the same ring formed by bonding of R ¹ and R ² to each other.

Examples of the ring formed by bonding R ⁵¹ and R ⁵² to each other include the same ring formed by bonding of R ¹ and R ² to each other.

Examples of the ring formed by bonding R ⁶¹ and R ⁶² to each other include the same ring formed by bonding of R ¹ and R ² to each other.

Examples of the ring formed by bonding R ⁹¹ and R ⁹² to each other include the same ring formed by bonding of R ¹ and R ² to each other.

Examples of the ring formed by bonding R ¹⁰¹ and R ¹⁰² to each other are the same as the ring formed by bonding R ¹ and R ² to each other.

Examples of the ring formed by bonding R ¹¹¹ and R ¹¹² to each other include the same ring formed by bonding of R ¹ and R ² to each other.

The divalent linking group represented by R ⁶ , R ⁷ and R ⁸ represents a divalent aliphatic hydrocarbon group having 1 to 18 carbon atoms which may have a substituent or a divalent aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent. -CH ₂ - contained in the divalent aliphatic hydrocarbon group and the divalent aromatic hydrocarbon group is -O-, -S-, -NR ^1B - (R ^1B represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms), - It may be substituted with CO-, -SO ₂ -, -SO-, -PO ₃ -.

Moreover, as a substituent which the said divalent aliphatic hydrocarbon group and the divalent aromatic hydrocarbon group may have, a halogen atom, a hydroxyl group, a carboxy group, an amino group, etc. are mentioned.

The divalent linking group represented by R ⁶ , R ⁷ and R ⁸ is preferably a divalent aliphatic hydrocarbon group having 1 to 18 carbon atoms which may each independently have a substituent, and is preferably a divalent aliphatic hydrocarbon group having 1 to 12 carbon atoms which may have a substituent. It is more preferable that it is an aliphatic hydrocarbon group.

Specific examples of the divalent linking group represented by R ⁶ , R ⁷ and R ⁸ include the linking groups described below. In the formula, * represents the number of bonds.

R ⁶ and R ⁷ are each independently preferably a divalent aliphatic hydrocarbon group having 1 to 18 carbon atoms which may have a substituent or a linking group represented by the following formula, and a divalent aliphatic group having 1 to 12 carbon atoms which may have a substituent It is more preferable that it is a hydrocarbon group or a coupling group represented by the following formula.

R ⁸ is preferably a divalent aliphatic hydrocarbon group having 1 to 18 carbon atoms which may have a substituent or a linking group represented by the following formula. In the formula, * represents the number of bonds.

Examples of the trivalent linking group represented by R ⁹ and R ¹⁰ include a trivalent aliphatic hydrocarbon group having 1 to 18 carbon atoms which may each independently have a substituent or a trivalent aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent. . -CH ₂ - contained in the trivalent aliphatic hydrocarbon group is -O-, -S-, -CS-, -CO-, -SO-, -NR ^11B - (R ^11B is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms) may be substituted with ).

A halogen atom, a hydroxyl group, a carboxy group, an amino group, etc. are mentioned as a substituent which the said trivalent aliphatic hydrocarbon group and the said trivalent aromatic hydrocarbon group may have.

The trivalent linking group represented by R ⁹ and R ¹⁰ is preferably a trivalent aliphatic hydrocarbon group having 1 to 12 carbon atoms which may each independently have a substituent.

Specific examples of the trivalent linking group represented by R ⁹ and R ¹⁰ include the linking groups described below. In the formula, * represents the number of bonds.

Examples of the tetravalent linking group represented by R ¹¹ include a tetravalent aliphatic hydrocarbon group having 1 to 18 carbon atoms which may have a substituent or a tetravalent aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent. -CH ₂ - contained in the tetravalent aliphatic hydrocarbon group is -O-, -S-, -CS-, -CO-, -SO-, -NR ^11C - (R ^11C is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms) may be substituted with ).

A halogen atom, a hydroxyl group, a carboxy group, an amino group, etc. are mentioned as a substituent which the said tetravalent aliphatic hydrocarbon group and the said tetravalent aromatic hydrocarbon group may have.

The tetravalent linking group represented by R ¹¹ is preferably a tetravalent aliphatic hydrocarbon group having 1 to 12 carbon atoms which may each independently have a substituent.

Specific examples of the tetravalent linking group represented by R ¹¹ include the linking groups described below. In the formula, * represents the number of bonds.

It is preferable that it is a C1-C15 alkyl group, and, as for R< ¹ >, it is more preferable that it is a C1-C10 alkyl group.

It is preferable that it is a C1-C15 alkyl group, and, as for R< ² >, it is more preferable that it is a C1-C10 alkyl group.

R ¹ and R ² are preferably linked to each other to form a ring, more preferably form an aliphatic ring, more preferably an aliphatic ring having no unsaturated bond, and a pyrrolidine ring or piperidine ring structure Especially preferred.

R ³ is a nitro group, a cyano group, a halogen atom, -OCF ₃ , -SCF ₃ , -SF ₅ , -SF ₃ , a fluoroalkyl group (preferably having 1 to 25 carbon atoms), a fluoroaryl group (preferably having 1 to 25 carbon atoms) 6-18), -CO-OR ^111A or -SO ₂ -R ^112A (R ^111A and R ^112A each independently represent an alkyl group having 1 to 24 carbon atoms) is preferable;

Cyano group, fluorine atom, chlorine atom, -OCF ₃ , -SCF ₃ , fluoroalkyl group, -CO-OR ^111A or -SO ₂ -R ^112A (R ^111A and R ^112A are each independently the number of carbon atoms that may have a halogen atom 1 to 24 alkyl groups are shown.), more preferably a cyano group or a fluorine atom, and particularly preferably a cyano group.

R ⁴ and R ⁵ are each independently a nitro group, a cyano group, a halogen atom, -OCF ₃ , -SCF ₃ , -SF ₅ , -SF ₃ , a fluoroalkyl group, a fluoroaryl group, -CO-OR ²²² or - SO ₂ -R ²²² (R ²²² is preferably a hydrogen atom, an optionally substituted alkyl group having 1 to 25 carbon atoms, or an optionally substituted aromatic hydrocarbon group having 6 to 18 carbon atoms);

Nitro group, cyano group, fluorine atom, chlorine atom, -OCF ₃ , -SCF ₃ , fluoroalkyl group, -CO-OR ²²² or -SO ₂ -R ²²² (R ²²² is a hydrogen atom, optionally having 1 carbon atom) It is more preferable that it is a C6-C18 aromatic hydrocarbon group which may have a -25 alkyl group or a substituent.),

Cyano group, -CO-OR ²²² or -SO ₂ -R ²²² (R ²²² represents a hydrogen atom, an optionally substituted alkyl group having 1 to 25 carbon atoms, or an optionally substituted aromatic hydrocarbon group having 6 to 18 carbon atoms.) It is more preferable that it is, and it is especially preferable that it is a cyano group.

At least one of R ⁴ and R ⁵ is preferably a cyano group, R ⁴ is a cyano group, and R ⁵ is a cyano group, -CO-OR ²²² or -SO ₂ -R ²²² (R2 ²² is a hydrogen atom, a substituent It represents the C1-C25 alkyl group which it may have, or the C6-C18 aromatic hydrocarbon group which may have a substituent.) is more preferable.

R ⁴ and R ⁵ preferably have the same structure.

It is preferable that R ⁴ and R ⁵ together be a cyano group.

R ⁴¹ , R ⁵¹ , R ⁶¹ , R ⁹¹ , R ¹⁰¹ and R ¹¹¹ are each independently preferably an alkyl group having 1 to 15 carbon atoms, more preferably an alkyl group having 1 to 10 carbon atoms.

R ¹² , R ⁴² , R ⁵² , R ⁶² , R ⁷² , R ⁸² , R ⁹² , R ¹⁰² and R ¹¹² are each independently preferably an alkyl group having 1 to 15 carbon atoms, and an alkyl group having 1 to 10 carbon atoms. more preferably.

R ⁴¹ and R ⁴² are preferably linked to each other to form a ring, more preferably an aliphatic ring, still more preferably an aliphatic ring having no unsaturated bond, particularly preferably a pyrrolidine ring or a piperidine ring It is desirable to have a structure.

R ⁵¹ and R ⁵² are preferably linked to each other to form a ring, more preferably an aliphatic ring, still more preferably an aliphatic ring having no unsaturated bond, particularly preferably a pyrrolidine ring or a piperidine ring It is desirable to have a structure.

R ⁶¹ and R ⁶² are preferably linked to each other to form a ring, more preferably an aliphatic ring, still more preferably an aliphatic ring having no unsaturated bond, particularly preferably a pyrrolidine ring or a piperidine ring It is desirable to have a structure.

R ⁹¹ and R ⁹² are preferably linked to each other to form a ring, more preferably an aliphatic ring, still more preferably an aliphatic ring having no unsaturated bond, particularly preferably a pyrrolidine ring or a piperidine ring It is desirable to have a structure.

R ¹⁰¹ and R ¹⁰² are preferably linked to each other to form a ring, more preferably an aliphatic ring, still more preferably an aliphatic ring having no unsaturated bond, particularly preferably a pyrrolidine ring or a piperidine ring It is desirable to have a structure.

R ¹¹¹ and R ¹¹² are preferably linked to each other to form a ring, more preferably an aliphatic ring, still more preferably an aliphatic ring having no unsaturated bond, particularly preferably a pyrrolidine ring or a piperidine ring It is desirable to have a structure.

R ¹³ , R ²³ , R ³³ , R ⁴³ , R ⁵³ , R ⁶³ , R ⁷³ , R ⁸³ , R ⁹³ , R ¹⁰³ and R ¹¹³ are each independently a nitro group; cyano group; halogen atom; -OCF ₃ ; -SCF ₃ ; -SF ₅ ; -SF ₃ ; a fluoroalkyl group having 1 to 25 carbon atoms; a fluoroaryl group having 6 to 18 carbon atoms; -CO-OR ^111A or -SO ₂ -R ^112A (R ^111A and R ^112A each independently represent an alkyl group having 1 to 24 carbon atoms which may have a halogen atom.)

cyano group; fluorine atom; chlorine atom; -OCF ₃ ; -SCF ₃ ; a fluoroalkyl group having 1 to 12 carbon atoms; It is more preferable that -CO-OR ^111A or -SO ₂ -R ^112A (R ^111A and R ^112A each independently represent an alkyl group having 1 to 24 carbon atoms which may have a halogen atom),

It is especially preferable that it is a cyano group.

R ¹⁴ , R ²⁴ , R ³⁴ , R ⁴⁴ , R ⁵⁴ , R ⁶⁴ , R ⁷⁴ , R ⁸⁴ , R ⁹⁴ , R ¹⁰⁴ , R ¹¹⁴ , R ¹⁵ , R ²⁵ , R ³⁵ , R ⁷⁵ and R ⁸⁵ are each independently a nitro group, a cyano group, a halogen atom, -OCF ₃ , -SCF ₃ , -SF ₅ , -SF ₃ , -CO-OR ²²² , -SO ₂ -R ²²² (R ²²² is the number of carbon atoms that may have a halogen atom an alkyl group of 1 to 25 is preferred), a fluoroalkyl group having 1 to 25 carbon atoms, or a fluoroaryl group having 6 to 18 carbon atoms;

A nitro group, a cyano group, a fluorine atom, a chlorine atom, -OCF ₃ , -SCF ₃ , a fluoroalkyl group, -CO-OR ²²² or -SO ₂ -R ²²² (R ²²² represents 1 to 25 carbon atoms which may have a halogen atom) represents an alkyl group of ) is more preferable,

It is more preferably a cyano group, -CO-OR ²²² or -SO ₂ -R ²²² (R ²²² represents an alkyl group having 1 to 25 carbon atoms which may have a halogen atom.)

It is especially preferable that it is a cyano group.

It is preferable that R ¹⁴ and R ¹⁵ have the same structure.

It is preferable that R ²⁴ and R ²⁵ have the same structure.

It is preferable that R ³⁴ and R ³⁵ have the same structure.

It is preferable that R ⁷⁴ and R ⁷⁵ have the same structure.

It is preferable that R ⁸⁴ and R ⁸⁵ have the same structure.

The compound represented by formula (I) (hereinafter sometimes referred to as compound (I)) is a compound represented by formula (I-1A), a compound represented by formula (I-2A), or a compound represented by formula (I-3A). It is more preferable that it is any one of the compounds represented by ).

[Wherein, Rx ₁ , Rx ₂ , Rx ₃ , Rx ₄ , Rx ₅ , Rx ₆ , Rx ₇ and Rx ₈ each independently represent a hydrogen atom or a substituent.]

Examples of the substituent represented by Rx ₁ to Rx ₈ include the same substituents that the ring W ¹ may have.

As compound (I), the compound described below is mentioned, for example.

Compound (I) is a formula (1-1) to formula (1-4), formula (1-7), formula (1-8), formula (1-10), formula (1-12), formula (1) -20) to formula (1-25), formula (1-54) to formula (1-57), formula (1-59), formula (1-63) to formula (1-68), formula (1- 70) to formula (1-78), formula (1-80), formula (1-124) to formula (1-132), formula (1-135), formula (1-137) to formula (1-142) ), a compound represented by the formulas (1-158) to (1-172), (1-218) to (1-227),

Formula (1-4), Formula (1-7), Formula (1-10), Formula (1-12), Formula (1-20), Formula (1-22), Formula (1-54), Formula (1-55), formula (1-56), formula (1-59), formula (1-63) to formula (1-65), formula (1-66), formula (1-71), formula ( 1-124), Formula (1-125), Formula (1-126), Formula (1-128), Formula (1-131), Formula (1-158), Formula (1-160), Formula (1) -164), formula (1-169), it is more preferable that it is a compound represented by formula (1-218) - formula (1-228),

Formula (1-55), Formula (1-56), Formula (1-59), Formula (1-64), Formula (1-125), Formula (1-218) to Formula (1-228) It is more preferable that it is a compound which becomes

Examples of the compound represented by the formula (II) (hereinafter sometimes referred to as compound (II)) include the compounds described below.

As compound (II), Formula (2-1), Formula (2-2), Formula (2-5) - Formula (2-12), Formula (2-24) - Formula (2-28), Formula (2) -32), formula (2-33), formula (2-38) - formula (2-44), formula (2-70), formula (2-71), formula (2-103), formula (2- 104), preferably a compound represented by Formula (2-1), Formula (2-2), Formula (2-5) to Formula (2-10), Formula (2-103), Formula (2- 104), a compound represented by a formula (2-105) or a formula (2-106) is more preferable.

Examples of the compound represented by the formula (III) (hereinafter sometimes referred to as compound (III)) include the compounds described below.

Examples of the compound represented by the formula (IV) (hereinafter sometimes referred to as compound (IV)) include the compounds described below.

Examples of the compound represented by the formula (V) (hereinafter sometimes referred to as compound (V)) include the compounds described below.

As compound (V), Formula (5-1) - Formula (5-3), Formula (5-6), Formula (5-7), Formula (5-9), Formula (5-15), Formula (5) -21), formula (5-23), formula (5-25), formula (5-26), formula (5-32), formula (5-36), a compound represented by formula (5-38) It is preferable, and it is more preferable that it is a compound represented by Formula (5-1) - Formula (5-3), Formula (5-21), Formula (5-25), Formula (5-36).

Examples of the compound represented by the formula (VI) (hereinafter sometimes referred to as compound (VI)) include the compounds described below.

As compound (VI), Formula (6-1), Formula (6-2), Formula (6-4), Formula (6-5), Formula (6-7), Formula (6-8), Formula (6) -9), Formula (6-12), Formula (6-15), Formula (6-18), Formula (6-19), Formula (6-22), Formula (6-23), Formula (6- 50), a compound represented by the formula (6-57), the formula (6-69), the formula (6-80), the formula (6-85), and the formula (6-94), and the formula (6- 1), the compound represented by the formula (6-2), the formula (6-4), the formula (6-8), the formula (6-15), the formula (6-22), the formula (6-80) more preferably.

Examples of the compound represented by the formula (VII) (hereinafter sometimes referred to as compound (VII)) include the compounds described below.

As compound (VII), formula (7-1) - formula (7-9), formula (7-12), formula (7-14), formula (7-17), formula (7-42) - formula (7) -44), it is preferable that it is a compound represented by Formula (7-57), It is more preferable that it is a compound represented by Formula (7-1) - Formula (7-8).

Examples of the compound represented by the formula (VIII) (hereinafter sometimes referred to as compound (VIII)) include the compounds described below.

As compound (VIII), Formula (8-1), Formula (8-2), Formula (8-4), Formula (8-5), Formula (8-11), Formula (8-13) - Formula (8) -17), Formula (8-25), Formula (8-26), Formula (8-47), Formula (8-48) is preferably a compound represented by Formula (8-1), Formula (8) It is more preferable that it is a compound represented by -4), a formula (8-5), a formula (8-15), a formula (8-17), and a formula (8-25).

<Method for producing compound (I)>

Compound (I) is prepared in the same manner as in the preparation method of compound (Y), except that compound (Y-A) is replaced with a compound represented by formula (I-A) (hereinafter sometimes referred to as compound (I-A).) can

[Wherein, the rings W ¹ and R ¹ to R ³ have the same meanings as above.]

As compound (I-A), the compound etc. described below are mentioned, for example.

Compound (I-A) is a compound represented by formula (I-C) (hereinafter sometimes referred to as compound (I-C)) and a compound represented by formula (I-D) (hereinafter sometimes referred to as compound (I-D).) can be obtained by reacting

[Wherein, rings W ¹ , R ¹ , R ² and R ³ have the same meanings as above. E ₁ represents a leaving group.]

Examples of the leaving group represented by E ₁ include a halogen atom, p-toluenesulfonyl group, and trifluoromethylsulfonyl group.

The reaction of the compound (I-C) and the compound (I-D) is carried out by mixing the compound (I-C) and the compound (I-D).

The usage-amount of compound (I-D) is 0.1-5 mol normally with respect to 1 mol of compound (I-C), and it is preferable that it is 0.5-2 mol.

The reaction between compound (I-C) and compound (I-D) may be carried out in the presence of a solvent. Examples of the solvent include the same solvents used for the reaction of the compound (Y-C) and the compound (Y-D).

The reaction time between compound (I-C) and compound (I-D) is usually 0.1 to 10 hours.

The reaction temperature of compound (I-C) and compound (I-D) is usually -50 to 150°C.

As compound (I-C), the compound described below is mentioned, for example.

A commercial item may be used for compound (I-4), and the thing similar to the specific example of compound (Y-D) is mentioned.

Compound (I-C) is a compound represented by formula (I-E) (hereinafter sometimes referred to as compound (I-E)) and a compound represented by formula (I-F) (hereinafter sometimes referred to as compound (I-F).) It can be obtained by reacting

[Wherein, W ¹ , R ¹ and R ² have the same meanings as above.]

The reaction of compound (I-E) and compound (I-F) is carried out by mixing compound (I-E) and compound (I-F).

The usage-amount of compound (I-F) is 0.1-5 mol normally with respect to 1 mol of compound (I-E), and it is preferable that it is 0.5-2 mol.

The reaction between compound (I-E) and compound (I-F) may be carried out in the presence of a solvent. Examples of the solvent include the same solvents used for the reaction between compound (Y-E) and compound (Y-F).

The reaction time between compound (I-E) and compound (I-F) is usually 0.1 to 10 hours.

The reaction temperature of compound (I-E) and compound (I-F) is usually -50 to 150°C.

As compound (I-E), the compound etc. described below are mentioned, for example.

Examples of the compound (I-F) include the same compounds as those of the compound (Y-F).

Compound (I), instead of using the above-described compound (I-A) and compound (Y-B), a compound represented by the formula (I-G) (hereinafter sometimes referred to as compound (I-G)) and compound (I-F) It can also be obtained by using it.

[In formula (IG), rings W ¹ , R ³ , R ⁴ and R ⁵ have the same meanings as above.]

As compound (I-G), the compound described below is mentioned, for example.

<Method for producing compound (II) to compound (VIII)>

Compound (II) can be obtained, for example, by reacting 2 molar equivalents of compound (I-G) with 1 molar equivalent of the compound represented by formula (II-1).

[Wherein, R ² , R ¹² and R ⁶ have the same meanings as above.]

As a compound represented by Formula (II-1), the compound etc. described below are mentioned, for example.

Compound (III) can be obtained, for example, by reacting 2 molar equivalents of compound (I-G) with 1 molar equivalent of the compound represented by formula (III-1).

[Wherein, ring W ¹¹¹ has the same meaning as above.]

As a compound represented by Formula (III-1), the compound etc. which were described below are mentioned, for example.

Compound (IV) can be obtained, for example, by reacting 2 molar equivalents of compound (I-G) with 1 molar equivalent of the compound represented by formula (IV-1).

[In the formula, ring W ¹¹² , ring W ¹¹³ , and R ⁷ have the same meaning as above.]

Examples of the compound represented by the formula (IV-1) include the compounds described below.

Compound (V) can be obtained, for example, by reacting 2 molar equivalents of compound (I-A) with 1 molar equivalent of the compound represented by formula (V-1).

[Wherein, R ⁴ , R ⁸ and R ⁴⁴ have the same meaning as above.]

As a compound represented by Formula (V-1), the compound etc. described below are mentioned, for example.

Compound (VI) can be obtained, for example, by reacting 3 molar equivalents of compound (I-A) with 1 molar equivalent of the compound represented by formula (VI-1).

[Wherein, R ⁴ , R ⁸ , R ⁵⁴ and R ⁶⁴ have the same meaning as above.]

Examples of the compound represented by the formula (VI-1) include the compounds described below.

Compound (VII) can be obtained, for example, by reacting 3 molar equivalents of compound (I-G) with 1 molar equivalent of the compound represented by formula (VII-1).

[Wherein, R ² , R ¹⁰ , R ⁷² and R ⁸² have the same meaning as above.]

Examples of the compound represented by the formula (VII-1) include the compounds described below.

Compound (VIII) can be obtained, for example, by reacting 4 molar equivalents of compound (I-A) with 1 molar equivalent of the compound represented by formula (VIII-1).

[Wherein, R ⁴ , R ¹¹ , R ⁹⁴ , R ¹⁰⁴ and R ¹¹⁴ have the same meaning as above.]

Examples of the compound represented by the formula (VIII-1) include the compounds described below.

Content of the light selective absorption compound (B) is 0.01-50 mass parts normally with respect to 100 mass parts of resin (A), It is preferable that it is 0.1-20 mass parts, It is more preferable that it is 0.5-10 mass parts, It is especially preferable is 1.0 to 5 parts by mass.

<Light selective absorption resin (C)>

The light-selective absorption resin (C) is a resin showing maximum absorption at a wavelength of 300 nm or more and less than 360 nm. The light-selective absorption resin (C) preferably exhibits maximum absorption at a wavelength of 320 nm or more and 355 nm or less, and more preferably exhibits maximum absorption at a wavelength of 330 nm or more and 350 nm or less.

In order for the light-selective absorption resin (C) to show maximum absorption at a wavelength of 300 nm or more and less than 360 nm, a structural unit derived from a monomer exhibiting maximum absorption at a wavelength of 300 nm or more and less than 360 nm (hereinafter referred to as structural unit (C)) It is preferable to include). The monomer exhibiting maximum absorption at a wavelength of 300 nm or more and less than 360 nm is preferably a monomer exhibiting maximum absorption at a wavelength of 320 nm or more and 355 nm or less, and a monomer exhibiting maximum absorption at a wavelength of 330 nm or more and 350 nm or less. more preferably.

Monomers showing maximum absorption at a wavelength of 300 nm or more and less than 360 nm are, for example, a monomer having a benzotriazole skeleton, a monomer having a benzoimidazole skeleton, a monomer having a triazine skeleton, a monomer having a benzophenone skeleton, cyanoacryl The monomer etc. which have a rate skeleton are mentioned. It is preferable that the monomer which shows maximum absorption at a wavelength of 300 nm or more and wavelength less than 360 nm is a monomer which has a benzophenone skeleton, a monomer which has a benzotriazole skeleton, or a monomer which has a triazine skeleton.

A monomer exhibiting maximum absorption at a wavelength of 300 nm or more and less than 360 nm at a wavelength usually has a polymerizable group in the molecule. Examples of the polymerizable group in the monomer exhibiting maximum absorption at a wavelength of 300 nm or more and less than 360 nm include a vinyl group, α-methylvinyl group, acryloyl group, methacryloyl group, allyl group, styryl group, (meth)acrylamide It is preferable that they are ethylenically unsaturated groups, such as group and (meth)acryloyloxy group.

The monomer exhibiting maximum absorption at a wavelength of 300 nm or more and less than 360 nm at a wavelength includes, for example, the monomers described below.

2-[2-(2,4-dihydroxyphenyl)-2H-benzotriazol-5-yloxy]ethyl methacrylate;

2-[2-(4-ethoxy-2-hydroxyphenyl)-2H-benzotriazol-5-yloxy]ethyl methacrylate;

2-[2-(4-butoxy-2-hydroxyphenyl)-2H-benzotriazol-5-yloxy]ethyl methacrylate;

2-[2-(4-benzoyloxy-2-hydroxyphenyl)-2H-benzotriazol-5-yloxy]ethyl methacrylate;

4-[2-(2,4-dihydroxyphenyl)-2H-benzotriazol-5-yloxy]butyl methacrylate;

4-[2-(4-ethoxy-2-hydroxyphenyl)-2H-benzotriazol-5-yloxy]butyl methacrylate;

4-[2-(4-butoxy-2-hydroxyphenyl)-2H-benzotriazol-5-yloxy]butyl methacrylate;

4-[2-(2-hydroxy-4-octyloxyphenyl)-2H-benzotriazol-5-yloxy]butyl methacrylate;

4-[2-(4-benzoyloxy-2-hydroxyphenyl)-2H-benzotriazol-5-yloxy]butyl methacrylate;

2-[2-(2-hydroxy-4-octyloxyphenyl)-2H-benzotriazol-5-yloxy]ethyl methacrylate;

2-[2-(4-octyloxy-2-hydroxyphenyl)-2H-benzotriazol-5-yloxy]ethyl methacrylate;

2-[2-(4-methoxy-5-tertbutyl-2-hydroxyphenyl)-2H-benzotriazol-5-yloxy]ethyl methacrylate;

2-[2-(4-methoxy-3-tertbutyl-2-hydroxyphenyl)-2H-benzotriazol-5-yloxy]ethyl methacrylate;

2-[2-(4-methoxy-3-methyl-2-hydroxyphenyl)-2H-benzotriazol-5-yloxy]ethyl methacrylate;

2-[2-hydroxy-5-(methacryloyloxyethyl)phenyl]-2H-benzotriazole;

2-[2-hydroxy-5-(methacryloyl)phenyl]-2H-benzotriazole;

2-[2-hydroxy-5-(methacryloyloxypropyl)phenyl]-5-chloro-2H-benzotriazole;

2-[2-hydroxy-5-(methacryloyloxypropyl)phenyl]-2H-benzotriazole;

N-[3-benzotriazol-2-yl-2-hydroxy-5-(1,1,3,3-tetramethylbutyl)-benzoyl]-2-methylmethacrylamide;

2-[2-(2,4-dihydroxyphenyl)-2H-benzotriazol-5-yloxy]ethyl acrylate;

2-[2-(4-ethoxy-2-hydroxyphenyl)-2H-benzotriazol-5-yloxy]ethyl acrylate;

2-[2-(4-butoxy-2-hydroxyphenyl)-2H-benzotriazol-5-yloxy]ethyl acrylate;

2-[2-(4-benzoyloxy-2-hydroxyphenyl)-2H-benzotriazol-5-yloxy]ethyl acrylate;

4-[2-(2,4-dihydroxyphenyl)-2H-benzotriazol-5-yloxy]butyl acrylate;

4-[2-(4-ethoxy-2-hydroxyphenyl)-2H-benzotriazol-5-yloxy]butyl acrylate;

4-[2-(4-butoxy-2-hydroxyphenyl)-2H-benzotriazol-5-yloxy]butyl acrylate;

4-[2-(2-hydroxy-4-octyloxyphenyl)-2H-benzotriazol-5-yloxy]butyl acrylate;

2-[2-(2-hydroxy-4-octyloxyphenyl)-2H-benzotriazol-5-yloxy]ethyl acrylate;

4-[2-(4-benzoyloxy-2-hydroxyphenyl)-2H-benzotriazol-5-yloxy]butyl acrylate;

2-[2-(4-octyloxy-2-hydroxyphenyl)-2H-benzotriazol-5-yloxy]ethyl acrylate;

2-[2-(4-methoxy-5-tertbutyl-2-hydroxyphenyl)-2H-benzotriazol-5-yloxy]ethyl acrylate;

2-[2-(4-methoxy-3-tertbutyl-2-hydroxyphenyl)-2H-benzotriazol-5-yloxy]ethyl acrylate;

2-[2-(4-methoxy-3-methyl-2-hydroxyphenyl)-2H-benzotriazol-5-yloxy]ethyl acrylate;

2-[2-hydroxy-5-(acryloyloxyethyl)phenyl]-2H-benzotriazole;

2-[2-hydroxy-5-(acryloyl)phenyl]-2H-benzotriazole;

2-[2-hydroxy-5-(methacryloyloxypropyl)phenyl]-5-chloro-2H-benzotriazole;

2-[2-hydroxy-5-(methacryloyloxypropyl)phenyl]-2H-benzotriazole;

N-[3-benzotriazol-2-yl-2-hydroxy-5-(1,1,3,3-tetramethylbutyl)-benzoyl]-2-methylacrylamide;

2-hydroxy-4-acryloyloxybenzophenone,

2-hydroxy-4-methacryloyloxybenzophenone,

2-hydroxy-4-(2-acryloyloxy)ethoxybenzophenone;

2-hydroxy-4-(2-methacryloyloxy)ethoxybenzophenone;

2-hydroxy-4-(2-methyl-2-acryloyloxy)ethoxybenzophenone;

2,4-diphenyl-6-[2-hydroxy-4-(2-methacryloyloxyethoxy)phenyl]-s-triazine;

2,4-diphenyl-6-[2-hydroxy-4-(2-acryloyloxyethoxy)phenyl]-s-triazine;

2,4-bis(2-methylphenyl)-6-[2-hydroxy-4-(3-methacryloyloxy-2-hydroxypropyloxy)phenyl]-s-triazine;

2,4-bis(2-methylphenyl)-6-[2-hydroxy-4-(3-acryloyloxy-2-hydroxypropyloxy)phenyl]-s-triazine;

2,4-bis(2-methoxyphenyl)-6-[2-hydroxy-4-(2-acryloyloxyethoxy)phenyl]-s-triazine;

2,4-bis(2-methoxyphenyl)-6-[2-hydroxy-4-(2-methacryloyloxyethoxy)phenyl]-s-triazine;

2,4-bis(2-ethylphenyl)-6-[2-hydroxy-4-(2-methacryloyloxyethoxy)phenyl]-s-triazine;

2,4-bis(2-ethylphenyl)-6-[2-hydroxy-4-(2-acryloyloxyethoxy)phenyl]-s-triazine;

2,4-bis(2-ethoxyphenyl)-6-[2-hydroxy-4-(2-methacryloyloxyethoxy)phenyl]-s-triazine;

2,4-bis(2-ethoxyphenyl)-6-[2-hydroxy-4-(2-acryloyloxyethoxy)phenyl]-s-triazine and the like.

The compound shown below may be sufficient as the monomer which shows maximum absorption at a wavelength of 300 nm or more and less than 360 nm of wavelength.

A monomer having a maximum absorption wavelength with a wavelength of 300 nm or more and less than 360 nm may be a commercially available product, specifically, "RUVA-93" (Otsuka Chemical Co., Ltd.), "CHISORB 5687" (Double bond Chemical), " Tinuvin R 796" (BASF) etc. are mentioned.

The light selective absorption resin (C) may be a copolymer containing the structural unit (C) or a homopolymer containing the structural unit (C). It is preferable that the light selective absorption resin (C) is a copolymer containing a structural unit (C).

It is preferable that the light selective absorption resin (C) contains structural units other than a structural unit (C). Examples of structural units other than the structural unit (C) include structural units derived from monomers forming the above-mentioned resin (A). Specifically, the structural unit derived from the (meth)acrylic acid ester represented by the above formula (a), the structural unit derived from the monomer having a polar functional group, the structural unit derived from the styrene-based monomer, and the vinyl-based monomer and structural units derived from the above-described (meth)acrylamide-based monomers.

The structural unit other than the structural unit (C) is preferably a structural unit derived from (meth)acrylic acid ester represented by the above formula (a), a structural unit derived from a monomer having a polar functional group, etc. The structural unit derived from the (meth)acrylic acid ester represented by a), the monomer which has a hydroxyl group, the structural unit derived from the (meth)acrylamide type monomer, etc. are more preferable. In particular, it is preferable that it is a structural unit derived from normal butyl acrylate, methyl acrylate, 2-ethylhexyl acrylate, normal octyl acrylate, etc.

The light selective absorption resin (C) preferably contains 0.1 to 90 mass% of the structural unit (C) with respect to all the structural units, more preferably 1 to 75 mass%, and contains 5 to 60 mass% It is more preferable, and it is especially preferable to contain 10-50 mass %.

Specific examples of the light-selective absorption resin (C) include a resin described in JP 2012-25811 A , a resin including the structural units described below, and the like.

The light selective absorption resin (C) may be a commercially available product or may be synthesized by a known method (eg, JP 2012-25811 A ).

As a commercial item of the light selective absorption resin (C), the Vana resin UVR series (Shin-Nakamura Chemical Co., Ltd.) etc. are mentioned.

Content of light selective absorption resin (C) is 1-50 mass parts normally with respect to 100 mass parts of resin (A), It is preferable that it is 5-40 mass parts, It is more preferable that it is 7-30 mass parts, It is especially preferable is 10 to 25 parts by weight.

The content ratio (mass ratio) of the light selective absorption resin (C) and the light selective absorption compound (B) is usually light selective absorption resin (C)/light selective absorption compound (B) = 100/100 to 100/30, 100 It is preferable that it is /90-100/25.

The pressure-sensitive adhesive composition of the present invention may further contain a radical curable component (E), an initiator (D), and a crosslinking agent (F).

<Radically curable component (E)>

Examples of the radical curable component (E) include a monomer or an oligomer that is cured by a radical polymerization reaction.

Examples of the radical-curable component (E) include monofunctional or polyfunctional (meth)acrylate-based compounds, styrene-based compounds, and vinyl-based compounds.

The adhesive composition of this invention may contain 2 or more types of radical curable component (E).

As the (meth)acrylate-based compound, a (meth)acrylate monomer having at least one (meth)acryloyloxy group in the molecule, a (meth)acrylamide monomer, and at least two (meth)acryloyl groups in the molecule (meth)acryloyl group containing compounds, such as a (meth)acryl oligomer, are mentioned. The (meth)acryl oligomer is preferably a (meth)acrylate oligomer having at least two (meth)acryloyloxy groups in the molecule. A (meth)acrylic-type compound may be used individually by 1 type, and may use 2 or more types together.

As a (meth)acrylate monomer, the monofunctional (meth)acrylate monomer which has one (meth)acryloyloxy group in a molecule|numerator, and the bifunctional (meth)acrylate which has two (meth)acryloyloxy groups in a molecule|numerator Monomers and polyfunctional (meth)acrylate monomers having three or more (meth)acryloyloxy groups in the molecule are exemplified.

Alkyl (meth)acrylate is mentioned as a monofunctional (meth)acrylate monomer. Alkyl (meth)acrylate WHEREIN: When carbon number of the alkyl group is 3 or more, any of linear, branched, and cyclic|annular form may be sufficient. Examples of the alkyl (meth) acrylate include methyl (meth) acrylate, ethyl (meth) acrylate, isopropyl (meth) acrylate, butyl (meth) acrylate, isobutyl (meth) acrylate, t-butyl (meth) acrylate ) acrylate and 2-ethylhexyl (meth)acrylate.

Moreover, as a monofunctional (meth)acrylate monomer, Aralkyl (meth)acrylates, such as benzyl (meth)acrylate; (meth)acrylates of terpene alcohols such as isobornyl (meth)acrylate; (meth)acrylates having a tetrahydrofurfuryl structure such as tetrahydrofurfuryl (meth)acrylate; A cycloalkyl group at the alkyl group moiety, such as cyclohexyl (meth) acrylate, cyclohexylmethyl methacrylate, dicyclopentanyl acrylate, dicyclopentenyl (meth) acrylate, and 1,4-cyclohexanedimethanol monoacrylate (meth)acrylate having; aminoalkyl (meth)acrylates such as N,N-dimethylaminoethyl (meth)acrylate; 2-phenoxyethyl (meth) acrylate, dicyclopentenyloxyethyl (meth) acrylate, ethyl carbitol (meth) acrylate, phenoxy polyethylene glycol (meth) acrylate having an ether bond in the alkyl moiety (meth)acrylate, etc. are also mentioned.

Moreover, as a monofunctional (meth)acrylate monomer, the monofunctional (meth)acrylate which has a hydroxyl group in an alkyl part; and monofunctional (meth)acrylates having a carboxyl group in the alkyl moiety. Examples of the monofunctional (meth)acrylate having a hydroxyl group in the alkyl moiety include 2-hydroxyethyl (meth)acrylate, 2- or 3-hydroxypropyl (meth)acrylate, and 4-hydroxybutyl (meth)acrylate. and 2-hydroxy-3-phenoxypropyl (meth)acrylate, trimethylolpropane mono(meth)acrylate, and pentaerythritol mono(meth)acrylate. Examples of the monofunctional (meth)acrylate having a carboxyl group in the alkyl moiety include 2-carboxyethyl (meth)acrylate, ω-carboxy-polycaprolactone (n=2) mono(meth)acrylate, 1-[2-( Meth)acryloyloxyethyl]phthalic acid, 1-[2-(meth)acryloyloxyethyl]hexahydrophthalic acid, 1-[2-(meth)acryloyloxyethyl]succinic acid, 4-[2-( meth)acryloyloxyethyl] trimellitic acid, N-(meth)acryloyloxy-N',N'-dicarboxymethyl-p-phenylenediamine, etc. are mentioned.

The (meth)acrylamide monomer is preferably (meth)acrylamide having a substituent at the N-position. A typical example of the substituent at the N-position is an alkyl group, but may form a ring together with a nitrogen atom of (meth)acrylamide, and this ring is an oxygen atom in addition to a carbon atom and a nitrogen atom of (meth)acrylamide. may have as a ring member. Further, a substituent such as alkyl or oxo (=O) may be bonded to the carbon atom constituting the ring.

As N-substituted (meth)acrylamide, N-methyl (meth)acrylamide, N-ethyl (meth)acrylamide, N-isopropyl (meth)acrylamide, N-n-butyl (meth)acrylamide, N-t-butyl N-alkyl (meth)acrylamide such as (meth)acrylamide and N-hexyl (meth)acrylamide; and N,N-dialkyl (meth)acrylamide such as N,N-dimethyl (meth)acrylamide and N,N-diethyl (meth)acrylamide. In addition, the N- substituent may be an alkyl group having a hydroxyl group, and examples thereof include N-hydroxymethyl (meth)acrylamide, N-(2-hydroxyethyl) (meth)acrylamide, N-(2-hydroxypropyl). ) (meth)acrylamide, etc. are mentioned. In addition, specific examples of the N-substituted (meth)acrylamide forming the above-described 5-membered ring or 6-membered ring include N-acryloylpyrrolidine, 3-acryloyl-2-oxazolidinone, and 4-acryloyl Morpholine, N-acryloylpiperidine, N-methacryloylpiperidine, etc. are mentioned.

As a bifunctional (meth)acrylate monomer,

Ethylene glycol di(meth)acrylate, 1,3-butanediol di(meth)acrylate, 1,4-butanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,9- alkylene glycol di(meth)acrylates such as nonanediol di(meth)acrylate and neopentyl glycol di(meth)acrylate;

Diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, dipropylene glycol di (meth) acrylate, tripropylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, polyoxyalkylene glycol di(meth)acrylates such as polypropylene glycol di(meth)acrylate and polytetramethylene glycol di(meth)acrylate;

di(meth)acrylates of halogen-substituted alkylene glycols such as tetrafluoroethylene glycol di(meth)acrylate;

di(meth)acrylates of aliphatic polyols such as trimethylolpropane di(meth)acrylate, ditrimethylolpropane di(meth)acrylate, and pentaerythritol di(meth)acrylate;

hydrogenated dicyclopentadiene or di(meth)acrylate of tricyclodecanedialkanol such as hydrogenated dicyclopentadienyldi(meth)acrylate and tricyclodecanedimethanoldi(meth)acrylate;

di(meth)acrylate of dioxane glycol or dioxane dialkanol such as 1,3-dioxane-2,5-diyldi(meth)acrylate [alias: dioxane glycol di(meth)acrylate];

di(meth)acrylates of alkylene oxide adducts of bisphenol A or bisphenol F such as bisphenol A ethylene oxide adduct diacrylate and bisphenol F ethylene oxide adduct diacrylate;

Epoxy di(meth)acrylate of bisphenol A or bisphenol F, such as an acrylic acid adduct of bisphenol A diglycidyl ether and an acrylic acid adduct of bisphenol F diglycidyl ether;

silicone di(meth)acrylate;

di(meth)acrylate of hydroxypivalic acid neopentyl glycol ester;

2,2-bis[4-(meth)acryloyloxyethoxyethoxyphenyl]propane;

2,2-bis[4-(meth)acryloyloxyethoxyethoxycyclohexyl]propane;

di(meth)acrylate of 2-(2-hydroxy-1,1-dimethylethyl)-5-ethyl-5-hydroxymethyl-1,3-dioxane];

tris(hydroxyethyl)isocyanurate di(meth)acrylate; and the like.

Examples of the trifunctional or higher polyfunctional (meth)acrylate monomer include glycerin tri(meth)acrylate, alkoxylated glycerin tri(meth)acrylate, trimethylolpropane tri(meth)acrylate, and ditrimethylolpropane tri(meth)acryl. Rate, ditrimethylolpropane tetra (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol tetra (meth) acrylate, dipentaerythritol penta ( poly(meth)acrylates of trifunctional or higher aliphatic polyols such as meth)acrylate and dipentaerythritol hexa(meth)acrylate; poly(meth)acrylates of trifunctional or more halogen-substituted polyols; tri(meth)acrylate of an alkylene oxide adduct of glycerin;

tri(meth)acrylate of the alkylene oxide adduct of trimethylolpropane; 1,1,1-tris[(meth)acryloyloxyethoxyethoxy]propane; Tris(hydroxyethyl) isocyanurate tri(meth)acrylate etc. are mentioned.

Moreover, you may use a commercial item. As a commercial item, A-DPH-12E, A-TMPT, A-9300 (made by Shin-Nakamura Chemical Co., Ltd.) etc. are mentioned, for example.

As a (meth)acryl oligomer, a urethane (meth)acryl oligomer, a polyester (meth)acryl oligomer, an epoxy (meth)acryl oligomer, etc. are mentioned.

A urethane (meth)acryl oligomer is a compound which has a urethane bond (-NHCOO-) and at least two (meth)acryloyl groups in a molecule|numerator. Specifically, a urethanation reaction product of a hydroxyl group-containing (meth)acrylic monomer and polyisocyanate each having at least one (meth)acryloyl group and at least one hydroxyl group in the molecule, or terminal isocyanate obtained by reacting a polyol with a polyisocyanate It may be a urethanation reaction product of a Naito group-containing urethane compound and a (meth)acrylic monomer each having at least one (meth)acryloyl group and at least one hydroxyl group in the molecule.

The hydroxyl group-containing (meth)acrylic monomer used in the urethanation reaction may be, for example, a hydroxyl group-containing (meth)acrylate monomer, and specific examples thereof include 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth) ) acrylate, 2-hydroxybutyl (meth) acrylate, 2-hydroxy-3-phenoxypropyl (meth) acrylate, glycerin di (meth) acrylate, trimethylolpropane di (meth) acrylate, penta erythritol tri(meth)acrylate and dipentaerythritol penta(meth)acrylate. Specific examples other than the hydroxyl group-containing (meth)acrylate monomer include N-hydroxyalkyl (meth)acrylamide monomers such as N-hydroxyethyl (meth)acrylamide and N-methylol (meth)acrylamide. .

Examples of the polyisocyanate used for the urethanation reaction with the hydroxyl group-containing (meth)acrylic monomer include hexamethylene diisocyanate, lysine diisocyanate, isophorone diisocyanate, dicyclohexylmethane diisocyanate, tolylene diisocyanate, xylylene diisocyanate, Among these diisocyanates, diisocyanates obtained by hydrogenating aromatic isocyanates (eg, hydrogenated tolylene diisocyanate, hydrogenated xylylene diisocyanate, etc.), triphenylmethane triisocyanate, di- or tri- such as dibenzylbenzene triisocyanate Polyisocyanate obtained by multiplying isocyanate and said diisocyanate, etc. are mentioned.

Moreover, as a polyol used in order to set it as a terminal isocyanato group containing urethane compound by reaction with polyisocyanate, polyester polyol, polyether polyol, etc. other than an aromatic, aliphatic or alicyclic polyol can be used. Examples of the aliphatic and alicyclic polyols include 1,4-butanediol, 1,6-hexanediol, ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, neopentyl glycol, trimethylolethane, trimethylolpropane, and ditrimethylol. Propane, pentaerythritol, dipentaerythritol, dimethylol heptane, dimethylol propionic acid, dimethylol butanoic acid, glycerin, hydrogenated bisphenol A, etc. are mentioned.

A polyester polyol is obtained by the dehydration condensation reaction of the above-mentioned polyol and polybasic carboxylic acid or its anhydride. Examples of polybasic carboxylic acids or their anhydrides are expressed by adding "(anhydride)" to what may be anhydride, (anhydride) succinic acid, adipic acid, (anhydride) maleic acid, (anhydride) itaconic acid, (anhydride) trimellitic acid, (anhydrous) pyromellitic acid, (anhydrous) phthalic acid, isophthalic acid, terephthalic acid, hexahydro (anhydrous) phthalic acid, and the like.

The polyether polyol may be, in addition to polyalkylene glycol, polyoxyalkylene-modified polyol obtained by reaction of the above-described polyol or dihydroxybenzene with alkylene oxide.

A polyester (meth)acrylate oligomer means the oligomer which has an ester bond and at least two (meth)acryloyloxy groups in a molecule|numerator.

The polyester (meth)acrylate oligomer can be obtained, for example, by subjecting (meth)acrylic acid, a polybasic carboxylic acid or anhydride thereof, and a polyol to a dehydration condensation reaction.

Examples of the polybasic carboxylic acid or anhydride thereof include succinic anhydride, adipic acid, maleic anhydride, itaconic anhydride, trimellitic anhydride, pyromellitic anhydride, hexahydrophthalic anhydride, phthalic acid, succinic acid, maleic acid, itaconic acid, trimellitic acid, pyromellitic acid, hexahydrophthalic acid, phthalic acid, isophthalic acid, terephthalic acid, and the like.

Examples of the polyol include 1,4-butanediol, 1,6-hexanediol, ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, neopentyl glycol, trimethylolethane, trimethylolpropane, ditrimethylolpropane, pentaerythritol. , dipentaerythritol, dimethylol heptane, dimethylol propionic acid, dimethylol butanoic acid, glycerin, and hydrogenated bisphenol A.

An epoxy (meth)acrylic oligomer can be obtained by addition reaction of polyglycidyl ether and (meth)acrylic acid. Epoxy(meth)acryl oligomers have at least two (meth)acryloyloxy groups in the molecule.

As polyglycidyl ether, ethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, tripropylene glycol diglycidyl ether, 1,6-hexanediol diglycidyl ether, bisphenol A diglycidyl Ether etc. are mentioned.

Examples of the styrene-based compound include styrene; alkyl styrenes such as methyl styrene, dimethyl styrene, trimethyl styrene, ethyl styrene, diethyl styrene, triethyl styrene, propyl styrene, butyl styrene, hexyl styrene, heptyl styrene, and octyl styrene; halogenated styrenes such as fluorostyrene, chlorostyrene, bromostyrene, dibromostyrene, and iodostyrene; nitrostyrene; acetyl styrene; methoxystyrene; and divinylbenzene.

Examples of the vinyl-based monomer include fatty acid vinyl esters such as vinyl acetate, vinyl propionate, vinyl butyrate, vinyl 2-ethylhexanoate, and vinyl laurate; vinyl halides such as vinyl chloride and vinyl bromide; vinylidene halides such as vinylidene chloride; 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.

It is preferable that it is a (meth)acrylate compound, and, as for a radically curable component (E), it is more preferable that it is a polyfunctional (meth)acrylate compound. The polyfunctional (meth)acrylate compound is preferably trifunctional or more.

Content of a radically curable component (E) is 0.5-100 mass parts normally with respect to 100 mass parts of resin (A), It is preferable that it is 1-70 mass parts, It is more preferable that it is 3-50 mass parts, It is 5-30 mass It is more preferable that it is negative, and it is especially preferable that it is 7.5-20 mass parts.

<Initiator (D)>

The initiator (D) should just be a compound which causes the polymerization reaction of the light-selective absorption compound (C) or the radically curable component (E) contained as needed. The initiator (D) may be either a compound causing a polymerization reaction by absorbing thermal energy (thermal polymerization initiator) or a compound causing a polymerization reaction by absorbing light energy (photo polymerization initiator). In addition, it is preferable that light here is an active energy ray like visible light, an ultraviolet-ray, an X-ray, or an electron beam.

As the thermal polymerization initiator, a compound that generates radicals by heating or the like (thermal radical generator), a compound that generates an acid by heating or the like (thermal acid generator), a compound that generates a base by heating or the like (thermal base generator), etc. can be heard

As a photoinitiator, a compound that generates a radical by absorbing light energy (photoradical generator), a compound that generates an acid by absorbing light energy (photoacid generator), a compound that generates a base by absorbing light energy A compound (photobase generator) etc. are mentioned.

It is preferable to select the thing suitable for the polymerization reaction of a radically curable component (E), It is preferable that it is a radical generator, and, as for an initiator (D), it is more preferable that it is an optical radical generator. As a radical generator, a thermal radical generator and an optical radical generator are mentioned, for example.

The initiator (D) may contain 2 or more types, and may use an optical radical generator and a thermal radical generator together.

Examples of the radical generator include an alkylphenone compound, a benzoin compound, a benzophenone compound, an oxime ester compound, and a phosphine compound. It is preferable that a radical generator is an optical radical generator, and it is more preferable that it is an oxime ester system optical radical generator from a reactive viewpoint of a polymerization reaction. By using an oxime ester radical generator, the reaction rate of a light-selective absorption compound (C) and a radical hardening component (E) can be raised even if it is a hardening condition with weak illumination intensity or light quantity.

Examples of the alkylphenone compound include an α-aminoalkylphenone compound, an α-hydroxyalkylphenone compound, and an α-alkoxyalkylphenone compound.

Examples of the α-aminoalkylphenone compound include 2-methyl-2-morpholino-1-(4-methylsulfanylphenyl)propan-1-one, 2-dimethylamino-1-(4-morpholinophenyl)- 2-benzylbutan-1-one, 2-dimethylamino-1-(4-morpholinophenyl)-2-(4-methylphenylmethyl)butan-1-one, etc. are mentioned, Preferably 2-methyl -2-morpholino-1-(4-methylsulfanylphenyl)propan-1-one, 2-dimethylamino-1-(4-morpholinophenyl)-2-benzylbutan-1-one, etc. can α-aminoalkylphenone compounds include Irgacua (registered trademark) 127, 184, 369, 369E, 379EG, 651, 907, 1173, 2959 (above, manufactured by BASF Japan Co., Ltd.), Sakeol (registered trademark) BEE ( You may use commercial items, such as the Seko Chemical company make).

Examples of the benzoin compound include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether.

As the benzophenone compound, for example, benzophenone, o-benzoyl methylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, 3,3',4,4'-tetra(tert-butylper) Oxycarbonyl) benzophenone, 2,4,6-trimethylbenzophenone, etc. are mentioned. A commercial item may be used for a benzophenone compound.

As the oxime ester compound, N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one -2-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethane-1-imine, N-acetoxy-1-[9 -ethyl-6-{2-methyl-4-(3,3-dimethyl-2,4-dioxacyclopentanylmethyloxy)benzoyl}-9H-carbazol-3-yl]ethane-1-imine; can The oxime compound is Irgacure OXE-01, OXE-02, OXE-03 (above, manufactured by BASF Japan), N-1919, NCI-730, NCI-831, NCI-930 (made by ADEKA), PBG3057 (TRONLY) You may use commercial items, such as a company make).

Examples of the phosphine compound include acylphosphine oxides such as phenyl (2,4,6-trimethylbenzoyl)phosphine oxide and diphenyl (2,4,6-trimethylbenzoyl)phosphine oxide. Examples of the phosphine compound include Argacure (registered product) TPO and Argacure 819 (manufactured by BASF Japan).

The acid generator may be an onium salt such as an aromatic iodonium salt or an aromatic sulfonium salt; aromatic diazonium salts; An iron-arene complex etc. are mentioned.

The aromatic iodonium salt is a compound having a diaryliodonium cation, and typically a diphenyliodonium cation is mentioned as the cation. The aromatic sulfonium salt is a compound having a triarylsulfonium cation, and examples of the cation include a triphenylsulfonium cation and a 4,4'-bis(diphenylsulfonio)diphenylsulfide cation. An aromatic diazonium salt is a compound which has a diazonium cation, and a benzene diazonium cation is mentioned typically as said cation. Also, the iron-arene complex is typically a cyclopentadienyl iron(II) arene cation complex salt.

The above-described cations are paired with anions (anions) to constitute a photocation generator. Examples of anions constituting the photocation generator include a special phosphorus anion [(Rf) _n PF _6-n ] ^- , hexafluorophosphate anion PF ₆ ^- , hexafluoroantimonate anion SbF ₆ ^- , pentafluoro rhohydroxyantimonate anion SbF ₅ (OH) ^- , hexafluoroacetate anion AsF ₆ ^- , tetrafluoroborate anion BF ₄ ^- , tetrakis(pentafluorophenyl)borate anion B(C ₆ F ₅ ) ₄ ^- and so on. Among them, special phosphorus anion [(Rf) _n PF _6-n ] ^- , hexafluorophosphate anion PF ₆ ^- , tetrakis (pentafluorophenyl) It is preferable that they are borate anion B(C ₆ F ₅ ) ₄ ^- , hexafluoroantimonate anion SbF ₆ ^- .

Examples of the photobase generator include carbamate compounds, α-aminoketone compounds, quaternary ammonium compounds, O-acyloxime compounds, and aminocyclopropenone compounds.

Examples of the carbamate compound include 1-(2-anthraquinonyl)ethyl 1-piperidinecarboxylate, 1-(2-anthraquinonyl)ethyl 1H-2-ethylimidazole-1-carboxylate. , 9-anthrylmethyl 1-piperidinecarboxylate, 9-anthrylmethyl N,N-diethylcarbamate, 9-anthrylmethyl N-propylcarbamate, 9-anthrylmethyl N-cyclo Hexylcarbamate, 9-anthrylmethyl 1H-imidazole-1-carboxylate, 9-anthrylmethyl N,N-dioctylcarbamate, 9-anthrylmethyl 1-(4-hydroxypiperi) Dean) carboxylate, 1-pyrenylmethyl 1-piperidinecarboxylate, bis[1-(2-anthraquinonyl)ethyl] 1,6-hexanediylbiscarbamate, bis(9-anthryl) methyl) 1,6-hexanediylbiscarbamate; and the like.

As ?-aminoketone compounds, for example, the following are known. 1-phenyl-2-(4-morpholinobenzoyl)-2-dimethylaminobutane, 2-(4-methylthiobenzoyl)-2-morpholinopropane, etc. are mentioned.

Examples of the quaternary ammonium compound serving as the photobase generator include 1-(4-phenylthiophenacyl)-1-azonia-4-azabicyclo[2,2,2]octanetetraphenylborate, 5-(4-phenyl). Thiophenacil)-1-aza-5-azoniabicyclo[4,3,0]-5-nonene tetraphenylborate, 8-(4-phenylthiophenacyl)-1-aza-8-azoniabi Cyclo[5,4,0]-7-undecenetetraphenylborate etc. are mentioned.

Examples of the aminocyclopropenone compound serving as the photobase generator include 2-diethylamino-3-phenylcyclopropenone, 2-diethylamino-3-(1-naphthyl)cyclopropenone, 2-pyrrolidinyl- 3-phenylcyclopropenone, 2-imidazolyl-3-phenylcyclopropenone, 2-isopropylamino-3-phenylcyclopropenone, etc. are mentioned.

Examples of the thermal base generator include carbamate derivatives such as 2-(4-biphenyl)-2-propyl carbamate and 1,1-dimethyl-2-cyanoethyl carbamate, urea and N,N,N a urea derivative such as '-trimethylurea, a dihydropyridine derivative such as 1,4-dihydronicotinamide, dicyandiamide, and a salt containing an acid and a base such as an organic salt or an inorganic salt.

Content of initiator (D) is 0.01-20 mass parts normally with respect to 100 mass parts of resin (A), It is preferable that it is 0.5-10 mass parts, It is more preferable that it is 1-7 mass parts, It is 1.5-5 mass parts More preferably, it is 2-4 mass parts especially preferably.

<Crosslinking agent (F)>

Examples of the crosslinking agent (F) include an isocyanate-based crosslinking agent, an epoxy-based crosslinking agent, an aziridine-based crosslinking agent, and a metal chelate-based crosslinking agent. It is preferable that it is an isocyanate type crosslinking agent.

As the isocyanate-based crosslinking agent, a compound having at least two isocyanate groups (-NCO) in the molecule is preferable, for example, an aliphatic isocyanate-based compound (such as hexamethylene diisocyanate), an alicyclic isocyanate-based compound (such as isophorone diisocyanate) , hydrogenated diphenylmethane diisocyanate, hydrogenated xylylene diisocyanate), aromatic isocyanate compounds (such as tolylene diisocyanate, xylylene diisocyanate diphenylmethane diisocyanate, naphthalene diisocyanate, triphenylmethane triisocyanate, etc.) have. In addition, the crosslinking agent (F) is an adduct (adduct) of the polyhydric alcohol compound of the isocyanate compound [eg, an adduct using glycerol, trimethylolpropane, etc.], an isocyanurate compound, a biuret compound, polyether Derivatives, such as a urethane prepolymer type isocyanate compound, which were addition-reacted with polyol, polyester polyol, acrylic polyol, polybutadiene polyol, polyisoprene polyol, etc. may be sufficient. A crosslinking agent (F) can be used individually or in combination of 2 or more types. Among these, an aromatic isocyanate-based compound (such as tolylene diisocyanate, xylylene diisocyanate), an aliphatic isocyanate-based compound (such as hexamethylene diisocyanate) or a polyhydric alcohol compound thereof (such as glycerol, trimethylolpropane) is typically added Sieve or isocyanurate form is mentioned. If the crosslinking agent (F) is an aromatic isocyanate compound and/or an adduct of these polyhydric alcohol compounds or isocyanurate compounds, this is because it is advantageous for the formation of an optimal crosslinking density (or crosslinked structure), the pressure-sensitive adhesive layer Durability can be improved. In particular, if it is a tolylene diisocyanate-based compound and/or an adduct of these polyhydric alcohol compounds, durability can be improved even when, for example, an adhesive layer is applied to a polarizing plate.

Content of a crosslinking agent (F) is 0.01-25 mass parts normally with respect to 100 mass parts of resin (A), Preferably it is 0.1-15 mass parts, More preferably, it is 0.15-7 mass parts, More preferably, It is 0.2-5 mass parts, Especially preferably, it is 0.25-2 mass parts.

The adhesive composition of this invention may contain the silane compound (G) further.

As the silane compound (G), for example, vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris(2-methoxyethoxy)silane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropyltri Ethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropylethoxydimethylsilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-chloropropylmethyldimethoxy silane, 3-chloropropyl trimethoxysilane, 3-methacryloyloxypropyl trimethoxysilane, 3-mercaptopropyl trimethoxysilane, etc. are mentioned.

The silane compound (G) may be a silicone oligomer. Specific examples of silicone oligomers are described in the form of a combination of monomers as follows.

3-Mercaptopropyltrimethoxysilane-tetramethoxysilane oligomer, 3-mercaptopropyltrimethoxysilane-tetraethoxysilane oligomer, 3-mercaptopropyltriethoxysilane-tetramethoxysilane oligomer, 3- mercaptopropyl group-containing oligomers such as mercaptopropyltriethoxysilane-tetraethoxysilane oligomers; Mercaptomethyltrimethoxysilane-tetramethoxysilane oligomer, mercaptomethyltrimethoxysilane-tetraethoxysilane oligomer, mercaptomethyltriethoxysilane-tetramethoxysilane oligomer, mercaptomethyltriethoxysilane- mercaptomethyl group-containing oligomers such as tetraethoxysilane oligomers; 3-Glycidoxypropyltrimethoxysilane-tetramethoxysilane copolymer, 3-glycidoxypropyltrimethoxysilane-tetraethoxysilane copolymer, 3-glycidoxypropyltriethoxysilane-tetramethoxy Silane copolymer, 3-glycidoxypropyltriethoxysilane-tetraethoxysilane copolymer, 3-glycidoxypropylmethyldimethoxysilane-tetramethoxysilane copolymer, 3-glycidoxypropylmethyldimethoxysilane 3-glycidoxy such as tetraethoxysilane copolymer, 3-glycidoxypropylmethyldiethoxysilane-tetramethoxysilane copolymer, and 3-glycidoxypropylmethyldiethoxysilane-tetraethoxysilane copolymer propyl group-containing copolymer; 3-Methacryloyloxypropyltrimethoxysilane-tetramethoxysilane oligomer, 3-methacryloyloxypropyltrimethoxysilane-tetraethoxysilane oligomer, 3-methacryloyloxypropyltriethoxysilane -Tetramethoxysilane oligomer, 3-methacryloyloxypropyltriethoxysilane-tetraethoxysilane oligomer, 3-methacryloyloxypropylmethyldimethoxysilane-tetramethoxysilane oligomer, 3-methacrylo Iloxypropylmethyldimethoxysilane-tetraethoxysilane oligomer, 3-methacryloyloxypropylmethyldiethoxysilane-tetramethoxysilane oligomer, 3-methacryloyloxypropylmethyldiethoxysilane-tetraethoxysilane methacryloyloxypropyl group-containing oligomers such as oligomers; 3-Acryloyloxypropyltrimethoxysilane-tetramethoxysilane oligomer, 3-acryloyloxypropyltrimethoxysilane-tetraethoxysilane oligomer, 3-acryloyloxypropyltriethoxysilane-tetrameth Toxysilane oligomer, 3-acryloyloxypropyltriethoxysilane-tetraethoxysilane oligomer, 3-acryloyloxypropylmethyldimethoxysilane-tetramethoxysilane oligomer, 3-acryloyloxypropylmethyldimethoxy Acryloyloxypropyl such as silane-tetraethoxysilane oligomer, 3-acryloyloxypropylmethyldiethoxysilane-tetramethoxysilane oligomer, and 3-acryloyloxypropylmethyldiethoxysilane-tetraethoxysilane oligomer group-containing oligomers; Vinyltrimethoxysilane-tetramethoxysilane oligomer, vinyltrimethoxysilane-tetraethoxysilane oligomer, vinyltriethoxysilane-tetramethoxysilane oligomer, vinyltriethoxysilane-tetraethoxysilane oligomer, vinylmethyl Contains vinyl groups such as dimethoxysilane-tetramethoxysilane oligomer, vinylmethyldimethoxysilane-tetraethoxysilane oligomer, vinylmethyldiethoxysilane-tetramethoxysilane oligomer, and vinylmethyldiethoxysilane-tetraethoxysilane oligomer oligomers; 3-Aminopropyltrimethoxysilane-tetramethoxysilane copolymer, 3-aminopropyltrimethoxysilane-tetraethoxysilane copolymer, 3-aminopropyltriethoxysilane-tetramethoxysilane copolymer, 3- Aminopropyltriethoxysilane-tetraethoxysilane copolymer, 3-aminopropylmethyldimethoxysilane-tetramethoxysilane copolymer, 3-aminopropylmethyldimethoxysilane-tetraethoxysilane copolymer, 3-aminopropyl amino group-containing copolymers such as methyldiethoxysilane-tetramethoxysilane copolymer and 3-aminopropylmethyldiethoxysilane-tetraethoxysilane copolymer;

The silane compound (G) may be a silane compound represented by the following formula (g1).

[Wherein, A represents an alkanediyl group having 1 to 20 carbon atoms or a divalent alicyclic hydrocarbon group having 3 to 20 carbon atoms, and -CH ₂ - constituting the alkanediyl group and the alicyclic hydrocarbon group is -O- or - may be substituted with CO-, R ⁴¹ represents an alkyl group having 1 to 5 carbon atoms, R ⁴² , R ⁴³ , R ⁴⁴ , R ⁴⁵ and R ⁴⁶ are each independently an alkyl group having 1 to 5 carbon atoms or an alkyl group having 1 to 5 carbon atoms represents an alkoxy group.]

Examples of the alkanediyl group having 1 to 20 carbon atoms represented by A include a methylene group, 1,2-ethanediyl group, 1,3-propanediyl group, 1,4-butanediyl group, 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 group, 1,16-hexadecanediyl group, 1,18-octadecanediyl group, and 1,20-icosandiyl group are mentioned. Examples of the divalent alicyclic hydrocarbon group having 3 to 20 carbon atoms include a 1,3-cyclopentanediyl group and a 1,4-cyclohexanediyl group. As a group in which -CH ₂ - constituting the alkanediyl group and the alicyclic hydrocarbon group is substituted with -O- or -CO-, -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 ⁴⁶ 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 represented alkoxy group having 1 to 5 carbon atoms 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 (g1) 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(tripropoxysilyl)hexane, 1,8-bis(trimethoxysilyl)octane, 1,8-bis(triethoxysilyl)octane, 1,8-bis(tripropoxysilyl) bis(triC1-5 alkoxysilyl)C1-10 alkane such as 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, 1,8-bis(dimethoxymethylsilyl)octane, bis(diC1-5 alkoxyC1-5alkylsilyl)C1-10 alkanes such as 1,8-bis(dimethoxyethylsilyl)octane; Bis(monoC1-5 alkoxy-diC1-5alkylsilyl)C1-10 alkane, such as 1,6-bis(methoxydimethylsilyl)hexane and 1,8-bis(methoxydimethylsilyl)octane, etc. are mentioned. have. Among these, 1,2-bis(trimethoxysilyl)ethane, 1,3-bis(trimethoxysilyl)propane, 1,4-bis(trimethoxysilyl)butane, 1,5-bis(trimethane) Bis(triC1-3alkoxysilyl)C1-10 alkanes such as oxysilyl)pentane, 1,6-bis(trimethoxysilyl)hexane, and 1,8-bis(trimethoxysilyl)octane are preferable, and particularly 1,6-bis(trimethoxysilyl)hexane and 1,8-bis(trimethoxysilyl)octane are preferred.

Content of a silane compound (G) is 0.01-20 mass parts normally with respect to 100 mass parts of resin (A), Preferably it is 0.1-10 mass parts, More preferably, it is 0.15-7 mass parts, More preferably is 0.2 to 5 parts by mass, particularly preferably 0.25 to 2 parts by mass.

The pressure-sensitive adhesive composition may further contain one or more additives such as an antistatic agent, a solvent, a crosslinking catalyst, a tackifier, a plasticizer, a softener, a pigment, a rust inhibitor, an inorganic filler, and light scattering fine particles.

The pressure-sensitive adhesive layer of the present invention is formed by, for example, dissolving or dispersing the pressure-sensitive adhesive composition of the present invention in a solvent to obtain a solvent-containing pressure-sensitive adhesive composition, then applying it to the surface of a substrate, drying it, and then irradiating with active energy rays can do. The pressure-sensitive adhesive layer of the present invention can also be said to be a photocured material of the pressure-sensitive adhesive composition.

A plastic film is suitable as a base material, and the peeling film to which the release process was specifically given is mentioned. As a peeling film, the thing in which the mold release process, such as silicone treatment, was given to one side of the film containing resin, such as a polyethylene terephthalate, polybutylene terephthalate, a polycarbonate, and a polyarylate, is mentioned.

Although the conditions (drying temperature, drying time) for drying the coating film formed from the adhesive composition containing a solvent can be set suitably with the composition or density|concentration, Preferably it is 1 to 60 minutes at 60-150 degreeC.

It is preferable that active energy ray irradiation after coating film drying is ultraviolet irradiation. It is preferable that the illuminance of the ultraviolet ray to be irradiated is 10 mW/cm 2 to 3000 mW/cm 2 . In addition, it is preferable that the accumulated light quantity of ultraviolet rays is 10 mJ/cm 2 to 5000 mJ/cm 2 .

The ultraviolet lamp which irradiates an ultraviolet-ray may be a mercury lamp, a metal halide lamp, or an LED lamp.

It is preferable that it is an adhesive layer which satisfy|fills following formula (3), and, as for the adhesive layer of this invention, it is more preferable that it is an adhesive layer which satisfy|fills Formula (4) further.

A(380)≥0.60 (3)

[In formula (3), A (380) represents the absorbance at a wavelength of 380 nm.]

A(380)/A(420)≥5 (4)

[In formula (4), A (380) represents the absorbance at a wavelength of 380 nm, and A (420) represents the absorbance at a wavelength of 420 nm.]

It shows that absorption in wavelength 380 nm is so high that the value of A (380) is large. When the value of A (380) is less than 0.60, the absorption at a wavelength of 380 nm is low, and deterioration of the member (for example, a display device such as an organic EL element or a liquid crystal retardation film, etc.) which is easily deteriorated by light in the vicinity of ultraviolet rays occurs. easy. The value of A (380) is preferably 0.75 or more, more preferably 0.85 or more, and particularly preferably 1.0 or more. Although there is no upper limit in particular, it is usually 10 or less.

A value of A(380)/A(420) indicates an absorption size at a wavelength of 380 nm with respect to an absorption size at a wavelength of 420 nm, and a larger value indicates that there is specific absorption in a wavelength region near ultraviolet rays. The value of A(380)/A(420) is preferably 5 or more, more preferably 20 or more, still more preferably 50 or more, and particularly preferably 100 or more.

The thickness of the pressure-sensitive adhesive layer of the present invention is usually less than 200 µm, preferably 100 µm or less, more preferably 20 µm or less, still more preferably 12 µm or less or less than 12 µm, still more preferably 10 µm or less. ㎛ or less, particularly preferably 7 ㎛ or less. Moreover, it is 0.1 micrometer or more normally, Preferably it is 0.5 micrometer or more, More preferably, it is 1 micrometer or more, More preferably, it is 2 micrometers or more.

According to the present invention, for example, even in the adhesive layer of a thin film having a thickness of less than 12 µm, ultraviolet rays can be sufficiently absorbed, which is advantageous from the viewpoint of thinning the display device.

The gel fraction of the adhesive layer of this invention is 50-99.9 mass % normally, It is preferable that it is 60-99 mass %, More preferably, it is 70-95 mass %, More preferably, it is 75-90 mass %.

<Optical film with adhesive layer>

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.

The optical film with an adhesive layer in which the optical film was laminated|stacked on the at least one surface of the adhesive layer of this invention is also contained in this invention.

The optical film with an adhesive layer of this invention is formed by dissolving or dispersing the said adhesive composition in a solvent to make a solvent-containing adhesive composition, then, apply|coating this to the surface of an optical film, drying it, and performing active energy ray irradiation can do. Moreover, it can obtain also by forming an adhesive layer on a peeling film in the same manner, and laminating|stacking (transferring) this adhesive layer on the surface of an optical film.

An optical film is a film having an optical function such as transmitting, reflecting, or absorbing light rays. A single-layered film may be sufficient as an optical film, and a multilayered film may be sufficient as it. Examples of the optical film include a polarizing film, a retardation film, a brightness enhancing film, an anti-glare film, an antireflection film, a diffusion film, a light collecting film, and the like, and a polarizing film, retardation film, or laminated film thereof is preferable.

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

The brightness improving film is used for the purpose of improving the brightness in a liquid crystal display to which a polarizing plate is applied. Specifically, a reflective polarization separation sheet designed to produce anisotropy in reflectance by laminating several thin films with different refractive index anisotropy, an alignment film of cholesteric liquid crystal polymer, or an alignment liquid crystal layer supported on a base film A circularly polarized light separation sheet etc. are mentioned.

A polarizing film is a film having a property of absorbing linearly polarized light having an oscillation plane parallel to the absorption axis and transmitting linearly polarized light having an oscillation plane perpendicular to the absorption axis (parallel to the transmission axis), for example, a polyvinyl alcohol-based film. A film in which a dichroic dye is adsorbed and oriented to a resin film can be used.

Examples of the dichroic dye include iodine and dichroic organic dyes.

The degree of saponification 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 may be used. The polymerization degree of the polyvinyl alcohol-based resin is usually 1,000 to 10,000, preferably 1,500 to 5,000.

Usually, what formed the polyvinyl alcohol-type resin into a film 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 1-150 µm, and in consideration of the ease of stretching, etc., it is preferably 10 µm or more.

For the polarizing film, for example, a process of uniaxial stretching with respect to a raw film, a process of dyeing the film with a dichroic dye to adsorb the dichroic dye, a process of treating the film with an aqueous boric acid solution, and a process of washing the film are performed, and finally It is prepared by drying with The thickness of a polarizing film is 1-30 micrometers normally, From a viewpoint of thinning of an optical film with an adhesive layer, Preferably it is 20 micrometers or less, More preferably, it is 15 micrometers or less, Especially preferably, it is 10 micrometers or less.

It is preferable that at least one surface of a polarizing film is a polarizing plate in which the protective film is formed through the adhesive agent.

A well-known adhesive agent is used as an adhesive agent, and a water-based adhesive agent may be sufficient, and an active energy ray hardening type adhesive agent may be sufficient.

As the water-based adhesive, a common water-based adhesive (eg, an adhesive containing a polyvinyl alcohol-based resin aqueous solution, a water-based two-component urethane emulsion adhesive, an aldehyde compound, an epoxy compound, a melamine compound, a methylol compound, an isocyanate compound, an amine compound, a polyvalent metal salt crosslinking agents, etc.) are mentioned. Among these, an aqueous adhesive containing a polyvinyl alcohol-based aqueous resin solution can be suitably used. Moreover, when using a water-system adhesive agent, after bonding a polarizing film and a protective film, in order to remove the water contained in a water-system adhesive agent, it is preferable to perform the process of drying. After the drying step, for example, a curing step of curing at a temperature of about 20 to 45°C may be provided. The adhesive layer formed of the water-based adhesive is usually 0.001 to 5 m.

Active energy ray-curable adhesive refers to an adhesive that is cured by irradiating active energy rays such as ultraviolet rays or electron beams, for example, a curable composition containing a polymerizable compound and a photopolymerization initiator, a curable composition containing a photoreactive resin, a binder resin and A curable composition containing a photoreactive crosslinking agent, etc. are mentioned, Preferably it is an ultraviolet curable adhesive agent.

As a method of bonding a polarizing film and a protective film, the method of giving surface activation processing, such as a saponification process, a corona treatment, a plasma processing, to these at least any one bonding surface, etc. are mentioned. When a protective film is bonded on both surfaces of a polarizing film, the adhesive agent for bonding these resin films together may be sufficient as an adhesive agent of the same type, or a different type of adhesive agent may be sufficient as it.

As a protective film, it is preferable that it is a film formed from the thermoplastic resin which has translucency. Specifically, polyolefin resin; Cellulose-based resin; polyester-based resin; (meth)acrylic resin; or a film including a mixture or copolymer thereof. When a protective film is formed on both surfaces of a polarizing film, the film containing another thermoplastic resin may be sufficient as the protective film used, and the film containing the same thermoplastic resin may be sufficient as it.

When a protective film is laminated|stacked on at least one surface of a polarizing film, it is preferable that a protective film is a protective film containing polyolefin resin and a cellulose resin. By using these films, the shrinkage|contraction of the polarizing film in a high-temperature environment can be suppressed effectively, without impairing the optical characteristic of a polarizing film. Moreover, an oxygen shielding layer may be sufficient as a protective film.

As a preferable structure of a polarizing plate, it is a polarizing plate in which the protective film was laminated|stacked on at least one surface of a polarizing film via an adhesive bond layer. When a protective film is laminated|stacked only on one side of a polarizing film, it is more preferable to laminate|stack on the visual recognition side. It is preferable that the protective film laminated|stacked on the viewer side is a protective film containing a triacetyl cellulose-type resin or a cycloolefin-type resin. An unstretched film may be sufficient as a protective film, and it may extend|stretch in arbitrary directions, and may have retardation. Surface treatment layers, such as a hard-coat layer and an anti-glare layer, may be formed in the surface of the protective film laminated|stacked on the visual recognition side.

When the protective film is laminated on both surfaces of the polarizing film, the protective film on the panel side (the side opposite to the viewing side) is preferably a protective film or retardation film containing a triacetyl cellulose-based resin, a cycloolefin-based resin, or an acrylic resin. . The retardation film mentioned later may be a zero retardation film.

The retardation film is an optical film showing optical anisotropy, for example, polyvinyl alcohol, polycarbonate, polyester, polyarylate, polyimide, polyolefin, polycycloolefin, polystyrene, polysulfone, polyethersulfone, polyvinylidene fluoride/ and a stretched film obtained by stretching a polymer film containing polymethyl methacrylate, acetyl cellulose, saponified ethylene-vinyl acetate copolymer, polyvinyl chloride, etc. to about 1.01 to 6 times. It is preferable that it is the polymer film which uniaxially or biaxially stretched the acetyl cellulose, polyester, a polycarbonate film, or a cycloolefin resin film among a stretched film. The retardation film may be a retardation film in which optical anisotropy is expressed by applying and orienting a liquid crystal compound to a substrate.

Further, in the present 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, and the like.

The zero retardation film is -15 to 15 nm in both the front retardation ( _{Re) and the retardation (R th )} in the thickness direction, and refers to an optically isotropic film. Examples of the zero retardation film include a resin film containing a cellulose-based resin, a polyolefin-based resin (chain polyolefin-based resin, polycycloolefin-based resin, etc.) or a polyethylene terephthalate-based resin, and the retardation value can be easily controlled, A cellulosic resin or polyolefin resin is preferable at the point that it is also easy to obtain. The zero retardation film can be used also as a protective film. As a zero retardation film, "Z-TAC" (trade name) sold by Fujifilm Co., Ltd., "Zerotac (registered trademark)" sold by Konica Minolta Opt Co., Ltd., sold by Nippon Xeon Co., Ltd. "ZF-14" (brand name) etc. are mentioned.

The optical film of this invention WHEREIN: As for the retardation film, the retardation film which expressed optical anisotropy by application|coating and orientation of a liquid crystalline compound is preferable.

As a film in which optical anisotropy was expressed by application|coating and orientation of a liquid crystalline compound, the following 1st aspect - 5th aspect are mentioned.

1st form: retardation film in which the rod-shaped liquid crystal compound was oriented in the horizontal direction with respect to the supporting base material

Second form: retardation film in which the rod-shaped liquid crystal compound is oriented in a direction perpendicular to the supporting substrate

Third form: retardation film in which the direction of orientation of the rod-shaped liquid crystal compound is changed in a spiral in plane

4th form: retardation film in which disc-shaped liquid crystal compound is diagonally oriented

Fifth aspect: a biaxial retardation film in which a disk-shaped liquid crystal compound is oriented in a direction perpendicular to a supporting substrate

For example, a 1st aspect, a 2nd aspect, and a 5th aspect are used preferably for the optical film used for an organic electroluminescent display. Alternatively, these types of retardation films may be laminated and used.

When the retardation film is a layer containing a polymer in an orientation state of the polymerizable liquid crystal compound (hereinafter, sometimes referred to as an "optically anisotropic layer"), the retardation film preferably has reverse wavelength dispersion. Reverse wavelength dispersion is an optical characteristic in which the liquid crystal alignment in-plane retardation value at a short wavelength becomes smaller than the liquid crystal alignment in-plane retardation value at a long wavelength, and preferably, the retardation film satisfies the following formulas (7) and (8) will be. In addition, 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 the first aspect and has reverse wavelength dispersion, it is preferable because coloring at the time of black display in a display device is reduced, and 0.82≤Re in the above formula (7) (450)/Re(550) ? 0.93 is more preferable. Further, 120≤Re(550)≤150 is preferable.

As a polymerizable liquid crystal compound in the case where the retardation film is a film having an optically anisotropic layer, "3.8.6 network (completely crosslinked type)" )", "6.5.1 Liquid crystal material b. A compound having a polymerizable group among the compounds described in "polymerizable nematic liquid crystal material", and JP-A-2010-31223, JP-A-2010-270108 , JP-A-2011-6360 , JP 2011- The polymerizable liquid crystal compound of Unexamined-Japanese-Patent No. 207765, 2011-162678, Unexamined-Japanese-Patent No. 2016-81035, International Publication No. 2017/043438, and Unexamined-Japanese-Patent No. 2011-207765, etc. are mentioned.

As for the method of manufacturing a retardation film with the polymer in the orientation state of a polymeric liquid crystal compound, the method etc. of Unexamined-Japanese-Patent No. 2010-31223 are mentioned, for example.

In the case of the second aspect, 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 R _th in the thickness direction is -10 to - What is necessary is just to adjust in the range of 300 nm, Preferably it is the range of -20 to -200 nm. The retardation value in the thickness direction (R _th ), which means the refractive index anisotropy in the thickness direction, is calculated from the phase difference value (R ₅₀ ) and the in-plane retardation value (R ₀ ) measured by tilting the in-plane fast axis by 50 degrees with the inclination axis can do. That is, the retardation value (R _th ) in the thickness direction is the in-plane retardation value (R ₀ ), the retardation value measured by tilting the fast axis by 50 degrees with the inclination axis (R ₅₀ ), the thickness (d) and retardation of the retardation film From the average refractive index (n ₀ ) of the film, n _x , n _y and n _z can be obtained by the following formulas (10) to (12), and can be calculated by substituting these into the formula (9).

R _th =[(n _x +n _y )/2-n _z ]×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

As a film in which optical anisotropy is expressed by application and orientation of a liquid crystalline compound or a film in which optical anisotropy is expressed by application of an inorganic layered compound, a film called a temperature compensation retardation film, manufactured by JX Nikko Nisseki Energi Co., Ltd. "NH Film" (trade name; film with an oblique orientation of rod-shaped liquid crystal) sold by Fujifilm, "WV film" sold by FUJIFILM (brand name; film with disc-shaped liquid crystal oriented obliquely), Sumitomo Chemical ( "VAC film" (trade name; fully biaxially oriented film) sold by Sumitomo Chemical Co., Ltd. and "new VAC film" (trade name; biaxially oriented film) sold by Sumitomo Chemical Co., Ltd. are mentioned.

The retardation film may be a multilayer film having two or more layers. For example, a protective film is laminated on one side or both sides of the retardation film, or two or more retardation films are laminated through an adhesive or an adhesive.

An example of the laminated body in which the peeling film was provided in the adhesive layer of this invention, the optical film with an adhesive layer of this invention, and an example of the laminated structure of an optical laminated body are shown in FIGS.

The laminate 10 in which the release film is provided on the pressure-sensitive adhesive layer shown in FIG. 1 is a release film (separate film) on the pressure-sensitive adhesive layer 1 surface for temporary protection of the pressure-sensitive adhesive layer 1 surface formed from the pressure-sensitive adhesive composition of the present invention. )(2) is attached.

The optical film 10A with an adhesive layer described in FIG. 2 is the protective film 3, the adhesive bond layer 4, the polarizing film 5, the adhesive layer 1 formed from the adhesive composition of this invention, and the peeling film 2 ) is an optical film with a pressure-sensitive adhesive layer containing. The protective film 3, the adhesive layer 4, and the polarizing film 5 constitute the polarizing plate 100 (optical film 40). The protective film 3 may have a phase difference. Moreover, on the protective film 3, the hard-coat layer etc. may be further laminated|stacked.

The optical film 10B with an adhesive layer described in FIG. 3 is the protective film 3, the adhesive bond layer 4, the polarizing film 5, the adhesive bond layer 7, the protective film 6, The adhesive composition of this invention It is an optical film with a pressure-sensitive adhesive layer comprising a pressure-sensitive adhesive layer (1), retardation film (8) formed of. The protective film 3 , the adhesive layer 4 , the polarizing film 5 , the adhesive layer 7 , and the protective film 6 constitute the polarizing plate 100 (optical film 40 ).

The optical laminated body 10C described in FIG. 4 and the optical laminated body 10D described in FIG. 5 were formed from the protective film 3, the adhesive bond layer 4, the polarizing film 5, and the adhesive composition of this invention It is an optical laminated body containing the adhesive layer 1, the retardation film 110 (optical film 40), the adhesive layer 1a, and the light emitting element 30 (liquid crystal cell, organic electroluminescent cell). The protective film 3, the adhesive layer 4, and the polarizing film 5 constitute the polarizing plate 100 (optical film 40). The pressure-sensitive adhesive layer 1a may be a pressure-sensitive adhesive layer made of a known pressure-sensitive adhesive composition, or may be a pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition of the present invention.

As shown in FIGS. 4 and 5, when the retardation film is a multilayer film, as shown in FIG. 4, a quarter-wave retardation layer 70 that imparts a phase difference of 1/4 wavelength to the transmitted light and the transmitted light A configuration comprising a retardation film 110 (optical film 40) in which a half-wave retardation layer 50 that imparts a retardation of half a wavelength is laminated through an adhesive layer or an adhesive layer 60 can be heard In addition, as shown in FIG. 5 , a retardation film 110 (optical film 40) in which a quarter-wave retardation layer 50a and a positive C layer 80 are laminated through an adhesive layer or an adhesive layer 60 )) may be included.

The quarter-wave retardation layer 70 and the 1/2-wave retardation layer 50 that imparts a phase difference of 1/4 wavelength to the transmitted light and the half-wave retardation layer 50 of FIG. 4 are of the first type. An optical film or the optical film of a 5th aspect may be sufficient. In the case of the structure of FIG. 4, it is more preferable that at least one is a 5th aspect.

In the case of the configuration of FIG. 5 , the 1/4 wavelength retardation layer 50a is preferably an optical film of the first aspect, and more preferably, further satisfies the formulas (7) and (8).

<Liquid crystal display device>

An optical film with a pressure-sensitive adhesive layer comprising the pressure-sensitive adhesive composition of the present invention and a pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition is an optical laminate laminated on a display element such as an organic EL element and a liquid crystal cell, and an organic EL display device or a liquid crystal display device It can be used for display devices such as

Example

Hereinafter, although an Example and a comparative example are shown and this invention is demonstrated more concretely, this invention is not limited by these examples. In the examples, percentages and parts indicating the content or the amount used are based on mass unless otherwise specified.

(Synthesis Example 1) Synthesis of the compound represented by the formula (UVA-1)

The inside of a 500 mL-4 necked flask equipped with a Dimrode cooling tube and a thermometer was made into nitrogen atmosphere, 20 parts of dimedone, 11.2 parts of pyrrolidine, and 200 parts of toluene were added, and it refluxed and stirred for 5 hours. The solvent was distilled off from the obtained mixture, and it refine|purified, and 27.4 parts of compounds represented by Formula (M-3) were obtained.

In a nitrogen atmosphere, 1.0 parts of the compound represented by the obtained formula (M-3), 2.8 parts of para-toluenesulfonylcyanide, and 10 parts of acetonitrile were mixed. The resulting mixture was stirred at 0 to 5°C for 5 hours. The solvent was distilled off from the obtained mixture, and it refine|purified, and obtained 0.6 part of compound represented by Formula (M-4).

In a nitrogen atmosphere, 4.8 parts of the compound represented by the formula (M-4), 4.6 parts of methyl triflate, and 24 parts of acetonitrile were mixed and stirred at 20 to 30°C for 3 hours. 1.9 parts of malononitrile, 3 parts of triethylamine, and 24 parts of acetonitrile were added to the obtained mixture, and it stirred at 20-30 degreeC for 3 hours. The solvent was distilled off from the obtained mixture, and it refine|purified, and obtained 2.9 parts of the compound (Hereinafter, it may be called compound (UVA-1)) represented by Formula (UVA-1).

LC-MS measurement and ¹ H-NMR analysis were performed to confirm that the compound (UVA-1) was produced.

¹ H-NMR (CDCl3) δ: 0.99 (s, 6H), 1.90-1.96 (m, 4H), 2.48-2.51 (m, 4H), 3.70-3.88 (dt, 4H)

LC-MS; [M+H] ⁺ =267.5

<Measurement of maximum absorption wavelength and gram extinction coefficient ε>

A 2-butanone solution (0.006 g/L) of the obtained compound (UVA-1) was placed in a 1 cm quartz cell, and the quartz cell was set in a spectrophotometer UV-2450 (manufactured by Shimadzu Corporation), The absorbance in the wavelength range of 300 to 800 nm was measured for every 1 nm step by the double beam method. The gram extinction coefficient for each wavelength was calculated from the obtained absorbance value, the concentration of the compound (UVA-1) in the solution, and the optical path length of the quartz cell.

ε(λ)=A(λ)/CL

[wherein ε(λ) represents the gram extinction coefficient (L/(g·cm)) of compound (UVA-1) at a wavelength of λ nm, and A(λ) represents the absorbance at a wavelength of λ nm where C represents the concentration (g/L) of the compound (UVA-1) in the solution, and L represents the optical path length (cm) of the quartz cell.]

The maximum absorption wavelength of the obtained compound (UVA-1) was 380.2 nm. ε(380) of the obtained compound (UVA-1) was 184.8 L/(g·cm), ε(420) was 0.5 L/(g·cm), and ε(380)/ε(420) was 369.6.

(Polymerization Example 1): Preparation of acrylic resin (A1)

A mixed solution of 81.8 parts of ethyl acetate, 96 parts of butyl acrylate, 3 parts of 2-hydroxyethylmethyl acrylate, and 1 part of acrylic acid was introduced into a reaction vessel equipped with a cooling tube, a nitrogen introduction tube, a thermometer and a stirrer as a solvent, and was heated with nitrogen gas. The internal temperature was raised to 55°C while replacing the air in the device to make it oxygen-free. Then, the whole amount of the solution which melt|dissolved 0.14 part of azobisisobutyronitrile (polymerization initiator) in 10 parts of ethyl acetate was added. After adding the initiator, this temperature was maintained for 1 hour, and then ethyl acetate was continuously added into the reaction vessel at an addition rate of 17.3 parts/hr while maintaining the internal temperature at 54 to 56°C, and the concentration of the acrylic resin was 35%. At this point, the addition of ethyl acetate was stopped, and the temperature was kept at this temperature until 12 hours had elapsed from the start of the addition of ethyl acetate. Finally, ethyl acetate was added to adjust the concentration of the acrylic resin to 20% to prepare an ethyl acetate solution of the acrylic resin. As for the obtained acrylic resin, the weight average molecular weight (Mw) of polystyrene conversion by GPC was 1.47 million, and Mw/Mn was 5.5. Let this be an acrylic resin (A1). In addition, the obtained acrylic resin (A1) did not show maximum absorption in the range of wavelength 300 nm - 780 nm.

(Polymerization Example 2): Preparation of light selective absorption resin (C)

To a reaction vessel equipped with a cooling tube, a nitrogen introduction tube, a thermometer and a stirrer, 50 parts of toluene, 50 parts of methyl ethyl ketone, 50 parts of methyl methacrylate, 2-[2-(2-hydroxy-4-octyloxyphenyl)- 50 parts of 2H-1,2,3-benzotriazol-5-yloxy]ethyl methacrylate and 0.6 parts of azobisisobutyronitrile (polymerization initiator) were added, and the air in the device was replaced with nitrogen gas to eliminate oxygen while raising the internal temperature to 90°C, and refluxing for 10 hours to carry out polymerization. Then, 10 parts of toluene and 10 parts of methyl ethyl ketone were added so that the concentration of the light selective absorption resin (C) was 40%.

In addition, the photoselective absorption resin (C) showed maximum absorption at a wavelength of 348 nm.

(Example 1): Preparation of the pressure-sensitive adhesive composition (1)

With respect to 100 parts of solid content of the ethyl acetate solution (resin concentration: 20%) of the acrylic resin (A1) as the resin (A), a crosslinking agent (F) (manufactured by Tosoh Corporation: trade name "Colonate L", an isocyanate compound , solid content 75%) 0.3 parts, silane compound (G) (manufactured by Shin-Etsu Chemical Co., Ltd.: trade name "KBM3066") 0.28 parts, radical curable component (E) (manufactured by Shin-Nakamura Chemical Co., Ltd.: Trade name "A-DPH-12E", hexafunctional (meth)acrylate compound) 10 parts, initiator (D) (made by ADEKA Corporation: trade name "NCI-730", optical radical generator which is an oxime ester compound) ) 1.5 parts, 2 parts of the light-selective absorption compound (B) (compound (UVA-1)), and 10 parts of the solid content of the solution containing the light-selective absorption resin (C) synthesized in Polymerization Example 2 are mixed, and the solid content concentration is 14% Ethyl acetate was added so that the pressure-sensitive adhesive composition (1) was obtained. Here, the compounding quantity of the said crosslinking agent is a part by mass as an active ingredient.

Examples 2 to 5 and Comparative Examples 1 to 5

As shown in Table 1, except having changed each component and content of each component, it carried out similarly to Example 1, and produced the adhesive composition (2) - the adhesive composition (10). In addition, the compounding quantity of a crosslinking agent is mass parts as an active ingredient, and an acrylic resin (A1) and a light selective absorption resin (C) are mass parts of solid content.

The abbreviation in Table 1 shows what was described below, respectively.

<Resin (A)>

Acrylic resin (A1): Acrylic resin (A1) prepared in Polymerization Example 1

<Light Selective Absorption Compound (B)>

Compound (UVA-1): a compound represented by the formula (UVA-1) synthesized in Synthesis Example 1

<Light selective absorption resin (C)>

Light selective absorption resin (C): Light selective absorption resin (C) prepared in Polymerization Example 2

<Initiator (D)>

NCI-730: manufactured by ADEKA Corporation, trade name: NCI-730, oxime ester-based photoradical generator

<Radically curable component (E)>

A-DPH-12E: manufactured by Shin-Nakamura Chemical Co., Ltd., trade name: A-DPH-12E, hexafunctional (meth)acrylate compound

<Crosslinking agent (F)>

Colonate L: manufactured by Tosoh Corporation, trade name: Colonate L, isocyanate-based crosslinking agent

<Silane compound (G)>

KBM3066: manufactured by Shin-Etsu Chemical Co., Ltd., trade name: KBM3066, silane coupling agent

<Ultraviolet absorbent>

SB107: Cipro Chemicals Co., Ltd., benzophenone-based ultraviolet absorber, trade name: SEESORB107, maximum absorption wavelength λmax=350 nm

SB707: Cipro Chemicals Co., Ltd., benzotriazole-based ultraviolet absorber, trade name: SEESORB707, maximum absorption wavelength λmax=343 nm

RUVA-93: manufactured by Otsuka Chemical Co., Ltd., benzotriazole-based ultraviolet absorber, trade name: RUVA-93, maximum absorption wavelength λmax=337 nm

<Preparation of adhesive layer>

Each pressure-sensitive adhesive composition prepared above is applied to the release treatment side of a separate film containing a polyethylene terephthalate film subjected to release treatment (trade name “PLR-382190” obtained from Lintech Co., Ltd.), after drying using an applicator. The coating was applied to a thickness of 5 μm, and dried at 100° C. for 1 minute. Then, from the separate film side, using an ultraviolet irradiation device (“electrodeless UV lamp system H bulb” manufactured by Fusion UV Systems), UV-A (wavelength 320 to 390 nm) was irradiated at 500 mW, and the accumulated light amount was 500 mJ. It adjusted so that it might become possible, and the adhesive layer (pressure-sensitive adhesive sheet) was produced by irradiating an ultraviolet-ray.

<Measurement of absorbance of adhesive layer>

Each of the obtained pressure-sensitive adhesive layers was bonded to glass and the separate film was peeled off, and then a cycloolefin polymer (COP) film (ZF-14 manufactured by Nippon Zeon Corporation) was bonded to the pressure-sensitive adhesive layer to form a COP film/adhesive layer/glass A laminate having the configuration was produced. The produced laminate was set in a spectrophotometer UV-2450 (manufactured by Shimadzu Corporation), and absorbance was measured in a wavelength range of 300 to 800 nm in 1 nm steps by a double beam method. Table 2 shows the absorbance A (380) of the produced pressure-sensitive adhesive layer at a wavelength of 380 nm. In addition, both the absorbance of the glass in wavelength 380nm and the absorbance of a COP film are 0. A result is shown in Table 2.

<Evaluation of the bleed resistance of the adhesive layer>

A separate film was further laminated|stacked on the surface of the obtained adhesive layer, and the adhesive layer with a double-sided separate film was obtained. The obtained pressure-sensitive adhesive layer with a double-sided separate film was stored in air at 23 to 25°C for one month. The presence or absence of crystallization of the compound in surface was confirmed for the adhesive layer with a double-sided separate film after storage using the microscope. When there was no crystallization, it was set as "○", and when there was crystallization, it was set as "x". Table 2 shows the evaluation results.

Even if the pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition of the present invention is a thin layer having a thickness of less than 12 µm, the absorbance at a wavelength of 380 nm is high as 0.50 or more, has sufficient ultraviolet absorption performance, and has good bleed resistance.

The adhesive composition of this invention and the optical film with an adhesive layer containing the adhesive layer formed from the said adhesive composition are used suitably for a liquid crystal panel and a liquid crystal display device.

1: pressure-sensitive adhesive layer formed of the pressure-sensitive adhesive composition of the present invention, 1a: pressure-sensitive adhesive layer, 2: release film, 10: laminate, 10A, 10B: optical film with a pressure-sensitive adhesive layer, 10C, 10D: optical laminate, 3, 6: protection Film, 4, 7: adhesive layer, 5: polarizing film, 8: retardation film, 30: light emitting element, 40: optical film, 70, 50a: 1/4 wavelength retardation layer, 60: adhesive layer or pressure-sensitive adhesive layer, 50: 1/2 wavelength retardation layer, 80: positive C layer, 100: polarizing plate, 110: retardation film.

Claims (23)

resin (A);
A photoselective absorption compound (B) containing a merocyanine structure in a molecule and exhibiting maximum absorption at a wavelength of 360 nm or more, and
A pressure-sensitive adhesive composition comprising a light-selective absorption resin (C) having a maximum absorption at a wavelength of 300 nm or more and less than 360 nm. The pressure-sensitive adhesive composition according to claim 1, further comprising a radical curable component (E). The pressure-sensitive adhesive composition according to claim 2, wherein the radical curable component (E) is a (meth)acrylate-based compound. The pressure-sensitive adhesive composition according to claim 2 or 3, wherein the radical curable component (E) is a polyfunctional (meth)acrylate-based compound. The pressure-sensitive adhesive composition according to any one of claims 1 to 4, further comprising a radical initiator (D). The pressure-sensitive adhesive composition according to claim 5, wherein the radical initiator (D) is an optical radical generator. The pressure-sensitive adhesive composition according to claim 5 or 6, wherein the radical initiator (D) is an oxime ester-based photo-radical generator. The pressure-sensitive adhesive composition according to any one of claims 1 to 7, further comprising a crosslinking agent (F). The pressure-sensitive adhesive composition according to claim 8, wherein the crosslinking agent (F) is an isocyanate-based crosslinking agent. The adhesive composition of any one of Claims 1-9 whose glass transition temperature of resin (A) is 40 degrees C or less. The pressure-sensitive adhesive composition according to claim 10, wherein the resin (A) having a glass transition temperature of 40°C or less is a (meth)acrylic resin. The pressure-sensitive adhesive according to any one of claims 1 to 11, wherein the photoselective absorption compound (B) containing a merocyanine structure in a molecule and exhibiting maximum absorption at a wavelength of 360 nm or more satisfies the following formula (1) composition.
ε(380)≥25 (1)
[In formula (1), ε(380) represents the gram extinction coefficient at a wavelength of 380 nm of the light-selective absorption compound (B) having a merocyanine structure in the molecule and exhibiting maximum absorption at a wavelength of 360 nm or more. The unit of the gram extinction coefficient is L/(g·cm)] The pressure-sensitive adhesive according to any one of claims 1 to 12, wherein the photoselective absorption compound (B) containing a merocyanine structure in a molecule and exhibiting maximum absorption at a wavelength of 360 nm or more satisfies the following formula (2) composition.
ε(380)/ε(420)≥20 (2)
[In formula (2), ε(380) is the gram extinction coefficient of the resin at a wavelength of 380 nm of the photoselective absorption compound (B) that contains a merocyanine structure in the molecule and exhibits maximum absorption at a wavelength of 360 nm or more. indicate,
ε (420) represents the gram extinction coefficient of the light-selective absorption compound (B) at a wavelength of 420 nm of the light-selective absorption compound (B) having a merocyanine structure in the molecule and exhibiting maximum absorption at a wavelength of 360 nm or more .] The photoselective absorption compound (B) which contains a merocyanine structure in a molecule|numerator and shows maximum absorption at a wavelength of 360 nm or more according to any one of Claims 1-13 is a compound represented by Formula (Y) adhesive composition.

[In formula (Y),
R ^Y3 , R ^Y4 and R ^Y5 each independently represent an electron withdrawing group.
R ^Y1 , R ^Y2 , R ^Y6 and R ^Y7 are each independently a hydrogen atom, a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxy group, a thiol group, a carboxy group, -SCF ₃ , -SF ₅ , -SF ₃ , - SO ₃ H, —SO ₂ H, 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, and —CH contained in the aliphatic hydrocarbon group or aromatic hydrocarbon group ₂ - or -CH= is -NR ^1A -, -SO ₂ -, -CO-, -O-, -COO-, -OCO-, -CONR ^2A -, -NR ^3A -CO-, -S-, -SO-, -SO ₂ -, -CF ₂ -, or -CHF- may be substituted.
R ^1A , R ^2A and R ^3A each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
R ^Y1 and R ^Y2 may be linked to each other to form a ring.
R ^Y1 and R ^Y6 may be linked to each other to form a ring.
R ^Y4 and R ^Y5 may be linked to each other to form a ring.] The photoselective absorption compound (B) which contains a merocyanine structure in a molecule|numerator and shows maximal absorption at a wavelength of 360 nm or more according to any one of Claims 1-13, molecular weight is 3000 or less, and has the formula (X ), which is a compound having a partial structure represented by the pressure-sensitive adhesive composition.

[In formula (X), ring W ¹ represents a ring structure having at least one double bond as a component of the ring and not having aromaticity.
R ³ is a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a thiol group, a carboxy group, -SF ₅ , -SF ₃ , -SO ₃ H, -SO ₂ H, optionally having 1 to 25 carbon atoms represents an aliphatic hydrocarbon group or an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent, and -CH ₂ - or -CH= contained in the aliphatic hydrocarbon group or aromatic hydrocarbon group is -O-, -S-, -NR ^1xA -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -CONR ^2xA -, -NR ^3xA -CO-, -O-CO-NR ^4xA -, -NR ^5xA -CO-O-, -NR ^6xA -CO-NR ^7xA -, -CO-S-, -S-CO-S-, -S-CO-NR ^8xA -, -NR ^9xA -CO-S-, -CS -, -O-CS-, -CS-O-, -NR ^10xA -CS-, -NR ^11xA -CS-S-, -S-CS-, -CS-S-, -S-CS-S-, -SO- or -SO ₂ - may be substituted.
R ^1xA , R ^2xA , R ^3xA , R 4xA , R ^5xA , R ^6xA , R ^7xA , R ^8xA , R ^x9A , R ^10xA and R ^11xA each independently ^represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.] The pressure-sensitive adhesive composition according to claim 15, wherein the compound having a molecular weight of 3000 or less and having a partial structure represented by the formula (X) is any one of the compounds represented by the compound represented by the formula (I) to the compound represented by the formula (VIII).

[In formulas (I) to (VIII),
Rings W ¹ and R ³ have the same meanings as above.
Ring W ² , Ring W ³ , Ring W ⁴ , Ring W ⁵ , Ring W ⁶ , Ring W ⁷ , Ring W ⁸ , Ring W ⁹ , Ring W ¹⁰ , Ring W ¹¹ and Ring W ¹² are each independently It represents a ring structure having at least one double bond as a component.
Ring W ¹¹¹ represents a ring having at least two nitrogen atoms as a component.
Ring W ¹¹² and ring W ¹¹³ each independently represent a ring having at least one nitrogen atom as a constituent element.
R ¹ , R ⁴¹ , R ⁵¹ , R ⁶¹ , R ⁹¹ , R ¹⁰¹ , R ¹¹¹ , R ² , R ¹² , R ⁴² , R ⁵² , R ⁶² , R ⁷² , R ⁸² , R ⁹² , R ¹⁰² and R ¹¹² . are each independently a hydrogen atom, a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a thiol group, a carboxy group, -SF ₅ , -SF ₃ , -SO ₃ H, -SO ₂ H, which may have a substituent represents an aliphatic hydrocarbon group having 1 to 25 carbon atoms or an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent, and -CH ₂ - or -CH= contained in the aliphatic hydrocarbon group or aromatic hydrocarbon group is -NR ^12A -, - SO ₂ -, -CO-, -O-, -COO-, -OCO-, -CONR ^13A -, -NR ^14A -CO-, -S-, -SO-, -CF ₂ - or -CHF- it may be good
R ¹³ , R ²³ , R ³³ , R ⁴³ , R ⁵³ , R ⁶³ , R ⁷³ , R ⁸³ , R ⁹³ , R ¹⁰³ and R ¹¹³ are each independently a heterocyclic group, a halogen atom, a nitro group, a cyano group, or a hydroxyl group , thiol group, carboxyl group, -SF ₅ , -SF ₃ , -SO ₃ H, -SO ₂ H, an aliphatic hydrocarbon group having 1 to 25 carbon atoms which may have a substituent or an aromatic hydrocarbon having 6 to 18 carbon atoms which may have a substituent group and -CH ₂ - or -CH= contained in this aliphatic hydrocarbon group or aromatic hydrocarbon group is -O-, -S-, -NR ^1A -, -CO-, -CO-O-, -O-CO -, -O-CO-O-, -CONR ^2A -, -NR ^3A -CO-, -O-CO-NR ^4A -, -NR ^5A -CO-O-, -NR ^6A -CO-NR ^7A -, -CO-S-, -S-CO-S-, -S-CO-NR ^8A -, -NR ^9A -CO-S-, -CS-, -O-CS-, -CS-O-, -NR ^10A -CS-, -NR ^11A -CS-S-, -S-CS-, -CS-S-, -S-CS-S-, -SO-, or -SO ₂ - may be substituted.
R ^1A , R ^2A , R ^3A , R ^4A , R ^5A , R ^6A , R ^7A , R ^8A , R ^9A , R ^10A , R ^11A , R ^12A , R ^13A and R ^14A are each independently a hydrogen atom or carbon number An alkyl group of 1-6 is represented.
R ⁴ , R ¹⁴ , R ²⁴ , R ³⁴ , R ⁴⁴ , R ⁵⁴ , R ⁶⁴ , R ⁷⁴ , R ⁸⁴ , R ⁹⁴ , R ¹⁰⁴ , R ¹¹⁴ , R ⁵ , R ¹⁵ , R ²⁵ , R ³⁵ , R ⁷⁵ and R ⁸⁵ each independently represents an electron withdrawing group.
R ¹ and R ² may be bonded to each other to form a ring.
R ⁴¹ and R ⁴² may be bonded to each other to form a ring.
R ⁵¹ and R ⁵² may be bonded to each other to form a ring.
R ⁶¹ and R ⁶² may be bonded to each other to form a ring.
R ⁹¹ and R ⁹² may be bonded to each other to form a ring.
R ¹⁰¹ and R ¹⁰² may combine with each other to form a ring.
R ¹¹¹ and R ¹¹² may be bonded to each other to form a ring.
R ² and R ³ may be bonded to each other to form a ring.
R ¹² and R ¹³ may be bonded to each other to form a ring.
R ⁴² and R ⁴³ may be bonded to each other to form a ring.
R ⁵² and R ⁵³ may be bonded to each other to form a ring.
R ⁶² and R ⁶³ may be bonded to each other to form a ring.
R ⁷² and R ⁷³ may be bonded to each other to form a ring.
R ⁸² and R ⁸³ may be bonded to each other to form a ring.
R ⁹² and R ⁹³ may be bonded to each other to form a ring.
R ¹⁰² and R ¹⁰³ may be bonded to each other to form a ring.
R ¹¹² and R ¹¹³ may be bonded to each other to form a ring.
R ⁴ and R ⁵ may be bonded to each other to form a ring.
R ¹⁴ and R ¹⁵ may be bonded to each other to form a ring.
R ²⁴ and R ²⁵ may be bonded to each other to form a ring.
R ³⁴ and R ³⁵ may combine with each other to form a ring.
R ⁷⁴ and R ⁷⁵ may be bonded to each other to form a ring.
R ⁸⁴ and R ⁸⁵ may be bonded to each other to form a ring.
R ⁶ and R ⁸ each independently represent a divalent linking group.
R ⁷ represents a single bond or a divalent linking group.
R ⁹ and R ¹⁰ each independently represent a trivalent linking group.
R ¹¹ represents a tetravalent linking group.] A pressure-sensitive adhesive layer formed of the pressure-sensitive adhesive composition according to any one of claims 1 to 16. The pressure-sensitive adhesive layer according to claim 17, which satisfies the following formula (3).
A(380)≥0.60 (3)
[In formula (3), A (380) represents the absorbance at a wavelength of 380 nm.] The pressure-sensitive adhesive layer according to claim 17 or 18, further satisfying the following formula (4).
A(380)/A(420)≥5 (4)
[In formula (4), A (380) represents the absorbance at a wavelength of 380 nm, and A (420) represents the absorbance at a wavelength of 420 nm.] The pressure-sensitive adhesive layer according to any one of claims 17 to 19, wherein the pressure-sensitive adhesive layer has a film thickness of 10 µm or less. The optical film with an adhesive layer in which the optical film was laminated|stacked on at least one surface of the adhesive layer in any one of Claims 17-20. The optical film with a pressure-sensitive adhesive layer according to claim 21, wherein the optical film is a polarizing plate. The image display device containing the optical film with an adhesive layer of Claim 21 or 22.

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