TWI819053B - Resin and adhesive composition - Google Patents

Abstract

Resin (A) contains a structural unit having an indole structure. The resin (A) is preferably a resin containing a structural unit having an indole structure in the side chain, and preferably has a glass transition temperature of 40℃ or lower. Moreover, resin (A) is preferably a resin which satisfy the formula (1).

ε(405) ≧ 0.02 (1)

[In formula (1), ε (405) represents the gram extinction coefficient of the resin (A) at a wavelength of 405 nm. The unit of the gram extinction coefficient is L / (g ． cm).]

Description

Resin and adhesive compositions

The present invention relates to an optical laminate in which an adhesive layer formed of a resin, an adhesive composition containing the resin, and the adhesive composition is laminated.

Various components such as organic EL elements, display elements such as liquid crystal cells, and optical films such as polarizing plates are used in display devices (EPD: flat panel displays) such as organic electroluminescence displays (organic EL display devices) and liquid crystal display devices. Among these components, organic EL light-emitting elements, liquid crystal compounds, and the like are organic substances and are prone to degradation due to ultraviolet rays (UV). Furthermore, it is known that liquid crystal retardation films and organic EL light-emitting elements formed by aligning and photocuring polymerizable liquid crystal compounds tend to deteriorate not only by ultraviolet rays but also by short-wavelength visible light. In order to solve the above-mentioned problems, it is known to provide a layer containing a light compound that absorbs short-wavelength visible light. For example, Patent Document 1 describes a polarizing plate with an adhesive layer formed of an adhesive composition containing n-butyl acrylate, 2-hydroxyethyl acrylate, and N,N-di Copolymer of methacrylamide and indole ultraviolet absorber.

[Prior technical literature] [Patent Document]

[Patent Document 1] Japanese Patent Application Publication No. 2017-48340

However, when the adhesive layer containing an ultraviolet absorber described in Patent Document 1 is used as an optical laminate, it is possible to suppress deterioration due to ultraviolet rays and short-wavelength visible light. However, it has been found that migration of the ultraviolet absorber to other layers occurs. and other problems that impair optical properties. Among them, it was found that in a laminated body having a liquid crystal-based retardation film, the degradation in optical properties (change in retardation value) caused by migration of the ultraviolet absorber to other layers becomes significant.

The present invention includes the following inventions.

[1] A resin (A) containing a structural unit having an indole structure.

[2] The resin according to [1], wherein the glass transition temperature of the resin (A) is 40°C or lower.

[3] The resin according to [1] or [2], wherein the resin (A) satisfies the following formula (1),

ε(405)≧0.02 (1)

[In the formula (1), ε (405) represents the gram absorption coefficient of the resin (A) at a wavelength of 405 nm, and the unit of the gram absorption coefficient is L/(g·cm)].

[4] The resin according to any one of [1] to [3], wherein the resin (A) satisfies the following formula (2),

ε(405)/ε(440)≧5 (2)

[In the formula (2), ε(405) represents the gram absorption coefficient of the resin (A) at a wavelength of 405 nm, and ε(440) represents the gram absorption coefficient of the resin at a wavelength of 440 nm].

[5] The resin according to any one of [1] to [4], wherein the resin (A) is a resin containing a structural unit having an indole structure in a side chain.

[6] The resin according to [5], wherein the structural unit having an indole structure in the side chain is a structural unit derived from a light-selective absorbing compound having a polymerizable group and an indole structure.

[7] The resin according to [6], wherein the light-selective absorbing compound having a polymerizable group and an indole structure is a compound satisfying the following formula (1-a),

ε(405)≧5 (1-a)

[In formula (1-a), ε(405) represents the gram absorption coefficient of a compound having a polymerizable group and an indole structure at a wavelength of 405 nm, and the unit of the gram absorption coefficient is L/(g·cm)].

[8] The resin according to [7], wherein the light-selective absorbing compound having a polymerizable group and an indole structure is a compound satisfying the following formula (2-a);

ε(405)/ε(440)≧10 (2-a)

[In formula (2-a), ε(405) represents the gram absorption coefficient of a compound having a polymerizable group and an indole structure at a wavelength of 405 nm, and ε(440) represents a compound having a polymerizable group and an indole structure at a wavelength of 440 nm. gram absorption coefficient of the compound].

[9] The resin according to [5], wherein the structural unit having an indole structure in the side chain is a structural unit derived from a compound represented by formula (I) or a structural unit derived from a compound represented by formula (II);

[In formula (I), R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ each independently represent a hydrogen atom, a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a carboxyl group, and may have The substituent is an aliphatic hydrocarbon group having 1 to 25 carbon atoms or an aromatic hydrocarbon group having 6 to 18 carbon atoms that may have a substituent, and -CH ₂ - contained in the aliphatic hydrocarbon group or aromatic hydrocarbon group may be -NR ^1A -, -SO ₂ -, -CO-, -O-, -S- or -CF ₂ -substitution;

R ^1A represents a hydrogen atom, an alkyl group with 1 to 25 carbon atoms, or an aromatic hydrocarbon group with 6 to 18 carbon atoms;

E ¹ represents electron withdrawing group;

Z represents the linking group;

A represents a polymerizable group;

In formula (II), R ¹² and R ¹⁷ each independently represent a hydrogen atom, a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a carboxyl group, an aliphatic hydrocarbon group having 1 to 25 carbon atoms which may have a substituent, or An aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent. -CH ₂ - contained in the aliphatic hydrocarbon group or aromatic hydrocarbon group may be -NR ^11A -, -SO ₂ -, -CO-, -O- , -S- or -CF ₂ -substitution;

R ¹¹ , R ¹³ , R ¹⁴ , R ¹⁵ and R ¹⁶ each independently represent a hydrogen atom, a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a carboxyl group, a group containing a polymerizable group, and may have a substituent. 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 - contained in the aliphatic hydrocarbon group or aromatic hydrocarbon group may be -NR ^12A -, -SO ₂ -, -CO-, -O-, -S- or -CF ₂ -substituted;

However, at least one of R ¹¹ , R ¹³ , R ¹⁴ , R ¹⁵ and R ¹⁶ represents a group containing a polymerizable group;

R ^11A and R ^12A each independently represent a hydrogen atom, an alkyl group with 1 to 25 carbon atoms, or an aromatic hydrocarbon group with 6 to 18 carbon atoms;

E ¹¹ represents an electron-withdrawing group].

[10] The resin according to [9], wherein R ² is a phenyl group.

[11] The resin according to [9], wherein the compound represented by formula (I) is a compound represented by formula (III);

[R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ and E ¹ represent the same meanings as above;

R ⁷ represents a hydrogen atom, methyl or phenyl;

Z ¹ represents an alkanediyl group having 1 to 12 carbon atoms, a divalent aromatic hydrocarbon group having 6 to 18 carbon atoms, -OR ^2A -＊1, -SR ^2B -＊1 or -NR ^1D -R ^2C -＊1;

Z ² represents single bond, ＊2-CO-O-, ＊2-O-CO-, ＊2-S(=O) ₂ -, ＊2-O-SO ₂ -, ＊2-CO-NR ^1B - ,＊2-NR ^1C -CO-,＊2-R ^2D OP(=O)-OR ^2E -,＊2-NR ^1E -CO-O-,＊2-O-CO-NR ^1F -,＊2- (OR ^2F ) _s1 -, *2-CO-S-, *2-S-CO- or perfluoroalkyldiyl with 1 to 4 carbon atoms;

R ^1B , R ^1C , R ^1D , R ^1E and R ^1F each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms;

R ^2A , R ^2B , R ^2C , R ^2D , R ^2E and R ^2F each independently represent a divalent hydrocarbon group having 1 to 18 carbon atoms;

*1 indicates the bond with Z ² ;

*2 indicates the bonding bond with Z ¹ ].

[12] The resin according to any one of [1] to [11], wherein the resin (A) further has at least one structural unit selected from the structural units described in the following group A;

Group A: Structural unit derived from (meth)acrylate, structural unit derived from styrenic monomer, structural unit derived from vinyl monomer, structural unit derived from epoxy compound, represented by formula (a) The structural unit, the structural unit represented by formula (b) and the structural unit represented by formula (c);

[In the formula, R ^a1 represents a divalent hydrocarbon group;

R ^b1 and R ^b2 each independently represent a hydrogen atom or a hydrocarbon group;

R ^c1 and R ^c2 each independently represent a divalent hydrocarbon group].

[13] The resin according to [12], wherein the content of at least one structural unit derived from the structural units selected from the group A is 50 mass % or more relative to all the structural units of the resin (A).

[14] An adhesive composition containing the resin according to any one of [1] to [13].

[15] The adhesive composition according to [14], further comprising a cross-linking agent (B).

[16] An adhesive layer formed from the adhesive composition described in [14] or [15].

[17] The adhesive layer according to [16], which satisfies the following formula (3),

A(405)≧0.5 (3)

[In formula (3), A (405) represents the absorbance at a wavelength of 405 nm].

[18] The adhesive layer according to [17], which satisfies the following formula (4),

A(405)/A(440)≧5 (4)

[In formula (4), A (405) represents the absorbance at a wavelength of 405 nm; A (440) represents the absorbance at a wavelength of 440 nm].

[19] An optical laminate in which an optical film is laminated on at least one surface of the adhesive layer according to any one of [16] to [18].

[20] The optical laminate according to [19], wherein the optical film is a polarizing plate.

[21] An image display device including the optical laminate according to [20].

[22] A compound represented by formula (I) or formula (IV),

[In formula (I), R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ each independently represent a hydrogen atom, a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a carboxyl group, and may have The substituent is an aliphatic hydrocarbon group having 1 to 25 carbon atoms or an aromatic hydrocarbon group having 6 to 18 carbon atoms that may have a substituent, and -CH ₂ - contained in the aliphatic hydrocarbon group or aromatic hydrocarbon group may be -NR ^1A -, -SO ₂ -, -CO-, -O-, -S- or -CF ₂ -substitution;

R ^1A represents a hydrogen atom, an alkyl group with 1 to 25 carbon atoms, or an aromatic hydrocarbon group with 6 to 18 carbon atoms;

E ¹ represents an electron-withdrawing group;

Z represents the linking group;

A represents a polymerizable group;

In formula (IV), R ¹² and R ¹⁷ each independently represent a hydrogen atom, a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a carboxyl group, an aliphatic hydrocarbon group having 1 to 25 carbon atoms which may have a substituent, or An aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent, and -CH ₂ - contained in the aliphatic hydrocarbon group or aromatic hydrocarbon group may be -NR ^11A -, -SO ₂ -, -CO-, -O-, -S- or -CF ₂ -substitution;

R ¹¹ , R ¹³ , R ¹⁴ , R ¹⁵ and R ¹⁶ each independently represent a hydrogen atom, a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a carboxyl group, a group containing a polymerizable group, and may have a substituent an aliphatic hydrocarbon group with 1 to 25 carbon atoms or an aromatic hydrocarbon group with 6 to 18 carbon atoms that may have a substituent, and -CH ₂ - contained in the aliphatic hydrocarbon group or aromatic hydrocarbon group may be -NR ^12A -, - SO ₂ -, -CO-, -O-, -S- or -CF ₂ -substituted;

However, at least one of R ¹¹ , R ¹³ , R ¹⁴ , R ¹⁵ and R ¹⁶ represents a group containing a polymerizable group;

R ^11A and R ^12A each independently represent a hydrogen atom, an alkyl group with 1 to 25 carbon atoms, or an aromatic hydrocarbon group with 6 to 18 carbon atoms;

E ¹¹ represents an electron-withdrawing group].

[23] The compound according to [22], wherein R ² is phenyl.

[24] The compound according to [22], wherein the compound represented by formula (I) is a compound represented by formula (III);

[R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ and E ¹ represent the same meanings as above;

R ⁷ represents a hydrogen atom, cyano group, methyl group or phenyl group;

Z ¹ represents an alkanediyl group having 1 to 12 carbon atoms, a divalent aromatic hydrocarbon group having 6 to 18 carbon atoms, -OR ^2A -＊1, -SR ^2B -＊1 or -NR ^1D -R ^2C -＊1;

Z ² represents single bond, ＊2-CO-O-, ＊2-O-CO-, ＊2-S(=O) ₂ -, ＊2-O-SO ₂ -, ＊2-CO-NR ^1B - ,＊2-NR ^1C -CO-,＊2-R ^2D OP(=O)-OR ^2E -,＊2-NR ^1E -CO-O-,＊2-O-CO-NR ^1F -,＊2- (OR ^2F ) _s1 -, *2-CO-S-, *2-S-CO- or perfluoroalkyldiyl with 1 to 4 carbon atoms;

R ^1B , R ^1C , R ^1D , R ^1E and R ^1F each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms;

R ^2A , R ^2B , R ^2C , R ^2D , R ^2E and R ^2F each independently represent a divalent hydrocarbon group having 1 to 18 carbon atoms;

*1 indicates the bond with Z ² ;

*2 indicates the bonding bond with Z ¹ ].

[25] The compound according to any one of [22] to [24], wherein E ¹ is a cyano group.

The present invention provides an adhesive layer capable of suppressing deterioration of organic EL light-emitting elements and liquid crystal retardation films, and an adhesive composition forming the adhesive layer. Furthermore, the invention provides a resin capable of forming an adhesive composition that can effectively suppress deterioration of organic EL light-emitting elements and liquid crystal retardation films.

1‧‧‧Adhesive layer

2‧‧‧Peel-off film

10A, 10B, 10C, 10D‧‧‧Optical laminated body

8‧‧‧Protective film

7‧‧‧Adhesive layer

7a‧‧‧Adhesive layer

9‧‧‧Polarizing film

30‧‧‧Light-emitting components

40‧‧‧Optical film

50, 50a‧‧‧1/4 wavelength phase difference layer

60‧‧‧Adhesive layer or adhesive layer

70‧‧‧1/2 wavelength phase difference layer

80‧‧‧C Floor

100‧‧‧Polarizing plate

110‧‧‧Phase difference film

Figure 1 shows an example of the layer structure of the adhesive layer of the present invention.

Figure 2 shows an example of the layer structure of the optical laminate of the present invention.

Fig. 3 shows an example of the layer structure of the optical laminate of the present invention.

Fig. 4 shows an example of the layer structure of the optical laminate of the present invention.

Fig. 5 shows an example of the layer structure of the optical laminate of the present invention.

〈Adhesive composition〉

The adhesive composition of the present invention contains resin (A) containing a structural unit having an indole structure. The adhesive composition of the present invention further includes a cross-linking agent (B), a silane compound (D), an antistatic agent, etc.

〈Resin(A)〉

The resin (A) of the present invention is a resin containing a structural unit having an indole structure, preferably a resin containing a structural unit derived from a light-selective absorbing compound having an indole structure.

The glass transition temperature (T _g ) of the resin (A) is preferably 40°C or lower, more preferably 20°C or lower, even more preferably 10°C or lower, particularly preferably 0°C or lower. Furthermore, the glass transition temperature (T _g ) of the resin (A) is usually -80°C or higher, preferably -60°C or higher, and more preferably -50°C or higher. When the glass transition temperature (T _g ) of the resin (A) is 40° C. or lower, it is advantageous in improving the adhesion of the adhesive layer formed of the adhesive composition containing the resin (A) to the adherend. Furthermore, when the glass transition temperature (T _g ) of the resin (A) is -80° C. or higher, it is advantageous in improving the heat resistance of the adhesive layer formed of the adhesive composition containing the resin (A). In addition, the glass transition temperature can be measured by a differential scanning calorimeter (DSC).

The resin (A) is preferably a resin that satisfies the following formula (1).

ε(405)≧0.02 (1)

[In formula (1), ε(405) represents the gram absorption coefficient of the resin at a wavelength of 405 nm; the unit of the gram absorption coefficient is L/(g‧cm)].

In addition, the gram absorption coefficient of the resin (A) can be measured by the method described in the Examples.

The larger the value of ε (405) of resin (A), the easier it is to absorb light with a wavelength of 405 nm. The value of ε(405) is preferably 0.02L/(g‧cm) or more, more preferably 0.1L/(g‧cm) or more, even more preferably 0.2L/(g‧cm) or more, usually 10L/( g‧cm) or less.

When the adhesive composition containing resin (A) is applied to display devices such as organic EL display devices and liquid crystal display devices, when the ε(405) of the resin (A) is 0.02L/(g‧cm) or more, due to the near 400 nm It has good visible light absorption performance and can suppress deterioration caused by visible light in retardation films and organic EL light-emitting elements used in display devices such as organic EL displays and liquid crystal displays.

The resin (A) is preferably a resin that satisfies the following formula (2).

ε(405)/ε(440)≧5 (2)

[In the formula (2), ε(405) represents the gram absorption coefficient of the resin at a wavelength of 405 nm, and ε(440) represents the gram absorption coefficient of the resin at a wavelength of 440 nm].

The larger the value of ε(405)/ε(440) of the resin (A), the more selectively it can absorb light with a wavelength near 400 nm. The value of ε(405)/ε(440) is preferably 5 or more, more preferably 10 or more, and still more preferably 30 or more.

When ε(405)/ε(440) of resin (A) is 5 or more, when the adhesive composition containing resin (A) is applied to display devices such as organic EL display devices and liquid crystal display devices, it will not hinder the performance of the display device. Color expression, and can absorb visible light near 400nm to suppress photodegradation of the retardation film.

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

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

The light-selective absorbing compound having a polymerizable group and an indole structure preferably satisfies the following formula (1-a), and more preferably satisfies the following formula (2-a).

ε(405)≧5 (1-a)

[In formula (1-a), ε(405) represents the gram absorption coefficient of a compound having a polymerizable group and an indole structure at a wavelength of 405 nm, and the unit of the gram absorption coefficient is L/(g·cm)].

ε(405)/ε(440)≧10 (2-a)

[In formula (2-a), ε(405) represents the gram absorption coefficient of a compound having a polymerizable group and an indole structure at a wavelength of 405 nm, and ε(440) represents a compound having a polymerizable group and an indole structure at a wavelength of 440 nm. Gram absorption coefficient of compounds with indole structure].

For compounds with a polymerizable group and an indole structure, the value of ε(405) is preferably 5L/(g‧cm) or more, more preferably 10L/(g‧cm) or more, and even more preferably 20L/(g‧cm ) or more, more preferably 30L/(g‧cm) or more, usually 500L/(g‧cm) or less. The larger the value of ε (405), the easier it is to absorb light with a wavelength of 405 nm, and it is easier to suppress the degradation of visible light caused by ultraviolet rays and short wavelengths.

For a compound having a polymerizable group and an indole structure, the value of ε(405)/ε(440) is preferably 10 or more, and more preferably 15 or more. A compound with a larger value of ε(405)/ε(440) does not hinder the color expression of a display device and can absorb light with a wavelength near 405 nm to suppress light degradation of display devices such as retardation films and organic EL elements.

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

[In formula (I), R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ each independently represent a hydrogen atom, a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a carboxyl group, and may have The substituent is an aliphatic hydrocarbon group having 1 to 25 carbon atoms or an aromatic hydrocarbon group having 6 to 18 carbon atoms that may have a substituent, and -CH ₂ - contained in the aliphatic hydrocarbon group or aromatic hydrocarbon group may be -NR ^1A -, -SO ₂ -, -CO-, -O-, -S- or -CF ₂ -substitution;

R ^1A represents a hydrogen atom, an alkyl group with 1 to 25 carbon atoms, or an aromatic hydrocarbon group with 6 to 18 carbon atoms;

E ¹ represents an electron-withdrawing group;

Z represents the linking group;

A represents a polymerizable group;

In formula (II), R ¹² and R ¹⁷ each independently represent a hydrogen atom, a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a carboxyl group, an aliphatic hydrocarbon group having 1 to 25 carbon atoms which may have a substituent, or An aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent, and -CH ₂ - contained in the aliphatic hydrocarbon group or aromatic hydrocarbon group may be -NR ^11A -, -SO ₂ -, -CO-, -O-, -S- or -CF ₂ -substitution;

R ¹¹ , R ¹³ , R ¹⁴ , R ¹⁵ and R ¹⁶ each independently represent a hydrogen atom, a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a carboxyl group, a group containing a polymerizable group, and may have a substituent. 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 - contained in the aliphatic hydrocarbon group or aromatic hydrocarbon group may be -NR ^12A -, -SO ₂ -, -CO-, -O-, -S- or -CF ₂ -substituted;

However, at least one of R ¹¹ , R ¹³ , R ¹⁴ , R ¹⁵ and R ¹⁶ represents a group containing a polymerizable group;

R ^11A and R ^12A each independently represent a hydrogen atom, an alkyl group with 1 to 25 carbon atoms, or an aromatic hydrocarbon group with 6 to 18 carbon atoms;

E ¹¹ represents an electron-withdrawing group].

Examples of the electron-withdrawing group represented by E ¹ and E ¹¹ include a cyano group, a nitro group, a halogen atom, an alkyl group substituted with a halogen atom, and a group represented by formula (I-1).

＊-X ¹ -R ¹¹¹ (I-1)

[In the formula, R ¹¹¹ represents a hydrogen atom or a hydrocarbon group having 1 to 25 carbon atoms, and at least one of the methylene groups contained in the alkyl group may be substituted with an oxygen atom.

X ¹ means -CO-＊3, -COO-＊3, -CS-＊3, -CSS-＊3, -CSNR ¹¹² -＊3, -CONR ¹¹³ -＊3, -CNR ¹¹⁴ -＊3 or -SO _2- *3.

R ¹¹² , R ¹¹³ and R ¹¹⁴ each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group.

*3 indicates the bond with R ¹¹¹ .

* indicates a bond with a carbon atom. ]

Examples of the halogen atom include fluorine atom, chlorine atom, bromine atom and iodine atom.

Examples of alkyl groups substituted by halogen atoms include: monofluoromethyl, monofluoroethyl, monochloromethyl, monochloroethyl, monobromomethyl, monobromoethyl, monoiodomethyl, and monoiodoethyl , difluoromethyl, difluoroethyl, dichloromethyl, dichloroethyl, dibromomethyl, dibromoethyl, diiodomethyl, diiodoethyl, trifluoromethyl, trichloromethyl , tribromomethyl, triiodomethyl halogenated alkyl, etc. The carbon number of the alkyl group substituted by a halogen atom is usually 1 to 25.

Examples of the hydrocarbon group having 1 to 25 carbon atoms represented by R ¹¹¹ include methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, n-pentyl, and isopentyl. , n-hexyl, isohexyl, n-octyl, isooctyl, n-nonyl, isononyl, n-decyl, isodecyl, n-dodecyl, isododecanyl, undecyl, nutmeg Linear or branched chain alkyl groups with 1 to 25 carbon atoms such as hexadecyl, stearyl, etc.; cycloalkyl groups with 3 to 25 carbon atoms such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc. ; cycloalkylalkyl groups with 4 to 25 carbon atoms such as cyclopropylmethyl and cyclohexylmethyl; aryl groups with 6 to 25 carbon atoms such as phenyl, naphthyl, anthracenyl and biphenyl groups; benzyl, benzene Aralkyl groups with 7 to 25 carbon atoms such as ethyl group, naphthylmethyl group, and phenyl group.

Examples of the alkyl group having 1 to 6 carbon atoms represented by R ¹¹² , R ¹¹³ and R ¹¹⁴ include methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, etc. .

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

The polymerizable group represented by A is not particularly limited. For example, it may be a cationic polymerizable group, an anionic polymerizable group, or a radical polymerizable group. More specifically, examples include: alkenyl groups such as vinyl; epoxy groups; oxetanyl groups; vinyl ether groups; acrylonitrile groups; methacrylonitrile groups; vinyl groups, α-methylvinyl groups, and propylene groups. Ethylenically unsaturated groups such as acyl group, methacrylyl group, allyl group, styryl group, acrylamide group, methacrylamide group, etc.

Examples of the halogen atom represented by R ¹ to R ⁶ and R ¹¹ to R ¹⁷ include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

環基、吲哚環基、異吲哚環基、喹啉環基、噻吩環基、吡咯環基、噻唑啉環基、呋喃環基、吡啶環基、二噁烷環基、嗎啉環基、噻

環基、三唑環基、四唑環基、二氧呋喃環基、吡

環基、嘌呤環基等碳數4至30的脂肪族雜環基或碳數3至20的芳香族雜環基等。該等的雜環基可為不飽和鍵經氫化的結構，又，也可為環狀骨架經縮環的結構(例如苯，並咪唑環)、雜環上的氫原子更經雜環基、鹵原子、硝基、氰基、羥基、羧基等取代而成者。 Examples of the heterocyclic group represented by R ¹ to R ⁶ and R ¹¹ to R ¹⁷ include a group obtained by removing one hydrogen atom from the heterocyclic ring. Specific examples include: pyrrolidine ring, pyrroline ring group, imidazolinidine ring group, imidazoline ring group, oxazoline ring group, thiazoline ring group, piperidine ring group, morpholine ring group, piperazoline ring group

Ring group, indole ring group, isoindole ring group, quinoline ring group, thiophene ring group, pyrrole ring group, thiazoline ring group, furan ring group, pyridine ring group, dioxane ring group, morpholine ring group , thiophene

Ring group, triazole ring group, tetrazole ring group, dioxofuran ring group, pyridine

An aliphatic heterocyclic group having 4 to 30 carbon atoms, such as a ring group or a purine ring group, or an aromatic heterocyclic group having 3 to 20 carbon atoms. Such heterocyclic groups can be structures in which unsaturated bonds are hydrogenated, and they can also be structures in which the cyclic skeleton is condensed (such as benzene, imidazole ring). It is formed by substitution of halogen atom, nitro group, cyano group, hydroxyl group, carboxyl group, etc.

Examples of the aliphatic hydrocarbon group having 1 to 25 carbon atoms represented by R ¹ to R ⁶ and R ¹¹ to R ¹⁷ include: methyl, ethyl, n-propyl, isopropyl, n-butyl, tertiary butyl, tertiary butyl, Butyl, n-pentyl, isopentyl, n-hexyl, isohexyl, n-octyl, isooctyl, n-nonyl, isononyl, n-decyl, isodecyl, n-dodecyl, isododecanyl Alkyl, undecyl, myristyl, hexadecyl, stearyl and other linear or branched chain alkyl groups with 1 to 25 carbon atoms; cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl cycloalkyl groups having 3 to 25 carbon atoms; cycloalkylalkyl groups having 4 to 25 carbon atoms, such as cyclopropylmethyl and cyclohexylmethyl; from the viewpoint of solubility, 2-ethyl is preferred Hexyl, 2-butyloctyl and other branched chain alkyl groups having 3 to 25 carbon atoms.

Examples of the substituents that the aliphatic hydrocarbon group having 1 to 25 carbon atoms represented by R ¹ to R ⁶ and R ¹¹ to R ¹⁷ may have include: heterocyclic group, halogen atom, nitro group, cyano group, hydroxyl group, carboxyl group, acetamide group, amine group, alkylamino group with 1 to 12 carbon atoms, etc. Examples of the heterocyclic group include the same ones as the heterocyclic group represented by R ¹ .

Examples of the aromatic hydrocarbon groups having 6 to 18 carbon atoms represented by R ¹ to R ⁶ and R ¹¹ to R ¹⁷ include aromatic hydrocarbon groups having 6 to 18 carbon atoms such as phenyl, naphthyl, anthracenyl, biphenyl, and methylphenyl groups. groups; benzyl, phenethyl, naphthylmethyl, phenoxy and other aralkyl groups with 7 to 18 carbon atoms, etc. -CH ₂ - in the aromatic hydrocarbon group having 6 to 18 carbon atoms represented by R ¹ to R ⁶ and R ¹¹ to R ¹⁷ via -SO ₂ -, -CO-, -O-, -S- or -CF ₂ - Examples of the substituted group include aryloxy groups such as phenoxy group and naphthyloxy group. From the viewpoint of wavelength selectivity, the aromatic hydrocarbon group having 6 to 18 carbon atoms represented by R ¹ to R ⁶ and R ¹¹ to R ¹⁷ is preferably an aralkyl group having 7 to 18 carbon atoms or an aralkyl group having 6 to 18 carbon atoms. The aromatic oxygen group is more preferably a benzyl group or an aromatic oxygen group having 6 to 18 carbon atoms.

Examples of substituents that the aromatic hydrocarbon group having 6 to 18 carbon atoms represented by R ¹ to R ⁶ and R ¹¹ to R ¹⁷ may have include heterocyclic group, halogen atom, nitro group, cyano group, hydroxyl group, carboxyl group, and acetamide. group, amine group, alkylamino group with 1 to 12 carbon atoms, etc. Examples of the heterocyclic group include the same ones as the heterocyclic group represented by R ¹ .

The group containing a polymerizable group represented by R ¹¹ , R ¹³ , R ¹⁴ , R ¹⁵ and R ¹⁶ is not particularly limited as long as it has a polymerizable group at its terminal. Specific examples include formula (I-2 ) represents the basis.

＊-R ¹¹⁵ -X ² (I-2)

[In formula (I-2), X ² represents a polymerizable group,

R ¹¹⁵ represents an alkylenediyl group having 1 to 12 carbon atoms, and -CH ₂ - contained in the alkylenediyl group may be substituted by -O-, -CO-, -CS- or -NR ¹¹⁶ -,

R ¹¹⁶ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms,

*Indicates a bond with a carbon atom or a nitrogen atom].

^Examples of the polymerizable group represented by , acrylamide group, methacrylamide group and other ethylenically unsaturated groups.

Examples of the alkylenediyl group having 1 to 12 carbon atoms represented by ^R115 include methylene, ethylidene, propane-1,3-diyl, butane-1,4-diyl, and pentane-1,5- Diyl, hexane-1,6-diyl, ethane-1,1-diyl, propane-1,2-diyl, butane-1,3-diyl, 2-methylpropane-1, 3-diyl, 2-methylpropane-1,2-diyl, pentane-1,4-diyl and 2-methylbutane-1,4-diyl, etc.

Examples of the alkyl group having 1 to 6 carbon atoms represented by R ¹¹⁶ include the same ones as the alkyl group having 1 to 6 carbon atoms represented by R ¹¹² .

At least one of R ¹¹ , R ¹³ , R ¹⁴ , R ¹⁵ and R ¹⁶ represents a group containing a polymerizable group.

More preferably, at least one of R ¹³ , R ¹⁴ , R ¹⁵ and R ¹⁶ is a group containing a polymerizable group, and more preferably, any one of R ¹³ , R ¹⁴ , R ¹⁵ or R ¹⁶ is a group containing a polymerizable group. The base.

R ² is preferably an aromatic hydrocarbon group or heterocyclic group having 6 to 18 carbon atoms, more preferably an aromatic hydrocarbon group having 6 to 18 carbon atoms or an aromatic heterocyclic group having 3 to 20 carbon atoms.

The polymerizable group represented by A is preferably an ethylenically unsaturated group.

E ¹ and E ¹¹ are preferably each independently a cyano group.

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

[R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ and E ¹ represent the same meanings as above;

R ⁷ represents a hydrogen atom, cyano group, methyl group or phenyl group;

Z ¹ represents an alkanediyl group having 1 to 12 carbon atoms, a divalent aromatic hydrocarbon group having 6 to 18 carbon atoms, -OR ^2A -＊1, -SR ^2B -＊1 or -NR ^1D -R ^2C -＊1;

Z ² represents single bond, ＊2-CO-O-, ＊2-O-CO-, ＊2-S(=O) ₂ -, ＊2-O-SO ₂ -, ＊2-CO-NR ^1B - ,＊2-NR ^1C -CO-,＊2-R ^2D OP(=O)-OR ^2E -,＊2-NR ^1E -CO-O-,＊2-O-CO-NR ^1F -,＊2- (OR ^2F ) _s1 -, *2-CO-S-, *2-S-CO- or perfluoroalkyldiyl with 1 to 4 carbon atoms;

R ^1B , R ^1C , R ^1D , R ^1E and R ^1F each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms;

R ^2A , R ^2B , R ^2C , R ^2D , R ^2E and R ^2F each independently represent a divalent hydrocarbon group having 1 to 18 carbon atoms;

*1 indicates the bond with Z ² ;

*2 indicates the bonding bond with Z ¹ ].

Examples of the alkylenediyl group having 1 to 12 carbon atoms represented by Z ¹ include the same ones as the alkylenediyl group having 1 to 12 carbon atoms represented by R ¹¹⁵ .

Examples of the divalent aromatic hydrocarbon group having 6 to 18 carbon atoms represented by Z ¹ include phenylene group, naphthylene group, and the like.

Examples of the alkyl group having 1 to 6 carbon atoms represented by R ^1B , R ^1C , R ^1D , R ^1E and R ^1F include the alkyl group having 1 to 6 carbon atoms represented by R ¹¹² .

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

Z ¹ is preferably -OR ^2A -*1 (R ^2A is more preferably an alkanediyl group having 1 to 8 carbon atoms, and even more preferably an alkanediyl group having 4 to 8 carbon atoms).

Z ² is preferably *2-O-CO-, *2-O-SO ₂ -, or *2-NR ^1C -CO- (R ^1C is more preferably a hydrogen atom).

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

[R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R ¹⁷ and E ¹¹ have the same meaning as above, but at least one of R ¹³ , R ¹⁴ , R ¹⁵ and R ¹⁶ means including polymerizable group].

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

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

The compound represented by formula (I) in which A is an ethylenically unsaturated group can be obtained, for example, by reacting a compound represented by formula (Ia) and a compound represented by formula (c1).

[R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ and E ¹ in the formula (Ia) represent the same meanings as above, Z ³ in the formula (c1) represents a divalent linking group, and A ¹ represents Ethylene polymerizable group].

The usage amount of the compound represented by formula (c1) is preferably 0.5 to 5 moles relative to 1 mole of the compound represented by formula (Ia).

The reaction between the compound represented by formula (Ia) and the compound represented by formula (c1) can be carried out using a conventional esterification reaction, and is preferably carried out in the presence of a base and a carbodiimide condensing agent. Examples of the base include triethylamine, diisopropylethylamine, pyridine, piperidine, pyrrolidine, proline, N,N-dimethylaminopyridine, and the like. Examples of carbodiimide condensing agents include: N,N-dicyclohexylcarbodiimide, N,N-diisopropylcarbodiimide, 1-ethyl-3-(3-dimethylaminopropane) base) carbodiimide hydrochloride, etc. The usage amount of the base is preferably 0.001 to 0.5 mol relative to 1 mol of the compound represented by formula (Ia). The usage amount of the carbodiimide condensing agent is preferably 0.5 to 5 moles relative to 1 mole of the compound represented by formula (Ia).

The reaction between the compound represented by formula (Ia) and the compound represented by formula (c1) is preferably carried out in an organic solvent. Examples of organic solvents include: toluene, acetonitrile, methylene chloride, chloroform, etc.

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

The reaction between the compound represented by formula (Ia) and the compound represented by formula (c1) is carried out by mixing the compound represented by formula (Ia) and the compound represented by formula (c1).

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

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

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

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

[R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ and E ¹ in the formula have the same meanings as above].

The usage amount of the compound represented by the formula (c2) is preferably 0.5 to 5 moles relative to 1 mole of the compound represented by the formula (Ib).

The reaction between the compound represented by formula (Ib) and the compound represented by formula (c2) is preferably carried out in the presence of a base. Examples of the base include pyridine, pyrrolidine, piperidine, triethylamine, diisopropylethylamine, and the like. The usage amount of the base is preferably 0.5 to 5 moles relative to 1 mole of the compound represented by formula (Ib).

The reaction between the compound represented by formula (Ib) and the compound represented by formula (c2) is preferably carried out in an organic solvent. Examples of organic solvents include: acetonitrile, isopropyl alcohol, toluene, chloroform, dichloromethane, etc.

The reaction between the compound represented by formula (Ib) and the compound represented by formula (c2) is carried out by mixing the compound represented by formula (Ib) and the compound represented by formula (c2).

The reaction temperature of the compound represented by formula (Ib) and the compound represented by formula (c2) is preferably 0 to 120°C, and the reaction time is usually 1 to 50 hours.

Resin (A) may be a homopolymer having a structural unit having an indole structure, or a copolymer including a structural unit having an indole structure and other structural units. The resin (A) is preferably a copolymer.

Examples of structural units other than the structural unit having an indole structure that the resin (A) may contain include structural units described in the following group A.

Group A: Structural unit derived from (meth)acrylate, structural unit derived from styrenic monomer, structural unit derived from vinyl monomer, structural unit derived from epoxy compound, represented by formula (a) The structural unit, the structural unit represented by formula (b) and the structural unit represented by formula (c);

[In the formula, R ^a1 represents a divalent hydrocarbon group;

R ^b1 and R ^b2 each independently represent a hydrogen atom or a hydrocarbon group;

R ^c1 and R ^c2 each independently represent a divalent hydrocarbon group].

(Meth)acrylic acid esters include: (meth)acrylic acid methyl ester, (meth)ethyl acrylate, (meth)acrylic acid n-propyl ester, (meth)acrylic acid n-butyl ester, (meth)acrylic acid n-pentyl ester Ester, n-hexyl (meth)acrylate, n-heptyl (meth)acrylate, n-octyl (meth)acrylate, (meth)propylene Linear chain of (meth)acrylic acid such as n-nonyl acid, n-decyl (meth)acrylate, n-dodecyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, etc. alkyl ester;

Isopropyl (meth)acrylate, isobutyl (meth)acrylate, tert-butyl (meth)acrylate, isopentyl (meth)acrylate, isohexyl (meth)acrylate, (meth)acrylic acid 2-Ethylhexyl, isooctyl (meth)acrylate, isononyl (meth)acrylate, isostearyl (meth)acrylate, isopentyl (meth)acrylate and other (meth)acrylic acids branched alkyl esters;

Cyclohexyl (meth)acrylate, isonorbornyl (meth)acrylate, adamantyl (meth)acrylate, dicyclopentyl (meth)acrylate, cyclododecyl (meth)acrylate, Methylcyclohexyl (meth)acrylate, trimethylcyclohexyl (meth)acrylate, tert-butylcyclohexyl (meth)acrylate, α-ethoxycyclohexyl acrylate, etc. (Methyl) Alkyl esters of acrylic acid containing an alicyclic skeleton; esters of (meth)acrylic acid containing an aromatic ring skeleton such as phenyl (meth)acrylate; etc.

Examples of the structural unit derived from (meth)acrylate include substituent-containing (meth)acrylic acid alkyl ester in which a substituent is introduced into the alkyl group of (meth)acrylic acid alkyl ester. The substituent of the substituent-containing alkyl (meth)acrylate is a group that replaces the hydrogen atom of the alkyl group, and specific examples thereof include a phenyl group, an alkoxy group, and a phenoxy group. Specific examples of (meth)acrylic acid alkyl esters containing substituents include: (meth)acrylic acid 2-methoxyethyl ester, (meth)acrylic acid ethoxymethyl ester, (meth)acrylic acid phenoxy ethyl ester, 2-(2-phenoxyethoxy)ethyl (meth)acrylate, phenoxydiethylene glycol (meth)acrylate, phenoxy poly(ethylene glycol) (meth)acrylate Alcohol) ester, etc.

These (meth)acrylates can be used individually or in plural different types.

The resin (A) of the present invention preferably contains an alkyl (meth)acrylate (meth)acrylate and is a homopolymer having a glass transition temperature Tg of less than 0°C and is derived from the alkyl (meth)acrylate (a1). The structural unit and the structural unit derived from the alkyl (meth)acrylate (a2) belonging to the homopolymer have a glass transition temperature Tg of 0° C. or higher. This system improves the high-temperature durability of the adhesive layer. For the Tg of the homopolymer of the alkyl (meth)acrylate, the value from literature such as Polymer Handbook (Wiley-Interscience) can be used.

Specific examples of (meth)acrylic acid alkyl ester (a1) include: ethyl acrylate, n- and iso-propyl acrylate, n- and iso-butyl acrylate, n-pentyl acrylate, n- and iso-hexyl acrylate Esters, n-heptyl acrylate, n- and iso-octyl acrylate, 2-ethylhexyl acrylate, n- and iso-nonyl acrylate, n- and iso-decyl acrylate, n-dodecyl acrylate Alkyl (meth)acrylate, such as ester, has an alkyl group with a carbon number of about 2 to 12.

Only one type of (meth)acrylic acid alkyl ester (a1) may be used, or two or more types may be used in combination. In addition, from the viewpoint of followability and reworkability when laminating an optical film, n-butyl acrylate, n-octyl acrylate, 2-ethylhexyl acrylate, etc. are preferred.

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

Only one type of (meth)acrylic acid alkyl ester (a2) may be used, or two or more types may be used in combination. Furthermore, from the viewpoint of high-temperature durability, the (meth)acrylic acid alkyl ester (a2) preferably contains methyl acrylate, cyclohexyl acrylate, and isorbornyl acrylate, and more preferably contains methyl acrylate.

In addition, the structural unit derived from (meth)acrylic acid ester may also include the structural unit derived from (meth)acrylic acid ester having a polar functional group.

Examples of (meth)acrylate monomers having polar functional groups include: (meth)acrylic acid 1-hydroxymethyl ester, (meth)acrylic acid 1-hydroxyethyl ester, (meth)acrylic acid 1-hydroxyheptyl ester, (meth)acrylic acid 1-hydroxyheptyl ester, Methacrylate 1-hydroxybutyl ester, 1-hydroxypentyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, 2-hydroxypentyl (meth)acrylate, 2-hydroxyhexyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 3-hydroxybutyl (meth)acrylate, (meth)acrylic acid 3 -Hydroxypentyl ester, 3-hydroxyhexyl (meth)acrylate, 3-hydroxyheptyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, 4-hydroxypentyl (meth)acrylate, ( 4-hydroxyhexyl methacrylate, 4-hydroxyheptyl (meth)acrylate, 4-hydroxyoctyl (meth)acrylate, 2-chloro-2-hydroxypropyl (meth)acrylate, (meth)acrylate )3-chloro-2-hydroxypropyl acrylate, 2-hydroxy-3-phenoxypropyl (meth)acrylate, 5-hydroxypentyl (meth)acrylate, 5-hydroxyhexyl (meth)acrylate , 5-hydroxyheptyl (meth)acrylate, 5-hydroxyoctyl (meth)acrylate, 5-hydroxynonyl (meth)acrylate, 6-hydroxyhexyl (meth)acrylate, (meth)acrylic acid 6-hydroxyheptyl ester, 6-hydroxyoctyl (meth)acrylate, 6-hydroxynonyl (meth)acrylate, 6-hydroxydecyl (meth)acrylate, 7-hydroxyheptyl (meth)acrylate, 7-hydroxyoctyl (meth)acrylate, 7-hydroxynonyl (meth)acrylate, 7-hydroxydecyl (meth)acrylate, 7-hydroxyundecyl (meth)acrylate, (meth)acrylate ) 8-hydroxyoctyl acrylate, 8-hydroxynonyl (meth)acrylate, 8-hydroxydecyl (meth)acrylate, 8-hydroxyundecyl (meth)acrylate, 8-(meth)acrylate -Hydroxydodecyl ester, 9-hydroxynonyl (meth)acrylate, 9-hydroxydecyl (meth)acrylate, 9-hydroxyundecyl (meth)acrylate, (meth)acrylic acid 9 -Hydroxydodecyl ester, 9-hydroxytridecyl (meth)acrylate, 10-hydroxydecyl (meth)acrylate, 10-hydroxyundecyl (meth)acrylate, (meth)acrylate ) 10-hydroxydodecyl acrylate, 10-hydroxytridecyl (meth)acrylate, 10-hydroxytetradecyl (meth)acrylate, 11-hydroxyundecane (meth)acrylate ester, 11-hydroxydodecyl (meth)acrylate, 11-hydroxytridecyl (meth)acrylate, 11-hydroxytetradecyl (meth)acrylate, (meth)acrylic acid 11-Hydroxypentadecyl ester, (methyl) 12-hydroxydodecyl acrylate, 12-hydroxytridecyl (meth)acrylate, 12-hydroxytetradecyl (meth)acrylate, 13-hydroxypentadecyl (meth)acrylate Ester, 14-hydroxytetradecyl (meth)acrylate, 14-hydroxypentadecyl (meth)acrylate, 15-hydroxypentadecyl (meth)acrylate, (meth)acrylic acid 15 - (Meth)acrylate having a hydroxyl group such as hydroxyheptadecyl ester and the like.

Examples of styrenic monomers include: styrene; methylstyrene, dimethylstyrene, trimethylstyrene, ethylstyrene, diethylstyrene, triethylstyrene, propylstyrene, Alkyl styrenes such as butylstyrene, hexylstyrene, heptylstyrene, and octylstyrene; halogenated styrenes such as fluorostyrene, chlorostyrene, bromostyrene, dibromostyrene, and iodostyrene; nitrate styrene; acetyl styrene; methoxystyrene; and divinylbenzene.

Examples of vinyl monomers include: vinyl acetate, vinyl propionate, vinyl butyrate, vinyl 2-ethylhexanoate, vinyl laurate and other fatty acid vinyl esters; vinyl chloride, vinyl bromide and other halogenated ethylenes; Vinylidene halides such as vinyl chloride; nitrogen-containing heteroaromatic vinyls such as vinylpyridine, vinylpyrrolidone, and vinylpyrrolidone; conjugated dienes such as butadiene, isoprene, chloroprene, etc.; and acrylonitrile , methacrylonitrile and other unsaturated nitriles.

The so-called epoxy compound refers to a compound having an epoxy group in the molecule. The epoxy group may also be an epoxy group bonded to an alicyclic ring such as an epoxycyclopentane structure or an epoxycyclohexane structure.

Epoxy compounds include: 3,4-epoxycyclohexanecarboxylic acid 3,4-epoxycyclohexylmethyl ester, 3,4-epoxy-6-methylcyclohexanecarboxylic acid 3,4 -Epoxy-6-methylcyclohexylmethyl ester, vinylene bis(3,4-epoxycyclohexanecarboxylate), adipate bis(3,4-epoxycyclohexylmethyl ester) ), adipate bis(3,4-epoxy-6-methylcyclohexylmethyl ester), diethylene glycol bis(3,4-epoxycyclohexylmethyl ether), ethylene glycol bis( 3,4-epoxycyclohexyl methyl ether), 2,3,14,15-diepoxy-7,11,18,21-tetraoxy Trispiro[5.2.2.5.2.2]undecane, 3-(3,4-epoxycyclohexyl)-8,9-epoxy-1,5dioxspiro[5.5]undecan , 4-vinylcyclohexene dioxide, limonene dioxide, bis(2,3-epoxycyclopentyl ether), dicyclopentadiene dioxide, 1,4-butanediol bicyclo Oxypropyl ether, 1,6-hexanediol diepoxypropyl ether, neopentyl glycol diepoxypropyl ether, trimethylolpropane triepoxypropyl ether, pentaerythritol tetraepoxypropyl ether, etc. .

The compound derived from the structural unit represented by formula (a) can be synthesized, for example, by the reaction of a diisocyanate compound and a polyol.

The compound of the structural unit represented by the derivative formula (b) can be synthesized, for example, by reacting a halogenated silane or a silane having a hydroxyl group.

The compound derived from the structural unit represented by formula (c) can be synthesized, for example, by reaction of polycarboxylic acid and polyol.

The structural unit selected from the structural units described in Group A is preferably a structural unit derived from (meth)acrylate. The structural unit derived from (meth)acrylate is preferably an alkyl (meth)acrylate and an alkyl (meth)acrylate having a hydroxyl group.

The resin (A) of the present invention may further contain other structural units (sometimes called structural units (aa)). Specifically, structural units derived from a (meth)acrylamide-based monomer, structural units derived from a monomer having a carboxyl group, structural units derived from a monomer having a heterocyclic group, structural units derived from a monomer having a carboxyl group, Structural units of monomers with substituted or unsubstituted amine groups, etc.

Examples of (meth)acrylamide-based monomers include: N-hydroxymethyl(meth)acrylamide, N-(2-hydroxyethyl)(meth)acrylamide, N-(3-hydroxypropyl) (meth)acrylamide, N-(4-hydroxybutyl)(meth)acrylamide, N-(5-hydroxypentyl)(meth)acrylamide, N-(6-hydroxy Hexyl)(meth)acrylamide, N,N-dimethyl(meth)acrylamide, N,N-diethyl(meth)propylene Amide, N-isopropyl(meth)acrylamide, N-(3-dimethylaminopropyl)(meth)acrylamide, N-(1,1-dimethyl-3- Oxybutyl)(meth)acrylamide, N-[2-(2-oxo-1-imidazolinyl)ethyl](meth)acrylamide, 2-acrylamide-2-methyl Propane-1-propanesulfonic acid, N-(methoxymethyl)acrylamide, N-(ethoxymethyl)(meth)acrylamide, N-(propoxymethyl)(methyl )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-methyl Propoxy)ethyl](meth)acrylamide, N-[2-(2-methylpropoxy)ethyl](meth)acrylamide, N-(2-butoxyethyl) (meth)acrylamide, N-[2-(1,1-dimethylethoxy)ethyl](meth)acrylamide, etc. Among them, N-(methoxymethyl)acrylamide, N-(ethoxymethyl)acrylamide, N-(propoxymethyl)acrylamide, N-(butoxymethyl)acrylamide Meth)acrylamide and N-(2-methylpropoxymethyl)acrylamide.

Examples of the monomer having a carboxyl group include: (meth)acrylic acid, carboxyalkyl (meth)acrylate (for example, carboxyethyl (meth)acrylate, carboxypentyl (meth)acrylate), maleic acid, Maleic anhydride, fumaric acid, crotonic acid, preferably acrylic acid.

Monomers with heterocyclic groups include: acryloylmorpholine, vinylcaprolactam, N-vinyl-2-pyrrolidone, vinylpyridine, (meth)acrylic acid tetrahydrofurfuryl ester, caprolactone modified Tetrahydrofurfuryl acrylate, 3,4-epoxycyclohexylmethyl (meth)acrylate, glycidyl (meth)acrylate, 2,5-dihydrofuran, etc.

Examples of the monomer having a substituted or unsubstituted amine group include: (meth)aminoethyl acrylate, (meth)acrylic acid N,N-dimethylaminoethyl, (meth)acrylic acid dimethylamine Propyl ester, etc.

The structural unit having an indole structure and the structural unit (aa) selected from other than the structural units of Group A are preferably monomers having a carboxyl group.

The content of the structural unit having an indole structure is preferably 0.01 to 50 parts by mass, more preferably 0.1 to 20 parts by mass, and even more preferably 0.5 to 15 parts by mass relative to 100 parts by mass of all structural units contained in the resin (A) share.

The content of at least one structural unit selected from the structural units described in Group A is preferably 50 parts by mass or more, more preferably 55 to 99.99 parts by mass, based on 100 parts by mass of all structural units of the resin (A), and even more preferably 60 to 85 parts by mass.

When the resin (A) contains the structural unit (aa), it is preferably 20 parts by mass or less, more preferably 0.5 parts by mass or more and 15 parts by mass or less, still more preferably 0.5, relative to 100 parts by mass of all the structural units of the resin (A). The amount is not less than 10 parts by mass and not more than 10 parts by mass, particularly preferably not less than 1 part by mass and not more than 7 parts by mass.

When the resin (A) contains a structural unit derived from an alkyl (meth)acrylate having a hydroxyl group, the content of the structural unit is preferably 20 parts by mass or less based on 100 parts by mass of all the structural units of the resin (A), and more preferably It is ideally 0.5 parts by mass or more and 15 parts by mass or less, more preferably 0.5 parts by mass or more and 10 parts by mass or less, particularly preferably 1 part by mass or more and 7 parts by mass or less.

From the viewpoint of preventing an increase in the peeling force of a separator film that can be laminated on the outer surface of an adhesive layer formed of an adhesive composition, it is preferable that the monomer having an amine group is not substantially included. Here, all To say that the monomer having an amine group is not substantially included means that the content of the structural unit derived from the monomer having an amine group is 0.1 parts by mass or less in 100 parts by mass of all the structural units constituting the resin (A).

From the viewpoint of the reactivity of the resin (A) and the cross-linking agent (B) described below, the resin (A) preferably contains a structural unit derived from an alkyl (meth)acrylate having a hydroxyl group or a structural unit derived from an alkyl (meth)acrylate having a carboxyl group. The structural unit of the (meth)acrylic acid alkyl ester more preferably contains one of a structural unit derived from the (meth)acrylic acid alkyl ester having a hydroxyl group and a structural unit derived from the (meth)acrylic acid alkyl ester having a carboxyl group. The (meth)acrylic acid alkyl ester having a hydroxyl group is preferably 2-hydroxyethyl acrylate, 3-hydroxypropyl acrylate, 4-hydroxybutyl acrylate, 5-hydroxypentyl acrylate, or 6-hydroxyhexyl acrylate. In particular, good durability can be obtained by using 2-hydroxyethyl acrylate, 4-hydroxybutyl acrylate, and 5-hydroxypentyl acrylate. As the monomer having a carboxyl group, acrylic acid is preferably used.

The weight average molecular weight (Mw) of the resin (A) of the present invention is preferably 300,000 to 2.5 million, more preferably 500,000 to 2,000,000. When the weight average molecular weight is 300,000 or more, the durability of the adhesive layer in high-temperature environments is improved, and undesirable phenomena such as floating and peeling between the adherend and the adhesive layer and aggregation and damage of the adhesive layer are easily suppressed. When the weight average molecular weight is 2.5 million or less, it is advantageous from the viewpoint of applicability when the processing adhesive composition is formed into a sheet (coated on a base material), for example. From the viewpoint of achieving both the durability of the adhesive layer and the coating properties of the adhesive composition, the weight average molecular weight is preferably 600,000 to 1.8 million, more preferably 700,000 to 1.7 million, and even more preferably 1 million to 1.8 million. 1.6 million. Furthermore, the molecular weight distribution (Mw/Mn) expressed as the ratio of the weight average molecular weight (Mw) and the number average molecular weight (Mn) is usually 2 to 10, and preferably 3 to 8. The weight average molecular weight can be analyzed by gel permeation chromatography and is a value converted to polystyrene.

When the resin (A) of the present invention is dissolved in ethyl acetate and becomes a solution with a concentration of 20% by mass, the viscosity at 25°C is preferably 20 Pa‧s or less, and more preferably 0.1 to 15 Pa‧s. A viscosity within this range is advantageous from the viewpoint of coating properties when applying the adhesive composition to a base material. Additionally, viscosity can be measured with a Brookfield viscometer.

The resin (A) of the present invention can be produced by conventional methods such as solution polymerization, bulk polymerization, suspension polymerization, and emulsion polymerization. The solution polymerization is particularly preferred. Examples of the solution polymerization method include mixing a monomer having an indole structure, a monomer derived into a structural unit described in Group A as required, and an organic solvent, adding a thermal polymerization initiator in a nitrogen environment, and heating at 40 to 90 ℃, preferably about 50 to 80 ℃, stirring for 3 to 15 hours. In order to control the reaction, monomers and thermal polymerization initiators can also be added continuously or intermittently during polymerization. The monomer and thermal polymerization initiator may be added to an organic solvent.

As the polymerization initiator, a thermal polymerization initiator or a photopolymerization initiator can be used. Examples of the photopolymerization initiator include 4-(2-hydroxyethoxy)phenyl(2-hydroxy-2-propyl)one and the like. Examples of thermal polymerization initiators include: 2,2'-azobisisobutyronitrile, 2,2'-azobis(2-methylbutyronitrile), 1,1'-azobis(cyclohexane- 1-carbonitrile), 2,2'-azobis(2,4-dimethylvaleronitrile), 2,2'-azobis(2,4-dimethyl-4-methoxyvaleronitrile) ), dimethyl-2,2'-azobis(2-methylpropionate), 2,2'-azobis(2-hydroxymethylpropionitrile) and other azo compounds; dodecane Hydroperoxide, tert-butyl hydroperoxide, benzoyl peroxide, tert-butyl peroxybenzoate, cumene hydroperoxide, diisopropyl peroxydicarbonate, dipropylene peroxydicarbonate ester, tert-butyl peroxyneodecanoate, tert-butyl peroxypivalate, (3,5,5-trimethylhexyl) peroxide and other organic peroxides; potassium persulfate, peroxyperoxide Inorganic peroxides such as ammonium sulfate and hydrogen peroxide. Furthermore, a redox-based initiator using a peroxide and a reducing agent in combination can also be used.

The proportion of the polymerization initiator is approximately 0.001 to 5 parts by mass relative to 100 parts by mass of the total amount of monomers constituting the resin (A). The polymerization method using active energy rays (for example, ultraviolet rays, etc.) can also be used for the polymerization of the resin (A).

Examples of organic solvents include: aromatic hydrocarbons such as toluene and xylene; esters such as ethyl acetate and butyl acetate; aliphatic alcohols such as propanol and isopropyl alcohol; acetone, methyl ethyl ketone, and methyl isobutyl Ketones, etc.

In 100 mass % of the solid content of the adhesive composition, the content of the resin (A) is usually 60 mass % to 99.99 mass %, more preferably 70 mass % to 99.9 mass %, more preferably 80 mass % to 99.7 mass % .

〈Crosslinking agent (B)〉

The adhesive composition of the present invention may contain a cross-linking agent (B).

Examples of the cross-linking agent (B) include: isocyanate-based cross-linking agents, epoxy-based cross-linking agents, aziridine-based cross-linking agents, metal chelate-based cross-linking agents, etc., especially from the application of adhesive compositions From the viewpoint of the life span, durability of the adhesive layer, and cross-linking speed, an isocyanate-based cross-linking agent is preferred.

The isocyanate compound is preferably a compound having at least two isocyanate groups (-NCO) in the molecule. Examples thereof include: aliphatic isocyanate compounds (for example, hexamethylene diisocyanate, etc.), alicyclic isocyanate compounds ( For example, isophorone diisocyanate, hydrogenated diphenylmethane diisocyanate, hydrogenated xylylene diisocyanate, etc.), aromatic isocyanate compounds (for example, tolylene diisocyanate, xylylene diisocyanate, xylylenemethane diisocyanate, etc.) Isocyanate, naphthyl diisocyanate, triphenylmethane triisocyanate, etc.). Furthermore, the cross-linking agent (B) may be an adduct (adduct) of the aforementioned isocyanate compound and a polyol compound [for example, an adduct of glycerol, trimethylolpropane, etc.], and an isocyanate compound. Urea ester compounds, Urethane prepolymer type formed by addition reaction of biuret type compound, polyether polyol, polyester polyol, acrylic polyol, polybutadiene polyol, polyisoprene polyol, etc. Derivatives of isocyanate compounds, etc. The cross-linking agent (B) can be used alone or in combination of two or more types. Among these, representative ones include aromatic isocyanate-based compounds (for example, tolylene diisocyanate, xylylene diisocyanate), aliphatic isocyanate-based compounds (for example, hexamethylene diisocyanate), or the Adducts or isocyanurates derived from polyol compounds such as glycerol and trimethylolpropane. When the cross-linking agent (B) is an adduct derived from an aromatic isocyanate compound and/or the polyol compound or isocyanurate, the optimal cross-linking density (or cross-linked structure) It is beneficial to the formation of the adhesive layer, so it can improve the durability of the adhesive layer. In particular, when the adducts are derived from tolyl diisocyanate and/or these polyol compounds, for example, even when the adhesive layer is applied to a polarizing plate, the durability can be improved.

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

The adhesive composition of the present invention may further contain a silane compound (D).

Examples of the silane compound (D) include vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris(2-methoxyethoxy)silane, and 3-epoxypropylpropyltrimethoxysilane. Silane, 3-epoxypropylpropyltriethoxysilane, 3-epoxypropylpropylmethyldimethoxysilane, 3-epoxypropylpropylethoxydimethylsilane, 2- (3,4-Epoxycyclohexyl)ethyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloxypropyl Trimethoxysilane, 3-mercaptopropyltrimethoxysilane, etc.

The silane compound (D) may also be a polysiloxane oligomer. Specific examples of polysiloxane oligomers in the form of a combination of monomers are as follows.

3-Mercaptopropyltrimethoxysilane-tetramethoxysilane oligomer, 3-Mercaptopropyltrimethoxysilane-tetraethoxysilane oligomer, 3-Mercaptopropyltriethoxysilane-tetraethoxysilane Methoxypropyl-containing oligomers such as methoxysilane oligomer and 3-mercaptopropyltriethoxysilane-tetraethoxysilane oligomer; mercaptomethyltrimethoxysilane-tetramethoxy Silane oligomer, mercaptomethyltrimethoxysilane-tetraethoxysilane oligomer, methyltriethoxysilane-tetramethoxysilane oligomer, mercaptomethyltriethoxysilane- Tetraethoxysilane oligomer and other mercaptomethyl-containing oligomers; 3-glycidoxypropyltrimethoxysilane-tetramethoxysilane oligomer, 3-glycidoxypropyl Trimethoxysilane-tetraethoxysilane oligomer, 3-glycidoxypropyltriethoxysilane-tetramethoxysilane oligomer, 3-glycidoxypropyltriethyl Oxysilane-tetraethoxysilane oligomer, 3-glycidoxypropylmethyldimethoxysilane-tetramethoxysilane oligomer, 3-glycidoxypropylmethyl Dimethoxysilane-tetraethoxysilane oligomer, 3-glycidoxypropylmethyldiethoxysilane-tetramethoxysilane oligomer, 3-glycidoxypropyl Methyldiethoxysilane-tetraethoxysilane oligomer and other oligomers containing 3-glycidoxypropyl; 3-methacryloxypropyltrimethoxysilane-tetramethyl Oxysilane oligomer, 3-methacryloxypropyltrimethoxysilane-tetraethoxysilane oligomer, 3-methacryloxypropyltriethoxysilane-tetramethoxysilane Silane oligomer, 3-methacryloxypropyltriethoxysilane-tetraethoxysilane oligomer, 3-methacryloxypropylmethyldimethoxysilane-tetraethoxysilane Methoxysilane oligomer, 3-methacryloxypropylmethyldimethoxysilane-tetraethoxysilane oligomer, 3-methacryloxypropylmethyldiethoxy Silane-tetramethoxysilane oligomer, 3-methacryloxypropylmethyldiethoxysilane-tetraethoxysilane oligomer and other oligos containing methacryloxypropyl Polymer; 3-acryloxypropyltrimethoxysilane-tetramethoxysilane oligomer, 3-acryloxypropyltrimethoxysilane-tetraethoxysilane oligomer, 3-propylene acyloxypropyl Triethoxysilane-tetramethoxysilane oligomer, 3-acryloxypropyltriethoxysilane-tetraethoxysilane oligomer, 3-acryloxypropylmethyldimethyl Oxysilane-tetramethoxysilane oligomer, 3-acryloxypropylmethyldimethoxysilane-tetraethoxysilane oligomer, 3-acryloxypropylmethyldiethyl Oxysilane-tetramethoxysilane oligomer, 3-acryloxypropylmethyldiethoxysilane-tetraethoxysilane oligomer, and other acryloxypropyl-containing oligomers ; Vinyltrimethoxysilane-tetramethoxysilane oligomer, vinyltrimethoxysilane-tetraethoxysilane oligomer, vinyltriethoxysilane-tetramethoxysilane oligomer, Vinyltriethoxysilane-tetraethoxysilane oligomer, vinylmethyldimethoxysilane-tetramethoxysilane oligomer, vinylmethyldimethoxysilane-tetraethoxy Vinyl-containing oligomers such as silane oligomers, vinylmethyldiethoxysilane-tetramethoxysilane oligomers, vinylmethyldiethoxysilane-tetraethoxysilane oligomers, etc. Material; 3-aminopropyltrimethoxysilane-tetramethoxysilane oligomer, 3-aminopropyltrimethoxysilane-tetraethoxysilane oligomer, 3-aminopropyltriethyl Oxysilane-tetramethoxysilane oligomer, 3-aminopropyltriethoxysilane-tetraethoxysilane oligomer, 3-aminopropylmethyldimethoxysilane-tetramethyl Oxysilane oligomer, 3-aminopropylmethyldimethoxysilane-tetraethoxysilane oligomer, 3-aminopropylmethyldiethoxysilane-tetramethoxysilane oligomer Polymers, amine group-containing oligomers such as 3-aminopropylmethyldiethoxysilane-tetraethoxysilane oligomers, etc.

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

(In the formula, A ¹ represents an alkanediyl group with 1 to 20 carbon atoms or a divalent alicyclic hydrocarbon group with 3 to 20 carbon atoms. -CH ₂ - constituting the alkanediyl group and the alicyclic hydrocarbon group can be -O - or -CO-substitution, R ⁴¹ represents an alkyl group having 1 to 5 carbon atoms, R ⁴² , R ⁴³ , R ⁴⁴ , R ⁴⁵ and R ⁴⁶ respectively independently represent an alkyl group having 1 to 5 carbon atoms or an alkyl group having 1 to 5 carbon atoms. 5 alkoxy group).

Examples of the alkanediyl group having 1 to 20 carbon atoms represented by A ¹ include: methylene, 1,2-ethanediyl, 1,3-propanediyl, 1,4-butanediyl, 1,5- Pentanediyl, 1,6-hexanediyl, 1,7-heptanediyl, 1,8-octanediyl, 1,9-nonanediyl, 1,10-decanediyl, 1,12-dodecanediyl, 1,14-tetradecanediyl, 1,16-hexadecanediyl, 1,18-octadecanediyl, 1,20-eicosanediyl. Examples of the divalent alicyclic hydrocarbon group having 3 to 20 carbon atoms include 1,3-cyclopentanediyl and 1,4-cyclohexanediyl. The -CH ₂ - constituting the alkanediyl group and the alicyclic hydrocarbon group substituted by -O- or -CO- may include: -CH ₂ CH ₂ -O-CH ₂ CH ₂ -, -CH ₂ CH ₂ - O-CH ₂ CH ₂ -O-CH ₂ CH ₂ -, -CH ₂ CH ₂ -O-CH ₂ CH ₂ -O-CH ₂ CH ₂ -O-CH ₂ CH ₂ -, -CH ₂ CH ₂ -CO -O-CH ₂ CH ₂ -, -CH ₂ CH ₂ -O-CH ₂ CH ₂ -CO-O-CH ₂ CH ₂ -, -CH ₂ CH ₂ CH ₂ CH ₂ -O-CH ₂ CH ₂ - and -CH ₂ CH ₂ CH ₂ CH ₂ -O-CH ₂ CH ₂ CH ₂ CH ₂ -.

Examples of alkyl groups with 1 to 5 carbon atoms represented by R ⁴¹ to R ⁴⁵ include: methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl and pentyl, R ⁴² to R Examples of alkoxy groups with 1 to 5 carbon atoms represented by ⁴⁵ include: methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, tert-butoxy and pentyloxy .

Examples of the silane compound represented by formula (d1) include: (trimethoxysilyl)methane, 1,2-bis(trimethoxysilyl)ethane, and 1,2-bis(triethoxysilyl)ethane. alkane, 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)octane and other bis(trimethoxysilyl)octane C1-5 alkoxysilyl) C1-10 alkane; bis(dimethoxymethylsilyl)methane, 1,2-bis(dimethoxymethylsilyl)ethane, 1,2-bis(dimethoxymethylsilyl)ethane (Dimethoxyethylsilyl)ethane, 1,4-bis(dimethoxymethylsilyl)butane, 1,4-bis(dimethoxyethylsilyl)butane, 1 ,6-bis(dimethoxymethylsilyl)hexane, 1,6-bis(dimethoxyethylsilyl)hexane, 1,8-bis(dimethoxymethylsilyl) Octane, 1,8-bis(dimethoxyethylsilyl)octane and other bis(diC1-5alkoxyC1-5alkylsilyl)C1-10alkanes; 1,6-bis(methane Oxydimethylsilyl)hexane, 1,8-bis(methoxydimethylsilyl)octane and other bis(monoC1-5alkoxydiC1-5alkylsilyl)C1-10 Alkane etc. Among these, 1,2-bis(trimethoxysilyl)ethane, 1,3-bis(trimethoxysilyl)propane, and 1,4-bis(trimethoxysilyl)butane are preferred. alkane, 1,5-bis(trimethoxysilyl)pentane, 1,6-bis(trimethoxysilyl)hexane, 1,8-bis(trimethoxysilyl)octane, etc. Trimethoxysilyl) C1-10 alkane, particularly preferably 1,6-bis(trimethoxysilyl)hexane or 1,8-bis(trimethoxysilyl)octane.

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

The adhesive composition may further contain an antistatic agent.

Examples of the antistatic agent include surfactants, siloxane compounds, conductive polymers, ionic compounds, etc., and preferably ionic compounds. Examples of ionic compounds include commonly used ones. Examples of the cation component constituting the ionic compound include organic cations, inorganic cations, and the like. Examples of organic cations include pyridinium cations, pyrrolidine cations, piperidinium cations, imidazole cations, ammonium cations, sulfonium cations, and phosphonium cations. Examples of inorganic cations include alkali metal cations such as lithium cations, potassium cations, sodium cations, and cesium cations; and alkaline earth metal cations such as magnesium cations and calcium cations. In particular, from the viewpoint of compatibility with (meth)acrylic resin, pyridine cations, imidazole cations, pyrrolidine cations, lithium cations, and potassium cations are preferred. The anion component constituting the ionic compound may be either an inorganic anion or an organic anion. However, from an antistatic point of view, an anion component containing a fluorine atom is more preferred. Examples of anionic components containing fluorine atoms include: hexafluorophosphate anion (PF ₆ ^- ), bis(trifluoromethanesulfonyl)imide anion [(CF ₃ SO ₂ ) ₂ N ^- ], bis(fluorosulfonate) acyl)acyl imine anion [(FSO ₂ ) ₂ N ^- ], tetrakis (pentafluorophenyl) borate anion [(C ₆ F ₅ ) ₄ B ^- ], etc. These ionic compounds can be used individually or in combination of 2 or more types. Particularly preferred are bis(trifluoromethanesulfonyl)imide anion [(CF ₃ SO ₂ ) ₂ N ^- ], bis(fluorosulfonyl)imide anion [(FSO 2 ) 2 N - ], tetrafluoromethanesulfonyl imide anion [(FSO ₂ ) ₂ N ^- ], (Pentafluorophenyl)borate anion [(C ₆ F ₅ ) ₄ B ^- ].

In terms of the stability of the antistatic function of the adhesive layer formed of the adhesive composition over time, an ionic compound that is solid at room temperature is more desirable.

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

The adhesive composition may contain one or more solvents, cross-linking catalysts, tackifiers, plasticizers, softeners, pigments, anti-rust agents, inorganic fillers, light-scattering particles and other additives.

〈Adhesive layer〉

The adhesive layer of the present invention can be formed by, for example, dissolving or dispersing the aforementioned adhesive composition in a solvent to prepare an adhesive composition containing a solvent, and then coating the adhesive composition on the surface of the substrate and drying it.

A suitable base material is a plastic film, and specifically, a release film subjected to a release treatment can be cited. Examples of the release film include a film made of resin such as polyethylene terephthalate, polybutylene terephthalate, polycarbonate, polyarylate, etc., which has been subjected to polysiloxane plasma treatment on one side. handler.

The adhesive layer of the present invention is preferably an adhesive layer that satisfies the following formula (3), and is more preferably an adhesive layer that satisfies the following formula (4).

A(405)≧0.5 (3)

[In formula (3), A (405) represents the absorbance at a wavelength of 405 nm].

A(405)/A(440)≧5 (4)

[In formula (4), A (405) represents the absorbance at a wavelength of 405 nm; A (440) represents the absorbance at a wavelength of 440 nm].

The larger the value of A(405), the higher the absorption at the wavelength of 405nm. When the value of A(405) is less than 0.5, the absorption at a wavelength of 405 nm is low, and the organic EL light-emitting element and the liquid crystal retardation film are likely to be deteriorated by light having a wavelength near 400 nm. The value of A(405) is preferably 0.6 or more, more preferably 0.8 or more, and particularly preferably 1.0 or more. The upper limit is not particularly limited, but is usually 10 or less.

The value of A(405)/A(440) represents the magnitude of absorption at a wavelength of 405 nm relative to the magnitude of absorption at a wavelength of 440 nm. The larger the value of A(405)/A(440), the greater the specific absorption in the wavelength region near 405 nm. When the adhesive layer of the present invention is applied to display devices such as organic EL display devices and liquid crystal display devices, it will not It hinders the color expression of the display device, and absorbs light near 400nm to suppress light degradation of organic EL light-emitting elements and liquid crystal retardation films. The value of A(405)/A(440) is preferably 10 or more, more preferably 30 or more, and even more preferably 60 or more.

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

〈Optical laminated body〉

The adhesive composition of the present invention and the adhesive layer formed from the adhesive composition can be used, for example, for laminating optical films.

An optical laminate in which an optical film is laminated on at least one side of the adhesive layer of the present invention is also included in the present invention.

The optical laminate system of the present invention can be formed by dissolving or dispersing the aforementioned adhesive composition in a solvent to form an adhesive composition containing a solvent, and then coating the composition on the surface of the optical film and drying it. Furthermore, it can also be obtained by forming an adhesive layer on a release film in the same manner and laminating (transferring) the adhesive layer to the surface of the optical film.

The optical laminate including the adhesive layer of the present invention will be described using the drawings.

An example of the layer structure of the adhesive layer of the present invention and the optical laminate of the present invention is shown in FIGS. 1 to 5 .

The adhesive layer 1 shown in Figure 1 is in a state of being attached to the adhesive layer 2 on the adhesive layer 1 in order to temporarily protect the adhesive layer.

The optical laminated body 10A shown in FIG. 2 is an optical laminated body including the optical film 40, the adhesive layer 1 of the present invention, and the release film 2.

The optical laminated body 10B shown in FIG. 3 is an optical laminated body including a protective film 8, an adhesive layer 7, a polarizing film 9, an adhesive layer 7, a protective film 8, an adhesive layer 1 of the present invention, and a release film 2.

The optical laminated body 10C shown in FIG. 4 and the optical laminated body 10D shown in FIG. 5 include a protective film 8, an adhesive layer 7, a polarizing film 9, an adhesive layer 7, a protective film 8, and the adhesive layer 1 of the present invention. , the optical laminate of the retardation film 110, the adhesive layer 7a, and the light-emitting element 30 (liquid crystal cell, organic EL cell).

The optical film 40 is a film with optical functions such as penetration, reflection, and light absorption. The optical film 40 may be a single-layer film or a multi-layer film. Examples of the optical film 40 include: polarizing film, retardation film, brightness enhancing film, anti-glare film, anti-reflection film, diffusion film, light condensing film, window film, etc. Preferably, it is a polarizing film, retardation film, window film or Such laminated films.

The light-condensing film is used for light path control and other purposes, so it can be a lens array sheet, a lens array sheet, a sheet with dots, etc.

The brightness enhancement film is used for the purpose of improving the brightness of a liquid crystal display device to which a polarizing plate is applied. Specific examples include: a reflective polarizing separator sheet designed to produce anisotropy in reflectance by laminating a plurality of films with mutually different refractive index anisotropies; an alignment film of a cholesteric liquid crystal polymer; The circularly polarized light separator of the aligned liquid crystal layer is supported on the base film.

Window film refers to the front panel of flexible display devices such as flexible displays, and is generally placed on the outermost surface of the display device. Examples of window films include resin films made of polyimide resin. The window film may be a mixed film of organic and inorganic materials, such as a resin film including polyimide and silicon oxide. Furthermore, the window film can also be equipped with a hard coating on its surface to provide surface hardness, antifouling properties, and fingerprint resistance. Examples of window films include those described in Japanese Patent Application Laid-Open No. 2017-94488.

The polarizing film is a film that has the property of absorbing linearly polarized light having a vibration plane parallel to its absorption axis and transmitting linearly polarized light having a vibration plane perpendicular to the absorption axis (parallel transmission axis). It can be used, for example, in polyethylene. The alcohol-based film is a film in which dichroic pigments are adsorbed and aligned.

Examples of dichroic dyes include iodine, dichroic organic dyes, and the like.

The degree of saponification of the polyvinyl alcohol-based resin is usually 85 mol% or more and 100 mol% or less, preferably 98 mol% or more. The polyvinyl alcohol-based resin may be modified, and for example, aldehyde-modified polyvinyl formal or polyvinyl acetal may be used. The degree of polymerization of the polyvinyl alcohol-based resin is usually from 1,000 to 10,000, preferably from 1,500 to 5,000.

Generally, a film formed of a polyvinyl alcohol-based resin is used as a raw material film for a polarizing film. The polyvinyl alcohol-based resin can be formed into a film by a conventional method. The thickness of the raw material film is usually 1 to 150 μm, but is preferably 10 μm or more in consideration of ease of stretching and the like.

The polarizing film system, for example, performs the following steps on the raw film: a step of uniaxial stretching, a step of dyeing the film with a dichroic dye to adsorb the dichroic dye, a step of treating the film with a boric acid aqueous solution, and a step of washing the film with water, and finally , dried and manufactured. The thickness of the polarizing film is usually 1 to 30 μm. From the viewpoint of thinning the optical laminate with an adhesive layer, it is preferably 20 μm or less, more preferably 15 μm or less, and particularly preferably 10 μm or less.

It is preferable that at least one side surface of the polarizing film is provided with a protective film via an adhesive.

The adhesive can use a conventional adhesive, and it can be a water-based adhesive or an active energy ray-hardening adhesive.

Examples of the water-based adhesive include commonly used water-based adhesives (for example, adhesives composed of polyvinyl alcohol-based resin aqueous solutions, water-based two-component urethane-based emulsion adhesives, aldehyde compounds, epoxy compounds, melamine-based compounds, hydroxyl compounds, etc. Cross-linking agents such as methyl compounds, isocyanate compounds, amine compounds, polyvalent metal salts, etc.). Among these, a water-based adhesive composed of a polyvinyl alcohol-based resin aqueous solution can be suitably used. In addition, when using a water-based adhesive, it is preferable to dry the polarizing film and the protective film in order to remove the water contained in the water-based adhesive. steps. After the drying step, an aging step of aging at a temperature of about 20 to 45° C. may be provided. The adhesive layer formed of a water-based adhesive is usually 0.001 to 5 μm.

The so-called active energy ray curable adhesive refers to an adhesive that is cured by irradiation with active energy rays such as ultraviolet rays and electron rays. Examples include curable compositions containing a polymerizable compound and a photopolymerization initiator, and adhesives containing photoreaction A curable composition of a flexible resin, a curable composition containing a binder resin and a photoreactive cross-linking agent, etc. are preferably ultraviolet curable adhesives.

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

The protective film is preferably a film formed of a translucent thermoplastic resin. Specific examples include commercially available films made of polyolefin-based resins; cellulose-based resins; polyester-based resins; (meth)acrylic resins; or mixtures and copolymers thereof. When laminating protective films on both sides of the polarizing film, the protective films used may be films composed of different thermoplastic resins, or may be films composed of the same thermoplastic resin.

When the protective film is laminated on at least one side surface of the polarizing film, the protective film is preferably a protective film composed of polyolefin-based resin or cellulose-based resin. By using these films, the optical properties of the polarizing film are not impaired, and the shrinkage of the polarizing film in high-temperature environments can be effectively suppressed. In addition, the protective film may also be an oxygen shielding layer.

A preferred configuration of the polarizing plate is one in which a protective film is laminated on at least one side of the polarizing film via an adhesive layer. When the protective film is laminated on only one side of the polarizing film, it is preferably laminated on the viewing side. The protective film laminated on the viewing side is preferably made of triacetyl cellulose. Protective film composed of aliphatic or cycloolefin resin. The surface with a protective film on the viewing side can also be provided with surface treatment layers such as a hard coating layer and an anti-glare layer.

When the protective film is laminated on both sides of the polarizing film, the protective film on the panel side (the side opposite to the viewing side) is preferably a protective film composed of triacetyl cellulose-based resin, cycloolefin-based resin, or acrylic resin, or Retardation film. The retardation film may be a zero-retardation film described below.

The retardation film is an optical film showing optical anisotropy, and examples thereof include polyvinyl alcohol, polycarbonate, polyester, polyarylate, polyimide, polyolefin, polycycloolefin, and polystyrene. , polymer membranes composed of polystyrene, polyether styrene, polyvinylidene fluoride/polymethyl methacrylate, acetyl cellulose, saponified products of ethylene-vinyl acetate copolymer, polyvinyl chloride, etc. 1.01 to about 6 times the obtained stretched film, etc. Among the stretched films, preferred ones are polymer films obtained by uniaxially or biaxially stretching acetyl cellulose, polyester, polycarbonate films, and cycloolefin resin films. Furthermore, the retardation film may be a retardation film in which a liquid crystalline compound exhibits optical anisotropy by coating/aligning it on a substrate.

In addition, in this specification, the retardation film includes a zero-retardation film, and also includes films called uniaxial retardation film, low photoelastic modulus retardation film, wide viewing angle retardation film, and the like.

The so-called zero-retardation film refers to a film whose front-side retardation R _e and thickness direction retardation R _th are both -15 to 15 nm, and which is optically isotropic. Examples of the zero-retardation film include resin films composed of cellulose-based resins, polyolefin-based resins (chain polyolefin-based resins, polycycloolefin-based resins, etc.) or polyethylene terephthalate-based resins. In terms of controlling the retardation value and making it easy to obtain, a cellulose-based resin or a polyolefin-based resin is preferred. Zero retardation film can also be used as a protective film. Examples of zero-retardation films include "Z-TAC" (trade name) sold by FUJI FILM Co., Ltd., "ZF-14" (trade name) sold by Japan ZEON Co., Ltd., etc.

In the optical film of the present invention, the retardation film is preferably one that expresses optical anisotropy by coating/aligning a liquid crystal compound.

Examples of retardation films that exhibit optical anisotropy by coating/alignment of liquid crystal compounds include the following first to fifth aspects.

The first form: a retardation film in which rod-shaped liquid crystal compounds are aligned in the horizontal direction relative to the supporting substrate;

Second form: a retardation film in which rod-shaped liquid crystal compounds are aligned in the vertical direction relative to the supporting substrate;

The third form: a retardation film in which the rod-shaped liquid crystal compound changes the alignment direction in a spiral manner within the plane;

The fourth form: a retardation film in which a disk-shaped liquid crystal compound is tilted and aligned;

Fifth form: a biaxial retardation film in which a disc-shaped liquid crystal compound is aligned in a vertical direction with respect to a supporting base material.

For example, the first form, the second form, and the fifth form are suitable for the optical film used in the organic electroluminescence display. Furthermore, retardation films of these forms may be laminated and used.

When the retardation film is a layer composed of a polymer in an aligned state of a polymerizable liquid crystal compound (hereinafter, may be referred to as an "optically anisotropic layer"), the retardation film preferably has reverse wavelength dispersion. The so-called reverse wavelength dispersion refers to the optical property that the phase difference value in the short-wavelength liquid crystal alignment plane is smaller than the phase difference value in the long-wavelength liquid crystal alignment plane. Ideally, the optical film satisfies the following formulas (7) and (8). ). In addition, R _e (λ) is expressed as the in-plane phase difference value of light with respect to the wavelength λ nm.

Re(450)/Re(550)≦1 (7)

1≦Re(630)/Re(550) (8)

In the optical film of the present invention, when the retardation film is in the first form and has reverse wavelength dispersion, it is preferable because it reduces coloration during black display of the display device. In the above formula (7), it is more preferable that it is 0.82 ≦Re(450)/Re(550)≦0.93. More ideally, 120≦Re(550)≦150.

Examples of polymerizable liquid crystal compounds when the retardation film has an optically anisotropic layer include: "3.8.6 Cross-linking (Compiled by the Liquid Crystal Handbook Editorial Committee, Maruzen Co., Ltd., issued on October 30, 2012)" Compounds having a polymerizable group among the compounds described in "6.5.1 Liquid crystal material b. Polymerizable nematic liquid crystal material", and Japanese Patent Application Laid-Open No. 2010-31223, Japanese Patent Application Laid-Open No. 2010-270108 Gazette, Japanese Patent Application Publication No. 2011-6360, Japanese Patent Application Publication No. 2011-207765, Japanese Patent Application Publication No. 2011-162678, Japanese Patent Application Publication No. 2016-81035, International Publication No. 2017/043438 and Japanese Patent Application Publication No. 2011 -Polymerizable liquid crystal compounds described in Publication No. 207765, etc.

Examples of a method for producing a retardation film from a polymer in an aligned state of a liquid crystal compound include the method described in Japanese Patent Application Laid-Open No. 2010-31223.

In the second form, the in-plane retardation value Re(550) can be adjusted to the range of 0 to 10nm, preferably 0 to 5nm, and the thickness direction retardation value _Rth can be adjusted to -10 to -300nm. The range is preferably -20 to -200nm. The phase difference value R _th in the thickness direction, which means the refractive index anisotropy in the thickness direction, can be measured from the phase difference value R 50 and the in-plane phase measured using the in-plane forward axis as the tilt axis and tilting it at ₅₀ degrees. The difference R ₀ is calculated. That is, the phase difference value R _th in the thickness direction can be measured from the in-plane phase difference value R ₀ , the phase difference value R ₅₀ measured by inclining the in-plane advancement axis by 50 degrees, and the phase difference film. The thickness d of the retardation film and the average refractive index n ₀ of the retardation film are calculated by obtaining n _x , _ny and n _z from the following equations (10) to (12), and substituting these into equation (9).

R _th =[(n _x +n _y )/2-n _z ]×d (9)

R ₀ =(n _x -n _y )×d (10)

(n _x +n _y +n _z )/3=n ₀ (12)

Here,

Examples of retardation films that express optical anisotropy by coating/aligning liquid crystalline compounds and retardation films that express optical anisotropy by coating with inorganic layered compounds are called temperature-compensated retardation. Poor film, "NH FILM" (trade name, rod-shaped liquid crystal is a tilt-aligned film) sold by JX Nippon Oil & Energy Co., Ltd., "WV FILM" sold by Fuji Film (FUJI FILM Co., Ltd.) "(trade name, disc-shaped liquid crystal is tilt-aligned film), "VAC FILM" sold by Sumitomo Chemical Co., Ltd. (trade name, completely biaxially aligned film), "VAC FILM" sold by Sumitomo Chemical Co., Ltd. new VAC FILM" (trade name, biaxially aligned film), etc.

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

When the retardation film is a multilayer film, the structure of the optical laminated body including the optical film of the present invention can be exemplified as shown in Figure 4, including a phase difference that imparts 1/4 of the wavelength of the transmitted light. The wavelength retardation layer 50 and the 1/2-wavelength retardation layer 70 that imparts a phase difference of 1/2 wavelength to the transmitted light are laminated via an adhesive layer or adhesive layer 60 to form the retardation film 110 . Moreover, as shown in FIG. 5, the structure including the optical film 40 which laminated|stacked the 1/4 wavelength retardation layer 50a and the positive C layer 80 via the adhesive layer or the adhesive layer 60 can also be mentioned.

The 1/4-wavelength retardation layer 50 in Figure 4 that imparts a phase difference of 1/4 wavelength and the 1/2-wavelength phase difference layer 70 that imparts a phase difference of 1/2 wavelength to the transmitted light may be the above-mentioned first The optical film of the fifth form may also be the optical film of the fifth form. In the composition of Figure 4, it is more ideal that at least one of them is in the fifth form.

In the configuration of FIG. 5 , the quarter-wavelength retardation layer 50 a is preferably the optical film of the above-mentioned first form, and more preferably satisfies equations (7) and (8).

The adhesive layer 7a in Figures 4 and 5 is a layer formed of an adhesive composition. The adhesive layer 7a may use a conventional adhesive composition or the adhesive composition of the present invention.

〈Liquid crystal display device〉

The resin of the present invention, the adhesive composition containing the resin, and the optical laminate containing the adhesive layer formed from the adhesive composition can be laminated on display elements such as organic EL elements and liquid crystal cells, and can be used in organic Display devices (FPD: flat panel display) such as EL display devices and liquid crystal display devices.

[Example]

Hereinafter, the present invention will be described in more detail through Examples and Comparative Examples. "%" and "parts" in Examples, Comparative Examples, and Polymerization Examples are "mass %" and "mass parts" unless otherwise specified.

[Example 1]: Synthesis of a light-selective absorbing compound having an indole structure and a polymerizable group

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

Identification of compounds represented by formula (2)

¹ H-NMR (CDCl ₃ ) δ: 3.70 (s, 3H), 7.30-7.42 (dt, 2H), 7.50-7.55 (m, 2H), 7.60-7.64 (m, 3H), 7.68 (d, 1H) ,7.93(s,1H),8.26(d,1H)

After replacing the inside of a 100 mL four-necked flask equipped with a thermometer with a nitrogen environment, 5 parts of the compound represented by formula (2), 2.3 parts of 4-hydroxybutyl acrylate, and N,N-dimethyl-4-amino were fed. 0.4 parts of pyridine, 0.2 parts of 2,6-di-tert-butyl-4-methylphenol and 50 parts of chloroform and cooled to 0°C. While adding 2.2 parts of N,N'-diisopropylcarbodiimide dropwise to the obtained mixture, the temperature was maintained at 0 to 5°C. After the dropwise addition, the resulting mixture was kept at 10°C for 4 hours. The resulting mixture was filtered to obtain a filtrate. The resulting filtrate was concentrated to obtain oil. 50 parts of toluene and 50 parts of water were mixed with the obtained oil, and the liquid was separated to obtain a toluene layer. The obtained toluene layer was concentrated to obtain yellow crude crystals. The crude crystal is recrystallized with isopropanol to obtain the compound represented by formula (3) (2-cyano-3-(1-methyl-2-phenyl-1H-indol-3-yl)-2-acrylic acid -4-propenyloxybutyl ester) 4.9 parts. The maximum absorption wavelength of the compound represented by formula (3) is 386 nm.

Identification of the compound represented by formula (3)

¹ H-NMR (CDCl ₃ ) δ: 1.75-1.80 (m, 4H), 3.70 (s, 3H), 4.15-4.20 (t, 2H), 4.23-4.27 (t, 2H), 5.78-5.82 (dd, 1H),6.06-6.14(dd,1H),6.36-6.41(dd,1H),7.35-7.43(m,5H),7.54-7.57(m,3H),8.12(s,1H),8.42-8.45( m,1H)

The methyl ethyl ketone solution (0.006 g/L) of the obtained compound represented by formula (3) was poured into a 1 cm quartz dish, and the quartz dish was set on a spectrophotometer UV-2450 (manufactured by Shimadzu Corporation). Double-beam method, measuring absorbance in the wavelength range from 300 to 800 nm with a step size of 1 nm. From the obtained absorbance value, the concentration of the compound in the solution, and the optical path length of the quartz dish, the gram absorption coefficient for each wavelength is calculated. As a result, ε(405)=34.9L/(g‧cm), ε(440)=2.0L/(g‧cm), ε(405)/ε(440)=17.5.

ε(λ)=A(λ)/CL

[In the formula, ε(λ) represents the gram absorption coefficient of the compound represented by formula (3) at the wavelength λ nm, A(λ) represents the absorbance at the wavelength λ nm, C represents the concentration g/L, and L represents quartz. The optical path length of the dish is cm. 〕

[Example 2]: Synthesis of a light-selective absorbing compound having an indole structure and a polymerizable group

Except using 2 parts of 2-hydroxyethyl acrylate instead of 2.3 parts of 4-hydroxybutyl acrylate, the same procedure as in Example 1 was carried out to obtain the compound represented by formula (4) (2-cyano-3- (1-methyl-2-phenyl-1H-indol-3-yl)-2-acrylic acid-2-propenyloxyethyl ester) 4.3 parts. The maximum absorption wavelength of the compound represented by formula (4) is 388 nm. Perform the same procedure as Example 1 to obtain the gram absorption coefficient, ε(405)=45.4L/(g‧cm), ε(440)=1.0L/(g‧cm), ε(405)/ε( 440)=445.4.

Identification of the compound represented by formula (4)

¹ H-NMR (CDCl ₃ ) δ: 3.70 (s, 3H), 4.38-4.43 (dt, 2H), 4.43-4.48 (dt, 2H), 5.83-5.86 (dd, 1H), 6.09-6.17 (dd, 1H),6.4-6.45(dd,1H),7.35-7.45(m,5H),7.52-7.58(m,3H),8.12(s,1H),8.42-8.45(m,1H)

[Example 3]: Synthesis of resin (A-1) containing a structural unit having an indole structure

Into a reaction vessel equipped with a cooling tube, a nitrogen introduction tube, a thermometer, and a stirrer, 141 parts of ethyl acetate, 94 parts of butyl acrylate, and 3 parts of 2-hydroxyethyl acrylate as solvents were fed, and the formula

(3) For a mixed solution of 3 parts of the compound shown in (3), the air in the device was replaced with nitrogen so that it did not contain oxygen, and the internal temperature was set to 60°C. To the obtained mixture, the entire amount of a solution in which 0.63 parts of azoisobutyronitrile (polymerization initiator) was dissolved in 10 parts of ethyl acetate was added. The obtained mixture was maintained at 60° C. for 7 hours, and then the entire amount of a solution containing 0.0012 parts of 4-methoxyphenol (polymerization inhibitor) dissolved in 5 parts of ethyl acetate was added to the obtained mixture. Ethyl acetate was added to the obtained mixture, and the concentration of the resin (A-1) having an indole structure was adjusted so that it became 20%, thereby preparing ethyl acetate of the resin (A-1) having an indole structure. solution. The obtained resin (A-1) having an indole structure had a polystyrene-converted weight average molecular weight Mw of 740,000 by GPC, and Mw/Mn was 5.2. The glass transition temperature by DSC was -51°C.

<Measurement of Gram Absorption Coefficient ε>

The obtained methyl ethyl ketone solution (0.11 g/L) of the resin (A-1) was poured into a 1 cm quartz dish, and the quartz dish was set on a spectrophotometer UV-2450 (manufactured by Shimadzu Corporation). Beam method, measuring absorbance in the wavelength range from 300 to 800 nm with a step size of 1 nm. From the obtained absorbance value, the concentration of the resin (A) in the solution, and the optical path length of the quartz cell, the gram absorption coefficient for each wavelength was calculated. As a result, the resin (A-1) has ε(405)=0.442L/(g‧cm), ε(440)=0.008L/(g‧cm), and ε(405)/ε(440)=53.3.

ε(λ)=A(λ)/CL

[In the formula, ε(λ) represents the gram absorption coefficient of the resin (A) at the wavelength λ nm, A(λ) represents the absorbance at the wavelength λ nm, C represents the concentration g/L, and L represents the light of the quartz dish. Diameter length cm. 〕

[Example 4]: Synthesis of resin (A-2) containing a structural unit having an indole structure

Into a reaction vessel equipped with a cooling tube, a nitrogen introduction tube, a thermometer, and a stirrer, 141 parts of ethyl acetate, 94 parts of butyl acrylate, 3 parts of 2-hydroxyethyl acrylate, and the compound represented by formula (4) were fed as solvents. 3 parts of the mixed solution were replaced with nitrogen gas to make the air in the device free of oxygen, and the internal temperature was set to 60°C. To the obtained mixture, the entire amount of a solution containing 0.63 parts of azoisobutyronitrile (polymerization initiator) dissolved in 10 parts of ethyl acetate was added. The obtained mixture was maintained at 60° C. for 7 hours, and then the entire amount of a solution containing 0.0012 parts of 4-methoxyphenol (polymerization inhibitor) was dissolved in 5 parts of ethyl acetate in the obtained mixture. Ethyl acetate was added to the obtained mixture, and the concentration of the resin (A-2) having an indole structure was adjusted so that the concentration thereof became 20%, thereby preparing ethyl acetate of the resin (A-2) having an indole structure. solution. The obtained resin (A-2) having an indole structure had a polystyrene-converted weight average molecular weight Mw of 670,000 by GPC, and Mw/Mn was 4.9. The glass transition temperature by DSC is -50°C. Furthermore, the gram absorption coefficient of resin (A-2) was measured using the same method as Example 3. The results showed that ε(405)=0.336L/(g·cm), ε(440)=0.035L/(g ‧cm), ε(405)/ε(440)=9.5.

[Polymerization Example 1]: Preparation of acrylic resin (A-3)

141 parts of ethyl acetate, 94 parts of butyl acrylate, and 3 parts of 2-hydroxyethyl acrylate were fed, the air in the device was replaced with nitrogen so that it did not contain oxygen, and the internal temperature was set to 60°C. To the obtained mixture, the entire amount of a solution containing 0.63 parts of azoisobutyronitrile (polymerization initiator) dissolved in 10 parts of ethyl acetate was added. The obtained mixture was maintained at 60° C. for 7 hours, and then, the entire amount of a solution containing 0.0012 parts of 4-methoxyphenol (polymerization inhibitor) dissolved in 5 parts of ethyl acetate was added to the obtained mixture. Ethyl acetate was added to the obtained mixture, and the concentration of the resin (A-3) having an indole structure was adjusted so that it became 20%, thereby preparing ethyl acetate of the resin (A-3) having an indole structure. solution. The obtained resin (A-3) having an indole structure was converted into polystyrene by GPC. The weight average molecular weight Mw is 600,000, and Mw/Mn is 6.0. The glass transition temperature by DSC is -49°C. Furthermore, when the gram absorption coefficient of the resin (A-3) was measured using the same method as in Example 3, it was found that there was no absorption at a wavelength of 405 nm and a wavelength of 440 nm, and the absorbance was 0 in both cases.

〈Preparation of adhesive composition and adhesive layer〉

(a) Preparation of adhesive composition

[Example 5] Preparation of adhesive composition (1)

In the obtained ethyl acetate solution (resin concentration: 20%) of the resin (A-1) having an indole structure, a cross-linking agent (CORONATE L, solid content 75%) was mixed with respect to 100 parts of the solid content of the solution. : TOSOH Co., Ltd.) and 0.5 part of a silane compound (KBM-403, produced by Shin-Etsu Chemical Industry Co., Ltd.), and further added 2-butanone so that the solid content concentration became 14%, to obtain an adhesive composition (1). . In addition, the compounding amount of the above-mentioned cross-linking agent (CORONATE L) is the mass part as the active ingredient.

[Example 6] Preparation of adhesive composition (2)

In the obtained ethyl acetate solution (resin concentration: 20%) of the resin (A-2) having an indole structure, a cross-linking agent (CORONATE L, solid content 75%) was mixed with respect to 100 parts of the solid content of the solution. : TOSOH Co., Ltd.) and 0.5 part of a silane compound (KBM-403, produced by Shin-Etsu Chemical Industry Co., Ltd.), and further added 2-butanone so that the solid content concentration became 14%, to obtain an adhesive composition (2). . In addition, the compounding amount of the above-mentioned cross-linking agent (CORONATE L) is the mass part as the active ingredient.

[Comparative Example 1]: Preparation of adhesive composition (3)

To an ethyl acetate solution of acrylic resin (A-3) (resin concentration: 20%), 0.5 of a cross-linking agent (CORONATE L, solid content 75%: manufactured by TOSOH Co., Ltd.) was mixed with respect to 100 parts of the solid content of the solution. parts, 0.5 parts of a silane compound (KBM-403 manufactured by Shin-Etsu Chemical Industries, Ltd.) and 3 parts of a light-absorbing compound (UV absorber; BONASORB UA-3911 manufactured by ORIENT Chemical Industries, Ltd.), and further adjust the solid content concentration to 2-Butanone was added so that it would become 14%, and the adhesive composition (3) was obtained. In addition, the compounding amount of the above-mentioned cross-linking agent (CORONATE L) is the mass part as the active ingredient.

[Preparation Example 1]: Preparation of adhesive composition (4)

To an ethyl acetate solution of acrylic resin (A-3) (resin concentration: 20%), 0.5 of a cross-linking agent (CORONATE L, solid content 75%: manufactured by TOSOH Co., Ltd.) was mixed with respect to 100 parts of the solid content of the solution. parts and 0.5 parts of a silane compound (KBM-403 manufactured by Shin-Etsu Chemical Industry Co., Ltd.), and 2-butanone was further added so that the solid content concentration became 14%, thereby obtaining an adhesive composition (4).

(b) Preparation of adhesive layer

On the release-treated surface of release-treated polyethylene terephthalate (SP-PLR382050 manufactured by Lintec Corporation, hereinafter referred to as "separator film"), use an applicator to apply each of the adhesive compositions prepared above , dry at 100°C for 1 minute to create an adhesive layer. The thickness of the adhesive layer obtained was 15 μm.

In addition, the adhesive layer formed of the adhesive composition obtained in Example 5 was used as the adhesive layer (1), and the adhesive layer formed of the adhesive composition obtained in Example 6 was used as the adhesive layer (2). From the comparison The adhesive layer formed from the adhesive composition obtained in Example 1 is used as the adhesive layer (3), and the adhesive layer formed from the adhesive composition obtained in Example 1 is used as the adhesive layer (4).

〈Measurement of absorbance of adhesive layer〉

The obtained adhesive layer (1) was bonded to an alkali-free glass [trade name "EAGLE The company manufactures ZF-14) and produces laminates for adhesive layer evaluation. The prepared laminate for adhesive layer evaluation was set in a spectrophotometer UV-2450 (manufactured by Shimadzu Corporation), and the absorbance was measured in the wavelength range of 300 to 800 nm with a step size of 1 nm by the double-beam method. In addition, the absorbance of the alkali-free glass simple substance and the cycloolefin-based resin film simple substance is both 0 at the wavelength of 405 nm and the wavelength of 440 nm.

Similarly, the absorbance of the adhesive layer (2) and the adhesive layer (3) was also measured. The absorbance of the adhesive layer (1) to the adhesive layer (3) is shown in Table 1.

[Table 1]

〈Production of optical laminate〉

(i) Production of polarizing film

After immersing a polyvinyl alcohol film ("Kuraray Poval film VF-PE#3000", manufactured by Kuraray Co., Ltd.) with an average degree of polymerization of about 2400, a saponification degree of 99.9 mol% or more, and a thickness of 30 μm in pure water at 37°C, It was immersed in an aqueous solution containing iodine and potassium iodide (iodine/potassium iodide/water (weight ratio)=0.04/1.5/100) at 30°C. Then, it was immersed in an aqueous solution containing potassium iodide and boric acid (potassium iodide/boric acid/water (weight ratio)=12/3.6/100) at 56.5°C. Then, the membrane was treated with pure water at 10°C After washing, it was dried at 85° C. to obtain a polarizing film A with a thickness of about 12 μm in which iodine is adsorbed and aligned with polyvinyl alcohol. Extension is mainly performed in the steps of iodine staining and boric acid treatment, and the total extension magnification is 5.3 times.

(ii) Production of polarizing plates

On one side of the polarizing film obtained in (i), a triacetyl cellulose film with a thickness of 25 μm was laminated via an adhesive composed of an aqueous polyvinyl alcohol resin solution and a transparent hard coat layer of 7 μm was provided. The protective film ("25KCHCN-TC", manufactured by Toppan Printing Co., Ltd.) is produced by laminating a 23 μm-thick cyclic olefin resin film ("ZF14-023" manufactured by Japan ZEON Corporation) on the side opposite to the transparent protective film. Output optical film A (polarizing plate, thickness 67 μm).

(iii) Preparation of composition for forming photo-alignment film

The compound having the following structure was synthesized using the method described in Japanese Patent Application Laid-Open No. 2013-33248. 5 parts of the following compound and 95 parts of cyclohexanone were mixed as components, and the resulting mixture was stirred at 80° C. for 1 hour, thereby obtaining a composition for forming a photo-alignment film.

(iv) Preparation of a composition containing a polymerizable liquid crystal compound.

The polymerizable liquid crystal compound A having the following structure was synthesized using the method described in Japanese Patent Application Laid-Open No. 2010-31223. The maximum absorption wavelength λ _max (LC) of the polymerizable liquid crystal compound A is 350 nm.

Mix 12 parts of polymerizable liquid crystal compound A with the following structure, 0.12 parts of polyacrylate compound (leveling agent; BYK-361N manufactured by BYK-Chemie Co., Ltd.), and polymerization initiator (CIBA special 0.72 parts of Irgacure 369 (manufactured by the company) and 100 parts of cyclopentanone were added to obtain a composition containing a polymerizable liquid crystal compound.

(v) Fabrication of optically anisotropic layer

The cycloolefin-based resin film (ZF-14 manufactured by Japan ZEON Co., Ltd.) was treated with a corona treatment device (AGF-B10, manufactured by Kasuga Electric Co., Ltd.) at an output of 0.3kW and a processing speed of 3m/min. 1 Second-rate. The photo-alignment film forming composition obtained in (iii) was applied with a bar coater on the corona-treated surface, dried at 80°C for 1 minute, and then used a polarized UV irradiation device (SPOT CURE SP-7; USHIO Electric Co., Ltd. (made), polarized UV exposure was carried out with a cumulative light amount of 100mJ/ ^cm2 . The film thickness of the obtained alignment film was 100 nm when measured with an ellipsometer.

Then, the coating liquid composed of the composition A containing the polymerizable liquid crystal compound obtained in (iv) was applied on the alignment film with a bar coater, dried at 120° C. for 1 minute, and a high-pressure mercury lamp (UNICURE VB-15201BY- A. Manufactured by USHIO Denki Co., Ltd.), irradiate ultraviolet light (accumulated light intensity at wavelength 313 nm in a nitrogen environment: 500 mJ/cm ² ) from the surface side coated with a composition containing a polymerizable liquid crystal compound to form a layer containing optical anisotropy 1 optical film. The film thickness of the obtained optically anisotropic layer 1 was 2 μm when measured with a laser microscope.

[Example 7]: Preparation of optical laminate (1)

The adhesive layer (1) is bonded to the cycloolefin-based resin film surface of the polarizing plate produced in the above (ii), and the separator film is peeled off. Then compare the surface of the adhesive layer (1) after peeling off the separator film with the optical anisotropy produced by (v). The opposite side of the cycloolefin-based resin film surface of the layer is bonded, and the cycloolefin-based resin film is peeled off. An adhesive layer (4) with a separator film is bonded to the surface of the optically anisotropic layer from which the cycloolefin-based resin film has been peeled off, thereby obtaining an optical laminate (1).

[Example 8]: Preparation of optical laminate (2)

The optical laminated body (2) was obtained in the same manner as in Example 7 except that the adhesive layer (2) was used instead of the adhesive layer (1).

[Comparative Example 2]: Production of optical laminate (3)

An optical laminated body (3) was obtained in the same manner as in Example 7 except that the adhesive layer (3) was used instead of the adhesive layer (1).

[Preparation Example 2]: Preparation of optical laminate (4)

An optical laminated body (4) was obtained in the same manner as in Example 5 except that the adhesive layer (4) was used instead of the adhesive layer (1).

〈Evaluation of Bleeding Resistance of Adhesive Layer〉

The obtained optical laminate (1) was cut into a size of 40 mm × 40 mm, and the separator film laminated on the adhesive layer (4) was peeled off, and then combined with alkali-free glass [trade name "EAGLE XG" manufactured by Corning Corporation] Fit. The obtained glass-attached optical laminate was used to confirm the precipitation of compound crystals in the plane using a microscope. Then, the obtained glass-coated optical laminate was put into an oven at a temperature of 23° C. and 60% for 500 hours, and the precipitation of compound crystals in the surface was confirmed using a microscope. It was confirmed that there was no increase in the precipitation of compound crystals. The evaluation results are shown in Table 2.

The bleeding resistance of the adhesive layer was evaluated in the same manner as above except that the optical laminate (2) was used instead of the optical laminate (1). The evaluation results are shown in Table 2.

The bleeding resistance of the adhesive layer was evaluated in the same manner as above except that the optical laminate (3) was used instead of the optical laminate (1). The evaluation results are shown in Table 2.

〈Confirmation of the influence of the phase difference change on the optical anisotropy layer due to the adhesive layer〉

The obtained optical laminate (1) was cut into a size of 40 mm × 40 mm, and the separator film laminated on the adhesive layer (4) was peeled off and laminated to alkali-free glass (trade name "EAGLE XG" manufactured by Corning Corporation). . The phase difference value at a wavelength of 450 nm of the obtained glass-attached optical laminate was measured with a birefringence measuring device (KOBRA-WR; manufactured by Oji Scientific Instruments Co., Ltd.). Then, the glass-coated optical laminate was put into an oven at a temperature of 80°C for 120 hours, taken out and left in an environment of 23°C and 50% for 24 hours, and then the phase difference value at a wavelength of 450 nm was measured again.

In the same manner as above, measurement was performed using the optical laminated body (4) instead of the optical laminated body (1).

The phase difference change of the optical laminated body (1) is calculated by subtracting the phase difference of the wavelength 450 nm of the optical laminated body (4) before and after the durability from the change amount of the phase difference value of the wavelength 450 nm before and after the durability of the optical laminated body (1). Calculated by the change in value. The phase difference change values are shown in Table 2.

The influence of the adhesive layer on the phase difference change of the optically anisotropic layer was confirmed in the same manner as above except that the optical laminated body (2) was used instead of the optical laminated body (1). The change value of the phase difference before and after durability is shown in Table 2.

The influence of the adhesive layer on the phase difference change of the optically anisotropic layer was confirmed in the same manner as above except that the optical laminated body (3) was used instead of the optical laminated body (1). The change value of the phase difference before and after durability is shown in Table 2.

〈Measurement of absorbance of optical films〉

The obtained optical laminate (1) was cut into a size of 40 mm × 40 mm, the separator film laminated on the adhesive layer (4) was peeled off, and the alkali-free glass (trade name "EAGLE XG" manufactured by Corning Incorporated) was attached to it. combine. Using a spectrophotometer with an integrating sphere (product name "V7100" manufactured by JASCO Corporation) on the measurement sample, the transmission axis direction and absorption axis direction of the optical layered body (1) in the wavelength range of 380 to 780 nm are measured. The transmittance spectrum was calculated from the transmission spectrum of the optical laminate (1) in the transmission axis direction, and the absorbance of the optical laminate (1) at a wavelength of 405 nm was calculated. In addition, the absorbance of TAC film monomer, COP film monomer and alkali-free glass monomer at wavelength 350nm, wavelength 405nm and wavelength 440nm are all 0.

〈Evaluation of weather resistance〉

Under the conditions of 63° C. and 50% humidity, the optical laminated body (1) was placed in a solar climate meter (model SUNSHINE WEATHER METER S80 manufactured by Suga Test Machine Co., Ltd.) for 24 hours, and a 24-hour weather resistance test was performed. The absorbance of the taken out sample was measured by the same method as the above-mentioned "Absorbance Measurement of Optical Film". From the measured absorbance, the absorbance retention rate of the sample at a wavelength of 405 nm was determined according to the following formula. The results are shown in Table 1. The higher the absorbance retention rate, the better the weather resistance without deterioration of the light selective absorption function.

Absorbance retention rate = (A(405) after durability test/A(405) before durability test)×100

[Table 2]

When an adhesive layer composed of an adhesive composition containing the resin (A) of the present invention is laminated on an optical film, a change in phase difference is suppressed. This is considered that, compared to an adhesive composition containing a light-selective absorbing compound having an indole structure alone, by incorporating a light-selective absorbing compound having a polymerizable group and an indole structure into a resin, it is possible to suppress Migration of photoselectively absorbing compounds with indole structures.

Furthermore, the adhesive layer formed from the adhesive composition containing the resin (A) of the present invention does not increase the precipitation of compounds and has good bleeding resistance even after a heat resistance test at 85°C for 120 hours. Furthermore, the adhesive layer formed from the adhesive composition containing the resin (A) of the present invention has a good A(405)/A(440) value.

[Industrial availability]

The resin of the present invention, the adhesive composition containing the resin, the adhesive layer formed from the adhesive composition, and the optical laminate containing the adhesive layer are suitable for use in liquid crystal panels and liquid crystal display devices.

1‧‧‧Adhesive layer

2‧‧‧Peel-off film

Claims (15)

An adhesive composition, which contains resin (A). The resin (A) contains a structural unit having an indole structure in the side chain, wherein the aforementioned structural unit having an indole structure in the side chain is derived from formula (III) ) or a structural unit derived from a compound represented by formula (II),

In formula (III), R ¹ , R ³ , R ⁴ , R ⁵ and R ⁶ each independently represent a hydrogen atom, a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a carboxyl group, and a carbon which may have a substituent. An aliphatic hydrocarbon group with 1 to 25 carbon atoms or an aromatic hydrocarbon group with 6 to 18 carbon atoms which may have a substituent, and -CH ₂ - contained in the aliphatic hydrocarbon group or aromatic hydrocarbon group may be -NR ^1A -, -SO ₂ - , -CO-, -O-, -S- or -CF ₂ -substitution; R ^1A represents a hydrogen atom, an alkyl group with 1 to 25 carbon atoms or an aromatic hydrocarbon group with 6 to 18 carbon atoms; E ¹ represents an electron-withdrawing group ; R ⁷ represents a hydrogen atom, cyano group, methyl or phenyl group; Z ¹ represents an alkanediyl group having 1 to 12 carbon atoms, a divalent aromatic hydrocarbon group having 6 to 18 carbon atoms, -OR ^2A -＊1, -SR ^2B -＊1 or -NR ^1D -R ^2C -＊1; Z ² represents single bond, ＊2-CO-O-, ＊2-O-CO-, ＊2-S(=O) ₂ -, ＊2 -O-SO ₂ -,＊2-CO-NR ^1B -,＊2-NR ^1C -CO-,＊2-R ^2D OP(=O)-OR ^2E -,＊2-NR ^1E - CO-O- , *2-O-CO-NR ^1F -, *2-(OR ^2F ) _s1 -, *2-CO-S-, *2-S-CO- or perfluoroalkyldiyl having 1 to 4 carbon atoms; R ^1B , R ^1C , R ^1D , R ^1E and R ^1F each independently represent a hydrogen atom or an alkyl group with 1 to 6 carbon atoms; R ^2A , R ^2B , R ^2C , R ^2D , R ^2E and R ^2F each independently represent Represents a divalent hydrocarbon group having 1 to 18 carbon atoms; *1 represents a bond with Z ² ; *2 represents a bond with Z ¹ ; in formula (II), R ¹² and R ¹⁷ each independently represent a hydrogen atom , heterocyclic group, halogen atom, nitro group, cyano group, hydroxyl group, carboxyl group, 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, the aliphatic -CH ₂ - contained in the family hydrocarbon group or aromatic hydrocarbon group may be substituted by -NR ^11A -, -SO ₂ -, -CO-, -O-, -S- or -CF ₂ -; R ¹¹ , R ¹³ , R ¹⁴ , R ¹⁵ and R ¹⁶ each independently represent a hydrogen atom, a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a carboxyl group, a group containing a polymerizable group, and a C 1 to 25 fat which may have a substituent an aliphatic hydrocarbon group or an aromatic hydrocarbon group having 6 to 18 carbon atoms that may have a substituent; -CH ₂ - contained in the aliphatic hydrocarbon group or aromatic hydrocarbon group may be -NR ^12A -, -SO ₂ -, -CO-, - O-, -S- or -CF ₂ -substitution; however, at least one of R ¹¹ , R ¹³ , R ¹⁴ , R ¹⁵ and R ¹⁶ represents a group containing a polymerizable group; R ^11A and R ^12A are independently represents a hydrogen atom, an alkyl group with 1 to 25 carbon atoms, or an aromatic hydrocarbon group with 6 to 18 carbon atoms; E ¹¹ represents an electron-withdrawing group; the aforementioned electron-withdrawing group is a cyano group, a nitro group, a halogen atom, or an alkane substituted by a halogen atom group, or a group represented by formula (I-1), *-X ¹ -R ¹¹¹ (I-1) In formula (I-1), R ¹¹¹ represents a hydrogen atom or a hydrocarbon group having 1 to 25 carbon atoms, and the alkyl group ^{At least} one of the methylene groups contained may be substituted by an oxygen atom; CONR ¹¹³ -＊3, -CNR ¹¹⁴ -＊3 or -SO ₂ -＊3; R ¹¹² , R ¹¹³ and R ¹¹⁴ each independently represent a hydrogen atom, an alkyl group with 1 to 6 carbon atoms or a phenyl group; ＊3 represents Bond with R ¹¹¹ ; * indicates bond with carbon atom. For the adhesive composition described in item 1 of the patent application, the glass transition temperature of the resin (A) is 40°C or lower. The adhesive composition described in Item 1 or 2 of the patent application, wherein the resin (A) is a resin satisfying the following formula (1), ε(405)≧0.02 (1) In the formula (1), ε (405) represents the gram absorption coefficient of resin (A) at a wavelength of 405 nm, and the unit of gram absorption coefficient is L/(g·cm). The adhesive composition described in Item 1 or 2 of the patent application, wherein the resin (A) is a resin that satisfies the following formula (2), ε(405)/ε(440)≧5 (2) Formula (2) In 2), ε(405) represents the gram absorption coefficient of the resin (A) at a wavelength of 405 nm, and ε(440) represents the gram absorption coefficient of the resin at a wavelength of 440 nm. The adhesive composition described in item 1 or 2 of the patent application, wherein the compound represented by formula (III) or the compound represented by formula (II) is a compound satisfying the following formula (1-a), ε (405 )≧5 (1-a) In formula (1-a), ε(405) represents the gram absorption coefficient of a compound having a polymerizable group and an indole structure at a wavelength of 405 nm. The unit of the gram absorption coefficient is L/( g‧cm). The adhesive composition described in Item 5 of the patent application, wherein the compound represented by formula (III) or the compound represented by formula (II) is a compound satisfying the following formula (2-a), ε(405)/ ε(440)≧10 (2-a) In formula (2-a), ε(405) represents the gram absorption coefficient of a compound having a polymerizable group and an indole structure at a wavelength of 405 nm, and ε(440) represents The gram absorption coefficient of a compound having a polymerizable group and an indole structure at a wavelength of 440 nm. The adhesive composition described in claim 1 or 2, wherein the resin (A) further has at least one structural unit selected from the structural units described in the following group A. Group A: derived from (A acrylic acid ester, a structural unit derived from a styrenic monomer, a structural unit derived from a vinyl monomer, a structural unit derived from an epoxy compound, a structural unit represented by formula (a), a structural unit represented by formula (b) ) and the structural unit represented by formula (c);

In the formula, R ^a1 represents a divalent hydrocarbon group; R ^b1 and R ^b2 each independently represent a hydrogen atom or a hydrocarbon group; R ^c1 and R ^c2 each independently represent a divalent hydrocarbon group. The adhesive composition described in claim 7, wherein the content of at least one structural unit selected from the structural units described in group A is 50 mass % or more relative to all the structural units of the resin (A). For example, the adhesive composition described in Item 1 or 2 of the patent application further includes a cross-linking agent (B). An adhesive layer formed from the adhesive composition described in any one of items 1 to 9 of the patent application scope. Such as the adhesive layer described in item 10 of the patent application, the adhesive layer satisfies the following formula (3), A (405) ≧ 0.5 (3) In formula (3), A (405) represents a wavelength of 405 nm absorbance in . For example, the adhesive layer described in item 11 of the patent application scope further satisfies the following formula (4), A(405)/A(440)≧5 (4) In formula (4), A(405) Expresses the absorbance at a wavelength of 405 nm; A (440) expresses the absorbance at a wavelength of 440 nm. An optical laminate in which an optical film is laminated on at least one area of the adhesive layer described in any one of items 10 to 12 of the patent application scope. The optical laminate described in claim 13, wherein the optical film is a polarizing plate. An image display device including the optical laminated body described in Item 14 of the patent application.

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