KR20220036875A - Colored curable resin composition - Google Patents

Abstract

An object of the present invention is to provide a colored curable resin composition capable of forming a thin deep-color cured film. The colored curable resin composition of the present invention includes a coloring agent (A), a resin (B), a polymerizable compound (C), and a polymerization initiator (D). The coloring agent (A) includes a compound represented by Formula (a). The hydroxyl value of the polymerizable compound (C) is 100 mgKOH/g or more.

Description

Colored curable resin composition {COLORED CURABLE RESIN COMPOSITION}

[0001] The present invention relates to a colored curable resin composition, and a color filter and a display device using the same.

[0002] A color filter used in a display device such as a liquid crystal display device, an electroluminescent display device, and a plasma display, or a solid-state imaging device such as a CCD or CMOS sensor, is manufactured from a colored curable resin composition. As a blue color material used for such colored curable resin composition, C.I. represented by Formula (i) which has a triarylmethane skeleton. Pigment Blue 24 is known (Non-Patent Document 1).

[0003]

[0004] 1. Color Index International (British Dyeing Society, American Textile Chemical Technology and Dyeing Technology Association)

[0005] However, when forming a hyperchromic cured film from the colored curable resin composition containing the blue color material, the film thickness may become thick. Therefore, this invention aims at provision of the display device containing the colored curable resin composition which can form the hyperchromic cured film which is a thin film, the color filter formed from this colored curable resin composition, and this color filter.

[0006] The gist of the present invention is as follows.

[1] contains a colorant (A), a resin (B), a polymerizable compound (C), and a polymerization initiator (D),

The said coloring agent (A) contains the compound represented by Formula (a),

The colored curable resin composition in which the hydroxyl value of the said polymeric compound (C) is 100 mgKOH/g or more.

[In formula (a),

R ⁴¹ to R ⁴⁴ are each independently a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, or carbon number which may have a substituent An aralkyl group of 7 to 30 is represented, and the aromatic hydrocarbon group and the substituent which the aralkyl group may have may be -SO ₃ ^- or -SO ₂ -N ^- -SO ₂ -R ^f , and the number of carbon atoms in the saturated hydrocarbon group When is 2 to 20, -CH ₂ - contained in the saturated hydrocarbon group may be substituted with -O- or -CO-. However, in the saturated hydrocarbon group having 2 to 20 carbon atoms, adjacent -CH ₂ - is not simultaneously substituted with -O-, and the terminal -CH ₂ - is not substituted with -O- or -CO-. R ⁴¹ and R ⁴² may be bonded to each other to form a ring together with the nitrogen atom to which they are bonded, or R ⁴³ and R ⁴⁴ may be bonded to each other to form a ring together with the nitrogen atom to which they are bonded.

R ⁴⁷ to R ⁵⁴ each independently represent a hydrogen atom, a halogen atom, a nitro group, a hydroxyl group, -SO ₃ ^- , -SO ₂ -N ^- -SO ₂ -R ^f , or optionally a substituent having 1 to 20 carbon atoms represents a phosphorus saturated hydrocarbon group, and when the saturated hydrocarbon group has 2 to 20 carbon atoms, -CH ₂ - constituting the saturated hydrocarbon group may be substituted with -O- or -CO-, and R ⁴⁸ and R ⁵² are It may combine with each other to form -NH-, -S-, or -SO ₂ -. However, in this saturated hydrocarbon group, adjacent -CH ₂ - is not simultaneously substituted with -O-, and terminal -CH ₂ - is not substituted with -O- or -CO-.

Ring T ¹ represents an aromatic heterocycle having 3 to 10 carbon atoms, and the aromatic heterocycle is a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, a substituted or unsubstituted amino group, or 6 carbon atoms which may have a substituent. You may have an aromatic hydrocarbon group of -20, -SO ₃ ^- or -SO ₂ -N ^- -SO ₂ -R ^f . -SO ₃ ^- or -SO ₂ -N ^- -SO ₂ -R ^f may be sufficient as the substituent which this aromatic hydrocarbon group may have.

M ^r+ represents an r-valent metal ion.

k represents the sum of the number of -SO ₃ ^- and the number of -SO ₂ -N ^- -SO ₂ -R ^f which the compound represented by formula (a) has.

r represents an integer of 1 or more.

R ^f represents a C1-C12 fluoroalkyl group.

However, the compound represented by formula (a) has at least one -SO ₃ ^- or -SO ₂ -N ^- -SO ₂ -R ^f ]

[2] The colored curable resin composition according to [1], wherein the polymerizable compound (C) has a hydroxyl value of 200 mgKOH/g or more.

[3] The colored curable resin composition according to [1] or [2], wherein the colorant (A) further contains a xanthene dye.

[4] The colored curable resin composition according to [3], wherein the xanthene dye is a compound represented by the formula (1).

[In formula (1), R ¹ to R ⁴ each independently represent a hydrogen atom, -R ⁸ or a monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms, or R ¹ and R ² and R ³ and R ⁴ together form a ring containing a nitrogen atom, respectively. A hydrogen atom included in the aromatic hydrocarbon group is a halogen atom, -OH, -OR ⁸ , -SO ₃ ^- , -SO ₃ H, -SO ₃ -M ⁺ , -CO ² H, -CO ₂ R ₈ , ^-SO ₃ R ⁸ or -SO ₂ NR ⁹ R ¹⁰ may be substituted.

R ⁵ is -OH, -SO ₃ ^- , -SO ₃ H, -SO ₃ -M ⁺ , -CO ₂ H ^, -CO ₂ -M ⁺ , -CO ² R ⁸ , -SO ₃ R ₈ or ^-SO ₂ NR ⁹ R ¹⁰ is represented.

m represents the integer of 0-5, and when m is an integer of 2 or more, some R< ⁵ > may be same or different.

R ⁶ and R ⁷ each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.

M ⁺ represents ⁺ N(R ¹¹ ) ₄ , Na ⁺ or K ⁺ , and X represents a halogen atom.

a represents 0 or 1.

R ⁸ represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, and the hydrogen atom contained in the saturated hydrocarbon group may be substituted with an aromatic hydrocarbon group having 6 to 10 carbon atoms, a carboxy group, or a halogen atom, and is included in the saturated hydrocarbon group -CH ₂ - used may be substituted with -S-, -O-, -CO- or -NR ¹¹ -. However, in this saturated hydrocarbon group, adjacent -CH ₂ - is not simultaneously substituted with -O-. R ¹¹ represents a hydrogen atom, a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms, and when two or more R ¹¹ are present, all or part of these may be the same.

R ⁹ and R ¹⁰ each independently represent a hydrogen atom or a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, the hydrogen atom contained in the saturated hydrocarbon group may be substituted with —OH or a halogen atom, and the saturated hydrocarbon group -CH ₂ - contained in the group may be substituted with -S-, -O-, -CO-, -NH- or -NR ⁸ -. However, in this saturated hydrocarbon group, adjacent -CH ₂ - is not simultaneously substituted with -O-.

R ⁹ and R ¹⁰ may be bonded to each other to form a 3- to 10-membered heterocyclic ring containing a nitrogen atom.]

[5] A color filter formed from the colored curable resin composition according to any one of [1] to [4].

[6] A display device comprising the color filter according to [5].

ADVANTAGE OF THE INVENTION According to this invention, the colored curable resin composition which can form the hyperchromic cured film which is a thin film, the color filter formed from this colored curable resin composition, and the display apparatus containing this color filter can be provided.

[0008] The colored curable resin composition of the present invention contains a colorant (A), a resin (B), a polymerizable compound (C), and a polymerization initiator (D).

A coloring agent (A) contains the compound (Hereinafter, it may call a compound (a)) represented by Formula (a).

It is preferable that the colored curable resin composition of this invention contains a solvent (Hereinafter, it may call a solvent (E)) further.

The colored curable resin composition of this invention may also contain a leveling agent (it may call a leveling agent (F) hereafter).

In this specification, the compound illustrated as each component can be used individually or in combination of multiple types, unless otherwise indicated.

[0009] <Colorant (A)>

<<Compound (a)>>

A coloring agent (A) contains a compound (a). Hereinafter, although the present invention will be described in detail using formula (a), the compound (a) also includes tautomers and salts thereof.

[0010]

[In formula (a),

R ⁴¹ to R ⁴⁴ are each independently a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, or carbon number which may have a substituent An aralkyl group of 7 to 30 is represented, and the aromatic hydrocarbon group and the substituent which the aralkyl group may have may be -SO ₃ ^- or -SO ₂ -N ^- -SO ₂ -R ^f , and the number of carbon atoms in the saturated hydrocarbon group When is 2 to 20, -CH ₂ - contained in the saturated hydrocarbon group may be substituted with -O- or -CO-. However, in the saturated hydrocarbon group having 2 to 20 carbon atoms, adjacent -CH ₂ - is not simultaneously substituted with -O-, and the terminal -CH ₂ - is not substituted with -O- or -CO-. R ⁴¹ and R ⁴² may combine to form a ring together with the nitrogen atom to which they are bonded, or R ⁴³ and R ⁴⁴ may combine to form a ring together with the nitrogen atom to which they are bonded.

R ⁴⁷ to R ⁵⁴ each independently represent a hydrogen atom, a halogen atom, a nitro group, a hydroxyl group, -SO ₃ ^- , -SO ₂ -N ^- -SO ₂ -R ^f , or optionally a substituent having 1 to 20 carbon atoms represents a phosphorus saturated hydrocarbon group, and when the saturated hydrocarbon group has 2 to 20 carbon atoms, -CH ₂ - constituting the saturated hydrocarbon group may be substituted with -O- or -CO-, and R ⁴⁸ and R ⁵² are It may combine with each other to form -NH-, -S-, or -SO ₂ -. However, in this saturated hydrocarbon group, adjacent -CH ₂ - is not simultaneously substituted with -O-, and terminal -CH ₂ - is not substituted with -O- or -CO-.

Ring T ¹ represents an aromatic heterocycle having 3 to 10 carbon atoms, and the aromatic heterocycle is a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, a substituted or unsubstituted amino group, or 6 carbon atoms which may have a substituent. You may have an aromatic hydrocarbon group of -20, -SO ₃ ^- or -SO ₂ -N ^- -SO ₂ -R ^f . -SO ₃ ^- or -SO ₂ -N ^- -SO ₂ -R ^f may be sufficient as the substituent which this aromatic hydrocarbon group may have.

M ^r+ represents an r-valent metal ion.

k represents the sum of the number of -SO ₃ ^- and the number of -SO ₂ -N ^- -SO ₂ -R ^f which the compound represented by formula (a) has.

r represents an integer of 1 or more.

R ^f represents a C1-C12 fluoroalkyl group.

However, the compound represented by formula (a) has at least one -SO ₃ ^- or -SO ₂ -N ^- -SO ₂ -R ^f ]

[0011] The aromatic heterocyclic ring represented by Ring T ¹ may be monocyclic or condensed. Carbon number of the aromatic heterocyclic ring represented by ring T ¹ becomes like this. Preferably it is 3-10, More preferably, it is 3-8. Moreover, it is preferable that it is a 5- to 10-membered ring, and, as for an aromatic heterocyclic ring, it is more preferable that it is a 5- to 9-membered ring. Examples of the monocyclic aromatic heterocyclic ring include a 5-membered ring containing a nitrogen atom such as a pyrrole ring, an oxazole ring, a pyrazole ring, an imidazole ring, and a thiazole ring; 5-membered rings which do not contain a nitrogen atom, such as a furan ring and a thiophene ring; 6-membered ring containing a nitrogen atom, such as a pyridine ring, a pyrimidine ring, a pyridazine ring, and a pyrazine ring; etc. are mentioned, As an aromatic heterocyclic ring which is a condensed ring, Condensed ring containing nitrogen atoms, such as an indole ring, a benzimidazole ring, a benzothiazole ring, and a quinoline ring; Condensed rings which do not contain nitrogen atoms, such as a benzofuran ring; and the like.

[0012] Examples of the substituent that the aromatic heterocyclic ring of Ring T ¹ may have include a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, a substituted or unsubstituted amino group, and an aromatic hydrocarbon having 6 to 20 carbon atoms which may have a substituent. group, -SO ₃ ^- or -SO ₂ -N ^- -SO ₂ -R ^f , etc., preferably a saturated hydrocarbon group having 1 to 10 carbon atoms, a substituted or unsubstituted amino group, or a carbon number that may have a substituent and 6-10 aromatic hydrocarbon groups. Ring T ¹ preferably has an amino group which may have a substituent, and as the substituent which the amino group may have, a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, or a saturated hydrocarbon group having 6 to 10 carbon atoms which may have a substituent A phosphorus aromatic hydrocarbon group, a C7-30 aralkyl group which may have a substituent, etc. are preferable.

Among these, as the aromatic heterocycle of the ring T ¹ , an aromatic heterocycle containing a nitrogen atom is preferable, and a 5-membered aromatic heterocycle containing a nitrogen atom is more preferable.

[0013] Ring T ¹ is preferably a ring represented by formula (t1).

[0014]

[0015] [In formula (t1),

X2 represents -O-, -N(R ⁵⁷ )-, or -S-.

R ⁵⁷ represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms.

R ⁴⁵ and R ⁴⁶ are each independently a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 7 to carbon atoms which may have a substituent 30 represents an aralkyl group.

R ⁵⁵ represents a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent.

In R ⁴⁵ , R ⁴⁶ and R ⁵⁵ , when the saturated hydrocarbon group has 2 to 20 carbon atoms, —CH ₂ — contained in the saturated hydrocarbon group may be substituted with —O— or —CO—. However, in the saturated hydrocarbon group having 2 to 20 carbon atoms, adjacent -CH ₂ - is not simultaneously substituted with -O-, and the terminal -CH ₂ - is not substituted with -O- or -CO-.

R ⁴⁵ and R ⁴⁶ may combine to form a ring together with the nitrogen atom to which they are bonded.

* indicates a bond with a carbocation.]

[0016] Also, the ring T ¹ is preferably a ring represented by the formula (t2).

[0017]

[0018] [In formula (t2),

Ring T ³ represents an aromatic heterocyclic ring having 3 to 10 carbon atoms and having a nitrogen atom.

R ⁵⁸ is a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, -SO ₃ ^- , or -SO ₂ -N ^- -SO ₂ -R ^f indicates

R ⁵⁹ represents a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, or an aralkyl group having 7 to 30 carbon atoms which may have a substituent.

k2 represents 0, 1, or 2.

* indicates a bond with a carbocation.]

[0019] The ring represented by the formula (t2) is more preferably a ring represented by the formula (t2-1).

[0020]

[0021] In formula (t2-1),

R ⁶⁰ represents a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent.

R ⁶¹ represents -SO ₃ ^- or -SO ₂ -N ^- -SO ₂ -R ^f .

R ⁵⁹ has the same meaning as above.

* indicates a bond with a carbocation.]

[0022] The ring T ¹ is preferably a ring represented by formula (t1) or formula (t2), and more preferably a ring represented by formula (t1).

[0023] A saturated hydrocarbon group having 1 to 20 carbon atoms represented by R ⁴¹ to R ⁵⁵ and R ⁵⁸ to R ⁶⁰ , a saturated hydrocarbon group having 1 to 20 carbon atoms which the ring T ¹ may have, and a ring T ¹ may have The saturated hydrocarbon group having 1 to 20 carbon atoms which the amino group may have may be linear, branched, or cyclic. Examples of the linear or branched saturated hydrocarbon group include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, a dodecyl group, a hexadecyl group, an icosyl group, and the like. of a straight-chain alkyl group; Branched alkyl groups, such as an isopropyl group, an isobutyl group, an isopentyl group, a neopentyl group, and 2-ethylhexyl group, etc. are mentioned. Carbon number of this saturated hydrocarbon group becomes like this. Preferably it is 1-10, More preferably, it is 1-8, More preferably, it is 1-6.

The cyclic saturated hydrocarbon group may be monocyclic or polycyclic, and examples of the cyclic saturated hydrocarbon group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, an adamantyl group, and the like. of alicyclic saturated hydrocarbon groups. The number of carbon atoms of the cyclic saturated hydrocarbon group is preferably 3 to 10, more preferably 6 to 10.

[0025] As the saturated hydrocarbon group represented by R ⁴¹ to R ⁵⁵ and R ⁵⁸ to R ⁶⁰ , the saturated hydrocarbon group which the ring T ¹ may have, and the amino group which the ring T ¹ may have, the saturated hydrocarbon group which may have, A methyl group, an ethyl group, an isopropyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, an isobutyl group, 2-ethylhexyl group, a cyclohexyl group, an adamantyl group, etc. are preferable.

[0026] The saturated hydrocarbon group represented by R ⁴¹ to R ⁵⁵ and R ⁵⁸ to R ⁶⁰ , the saturated hydrocarbon group that the ring T ¹ may have, and the saturated hydrocarbon group that the amino group that the ring T ¹ may have may be substituted Or you may have an unsubstituted amino group or a halogen atom as a substituent. As a substituted amino group, alkylamino groups, such as a dimethylamino group and a diethylamino group, are mentioned. Moreover, as a halogen atom, a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom are mentioned. When the halogen atom is a fluorine atom, the saturated hydrocarbon group having a fluorine atom as a substituent is preferably a perfluoroalkyl group such as a trifluoromethyl group, a perfluoroethyl group or a perfluoropropyl group.

[0027] In addition, as the alkyl group having 1 to 10 carbon atoms represented by R ⁵⁷ , a group having 1 to 10 carbon atoms among the linear or branched saturated hydrocarbon groups exemplified as the saturated hydrocarbon group represented by R ⁴¹ is selected. can be heard

[0028] When the saturated hydrocarbon group represented by R ⁴¹ to R ⁵⁵ has 2 to 20 carbon atoms, -CH ₂ - contained in the saturated hydrocarbon group may be substituted with -O- or -CO-. However, in the saturated hydrocarbon group having 2 to 20 carbon atoms, adjacent -CH ₂ - is not simultaneously substituted with -O-, and the terminal -CH ₂ - is not substituted with -O- or -CO-. In this case, as the saturated hydrocarbon group, a linear or branched saturated hydrocarbon group (that is, a linear or branched alkyl group) is preferable, and a linear saturated hydrocarbon group (ie, a linear alkyl group) is more preferable. . The saturated hydrocarbon group in which -CH ₂ - may be substituted with -O- or -CO- preferably has 2 to 10 carbon atoms, more preferably 2 to 8 carbon atoms. In addition, when -CH ₂ - is substituted with -O- or -CO-, the number of carbon atoms between the terminal and -O- or -CO- or between -O- or -CO- and -O- or -CO- is 1 or more, preferably 1-5, more preferably 2-3, still more preferably 2.

In addition, the aromatic hydrocarbon group represented by R ⁴¹ to R ⁴⁶ , R ⁵⁵ and R ⁵⁸ to R ⁶⁰ , the aromatic hydrocarbon group which the ring T ¹ may have, and the amino group which the ring T ¹ may have may have Carbon number of an aromatic hydrocarbon group becomes like this. Preferably it is 6-20, More preferably, it is 6-15, More preferably, it is 6-12. Examples of the aromatic hydrocarbon group include a phenyl group, a tolyl group, a xylyl group, a naphthyl group, an anthryl group, a phenanthryl group, a biphenyl group, and a terphenyl group, and preferably a phenyl group, a naphthyl group, a tolyl group, It is a silyl group. Moreover, this aromatic hydrocarbon group may have 1 or 2 or more substituents. Examples of the substituent include a halogen atom such as a fluorine atom, a chlorine atom, an iodine atom and a bromine atom; an alkoxy group having 1 to 6 carbon atoms, such as a methoxy group and an ethoxy group; hydroxyl group; sulfamoyl group; an alkylsulfonyl group having 1 to 6 carbon atoms such as a methylsulfonyl group; an alkoxycarbonyl group having 1 to 6 carbon atoms, such as a methoxycarbonyl group and an ethoxycarbonyl group; -SO ₃ ^- ; -SO ₂ -N ^- -SO ₂ -R ^f ; etc. are mentioned, -SO ₃ ^- or -SO ₂ -N ^- -SO ₂ -R ^f may be sufficient. However, -SO ₃ ^- and -SO ₂ -N ^- -SO ₂ -R ^f are those directly bonded to the aromatic hydrocarbon ring of the aromatic hydrocarbon group, that is, those having a hydrogen atom bonded to the aromatic hydrocarbon ring substituted. desirable. As the substituent in the aromatic hydrocarbon group represented by R ⁵⁵ , a halogen atom is preferable.

Specific examples of the aromatic hydrocarbon group which may have a substituent include, for example, a group represented by the following formula. The group represented by the following formula may further have at least one -SO ₃ ^- or -SO ₂ -N ^- -SO ₂ -R ^f . In the following formula, * represents a bond with a nitrogen atom or a carbon atom.

[0031]

[0032]

[0033] As the aralkyl group which the aralkyl group represented by R ⁴¹ to R ⁴⁶ and R ⁵⁹ and the amino group which the ring T ¹ may have may have, in the group described as the aromatic hydrocarbon group, a methylene group, an ethylene group, a propylene group, etc. The group etc. which the C1-C10 (preferably C1-C5) alkanediyl group couple|bonded are mentioned. Carbon number of this aralkyl group becomes like this. Preferably it is 7-30, More preferably, it is 7-20, More preferably, it is 7-17. Moreover, this aralkyl group may have 1 or 2 or more substituents. Examples of the substituent include a halogen atom such as a fluorine atom, a chlorine atom, an iodine atom and a bromine atom; an alkoxy group having 1 to 6 carbon atoms, such as a methoxy group and an ethoxy group; hydroxyl group; sulfamoyl group; an alkylsulfonyl group having 1 to 6 carbon atoms such as a methylsulfonyl group; an alkoxycarbonyl group having 1 to 6 carbon atoms, such as a methoxycarbonyl group and an ethoxycarbonyl group; -SO ₃ ^- ; -SO ₂ -N ^- -SO ₂ -R ^f ; and the like.

[0034] A ring formed by combining R ⁴¹ and R ⁴² together with the nitrogen atom to which they are bonded, a ring formed by combining R ⁴³ and R ⁴⁴ with the nitrogen atom to which they are bonded, and R ⁴⁵ and R ⁴⁶ bonding to each other Examples of the ring formed together with the nitrogen atom to which they are bonded include nitrogen-containing non-aromatic 4- to 7-membered rings such as a pyrrolidine ring, a morpholine ring, a piperidine ring, and a piperazine ring. and preferably a 4- to 7-membered ring having only one nitrogen atom as a hetero atom such as a pyrrolidine ring or a piperidine ring.

Among them, R ⁴¹ to R ⁴⁴ , R ⁵⁵ , R ⁵⁸ to R ⁶⁰ are each independently preferably a saturated hydrocarbon group having 1 to 20 carbon atoms or an aromatic hydrocarbon group which may have a substituent, and each independently It is more preferable that it is a C1-C8 saturated hydrocarbon group or group represented by a following formula. In particular, R ⁴¹ and R ⁴³ are each independently preferably a saturated hydrocarbon group having 1 to 20 carbon atoms, and more preferably each independently a saturated hydrocarbon group having 1 to 8 carbon atoms. R ⁴² and R ⁴⁴ are each independently preferably an aromatic hydrocarbon group which may have a substituent, and are each independently a phenyl group which may have a substituent, a tolyl group which may have a substituent, and a xylyl group which may have a substituent more preferably. R ⁵⁵ is more preferably an aromatic hydrocarbon group which may have a substituent.

R ⁵⁵ , R ⁵⁸ to R ⁶⁰ are still more preferably a group represented by the following formula. The group represented by the following formula may further have at least one -SO ₃ ^- or -SO ₂ -N ^- -SO ₂ -R ^f . In the following formula, * represents a bond with a nitrogen atom or a carbon atom.

[0036]

[0037]

[0038] R ⁴⁵ to R ⁴⁶ are each independently, at least one -CH ₂ - constituting a saturated hydrocarbon group having 1 to 20 carbon atoms or an alkyl group having 2 to 20 carbon atoms is substituted with -O- or -CO- It is preferably a group or an aromatic hydrocarbon group which may have a substituent, or R ⁴⁵ and R ⁴⁶ are bonded to form a ring together with the nitrogen atom to which they are bonded. R ⁴⁵ to R ⁴⁶ are each independently a saturated hydrocarbon group having 1 to 8 carbon atoms, an alkoxyalkyl group, or a group represented by the following formula, or R ⁴⁵ and R ⁴⁶ are bonded to each other to form only one nitrogen atom as a hetero atom It is more preferable that the branches form a 4- to 7-membered ring, and each independently a saturated hydrocarbon group having 1 to 8 carbon atoms, an alkoxyalkyl group, or a group represented by the following formula is still more preferable. The group represented by the following formula may further have at least one -SO ₃ ^- or -SO ₂ -N ^- -SO ₂ -R ^f as a substituent. In the following formula, * represents a bond with a nitrogen atom.

[0039]

[0040]

Among them, R ⁴⁵ is a saturated hydrocarbon group having 1 to 4 carbon atoms, and R ⁴⁶ is preferably an o-tolyl group.

[0042] R ⁴⁷ to R ⁵⁴ are each independently a hydrogen atom, a halogen atom, or a linear or branched saturated hydrocarbon group having 1 to 8 carbon atoms, and each independently a hydrogen atom, a methyl group, a fluorine atom Or it is more preferable that it is a chlorine atom, and it is still more preferable that it is a hydrogen atom each independently.

Moreover, as R ⁵⁷ , a hydrogen atom or an alkyl group having 1 to 5 carbon atoms is preferable.

R ⁶¹ is preferably a hydrogen atom.

Examples of the r-valent metal ion represented by M ^r+ include alkali metal ions such as lithium ions, sodium ions, and potassium ions; alkaline earth metal ions such as beryllium ions, magnesium ions, calcium ions, strontium ions, and barium ions; Transition metal ions, such as a titanium ion, a zirconium ion, a chromium ion, a manganese ion, an iron ion, a cobalt ion, a nickel ion, and a copper ion; Typical metal ions, such as a zinc ion, a cadmium ion, an aluminum ion, an indium ion, a tin ion, a lead ion, and a bismuth ion, etc. are mentioned. r becomes like this. Preferably it is 1 or more, More preferably, it is 2 or more, Preferably it is 5 or less, More preferably, it is 4 or less, More preferably, it is 3 or less.

As M ^r+ , an alkaline earth metal ion, a typical metal ion, etc. are more preferable, an alkaline earth metal ion and a zinc ion are still more preferable, and an alkaline earth metal ion is still more preferable.

In formula (a), the number of M ^r+ is 1 than the sum (k) of the number of -SO ₃ ^- and -SO ₂ -N ^- -SO ₂ -R ^f of the compound (a) the number of dogs is small. For this reason, the compound (a) becomes a compound having a valence of 0, that is, electrically neutral.

[0045] Examples of the fluoroalkyl group having 1 to 12 carbon atoms represented by R ^f include monofluoromethyl group, difluoromethyl group, perfluoromethyl group, monofluoroethyl group, difluoroethyl group, trifluoroethyl group, tetrafluoro Roethyl group, perfluoroethyl group, monofluoropropyl group, difluoropropyl group, trifluoropropyl group, tetrafluoropropyl group, pentafluoropropyl group, hexafluoropropyl group, perfluoropropyl group, Monofluorobutyl group, difluorobutyl group, trifluorobutyl group, tetrafluorobutyl group, pentafluorobutyl group, hexafluorobutyl group, heptafluorobutyl group, octafluorobutyl group, perfluoro A robutyl group etc. are mentioned. Among them, as the fluoroalkyl group represented by R ^f , a perfluoroalkyl group is preferable. Moreover, carbon number of the fluoroalkyl group represented by R ^f becomes like this. Preferably it is 1-10, More preferably, it is 1-5, More preferably, it is 1-3.

[0046] In formula (a), R ⁴¹ to R ⁴⁴ , R ⁴⁷ to R ⁵⁴ and ring T ¹ have at least one —SO ₃ ^— or —SO ₂ —N ^— —SO ₂ —R ^f . The sum (k) of the number of -SO ₃ ^- and -SO ₂ -N ^- -SO ₂ -R ^f in R ⁴¹ to R ⁴⁴ , R ⁴⁷ to R ⁵⁴ and the ring T ¹ is 1 or more, preferably It is 1 or more and 7 or less, More preferably, it is 2 or more and 7 or less, Even more preferably, it is 2 or more and 4 or less, More preferably, it is 2 or 3, Especially preferably, it is 2.

-SO ₃ ^- or -SO ₂ -N ^- -SO ₂ -R ^f preferably satisfies at least one condition selected from the following (Ia) to (Id), (Ia) and ( It is more preferable to satisfy at least one condition selected from Ib).

(Ia) included as any one of R ⁴⁷ to R ⁵⁴

(Ib) bonded to any one of the aromatic hydrocarbon groups having 6 to 20 carbon atoms which may have a substituent represented by R ⁴¹ to R ⁴⁴

(Ic) bonded to any one of the aralkyl groups having 7 to 30 carbon atoms which may have a substituent represented by R ⁴¹ to R ⁴⁴

(Id) bonded to any one of the aromatic hydrocarbon group having 6 to 20 carbon atoms replacing the hydrogen atom of the aromatic heterocyclic ring represented by T ¹

However, when -SO ₃ ^- or -SO ₂ -N ^- -SO ₂ -R ^f is bonded to an aromatic hydrocarbon group or an aralkyl group, -SO ₃ ^- or -SO ₂ -N ^- -SO ₂ - R ^f is preferably directly bonded to an aromatic hydrocarbon group or an aromatic hydrocarbon ring of an aralkyl group. That is, it is preferable that -SO ₃ ^- or -SO ₂ -N ^- -SO ₂ -R ^f has substituted a hydrogen atom bonded to the aromatic hydrocarbon ring.

-SO ₃ ^- or -SO ₂ -N ^- -SO ₂ -R ^f is an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent representing R ⁴¹ to R ⁴⁴ or a substituent representing R ⁴¹ to R ⁴⁴ In the aromatic hydrocarbon ring (for example, a benzene ring) in the optionally C7-30 aralkyl group, it is preferable to couple|bond with the para position with respect to the bonding position with a nitrogen atom.

When a plurality of -SO ₃ ^- or -SO ₂ -N ^- -SO ₂ -R ^f is included in compound (a), a plurality of -SO ₃ ^- or -SO ₂ -N ^- -SO ₂ -R ^f is, Although you may couple|bond with the same aromatic hydrocarbon ring, it is preferable to couple|bond with different aromatic hydrocarbon rings.

[0049] The compound (a) preferably does not have an ethylenically unsaturated bond.

[0050] In the compound (a), R ⁴¹ and R ⁴³ are each independently a saturated hydrocarbon group having 1 to 10 carbon atoms (a hydrogen atom included in the saturated hydrocarbon group is substituted with a substituted or unsubstituted amino group or a halogen atom, may be present, and when the saturated hydrocarbon group has 2 to 10 carbon atoms, -CH ₂ - contained in the saturated hydrocarbon group may be substituted with -O- or -CO-), and R ⁴² and R ⁴⁴ are , each independently of the phenyl group which may have a substituent, the tolyl group which may have a substituent, or the xylyl group which may have a substituent (The said phenyl group, a tolyl group, and the substituent which the xylyl group may have are -SO ₃ ^- or -SO ₂ -N ^- -SO ₂ -R ^f ), R ⁴⁷ to R ⁵⁴ is a hydrogen atom, and ring T ¹ is a 5-membered ring containing a nitrogen atom (the 5-membered ring has a number of carbon atoms) It may have a saturated hydrocarbon group of 1 to 10, a substituted or unsubstituted amino group, or an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent, The substituent that the aromatic hydrocarbon group may have is -SO ₃ ^- or -SO ₂ -N ^- -SO ₂ -R ^f may be used.) or a compound represented by the formula (a-1) (hereinafter, sometimes referred to as "compound (a-1)") is preferable.

[0051]

[0052] In formula (a-1),

R ^47A to R ^54A each independently represent a hydrogen atom, —SO ₃ ^— , or a saturated hydrocarbon group having 1 to 10 carbon atoms.

R ^41A and R ^43A are each independently a hydrogen atom, a saturated hydrocarbon group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, or aral having 7 to 30 carbon atoms which may have a substituent A alkyl group is represented, and -SO ₃ ^- may be sufficient as the substituent which the said aromatic hydrocarbon group and this aralkyl group may have.

R ^11A to R ^20A each independently represent —SO ₃ ^— , a hydrogen atom, a saturated hydrocarbon group having 1 to 10 carbon atoms, or a halogen atom.

R ^45A , R ^46A and R ^55A each independently represent a hydrogen atom, a saturated hydrocarbon group having 1 to 10 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, and the aromatic hydrocarbon group -SO ₃ ^- may be sufficient as the substituent which you may have.

In the above R ^47A to R ^54A , R ^41A , R ^43A , R ^11A to R ^20A , R ^45A , R ^46A and R ^55A , when the number of carbon atoms in the saturated hydrocarbon group is 2 to 10, included in the saturated hydrocarbon group - CH ₂ - may be substituted with -O- or -CO-. However, in the saturated hydrocarbon group having 2 to 10 carbon atoms, adjacent -CH ₂ - is not simultaneously substituted with -O-, and terminal -CH ₂ - is not substituted with -O- or -CO-.

M ^r+ represents an r-valent metal ion.

k represents the number of SO ₃ ⁻ groups included in the compound represented by the formula (a-1).

However, the compound represented by Formula (a-1) has at least two SO ₃ ^- groups.

r represents an integer of 2 or more.]

[0053] As the saturated hydrocarbon group having 1 to 10 carbon atoms represented by R ^47A to R ^54A , R ^41A , R ^43A , R ^11A to R ^20A , R ^45A , R ^46A and R ^55A , the saturated hydrocarbon group exemplified by R ⁴¹ is and a group having 1 to 10 carbon atoms.

[0054] The substituents that the saturated hydrocarbon group having 1 to 10 carbon atoms represented by R ^45A , R ^46A and R ^55A may have are the same as those exemplified as the substituents that the saturated hydrocarbon group represented by R ⁴¹ may have.

The aromatic hydrocarbon group having 6 to 20 carbon atoms represented by R ^41A , R ^43A , R ^45A , R ^46A and R ^55A is the same as the group exemplified as the aromatic hydrocarbon group having 6 to 20 carbon atoms represented by R ⁴¹ .

The aralkyl group having 7 to 30 carbon atoms represented by R ^41A and R ^43A is the same as the group exemplified as the aralkyl group having 7 to 30 carbon atoms represented by R ⁴¹ .

Substituents which the aromatic hydrocarbon group having 6 to 20 carbon atoms represented by R ^41A , R ^43A , R ^45A , R ^46A and R ^55A , and the aralkyl group having 7 to 30 carbon atoms represented by R ^41A and R ^43A may have As examples, halogen atoms such as fluorine atom, chlorine atom, iodine atom and bromine atom; an alkoxy group having 1 to 6 carbon atoms, such as a methoxy group and an ethoxy group; hydroxyl group; sulfamoyl group; an alkylsulfonyl group having 1 to 6 carbon atoms such as a methylsulfonyl group; an alkoxycarbonyl group having 1 to 6 carbon atoms, such as a methoxycarbonyl group and an ethoxycarbonyl group; -SO ₃ ^- ; and the like.

[0058] Examples of the halogen atom represented by R ^11A to R ^20A include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and a fluorine atom is preferable.

[0059] R ^47A to R ^54A are each independently, more preferably a hydrogen atom, -SO ₃ ^- , or a methyl group, and still more preferably a hydrogen atom or a methyl group.

R ^41A and R ^43A are each independently a saturated hydrocarbon group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, or an aralkyl group having 7 to 30 carbon atoms which may have a substituent It is preferable,

each independently, a saturated hydrocarbon group having 1 to 8 carbon atoms; phenyl group; tolyl group; naphthyl group; methylnaphthyl group; an unsubstituted aralkyl group; or at least one selected from a halogen atom, a methoxy group, an ethoxy group, a sulfamoyl group, a methylsulfonyl group, a methoxycarbonyl group, and an ethoxycarbonyl group, more preferably an aralkyl group substituted with one type,

Each independently, it is more preferable that it is a C1-C4 linear alkyl group.

From the viewpoint of heat resistance and light resistance, at least one of R ^11A to R ^12A is preferably a halogen atom or a saturated hydrocarbon group having 1 to 10 carbon atoms, and at least either one is a halogen atom or a saturated hydrocarbon group having 1 to 8 carbon atoms It is more preferable that it is a saturated hydrocarbon group, and it is still more preferable that at least either one is a fluorine atom or a C1-C4 saturated hydrocarbon group.

From the viewpoint of heat resistance and light resistance, at least one of R ^13A to R ^14A is preferably a halogen atom or a saturated hydrocarbon group having 1 to 10 carbon atoms, and at least either one is a halogen atom or a saturated hydrocarbon group having 1 to 8 carbon atoms It is more preferable that it is a saturated hydrocarbon group, and it is still more preferable that at least either one is a fluorine atom or a C1-C4 saturated hydrocarbon group.

[0063] R ^15A to R ^20A are each independently a hydrogen atom, -SO ₃ ^- , or a saturated hydrocarbon group having 1 to 10 carbon atoms, and a hydrogen atom, -SO ₃ ^- or a C1-C4 saturated hydrocarbon group is more preferable, and it is still more preferable that it is a hydrogen atom, -SO ₃ ^- , or a methyl group.

R ^45A , R ^46A and R ^55A are each independently preferably a saturated hydrocarbon group having 1 to 10 carbon atoms or an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent,

an aromatic hydrocarbon group having 6 to 10 carbon atoms which may be substituted with a halogen atom, an alkoxy group having 1 to 4 carbon atoms, a hydroxy group, or a methylsulfonyl group; Or it is more preferably a saturated hydrocarbon group having 1 to 8 carbon atoms,

It is more preferable that it is a C1-C8 saturated hydrocarbon group or an aromatic hydrocarbon group represented by the following formula.

[0065] In particular, R ⁴⁵ and R ⁴⁶ are preferably a saturated hydrocarbon group having 1 to 6 carbon atoms, and the other is preferably an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent; Either one is a C1-C6 saturated hydrocarbon group, and it is more preferable that the other is an aromatic hydrocarbon group represented by a following formula. It is preferable that R ⁵⁵ is a C6-C20 aromatic hydrocarbon group which has a halogen atom, and it is more preferable that it is a C6-C20 aromatic hydrocarbon group which has two or more halogen atoms. The number of halogen atoms in the aromatic hydrocarbon group represented by R ⁵⁵ is preferably 1 to 6, more preferably 1 to 4, still more preferably 2 to 3. It is preferable that this halogen atom is a fluorine atom.

It is also preferable that R ⁵⁵ is an aromatic hydrocarbon group represented by the following formula. In the following formula, * represents a bond with a carbon atom.

[0066]

[0067]

In Formula (a-1), the number of -SO ₃ ^- is 2 or more, preferably 6 or less, and more preferably 4 or less.

[0069] -SO ₃ ^- is,

(ia) included as any one of R ^47A ~ R ^54A , R ^11A ~ R ^20A ,

(ib) an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent represented by R ^41A and R ^43A , and an aralkyl group having 7 to 30 carbon atoms which may have a substituent represented by R ^41A or R ^43A connected or

(ic) is bonded to any one of the aromatic hydrocarbon groups having 6 to 20 carbon atoms which may have a substituent represented by R ^45A , R ^46A , or R ^55A , or

It is preferable to exist as a combination of these (ia)-(ic),

It is more preferable to exist as a combination of (ia), (ib) or (ia) to (ib),

It is more preferred to exist as (ia).

Moreover, among R ^47A -R ^54A and R ^11A -R ^20A , it is especially preferable that -SO ₃ ^- is included as R ^16A and R ^19A .

[0070] In (ia) to (ic), -SO ₃ ^- is preferably directly bonded to an aromatic hydrocarbon group or an aromatic hydrocarbon ring of an aralkyl group. That is, it is preferable that -SO ₃ ^- has substituted a hydrogen atom bonded to the aromatic hydrocarbon ring.

Although two or more -SO ₃ ^- may couple|bond with the same aromatic hydrocarbon ring, it is preferable to couple|bond with different aromatic hydrocarbon rings.

[0071] As the compound (a), as shown in Tables 1 to 9 below, compounds 1 to 514 represented by formulas (a-2) and the like are exemplified.

However, the compound represented by the formula (a-2) has two -SO ₃ ^- , and the -SO ₃ ^- is any two of the hydrogen atoms represented by R ^h and R ^11A to R ^14A . is substituted, preferably any two of the hydrogen atoms represented by R ^h are substituted, and more preferably, in the benzene ring bonded to the nitrogen atom, in the para position with respect to the bonding position with the nitrogen atom. It is substituted for the position R ^h .

[0073]

[0074] [Table 1]

[0075] [Table 2]

[0076] [Table 3]

[0077] [Table 4]

[0078] [Table 5]

[0079] [Table 6]

[0080] [Table 7]

[0081] [Table 8]

[0082] [Table 9]

In Tables 1 to 9, Me represents a methyl group, Et represents an ethyl group, iPr represents an isopropyl group, Bt represents an n-butyl group, and Ph1 to Ph10 represent groups represented by the following formulas, respectively. Among Ph1-Ph10, * represents a bond.

[0084]

Among them, as compound (a),

Compound 31 to compound 90, compound 121 to compound 180, compound 211 to compound 334, compound 365 to compound 424, and compound 455 to compound 514 are preferred;

Compound 46 to compound 60, compound 61 to compound 90, compound 136 to compound 150, compound 226 to compound 240, compound 271 to compound 334, compound 380 to compound 394, and compound 470 to compound 484 are more preferable,

Compound 46 to compound 60, compound 61 to compound 90, compound 136 to compound 150, compound 226 to compound 240, compound 271 to compound 304, compound 380 to compound 394, and compound 470 to compound 484 are more preferable,

Compound 46 to compound 60, compound 61 to compound 90, compound 136 to compound 150, compound 226 to compound 240, compound 271 to compound 294, compound 380 to compound 394, and compound 470 to compound 484 are more preferable,

Compound 46 to compound 60, compound 61 to compound 90, compound 136 to compound 150, compound 226 to compound 240, compound 279 to compound 294, compound 380 to compound 394, and compound 470 to compound 484 are particularly more preferred.

According to these compounds, especially high heat resistance and light resistance are made compatible, and brightness can become more favorable.

[0086] The compound (a) having -SO ₃ ^- is, for example, sulfonation of the compound represented by the formula (aC) (hereinafter sometimes referred to as compound (aC)), and furthermore, r-valent metal ions It can be prepared by reacting with a halide (preferably chloride), acetate, phosphate, sulfate, silicate or cyanide containing

[0087]

[0088] In formula (aC),

R ^1c to R ^4c are each independently a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 7 to carbon atoms which may have a substituent When an aralkyl group of 30 is represented and the saturated hydrocarbon group has 2 to 20 carbon atoms, -CH ₂ - contained in the saturated hydrocarbon group may be substituted with -O- or -CO-. However, in the saturated hydrocarbon group having 2 to 20 carbon atoms, adjacent -CH ₂ - is not simultaneously substituted with -O-, and the terminal -CH ₂ - is not substituted with -O- or -CO-. R ^1c and R ^2c may combine to form a ring together with the nitrogen atom to which they are bonded, or R ^3c and R ^4c may combine to form a ring together with the nitrogen atom to which they are bonded.

R ^7c to R ^14c each independently represent a hydrogen atom, a halogen atom, a nitro group, a hydroxy group, or a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and when the saturated hydrocarbon group has 2 to 20 carbon atoms , -CH ₂ - constituting the saturated hydrocarbon group may be substituted with -O- or -CO-. However, in this saturated hydrocarbon group, adjacent -CH ₂ - is not simultaneously substituted with -O-, and terminal -CH ₂ - is not substituted with -O- or -CO-. R ^8c and R ^12c may be bonded to each other to form -NH-, -S-, or -SO ₂ -.

Ring T ¹⁰ represents an aromatic heterocycle having 3 to 10 carbon atoms, and the aromatic heterocycle is a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, a substituted or unsubstituted amino group, or a carbon number which may have a substituent You may have an aromatic hydrocarbon group of 6-20.

M ^1c represents Cl ⁻ , phosphate ion, perchlorate ion, BF ₄ ⁻ or PF ₆ . ^]

[0089] The compound (a) having -SO ₂ -N ^- -SO ₂ -R ^f has a -SO ₃ ^- group, and -SO ₂ -N ^- -SO ₂ -R ^f with the compound (a) not having , It can be produced by reacting the compound represented by the formula (IB), and further reacting with a halide (preferably a chloride) containing an r-valent metal ion, an acetate, a phosphate, a sulfate, a silicate, or a cyanide.

[0090]

[In formula (IB), R ^f has the same meaning as above.]

[0092] As a method of sulfonation, various known methods, for example, Journal of Organic Chemistry, (1994), vol. 59, #11, p.3232-3236.

[0093] Compound (a) contains a dispersing agent and is subjected to dispersion treatment to obtain a dispersion in which the compound (a) is uniformly dispersed in a solution.

[0094] Examples of the dispersant include cationic, anionic, nonionic, amphoteric, polyester, polyamine, and acrylic surfactants. These dispersants may be used independently and may be used in combination of 2 or more type. As a dispersant, as a trade name, KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Florene (manufactured by KYOEISHA CHEMICAL Co., LTD.), Solsperse (manufactured by Zeneca Co., Ltd.), EFKA (manufactured by CIBA Co., Ltd.) ), Ajispar (manufactured by Ajinomoto Fine-Techno Co., Inc.), Disperbyk (manufactured by BYK-Chemie), BYK (manufactured by BYK-Chemie), and the like.

When using a dispersing agent, the usage-amount with respect to compound (a) becomes like this. Preferably it is 1 mass % or more and 100 mass % or less, More preferably, they are 15 mass % or more and 100 mass % or less. When the amount of the dispersant used is within the above range, a dispersion liquid in a uniformly dispersed state can be obtained.

[0095] The content of compound (a) in the dispersion is preferably 1 mass % or more and 80 mass % or less, more preferably 1 mass % or more and 50 mass % or less, and still more preferably 1 mass % or more and 30 mass % or less. mass% or less.

[0096] <<xanthene dye>>

It is preferable that a coloring agent (A) contains a xanthene dye further. As the xanthene dye, a known xanthene dye can be used. Among them, it is preferable to include a compound represented by the formula (1) (hereinafter also referred to as “compound (1)”) as a main component. In addition, in the present specification, "included as a main component" means preferably 50 mass % or more, more preferably 70 mass % or more, still more preferably 90 mass % or more, particularly preferably 98 mass % or more. , and the upper limit may be 100% by mass.

[0097]

[In formula (1), R ¹ to R ⁴ each independently represent a hydrogen atom, -R ⁸ or a monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms, or R ¹ and R ² and R ³ and R ⁴ together form a ring containing a nitrogen atom, respectively. A hydrogen atom included in the aromatic hydrocarbon group is a halogen atom, -OH, -OR ⁸ , -SO ₃ ^- , -SO ₃ H, -SO ₃ -M ⁺ , -CO ² H, -CO ₂ R ₈ , ^-SO ₃ R ⁸ or -SO ₂ NR ⁹ R ¹⁰ may be substituted.

R ⁵ is -OH, -SO ₃ ^- , -SO ₃ H, -SO ₃ -M ⁺ , -CO ₂ H ^, -CO ₂ -M ⁺ , -CO ² R ⁸ , -SO ₃ R ₈ or ^-SO ₂ NR ⁹ R ¹⁰ is represented.

m represents the integer of 0-5, and when m is an integer of 2 or more, some R< ⁵ > may be same or different.

R ⁶ and R ⁷ each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.

M ⁺ represents ⁺ N(R ¹¹ ) ₄ , Na ⁺ or K ⁺ , and X represents a halogen atom.

a represents 0 or 1.

R ⁸ represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, and the hydrogen atom contained in the saturated hydrocarbon group may be substituted with an aromatic hydrocarbon group having 6 to 10 carbon atoms, a carboxy group or a halogen atom, and contained in the saturated hydrocarbon group -CH ₂ - may be substituted with -S-, -O-, -CO-, or -NR ¹¹ -. However, in this saturated hydrocarbon group, adjacent -CH ₂ - is not simultaneously substituted with -O-. R ¹¹ represents a hydrogen atom, a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms, and when two or more R ¹¹ are present, all or part of these may be the same.

R ⁹ and R ¹⁰ each independently represent a hydrogen atom or a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, the hydrogen atom contained in the saturated hydrocarbon group may be substituted with —OH or a halogen atom, and the saturated aliphatic group -CH ₂ - contained in the hydrocarbon group may be substituted with -S-, -O-, -CO-, -NH- or -NR ⁸ -. However, in this saturated hydrocarbon group, adjacent -CH ₂ - is not simultaneously substituted with -O-.

R ⁹ and R ¹⁰ may be bonded to each other to form a 3- to 10-membered heterocyclic ring containing a nitrogen atom.]

[0098] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

Examples of the monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms in R ¹ to R ⁴ include a phenyl group, a toluyl group, a xylyl group, a mesityl group, a propylphenyl group, and a butylphenyl group.

[0100] Examples of the ring formed by R ¹ and R ² together and the ring formed by R ³ and R ⁴ together include the following rings. In the following rings, * represents a bond.

[0101]

[0102] Examples of the monovalent saturated hydrocarbon group having 1 to 20 carbon atoms in R ⁸ to R ¹¹ include the same groups as those exemplified as the saturated hydrocarbon group having 1 to 20 carbon atoms represented by R ⁴¹ .

[0103] With respect to R ⁸ , as an aromatic hydrocarbon group having 6 to 10 carbon atoms which may be substituted with a hydrogen atom contained in a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, the aromatic hydrocarbon group having 6 to 10 carbon atoms represented by R ¹ to R ⁴ The same group as the group illustrated as a monovalent|monohydric aromatic hydrocarbon group is mentioned.

[0104] Examples of the aralkyl group having 7 to 10 carbon atoms in R ¹¹ in the formula (1) include a benzyl group, a phenylethyl group, and a phenylbutyl group.

[0105] M ⁺ is ⁺ N(R ¹¹ ) ₄ , Na ⁺ or K ⁺ , preferably ⁺ N(R ¹¹ ) ₄ . It is preferable that ⁺ N(R ¹¹ ) ₄ is a monovalent saturated hydrocarbon group in which at least two of the four R ¹¹ are carbon atoms of 5 to 20 carbon atoms. Moreover, 20-80 are preferable and, as for total carbon number of four R< ¹¹ >, 20-60 are more preferable.

[0106] The xanthene dye more preferably contains the compound represented by formula (2) as a main component.

[0107]

[0108] In [Formula (2), R ²¹ to R ²⁴ represent, independently of each other, a hydrogen atom, -R ²⁶ or a monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms, and the hydrogen atom contained in the aromatic hydrocarbon group is, -CO ₂ H, -SO ₃ ^- , -SO ₃ ^{-Ma +} , -SO ₃ H, -SO ₃ R ²⁶ or -SO ₂ NHR ²⁶ may be substituted. X represents a halogen atom. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

a1 represents 0 or 1. m1 represents the integer of 0-5. When m1 is an integer of 2 or more, a plurality of R ²⁵ may be the same or different. Ma ⁺ represents ⁺ N(R ²⁷ ) ₄ , Na ⁺ or K ⁺ .

R ²⁵ represents -SO ₃ ^- , -SO ₃ ^{-Ma +} , -SO ₃ H or -SO ₂ NHR ²⁶ .

R ²⁶ represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, and the hydrogen atom contained in the saturated hydrocarbon group may be substituted with a carboxy group. Four R ²⁷ represent, independently of each other, a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms or a benzyl group.]

Examples of the monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms in R ²¹ to R ²⁴ in Formula (2) include the same groups as those exemplified as the aromatic hydrocarbon group in R ¹ to R ⁴ .

[0110] Examples of the monovalent saturated hydrocarbon group having 1 to 20 carbon atoms for R ²⁶ and R ²⁷ include the same groups as those exemplified as the saturated hydrocarbon group for R ⁸ to R ¹¹ . -R ²⁶ in R ²¹ to R ²⁴ in formula (2) is each independently preferably a linear alkyl group having 1 to 4 carbon atoms which may be substituted with a carboxy group, and more preferably a methyl group or an ethyl group. Moreover, as R ²⁶ in -SO ₃ R ²⁶ and -SO ₂ NHR ²⁶ , a branched-chain alkyl group having 3 to 20 carbon atoms is preferable, more preferably a branched-chain alkyl group having 6 to 12 carbon atoms, and 2-ethyl A hexyl group is more preferable.

[0111] M ^a+ is ⁺ N(R ²⁷ ) ₄ , Na ⁺ or K ⁺ , preferably ⁺ N(R ²⁷ ) ₄ . It is preferable that ⁺ N(R ²⁷ ) ₄ is a monovalent saturated hydrocarbon group in which at least two of four R ²⁷ are carbon atoms of 5 to 20 carbon atoms. Moreover, 20-80 are preferable and, as for total carbon number of four ^R27 , 20-60 are more preferable.

[0112] In formula (2), when R ²¹ and R ²³ are hydrogen atoms, and R ²² and R ²⁴ are monovalent aromatic hydrocarbon groups having 6 to 10 carbon atoms, and a hydrogen atom included in the aromatic hydrocarbon group is substituted, The substituted group is preferably -SO ₃ ^- , -SO ₃ -M ⁺ , -SO ³ H, -SO ₃ R ²⁶ or -SO ₂ ^{NHR 26} _. Further, R ²¹ and R ²³ are hydrogen atoms, and R ²² and R ²⁴ are a monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms (preferably a phenyl group, a toluyl group, or a xylyl group), and included in the aromatic hydrocarbon group It is more preferable that the hydrogen atom to be formed may be substituted _with -SO ₃ -M ⁺ or -SO ² NHR ²⁶ . When R ²¹ to R ²⁴ are these groups, it is advantageous in forming a color filter having excellent heat resistance.

[0113] In formula (2), R ²⁵ is preferably -SO ₃ ^- or SO ₂ NHR ²⁶ .

[0114] In formula (2), a1 is preferably 0.

[0115] The xanthene dye preferably contains, as a main component, any one or more of the compounds represented by formulas (1-1) to (1-39). In addition, in formula, Ra represents a 2-ethylhexyl group.

[0116]

[0117]

[0118]

[0119]

[0120]

[0121] Compounds represented by formulas (1-1) to (1-16) are, for example, -SO ₂ obtained by chlorinating a dye or a dye intermediate having -SO ₃ H by a prescribed method. It can be produced by reacting a dye or a dye intermediate having Cl with an amine represented by R ⁸ -NH ₂ .

In addition, the dye produced by the method described in the upper right column to the lower left column on page 3 of Japanese Patent Application Laid-Open No. H03-78702 can also be produced by a method of reacting with an amine after chlorination in the same manner as above.

[0122] The compound represented by formulas (1-17) to (1-32) can be produced according to the method described in the upper right column to the lower left column on page 3 of Japanese Patent Application Laid-Open No. H03-78702. Examples of such a method include a method in which the compound represented by the formula (1a) is reacted with the compound represented by the formula (1b) and the compound represented by the formula (1c). In formulas (1b) and (1c), R ¹ to R ⁴ each have the same meanings as above.

[0123]

[0124] The compounds represented by formulas (1-33) to (1-39) can be produced according to the method described in Japanese Patent Application Laid-Open No. 2017-226814.

[0125] <<Other Coloring Agents>>

The colorant (A) is, in addition to the compound (a) and the xanthene dye, other dyes (hereinafter sometimes referred to as dye (A1).) and other pigments (hereinafter sometimes referred to as pigment (A2).) One or both may be included.

[0126] The dye (A1) is not particularly limited, and a known dye can be used, and a solvent dye, an acid dye, a direct dye, a mordant dye, etc. are mentioned. As a dye, for example, a compound classified as having a color other than a pigment in the color index (published by The Society of Dyers and Colorists), or a dyeing note (SHIKISENSHA CO., LTD. and the known dyes that have been described. In addition, according to the chemical structure, azo dye, cyanine dye, triphenylmethane dye, phthalocyanine dye, anthraquinone dye, naphthoquinone dye, quinoneimine dye, methine dye, azomethine dye, squarylium dye, a Creidine dye, styryl dye, coumarin dye, quinoline dye, nitro dye, etc. are mentioned. Among these, organic solvent-soluble dyes are preferable.

[0127] Specifically, dyes having the following color index (C.I.) numbers are exemplified.

For example, C.I. Acid Yellow 1, 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112, 113, 114, 116, 119, 123, 128, 134, 135, 138, 139, 140, 144, 150, 155, 157, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251;

C.I. Solvent Yellow 14, 15, 23, 24, 25, 38, 62, 63, 68, 79, 81, 82, 83, 89, 94, 98, 99, 162;

C.I. Direct Yellow 2, 4, 28, 33, 34, 35, 38, 39, 43, 44, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129, 132, 136, 138, 141;

C.I. Disperse Yellow 51, 54, 76;

C.I. Reactive Yellow 2, 76, 116;

C.I. acid orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 149, 162, 169, 173;

C.I. Solvent Orange 2, 7, 11, 15, 26, 41, 54, 56, 99;

C.I. Direct Orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107;

C.I. Reactive Orange 16;

C.I. Acid Red 1, 4, 8, 14, 17, 18, 26, 27, 29, 31, 33, 34, 35, 37, 40, 42, 44, 50, 57, 66, 73, 76, 80, 88, 91, 95, 97, 98, 103, 106, 111, 114, 129, 133, 134, 138, 143, 145, 150, 151, 155, 158, 160, 172, 176, 182, 183, 195, 198, 206, 211, 215, 216, 217, 227, 228, 249, 252, 257, 258, 260, 261, 266, 268, 270, 274, 277, 280, 281, 308, 312, 315, 316, 339, 341, 345, 346, 349, 382, 383, 394, 401, 412, 417, 418, 422, 426;

C.I. Solvent Red 24, 49, 90, 91, 111, 118, 119, 122, 124, 125, 127, 130, 132, 143, 145, 146, 150, 151, 155, 160, 168, 169, 172, 175, 181, 207, 222, 227, 230, 245, 247;

C.I. Direct Red 79, 82, 83, 84, 91, 92, 96, 97, 98, 99, 105, 106, 107, 172, 173, 176, 177, 179, 181, 182, 184, 204, 207, 211, 213, 218, 220, 221, 222, 232, 233, 234, 241, 243, 246, 250;

C.I. Mordant Red 1, 2, 3, 4, 9, 11, 12, 14, 17, 18, 19, 22, 23, 24, 25, 26, 29, 30, 32, 33, 36, 37, 38, 39, 41, 42, 43, 45, 46, 48, 52, 53, 56, 62, 63, 71, 74, 76, 78, 85, 86, 88, 90, 94, 95;

C.I. Acid Violet 34;

C.I. Disperse Violet 26, 27;

C.I. solvent violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60;

C.I. Solvent Blue 14, 18, 35, 36, 45, 58, 59, 59:1, 63, 68, 69, 78, 79, 83, 94, 97, 98, 100, 101, 102, 104, 105, 111, 112, 122, 128, 132, 136, 139;

C.I. acid blue 25, 27, 40, 45, 78, 80, 112;

C.I. Direct Blue 40;

C.I. Disperse Blue 1, 14, 56, 60;

C.I. Solvent Green 1, 3, 5, 28, 29, 32, 33;

C.I. acid green 3, 5, 9, 25, 27, 28, 41;

C.I. Basic Green 1;

C.I. vat green 1 and the like are exemplified.

[0128] As the pigment, known pigments can be used, and for example, pigments classified as pigments in the Color Index (published by The Society of Dyers and Colorists) are exemplified. You may combine 2 or more types.

Specifically, C.I. Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 129, 137, 138 , 139, 147, 148, 150, 153, 154, 166, 173, 185, 194, 214 yellow pigments;

C.I. Orange pigments, such as pigment orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73;

C.I. Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 180, 192, 209, 215, 216, 224, 242, 254, 255, 264, 265, 266, 268 , 269, 273 and other red pigments;

C.I. Blue pigments, such as pigment blue 15, 15:3, 15:4, 15:6, 60;

C.I. Violet pigments, such as Pigment Violet 1, 19, 23, 29, 32, 36, 38;

C.I. The green pigment of Pigment Green 7, 36, 58, and 59 is mentioned.

[0129] The pigment (A2) is, if necessary, a rosin treatment, a surface treatment using a pigment derivative having an acidic or basic group introduced therein, a graft treatment to the pigment surface with a polymer compound, etc., and a sulfuric acid atomization method (微粒). chemical method), washing treatment with an organic solvent or water for removing impurities, removal treatment of ionic impurities by an ion exchange method, etc. may be performed.

It is preferable that a pigment (A2) has a uniform particle diameter. By containing a dispersing agent and performing a dispersion process, the pigment dispersion liquid in the state in which the pigment was uniformly disperse|distributed in the solution can be obtained.

[0130] As the dispersing agent, the above-described dispersing agent may be used. When using a dispersing agent, the usage-amount becomes like this with respect to the total amount of a pigment (A2). Preferably they are 1 mass % or more and 100 mass % or less, More preferably, they are 5 mass % or more and 50 mass % or less. When the amount of the pigment dispersant used is within the above range, a pigment dispersion liquid in a uniformly dispersed state can be obtained.

The content of compound (a) in the colorant (A) is preferably 50 mass % or more, more preferably 60 mass % or more, still more preferably 70 mass % or more, particularly preferably 80 mass % or more. % or more, 100 mass % may be sufficient, 98 mass % or less may be sufficient, and 95 mass % or less may be sufficient.

[0132] The content of the xanthene dye in the colorant (A) is preferably 1% by mass or more, more preferably 3% by mass or more, still more preferably 5% by mass or more, and preferably 30% by mass or less And more preferably, it is 20 mass % or less, More preferably, it is 10 mass % or less.

[0133] The total content of the compound (a) and the xanthene dye in the colorant (A) is preferably 75 mass % or more, more preferably 85 mass % or more, still more preferably 95 mass % or more, Especially preferably, it is 98 mass % or more, and 100 mass % may be sufficient.

[0134] The content of the colorant (A) is preferably 5 mass % or more and 60 mass % or less, more preferably 8 mass % or more and 55 mass % or less, with respect to the total amount of solid content, further preferably Preferably, it is 10 mass % or more and 50 mass % or less. When the content of the colorant (A) is within the above range, the color density when a color filter is used is sufficient, and the resin (B) and the polymerizable compound (C) can be contained in the composition in a required amount, so that the mechanical strength is reduced Sufficient patterns can be formed.

[0135] Here, the "total amount of solid content" in the present specification refers to an amount obtained by subtracting the content of the solvent from the total amount of the colored curable resin composition. The total amount of solid content and content of each component with respect to this can be measured, for example by well-known analytical means, such as liquid chromatography or gas chromatography.

[0136] <Resin (B)>

Although resin (B) is not specifically limited, It is preferable that it is alkali-soluble resin. Examples of the resin (B) include the following resins [K1] to [K6].

resin [K1]; A structural unit derived from at least one (a) (hereinafter sometimes referred to as “(a)”) selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic acid anhydrides, and having 2 to 4 carbon atoms a copolymer having a structural unit derived from a monomer (b) having a cyclic ether structure and an ethylenically unsaturated bond (hereinafter sometimes referred to as “(b)”);

resin [K2]; The structural unit derived from (a), the structural unit derived from (b), and the monomer (c) copolymerizable with (a) (however, it is different from (a) and (b).) (hereinafter “(c) a copolymer having a structural unit derived from);

resin [K3]; a copolymer having the structural unit derived from (a) and the structural unit derived from (c);

resin [K4]; a copolymer having a structural unit derived from (c) and a structural unit obtained by adding (b) to the structural unit derived from (a);

resin [K5]; a copolymer having a structural unit obtained by adding (a) to the structural unit derived from (b) and a structural unit derived from (c);

resin [K6]; A copolymer having a structural unit derived from (c) and a structural unit obtained by adding (a) to the structural unit derived from (b) and further adding a carboxylic acid anhydride.

Specific examples of (a) include unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, o-, m-, and p-vinylbenzoic acid;

Maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyl unsaturated dicarboxylic acids such as tetrahydrophthalic acid and 1,4-cyclohexenedicarboxylic acid;

Methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo[2.2.1]hept-2-ene, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene , 5-Carboxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-carboxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-carboxy-6-methylbicyclo Bicyclo unsaturated compounds containing a carboxy group, such as [2.2.1]hept-2-ene and 5-carboxy-6-ethylbicyclo[2.2.1]hept-2-ene;

Maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride , unsaturated dicarboxylic acid anhydrides such as dimethyltetrahydrophthalic anhydride and 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride;

Unsaturated mono[(meth)acryl] of polyvalent carboxylic acid having more than divalence, such as succinic acid mono[2-(meth)acryloyloxyethyl] and phthalic acid mono[2-(meth)acryloyloxyethyl] royloxyalkyl]esters;

and unsaturated acrylates containing a hydroxyl group and a carboxyl group in the same molecule, such as α-(hydroxymethyl)acrylic acid.

Among these, acrylic acid, methacrylic acid, maleic anhydride, etc. are preferable from a viewpoint of copolymerization reactivity or a viewpoint of the solubility with respect to the aqueous alkali solution of resin obtained.

[0138] (b), for example, a cyclic ether structure having 2 to 4 carbon atoms (eg, at least one selected from the group consisting of an oxirane ring, an oxetane ring and a tetrahydrofuran ring) and an ethylenically unsaturated bond Eggplant refers to a polymerizable compound. As for (b), the monomer which has a C2-C4 cyclic ether and a (meth)acryloyloxy group is preferable.

In addition, in this specification, "(meth)acrylic acid" shows at least 1 sort(s) chosen from the group which consists of acrylic acid and methacrylic acid. Notations, such as "(meth)acryloyl" and "(meth)acrylate", also have the same meaning.

[0139] As (b), for example, a monomer (b1) having an oxiranyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as “(b1)”), a monomer having an oxetanyl group and an ethylenically unsaturated bond (b2) ) (hereinafter sometimes referred to as “(b2)”), and a monomer (b3) having a tetrahydrofuryl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as “(b3)”).

[0140] As (b1), for example, a monomer (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized (hereinafter sometimes referred to as “(b1-1)”), an alicyclic A monomer (b1-2) (hereinafter, sometimes referred to as “(b1-2)”) having a structure in which a formula unsaturated hydrocarbon is epoxidized is mentioned.

[0141] As (b1-1), glycidyl (meth) acrylate, β-methylglycidyl (meth) acrylate, β-ethyl glycidyl (meth) acrylate, glycidyl vinyl ether, o -Vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether, α-methyl-o-vinylbenzyl glycidyl ether, α-methyl-m-vinylbenzyl glycidyl Ether, α-methyl-p-vinylbenzylglycidyl ether, 2,3-bis(glycidyloxymethyl)styrene, 2,4-bis(glycidyloxymethyl)styrene, 2,5-bis(glycidyl) Cydyloxymethyl) styrene, 2,6-bis (glycidyloxymethyl) styrene, 2,3,4-tris (glycidyloxymethyl) styrene, 2,3,5-tris (glycidyloxymethyl) ) Styrene, 2,3,6-tris (glycidyloxymethyl) styrene, 3,4,5-tris (glycidyloxymethyl) styrene, 2,4,6-tris (glycidyloxymethyl) styrene and the like.

[0142] As (b1-2), vinylcyclohexene monoxide, 1,2-epoxy-4-vinylcyclohexane (eg, Seroxide 2000; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth) acrylate (eg, Cyclomer A400; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (eg, Cyclomer M100; manufactured by Daicel Corporation), a compound represented by formula (I) and a formula ( The compound represented by II), etc. are mentioned.

[0143]

[0144] [In formulas (I) and (II), R ^a and R ^b represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the hydrogen atom contained in the alkyl group may be substituted with a hydroxyl group .

X ^a and X ^b represent a single bond, *-R ^c -, *-R ^c -O-, *-R ^c -S-, or *-R ^c -NH-.

R ^c represents an alkanediyl group having 1 to 6 carbon atoms.

* indicates a bond with O.]

[0145] Examples of the alkyl group having 1 to 4 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, and a tert-butyl group.

Examples of the alkyl group in which a hydrogen atom is substituted with hydroxy include a hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 1-hydroxypropyl group, 2-hydroxypropyl group, 3-hydroxypropyl group, and 1-hydroxy group. and a hydroxy-1-methylethyl group, a 2-hydroxy-1-methylethyl group, a 1-hydroxybutyl group, a 2-hydroxybutyl group, a 3-hydroxybutyl group and a 4-hydroxybutyl group.

R ^a and R ^b preferably include a hydrogen atom, a methyl group, a hydroxymethyl group, a 1-hydroxyethyl group and a 2-hydroxyethyl group, and more preferably a hydrogen atom and a methyl group.

[0146] Examples of the alkanediyl group include a methylene group, an ethylene group, a propane-1,2-diyl group, a propane-1,3-diyl group, a butane-1,4-diyl group, a pentane-1,5-diyl group, A hexane-1,6-diyl group etc. are mentioned.

As X ^a and X ^b , Preferably, a single bond, a methylene group, an ethylene group, *-CH ₂ -O- and *-CH ₂ CH ₂ -O- are mentioned, More preferably, a single bond, *- CH ₂ CH ₂ -O- (* indicates a bond with O).

[0147] Examples of the compound represented by formula (I) include compounds represented by any one of formulas (I-1) to (I-15). Among them, formula (I-1), formula (I-3), formula (I-5), formula (I-7), formula (I-9) or formula (I-11) to formula (I-15) ) is preferable, and a compound represented by Formula (I-1), Formula (I-7), Formula (I-9) or Formula (I-15) is more preferable.

[0148]

[0149]

[0150] Examples of the compound represented by formula (II) include compounds represented by any one of formulas (II-1) to (II-15). Among them, formula (II-1), formula (II-3), formula (II-5), formula (II-7), formula (II-9) or formula (II-11) to formula (II-15) ) is preferable, and the compound represented by Formula (II-1), Formula (II-7), Formula (II-9), or Formula (II-15) is more preferable.

[0151]

[0152]

[0153] The compound represented by the formula (I) and the compound represented by the formula (II) may be used independently, respectively, or two or more types may be used in combination. When the compound represented by the formula (I) and the compound represented by the formula (II) are used in combination, their content ratio [the compound represented by the formula (I): the compound represented by the formula (II)] is based on a molar basis, Preferably it is 5:95-95:5, More preferably, it is 20:80-80:20.

[0154] As (b2), a monomer having an oxetanyl group and a (meth)acryloyloxy group is more preferable. As (b2), 3-methyl-3-methacryloyloxymethyloxetane, 3-methyl-3-acryloyloxymethyloxetane, 3-ethyl-3-methacryloyloxymethyloxetane, 3 -Ethyl-3-acryloyloxymethyloxetane, 3-methyl-3-methacryloyloxyethyloxetane, 3-methyl-3-acryloyloxyethyloxetane, 3-ethyl-3-methacryl Royloxyethyloxetane, 3-ethyl-3-acryloyloxyethyloxetane, etc. are mentioned.

[0155] As (b3), a monomer having a tetrahydrofuryl group and a (meth)acryloyloxy group is more preferable. Specific examples of (b3) include tetrahydrofurfuryl acrylate (eg, Viscoat V#150, manufactured by OSAKA ORGANIC CHEMICAL INDUSTRY LTD), tetrahydrofurfuryl methacrylate, and the like.

[0156] As (b), it is preferable that it is (b1) from the viewpoint that the reliability of the obtained color filter, such as heat resistance and chemical resistance, can be further improved. Furthermore, (b1-2) is more preferable at the point which is excellent in the storage stability of colored curable resin composition.

[0157] As (c), methyl (meth) acrylate, ethyl (meth) acrylate, n-butyl (meth) acrylate, sec-butyl (meth) acrylate, tert-butyl (meth) acrylate, 2 -Ethylhexyl (meth) acrylate, dodecyl (meth) acrylate, lauryl (meth) acrylate, stearyl (meth) acrylate, cyclopentyl (meth) acrylate, cyclohexyl (meth) acrylate, 2 -Methylcyclohexyl (meth) acrylate, tricyclo [5.2.1.0 ^2,6 ] decan-8-yl (meth) acrylate (in the technical field, it is called "dicyclopentanyl (meth) acrylate" as a common name Also called "tricyclodecyl (meth) acrylate" in some cases), tricyclo [5.2.1.0 ^2,6 ] decen-8-yl (meth) acrylate (in the technical field, Commonly referred to as "dicyclopentenyl (meth)acrylate"), dicyclopentanyloxyethyl (meth)acrylate, isobornyl (meth)acrylate, adamantyl (meth)acrylate, allyl (meth)acrylic acid esters such as (meth)acrylate, propargyl (meth)acrylate, phenyl (meth)acrylate, naphthyl (meth)acrylate, and benzyl (meth)acrylate;

hydroxy group-containing (meth)acrylic acid esters such as 2-hydroxyethyl (meth)acrylate and 2-hydroxypropyl (meth)acrylate;

dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate, and diethyl itaconic acid;

Bicyclo[2.2.1]hept-2-ene, 5-methylbicyclo[2.2.1]hept-2-ene, 5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxybi Cyclo[2.2.1]hept-2-ene, 5-hydroxymethylbicyclo[2.2.1]hept-2-ene, 5-(2'-hydroxyethyl)bicyclo[2.2.1]hept-2 -ene, 5-methoxybicyclo[2.2.1]hept-2-ene, 5-ethoxybicyclo[2.2.1]hept-2-ene, 5,6-dihydroxybicyclo[2.2.1]hept bicyclo unsaturated compounds such as -2-ene;

N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimidebenzoate, N-succinimidyl-4-maleimidebutyrate, N-succinimidyl- dicarbonylimide derivatives such as 6-maleimide caproate, N-succinimidyl-3-maleimide propionate, and N-(9-acridinyl) maleimide;

Styrene, α-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, p-methoxystyrene, acrylonitrile, methacrylonitrile, vinyl chloride, vinylidene chloride, acrylamide, methacrylamide, acetic acid vinyl, 1,3-butadiene, isoprene, 2,3-dimethyl-1,3-butadiene, and the like.

Among them, from the viewpoint of copolymerization reactivity and heat resistance, 2-hydroxyethyl (meth)acrylate, styrene, vinyltoluene, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, and bicyclo [2.2.1] Hept-2-ene and the like are preferable.

[0158] In the resin [K1], the ratio of the structural units derived from each of the total structural units constituting the resin [K1],

a structural unit derived from (a); 2 to 60 mol%

a structural unit derived from (b); 40-98 mol%

It is preferable that

a structural unit derived from (a); 10-50 mol%

a structural unit derived from (b); 50-90 mol%

It is more preferable that

When the ratio of the structural unit of resin [K1] exists in said range, the storage stability of colored curable resin composition, developability at the time of forming a colored pattern, and solvent resistance of the color filter obtained ) can be excellent.

[0159] Resin [K1] is, for example, described in the document "Experimental Method of Polymer Synthesis" (published by Takayuki Otsu, Kagaku-Dojin Publishing Company, INC. 1st Edition 1st Edition published on March 1, 1972) It can be prepared by referring to the method and the cited literature described in the document.

[0160] Specifically, a predetermined amount of (a) and (b), a polymerization initiator, a solvent, etc. are placed in a reaction vessel, for example, by replacing oxygen with nitrogen to create a deoxygenated atmosphere, while stirring , heating and warming methods are mentioned. In addition, the polymerization initiator, a solvent, etc. used here are not specifically limited, Those normally used in the said field|area can be used. For example, as the polymerization initiator, an azo compound (2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), etc.) or an organic peroxide (benzoyl peroxide, etc.) What is necessary is just to melt|dissolve each monomer as a solvent, The solvent etc. which are mentioned later as a solvent (E) of the colored curable resin composition of this invention are mentioned.

[0161] In addition, the obtained copolymer may be used as it is, a solution after the reaction, a concentrated or diluted solution, or extracted as a solid (powder) by a method such as re-precipitation. ) may be used. In particular, by using the solvent contained in the colored curable resin composition of the present invention as a solvent during this polymerization, the solution after the reaction can be used as it is for the preparation of the colored curable resin composition of the present invention. The manufacturing process of colored curable resin composition can be simplified.

[0162] In the resin [K2], the ratio of the structural units derived from each of the total structural units constituting the resin [K2],

a structural unit derived from (a); 2-45 mol%

a structural unit derived from (b); 2-95 mol%

a structural unit derived from (c); 1-65 mol%

It is preferable that

a structural unit derived from (a); 5-40 mol%

a structural unit derived from (b); 5-80 mol%

a structural unit derived from (c); 5 to 60 mol%

It is more preferable that

When the ratio of the structural unit of the resin [K2] is within the above range, the storage stability of the colored curable resin composition, the developability at the time of forming a colored pattern, and the solvent resistance, heat resistance and mechanical strength of the obtained color filter are excellent can do.

[0163] The resin [K2] can be produced, for example, in the same manner as described for the production method of the resin [K1].

[0164] In the resin [K3], the ratio of the structural units derived from each of the total structural units constituting the resin [K3],

a structural unit derived from (a); 2 to 60 mol%

a structural unit derived from (c); 40-98 mol%

It is preferable that

a structural unit derived from (a); 10-50 mol%

a structural unit derived from (c); 50-90 mol%

It is more preferable that

The resin [K3] can be produced, for example, in the same manner as described as the method for producing the resin [K1].

[0165] Resin [K4] obtains a copolymer of (a) and (c), and (a) has a cyclic ether having 2 to 4 carbon atoms and/or a carboxylic acid It can be prepared by adding to anhydride.

First, the copolymer of (a) and (c) is prepared in the same manner as described as the method for producing the resin [K1]. In this case, it is preferable that the ratio of the structural unit derived from each is the same ratio as that illustrated for resin [K3].

[0166] Next, a part of the carboxylic acid and/or carboxylic acid anhydride derived from (a) in the copolymer is reacted with the cyclic ether having 2 to 4 carbon atoms in (b).

Following the preparation of the copolymers of (a) and (c), the atmosphere in the flask is substituted from nitrogen to air, and (b), a catalyst for the reaction of a carboxylic acid or carboxylic anhydride with a cyclic ether (such as tris( dimethylaminomethyl)phenol) and a polymerization inhibitor (eg, hydroquinone, etc.) are put in a flask, and the resin [K4] can be prepared by, for example, reacting at 60 to 130° C. for 1 to 10 hours.

As for the usage-amount of (b), 5-80 mol is preferable with respect to (a) 100 mol, More preferably, it is 10-75 mol. By setting it as this range, the storage stability of colored curable resin composition, developability at the time of forming a pattern, and the balance of solvent resistance, heat resistance, mechanical strength, and sensitivity of the pattern obtained can become favorable. Since the reactivity of the cyclic ether is high and unreacted (b) hardly remains, as (b) used in the resin [K4], (b1) is preferable, and (b1-1) is more preferable. Do.

As for the usage-amount of the said reaction catalyst, 0.001-5 mass parts is preferable with respect to 100 mass parts of total amounts of (a), (b), and (c). As for the usage-amount of the said polymerization inhibitor, 0.001-5 mass parts is preferable with respect to 100 mass parts of total amounts of (a), (b), and (c).

Reaction conditions, such as a preparation method, reaction temperature, and time, can be suitably adjusted in consideration of manufacturing equipment, the amount of heat generated by polymerization, and the like. In addition, similarly to polymerization conditions, the preparation method and reaction temperature can be adjusted suitably in consideration of manufacturing equipment, the calorific value by polymerization, etc.

[0167] The resin [K5] is the first step, in the same manner as the above-described method for producing the resin [K1], to obtain a copolymer of (b) and (c). As for the obtained copolymer, the solution after the reaction may be used as it is, a concentrated or diluted solution may be used, and what was extracted as a solid (powder) by methods, such as reprecipitation, may be used.

The ratio of the structural units derived from (b) and (c) is, respectively, with respect to the total number of moles of all the structural units constituting the copolymer,

a structural unit derived from (b); 5-95 mol%

a structural unit derived from (c); 5-95 mol%

It is preferable that

a structural unit derived from (b); 10-90 mol%

a structural unit derived from (c); 10-90 mol%

It is more preferable that

[0168] Further, under the same conditions as in the production method of the resin [K4], the carboxylic acid or carboxylic acid of (a) in the cyclic ether derived from (b) possessed by the copolymers of (b) and (c) By reacting the acid anhydride, the resin [K5] can be obtained.

As for the usage-amount of (a) made to react with said copolymer, 5-80 mol is preferable with respect to 100 mol of (b). Since the reactivity of cyclic ether is high and unreacted (b) hardly remains, as (b) used for resin [K5], (b1) is preferable and (b1-1) is more preferable.

[0169] The resin [K6] is a resin in which a carboxylic acid anhydride is further reacted with the resin [K5]. A carboxylic acid anhydride is made to react with the hydroxyl group which arises by reaction of a cyclic ether with carboxylic acid or carboxylic acid anhydride.

Examples of the carboxylic acid anhydride include maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinyl phthalic anhydride, 4-vinyl phthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3, 6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride, etc. are mentioned. As for the usage-amount of carboxylic anhydride, 0.5-1 mol is preferable with respect to 1 mol of usage-amounts of (a).

[0170] Specifically, as the resin (B), 3,4-epoxycyclohexylmethyl (meth)acrylate/(meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decylacrylic resin [K1], such as a rate/(meth)acrylic acid copolymer; Glycidyl (meth) acrylate / benzyl (meth) acrylate / (meth) acrylic acid copolymer, glycidyl (meth) acrylate / styrene / (meth) acrylic acid copolymer, 3,4-epoxytricyclo [5.2 .1.0 ^2,6 ]decylacrylate/(meth)acrylic acid/N-cyclohexylmaleimide copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decylacrylate/(meth)acrylic acid/N- Resin [K2], such as a cyclohexylmaleimide/2-hydroxyethyl (meth)acrylate copolymer and 3-methyl-3- (meth)acryloyloxymethyloxetane/(meth)acrylic acid/styrene copolymer; resins [K3] such as benzyl (meth)acrylate/(meth)acrylic acid copolymer and styrene/(meth)acrylic acid copolymer; Resin obtained by adding glycidyl (meth) acrylate to benzyl (meth) acrylate/(meth) acrylic acid copolymer, glycidyl (meth) to tricyclodecyl (meth) acrylate/styrene/(meth)acrylic acid copolymer ) Resin to which acrylate was added, resin [K4], such as a resin which added glycidyl (meth)acrylate to tricyclodecyl (meth)acrylate/benzyl (meth)acrylate/(meth)acrylic acid copolymer; Tricyclodecyl (meth) acrylate / glycidyl (meth) acrylate copolymer of (meth) acrylic acid reacted, tricyclodecyl (meth) acrylate / styrene / glycidyl (meth) acrylate resin [K5] such as a resin obtained by reacting (meth)acrylic acid with a copolymer; and resin [K6] such as a resin obtained by reacting a copolymer of tricyclodecyl (meth)acrylate/glycidyl (meth)acrylate with (meth)acrylic acid and further reacting with tetrahydrophthalic anhydride. there is.

Especially, as resin (B), resin [K1] and resin [K2] are preferable, and resin [K1] is especially preferable.

The weight average molecular weight of the resin (B) in terms of polystyrene is preferably 3,000 or more and 100,000 or less, more preferably 5,000 or more and 50,000 or less, and still more preferably 5,000 or more and 30,000 or less. When the molecular weight is within the above range, the hardness of the color filter is improved, the residual film rate is high, the solubility in the developer of the unexposed part is good, and the resolution of the coloring pattern is improved. can

The degree of dispersion [weight average molecular weight (Mw)/number average molecular weight (Mn)] of the resin (B) is preferably 1.1 or more and 6 or less, and more preferably 1.2 or more and 4 or less.

[0173] The acid value of the resin (B), in terms of solid content, is preferably 50 mg-KOH/g or more and 170 mg-KOH/g or less, more preferably 60 mg-KOH/g or more and 150 mg-KOH/g g or less, more preferably 70 mg-KOH/g or more and 135 mg-KOH/g or less. Here, the acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of the resin (B), and can be obtained by titration using, for example, an aqueous potassium hydroxide solution.

[0174] The content of the resin (B) is preferably 7 mass % or more and 65 mass % or less, more preferably 13 mass % or more and 60 mass % or less, and still more preferably 17 mass % or more with respect to the total amount of solid content. % or more and 55 mass % or less. When the content of the resin (B) is within the above range, a colored pattern can be formed, and the resolution and residual film rate of the colored pattern can be improved.

[0175] <Polymerizable compound (C)>

A polymerizable compound (C) is a compound which can superpose|polymerize with the active radical and/or acid generated from a polymerization initiator (D), The hydroxyl value is 100 mgKOH/g or more. According to the colored curable resin composition of this invention containing a polymeric compound (C), thin film formation of the cured film obtained becomes possible. Moreover, the brightness of the cured film obtained in a preferable aspect can become favorable.

[0176] The polymerizable compound (C) may consist of one polymerizable compound having a hydroxyl value of 100 mgKOH/g or more, or may contain two or more polymerizable compounds having a hydroxyl value of 100 mgKOH/g or more. The polymerizable compound (C) may be a mixture of one or more polymerizable compounds having a hydroxyl value of 100 mgKOH/g or more and one or more polymerizable compounds having a hydroxyl value of less than 100 mgKOH/g. When 2 or more types of polymeric compounds are included as a polymeric compound (C), the hydroxyl value of a polymeric compound (C) points out the hydroxyl value of a mixture. In addition, the hydroxyl value of a polymeric compound (C) is measured according to description of the Example mentioned later.

[0177] The hydroxyl value of the polymerizable compound (C) is preferably 110 mgKOH/g or more, more preferably 180 mgKOH/g or more, still more preferably 200 mgKOH/g or more, particularly preferably 250 mgKOH/g or more. When the hydroxyl value of a polymeric compound (C) exists in the said range, thin film formation of the cured film obtained will become possible, and the brightness of the cured film obtained in a preferable aspect may become favorable. Further, from the viewpoint of ease of availability, the hydroxyl value of the polymerizable compound (C) is preferably 500 mgKOH/g or less, more preferably 450 mgKOH/g or less, still more preferably 400 mgKOH/g or less, Even more preferably, it is 350 mgKOH/g or less, Especially preferably, it is 300 mgKOH/g or less.

[0178] Examples of the polymerizable compound (C) include compounds having a polymerizable ethylenically unsaturated bond and a hydroxyl group. The average number of double bonds of the polymerizable compound (C) is 1.0 or more, preferably 2.0 or more, more preferably 2.5 or more, and more preferably 4.0 or less, more preferably 3.5 or less, still more preferably 3.0 or less. am. In addition, the average number of double bonds of a polymeric compound (C) can be measured by analytical means, such as HPLC (high-performance liquid chromatography), for example.

[0179] Specific examples of the polymerizable compound having a hydroxyl value of 100 mgKOH/g or more include pentaerythritol tri (meth) acrylate, pentaerythritol di (meth) acrylate, pentaerythritol mono (meth) acrylate, ethylene glycol modified Pentaerythritol tri(meth)acrylate, propylene glycol modified pentaerythritol triacrylate, trimethylolpropane di(meth)acrylate, ethylene glycol modified trimethylolpropane di(meth)acrylate, ethylene glycol modified glycerin di(meth) ) acrylate, propylene glycol modified glycerin di(meth)acrylate, ditrimethylolpropane tri(meth)acrylate, ethylene glycol modified ditrimethylolpropane tri(meth)acrylate, propylene glycol modified ditrimethylolpropane triacrylate and dipentaerythritol pentaacrylate. It is preferable that pentaerythritol tri(meth)acrylate is included at least, and, as for a polymeric compound (C), it is more preferable that pentaerythritol triacrylate is included. When a polymeric compound (C) contains pentaerythritol tri(meth)acrylate (preferably pentaerythritol triacrylate), it is preferable that the content rate is 10 mass % or more in a polymeric compound (C). And more preferably, it is 25 mass % or more, More preferably, it is 40 mass % or more, and may be 100 mass %, 90 mass % or less may be sufficient, and 80 mass % or less may be sufficient.

[0180] The content of the polymerizable compound having a hydroxyl value of 100 mgKOH/g or more in the polymerizable compound (C) is preferably 60 mass % or more, more preferably 70 mass % or more, still more preferably 80 mass % or more. % or more, 100 mass % may be sufficient, 98 mass % or less may be sufficient, and 93 mass % or less may be sufficient.

[0181] When the polymerizable compound (C) is a mixture of two or more polymerizable compounds, as long as the hydroxyl value as the mixture is not less than 100 mgKOH/g, the polymerizable compound (C) has a hydroxyl value of less than 100 mgKOH/g The polymerizable compound may be included. Specific examples of the polymerizable compound having a hydroxyl value of less than 100 mgKOH/g include trimethylolpropane tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol pentamethacrylate, and dipentaerythritol hexa (meth). ) acrylate, tripentaerythritol octa (meth) acrylate, tetrapentaerythritol deca (meth) acrylate, tris (2- (meth) acryloyloxyethyl) isocyanurate, ethylene glycol modified pentaerythritol Tetra (meth) acrylate, ethylene glycol modified dipentaerythritol hexa (meth) acrylate, propylene glycol modified pentaerythritol tetra (meth) acrylate, propylene glycol modified dipentaerythritol hexa (meth) acrylate, caprolactone Modified pentaerythritol tetra(meth)acrylate and caprolactone modified dipentaerythritol hexa(meth)acrylate are mentioned.

[0182] The content of the polymerizable compound (C) is preferably 7 mass % or more, more preferably 13 mass % or more, still more preferably 20 mass % or more, and 65 mass % or more with respect to the total amount of solid content. % or less, more preferably 55 mass % or less, still more preferably 45 mass % or less. When the content rate of a polymeric compound (C) exists in said range, thin film formation of the cured film obtained may become possible, and the residual film rate at the time of coloring pattern formation, and the chemical-resistance of a color filter may improve.

[0183] <Polymerization Initiator (D)>

The polymerization initiator (D) is not particularly limited as long as it is a compound capable of initiating polymerization by generating active radicals, acids, etc. under the action of light or heat, and a known polymerization initiator can be used. Examples of the polymerization initiator generating active radicals include an alkylphenone compound, a triazine compound, an acylphosphine oxide compound, an O-acyloxime compound, and a biimidazole compound.

[0184] The O-acyloxime compound is a compound having a partial structure represented by formula (d1). Hereinafter, * represents a bond.

[0185]

[0186] Examples of the O-acyloxime compound include N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfa). Nylphenyl) octan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine, N-acetoxy-1- [9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethane-1-imine, N-acetoxy-1-[9-ethyl-6-{2-methyl-4- (3,3-Dimethyl-2,4-dioxacyclopentanylmethyloxy)benzoyl}-9H-carbazol-3-yl]ethan-1-imine, N-acetoxy-1-[9-ethyl-6- (2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropan-1-imine, N-benzoyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H- Carbazol-3-yl]-3-cyclopentylpropan-1-one-2-imine, N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2- immigration can be You may use commercial items, such as Irgacure OXE01, OXE02 (above, BASF company make), N-1919 (made by ADEKA company), and PBG-327 (Changzhou Tronly New Electronic Materials Co., Ltd. product). Among them, the O-acyloxime compound is N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl) Octan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine, and N-acetyloxy-1-(4 -Phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine is preferably at least one selected from the group consisting of, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octane-1 At least one selected from the group consisting of -one-2-imine and N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine is more preferable. With these O-acyl oxime compounds, a color filter with high brightness can be obtained.

[0187] The alkylphenone compound is a compound having a partial structure represented by formula (d2) or a partial structure represented by formula (d3). In these partial structures, the benzene ring may have a substituent.

[0188]

[0189] Examples of the compound having a partial structure represented by formula (d2) include 2-methyl-2-morpholino-1-(4-methylsulfanylphenyl)propan-1-one, 2-dimethylamino- 1-(4-morpholinophenyl)-2-benzylbutan-1-one, 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl) phenyl]butan-1-one. You may use commercial items, such as Irgacure 369, 907, 379 (above, BASF Corporation make).

As the compound having a partial structure represented by formula (d3), for example, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1-[4-(2) -Hydroxyethoxy)phenyl]propan-1-one, 1-hydroxycyclohexylphenylketone, an oligomer of 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propan-1-one; α,α-diethoxyacetophenone and benzyl dimethyl ketal.

From a viewpoint of a sensitivity, as an alkylphenone compound, the compound which has a partial structure represented by Formula (d2) is preferable.

[0190] As the triazine compound, for example, 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, 2,4-bis(trichloromethyl) )-6-(4-methoxynaphthyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5-triazine, 2, 4-bis(trichloromethyl)-6-(4-methoxystyryl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(5-methylfuran) -2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)ethenyl]-1,3,5 -triazine, 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl)ethenyl]-1,3,5-triazine, 2,4-bis( trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)ethenyl]-1,3,5-triazine.

[0191] Examples of the acylphosphine oxide compound include 2,4,6-trimethylbenzoyldiphenylphosphine oxide. You may use commercial items, such as Irgacure (trademark) 819 (made by BASF).

[0192] Examples of the biimidazole compound include 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2, 3-dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole (see, for example, Japanese Patent Application Laid-Open Nos. H06-75372, H06-75373, etc.), 2,2' -bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra( Alkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(dialkoxyphenyl)biimidazole, 2,2'-bis(2-chloro Phenyl)-4,4',5,5'-tetra(trialkoxyphenyl)biimidazole (see, for example, Japanese Patent Publication Nos. S48-38403 and S62-174204), 4,4 and biimidazole compounds in which the phenyl group at the ',5,5'-position is substituted with a carboalkoxy group (see, for example, Japanese Patent Application Laid-Open No. H07-10913, etc.).

[0193] Examples of the polymerization initiator (D) include benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether; Benzophenone, o-benzoyl methyl benzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, 3,3',4,4'-tetra(tert-butylperoxycarbonyl)benzophenone, benzophenone compounds such as 2,4,6-trimethylbenzophenone; quinone compounds such as 9,10-phenanthrenequinone, 2-ethylanthraquinone and camphorquinone; 10-butyl-2-chloroacridone, benzyl, methyl phenylglyoxylate, titanocene compound, etc. are mentioned. It is preferable to use these in combination with the polymerization initiation adjuvant (D1) (particularly amines) mentioned later.

[0194] As the acid generator, for example, 4-hydroxyphenyldimethylsulfonium p-toluenesulfonate, 4-hydroxyphenyldimethylsulfonium hexafluoroantimonate, 4-acetoxyphenyldimethylsulfonium p-toluene Sulfonate, 4-acetoxyphenyl methyl benzylsulfonium hexafluoroantimonate, triphenylsulfonium p-toluenesulfonate, triphenylsulfonium hexafluoroantimonate, diphenyliodonium p-toluene Onium salts, such as a sulfonate and diphenyl iodonium hexafluoroantimonate, nitrobenzyl tosylate, benzointosylate, etc. are mentioned.

[0195] The polymerization initiator (D) is preferably a polymerization initiator containing at least one selected from the group consisting of an alkylphenone compound, a triazine compound, an acylphosphine oxide compound, an O-acyloxime compound, and a biimidazole compound. And the polymerization initiator containing an O- acyl oxime compound is more preferable.

[0196] The content of the polymerization initiator (D) is preferably 0.1 parts by mass or more and 30 parts by mass or less, more preferably 1 part by mass, with respect to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). It is more than part and 20 mass parts or less. When content of a polymerization initiator (D) exists in said range, since it becomes highly sensitive and exposure time can be shortened, productivity of a color filter improves.

[0197] <Polymerization initiation aid (D1)>

A polymerization initiation adjuvant (D1) is a compound used in order to accelerate|stimulate superposition|polymerization of the polymeric compound which superposition|polymerization was started by a polymerization initiator, or a sensitizer. When a polymerization initiator auxiliary (D1) is included, it is used in combination with a polymerization initiator (D) normally.

Examples of the polymerization initiation auxiliary (D1) include an amine compound, an alkoxyanthracene compound, a thioxanthone compound, and a carboxylic acid compound.

[0198] As the amine compound, triethanolamine, methyldiethanolamine, triisopropanolamine, 4-dimethylamino methyl benzoate, 4-dimethylamino ethyl benzoate, 4-dimethylamino benzoate isoamyl, benzoate 2-dimethylaminoethyl, 4-dimethylaminobenzoic acid 2-ethylhexyl, N,N-dimethylparatoluidine, 4,4'-bis(dimethylamino)benzophenone (commonly known as Michler's ketone), 4,4'-bis(diethylamino)benzophenone , 4,4'-bis(ethylmethylamino)benzophenone etc. are mentioned, Especially, 4,4'-bis(diethylamino)benzophenone is preferable. You may use commercial items, such as EAB-F (made by HODOGAYA CHEMICAL CO., LTD.).

[0199] Examples of the alkoxyanthracene compound include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene, 9 , 10-dibutoxy anthracene, 2-ethyl-9, 10-dibutoxy anthracene, etc. are mentioned.

[0200] As the thioxanthone compound, 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, 1-chloro-4 -Propoxythioxanthone, etc. are mentioned.

[0201] As the carboxylic acid compound, phenylsulfanylacetic acid, methylphenylsulfanylacetic acid, ethylphenylsulfanylacetic acid, methylethylphenylsulfanylacetic acid, dimethylphenylsulfanylacetic acid, methoxyphenylsulfanylacetic acid, dimethoxyphenylsulfa nylacetic acid, chlorophenylsulfanylacetic acid, dichlorophenylsulfanylacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, naphthoxyacetic acid, etc. are mentioned.

[0202] When using these polymerization initiation aids (D1), their content is preferably 0.1 parts by mass or more and 30 parts by mass or less with respect to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). , More preferably, they are 1 mass part or more and 20 mass parts or less. When the amount of the polymerization initiation auxiliary (D1) is within this range, it is possible to form a coloring pattern with higher sensitivity, so that the productivity of the color filter can be improved.

[0203] <Solvent (E)>

The solvent (E) is not specifically limited, The solvent normally used in this field|area can be used. For example, ester solvents (solvents containing -COO- in the molecule and not containing -O-), ether solvents (solvents containing -O- in the molecule and not containing -COO-), ether ester solvents ( Solvents containing -COO- and -O- in the molecule), ketone solvents (solvents containing -CO- in the molecule and not containing -COO-), alcohol solvents (containing OH in the molecule, -O- , -CO- and -COO--free solvent), an aromatic hydrocarbon solvent, an amide solvent, and dimethyl sulfoxide.

[0204] As the ester solvent, methyl lactate, ethyl lactate, butyl lactate, 2-hydroxyisobutanoate, ethyl acetate, n-butyl acetate, isobutyl acetate, pentyl formate, isopentyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexanol acetate, γ-butyrolactone, and the like.

[0205] As the ether solvent, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl Ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetra Hydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenetol and Methylanisole etc. are mentioned.

[0206] As the ether ester solvent, methyl methoxy acetate, ethyl methoxy acetate, butyl methoxy acetate, methyl ethoxy acetate, ethyl ethoxy acetate, 3-methoxy methyl propionate, 3-methoxy ethyl propionate, 3-e Methyl oxypropionate, 3-ethoxy ethyl propionate, 2-methoxy methyl propionate, 2-methoxy ethyl propionate, 2-methoxypropyl propionate, 2-ethoxy methyl propionate, 2-ethoxy ethyl propionate, 2-methoxy -2-methylpropionate, 2-ethoxy-2-methylpropionate ethyl, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate; and propylene glycol monopropyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, and diethylene glycol monobutyl ether acetate.

[0207] As a ketone solvent, 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentane on, cyclopentanone, cyclohexanone, isophorone, and the like.

[0208] Examples of the alcohol solvent include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol and glycerin.

[0209] Examples of the aromatic hydrocarbon solvent include benzene, toluene, xylene and mesitylene.

[0210] Examples of the amide solvent include N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.

[0211] Among the above solvents, organic solvents having a boiling point of 120°C or higher and 180°C or lower at 1 atm are preferable from the viewpoint of coating properties and drying properties. As a solvent, Propylene glycol monomethyl ether acetate, ethyl lactate, propylene glycol monomethyl ether, 3-ethoxy ethyl propionate, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, 4-hydroxy -4-methyl-2-pentanone and N,N-dimethylformamide are preferred, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate, ethyl 3-ethoxypropionate, and 4-hydroxy- 4-methyl-2-pentanone is more preferable.

[0212] The content of the solvent (E) is preferably 70 mass % or more and 95 mass % or less, and more preferably 75 mass % or more and 92 mass % or less with respect to the total amount of the colored curable resin composition of the present invention. In other words, the total content of solid content of colored curable resin composition becomes like this. Preferably they are 5 mass % or more and 30 mass % or less, More preferably, they are 8 mass % or more and 25 mass % or less. When the content rate of the solvent (E) is within the above range, flatness at the time of application becomes good, and since color density does not run short when a color filter is formed, display characteristics can become favorable.

[0213] <Leveling agent (F)>

As a leveling agent (F), a silicone type surfactant, the silicone type surfactant etc. which have a silicone type surfactant, a fluorine type surfactant, and a fluorine atom are mentioned. These may have a polymeric group in a side chain.

As a silicone type surfactant, the surfactant etc. which have a siloxane bond in a molecule|numerator are mentioned. Specifically, Toray Silicone DC3PA, Toray Silicone SH7PA, Toray Silicone DC11PA, Toray Silicone SH21PA, Toray Silicone SH28PA, Toray Silicone SH29PA, Toray Silicone SH30PA, Toray Silicone SH8400 (manufactured by Dow Corning Toray Co., Ltd.), KP321, KP322 , KP323, KP324, KP326, KP340, KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452 and TSF4460 (manufactured by Momentive Performance Materials Japan LLC), etc. can be heard

[0214] Examples of the fluorine-based surfactant include surfactants having a fluorocarbon chain in the molecule. Specifically, Fluorad (registered trademark) FC430, Fluorad FC431 (manufactured by Sumitomo 3M Limited), Megapac (registered trademark) F142D, Megapac F171, Megapac F172, Megapac F173, Megapac F177, Megapac F183, Megapac F554, Megapac R30, Megapac RS-718-K (manufactured by DIC CORPORATION), eftop (registered trademark) EF301, eftop EF303, eftop EF351, eftop EF352 (Mitsubishi Materials Electronic Chemicals Co., Ltd. manufacture), Sufflon (trademark) S381, Sufflon S382, Sufflon SC101, Sufflon SC105 (manufactured by Asahi Glass Co., Ltd.), and E5844 (manufactured by Daikin Fine Chemical Genkyusho), and the like.

[0215] Examples of the silicone-based surfactant having a fluorine atom include a surfactant having a siloxane bond and a fluorocarbon chain in the molecule. Specific examples thereof include Megapac (registered trademark) R08, Megapac BL20, Megapac F475, Megapac F477, and Megapac F443 (manufactured by DIC CORPORATION).

[0216] The content rate of the leveling agent (F) is preferably 0.001 mass % or more and 0.2 mass % or less, more preferably 0.002 mass % or more and 0.2 mass % or less, further preferably 0.001 mass % or more and 0.2 mass % or less with respect to the total amount of the colored curable resin composition. is 0.01 mass % or more and 0.2 mass % or less. In addition, the said dispersing agent is not contained in this content rate. When the content rate of a leveling agent (F) exists in said range, the flatness of a color filter can be made favorable.

[0217] <Other ingredients>

The colored curable resin composition of this invention may contain well-known additives in the said technical field, such as a filler, another high molecular compound, an adhesion promoter, an optical stabilizer, and a chain transfer agent, as needed.

As the adhesion promoter, vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris(2-methoxyethoxy)silane, 3-glycidyloxypropyltrimethoxysilane, 3-glycidyloxypropylmethyldimethoxy Silane, 3-glycidyloxypropylmethyldiethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3 -Methacryloyloxypropyltrimethoxysilane, 3-sulfanylpropyltrimethoxysilane, 3-isocyanatopropyltriethoxysilane, N-2-(aminoethyl)-3-aminopropylmethyldimethoxysilane , N-2-(aminoethyl)-3-aminopropylmethyldiethoxysilane, N-2-(aminoethyl)-3-aminopropyltrimethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyl triethoxysilane, N-phenyl-3-aminopropyltrimethoxysilane, and N-phenyl-3-aminopropyltriethoxysilane; and the like.

[0218] <Method for producing colored curable resin composition>

The colored curable resin composition of this invention is a coloring agent (A), resin (B), a polymeric compound (C), and a polymerization initiator (D), and the solvent (E) and leveling agent (F) used as needed, for example, ), polymerization initiation auxiliary (D1), and other components can be mixed.

[0219] The colorant (A) is mixed with a part or all of the solvent (E) in advance and, if necessary, dispersed using a bead mill or the like until the average particle diameter is about 0.2 μm or less. You can use it as it is. At this time, you may mix|blend a part or all of the said dispersing agent and resin (B) as needed. Thus, it is preferable to prepare the target coloring composition by mixing the remaining component with the dispersion liquid so that it may become a predetermined|prescribed density|concentration. When using a bead mill, the diameter of the bead is preferably 0.05 mm or more and 0.5 mm or less, and the material of the bead is glass, ceramic, metal, or the like.

[0220] <Method for manufacturing color filter>

As a method of manufacturing the colored pattern of a color filter from the colored curable resin composition of this invention, the photolithographic method, the inkjet method, the printing method, etc. are mentioned. Especially, the photolithographic method is preferable. The photolithography method is a method of applying the colored curable resin composition to a substrate, drying it to form a composition layer, exposing the composition layer through a photomask, and developing. In the photolithography method, the colored coating film which is the hardened|cured material of the said composition layer can be formed by not using and/or not developing a photomask at the time of exposure.

[0221] The film thickness of the color filter (cured film) is, for example, 0.1 µm or more and 30 µm or less, preferably 0.1 µm or more and 20 µm or less, and more preferably 0.5 µm or more and 6 µm or less.

[0222] As the substrate, a glass plate such as quartz glass, borosilicate glass, alumina silicate glass, and soda lime glass coated with silica, a resin plate such as polycarbonate, polymethyl methacrylate, polyethylene terephthalate, silicone, the substrate Those in which aluminum, silver, a silver/copper/palladium alloy thin film, etc. were formed on it are used. On these board|substrates, another color filter layer, a resin layer, a transistor, a circuit, etc. may be formed. Moreover, you may use the board|substrate which performed the HMDS process on the silicon substrate.

[0223] Formation of each color pixel by the photolithography method can be performed under known or customary apparatus and conditions. For example, it can be produced as follows. First, a coloring composition is apply|coated on a board|substrate, volatile components, such as a solvent, are removed and dried by heat-drying (pre-bake) and/or drying under reduced pressure, and a smooth composition layer is obtained. Examples of the coating method include a spin coating method, a slit coating method, a slit-and-spin coating method, and the like. 30 degreeC or more and 120 degrees C or less are preferable and, as for the temperature in the case of heat-drying, 50 degreeC or more and 110 degrees C or less are more preferable. Moreover, as a heating time, it is preferable that they are 10 second or more and 60 minutes or less, and it is more preferable that they are 30 second or more and 30 minutes or less. When performing reduced-pressure drying, it is preferable to carry out at the temperature range of 20-25 degreeC under the pressure of 50-150 Pa. The film thickness of the composition layer is not specifically limited, What is necessary is just to select suitably according to the film thickness of the target color filter.

[0224] Next, the composition layer is exposed through a photomask for forming a desired colored pattern. The pattern on the said photomask is not specifically limited, The pattern according to the intended use is used. In addition, in order to form a colored coating film, it exposes without using a photomask. As a light source used for exposure, the light source which generate|occur|produces the light which is a wavelength of 250-450 nm is preferable. For example, light of less than 350 nm is cut using a filter that cuts this wavelength range, or light around 436 nm, 408 nm, or 365 nm is selectively extracted using a bandpass filter that extracts these wavelength ranges. do. Specifically, a mercury lamp, a light emitting diode, a metal halide lamp, a halogen lamp, etc. are mentioned. Since it is possible to uniformly irradiate a parallel light beam to the entire exposure surface or to perform precise alignment between the photomask and the substrate, it is recommended to use a reduced projection exposure apparatus such as a mask aligner and a stepper or a proximity exposure apparatus. desirable.

[0225] By developing the composition layer after exposure in contact with a developer, a colored pattern is formed on the substrate. By development, the unexposed portion of the composition layer is dissolved in the developer and removed. As a developing solution, the aqueous solution of alkaline compounds, such as potassium hydroxide, sodium hydrogencarbonate, sodium carbonate, and tetramethylammonium hydroxide, is preferable, for example. The concentration in the aqueous solution of these alkaline compounds is preferably 0.01% by mass or more and 10% by mass or less, and more preferably 0.03% by mass or more and 5% by mass or less. Moreover, the developing solution may contain surfactant. Any of a puddle method, a dipping method, a spray method, etc. may be sufficient as the image development method. Moreover, you may incline a board|substrate at an arbitrary angle at the time of image development.

It is preferable to wash with water after image development.

[0226] Furthermore, it is preferable to post-bake the obtained colored pattern and colored coating film. 80 degreeC or more and 250 degrees C or less are preferable and, as for post-baking temperature, 100 degreeC or more and 245 degrees C or less are more preferable. 1 minute or more and 120 minutes or less are preferable and, as for post-baking time, 2 minutes or more and 30 minutes or less are more preferable.

[0227] The colored pattern and the colored coating film thus obtained are useful as a color filter, and the color filter is a color used in a display device (eg, a liquid crystal display device, an organic EL device, etc.), electronic paper, a solid-state image sensor, and the like. It is useful as a filter.

[Example]

[0228] Hereinafter, the present invention will be described in more detail by way of Examples, but the present invention is not limited by these Examples. In the examples, percentages and parts indicating the content or the amount used are based on mass unless otherwise specified.

[0229] In the following, the structure of the compound was confirmed by mass spectrometry (LC; 1200 manufactured by Agilent Technologies, Inc., MASS; LC/MSD manufactured by Agilent Technologies, Inc.).

[0230] [Colorant Synthesis Example 1]

The following reaction was performed in nitrogen atmosphere. In a flask equipped with a cooling tube and a stirring device, 26.4 parts of potassium thiocyanate and 156 parts of acetonitrile were added, followed by stirring at room temperature for 30 minutes. 40.0 parts of 2,6-difluorobenzoic acid chloride (manufactured by Tokyo Chemical Industry Co., Ltd.) was added dropwise to the flask over 30 minutes, followed by stirring at room temperature for 1 hour. 30.6 parts of N-ethyl-o-toluidine (manufactured by Tokyo Chemical Industry Co., Ltd.) was added dropwise to the flask over 30 minutes, followed by stirring at room temperature for 1 hour. An aqueous solution in which 79.2 parts of sodium monochloroacetate was dissolved in 120 parts of ion-exchanged water was added to the flask, and 60.4 parts of a 30% aqueous sodium hydroxide solution was added thereto, followed by stirring at room temperature for 18 hours. After adding 600 parts of ion-exchanged water to the flask, the mixture was stirred for 1 hour, and the precipitated yellowish-white solid was obtained by filtration. The obtained off-white solid was washed with 120 parts of acetonitrile and then washed with 560 parts of ion-exchanged water. The washed off-white solid, 156 parts of ion-exchanged water, 35.0 parts of 99% acetic acid (manufactured by Wako Pure Chemical Industries, Ltd.) and 156 parts of toluene were added to a flask equipped with a stirring device, followed by stirring at room temperature for 2 hours. After 80.8 parts of 30% sodium hydroxide aqueous solution was dripped here over 10 minutes, it stirred for 5 minutes, and the water layer was removed by liquid separation operation. After adding 156 parts of ion-exchanged water to the obtained organic layer for liquid-separation washing, 156 parts of ion-exchanged water and 0.1 part of 35% hydrochloric acid were added and liquid-separation washing|cleaning was carried out. The obtained organic layer was concentrated with an evaporator and dried under reduced pressure at 35°C to obtain a compound represented by the formula (B-I-1) as a white solid. The yield (收量) was 43.4 parts, and the yield (收率) was 58.0%.

[0231]

[0232] The following reaction was carried out in a nitrogen atmosphere. 13.2 parts of the compound represented by Formula (BI-1), 19.0 parts of the compound represented by Formula (CI-1), and 38 parts of toluene were thrown into the flask provided with the cooling tube and the stirring device, Then, phosphorus oxychloride 9.2 parts were added and stirred at 100° C. for 7 hours. The reaction mixture was then cooled to room temperature, and then diluted with 29 parts of methylethylketone. Next, a mixed solution of 114 parts of ion-exchanged water and 10 parts of a 35% aqueous hydrochloric acid solution was poured into the diluted reaction mixture, and the water layer was removed by a liquid separation operation. After distilling off the solvent with an evaporator with respect to the obtained organic layer, the compound represented by Formula (X-II-1) was obtained as a bluish purple solid by drying at 60 degreeC under reduced pressure. The yield (得量) of the blue-violet solid was 39.4 parts.

[0233]

[0234]

[0235] The following reaction was performed in a nitrogen atmosphere. 38.4 parts of the compound represented by Formula (X-II-1) and 112 parts of methylene chloride were added to a flask equipped with a cooling tube and a stirring device, followed by stirring for 30 minutes. After cooling the reaction solution on ice and maintaining the internal temperature at 10°C, 31.6 parts of chlorosulfonic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) was added, and then the temperature of the reaction solution was raised to room temperature for 9 hours stirred for a while. Next, the reaction solution was cooled on ice and diluted with a mixed solution of 64 parts of N,N-dimethylformamide and 4.9 parts of ion-exchanged water while maintaining the internal temperature at 10°C. The diluted reaction solution was poured into 1120 parts of toluene and stirred for 30 minutes to precipitate a viscous solid. After discharging the oil layer by decantation, 320 parts of toluene was added to the obtained viscous solid and stirred for 30 minutes. The oil layer was discharged by decantation, and 832 parts of 20% saline was added to the obtained viscous solid, stirred for 1 hour, and then filtered to obtain a blue solid. The obtained blue solid was washed with 576 parts of 20% brine, and dried under reduced pressure at 35°C. The obtained solid and 128 parts of methanol were put into a flask equipped with a stirring device, stirred for 30 minutes, filtered, and separated into a solid and a filtrate. This filtrate is called filtrate A3. The solid obtained by filtration was washed with 192 parts of methanol, and the solid and the filtrate were separated by filtration. This filtrate is called filtrate B3. The filtrate A3 and the filtrate B3 were mixed, the solvent was removed by an evaporator, and then dried under reduced pressure at 40°C to obtain the compound represented by the formula (X-I-1) as a blue-violet solid. The yield of the blue-violet solid was 38.3 parts.

[0236]

[0237] 28.0 parts of the compound represented by Formula (XI-1), 43.2 parts of barium chloride dihydrate, and 356 parts of ion-exchanged water were added to a flask equipped with a cooling tube and a stirring device, followed by stirring at 40°C for 2 hours , the reaction suspension was filtered. The solid obtained by filtration and 350 parts of ion-exchanged water were added to a flask equipped with a stirring device, stirred for 30 minutes, and the suspension was filtered. The obtained solid was washed with 280 parts of ion-exchanged water, and then dried under reduced pressure at 60°C to obtain the compound represented by the formula (A-I-1) as a blue-violet solid. The yield was 24.5 parts and the yield was 81.7%.

[0238]

[0239] Identification of the compound represented by formula (A-I-1)

(Mass spectrometry) Ionization mode = ESI-: m/z = 949.5 [M-Ba+2H] ^-

Exact Mass [M-Ba]: 947.28

[0240] [Colorant Synthesis Example 2]

40.5 parts of the compound represented by formula (1a) and 60.5 parts of 2,6-xylidine (manufactured by Tokyo Chemical Industry Co., Ltd.) are mixed under light-shielding conditions, and in 200 parts of N-methylpyridone, 8 stirred for hours.

After cooling the resulting reaction solution to room temperature, it was added to a mixed solution of 1200 parts of water and 75 parts of 35% hydrochloric acid and stirred at room temperature for 1 hour to precipitate crystals. The precipitated crystals were obtained as a residue of suction filtration, washed with 100 parts of methanol, and then dried under reduced pressure at 60°C overnight to obtain 49 parts of the compound represented by the formula (1-32). The yield was 85%.

[0241]

[0242]

[0243] [Resin Synthesis Example 1]

An appropriate amount of nitrogen was poured into a flask equipped with a reflux condenser, a dropping funnel, and a stirrer to replace with a nitrogen atmosphere, 280 parts of propylene glycol monomethyl ether acetate were placed, and the mixture was heated to 80°C while stirring. Then, 38 parts of acrylic acid, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decan-8-ylacrylate and 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decan-9-ylacrylic A mixed solution of 289 parts of a mixture (content ratio of 1:1) and 125 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. On the other hand, a solution obtained by dissolving 33 parts of 2,2-azobis(2,4-dimethylvaleronitrile) in 235 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After completion of the dropwise addition, the mixture was maintained at 80° C. for 4 hours and then cooled to room temperature to obtain a copolymer (resin B1) solution having a solid content of 35.1% and a viscosity of 125 mPas measured by a type B viscometer (23° C.). The resulting copolymer had a weight average molecular weight (Mw) of 9.2×10 ³ , a dispersion degree of 2.08, and an acid value in terms of solid content of 77 mg-KOH/g. Resin B1 has the following structural units.

[0244]

[0245] The polystyrene equivalent weight average molecular weight (Mw) and number average molecular weight (Mn) of the resin were measured by GPC method under the following conditions.

Device ; HLC-8120GPC (manufactured by TOSOH CORPORATION)

column ; TSK-GELG2000HXL

column temperature ; 40℃

menstruum ; THF

flow rate ; 1.0mL/min

test solution solids concentration; 0.001 to 0.01 mass %

injection volume ; 50 μL

detector ; RI

Calibration standards ; TSK STANDARD POLYSTYRENE

F-40, F-4, F-288, A-2500, A-500

(manufactured by TOSOH CORPORATION)

Ratio (Mw/Mn) of the polystyrene conversion weight average molecular weight and number average molecular weight obtained above was made into dispersion degree.

[0246] [Preparation of colorant dispersion 1]

23.1 parts of the compound represented by formula (AI-1), 28.8 parts of a dispersing agent (BYKLPN-6919 manufactured by BYK-Chemie; 60% solution of propylene glycol monomethyl ether acetate), 5.8 parts of resin B1 (in terms of solid content), 4 -Hydroxy-4-methyl-2-pentanone was mixed with 28.9 parts of propylene glycol monomethyl ether acetate and 202 parts of propylene glycol monomethyl ether acetate, 600 parts of 0.4 μm zirconia beads were added, and a paint conditioner (manufactured by LAU) was used for 1 hour. Shaking was performed. Thereafter, the zirconia beads were removed by filtration to obtain a colorant dispersion liquid 1.

[0247] [Comparative Example 1]

[Preparation of colored curable resin composition 1]

The coloring agent dispersion liquid 1, the compound represented by Formula (1-32), resin, a polymeric compound, a polymerization initiator, a solvent, and a leveling agent were mixed so that it might become a composition shown below, and the colored curable resin composition 1 was obtained. Colored curable resin composition 1 is a compound represented by the compound represented by 2.5 parts of Formula (A-I-1), and 0.2 part of Formula (1-32) as a coloring agent (A); As a dispersing agent, 1.9 parts (in terms of solid content) of BYKLPN-6919 (made by BYK-Chemie); As the resin (B), 7.8 parts (in terms of solid content) of Resin B1; As the polymerizable compound (C), 5.2 parts of KAYARAD (registered trademark) DPHA (manufactured by Nippon Kayaku Co., Ltd., dipentaerythritol hexaacrylate, hydroxyl value: 10 mgKOH/g); As polymerization initiator (D), 0.4 parts of PBG-327 (manufactured by Changzhou Troly New Electronic Materials Co., Ltd., N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2 -imines, oxime compounds); As the solvent (E), 78.9 parts of propylene glycol monomethyl ether acetate, 3.1 parts of 4-hydroxy-4-methyl-2-pentanone; As the leveling agent (F), 0.01 part (in terms of solid content) of Toray silicone SH8400 (manufactured by Dow Corning Toray Co., Ltd., polyether-modified silicone oil); is a colored curable resin composition.

[0248] [Comparative Example 2]

[Preparation of colored curable resin composition 2]

The coloring agent dispersion liquid 1, the compound represented by Formula (1-32), resin, a polymeric compound, a polymerization initiator, a solvent, and a leveling agent were mixed so that it might become a composition shown below, and the colored curable resin composition 2 was obtained. Colored curable resin composition 2 is a compound represented by the compound represented by 2.5 parts of Formula (A-I-1), and 0.2 part of Formula (1-32) as a coloring agent (A); As a dispersing agent, 1.9 parts (in terms of solid content) of BYKLPN-6919 (made by BYK-Chemie); As the resin (B), 7.8 parts (in terms of solid content) of Resin B1; As the polymerizable compound (C), 3.8 parts of KAYARAD (registered trademark) DPHA (manufactured by Nippon Kayaku Co., Ltd., dipentaerythritol hexaacrylate, hydroxyl value: 10 mgKOH/g), 1.5 parts of Aronix (registered trademark) M-933 (manufactured by TOAGOSEI CO., LTD., hydroxyl value: 280 mgKOH/g); As polymerization initiator (D), 0.4 parts of PBG-327 (manufactured by Changzhou Troly New Electronic Materials Co., Ltd., N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2 -imines, oxime compounds); As the solvent (E), 78.9 parts of propylene glycol monomethyl ether acetate, 3.1 parts of 4-hydroxy-4-methyl-2-pentanone; As the leveling agent (F), 0.01 part (in terms of solid content) of Toray silicone SH8400 (manufactured by Dow Corning Toray Co., Ltd., polyether-modified silicone oil); is a colored curable resin composition.

In addition, the hydroxyl value as a mixture of a polymeric compound (C) was 86 mgKOH/g.

[0249] [Comparative Example 3]

[Preparation of colored curable resin composition 3]

The coloring agent dispersion liquid 1, resin, a polymeric compound, a polymerization initiator, a solvent, and a leveling agent were mixed so that it might become a composition shown below, and the colored curable resin composition 3 was obtained. Colored curable resin composition 3 is a compound represented by 2.7 parts of Formula (A-I-1) as a coloring agent (A); As a dispersing agent, 2.0 parts (in terms of solid content) of BYKLPN-6919 (made by BYK-Chemie); As the resin (B), 7.7 parts (in terms of solid content) of Resin B1; As the polymerizable compound (C), 5.2 parts of KAYARAD (registered trademark) DPHA (manufactured by Nippon Kayaku Co., Ltd., dipentaerythritol hexaacrylate, hydroxyl value: 10 mgKOH/g); As polymerization initiator (D), 0.4 parts of PBG-327 (manufactured by Changzhou Troly New Electronic Materials Co., Ltd., N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2 -imines, oxime compounds); As the solvent (E), 78.6 parts of propylene glycol monomethyl ether acetate, 3.4 parts of 4-hydroxy-4-methyl-2-pentanone; As the leveling agent (F), 0.01 part (in terms of solid content) of Toray silicone SH8400 (manufactured by Dow Corning Toray Co., Ltd., polyether-modified silicone oil); is a colored curable resin composition.

[0250] [Example 1]

[Preparation of colored curable resin composition 4]

The coloring agent dispersion liquid 1, the compound represented by Formula (1-32), resin, a polymeric compound, a polymerization initiator, a solvent, and a leveling agent were mixed so that it might become a composition shown below, and the colored curable resin composition 4 was obtained. Colored curable resin composition 4 is a compound represented by 2.5 parts of formula (A-I-1), and 0.2 part of compound represented by Formula (1-32) as a coloring agent (A); As a dispersing agent, 1.9 parts (in terms of solid content) of BYKLPN-6919 (made by BYK-Chemie); As the resin (B), 7.8 parts (in terms of solid content) of Resin B1; As the polymerizable compound (C), 5.2 parts of A-TMM-3LM-N (manufactured by SHIN-NAKAMURA CHEMICAL CO., LTD., hydroxyl value: 110 mgKOH/g); As polymerization initiator (D), 0.4 parts of PBG-327 (manufactured by Changzhou Troly New Electronic Materials Co., Ltd., N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2 -imines, oxime compounds); As the solvent (E), 78.9 parts of propylene glycol monomethyl ether acetate, 3.1 parts of 4-hydroxy-4-methyl-2-pentanone; As the leveling agent (F), 0.01 part (in terms of solid content) of Toray silicone SH8400 (manufactured by Dow Corning Toray Co., Ltd., polyether-modified silicone oil); is a colored curable resin composition.

[0251] [Example 2]

[Preparation of colored curable resin composition 5]

The coloring agent dispersion liquid 1, the compound represented by Formula (1-32), resin, a polymeric compound, a polymerization initiator, a solvent, and a leveling agent were mixed so that it might become a composition shown below, and the colored curable resin composition 5 was obtained. Colored curable resin composition 5 is a compound represented by 2.5 parts of formula (A-I-1), and 0.2 part of compound represented by Formula (1-32) as a coloring agent (A); As a dispersing agent, 1.9 parts (in terms of solid content) of BYKLPN-6919 (made by BYK-Chemie); As the resin (B), 7.8 parts (in terms of solid content) of Resin B1; As the polymerizable compound (C), 5.2 parts of Aronix (registered trademark) M-933 (manufactured by TOAGOSEI CO., LTD., hydroxyl value: 280 mgKOH/g); As polymerization initiator (D), 0.4 parts of PBG-327 (manufactured by Changzhou Troly New Electronic Materials Co., Ltd., N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2 -imines, oxime compounds); As the solvent (E), 78.9 parts of propylene glycol monomethyl ether acetate, 3.1 parts of 4-hydroxy-4-methyl-2-pentanone; As the leveling agent (F), 0.01 part (in terms of solid content) of Toray silicone SH8400 (manufactured by Dow Corning Toray Co., Ltd., polyether-modified silicone oil); is a colored curable resin composition.

[0252] [Example 3]

[Preparation of colored curable resin composition 6]

The coloring agent dispersion liquid 1, the compound represented by Formula (1-32), resin, a polymeric compound, a polymerization initiator, a solvent, and a leveling agent were mixed so that it might become a composition shown below, and the colored curable resin composition 6 was obtained. Colored curable resin composition 6 is a compound represented by the compound represented by 2.5 parts of Formula (A-I-1), and 0.2 part of Formula (1-32) as a coloring agent (A); As a dispersing agent, 1.9 parts (in terms of solid content) of BYKLPN-6919 (made by BYK-Chemie); As the resin (B), 7.8 parts (in terms of solid content) of Resin B1; As the polymerizable compound (C), 2.5 parts of A-TMM-3LM-N (manufactured by SHIN-NAKAMURA CHEMICAL CO., LTD., hydroxyl value: 110 mgKOH/g), 2.8 parts of Aronix (registered trademark) M-933 (TOAGOSEI) manufactured by CO., LTD., hydroxyl value: 280 mgKOH/g); As polymerization initiator (D), 0.4 parts of PBG-327 (manufactured by Changzhou Troly New Electronic Materials Co., Ltd., N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2 -imines, oxime compounds); As the solvent (E), 78.9 parts of propylene glycol monomethyl ether acetate, 3.1 parts of 4-hydroxy-4-methyl-2-pentanone; As the leveling agent (F), 0.01 parts (in terms of solid content) of Toray silicone SH8400 (manufactured by Dow Corning Toray Co., Ltd., polyether-modified silicone oil); is a colored curable resin composition. In addition, the hydroxyl value as a mixture of a polymeric compound (C) was 200 mgKOH/g.

[0253] [Example 4]

[Preparation of colored curable resin composition 7]

The coloring agent dispersion liquid 1, resin, a polymeric compound, a polymerization initiator, a solvent, and a leveling agent were mixed so that it might become a composition shown below, and the colored curable resin composition 7 was obtained. Colored curable resin composition 7 is a compound represented by 2.7 parts of Formula (A-I-1) as a coloring agent (A); As a dispersing agent, 2.0 parts (in terms of solid content) of BYKLPN-6919 (made by BYK-Chemie); As the resin (B), 7.7 parts (in terms of solid content) of Resin B1; As the polymerizable compound (C), 5.2 parts of Aronix (registered trademark) M-933 (manufactured by TOAGOSEI CO., LTD., hydroxyl value: 280 mgKOH/g); As polymerization initiator (D), 0.4 parts of PBG-327 (manufactured by Changzhou Troly New Electronic Materials Co., Ltd., N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2 -imines, oxime compounds); As the solvent (E), 78.6 parts of propylene glycol monomethyl ether acetate, 3.4 parts of 4-hydroxy-4-methyl-2-pentanone; As the leveling agent (F), 0.01 part (in terms of solid content) of Toray silicone SH8400 (manufactured by Dow Corning Toray Co., Ltd., polyether-modified silicone oil); is a colored curable resin composition.

[0254] [Measurement of the hydroxyl value of the polymerizable compound]

According to JIS K 0070-1992, an acetylation reagent is added to the sample, heated in a glycerin bath, left to cool, and then a phenolphthalein solution is added as an indicator and titrated with a potassium hydroxide ethanol solution. and measured. The measurement results are as described above.

[0255] [Production of colored coating film (color filter)]

On a 5 cm square glass substrate (Eagle 2000; manufactured by Corning Incorporated), the colored curable resin compositions 1 to 7 were applied by spin coating so that the film thickness after post-baking was 2.5 μm, respectively, and then 100° C. was pre-baked for 3 minutes to form a coloring composition layer. After standing to cool, using an exposure machine (TME-150RSK; manufactured by TOPCON CORPORATION), the coloring composition layer was irradiated with light at an exposure amount (365 nm standard) of 80 mJ/cm ² in an atmospheric atmosphere. Then, it post-baked at 230 degreeC for 30 minute(s) within oven, and obtained the colored coating film.

[0256] [Measurement of film thickness change rate]

The chromaticity and the film thickness of the obtained colored coating film were measured, and the film thickness 1 when the y value was adjusted to 0.092, the x value 1, and the Y value 1 were computed. Thereafter, the colored coating film was heated in an oven at 230°C for 3 hours. The chromaticity and the film thickness of the colored coating film after heating were measured, the film thickness 2 when the y value was set to 0.092, the x value 2 and the Y value 2 were calculated, and the rate of change of the film thickness was calculated based on the following formula. A result is shown in Table 10.

Film thickness change rate = (film thickness 2 / film thickness 1) x 100

[0257] In addition, a film thickness measuring apparatus (DEKTAK3; manufactured by Japan Vacuum Engineering Co., Ltd.) was used to measure the film thickness of the colored coating film. Chromaticity was obtained from spectral data measured with a colorimeter (OSP-SP-200; manufactured by Olympus Corporation) and a characteristic function of the C light source as xy chromaticity coordinates (x, y) and stimulus value Y in the XYZ colorimetric system of CIE.

In addition, color difference ΔE*ab was calculated by the method described in JIS Z 8730:2009 (7. Color difference calculation method) from the chromaticity measurement values before and after heating. A result is shown in Table 10.

[0258] [Table 10]

[0259] From the above results, in the colored curable resin composition of the present invention, the film thickness tends to increase by heating, but the film thickness change rate is small. That is, it can be said that a dark color can be maintained by suppressing the phenomenon of color fading by heating. Moreover, the color change by heating is also small, and the color filter of high brightness can be obtained.

[Industrial Applicability]

[0260] According to the colored curable resin composition of the present invention, it is possible to provide a hyperchromic cured film that is a thin film. The color filter formed from the colored curable resin composition of this invention is useful as a color filter used for a display apparatus (For example, a liquid crystal display device, an organic electroluminescent display apparatus, electronic paper, etc.) and a solid-state image sensor.

Claims (6)

a colorant (A), a resin (B), a polymerizable compound (C), and a polymerization initiator (D);
The said coloring agent (A) contains the compound represented by Formula (a),
The colored curable resin composition in which the hydroxyl value of the said polymeric compound (C) is 100 mgKOH/g or more.

[In formula (a),
R ⁴¹ to R ⁴⁴ are each independently a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, or carbon number which may have a substituent An aralkyl group of 7 to 30 is represented, and the aromatic hydrocarbon group and the substituent which the aralkyl group may have may be -SO ₃ ^- or -SO ₂ -N ^- -SO ₂ -R ^f , and the number of carbon atoms in the saturated hydrocarbon group When is 2 to 20, -CH ₂ - contained in the saturated hydrocarbon group may be substituted with -O- or -CO-. However, in the saturated hydrocarbon group having 2 to 20 carbon atoms, adjacent -CH ₂ - is not simultaneously substituted with -O-, and the terminal -CH ₂ - is not substituted with -O- or -CO-. R ⁴¹ and R ⁴² may be bonded to each other to form a ring together with the nitrogen atom to which they are bonded, or R ⁴³ and R ⁴⁴ may be bonded to each other to form a ring together with the nitrogen atom to which they are bonded.
R ⁴⁷ to R ⁵⁴ each independently represent a hydrogen atom, a halogen atom, a nitro group, a hydroxyl group, -SO ₃ ^- , -SO ₂ -N ^- -SO ₂ -R ^f , or optionally a substituent having 1 to 20 carbon atoms represents a phosphorus saturated hydrocarbon group, and when the saturated hydrocarbon group has 2 to 20 carbon atoms, -CH ₂ - constituting the saturated hydrocarbon group may be substituted with -O- or -CO-, and R ⁴⁸ and R ⁵² are It may combine with each other to form -NH-, -S-, or -SO ₂ -. However, in this saturated hydrocarbon group, adjacent -CH ₂ - is not simultaneously substituted with -O-, and terminal -CH ₂ - is not substituted with -O- or -CO-.
Ring T ¹ represents an aromatic heterocycle having 3 to 10 carbon atoms, and the aromatic heterocycle is a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, a substituted or unsubstituted amino group, or 6 carbon atoms which may have a substituent. You may have an aromatic hydrocarbon group of -20, -SO ₃ ^- or -SO ₂ -N ^- -SO ₂ -R ^f . -SO ₃ ^- or -SO ₂ -N ^- -SO ₂ -R ^f may be sufficient as the substituent which this aromatic hydrocarbon group may have.
M ^r+ represents an r-valent metal ion.
k represents the sum of the number of -SO ₃ ^- and the number of -SO ₂ -N ^- -SO ₂ -R ^f which the compound represented by Formula (a) has.
r represents an integer of 1 or more.
R ^f represents a C1-C12 fluoroalkyl group.
However, the compound represented by formula (a) has at least one -SO ₃ ^- or -SO ₂ -N ^- -SO ₂ -R ^f ] According to claim 1,
The colored curable resin composition whose hydroxyl value of the said polymeric compound (C) is 200 mgKOH/g or more. 3. The method of claim 1 or 2,
The colored curable resin composition in which the said coloring agent (A) contains a xanthene dye further. 4. The method of claim 3,
The colored curable resin composition in which the said xanthene dye is a compound represented by Formula (1).

[In formula (1), R ¹ to R ⁴ each independently represent a hydrogen atom, -R ⁸ or a monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms, or R ¹ and R ² and R ³ and R ⁴ together form a ring containing a nitrogen atom, respectively. A hydrogen atom included in the aromatic hydrocarbon group is a halogen atom, -OH, -OR ⁸ , -SO ₃ ^- , -SO ₃ H, -SO ₃ -M ⁺ , -CO ² H, -CO ₂ R ₈ , ^-SO ₃ R ⁸ or -SO ₂ NR ⁹ R ¹⁰ may be substituted.
R ⁵ is -OH, -SO ₃ ^- , -SO ₃ H, -SO ₃ -M ⁺ , -CO ₂ H ^, -CO ₂ -M ⁺ , -CO ² R ⁸ , -SO ₃ R ₈ or ^-SO ₂ NR ⁹ R ¹⁰ is represented.
m represents the integer of 0-5, and when m is an integer of 2 or more, some R< ⁵ > may be same or different.
R ⁶ and R ⁷ each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
M ⁺ represents ⁺ N(R ¹¹ ) ₄ , Na ⁺ or K ⁺ , and X represents a halogen atom.
a represents 0 or 1.
R ⁸ represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, and the hydrogen atom contained in the saturated hydrocarbon group may be substituted with an aromatic hydrocarbon group having 6 to 10 carbon atoms, a carboxy group, or a halogen atom, and contained in the saturated hydrocarbon group -CH ₂ - used may be substituted with -S-, -O-, -CO- or -NR ¹¹ -. However, in this saturated hydrocarbon group, adjacent -CH ₂ - is not simultaneously substituted with -O-. R ¹¹ represents a hydrogen atom, a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms, and when two or more R ¹¹ are present, all or part of these may be the same.
R ⁹ and R ¹⁰ each independently represent a hydrogen atom or a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, the hydrogen atom contained in the saturated hydrocarbon group may be substituted with —OH or a halogen atom, and the saturated hydrocarbon group -CH ₂ - contained in the group may be substituted with -S-, -O-, -CO-, -NH- or -NR ⁸ -. However, in this saturated hydrocarbon group, adjacent -CH ₂ - is not simultaneously substituted with -O-.
R ⁹ and R ¹⁰ may be bonded to each other to form a 3- to 10-membered heterocyclic ring containing a nitrogen atom.] The color filter formed from the colored curable resin composition in any one of Claims 1-4. A display device comprising the color filter according to claim 5 .