TWI687764B - Coloring curable resin composition, dispersion liquid, color filter and display device - Google Patents

Abstract

The present invention further improves the chromaticity of the color-curable resin composition that can be used to manufacture color filters and the like. The colored curable resin composition contains a colorant (A), a resin (B), a polymerizable compound (C), and a polymerization initiator (D), and the colorant (A) includes a compound represented by formula (I) ( A1), and a coloring agent (A2) having a maximum absorption wavelength in chloroform of 500 nm or more and 700 nm or less.

Description

Coloring curable resin composition, dispersion liquid, color filter and display device Field of invention

The present invention relates to a color-curable resin composition containing a specific compound having a multiple methyl structure.

Background of the invention

Polymethyl compounds such as Fenjing are used in optical filters, for example (Patent Document 1). In the column of Examples of Patent Document 1, optical filters were manufactured using iodized salts of the following compounds No. 2 and No. 3.

However, in Patent Document 1, there is no evaluation of the brightness of the color filter.

Colorants with a maximum absorption wavelength of 500 nm or more and 700 nm or less are expected to further improve their brightness. As an example of using such a coloring agent, Patent Document 2 discloses an example of combining a specific xanthene dye with Pigment Red 254 For example, Patent Document 3 discloses an example of combining Pigment Red 242 and Pigment Red 177. For such a combined colorant, it is desired to further increase the brightness.

Existing technical literature Patent Literature

Patent Literature 1: Japanese Patent Laid-Open No. 2005-194509

Patent Document 2: Japanese Patent Laid-Open No. 2013-140348

Patent Document 3: Japanese Patent Laid-Open No. 11-14824

Summary of the invention

An object of the present invention is to further improve the chromaticity of a color-curable resin composition that can be used for manufacturing color filters and the like.

The present invention includes the following inventions.

[1] A colored curable resin composition comprising a colorant (A), a resin (B), a polymerizable compound (C), and a polymerization initiator (D), the colorant (A) comprising the formula (I) ) Represents the compound (A1) and the coloring agent (A2) having a maximum absorption wavelength in chloroform of 500 nm or more and 700 nm or less.

(In the formula, R ¹ , R ² , R ³ , R ⁴ , R ⁶ , R ⁷ and R ⁸ each independently represent a hydrogen atom, a hydroxyl group, a nitro group, a cyano group, a halogen atom, a carboxyl group, a sulfonic acid group, a carbon atom Alkyl groups with 1 to 20 carbon atoms, aryl groups with 6 to 30 carbon atoms, arylalkyl groups with 7 to 30 carbon atoms, arylalkenyl groups with 8 to 30 carbon atoms, and 2 to 30 carbon atoms (preferably Ground 2~20) containing heterocyclic groups or metallocene groups, R ⁵ represents a hydrogen atom, a C 1-20 alkyl group, a C 6-30 aryl group, a C 7-30 Arylalkyl, arylalkenyl having 8 to 30 carbon atoms, or heterocyclic group containing 2 to 30 carbon atoms, R ⁹ represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms or a cyano group , X represents >CR ¹⁰ R ¹¹ , an oxygen atom or a sulfur atom, R ¹⁰ and R ¹¹ each independently represent an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, and 7 to 30 carbon atoms Arylalkyl, arylalkenyl having 8 to 30 carbon atoms, or a heterocyclic group or metallocene group having 2 to 30 carbon atoms (preferably 2 to 20), R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ and R ¹¹ represent methylene groups in the alkyl group having 1 to 20 carbon atoms and 7 to 30 carbon atoms The arylalkyl group and the methylene group in the arylalkenyl group having 8 to 30 carbon atoms are sometimes replaced by -O-, -S-, -CO-, -COO-, -OCO-, -COS-, -OCS-, -SO ₂ -, -NH-, -CONH-, -NHCO-, -SO ₂ NH-, -NH-SO ₂ -, -N=CH- or -CH=CH- are not related to oxygen atoms Substitution under ortho-conditions, the alkyl portion of the groups shown by R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ and R ¹¹ may have branches The side chain may also be a cyclic alkyl group and may have a substituent, R ¹ and R ² , R ² and R ³ , R ³ and R ⁴ , R ⁴ and R ⁵ , R ¹ and R ¹⁰ , R ⁶ and R ⁸ , R ⁸ and R ⁹ and R ¹⁰ and R ¹¹ may each form a ring together, the formed ring may have a substituent, G represents an oxygen atom, a sulfur atom or a group selected from the following <Group 1>, A is in m =1 is not a bonding end, when m≧2, it means a single bond, nitrogen atom, -NR ¹² -, oxygen atom, sulfur atom, -SO ₂ -, -SO-, phosphorus atom, -PR ¹³ -, E ^{m +} (J ^-) organic group _{^{m, (m +) m L}} m- or satisfies the following (i) ~ (v) any one of conditions, E represents a m-valent cation, J represents a monovalent anion, m Represents a monovalent cation, L represents an m-valent anion, R ¹² and R ¹³ each independently represent the number of hydrogen atoms and carbon atoms 1 to 8 alkyl groups, 6 to 30 carbon atoms (preferably 6 to 20) aryl groups, 7 to 30 carbon atoms (preferably 7 to 20) arylalkyl groups, or 8 to 30 carbon atoms Arylalkenyl, alkyl, aryl, arylalkyl, and arylalkenyl represented by R ¹² and R ¹³ may sometimes be substituted with a halogen atom, hydroxyl, or nitro, and may have a substituent that forms a salt , The methylene group in the alkyl group, arylalkyl group, and arylalkenyl group represented by R ¹² and R ¹³ may be -COO-, -O-, -OCO-, -NHCO-, -NH-,- CONH- is replaced under the condition that oxygen atoms are not adjacent.

m is 1~6, when m≧2, A is connected to any one or more substituents of R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ and R ⁹ , there is A plurality of R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , n, X, and G may be the same or different, and n is 0 or 1. )

<group 1>

(In the formula, R and R'each independently represent an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms (preferably 6 to 20), and an aryl group having 7 to 30 carbon atoms (preferably 7 to 20) An arylalkyl group, or an arylalkenyl group having 8 to 30 carbon atoms, * means to bind to an adjacent group at the * portion.)

(i) m=2, and A is represented by the following formula (1).

【Chemical Formula 4】＊-Z ¹ -X ¹ -Z ² -＊ (1)

(In the formula, X ¹ represents -NR ¹⁴ -, a divalent aliphatic hydrocarbon group having 1 to 35 carbon atoms, a divalent alicyclic hydrocarbon group having 3 to 35 carbon atoms, and a divalent carbon atom having 6 to 35 carbon atoms. A hydrocarbon group containing an aromatic ring or a heterocyclic group containing 2 to 35 carbon atoms or a group represented by the following (1-A) to (1-C), Z ¹ and Z ² are each independent Represents direct bonding, -O-, -S-, -SO ₂ -, -SO-, -NR ¹⁴ -, -PR ¹⁵ -, -CO-, or a combination of these, R ¹⁴ and R ¹⁵ are each independently Represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms (preferably 6 to 20), an arylalkyl group having 7 to 30 carbon atoms (preferably 7 to 20), Or an arylalkenyl group having 8 to 30 carbon atoms, the alkyl group, aryl group, arylalkyl group, and arylalkenyl group represented by R ¹⁴ and R ¹⁵ may sometimes be substituted with a halogen atom, a hydroxyl group, or a nitro group, R The methylene group in the alkyl group, arylalkyl group, and arylalkenyl group represented by ¹⁴ and R ¹⁵ may be replaced by -COO-, -O-, -OCO-, -NHCO-, -NH-, -CONH- When the oxygen atoms are not adjacent to each other, * means that the * part is bonded to the adjacent group.

However, the group represented by the general formula (1) is in the range of 1 to 35 carbon atoms. )

(In the formula, R ²¹ represents a phenyl group which may be substituted with an alkyl group or an alkoxy group having 1 to 10 carbon atoms, or a cycloalkyl group having 3 to 10 carbon atoms, and R ²² represents an alkyl group having 1 to 10 carbon atoms. Group, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or a halogen atom, and the alkyl group, alkoxy group, and alkenyl group represented by R ²¹ and R ²² are substituted with a halogen atom or not Substitution, d is an integer from 0 to 4, * means that it is bonded to the adjacent group at the * part.)

(* in the formula means that it is bonded to the adjacent group at the * part)

(In the formula, R ²³ and R ²⁴ each independently represent an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms (preferably 6 to 20), and an aryl group having 6 to 30 carbon atoms (preferably 6 ~20) aryloxy group, arylthio group having 6-30 carbon atoms (preferably 6-20), arylalkyl group having 7-30 carbon atoms (preferably 7-20), 8-8 carbon atoms 30, an arylalkenyl group, or a heterocyclic group or a halogen atom having 2 to 30 carbon atoms (preferably 2 to 20), an alkyl group, an aryl group, an aryloxy group represented by R ²³ and R ²⁴ , Arylthio, arylalkyl, arylalkenyl, and heterocyclic group-containing groups are substituted or unsubstituted with halogen atoms, and alkyl, arylalkyl, and arylalkenes represented by R ²³ and R ²⁴ The methylene group in the group is sometimes replaced by an unsaturated bond, -O- or -S- under the condition that the oxygen atoms are not adjacent, R ²³ can form a ring between adjacent R ²³ , e represents 0~4 Number, f represents the number of 0-8, g represents the number of 0-4, h represents the number of 0-4, the sum of the number of g and h is 2-4, * means that it is bound to the adjacent group in the * part .)

(ii) m=3, and A is represented by the following formula (2).

(In the formula, X ² represents a carbon atom substituted with R ²⁵ , a trivalent aliphatic hydrocarbon group having 1 to 35 carbon atoms, a trivalent carbon atom having 3 to 35 alicyclic hydrocarbon groups, and a trivalent carbon number A hydrocarbon group containing an aromatic ring of 6 to 35 or a heterocyclic group containing a trivalent carbon number of 2 to 35, and R ²⁵ represents a hydrogen atom, an alkyl group of 1 to 8 carbon atoms, and a carbon atom of 6 to 30 ( (Preferably 6-20) aryl group, arylalkyl group having 7-30 carbon atoms (preferably 7-20), or arylalkenyl group having 8-30 carbon atoms, aliphatic hydrocarbon group represented by X ² The methylene group in is also sometimes separated by -COO-, -O-, -OCO-, -NHCO-, -NH-, -CONH-, -O-CONH-, -NHCO-O- on the oxygen atom. Substitution under conditions, Z ¹ to Z ³ are each independently the same as the groups represented by Z ¹ and Z ² in the above general formula (1), and * means to bond with an adjacent group at the * portion.

However, the group represented by the general formula (2) is in the range of 1 to 35 carbon atoms. )

(iii) m=4, and A is represented by the following formula (3).

(In the formula, X ³ represents the content of carbon atoms, a tetravalent aliphatic hydrocarbon group having 1 to 35 carbon atoms, a tetravalent carbon atom having 3 to 35 alicyclic hydrocarbon groups, and a tetravalent carbon atom having 6 to 35 carbon atoms. A hydrocarbon group of an aromatic ring or a heterocyclic group having a tetravalent carbon number of 2 to 35, and the methylene group in the aliphatic hydrocarbon group represented by X ³ may also be substituted by -COO-, -O-, -OCO-, -NHCO-, -NH-, -CONH-, -O-CONH-, -NHCO-O- are replaced under the condition that the oxygen atoms are not adjacent, Z ¹ ~ Z ⁴ are each independently from the above general formula (1) The groups represented by Z ¹ and Z ² are the same, and * means that they are bonded to adjacent groups at the * portion.

However, the group represented by the general formula (3) is in the range of 1 to 35 carbon atoms. )

(iv) m=5, and A is represented by the following formula (4).

(In the formula, X ⁴ represents a pentavalent aliphatic hydrocarbon group having 2 to 35 carbon atoms, a pentavalent carbon atom having 3 to 35 alicyclic hydrocarbon groups, and a pentavalent carbon atom having 6 to 35 carbon atoms. Hydrocarbon groups or heterocyclic groups containing pentavalent carbon atoms of 2 to 35, and the methylene group in the aliphatic hydrocarbon group represented by X ⁴ may sometimes be -COO-, -O-, -OCO-, -NHCO- , -NH-, -CONH-, -O-CONH-, -NHCO-O- are replaced under the condition that oxygen atoms are not adjacent, Z ¹ ~ Z ⁵ are each independently from Z ¹ in the above general formula (1) It is the same as the group represented by Z ² , and * means that it is bonded to the adjacent group at the * part.

However, the group represented by the general formula (4) is in the range of 2 to 35 carbon atoms. )

(v) m=6, and A is represented by the following formula (5).

【Chemical Formula 11】

(In the formula, X ⁵ represents an aliphatic hydrocarbon group having a hexavalent carbon number of 2 to 35, an alicyclic hydrocarbon group having a hexavalent carbon number of 3 to 35, and an aromatic ring-containing group having a hexavalent carbon number of 6 to 35. Hydrocarbon groups or hexavalent carbon atoms containing heterocyclic groups of 2 to 35, the methylene group in the aliphatic hydrocarbon group represented by X ⁵ may also be -COO-, -O-, -OCO-, -NHCO- , -NH -, - CONH -, - O-CONH -, - NHCO-O- replacing oxygen atoms are not adjacent in the conditions, Z ¹ ~ Z ⁶ each independently the general formula (1) Z ¹ It is the same as the group represented by Z ² , and * means that it is bonded to the adjacent group at the * part.

However, the group represented by the general formula (5) is in the range of 2 to 35 carbon atoms. )

[2] The coloring curable resin composition according to [1], wherein the compound (A1) is represented by formula (II).

【Chemical Formula 12】

(In the formula, ring D represents a five-membered ring or a six-membered ring. The five-membered ring or six-membered ring represented by ring D may be fused with other rings or may be substituted. R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , X, G, A and m are the same as the above general formula (I), when m≧2, there are multiple R ¹ , R ² , R ³ , R ⁴ , (R ⁵ , R ⁶ , R ⁷ , X, D, and G may be the same or different.)

[3] The coloring curable resin composition according to [1] or [2], wherein the compound (A1) is represented by formula (III).

(In the formula, X ¹¹ , X ¹² and X ¹³ each independently represent -O-, -S-, -C(=O)-, -C(=S)-, -N(R ³¹ )-, -N = Or -C(R ³² )=, the bond between X ¹¹ and X ¹² and X ¹² and X ¹³ is a single bond, a double bond or a conjugated double bond, R ³¹ represents a hydrogen atom and a carbon number of 1~20 Alkyl group, aryl group having 6-30 carbon atoms, arylalkyl group having 7-30 carbon atoms, arylalkenyl group having 8-30 carbon atoms, or 2-30 carbon atoms (preferably 2-20) The heterocyclic group, the alkyl group, aryl group, arylalkyl group, and arylalkenyl group represented by R ³¹ are sometimes substituted by halogen atoms, hydroxyl groups, carboxyl groups, sulfonic acid groups, nitro groups, sulfonamide groups Or, the sulfonamide group in which the alkyl group is bound to N is substituted, and the carboxyl group and the sulfonic acid group sometimes form a salt, and the methylene group in the alkyl group, arylalkyl group, and arylalkenyl group represented by R ³¹ also has Is replaced by -COO-, -O-, -OCO-, -NHCO-, -NH-, -CONH-, -SO ₂ -NH-, or -NH-SO ₂ -without oxygen atoms adjacent to each other, R ³² represents an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or an arylalkenyl group having 8 to 30 carbon atoms.

R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , X, A and m are the same as the above general formula (I), when m≧2, there are multiple R ¹ and R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , X ¹¹ , X ¹² and X ¹³ may be the same or different. )

[4] The coloring curable resin composition according to [1] or [2], wherein the compound (A1) is represented by formula (IV).

【Chemical Formula 14】

(Wherein, X ¹⁴ , X ¹⁵ , X ¹⁶ and X ¹⁷ each independently represent -O-, -S-, -C(=O)-, -C(=S)-, -N(R ³⁵ )- , -C(R ³⁶ )(R ³⁷ )-, -N= or -C(R ³⁸ )=, the bond between X ¹⁴ and X ¹⁵ , X ¹⁵ and X ¹⁶ and X ¹⁶ and X ¹⁷ is a single bond, Double bond or conjugated double bond, R ³⁵ each independently represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or An arylalkenyl group having 8 to 30 carbon atoms, or a heterocyclic group containing 2 to 30 carbon atoms (preferably 2 to 20), the alkyl group, aryl group, arylalkyl group described in R ³⁵ , Or the arylalkenyl group is sometimes substituted with a halogen atom, a hydroxyl group, a carboxyl group, a sulfonic acid group or a nitro group, and the carboxyl group and the sulfonic acid group sometimes form a salt, and the alkyl group, arylalkyl group, and aryl group represented by R ³⁵ The methylene group in the alkenyl group is sometimes replaced by -COO-, -O-, -OCO-, -NHCO-, -NH-, -CONH-, -SO ₂ -NH- or -NH-SO ₂ -in oxygen Substitution under conditions where the atoms are not adjacent, R ³⁶ , R ³⁷ and R ³⁸ each independently represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, and 7 to 30 carbon atoms Arylalkyl, or arylalkenyl having 8 to 30 carbon atoms, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , X, A, and m and the above general formula ( I) Same.)

[5] The color-curable resin composition according to any one of [1] to [3], wherein the compound (A1) is represented by formula (V).

(In the formula, R ¹ , R ² , R ³ , R ⁴ , R ⁶ , R ⁷ and X are the same as the above general formula (I), X ¹¹ , X ¹² and X ¹³ are the same as the above general formula (III), X ¹ , Z ¹ and Z ² are the same as the above general formula (1).)

[6] The coloring curable resin composition according to any one of [1], [2], or [4], wherein the compound (A1) is represented by formula (VI).

【Chemical Formula 16】

(In the formula, R ¹ , R ² , R ³ , R ⁴ , R ⁶ , R ⁷ and X are the same as the above general formula (I), X ¹⁴ , X ¹⁵ , X ¹⁶ and X ^{17 are the} same as the above general formula (IV) Same, X ¹ , Z ¹ and Z ² are the same as the above general formula (1).)

[7] The color-curable resin composition according to any one of [1] to [3], wherein the compound (A1) is represented by the general formula (VII).

(In the formula, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and X are the same as the above general formula (I), X ¹¹ is the same as the above general formula (III), R ³¹ is the above When X ¹³ in the general formula (III) is represented by -N(R ³¹ )-, R ^{31 is the} same, and any one or more of R ¹ , R ² , R ³ , R ⁴ , R ^5, and R ³¹ are selected from nitro; C1-20 alkyl groups substituted or unsubstituted by hydroxyl, carboxyl, sulfonic acid groups or halogen atoms; methylene groups in C1-C20 alkyl groups are -SO ₂ -NH- or -NH -SO ₂ -Substituted groups; those with 6 to 30 carbon atoms (preferably 6 to 20) carbon atoms substituted with hydroxy, carboxy, sulfonate, sulfonamide, or sulfonamide groups in which the alkyl is bound to N Aryl; arylalkyl having 7 to 30 carbon atoms (preferably 7 to 20) or aryl alkenyl having 8 to 30 carbon atoms substituted with hydroxyl, carboxyl or sulfonic acid groups; 1 to 20 carbon atoms Alkyl group, aryl group having 6 to 30 carbon atoms (preferably 6 to 20), or arylalkyl group having 7 to 30 carbon atoms (preferably 7 to 20), or aryl group having 8 to 30 carbon atoms Alkenyl has a group that forms a substituent of a salt.)

[8] The color-curable resin composition according to any one of [1], [2], or [4], wherein the compound (A1) is represented by formula (VIII).

(In the formula, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and X are the same as the above general formula (I), R ³⁵ is the same as X ¹⁵ and X in the above general formula (IV) ^{When 17 is} represented by -N(R ³⁵ )-, R ^{35 is the} same, and a plurality of R ^{35 are the} same or different. Any one or more of R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ³⁵ is selected from nitrate Group; substituted or unsubstituted C 1-20 alkyl group with hydroxyl, carboxyl, sulfonic acid group or halogen atom; methylene group in C 1-20 alkyl group is -SO ₂ -NH- or -NH-SO ₂ -Substituted group; aryl group having 6 to 30 carbon atoms (preferably 6 to 20) substituted with hydroxyl, carboxyl or sulfonic acid group; carbon atom substituted with hydroxyl, carboxyl or sulfonic acid group Arylalkyl having 7 to 30 (preferably 7 to 20); arylalkenyl having 8 to 30 carbon atoms substituted with hydroxyl, carboxyl or sulfonic acid groups; alkyl, carbon having 1 to 20 carbon atoms The aryl group having 6 to 30 atoms (preferably 6 to 20), the arylalkyl group having 7 to 30 carbon atoms (preferably 7 to 20), or the aryl alkenyl group having 8 to 30 carbon atoms has formed Salt substituent group.)

[9] The coloring curable resin composition according to any one of [1] to [8], wherein the colorant (A2) is a dye.

[10] The coloring curable resin composition according to [9], wherein the dye is a xanthene dye.

[11] The coloring curable resin composition according to [10], wherein the xanthene dye is represented by the following formula (1a).

[In formula (1a), R ^1a to R ^4a independently represent a hydrogen atom, a C 1-20 monovalent saturated hydrocarbon group which may have a substituent, and a C 6-10 monovalent which may have a substituent. Aromatic hydrocarbon group, or group represented by formula (i), *-R ^50a -Si(R ^29a ) ₃ (i)

(R ^29a represents a hydrogen atom, a hydroxyl group, a C 1-4 alkyl group or a C 1-4 alkoxy group, and a plurality of R ^29a may be the same as or different from each other. R ^50a represents a C 1-10 Alkanediyl, -CH ₂ -that constitutes the alkanediyl can be replaced by -O-, -CO-, -NR ^12a -, -OCO-, -COO-, -OCONH-, -NHCOO-, -CONH-, or- NHCO- is replaced under the condition that oxygen atoms are not adjacent.

* Indicates a bonding end with a nitrogen atom. )

In R ^1a to R ^4a , the methylene group (-CH ₂ -) contained in this saturated hydrocarbon group may also be replaced by -O-, -CO-, -NR ^11a -, -OCO-, -COO-, -OCONH- , -NHCOO-, -CONH- or -NHCO- are substituted under the condition that the oxygen atoms are not adjacent, R ^1a and R ^2a may also form a ring containing a nitrogen atom together, R ^3a and R ^4a may form a nitrogen atom-containing ring together Ring.

R ^5a represents _{^{-OH, -SO 3 -, -SO 3}} H, -SO 3 - Z +, -CO 2 H, -CO 2 - Z +, -CO 2 R 8a, -SO 3 R 8a or -SO ₂ NR ^9a R ^10a .

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

ma represents an integer from 0 to 5. When ma is 2 or more, a plurality of R ^5a may be the same or different.

a represents an integer of 0 or 1.

Xa represents a halogen atom.

Z ⁺ represents ⁺ N(R ^11a ) ₄ , Na ⁺ or K ⁺ , and the four R ^11a may be the same or different.

R ^8a represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, and the hydrogen atom contained in the saturated hydrocarbon group may be replaced by a halogen atom.

R ^9a and R ^10a independently represent a hydrogen atom or a C 1-20 monovalent saturated hydrocarbon group which may have a substituent, and the methylene group (-CH ₂ -) contained in the saturated hydrocarbon group may also be -O -, -CO-, -NR ^11a -, -OCO-, -COO-, -OCONH-, -NHCOO-, -CONH-, or -NHCO- are replaced without oxygen atoms adjacent to each other, R ^9a and R ^10a It can combine with each other to form a 3- to 10-membered heterocyclic ring containing a nitrogen atom.

R ^11a 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. ]

[12] A dispersion liquid comprising the compound (A1) according to any one of [1] to [8], a dispersant and an organic solvent.

[13] The dispersion liquid described in [12], wherein the dispersant is (1) a dispersant with an amine value of 0 to 200 mgKOH/g, (2) a dispersant with an acid value of 0 to 200 mgKOH/g, or (3) Any of dispersants having an amine value of 0 to 200 mgKOH/g and an acid value of 0 to 200 mgKOH/g.

[14] The dispersion liquid according to [12] or [13], wherein the organic solvent contains an alkylene glycol monoalkyl ether acetate, and the alkylene glycol monoalkyl ether acetate The content of R is 40% by mass or more and 99% by mass or less relative to the total amount of solvent.

[15] A color filter formed from the coloring curable resin composition according to any one of [1] to [11].

[16] A display device including the color filter described in [15].

By combining multiple methyl compounds and compounds with specific structures A combination of colorants with specific absorption wavelengths can improve lightness. More preferably, when the film thickness and the color coordinates are compared and compared, the brightness can be improved.

detailed description

<Colorant (A)>

<Multiple methyl compound (A1)>

The coloring curable resin composition of the present invention contains a colorant (A), a resin (B), a polymerizable compound (C), and a polymerization initiator (D), and the colorant (A) contains the formula (I) Compound (A1) (in this specification, for convenience, referred to as a polymethyl compound) and a colorant (A2) having a maximum absorption wavelength in chloroform of 500 nm or more and 700 nm or less. The polymethyl compound of formula (I) is excellent in light resistance.

(In the formula, R ¹ , R ² , R ³ , R ⁴ , R ⁶ , R ⁷ and R ⁸ each independently represent a hydrogen atom, a hydroxyl group, a nitro group, a cyano group, a halogen atom, a carboxyl group, a sulfonic acid group, a carbon atom Contains 1 to 20 alkyl groups, 6 to 30 carbon atoms aryl groups, 7 to 30 carbon atoms arylalkyl groups, 8 to 30 carbon atoms arylalkenyl groups, and 2 to 20 carbon atoms Heterocyclic group or metallocene group, R ⁵ represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, a carbon atom 8 to 30 arylalkenyl groups, or 2 to 30 carbon atoms containing heterocyclic groups, R ⁹ represents a hydrogen atom, a C 1-20 alkyl group or cyano group, X represents> CR ¹⁰ R ^11. Oxygen atom or sulfur atom, R ¹⁰ and R ¹¹ each independently represent an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, carbon Aryl alkenyl groups with 8 to 30 atoms, heterocyclic groups or metallocene groups with 2 to 20 carbon atoms, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , The methylene group in the alkyl group having 1 to 20 carbon atoms, the arylalkyl group having 7 to 30 carbon atoms, and the aromatic group having 8 to 30 carbon atoms in the alkyl group having 1 to 20 carbon atoms represented by R ⁸ , R ⁹ , R ¹⁰ and R ¹¹ The methylene group in the alkenyl group is sometimes replaced by -O-, -S-, -CO-, -COO-, -OCO-, -COS-, -OCS-, -SO ₂ -, -NH-, -CONH -, -NHCO-, -SO ₂ NH-, -NH-SO ₂ -, -N=CH- or -CH=CH- are replaced under the condition that the oxygen atoms are not adjacent, R ¹ , R ² , R ³ , The alkyl portion of the group represented by R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ and R ¹¹ may have a branched side chain or a cyclic alkyl group and may have a substituent , R ¹ and R ² , R ² and R ³ , R ³ and R ⁴ , R ⁴ and R ⁵ , R ¹ and R ¹⁰ , R ⁶ and R ⁸ , R ⁸ and R ⁹ and R ¹⁰ and R ¹¹ may each Form a ring together, the formed ring may have a substituent, G represents an oxygen atom, a sulfur atom or a group selected from the following <Group 1>, A is not a bonding end when m=1, and represents when m≧2 a single bond, a nitrogen atom, -NR ¹² -, oxygen atom, sulfur atom, -SO ₂ -, - SO-, a phosphorus ^{atom, -PR 13 -, E m +} (J -) m, (m +) m L m- Or an organic group that satisfies any one of the following conditions (i) to (v), E represents an m-valent cation, J represents a monovalent anion, M represents a monovalent cation, L represents an m-valent anion, R ¹² And R ¹³ each independently represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, and an aryl group having 6 to 20 carbon atoms , An arylalkyl group having 7 to 20 carbon atoms or an arylalkenyl group having 8 to 30 carbon atoms, and the alkyl, aryl, arylalkyl, and arylalkenyl groups represented by R ¹² and R ¹³ also have When substituted by a halogen atom, a hydroxyl group or a nitro group, may have a substituent that forms a salt, and the methylene group in the alkyl group, arylalkyl group, and arylalkenyl group represented by R ¹² and R ¹³ may be -COO -, -O-, -OCO-, -NHCO-, -NH-, and -CONH- are substituted under the condition that oxygen atoms are not adjacent.

m is 1~6, when m≧2, A is connected to any one or more substituents of R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ and R ⁹ , n It is 0 or 1 (preferably 1). )

<group 1>

【Chemical Formula 21】

(In the formula, R and R'each independently represent an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, or 8 to 30 carbon atoms. Arylalkenyl, * means to bond with the adjacent group at the * part.)

(i) m=2, and A is represented by the following formula (1).

【Chemical Formula 22】＊-Z ¹ -X ¹ -Z ² -＊ (1)

(In the formula, X ¹ represents -NR ¹⁴ -, a divalent aliphatic hydrocarbon group having 1 to 35 carbon atoms, a divalent alicyclic hydrocarbon group having 3 to 35 carbon atoms, and a divalent carbon atom having 6 to 35 carbon atoms. A hydrocarbon group containing an aromatic ring or a heterocyclic group containing 2 to 35 carbon atoms or a group represented by the following (1-A) to (1-C), Z ¹ and Z ² are each independent Represents direct bonding, -O-, -S-, -SO ₂ -, -SO-, -NR ¹⁴ -, -PR ¹⁵ -, -CO-, or a combination thereof, and R ¹⁴ and R ¹⁵ each independently represent Hydrogen atom, alkyl group having 1 to 10 carbon atoms, aryl group having 6 to 20 carbon atoms, arylalkyl group having 7 to 20 carbon atoms, or arylalkenyl group having 8 to 30 carbon atoms, R ¹⁴ The alkyl group, aryl group, arylalkyl group, and arylalkenyl group represented by R ¹⁵ may also be substituted with a halogen atom, a hydroxyl group, or a nitro group. The alkyl group, arylalkyl group represented by R ¹⁴ and R ¹⁵ , The methylene group in the arylalkenyl group can be replaced by -COO-, -O-, -OCO-, -NHCO-, -NH-, and -CONH- under the condition that the oxygen atom is not adjacent. However, the above (The group represented by formula (1) is in the range of 1 to 35 carbon atoms, * means that the * part is bonded to the adjacent group.)

(In the formula, R ²¹ represents a phenyl group which may be substituted with an alkyl group or an alkoxy group having 1 to 10 carbon atoms, or a cycloalkyl group having 3 to 10 carbon atoms, and R ²² represents an alkyl group having 1 to 10 carbon atoms. Group, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms or a halogen atom, and the alkyl group, alkoxy group and alkenyl group represented by R ²¹ and R ²² are substituted with a halogen atom or are unsubstituted Substitution, d is an integer from 0 to 4, * means that it is bonded to the adjacent group at the * part.)

(In the formula, * means that the * part is bonded to the adjacent group)

(In the formula, R ²³ and R ²⁴ each independently represent an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, and 6 to 20 carbon atoms. Arylthio group, arylalkyl group having 7 to 20 carbon atoms, arylalkenyl group having 8 to 30 carbon atoms, heterocyclic group or halogen atom having 2 to 20 carbon atoms, R ²³ and R alkyl group represented by ^24, aryl group, aryloxy group, arylthio group, arylalkyl group, arylalkenyl group, and a heterocyclic group is substituted by a halogen atom or an unsubstituted, R ²³ and R ²⁴ Suo The methylene groups in the shown alkyl, arylalkyl, and arylalkenyl groups are sometimes replaced by unsaturated bonds, -O- or -S- under conditions where the oxygen atoms are not adjacent, and R ²³ may be adjacent R ²³ forms a ring, e represents a number from 0 to 4, f represents a number from 0 to 8, g represents a number from 0 to 4, h represents a number from 0 to 4, the total number of g and h is 2~ 4. * means to bind to the adjacent group at the * part.)

(ii) m=3, and A is represented by the following formula (2).

(In the formula, X ² represents a carbon atom substituted with R ²⁵ , a trivalent aliphatic hydrocarbon group having 1 to 35 carbon atoms, a trivalent carbon atom having 3 to 35 alicyclic hydrocarbon groups, and a trivalent carbon number 6 to 35 hydrocarbon groups containing aromatic rings or heterocyclic groups containing trivalent carbon atoms of 2 to 35, R ²⁵ represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, and a carbon atom having 6 to 20 carbon atoms The aryl group, or the arylalkyl group having 7 to 20 carbon atoms, or the arylalkenyl group having 8 to 30 carbon atoms, and the methylene group in the aliphatic hydrocarbon group represented by X ² may also be -COO-,- O-, -OCO-, -NHCO-, -NH-, -CONH-, -O-CONH-, -NHCO-O- are replaced under the condition that oxygen atoms are not adjacent, Z ¹ ~Z ³ are independently The groups represented by Z ¹ and Z ² in the above general formula (1) are the same, and * means to be bonded to an adjacent group at the * portion.

However, the group represented by the general formula (3) is in the range of 1 to 35 carbon atoms. )

(iii) m=4, and A is represented by the following formula (3).

【Chemical Formula 27】

(In the formula, X ³ represents the content of carbon atoms, a tetravalent aliphatic hydrocarbon group having 1 to 35 carbon atoms, a tetravalent carbon atom having 3 to 35 alicyclic hydrocarbon groups, and a tetravalent carbon atom having 6 to 35 carbon atoms. A hydrocarbon group of an aromatic ring or a heterocyclic group having a tetravalent carbon number of 2 to 35, and the methylene group in the aliphatic hydrocarbon group represented by X ³ may also be substituted by -COO-, -O-, -OCO-, -NHCO-, -NH-, -CONH-, -O-CONH-, -NHCO-O- are replaced under the condition that the oxygen atoms are not adjacent, Z ¹ ~ Z ⁴ are each independently from the above general formula (1) The groups represented by Z ¹ and Z ² are the same, and * means that they are bonded to adjacent groups at the * portion.

However, the group represented by the general formula (3) is in the range of 1 to 35 carbon atoms. )

(iv) m=5, and A is represented by the following formula (4).

【Chemical Formula 28】

(In the formula, X ⁴ represents a pentavalent aliphatic hydrocarbon group having 2 to 35 carbon atoms, a pentavalent carbon atom having 3 to 35 alicyclic hydrocarbon groups, and a pentavalent carbon atom having 6 to 35 carbon atoms. Hydrocarbon groups or pentavalent carbon atoms containing heterocyclic groups of 2 to 35, the methylene group in the aliphatic hydrocarbon group represented by X ⁴ may also be -COO-, -O-, -OCO-, -NHCO -, -NH-, -CONH-, -O-CONH-, -NHCO-O- are replaced under the condition that oxygen atoms are not adjacent, Z ¹ ~ Z ⁵ are each independently from Z in the above general formula (1) The groups shown by ¹ and Z ² are the same, and * means that they are bonded to adjacent groups at the * part.

However, the group represented by the general formula (4) is in the range of 2 to 35 carbon atoms. )

(v) m=6, and A is represented by the following formula (5).

【Chemical Formula 29】

(In the formula, X ⁵ represents an aliphatic hydrocarbon group having a hexavalent carbon number of 2 to 35, an alicyclic hydrocarbon group having a hexavalent carbon number of 3 to 35, and an aromatic ring-containing group having a hexavalent carbon number of 6 to 35. Hydrocarbon groups or hexavalent carbon atoms containing heterocyclic groups of 2 to 35, the methylene group in the aliphatic hydrocarbon group represented by X ⁵ may also be -COO-, -O-, -OCO-, -NHCO- , -NH-, -CONH-, -O-CONH-, -NHCO-O- are replaced under the condition that oxygen atoms are not adjacent, Z ¹ ~ Z ⁶ are each independently from Z ¹ in the above general formula (1) It is the same as the group represented by Z ² , and * means that it is bonded to the adjacent group at the * part.

However, the group represented by the general formula (5) is in the range of 2 to 35 carbon atoms. )

The number of carbon atoms represented by R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ and R ¹¹ in the general formula (I) is 1-20 The alkyl group includes methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, isobutyl, pentyl, isopentyl, tert-pentyl, hexyl, cyclohexyl, Cyclohexylmethyl, cyclohexylethyl, heptyl, isoheptyl, tert-heptyl, n-octyl, isooctyl, tert-octyl, 2-ethylhexyl, nonyl, isononyl, decyl, ten Monoalkyl, dodecyl, tridecyl, tetradecyl, etc. as R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ¹⁰ and R ¹¹ Examples of the aryl group having 6 to 30 carbon atoms include aromatic hydrocarbon rings having a monocyclic or fused ring structure such as phenyl, naphthyl, biphenyl, anthracene-1-yl, and phenanthrene-1-yl. (Only refers to the part of the ring structure. The following is the same in "aromatic hydrocarbon ring") or its connecting structure as R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R The arylalkyl group having 7 to 30 carbon atoms and the arylalkenyl group having 8 to 30 carbon atoms represented by ¹⁰ and R ¹¹ include benzyl, phenethyl, 2-phenylpropyl, 3-benzene An alkyl or alkenyl group in which a monocyclic or condensed ring aromatic hydrocarbon ring or a connecting structure thereof, such as a propylpropyl group, diphenylmethyl group, triphenylmethyl group, styryl group, and cinnamyl group, is bonded.

R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ¹⁰ and R ¹¹ are also represented as heterocyclic groups containing 2 to 30 carbon atoms. In the heterocyclic group having 2 to 30 carbon atoms, the so-called heterocyclic group means a group containing at least one heterocyclic ring, and the carbon atom number means the number of carbon atoms in the entire group. In the following description, when the number of carbon atoms of a group containing a heterocyclic ring is defined, all mean the number of carbon atoms of the entire group. Examples of the heterocyclic group having 2 to 30 carbon atoms include pyridyl, pyrimidinyl, pyridazinyl, piperazinyl, piperidinyl, pyranyl, pyrazolyl, triazinyl, and pyrrole. Alkyl, quinolinyl, isoquinolinyl, imidazolyl, benzimidazolyl, triazolyl, furanyl, furanyl, benzofuranyl, thienyl, thienyl, benzothienyl, thiadiazolyl , Thiazolyl, benzothiazolyl, oxazolyl, benzoxazolyl, isothiazolyl, isoxazolyl, indolyl, jilonidine, morpholinyl, thiomorpholinyl, 2-pyrrolidone The monocyclic or condensed ring structures of -1-yl, 2-piperidone-1-yl, 2,4-dioxoimidazolidin-3-yl, 2,4-dioxoxazolidin-3-yl, etc. Heterocycle (only refers to the ring structure part. The same applies to the "single ring or condensed ring structure heterocycle" hereinafter) or its connecting structure.

Examples of the metallocene group represented by R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ¹⁰ and R ¹¹ include ferrocenyl, nickelocenyl, di Examples of the halogen atom represented by R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ^7, and R ⁸ include cobalocene, ferrocenyl alkyl, ferrocene alkoxy, etc. Fluorine, chlorine, bromine, iodine.

R ¹ and R ² , R ² and R ³ , R ³ and R ⁴ , R ⁴ and R ⁵ , R ¹ and R ¹⁰ , R ⁶ and R ⁸ , R ⁸ and R ^{9 in} the general formula (I) The ring structure formed by connecting R ¹⁰ and R ¹¹ includes piperidine ring, piperazine ring, pyrrolidine ring, morpholine ring, thiomorpholine ring, pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring , Triazine ring, quinoline ring, isoquinoline ring, imidazole ring, oxazole ring, imidazolidine ring, pyrazolidine ring, isoxazolidine ring, iminooxazolidine ring, isothiazolidine ring, winding Tannin ring, thiooxazolinone ring, hythione ring, indandione ring, thioindene ring, pyrazolone ring, pyridone ring, pyrazolidinedione ring, rhodanine ring, barbie Earth acid ring, thiobarbituric acid ring, oxazolone ring, hydantoin ring, hythionine ring, succinimide ring, maleimide ring, etc. These rings are sometimes linked with other rings It is fused, and may have the same properties as R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ and R ¹¹ in the general formula (I) The same substituents as the illustrated alkyl group having 1 to 20 carbon atoms.

R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ and R ¹¹ in the general formula (I) have 1 to 20 carbon atoms Alkyl, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ¹⁰ and R ^{11 have} 6 to 30 carbon atoms, R ¹ and R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ¹⁰ and R ¹¹ represent an arylalkyl group having 7 to 30 carbon atoms and an arylalkenyl group having 8 to 30 carbon atoms , And heterocyclic groups containing 2 to 30 carbon atoms represented by R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ¹⁰ and R ¹¹ may have substitution base. Examples of the substituent of the alkyl group having 1 to 20 carbon atoms include substituents other than the alkyl group and the arylalkyl group among the substituents exemplified below. As an aryl group having 6 to 30 carbon atoms, an aromatic hydrocarbon ring preferably having a monocyclic or condensed ring structure (refers only to a part of the ring structure. The following is the same in the "aromatic hydrocarbon ring") or a connection structure thereof Examples of the substituent include substituents other than the aryl group among the substituents exemplified below. An arylalkyl group having 7 to 30 carbon atoms or an arylalkenyl group having 8 to 30 carbon atoms, preferably an aromatic hydrocarbon ring having a monocyclic or condensed ring structure or an alkyl group to which the connecting structure is bonded or Examples of the substituent of the alkenyl group include the substituents exemplified below. However, among the substituents exemplified below, an aromatic system in which an alkyl group, an arylalkyl group, and an arylalkenyl group are substituted with an arylalkyl group having 7 to 30 carbon atoms or an arylalkenyl group having 8 to 30 carbon atoms Hydrocarbon ring. Examples of the heterocyclic group-containing group having 2 to 30 carbon atoms, preferably a monocyclic ring or condensed ring-structured heterocyclic ring or a connecting structure of the substituent include those other than the heterocyclic ring-containing group among the substituents exemplified below Of substituents.

It should be noted that R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ and R ¹¹ are the above-mentioned C 1-20 alkyl, carbon Containing aryl groups with 6 to 30 atoms, arylalkyl groups with 7 to 30 carbon atoms, arylalkenyl groups with 8 to 30 carbon atoms, or heterocyclic group-containing groups with 2 to 30 carbon atoms In the case of a group of carbon atoms, and when these groups have a substituent containing a carbon atom in the following substituents, the number of carbon atoms of the entire group including the substituent is set to satisfy a predetermined range. That is, when the alkyl group having 1 to 20 carbon atoms has a substituent containing carbon atoms, the range of carbon atoms is 1 to 20, and the aryl group having 6 to 30 carbon atoms has a substituent containing carbon atoms. The number of carbon atoms in the range is 6 to 30, and the arylalkyl group having 7 to 30 carbon atoms has a substituent containing carbon atoms. The range of carbon atoms is 7 to 30, and the number of carbon atoms is 8 to 30. When the aryl alkenyl group has a substituent containing a carbon atom, the number of carbon atoms ranges from 8 to 30, and the heterocyclic group having 2 to 30 carbon atoms has a substituent containing a carbon atom. The number of carbon atoms ranges from 2 to 30.

Exemplary substituents: Examples of the substituents include methyl, ethyl, propyl, isopropyl, cyclopropyl, butyl, sec-butyl, tert-butyl, isobutyl, pentyl, and isopentyl. Group, tert-amyl, cyclopentyl, hexyl, 2-hexyl (or hexane-2-yl), 2-ethylhexyl, 3-hexyl (or hexane-3-yl), cyclohexyl, dicyclohexyl, 1-methylcyclohexyl, heptyl, 2-heptyl, 3-heptyl, isoheptyl, t-heptyl, n-octyl, isooctyl, t-octyl, nonyl, isononyl, decyl, Alkyl groups such as lauryl; methoxy, ethoxy, propoxy, isopropoxy, butoxy, sec-butoxy, tert-butoxy, isobutoxy, pentoxy, isopentoxy Group, tert-pentyloxy, hexyloxy, cyclohexyloxy, heptyloxy, isoheptyloxy, tert-heptyloxy, n-octyloxy, isooctyloxy, tert-octyloxy, 2-ethylhexyl Alkoxy groups such as oxy, nonyloxy, decyloxy, etc.; methylthio, ethylthio, propylthio, isopropylthio, butylthio, sec-butylthio, tert-butylthio, isobutylthio Group, pentylthio group, isopentylthio group, tert-pentylthio group, hexylthio group, cyclohexylthio group, heptylthio group, isoheptylthio group, tert-heptylthio group, n-octylthio group, isooctylthio group, tert-butylthio group Octylthio, Alkylthio groups such as 2-ethylhexylthio; vinyl, 1-methylvinyl, 2-methylvinyl, 2-propenyl, 1-methyl-3-propenyl (or 1-methyl -2-propenyl), 3-butenyl, 1-methyl-3-butenyl, isobutenyl, 3-pentenyl, 4-hexenyl, cyclohexenyl, dicyclohexenyl, heptyl Alkenyl groups such as alkenyl, octenyl, decenyl, pentadecenyl, eicosyl, and tricosene; benzyl, phenethyl, diphenylmethyl, triphenyl Arylalkyl or arylalkenyl such as methyl, styryl, cinnamyl; aryl such as phenyl, naphthyl, preferably aromatic hydrocarbon ring; aryloxy such as phenoxy, naphthyloxy Arylthio groups such as phenylthio and naphthylthio; pyridyl, pyrimidinyl, pyridazinyl, piperidinyl, pyranyl, pyrazolyl, triazinyl, pyrrolyl, quinolinyl, isoquinyl Porphyrinyl, imidazolyl, benzimidazolyl, triazolyl, furyl, furyl, benzofuranyl, thienyl, thienyl, benzothienyl, thiadiazolyl, thiazolyl, benzothiazolyl, Oxazolyl, benzoxazolyl, isothiazolyl, isoxazolyl, indolyl, 2-pyrrolidone-1-yl, 2-piperidone-1-yl, 2,4-dioxazolidinyl- Heterocyclic groups such as 3-yl, 2,4-dioxazolidin-3-yl, etc., preferably monocyclic or fused ring structures; halogen atoms such as fluorine, chlorine, bromine, and iodine; Acetyl, 2-chloroethynyl, propionyl, octyl, phenylcarbonyl (benzyl), phthaloyl, 4-trifluoromethylbenzyl, neopentyl, salicyl, Acyl groups such as oxalyl, stearyl, methoxycarbonyl, ethoxycarbonyl, tert-butoxycarbonyl, n-octadecyloxycarbonyl, aminomethylamyl, etc.; acetoxy, benzoyl Acyloxy groups such as acyloxy; amino, ethylamino, dimethylamino, diethylamino, butylamino, cyclopentylamino, 2-ethylhexylamino, twelve Alkylamino, aniline, chlorophenylamino, toluyl, methoxyaniline, N-methyl-anilino, diphenylamino, Naphthylamino, 2-pyridylamino, methoxycarbonylamino, phenoxycarbonylamino, acetylamino, benzylamino, methylamino, neopentylamino Group, laurylamino group, aminomethylamino group, N,N-dimethylaminocarbonylamino group, N,N-diethylaminocarbonylamino group, morpholinocarbonylamino group, methyl Oxycarbonylamino, ethoxycarbonylamino, tert-butoxycarbonylamino, n-octadecyloxycarbonylamino, N-methyl-methoxycarbonylamino, phenoxycarbonylamino, Amino groups such as sulfamoylamino, N,N-dimethylaminosulfamoylamino, methylsulfonylamido, butylsulfonylamido, phenylsulfonylamido, etc. or Substituted amine group; sulfonamide group, sulfonamide group-containing group, carboxylic acid group, cyano group, sulfonic acid group, hydroxyl group, nitro group, mercapto group, amide imino group, amine methyl amide group, phosphate group, etc. These groups can be further substituted. In addition, the acidic groups such as the carboxylic acid group, sulfonic acid group, and phosphoric acid group can form salts with various cations, and the substituted amine groups can form salts with various anions after quaternization. Examples of the cations include alkali metal ions, alkaline earth metal ions, transition metal cations, ammonium with 4 or more carbon atoms, amidinium, guanidinium cations, and the like. As anions, for example, as a monovalent anion, chloride can be cited. Ions, bromide ions, iodide ions, fluoride ions and other halide ions; perchlorate ions, chlorate ions, thiocyanate ions, hexafluorophosphate ions, hexafluoroantimonate ions, tetrafluoroborate ions, etc. Inorganic anions; methanesulfonic acid ion, dodecylsulfonic acid ion, benzenesulfonic acid ion, toluenesulfonic acid ion, trifluoromethanesulfonic acid ion, pentafluorobenzenesulfonic acid ion, diphenylamine-4-sulfonic acid Ion, 2-amino-4-methyl-5-chlorobenzenesulfonic acid ion, 2-amino-5-nitrobenzenesulfonic acid ion, phthalocyanine sulfonic acid ion, perfluoro-4-ethylcyclohexane Sulfonic acid ion, naphthalene monosulfonic acid, naphthalene disulfonic acid, naphthalene trisulfonic acid, naphthylamine monosulfonic acid Organic sulfonic acid anions of acids, naphthylamine disulfonic acid, naphthylamine trisulfonic acid, naphthol monosulfonic acid, naphthol disulfonic acid, naphthol trisulfonic acid, etc.; thiocyanate ion, phosphotungstic molybdic acid Ion, phosphotungstic acid ion, phosphomolybdic acid ion, tannic acid ion, tartaric acid ion, palmitic acid ion, stearic acid ion, oleic acid ion, linoleic acid ion, octyl phosphate ion, dodecyl phosphate ion, ten Organic phosphate anions such as octaalkyl phosphate ion, phenyl phosphate ion, nonylphenyl phosphate ion, 2,2'-methylenebis(4,6-di-tert-butylphenyl)phosphonic acid ion , Bis-trifluoromethylsulfonyl imide ion, bis-perfluorobutane sulfonimide ion, tetrakis(pentafluorophenyl) borate ion, tris(fluoroalkylsulfonyl) carbon anion, tetrakis(pentafluoro Phenyl) borate anions etc.

As R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ and R ¹¹ (R ¹²⁵ in Group 2 described later) in the general formula (I) And R ¹²⁶ , R ³¹ in the general formula (III), and R ³⁵ in the general formula (IV) are the same) C 1-20 alkyl groups, preferably unsubstituted groups, fluorine, chlorine , Bromine and other halogen atoms; substituted amine group; sulfonamide group, sulfonamide group, carboxyl group, cyano group, sulfo group, hydroxyl group, nitro group, mercapto group, amide imino group, amine formyl group, sulfamoyl group , Phosphate groups and other substituted groups, methylene chains in alkyl groups replaced by SO ₂ NH, NHSO ₂ , O, NHCO, CONH, alkyl groups (including substituted alkyl groups) form salts Group.

As R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ¹⁰ and R ¹¹ (R ¹²⁵ and R ¹²⁶ in Group 2 described later, in the general formula (III) R ³¹ , the same as R ³⁵ in the general formula (IV) C 6-30 aryl group, preferably an unsubstituted group, the above-mentioned alkyl group, arylalkyl group, arylalkenyl group, Halogen atoms such as fluorine, chlorine, bromine, and iodine; substituted amine groups; sulfonamide, sulfonyl, carboxyl, cyano, sulfo, hydroxy, nitro, mercapto, imidate, amine-formamide , Methylene groups in the substituted groups such as sulfonamide group, phosphoric acid group, alkyl group substituted with aryl group or arylalkenyl group are -SO ₂ -NH- or -NH-SO ₂ -, O, NHCO , A group replaced by CONH, a group where an aryl group forms a salt (including an aryl group having a substituent.)

As R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ¹⁰ and R ¹¹ (R ¹²⁵ and R ¹²⁶ in Group 2 described later, in the general formula (III) R ³¹ and R ³⁵ in the general formula (IV) are the same) C 7-30 arylalkyl groups or C 8-30 arylalkenyl groups, preferably unsubstituted groups, The above-mentioned alkyl, alkoxy, fluorine, chlorine, bromine and other halogen atoms replace the amine group; sulfonamide group, sulfonyl group, carboxyl group, cyano group, sulfo group, hydroxyl group, nitro group, mercapto group, amide imino group, Groups substituted with aminomethyl amide, sulfonamide, phosphate, etc., the methylene chain in the arylalkyl group are oxygen atoms, -SO ₂ -NH- or -NH-SO ₂ -, O, The group substituted by NHCO and CONH, and the alkyl group (including the alkyl group having a substituent) form a salt group.

In the above general formula (I), R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ¹⁰ and R ^{11 have} an alkyl group having 1 to 20 carbon atoms The terminal methyl group, aryl group having 6 to 30 carbon atoms, arylalkyl group having 7 to 30 carbon atoms, and arylalkenyl group having 8 to 30 carbon atoms may have a carboxyl group, a sulfo group and a phosphate group, etc. The acidic group of the compound forms a salt substituent with various cations, or may have a substituent that forms a salt with various anions after quaternization of the substituted amine group.

Among the substituents forming such salts, examples of cations that form salts with acidic groups include alkaline earth metal ions such as magnesium, calcium, strontium, and barium, typical metal ions such as aluminum, zinc, nickel, cobalt, and copper. Vanadium and other transition metals Ions, ammonium with 4 or more carbon atoms, etc., as anions forming salts with quaternized substituted amine groups, examples of monovalent anions include chloride ions, bromide ions, iodide ions, fluoride ions, etc. Halide ions; inorganic anions such as perchloric acid ions, hexafluorophosphate ions, hexafluoroantimonate ions, tetrafluoroborate ions; organic sulfonic acid anions such as methanesulfonate ions, dodecylsulfonate ions; Heteropoly acid ions such as phosphomolybdate ions, bis(trifluoromethylsulfonyl)imide ions, bis(perfluorobutanesulfonyl)imide ions, tetrakis(pentafluorophenyl)borate ions, tris (Fluoroalkylsulfonyl) carbon anion, tetrakis(pentafluorophenyl) borate anion, etc.

In the above general formula (I), the salt-forming substituent can be obtained by using a precipitant that lakes acid dyes or a precipitant that lakes basic dyes. As the precipitating agent for lake acidic dyes, for example, barium chloride, aluminum chloride, alkaline earth metal salts, manganese salts, sodium salts, etc. can be used. Using phosphotungstic molybdic acid, phosphotungstic acid, phosphomolybdic acid, silicotungstic molybdic acid, silicomolybdic acid, tannic acid, tartaric acid, kaolin, smectite, higher fatty acids, etc., heating and filtering in aqueous solution or aqueous dispersion as needed And get.

In the above general formula (I), when m=1, A is not a bonding end. That is, the above general formula (I) is represented by the following general formula (I-1).

【Chemical Formula 30】

(In the formula, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , n, G and X are the same as the above general formula (I).)

It should be noted that, when n is 1, the polymethyl compound represented by the above general formula (I-1) may take the structure shown in the following general formula, and may be any structural formula. In addition, The structural isomers represented by any structural formula are used separately or as a mixture thereof. Furthermore, in terms of the following formula, the NR ⁵ group and the R ⁶ group have a cis arrangement (Z arrangement) with respect to the double bond, but they also include a case where they have a trans arrangement (E arrangement). Formula (I) is defined to include all geometric isomers due to carbon-carbon double bonds.

(In the formula, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , G and X are the same as the above general formula (I-1).)

Examples of the formula (I) A is a -NR ¹² - when R ^{12 is} represented by -PR ¹³ - ¹³ when R represents or a number of groups in which R and R 'are represented by 11 to 10 carbon atoms is Alkyl groups, aryl groups having 6 to 30 carbon atoms (preferably 6 to 20), arylalkyl groups having 7 to 30 carbon atoms (preferably 7 to 20), or aryl alkenes having 8 to 30 carbon atoms The group includes the groups exemplified in the description of the general formula (I).

The above general formula (I) A is the E ^{_m +} (J ^{-) m} represents, more specifically, refers to a portion other than the case where m ≧ 2 of formula (I) in A is used as the m J ^- The monovalent anions of these are in the state of being bound to the m-valent cation as Em ⁺ (A). In the case of the exemplified compounds described later, this corresponds to compounds No. 84, No. 85, No. 87 to No. 90.

The m-valent cations representing E, as divalent cations, include alkaline earth metal ions such as magnesium, calcium, strontium, and barium; transition metal cations such as zinc, copper, and nickel, etc., and trivalent cations include Typical metal ions such as aluminum; transition metal cations such as cobalt and iron, etc. Examples of cations having a valence of 4 or more include transition metal cations such as manganese.

A in the above general formula (I) is represented by (M ⁺ ) _m L ^m- , and more specifically, when m≧2, the part other than A in the general formula (I) becomes m as M ⁺ Monovalent cations, these cations are bound to the m-valent anion as L ^m+ (A). In the case of the exemplified compounds described later, this corresponds to compounds No. 86 and No. 91 to No. 95.

The m-valent anion representing L includes divalent anions such as chromate ions and the like, and trivalent anions include phosphomolybdate ions, phosphotungstate ions, phosphotungsten molybdate ions and vanadate ions. Examples of the tetravalent anions include silicotungstic acid ions and the like, and examples of the anions of more than five valences include phosphorus vanadium Molybdate ions, molybdate ions, etc.

In the above general formulas (1) to (5), the so-called alicyclic hydrocarbon group having 3 to 35 carbon atoms means that it contains at least one saturated monocyclic or polycyclic hydrocarbon group having 3 to 35 carbon atoms. Ring hydrocarbon group means a hydrocarbon group having 6 to 35 carbon atoms including at least one aromatic ring.

Examples of the divalent aliphatic hydrocarbon group having 1 to 35 carbon atoms represented by X ¹ in the general formula (1) include methane, ethane, propane, isopropane, butane, sec-butane, and tert-butane , Isobutane, hexane, 2-methylhexane, 3-methylhexane, heptane, 2-methylheptane, 3-methylheptane, isoheptane, tert-heptane, 1-methyl Octane, isooctane, tert-octane, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, 2,4-dimethylcyclobutane, 4-methylcyclohexane, etc. Is a divalent group substituted with Z ¹ and Z ² , and the methylene group in these groups is sometimes substituted by -O-, -S-, -CO-, -COO-, -OCO-,- NH- or a combination of these groups is replaced under the condition that the oxygen atoms are not adjacent, and the divalent alicyclic hydrocarbon group having 3 to 35 carbon atoms includes cyclopentyl, cyclohexyl, cycloheptyl , Cyclooctyl, cyclodecyl, 1-adamantyl, 2-adamantyl, n-adamantyl, 2-methyladamantyl, norbornyl, isonorbornyl, perhydronaphthyl, perhydrogen Anthryl, bicyclo[1.1.0]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.0]pentyl, bicyclo[3.1.0]hexyl, bicyclo[2.1.1]hexyl, bicyclo[2.2. 0] Hexyl, bicyclic [4.1.0] heptyl, bicyclic [3.2.0] heptyl, bicyclic [3.1.1] heptyl, bicyclic [2.2.1] heptyl, bicyclic [5.1.0] octyl, bicyclic [4.2.0] octyl, bicyclic [4.1.1] octyl, bicyclic [3.3.0] octyl, bicyclic [3.2.1] octyl, bicyclic [2.2.2] octyl, spiro [4,4] Nonyl, spiro[4,5]decyl, decahydronaphthalene, tricyclodecyl, tetracyclododecyl, cedarol, cyclododecyl, etc. are substituted by Z ¹ and Z ² Valence groups and the like, examples of the divalent C 6-35 aromatic ring-containing hydrocarbon group include divalent groups in which phenylene, naphthyl, and biphenyl groups are substituted with Z ¹ and Z ² Groups such as divalent C 2 to 35 heterocyclic group-containing groups include pyridine, pyrazine, piperidine, piperazine, pyrimidine, pyridazine, triazine, hexahydrotriazine, furan , Dihydrofuran, chroman, xanthene, thiophene, tetrahydrothiophene and other groups are substituted by Z ¹ and Z ² divalent groups.

These groups may be further substituted with halogen atoms, cyano groups, nitro groups, or alkoxy groups having 1 to 10 carbon atoms.

As the alkyl group having 1 to 10 carbon atoms, the aryl group having 6 to 30 carbon atoms (preferably 6 to 20) and 7 carbon atoms represented by R ¹⁴ and R ¹⁵ in the general formula (1), Examples of the halogen atom substituted with an arylalkyl group of ~30 (preferably 7-20) or an arylalkenyl group having 8-30 carbon atoms include the groups exemplified in the description of the above general formula (I).

In the above general formula (1-A), examples of the C 3-10 cycloalkyl represented by R ²¹ include cyclopropyl, cyclobutyl, cyclopentyl, cycloheptyl, cyclooctyl, and the like. These groups are substituted with a C 1-10 alkyl group or a C 1-10 alkoxy group, etc. As the above C 1-10 alkyl group and the carbon atom represented by R ²² The alkyl group having 1 to 10 includes the groups exemplified in the description of the general formula (I), and the alkoxy group having 1 to 10 carbon atoms represented by the alkoxy group and R ²² includes methyl group. Oxy, ethoxy, propoxy, isopropoxy, butoxy, sec-butoxy, tert-butoxy, isobutoxy, pentoxy, isopentoxy, tert-pentoxy, hexyl Oxygen, cyclohexyloxy, heptyloxy, isoheptyloxy, tert-heptyloxy, n-octyloxy, isooctyloxy, tert-octyloxy, 2-ethylhexyloxy, nonyloxy, decyl Oxygen groups and the like, examples of the alkenyl group having 2 to 10 carbon atoms represented by R ²² include vinyl group, allyl group, 1-propenyl group, isopropenyl group, 2-butenyl group, 1,3-butane Alkenyl, 2-pentenyl, 2-octenyl, etc., and the alkyl, alkoxy, and alkenyl groups in R ²² may be substituted with halogen atoms, and there is no restriction on the substitution position.

In the above general formula (1-C), R ²³ and R ²⁴ represent an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms (preferably 6 to 20), and 7 carbon atoms The arylalkyl group of ~30 (preferably 7-20), the arylalkenyl group having 8-30 carbon atoms, and the halogen atom can be exemplified by the groups exemplified in the description of the above general formula (I) as The aryloxy group having 6 to 30 carbon atoms (preferably 6 to 20) represented by R ²³ and R ²⁴ includes phenoxy, naphthoxy, 2-methylphenoxy, 3-methylphenoxy Group, 4-methylphenoxy, 4-vinylphenoxy, 3-isopropylphenoxy, 4-isopropylphenoxy, 4-butylphenoxy, 4-tert-butyl Phenoxy, 4-hexylphenoxy, 4-cyclohexylphenoxy, 4-octylphenoxy, 4-(2-ethylhexyl)phenoxy, 2,3-dimethylphenoxy , 2,4-dimethylphenoxy, 2,5-dimethylphenoxy, 2.6-dimethylphenoxy, 3.4-dimethylphenoxy, 3,5-dimethylphenoxy Group, 2,4-di-tert-butylphenoxy, 2,5-di-tert-butylphenoxy, 2,6-di-tert-butylphenoxy, 2.4-di-tert-pentylphenoxy Group, 2,5-tert-pentylphenoxy, 4-cyclohexylphenoxy, 2,4,5-trimethylphenoxy, ferrocenyloxy and other groups and these groups are halogenated The atom-substituted group is exemplified by the arylthio group having 6 to 30 carbon atoms (preferably 6 to 20), and the oxygen atom of the above aryloxy group having 6 to 30 carbon atoms (preferably 6 to 20) is exemplified. A group substituted with a sulfur atom, etc. Examples of the arylalkenyl group having 8 to 30 carbon atoms (preferably 8 to 20) include the aryloxy group having 6 to 30 carbon atoms (preferably 6 to 20). The oxygen atom is used for alkenyl such as vinyl, allyl, 1-propenyl, isopropenyl, 2-butenyl, 1,3-butadienyl, 2-pentenyl, 2-octenyl, etc. Substituted groups, etc. Examples of the heterocyclic group containing 2 to 30 carbon atoms (preferably 2 to 20) include pyridine, pyrazine, piperidine, piperazine, pyrimidine, pyridazine, triazine, Groups such as hexahydrotriazine, furan, tetrahydrofuran, chroman, xanthene, thiophene, thiofuran, etc., and groups in which these groups are substituted with halogen atoms, etc.

Examples of the trivalent aliphatic hydrocarbon group having 1 to 35 carbon atoms represented by X ² in the general formula (2) include the aliphatic hydrocarbon group exemplified in the description of X ¹ in the general formula (1). ¹ , trivalent groups substituted with Z ² and Z ³ , the methylene group in these groups may be -O-, -S-, -CO-, -CO-O-, -O-CO-, -SO ₂ -, -NH- or a group formed by combining them is interrupted under the condition that the oxygen atoms are not adjacent, and the trivalent C3-35 alicyclic hydrocarbon group includes the above general formula ( The trivalent group in which the alicyclic hydrocarbon group exemplified in the description of X ¹ in 1) is substituted with Z ¹ , Z ^2, and Z ^{3 is} an aromatic ring-containing hydrocarbon group having a trivalent carbon number of 6 to 35, The trivalent group in which the aromatic ring-containing hydrocarbon group exemplified in the description of X ¹ in the above general formula (1) is substituted with Z ¹ , Z ² and Z ³ is exemplified, and the number of trivalent carbon atoms is 2 to 35 Examples of the heterocyclic group-containing group include trivalent groups in which the heterocyclic group-containing group exemplified in the description of X ¹ in the general formula (1) is substituted with Z ¹ , Z ^2, and Z ³ .

As an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 30 carbon atoms (preferably 6 to 20) represented by R ²⁵ , and an aryl alkane having 7 to 30 carbon atoms (preferably 7 to 20) Examples of the group or the arylalkenyl group having 8 to 30 carbon atoms include the groups exemplified in the description of the general formula (I).

Examples of the tetravalent aliphatic hydrocarbon group having 1 to 35 carbon atoms represented by X ³ in the general formula (3) include the aliphatic hydrocarbon group exemplified in the description of X ¹ in the general formula (1). ¹ , Z ² , Z ³ and Z ⁴ substituted tetravalent groups can be -O-, -S-, -CO-, -COO-, -OCO-, -NH- or a combination of them The group of is interrupted under the condition that the oxygen atom is not adjacent, and examples of the tetravalent alicyclic hydrocarbon group having 3 to 35 carbon atoms include the alicyclic formula exemplified in the description of X ¹ in the above general formula (1) The tetravalent group in which the hydrocarbon group is substituted with Z ¹ , Z ² , Z ³ and Z ^{4 is} exemplified by X in the general formula (1) as the tetravalent C 6-35 aromatic ring-containing hydrocarbon group ^The tetravalent group in which the aromatic ring-containing hydrocarbon group exemplified in the description of ¹ is substituted with Z ¹ , Z ² , Z ^3, and Z ⁴ is a heterocyclic group containing a tetravalent carbon atom having 2 to 35 carbon atoms, The tetravalent group in which the heterocyclic group-containing group exemplified in the description of X ¹ in the above general formula (1) is substituted with Z ¹ , Z ² , Z ³ and Z ^{4 can} be cited.

Examples of the pentavalent aliphatic hydrocarbon group having 2 to 35 carbon atoms represented by X ⁴ in the general formula (4) include the aliphatic hydrocarbon group exemplified in the description of X ¹ in the general formula (1). ^{1. The} pentavalent group substituted by Z ² , Z ³ , Z ⁴ and Z ⁵ may be substituted by -O-, -S-, -CO-, -CO-O-, -O-CO-, -SO ₂ -, -NH- or a group formed by combining them is interrupted under the condition that oxygen atoms are not adjacent, and examples of the pentavalent C3-C35 alicyclic hydrocarbon group include the above general formula (1) The pentavalent group in which the alicyclic hydrocarbon group exemplified in the description of X ¹ in Z ¹ , Z ² , Z ³ , Z ⁴ and Z ^{5 is} substituted as a pentavalent carbon atom having 6 to 35 carbon atoms The cyclic hydrocarbon group includes a pentavalent group in which the aromatic ring-containing hydrocarbon group exemplified in the description of X ¹ in the general formula (3) is substituted with Z ¹ , Z ² , Z ³ , Z ⁴ and Z ⁵ , Examples of the pentavalent carbon atom-containing heterocyclic group having 2 to 35 carbon atoms include the heterocyclic group-containing groups exemplified in the description of X ¹ in the above general formula (1) by Z ¹ , Z ² , and Z ³ , A pentavalent group substituted by Z ⁴ and Z ⁵ .

Examples of the hexavalent aliphatic hydrocarbon group having 2 to 35 carbon atoms represented by X ⁵ in the general formula (5) include the aliphatic hydrocarbon group exemplified in the description of X ¹ in the general formula (1) by Z Hexavalent groups substituted by ¹ , Z ² , Z ³ , Z ⁴ , Z ⁵ and Z ⁶ may be substituted by -O-, -S-, -CO-, -COO-, -OCO-, -SO ₂ -, -NH- or a group formed by combining them is interrupted under the condition that the oxygen atoms are not adjacent, and the hexavalent carbon atom having 3 to 35 alicyclic hydrocarbon groups can be exemplified in the above general formula (1) The alicyclic hydrocarbon group exemplified in the description of X ^{1 is} a hexavalent group substituted with Z ¹ , Z ² , Z ³ , Z ⁴ , Z ⁵ and Z ⁶ , and has a carbon number of 6 to 35 as hexavalent Examples of the aromatic ring-containing hydrocarbon group include those in which the aromatic ring-containing hydrocarbon group exemplified in the description of X ¹ in the above general formula (1) is substituted with Z ¹ , Z ² , Z ³ , Z ⁴ , Z ⁵ and Z ⁶ The valent group includes a heterocyclic group having 2 to 35 carbon atoms and hexavalent carbon atoms, and the heterocyclic group-containing group exemplified in the description of X ¹ in the general formula (1) above is represented by Z ¹ , A hexavalent group substituted with Z ² , Z ³ , Z ⁴ , Z ⁵ and Z ⁶ .

In the compound represented by the above general formula (I), the ring formed by R ⁸ and R ⁹ is selected from the following group 2 compounds: when m is 2, X ¹ is a compound selected from the group of the following group 3; m When X is 3, X ² is a compound selected from the following group 4; when m is 4, X ³ is a compound selected from the group 5; when m is 5, X ⁴ is a group selected from the following 6 Compound of the group in; when m is 6, X ⁵ is a compound of the group selected from the group 7 below, and it is preferable because the raw materials are easily obtained and manufactured, and the heat resistance is high.

<group 2>

(In the formula, R ¹²⁵ represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, and an aryl group having 8 to 30 carbon atoms. Alkenyl group, C 2-30 (preferably 2-20) heterocyclic group-containing group or metallocene group, alkyl group represented by R ¹²⁵ , aryl group, arylalkyl group, and arylalkenyl group It may also be substituted by halogen atom, hydroxyl group, carboxyl group, sulfonate group, nitro group, sulfonamide group, sulfonamide group in which alkyl group is bound to N, etc. The carboxyl group and sulfonate group sometimes form a salt, which is formed by R ¹²⁵ The methylene groups in the represented alkyl, arylalkyl, and arylalkenyl groups are sometimes replaced by -COO-, -O-, -OCO-, -NHCO-, -NH-, -CONH-, -SO ₂ -NH- or -NH-SO ₂ -is replaced under the condition that oxygen atoms are not adjacent, R ¹²⁶ represents a hydrogen atom, a hydroxyl group, a nitro group, a cyano group, a halogen atom, a carboxyl group, a sulfonic acid group, and a carbon number of 1 to 20 Alkyl group, aryl group having 6 to 30 carbon atoms, arylalkyl group having 7 to 30 carbon atoms, aryl alkenyl group having 8 to 30 carbon atoms, 2 to 30 carbon atoms (preferably 2 to 20 carbon atoms) ) Of a heterocyclic group or a metallocene group, the alkyl group, aryl group, arylalkyl group, arylalkenyl group, heterocyclic group or metallocene group represented by R ¹²⁶ may be sometimes substituted with a halogen atom, a hydroxyl group or a nitro group, The methylene group in the alkyl group, arylalkyl group, and arylalkenyl group represented by R ¹²⁶ is sometimes substituted by -COO-, -O-, -OCO-, -NHCO-, -NH-, -CONH- The oxygen atoms are replaced without being adjacent.

＊Means bonding with adjacent group in ＊)

In the above group 2, the alkyl group having 1 to 20 carbon atoms, the aryl group having 6 to 30 carbon atoms, the arylalkyl group having 7 to 30 carbon atoms, and the number of carbon atoms represented by R ¹²⁵ or R ¹² 8 to 30 arylalkenyl groups, heterocyclic groups having 2 to 30 carbon atoms (preferably 2 to 20) or metallocene groups include the alkyl groups and aryl groups exemplified in the description of the general formula (I) above , Arylalkyl, arylalkenyl, heterocyclic or metallocene.

<group 3>

(In the formula, R ²⁷ represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms (preferably 6 to 20), and an aryl group having 7 to 30 carbon atoms (preferably 7 to 20) Arylalkyl group, or arylalkenyl group having 8 to 30 carbon atoms, the alkyl group, aryl group, arylalkyl group, and arylalkenyl group represented by R ²⁷ may also be sometimes halogen atom, hydroxyl group or nitro group Substituted, the methylene group in the alkyl group, arylalkyl group, and arylalkenyl group represented by R ²⁷ is sometimes substituted by -COO-, -O-, -OCO-, -NHCO-, -NH-, -CONH -Substitution under the condition that oxygen atoms are not adjacent, p represents an integer from 1 to 3, q represents an integer from 0 to 3 (preferably 1 to 3), r represents an integer from 1 to 19, * means that in * Adjacent groups combine.)

In the above group 3, as the alkyl group having 1 to 10 carbon atoms, the aryl group having 6 to 30 carbon atoms (preferably 6 to 20) represented by R ²⁷ , and the aryl group having 7 to 30 carbon atoms (preferably 7 to 20) The arylalkyl group and the arylalkenyl group having 8 to 30 carbon atoms include the alkyl group, aryl group, arylalkyl group or arylalkenyl group exemplified in the description of the general formula (I) above In the group satisfying the specified number of carbon atoms.

<group 4>

(In the formula, * means that the * part is bonded to the adjacent group)

<Group 5>

【Chemical Formula 35】

(In the formula, * means that the * part is bonded to the adjacent group)

<Group 6>

(In the formula, * means that the * part is bonded to the adjacent group)

<Group 7>

(In the formula, * means that the * part is bonded to the adjacent group)

As specific examples of the polymethyl compound represented by the general formula (I) of the present invention, the following compounds No. 1 to No. 107 can be mentioned.

【Chemical Formula 38】

【Chemical Formula 39】

【Chemical Formula 40】

【Chemical Formula 41】

【Chemical Formula 42】

【Chemical Formula 43】

【Chemical Formula 43】

【Chemical Formula 46】

【Chemical Formula 47】

【Chemical Formula 49】

【Chemical Formula 51】

【Chemical Formula 44】

【Chemical Formula 45】

【Chemical Formula 54】

【Chemical Formula 55】

Among the polymethyl compounds used in the present invention, compounds represented by the following general formula (II) are preferred.

(In the formula, ring D represents a five-membered ring or a six-membered ring. The five-membered ring or six-membered ring represented by ring D may be fused with another ring or substituted. R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , X, G, A and m are the same as the above general formula (I), when m≧2, there are multiple R ¹ , R ² , R ³ , R ⁴ , R ⁵ , (R ⁶ , R ⁷ , X, D, and G may be the same or different.)

In the above general formula (II), examples of the five-membered ring represented by the ring D include pyrazolone, rhodanine, thiooxazolinone, and prothionine. As the six-membered ring represented by the ring D, Barbituric acid, thiobarbituric acid, 3-cyano-1-alkyl-6-hydroxy-4-methyl-2-pyridone and the like can be mentioned. Ring D may have carbons represented by R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ and R ¹¹ in the general formula (I) The same substituents as alkyl groups with 1 to 20 atoms.

In addition, A in the said general formula (II) is the same as the said general formula (I), and when m=1, A is not a bonding end. That is, the above general formula (II) is represented by the following general formula (II-1).

(In the formula, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , G, and X are the same as the above general formula (I), and the ring D is the same as the above general formula (II).)

Among the compounds represented by the above general formula (II), in particular, the compounds represented by the following general formula (III) or (IV) are easy to synthesize and have high heat resistance, which is preferable.

【Chemical Formula 58】

(In the formula, X ¹¹ , X ¹² and X ¹³ each independently represent -O-, -S-, -C(=O)-, -C(=S)-, -N(R ³¹ )-, -N = Or -C(R ³² )=, the bond between X ¹¹ and X ¹² and X ¹² and X ¹³ is a single bond, a double bond or a conjugated double bond, and R ³¹ represents a hydrogen atom and a carbon number of 1 to 20 Alkyl group, aryl group having 6 to 30 carbon atoms, arylalkyl group having 7 to 30 carbon atoms, arylalkenyl group having 8 to 30 carbon atoms, or 3 to 30 carbon atoms (preferably 2 to 20) The heterocyclic group, the alkyl group, aryl group, arylalkyl group, and arylalkenyl group represented by R ³¹ are sometimes substituted by halogen atoms, hydroxyl groups, carboxyl groups, sulfonic acid groups, nitro groups, sulfonamide groups Or, the sulfonamide group in which the alkyl group is bound to N is substituted, and the carboxyl group and the sulfonic acid group sometimes form a salt, and the methylene group in the alkyl group, arylalkyl group, and arylalkenyl group represented by R ³¹ also has Is replaced by -COO-, -O-, -OCO-, -NHCO-, -NH-, -CONH-, -SO ₂ -NH-, or -NH-SO ₂ -without oxygen atoms adjacent to each other, R ³² represents an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or an arylalkenyl group having 8 to 30 carbon atoms.

R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , X, A and m are the same as the above general formula (I), when m≧2, there are multiple R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , X ¹¹ , X ¹² and X ¹³ may be the same or different. )

(Wherein, X ¹⁴ , X ¹⁵ , X ¹⁶ and X ¹⁷ each independently represent -O-, -S-, -C(=O)-, -C(=S)-, -N(R ³⁵ )- , -C(R ³⁶ )(R ³⁷ )-, -N= or -C(R ³⁸ )=, the bond between X ¹⁴ and X ¹⁵ , X ¹⁵ and X ¹⁶ and X ¹⁶ and X ¹⁷ is a single bond, Double bond or conjugated double bond, R ³⁵ each independently represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, carbon An arylalkenyl group having 8 to 30 atoms, or a heterocyclic group containing 3 to 30 carbon atoms (preferably 2 to 20), an alkyl group represented by R ³⁵ , an aryl group, an arylalkyl group, and The arylalkenyl group is sometimes substituted with a halogen atom, a hydroxyl group, a carboxyl group, a sulfonic acid group, or a nitro group, and the carboxyl group and the sulfonic acid group sometimes form a salt, and the alkyl group, arylalkyl group, and aryl group represented by R ³⁵ The methylene group in the alkenyl group is sometimes replaced by -COO-, -O-, -OCO-, -NHCO-, -NH-, -CONH-, -SO ₂ -NH-, or -NH-SO ₂ -, R ³⁶ , R ³⁷ and R ³⁸ each independently represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or the number of carbon atoms 8 to 30 arylalkenyl groups, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , X, A and m are the same as the above general formula (I).)

In the above general formula (III), the alkyl group having 1 to 20 carbon atoms, the aryl group having 6 to 30 carbon atoms, the arylalkyl group having 7 to 30 carbon atoms, and the arylalkenyl group represented by R ³¹ And a heterocyclic group containing 2 to 30 carbon atoms, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, and an aryl alkane having 7 to 30 carbon atoms represented by R ³² Examples of the group and the arylalkenyl group having 8 to 30 carbon atoms include the alkyl groups, aryl groups, arylalkyl groups, arylalkenyl groups, and heterocyclic group-containing groups exemplified in the description of the above general formula (I) .

It should be noted that A in the above general formula (III) is the same as the above general formula (I), and when m=1, A is not a bonding end. That is, the above general formula (III) is represented by the following general formula (III-1).

(In the formula, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and X are the same as the above general formula (I), X ¹¹ , X ¹² and X ^{13 are the} same as the above general formula (III) the same.)

The polymethyl compound represented by the above general formula (III-1) may take the structure shown in the following general formula, and may be of any structural formula, and in addition, the structural isomers of any structural formula may be separated , Or can be used as a mixture of them. Furthermore, in the following formula, the NR ⁵ group and the R ⁶ group have a cis configuration (Z configuration) with respect to the double bond, but they also include a case where they have a trans configuration (E configuration). Formula (III) is defined to include all geometric isomers due to carbon-carbon double bonds.

(In the formula, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , X, X ¹¹ , X ¹² and X ^{13 are the} same as the general formula (III-1) above.)

In addition, in the above general formula (IV), as a C 1-20 alkyl group represented by R ³⁵ , an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, a carbon atom The arylalkenyl group of 8-30, the heterocyclic group containing 2-30 carbon atoms, the alkyl group of 1-20 carbon atoms represented by R ³⁶ , R ³⁷ and R ³⁸ , and the number of carbon atoms 6~ Examples of the aryl group of 30, the arylalkyl group of 7 to 30 carbon atoms or the arylalkenyl group of 8 to 30 carbon atoms include the alkyl groups, aryl groups, and aromatic groups exemplified in the description of the above general formula (I) Group, arylalkenyl group, heterocyclic group, etc.

In addition, A in the said general formula (IV) is the same as the said general formula (I), and when m=1, A is not a bonding end. That is, the above general formula (IV) is represented by It is represented by the general formula (IV-1).

(In the formula, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and X are the same as the above general formula (I), X ¹⁴ , X ¹⁵ , X ¹⁶ and X ^{17 are the} same as the above general formula (IV) Same.)

The polymethyl compound represented by the above general formula (IV-1) may have the structure shown in the following general formula, and may be of any structural formula. In addition, the structural isomers represented by any of the structural formulas may be separated Used instead, or as a mixture of them. Furthermore, in terms of the following formula, the NR ⁵ group and the R ⁶ group have a cis arrangement (Z arrangement) with respect to the double bond, but they also include a case where they have a trans arrangement (E arrangement). Formula (III) is defined to include all geometric isomers due to carbon-carbon double bonds.

(In the formula, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , X, X ¹⁴ , X ¹⁵ , X ¹⁶ and X ^{17 are the} same as the above general formula (IV-1).)

Among the compounds represented by the above general formula (III), the compound represented by the following general formula (V) is preferable as the compound with m≧2 from the viewpoint of light resistance.

(In the formula, R ¹ , R ² , R ³ , R ⁴ , R ⁶ , R ⁷ and X are the same as the above general formula (I), X ¹¹ , X ¹² and X ¹³ are the same as the above general formula (III), X ¹ , Z ¹ and Z ² are the same as the above general formula (1).)

In a preferred form in formula (V), any one or more of R ¹ , R ² , R ³ , R ⁴ and R ³¹ are selected from nitro; substituted or unsubstituted by hydroxyl, carboxy, sulfonate or halogen atoms Alkyl groups with 1 to 20 carbon atoms; groups with methylene groups replaced with -SO ₂ -NH- or -NH-SO ₂ -in alkyl groups with 1 to 20 carbon atoms; hydroxyl, carboxyl or sulfonate An acid group, a sulfonamide group, or an aryl group having 6 to 30 carbon atoms (preferably 6 to 20) substituted with a sulfonamide group in which an alkyl group is bound to N; substituted by a hydroxyl group, a carboxyl group or a sulfonic acid group Arylalkyl having 7 to 30 carbon atoms (preferably 7 to 20) or arylalkenyl having 8 to 30 carbon atoms; alkyl having 1 to 20 carbon atoms and 6 to 30 carbon atoms (preferably The aryl group of 6-20), the arylalkyl group of 7-30 carbon atoms (preferably 7-20), or the arylalkenyl group of 8-30 carbon atoms have the group which formed the substituent of a salt.

In addition, in the formula (V), it is preferable that R ¹ and R ² do not form a ring together.

The polymethyl compound represented by the above general formula (V) may have the structure shown in the following general formula, and may be of any structural formula. In addition, structural isomers represented by any of the structural formulas may be separated and used. , Or as a mixture of them. In addition, it may be geometric isomers other than the following figure (the following formula), and formula (V) is defined as including all geometric isomers due to the C-C double bond.

【Chemical Formula 65】

(In the formula, R ¹ , R ² , R ³ , R ⁴ , R ⁶ , R ⁷ , X, X ¹¹ , X ¹² , X ¹³ , X ¹ , Z ¹ and Z ² are the same as the above general formula (V). )

In addition, as the compound represented by the above general formula (III), m=1 is preferably a compound represented by the following general formula (VII) from the viewpoint of solubility.

【Chemical Formula 66】

(In the formula, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and X are the same as the above general formula (I), X ¹¹ is the same as the above general formula (III), R ³¹ is the above When X ¹³ in the general formula (III) is represented by -N(R ³¹ )-, R ^{31 is the} same, and any one or more of R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ³¹ are selected from nitro; C1-20 alkyl groups substituted or unsubstituted by hydroxyl, carboxyl, sulfonic acid groups or halogen atoms; methylene groups in C1-C20 alkyl groups are -SO ₂ -NH- or -NH -SO ₂ -Substituted group; the number of carbon atoms substituted with hydroxy, carboxy, sulfonate, sulfonamide, or sulfonamide with alkyl group bonded to N is 7-30 (preferably 6-20 ); an arylalkyl group having 7 to 30 carbon atoms (preferably 7 to 20) carbon atoms substituted by a hydroxyl group, a carboxyl group or a sulfonic acid group; a carbon atom number 8 substituted by a hydroxyl group, a carboxyl group or a sulfonic acid group ~30 arylalkenyl; C1-C20 alkyl, C6-C30 (preferably 6-20) aryl, C7-C30 (preferably 7-20) aryl (Alkyl groups or arylalkenyl groups having 8 to 30 carbon atoms have a group that forms a substituent for a salt.)

The polymethyl compound represented by the above general formula (VII) may have the structure shown in the following general formula, and may be of any structural formula. In addition, structural isomers represented by any of the structural formulas may be separated and used. , Or as a mixture of them. In addition, it may be a geometric isomer other than the following formula, and formula (VII) is defined to include all geometric isomers due to carbon-carbon double bonds.

(In the formula, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , X, X ¹¹ and R ³¹ are the same as the above general formula (VII).)

Among the compounds represented by the general formula (IV), m≧2 is preferably a compound represented by the following general formula (VI) from the viewpoint of light resistance.

(In the formula, R ¹ , R ² , R ³ , R ⁴ , R ⁶ , R ⁷ and X are the same as the above general formula (I), X ¹⁴ , X ¹⁵ , X ¹⁶ and X ^{17 are the} same as the above general formula (IV) Same, X ¹ , Z ¹ and Z ² are the same as the above general formula (1).)

The polymethyl compound represented by the above general formula (VI) may have the structure shown in the following figure, but it may be of any structural formula, and in addition, structural isomers represented by any of the structural formulas may be separated and used, Or it can be used as a mixture of them. In addition, it may be a geometric isomer other than the following figure (the following formula), and formula (VI) is defined to include all geometric isomers due to carbon-carbon double bonds.

(In the formula, R ¹ , R ² , R ³ , R ⁴ , R ⁶ , R ⁷ , X, X ¹⁴ , X ¹⁵ , X ¹⁶ , X ¹⁷ , X ¹ , Z ¹ and Z ² and the above general formula (VI )the same.)

In addition, among the compounds represented by the above general formula (IV), the compound represented by the following general formula (VIII) is preferable as the compound of m=1 from the viewpoint of solubility.

(In the formula, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and X are the same as the above general formula (I), R ³⁵ is the same as X ¹⁵ and X in the above general formula (IV) ^{When 17 is} represented by -N(R ³⁵ )-, R ^{35 is the} same, and a plurality of R ^{35 are the} same or different. Any one or more of R ¹ , R ² , R ³ , R ⁴ , R ^5, and R ³⁵ is selected from nitrate Group; substituted or unsubstituted C 1-20 alkyl group with hydroxyl, carboxyl, sulfonic acid group or halogen atom; methylene group in C 1-20 alkyl group is -SO ₂ -NH- or -NH-SO ₂ -Substituted group; aryl group with 7 to 30 carbon atoms (preferably 6 to 20) substituted with hydroxyl, carboxyl or sulfonic acid group; substituted with hydroxyl, carboxyl or sulfonic acid group Arylalkyl having 7 to 30 carbon atoms (preferably 7 to 20); arylalkenyl having 8 to 30 carbon atoms substituted with hydroxyl, carboxyl or sulfonic acid groups; having 1 to 20 carbon atoms Alkyl groups, aryl groups having 6 to 30 carbon atoms (preferably 6 to 20), arylalkyl groups having 7 to 30 carbon atoms (preferably 7 to 20), or aryl alkenes having 8 to 30 carbon atoms The group has a group that forms a substituent of a salt.)

In the above general formula (VII) or (VIII), the so-called alkyl group having 1 to 20 carbon atoms, the aryl group having 7 to 30 carbon atoms (preferably 6 to 20), and the aryl group having 7 to 30 carbon atoms (preferably 7 ~20) arylalkyl, or arylalkenyl having 8-30 carbon atoms forms a salt substituent, as mentioned above, refers to alkyl, aryl, arylalkyl, or arylalkenyl The terminal alkyl group in the group has an acidic group such as a carboxyl group, a sulfo group, and a phosphoric acid group and a substituent that forms a salt with various cations, or has a substituent that forms a salt with various anions after quaternization of the substituted amine group.

Among the above-mentioned salt-forming substituents, as a preferable part excluding an alkyl group, an aryl group, an arylalkyl group, or an arylalkenyl group, a carboxyl group or a sulfo group may be combined with zinc, copper, nickel, etc., respectively. Transition metal cations; alkaline earth metals such as barium and other cations form part of the salt, and quaternized products of substituted amine groups such as dialkylamine groups with 1 to 20 carbon atoms and phosphomolybdate ions, Anions such as phosphotungstic acid ions, phosphotungstic molybdate ions, vanadate ions, etc. form part of the salt.

In the polymethyl compound represented by the general formula (VIII), the formula (VIII) is defined as a geometric isomer including all carbon-carbon double bonds.

In the above formulas, R ³⁵ is alkyl, arylalkyl case, an alkenyl group or an aryl group, each group of methylene R ¹ ~ R ^10, etc. Likewise, be -O -, - S-, -CO-, -COO-, -OCO-, -COS-, -OCS-, -SO ₂ -, -NH-, -CONH-, -NHCO-, -SO ₂ NH-, -NH-SO ₂ -, -N=CH- or -CH=CH- are replaced under the condition that the oxygen atoms are not adjacent.

A particularly preferred polymethyl compound is any one of R ¹ to R ⁴ in the above formulas (I) to (VIII) is a strong electron-withdrawing group selected from the group consisting of nitro, cyano, halogen atom and sulfonic acid group Compounds of a sexual group; or in the above formula (VIII), compounds containing any one or more of -OH group, -O- group, -SH group, and -S- group are included. In addition, -OH group and -SH group are introduced as a substituent. In addition, the -O- group and the -S- group are introduced by replacing any one of R ¹ to R ⁸ and R ³⁵ with an alkyl group, an arylalkyl group, or an arylalkenyl group, and a methylene group thereof.

Furthermore, in each of the above formulas (I) to (VIII), a compound having a sulfonic acid group in a part thereof is also preferred (as specific examples, it is compound No. 11, 15, 37, 59, 60, 77 to 80, 84 , 85, 88~90), a compound having a sulfonamide group in a part thereof (as specific examples, it is compound No. 23, 24, 38~43, 45, 46, 71, 73~80, 92, 94~ 97, etc.), or compounds where m is 2 or more (as specific examples, compound Nos. 25-29, 44-48, 53, 54, 56, 56, 63, 65, 73-75, 77, 84-97, etc.) . If it has a sulfonamide group, the reliability is improved. In addition, if m is 2 or more, sublimation can be suppressed.

The polymethyl compound represented by the above general formula (I) is not particularly limited by the production method thereof, and can be obtained by a method using a well-known general reaction. For example, when the compound G is an oxygen atom and m=1 and n=1, as shown in the following reaction formula 1, a reaction product of a compound having an active methylene group and a quaternary indole salt and an amidine compound can be used. Method synthesis.

Reaction 1

【Chemical Formula 71】

(In the formula, R ⁴¹ , R ⁴² and R ⁴³ represent an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or 8 carbon atoms. ~30 arylalkenyl group, An ^q- represents an anion of q valence, q is 1 or 2, p represents a coefficient that keeps the charge neutral, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ and X are the same as the general formula (I) above.)

In addition, in the above general formula (I), when G is an oxygen atom, m=1, n=1, R ⁸ and R ^{9 are} connected to form a ring D, as shown in the following reaction formula 2, the active sub The methyl compound is synthesized by the reaction product of the reaction product of the quaternary pseudo-indole salt and the amidine compound.

Reaction 2

(In the formula, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and X are the same as the above general formula (I), R ⁴¹ , R ⁴² , R ⁴³ , An ^q- , q and p is the same as the above Reaction Formula 1, and the ring D is the same as the above General Formula (II).)

In addition, G is an oxygen atom, m=2, n=1, A is represented by the above general formula In the case of the linking group represented by (1), as shown in the following Reaction Formula 3, an alkyl dihalide can be reacted with two equivalents of the pseudoindole compound, and then synthesized in the same manner as in the above Reaction Formula 1. The polymethyl compound represented by n=3 or more can also be synthesized according to the route shown in Reaction Scheme 3 below.

Reaction 3

(In the formula, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ and X are the same as the above general formula (I), R ⁴¹ , R ⁴² , R ⁴³ , An ^q- , q, and p are the same as in the above reaction formula 1, X ^* is a halogen atom.)

The amount of the polymethine compound (A1) is 100 parts by mass relative to the total amount of the polymethine compound (A1) and the coloring agent (A2) having a maximum absorption wavelength of 500 nm or more and 700 nm or less, for example, 1 part by mass The above, preferably 30 parts by mass or more, more preferably 50 parts by mass or more, for example, 99 parts by mass or less, preferably 90 parts by mass or less. In particular, when the coloring agent (A2) is a xanthene dye (a) described later, the amount of the multiple methyl compound (A1) is 100 relative to the total of the multiple methyl compound (A1) and the xanthene dye (a). The part by mass is, for example, 50 parts by mass or more, preferably 70 parts by mass or more, more preferably 80 parts by mass or more, for example, 97 parts by mass or less, preferably 95 parts by mass or less, more preferably 90 parts by mass or less.

<Coloring agent (A2) with a maximum absorption wavelength of 500 nm or more and 700 nm or less: xanthene dye (a)>

The multiple methyl compound (A1) is used in combination with a coloring agent (pigment) (A2) having a maximum absorption wavelength of 500 nm or more and 700 nm or less. This colorant (A2) does not contain a polymethyl compound (A1). In addition, the maximum absorption wavelength of the coloring agent (A2) used the result measured in the chloroform solvent. As the coloring agent (A2) having a maximum absorption wavelength of 500 nm or more and 700 nm or less, for example, xanthene dye (a) can be mentioned. The xanthene dye (a) used in the present invention is a dye containing a compound having a xanthene skeleton in the molecule. The xanthene dye (a) is preferably a rhodamine dye, and more preferably contains a compound represented by formula (1a) (Hereinafter sometimes referred to as "compound (1a)".) Dyes. Compound (1a) may be its tautomer. In addition, it may be combined with a xanthene dye or rhodamine dye other than the compound (1a).

[In formula (1a), R ^1a to R ^4a independently represent a hydrogen atom, a C 1-20 monovalent saturated hydrocarbon group which may have a substituent, and a C 6-10 monovalent which may have a substituent. Aromatic hydrocarbon group, or group represented by formula (i), *-R ^50a -Si(R ^29a ) ₃ (i)

(R ^29a represents a hydrogen atom, a hydroxyl group, a C 1-4 alkyl group or a C 1-4 alkoxy group, and a plurality of R ^29a may be the same as or different from each other.

R ^50a represents an alkanediyl group having 1 to 10 carbon atoms, and -CH ₂ -constituting the alkanediyl group may be replaced by -O-, -CO-, -NR ^12a -, -OCO-, -COO-, -OCONH-, -NHCOO-, -CONH- or -NHCO- is replaced under the condition that the oxygen atoms are not adjacent.

* Indicates a bonding end with a nitrogen atom. )

In R ^1a to R ^4a , the methylene group (-CH ₂ -) contained in this saturated hydrocarbon group may also be replaced by -O-, -CO-, -NR ^11a -, -OCO-, -COO-, -OCONH- , -NHCOO-, -CONH- or -NHCO- are replaced under the condition that the oxygen atoms are not adjacent, R ^1a and R ^2a may sometimes form a ring containing a nitrogen atom together, R ^3a and R ^4a may form a nitrogen atom-containing ring together Ring.

R ^5a represents _{^{-OH, -SO 3 -, -SO 3}} H, -SO 3 - Z +, -CO 2 H, -CO 2 - Z +, -CO 2 R 8a, -SO 3 R 8a or -SO ₂ NR ^9a R ^10a .

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

ma represents an integer from 0 to 5. When m is 2 or more, a plurality of R ⁵ may be the same or different.

a represents an integer of 0 or 1.

Xa represents a halogen atom.

Z ⁺ represents ⁺ N(R ^11a ) ₄ , Na ⁺ or K ⁺ , and the four R ^11a may be the same or different.

R ^8a represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, and the hydrogen atom contained in the saturated hydrocarbon group may be replaced by a halogen atom.

R ^9a and R ^10a independently represent a hydrogen atom or a C 1-20 monovalent saturated hydrocarbon group which may have a substituent, and the methylene group (-CH ₂ -) contained in the saturated hydrocarbon group may also be -O -, -CO-, -NR ^11a -, -OCO-, -COO-, -OCONH-, -NHCOO-, -CONH-, or -NHCO- are replaced when the oxygen atoms are not adjacent, R ⁹ and R ¹⁰ It can combine with each other to form a 3- to 10-membered heterocyclic ring containing a nitrogen atom.

R ^11a 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. ]

In formula (1a), when -SO ₃ ^- exists, the number is one.

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

The monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms may have a substituent. Examples of the aromatic hydrocarbon group may have a substituent include a halogen ^{atom, -R 8a, -OH, -OR 8a} , -SO 3 -, -SO 3 H, -SO 3 - Z +, -CO 2 H, - CO ₂ R ^8a , -SR ^8a , -SO ₂ R ^8a , -SO ₃ R ^8a or -SO ₂ NR ^9a R ^10a , it is preferable that these substituents replace the hydrogen atoms contained in the aromatic hydrocarbon group. Among these, as a substituent group, preferably _{^{-R 8a, -SO 3 -, -SO}} 3 H, -SO 3 - Z + and -SO ₂ NR ^9a R ^10a, and more preferably -R ^8a, -SO ₃ ^- Z ⁺ and -SO ₂ NR ^9a R ^10a . In this case, -R ^{8a is} more preferably a monovalent saturated hydrocarbon group having 1 to 10 carbon atoms, and still more preferably an alkyl group having 1 to 5 carbon atoms. In addition, as -SO ₃ ^- Z ^{+ in} this case, -SO ₃ ^- N ⁺ (R ^11a ) ₄ is preferred.

Examples of monovalent saturated hydrocarbon groups having 1 to 20 carbon atoms in R ^1a to R ^4a and R ^8a to R ^11a include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, and octyl Straight-chain alkyl groups such as phenyl, nonyl, decyl, dodecyl, hexadecyl, eicosyl, etc.; isopropyl, isobutyl, isopentyl, neopentyl, 2-ethyl Branched chain alkyl groups such as hexyl; cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, tricyclodecyl, etc. C3-20 alicyclic saturated hydrocarbon groups.

The methylene group (-CH ₂ -) contained in the saturated hydrocarbon group may be replaced by -O-, -CO-, -NR ^11a -, -OCO-, -COO-, -OCONH-, -NHCOO-, -CONH- Or -NHCO- is replaced without oxygen atoms being adjacent.

Examples of the group in which the methylene group (-CH ₂ -) contained in the saturated hydrocarbon group is replaced with -O- include the following groups (* indicates a bonding end).

Examples of the group in which the methylene group (-CH ₂ -) contained in the saturated hydrocarbon group is replaced by -CO- include the following groups (* indicates a bonding end).

Examples of the group in which the methylene group (-CH ₂ -) contained in the saturated hydrocarbon group is replaced by -NR ^11a -include the following groups (* indicates a bonding end).

Examples of the group in which the methylene group (-CH ₂ -) contained in the saturated hydrocarbon group is replaced by -OCO- include the following groups (* indicates a bonding end).

Examples of the group in which the methylene group (-CH ₂ -) contained in the saturated hydrocarbon group is replaced by -COO- include the following groups (* indicates a bonding end).

Examples of the group in which the methylene group (-CH ₂ -) contained in the saturated hydrocarbon group is replaced by -OCONH- include the following groups (* indicates a bonding end).

Examples of the group in which the methylene group (-CH ₂ -) contained in the saturated hydrocarbon group is replaced by -NHCOO- include the following groups (* indicates a bonding end).

Examples of the group in which the methylene group (-CH ₂ -) contained in the saturated hydrocarbon group is replaced by -CONH- include the following groups (* indicates a bonding end).

Examples of the group in which the methylene group (-CH ₂ -) contained in the saturated hydrocarbon group is replaced by -NHCO- include the following groups (* indicates a bonding end).

The hydrogen atom contained in the saturated hydrocarbon group in R ^1a to R ^4a may be substituted with, for example, a C 6-10 aromatic hydrocarbon group or halogen atom as a substituent. The aromatic hydrocarbon group may be substituted with R ^1a of hydrogen atoms of the saturated hydrocarbon group R ^4a ~ 6 ~ 10 include the aromatic hydrocarbon group as the examples of R in the number of carbon ^{atoms. 1A} ~ R ^4a 6 to 10 shown in the same Group.

The hydrogen atom contained in the saturated hydrocarbon group in R ^9a and R ^10a may be substituted with, for example, a hydroxyl group or a halogen atom as a substituent.

Examples of the ring formed by R ^1a and R ^2a together and the ring formed by R ^3a and R ^4a together include the following rings.

Examples of -OR ^8a include methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, 2-ethylhexyloxy and Alkoxy groups such as alkoxy groups.

Examples of -CO ₂ R ⁸ include methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, tert-butoxycarbonyl, hexoxycarbonyl, eicosoxycarbonyl, and the like. .

Examples of -SR ^8a include alkylsulfanes such as methylsulfanyl, ethylsulfanyl, butylsulfanyl, hexylsulfanyl, decylsulfanyl, and eicosylsulfanyl. Base etc.

Examples of -SO ₂ R ^8a include alkyl groups such as methylsulfonyl, ethylsulfonyl, butylsulfonyl, hexylsulfonyl, decylsulfonyl, and eicosylsulfonyl. Sulfonyl and so on.

Examples of -SO ₃ R ^8a include methoxysulfonyl, ethoxysulfonyl, propoxysulfonyl, tert-butoxysulfonyl, hexyloxysulfonyl and eicosane Alkoxysulfonyl and the like such as oxysulfonyl.

Examples of -SO ₂ NR ^9a R ^10a include sulfamoyl; N-methylsulfamoyl, N-ethylsulfamoyl, N-propylsulfamoyl, N-isopropylamine Sulfonyl, N-butylaminesulfonyl, N-isobutylaminesulfonyl, N-sec-butylaminesulfonyl, N-tert-butylaminesulfonyl, N-pentylamine Sulfonyl, N-(1-ethylpropyl) sulfonamide, N-(1,1-dimethylpropyl) sulfonamide, N-(1,2-dimethylpropyl) Sulfasalamide, N-(2,2-dimethylpropyl) Sulfasyl, N-(1-Methylbutyl) Sulfasyl, N-(2-Methylbutyl) Sulfasyl Acyl, N-(3-methylbutyl) sulfamoyl, N-cyclopentylaminosulfamoyl, N-hexylaminosulfamoyl, N-(1,3-dimethylbutyl)amine Sulfonyl, N-(3,3-dimethylbutyl) sulfonamide, N-heptyl sulfonamide, N-(1-methylhexyl) sulfonamide, N-(1, 4-Dimethylpentyl) sulfamoyl, N-octyl sulfamoyl, N-(2-ethylhexyl) sulfamoyl, N-(1,5-dimethylhexyl) sulfa N-1 substituted sulfamoyl groups such as acetyl group, N-(1,1,2,2-tetramethylbutyl) sulfamoyl group; N,N-dimethyl sulfamoyl group, N,N -Ethylmethylsulfamoyl, N,N-diethylaminesulfamoyl, N,N-propylmethylsulfamoyl, N,N-isopropylmethylsulfamoyl, N ,N-tert-butylmethylsulamide, N,N-butylethylsulamide, N,N-bis(1-methylpropyl)sulamide, N,N-heptylmethyl N, N-2 substituted for sulfamoyl, etc.

As R ^5a, preferably ^{_{-CO 2 H, -CO 2 -Z +}} , -CO 2 R 8a, -SO 3 -, -SO 3 - Z +, -SO 3 H or -SO ₂ NHR ^9a, more preferably -SO _{^{3 -, -SO 3 - Z +}} , -SO 3 H or -SO ₂ NHR ^9.

ma is preferably 1 to 4, more preferably 1 or 2.

As the compound (1a), a phenyl group substituted with a (R ^5a ) _ma group in formula (1a) is preferably a compound having any one of the following formulas (R ^5a -1) to (R ^5a -37), and more preferably ( Any one of R ^5a -1) to (R ^5a -25) is more preferably (R ^5a -1) to (R ^5a -5), and particularly preferably (R ^5a -1). In addition, in the following formulas (R ^5a -1) to (R ^5a -37), R ^40a and R ^41a represent a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, preferably a branched chain having 6 to 12 carbon atoms The alkyl group is more preferably 2-ethylhexyl.

【Chemical Formula 85】

【Chemical Formula 86】

As the alkyl group having 1 to 6 carbon atoms in R ^6a and R ^7a , the alkyl group having 1 to 6 carbon atoms in the above-exemplified alkyl groups may be mentioned. Among them, R ^6a and R ^{7a are} preferably hydrogen atoms.

R ^9a and R ^10a may represent a 3- to 10-membered nitrogen-containing heterocyclic ring together with a nitrogen atom. Examples of the heterocycle include the following heterocycles.

Examples of the aralkyl group having 7 to 10 carbon atoms in R ^11a include benzyl, phenylethyl, and phenylbutyl.

Z ⁺ is ⁺ N(R ^11a ) ₄ , Na ⁺ or K ⁺ , preferably ⁺ N(R ^11a ) ₄ .

As the above ⁺ N(R ^11a ) ₄ , it is preferable that at least two of the four R ^11a are monovalent saturated hydrocarbon groups having 5 to 20 carbon atoms. In addition, the total carbon number of the four R ^11a is preferably 20 to 80, and more preferably 20 to 60. In the case where ⁺ N(R ^11a ) ₄ is present in the compound (1a), if R ^11a is these groups, the color-curable resin composition of the present invention containing the compound (1a) can form a color filter with few foreign substances Device.

Xa is a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom or an iodine atom, preferably a chlorine atom or a bromine atom, and more preferably a chlorine atom.

a is 0 or 1, more preferably 0.

In addition, R ^1a to R ^4a may represent a group represented by the following formula (i).

＊-R ^50a -Si(R ^29a ) ₃ (i)

(R ^29a represents a hydrogen atom, a hydroxyl group, a C 1-4 alkyl group or a C 1-4 alkoxy group, and a plurality of R ^29a may be the same as or different from each other.

R ^50a represents an alkanediyl group having 1 to 10 carbon atoms, and -CH ₂ -constituting the alkanediyl group may be replaced by -O-, -CO-, -NR ^11a -, -OCO-, -COO-, -OCONH-, -NHCOO-, -CONH- or -NHCO- is replaced under the condition that the oxygen atoms are not adjacent.

* Indicates a bonding end with a nitrogen atom. )

R ^29a represents a hydrogen atom, a hydroxyl group, a C 1-4 alkyl group or a C 1-4 alkoxy group, and a plurality of R ^29a may be the same as or different from each other.

Examples of the C 1-4 alkyl represented by R ^29a include methyl, ethyl, propyl, and butyl.

Examples of the alkoxy group having 1 to 4 carbon atoms represented by R ^29a include methoxy, ethoxy, propoxy, and tert-butoxy.

R ^29a is preferably a hydroxyl group or an alkoxy group having 1 to 4 carbon atoms, more preferably an alkoxy group having 1 to 4 carbon atoms, further preferably a methyl group, an ethyl group, a methoxy group, an ethoxy group, and particularly preferably Methoxy or ethoxy.

Examples of the C 1-10 alkanediyl represented by R ^50a include methylene, ethylidene, trimethylene, tetramethylene, pentamethylene, hexamethylene, isopropylidene, Isobutylidene, 2-methyltrimethylene, isoamylidene, isohexylidene, isooctylidene, 2-ethylidenehexyl, etc., among which the C1-C6 alkanediyl group is preferred, and the carbon number is more preferred 1~4 alkanediyl.

The methylene group (-CH ₂ -) constituting the alkanediyl group represented by R ^50a may be replaced by -O-, -CO-, -NR ^11a -, -OCO-, -COO-, -OCONH-, -NHCOO- , -CONH- or -NHCO- is replaced under the condition that the oxygen atoms are not adjacent.

Examples of the group represented by formula (i) include groups represented by the following formulas (i-1) to (i-24).

【Chemical Formula 89】

Examples of the group in which the methylene group (-CH ₂ -) constituting R ^50a in the formula (i) is replaced by -O- include, for example, groups shown below (* indicates a bonding end).

Examples of the group in which the methylene group (-CH ₂ -) constituting R ^50a in the formula (i) is replaced with -CO- include the groups shown below (* indicates a bonding end).

【Chemical Formula 92】

Examples of the group in which methylene (-CH ₂ -) constituting R ^50a is replaced by -NR ^11a -in formula (i) include, for example, groups shown below (* represents a bonding end).

【Chemical Formula 95】

Examples of the group in which the methylene group (-CH ₂ -) constituting R ^50a in the formula (i) is replaced by -OCO- include, for example, groups shown below (* represents a bonding end).

Examples of the group in which the methylene group (-CH ₂ -) constituting R ^50a in the formula (i) is replaced by -COO- include, for example, the groups shown below (* indicates a bonding end).

Examples of the group in which the methylene group (-CH ₂ -) constituting R ^50a in the formula (i) is replaced by -OCONH- include, for example, the groups shown below (* represents a bonding end).

Examples of the group in which the methylene group (-CH ₂ -) constituting R ^50a in the formula (i) is replaced by -NHCOO- include, for example, the groups shown below (* indicates a bonding end).

【Chemical Formula 102】

Examples of the group in which the methylene group (-CH ₂ -) constituting R ^50a in the formula (i) is replaced by -CONH- include, for example, the groups shown below (* represents a bonding end).

Examples of the group in which the methylene group (-CH ₂ -) constituting R ^50a in the formula (i) is replaced by -NHCO- include, for example, groups shown below (* indicates a bonding end).

【Chemical Formula 106】

When the compound (1a) has a substituent represented by the formula (i), as the formula (i), R ^29a is preferably a substituent of a hydroxyl group or a C 1-4 alkoxy group, and more preferably R ^29a is a hydroxyl group Or a C1-C4 alkoxy group and ^R50a are a C1-C10 alkanediyl substituent, More preferably, it is a substituent represented by the following formula (ii).

In formula (ii), n represents an integer of 1 to 8, R ^12a represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and a plurality of OR ^12a may be the same as or different from each other.

* Indicates a bonding end with a nitrogen atom.

n is preferably 1 to 6, more preferably 1 to 5, and still more preferably 1 to 4.

Examples of the C 1-4 alkyl represented by R ^12a include methyl, ethyl, propyl, and butyl.

R ^12a is preferably a hydrogen atom, methyl, ethyl, or propyl, and more preferably a hydrogen atom, methyl, or ethyl.

Examples of the group represented by formula (ii) include groups represented by the following formulas (ii-1) to (ii-12). As the group represented by the formula (ii), a group represented by the formula (ii-2), a group represented by the formula (ii-3), a group represented by the formula (ii-5), and a formula The group represented by (ii-6) is more preferably a group represented by formula (ii-3).

Examples of preferred compounds of the xanthene dye (1a) include compounds represented by the following formulae (I-1) to (I-170). In the formula, R ^40a represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, preferably a branched chain alkyl group having 6 to 12 carbon atoms, and more preferably 2-ethylhexyl group.

Among them, as the xanthene dye (1a), more preferably, for example, there is one substituent represented by formula (i) in R ^1a to R ^4a and the remaining groups are carbon numbers 1 to which may have a substituent 20 monovalent saturated hydrocarbon-based compounds (for example, compounds (I-1) to (I-4), (I-13) to (I-16), (I-25) to (I-28), ( I-37) ~ (I- 40), (I-55) ~ (I-110), (I-117), (I-120) , etc.), R ^1a ~ R ^4a in the presence of 2 represented by the formula (i ) Represents the substituent and the remaining group is a compound having a C 1-20 monovalent saturated hydrocarbon group which may have a substituent (for example, compound (I-49) to (I-54), compound (I-111 )~(I-116), compounds (I-119), (I-121), (I-122), compounds having two xylyl groups in R ^1a to R ^4a (for example, compound (I-124 ) ~ (I-146), (I-151), (I-153), (I-155), (I-156), etc.), compounds having 2 tolyl groups in R ^1a ~ R ^4a (e.g. , Compounds (I-147), (I-150), (I-152), (I-154), etc.), R ^1a to R ^{4a are} all monovalent saturated with 1 to 20 carbon atoms which may have a substituent Hydrocarbon-based compounds (for example, compounds (I-160) to (I-170), etc.).

More preferably, it is compound (I-1)~(I-4), (I-13)~(I-16), (I-25)~(I-28), (I-124)~(I -147), (I-150)~(I-156), (I-160)~(I-167), (I-50), (I-51), (I-53), (I-54 ), (I-119), (I-121), (I-122).

【Chemical Formula 110】

【Chemical Formula 111】

【Chemical Formula 112】

【Chemical Formula 113】

【Chemical Formula 114】

【Chemical Formula 115】

【Chemical Formula 116】

【Chemical Formula 117】

【Chemical Formula 118】

【Chemical Formula 119】

【Chemical Formula 120】

【Chemical Formula 123】

【Chemical Formula 124】

【Chemical Formula 125】

【Chemical Formula 126】

【Chemical Formula 130】

Xanthene dye (a) can use commercially available xanthene dye (e.g. For example, "Chugai Aminol Fast Pink R-H/C" manufactured by Chugai Chemicals Co., Ltd. and "Rhodamin 6G" manufactured by Taoka Chemical Industry Co., Ltd.). Alternatively, commercially available xanthene dye can be used as an initial raw material, and it can be synthesized by referring to Japanese Patent Application Publication No. 2010-32999.

Examples of such xanthene dyes (a) include CI Acid Red 51 (the description of CI Acid Red is omitted below, and only the description of the serial number is used. Others are also the same.), 52, 87, 92, 94, 289, 388, etc. CI acid red dyes; CI acid violet dyes such as CI acid violet 9, 30, 102; CI basic red 1 (Rhodamine 6G), 2, 3, 4, 8, 10 (Rhodamine B), 11 CI basic red dyes such as CI; CI basic violet dyes such as CI basic violet 10, 11, 25; CI solvent red dyes such as CI solvent red 218; CI mordant red dyes such as CI mordant red 27; CI reactive red CI reactive red dye such as 36 (Rose Red B); sulforhodamine G; xanthene dye described in Japanese Patent Application Laid-Open No. 2010-32999; and xanthene dye described in Patent No. 4492760; etc.

The ratio of xanthene dye (a) is, for example, 10 parts by mass or more, preferably 30 parts by mass or more, and may be 50 parts by mass or more with respect to 100 parts by mass of the coloring agent (A2) having a maximum absorption wavelength of 500 nm or more and 700 nm or less. Or more than 70 parts by mass. Furthermore, it may be 80 parts by mass or more, preferably 90 parts by mass or more, more preferably 95 parts by mass or more, and may be 100 parts by mass.

In addition, the total amount of the multiple methyl compound (A1) and the coloring agent (A2) having a maximum absorption wavelength of 500 nm to 700 nm is, for example, 80 parts by mass or more with respect to 100 parts by mass of the entire colorant (A). It is preferably 90 parts by mass or more, more preferably 95 parts by mass or more, and may be 100 parts by mass.

The maximum absorption wavelength of the colorant (A2) is preferably 580 nm or less, and more preferably 570 nm or less.

<Other colorants (b) from 500nm to 700nm and other colorants (A3)>

In the present invention, as a coloring agent (A2) having a maximum absorption wavelength of 500 nm or more and 700 nm or less, coloring agents other than the xanthene dye (a) (hereinafter referred to as other colorants of 500 nm or more and 700 nm or less) (b) ). Examples of other colorants (b) of 500 nm or more and 700 nm or less include tertiary methyl indolium compounds, tertiary methyl benzoxazolium compounds, tertiary methyl benzothiazolium compounds, and indolyl trimethylthiazoles. Trimethine cyanine pigments such as onium compounds; pentamethine cyanine pigments such as pentamethylene oxazolium compounds, pentamethylene thiazolium compounds; squaric acid pigments; methylimine pigments; azo pigments; Pyrrolomethylene pigment; azo metal complex: phthalocyanine pigment; naphthalocyanine pigment; porphyrin pigment; dipyrromethene metal chelate compound, etc.

In addition, in the present invention, a coloring agent other than the polymethine compound (A1) and the coloring agent (A2) having a maximum absorption wavelength of 500 nm or more and 700 nm or less (hereinafter referred to as other coloring agents (A3)) may also be used.

If the other coloring agents (b) and other coloring agents (A3) having a maximum absorption wavelength of 500 nm or more and 700 nm or less are divided into pigments and dyes and exemplified together, as described below. In the following examples, colorants with a maximum absorption wavelength of 500 nm to 700 nm are equivalent to the colorant (b), and colorants with a maximum absorption wavelength of less than 500 nm are equivalent to other colorants (A3).

Examples of pigments that can be used as other colorants (b) of 500 nm or more and 700 nm or less and other colorants (A3) include CI Pigment Yellow 1 (the description of CI Pigment Yellow is omitted below, and only the serial number is used.), 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 194, 214 and other yellow pigments; CI Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73 Orange pigments; CI Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 175, 176, 177, 180, 192, 209, 215, 216, 224, 242, 254, 255, Red pigments of 264, 265, etc.; CI pigment blue 15, 15:3, 15:4, 15:6, 60, 80, etc. blue pigment; CI pigment violet 1, 19, 23, 29, 32, 36, 38 Etc. purple pigment; CI pigment green 7, 36, 58 etc. green pigment; etc.

Dyes that can be used as other colorants (b) from 500 nm to 700 nm and other colorants (A3) include oil-soluble dyes, acid dyes, basic dyes, direct dyes, mordant dyes, amine salts of acid dyes, Dyes such as sulfonamide derivatives of acid dyes include, for example, compounds classified as dyes in the color index (published by The Society of Dyers and Colourists), and well-known dyes described in Dyeing Notes (Dyeing Corporation). In addition, according to the chemical structure, azo dye, cyanine dye, triphenylmethane dye, xanthene dye, phthalocyanine dye, naphthoquinone dye, quinone dye Amine dye, methine dye, methyleneamine dye, squaric acid dye, acridine dye, styryl dye, coumarin dye, quinoline dye and nitro dye, etc. Among these, organic solvent-soluble dyes are preferred.

Specifically, CI Solvent Yellow 4, 14, 15, 23, 24, 38, 62, 63, 68, 82, 94, 98, 99, 162; CI Solvent Red 45, 49, 125, 130; CI Solvent Orange 2, 7, 11, 15, 26, 56; CI Solvent Blue 4, 5, 37, 67, 70, 90; CI Solvent Green 1, 4, 5, 7, 34, 35, etc. CI Solvent Dye, CI 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; CI Acid Red 1, 4 , 8, 14, 17, 18, 26, 27, 29, 31, 34, 35, 37, 42, 44, 50, 57, 66, 73, 88, 91, 97, 103, 111, 114, 129, 133 , 134, 138, 143, 145, 150, 151, 158, 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 ; CI Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 169, 173; CI Acid Violet 6B, 7, 17, 19; CI Acid Blue 1, 7, 9, 15, 18, 22, 29, 42, 59, 60, 62, 70, 72, 74, 82, 83, 86, 87, 90, 92, 93 , 100, 102, 103, 104, 113, 117, 120, 126, 130, 131, 142, 147, 151, 154, 158, 161, 166, 167, 168, 170, 171, 184, 187, 192, 199 , 210, 229, 234, 236, 242, 243, 256, 259, 267, 285, 296, 315, 335; CI Acid Green 1, 3, 5, 9, 16, 50, 58, 63, 65, 80, 104, 105, 106, 109 and other CI acid dyes, CI Direct Yellow 2, 33, 34, 35, 38, 39, 43, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129, 136, 138, 141; CI 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; CI Direct Orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107; CI Direct Violet 47, 52, 54, 59, 60, 65, 66 , 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104; CI Direct Blue 1, 2, 6, 8, 15, 15, 22, 25, 41, 57, 71, 76, 78, 80, 81, 84, 85, 86, 90, 93, 94, 95, 97, 98, 99, 100, 101, 106, 107, 108, 109, 113, 114, 115, 117, 119, 120, 137, 149, 150, 153, 155, 156, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 168, 170, 171, 172, 173, 188, 189, 190, 192, 193, 194, 195, 196, 198, 199, 200, 201, 202, 203, 207, 209, 210, 212, 213, 214, 222, 225, 226, 228, 229, 236, 237, 238, 242, 243, 244, 245, 246, 247, 248, 249, 250, 251, 252, 256, 257, 259, 260, 268, 274, 275, 293; CI Direct Green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 77, 79, 82, etc. CI disperse dyes such as CI disperse yellow 54, 76, CI basic blue 1, 3, 5, 7, 9, 19, 24, 25, 26, 28, 29, 40, 41, 54, 58, 59, 64, 65, 66, 67, 68; CI Basic Green 1; CI Basic Dyes, CI Reactive Yellow 2, 76, 116; CI Reactive Orange 16; CI Reactive Dyes, CI Mordant Yellow 5, 8, 10, etc. 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65; CI mordant red 1, 2, 4, 9, 12, 14, 17, 18, 19, 22, 23 , 24, 25, 26, 30, 32, 33, 36, 37, 38, 39, 41, 43, 45, 46, 48, 53, 56, 63, 71, 74, 85, 86, 88, 90, 94 , 95; CI mordant orange 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47, 48; CI mordant violet 1, 2, 4, 5, 7, 14, 22, 24, 30, 31, 32, 37, 40, 41, 44, 45, 47, 48, 53, 58; CI mordant blue 1, 2, 3, 7, 9, 12, 13, 15, 16, 19, 20, 21, 22, 26, 30 , 31, 39, 40, 41, 43, 44, 49, 53, 61, 74, 77, 83, 84; CI mordant green 1, 3, 4, 5, 10, 15, 26, 29, 33, 34, CI mordant dyes such as 35, 41, 43, 53, etc., CI vat dyes such as CI vat green 1, etc.

<dispersed processing>

When the solubility of the colorant (A) is low and the dispersibility is low, dispersion treatment may be performed. For example, the polymethyl compound (A1), the pigment may be subjected to rosin treatment if necessary, surface treatment using a pigment derivative into which an acidic group or a basic group has been introduced, and the use of a polymer compound on the surface of the colorant Grafting treatment, micronization treatment using sulfuric acid micronization method, etc., or cleaning treatment using organic solvent, water, etc. for removing impurities, ion removal method using ionic impurities, etc.

In addition, the coloring agent (A) may be prepared as a coloring agent dispersion liquid in advance, and then mixed with a resin (B), a polymerizable compound (C), a polymerization initiator (D), etc. to prepare a composition. In particular, the polymethine compound (A1) and the pigment are preferably dispersed in an organic solvent using a dispersant to prepare a dispersion liquid. The dispersion may contain only multiple methyl compounds (A1) or pigments as colorants, and multiple methyl compounds (A1) or pigments may be used with colorants (A2) and/or other that have a maximum absorption wavelength of 500 nm to 700 nm Contains the coloring agent (A3). The multiple methyl compound (A1) may be used alone or in combination of two or more.

The coloring agent (A) may be any of a polymethyl compound (A1) and a pigment, and the dispersing agent used for its dispersion may use various known pigment dispersing agents. The pigment dispersant may be any of a cationic, anionic, nonionic, and amphoteric dispersant, and examples include polyester-based, polyamine-based, and acrylic-based pigment dispersants.

(共榮社化學(株)製造)、

(

(株)製造)、EFKA(BASF社製造)、

(味之素

(株)製造)、Disperbyk(

社製造)等。 These pigment dispersants may be used alone or in combination of two or more. The pigment dispersant is represented by a trade name, and KP (made by Shin-Etsu Chemical Co., Ltd.),

(Made by Kyoeisha Chemical Co., Ltd.),

(

(Manufactured by a company), EFKA (manufactured by BASF),

(Ajinomoto

(Manufactured by a company), Disperbyk (

Co., Ltd.).

Preferred dispersants are (1) dispersants with amine value of 0 to 200 mgKOH/g (a), (2) dispersants with acid value of 0 to 200 mgKOH/g (b), or (3) amine value of 0 to Dispersant (c) with 200mgKOH/g and acid value of 0~200mgKOH/g.

The amine value of the dispersant (a) is preferably 1 mgKOH/g or more, more preferably 5 mgKOH/g or more, and further preferably 100 mgKOH/g or less, and more preferably 70 mgKOH/g or less.

The acid value of the dispersant (b) is preferably 1 mgKOH/g or more, more preferably 10 mgKOH/g or more, and further preferably 100 mgKOH/g or less, more preferably 50 mgKOH/g or less.

The amine value of the dispersant (c) is preferably 1 mgKOH/g or more, more preferably 5 mgKOH/g or more, and further preferably 100 mgKOH/g or less, and more preferably 70 mgKOH/g or less. The acid value of the dispersant (c) is preferably 1 mgKOH/g or more, more preferably 10 mgKOH/g or more, and further preferably 100 mgKOH/g or less, more preferably 50 mgKOH/g or less.

The amount of the dispersing agent is, for example, 10 parts by mass or more, preferably 20 parts by mass or more, and more preferably 30 parts by mass in terms of the solid content of the dispersing agent with respect to a total of 100 parts by mass of the multiple methyl compound (A1) and the pigment. The part or more is, for example, 100 parts by mass or less, preferably 90 parts by mass or less, and more preferably 80 parts by mass or less.

Examples of the organic solvent used in the preparation of the dispersion include ester solvents (solvents containing -COO- in the molecule and no -O-), and ether solvents (containing -O- in the molecule and -COO-free). Solvent), ether ester solvents (solvents containing -COO- and -O- in the molecule), ketone solvents (solvents containing -CO- in the molecule, and -COO- free), alcohol solvents (containing OH in the molecule , -O-, -CO- and -COO-free solvents), aromatic hydrocarbon solvents, amide solvents, halogenated alkyl solvents, dimethyl sulfoxide, etc.

Examples of the ester solvent include methyl lactate, ethyl lactate, butyl lactate, 2-hydroxyisobutyric acid methyl ester, ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, and isoamyl acetate. Butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexyl Alcohol acetate, γ-butyrolactone, etc.

Examples of ether solvents include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, and diethylene glycol mono Ethyl 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, tetrahydropyran, 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, phenethyl ether, methyl anisole, etc.

Examples of ether ester solvents include methyl methoxyacetate, ethyl methoxyacetate, methoxybutyl acetate, methyl ethoxyacetate, ethyl ethoxyacetate, and methyl 3-methoxypropionate Ester, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate Ester, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, 2-ethyl Carboxylic acid monoalkoxyalkyl esters such as oxy-2-methylpropionic acid ethyl ester, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, etc. ; Propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, Alkylene glycol monoalkyl ether acetates such as diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, dipropylene glycol methyl ether acetate, etc., preferably propylene glycol monomethyl ether Alkyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, etc. The glycol monoalkyl ether acetate is more preferably propylene glycol monomethyl ether acetate.

Examples of ketone solvents include diacetone alcohol (4-hydroxy-4-methyl-2-pentanone), acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, and 4-methyl The aliphatic alcohol having a ketone group such as 2-methyl-2-pentanone, cyclopentanone, cyclohexanone, and isophorone is preferably diacetone alcohol (4-hydroxy-4-methyl-2-pentanone).

Examples of alcohol solvents include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerin.

Examples of the aromatic hydrocarbon solvent include benzene, toluene, xylene, mesitylene and the like.

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

Examples of halogenated alkyl solvents include carbon tetrachloride, carbon tetrabromide, trichlorobromomethane, and chloroform.

Only one type of these solvents may be used, or a plurality of types may be used in combination. Among them, the use of ether ester solvents, ketone solvents, alcohol solvents, halogenated alkyl solvents or mixed solvents thereof is preferred, and the use of ether ester solvents, ketone solvents, halogenated alkyl solvents or mixed solvents thereof is more preferred.

A particularly preferred solvent must contain an ether ester solvent, such as alkylene glycol monoalkyl ether acetate, especially propylene glycol monomethyl ether acetate, the content of which is 100 parts by mass relative to the total amount of solvent, for example, is 40 parts by mass or more, preferably 50 parts by mass or more, and more preferably 60 parts by mass or more, for example, 99 parts by mass or less, preferably 95 parts by mass or less, more preferably 90 parts by mass or less.

The ratio of the solvent relative to 100 parts by mass of the entire colorant dispersion is, for example, 55 parts by mass or more, preferably 60 parts by mass or more, more preferably 65 parts by mass or more, for example, 99 parts by mass or less, preferably 95 parts by mass It is 90 parts by mass or less, more preferably 90 parts by mass or less.

<Colored curable resin composition>

For the colorant (A), leave it as it is or all or one After partially preparing a coloring agent dispersion liquid as needed, by mixing with the resin (B), the polymerizable compound (C), and the polymerization initiator (D), a colored curable resin composition can be obtained.

The amount of the colorant (A) is, for example, 10 parts by mass or more, preferably 20 parts by mass or more, and more preferably 30 parts by mass or more, for example, 60 parts by mass relative to 100 parts by mass of the total solid content of the colored curable resin composition. It is less than 50 parts by mass, preferably 50 parts by mass or less, and more preferably 45 parts by mass or less.

<Resin (B)>

The resin (B) is not particularly limited, but is preferably an alkali-soluble resin. The alkali-soluble resin (B) (hereinafter sometimes referred to as "resin (B)") contains at least one monomer (a) selected from the group consisting of unsaturated carboxylic acid and unsaturated carboxylic anhydride (hereinafter sometimes referred to as It is a copolymer of structural units of "(a)").

The resin (B) is preferably a structural unit derived from a monomer (b) (hereinafter sometimes referred to as "(b)") having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond, and other structures Copolymer of units. Examples of other structural units include monomers (c) copolymerizable with monomers (a) (however, they are different from monomers (a) and monomers (b). Hereinafter, they are sometimes referred to as "(c)") Structural unit with a ethylenically unsaturated bond.

Specific examples of (a) include unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, o-, m-, and p-vinylbenzoic acid; and unsaturated dicarboxylic acids such as maleic 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 Bicyclic unsaturated containing carboxyl group Compounds; unsaturated dicarboxylic acid anhydrides such as maleic anhydride; unsaturated acrylic esters such as α-(hydroxymethyl)acrylic acid containing hydroxyl and carboxyl groups in the same molecule.

Among these, acrylic acid, methacrylic acid, maleic anhydride, etc. are preferable from the viewpoint of copolymerization reactivity and the solubility of the obtained resin in an alkaline aqueous solution.

Examples of (b) include a cyclic ether structure having 2 to 4 carbon atoms (for example, at least one selected from the group consisting of an ethylene oxide ring, an oxetane ring, and a tetrahydrofuran ring) and ethylenic Saturated bond polymerizable compound.

(b) It is preferably a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth)acryloyloxy group.

In addition, in this specification, "(meth)acrylic acid" means at least 1 sort(s) selected from the group consisting of acrylic acid and methacrylic acid. The descriptions of "(meth)acryloyl" and "(meth)acrylate" have the same meaning.

Examples of (b) include monomers (b1) having an epoxyethyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b1)"), oxetanyl groups and ethylenic unsaturation. A monomer (b2) of a bond (hereinafter sometimes referred to as "(b2)"), a monomer (b3) having a tetrahydrofuranyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b3)"), and the like.

Examples of (b1) include monomers (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized (hereinafter sometimes referred to as "(b1-1)" ), a monomer (b1-2) having a structure in which an alicyclic unsaturated hydrocarbon is epoxidized (hereinafter sometimes referred to as "(b1-2)").

Examples of (b1-1) include: (meth)acrylic acid glycidol Ester, β-methyl glycidyl (meth)acrylate, β-ethyl glycidyl (meth)acrylate, glycidyl vinyl ether, o-vinyl benzyl glycidyl ether, m-vinyl benzyl Glycidyl ether, p-vinyl benzyl glycidyl ether, α-methyl-o-vinyl benzyl glycidyl ether, α-methyl-m-vinyl benzyl glycidyl ether, α-methyl- P-vinylbenzyl glycidyl ether, 2,3-bis(glycidoxymethyl)styrene, 2,4-bis(glycidoxymethyl)styrene, 2,5-bis(glycidyl) Oxymethyl)styrene, 2,6-bis(glycidoxymethyl)styrene, 2,3,4-tri(glycidoxymethyl)styrene, 2,3,5-tri( Glycidoxymethyl)styrene, 2,3,6-tris(glycidoxymethyl)styrene, 3,4,5-tris(glycidoxymethyl)styrene, 2,4, 6-Tris (glycidoxymethyl) styrene, etc.

Examples of (b1-2) include vinylcyclohexene monooxide, 1,2-epoxy-4-vinylcyclohexane (for example, Celloxide 2000; manufactured by Diacel Corporation), 3,4 -Epoxycyclohexylmethyl (meth)acrylate (for example, Cyclomer A400; manufactured by Diacel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (for example, Cyclomer M100; ) Manufactured by Diacel), the compound represented by formula (II), the compound represented by formula (III), and the like.

[Formula (II) and of formula (III), R ^a is and R ^b represents a hydrogen atom, or an alkyl group having 1 to 4 carbon atoms, the hydrogen atoms contained in the alkyl group may be substituted with a hydroxyl group.

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

R ^c represents a C1-C6 alkanediyl group.

* Indicates the bonding end with O. ]

Examples of the compound represented by formula (II) include compounds represented by any of formula (II-1) to formula (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) are preferred ), the compound represented by formula (II-1), formula (II-7), formula (II-9) or formula (II-15) is more preferable.

Examples of the compound represented by formula (III) include compounds represented by any of formula (III-1) to formula (III-15). Among them, the formula (III-1), Compounds represented by formula (III-3), formula (III-5), formula (III-7), formula (III-9) or formula (III-11) to formula (III-15) are more preferably formula (III III-1), the compound represented by the formula (III-7), the formula (III-9) or the formula (III-15).

The compound represented by the formula (II) and the compound represented by the formula (III) may be used alone, or the compound represented by the formula (II) and the compound represented by the formula (III) may be used in combination. When these are used together, the content ratio of the compound represented by the formula (II) and the compound represented by the formula (III) is preferably 5:95 to 95:5 on a molar basis, and more preferably 10:90 to 90: 10, more preferably 20:80 to 80:20.

Examples of (c) include methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, sec-butyl (meth)acrylate, and tert-butyl (meth)acrylate. Ester, 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 ]decane-8-yl (meth)acrylate (in this technical field Among them, as a common name, it is called "dicyclopentyl (meth)acrylate". In addition, it is sometimes called "tricyclodecyl (meth)acrylate".), tricyclic [5.2.1.0 ^2,6 ] Decene-8-yl (meth)acrylate (in this technical field, as a common name, it is called "dicyclopentenyl (meth)acrylate"), dicyclopentyloxy (meth)acrylate Ethyl ester, isobornyl (meth)acrylate, adamantyl (meth)acrylate, aryl (meth)acrylate, propargyl (meth)acrylate, phenyl (meth)acrylate, (meth) ) (Meth) acrylates such as naphthyl acrylate, benzyl (meth) acrylate; 2-hydroxyethyl (meth) acrylate, 2-hydroxy propyl (meth) acrylate, etc. Esters; dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate, itaconic acid diethyl ester; bicyclo[2.2.1]hept-2-ene, 5-methylbicyclo[2.2. 1]Hept-2-ene, 5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxybicyclo[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-ethoxy Bicyclo[2.2.1]hept-2-ene, 5,6-dihydroxybicyclo[2.2.1]hept-2-ene, 5,6-di(hydroxymethyl)bicyclo[2.2.1]hept-2- Ene, 5,6-bis(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5,6-dimethoxybicyclo[2.2.1]hept-2-ene, 5,6 -Diethoxybicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-ethylbicyclo[2.2.1 ]Hept-2-ene, 5-hydroxymethyl-5-methylbicyclo[2.2.1]hept-2-ene, 5-tert-butoxycarbonyl bicyclo[2.2.1]hept-2-ene, 5- Cyclohexyloxycarbonyl bicyclo[2.2.1]hept-2-ene, 5-phenoxycarbonyl bicyclo[2.2.1]hept-2-ene, 5,6-bis(tert-butoxycarbonyl)bicyclo[2.2 .1] Bicyclic unsaturated compounds such as hept-2-ene, 5,6-bis(cyclohexyloxycarbonyl) bicyclo[2.2.1]hept-2-ene; N-phenylmaleimide, N -Cyclohexylmaleimide, N-benzylmaleimide, N-succinimide-3 -Maleimide benzoate, N-succinimide-4-maleimide butyrate, N-succinimide-6-maleimide hexanoate, N -Succinimide-3-maleimide propionate, N-(9-acridinyl)maleimide and other dicarbonyl amide imine derivatives; styrene, α-methylbenzene Ethylene, m-methylstyrene, p-methylstyrene, vinyltoluene, p-methoxystyrene, acrylonitrile, methacrylonitrile, vinyl chloride, vinylidene chloride, propylene amide, methacryl amide , Vinyl acetate, 1,3-butadiene, isoprene, 2,3-dimethyl-1,3-butadiene, etc.

Among these, styrene, vinyl toluene, benzyl (meth)acrylate, tricyclo[5.2.1.0 ^2,6 ]decane-8-yl (methyl) are preferred from the viewpoint of copolymerization reactivity and heat resistance Acrylic ester, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo[2.2.1]hept-2-ene.

The structural unit having an ethylenically unsaturated bond is preferably a structural unit having a (meth)acryloyl group. The resin having such a structural unit can be obtained by allowing a monomer having an ethylenically unsaturated bond in a group that can react with a group having (a), (b) to have a structure derived from (a), (b) The polymer of the unit is obtained by addition.

Examples of such a structural unit include a structural unit in which glycidyl (meth)acrylate and (meth)acrylic acid unit are added, and a structure in which 2-hydroxyethyl (meth)acrylate and maleic anhydride unit are added Units, structural units in which (meth)acrylic acid and glycidyl (meth)acrylate units are added, etc. Also. When these structural units have a hydroxyl group, the structural unit to which carboxylic acid anhydride is further added can also be listed as a structural unit having an ethylenically unsaturated bond.

Specific examples of the resin (B) include: (meth)acrylic acid 3,4-epoxycyclohexyl methyl ester/(meth)acrylic acid copolymer, 3,4-epoxy tricyclo[5.2.1.0 ^2.6 ]Decyl (meth)acrylate/(meth)acrylic copolymer and other resins; glycidyl (meth)acrylate/benzyl (meth)acrylate/(meth)acrylic copolymer, (meth) Glycidyl acrylate/styrene/(meth)acrylic acid copolymer, 3,4-epoxy tricyclo[5.2.1.0 ^2.6 ]decyl(meth)acrylate/(meth)acrylic acid/N-cyclohexyl Laimide copolymer, 3,4-epoxy tricyclo[5.2.1.0 ^2.6 ]decyl(meth)acrylate/(meth)acrylic acid/vinyltoluene copolymer, 3-methyl-3-( Resin such as meth)acryloyloxymethyloxetane/(meth)acrylic acid/styrene copolymer; benzyl (meth)acrylate/(meth)acrylic acid copolymer, styrene/(methyl )Acrylic acid copolymer, benzyl (meth)acrylate/tricyclodecyl (meth)acrylate/(meth)acrylic acid copolymer resin; make glycidyl (meth)acrylate and benzyl (meth)acrylate /Addition of (meth)acrylic acid copolymer, addition of glycidyl (meth)acrylate and tricyclodecyl (meth)acrylate/styrene/(meth)acrylic acid copolymer Resins, resins such as resins obtained by adding glycidyl (meth)acrylate and tricyclodecyl (meth)acrylate/benzyl (meth)acrylate/(meth)acrylic acid copolymer; )Acrylic acid and tricyclodecyl (meth) acrylate/glycidyl (meth) acrylate copolymer reaction resin, (meth) acrylic acid and (meth) acrylic tricyclodecyl/styrene/ Resin and other resins obtained by reacting a copolymer of glycidyl (meth)acrylate; reacting a copolymer of (meth)acrylic acid with tricyclodecyl (meth)acrylate/glycidyl (meth)acrylate, and then Resins such as resins obtained by reacting tetrahydrophthalic anhydride with the obtained resin.

The polystyrene-equivalent weight average molecular weight of the resin (B) is preferably 3,000 to 100,000, more preferably 5,000 to 50,000, and still more preferably 5,000 to 30,000. If the molecular weight is in the above range, the hardness of the coating film will increase, the residual film rate will also be high, the solubility of the unexposed portion in the developer will be good, and the resolution of the colored pattern will tend to increase.

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

The acid value (solid content) of the resin (B) is preferably 50 to 170 mg-KOH/g, more preferably 60 to 150 mg-KOH/g, and still more preferably 70 to 135 mg-KOH/g. 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 determined by, for example, titration using an aqueous potassium hydroxide solution.

The content of the resin (B) is preferably 7 to 65 parts by mass, more preferably 13 to 60 parts by mass, and still more preferably 17 to 55 parts by mass relative to 100 parts by mass of the total solid content of the colored curable resin composition. If the content of the resin (B) is within the above range, a colored pattern can be formed, and the resolution and the residual film rate of the colored pattern tend to increase.

<Polymerizable compound (C)>

The polymerizable compound (C) is a compound that can be polymerized using the active radical and/or acid generated by the polymerization initiator (D), and examples thereof include 1, 2, or 3 or more polymerizable olefins. The unsaturated bond compound and the like are preferably (meth)acrylate compounds.

Examples of the polymerizable compound having one ethylenically unsaturated bond include nonylphenyl carbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, and 2-ethylhexyl carbitol acrylate Ester, 2-hydroxyethyl acrylate, N-vinylpyrrolidone, etc. and the above (a), (b) and (c).

Examples of the polymerizable compound having two ethylenically unsaturated bonds include 1,6-hexanediol di(meth)acrylate, ethylene glycol di(meth)acrylate, and neopentyl glycol di(meth)acrylate. Meth)acrylate, triethylene glycol di(meth)acrylate, bis(acryloxyethyl) ether of bisphenol A, 3-methylpentanediol di(meth)acrylate, etc.

Among them, the polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds. Examples of such a polymerizable compound include trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, and dipentaerythritol penta(methyl). Acrylate, dipentaerythritol hexa(meth)acrylate, tripentaerythritol octa(meth)acrylate, tripentaerythritol hexa(meth)acrylate, tetrapentaerythritol deca(meth)acrylate, four season pentaerythritol hexa(meth)acrylate Acrylic ester, tris(2-(meth)acryloyloxyethyl) isocyanurate, ethylene glycol modified pentaerythritol tetra(meth)acrylate, ethylene glycol modified dipentaerythritol hexa(methyl) Acrylate, propylene glycol modified pentaerythritol tetra (meth) acrylate, propylene Diol-modified dipentaerythritol hexa(meth)acrylate, caprolactone-modified pentaerythritol tetra(meth)acrylate, caprolactone-modified dipentaerythritol hexa(meth)acrylate, etc. Among them, preferred is dipentaerythritol penta (Meth)acrylate and dipentaerythritol hexa(meth)acrylate.

The weight average molecular weight of the polymerizable compound (C) is preferably 150 or more and 2,900 or less, and more preferably 250 or more and 1,500 or less.

The content of the polymerizable compound (C) is preferably 7 to 65 parts by mass, more preferably 13 to 60 parts by mass, and still more preferably 15 to 55 parts by mass relative to 100 parts by mass of the total solid content of the colored curable resin composition. .

The content ratio of the resin (B) and the polymerizable compound (C) [resin (B): polymerizable compound (C)] is preferably 20:80 to 80:20 on a mass basis, and more preferably 35:65 to 80: 20.

If the content of the polymerizable compound (C) is within the above-mentioned range, there is a tendency that the residual film rate during the formation of the colored pattern and the chemical resistance of the color filter are improved.

<polymerization initiator (D)>

The polymerization initiator (D) is not particularly limited as long as it can generate active radicals, acids, etc. to initiate polymerization by the action of light and heat, and a known polymerization initiator can be used.

Examples of the polymerization initiator (D) include O-acyl oxime compounds, alkyl phenyl ketone compounds, biimidazole compounds, triazine compounds, and acyl phosphine oxide compounds.

Examples of the O-acyl oxime compound include N-benzyloxy-1-(4-phenylsulfanylphenyl)butane-1-one-2-imine and N-benzoyl Oxygen Yl-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine, N-benzyloxy-1-(4-phenylsulfanylphenyl)-3 -Cyclopentylpropane-1-one-2-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzyl)-9H-carbazole-3- Yl]ethane-1-imine, N-acetoxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethyl-2,4-diox Heterocyclopentylmethoxy)benzyl}-9H-carbazol-3-yl]ethane-1-imine, N-acetoxy-1-[9-ethyl-6-(2 -Methylbenzyl)-9H-carbazol-3-yl]-3-cyclopentylpropane-1-imine, N-benzyloxy-1-[9-ethyl-6-( 2-methylbenzyl)-9H-carbazol-3-yl]-3-cyclopentylpropane-1-one-2-imine and the like. Commercial products such as Irgacure OXE01, OXE02 (above manufactured by BASF), N-1919 (made by ADEKA) can also be used. Among them, the O-acyl oxime compound is preferably selected from N-benzyloxy-1-(4-phenylsulfanylphenyl)butane-1-one-2-imine, N-benzyloxy Yl-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine and N-benzyloxy-1-(4-phenylsulfanylphenyl)-3 -At least one member of the group consisting of -cyclopentylpropane-1-one-2-imine, more preferably N-benzyloxy-1-(4-phenylsulfanylphenyl)octane-1 -Keto-2-imine. In the case of these O-acyl oxime compounds, a high-clarity color filter tends to be obtained.

Examples of the alkylphenyl ketone compounds include 2-methyl-2-morpholino-1-(4-methylsulfanylphenyl)propane-1-one and 2-dimethylamino -1-(4-morpholinophenyl)-2-benzylbutane-1-one, 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1 -[4-(4-morpholinyl)phenyl]butane-1-one and the like. Commercial products such as Irgacure 369, 907, and 379 (above are manufactured by BASF Corporation) can be used.

Examples include: 2-hydroxy-2-methyl-1-phenylpropane-1-one, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy)phenyl]propane- 1-ketone, 1-hydroxycyclohexylphenyl ketone, 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propane-1-one Oligomers, α,α-diethoxyacetophenone, benzoyl dimethyl ketal, etc.

As the biimidazole compound, there may be mentioned: 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3- Dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole (for example, refer to Japanese Patent Laid-Open No. 6-75372, Japanese Patent Laid-Open No. 6-75373, etc.), 2,2' -Bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'- Tetrakis(alkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetrakis(dialkoxyphenyl)biimidazole, 2,2 '-Bis(2-chlorophenyl)-4,4',5,5'-tetra(trialkoxyphenyl)biimidazole (for example, see Japanese Patent Publication No. 48-38403, Japanese Patent Publication No. 62 -174204, etc.), an imidazole compound in which a phenyl group in 4,4',5,5'-position is substituted with an alkoxycarbonyl group (for example, refer to Japanese Patent Laid-Open No. 7-10913, etc.), etc. Among them, compounds represented by the following formula and mixtures thereof are preferred.

Examples of the triazine compound include 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine and 2,4-bis(tris Chloromethyl)-6-(4-methoxynaphthyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5-tri Azine, 2,4-bis(trichloromethyl)-6-(4-methoxystyryl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6- [2-(5-methylfuran-2-yl)vinyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl )Vinyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl)vinyl] -1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl) Vinyl]-1,3,5-triazine, etc.

Examples of the above-mentioned acylphosphine oxide compound include 2,4,6-trimethylbenzyldiphenylphosphine oxide and the like.

Furthermore, 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; diphenyl Methone, methyl phthalate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, 3,3',4,4'- Benzophenone compounds such as tetra(tert-butylperoxycarbonyl)benzophenone, 2,4,6-trimethylbenzophenone; 9,10-phenanthrenequinone, 2-ethylanthraquinone, camphorquinone Other quinone compounds; 10-butyl-2-chloroacridone, benzoyl, methyl phenylglyoxylate, titanocene compounds, etc.

These polymerization initiators are preferably used in combination with a polymerization initiation aid (D1) (especially amines) described later.

The polymerization initiator (D) is preferably a polymerization initiator containing at least one selected from the group consisting of alkyl phenyl ketone compounds, triazine compounds, acylphosphine oxide compounds, O-acyloxime compounds and biimidazole compounds It is more preferably a polymerization initiator containing an O-acyl oxime compound.

The content of the polymerization initiator (D) is preferably 0.01 to 40 parts by mass, more preferably 0.05 to 35 parts by mass, and still more preferably 0.1 to the total amount of 100 parts by mass of the resin (B) and the polymerizable compound (C). 32 parts by mass, more preferably 1 to 30 parts by mass.

<Polymerization Initiator (D1)>

The colored curable resin composition may contain a polymerization initiator (D1) if necessary. The polymerization initiator (D1) is used to promote the polymerization initiated by the polymerization initiator Polymerized compound, or sensitizer. When the polymerization initiator (D1) is contained, it is usually used in combination with the polymerization initiator (D).

Examples of the polymerization initiator (D1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds, and carboxylic acid compounds.

Examples of the amine compound include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, and 4-diethylaminobenzoate. Isoamyl methylaminobenzoate, 2-dimethylaminoethyl benzoate, 2-ethylhexyl 4-dimethylaminobenzoate, N,N-dimethyl p-toluidine, 4 ,4'-bis(dimethylamino)benzophenone (commonly known as Michinone), 4,4'-bis(diethylamino)benzophenone, 4,4'-bis(ethyl Among them, methylamino) benzophenone and the like, among which 4,4′-bis(diethylamino)benzophenone is preferred. Commercial products such as EAB-F (Hodogaya Chemical Industry Co., Ltd.) can also be used.

Examples of the alkoxyanthracene compounds include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, and 2-ethyl Base-9,10-diethoxyanthracene, 9,10-dibutoxyanthracene, 2-ethyl-9,10-dibutoxyanthracene, etc.

Examples of the above thioxanthone compounds include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, 1-chloro-4-propoxythioxanthone, etc.

Examples of the carboxylic acid compound include phenylsulfanylacetic acid, methylphenylsulfanylacetic acid, ethylphenylsulfanylacetic acid, methylethylphenylsulfanylacetic acid, and dimethylbenzene Sulfanyl acetic acid, methoxyphenyl sulfanyl acetic acid, dimethoxyphenyl sulfanyl acetic acid, chlorophenyl sulfanyl acetic acid Acid, dichlorophenylsulfanylacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, naphthoxyacetic acid, etc.

When using these polymerization initiators (D1), the content is preferably 0.1 to 30 parts by mass, and more preferably 1 to 20 parts by mass relative to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). Copies. If the amount of the polymerization initiation aid (D1) is within this range, there is a tendency that the coloring pattern can be further formed with high sensitivity, and the productivity of the color filter is improved.

<Solvent (E)>

The colored curable resin composition usually contains a solvent (E). The solvent (E) is not particularly limited, and a solvent generally used in this field 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-), and ether ester solvents (containing in the molecule) -COO- and -O- solvents), ketone solvents (solvents containing -CO- in the molecule and not containing -COO-), alcohol solvents (molecules containing OH in the molecule and not containing -O-, -CO- and -COO -Solvent), aromatic hydrocarbon solvents, amide solvents, halogenated alkyl solvents, dimethyl sulfoxide, etc.

Examples of the ester solvent include methyl lactate, ethyl lactate, butyl lactate, 2-hydroxyisobutyric acid methyl ester, ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, and isopentyl acetate. Ester, 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 are preferably ethyl lactate.

Examples of ether solvents include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, and 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, tetrahydropyran, 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, phenethyl ether, methyl anisole, etc., preferably propylene glycol monomethyl ether, ethylene glycol Monomethyl ether, ethylene glycol monobutyl ether, 3-methoxy-1-butanol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether.

Examples of ether ester solvents include: methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, and 3-methoxypropyl Methyl acid ester, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, 2-methoxypropionate Ethyl acetate, 2-methoxypropionate propyl ester, 2-ethoxypropionate methyl ester, 2-ethoxypropionate ethyl ester, 2-methoxy-2-methylpropionate methyl ester, 2 -Ethyl ethoxy-2-methylpropionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, Propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate , Diethylene glycol monobutyl ether acetate, dipropylene glycol methyl ether acetate, etc., preferably 3-ethoxyethyl propionate, 3-methoxybutyl acetate, propylene glycol monomethyl ether Acetate.

Examples of ketone solvents include 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2 -Pentanone, cyclopentanone, cyclohexanone, isophorone, etc., preferably 4-hydroxy-4-methyl-2-pentan ketone.

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

Examples of the aromatic hydrocarbon solvent include benzene, toluene, xylene, mesitylene and the like.

Examples of the amide solvent include N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, etc., preferably N,N-dimethylformamide. .

Examples of the halogenated alkyl solvent include carbon tetrachloride, carbon tetrabromide, trichlorobromomethane, and chloroform, and chloroform is preferred.

These solvents may be used alone or in combination of two or more. Among them, the use of ether ester solvents, ketone solvents, halogenated alkyl solvents, or mixed solvents of these is more preferred. The ratio of the ether ester solvent is, for example, 30 to 90 parts by mass, and preferably 40 to 80 parts by mass with respect to a total of 100 parts by mass of all solvents. The ratio of the ketone solvent is, for example, 1 to 50 parts by mass, preferably 5 to 30 parts by mass relative to 100 parts by mass of the total solvent. In addition, the ratio of the halogenated alkyl solvent is, for example, 1 to 50 parts by mass, and preferably 5 to 30 parts by mass relative to 100 parts by mass of the total solvent.

The content of the solvent (E) is preferably 70 to 95% by mass relative to the total amount of the colored curable resin composition, and more preferably 75 to 92% by mass. In other words, the solid content of the colored curable resin composition is preferably 5 to 30% by mass, and more preferably 8 to 25% by mass. When the content of the solvent (E) is in the above range, the flatness during coating becomes good, and the color density is not insufficient when forming the color filter, so the display characteristics tend to be good.

<leveling agent (F)>

The colored curable resin composition may contain a leveling agent (F). Examples of the leveling agent (F) include silicone-based surfactants, fluorine-based surfactants, and silicone-based surfactants having fluorine atoms. These surfactants may have a polymerizable group in the side chain.

Examples of the silicone-based surfactant include surfactants having a siloxane bond in the molecule. Specific examples include Toray Silicone DC3PA, Toray Silicone SH7PA, Toray Silicone DC11PA, Toray Silicone SH21PA, Toray Silicone SH28PA, Toray Silicone SH29PA, Toray Silicone SH30PA, Toray Silicone SH8400 (trade name: manufactured by Toray Dow Corning 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 (made by Momentive Performance Materials Japan contract company) )Wait.

Examples of the above-mentioned fluorine-based surfactants include surfactants having a fluorocarbon chain in the molecule. Specifically, Fluorad (registered trademark) FC430, Fluorad FC431 (made by Sumitomo 3M Co., Ltd.), Megafac (registered trademark) F142D, Megafac F171, Megafac F172, Megafac F173, Megafac F177, Megafac F183, Megafac F554 , Megafac R30, Megafac RS-718-K (manufactured by DIC Corporation), EFTOP (registered trademark) EF301, EFTOP EF303, EFTOP EF351, EFTOP EF352 (manufactured by Mitsubishi Materials Electronics Co., Ltd.), Surflon (registered trademark) S381 , Surflon S382, Surflon SC101, Surflon SC105 (Xu Nitra (manufactured by Co., Ltd.) and E5844 (manufactured by Daikin Fine Chemical Co., Ltd.), etc.

Examples of the above-mentioned organic silicon-based surfactant having a fluorine atom include surfactants having a siloxane bond and a fluorocarbon chain in the molecule. Specifically, Megafac (registered trademark) R08, Megafac BL20, Megafac F475, Megafac F477, Megafac F443 (manufactured by DIC Corporation) and the like can be mentioned.

When the leveling agent (F) is contained, its content relative to the total amount of the colored curable resin composition is preferably 0.001% by mass or more and 0.2% by mass or less, and more preferably 0.002% by mass or more and 0.1% by mass or less It is more preferably 0.005 mass% or more and 0.07 mass% or less. If the content of the leveling agent (F) is within the above range, the flatness of the color filter can be improved.

<Antioxidant (G)>

From the viewpoint of improving the heat resistance and light resistance of the colorant, it is preferable to use the antioxidant alone or in combination of two or more kinds. The antioxidant is not particularly limited as long as it is an industrially generally used antioxidant, and phenol-based antioxidants, phosphorus-based antioxidants, sulfur-based antioxidants, and the like can be used.

1010(Irganox 1010：季戊四醇四[3-(3,5-二-叔-丁基-4-羥基苯基)丙酸酯]、BASF(株)製)、

1076(Irganox 1076：十八烷基-3-(3,5-二-叔-丁基-4-羥基苯基)丙酸酯、BASF(株)製)、

1330(Irganox 1330：3,3’,3”,5,5’,5”-六-叔-丁基-a,a’,a”-(均三甲苯-2,4,6-三基)三-對-甲酚、BASF(株)製)、

3114 (Irganox 3114：1,3,5-三(3,5-二-叔-丁基-4-羥基苄基)-1,3,5-三嗪-2,4,6(1H,3H,5H)-三酮、BASF(株)製)、

3790(Irganox 3790：1,3,5-三((4-叔-丁基-3-羥基-2,6-二甲苯基)甲基)-1,3,5-三嗪-2,4,6(1H,3H,5H)-三酮、BASF(株)製)、

1035(Irganox 1035：硫代二伸乙基雙[3-(3,5-二-叔-丁基-4-羥基苯基)丙酸酯]、BASF(株)製)、

1135(Irganox 1135：苯丙酸、3,5-雙(1,1-二甲基乙基)-4-羥基、C7-C9側鏈烷基酯、BASF(株)製)、

1520L(Irganox 1520L：4,6-雙(辛硫基甲基)-鄰-甲酚、BASF(株)製)、

3125(Irganox 3125、BASF(株)製)、

565(Irganox 565：2,4-雙(正-辛硫基)-6-(4-羥基3’,5’-二-叔-丁基苯胺基)-1,3,5-三嗪、BASF(株)製)、

AO-80(

AO-80：3,9-雙(2-(3-(3-叔-丁基-4-羥基-5-甲基苯基)丙醯氧基)-1,1-二甲基乙基)-2,4,8,10-四氧雜螺(5,5)十一烷、(株)ADEKA製)、

BHT(Sumilizer BHT、住友化學(株)製)、

GA-80(Sumilizer GA-80、住友化學(株)製)、

GS(Sumilizer GS、住友化學(株)製)、

1790(Cyanox 1790、(株)

製)及維生素E(

(株)製)等。 Examples of the phenolic antioxidants include

1010 (Irganox 1010: pentaerythritol tetra[3-(3,5-di-tert-butyl-4-hydroxyphenyl) propionate], manufactured by BASF Co., Ltd.),

1076 (Irganox 1076: octadecyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl) propionate, manufactured by BASF Co., Ltd.),

1330 (Irganox 1330: 3,3',3",5,5',5"-hexa-tert-butyl-a,a',a"-(mesitylene-2,4,6-triyl) Tri-p-cresol, manufactured by BASF Co., Ltd.),

3114 (Irganox 3114: 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)-1,3,5-triazine-2,4,6(1H,3H, 5H)-Trione, manufactured by BASF Co., Ltd.,

3790 (Irganox 3790: 1,3,5-tris((4-tert-butyl-3-hydroxy-2,6-xylyl)methyl)-1,3,5-triazine-2,4, 6(1H,3H,5H)-trione, manufactured by BASF Co., Ltd.,

1035 (Irganox 1035: thiodiethylidene bis[3-(3,5-di-tert-butyl-4-hydroxyphenyl) propionate], manufactured by BASF Co., Ltd.),

1135 (Irganox 1135: phenylpropionic acid, 3,5-bis(1,1-dimethylethyl)-4-hydroxyl, C7-C9 side chain alkyl ester, manufactured by BASF Co., Ltd.),

1520L (Irganox 1520L: 4,6-bis(octylthiomethyl)-o-cresol, manufactured by BASF Co., Ltd.),

3125 (Irganox 3125, manufactured by BASF Co., Ltd.),

565 (Irganox 565: 2,4-bis(n-octylthio)-6-(4-hydroxy3',5'-di-tert-butylanilino)-1,3,5-triazine, BASF Co., Ltd.),

AO-80(

AO-80: 3,9-bis(2-(3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propionyloxy)-1,1-dimethylethyl) -2,4,8,10-tetraoxaspiro (5,5) undecane, manufactured by ADEKA Co., Ltd.),

BHT (Sumilizer BHT, manufactured by Sumitomo Chemical Co., Ltd.),

GA-80 (Sumilizer GA-80, manufactured by Sumitomo Chemical Co., Ltd.),

GS (Sumilizer GS, Sumitomo Chemical Co., Ltd.),

1790 (Cyanox 1790, Co., Ltd.)

System) and vitamin E (

Co., Ltd. etc.

168(Irgafos 168：三(2,4-二-叔-丁基苯基)亞磷酸酯、BASF(株)製)、

12(Irgafos 12：三[2-[[2,4,8,10- 四-叔-丁基二苯并[d、f][1,3,2]二氧雜膦-6-基]氧]乙基]胺、BASF(株)製)、

38(Irgafos 38：雙(2,4-雙(1,1-二甲基乙基)-6-甲基苯基)乙基酯亞磷酸、BASF(株)製)、

329K((株)ADEKA製)、

PEP36((株)ADEKA製)、

PEP-8((株)ADEKA製)、Sandstab P-EPQ(

社製)、

618(Weston 618、GE社製)、

619G(Weston 619G、GE社製)、

626(Ultranox 626、GE社製)及

GP(Sumilizer GP：6-[3-(3-叔-丁基-4-羥基-5-甲基苯基)丙氧基]-2,4,8,10-四-叔-丁基二苯并[d,f][1.3.2]二氧雜磷雜環庚烯)(住友化學(株)製)等。 Examples of the phosphorus-based antioxidants include

168 (Irgafos 168: tris (2,4-di-tert-butylphenyl) phosphite, manufactured by BASF Co., Ltd.),

12(Irgafos 12: tri[2-[[2,4,8,10-tetra-tert-butyldibenzo[d, f][1,3,2]dioxaphosphine-6-yl]oxy ]Ethyl]amine, manufactured by BASF Co., Ltd.,

38 (Irgafos 38: bis(2,4-bis(1,1-dimethylethyl)-6-methylphenyl) ethyl ester phosphorous acid, manufactured by BASF Co., Ltd.),

329K (made by Adeka Co., Ltd.),

PEP36 (made by ADEKA Co., Ltd.),

PEP-8 (manufactured by ADEKA Corporation), Sandstab P-EPQ (

Social system),

618 (Weston 618, manufactured by GE),

619G (Weston 619G, manufactured by GE),

626 (Ultranox 626, manufactured by GE) and

GP (Sumilizer GP: 6-[3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propoxy]-2,4,8,10-tetra-tert-butyldiphenyl And [d, f] [1.3.2] dioxaphosphacycloheptene) (made by Sumitomo Chemical Co., Ltd.), etc.

Examples of the sulfur-based antioxidants include dialkylthiodipropionate compounds such as dilauryl thiodipropionate, dimyristyl, and distearyl, and tetrakis[methylene(3-decyl Dialkylthio) propionate] β-alkylmercaptopropionate compounds of polyols such as methane.

<other ingredients>

The color-curable resin composition of the present invention may contain additives known in the technical field such as fillers, other polymer compounds, adhesion promoters, light stabilizers, chain transfer agents, etc., as necessary.

<Manufacturing method of color filter>

As a method of producing a colored pattern from the color-curable resin composition of the present invention, a photolithography method, an inkjet method, a printing method, etc. may be mentioned. Among them, photolithography is preferred. The photolithography method is to coat the above colored curable resin composition A method of drying the substrate to form a coloring composition layer, exposing the coloring composition layer through a photomask and developing it. In the photolithography method, a colored coating film that is a cured product of the coloring composition layer can be formed by not using a photomask and/or not developing during exposure. The coloring pattern and colored coating film thus formed are the color filters of the present invention.

The film thickness of the manufactured color filter is not particularly limited, and can be appropriately adjusted according to the purpose, use, etc., and is usually 0.1 to 30 μm, preferably 0.1 to 20 μm, and more preferably 0.5 to 6 μm.

As the substrate, a glass plate, a resin plate, silicon, a substrate in which aluminum, silver, silver/copper/palladium alloy thin film, or the like is formed on the substrate can be used. Other color filter layers, resin layers, transistors, circuits, etc. may be formed on these substrates.

The formation of pixels of each color by the photolithography method can be performed by a known or conventional device and conditions. For example, it can be produced as follows.

First, the colored curable resin composition is applied on a substrate and dried by heating (pre-baking) and/or drying under reduced pressure, thereby removing volatile components such as a solvent and drying it to obtain a smooth coloring composition layer.

Examples of the coating method include a spin coating method, a slit coating method, a slit, and a spin coating method.

Next, the coloring composition layer is exposed via a photomask for forming a target coloring pattern.

In order to uniformly irradiate parallel light to the entire exposure surface or to perform accurate alignment of the photomask and the substrate on which the colored composition layer is formed, it is preferable to use an exposure device such as a mask aligner and a stepper.

The coloring composition layer after exposure is brought into contact with a developing solution to perform development, thereby forming a coloring pattern on the substrate. By development, the unexposed portion of the coloring composition layer is dissolved in the developer and removed. As the developing solution, for example, an aqueous solution of an alkaline compound such as potassium hydroxide, sodium bicarbonate, sodium carbonate, and tetramethylammonium hydroxide is preferable.

The development method may be any of a puddle method, a dipping method, a spray method, and the like. Furthermore, during development, the substrate can be tilted at an arbitrary angle.

After development, it is preferably washed with water.

Furthermore, it is preferable to post-bake the obtained coloring pattern.

By using the coloring curable resin composition of the present invention, a color filter with particularly high brightness can be manufactured. This color filter is useful as a color filter used in a display device (for example, liquid crystal display device, organic EL device, electronic paper, etc.) and a solid-state imaging element.

[Example]

Hereinafter, the present invention will be described more specifically by giving examples, but the present invention is of course not limited by the following examples, and of course it may be suitable before it can be adapted. The scope of the purpose described later is appropriately changed and implemented, and they are all included in the technical scope of the present invention.

(1) Multiple methyl compounds

Multiple methyl compound synthesis examples 1 to 54

Mix 0.01 mol of pseudoindole intermediate and 16 g of pyridine or acetonitrile, add 0.012 mol of acetic anhydride dropwise, and stir at room temperature to 50°C for 1 hour. Add 0.01 moles of active methylene compound and 0.02 moles of triethylamine at room temperature ~50 Stir at ℃ for 1~3 hours. The obtained solid was purified by refluxing with methanol, and the solid was dried at 120°C to obtain the target substance. The analysis results are shown in [Table 1] to [Table 6].

[Multiple methyl compound synthesis example 55] Production of compound No. 84 0.2 g of compound No. 31 and 20 g of ion-exchanged water were mixed, and a sodium hydroxide aqueous solution was added dropwise to homogenize the solution. An aqueous solution of 0.062 g of barium chloride dihydrate was charged therein, and stirred for 30 minutes. The obtained solid was filtered, washed with water, and dried to obtain 0.19 g of the target product (yield 82.5%).

[Multiple methyl compound synthesis example 56] Production of compound No. 85 The object 0.07 was obtained in the same manner as multiple methyl compound synthesis example 55 except that copper sulfate 5 hydrate was used instead of barium chloride dihydrate. g (yield 33.3%).

[Multiple methyl compound synthesis example 57] Preparation of compound No. 86 In addition to using compound No. 38 in place of compound No. 31, and using phosphotungstic acid instead of barium chloride 2 hydrate, it is compatible with multiple methyl compounds In Synthesis Example 55, 0.16 g of the target product was obtained in the same manner (yield: 60.0%).

[Coating Fluid Examples 1 to 6 and Comparative Coating Fluid Example 1]

Compound No. 1, No. 30, No. 31, No. 34, No. 40, No. 46 and Comparative Compound No. 1 were mixed with 0.4 g of 0.5 wt% acetone solution and polymethyl methacrylate (hereinafter also referred to as 3.0 g of a 25 wt% toluene solution of PMMA) was mixed, and ultrasonic irradiation was performed for 15 minutes to prepare a coating liquid.

【Chemical Formula 138】

The coating liquid obtained above was applied to a 188 μm thick polyethylene terephthalate film subjected to easy adhesion treatment using a bar coater #30, and then dried at 70° C. for 15 minutes to prepare Optical filter (film thickness 7~8μm).

[Evaluation Examples 1 to 6 and Comparative Evaluation Example 1]

試驗機(株)製

TS-2)照射光48小時，評價了耐光性。評價中，測定了光照射前後的各光學濾波器的吸收極大波長下的吸光度，將初期值(光照射前)設為100，算出光照射後的相對值(吸光度保持率)，比較了耐光性。將結果示於[表7]。 For the optical filters obtained in Coating Liquid Examples 1 to 6 and Comparative Coating Liquid Example 1, a xenon light resistance tester (

Test Machine Co., Ltd.

TS-2) The light resistance was evaluated by irradiating light for 48 hours. In the evaluation, the absorbance at the absorption maximum wavelength of each optical filter before and after light irradiation was measured, the initial value (before light irradiation) was set to 100, the relative value after light irradiation (absorbance retention ratio) was calculated, and the light resistance was compared . The results are shown in [Table 7].

As can be seen from [Table 7], the optical filters of Comparative Evaluation Example 1 are poor in light resistance, and the optical filters of Evaluation Examples 1 to 6 are excellent in light resistance.

(2) Colored curable resin composition

In each polymethyl compound obtained as described above, the following compound Nos. 1, 6, 19, 37, and 97 were used.

Colorant (A2): Synthetic example of xanthene dye (a)

50.0 parts of the compound represented by the formula (X-1) and 350 parts of isopropanol (manufactured by Wako Pure Chemical Industries, Ltd.) were mixed at room temperature, and diethylamine ( (Tokyo Chemical Industry Co., Ltd.) 18.1 parts, and it stirred at 20 degreeC for 3 hours. The reaction solution was poured into 2100 parts of 10% hydrochloric acid. The obtained precipitate was obtained as a residue of suction filtration, washed with 373 parts of ion-exchanged water, and then dried to obtain 23.6 parts of the compound represented by formula (X-2). The yield was 43%.

Identification of the compound represented by formula (X-2)

(Mass analysis) ionization mode=ESI+: m/z=[M+H]+442.1 exact mass: 441.1

5.0 parts of the compound represented by formula (X-2) and 35 parts of N-methylpyrrolidone (manufactured by Wako Pure Chemical Industries, Ltd.) were mixed at room temperature, and dipropylamine was added dropwise to the mixture at a temperature exceeding 20°C (Tokyo Chemical Industry Co., Ltd.) 3.4 parts, the temperature was raised to 80°C, and the mixture was stirred for 3 hours. After cooling the reaction liquid to room temperature, 3.4 parts of concentrated hydrochloric acid was added, and the resulting mixture was poured into 315 parts of saturated brine. The obtained precipitate was obtained as a residue of suction filtration, washed with 630 parts of ion-exchanged water, and then dried to obtain a formula represented by formula (I-161) Compound 3.9 parts. The yield was 69%.

Identification of the compound represented by formula (I-161)

(Mass analysis) ionization mode=ESI+: m/z=[M+H]+507.7 exact mass: 506.7

Determination of the absorbance of the compound represented by formula (1-161)

0.35g of the compound represented by the formula (1-161) was dissolved in chloroform, so that the volume becomes 250cm ^3, in which the 2cm ³ was diluted with chloroform, be 100cm ^3, prepared at a concentration 0.028g / L solution. For the solution, an ultraviolet-visible spectrophotometer (V-650DS; manufactured by Japan Spectroscopy Co., Ltd.) (quartz cell, optical path length; 1 cm) was used to measure the maximum absorption wavelength (λ _max ) and the maximum absorption wavelength (λ _max ). As a result of absorbance, the maximum absorption wavelength (λ _max ) was 549 nm, and the absorbance at the maximum absorption wavelength (λ _max ) was 6.06.

Resin (B) synthesis example

製)225份、乙烯基甲苯(異構體混合物)81份、1-甲氧基-2-丙基乙酸酯80份的混合溶液。另一方面，歷時5小時滴 入將聚合引發劑2,2-偶氮雙(2,4-二甲基戊腈)30份溶解於1-甲氧基-2-丙基乙酸酯160份中的溶液。引發劑溶液的滴入結束後，在同溫度下保持4小時，製備由下述式所示的結構單元組成的樹脂(B-1)。將反應液冷卻到室溫，用B型黏度(23℃)測定的黏度為246mPas。樹脂(B-1)溶液的固形分為37.5重量%，固形分換算的酸值為115mg-KOH/g。生成的樹脂(B-1)的重均分子量Mw(聚苯乙烯換算)為10600，分子量分佈[Mw/Mn]為2.01。 In a flask equipped with a reflux cooler, a dropping funnel, and a stirrer, an appropriate amount of nitrogen was passed through and replaced with a nitrogen atmosphere. 371 parts of 1-methoxy-2-propyl acetate was charged and heated to 85℃. Next, 54 parts of acrylic acid, a mixture of 3,4-epoxy tricyclo[5.2.1.0 ^2,6 ]decane-8 or/and 9-yl acrylate (trade name "E-DCPA", Corporation

A mixed solution of 225 parts, 81 parts of vinyl toluene (isomer mixture), and 80 parts of 1-methoxy-2-propyl acetate. On the other hand, 30 parts of 2,2-azobis(2,4-dimethylvaleronitrile), a polymerization initiator, was dissolved in 160 parts of 1-methoxy-2-propylacetate dropwise over 5 hours In the solution. After the dropping of the initiator solution was completed, it was kept at the same temperature for 4 hours to prepare a resin (B-1) composed of a structural unit represented by the following formula. The reaction solution was cooled to room temperature, and the viscosity measured with a B-type viscosity (23°C) was 246 mPas. The solid content of the resin (B-1) solution is 37.5% by weight, and the acid value in terms of solid content is 115 mg-KOH/g. The weight average molecular weight Mw (in terms of polystyrene) of the produced resin (B-1) was 10600, and the molecular weight distribution [Mw/Mn] was 2.01.

The polystyrene-equivalent weight average molecular weight (Mw) and number average molecular weight (Mn) of the resin are measured under the following conditions using the GPC method.

Device; HLC-8120GPC (manufactured by Tosoh Corporation)

Column; TSK-GELG2000HXL

Column temperature; 40℃

Solvent; THF

Flow rate; 1.0mL/min

Solid concentration of tested liquid; 0.001~0.01% by mass

Injection volume; 50μL

Detector; RI

Standard material for calibration; TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Corporation)

The ratio of the weight-average molecular weight and the number-average molecular weight (Mw/Mn) in terms of polystyrene obtained above was used as the molecular weight distribution.

Example 1

The following components were mixed to obtain a colored curable resin composition.

(註冊商標)OXE-01；BASF社製；O-醯基肟化合物) 12份；溶劑(E)：丙二醇單甲基醚乙酸酯 530份；溶劑(E)：4-羥基-4-甲基-2-戊酮 179份；溶劑(E)：三氯甲烷 179份；流平劑(F)：聚醚改性矽油(

SH8400；東麗道康寧(株)製)0.1份；抗氧化劑 3份 Multiple methyl compound (A1): Compound No. 19 25.5 parts; Multiple methyl compound (A1): Compound No. 6 10.6 parts; Colorant (A2): Xanthene dye (a): Formula (I-161 ) 6.4 parts of the compound shown; resin (B): resin B-1 (solid content conversion) 55 parts; polymerizable compound (C): dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; Nippon Kayaku Co., Ltd. )) 45 parts; polymerization initiator (D): N-benzyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine (

(Registered trademark) OXE-01; manufactured by BASF; O-acyl oxime compound) 12 parts; solvent (E): 530 parts of propylene glycol monomethyl ether acetate; solvent (E): 4-hydroxy-4-methyl Yl-2-pentanone 179 parts; solvent (E): chloroform 179 parts; leveling agent (F): polyether modified silicone oil (

SH8400; Toray Dow Corning Co., Ltd. 0.1 parts; antioxidant 3 parts

Comparative example 1

[Preparation of pigment dispersion liquid b1]

Colorant (A2): Other colorants from 500 nm to 700 nm (b): C.1. Pigment Red 254 (pigment) 21.1 parts; acrylic pigment dispersant 7.4 parts; resin (B): resin B-1 (Conversion of solid content) 10.7 parts; solvent (E): 156 parts of propylene glycol monomethyl ether acetate were mixed, and the pigment was sufficiently dispersed using a bead mill to obtain pigment dispersion liquid b1.

The maximum absorption wavelength (λ _max ) of the pigment dispersion liquid b1 in chloroform is 551 nm.

The following components were mixed to obtain a colored curable resin composition.

(註冊商標)OXE-01；BASF社製；O-醯基肟化合物)12份；溶劑(E)：丙二醇單甲基醚乙酸酯 281份；溶劑(E)：4-羥基-4-甲基-2-戊酮 250份； 流平劑(F)：聚醚改性矽油(

SH8400；東麗道康寧(株)製)0.1份；抗氧化劑 3份 Colorant (A2): 592 parts of pigment dispersion b1; colorant (A2): xanthene dye (a): 4.1 parts of compound represented by formula (1-161); resin (B): resin B-1 (solid form 22.8 parts; polymerizable compound (C): dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 45 parts; polymerization initiator (D): N-benzoyloxy Yl-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine (

(Registered trademark) OXE-01; manufactured by BASF; O-acyl oxime compound) 12 parts; solvent (E): 281 parts of propylene glycol monomethyl ether acetate; solvent (E): 4-hydroxy-4-methyl 250 parts of 2-methyl-2-pentanone; leveling agent (F): polyether modified silicone oil (

SH8400; Toray Dow Corning Co., Ltd. 0.1 parts; antioxidant 3 parts

<Production of color filter>

(株)製)在大氣氣氛下、以150mJ/cm²的曝光量(365nm基準)光照射。作為光掩模，使用了形成了100μm線和間隙圖案的光掩模。將光照射後的形成了著色組合物層的玻璃基板在包含非離子系表面活性劑0.12%和氫氧化鉀0.04%的水系顯影液中在24℃下浸漬顯影60秒，水洗後，在烘箱中、210℃下進行25分鐘後烘焙，得到了濾色器。 On a 5 cm square glass substrate (Eagle 2000; manufactured by Corning Incorporated), a colored curable resin composition was applied by a spin coating method, and prebaked at 100° C. for 3 minutes to form a colored composition layer. After cooling, the interval between the glass substrate on which the colored composition layer was formed and the photomask made of quartz glass was 100 μm, and an exposure machine (TME-150RSK;

(Manufactured by Co., Ltd.) Under an atmospheric atmosphere, light is irradiated at an exposure amount of 150 mJ/cm ² (365 nm standard). As the photomask, a photomask in which a 100 μm line and gap pattern was formed was used. The glass substrate on which the coloring composition layer was formed after light irradiation was immersed and developed in an aqueous developer containing 0.12% of nonionic surfactant and 0.04% of potassium hydroxide at 24°C for 60 seconds, after washing with water, in an oven After baking at 210°C for 25 minutes, a color filter was obtained.

<Measurement of film thickness>

For the obtained color filter, the film thickness was measured using a film thickness measuring device (DEKTAK3; manufactured by Japan Vacuum Technology Co., Ltd.). The results are shown in Table 8.

<colorimetric evaluation>

For the obtained color filter, the spectrometer was measured using a color measuring machine (OSP-SP-200; manufactured by Olympus Corporation), and the characteristic function of the C light source was used to measure the xy chromaticity coordinates in the XYZ color system of CIE (x, y) and tristimulus value Y. The larger the value of Y, the higher the brightness. Table 8 shows the results.

Example 2

[Preparation of pigment dispersion b2]

Colorant (A2): Other colorants from 500 nm to 700 nm (b): CI Pigment Red 242 (pigment) 23.4 parts; acrylic pigment dispersant 11.9 parts; resin (B): resin B-1 (solid content) (Conversion) 5.2 parts; solvent (E): 154 parts of propylene glycol monomethyl ether acetate were mixed, and the bead mill was used to disperse the pigment sufficiently to obtain pigment dispersion liquid b2.

The maximum absorption wavelength (λ _max ) of the pigment dispersion liquid b2 in chloroform is 502 nm.

[Preparation of pigment dispersion b3]

Colorant (A2): Other colorants from 500 nm to 700 nm (b): CI Pigment Red 177 (pigment) 21.5 parts; acrylic pigment dispersant 11.4 parts; resin (B): resin B-1 (solid content) (Conversion) 6.1 parts; solvent (E): 156 parts of propylene glycol monomethyl ether acetate were mixed, and the pigment was fully dispersed using a bead mill to obtain a pigment dispersion liquid b3.

The maximum absorption wavelength (λ _max ) of the pigment dispersion b3 in chloroform is 562 nm.

The following components were mixed to obtain a colored curable resin composition.

(註冊商標)OXE-01；BASF社製；O-醯基肟化合物) 8份；溶劑(E)：丙二醇單甲基醚乙酸酯 371份；溶劑(E)：4-羥基-4-甲基-2-戊酮 225份；流平劑(F)：聚醚改性矽油(

SH8400；東麗道康寧(株)製)0.1份 Multiple methyl compound (A1): 8.3 parts of compound No.1; colorant (A2): 173 parts of pigment dispersion liquid b2; colorant (A2): 490 parts of pigment dispersion liquid b3; resin (B): resin B- 1 (solid content conversion) 35 parts; polymerizable compound (C): dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 45 parts; polymerization initiator (D): N-benzene Methoxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine (

(Registered trademark) OXE-01; manufactured by BASF; O-acyl oxime compound) 8 parts; solvent (E): 371 parts of propylene glycol monomethyl ether acetate; solvent (E): 4-hydroxy-4-methyl 225 parts of 2-methyl-2-pentanone; leveling agent (F): polyether modified silicone oil (

SH8400; Toray Dow Corning Co., Ltd. 0.1 parts

Comparative example 2

The following components were mixed to obtain a colored curable resin composition.

(註冊商標)OXE-01；BASF社製；O-醯基肟化合物) 8份；溶劑(E)：丙二醇單甲基醚乙酸酯 315份；溶劑(E)：4-羥基-4-甲基-2-戊酮 260份；流平劑(F)：聚醚改性矽油(

SH8400；東麗道康寧(株)製)0.1份 Colorant (A2): 372 parts of pigment dispersion b2; Colorant (A2): 538 parts of pigment dispersion b3; Resin (B): 28.1 parts of resin B-1 (solid content conversion); Polymerizable compound (C): Dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 45 parts; polymerization initiator (D): N-benzyloxy-1-(4-phenylsulfanylbenzene Group) Octane-1-one-2-imine (

(Registered trademark) OXE-01; manufactured by BASF; O-acyl oxime compound) 8 parts; solvent (E): 315 parts of propylene glycol monomethyl ether acetate; solvent (E): 4-hydroxy-4-methyl 260 parts of 2-methyl-2-pentanone; leveling agent (F): polyether modified silicone oil (

SH8400; Toray Dow Corning Co., Ltd. 0.1 parts

The compositions of Example 2 and Comparative Example 2 were evaluated in the same manner as in Example 1 except that the post-baking temperature was changed to 230°C. The results are shown in Table 9.

Example 3 (Preparation of dispersion liquid)

社：DESPERBYK-2001(商品名)、酸值19mgKOH/g、胺值29mgKOH/g)17份、作為樹脂的樹脂(B-1)4份(固形分)、丙二醇單甲基醚乙酸酯158份、4-羥基-4-甲基-2-戊酮10份後，裝入0.4μm的氧化鋯珠粒600份，使用油漆調理器(Red Devil社製)振盪6小時，製作分散液X。 Weigh 10 parts of the multiple methyl compound of Compound No. 97, 1 part of the multiple methyl compound of Compound No. 37, and a dispersant solution (

Company: DESPERBYK-2001 (trade name), acid value 19 mgKOH/g, amine value 29 mgKOH/g) 17 parts, resin as resin (B-1) 4 parts (solid content), propylene glycol monomethyl ether acetate 158 Parts and 10 parts of 4-hydroxy-4-methyl-2-pentanone, 600 parts of 0.4 μm zirconia beads were charged, and shaken for 6 hours using a paint conditioner (manufactured by Red Devil) to prepare dispersion X.

This is the same as Comparative Example 1 except that the pigment dispersion liquid b1 of Comparative Example 1 is replaced with the dispersion liquid X. The color filter produced using the obtained coloring curable resin composition has high brightness compared with Comparative Example 1.

Claims (13)

A coloring curable resin composition comprising a colorant (A), a resin (B), a polymerizable compound (C), and a polymerization initiator (D), the colorant (A) comprising the formula (I) Compound (A1) and a coloring agent (A2) having a maximum absorption wavelength in chloroform of 500 nm or more and 700 nm or less, wherein the colorant (A2) is a xanthene dye, and the xanthene dye is represented by the following formula (1a) Means,

In the formula, R ¹ , R ² , R ³ , R ⁴ , R ⁶ , R ⁷ and R ⁸ each independently represent a hydrogen atom, a hydroxyl group, a nitro group, a cyano group, a halogen atom, a carboxyl group, a sulfonic acid group, and the number of carbon atoms 1-20 alkyl groups, aryl groups having 6-30 carbon atoms, arylalkyl groups having 7-30 carbon atoms, arylalkenyl groups having 8-30 carbon atoms, or containing 2-30 carbon atoms Heterocyclic group or metallocene group, R ⁵ represents hydrogen atom, alkyl group having 1 to 20 carbon atoms, aryl group having 6 to 30 carbon atoms, arylalkyl group having 7 to 30 carbon atoms, carbon atom 8 to 30 arylalkenyl groups, or 2 to 30 carbon atoms containing heterocyclic groups, R ⁹ represents a hydrogen atom, a C 1 to 20 alkyl group or a cyano group, X represents >CR ¹⁰ R ^11. Oxygen atom or sulfur atom, R ¹⁰ and R ¹¹ each independently represent an alkyl group having 1 to 20 carbon atoms, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , A methylene group in the alkyl group having 1 to 20 carbon atoms represented by R ⁹ , R ¹⁰ and R ¹¹ , and an arylalkyl group having 7 to 30 carbon atoms or an arylene having 8 to 30 carbon atoms The methylene group in the group is sometimes replaced by -O-, -S-, -CO-, -COO-, -OCO-, -COS-, -OCS-, -SO ₂ -, -NH-, -CONH-, -NHCO-, -SO ₂ NH-, -NH-SO ₂ -, -N=CH- or -CH=CH- are replaced under the condition that oxygen atoms are not adjacent, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ and R ¹¹ may have a branched side chain in the alkyl portion of the group represented by R ⁹ , may be a cyclic alkyl group, may have a substituent, R ¹ and R ² , R ² and R ³ , R ³ and R ⁴ , R ⁴ and R ⁵ , R ¹ and R ¹⁰ , R ⁶ and R ⁸ , R ⁸ and R ⁹ and R ¹⁰ and R ¹¹ may each be formed together Ring, the formed ring may have a substituent, G represents an oxygen atom, a sulfur atom or a group selected from the following <Group 1>, A is not a bonding end when m=1, and represents a single when m≧2 bond, a nitrogen atom, -NR ¹² -, oxygen atom, sulfur atom, -SO ₂ -, - SO-, a phosphorus ^{atom, -PR 13 -, E m +} (J -) m, (m +) m L m- or An organic group that satisfies any of the following conditions (i) to (v), E represents an m-valent cation, J represents a monovalent anion, M represents a monovalent cation, L represents an m-valent anion, R ¹² and R ¹³ each independently represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or an aryl group having 8 to 30 carbon atoms Alkenyl, alkyl, aryl, arylalkyl, and arylalkenyl represented by R ¹² and R ¹³ are sometimes The nitro group may have a substituent that forms a salt. The methylene group in the alkyl group, arylalkyl group, and arylalkenyl group represented by R ¹² and R ¹³ may be substituted by -COO-, -O-,- OCO-, -NHCO-, -NH-, and -CONH- are replaced under the condition that the oxygen atoms are not adjacent, m is 1~6, when m≧2, A and R ¹ , R ² , R ³ , R ⁴ , One or more substituents of R ⁵ , R ⁶ , R ⁷ , R ⁸ and R ⁹ are connected, and there are multiple R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ , R ⁹ , n, X and G can be the same or different, n is 0 or 1, <group 1>

In the formula, R and R'each independently represent an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or 8 to 30 carbon atoms The arylalkenyl group of * means that it is bonded to the adjacent group at the * part, (i) is m=2, and A is represented by the following formula (1),

In the formula, X ¹ represents -NR ¹⁴ -, a divalent aliphatic hydrocarbon group having 1 to 35 carbon atoms, a divalent alicyclic hydrocarbon group having 3 to 35 carbon atoms, and a divalent carbon atom having 6 to 35 carbon atoms. A hydrocarbon group containing an aromatic ring or a heterocyclic group containing 2 to 35 carbon atoms or a group represented by the following (1-A) to (1-C), Z ¹ and Z ² are each independently Represents direct bonding, -O-, -S-, -SO ₂ -, -SO-, -NR ¹⁴ -, -PR ¹⁵ -, -CO-, or a combination of these, and R ¹⁴ and R ¹⁵ each independently represent Hydrogen atom, alkyl group having 1 to 10 carbon atoms, aryl group having 6 to 30 carbon atoms, arylalkyl group having 7 to 30 carbon atoms, or arylalkenyl group having 8 to 30 carbon atoms, R ¹⁴ The alkyl group, aryl group, arylalkyl group, and arylalkenyl group represented by R ¹⁵ may also be substituted with a halogen atom, a hydroxyl group, or a nitro group. The alkyl group, arylalkyl group represented by R ¹⁴ and R ¹⁵ , And the methylene group in the arylalkenyl group can be replaced by -COO-, -O-, -OCO-, -NHCO-, -NH-, and -CONH- under the condition that the oxygen atom is not adjacent, * means that ＊Part is bound to the adjacent group, but the group represented by the above general formula (1) is in the range of 1 to 35 carbon atoms,

In the formula, R ²¹ represents a phenyl group which may be substituted with an alkyl group or an alkoxy group having 1 to 10 carbon atoms, or a cycloalkyl group having 3 to 10 carbon atoms, and R ²² represents an alkyl group having 1 to 10 carbon atoms. , An alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms or a halogen atom, and the alkyl group, alkoxy group and alkenyl group represented by R ²¹ and R ²² are substituted with halogen atoms or unsubstituted , D is an integer from 0 to 4, * means that the * part is bound to the adjacent group,

* In the formula means that the * part is bound to the adjacent group, [Chemical formula 6]

In the formula, R ²³ and R ²⁴ each independently represent an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, and one having 6 to 30 carbon atoms. Arylthio, arylalkyl having 7 to 30 carbon atoms, arylalkenyl having 8 to 30 carbon atoms, heterocyclic group or halogen atom having 2 to 30 carbon atoms, R ²³ and R ²⁴ The alkyl group, aryl group, aryloxy group, arylthio group, arylalkyl group, arylalkenyl group, and heterocyclic group are substituted with halogen atoms or unsubstituted, as shown in R ²³ and R ²⁴ The methylene groups in the alkyl, arylalkyl, and arylalkenyl groups are sometimes replaced by unsaturated bonds, -O- or -S- under the condition that the oxygen atoms are not adjacent, R ²³ can be adjacent R ²³ forms a ring, e represents a number of 0~4, f represents a number of 0-8, g represents a number of 0-4, h represents a number of 0-4, and the total number of g and h is 2-4 , * Means to bond with the adjacent group at the * part, (ii) is m=3, A is represented by the following formula (2), [Chemical formula 7]

In the formula, X ² represents a carbon atom substituted with R ²⁵ , a trivalent aliphatic hydrocarbon group having 1 to 35 carbon atoms, a trivalent alicyclic hydrocarbon group having 3 to 35 carbon atoms, and a trivalent carbon number of 6 ~35 Aromatic ring-containing hydrocarbon group or trivalent C2-35 heterocyclic group-containing group, R ²⁵ represents a hydrogen atom, a C1-C8 alkyl group, a C6-C30 aromatic group In the group, the arylalkyl group having 7 to 30 carbon atoms, or the arylalkenyl group having 8 to 30 carbon atoms, the methylene group in the aliphatic hydrocarbon group represented by X ² may also be -COO-, -O- , -OCO-, -NHCO-, -NH-, -CONH-, -O-CONH-, -NHCO-O- are replaced under the condition that the oxygen atoms are not adjacent, Z ¹ ~ Z ³ are each independently The groups represented by Z ¹ and Z ² in the formula (1) are the same, * means that they are bonded to the adjacent group at the * part, but the group represented by the general formula (2) above has 1 to 1 carbon atoms Within the range of 35, (iii) is m=4, A is represented by the following formula (3), [Chemical Formula 8]

In the formula, X ³ represents a carbon atom, a tetravalent aliphatic hydrocarbon group having 1 to 35 carbon atoms, a tetravalent carbon atom having 3 to 35 alicyclic hydrocarbon groups, and a tetravalent carbon atom having 6 to 35 carbon atoms. A ring-shaped hydrocarbon group or a tetravalent carbon atom containing a heterocyclic group having 2 to 35 carbon atoms, the methylene group in the aliphatic hydrocarbon group represented by X ³ may sometimes be -COO-, -O-, -OCO-,- NHCO-, -NH-, -CONH-, -O-CONH-, -NHCO-O- are replaced under the condition that oxygen atoms are not adjacent, Z ¹ ~ Z ⁴ are each independently from the above in the general formula (1) The groups represented by Z ¹ and Z ² are the same, * means that the * portion is bonded to an adjacent group, but the group represented by the general formula (3) is in the range of 1 to 35 carbon atoms, ( iv) m=5, A is represented by the following formula (4),

In the formula, X ⁴ represents a pentavalent aliphatic hydrocarbon group having 2 to 35 carbon atoms, a pentavalent carbon atom having 3 to 35 alicyclic hydrocarbon groups, and a pentavalent carbon atom having 6 to 35 aromatic ring-containing hydrocarbon groups Or a pentavalent C2-C35 heterocyclic group-containing group, the methylene group in the aliphatic hydrocarbon group represented by X ⁴ may also be replaced by -COO-, -O-, -OCO-, -NHCO-, -NH-, -CONH-, -O-CONH-, -NHCO-O- are replaced under the condition that the oxygen atoms are not adjacent, Z ¹ ~ Z ⁵ are each independently from Z ¹ and Z ¹ in the above general formula (1) The groups represented by Z ² are the same, * means that the * portion is bonded to an adjacent group, but the group represented by the above general formula (4) is in the range of 2 to 35 carbon atoms, and (v) is m=6, A is expressed by the following formula (5),

In the formula, X ⁵ represents an aliphatic hydrocarbon group having a hexavalent carbon number of 2 to 35, an alicyclic hydrocarbon group having a hexavalent carbon number of 3 to 35, and an aromatic ring-containing hydrocarbon group having a hexavalent carbon number of 6 to 35 Or a heterocyclic group having 2 to 35 carbon atoms and 2 to 35 carbon atoms, the methylene group in the aliphatic hydrocarbon group represented by X ⁵ may also be substituted by -COO-, -O-, -OCO-, -NHCO-, -NH-, -CONH-, -O-CONH-, -NHCO-O- are replaced under the condition that the oxygen atoms are not adjacent, Z ¹ ~ Z ⁶ are independently from Z ¹ and Z ¹ in the above general formula (1) The group shown by Z ² is the same, * means that the * part is bonded to an adjacent group, but the group represented by the above general formula (5) is in the range of 2 to 35 carbon atoms,

In formula (1a), R ^1a to R ^4a independently represent a hydrogen atom, a C 1-20 monovalent saturated hydrocarbon group which may have a substituent, and a C 6-10 monovalent aromatic group which may have a substituent Group hydrocarbon group, or a group represented by formula (i), *-R ^50a -Si(R ^29a ) ₃ (i) R ^29a represents a hydrogen atom, a hydroxyl group, a C 1-4 alkyl group or a C 1-4 carbon number Alkoxy groups, a plurality of R ^29a may be the same as or different from each other, R ^50a represents a C1-C10 alkanediyl group, -CH ₂ -constituting the alkanediyl group may be -O-, -CO-, -NR ^12a -, -OCO-, -COO-, -OCONH-, -NHCOO-, -CONH-, or -NHCO- are substituted under the condition that the oxygen atom is not adjacent, * indicates the bonding end to the nitrogen atom, R ^{In 1a} to R ^4a , the methylene group (-CH ₂ -) contained in this saturated hydrocarbon group is sometimes replaced by -O-, -CO-, -NR ^11a -, -OCO-, -COO-, -OCONH-, -NHCOO-, -CONH- or -NHCO- is substituted under the condition that the oxygen atoms are not adjacent, R ^1a and R ^2a may also form a ring containing a nitrogen atom together, R ^3a and R ^4a may form a ring containing a nitrogen atom together , R ^5a represents _{^{-OH, -SO 3 -, -SO 3}} H, -SO 3 - Z +, -CO 2 H, -CO 2 - Z +, -CO 2 R 8a, -SO 3 R 8a or -SO ₂ NR ^9a R ^10a , R ^6a and R ^7a independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, ma represents an integer of 0 to 5, when ma is 2 or more, a plurality of R ^5a may be the same or Different, a represents an integer of 0 or 1, Xa represents a halogen atom, Z ⁺ represents ⁺ N(R ^11a ) ₄ , Na ⁺ or K ⁺ , the four R ^11a may be the same or different, and R ^8a represents the carbon number 1~ 20 monovalent saturated hydrocarbon group, the hydrogen atom contained in the saturated hydrocarbon group may be replaced by a halogen atom, R ^9a and R ^10a independently represent a hydrogen atom or a monovalent saturation of 1 to 20 carbon atoms which may have a substituent Hydrocarbon group, the methylene group (-CH ₂ -) contained in the saturated hydrocarbon group is sometimes replaced by -O-, -CO-, -NR ^11a -, -OCO-, -COO-, -OCONH-, -NHCOO-, -CONH- or -NHCO- is substituted under the condition that oxygen atoms are not adjacent, R ^9a and R ^10a can combine with each other to form a heterocyclic ring containing a 3- to 10-membered ring containing a nitrogen atom, and R ^11a represents a hydrogen atom and a carbon number 1 to 20 monovalent saturated hydrocarbon group or aralkyl group having 7 to 10 carbon atoms. The color-curable resin composition according to claim 1, wherein the compound (A1) is represented by formula (II):

In the formula, ring D represents a five-membered ring or six-membered ring, and the five-membered ring or six-membered ring represented by ring D may be fused with other rings or may be substituted. R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , X, G, A and m are the same as the above general formula (I), when m≧2, there are multiple R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , X, D, and G may be the same or different. The color-curable resin composition according to claim 2, wherein the compound (A1) is represented by formula (III): [Chemical formula 12]

In the formula, X ¹¹ , X ¹² and X ¹³ each independently represent -O-, -S-, -C(=O)-, -C(=S)-, -N(R ³¹ )-, -N= Or -C(R ³² )=, the bond between X ¹¹ and X ¹² and X ¹² and X ¹³ is a single bond, a double bond or a conjugated double bond, R ³¹ represents a hydrogen atom, an alkane having 1 to 20 carbon atoms Group, aryl group having 6 to 30 carbon atoms, arylalkyl group having 7 to 30 carbon atoms, or arylalkenyl group having 8 to 30 carbon atoms, or heterocyclic group having 2 to 30 carbon atoms , The alkyl group, aryl group, arylalkyl group, and arylalkenyl group represented by R ³¹ are sometimes bound to N by halogen atom, hydroxyl group, carboxyl group, sulfonic acid group, nitro group, sulfonamide group, or alkyl group The sulfonamide group is substituted, the carboxyl group and the sulfonic acid group sometimes form a salt, and the methylene group in the alkyl group, arylalkyl group, and arylalkenyl group represented by R ³¹ is sometimes substituted by -COO- O-, -OCO-, -NHCO-, -NH-, -CONH-, -SO ₂ -NH- or -NH-SO ₂ -are replaced under the condition that oxygen atoms are not adjacent, R ³² represents the number of carbon atoms 1 ~20 alkyl group, aryl group having 6-30 carbon atoms, arylalkyl group having 7-30 carbon atoms, or arylalkenyl group having 8-30 carbon atoms, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , X, A and m are the same as the above general formula (I), when m≧2, there are multiple R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , X ¹¹ , X ¹² and X ¹³ may be the same or different. The color-curable resin composition according to claim 2, wherein the compound (A1) is represented by formula (IV):

In the formula, X ¹⁴ , X ¹⁵ , X ¹⁶ and X ¹⁷ each independently represent -O-, -S-, -C(=O)-, -C(=S)-, -N(R ³⁵ )-, -C(R ³⁶ )(R ³⁷ )-, -N= or -C(R ³⁸ )=, the bond between X ¹⁴ and X ¹⁵ , X ¹⁵ and X ¹⁶ and X ¹⁶ and X ¹⁷ is single bond, double bond Bond or conjugated double bond, R ³⁵ each independently represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, and a carbon atom The arylalkenyl group of 8-30 or the heterocyclic group containing 2-30 carbon atoms, the alkyl group, aryl group, arylalkyl group, or arylalkenyl group represented by R ³⁵ may be halogen Atom, hydroxyl, carboxyl, sulfonic acid group or nitro group substitution, the carboxyl group and sulfonic acid group sometimes form a salt, the alkyl group represented by R ³⁵ , arylalkyl group, and arylalkenyl group also have methylene Is replaced by -COO-, -O-, -OCO-, -NHCO-, -NH-, -CONH-, -SO ₂ -NH-, or -NH-SO ₂ -without oxygen atoms adjacent to each other, R ³⁶ , R ³⁷ and R ³⁸ each independently represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or a carbon atom The arylalkenyl groups of 8 to 30, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , X, A and m are the same as the above general formula (I). The coloring curable resin composition according to any one of claims 1 to 3, wherein the compound (A1) is represented by the formula (V):

In the formula, R ¹ , R ² , R ³ , R ⁴ , R ⁶ , R ⁷ and X are the same as the above general formula (I), X ¹¹ , X ¹² and X ¹³ are the same as the above general formula (III), X ¹ , Z ¹ and Z ² are the same as the above general formula (1). The coloring curable resin composition according to any one of claims 1, 2, or 4, wherein the compound (A1) is represented by formula (VI):

In the formula, R ¹ , R ² , R ³ , R ⁴ , R ⁶ , R ⁷ and X are the same as the above general formula (I), X ¹⁴ , X ¹⁵ , X ¹⁶ and X ¹⁷ are the same as the above general formula (IV) , X ¹ , Z ¹ and Z ² are the same as the above general formula (1). The coloring curable resin composition according to any one of claims 1 to 3, wherein the compound (A1) is represented by the general formula (VII): [Chemical Formula 16]

In the formula, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and X are the same as the above general formula (I), X ¹¹ is the same as the above general formula (III), R ³¹ is the same as the above When X ¹³ in formula (III) is represented by -N(R ³¹ )-, R ^{31 is the} same, and any one or more of R ¹ , R ² , R ³ , R ⁴ , R ^5, and R ³¹ are selected from nitro; Hydrocarbon, carboxyl, sulfonic acid or halogen atom substituted or unsubstituted C 1-20 alkyl; methylene in C 1-20 alkyl is -SO ₂ -NH- or -NH- SO ₂ -Substituted group; aryl group with 6 to 30 carbon atoms substituted by hydroxy, carboxy, sulfonate, sulfonamide, or sulfonamide with alkyl bonded to N; substituted by hydroxy, carboxy, or Sulfonic acid-substituted arylalkyl groups with 7-30 carbon atoms or arylalkenyl groups with 8-30 carbon atoms; alkyl groups with 1-20 carbon atoms, aryl groups with 6-30 carbon atoms, carbon The arylalkyl group having 7 to 30 atoms or the arylalkenyl group having 8 to 30 carbon atoms has a group in which a substituent for forming a salt is formed. The coloring curable resin composition according to any one of claims 1, 2, or 4, wherein the compound (A1) is represented by formula (VIII): [Chemical Formula 17]

In the formula, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and X are the same as the above general formula (I), and R ³⁵ is the same as X ¹⁵ and X ¹⁷ in the above general formula (IV) When R is represented by -N(R ³⁵ )-, R ^{35 is the} same, a plurality of R ^{35 are the} same or different, and any one or more of R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ³⁵ are selected from nitro ; C 1-20 alkyl groups substituted or unsubstituted by hydroxyl, carboxyl, sulfonic acid groups or halogen atoms; methylene groups in C 1-20 alkyl groups are -SO ₂ -NH- or- NH-SO ₂ -substituted groups; aryl groups with 6 to 30 carbon atoms substituted with hydroxyl, carboxyl or sulfonic acid groups; arylalkanes with 7 to 30 carbon atoms substituted with hydroxyl, carboxyl or sulfonic acid groups Group; arylalkenyl group having 8 to 30 carbon atoms substituted with hydroxyl, carboxyl or sulfonic acid group; alkyl group having 1 to 20 carbon atoms, aryl group having 6 to 30 carbon atoms, or 7 to 7 carbon atoms The arylalkyl group of 30, or the arylalkenyl group of 8-30 carbon atoms has the group which formed the substituent of a salt. A dispersion liquid containing the compound (A1) according to any one of claims 1 to 8, a dispersant and an organic solvent. The dispersion liquid according to claim 9, wherein the dispersant is (1) Dispersant with an amine value of 0 to 200 mgKOH/g, (2) Dispersant with an acid value of 0 to 200 mgKOH/g, or (3) Amine value of 0 to 200 mgKOH/g and acid value of 0 to 200 mgKOH/g Any of g dispersants. The dispersion liquid according to claim 9 or 10, wherein the organic solvent contains alkylene glycol monoalkyl ether acetate, and the content of the alkylene glycol monoalkyl ether acetate is relative to the total amount of the solvent The amount is 40% by mass or more and 99% by mass or less. A color filter formed from the color-curable resin composition according to any one of claims 1 to 8. A display device including the color filter according to claim 12.