KR20150034626A - Colored curable resin composition - Google Patents

Abstract

The present invention provides a colored curable resin composition comprising: one or more kinds of colorants (A1) selected from the group of C.I. pigment yellow 138, a green pigment and a yellow pigment, Squarylium dye (A2), resin (B), polymer compounds (C), polymerization initiator (D) and solvent (E).

Description

COLORED CURABLE RESIN COMPOSITION [0002]

The present invention relates to a colored curable resin composition and the like.

The colored curable resin composition is used for producing a color filter such as a liquid crystal display device.

As a green colorant used in such a tinctorial resin composition, there may be mentioned C.I. Pigment Green 58 and squarylium dyes are known (Japanese Patent Laid-Open No. 2003-161827, DIC TECHNICAL REVIEW NO. 14/2008).

(II-0-1) is disclosed in JP-A No. 60-169453, and JP-A-60-248652 discloses a compound represented by the formula (II- 0-2). ≪ / RTI >

The present invention provides the following [1] to [10].

[1] C.I. At least one colorant (A1) selected from the group consisting of Pigment Yellow 138, green pigment and yellow dye,

A squarylium dye (A2)

The resin (B)

The polymerizable compound (C)

The polymerization initiator (D)

Solvent (E)

And a coloring curable resin.

[2] As the colorant (A1), C.I. Pigment Yellow 138. The colored curable resin composition according to < 1 >

[3] The colored curable resin composition according to [1], which contains a yellow dye as the colorant (A1).

[4] A coating film formed from the colored curable resin composition according to any one of [1] to [3].

[5] A color filter formed from the colored curable resin composition according to any one of [1] to [3].

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

[7] A compound represented by the formula (II-1).

[Wherein R ^1a to R ^4a each independently represent a hydrogen atom, a halogen atom, a hydroxy group or a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms. The hydrogen atom or the methyl group contained in the monovalent saturated hydrocarbon group may be substituted with a halogen atom, a hydroxy group or an alkylamino group having 1 to 8 carbon atoms, and an oxygen atom or a sulfur atom is inserted between the carbon atoms constituting the monovalent saturated hydrocarbon group .

R ^5a and R ^6a each independently represent a hydrogen atom or a hydroxy group.

R ^7a and R ^8a each independently represent a monovalent saturated hydrocarbon group having 8 to 20 carbon atoms or a group represented by the formula (i-1).

In the above formula, R ^14a represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms or a monovalent unsaturated hydrocarbon group having 2 to 20 carbon atoms, and m1 represents an integer of 1 to 5. When m1 is 2 or more, plural R < ^{14a >} may be the same or different. * Represents the number of bonds with carbon atoms (hands).

R ^9a to R ^12a each independently represent a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms or a group represented by the formula (i-1). The hydrogen atom or the methyl group contained in the monovalent saturated hydrocarbon group may be substituted with a halogen atom, a hydroxy group or an alkylamino group having 1 to 8 carbon atoms, and an oxygen atom or a sulfur atom is inserted between the carbon atoms constituting the monovalent saturated hydrocarbon group It may be.]

[8] The compound represented by the formula (II-2).

[Wherein R ^1b to R ^4b each independently represent a hydrogen atom, a halogen atom, a hydroxy group or a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms. The hydrogen atom or the methyl group contained in the monovalent saturated hydrocarbon group may be substituted with a halogen atom, a hydroxy group or an alkylamino group having 1 to 8 carbon atoms, and an oxygen atom or a sulfur atom is inserted between the carbon atoms constituting the monovalent saturated hydrocarbon group .

Each of R ^5b to R ^8b independently represents a hydrogen atom or a hydroxy group.

Ar ^1b and Ar ^2b each independently represent a group represented by the formula (i-2).

In the above formula, R ^12b represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms or a monovalent unsaturated hydrocarbon group having 2 to 20 carbon atoms, and m2 represents an integer of 1 to 5. When m2 is 2 or more, plural ^R12b may be the same or different. * Represents the number of bonds with nitrogen atoms.

R ^9b and R ^10b each independently represent a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms or a group represented by the formula (i-2). The hydrogen atom or the methyl group contained in the monovalent saturated hydrocarbon group may be substituted with a halogen atom, a hydroxy group or an alkylamino group having 1 to 8 carbon atoms, and an oxygen atom or a sulfur atom is inserted between the carbon atoms constituting the monovalent saturated hydrocarbon group It may be.]

[9] A colorant comprising the compound according to [7] or [8].

[10] A colored curable resin composition comprising a compound, a resin, a polymerizable compound, a polymerization initiator and a solvent according to [7] or [8].

[11] A coating film formed using the tinting curable resin composition according to [10].

[12] A color filter formed using the tinting curable composition according to [10].

[13] A display device comprising the color filter according to [12].

The colored curable resin composition of the present invention comprises the colorant (A1), the squarylium dye (A2), the resin (B), the polymerizable compound (C), the polymerization initiator (D) . Hereinafter, the colored curable resin composition may be referred to as " colored curable resin composition (1) ".

<Colorant>

The colored curable resin composition (1) contains, as the colorant (A), C.I. Pigment Yellow 138, a green pigment, and a yellow dye, and a squarylium dye (A2).

C.I. Pigment Yellow 138 is a pigment classified as pigment in the color index represented by the following formula (The Society of Dyers and Colourists).

Green pigments include C.I. pigment classified as pigment in the color index (The Society of Dyers and Colourists). Pigment Green 1 (hereinafter, the description of the CI Pigment Green is omitted and only numbers are given), 2, 4, 7, 8, 10, 13, 14, 15, 17, 18, 19, 26, 36, 45 , 48, 50, 51, 54, 55, 58, and the like. Among them, C.I. Pigment Green 58 is preferred.

As yellow dyes, the color index (published by The Society of Dyers and Colourists) is C.I. Solvent Yellow, C.I. Acid Yellow, C.I. Direct Yellow, C.I. Compounds classified as modern yellow, coumarin dyes, gold azo dyes, pyridone azo dyes, barbitur azo dyes, quinophthalone dyes, methine dyes and cyanine dyes.

Specifically, C.I. Solvent Yellow 4, 14, 15, 23, 24, 38, 62, 63, 68, 82, 94, 98, 99, 162;

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

C.I. Direct Yellow 2, 33, 34, 35, 38, 39, 43, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 136, 138, 141;

C.I. Modern Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65; And the like.

The coumarin dyes include, for example, the following dyes.

Examples of the coupling azo dye include the following dyes.

Examples of pyridone azo dyes include the following dyes.

The barbitur azo dyes include, for example, the following dyes.

The quinophthalone dyes include, for example, the following dyes.

The methine dyes include, for example, the following dyes.

The cyanine dyes include, for example, the following dyes.

The yellow dyes are preferably coumarine dyes, binding azo dyes, pyridone azo dyes, barbitur azo dyes, quinophthalone dyes, methine dyes and cyanine dyes, more preferably coumarine dyes, pyridone azo dyes and quinophthalone dyes Do.

The colored curable resin composition (1) contains a squarylium dye (A2) as a colorant.

Examples of the squarylium dye (A2) include, but are not limited to, known squarylium dyes and compounds represented by the following formulas (II-1) and (II-2).

Specific examples of the squarylium dye (A2) include compounds described in JP-A-2013-76926, compounds represented by the formula (AII), and tautomers thereof.

(Wherein R ¹ to R ⁴ each independently represent a hydrogen atom, a halogen atom, a hydroxy group, a phenyl group which may have a substituent or a monovalent saturated hydrocarbon group of 1 to 20 carbon atoms.

R ⁵ to R ⁸ each independently represent a hydrogen atom, a hydroxy group, a mercapto group, an alkoxy group having 1 to 5 carbon atoms, or a trifluoromethyl group.

R ⁹ to R ¹² each independently represent a monovalent saturated hydrocarbon group of 1 to 20 carbon atoms, and the hydrogen atom contained in the monovalent saturated hydrocarbon group may be a halogen atom, a cyano group, a carbamoyl group, a sulfamoyl group, Or an oxygen atom or a sulfur atom may be inserted between the carbon atoms constituting the saturated hydrocarbon group.)

[Wherein R ^1a to R ^4a each independently represent a hydrogen atom, a halogen atom, a hydroxy group or a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms. The hydrogen atom or the methyl group contained in the monovalent saturated hydrocarbon group may be substituted with a halogen atom, a hydroxy group or an alkylamino group having 1 to 8 carbon atoms, and an oxygen atom or a sulfur atom is inserted between the carbon atoms constituting the monovalent saturated hydrocarbon group .

R ^5a and R ^6a each independently represent a hydrogen atom or a hydroxy group.

R ^7a and R ^8a each independently represent a monovalent saturated hydrocarbon group having 8 to 20 carbon atoms or a group represented by the following formula (i-1).

In the above formula, R ^14a represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms or a monovalent unsaturated hydrocarbon group having 2 to 20 carbon atoms, and m1 represents an integer of 1 to 5. When m1 is 2 or more, plural R &lt; ^{14a &gt;} may be the same or different. * Represents the number of bonds with carbon atoms.

R ^9a to R ^12a each independently represent a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms or a group represented by the formula (i-1). The hydrogen atom or the methyl group contained in the monovalent saturated hydrocarbon group may be substituted with a halogen atom, a hydroxy group or an alkylamino group having 1 to 8 carbon atoms, and an oxygen atom or a sulfur atom is inserted between the carbon atoms constituting the monovalent saturated hydrocarbon group It may be.]

[Wherein R ^1b to R ^4b each independently represent a hydrogen atom, a halogen atom, a hydroxy group or a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms. The hydrogen atom or the methyl group contained in the monovalent saturated hydrocarbon group may be substituted with a halogen atom, a hydroxy group or an alkylamino group having 1 to 8 carbon atoms, and an oxygen atom or a sulfur atom is inserted between the carbon atoms constituting the monovalent saturated hydrocarbon group .

Each of R ^5b to R ^8b independently represents a hydrogen atom or a hydroxy group.

Ar ^1b and Ar ^2b each independently represent a group represented by the following formula (i-2).

In the above formula, R ^12b represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms or a monovalent unsaturated hydrocarbon group having 2 to 20 carbon atoms, and m2 represents an integer of 1 to 5. When m2 is 2 or more, plural ^R12b may be the same or different. * Represents the number of bonds with nitrogen atoms.

R ^9b and R ^10b each independently represent a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms or a group represented by the formula (i-2). The hydrogen atom or the methyl group contained in the monovalent saturated hydrocarbon group may be substituted with a halogen atom, a hydroxy group or an alkylamino group having 1 to 8 carbon atoms, and an oxygen atom or a sulfur atom is inserted between the carbon atoms constituting the monovalent saturated hydrocarbon group It may be.]

The squarylium dye (A2) is preferably a compound represented by the formula (AII). Hereinafter, the compound represented by the formula (AII) will be described in detail.

In the formula (AII), examples of the halogen atom in R ¹ to R ⁴ include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

Examples of the saturated hydrocarbon group for R ¹ to R ⁴ and R ⁹ to R ¹² include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, A straight chain alkyl group having 1 to 20 carbon atoms such as a hexadecyl group and an icosyl group;

Branched alkyl groups having 3 to 20 carbon atoms such as isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, neopentyl and 2-ethylhexyl;

And alicyclic saturated hydrocarbon groups having 3 to 20 carbon atoms such as cyclopropyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group and tricyclodecyl group.

Examples of the substituent which the phenyl group in R ¹ to R ⁴ may have include a halogen atom, a cyano group, a hydroxyl group, and an amino group.

In the formula (AII), it is preferable that R ¹ to R ⁴ are each independently a hydrogen atom.

R ⁵ to R ⁸ each independently represent a hydrogen atom, a hydroxyl group, or an alkoxy group having 1 to 5 carbon atoms, and more preferably a hydrogen atom, a hydroxy group, a methoxy group or an ethoxy group.

R ⁹ to R ¹² each independently represent an alkyl group having 1 to 10 carbon atoms (in the alkyl group, the hydrogen atom may have a hydroxy group or an oxygen atom may be inserted between the carbon atoms).

In formula (AII)

A group represented by X ¹ ,

When a group represented by a X ^2, X ¹ or a group or groups represented by X ² is, for example represented by the formula (A2-1) ~ formula (A2-7), the formula (A3-1) ~ formula (A3- 6). * Represents the number of bonds with carbon atoms.

(AII-1) to a compound (AII-14) shown in Table 1 and a compound (AII-15) having a substituent shown in Table 2 and Table 3 to a compound (AII-68), but the present invention is not limited thereto.

[Table 2]

The compound (AII-1) to the compound (AII-7), the compound (AII-16), the compound (AII-23) 29) and compound (AII-62) are more preferable, and compound (AII-2), compound -2), the compound (AII-23) and the compound (AII-29) are more preferable.

As a method for producing the compound represented by the formula (AII), for example, a method described in JP-A-2002-363434, a method of reacting an amine derivative with scarboxylic acid (3,4-dihydroxy-3-cyclobutene- 2-dione).

The ratio of the content of the colorant (A1) to the content of the squarylium dye (A2) in the colored curable resin composition (1) is preferably 60:40 to 99.9: 0.1, more preferably 70:30 to 99: Is more preferable. , The color filter formed from the colored curable resin composition (1) containing the colorant (A) has high brightness and good contrast.

In the colored curable resin composition (1), the content of the squarylium dye (A2) is preferably 70 to 100% by mass, more preferably 80 to 100% by mass with respect to the total amount of the dyes, And more preferably 85 to 100 mass%.

The content of the colorant (A) is preferably from 5 to 60 mass%, more preferably from 8 to 55 mass%, and still more preferably from 10 to 50 mass%, based on the total solid content. When the content of the colorant (A) is within the above range, the color density of the color filter is sufficient and the resin (B) or the polymerizable compound (C) can be contained in a required amount in the composition. A sufficient pattern can be formed. Here, the "total amount of solid content" in the present specification means the amount excluding the content of the solvent in the total amount of the colored curable resin composition. The total amount of the solid content and the content of each component in the total amount can be measured by known analytical means such as liquid chromatography or gas chromatography.

&Lt; Resin (B) >

The resin (B) is not particularly limited, but is preferably an alkali-soluble resin. Examples of the resin (B) include the following resins [K1] to [K6].

Resin [K1]; (Ba) (hereinafter sometimes referred to as (Ba)) selected from the group consisting of an unsaturated carboxylic acid and an unsaturated carboxylic acid anhydride, a cyclic ether structure having a carbon number of 2 to 4 and an ethylenic unsaturated bond (Hereinafter sometimes referred to as &quot; (Bb) &quot;);

Resin [K2]; (Bc) which is copolymerizable with (Ba) and (Bb), and (Ba) (with the exception of (Ba) and (Bb)) (hereinafter sometimes referred to as "(Bc)");

Resin [K3]; (Ba) and (Bc);

Resin [K4]; A resin obtained by reacting (Bb) a copolymer of (Ba) and (Bc);

Resin [K5]; (Ba) with a copolymer of (Bb) and (Bc);

Resin [K6]; (Ba) is reacted with a copolymer of (Bb) and (Bc), and the carboxylic acid anhydride is further reacted.

(Ba) include specifically unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, o-, m- and p-vinylbenzoic acid;

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

5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo [2.2.1] hept-2-ene, 5,6-dicarboxybicyclo [2.2.1] hept- 5-ethylbicyclo [2.2.1] hept-2-ene, 5-carboxy-6-methylbicyclo [2.2.1] hept- [2.2.1] hept-2-ene, and 5-carboxy-6-ethylbicyclo [2.2.1] hept-2-ene;

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

(Meth) acryloyloxyalkyl (meth) acrylate of a divalent or higher polyvalent carboxylic acid such as mono [2- (meth) acryloyloxyethyl] succinate, mono [2- ] Esters;

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

Of these, acrylic acid, methacrylic acid and maleic anhydride are preferable from the viewpoint of copolymerization reactivity and the solubility of the resulting resin in an aqueous alkali solution.

(Bb) refers to a polymerizable compound having an ethylenic unsaturated bond and a cyclic ether structure having 2 to 4 carbon atoms (for example, at least one member selected from the group consisting of oxiran ring, oxetane ring and tetrahydrofuran ring) . (Bb) is preferably a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth) acryloyloxy group.

In the present specification, the term "(meth) acrylic acid" refers to at least one kind selected from the group consisting of acrylic acid and methacrylic acid. Quot ;, &quot; (meth) acryloyl &quot;, and &quot; (meth) acrylate &quot;

(Bb), a monomer having an oxiranyl group and an ethylenically unsaturated bond, a monomer having an oxetanyl group and an ethylenically unsaturated bond, a monomer having an ethylenically unsaturated bond and a tetrahydrofuryl group, and the like.

(Bb) is preferably a monomer having an oxiranyl group and an ethylenically unsaturated bond in that the reliability of the obtained color filter can be further improved, such as heat resistance, chemical resistance and the like.

(Meth) acrylate, sec-butyl (meth) acrylate, tert-butyl (meth) acrylate, 2- (Meth) acrylate, cyclohexyl (meth) acrylate, dodecyl (meth) acrylate, lauryl (meth) acrylate, stearyl (Meth) acrylate, tricyclo [5.2.1.0 ^2,6 ] decan-8-yl (meth) acrylate (also referred to in the art as "dicyclopentanyl (meth) acrylate" (Tricyclodecyl (meth) acrylate), tricyclo [5.2.1.0 ^2,6 ] decen-8-yl (meth) acrylate (also referred to in the art as "dicyclohexyl (Meth) acrylate "), dicyclopentane (Meth) acrylate, isobornyl (meth) acrylate, adamantyl (meth) acrylate, allyl (meth) acrylate, propargyl (Meth) acrylates such as methyl (meth) acrylate, ethyl (meth) acrylate and benzyl (meth) acrylate;

(Meth) acrylic acid esters having a hydroxyl group such as 2-hydroxyethyl (meth) acrylate and 2-hydroxypropyl (meth) acrylate;

Dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate, and diethyl itaconate;

2-ene, 5-methylbicyclo [2.2.1] hept-2-ene, 5-ethylbicyclo [2.2.1] hept- 2.2.1] hept-2-ene, 5- (2'-hydroxyethyl) bicyclo [2.2.1] hept- 2.2.1] hept-2-ene, 5-methoxybicyclo [2.2.1] (2'-hydroxyethyl) bicyclo [2.2.1] hept-2-ene, 5,6-di (hydroxymethyl) bicyclo [2.2.1] hept- Ene, 5,6-dimethoxybicyclo [2.2.1] hept-2-ene, 5,6-diethoxybicyclo [2.2.1] hept- 2.2.1] hept-2-ene, 5-hydroxymethyl-5-methylbicyclo [2.2.1] hept- 2-ene, 5-tert-butoxycarbonylbicyclo [2.2.1] hept-2-ene, 5-cyclohexyloxycarbonylbicyclo [2.2.1] hept- Cyclohexyl [2.2.1] hept-2-ene, 5,6-bis 2,6-bis (cyclohexyloxycarbonyl) bicyclo [2.2.1] hept-2-ene and the like such as bis (tert-butoxycarbonyl) bicyclo [2.2.1] hept- Cyclo-unsaturated compounds;

N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimide benzoate, N-succinimidyl-4-maleimide butyrate, N- Dicarbonylimide derivatives such as N-succinimidyl-3-maleimidepropionate and N- (9-acridinyl) maleimide;

And examples thereof include styrene,? -Methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, p-methoxystyrene, acrylonitrile, methacrylonitrile, vinyl chloride, vinylidene chloride, acrylamide, methacrylamide, Vinyl, 1,3-butadiene, isoprene, 2,3-dimethyl-1,3-butadiene and the like.

Of these, styrene, vinyltoluene, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide and bicyclo [2.2.1] hept-2- ene are preferred from the viewpoint of copolymerization reactivity and heat resistance Do.

Specific examples of the resin (B) include 3,4-epoxycyclohexylmethyl (meth) acrylate / (meth) acrylic acid copolymer, 3,4-epoxytricyclo [5.2.1.0 ^2.6 ] decyl acrylate / A resin [K1] such as an acrylic acid copolymer; (Meth) acrylate / benzyl (meth) acrylate / (meth) acrylic acid copolymer, glycidyl (meth) acrylate / styrene / (meth) acrylic acid copolymer, 3,4-epoxytricyclo [5.2 .1.0 ^2.6] decyl acrylate / (meth) resins such as acrylic acid / N- cyclohexyl maleimide copolymer, 3-methyl-3- (meth) acryloyloxyethyl-methyl oxetane / (meth) acrylic acid / styrene copolymer [K2]; Resins [K3] such as benzyl (meth) acrylate / (meth) acrylic acid copolymer and styrene / (meth) acrylic acid copolymer; A resin obtained by adding glycidyl (meth) acrylate to a benzyl (meth) acrylate / (meth) acrylic acid copolymer and a resin obtained by adding glycidyl (meth) acrylate to a tricyclodecyl (meth) acrylate / styrene / (meth) ) Resin, a resin obtained by adding glycidyl (meth) acrylate to a tricyclodecyl (meth) acrylate / benzyl (meth) acrylate / (meth) acrylic acid copolymer; A resin obtained by reacting a copolymer of tricyclodecyl (meth) acrylate / glycidyl (meth) acrylate with (meth) acrylic acid, a resin obtained by reacting tricyclodecyl (meth) acrylate / styrene / glycidyl (meth) A resin [K5] such as a resin obtained by reacting a (meth) acrylic acid with a copolymer; A resin such as a resin obtained by further reacting a resin obtained by reacting (meth) acrylic acid with a copolymer of tricyclodecyl (meth) acrylate / glycidyl (meth) acrylate and tetrahydrophthalic anhydride, and the like .

Among them, resin (K) and resin (K2) are preferable as resin (B).

For example, the resin [K1] can be synthesized by the method described in the "Experimental Method of Polymer Synthesis" (published by Otsu Takayuki, First Edition, First Edition, First Edition, March 1, 1972, . &Lt; / RTI &gt;

As the obtained copolymer, the solution after the reaction may be used as it is, or a concentrated or diluted solution may be used, or a solid (powder) extracted by re-precipitation or the like may be used. Particularly, by using the solvent contained in the colored curable resin composition of the present invention as a solvent in the polymerization, the solution after the reaction can be directly used for preparing the colored curable resin composition of the present invention. Thus, the colored curable resin composition Can be simplified.

The weight average molecular weight of the resin (B) in terms of polystyrene is preferably 3,000 to 100,000, more preferably 5,000 to 50,000, and still more preferably 5,000 to 30,000. When the molecular weight is within the above range, the hardness of the color filter is improved, the residual film ratio is high, the solubility of the unexposed portion in the developing solution is good, and the resolution of the coloring pattern tends to be improved.

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 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 necessary to neutralize 1 g of the resin (B), and can be determined by titration using, for example, an aqueous potassium hydroxide solution.

The content of the resin (B) is preferably from 7 to 65% by mass, more preferably from 13 to 60% by mass, and still more preferably from 17 to 55% by mass, based on the total solid content. When the content of the resin (B) is within the above range, a colored pattern can be formed, and the resolution and residual film ratio of the colored pattern tends to be improved.

&Lt; Polymerizable compound (C) >

The polymerizable compound (C) is a compound which can be polymerized by an active radical and / or an acid generated from the polymerization initiator (D). As the polymerizable compound (C), a compound having a polymerizable ethylenically unsaturated bond and the like can be mentioned, and a (meth) acrylic acid ester compound is preferable.

Among them, the polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenic unsaturated bonds. Examples of such polymerizable compounds include trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa Acrylate, tetrapentaerythritol hexa (meth) acrylate, tripentaerythritol hexa (meth) acrylate, tripentaerythritol hexa (meth) acrylate, (Meth) acryloyloxyethyl) isocyanurate, ethylene glycol modified pentaerythritol tetra (meth) acrylate, ethylene glycol modified dipentaerythritol hexa (meth) acrylate, propylene glycol modified pentaerythritol tetra Propylene glycol-modified dipentaerythritol hexa (meth) acrylate, capro Tone and the like can be modified pentaerythritol tetra (meth) acrylate, caprolactone-modified dipentaerythritol hexa (meth) acrylate.

Among them, dipentaerythritol penta (meth) acrylate and dipentaerythritol hexa (meth) acrylate are preferable.

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

The content of the polymerizable compound (C) is preferably from 7 to 65% by mass, more preferably from 13 to 60% by mass, and still more preferably from 17 to 55% by mass, based on the total solid content. When the content of the polymerizable compound (C) is within the above range, the residual film ratio at the time of forming the coloring pattern and the chemical resistance of the color filter tend to be improved.

&Lt; Polymerization initiator (D) >

The polymerization initiator (D) is not particularly limited as long as it is a compound capable of generating an active radical or an acid by the action of light or heat to initiate polymerization of the polymerizable compound (C), and a known polymerization initiator can be used .

Examples of the polymerization initiator that generates an active radical include O-acyloxime compounds, alkylphenone compounds, triazine compounds, acylphosphine oxide compounds, and nonimidazole compounds.

Examples of the O-acyloxime compound include N-benzoyloxy-1- (4-phenylsulfanylphenyl) butan-1-one-2-imine, N-benzoyloxy- 2-imine, N-benzoyloxy-1- (4-phenylsulfanylphenyl) -3-cyclopentylpropan- Yl] ethane-1-imine, N-acetoxy-1- [9-ethyl-6- {2-methyl-4- (3,3 -Dimethyl-2,4-dioxacyclopentanylmethyloxy) benzoyl} -9H-carbazol-3-yl] ethan- 1-imine, N- acetoxy- 1- [ Benzoyl) -9H-carbazol-3-yl] -3-cyclopentylpropan- 1-imine, N-benzoyloxy- -Yl] -3-cyclopentylpropan-1-one-2-imine and the like. Commercially available products such as Irgacure (registered trademark) OXE01, OXE02 (manufactured by BASF) and N-1919 (manufactured by ADEKA) may be used. Among them, the O-acyloxime compound is preferably an N-benzoyloxy-1- (4-phenylsulfanylphenyl) butan- 1-one-2-imine and N-benzoyloxy-1- (4-phenylsulfanylphenyl) -3-cyclopentylpropan- , And N-benzoyloxy-1- (4-phenylsulfanylphenyl) octan-1-one-2-imine are more preferable. If these O-acyloxime compounds are used, a color filter having a high lightness tends to be obtained.

Examples of the alkylphenone compound include 2-methyl-2-morpholino-1- (4-methylsulfanylphenyl) propan- -Benzylbutan-1-one, 2- (dimethylamino) -2 - [(4-methylphenyl) methyl] -1- [4- (4-morpholinyl) phenyl] butan- 2-methyl-1- [4- (2-hydroxyethoxy) phenyl] propan-1-one, 1-hydroxycyclohexyl Phenyl ketone, oligomers of 2-hydroxy-2-methyl-1- (4-isopropenylphenyl) propane-1-one, α, α-diethoxyacetophenone and benzyl dimethyl ketal. IRGACURE (registered trademark) 369, 907, 379 (manufactured by BASF), or the like may be used.

Examples of the triazine compound include 2,4-bis (trichloromethyl) -6- (4-methoxyphenyl) -1,3,5-triazine, 2,4- (4-methoxynaphthyl) -1,3,5-triazine, 2,4-bis (trichloromethyl) -6-piperonyl-1,3,5-triazine, 2,4-bis (Trichloromethyl) -6- [2- (5-methylfuran-2-yl) -1,3,5-triazine, ) Ethenyl] -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (furan-2-yl) ethenyl] Bis (trichloromethyl) -6- [2- (4-diethylamino-2-methylphenyl) ethenyl] -1,3,5-triazine, 2,4- -6- [2- (3,4-dimethoxyphenyl) ethenyl] -1,3,5-triazine.

Examples of the acylphosphine oxide compound include 2,4,6-trimethylbenzoyldiphenylphosphine oxide and the like. A commercially available product such as Irgacure (registered trademark) 819 (manufactured by BASF) may be used.

Examples of the imidazole compound include 2,2'-bis (2-chlorophenyl) -4,4 ', 5,5'-tetraphenylbiimidazole, 2,2'-bis (2,3- ) -4,4 ', 5,5'-tetraphenylbiimidazole (see JP-A 6-75372, JP-A 6-75373, etc.), 2,2'-bis (2-chlorophenyl) -4,4 ', 5,5'-tetra (alkoxyphenyl) -4,4', 5,5'-tetraphenylbiimidazole, 2,2'- (2-chlorophenyl) -4,4 ', 5,5'-tetra (dialkoxyphenyl) biimidazole, 2,2'-bis 4,4 ', 5,5'-tetra (trialkoxyphenyl) biimidazole (Japanese Patent Publication No. 48-38403, Japanese Patent Laid-Open No. 62-174204, Imidazole compounds in which the phenyl group at the 5,5'-position is substituted by a carboalkoxy group (see JP-A-7-10913, etc.).

Examples of the polymerization initiator that generates an acid include 4-hydroxyphenyldimethylsulfonium p-toluenesulfonate, 4-hydroxyphenyldimethylsulfonium hexafluoroantimonate, 4-acetoxyphenyldimethylsulfonium p- Toluenesulfonate, triphenylsulfonium hexafluoroantimonate, diphenyliodonium p-toluene sulfonate, p-toluenesulfonate, triphenylsulfonium hexafluoroantimonate, diphenyliodonium p-toluene sulfonate, Onium salts such as sulfonate and diphenyliodonium hexafluoroantimonate, nitrobenzyltosylates, benzoin tosylates and the like can be given.

Examples of the polymerization initiator (D) include benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether; Benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenylsulfide, 3,3 ', 4,4'-tetra (tert- butylperoxycarbonyl) benzophenone Benzophenone compounds such as 2,4,6-trimethylbenzophenone; Quinone compounds such as 9,10-phenanthrenequinone, 2-ethyl anthraquinone, and campquinone; Butyl-2-chloroacridone, benzyl, methyl phenylglyoxylate, and titanocene compounds.

As the polymerization initiator (D), a polymerization initiator including at least one kind selected from the group consisting of O-acyloxime compounds, alkylphenone compounds, triazine compounds, acylphosphine oxide compounds and imidazole compounds is preferable, and O -Acyloxime compound is more preferable.

The content of the polymerization initiator (D) is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, based on 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). When the content of the polymerization initiator (D) is in the above range, the productivity is improved because the sensitivity is increased and the exposure time is shortened.

&Lt; Solvent (E) >

The solvent (E) is not particularly limited, and a solvent commonly used in the field can be used. For example, an ester solvent (a solvent containing -COO- in the molecule and not containing -O-), an ether solvent (a solvent containing -O- and no -COO- in the molecule), an ether ester solvent ( A solvent containing -COO- and -O- in a molecule), a ketone solvent (a solvent containing -CO- in the molecule and not including -COO-), an alcohol solvent (containing OH in the molecule, -O- , -CO- and -COO-), aromatic hydrocarbon solvents, amide solvents, dimethylsulfoxide and the like.

Examples of the ester solvent include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutyrate, ethyl acetate, n-butyl acetate, isobutyl acetate, pentyl formate, isopentyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate , Butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexanol acetone and? -Butyrolactone.

Examples of the ether solvent include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, Propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydrofuran , 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, A brush, and the like.

Examples of the ether ester solvent include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, Ethoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, ethyl 2-methoxypropionate, ethyl 2-methoxypropionate, ethyl 2-methoxypropionate, Methyl propionate, methyl propionate, methyl 2-ethoxy-2-methyl propionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, Monopropyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate And di, and the like ethylene glycol monobutyl ether acetate.

Examples of the ketone solvent include 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4- Cyclopentanone, cyclohexanone, isophorone, and the like.

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, and mesitylene.

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

Among these solvents, an organic solvent having a boiling point of 120 ° C or more and 210 ° C or less at 1 atm is preferable from the viewpoint of coatability and drying property. Examples of the solvent include propylene glycol monomethyl ether acetate, ethyl lactate, propylene glycol monomethyl ether, ethyl 3-ethoxypropionate, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, Methyl-2-pentanone and N, N-dimethylformamide are preferable, and propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, N, N-dimethylformamide, N-methylpyrrolidone and N- Ethyl 3-ethoxypropionate is more preferable.

The content of the solvent (E) is preferably 70 to 95% by mass, and more preferably 75 to 92% by mass, based on the total amount of the colored curable resin composition of the present invention. In other words, the total amount of solid content of the color-curable resin composition is preferably 5 to 30 mass%, more preferably 8 to 25 mass%. When the content of the solvent (E) is within the above range, the flatness at the time of coating becomes good, and the color characteristics are not insufficient when the color filter is formed, so that the display characteristics tend to be good.

&Lt; Other components >

The colored curable resin composition of the present invention may contain other dyes or pigments.

Examples of other dyes include dyes such as oil soluble dyes, acid dyes, amine salts of acid dyes and sulfonamide derivatives of acid dyes. For example, in the color index (The Society of Dyers and Colourists) , And known dyes described in dyeing notes (Shiken Sensha). These dyes may be used alone, or two or more dyes may be used in combination.

Specifically, C.I. Solvent Orange 2, 7, 11, 15, 26, 56, etc. C.I. Solvent dyes;

C.I. C.I., such as Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 169, Acid dyes;

C.I. Direct orange 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, Direct dyes;

C.I. C.I., such as Modern Orange 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, And modern dyes.

The pigment is not particularly limited and a known pigment can be used, and for example, a pigment classified in pigment in the color index (The Society of Dyers and Colourists) is cited.

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

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

The pigments may optionally be rosinized; Surface treatment using a pigment derivative in which an acidic group or a basic group is introduced; Grafting the surface of the pigment with a polymer compound or the like; Atomization treatment by sulfuric acid atomization method or the like; Or cleaning treatment with an organic solvent or water for removing impurities; Removal treatment of ionic impurities by ion exchange or the like; Or the like may be performed.

The pigment preferably has a uniform particle size. By containing a pigment dispersant and carrying out a dispersion treatment, a pigment dispersion in which the pigment is uniformly dispersed in a solution can be obtained.

Examples of the pigment dispersing agent include cationic surfactants, anionic surfactants, nonionic surfactants, amphoteric surfactants, polyester surfactants, polyamines surfactants and acrylic surfactants. These pigment dispersants may be used alone or in combination of two or more. (Trade name) manufactured by Shin-Etsu Chemical Co., Ltd.), fluorene (manufactured by Kyoeisha Kagaku Co., Ltd.), Solsperse (manufactured by Zeneca), EFKA (registered trademark) Azispher (manufactured by Ajinomoto Fine Techno Co., Ltd.), and Disperbyk (registered trademark) (manufactured by BICKEMISA).

The colored curable resin composition of the present invention may contain additives known in the art such as a polymerization initiator, a leveling agent, a filler, another polymer compound, an adhesion promoter, an antioxidant, a light stabilizer, good.

&Lt; Process for producing colored curable resin composition >

The colored curable resin composition (1) of the present invention contains the colorant (A1), the squarylium dye (A2), the resin (B), the polymerizable compound (C), the polymerization initiator (D) , And other components such as a leveling agent (F) and a polymerization initiation assistant.

The dye may be previously dissolved in a part or all of the solvent (E) to prepare a solution. The solution is preferably filtered with a filter having a pore diameter of about 0.01 to 1 mu m.

It is preferable that the pigment is mixed with a part or all of the solvent (E) in advance and dispersed using a bead mill or the like until the average particle diameter of the pigment becomes about 0.2 탆 or less. At this time, a part or the whole of the pigment dispersant and the resin (B) may be blended if necessary. The desired coloring curable resin composition can be prepared by mixing the remaining components in the thus obtained pigment dispersion to a predetermined concentration.

The colored curable resin composition after mixing is preferably filtered with a filter having a pore diameter of about 0.1 to 10 mu m.

<Manufacturing Method of Color Filter and the Like>

A coating film formed from the above-mentioned colored curable resin composition, and a color filter formed from the above-mentioned colored curable resin composition also fall within the scope of the present invention. A display device including the color filter is also included in the scope of the present invention.

Examples of the method for producing a colored pattern from the colored curable resin composition (1) include a photolithographic method, an inkjet method, and a printing method. Among them, a photolithographic method is preferable. The photolithographic method is a method in which the above-mentioned colored curable resin composition is applied to a substrate, followed by drying to form a colored composition layer, and the colored composition layer is exposed through a photomask and developed. In the photolithographic method, a colored coating film which is a cured product of the colored composition layer can be formed by not using a photomask and / or not developing it when exposed. The coloring pattern or colored coating film thus formed is the color filter.

The film thickness of the color filter to be produced is not particularly limited and can be appropriately adjusted depending on the purpose and application, and is, for example, from 0.1 to 30 μm, preferably from 0.1 to 20 μm, more preferably from 0.5 to 6 μm.

Examples of the substrate include glass plates such as quartz glass, borosilicate glass, alumina silicate glass and soda lime glass whose surface is coated with silica, resin plates such as polycarbonate, polymethylmethacrylate and polyethylene terephthalate, silicon, Aluminum, silver, silver / copper / palladium alloy thin film, or the like is formed. A separate color filter layer, a resin layer, a transistor, a circuit, or the like may be formed on these substrates.

The formation of each color pixel by the photolithographic method can be performed by a known or commonly used apparatus or condition. For example, it can be produced as follows.

First, a colored curable resin composition is coated on a substrate and heated and dried (pre-baked) and / or reduced-pressure drying to remove volatile components such as a solvent and dried to obtain a smooth colored composition layer.

Examples of the application method include a spin coat method, a slit coat method, and a slit and spin coat method.

The temperature for heating and drying is preferably 30 to 120 占 폚, more preferably 50 to 110 占 폚. The heating time is preferably 10 seconds to 60 minutes, more preferably 30 seconds to 30 minutes.

In the case of performing the reduced-pressure drying, it is preferable that the drying is carried out at a temperature of 20 to 25 캜 under a pressure of 50 to 150 Pa.

The film thickness of the coloring composition layer is not particularly limited and may be suitably selected in accordance with the intended thickness of the color filter.

Next, the coloring composition layer is exposed through a photomask for forming a desired coloring pattern. The pattern on the photomask is not particularly limited and a pattern according to the intended use is used.

As a light source used for exposure, a light source that generates light having a wavelength of 250 to 450 nm is preferable. For example, light having a wavelength of less than 350 nm is cut using a filter that cuts the wavelength region, or light having wavelengths around 436 nm, 408 nm, and 365 nm is extracted using a bandpass filter Or may be selectively extracted. Specific examples thereof include mercury lamps, light emitting diodes, metal halide lamps, and halogen lamps.

It is preferable to use an exposure apparatus such as a mask aligner and a stepper because it is possible to uniformly irradiate the entire exposure surface with a parallel light beam or accurately align the photomask with the substrate on which the coloring composition layer is formed.

The colored composition layer after exposure is brought into contact with a developing solution to develop a colored pattern on the substrate. By the development, the unexposed portion of the colored composition layer is dissolved and removed in the developer. As the developing solution, for example, an aqueous solution of an alkaline compound such as potassium hydroxide, sodium hydrogen carbonate, sodium carbonate, tetramethylammonium hydroxide or the like is preferable. The concentration of these alkaline compounds in the aqueous solution is preferably 0.01 to 10% by mass, and more preferably 0.03 to 5% by mass. In addition, the developer may contain a surfactant.

The developing method may be any of a puddle method, a dipping method and a spraying method. Further, the substrate may be inclined at an arbitrary angle at the time of development.

After development, it is preferable to wash with water.

Further, post-baking is preferably performed on the obtained coloring pattern. The post bake temperature is preferably 150 ° C to 250 ° C, more preferably 160 ° C to 235 ° C. The post baking time is preferably 1 to 120 minutes, more preferably 10 to 60 minutes.

According to the colored curable resin composition (1), a color filter having particularly excellent brightness can be produced. The color filter is useful as a color filter used in a display device (e.g., a liquid crystal display device, an organic EL device, an electronic paper, etc.) and a solid-state image pickup device.

&Lt; Compound represented by the formula (II-1) >

The compound represented by the formula (II-1) is a novel compound.

Each of R ^1a to R ^4a independently represents a hydrogen atom, a halogen atom, a hydroxy group or a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms. The hydrogen atom or the methyl group contained in the monovalent saturated hydrocarbon group may be substituted with a halogen atom, a hydroxy group or an alkylamino group having 1 to 8 carbon atoms, and an oxygen atom or a sulfur atom is inserted between the carbon atoms constituting the monovalent saturated hydrocarbon group .

R ^5a and R ^6a each independently represent a hydrogen atom or a hydroxy group.

R ^7a and R ^8a each independently represent a monovalent saturated hydrocarbon group having 8 to 20 carbon atoms or a group represented by the formula (i-1).

In the above formula, R ^14a represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms or a monovalent unsaturated hydrocarbon group having 2 to 20 carbon atoms, and m1 represents an integer of 1 to 5. When m1 is 2 or more, plural R &lt; ^{14a &gt;} may be the same or different. * Represents the number of bonds with carbon atoms.

R ^9a to R ^12a each independently represent a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms or a group represented by the formula (i-1). The hydrogen atom or the methyl group contained in the monovalent saturated hydrocarbon group may be substituted with a halogen atom, a hydroxy group or an alkylamino group having 1 to 8 carbon atoms, and an oxygen atom or a sulfur atom is inserted between the carbon atoms constituting the monovalent saturated hydrocarbon group It may be.]

In the present specification, the formula (II-1) and the following formula (II-2) each include a tautomer thereof.

Examples of the halogen atom represented by R ^1a to R ^4a include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

Examples of the monovalent saturated hydrocarbon group having 1 to 20 carbon atoms in R ^1a to R ^4a , R ^9a to R ^12a and R ^14a include methyl, ethyl, propyl, butyl, pentyl, hexyl, A straight chain alkyl group having 1 to 20 carbon atoms such as an octyl group, a nonyl group, a decyl group, a dodecyl group, a hexadecyl group and an eicosyl group;

Branched alkyl groups having 3 to 20 carbon atoms such as isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, neopentyl and 2-ethylhexyl;

And alicyclic saturated hydrocarbon groups having 3 to 20 carbon atoms such as cyclopropyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group and tricyclodecyl group.

Examples of the group in which the hydrogen atom or methyl group contained in these saturated hydrocarbon groups are substituted with a halogen atom, a hydroxy group or an alkylamino group having 1 to 8 carbon atoms include groups represented by the following formulas.

Examples of the alkylamino group having 1 to 8 carbon atoms include methylamino group, ethylamino group, n-propylamino group, n-butylamino group, n-pentylamino group, dimethylamino group, diethylamino group and dibutylamino group.

(In the formulas, * represents a bonding site.)

Examples of the group in which an oxygen atom or a sulfur atom is inserted between the carbon atoms constituting the saturated hydrocarbon group include groups represented by the following formulas.

(In the formulas, * represents a bonding site.)

Examples of the monovalent saturated hydrocarbon group having 8 to 20 carbon atoms in R ^7a and R ^8a include straight chain alkyl groups having 8 to 20 carbon atoms such as an octyl group, a nonyl group, a decyl group, a dodecyl group, a hexadecyl group and an icosyl group;

Methylheptyl group, 2-methylnodecyl group, 2-methylnonadecyl group, 2-ethylhexyl group, 2-methylbutyl group, Ethylheptyl group, 2-ethylheptyl group, 2-ethyloctyl group, 2-ethylnonyl group, 2-ethyldecyl group, 2-ethyldodecyl group, Propyldecyl group, 2-propylheptadecyl group, 2-butylhexyl group, 2-pentylheptyl group, 2-propylheptyl group, 2-propylheptyl group, 3-methylheptyl group, 3-methylnonyl group, 3-methyldecyl group, 3-methyldecyl group, 3-methyldecyl group, 2-heptyl group, Ethylhexyl group, 3-ethylhexyl group, 3-ethylnonyl group, 3-ethyldecyl group, 3-ethylhexyl group, 3-ethylhexyl group, Propylhexyl group, 3-propyloctyl group, 3-propylnonyl group, 3-ethylheptadecyl group, 3-ethylheptadecyl group, Propyldodecyl group, 3-propylheptadecyl group, 3-butylheptyl group, 3-pentyloctyl group, 3-hexylonyl group, 3-heptyldecyl group, Branched alkyl groups having 8 to 20 carbon atoms such as dimethyl hexyl group, 2,2-methyl ethylheptyl group, 2,3-dimethylhexyl group, 2,4-dimethylhexyl group and 2,5-dimethylhexyl group; Methylcyclooctyl group,

And a cycloalkyl group having 8 to 20 carbon atoms such as an ethylcyclohexyl group, a propylcyclopentyl group, a butylcyclobutyl group, a pentylcyclopropyl group, and an adamantyl group.

Examples of the monovalent unsaturated hydrocarbon group having 2 to 20 carbon atoms in R ^14a include a vinyl group, a propenyl group, a butenyl group, a pentenyl group, a hexenyl group, a heptenyl group, an octenyl group, a nonenyl group and a decenyl group .

Examples of the group represented by the formula (i-1) include the following groups. * Represents the number of bonds with carbon atoms.

As R ^1a to R ^4a , a hydrogen atom, a hydroxy group and a methyl group are preferable, and a hydrogen atom is more preferable.

R ^7a and R ^8a are preferably a straight chain alkyl group having 8 to 12 carbon atoms, a branched alkyl group having 8 to 16 carbon atoms, and a group represented by the formula (i-1), and examples thereof include an octyl group, a nonyl group, a decyl group, More preferably a branched alkyl group having 8 to 16 carbon atoms (particularly 2-ethylhexyl group) and a group represented by the formula (i-1), more preferably a 2-ethylhexyl group and a group represented by the formula (i-1). Each of R ^7a and R ^8a is preferably a branched alkyl group having 8 to 16 carbon atoms in view of good solubility in a solvent.

As R ^9a to R ^12a , an alkyl group having 2 to 20 carbon atoms and a group represented by the formula (i-1) are preferable, and an alkyl group having 2 to 8 carbon atoms and a group represented by the formula (i-1) are more preferable.

As R ^14a , an alkyl group having 1 to 4 carbon atoms is preferable, and a methyl group and an ethyl group are more preferable.

In the formula (II-1)

Is represented by X ^1a ,

When the group represented by X ^2a to, groups represented by X ^1a and X ^2a is, for example there may be mentioned a group represented by the formula (A2-1-1) ~ formula (A2-1-7). * Represents the number of bonds with carbon atoms.

In the formula (II-1)

Is represented by Y ¹ ,

When the group represented by Y in ^2, groups represented by Y ¹ or Y ² is, for example there may be mentioned groups represented by the formula (A3-1-1) ~ formula (A3-1-6). * Represents the number of bonds with carbon atoms.

Examples of the compound represented by the formula (II-1) include the compounds (AII-1-1) to (AII-1-21) shown in Table 4.

The compound (AII-1-1) to the compound (AII-1-7) are preferable, and the compound (AII-1-5) and the compound The compound (AII-1-6) is more preferable.

The compound represented by the formula (II-1) can be prepared by, for example, reacting a compound represented by the formula (IV-1) with scarboxylic acid (3,4- dihydroxy- &Lt; / RTI &gt;

Wherein R ^1a , R ^2a , R ^5a , R ^7a , R ^9a and R ^10a each have the same meaning as defined above.

The amount of the squaric acid to be used is preferably 0.5 mol or more and 0.8 mol or less, and more preferably 0.55 mol or more and 0.6 mol or less, relative to 1 mol of the compound represented by the formula (IV-I).

The reaction temperature is preferably 30 占 폚 to 180 占 폚, and more preferably 80 占 폚 to 140 占 폚. The reaction time is preferably 1 hour to 12 hours, more preferably 3 hours to 8 hours.

 The reaction is preferably carried out in an organic solvent in view of the yield. Examples of the organic solvent include hydrocarbon solvents such as toluene and xylene; Halogenated hydrocarbon solvents such as chlorobenzene, dichlorobenzene and chloroform; Alcohol solvents such as methanol, ethanol, isopropanol and butanol; A nitrohydrocarbon solvent such as nitrobenzene; Ketone solvents such as methyl isobutyl ketone; Amide solvents such as 1-methyl-2-pyrrolidone; These may be used in combination. Of these, a mixed solvent of butanol and toluene is preferred. The amount of the organic solvent used is preferably 30 parts by mass or more and 200 parts by mass or less, and more preferably 50 parts by mass or more and 150 parts by mass or less, based on 1 part by mass of the compound represented by the formula (IV-I).

The method of obtaining the compound represented by the formula (II-1) from the reaction mixture is not particularly limited, and various known methods can be employed. For example, after cooling, the precipitated crystals are collected by filtration. The crystals obtained by filtration are preferably washed with water or the like, and then dried successively. Further, if necessary, it may be further purified by a known technique such as recrystallization.

The compound represented by the formula (IV-I) can be synthesized by reacting the compound represented by the formula (IV-2) with the compound represented by the formula (IV-3).

[In each formula, R ^1a , R ^2a , R ^5a , R ^7a , R ^9a and R ^10a each have the same meaning as defined above.]

&Lt; Compound represented by the formula (II-2) >

The compound represented by the formula (II-2) is a novel compound. Such compounds also fall within the scope of the present application.

[Wherein R ^1b to R ^4b each independently represent a hydrogen atom, a halogen atom, a hydroxy group or a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms. The hydrogen atom or the methyl group contained in the monovalent saturated hydrocarbon group may be substituted with a halogen atom, a hydroxy group or an alkylamino group having 1 to 8 carbon atoms, and an oxygen atom or a sulfur atom is inserted between the carbon atoms constituting the monovalent saturated hydrocarbon group .

Each of R ^5b to R ^8b independently represents a hydrogen atom or a hydroxy group.

Ar ^1b and Ar ^2b each independently represent a group represented by the formula (i-2).

In the above formula, R ^12b represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms or a monovalent unsaturated hydrocarbon group having 2 to 20 carbon atoms, and m2 represents an integer of 1 to 5. When m2 is 2 or more, plural ^R12b may be the same or different. * Represents the number of bonds with nitrogen atoms.

R ^9b and R ^10b each independently represent a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms or a group represented by the formula (i-2). The hydrogen atom or the methyl group contained in the monovalent saturated hydrocarbon group may be substituted with a halogen atom, a hydroxy group or an alkylamino group having 1 to 8 carbon atoms, and an oxygen atom or a sulfur atom is inserted between the carbon atoms constituting the monovalent saturated hydrocarbon group It may be.]

Examples of the halogen atom in R ^1b to R ^4b include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

Examples of the groups represented by R ^1b to R ^4b , R ^9b , R ^10b and R ^12b include the groups exemplified as R ^1a to R ^4a in the formula (II-1).

Examples of the saturated hydrocarbon group for R ^9b , R ^10b and R ^12b include the groups exemplified as the saturated hydrocarbon groups represented by R ^1a to R ^4a in the formula (II-1).

Examples of the unsaturated hydrocarbon group for R ^12b include a vinyl group, a propenyl group, a butenyl group, a pentenyl group, a hexenyl group, a heptenyl group, an octenyl group, a nonenyl group and a decenyl group.

The group represented by the formula (i-2) includes the groups exemplified as the group represented by the above-mentioned formula (i-1).

As R ^1b to R ^4b , a hydrogen atom, a hydroxy group and a methyl group are preferable, and a hydrogen atom is more preferable.

R ^9b and R ^10b are preferably a straight chain alkyl group having 8 to 12 carbon atoms, a branched alkyl group having 8 to 16 carbon atoms and a group represented by the formula (i-2), and examples thereof include an octyl group, a nonyl group, a decyl group, More preferably a branched alkyl group having 8 to 16 carbon atoms (particularly 2-ethylhexyl group) and a group represented by the formula (i-2), and more preferably a branched alkyl group having 8 to 16 carbon atoms (particularly 2-ethylhexyl group) .

As R ^12b , an alkyl group having 1 to 4 carbon atoms is preferable, and a methyl group and an ethyl group are more preferable.

In the formula (II-2)

A group represented by X ^1b ,

When the group represented by X in ^2b, groups represented by X ^1b and X ^2b are, there may be mentioned a group represented by the formula (A2-2-1) ~ formula (A2-2-7). In each group, * represents the number of bonds with carbon atoms.

Examples of the compound represented by the formula (II-2) include the compounds (AII-2-1) to (AII-2-21) shown in Table 5.

From the viewpoint of raw material availability, the compounds (AII-2-8) to (AII-2-14) are more preferable, and the compound (AII-2-8) is more preferable.

The compound represented by the formula (II-2) can be produced, for example, by reacting the compound represented by the formula (IV-2-1) with squaric acid (3,4-dihydroxy-3-cyclobutene- Followed by reaction.

In formula (IV-1), R ^1b , R ^2b , R ^5b , R ^6b , R ^9b and Ar ¹ have the same meanings as defined above. The amount of the squaric acid to be used is preferably 0.5 mol or more and 0.8 mol or less, and more preferably 0.55 mol or more and 0.6 mol or less, relative to 1 mol of the compound represented by the formula (IV-2-I).

The reaction temperature is preferably 30 占 폚 to 180 占 폚, and more preferably 80 占 폚 to 140 占 폚. The reaction time is preferably 1 hour to 12 hours, more preferably 3 hours to 8 hours.

The reaction is preferably carried out in an organic solvent in view of the yield. Examples of the organic solvent include hydrocarbon solvents such as toluene and xylene; Halogenated hydrocarbon solvents such as chlorobenzene, dichlorobenzene and chloroform; Alcohol solvents such as methanol, ethanol, isopropanol and butanol; A nitrohydrocarbon solvent such as nitrobenzene; Ketone solvents such as methyl isobutyl ketone; Amide solvents such as 1-methyl-2-pyrrolidone; These may be used in combination. Of these, a mixed solvent of butanol and toluene is preferred. The amount of the organic solvent to be used is preferably 30 parts by mass or more and 200 parts by mass or less, more preferably 50 parts by mass or more and 150 parts by mass or less, relative to 1 part by mass of the compound represented by the formula (IV-2-I) .

The method of obtaining the compound represented by the formula (II-2) from the reaction mixture is not particularly limited, and various known methods may be employed. For example, after cooling, the precipitated crystals are collected by filtration. The crystals obtained by filtration are preferably washed with water or the like, and then dried successively. Further, if necessary, it may be further purified by a known technique such as recrystallization.

The compound represented by the formula (VI-2-1) can be produced by reacting the compound represented by the formula (IV-2-4) with the compound represented by the formula (IV-2-5). The compound represented by the formula (IV-2-4) can be produced by reacting the compound represented by the formula (IV-2-2) with the compound represented by the formula (IV-2-3).

In each formula, R ^1b , R ^2b , R ^5b , R ^6b , R ^9b , R ^12b and m 2 have the same meanings as defined above.

As a method for producing the compound represented by the formula (IV-2-1) from the compound represented by the formula (IV-2-4) and the compound represented by the formula (IV-2-5) , For example, a method described in J. Polymer Sciene Science Part A: Polymer Chemistry 2012, 50, 3788-3796.

As a method for producing the compound represented by the formula (IV-2-4) from the compound represented by the formula (IV-2-2) and the compound represented by the formula (IV-2-3) For example, Eur. J. Org. Chem. 2012, 3105-3111.

A colorant comprising a compound represented by the formula (II-1) or a compound represented by the formula (II-2) is also one of the present invention.

In the present specification, unless otherwise stated, the compound represented by the formula (II-1) and the compound represented by the formula (II-2) are collectively referred to as the "present compound".

The colorant of the present invention may contain a dye other than the compound of the present invention (hereinafter, this dye is referred to as "dye (A-1)") and a pigment.

Examples of the dye (A-1) include dyes such as oil dyes, acid dyes, amine salts of acid dyes and sulfonamide derivatives of acid dyes. For example, the dyes (A- Known compounds listed in Dyeing Note (Shika Sensha).

As the dye (A-1), according to the chemical structure, it is possible to use a coumarin dye, an amorphous azo dye, a pyridone azo dye, a barbitur azo dye, a quinophthalone dye, a methine dye, a cyanine dye, an anthraquinone dye, Xanthene dyes and phthalocyanine dyes. These dyes may be used alone or in combination of two or more.

Specifically, C.I. Solvent dyes, C.I. Acid dyes, C.I. Direct dye, C.I. And modern dyes.

C.I. As the solvent dye, C.I. Solvent Orange 2, 7, 11, 15, 26, 56, or C.I. Solvent yellow.

C.I. As the acid dye, C.I. Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 169, 173; Acid Yellow.

C.I. As the direct dye, C.I. Direct orange 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107; Direct Yellow.

C.I. As the modern dye, C.I. 43, 47, 48, or a combination of the above-described &lt; RTI ID = 0.0 &gt; CI Mordant yellow, and the like.

As the dye (A-1), yellow dyes are preferable, and yellow dyes such as coumarin dyes, binding azo dyes, pyridone azo dyes, barbitur azo dyes, quinophthalone dyes, methine dyes or cyanine dyes are preferable.

The pigment is not particularly limited and a known pigment can be used. Examples of the pigment include pigments classified as pigments in the color index (The Society of Dyers and Colourists).

As a specific example thereof, C.I. Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 137, 138, 139 , 147, 148, 150, 153, 154, 166, 173, 194 and 214;

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

The above-described C.I. And green pigments such as pigment green pigments.

As the pigment, C.I. Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 137, 139, 147 , 148, 150, 153, 154, 166, 173, 185, 194 and 214; C.I. Green pigments such as Pigment Green 7, 36 and 58 are preferable, and C.I. Pigment Yellow 138, 150, 185 and C.I. Pigment Green 58 is more preferable, and C.I. Pigment Yellow 138 and C.I. Pigment Green 58 is more preferable. By including the above-mentioned pigment, it is easy to optimize the transmission spectrum.

The content of the compound represented by the formula (II-1) is usually 3 to 100 mass%, preferably 4 to 50 mass%, and more preferably 5 to 30 mass%, based on the total amount of the colorant.

The content of the compound represented by the formula (II-2) is usually 3 to 100 mass%, preferably 4 to 50 mass%, and more preferably 5 to 30 mass%, based on the total amount of the colorant.

The compounds of the present invention are preferable because the color filters having a high lightness can be easily obtained if the contents are within the above ranges.

A colored curable resin composition comprising a compound represented by the formula (II-1) or (II-2), a resin (B), a polymerizable compound (C), a polymerization initiator (D) and a solvent (E) This colored curable resin composition is referred to as &quot; colored curable resin composition (A) &quot;) is also one of the present invention.

The colored curable resin composition (A) contains at least one compound of the present invention as a coloring agent. The colored curable resin composition may further contain the above-mentioned dye (A-1) or pigment as a colorant.

In the colored curable resin composition (A), the total content of the colorant is preferably 5 to 60 mass%, more preferably 8 to 55 mass%, and still more preferably 10 to 50 mass%, based on the total solid content Mass%. When the total content of the colorant is within the above range, the color density of the color filter is sufficient and the resin (B) or the polymerizable compound (C) can be contained in a required amount in the composition. Can be formed. Here, the "total amount of solid content" in the present specification means the amount excluding the content of the solvent in the total amount of the colored curable resin composition. The total amount of the solid content and the content of each component in the total amount can be measured by known analytical means such as liquid chromatography or gas chromatography.

&Lt; Resin (B) >

The resin (B) is not particularly limited, but is preferably an alkali-soluble resin. Examples of the resin (B) include the aforementioned resins [K1] to [K6].

Specific examples and preferable examples of the resin (B) are the same as those of the above-mentioned colored curable resin composition (1).

The content of the resin (B) in the colored curable resin composition (A) is preferably 7 to 65% by mass, more preferably 13 to 60% by mass, more preferably 17 To 55% by mass. When the content of the resin (B) is within the above range, a colored pattern can be formed, and the resolution and residual film ratio of the colored pattern tends to be improved.

&Lt; Polymerizable compound (C) >

The polymerizable compound (C) is a compound which can be polymerized by an active radical and / or an acid generated from the polymerization initiator (D). As the polymerizable compound (C), a compound having a polymerizable ethylenically unsaturated bond and the like can be mentioned, and a (meth) acrylic acid ester compound is preferable.

Specific examples and preferable examples of the polymerizable compound (C) are the same as those of the above-mentioned colored curable resin composition (1).

In the colored curable resin composition (A), the content of the polymerizable compound (C) is preferably from 7 to 65% by mass, more preferably from 13 to 60% by mass, Is from 17 to 55 mass%. When the content of the polymerizable compound (C) is within the above range, the residual film ratio at the time of forming a color pattern and the chemical resistance of the color filter tend to be improved.

&Lt; Polymerization initiator (D) >

The polymerization initiator (D) is not particularly limited as long as it is a compound capable of generating an active radical or an acid by the action of light or heat to initiate polymerization of the polymerizable compound (C), and a known polymerization initiator can be used .

Specific examples and preferable examples of the polymerization initiator (D) are the same as those of the above-mentioned colored curable resin composition (1).

The content of the polymerization initiator (D) in the colored curable resin composition (A) is preferably 0.1 to 30 parts by mass, more preferably 0.1 to 30 parts by mass based on 100 parts by mass of the total amount of the resin (B) Is 1 to 20 parts by mass. When the content of the polymerization initiator (D) is in the above range, the productivity is improved because the sensitivity is increased and the exposure time is shortened.

&Lt; Solvent (E) >

The solvent (E) is not particularly limited, and a solvent commonly used in the field can be used.

Specific examples and preferred examples of the solvent (E) are the same as those of the above-mentioned colored curable resin composition (1).

In the colored curable resin composition (A), the content of the solvent (E) is preferably 70 to 95% by mass, and more preferably 75 to 92% by mass, based on the total amount of the composition. When the content of the solvent (E) is within the above range, the flatness at the time of coating becomes good, and the color characteristics are not insufficient when the color filter is formed, so that the display characteristics tend to be good.

&Lt; Other components >

The colored curable resin composition (A) of the present invention may contain additives known in the art such as a polymerization initiator, a leveling agent, a filler, another polymer compound, an adhesion promoter, an antioxidant, a light stabilizer, May be included.

&Lt; Production method of colored curable resin composition (A)

The colored curable resin composition (A) contains a compound represented by the formula (II-1) or (II-2), a resin (B), a polymerizable compound (C), a polymerization initiator (D) And a leveling agent, a polymerization initiator, and other components which are used as needed.

The pigment (P) is preferably mixed with a part or the whole of the solvent (E) and dispersed with a bead mill or the like until the average particle diameter of the pigment becomes about 0.2 탆 or less. At this time, a part or the whole of the pigment dispersant and the resin (B) may be blended if necessary. The desired coloring curable resin composition can be prepared by mixing the remaining components in the thus obtained pigment dispersion to a predetermined concentration.

The dye may be previously dissolved in a part or all of the solvent (E) to prepare a solution. The solution is preferably filtered with a filter having a pore diameter of about 0.01 to 1 mu m.

The colored curable resin composition after mixing is preferably filtered with a filter having a pore diameter of about 0.1 to 10 mu m.

<Manufacturing Method of Color Filter and the Like>

Coating films and color filters formed from the colored curable resin composition (A) also fall within the scope of the present invention. A display device including the color filter is also included in the scope of the present invention.

The color filter means a film obtained by curing the colored curable resin composition (A) and a cured film having a specific pattern. The coating film refers to the color filter or a film obtained by coating on a substrate and drying.

The film thickness of the color filter is not particularly limited and may be appropriately adjusted according to the purpose or use, and is, for example, from 0.1 to 30 탆, preferably from 0.1 to 20 탆, more preferably from 0.5 to 6 탆.

As the substrate, the substrate exemplified for the color filter obtained from the colored curable resin composition (A) is used. A separate color filter layer, a resin layer, a transistor, a circuit, and the like may be formed on these substrates.

The coating film and the method of producing the color filter are not particularly limited. The coating film and the color filter can be made, for example, in the same manner as a coating film or color filter formed from the above-mentioned colored curable resin composition (1).

According to the colored curable resin composition (A), a color filter having particularly excellent brightness can be produced. The color filter is useful as a color filter used in a display device (e.g., a liquid crystal display device, an organic EL device, an electronic paper, etc.) and a solid-state image pickup device.

Example

Hereinafter, the present invention is described in more detail by way of examples, but the present invention is not limited to these examples. In the examples,% and parts representing the content or amount are based on mass unless otherwise specified.

In the following synthesis examples, the compound was identified (identified) by NMR (JNM-EX-270; manufactured by Nippon Denshi Co., Ltd.).

Synthesis Example 1: Synthesis of Compound Represented by Formula (AII-16)

18.7 parts of N, N-dibutyl aniline (manufactured by Tokyo Kasei Kogyo Co., Ltd.), 4.6 parts of 3,4-dihydroxy-3-cyclobutene-1,2-dione (manufactured by Tokyo Kasei Kogyo Co., 542.3 parts of butanol and 362.6 parts of toluene were mixed, and the resulting mixture was stirred for 5 hours at 125 DEG C while removing water generated using a Dean-Stark tube. After completion of the reaction, the solvent was distilled off and a small amount of toluene After the addition of 100 parts of hexane, the precipitated solid was collected by filtration, followed by filtration to obtain a solid. The solid was washed with 20 parts of tetrahydrofuran and then with 50 parts of hexane to obtain a solid. The resulting solid was dried under reduced pressure at 60 DEG C for 24 hours to obtain a compound represented by the formula (AII-16) 3.94 parts was obtained.

¹ H-NMR (270 MHz,? Value (ppm, based on TMS), CDCl ₃ ) of the compound represented by the formula (AII-16)

(d, 2H), 8.35 (d, 2H), 1.40 (m, 8H)

Synthesis Example 2: Synthesis of a compound represented by the formula (AII-23)

5.4 parts of N, N-dibutyl-3-aminophenol (manufactured by Tokyo Kasei Kogyo K.K.), 3,4-dihydroxy-3-cyclobutene-1,2-dione , 200.7 parts of 1-butanol and 134.1 parts of toluene were mixed. The resulting mixture was stirred at 125 &lt; 0 &gt; C for 5 hours, while the water generated using a Dean-Stark tube was removed. After completion of the reaction, the solvent was distilled off, a small amount of toluene was added, and 100 parts of water was added to discard the aqueous layer. The obtained organic layer was washed with water twice, and then 50 parts of hexane was added. The precipitated solid was collected by filtration. The solid obtained by filtration was dispersed in 5 parts of tetrahydrofuran, filtered, washed with 10 parts of tetrahydrofuran, and then washed with 25 parts of hexane. The resulting solid was dried under reduced pressure at 60 占 폚 for 24 hours to obtain 3.23 parts of a compound represented by the formula (AII-23).

¹ H-NMR (270 MHz,? Value (ppm, based on TMS), CDCl ₃ ) of the compound represented by the formula (AII-

(d, 2H), 6.30 (d, 2H), 7.30 (d, 2H) 12.07 (s, 2 H)

Synthesis Example 3: Synthesis of Compound Represented by Formula (AII-62)

, 2.5 parts of 3-ethoxy-N, N-diethylaniline (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 2.5 parts of 3,4-dihydroxy-3-cyclobutene-1,2-dione ], 103.7 parts of 1-butanol and 55.7 parts of toluene were mixed. The resulting mixture was stirred at 125 &lt; 0 &gt; C for 5 hours, while the water generated using a Dean-Stark tube was removed. After completion of the reaction, the solvent was distilled off, a small amount of toluene was added, and 50 parts of water was added to discard the aqueous layer. The obtained organic layer was washed with water twice, and then 25 parts of hexane was added. The precipitated solid was collected by filtration. The solid obtained by filtration was dispersed in 3 parts of tetrahydrofuran, filtered, and then washed with 4 parts of tetrahydrofuran and subsequently with 10 parts of hexane. The resulting solid was dried under reduced pressure at 60 DEG C for 24 hours to obtain 0.95 part of a compound represented by the formula (AII-62).

Formula ¹ H-NMR (270MHz, δ values (ppm, TMS standard), DMSO-d8) of the compound represented by (AII-62) δ 1.16 ( t, 12H), 1.42 (t, 6H), 3.52 (q, (D, 2H), 4.12 (q, 4H), 6.15 (s, 2H), 6.48

Synthesis Example 4

In a flask equipped with a stirrer, a thermometer, a reflux condenser, a dropping funnel and a gas inlet tube, nitrogen was flowed at 0.02 L / min to make a nitrogen atmosphere, and 305 parts of propylene glycol monomethyl ether acetate was added and heated to 70 DEG C with stirring . Then, 36 parts of acrylic acid; (Monomer represented by the formula (BI-1)} and 3,4-epoxytricyclo [5.2.1.0 ² (5-epoxytricyclo [5.2.1.0 ^2,6 ] decan- ^{, 6} ] decan-8-yl acrylate {that is, the monomer represented by the formula (BII-1)} {the molar ratio of each monomer in the mixture = 50: 50} was dissolved in 140 parts of propylene glycol monomethyl ether acetate To prepare a monomer solution. The monomer solution was added dropwise into a flask kept at 70 캜 for 4 hours using a dropping funnel. On the other hand, the polymerization initiator solution in which 30 parts of the polymerization initiator 2,2'-azobis (2,4-dimethylvaleronitrile) was dissolved in 225 parts of propylene glycol monomethyl ether acetate was added dropwise over 4 hours Lt; / RTI &gt; After completion of the dropwise addition of the polymerization initiator solution, the mixture was maintained at 70 캜 for 4 hours and then cooled to room temperature to obtain a polymer having a weight average molecular weight Mw of 9000, a molecular weight distribution of 2.0, a solid content of 33% and a solid acid value of 90 mg- To obtain a resin B1 solution.

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

Device; K2479 (manufactured by Shimadzu Seisakusho Co., Ltd.)

column; SHIMADZU Shim-pack GPC-80M

Column temperature; 40 ℃

menstruum; THF (tetrahydrofuran)

Flow rate; 1.0 ml / min

Detector; RI

Calibration standards; TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 [

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

Examples 1 to 6, Comparative Example 1 and Comparative Example 2

&Lt; Preparation of colored curable resin composition >

Each component was mixed so as to have the composition shown in Table 6 to obtain a colored curable resin composition.

^{1) The} pigment was mixed with the pigment dispersant and propylene glycol monomethyl ether acetate in the amount described in E- ¹³⁾ and dispersed in advance.

²⁾ E-1 ²⁾ represents the total content of propylene glycol monomethyl ether acetate.

Further, in Table 6, each component represents the following. The resin (B) represents a part by mass in terms of solid content.

A-1-1: A compound represented by the formula (AII-16)

A-1-2: A compound represented by the formula (AII-23)

A-1-3: A compound represented by the formula (AII-62)

A-2-1: C.I. Pigment Yellow 138

A-2-2: C.I. Pigment Green 58 [FASTOGEN (R) Green A110; Manufactured by DIC Corporation)

A-2-3: Pigment Yellow 150

Resin (B): Resin B1

Polymerizable compound (C): dipentaerythritol hexaacrylate [KAYARAD (R) DPHA; Manufactured by Nippon Kayaku Co., Ltd.]

Polymerization initiator (D): N-1919 (O-acyloxime compound, manufactured by ADEKA)

E-1: Propylene glycol monomethyl ether acetate

E-2: N-methylpyrrolidone

Leveling agent (F): Polyether-modified silicone oil (TORAY Silicone SH8400; Manufactured by Toray Dow Corning Co., Ltd.]

<Fabrication of colored coating film>

The colored curable resin composition was coated on a square glass substrate (Eagle XG; manufactured by Corning) with a side length of 5 cm by a spin coat method so that the film thickness after post-baking was 2.2 占 퐉, and then prebaked at 100 占 폚 for 3 minutes Respectively. After cooling down, an exposure machine [TME-150RSK; (Manufactured by Topcon Co., Ltd.) at an exposure amount of 60 mJ / cm &lt; 2 &gt; (based on 365 nm) in an air atmosphere. After the light irradiation, post-baking was carried out in an oven at 160 DEG C for 20 minutes to obtain a colored coating film (hereinafter, this colored coating film was referred to as a &quot; coating film &quot;).

&Lt; Measurement of film thickness &

With respect to the obtained coating film, a film thickness measuring device [DEKTAK3; Manufactured by Shin Kugi &amp; Co., Ltd., Japan) was used to measure the film thickness. The results are shown in Table 7.

&Lt; Evaluation of color &

With respect to the obtained coating film, a colorimeter [OSP-SP-200; (X, y) and a tristimulus value (Y) in an XYZ colorimetric system of CIE were measured using a characteristic function of a C light source. The larger the value of Y, the higher the brightness. The results are shown in Table 7.

<Measurement of contrast>

The glass substrate on which the coating film was formed was sandwiched between polarizing films (POLAX-38S, manufactured by LuKeo Co., Ltd.) to obtain measurement samples.

Using a contrast colorimeter (CT-1; manufactured by Tsubosaka Kikai Co., Ltd., detector: BM-5A, light source: F-10), the obtained coating film was subjected to contrast measurement with a blank value of 30000. The results are shown in Table 7.

From the above results, it was confirmed that the coloring pattern formed from the colored curable resin composition of the present invention was excellent in brightness and contrast. From this, it was found that it is possible to manufacture a display device having excellent color performance by using a colored pattern formed from the colored curable resin composition (1) as a color filter.

Example 7: Synthesis of a compound represented by the formula (AII-1-5)

5.0 parts of 3 '- (diethylamino) acetanilide (manufactured by Wako Pure Chemical Industries, Ltd.) and 50 parts of 10% sulfuric acid were mixed. The resulting mixture was stirred at 90 占 폚 for 5 hours. After the completion of the reaction, 20 parts of water was added, followed by neutralization with 15% of caustic soda water, and 100 parts of chloroform was added to discard the aqueous layer. The obtained organic layer was washed with water twice, and then the solvent was distilled off. The resulting oil was dried under reduced pressure at 60 占 폚 for 24 hours to obtain 4.8 parts of a compound represented by the formula (d1-1).

¹ H-NMR (270 MHz,? Value (ppm, based on TMS), CDCl ₃ ) of the compound represented by formula (d1-1)

2H), 6.16 (m, IH), 7.01 (t, IH)

3.0 parts of the compound represented by the formula (d1-1) and 7.6 parts of pyridine were mixed and cooled at 4 占 폚. 3.2 parts of 2-ethylhexyl chloride (Tokyo Kasei Kogyo Co., Ltd.) and 2.5 parts of pyridine was added dropwise to the resulting mixture over 1 hour, and the mixture was stirred at 4 캜 for 7 hours. 30 parts of water and 100 parts of 3% hydrochloric acid were added, and 100 parts of chloroform was added to discard the aqueous layer. The operation of washing with water was repeated twice, and then the solvent was distilled off. The residue was purified by silica gel column chromatography (eluent: chloroform / toluene = 1/1) and the obtained oil was dried under reduced pressure at 60 ° C for 24 hours to obtain 3.3 parts of a compound represented by the formula (d1-2).

¹ H-NMR (270 MHz,? Value (ppm, based on TMS), CDCl 3) of the compound represented by formula (d1-2)

(m, 4H), 2.66 (m, 1H), 3.28 (q, 4H), 3.99 (br, 1H), 7.21 (m, 1H), 7.31 (m, 1H)

2.1 parts of the compound represented by the formula (d1-2), 0.6 part of 3,4-dihydroxy-3-cyclobutene-1,2-dione (manufactured by Tokyo Kasei Kogyo Co., Ltd.), 87.9 parts of 1-butanol, Were mixed. The resulting mixture was stirred at 125 &lt; 0 &gt; C for 5 hours, while the water generated using a Dean-Stark tube was removed. After completion of the reaction, the solvent was distilled off, a small amount of toluene was added, and 100 parts of water was added to discard the aqueous layer. The obtained organic layer was washed with water twice, and then 50 parts of hexane was added. The precipitated solid was collected by filtration. The solid obtained by filtration was dispersed in 5 parts of tetrahydrofuran, filtered, and the solid was washed with 10 parts of tetrahydrofuran and then with 25 parts of hexane. The obtained solid was dried under reduced pressure at 60 占 폚 for 24 hours to obtain 0.2 part of a compound represented by the formula (AII-1-5).

¹ H-NMR (270 MHz,? Value (ppm, based on TMS), CDCl ₃ ) of the compound represented by the formula (AII-

4H), 2.65 (m, 2H), 2.65 (m, 2H), 1.64 (t, 2H) 2H), 8.50 (m, 2H), 12.00 (d, 2H), 3.53 (d, 2H)

Example 8: Synthesis of a compound represented by the formula (AII-2-8)

10.0 parts of 2,4-dimethylaniline (manufactured by Tokyo Kasei Kogyo Co., Ltd.), 17.0 parts of 2-ethylhexane bromide (manufactured by Tokyo Kasei Kogyo Co., Ltd.), 44.0 parts of tetrabutylammonium bromide [manufactured by Wako Pure Chemical Industries, Were mixed. The resulting mixture was stirred at 90 &lt; 0 &gt; C for 8 hours. After completion of the reaction, 50 parts of 10% aqueous sulfuric acid solution was added, and 100 parts of ethyl acetate was added to discard the aqueous layer. The obtained organic layer was washed twice with water and 10% hydrochloric acid, and then the solvent was distilled off. The obtained oil was dried under reduced pressure at 60 占 폚 for 24 hours to obtain 9.3 parts of a compound represented by the following formula (d2-1).

¹ H-NMR (270 MHz,? Value (ppm, based on TMS), DMSO-d 6) of the compound represented by the formula (d2-1)

3H), 2.91 (s, 3H), 2.91 (d, 2H), 4.37 (br, IH) ), 6.38 (d, 1 H), 6.75 (s, 1 H), 6.77 (d,

3.0 parts of a compound represented by the formula (d2-1), 2.2 parts of 3-bromophenol (manufactured by Tokyo Kasei Kogyo Co., Ltd.), 0.015 parts of palladium acetate, and 3.2 parts of tert-butoxysodium (manufactured by Tokyo Kasei Kogyo Co., Ltd.) , 0.055 part of tri-tert-butylphosphine (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 25.6 parts of toluene were mixed and stirred at 100 ° C for 15 hours. To the obtained mixture, 30 parts of ethyl acetate and 100 parts of water were added to discard the water layer. The obtained organic layer was washed with water twice, and then the solvent was distilled off. The residue was purified by silica gel chromatography (chloroform / hexane = 1/1) and the obtained oil was dried under reduced pressure at 60 ° C for 24 hours to obtain 1.9 parts of a compound represented by the following formula (d2-2).

¹ H-NMR (270MHz, δ values (ppm, TMS standard), DMSO-d6) of the compound represented by the formula (d2-2) 0.85 (m, 6H ), 1.23-1.42 (br, 8H), 1.55 (br 1H), 6.76 (s, 3H), 2.27 (s, 3H), 2.90 (d, 2H), 6.37 m, 4 H), 8.93 (s, 1 H)

4.4 parts of a compound represented by the formula (d2-2), 0.8 part of 3,4-dihydroxy-3-cyclobutene-1,2-dione (manufactured by Tokyo Kasei Kogyo Co., Ltd.), 90.0 parts of 1- 60.0 parts were mixed. The resulting mixture was stirred at 125 &lt; 0 &gt; C for 3 hours while removing the water produced using a Dean-Stark tube. After completion of the reaction, the solvent was distilled off, 15 parts of acetic acid was added, and the mixture was added dropwise to 100 parts of 18% saline. The precipitated solid was collected by filtration. The solid was filtered off and washed with hexane. The resulting solid was dried under reduced pressure at 60 占 폚 for 24 hours to obtain 4.9 parts of a compound represented by the formula (AII-2-8).

Formula ^{0.87 1 H-NMR ((ppm} , TMS standard), DMSO-d6 270MHz, δ value) of the compound represented by (AII-2-8) (m, 12H), 1.21-1.57 (m, 16H), 1.72 (m, 6H), 2.32 (s, 3H), 2.37 (s, 3H) 7.77-7.95 (m, 2H), 11.35 (s, 1 H), 12.06 (s, 1 H)

Test Example 1 and Test Example 2, Comparative Test Example 1 and Comparative Test Example 2

Propylene glycol monomethyl ether (hereinafter referred to as PGME), ethyl lactate (hereinafter, referred to as EL) are added to the compound represented by the formula (AII-1-5) and the compound represented by the formula (AII- ) And propylene glycol monomethyl ether acetate (hereinafter, referred to as PGMEA) were determined as follows.

<Solubility of dye>

In a 50 ml sample tube, the above compound and the solvent were mixed in the following proportions, respectively. Thereafter, the sample tube was tightly closed and the mixture was vibrated with an ultrasonic vibrator at 30 캜 for 3 minutes. Subsequently, the resulting mixture was allowed to stand at room temperature for 30 minutes, and subjected to suction filtration, and the residue (i.e., insoluble material) was visually observed. When the insoluble matter was not identified, it was determined that the solubility was good, and when it was confirmed that the insoluble matter was confirmed, the solubility was judged as poor and the result was rated as x.

Test Example 1: Use of a compound represented by the formula (AII-1-5).

0.05 g of the compound was dissolved in 1 g of the solvent (EL).

0.0 &gt; g &lt; / RTI &gt; of the compound was dissolved (dissolved) in 1 g of solvent (PGME)

Solubilize 0.01 g of the above compound per 1 g of the solvent (PGMEA)

Test Example 2: Use of a compound represented by the formula (AII-2-8).

Solubilize 0.1 g of the above compound per 1 g of solvent (PGME).

Solubilize 0.15 g of the above compound per 1 g of solvent (EL).

0.01 g of the above compound was dissolved in 1 g of a solvent (PGMEA).

Separately, the solubility of the compound represented by the formula (II-0-1) was determined as Comparative Test Example 1, and the solubility of the compound represented by the formula (II-0-2) And it was obtained in the same manner as in Example 2.

The results are shown in Tables 8 and 9.

Synthesis Example 7

In a flask equipped with a reflux condenser, a dropping funnel and a stirrer, nitrogen was appropriately flowed to make a nitrogen atmosphere, and 100 parts of propylene glycol monomethyl ether acetate was added and heated to 85 DEG C with stirring. Subsequently, 19 parts of methacrylic acid, 3,4-epoxytricyclo [5.2.1.0 ^2,6 ] decan-8-yl acrylate and 3,4-epoxytricyclo [5.2.1.0 ^2,6 ] Decane-9-yl acrylate (content ratio: 50/50 by mol) (trade name: E-DCPA, manufactured by Daicel Co., Ltd.) in 40 parts of propylene glycol monomethyl ether acetate. Was added dropwise over about 5 hours. On the other hand, a solution prepared by dissolving 26 parts of polymerization initiator 2,2'-azobis (2,4-dimethylvaleronitrile) in 120 parts of propylene glycol monomethyl ether acetate was dropped into a flask using a dropping pump for about 5 hours Respectively. After the dropping of the polymerization initiator was completed, the temperature was maintained at the same temperature for about 3 hours and then cooled to room temperature to obtain a solution of a copolymer (resin (B-1)) having a solid content of 43.5%. The obtained resin (B-1) had a weight average molecular weight of 8000, a molecular weight distribution of 1.98, and an acid value in terms of solid content of 53 mg-KOH / g.

The weight average molecular weight (Mw) and the number average molecular weight (Mn) of the resin in terms of polystyrene were measured by the GPC method under the following conditions.

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

column; TSK-GELG2000HXL

Column temperature; 40 ℃

menstruum; THF

Flow rate; 1.0 ml / min

Solid concentration of the test solution; 0.001 to 0.01 mass%

Dose; 50 μl

Detector; RI

Calibration standards; TSK STANDARD POLYSTYRENE

F-40, F-4, F-288, A-2500 and A-500 (manufactured by Tosoh Corporation)

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

Example 9, Example 10 and Comparative Example 3

&Lt; Preparation of colored curable resin composition >

Each component was mixed so as to have the composition shown in Table 10 to obtain a colored curable resin composition.

^{1) The} pigment was mixed with the pigment dispersant and propylene glycol monomethyl ether acetate in the amount described in E- ¹³⁾ and dispersed in advance.

2) E-1 ²⁾ represents the total content of propylene glycol monomethyl ether acetate.

Further, in Table 10, each component represents the following. Further, the resin (B-1) represents a part by mass in terms of solid content.

AII-1-5: A compound represented by the formula (AII-1-5)

AII-2-8: A compound represented by the formula (AII-2-8)

A-2-3: C.I. Pigment Yellow 150

A-2-2: C.I. Pigment Green 58 [FASTOGEN (R) Green A110; Manufactured by DIC Corporation)

Resin (B): Resin B1

Polymerizable compound (C): dipentaerythritol hexaacrylate [KAYARAD (R) DPHA; Manufactured by Nippon Kayaku Co., Ltd.]

Polymerization initiator (D): N-1919 (O-acyloxime compound, manufactured by ADEKA)

E-1: Propylene glycol monomethyl ether acetate

E-2: N-methylpyrrolidone

Leveling agent (F): Polyether-modified silicone oil (TORAY Silicone SH8400; Manufactured by Toray Dow Corning Co., Ltd.]

<Fabrication of Coating Film>

The colored curable resin composition was coated on a square glass substrate (Eagle XG; manufactured by Corning) having a side length of 5 cm by a spin-coat method so that the film thickness after post-baking was 2.2 占 퐉, Baked. After cooling, the substrate was irradiated with light at an exposure dose of 60 mJ / cm 2 (based on 365 nm) in an air atmosphere using an exposure apparatus (TME-150RSK; Topcon Co., Ltd.) Minute post-baking was carried out to obtain a coated film.

&Lt; Measurement of film thickness &

With respect to the obtained coating film, a film thickness measuring device [DEKTAK3; (Manufactured by Nihon Shinkuigi Co., Ltd.) was used to measure the film thickness. The results are shown in Table 10.

&Lt; Evaluation of color &

With respect to the obtained coating film, a colorimeter [OSP-SP-200; (X, y) and a tristimulus value (Y) in an XYZ colorimetric system of CIE were measured using a characteristic function of a C light source. The larger the value of Y, the higher the brightness. The results are shown in Table 10.

<Measurement of contrast>

The glass substrate on which the coating film was formed was sandwiched between polarizing films (POLAX-38S, manufactured by LuKeo Co., Ltd.) to obtain measurement samples.

Using a contrast colorimeter (CT-1; manufactured by Tsubosaka Kikai Co., Ltd., detector: BM-5A, light source: F-10), the obtained color coating film was subjected to contrast measurement with a blank value of 30000. The results are shown in Table 10.

From the above results, it was confirmed that the coloring pattern formed from the colored curable resin composition of the present invention was excellent in brightness and contrast. From this, it was found that it is possible to manufacture a display device having excellent color performance by using a coloring pattern formed from the colored curable resin composition (A) as a color filter.

The color-curable resin composition of the present invention is excellent as a color-curable resin composition used for a color filter of a display device such as a liquid crystal display device because the color filter produced by the color-curable resin composition of the present invention has high brightness and good contrast.

The compound of the present invention is excellent in solubility in an organic solvent. Therefore, when a colored curable resin composition containing a colorant containing the compound of the present invention is used, it is possible to produce a color filter of high quality with less occurrence of foreign matter.

Claims (13)

CI Pigment Yellow 138, a green pigment and a yellow dye, and at least one colorant (A1) selected from the group consisting of CI Pigment Yellow 138,
A squarylium dye (A2)
The resin (B)
The polymerizable compound (C)
The polymerization initiator (D)
Solvent (E)
And a coloring curable resin. The colorant according to claim 1, wherein the C.I. Pigment Yellow 138. &lt; / RTI &gt; The colored curable resin composition according to claim 1, which contains a yellow dye as the colorant (A1). A coating film formed from the colored curable resin composition according to any one of claims 1 to 3. A color filter formed from the colored curable resin composition according to any one of claims 1 to 3. A display device comprising the color filter according to claim 5. A compound represented by the formula (II-1).

[Wherein R ^1a to R ^4a each independently represent a hydrogen atom, a halogen atom, a hydroxy group or a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms. The hydrogen atom or the methyl group contained in the monovalent saturated hydrocarbon group may be substituted with a halogen atom, a hydroxy group or an alkylamino group having 1 to 8 carbon atoms, and an oxygen atom or a sulfur atom is inserted between the carbon atoms constituting the monovalent saturated hydrocarbon group .
R ^5a and R ^6a each independently represent a hydrogen atom or a hydroxy group.
R ^7a and R ^8a each independently represent a monovalent saturated hydrocarbon group having 8 to 20 carbon atoms or a group represented by the formula (i-1).

In the above formula, R ^14a represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms or a monovalent unsaturated hydrocarbon group having 2 to 20 carbon atoms, and m1 represents an integer of 1 to 5. When m1 is 2 or more, plural R &lt; ^{14a &gt;} may be the same or different. * Represents the number of bonds with carbon atoms (hands).
R ^9a to R ^12a each independently represent a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms or a group represented by the formula (i-1). The hydrogen atom or the methyl group contained in the monovalent saturated hydrocarbon group may be substituted with a halogen atom, a hydroxy group or an alkylamino group having 1 to 8 carbon atoms, and an oxygen atom or a sulfur atom is inserted between the carbon atoms constituting the monovalent saturated hydrocarbon group It may be.] A compound represented by the formula (II-2).

[Wherein R ^1b to R ^4b each independently represent a hydrogen atom, a halogen atom, a hydroxy group or a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms. The hydrogen atom or the methyl group contained in the monovalent saturated hydrocarbon group may be substituted with a halogen atom, a hydroxy group or an alkylamino group having 1 to 8 carbon atoms, and an oxygen atom or a sulfur atom is inserted between the carbon atoms constituting the monovalent saturated hydrocarbon group .
Each of R ^5b to R ^8b independently represents a hydrogen atom or a hydroxy group.
Ar ^1b and Ar ^2b each independently represent a group represented by the formula (i-2).

In the above formula, R ^12b represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms or a monovalent unsaturated hydrocarbon group having 2 to 20 carbon atoms, and m2 represents an integer of 1 to 5. When m2 is 2 or more, plural ^R12b may be the same or different. * Represents the number of bonds with nitrogen atoms.
R ^9b and R ^10b each independently represent a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms or a group represented by the formula (i-2). The hydrogen atom or the methyl group contained in the monovalent saturated hydrocarbon group may be substituted with a halogen atom, a hydroxy group or an alkylamino group having 1 to 8 carbon atoms, and an oxygen atom or a sulfur atom is inserted between the carbon atoms constituting the monovalent saturated hydrocarbon group It may be.] A colorant comprising the compound according to claim 7 or 8. A colored curable resin composition comprising a compound, a resin, a polymerizable compound, a polymerization initiator, and a solvent according to claim 7 or 8. A coating film formed using the colored curable resin composition according to claim 10. A color filter formed using the tinting curable composition according to claim 10. A display device comprising the color filter according to claim 12.