TW202244194A - Red coloring composition useful for thinning color filters and improving brightness thereof - Google Patents

Abstract

The present invention provides a red coloring composition useful for thinning color filters and improving brightness thereof. The red coloring composition of the present invention includes a colorant (A), a resin (B), a polymerizable compound (C), a polymerization initiator (D) and a solvent (E). The colorant (A) includes an orange colorant (A-1) satisfying a condition (X), a red colorant (A-2) and a yellow coloring agent (A-3) containing at least one selected from the group consisting of metal-containing azo dyes, isoindoline dyes and coumarin dyes. A content of the yellow colorant (A-3) is 250 parts by mass or less with respect to 100 parts by mass of the orange colorant (A-1). [Condition (X)] The absorbance at a wavelength of 480 nm is 0.40 or more, the absorbance at a wavelength of 530 nm is 0.55 or more and the absorbance at a wavelength of 580 nm is 0.20 or less.

Description

red coloring composition

The invention relates to a red coloring composition, a color filter, a display device and a solid-state imaging element.

Used in display devices such as liquid crystal display devices, electroluminescent display devices, and plasma displays, or solid-state imaging devices such as CCD (Charge Coupled Device) or CMOS (complementary metal oxide semiconductor) sensors The color filter is made of colored curable resin composition. C.I. Pigment Orange (Pigment Orange) 43 (Patent Documents 1 to 3) and C.I. Pigment Orange 64 (Patent Document 3) are known as coloring agents used in the colored curable resin composition for forming the color filter. ~5) etc. [Prior Art Literature] [Patent Document]

[Patent Document 1] Japanese Patent Laid-Open No. 11-310714 [Patent Document 2] Japanese Patent Laid-Open No. 2003-183511 [Patent Document 3] Japanese Patent Laid-Open No. 2016-212372 [Patent Document 4] Japanese Patent Laid-Open No. 2017-68159 [Patent Document 5] Japanese Patent Laid-Open No. 2012-173356

[Problem to be solved by the invention]

In recent years, the thinning of color filters has become a technical trend. However, part of the yellow-based colorant necessary for reproducing red color needs to be excessive due to insufficient absorption strength, and it may be difficult to reduce the thickness of the color filter. Also, a color filter containing a quinophthalone-based colorant represented by C.I. Pigment Yellow 138 as a colorant may have poor brightness.

An object of the present invention is to provide a red coloring composition useful for thinning a color filter and improving brightness. [Technical means to solve the problem]

That is, the gist of the present invention is as follows. [1] A red coloring composition comprising a colorant (A), a resin (B), a polymerizable compound (C), a polymerization initiator (D) and a solvent (E), The above-mentioned colorant (A) includes an orange colorant (A-1), a red colorant (A-2) satisfying the condition (X), and a metal-containing azo dye, isoindoline dye, and coumarin At least one yellow coloring agent (A-3) of the group consisting of pigments, Content of a yellow coloring agent (A-3) is 250 mass parts or less with respect to 100 mass parts of orange coloring agents (A-1). [Condition (X)] Preparation of the composition (X-1) which contains only the orange colorant (A-1) as a colorant, and the content of the orange colorant (A-1) in the solid content reaches 10% by mass. (X-1) When measuring the absorbance of a color filter with a film thickness of 1 μm, The absorbance at a wavelength of 480 nm is above 0.40, The absorbance at a wavelength of 530 nm is above 0.55, Absorbance at a wavelength of 580 nm is below 0.20. [2] The red coloring composition as described in [1], wherein the above-mentioned red coloring agent (A-2) satisfies the condition (Y). [Condition (Y)] A composition (Y) containing only the red colorant (A-2) as a colorant was prepared, and the content of the red colorant (A-2) in the solid content was 10% by mass. ) to measure the absorbance of a color filter with a film thickness of 1 μm, The absorbance at a wavelength of 440 nm is below 0.30, The absorbance at a wavelength of 480 nm does not reach 0.50, The absorbance at a wavelength of 530 nm is above 0.30, The absorbance at a wavelength of 580 nm is above 0.10. [3] The red coloring composition as described in [1] or [2], wherein the above-mentioned yellow coloring agent (A-3) satisfies the condition (Z). [Condition (Z)] Preparation of a composition (Z-1) containing only the yellow colorant (A-3) as a colorant, and the content of the yellow colorant (A-3) in the solid content is 10% by mass. (Z-1) When measuring the absorbance of a color filter with a film thickness of 1 μm, The absorbance at a wavelength of 440 nm is above 0.50, The absorbance at a wavelength of 480 nm is above 0.20, The absorbance at a wavelength of 530 nm is below 0.10, The absorbance at a wavelength of 580 nm is below 0.10. [4] The red coloring composition according to any one of [1] to [3], wherein the orange colorant (A-1) contains at least one selected from C.I. Pigment Orange 43 and C.I. Pigment Orange 64 above. [5] The red coloring composition as described in any one of [1] to [4], wherein the red colorant (A-2) is selected from the group consisting of C.I. Pigment Red 177, C.I. Pigment Red 254, and C.I. Pigment Red 269. , at least one of the group consisting of C.I. Pigment Red 291 and C.I. Acid Red 52. [6] The red coloring composition as described in any one of [1] to [5], wherein the yellow colorant (A-3) is selected from the group consisting of C.I. Pigment Yellow 139, C.I. Pigment Yellow 150 and C.I. Pigment Yellow 185 At least one of the groups formed. [7] A color filter formed of the red coloring composition as described in any one of [1] to [6]. [8] A display device comprising the color filter described in [7]. [9] A solid-state imaging device including the color filter described in [7]. [Effect of Invention]

According to the present invention, it is possible to provide a red coloring composition useful for thinning a color filter and improving brightness.

The red coloring composition of the present invention includes a colorant (hereinafter, sometimes referred to as colorant (A)), a resin (hereinafter, sometimes referred to as resin (B)), a polymerizable compound (hereinafter, sometimes referred to as polymerizable compound (C)), a polymerization initiator (hereinafter, may be referred to as a polymerization initiator (D)), and a solvent (hereinafter, may be referred to as a solvent (E)). The red coloring composition of this invention may contain a leveling agent (Hereinafter, it may be called a leveling agent (F)). In addition, in this specification, unless otherwise specified, the compound illustrated as each component can be used individually or in combination of plural types.

＜Colorant (A)＞ The colorant (A) includes an orange colorant (A-1) satisfying the condition (X), a red colorant (A-2), and a metal-containing azo colorant, isoindoline colorant, and coumarin colorant At least one yellow coloring agent (A-3) in the group formed.

＜Orange Colorant (A-1)＞ The orange colorant (A-1) is characterized by satisfying the condition (X). [Condition (X)] Preparation of the composition (X-1) which contains only the orange colorant (A-1) as a colorant, and the content of the orange colorant (A-1) in the solid content reaches 10% by mass. (X-1) When measuring the absorbance of a color filter with a film thickness of 1 μm, The absorbance at a wavelength of 480 nm is above 0.40, The absorbance at a wavelength of 530 nm is above 0.55, Absorbance at a wavelength of 580 nm is below 0.20.

In condition (X), The absorbance at a wavelength of 440 nm is preferably from 0.30 to 0.90, more preferably from 0.35 to 0.85, and still more preferably from 0.40 to 0.80. The absorbance at a wavelength of 480 nm is preferably from 0.41 to 0.95, more preferably from 0.50 to 0.90, and still more preferably from 0.60 to 0.85. The absorbance at a wavelength of 530 nm is preferably from 0.57 to 0.80, more preferably from 0.60 to 0.75, and still more preferably from 0.62 to 0.70. The absorbance at a wavelength of 570 nm is preferably from 0.01 to 0.25, more preferably from 0.05 to 0.20, and still more preferably from 0.10 to 0.18. The absorbance at a wavelength of 580 nm is preferably from 0.01 to 0.18, more preferably from 0.03 to 0.16, and still more preferably from 0.05 to 0.12.

Known dyes or pigments can be used as the orange colorant (A-1) satisfying the condition (X). The orange colorant (A-1) satisfying the condition (X) preferably contains at least one kind selected from C.I. Pigment Orange 43 and C.I. Pigment Orange 64.

The content of the orange colorant (A-1) in the total amount of the colorant (A) is preferably at least 1% by mass, more preferably at least 5% by mass, still more preferably at least 10% by mass, still more preferably It is 15 mass % or more, and is preferably 70 mass % or less, more preferably 65 mass % or less, still more preferably 60 mass % or less, still more preferably 50 mass % or less.

＜Red Colorant (A-2)＞ As the red coloring agent (A-2), known dyes and pigments that exhibit red can be used. Among these, the red coloring agent (A-2) that satisfies the condition (Y) is preferable as the red coloring agent (A-2). [Condition (Y)] A composition (Y) containing only the red colorant (A-2) as a colorant was prepared, and the content of the red colorant (A-2) in the solid content was 10% by mass. ) to measure the absorbance of a color filter with a film thickness of 1 μm, The absorbance at a wavelength of 440 nm is below 0.30, The absorbance at a wavelength of 480 nm does not reach 0.50, The absorbance at a wavelength of 530 nm is above 0.30, The absorbance at a wavelength of 580 nm is above 0.10.

In condition (Y), The absorbance at a wavelength of 440 nm is preferably from 0.01 to 0.30, more preferably from 0.03 to 0.30, and still more preferably from 0.05 to 0.29. The absorbance at a wavelength of 480 nm is preferably from 0.01 to 0.48, more preferably from 0.03 to 0.47, and still more preferably from 0.05 to 0.45. The absorbance at a wavelength of 530 nm is preferably from 0.31 to 0.60, more preferably from 0.33 to 0.55, still more preferably from 0.35 to 0.50, and more preferably from 0.31 to 0.39. The absorbance at a wavelength of 570 nm is preferably from 0.30 to 0.65, more preferably from 0.33 to 0.60, still more preferably from 0.35 to 0.55, and more preferably from 0.30 to 0.38. The absorbance at a wavelength of 580 nm is preferably from 0.11 to 0.50, more preferably from 0.11 to 0.45, still more preferably from 0.11 to 0.40.

The red colorant (A-2) satisfying the condition (Y) is preferably selected from the group consisting of C.I. Pigment Red 177, C.I. Pigment Red 254, C.I. Pigment Red 269, C.I. Pigment Red 291 and C.I. Acid Red 52 At least one or more, more preferably at least one selected from the group consisting of C.I. Pigment Red 177 and C.I. Pigment Red 269, most preferably C.I. Pigment Red 177.

The content of the red colorant (A-2) in the total amount of the colorant (A) is preferably at least 20% by mass, more preferably at least 25% by mass, still more preferably at least 30% by mass, and even more preferably It is 35 mass % or more, Preferably it is 95 mass % or less, More preferably, it is 90 mass % or less, More preferably, it is 85 mass % or less.

The content of the red colorant (A-2) is preferably from 1 to 10,000 parts by mass, more preferably from 50 to 5,000 parts by mass, and still more preferably from 100 to 2,500 parts by mass, based on 100 parts by mass of the orange colorant (A-1). share.

＜Yellow Colorant (A-3)＞ As the yellow coloring agent (A-3), at least one coloring agent selected from the group consisting of metal-containing azo dyes, isoindoline dyes, and coumarin dyes, which exhibits yellow color, can be used. Known dyes and pigments. Copper, nickel, cobalt, zinc etc. are mentioned as a metal contained in the said azo dye, Preferably it is nickel. Among the azo dyes, metals preferably form complexes with organic dyes through coordination bonds. The yellow coloring agent (A-3) is preferably a yellow coloring agent (A-3) satisfying the condition (Z). [Condition (Z)] Preparation of a composition (Z-1) containing only the yellow colorant (A-3) as a colorant, and the content of the yellow colorant (A-3) in the solid content is 10% by mass. (Z-1) When measuring the absorbance of a color filter with a film thickness of 1 μm, The absorbance at a wavelength of 440 nm is above 0.50, The absorbance at a wavelength of 480 nm is above 0.20, The absorbance at a wavelength of 530 nm is below 0.10, The absorbance at a wavelength of 580 nm is below 0.10.

In condition (Z), The absorbance at a wavelength of 440 nm is preferably from 0.55 to 1.10, more preferably from 0.60 to 1.05, and still more preferably from 0.65 to 1.00. The absorbance at a wavelength of 480 nm is preferably from 0.22 to 0.70, more preferably from 0.25 to 0.65, and still more preferably from 0.30 to 0.60. The absorbance at a wavelength of 530 nm is preferably from 0.01 to 0.09, more preferably from 0.02 to 0.07, and still more preferably from 0.03 to 0.05. The absorbance at a wavelength of 580 nm is preferably from 0.01 to 0.09, more preferably from 0.02 to 0.07.

The yellow colorant (A-3) satisfying the condition (Z) is preferably a pigment, and more preferably contains at least one selected from the group consisting of C.I. Pigment Yellow 139, C.I. Pigment Yellow 150, and C.I. Pigment Yellow 185.

The content of the yellow colorant (A-3) in the total amount of the colorant (A) is preferably at least 1% by mass, more preferably at least 2% by mass, still more preferably at least 3% by mass, and still more preferably It is 4 mass % or more, and is preferably 45 mass % or less, more preferably 40 mass % or less, still more preferably 35 mass % or less, still more preferably 30 mass % or less.

With respect to 100 parts by mass of the orange colorant (A-1), the content of the yellow colorant (A-3) is 250 parts by mass or less, preferably 200 parts by mass or less, more preferably 150 parts by mass or less, and more preferably 100 parts by mass or less, and preferably 10 parts by mass or more, more preferably 20 parts by mass or more, further preferably 25 parts by mass or more.

<Preferable combination of orange colorant (A-1), red colorant (A-2), yellow colorant (A-3)> The combination of the orange colorant (A-1), the red colorant (A-2), and the yellow colorant (A-3) may include combinations of the largest ones or the smallest ones among the ranges exemplified above. make an appropriate choice, among which A combination of the following three is preferred: Under condition (X), the orange colorant (A-1) has an absorbance of 0.41 to 0.95 at a wavelength of 480 nm, an absorbance of 0.57 to 0.80 at a wavelength of 530 nm, and an absorbance of 0.03 to 0.16 at a wavelength of 580 nm , Red colorant (A-2) under condition (Y), the absorbance at a wavelength of 440 nm is 0.05 to 0.29, the absorbance at a wavelength of 480 nm is 0.05 to 0.45, and the absorbance at a wavelength of 530 nm is 0.35 to 0.50 , the absorbance at a wavelength of 580 nm is not less than 0.11 and not more than 0.40, Yellow colorant (A-3) under condition (Z), the absorbance at a wavelength of 440 nm is 0.65 to 1.00, the absorbance at a wavelength of 480 nm is 0.22 to 0.70, and the absorbance at a wavelength of 530 nm is 0.01 to 0.09 , the absorbance at a wavelength of 580 nm is not less than 0.01 and not more than 0.09. A combination of the following three is also preferred: Under condition (X), the orange colorant (A-1) has an absorbance of 0.41 to 0.95 at a wavelength of 480 nm, an absorbance of 0.57 to 0.80 at a wavelength of 530 nm, and an absorbance of 0.01 to 0.18 at a wavelength of 580 nm , Red colorant (A-2) under condition (Y), the absorbance at a wavelength of 440 nm is 0.01 to 0.30, the absorbance at a wavelength of 480 nm is 0.01 to 0.48, and the absorbance at a wavelength of 530 nm is 0.31 to 0.39 , the absorbance at a wavelength of 580 nm is not less than 0.11 and not more than 0.50, Yellow colorant (A-3) under condition (Z), the absorbance at a wavelength of 440 nm is 0.55 to 1.10, the absorbance at a wavelength of 480 nm is 0.22 to 0.70, and the absorbance at a wavelength of 530 nm is 0.01 to 0.09 , the absorbance at a wavelength of 580 nm is not less than 0.01 and not more than 0.09. The best combination of the following three: Under condition (X), the orange colorant (A-1) has an absorbance of 0.41 to 0.95 at a wavelength of 480 nm, an absorbance of 0.57 to 0.80 at a wavelength of 530 nm, and an absorbance of 0.03 to 0.16 at a wavelength of 580 nm , Red colorant (A-2) under condition (Y), the absorbance at a wavelength of 440 nm is 0.05 to 0.29, the absorbance at a wavelength of 480 nm is 0.05 to 0.45, and the absorbance at a wavelength of 530 nm is 0.31 to 0.39 , the absorbance at a wavelength of 580 nm is not less than 0.11 and not more than 0.40, Yellow colorant (A-3) under condition (Z), the absorbance at a wavelength of 440 nm is 0.65 to 1.00, the absorbance at a wavelength of 480 nm is 0.22 to 0.70, and the absorbance at a wavelength of 530 nm is 0.01 to 0.09 , the absorbance at a wavelength of 580 nm is not less than 0.01 and not more than 0.09.

Also, a preferred combination of orange colorant (A-1), red colorant (A-2), and yellow colorant (A-3) is preferably at least 1 selected from C.I. Pigment Orange 43 and C.I. Pigment Orange 64. A combination of C.I. Pigment Red 177, and at least one selected from the group consisting of C.I. Pigment Yellow 139, C.I. Pigment Yellow 150, and C.I. Pigment Yellow 185.

Coloring agent (A) may contain orange coloring agent (A-1), red coloring agent (A-1), red coloring agent (A-3) and A colorant different from the orange colorant (A-1), red colorant (A-2) and yellow colorant (A-3) The colorant may be any of dye (hereinafter, sometimes referred to as dye (A1)) and pigment (hereinafter, sometimes referred to as pigment (A2)), and orange colorant (A-1), red colorant (A-2) and the coloring agent different from a yellow coloring agent (A-3) may contain one or both of these dyes (A1) and pigments (A2).

The dye (A1) is not particularly limited as long as it does not contain the orange colorant (A-1), the red colorant (A-2) and the yellow colorant (A-3). Known dyes can be used, and examples include: solvents Dyes, acid dyes, direct dyes, mordant dyes, etc. Examples of dyes include compounds classified as those having a hue other than pigments in the Dye Index (published by The Society of Dyers and Colourists), and known dyes described in Dyeing Notes (Yordye Co., Ltd.). Also, depending on the chemical structure, azo dyes, cyanine dyes, triphenylmethane dyes, dibenzopyran dyes, phthalocyanine dyes, anthraquinone dyes, naphthoquinone dyes, quinone imine dyes, methine dyes, etc. Dyes, methine azo dyes, squarylium dyes, acridine dyes, styryl dyes, coumarin dyes, quinoline dyes and nitro dyes, etc. Among these, organic solvent-soluble dyes are preferred.

Specifically, for example: C.I. Solvent Violet 11 (hereinafter, the description of C.I. Solvent Violet is omitted, and only the serial number is recorded), 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60; C.I. Solvent Blue 4, 5, 14, 18, 35, 36, 37, 45, 58, 59, 59: 1, 63, 67, 68, 69, 70, 78, 79, 83, 90, 94, 97, 98 , 100, 101, 102, 104, 105, 111, 112, 122, 128, 132, 136, 139; C.I. solvent green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35, etc. C.I. solvent dyes; C.I. Acid Violet 6B, 7, 9, 15, 16, 17, 19, 21, 23, 24, 25, 30, 34, 38, 49, 72, 102; C.I. Acid Blue 1, 3, 5, 7, 9, 11, 13, 15, 17, 18, 22, 23, 24, 25, 26, 27, 29, 34, 38, 40, 41, 42, 43, 45 , 48, 51, 54, 59, 60, 62, 70, 72, 74, 75, 78, 80, 82, 83, 86, 87, 88, 90, 90: 1, 91, 92, 93, 93: 1 ,96,99,100,102,103,104,108,109,110,112,113,117,119,120,123,126,127,129,130,131,138,140,142,143,147 ,150,151,154,158,161,166,167,168,170,171,175,182,183,184,187,192,199,203,204,205,210,213,229,234,236 , 242, 243, 256, 259, 267, 269, 278, 280, 285, 290, 296, 315, 324: 1, 335, 340; C.I. Acid Green 1, 3, 5, 6, 7, 8, 9, 11, 13, 14, 15, 16, 22, 25, 27, 28, 41, 50, 50: 1, 58, 63, 65, 80 , 104, 105, 106, 109 and other C.I. acid dyes; C.I. Direct Violet 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104; C.I. Direct Blue 1, 2, 3, 6, 8, 15, 22, 25, 28, 29, 40, 41, 42, 47, 52, 55, 57, 71, 76, 77, 78, 80, 81, 84 ,85,86,90,93,94,95,97,98,99,100,101,106,107,108,109,113,114,115,117,119,120,137,149,150,153 ,155,156,158,159,160,161,162,163,164,165,166,167,168,170,171,172,173,188,189,190,192,193,194,195,196 ,198,199,200,201,202,203,207,209,210,212,213,214,222,225,226,228,229,236,237,238,242,243,244,245,246 , 247, 248, 249, 250, 251, 252, 256, 257, 259, 260, 268, 274, 275, 293; C.I. Direct Green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 77, 79, 82 and other C.I. direct dyes; C.I. Disperse Violet 26, 27; C.I. disperse blue 1, 14, 56, 60 and other C.I. disperse dyes; C.I. Basic Blue 1, 3, 5, 7, 9, 19, 21, 22, 24, 25, 26, 28, 29, 40, 41, 45, 47, 54, 58, 59, 60, 64, 65, 66, 67, 68, 81, 83, 88, 89; C.I. Basic Violet 2; C.I. Basic dyes such as C.I. Basic Green 1; C.I. Mordant Violet 1, 1:1, 2, 3, 4, 5, 6, 7, 8, 10, 11, 14, 15, 16, 17, 18, 19, 21, 22, 23, 24, 27, 28 , 30, 31, 32, 33, 36, 37, 39, 40, 41, 44, 45, 47, 48, 49, 53, 58; C.I. Mordant Blue 1, 2, 3, 7, 8, 9, 12, 13, 15, 16, 19, 20, 21, 22, 23, 24, 26, 30, 31, 32, 39, 40, 41, 43 , 44, 48, 49, 53, 61, 74, 77, 83, 84; C.I. Mordant Green 1, 3, 4, 5, 10, 13, 15, 19, 21, 23, 26, 29, 31, 33, 34, 35, 41, 43, 53 and other C.I. mordant dyes; C.I. Vat Green 1, etc. C.I. Vat dyes, etc. These dyes can be properly selected according to the spectral spectrum of the desired color filter.

The pigment (A2) is not particularly limited, and known pigments can be used, for example, pigments classified as pigments in the Dye Index (published by The Society of Dyers and Colourists). As pigments, for example, yellow pigments such as C.I. Pigment Yellow 83 and 138 can be mentioned; C.I. Pigment Orange 36, 38, 62, 71, 72 and other orange pigments; C.I. Pigment Blue 15, 15:3, 15:4, 15:6, 60 and other blue pigments; C.I. Pigment Violet 1, 19, 23, 29, 32, 36, 38 and other purple pigments; C.I. Pigment Green 7, 36, 58 and other green pigments; C.I. Pigment Brown 23, 25 and other brown pigments; C.I. Pigment Black 1, 7 and other black pigments, etc.

Pigments may be subjected to rosin treatment, surface treatment using pigment derivatives introduced with acidic or basic groups, etc., grafting treatment on the surface of pigments with polymer compounds, micronization treatment using sulfuric acid micronization method, etc. Or cleaning treatment using organic solvent or water for removing impurities, removal treatment using ion exchange method for ionic impurities, etc. The pigment preferably has a uniform particle size. By carrying out dispersion treatment with a pigment dispersant, a pigment dispersion liquid in which the pigment is uniformly dispersed in the solution can be obtained.

As said pigment dispersant, cationic, anionic, nonionic, amphoteric, polyester type, polyamine type, acryl type, etc. surfactants are mentioned, for example. These pigment dispersants may be used alone or in combination of two or more. Examples of pigment dispersants include KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Flowlen (manufactured by Kyoeisha Chemical Co., Ltd.), Solsperse (manufactured by Zeneca Co., Ltd.), and EFKA (manufactured by CIBA Corporation) by trade name. , Ajisper (manufactured by Ajinomoto Fine-Techno. Co., Inc.), Disperbyk (manufactured by BYK-Chemie), etc. When using a pigment dispersant, the amount used is preferably from 1 mass % to 100 mass %, more preferably from 5 mass % to 50 mass %, based on the total amount of the pigment (A2). When the usage-amount of a pigment dispersant falls within the said range, the pigment dispersion liquid with uniform dispersion state tends to be obtained.

The content of the coloring agent (A) in the red coloring composition is preferably from 5% by mass to 70% by mass based on the total amount of solid content, more preferably from 10% by mass to 65% by mass, still more preferably It is not less than 20% by mass and not more than 60% by mass. If the content of the coloring agent (A) is within the above range, the color density when used as a color filter is sufficient, and a required amount of resin (B) or polymerizable compound (C) can be contained in the composition. Therefore, Patterns with sufficient mechanical strength can be formed.

Here, the "total amount of solid content" in this specification refers to the amount obtained by subtracting the content of the solvent from the total amount of the red coloring composition. The total amount of solid content and the content of each component relative thereto can be measured, for example, by known analysis methods such as liquid chromatography or gas chromatography.

＜Resin (B)＞ The resin (B) is preferably an alkali-soluble resin, and more preferably has at least one monomer selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic anhydrides (hereinafter sometimes referred to as "monomer ( a) Polymers of structural units of "). The resin (B) preferably has a structural unit derived from a monomer having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond (hereinafter, sometimes referred to as "monomer (b)"), and Copolymers of other structural units. Examples of other structural units include monomers derived from monomers (a) copolymerizable (however, they are different from monomers (a) and monomers (b). Hereinafter, they may be referred to as "monomer (c) )"), structural units with ethylenically unsaturated bonds, etc.

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

As the monomer (a), for example, unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid and o/m/p-vinylbenzoic acid can be mentioned; Maleic acid, fumaric acid, methylmaleic acid, methylfumaric acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyltetrahydrophthalic acid and 1,4-cyclohexenedicarboxylic acid Unsaturated dicarboxylic acids; Methyl-5-northene-2,3-dicarboxylic acid, 5-carboxybicyclo[2.2.1]hept-2-ene, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene, 5-carboxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-carboxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-carboxy-6-methylbicyclo[ 2.2.1] Hept-2-ene and 5-carboxy-6-ethylbicyclo[2.2.1]hept-2-ene and other carboxyl-containing bicyclic unsaturated compounds; Maleic anhydride, methylmaleic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride Diformic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride, etc. Unsaturated dicarboxylic acid anhydride; Unsaturated polycarboxylic acids with more than two valences such as mono[2-(meth)acryloxyethyl]succinate and mono[2-(meth)acryloxyethyl]phthalate Mono[(meth)acryloxyalkyl]esters; α-(Hydroxymethyl)acrylic acid, etc., are unsaturated acrylates containing hydroxyl and carboxyl groups in the same molecule.

Among them, acrylic acid, methacrylic acid, o/m/p-vinylbenzoic acid, and cis-butylene are preferred in terms of copolymerization reactivity or the solubility of the obtained resin in an aqueous alkaline solution. Alkenic anhydride, etc.

Monomer (b) refers to a cyclic ether structure having 2 to 4 carbon atoms (for example, selected from the group consisting of oxirane ring, oxetane ring and tetrahydrofuran ring (oxolane ring) at least one of) and a polymerizable compound with an ethylenically unsaturated bond. The monomer (b) is preferably a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth)acryloxy group.

As the monomer (b), for example, a monomer having an oxirane group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "monomer (b1)"), a monomer having an oxetanyl group and A monomer having an ethylenically unsaturated bond (hereinafter, sometimes referred to as "monomer (b2)"), a monomer having a tetrahydrofuryl group and an ethylenically unsaturated bond (hereinafter, sometimes referred to as "monomer (b3)") )Wait.

As the monomer (b1), for example, a monomer having a linear or branched unsaturated aliphatic hydrocarbon epoxidized structure (hereinafter sometimes referred to as "monomer (b1-1)") . A monomer having an epoxidized structure of an unsaturated alicyclic hydrocarbon (hereinafter, sometimes referred to as "monomer (b1-2)").

The monomer (b1-1) is preferably a monomer having a glycidyl group and an ethylenically unsaturated bond. Examples of the monomer (b1-1) include glycidyl (meth)acrylate, β-methylglycidyl (meth)acrylate, β-ethylglycidyl (meth)acrylate, glycidyl (meth)acrylate, Glyceryl vinyl ether, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether, α-methyl-o-vinylbenzyl glycidyl ether, α-methyl Base-m-vinylbenzyl glycidyl ether, α-methyl-p-vinylbenzyl glycidyl ether, 2,3-bis(glycidyloxymethyl)styrene, 2,4-bis(glycidyloxy 2,5-bis(glycidyloxymethyl)styrene, 2,5-bis(glycidyloxymethyl)styrene, 2,6-bis(glycidyloxymethyl)styrene, 2,3,4-tris(glycidyloxy methyl) styrene, 2,3,5-tris(glycidyloxymethyl)styrene, 2,3,6-tris(glycidyloxymethyl)styrene, 3,4,5-tris (glycidyloxymethyl)styrene, 2,4,6-tris(glycidyloxymethyl)styrene, etc.

As the monomer (b1-2), for example, vinylcyclohexene monoxide, 1,2-epoxy-4-vinylcyclohexane (for example, Celloxide (registered trademark) 2000, Daicel ( Co., Ltd.), 3,4-epoxycyclohexylmethyl (meth)acrylate (for example, Cyclomer (registered trademark) A400, manufactured by Daicel Co., Ltd.), 3,4-epoxycyclohexyl (meth)acrylate Hexyl methyl ester (for example, Cyclomer (registered trademark) M100, manufactured by Daicel Co., Ltd.), a compound represented by formula (BI), a compound represented by formula (BII), and the like.

[chemical 1]

[In formula (BI) and formula (BII), R ^a and R ^b independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the hydrogen atom contained in the alkyl group may be substituted with a hydroxyl group. X ^a and X ^b independently represent a single bond, *-R ^c -, *-R ^c -O-, *-R ^c -S-, or *-R ^c -NH-. R ^c represents an alkanediyl group having 1 to 6 carbon atoms. *Indicates the bond with O]

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

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

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

Examples of the alkanediyl group include methylene, ethylidene, propane-1,2-diyl, propane-1,3-diyl, butane-1,4-diyl, pentane-1 ,5-diyl, hexane-1,6-diyl, etc.

As X ^a and X ^b , preferably a single bond, methylene, ethylidene, *-CH ₂ -O-, *-CH ₂ CH ₂ -O-, more preferably a single bond , *-CH ₂ CH ₂ -O- (* represents a bond with O).

As a compound represented by formula (BI), the compound etc. which are represented by any one of formula (BI-1) - a formula (BI-15) are mentioned. Among them, formula (BI-1), formula (BI-3), formula (BI-5), formula (BI-7), formula (BI-9) and formula (BI-11) ~ formula (BI The compound represented by -15) is more preferably a compound represented by formula (BI-1), formula (BI-7), formula (BI-9) and formula (BI-15).

[Chem 2]

As the compound represented by formula (BII), a compound represented by any one of formula (BII-1) to formula (BII-15) can be exemplified, and among them, formula (BII-1) can be exemplified preferably. , the compounds represented by formula (BII-3), formula (BII-5), formula (BII-7), formula (BII-9) and formula (BII-11) ~ formula (BII-15), more preferably Examples thereof include compounds represented by formula (BII-1), formula (BII-7), formula (BII-9) and formula (BII-15).

[Chem 3]

The compound represented by formula (BI) and the compound represented by formula (BII) may be used alone or in combination of two or more. The compound represented by formula (BI) and the compound represented by formula (BII) can also be used together. When the compound represented by formula (BI) and the compound represented by formula (BII) are used together, the content ratio [compound represented by formula (BI): compound represented by formula (BII)] is expressed in moles On a base basis, it is preferably 5:95 to 95:5, more preferably 10:90 to 90:10, and still more preferably 20:80 to 80:20.

The monomer (b2) having an oxetanyl group and an ethylenically unsaturated bond is more preferably a monomer having an oxetanyl group and a (meth)acryloxy group. Examples of the monomer (b2) include: 3-methyl-3-(meth)acryloxymethyloxetane, 3-ethyl-3-(meth)acryloxy Methyloxetane, 3-methyl-3-(meth)acryloxyethyloxetane, 3-ethyl-3-(meth)acryloxyethyloxetane Cyclobutane etc.

As the monomer (b3) having a tetrahydrofuryl group and an ethylenically unsaturated bond, a monomer having a tetrahydrofuryl group and a (meth)acryloxy group is more preferable. Examples of the monomer (b3) include tetrahydrofurfuryl acrylate (for example, Viscoat V#150, manufactured by Osaka Organic Chemical Industry Co., Ltd.), tetrahydrofurfuryl methacrylate, and the like.

The monomer (b) is preferably a monomer (b1) from the point that reliability such as heat resistance and chemical resistance of the obtained color filter can be further improved. Furthermore, a monomer (b1-2) is more preferable at the point which is excellent in the storage stability of a coloring composition.

As the monomer (c), for example, methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, second-butyl (meth)acrylate, (meth)acrylate ) tertiary butyl acrylate, 2-ethylhexyl (meth)acrylate, dodecyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, (meth) ) cyclopentyl acrylate, cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, tricyclo[5.2.1.0 ^2,6 ]dec-8-yl (meth)acrylate ( In this technical field, it is called "dicyclopentyl (meth)acrylate" as a common name. Also, it is sometimes called "tricyclodecanyl (meth)acrylate"), tricyclodecanyl (meth)acrylate Cyclo[5.2.1.0 ^2,6 ]dec-9-yl ester, tricyclo[5.2.1.0 ^2,6 ]decen-8-yl (meth)acrylate (in this technical field, as a common name, called "Dicyclopentenyl (meth)acrylate"), tricyclo[5.2.1.0 ^2,6 ]decen-9-yl (meth)acrylate, dicyclopentyloxyethyl (meth)acrylate, Iso(meth)acrylate, adamantyl (meth)acrylate, allyl (meth)acrylate, propargyl (meth)acrylate, phenyl (meth)acrylate, (meth)acrylic acid (meth)acrylates such as naphthyl esters and benzyl (meth)acrylate; (meth)acrylates containing hydroxyl groups such as 2-hydroxyethyl (meth)acrylate and 2-hydroxypropyl (meth)acrylate; (Meth)acrylic acid 2,2,3,3,4,4,5,5-octafluoropentyl ester and other (meth)acrylic acid esters containing halogen atoms; diethyl maleate, trans-butene dicarboxylic acid diesters such as diethyl diethyl itaconate and itaconate; bicyclo[2.2.1]hept-2-ene, 5-methylbicyclo[2.2.1]hept-2-ene, 5-ethyl Bicyclo[2.2.1]hept-2-ene, 5-hydroxybicyclo[2.2.1]hept-2-ene, 5-hydroxymethylbicyclo[2.2.1]hept-2-ene, 5-(2'- Hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5-methoxybicyclo[2.2.1]hept-2-ene, 5-ethoxybicyclo[2.2.1]hept-2-ene, 5,6-Dihydroxybicyclo[2.2.1]hept-2-ene, 5,6-bis(hydroxymethyl)bicyclo[2.2.1]hept-2-ene, 5,6-bis(2'-hydroxy Ethyl)bicyclo[2.2.1]hept-2-ene, 5,6-dimethoxybicyclo[2.2.1]hept-2-ene, 5,6-diethoxybicyclo[2.2.1]heptene -2-ene, 5-hydroxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxymethyl -5-Methylbicyclo[2.2.1]hept-2-ene, 5-tert-butoxycarbonylbicyclo[2.2.1]hept-2-ene, 5-cyclohexyloxycarbonylbicyclo[2.2.1] Hept-2-ene, 5-phenoxycarbonylbicyclo[2.2.1]hept-2- ene, 5,6-bis(tert-butoxycarbonyl)bicyclo[2.2.1]hept-2-ene and 5,6-bis(cyclohexyloxycarbonyl)bicyclo[2.2.1]hept-2-ene Bicyclic unsaturated compounds such as; N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimide-3-maleimide Imine Benzoate, N-Succinimido-4-Maleimide Butyrate, N-Succinimido-6-Maleimide Hexanoate, N-Butyl Diimido-3-maleimide propionate and N-(9-acridyl)maleimide and other dicarbonyl imide derivatives; styrene, o-methylstyrene, m- Vinyl-containing aromatic compounds such as methylstyrene, p-methylstyrene, vinyltoluene, 9-vinylcarbazole, and p-methoxystyrene; vinyl-containing nitriles such as (meth)acrylonitrile; chlorine Halogenated hydrocarbons such as ethylene and vinylidene chloride; amides containing vinyl groups such as (meth)acrylamide; esters such as vinyl acetate; 1,3-butadiene, isoprene and 2,3-diene Dienes such as methyl-1,3-butadiene, etc. Among these, in terms of copolymerization reactivity and heat resistance, styrene, vinyl toluene, tricyclo[5.2.1.0 ^2,6 ]dec-8-yl (meth)acrylate, ( Tricyclo[5.2.1.0 ^2,6 ]decen-9-yl meth)acrylate, Tricyclo[5.2.1.0 2,6 ]decen-8-yl (meth)acrylate, Tricyclo[5.2.1.0 ^2,6 ]decen-8-yl (meth)acrylate Cyclo[5.2.1.0 ^2,6 ]decen-9-yl ester, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo[2.2 .1] Hept-2-ene, phenyl (meth)acrylate, 2,2,3,3,4,4,5,5-octafluoropentyl (meth)acrylate, 9-vinylcarbazole, ( Benzyl meth)acrylate, 2-hydroxyethyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, etc.

As the resin (B), specifically, 3,4-epoxycyclohexylmethyl (meth)acrylate/(meth)acrylic acid copolymer, 3,4-epoxycyclohexyl (meth)acrylate, Cyclo[5.2.1.0 ^2.6 ]decyl ester/(meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2.6 ]decyl (meth)acrylate/benzyl (meth)acrylate/(meth)acrylate base) acrylic acid copolymer, (meth)acrylic acid 3,4-epoxytricyclo[5.2.1.0 ^2.6 ]decyl ester/9-vinylcarbazole/(meth)acrylic acid copolymer, (meth)acrylic acid 3,4 - ^{Epoxytricyclo} [5.2.1.02.6]decyl ester/phenyl (meth)acrylate/o-vinylbenzoic acid copolymer, 3,4-epoxytricyclo[ ^5.2.1.02.6 ]decyl (meth)acrylate Esters/Phenyl(meth)acrylate/m-vinylbenzoic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2.6 ]decyl (meth)acrylate/phenyl(meth)acrylate/p-vinyl benzoic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2.6 ]decyl (meth)acrylate/phenyl (meth)acrylate/(meth)acrylic acid copolymer, (meth)acrylic acid 3 , 4-epoxytricyclo[5.2.1.0 ^2.6 ]decyl ester/2,2,3,3,4,4,5,5-octafluoropentyl ester/(meth)acrylic acid copolymer, Glycidyl (meth)acrylate/benzyl (meth)acrylate/(meth)acrylic acid copolymer, glycidyl (meth)acrylate/styrene/(meth)acrylic acid copolymer, (meth)acrylic acid 3,4-epoxytricyclo[5.2.1.0 ^2.6 ]decyl ester/(meth)acrylic acid/N-cyclohexylmaleimide copolymer, (meth)acrylic acid 3,4-epoxytricyclo[5.2 .1.0 ^2.6 ]decyl ester/(meth)acrylic acid/N-cyclohexylmaleimide/(meth)acrylate 2-hydroxyethyl ester copolymer, (meth)acrylate 3,4-epoxytricyclo[ 5.2.1.0 ^2.6 ]decyl ester/(meth)acrylic acid/vinyltoluene copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2.6 ]decyl (meth)acrylate/(meth)acrylic acid/(meth)acrylic acid base) 2-ethylhexyl acrylate copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2.6 ]decyl (meth)acrylate/tricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate Enyl ester/(meth)acrylic acid/N-cyclohexylmaleimide copolymer, 3-methyl-3-(meth)acryloxymethyloxetane/(meth)acrylic acid/ Styrene copolymer, benzyl (meth)acrylate/(meth)acrylic acid copolymer, styrene/(meth)acrylic acid copolymer, Japanese Patent Laid-Open No. 9-106071, Japanese Patent Laid-Open No. 2004-29518 Resins and the like described in the gazettes and Japanese Patent Application Laid-Open No. 2004-361455. Among them, the resin (B) is preferably a copolymer containing a structural unit derived from the monomer (a) and a structural unit derived from the monomer (b).

Resin (B) may combine two or more types, and in this case, resin (B) is at least as follows: Preferably, it contains at least one structural unit derived from monomer (a) and derived from monomer (b) The copolymer of the structural unit, more preferably at least one kind of copolymer comprising the structural unit derived from the monomer (a) and the structural unit derived from the monomer (b1), and more preferably at least one comprising the source A copolymer of structural units derived from monomer (a) and structural units derived from monomer (b1-2), more preferably comprising (meth)acrylic acid 3,4-epoxy tricyclic [5.2.1.0 ^2.6 ]decyl ester/(meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2.6 ]decyl (meth)acrylate/(meth)acrylic acid/N-cyclohexylmaleimide / 2-hydroxyethyl (meth)acrylate copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2.6 ]decyl (meth)acrylate/(meth)acrylic acid/vinyl toluene copolymer, (meth)acrylate Base) One or more of 3,4-epoxytricyclo[5.2.1.0 ^2.6 ]decyl acrylate/(meth)acrylic acid/2-ethylhexyl (meth)acrylate copolymer.

The polystyrene-equivalent weight average molecular weight (Mw) of the resin (B) is preferably from 1,000 to 100,000, more preferably from 2,000 to 50,000, further preferably from 3,000 to 30,000, still more preferably from 5,000 to 30,000. When the weight average molecular weight is within the above range, the solubility of the unexposed portion in the developing solution is high, and the remaining film rate and hardness of the obtained pattern tend to be high.

The degree of dispersion of the resin (B) [weight average molecular weight (Mw)/number average molecular weight (Mn)] is preferably from 1 to 6, more preferably from 1 to 5, still more preferably from 1 to 4.

The acid value (solid content conversion value) of the resin (B) is preferably not less than 10 mg-KOH/g and not more than 300 mg-KOH/g, more preferably not less than 20 mg-KOH/g and not more than 250 mg-KOH/g, More preferably, it is 25 mg-KOH/g to 200 mg-KOH/g, and more preferably 30 mg-KOH/g to 180 mg-KOH/g, especially preferably 40 mg-KOH/g to 150 mg -KOH/g or less. Here, the acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of the resin, and can be determined, for example, by titration using an aqueous potassium hydroxide solution.

The content of the resin (B) is preferably from 5 to 90% by mass, more preferably from 10 to 80% by mass, further preferably from 13 to 70% by mass, with respect to 100% by mass of the solid content of the red coloring composition, and further preferably More preferably, it is 15-60 mass %. When the content rate of resin (B) exists in the said range, there exists a tendency for the solubility to the developing solution of an unexposed part to be high.

＜Polymerizable compound (C)＞ The polymerizable compound (C) is a compound that can be polymerized by active radicals and/or acids generated from the polymerization initiator (D), for example, a compound having a polymerizable ethylenically unsaturated bond, preferably (meth)acrylate compounds.

Among them, the polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds. As such a polymerizable compound, for example, trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, Acrylates, dipentaerythritol hexa(meth)acrylate, tripentaerythritol octa(meth)acrylate, tripentaerythritol hepta(meth)acrylate, tetrapentaerythritol deca(meth)acrylate, tetrapentaerythritol nona(meth)acrylate Acrylates, Tris(2-(meth)acryloxyethyl)isocyanurate, Ethylene glycol-modified pentaerythritol tetra(meth)acrylate, Ethylene glycol-modified dipentaerythritol hexa(meth)acrylic acid Ester, propylene glycol modified pentaerythritol tetra(meth)acrylate, propylene glycol modified dipentaerythritol hexa(meth)acrylate, caprolactone modified pentaerythritol tetra(meth)acrylate, caprolactone modified dipentaerythritol hexa(meth)acrylate meth)acrylate. Among these, dipentaerythritol penta(meth)acrylate and dipentaerythritol hexa(meth)acrylate are preferable.

The content of the polymerizable compound (C) is preferably from 1 to 65% by mass, more preferably from 5 to 60% by mass, and still more preferably from 10 to 55% by mass based on the total amount of solid content. When the content rate of a polymeric compound (C) exists in the said range, there exists a tendency for the residual film rate at the time of forming a colored pattern and the chemical resistance of a color filter to improve.

＜Polymerization initiator (D)＞ The polymerization initiator (D) is not particularly limited as long as it is a compound that can generate active radicals, acids, etc. by the action of light or heat to initiate polymerization, and known polymerization initiators can be used. Examples of polymerization initiators that generate active radicals include O-acyl oxime compounds, benzophenone compounds, trioxane compounds, acyl phosphine oxide compounds, and biimidazole compounds.

Examples of the O-acyl oxime compound include N-benzoyloxy-1-(4-phenylthiophenyl)butan-1-one-2-imine, N-benzoyl Oxy-1-(4-phenylthiophenyl)octan-1-one-2-imine, N-benzoyloxy-1-(4-phenylthiophenyl)-3-cyclopentyl Diphenylsulfide O-acyl oxime compound with ether skeleton; N-acetyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethane-1 -Imine, N-acetyloxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethyl-2,4-dioxolylmethyl Oxy)benzoyl}-9H-carbazol-3-yl]ethane-1-imine, N-acetyloxy-1-[9-ethyl-6-(2-methylbenzyl Acyl)-9H-carbazol-3-yl]-3-cyclopentylpropane-1-imine, N-benzoyloxy-1-[9-ethyl-6-(2-methylbenzyl Acyl)-9H-carbazol-3-yl]-3-cyclopentylpropane-1-one-2-imine and other O-acyl oxime compounds with carbazole skeleton; 1-[7-(2-form O-acyl oxime compounds such as phenylbenzoyl)-9,9-dipropyl-9H-oxa-2-yl]ethanone O-acetyl oxime and the like. Irgacure (registered trademark) OXE01, OXE02 (manufactured by BASF), PBG-327 (manufactured by Changzhou Qiangli Electronic New Materials Co., Ltd.), N-1919 (manufactured by ADEKA), DFI-091 (manufactured by Daito Chemix ( Stock) manufacturing) and other commercially available products. Among them, the O-acyl oxime compound is preferably selected from N-benzoyloxy-1-(4-phenylthiophenyl)octan-1-one-2-imine, N-acetyloxy -1-(4-phenylthiophenyl)-3-cyclohexylpropane-1-one-2-imine, N-acetyloxy-1-[9-ethyl-6-{2-methyl -4-(3,3-Dimethyl-2,4-dioxolanylmethyloxy)benzoyl}-9H-carbazol-3-yl]ethane-1-imine and At least one species selected from the group consisting of 1-[7-(2-methylbenzoyl)-9,9-dipropyl-9H-fluorene-2-yl]ethanone O-acetyloxime. These O-acyl oxime compounds tend to provide a high-brightness color filter.

As the above-mentioned benzophenone compound, for example, 2-methyl-2-metholinyl-1-(4-methylthiophenyl)propan-1-one, 2-dimethylamino-1-( ( ( 2-Hydroxyethoxy)phenyl]propan-1-one, 1-hydroxycyclohexylphenylketone, 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propan-1-one oligomers, α,α-diethoxyacetophenone, benzoyl dimethyl ketal, etc. Commercially available items such as Irgacure (registered trademark) 369, 907, and 379 (the above are manufactured by BASF Corporation) can also be used.

As the above-mentioned trioxane compound, for example, 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-trioxophenyl, 2,4-bis( Trichloromethyl)-6-(4-Methoxynaphthyl)-1,3,5-trimethalone, 2,4-bis(trichloromethyl)-6-helianthyl-1,3,5- Trisalpine, 2,4-bis(trichloromethyl)-6-(4-methoxystyryl)-1,3,5-tristyryl, 2,4-bis(trichloromethyl)-6 -[2-(5-Methylfuran-2-yl)ethenyl]-1,3,5-trimethalone, 2,4-bis(trichloromethyl)-6-[2-(furan-2- Base) vinyl]-1,3,5-tri-methanyl, 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl)ethenyl ]-1,3,5-trimethoxy, 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)vinyl]-1,3,5- Three 𠯤 and so on.

As said acyl phosphine oxide compound, 2,4,6- trimethylbenzoyl diphenyl phosphine oxide etc. are mentioned. Commercial items such as Irgacure (registered trademark) 819 (manufactured by BASF Corporation) can also be used.

Examples of the biimidazole compound include: 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2, 3-dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole (for example, refer to Japanese Patent Laid-Open Publication No. 6-75372, Japanese Patent Laid-Open Publication No. 6-75373, etc.), 2 ,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5, 5'-tetrakis(alkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetrakis(dialkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetrakis(trialkoxyphenyl)biimidazole (for example, refer to Japanese Patent Publication No. 48-38403, Japan Japanese Patent Laid-Open Publication No. 62-174204, etc.), biimidazole compounds in which the phenyl at the 4,4', 5,5'-position is substituted by an alkoxycarbonyl group (for example, refer to Japanese Patent Laid-Open Publication No. 7-10913, etc.) Wait.

As a polymerization initiator that generates an acid, for example, 4-hydroxyphenyldimethylconduit p-toluenesulfonate, 4-hydroxyphenyldimethylconduit hexafluoroantimonate, 4-acetyloxy Phenyldimethylpercited p-toluenesulfonate, 4-acetyloxyphenyl-methyl-benzylpercited hexafluoroantimonate, triphenylcuredium p-toluenesulfonate, triphenylpercited hexafluoroantimony Onium salts such as diphenyliodonium p-toluenesulfonate, diphenyliodonium hexafluoroantimonate, etc., or nitrobenzyl toluenesulfonate, benzoin toluenesulfonate, etc.

Furthermore, examples of the polymerization initiator (D) include: benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether; , 4-phenylbenzophenone, 4-benzoyl-4'-methyl diphenyl sulfide, 3,3',4,4'-tetra(tertiary butylperoxycarbonyl) diphenyl Benzophenone compounds such as ketone and 2,4,6-trimethylbenzophenone; quinone compounds such as 9,10-phenanthrenequinone, 2-ethylanthraquinone, and camphorquinone; 10-butyl-2- Chloracridone, benzoyl, methyl phenylglyoxylate, titanocene compound, etc.

The polymerization initiator (D) preferably contains at least one kind selected from the group consisting of O-acyl oxime compounds, benzophenone compounds, trioxane compounds, acyl phosphine oxide compounds and biimidazole compounds. The polymerization initiator is more preferably a polymerization initiator containing an O-acyl oxime compound.

The content of the polymerization initiator (D) is preferably from 0.1 to 30 parts by mass, more preferably from 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 content of a polymerization initiator (D) exists in the said range, since there exists a tendency for a high sensitivity and shortening exposure time, the productivity of a color filter improves.

化合物及羧酸化合物等。 <Adjuvant for polymerization initiation (D1)> Auxiliary agent for polymerization initiation (D1) is a compound or a sensitizer for promoting the polymerization of a polymerizable compound whose polymerization starts with a polymerization initiator. In the case of containing the polymerization initiation aid (D1), it is usually used in combination with the polymerization initiation agent (D). Examples of the polymerization initiation aid (D1) include amine compounds, alkoxyanthracene compounds, and 9-oxothiophene

compounds and carboxylic acid compounds.

Examples of the amine compound include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, 4-dimethylaminobenzoate, Isoamyl benzoate, 2-dimethylaminoethyl benzoate, 2-ethylhexyl 4-dimethylaminobenzoate, N,N-dimethyl-p-toluidine, 4,4'-bis( Dimethylamino) benzophenone (commonly known as Micheler's ketone), 4,4'-bis(diethylamino)benzophenone, 4,4'-bis(ethylmethylamino)bis Benzophenone and the like, among which 4,4'-bis(diethylamino)benzophenone is preferred. Commercial items such as EAB-F (manufactured by Hodogaya Chemical Co., Ltd.) can also be used.

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

化合物，可例舉：2-異丙基9-氧硫𠮿

、4-異丙基9-氧硫𠮿

、2,4-二乙基9-氧硫𠮿

、2,4-二氯9-氧硫𠮿

、1-氯-4-丙氧基9-氧硫𠮿

等。As the above-mentioned 9-oxosulfur

Compounds, for example: 2-isopropyl 9-oxosulfur

, 4-isopropyl 9-oxosulfur 𠮿

, 2,4-Diethyl 9-oxosulfur 𠮿

, 2,4-dichloro-9-oxosulfur 𠮿

, 1-Chloro-4-propoxy 9-oxosulfur

Wait.

Examples of the carboxylic acid compound include: phenylthioacetic acid, methylphenylthioacetic acid, ethylphenylthioacetic acid, methylethylphenylthioacetic acid, dimethylphenylthioacetic acid, methoxybenzene Thioacetic acid, dimethoxyphenylthioacetic acid, chlorophenylthioacetic acid, dichlorophenylthioacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine Amino acid, naphthyloxyacetic acid, etc.

In the case of using these polymerization initiation aids (D1), the content is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass. When the amount of the polymerization initiation auxiliary agent (D1) is within this range, a colored pattern can be formed with high sensitivity, and the productivity of the color filter tends to be improved.

＜Solvent (E)＞ The solvent (E) is not particularly limited, and solvents generally used in this field can be used. For example, ester solvents (solvents containing -COO- and not containing -O- in the molecule), ether solvents (solvents containing -O- and not containing -COO- in the molecule), ether ester solvents (solvents containing -O- and not containing -COO- in the molecule), ether ester solvents (solvents containing Solvents containing -COO- and -O-), ketone solvents (solvents containing -CO- and not containing -COO- in the molecule), alcohol solvents (containing OH in the molecule and not containing -O-, -CO- and - COO-solvent), aromatic hydrocarbon solvent, amide solvent, dimethyl sulfide.

Examples of ester solvents include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutyrate, ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, isopentyl acetate ester, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetyl acetate, ethyl acetyl acetate, Cyclohexanol acetate and γ-butyrolactone, etc.

Examples of ether solvents include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, Diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol , tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, two Ethylene glycol dibutyl ether, anisole, phenetole and methyl anisole, etc.

Examples of ether ester solvents include: methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, 3-methoxypropane Methyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, 2-methoxypropionate Propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, 2 - Ethoxy-2-methylpropionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate Ester, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate and diethylene glycol monobutyl ether acetate, etc. .

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

The alcohol solvent may, for example, be methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol or glycerin.

The aromatic hydrocarbon solvent may, for example, be benzene, toluene, xylene or 1,3,5-trimethylbenzene.

The amide solvent may, for example, be N,N-dimethylformamide, N,N-dimethylacetamide or N-methylpyrrolidone.

Among the above-mentioned solvents, organic solvents having a boiling point at 1 atm of 120° C. to 180° C. are preferable in terms of coating properties and drying properties. As a solvent, propylene glycol monomethyl ether acetate, ethyl lactate, propylene glycol monomethyl ether, ethyl 3-ethoxypropionate, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, diethyl Glycol monoethyl ether, 4-hydroxy-4-methyl-2-pentanone and N,N-dimethylformamide, more preferably propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, 4-hydroxy- 4-Methyl-2-pentanone, ethyl lactate and ethyl 3-ethoxypropionate.

The content of the solvent (E) is preferably from 70 to 95% by mass, more preferably from 75 to 92% by mass, based on the total amount of the red coloring composition of the present invention. In other words, the total solid content of the red coloring composition is preferably from 5 to 30% by mass, more preferably from 8 to 25% by mass. When the content of the solvent (E) is within the above range, the flatness at the time of coating tends to be good, and the color density does not become insufficient when forming a color filter, so the display characteristics become good. .

＜Leveling agent (F)＞ The leveling agent (F) may, for example, be a silicone-based surfactant, a fluorine-based surfactant, or a silicone-based surfactant having a fluorine atom. These may have a polymerizable group in the side chain. As a silicone type surfactant, the thing which has a siloxane bond in a molecule|numerator, etc. are mentioned. Specifically, Toray Silicone DC3PA, Toray Silicone SH7PA, Toray Silicone DC11PA, Toray Silicone SH21PA, Toray Silicone SH28PA, Toray Silicone SH29PA, Toray Silicone SH30PA, Toray Silicone SH8400 (manufactured by Toray Dow Corning Co., Ltd.), KP321 , KP322, KP323, KP324, KP326, KP340, KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452 and TSF4460 (manufactured by Momentive High-Tech Materials Japan Co., Ltd.), etc. .

As said fluorine-type surfactant, what has a fluorocarbon chain in a molecule|numerator, etc. are mentioned. Specifically, Fluorad (registered trademark) FC430, Fluorad FC431 (manufactured by Sumitomo 3M Co., Ltd.), Megafac (registered trademark) F142D, Megafac F171, Megafac F172, Megafac F173, Megafac F177, Megafac F183, Megafac F554, Megafac R30, Megafac RS-718-K (manufactured by DIC Co., Ltd.), Eftop (registered trademark) EF301, Eftop EF303, Eftop EF351, Eftop EF352 (manufactured by Mitsubishi Materials Corporation, Inc.), Surflon (registered trademark) S381, Surflon S382 , Surflon SC101, Surflon SC105 (manufactured by AGC Co., Ltd.), E5844 (manufactured by Daikin Institute of Fine Chemicals Co., Ltd.), etc.

Examples of the above-mentioned silicone-based surfactant having a fluorine atom include a surfactant having a siloxane bond and a fluorocarbon chain in the molecule. Specifically, Megafac (registered trademark) R08, Megafac BL20, Megafac F475, Megafac F477, Megafac F443 (manufactured by DIC Co., Ltd.) etc. are mentioned.

The content of the leveling agent (F) is preferably from 0.001% by mass to 0.2% by mass based on the total amount of the red coloring composition, more preferably from 0.002% by mass to 0.2% by mass, still more preferably 0.005% by mass More than 0.2% by mass. In addition, the content rate of the said dispersing agent is not included in this content rate. When the content rate of a leveling agent (F) exists in the said range, the flatness of a color filter can be made favorable.

＜Other ingredients＞ The red coloring composition of the present invention may optionally contain additives known in the technical field such as polymerization initiation aids, fillers, other polymer compounds, adhesion promoters, light stabilizers, and chain transfer agents. Examples of adhesion promoters include: vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris(2-methoxyethoxy)silane, 3-glycidoxypropyltrimethoxy Silane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxy 3-Chloropropylmethyldimethoxysilane, 3-Chloropropyltrimethoxysilane, 3-Methacryloxypropyltrimethoxysilane, 3-Mercaptopropyltrimethoxysilane , 3-isocyanatopropyltriethoxysilane, N-2-(aminoethyl)-3-aminopropylmethyldimethoxysilane, N-2-(aminoethyl) -3-aminopropylmethyldiethoxysilane, N-2-(aminoethyl)-3-aminopropyltrimethoxysilane, 3-aminopropyltrimethoxysilane, 3- Aminopropyltriethoxysilane, N-phenyl-3-aminopropyltrimethoxysilane and N-phenyl-3-aminopropyltriethoxysilane, etc.

＜Manufacturing method of red coloring composition＞ The red coloring composition can be prepared, for example, by mixing a colorant (A), a resin (B), a polymerizable compound (C), a polymerization initiator (D), a solvent (E), and an optional leveling agent ( F), a polymerization initiation aid (D1), and other components are mixed and prepared. The colorant (A) may be contained in the pigment dispersion in advance. The target red coloring composition can be prepared by mixing the remaining components in the pigment dispersion so as to have a specific concentration. In the case of including a dye, the dye may be dissolved in part or all of the solvent (E) in advance to prepare a solution. Preferably, the solution is filtered through a filter with a pore size of about 0.01 to 1 μm. Preferably, the mixed red coloring composition is filtered through a filter having a pore diameter of about 0.01 to 10 μm.

＜Color Filter＞ As a method of manufacturing the coloring pattern of a color filter from the red coloring composition of this invention, a photolithography method, an inkjet method, a printing method, etc. are mentioned. Among them, photolithography is preferred. Photolithography is a method in which the above-mentioned red coloring composition is applied to a substrate, dried to form a composition layer, and the composition layer is exposed through a photomask to be developed. In photolithography, by not using a photomask and/or without developing during exposure, it is possible to form a colored coating film that is a cured product of the above-mentioned composition layer.

The film thickness of the color filter (cured film) is, for example, 30 μm or less, preferably 20 μm or less, more preferably 6 μm or less, further preferably 3 μm or less, still more preferably 1.5 μm or less, especially preferably 0.5 μm or less, preferably 0.1 μm or more, more preferably 0.2 μm or more, still more preferably 0.3 μm or more.

As the substrate, glass plates such as quartz glass, borosilicate glass, alumina silicate glass, soda lime glass coated with silica, or polycarbonate, polymethyl methacrylate, polyparaphenylene, etc. can be used. Resin boards such as ethylene diformate are formed by forming aluminum, silver, silver/copper/palladium alloy thin films on silicon or the above-mentioned substrates. On these substrates, other color filter layers, resin layers, transistors, circuits, etc. may also be formed. In addition, a substrate obtained by subjecting a silicon substrate to HMDS (hexamethyldisilazane) treatment may also be used.

The formation of pixels of each color by photolithography can be carried out by known or commonly used devices or conditions. For example, it can be produced as follows. First, a red coloring composition is coated on a substrate, and then heat-dried (pre-baked) and/or reduced-pressure dried to remove volatile components such as solvents and dried to obtain a smooth composition layer. As a coating method, a spin coat method, a slit coat method, a slit and spin coat method, etc. are mentioned. The temperature at the time of heat-drying becomes like this. Preferably it is 30-120 degreeC, More preferably, it is 50-110 degreeC. Moreover, as heating time, it is preferable that it is 10 seconds - 60 minutes, and it is more preferable that it is 30 seconds - 30 minutes. When performing reduced-pressure drying, it is preferable to carry out under the pressure of 50-150 Pa, and to carry out in the temperature range of 20-25 degreeC. The film thickness of the composition layer is not particularly limited, and may be appropriately selected according to the film thickness of the intended color filter.

Next, the composition layer is exposed through a photomask used to form a colored pattern of interest. The pattern on the photomask is not particularly limited, and a pattern corresponding to the target application is used. As a light source for exposure, a light source that generates light with a wavelength of 250 to 450 nm is preferable. For example, the light below 350 nm can be cut off with a filter that cuts off the wavelength range, or the light around 436 nm, 408 nm, and 365 nm can be selectively processed with a bandpass filter that extracts these wavelength ranges extract. Specifically, a mercury lamp, a light emitting diode, a metal halide lamp, a halogen lamp, etc. are mentioned. In order to uniformly irradiate the entire exposure surface with parallel light, or to accurately position the mask and the substrate, it is preferable to use a reduction projection exposure device such as a mask alignment exposure machine and a stepper exposure machine or an adjacent exposure device.

A colored pattern is formed on the substrate by contacting the exposed composition layer with a developing solution for development. By development, the unexposed portion of the composition layer is dissolved in a developing solution and removed. As a developing solution, for example, an aqueous solution of a basic compound such as potassium hydroxide, sodium bicarbonate, sodium carbonate, tetramethylammonium hydroxide is preferable. The concentration in the aqueous solution of these basic compounds is preferably from 0.01 to 10% by mass, more preferably from 0.03 to 5% by mass. Furthermore, the developer may contain a surfactant. The developing method may be any one of a liquid covering method, a dipping method, a spraying method, and the like. Furthermore, the substrate can be tilted at any angle during development. It is preferable to perform water washing after image development.

Furthermore, it is preferable to post-bak the obtained colored pattern. The post-baking temperature is preferably from 80 to 250°C, more preferably from 100 to 245°C. The post-baking time is preferably from 1 to 120 minutes, more preferably from 2 to 30 minutes.

The colored pattern and colored coating film obtained in this way can be used as a color filter, and the color filter can be used as a display device (such as a liquid crystal display device, an organic EL (Electroluminescence, electroluminescence) device, etc.), an electronic paper, etc. , Color filters used in solid-state imaging devices, etc. [Example]

Hereinafter, the present invention will be described in more detail with examples, but the present invention is not limited by these examples. In the examples, unless otherwise specified, % and parts indicating content or usage are based on mass.

[Resin Synthesis Example 1] Into a flask equipped with a reflux cooler, a dropping funnel, and a stirrer, an appropriate amount of nitrogen gas was introduced to form a nitrogen atmosphere, and 280 parts of propylene glycol monomethyl ether acetate was added, and heated to 80° C. while stirring. Then, 38 parts of acrylic acid, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]dec-8-yl acrylate and 3,4-epoxytricyclo[ 5.2.1.0 ^2,6 ] Dec-9-yl ester mixture (content ratio: 1:1) 289 parts dissolved in 125 parts of propylene glycol monomethyl ether acetate was added dropwise to the flask. On the other hand, 33 parts of the polymerization initiator 2,2-azobis(2,4-dimethylvaleronitrile) was dissolved in 235 parts of propylene glycol monomethyl ether acetate over about 6 hours using another drip pump. The resulting solution was added dropwise to the flask. After completion of the dropwise addition, it was kept at the same temperature for 4 hours, and then cooled to room temperature to obtain a copolymer (resin (B-1)) with a solid content of 35.1%. The weight average molecular weight Mw of the produced copolymer was 9200, the degree of dispersion was 2.08, and the acid value in terms of solid content was 77 mg-KOH/g. Resin (B-1) has the following structural units.

[chemical 4]

The weight average molecular weight (Mw) and number average molecular weight (Mn) of polystyrene conversion of resin were measured on the following conditions by the GPC(Gel Permeation Chromatography, gel permeation chromatography) method. Device: HLC-8120GPC (manufactured by Tosoh Co., Ltd.) Column: TSK-GELG2000HXL Column temperature: 40°C Solvent: THF Flow rate: 1.0 mL/min Concentration of solid components in the tested liquid: 0.001 to 0.01% by mass Injection volume: 50 μL Detector: RI Standard material for calibration: TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Co., Ltd.) The ratio (Mw/Mn) of the polystyrene-equivalent weight-average molecular weight and the number-average molecular weight obtained above was defined as the degree of dispersion.

[Preparation of Dispersion 1] 10.0 parts of C.I. Pigment Orange 43 (pigment), 7.8 parts of dispersant (BYKLPN-6919 manufactured by BYK, propylene glycol monomethyl ether acetate solution with 60% solid content) (calculated as solid content), resin (B-1 ) 7.8 parts (solid content conversion), 4-hydroxy-4-methyl-2-pentanone 22.2 parts were mixed, mixed with propylene glycol monomethyl ether acetate 154.8 parts, added 0.4 μm zirconia beads 600 parts, used A paint conditioner (manufactured by LAU) was shaken for 1 hour. Thereafter, dispersion liquid 1 was obtained by removing the zirconia beads by filtration.

[Preparation of Dispersion 2-10] Dispersion liquids 2-10 were obtained by the same method as dispersion liquid 1 except having changed to the composition shown in Table 1. In Table 2, each component represents the following compounds. PO43: C.I. Pigment Orange 43; Orange Colorant (A-1) PO64: C.I. Pigment Orange 64; Orange Colorant (A-1) PR254: C.I. Pigment Red 254; Red Colorant (A-2) PR291: C.I. Pigment Red 291; Red Colorant (A-2) PR177: C.I. Pigment Red 177; Red Colorant (A-2) PR269: C.I. Pigment Red 269; Red Colorant (A-2) PY138: C.I. Pigment Yellow 138 (Quinophthalone Pigment); Yellow Colorant PY150: C.I. Pigment Yellow 150 (nickel complex type azo pigment); yellow colorant (A-3) PY185: C.I. Pigment Yellow 185 (isoindoline pigment); yellow colorant (A-3) PY139: C.I. Pigment Yellow 139 (isoindoline pigment); yellow colorant (A-3) Solvent (E-1): 4-Hydroxy-4-methyl-2-pentanone Solvent (E-2): Propylene glycol monomethyl ether acetate Solvent (E-3): Propylene Glycol Monomethyl Ether

[Table 1] [Table 1] Dispersions 1 2 3 4 5 6 7 8 9 10 orange colorant PO43(A-1) 10.0 PO64(A-1) 10.0 red colorant PR254(A-2) 10.0 PR291(A-2) 10.0 PR177(A-2) 10.0 PR269(A-2) 10.0 yellow colorant PY138 (Quinophthalone series) 10.0 PY150(A-3) 10.0 PY185(A-3) 10.0 PY139(A-3) 10.0 Resin (B) (B-1) (Converted amount of solid content) 7.8 7.8 4.2 4.2 3.5 2.5 4.7 4.0 3.5 3.5 Dispersant (converted amount of solid content) 7.8 7.8 2.9 2.9 3.5 2.7 2.0 3.7 6.5 3.5 Solvent (E) (E-1) 22.2 22.2 (E-2) 154.8 154.8 52.6 52.6 51.1 28.4 56.5 49.4 90.8 54.0 (E-3) 3.9 3.9 34.8 4.2 4.0

[Preparation of Compositions X-1 to X-2, Compositions Y-1 to Y-4, and Compositions Z-1 to Z-4] The components shown in Table 2 were mixed to obtain compositions X-1 to X-2, compositions Y-1 to Y-4, and compositions Z-1 to Z-4. In Table 2, each component represents the following compounds. Resin (B-1): Resin (B-1) (solid content conversion) Polymerizable compound (C-1): dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) Polymerization initiator (D-1): N-Acetyloxy-1-(4-phenylthiophenyl)-3-cyclohexylpropan-1-one-2-imine (PBG-327; oxime compound ; Manufactured by Changzhou Qiangli Electronic New Material Co., Ltd.) Solvent (E-2): Propylene glycol monomethyl ether acetate Leveling agent (F-1): Polyether-modified silicone oil (solid content conversion) (Toray Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.)

[Examples 1 to 11, Comparative Examples 1 to 10] The components shown in Tables 3 to 4 were mixed to obtain a red coloring composition.

<Production of color filter (colored coating film)> [Compositions X-1 to X-2, Compositions Y-1 to Y-4, Compositions Z-1 to Z-4] By spin coating method Adjust the rotation speed so that the film thickness after post-baking becomes 1 μm, and apply compositions X-1 to X-2, compositions Y-1 to Y-4, and compositions Z-1 to Z-4 on 5 cm After being mounted on a square glass substrate (Eagle 2000; manufactured by Corning Incorporated), it was prebaked at 100° C. for 3 minutes to form a colored resin composition layer. After cooling, light irradiation was performed at an exposure amount of 60 mJ/cm ² (based on 365 nm) in an air atmosphere using an exposure machine (TME-150RSK; manufactured by TOPCON Co., Ltd.). Afterwards, bake in an oven at 230° C. for 20 minutes to obtain a color filter. [Red Coloring Composition] The red coloring composition was coated on a 5 cm square glass substrate (Eagle 2000; manufactured by Corning Incorporated) by a spin coating method. In this spin coating, the rotation speed is adjusted so that the film thickness after post-baking becomes the film thickness which exhibits predetermined chromaticity. Then, it was prebaked at 100° C. for 3 minutes to form a colored resin composition layer. After cooling, light irradiation was performed at an exposure amount of 60 mJ/cm ² (based on 365 nm) in an air atmosphere using an exposure machine (TME-150RSK; manufactured by TOPCON Co., Ltd.). Afterwards, bake in an oven at 230° C. for 20 minutes to obtain a color filter.

<Absorbance measurement test> The color filter obtained by the production method of the color filter was spectroscopically measured using a colorimeter (OSP-SP-200; manufactured by Olympus Co., Ltd.). [Compositions X-1 to X-2, Compositions Y-1 to Y-4, Compositions Z-1 to Z-4] About Compositions X-1 to X-2, Compositions Y-1 to Y -4. For color filters obtained from compositions Z-1 to Z-4, by converting the obtained transmission spectrum into absorbance according to the following formula (1), calculate the 440, 480, 530, 570 of the colored coating film , Absorbance at a wavelength of 580 nm. A=-log ₁₀ T...(1) (In the formula (1), A represents the absorbance, T represents the transmittance) [Red coloring composition] Regarding the color filter obtained from the red coloring composition, according to the obtained transmittance The spectrum calculates the chromaticity.

＜Film thickness measurement＞ About the obtained colored coating film, the film thickness was measured using the film thickness measuring apparatus (DEKTAK3; Nippon Vacuum Technology Co., Ltd. make).

＜Brightness measurement test＞ The color filter obtained by the production method of the color filter was spectroscopically measured using a colorimeter (OSP-SP-200; manufactured by Olympus Co., Ltd.). Using the obtained transmission spectrum, the chromaticity and brightness were calculated from the wavelength when the light from the C light source was transmitted.

[Table 2] [Table 2] combination X-1 X-2 Y-1 Y-2 Y-3 Y-4 Z-1 Z-2 Z-3 Z-4 Dispersion 1 PO43(A-1) 289 Dispersion 2 PO64(A-1) 289 Dispersion 3 PR254(A-2) 103 Dispersion 4 PR291(A-2) 103 Dispersion 5 PR177(A-2) 95 Dispersion 6 PR269(A-2) 104 Dispersion 7 PY138 (Quinophthalone series) 101 Dispersion 8 PY150(A-3) 95 Dispersion 9 PY185(A-3) 161 Dispersion 10 PY139(A-3) 104 Resin (B) (B-1) (Conversion of solid content) 55 55 60 60 61 62 59 60 60 61 Polymeric compound (C) (C-1) 35 35 35 35 35 35 35 35 35 35 Polymerization initiator (D) (D-1) 7 7 7 7 7 7 7 7 7 7 Solvent (E) (E-2) 554 554 521 521 509 496 499 519 479 507 Leveling agent (F) (F-1) 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 Absorbance test 440 nm 0.46 0.76 0.29 0.26 0.19 0.11 0.42 0.69 0.92 0.76 480 nm 0.42 0.88 0.45 0.41 0.23 0.18 0.06 0.23 0.39 0.57 530 nm 0.58 0.71 0.46 0.40 0.37 0.50 0.00 0.02 0.01 0.06 570 nm 0.06 0.19 0.39 0.39 0.35 0.52 0.00 0.01 0.00 0.02 580 nm 0.04 0.15 0.11 0.13 0.25 0.38 0.00 0.01 0.00 0.02

[Table 3] [Table 3] red coloring composition Ex.1 Ex.2 Ex.3 Ex.4 Ex.5 Ex.6 Ex.7 Ex.8 Ex.9 Ex.10 Ex.11 Dispersion 1 PO43(A-1) 290 251 292 500 528 Dispersion 2 PO64(A-1) 346 298 348 691 662 667 Dispersion 3 PR254(A-2) 82 Dispersion 4 PR291(A-2) 127 Dispersion 5 PR177(A-2) 580 606 578 567 595 565 Dispersion 6 PR269(A-2) 627 661 583 501 453 Dispersion 7 PY138 (Quinophthalone Series) Dispersion 8 PY150(A-3) 76 76 90 Dispersion 9 PY185(A-3) 126 127 150 95 94 Dispersion 10 PY139(A-3) 82 83 138 Resin (B) (B-1) (Conversion of solid content) 25 25 25 twenty three twenty four twenty four 36 38 36 25 twenty three Polymeric compound (C) (C-1) 35 35 35 35 35 35 35 35 35 35 35 Polymerization initiator (D) (D-1) 7 7 7 7 7 7 7 7 7 7 7 Solvent (E) (E-2) 580 571 569 556 550 545 389 370 340 351 345 Leveling agent (F) (F-1) 0.2 0.2 0.2 0.2 0.2 0.2 0.2 0.2 0.2 0.2 0.2 Colorant (A-3)/colorant (A-1) (mass ratio) 0.76 0.92 0.77 0.64 0.78 0.65 0.38 0.41 0.56 0.34 0.32 Chroma x 0.680 the y 0.317 Film thickness measurement (μm) 2.7 2.6 2.6 2.6 2.5 2.5 2.6 2.6 2.6 2.7 2.7 Brightness measurement Y(%) - 104 - 107 112 107 - - - - -

[Table 4] [Table 4] red coloring composition Co.1 Co.2 Co.3 Co.4 Co.5 Co.6 Co.7 Co.8 Co.9 Co.10 Dispersion 1 PO43(A-1) 697 353 403 1049 432 1302 Dispersion 2 PO64(A-1) 861 460 455 511 Dispersion 3 PR254(A-2) 164 167 Dispersion 4 PR291(A-2) 165 166 Dispersion 5 PR177(A-2) 566 482 470 537 530 456 457 519 Dispersion 6 PR269(A-2) 640 568 Dispersion 7 PY138 (Quinophthalone Series) 82 84 Dispersion 8 PY150(A-3) Dispersion 9 PY185(A-3) Dispersion 10 PY139(A-3) Resin (B) (B-1) (Conversion of solid content) 15 twenty two twenty one 28 twenty one 11 20 20 19 19 Polymeric compound (C) (C-1) 35 35 35 35 35 35 35 35 35 35 Polymerization initiator (D) (D-1) 7 7 7 7 7 7 7 7 7 7 Solvent (E) (E-2) 401 531 510 231 500 330 485 487 123 465 Leveling agent (F) (F-1) 0.2 0.2 0.2 0.2 0.2 0.2 0.2 0.2 0.3 0.2 Colorant (A-3)/colorant (A-1) (mass ratio) 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 Chroma x 0.680 the y 0.317 Film thickness measurement (μm) 2.8 2.9 2.9 3.0 2.8 2.8 2.8 2.8 2.8 2.8 Brightness measurement Y(%) - - - - 100 - - - - 100

Claims (9)

A red coloring composition comprising a colorant (A), a resin (B), a polymerizable compound (C), a polymerization initiator (D) and a solvent (E), The above-mentioned colorant (A) includes an orange colorant (A-1), a red colorant (A-2) satisfying the condition (X), and a metal-containing azo dye, isoindoline dye, and coumarin At least one yellow coloring agent (A-3) of the group consisting of pigments, The content of the yellow colorant (A-3) is 250 parts by mass or less with respect to 100 parts by mass of the orange colorant (A-1), [Condition (X)] Preparation of the composition (X-1) which contains only the orange colorant (A-1) as a colorant, and the content of the orange colorant (A-1) in the solid content reaches 10% by mass. (X-1) When measuring the absorbance of a color filter with a film thickness of 1 μm, The absorbance at a wavelength of 480 nm is above 0.40, The absorbance at a wavelength of 530 nm is above 0.55, Absorbance at a wavelength of 580 nm is below 0.20. The red coloring composition as claimed in item 1, wherein the above-mentioned red coloring agent (A-2) satisfies condition (Y), [Condition (Y)] A composition (Y) containing only the red colorant (A-2) as a colorant was prepared, and the content of the red colorant (A-2) in the solid content was 10% by mass. ) to measure the absorbance of a color filter with a film thickness of 1 μm, The absorbance at a wavelength of 440 nm is below 0.30, The absorbance at a wavelength of 480 nm does not reach 0.50, The absorbance at a wavelength of 530 nm is above 0.30, The absorbance at a wavelength of 580 nm is above 0.10. The red coloring composition as claimed in item 1 or 2, wherein the above-mentioned yellow coloring agent (A-3) satisfies condition (Z), [Condition (Z)] Preparation of a composition (Z-1) containing only the yellow colorant (A-3) as a colorant, and the content of the yellow colorant (A-3) in the solid content is 10% by mass. (Z-1) When measuring the absorbance of a color filter with a film thickness of 1 μm, The absorbance at a wavelength of 440 nm is above 0.50, The absorbance at a wavelength of 480 nm is above 0.20, The absorbance at a wavelength of 530 nm is below 0.10, The absorbance at a wavelength of 580 nm is below 0.10. The red coloring composition according to any one of claims 1 to 3, wherein the orange colorant (A-1) contains at least one selected from C.I. Pigment Orange 43 and C.I. Pigment Orange 64. The red coloring composition according to any one of Claims 1 to 4, wherein the above-mentioned red colorant (A-2) comprises the group selected from C.I. Pigment Red 177, C.I. Pigment Red 254, C.I. Pigment Red 269, C.I. Pigment Red 291 and C.I. At least one of the group consisting of Acid Red 52. The red coloring composition according to any one of Claims 1 to 5, wherein the above-mentioned yellow coloring agent (A-3) includes at least one selected from the group consisting of C.I. Pigment Yellow 139, C.I. Pigment Yellow 150 and C.I. 1 or more. A color filter formed of the red coloring composition according to any one of Claims 1 to 6. A display device comprising the color filter according to Claim 7. A solid-state imaging device, which includes the color filter according to claim 7.