JP7632708B2 - Azo pigment, colorant for color filter, coloring composition and color filter - Google Patents

Description

The present invention relates to a colorant for a color filter, a coloring composition, and a color filter formed using the same, which are used in the manufacture of color filters for use in color liquid crystal displays and color solid-state imaging devices.

A liquid crystal display device is a display device in which a liquid crystal layer sandwiched between two polarizing plates controls the degree of polarization of light that passes through the first polarizing plate, and controls the amount of light that passes through the second polarizing plate to display an image. The mainstream type uses twisted nematic (TN) liquid crystals. Other representative liquid crystal display types include the in-plane switching (IPS) type, in which a pair of electrodes are provided on one of the substrates and an electric field is applied in a direction parallel to the substrate, the vertical alignment (VA) type, in which nematic liquid crystals with negative dielectric anisotropy are vertically aligned, and the optically concave bend (OCB) type, in which the optical axes of uniaxial retardation films are perpendicular to each other to provide optical compensation. All of these types are in practical use.

Liquid crystal display devices are capable of displaying color by placing a color filter between two polarizing plates, and in recent years have come to be used in televisions, computer monitors, and other applications, which has led to an increased demand for color filters with higher contrast and brightness.

A color filter consists of fine stripe-shaped filter segments of two or more different hues arranged in parallel or crosswise rows on the surface of a transparent substrate such as glass, or fine filter segments arranged in a fixed vertical and horizontal array. The filter segments are very fine, ranging from a few microns to a few hundred microns in size, and are arranged in a regular pattern according to the hue.

In general, in color LCD devices, transparent electrodes for driving the liquid crystal are formed on top of the color filters by deposition or sputtering, and an alignment film for orienting the liquid crystal in a certain direction is formed on top of that. To obtain the full performance of these transparent electrodes and alignment films, they must be formed at high temperatures, generally above 200°C, and preferably above 230°C. For this reason, the current mainstream method for manufacturing color filters is the pigment dispersion method, which uses a pigment with excellent light and heat resistance as the colorant.

Quality requirements for color filters include brightness and contrast ratio. If a color filter with a low contrast ratio is used, it will disrupt the degree of polarization controlled by the liquid crystal, causing light to leak when it should be blocked (OFF state) and attenuating transmitted light when it should be transmitted (ON state), resulting in a blurred screen. For this reason, high contrast is essential to realizing a high-quality LCD display device.

Furthermore, if low-brightness color filters are used, the light transmittance is low, resulting in a dark screen; to make the screen brighter, it is necessary to increase the number of backlights, which are the light source. For this reason, there is a trend toward higher brightness color filters in order to curb increases in power consumption. Furthermore, as mentioned above, color liquid crystal devices have come to be used in televisions, computer monitors, etc., and as a result, there is an increasing demand for color filters with higher brightness, higher contrast, and higher reliability.

For the red filter segment, which is one of the three primary colors (red, green, and blue; RGB) of a color filter substrate, pigments with excellent light and heat resistance, such as diketopyrrolopyrrole pigments, anthraquinone pigments, or perylene pigments, are generally used alone or in combination as colorants.

Among the above pigment types, C.I. Pigment Red 254, a diketopyrrolopyrrole pigment, is used as the main pigment from the viewpoint of brightness, and C.I. Pigment Red 177, an anthraquinone pigment, is used from the viewpoint of contrast ratio. Of these, C.I. Pigment Red 177 has a lower spectral transmittance than C.I. Pigment Red 254 and a poor spectral shape, so there is a drawback in that the more C.I. Pigment Red 177 is added, the lower the brightness becomes. Therefore, there is a need to develop a substitute material for C.I. Pigment Red 177 that has excellent brightness.

In recent years, in order to achieve high brightness and high coloring power, it has been proposed to use azo pigments such as C.I. Pigment Red 269 and disazo pigments described in Patent Document 3 as the main pigments. However, since the affinity of the pigments to the solvent and the acidity of the pigment surface are different from those of C.I. Pigment Red 254 and C.I. Pigment Red 177, the pigments have inferior dispersibility, fluidity, and storage stability, and furthermore, they have inferior heat resistance and light resistance, and practical color filters have not been obtained. In addition, with azo pigments such as C.I. Pigment Red 269, there is a problem of a decrease in brightness due to color transfer to adjacent filter segments of other colors, and there is a high demand for migration properties.

Patent Documents 1 to 4 propose using C.I. Pigment Red 177, C.I. Pigment Red 269, and the disazo pigments described in Patent Documents 3 and 4 as main pigments in order to further improve the brightness of the red filter segment, but sufficient brightness and storage stability could not be obtained, and further improvements were required.

JP 2008-304521 A Special Publication No. 2007-533802 JP 2014-160160 A Patent No. 6368844

The object of the present invention is to provide a coloring composition for color filters that not only has excellent heat resistance, little coating foreign matter, good storage stability, solvent resistance and dye migration properties, but also has high brightness and contrast.

As a result of extensive research, the inventors discovered that the above problems could be solved by using an azo pigment having a specific structure as a colorant for color filters, and thus arrived at the present invention.

That is, the present invention relates to an azo pigment which is a compound represented by any one of the following general formulas (1) to (3).

General formula (1)

[In general formula (1), R ₁ to R ₅ each independently represent a hydrogen atom, a halogen atom, an alkyl group which may have a substituent, an alkoxyl group which may have a substituent, an aryloxy group which may have a substituent, a hydroxyl group, a cyano group, a nitro group, a carboxyl group, a sulfo group, -CONR ₆ R ₇ or -SO ₂ NR ₈ R _9. R ₆ to R ₉ each independently represent a hydrogen atom, an alkyl group which may have a substituent or a phenyl group which may have a substituent, except for the case where R ₁ , R ₃ and R ₄ are all hydrogen atoms.]
X ₁ to X ₄ each independently represent a hydrogen atom, an alkyl group which may have a substituent, an alkoxyl group which may have a substituent, a hydroxyl group, a cyano group, a nitro group, a carboxyl group, a sulfo group, or a halogen atom.]

General formula (2)

[In general formula (2), R ₁₀ to R ₁₄ each independently represent a hydrogen atom, a halogen atom, an alkyl group which may have a substituent, an alkoxyl group which may have a substituent, an aryloxy group which may have a substituent, a hydroxyl group, a cyano group, a nitro group, a carboxyl group, a sulfo group, -CONR ₁₅ R ₁₆ or -SO ₂ NR ₁₇ R _18. R ₁₅ to R ₁₈ each independently represent a hydrogen atom, an alkyl group which may have a substituent or a phenyl group which may have a substituent, except for the case where R ₁₀ , R ₁₂ and R ₁₃ are all hydrogen atoms.]
X ₅ to X ₁₂ each independently represent a hydrogen atom, an alkyl group which may have a substituent, an alkoxyl group which may have a substituent, a hydroxyl group, a cyano group, a nitro group, a carboxyl group, a sulfo group, or a halogen atom. A represents a direct bond, an alkylene group which may have a substituent, -O-, -S-, -CO-, -SO ₂ -, -COO-, -CONH-, or -SO ₂ NH-.]

General formula (3)

[In general formula (3), R ₁₉ to R ₂₃ each independently represent a hydrogen atom, a halogen atom, an alkyl group which may have a substituent, an alkoxyl group which may have a substituent, an aryloxy group which may have a substituent, a hydroxyl group, a cyano group, a nitro group, a carboxyl group, a sulfo group, -CONR ₂₄ R ₂₅ , or -SO ₂ NR ₂₆ R _{27. R 24} to R ₂₇ each independently represent a hydrogen atom, an alkyl group which may have a substituent, or a phenyl group which may have a substituent, except when R ₁₉ , R ₂₁ , and R ₂₂ are all hydrogen atoms.]

Another embodiment of the present invention relates to the azo pigment, wherein at least one of R ₁ to R _{5 in the general formula (1),} R ₁₀ to R _{14 in the general formula (2),} and R ₁₉ to R ₂₃ in the general formula (3) is -CONHY or -SO ₂ NHY (wherein Y represents a phenyl group which may have a substituent).

The present invention also relates to a colorant for color filters that contains the azo pigment.

The present invention also relates to a coloring composition for color filters, comprising a colorant and a binder resin, the colorant being the colorant for color filters described above.

The present invention also relates to the coloring composition for color filters, further comprising a resin-type dispersant having an acidic substituent.

The present invention also relates to the coloring composition for color filters, characterized in that the resin-type dispersant having an acidic substituent is a resin-type dispersant having an aromatic carboxyl group.

The present invention also relates to the coloring composition for color filters, which further contains a dye derivative, and is characterized in that the dye derivative contains a dye derivative having a basic substituent.

The present invention also relates to the coloring composition for color filters, characterized in that the colorant further comprises at least one selected from the group consisting of C.I. Pigment Red 242, C.I. Pigment Red 254, C.I. Pigment Red 291, C.I. Pigment Yellow 138, C.I. Pigment Yellow 139, C.I. Pigment Yellow 150, and a yellow pigment represented by the following general formula (4).

General formula (4)

[In general formula (4), Z ₁ to Z ₁₃ each independently represent a hydrogen atom, a halogen atom, an alkyl group which may have a substituent, an alkoxyl group which may have a substituent, an aryl group which may have a substituent, -SO ₃ H, -COOH, and monovalent to trivalent metal salts of these acidic groups, alkylammonium salts, a phthalimidomethyl group which may have a substituent, or a sulfamoyl group which may have a substituent.
Adjacent groups of Z ₁ to Z ₄ and/or Z ₁₀ to Z ₁₃ may be joined together to form an aromatic ring which may have a substituent.]

The present invention also relates to the coloring composition for color filters, further comprising a photopolymerizable monomer.

The present invention also relates to a color filter comprising a filter segment formed from the coloring composition for color filters on a substrate.

The present invention has the excellent effect of providing a color filter coloring composition and color filter that are excellent in heat resistance, have little coating foreign matter, and have good storage stability, solvent resistance, and dye migration properties, as well as high brightness and contrast.

The present invention will be described in detail below. In this specification, unless otherwise specified, the terms "(meth)acryloyl", "(meth)acrylic", "(meth)acrylic acid", "(meth)acrylate", or "(meth)acrylamide" refer to "acryloyl and/or methacryloyl", "acrylic and/or methacrylic", "acrylic acid and/or methacrylic acid", "acrylate and/or methacrylate", or "acrylamide and/or methacrylamide", respectively. In addition, "C.I." in this specification means Color Index (C.I.).

<Azo pigments>
First, the azo pigments of the present invention represented by the general formulas (1) to (3) will be described. In the present specification, the "azo pigments of the general formulas (1) to (3)" and the "colorant for color filters" will be abbreviated as "pigment" and "colorant", respectively.

General formula (1)

[In general formula (1), R ₁ to R ₅ each independently represent a hydrogen atom, a halogen atom, an alkyl group which may have a substituent, an alkoxyl group which may have a substituent, an aryloxy group which may have a substituent, a hydroxyl group, a cyano group, a nitro group, a carboxyl group, a sulfo group, -CONR ₆ R ₇ or -SO ₂ NR ₈ R _9. R ₆ to R ₉ each independently represent a hydrogen atom, an alkyl group which may have a substituent or a phenyl group which may have a substituent, except for the case where R ₁ , R ₃ and R ₄ are all hydrogen atoms.]
X ₁ to X ₄ each independently represent a hydrogen atom, an alkyl group which may have a substituent, an alkoxyl group which may have a substituent, a hydroxyl group, a cyano group, a nitro group, a carboxyl group, a sulfo group, or a halogen atom.]

In R ₁ to R ₅ , the "halogen atom" may include fluorine, bromine, chlorine, and iodine, with chlorine being preferred.

Examples of the "alkyl group which may have a substituent" in R ₁ to R ₅ include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a tert-butyl group, an isobutyl group, a tert-amyl group, a 2-ethylhexyl group, a stearyl group, a chloromethyl group, a trichloromethyl group, a trifluoromethyl group, a 2-methoxyethyl group, a 2-chloroethyl group, a 2-nitroethyl group, a cyclopentyl group, a cyclohexyl group, a dimethylcyclohexyl group, and the like. Of these, a methyl group and a trifluoromethyl group are preferred.

Examples of the "alkoxy group which may have a substituent" in R ₁ to R ₅ include a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, an n-octyloxy group, a 2-ethylhexyloxy group, a trifluoromethoxy group, a cyclohexyloxy group, a stearyloxy group, and a 2-(diethylamino)ethoxy group. Of these, a methoxy group and a trifluoromethoxy group are preferred, and a methoxy group is particularly preferred.

Examples of the "aryloxy group which may have a substituent" in R ₁ to R ₅ include a phenoxy group, a naphthyloxy group, a 4-methylphenyloxy group, a 3,5-chlorophenyloxy group, a 4-chloro-2-methylphenyloxy group, a 4-tert-butylphenyloxy group, a 4-methoxyphenyloxy group, a 4-diethylaminophenyloxy group, a 4-nitrophenyloxy group, and the like, and among these, a phenoxy group is preferable.

In R ₆ to R ₉ , examples of the "alkyl group which may have a substituent" include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a tert-butyl group, an isobutyl group, a tert-amyl group, a 2-ethylhexyl group, a stearyl group, a chloromethyl group, a trichloromethyl group, a trifluoromethyl group, a 2-methoxyethyl group, a 2-hydroxyethyl group, a 2-chloroethyl group, a 2-nitroethyl group, a cyclopentyl group, a cyclohexyl group, a dimethylcyclohexyl group, and the like, with a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a tert-butyl group, an isobutyl group, and a 2-hydroxyethyl group being preferred.

In R ₆ to R ₉ , examples of the substituent of the "phenyl group which may have a substituent" include the halogen atoms in R ₁ to R ₅ , the alkyl group which may have a substituent, the alkoxy group which may have a substituent, and the aryloxy group which may have a substituent, as well as a hydroxyl group, an amino group, -NR ₁₀₁ R ₁₀₂ , a sulfo group, -SO ₂ NR ₁₀₃ R ₁₀₄ , -COOR ₁₀₅ , -CONR ₁₀₆ R ₁₀₇ , a nitro group, and a cyano group.
R ₁₀₁ to R ₁₀₇ each independently represent a hydrogen atom or an alkyl group which may have a substituent, and the "alkyl group which may have a substituent" is preferably an alkyl group substituted with an amino group, a monoalkylamino group, or a dialkylamino group.

In X ₁ to X ₄ , the "alkyl group which may have a substituent" has the same meaning as in R ₁ to R ₅ .

In X ₁ to X ₄ , the "alkoxy group which may have a substituent" has the same meaning as in R ₁ to R ₅ .

General formula (2)

[In general formula (2), R ₁₀ to R ₁₄ each independently represent a hydrogen atom, a halogen atom, an alkyl group which may have a substituent, an alkoxyl group which may have a substituent, an aryloxy group which may have a substituent, a hydroxyl group, a cyano group, a nitro group, a carboxyl group, a sulfo group, -CONR ₁₅ R ₁₆ or -SO ₂ NR ₁₇ R _18. R ₁₅ to R ₁₈ each independently represent a hydrogen atom, an alkyl group which may have a substituent or a phenyl group which may have a substituent, except for the case where R ₁₀ , R ₁₂ and R ₁₃ are all hydrogen atoms.]
X ₅ to X ₁₂ each independently represent a hydrogen atom, an alkyl group which may have a substituent, an alkoxyl group which may have a substituent, a hydroxyl group, a cyano group, a nitro group, a carboxyl group, a sulfo group, or a halogen atom. A represents a direct bond or a divalent linking group. Examples of the divalent linking group include an alkylene group which may have a substituent, -O-, -S-, -CO-, -SO ₂ -, -COO-, -CONH-, and -SO ₂ NH-.]

In R ₁₀ to R ₁₄ , the "halogen atom", the "alkyl group which may have a substituent", the "alkoxy group which may have a substituent", and the "aryloxy group which may have a substituent" have the same meanings as those in R ₁ to R ₅ .

In R ₁₅ to R ₁₈ , the "alkyl group which may have a substituent" and the "phenyl group which may have a substituent" have the same meanings as those in R ₆ to R ₉ .

In X ₅ to X ₁₂ , the "alkyl group which may have a substituent" and the "alkoxy group which may have a substituent" have the same meanings as those in R ₁ to R ₅ .

In A, examples of the alkylene group which may have a substituent include a methylene group, an ethylene group, an n-propylene group, an n-butylene group, an n-hexylene group, an n-heptylene group, an n-octylene group, and an n-dodecylene group, and examples of the substituent include the "alkyl group which may have a substituent" represented by R ₁ to R ₅ .

In formula (2), A is preferably an alkylene group which may have a substituent, -O-, -S-, -CO- or -SO ₂ -, and among these, -SO ₂ - is particularly preferred.

General formula (3)

[In general formula (3), R ₁₉ to R ₂₃ each independently represent a hydrogen atom, a halogen atom, an alkyl group which may have a substituent, an alkoxyl group which may have a substituent, an aryloxy group which may have a substituent, a hydroxyl group, a cyano group, a nitro group, a carboxyl group, a sulfo group, -CONR ₂₄ R ₂₅ , or -SO ₂ NR ₂₆ R _{27. R 24} to R ₂₇ each independently represent a hydrogen atom, an alkyl group which may have a substituent, or a phenyl group which may have a substituent, except when R ₁₉ , R ₂₁ , and R ₂₂ are all hydrogen atoms.]

In R ₁₉ to R ₂₃ , the "halogen atom", the "alkyl group which may have a substituent", the "alkoxy group which may have a substituent", and the "aryloxy group which may have a substituent" have the same meanings as those in R ₁ to R ₅ .

In R ₂₄ to R ₂₇ , the "alkyl group which may have a substituent" and the "phenyl group which may have a substituent" have the same meanings as those in R ₆ to R ₉ .

From the viewpoint of storage stability, it is preferable that at least one of R ₁ to R _{5 in general formula (1),} R ₁₀ to R _{14 in general formula (2),} and R ₁₉ to R ₂₃ in general formula (3) is -CONHY or -SO ₂ NHY (Y represents a phenyl group which may have a substituent).

<Colorants for color filters>
The colorant for color filters of the present invention is characterized by containing an azo pigment consisting of a compound represented by any one of the general formulas (1) to (3). The colorant for color filters of the present invention may be used in combination with other colorants such as pigments or dyes other than the pigment consisting of a compound represented by any one of the general formulas (1) to (3) in order to adjust the chromaticity, etc., within the scope of not impairing the effects of the present invention. These pigments and dyes may be used alone or in a mixture of two or more kinds in any ratio as necessary.

Other colorants include, for example, red pigments such as C.I. Pigment Red 7, 14, 41, 48:1, 48:2, 48:3, 48:4, 57:1, 81, 81:1, 81:2, 81:3, 81:4, 122, 146, 168, 169, 176, 177, 178, 179, 184, 185, 187, 200, 202, 208, 210, 242, 246, 254, 255, 264, 269, 270, 272, 273, 274, 276, 277, 278, 279, 280, 281, 282, 283, 284, 285, 286, 287, 291, 295, or 296. Examples of red dyes include xanthene dyes, azo dyes (pyridone-based, barbituric acid-based, etc.), disazo dyes, anthraquinone dyes, methine dyes, etc. In addition, the dyes may be in the form of lake pigments made by turning these dyes into lakes, inorganic salts of acid dyes having acidic groups such as sulfonic acid and carboxylic acid, salt-forming compounds of acid dyes and nitrogen-containing compounds, sulfonic acid amide compounds of acid dyes, etc.

Also, orange pigments such as C.I. Pigment Orange 43, 71, or 73 and/or C.I. Pigment Yellow 1, 2, 3, 4, 5, 6, 10, 12, 13, 14, 1
5, 16, 17, 18, 24, 31, 32, 34, 35, 35:1, 36, 36:1, 37, 37:1, 40, 42, 43, 53, 55, 60, 61, 62, 63, 65, 73, 74, 77, 81, 83, 93, 9 4, 95, 97, 98, 100, 101, 104, 106, 108, 109, 110, 113, 114, 115, 116, 117, 118, 119, 120, 123, 126, 127, 128, 129, 138, 13 9, 147, 150, 151, 152, 153, 154, 155, 156, 161, 162, 164, 166, 167, 168, 169, 170, 171, 172, 173, 174, 175, 176, 177, 179, 180, 181, 182, 185, 187, 188, 193, 194, 198, 199, 213, 214, 218, 219, 220, 221, or a yellow pigment represented by the following general formula (4) can be used in combination. In addition, examples of orange dyes and/or yellow dyes include quinoline-based, azo-based (pyridone-based, barbituric acid-based, metal complex-based, etc.), disazo-based, methine-based, etc.

As the colorant to be used in combination, from the viewpoint of fastness such as heat resistance and light resistance and chromaticity range, azo-based, diketopyrrolopyrrole-based, anthraquinone-based, quinophthalone-based, and perylene-based pigments are preferred.Specific examples include C.I. Pigment Red 177, 242, 254, 269, 291, 295, and 296, C.I. Pigment Yellow 138, 139, 150, and 185, and a yellow pigment represented by the following general formula (4).
In particular, from the viewpoint of brightness and coloring power, C. I. Pigment Red 242, 254, 291, C. I. Pigment Yellow 138, 139, 150, and a yellow pigment represented by the following general formula (4) are more preferable.

General formula (4)

[In general formula (4), Z ₁ to Z ₁₃ each independently represent a hydrogen atom, a halogen atom, an alkyl group which may have a substituent, an alkoxyl group which may have a substituent, an aryl group which may have a substituent, -SO ₃ H, -COOH, and monovalent to trivalent metal salts of these acidic groups, alkylammonium salts, a phthalimidomethyl group which may have a substituent, or a sulfamoyl group which may have a substituent.
Adjacent groups of Z ₁ to Z ₄ and/or Z ₁₀ to Z ₁₃ may be joined together to form an aromatic ring which may have a substituent.

Here, halogen atoms include fluorine, chlorine, bromine, and iodine.

Alkyl groups which may have a substituent include linear or branched alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, neopentyl, n-hexyl, n-octyl, stearyl, and 2-ethylhexyl, as well as alkyl groups having a substituent such as trichloromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, 2,2-dibromoethyl, 2,2,3,3-tetrafluoropropyl, 2-ethoxyethyl, 2-butoxyethyl, 2-nitropropyl, benzyl, 4-methylbenzyl, 4-tert-butylbenzyl, 4-methoxybenzyl, 4-nitrobenzyl, and 2,4-dichlorobenzyl.

Alkoxyl groups which may have a substituent include linear or branched alkoxyl groups such as methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, isobutyloxy, tert-butyloxy, neopentyloxy, 2,3-dimethyl-3-pentoxy, n-hexyloxy, n-octyloxy, stearyloxy, and 2-ethylhexyloxy, as well as alkoxyl groups having a substituent such as trichloromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy, 2,2,3,3-tetrafluoropropyloxy, 2,2-ditrifluoromethylpropoxy, 2-ethoxyethoxy, 2-butoxyethoxy, 2-nitropropoxy, and benzyloxy.

In addition, examples of aryl groups that may have a substituent include aryl groups such as phenyl groups, naphthyl groups, and anthranyl groups, as well as aryl groups having a substituent such as p-methylphenyl groups, p-bromophenyl groups, p-nitrophenyl groups, p-methoxyphenyl groups, 2,4-dichlorophenyl groups, pentafluorophenyl groups, 2-aminophenyl groups, 2-methyl-4-chlorophenyl groups, 4-hydroxy-1-naphthyl groups, 6-methyl-2-naphthyl groups, 4,5,8-trichloro-2-naphthyl groups, anthraquinonyl groups, and 2-aminoanthraquinonyl groups.

Examples of the acidic group include _-SO3H and -COOH, and examples of the monovalent to trivalent metal salts of these acidic groups include sodium salts, potassium salts, magnesium salts, calcium salts, iron salts, aluminum salts, etc. Examples of the alkyl ammonium salts of acidic groups include ammonium salts of long-chain monoalkyl amines such as octylamine, laurylamine, and stearylamine, and quaternary alkyl ammonium salts such as palmityltrimethylammonium, dilauryldimethylammonium, and distearyldimethylammonium salts.

Examples of the "substituent" in the optionally substituted phthalimidomethyl group (C ₆ H ₄ (CO) ₂ N-CH ₂ --) and the optionally substituted sulfamoyl group (H ₂ NSO ₂ --) include the above-mentioned halogen atoms, optionally substituted alkyl groups, optionally substituted alkoxyl groups, optionally substituted aryl groups, etc.

In general formula (4), adjacent groups of Z ₁ to Z ₄ and/or Z ₁₀ to Z ₁₃ may be united to form an aromatic ring which may have a substituent. The aromatic ring mentioned here includes a hydrocarbon aromatic ring and a heteroaromatic ring, and examples of the hydrocarbon aromatic ring include a benzene ring, a naphthalene ring, an anthracene ring, and a phenanthrene ring, and examples of the heteroaromatic ring include a pyridine ring, a pyrazine ring, a pyrrole ring, a quinoline ring, a quinoxaline ring, a furan ring, a benzofuran ring, a thiophene ring, a benzothiophene ring, an oxazole ring, a thiazole ring, an imidazole ring, a pyrazole ring, an indole ring, and a carbazole ring.

Specific examples of the yellow pigment represented by general formula (4) used in the colorant for color filters of the present invention include the quinophthalone compounds (a) to (r) shown below, but the present invention is not limited to these. In addition, the quinophthalone compound used in the present invention can be produced, for example, by the method described in Japanese Patent Publication No. 2930774, but the present invention is not limited to these.

Dyes that can be used in combination are preferably those that exhibit a red or purple color and are in the form of an oil-soluble dye, an acid dye, a direct dye, or a basic dye.
Among these, xanthene oil-soluble dyes, xanthene basic dyes, and xanthene acid dyes are preferred because they have excellent hues. These dyes may also be in the form of lake pigments obtained by making these dyes into lakes, inorganic salts of acid dyes having acidic groups such as sulfonic acid and carboxylic acid, salt-forming compounds of acid dyes and nitrogen-containing compounds, and sulfonic acid amide compounds of acid dyes.

Xanthene oil-soluble dyes include C.I. Solvent Red 35, C.I. Solvent Red 36, C.I. Solvent Red 42, C.I. Solvent Red 43, C.I. Solvent Red 44, C.I. Solvent Red 45, C.I. Solvent Red 46, C.I. Solvent Red 47, C.I. Solvent Red 48, C.I. Solvent Red 49, C.I. Solvent Red 72, C.I. Solvent Red 73, C.I. Solvent Red 109, C.I. Solvent Red 140, C.I. Solvent Red 141, C.I. Solvent Red 237, C.I. Solvent Red 246, C.I. Examples of the rhodamine-based oil-soluble dyes having high color development properties include C.I. Solvent Red 35, C.I. Solvent Red 36, C.I. Solvent Red 49, C.I. Solvent Red 109, C.I. Solvent Red 237, C.I. Solvent Red 246, and C.I. Solvent Violet 2. Among these, C.I. Solvent Red 35, C.I. Solvent Red 36, C.I. Solvent Red 49, C.I. Solvent Red 109, C.I. Solvent Red 237, C.I. Solvent Red 246, and C.I. Solvent Violet 2 are more preferable.
Examples of xanthene-based basic dyes include C.I. Basic Red 1 (Rhodamine 6GCP), C.I. Basic Red 8 (Rhodamine G), C.I. Basic Violet 10 (Rhodamine B), etc. Among them, C.I. Basic Red 1 and C.I. Basic Violet 10 are preferably used because of their excellent color development properties.
As the xanthene acid dye, C.I. Acid Red 51 (Erythrosine (Food Red No. 3)), C.I. Acid Red 52 (Acid Rhodamine), C.I. Acid Red 87 (Eosine G (Food Red No. 103)), C.I. Acid Red 92 (Acid Phloxine PB (Food Red No. 104)), C.I. Acid Red 289, C.I. Acid Red 388, Rose Bengal B (Food Red No. 5), Acid Rhodamine G, and C.I. Acid Violet 9 are preferably used.
Among these dyes, it is most preferable to use C.I. Acid Red 52, which is a rhodamine acid dye, in particular because it has excellent color development, heat resistance, and light resistance.

When used in combination with the above red pigment, yellow pigment, orange pigment, or dye, the content of the pigment containing the compound represented by the above general formulas (1) to (3) is 10 to 90 mass%, preferably 20 to 80 mass%, of the total 100 mass% of the colorant. If the content of the pigment containing the compound represented by the above general formulas (1) to (3) is 10 mass% or less, the excellent effects of brightness and coloring power cannot be fully exhibited.

<Average primary particle size of pigment>
The average primary particle size of the pigment was measured (calculated) by the following method.
Propylene glycol monomethyl ether acetate was added to the pigment powder, a small amount of Disperbyk-161 was added as a resin-type dispersant, and the mixture was dispersed in an ultrasonic cleaner for 1 minute to prepare a measurement sample. Three photographs (three fields of view) were taken of this sample using a transmission electron microscope (JEM-1200EX manufactured by JEOL Ltd.) in which 100 or more primary particles of the pigment could be confirmed, and the size of 100 primary particles was measured in order from the top left of each photograph. Specifically, the minor axis diameter and major axis diameter of each primary particle of the pigment were measured in nm units, and the average was taken as the primary particle diameter of the pigment. A total of 300 distributions were created in 5 nm increments, and the median value of the 5 nm increments (for example, 8 nm when the particle diameter is 6 nm to 10 nm) was approximated as the particle diameter of the particles, and the number-average particle diameter was calculated based on the particle diameter and the number of particles.

<Fine particle size of colorant>
The pigments used in the present invention can be used after being finely divided. It is also preferable to use the pigments containing the compounds represented by the above general formulas (1) to (3) after being finely divided, but the method of finely dividing is not particularly limited, and for example, any of wet grinding, dry grinding, and dissolution precipitation methods can be used, and as exemplified in the present invention, salt milling treatment using a kneader method, which is a type of wet grinding, can be used.

The primary particle size of the finely divided pigment is preferably 20 nm or more, since this allows for good dispersion in the colorant carrier. It is also preferable that the primary particle size is 100 nm or less, since this allows for the formation of filter segments with a high contrast ratio. The particularly preferred range is 25 to 85 nm.

Salt milling is a process in which a mixture of pigment, water-soluble inorganic salt, and water-soluble organic solvent is mechanically kneaded while being heated using a kneader, trimix, two-roll mill, three-roll mill, ball mill, attritor, sand mill, or other kneading machine, and then the water-soluble inorganic salt and water-soluble organic solvent are removed by washing with water. The water-soluble inorganic salt acts as a crushing aid, and the high hardness of the inorganic salt is used to crush the pigment during salt milling. By optimizing the conditions for salt milling the pigment, it is possible to obtain a pigment with a very fine primary particle size, a narrow distribution range, and a sharp particle size distribution.

Sodium chloride, potassium chloride, sodium sulfate, etc. can be used as the water-soluble inorganic salt, but sodium chloride (table salt) is preferred from the viewpoint of cost. From the viewpoints of both processing efficiency and production efficiency, it is preferable to use 50 to 2000 parts by weight of the water-soluble inorganic salt per 100 parts by weight of the colorant, and it is most preferable to use 300 to 1000 parts by weight.

The water-soluble organic solvent is not particularly limited as long as it functions to wet the pigment and the water-soluble inorganic salt, dissolves (mixes) in water, and does not substantially dissolve the inorganic salt used. However, since the temperature rises during salt milling and the solvent becomes prone to evaporate, a high-boiling solvent with a boiling point of 120°C or higher is preferred from the standpoint of safety. For example, 2-methoxyethanol, 2-butoxyethanol, 2-(isopentyloxy)ethanol, 2-(hexyloxy)ethanol, diethylene glycol, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, triethylene glycol, triethylene glycol monomethyl ether, liquid polyethylene glycol, 1-methoxy-2-propanol, 1-ethoxy-2-propanol, dipropylene glycol, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, liquid polypropylene glycol, etc. may be used. The water-soluble organic solvent is preferably used in an amount of 5 to 1000 parts by weight, and most preferably 50 to 500 parts by weight, per 100 parts by weight of the colorant.

When the pigment is subjected to salt milling, a resin may be added as necessary. There are no particular limitations on the type of resin used, and natural resins, modified natural resins, synthetic resins, synthetic resins modified with natural resins, etc. can be used. The resin used is preferably solid at room temperature and insoluble in water, and more preferably partially soluble in the above organic solvents. The amount of resin used is preferably in the range of 5 to 200 parts by weight per 100 parts by weight of the colorant.

When the pigment is subjected to salt milling, a dye derivative, which will be described later, may be added as necessary. The structure of the dye derivative used is not particularly limited, and examples include compounds in which a basic substituent, an acidic substituent, or a phthalimidomethyl group which may have a substituent has been introduced into an organic pigment, an anthraquinone, an acridone, or a triazine. These may be used alone or in a mixture of two or more types.

The amount of these dye derivatives used is preferably 2 to 30 parts by weight, and most preferably 5 to 20 parts by weight, per 100 parts by weight of the colorant.

<Coloring composition for color filters>
The coloring composition for color filters of the present invention is composed of a binder resin in addition to the coloring agent described above.

<Binder resin>
The binder resin disperses, dyes, or penetrates the colorant, and examples of the binder resin include thermoplastic resins. When used in the form of an alkali development type color resist material, it is preferable to use an alkali-soluble vinyl resin copolymerized with an acidic group-containing ethylenically unsaturated monomer. In order to further improve the photosensitivity, an active energy ray curable resin having an ethylenically unsaturated double bond can also be used.

In particular, by using an active energy ray-curable resin having an ethylenically unsaturated double bond in the side chain in an alkali development type color resist material, when the resin is exposed to active energy rays to form a coating film, the colorant is fixed by three-dimensional crosslinking, improving heat resistance and suppressing fading of the colorant due to heat (deterioration of spectral characteristics). It also has the effect of suppressing aggregation and precipitation of the colorant components during the development process.

The binder resin should preferably have a spectral transmittance of 80% or more, and more preferably 95% or more, over the entire wavelength range of 400 to 700 nm in the visible light region.

The weight average molecular weight (Mw) of the binder resin is preferably in the range of 10,000 to 100,000, and more preferably in the range of 10,000 to 80,000, in order to disperse the colorant favorably. The number average molecular weight (Mn) is preferably in the range of 5,000 to 50,000, and the value of Mw/Mn is preferably 10 or less.

When the binder resin is used as a photosensitive coloring composition for color filters, the balance between the carboxyl groups that act as colorant adsorption groups and alkali-soluble groups during development, and the aliphatic and aromatic groups that act as affinity groups for the colorant carrier and solvent is important for the dispersibility, penetration, developability, and durability of the colorant, and it is preferable to use a resin with an acid value of 20 to 300 mgKOH/g. If the acid value is less than 20 mgKOH/g, the solubility in the developer is poor, making it difficult to form a fine pattern. If the acid value exceeds 300 mgKOH/g, no fine pattern will remain.

The binder resin is preferably used in an amount of 20 parts by mass or more per 100 parts by mass of the total colorant, since it has good film-forming properties and various resistances, and is preferably used in an amount of 1,000 parts by mass or less, since it has a high colorant concentration and can express good color characteristics.

Examples of thermoplastic resins used for the binder resin include acrylic resins, butyral resins, styrene-maleic acid copolymers, chlorinated polyethylene, chlorinated polypropylene, polyvinyl chloride, vinyl chloride-vinyl acetate copolymers, polyvinyl acetate, polyurethane resins, polyester resins, vinyl resins, alkyd resins, polystyrene resins, polyamide resins, rubber resins, cyclized rubber resins, celluloses, polyethylene (HDPE, LDPE), polybutadiene, and polyimide resins. Of these, it is preferable to use acrylic resins.

Examples of the vinyl alkali-soluble resin copolymerized with an acidic group-containing ethylenically unsaturated monomer include resins having an acidic group such as a carboxyl group or a sulfone group.
Specific examples of the alkali-soluble resin include an acrylic resin having an acidic group, an α-olefin/maleic acid (anhydride) copolymer, a styrene/styrene sulfonic acid copolymer, an ethylene/(meth)acrylic acid copolymer, an isobutylene/maleic acid (anhydride) copolymer, etc. Among these, at least one resin selected from an acrylic resin having an acidic group and a styrene/styrene sulfonic acid copolymer, and particularly an acrylic resin having an acidic group, is preferably used because of its high heat resistance and transparency.

Examples of the active energy ray-curable resin having an ethylenically unsaturated double bond include resins into which an ethylenically unsaturated double bond has been introduced by the following method (i) or (ii).

[Method (i)]
An example of the method (i) is a method in which an unsaturated ethylenic monomer having an epoxy group is copolymerized with one or more other monomers to obtain a copolymer, and a carboxyl group of an unsaturated monobasic acid having an unsaturated ethylenic double bond is subjected to an addition reaction with the side-chain epoxy group of the copolymer, and further, a polybasic acid anhydride is reacted with the resulting hydroxyl group to introduce an unsaturated ethylenic double bond and a carboxyl group.

Examples of unsaturated ethylenic monomers having an epoxy group include glycidyl (meth)acrylate, methyl glycidyl (meth)acrylate, 2-glycidoxyethyl (meth)acrylate, 3,4 epoxybutyl (meth)acrylate, and 3,4 epoxycyclohexyl (meth)acrylate, which may be used alone or in combination of two or more. Glycidyl (meth)acrylate is preferred from the viewpoint of reactivity with the unsaturated monobasic acid in the next step.

Examples of unsaturated monobasic acids include monocarboxylic acids such as (meth)acrylic acid, crotonic acid, o-, m-, and p-vinylbenzoic acid, and (meth)acrylic acid substituted with haloalkyl, alkoxyl, halogen, nitro, or cyano at the α-position. These may be used alone or in combination of two or more.

Examples of polybasic acid anhydrides include tetrahydrophthalic anhydride, phthalic anhydride, hexahydrophthalic anhydride, succinic anhydride, maleic anhydride, etc., which may be used alone or in combination of two or more. If necessary, for example to increase the number of carboxyl groups, it is also possible to use a tricarboxylic acid anhydride such as trimellitic anhydride, or a tetracarboxylic acid dianhydride such as pyromellitic dianhydride to hydrolyze the remaining anhydride groups. In addition, if tetrahydrophthalic anhydride or maleic anhydride, which has an unsaturated ethylenic double bond, is used as the polybasic acid anhydride, the number of unsaturated ethylenic double bonds can be further increased.

As a method similar to method (i), for example, there is a method in which an unsaturated ethylenic monomer having an epoxy group is added to some of the side chain carboxyl groups of a copolymer obtained by copolymerizing an unsaturated ethylenic monomer having a carboxyl group with one or more other monomers, thereby introducing an unsaturated ethylenic double bond and a carboxyl group.

[Method (ii)]
Method (ii) includes a method in which an unsaturated ethylenic monomer having a hydroxyl group is used and copolymerized with another monomer of an unsaturated monobasic acid having a carboxyl group or with another monomer, and the side chain hydroxyl group of the copolymer is reacted with an isocyanate group of an unsaturated ethylenic monomer having an isocyanate group.

Examples of the unsaturated ethylenic monomer having a hydroxyl group include hydroxyalkyl (meth)acrylates such as 2-hydroxyethyl (meth)acrylate, 2- or 3-hydroxypropyl (meth)acrylate, 2-, 3- or 4-hydroxybutyl (meth)acrylate, glycerol (meth)acrylate, or cyclohexanedimethanol mono(meth)acrylate, which may be used alone or in combination of two or more. In addition, polyether mono(meth)acrylates obtained by addition polymerization of ethylene oxide, propylene oxide, and/or butylene oxide to the above-mentioned hydroxyalkyl (meth)acrylates, and (poly)ester mono(meth)acrylates obtained by addition of (poly)γ-valerolactone, (poly)ε-caprolactone, and/or (poly)12-hydroxystearic acid, etc., may also be used. From the viewpoint of suppressing foreign matter in the coating, 2-hydroxyethyl (meth)acrylate or glycerol (meth)acrylate is preferred.

Examples of unsaturated ethylenic monomers having an isocyanate group include 2-(meth)acryloyloxyethyl isocyanate and 1,1-bis[(meth)acryloyloxy]ethyl isocyanate, but are not limited to these and two or more types can be used in combination.

<Organic Solvent>
The coloring composition of the present invention contains an organic solvent in order to facilitate the formation of a filter segment by thoroughly dispersing and penetrating the coloring agent in the coloring agent carrier and applying the composition to a substrate such as a glass substrate so as to give a dry film thickness of 0.2 to 5 μm. The organic solvent is selected in consideration of the good applicability of the coloring composition, the solubility of each component of the coloring composition, and safety.

Examples of organic solvents include 1,2,3-trichloropropane, 1-methoxy-2-propanol, ethyl lactate, 1,3-butanediol, 1,3-butylene glycol, 1,3-butylene glycol diacetate, 1,4-dioxane, 2-heptanone, 2-methyl-1,3-propanediol, 3,5,5-trimethyl-2-cyclohexen-1-one, 3,3,5-trimethylcyclohexanone, ethyl 3-ethoxypropionate, 3-methyl-1,3-butanediol, 3-methoxy-3-methyl-1-butanol, 3-methoxy-3-methylbutyl acetate, 3-methoxybutanol, 3-methoxybutyl acetate, 4-heptanone, m-xylene, m-diethylbenzene, m-dichlorobenzene, N,N-dimethylacetamide, N,N-dimethylformamide, n-butylalcohol, and the like. Coal, n-butylbenzene, n-propyl acetate, N-methylpyrrolidone, o-xylene, o-chlorotoluene, o-diethylbenzene, o-dichlorobenzene, p-chlorotoluene, p-diethylbenzene, sec-butylbenzene, tert-butylbenzene, γ-butyrolactone, isobutyl alcohol, isophorone, ethylene glycol diethyl ether, ethylene glycol dibutyl ether, ethylene glycol monoisopropyl ether, ethylene glycol monoethyl ether, ethylene glycol monoethyl ether acetate, ethylene glycol monotertiary butyl ether, ethylene glycol monobutyl ether, ethylene glycol monobutyl ether acetate, ethylene glycol monopropyl ether, ethylene glycol monohexyl ether , ethylene glycol monomethyl ether, ethylene glycol monomethyl ether acetate, diisobutyl ketone, diethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol monoisopropyl ether, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether, diethylene glycol monobutyl ether acetate, diethylene glycol monomethyl ether, cyclohexanol, cyclohexanol acetate, cyclohexanone, dipropylene glycol dimethyl ether, dipropylene glycol methyl ether acetate, dipropylene glycol monoethyl ether, dipropylene glycol monobutyl ether, dipropylene glycol monopropyl ether, dipropylene glycol Examples of the solvent include propylene glycol monomethyl ether, diacetone alcohol, triacetin, tripropylene glycol monobutyl ether, tripropylene glycol monomethyl ether, propylene glycol diacetate, propylene glycol phenyl ether, propylene glycol monoethyl ether, propylene glycol monoethyl ether acetate, propylene glycol monobutyl ether, propylene glycol monopropyl ether, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether propionate, benzyl alcohol, methyl isobutyl ketone, methylcyclohexanol, n-amyl acetate, n-butyl acetate, isoamyl acetate, isobutyl acetate, propyl acetate, dibasic acid esters, etc. These solvents can be used alone or in a mixture of two or more in any ratio as necessary.

The solvent can be used in an amount of 100 to 10,000 parts by weight, preferably 500 to 5,000 parts by weight, per 100 parts by weight of the colorant in the coloring composition.

<Photopolymerizable Monomer>
The photopolymerizable monomer that may be added to the colored composition of the present invention includes a monomer or oligomer that is cured by ultraviolet light, heat, or the like to form a transparent resin.

Examples of monomers and oligomers that harden when exposed to ultraviolet light or heat to produce a transparent resin include methyl (meth)acrylate, ethyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, cyclohexyl (meth)acrylate, β-carboxyethyl (meth)acrylate, polyethylene glycol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, triethylene glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, 1,6-hexanediol diglycidyl ether di(meth)acrylate, bisphenol A diglycidyl ether di(meth)acrylate, and bisphenol A diglycidyl ether di(meth)acrylate. Examples of the photopolymerizable compounds include, but are not limited to, various acrylic acid esters and methacrylic acid esters such as ethyl ether di(meth)acrylate, neopentyl glycol diglycidyl ether di(meth)acrylate, dipentaerythritol hexa(meth)acrylate, dipentaerythritol penta(meth)acrylate, tricyclodecanyl (meth)acrylate, ester acrylate, (meth)acrylic acid ester of methylol melamine, epoxy (meth)acrylate, and urethane acrylate, (meth)acrylic acid, styrene, vinyl acetate, hydroxyethyl vinyl ether, ethylene glycol divinyl ether, pentaerythritol trivinyl ether, (meth)acrylamide, N-hydroxymethyl (meth)acrylamide, N-vinylformamide, and acrylonitrile. These photopolymerizable compounds can be used alone or in a mixture of two or more kinds in any ratio as necessary.

The content of the photopolymerizable monomer is preferably 5 to 500 parts by mass per 100 parts by mass of the colorant, and more preferably 10 to 400 parts by mass from the viewpoints of photocurability and developability.

<Photopolymerization initiator>
The coloring composition of the present invention can be prepared in the form of a solvent-developable or alkali-developable photosensitive coloring composition by adding a photopolymerization initiator to cure the composition by ultraviolet irradiation and form a filter segment by a photolithography method.

Examples of the photopolymerization initiator include acetophenone-based compounds such as 4-phenoxydichloroacetophenone, 4-t-butyl-dichloroacetophenone, diethoxyacetophenone, 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropan-1-one, 1-hydroxycyclohexyl phenyl ketone, 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one, 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]-1-butanone, and 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1-one; benzoin, benzoin methyl ether, etc. benzoin compounds such as benzoin ether, benzoin ethyl ether, benzoin isopropyl ether, and benzil dimethyl ketal; benzophenone compounds such as benzophenone, benzoylbenzoic acid, benzoylbenzoic acid methyl, 4-phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, and 3,3',4,4'-tetra(t-butylperoxycarbonyl)benzophenone; thioxanthone such as thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, isopropylthioxanthone, 2,4-diisopropylthioxanthone, and 2,4-diethylthioxanthone. Ton-based compounds: 2,4,6-trichloro-s-triazine, 2-phenyl-4,6-bis(trichloromethyl)-s-triazine, 2-(p-methoxyphenyl)-4,6-bis(trichloromethyl)-s-triazine, 2-(p-tolyl)-4,6-bis(trichloromethyl)-s-triazine, 2-piperonyl-4,6-bis(trichloromethyl)-s-triazine, 2,4-bis(trichloromethyl)-6-styryl-s-triazine, 2-(naphth-1-yl)-4,6-bis(trichloromethyl)-s-triazine, 2-(4-methoxy-naphth-1-yl)-4,6-bis(trichloromethyl)-s-triazine, 2,4-trichloromethyl-(piperonyl) triazine-based compounds such as 2,4-trichloromethyl-(4'-methoxystyryl)-6-triazine; oxime ester-based compounds such as 1,2-octanedione, 1-[4-(phenylthio)-, 2-(O-benzoyloxime)], or O-(acetyl)-N-(1-phenyl-2-oxo-2-(4'-methoxy-naphthyl)ethylidene)hydroxylamine; phosphine-based compounds such as bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide or 2,4,6-trimethylbenzoyldiphenylphosphine oxide; quinone-based compounds such as 9,10-phenanthrenequinone, camphorquinone, and ethylanthraquinone; borate-based compounds; carbazole-based compounds; imidazole-based compounds; or titanocene-based compounds. These photopolymerization initiators may be used alone or in combination of two or more kinds at any ratio as required.

The content of the photopolymerization initiator is preferably 1 to 500 parts by mass per 100 parts by mass of the colorant, and more preferably 5 to 400 parts by mass from the viewpoint of photocurability and developability.

<Sensitizer>
Furthermore, the coloring composition for color filters of the present invention may contain a sensitizer.
Examples of sensitizers include unsaturated ketones such as chalcone derivatives and dibenzalacetone, 1,2-diketone derivatives such as benzil and camphorquinone, polymethine dyes such as benzoin derivatives, fluorene derivatives, naphthoquinone derivatives, anthraquinone derivatives, xanthene derivatives, thioxanthene derivatives, xanthone derivatives, thioxanthone derivatives, coumarin derivatives, ketocoumarin derivatives, cyanine derivatives, merocyanine derivatives, and oxonol derivatives, acridine derivatives, azine derivatives, thiazine derivatives, oxazine derivatives, indoline derivatives, azulene derivatives, azulenium derivatives, Examples of the sensitizer include squarylium derivatives, porphyrin derivatives, tetraphenylporphyrin derivatives, triarylmethane derivatives, tetrabenzoporphyrin derivatives, tetrapyrazinoporphyrazine derivatives, phthalocyanine derivatives, tetraazaporphyrazine derivatives, tetraquinoxalylporphyrazine derivatives, naphthalocyanine derivatives, subphthalocyanine derivatives, pyrylium derivatives, thiopyrylium derivatives, tetraphylline derivatives, annulene derivatives, spiropyran derivatives, spirooxazine derivatives, thiospiropyran derivatives, metal arene complexes, organic ruthenium complexes, and Michler's ketone derivatives. These sensitizers can be used alone or in combination of two or more at any ratio as required.

Further specific examples include, but are not limited to, sensitizers described in "Dye Handbook" edited by Makoto Okawara et al. (Kodansha, 1986), "Chemistry of Functional Dyes" edited by Makoto Okawara et al. (CMC, 1981), and "Special Functional Materials" edited by Chuzo Ikemori et al. (CMC, 1986). In addition, sensitizers that absorb light in the ultraviolet to near infrared range can also be contained.
Among the above sensitizers, particularly preferred sensitizers include thioxanthone derivatives, Michler's ketone derivatives, and carbazole derivatives. More specifically, 2,4-diethylthioxanthone, 2-chlorothioxanthone, 2,4-dichlorothioxanthone, 2-isopropylthioxanthone, 4-isopropylthioxanthone, 1-chloro-4-propoxythioxanthone, 4,4'-bis(dimethylamino)benzophenone, 4,4'-bis(diethylamino)benzophenone, 4,4'-bis(ethylmethylamino)benzophenone, N-ethylcarbazole, 3-benzoyl-N-ethylcarbazole, and 3,6-dibenzoyl-N-ethylcarbazole are used.

The content of the sensitizer is preferably 3 to 60 parts by mass relative to 100 parts by mass of the photopolymerization initiator contained in the coloring composition, and more preferably 5 to 50 parts by mass from the viewpoints of photocurability and developability.

<Multifunctional thiol>
The coloring composition for color filters of the present invention may contain a polyfunctional thiol. The polyfunctional thiol is a compound having two or more thiol (SH) groups. By using the polyfunctional thiol together with the above-mentioned photopolymerization initiator, it acts as a chain transfer agent in the radical polymerization process after light irradiation, and generates a thiyl radical that is not easily inhibited by oxygen, so that the coloring composition for color filters obtained has high sensitivity. In particular, a polyfunctional aliphatic thiol in which the SH group is bonded to an aliphatic group such as a methylene or ethylene group is preferred.

Examples of polyfunctional thiols include hexanedithiol, decanedithiol, 1,4-butanediol bisthiopropionate, 1,4-butanediol bisthioglycolate, ethylene glycol bisthioglycolate, ethylene glycol bisthiopropionate, trimethylolpropane tristhioglycolate, trimethylolpropane tristhiopropionate, trimethylolethane tris(3-mercaptobutyrate), trimethylolpropane tris(3-mercaptobutyrate), trimethylolpropane tris(3-mercaptobutyrate), trimethylolpropane tris(3-mercaptobutyrate), Examples of such polyfunctional thiols include pentaerythritol tetrakis(3-mercaptopropionate), pentaerythritol tetrakis(thioglycolate), pentaerythritol tetrakis(3-mercaptopropionate), dipentaerythritol hexakis(3-mercaptopropionate), trimercaptopropionic acid tris(2-hydroxyethyl)isocyanurate, 1,4-dimethylmercaptobenzene, 2,4,6-trimercapto-s-triazine, and 2-(N,N-dibutylamino)-4,6-dimercapto-s-triazine. These polyfunctional thiols can be used alone or in a mixture of two or more in any ratio as required.

The content of the polyfunctional thiol is preferably 0.05 to 100 parts by mass, and more preferably 1.0 to 50.0 parts by mass, based on 100 parts by mass of the colorant.
By using 0.05 parts by mass or more of a polyfunctional thiol, better development resistance can be obtained. When a monofunctional thiol having one thiol (SH) group is used, such improvement in development resistance cannot be obtained.

<Leveling Agent>
In order to improve the leveling property of the composition on a transparent substrate, it is preferable to add a leveling agent to the colored composition of the present invention. As the leveling agent, dimethylsiloxane having a polyether structure or a polyester structure in the main chain is preferable. Specific examples of dimethylsiloxane having a polyether structure in the main chain include FZ-2122 manufactured by Dow Corning Toray Co., Ltd. and BYK-333 manufactured by BYK-Chemie Co., Ltd. Specific examples of dimethylsiloxane having a polyester structure in the main chain include BYK-310 and BYK-37 manufactured by BYK-Chemie Co., Ltd.
0. Dimethylsiloxane having a polyether structure in the main chain and dimethylsiloxane having a polyester structure in the main chain can also be used in combination. The content of the leveling agent is usually preferably 0.003 to 1.0 part by mass relative to 100 parts by mass of the total mass of the colored composition.

Particularly preferred leveling agents are those that have hydrophobic and hydrophilic groups in the molecule, and are characterized by low solubility in water despite having hydrophilic groups, and low surface tension reducing ability when added to a coloring composition. Furthermore, those that have good wettability to glass plates despite their low surface tension reducing ability are useful, and those that can sufficiently suppress electrostatic charging in an amount added that does not cause defects in the coating film due to foaming are preferably used. As a leveling agent having such preferred characteristics, dimethylpolysiloxanes having polyalkylene oxide units can be preferably used. Examples of polyalkylene oxide units include polyethylene oxide units and polypropylene oxide units, and dimethylpolysiloxanes may have both polyethylene oxide units and polypropylene oxide units.

The bonding form of the polyalkylene oxide unit with the dimethylpolysiloxane may be any of a pendant type in which the polyalkylene oxide unit is bonded to the repeating unit of the dimethylpolysiloxane, a terminal modified type in which the polyalkylene oxide unit is bonded to the terminal of the dimethylpolysiloxane, and a linear block copolymer type in which the polyalkylene oxide unit is bonded alternately and repeatedly to the dimethylpolysiloxane. Dimethylpolysiloxanes having polyalkylene oxide units are commercially available from Dow Corning Toray Co., Ltd., and examples thereof include, but are not limited to, FZ-2110, FZ-2122, FZ-2130, FZ-2166, FZ-2191, FZ-2203, and FZ-2207.

Anionic, cationic, nonionic, or amphoteric surfactants can be added to the leveling agent as supplementary agents. Two or more types of surfactants may be mixed and used. Examples of anionic surfactants that can be added to the leveling agent as supplementary agents include polyoxyethylene alkyl ether sulfates, sodium dodecylbenzene sulfonate, alkali salts of styrene-acrylic acid copolymers, sodium alkyl naphthalene sulfonates, sodium alkyl diphenyl ether disulfonates, monoethanolamine lauryl sulfate, triethanolamine lauryl sulfate, ammonium lauryl sulfate, monoethanolamine stearate, sodium stearate, sodium lauryl sulfate, monoethanolamine styrene-acrylic acid copolymers, and polyoxyethylene alkyl ether phosphates.

Examples of cationic surfactants that can be added to the leveling agent as supplementary agents include alkyl quaternary ammonium salts and their ethylene oxide adducts. Examples of nonionic surfactants that can be added to the leveling agent as supplementary agents include polyoxyethylene oleyl ether, polyoxyethylene lauryl ether, polyoxyethylene nonylphenyl ether, polyoxyethylene alkyl ether phosphate esters, polyoxyethylene sorbitan monostearate, and polyethylene glycol monolaurate; alkyl betaines such as alkyl dimethylamino acetate betaine, amphoteric surfactants such as alkyl imidazolines, and fluorine-based and silicone-based surfactants.

<Ultraviolet absorbers, polymerization inhibitors>
The coloring composition for color filters of the present invention may contain an ultraviolet absorber or a polymerization inhibitor. By containing an ultraviolet absorber or a polymerization inhibitor, the shape and resolution of the pattern can be controlled.

Examples of ultraviolet absorbents include hydroxyphenyl triazines such as 2-[4-[(2-hydroxy-3-(dodecyl and tridecyl)oxypropyl)oxy]-2-hydroxyphenyl]-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine and 2-(2-hydroxy-4-[1-octyloxycarbonylethoxy]phenyl)-4,6-bis(4-phenylphenyl)-1,3,5-triazine; benzotriazoles such as 2-(5-methyl-2-hydroxyphenyl)benzotriazole, 2-(2H-benzotriazol-2-yl)-4,6-bis(1-methyl-1-phenylethyl)phenol and 2-(3-t-butyl-5-methyl-2-hydroxyphenyl)-5-chlorobenzotriazole; -dihydroxybenzophenone, 2-hydroxy-4-octoxybenzophenone, 2,2',4,4'-tetrahydroxybenzophenone and other benzophenones, salicylate systems such as phenyl salicylate, p-tert-butylphenyl salicylate and other salicylate systems, cyanoacrylate systems such as ethyl-2-cyano-3,3'-diphenylacrylate and other cyanoacrylates, hindered amine systems such as 2,2,6,6,-tetramethylpiperidine-1-oxyl (triacetone-amine-N-oxyl), bis(2,2,6,6-tetramethyl-4-piperidyl)-sebacate, poly[[6-[(1,1,3,3-tetrabutyl)amino]-1,3,5-triazine-2,4-diyl][(2,2,6,6-tetramethyl-4-piperidinyl)imino] and the like. These ultraviolet absorbents can be used alone or in combination of two or more types in any ratio as necessary.

Examples of polymerization inhibitors include hydroquinone derivatives and phenol compounds such as methylhydroquinone, t-butylhydroquinone, 2,5-di-t-butylhydroquinone, 4-benzoquinone, 4-methoxyphenol, 4-methoxy-1-naphthol, and t-butylcatechol; amine compounds such as phenothiazine, bis-(1-dimethylbenzyl)phenothiazine, and 3,7-dioctylphenothiazine; copper and manganese salt compounds such as copper dibutyldithiocarbamate, copper diethyldithiocarbamate, manganese diethyldithiocarbamate, and manganese diphenyldithiocarbamate; nitroso compounds such as 4-nitrosophenol, N-nitrosodiphenylamine, N-nitrosocyclohexylhydroxylamine, and N-nitrosophenylhydroxylamine, and ammonium salts or aluminum salts thereof. These polymerization inhibitors can be used alone or in a mixture of two or more types at any ratio as necessary.

The ultraviolet absorber and polymerization inhibitor can be used in an amount of 0.01 to 20 parts by mass, preferably 0.05 to 10 parts by mass, based on 100 parts by mass of the colorant in the colored composition.
By using 0.01 parts by mass or more of the ultraviolet absorber or polymerization inhibitor, better resolution can be obtained.

<Antioxidants>
The coloring composition for color filters of the present invention can contain an antioxidant to increase the transmittance of the coating film. The antioxidant prevents the photopolymerization initiator contained in the coloring composition for color filters from being oxidized and yellowed by the thermal process during heat curing or ITO annealing, and can therefore increase the transmittance of the coating film. Therefore, by containing an antioxidant, yellowing due to oxidation during the heating process can be prevented, and a high transmittance of the coating film can be obtained.

Preferred examples of the antioxidant include hindered phenol-based antioxidants, hindered amine-based antioxidants, phosphorus-based antioxidants, and sulfide-based antioxidants. Hindered phenol-based antioxidants, hindered amine-based antioxidants, and phosphorus-based antioxidants are more preferred. These antioxidants can be used alone or in combination of two or more types in any ratio as required.

Examples of the hindered phenol antioxidant include 2,4-bis[(laurylthio)methyl]-o-cresol, 1,3,5-tris(3,5-di-t-butyl-4-hydroxybenzyl), 1,3,5-tris(4-t-butyl-3-hydroxy-2,6-dimethylbenzyl), 2,4-bis-(n-octylthio)-6-(4-hydroxy-3,5-di-t-butylanilino)-1,3,5-triazine, and pentaerythritol tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate.

Hindered amine antioxidants include bis(2,2,6,6-tetramethyl-4-piperidyl)sebacate, bis(N-methyl-2,2,6,6-tetramethyl-4-piperidyl)sebacate, N,N'-bis(2,2,6,6-tetramethyl-4-piperidyl)-1,6-hexamethylenediamine, 2-methyl-2-(2,2,6,6-tetramethyl-4-piperidyl)amino-N-(2,2,6,6-tetramethyl-4-piperidyl)propionamide, tetrakis(2,2,6,6-tetramethyl-4-piperidyl)(1,2,3,4-butanetetracarboxylate, poly[{6-(1,1,3,3-tetramethylbutyl)imino-1,3,5-triazine-2,4-diyl}{(2,2,6,6-tetramethylbutyl)imino-1,3,5-triazine-2,4-diyl} Examples of such compounds include poly[(6-morpholino-1,3,5-triazine-2,4-diyl){(2,2,6,6-tetramethyl-4-piperidyl)imino}hexamethine{(2,2,6,6-tetramethyl-4-piperidyl)imino}], polycondensate of dimethyl succinate and 1-(2-hydroxyethyl)-4-hydroxy-2,2,6,6-tetramethylpiperidine, and N,N'-4,7-tetrakis[4,6-bis{N-butyl-N-(1,2,2,6,6-pentamethyl-4-piperidyl)amino}-1,3,5-triazine-2-yl]-4,7-diazadecane-1,10-diamine.

Phosphorus-based antioxidants include tris[2-[[2,4,8,10-tetrakis(1,1-dimethylethyl)dibenzo[d,f][1,3,2]dioxaphosphepin-6-yl]oxy]ethyl]amine, tris[2-[(4,6,9,11-tetra-tert-butyldibenzo[d,f][1,3,2]dioxaphosphepin-2-yl)oxy]ethyl]amine, and ethyl bis(2,4-ditert-butyl-6-methylphenyl)phosphite.

Examples of sulfide antioxidants include 2,2-thio-diethylenebis[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate], 2,4-bis[(octylthio)methyl]-o-cresol, and 2,4-bis[(laurylthio)methyl]-o-cresol.

The antioxidant is preferably used in an amount of 0.1 to 5 parts by mass per 100 parts by mass of the total solid content of the coloring composition for color filters. If the antioxidant is less than 0.1 parts by mass, the effect of increasing the transmittance is small, and if it is more than 5 parts by mass, the hardness is significantly reduced and the sensitivity of the coloring composition for color filters is significantly reduced.

<Other ingredients>
The coloring composition for color filters of the present invention may contain an adhesion improver such as a silane coupling agent in order to improve adhesion to a transparent substrate, or an amine compound having a function of reducing dissolved oxygen.

Examples of the silane coupling agent include vinyl silanes such as vinyltris(β-methoxyethoxy)silane, vinylethoxysilane, and vinyltrimethoxysilane, (meth)acrylic silanes such as γ-methacryloxypropyltrimethoxysilane, β-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, β-(3,4-epoxycyclohexyl)methyltrimethoxysilane, β-(3,4-epoxycyclohexyl)ethyltriethoxysilane, β-(3,4-epoxycyclohexyl)methyltriethoxysilane, γ-glycidoxypropyltrimethoxysilane, and γ-glycidoxypropyltrimethoxysilane. Examples of the epoxy silanes include N-β(aminoethyl)γ-aminopropyltrimethoxysilane, N-β(aminoethyl)γ-aminopropyltriethoxysilane, N-β(aminoethyl)γ-aminopropylmethyldiethoxysilane, γ-aminopropyltriethoxysilane, γ-aminopropyltrimethoxysilane, N-phenyl-γ-aminopropyltriethoxysilane, and N-phenyl-γ-aminopropyltriethoxysilane; and thiosilanes such as γ-mercaptopropyltrimethoxysilane and γ-mercaptopropyltriethoxysilane.

The silane coupling agent can be used in an amount of 0.01 to 10 parts by mass, preferably 0.05 to 5 parts by mass, per 100 parts by mass of the colorant in the coloring composition.

Examples of amine compounds include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 2-ethylhexyl 4-dimethylaminobenzoate, and N,N-dimethyl-p-toluidine.

<Method of producing coloring composition for color filter>
The coloring composition for color filters of the present invention can be produced by finely dispersing a colorant in a colorant carrier such as a resin and/or a solvent, together with a dispersion aid as necessary, using various dispersing means such as a kneader, a two-roll mill, a three-roll mill, a ball mill, a horizontal sand mill, a vertical sand mill, an annular bead mill, or an attritor (colorant dispersion). At this time, two or more types of colorants may be simultaneously dispersed in a colorant carrier, or they may be mixed together after being separately dispersed in a colorant carrier. The epoxy compound may be added at the stage of preparing the colorant dispersion, and the same effect can be obtained even if it is added later to the prepared colorant dispersion. When the solubility of a colorant such as a dye is high, specifically, when it is highly soluble in the solvent used and dissolved by stirring, and no foreign matter is confirmed, it is not necessary to produce it by finely dispersing it as described above.

When used as a photosensitive coloring composition (resist material) for color filters, it can be prepared as a solvent-developable or alkali-developable coloring composition. The solvent-developable or alkali-developable coloring composition can be prepared by mixing the colorant dispersion, a photopolymerizable monomer and/or a photopolymerization initiator, and, if necessary, a solvent, other pigment dispersants, and additives. The photopolymerization initiator may be added at the stage of preparing the coloring composition, or may be added later to the prepared coloring composition.

<Dispersion Aid>
When dispersing the colorant in the colorant carrier, not only the resin-type dispersant but also a dispersing aid such as a dye derivative, a surfactant, etc. may be appropriately contained. The dispersing aid has a large effect of preventing the re-aggregation of the colorant after dispersion, so that the coloring composition obtained by dispersing the colorant in the colorant carrier using the dispersing aid has good brightness and storage stability.

<Resin-type dispersant>
The coloring composition for color filters of the present invention preferably contains a resin-type dispersant.
The resin-type dispersant has a colorant-affinity site that has the property of adsorbing to the colorant and a site that is compatible with the colorant carrier, and functions to adsorb to the colorant and stabilize the dispersion of the colorant in the colorant carrier. Specifically, resin-type dispersants include polyurethane, polycarboxylate esters such as polyacrylate, unsaturated polyamides, polycarboxylic acids, polycarboxylate (partial) amine salts, polycarboxylate ammonium salts, polycarboxylate alkylamine salts, polysiloxanes, long-chain polyaminoamide phosphates, hydroxyl-containing polycarboxylate esters, and modified products thereof, poly(lower alkylene imines) and free carboxyl groups formed by reaction with polyesters, and their salts, oil-based dispersants, (meth)acrylic acid-styrene copolymers, (meth)acrylic acid-(meth)acrylic acid ester copolymers, styrene-maleic acid copolymers, polyvinyl alcohol, water-soluble resins and water-soluble polymer compounds such as polyvinylpyrrolidone, polyesters, modified polyacrylates, ethylene oxide / propylene oxide adducts, and phosphate esters are used, which can be used alone or in a mixture of two or more, but are not necessarily limited to these.

Commercially available resin-type dispersants include Disperbyk-101, 103, 107, 108, 110, 111, 116, 130, 140, 154, 161, 162, 163, 164, 165, 166, 170, 171, 174, 180, 181, 182, 183, 184, 185, 190, 2000, 2001, 2020, 2025, 2050, 2070, 2095, 2150, 2155, and others manufactured by BYK Japan. or Anti-Terra-U, 203, 204, or BYK-P104, P104S, 220S, 6919, or Lactimon, Lactimon-WS, or Bykumen, etc. manufactured by Lubrizol Japan Co., Ltd. SOLSPERSE-3000, 9000, 13000, 13240, 13650, 13940, 16000, 17000, 18000, 20000, 21000, 24000, 26000, 2700 0, 28000, 31845, 32000, 32500, 32550, 33500, 32600, 34750, 35100, 36600, 38500, 41000, 41090, 53095, 55000, 76500, etc., EFKA-46, 47, 48, 452, 4008, 4009, 4010, 4015, 4020, 4047, 4050, 4055, 4060, 4080, 4400, 4401, 4402 manufactured by BASF , 4403, 4406, 4408, 4300, 4310, 4320, 4330, 4340, 450, 451, 453, 4540, 4550, 4560, 4800, 5010, 5065, 5066, 5070, 7500, 7554, 1101, 120, 150, 1501, 1502, 1503, etc., and Ajisper PA111, PB711, PB821, PB822, PB824, etc. manufactured by Ajinomoto Fine-Techno Co., Ltd.

The resin-type dispersant used in the present invention is preferably one having an acidic substituent, and among them, one having an aromatic carboxyl group is preferred because it is particularly effective in preventing reagglomeration of the colorant after dispersion. As the resin-type dispersant having an aromatic carboxyl group, one containing the following (S1) or (S2) is preferred.
(S1) A resin-type dispersant which is a reaction product between a hydroxyl group of a hydroxyl group-containing polymer and an acid anhydride group of a tricarboxylic acid anhydride and/or a tetracarboxylic acid dianhydride.
(S2) A resin-type dispersant which is a polymer obtained by polymerizing an ethylenically unsaturated monomer in the presence of a reaction product between a hydroxyl group of a compound having a hydroxyl group and an acid anhydride group of a tricarboxylic acid anhydride and/or a tetracarboxylic acid dianhydride.

[Resin-type dispersant (S1)]
The resin-type dispersant (S1) can be produced by known methods such as those described in WO2008/007776, JP2008-029901A, and JP2009-155406A. The polymer (p) having a hydroxyl group is preferably a polymer having a hydroxyl group at the end, and can be obtained, for example, as a polymer obtained by polymerizing an ethylenically unsaturated monomer (r) in the presence of a compound (q) having a hydroxyl group. The compound (q) having a hydroxyl group is preferably a compound having a hydroxyl group and a thiol group in the molecule. Since it is preferable that the terminal hydroxyl group is a plurality of hydroxyl groups, among them, a compound (q1) having two hydroxyl groups and one thiol group in the molecule is preferably used.

That is, a more preferred example of a polymer having two hydroxyl groups at one end can be obtained as a polymer (p1) by polymerizing an ethylenically unsaturated monomer (r) including a monomer (r1) in the presence of a compound (q1) having two hydroxyl groups and one thiol group in the molecule. The hydroxyl groups of the polymer (p) having hydroxyl groups react with the acid anhydride groups of the tricarboxylic acid anhydride and/or tetracarboxylic acid dianhydride to form ester bonds, while the anhydride ring opens to produce a carboxylic acid.

[Resin-type dispersant (S2)]
The resin-type dispersant (S2) can be produced by known methods such as those described in JP-A-2009-155406, JP-A-2010-185934, and JP-A-2011-157416, and is obtained, for example, by polymerizing an ethylenically unsaturated monomer (r) in the presence of a reaction product between a hydroxyl group of a compound (q) having a hydroxyl group and an acid anhydride group of a tricarboxylic acid anhydride and/or a tetracarboxylic acid dianhydride. Among them, a polymer obtained by polymerizing an ethylenically unsaturated monomer (r) containing a monomer (r1) in the presence of a reaction product between a hydroxyl group of a compound (q1) having two hydroxyl groups and one thiol group in the molecule and an acid anhydride group of a tricarboxylic acid anhydride and/or a tetracarboxylic acid dianhydride is preferred.

The difference between (S1) and (S2) is whether the polymer moiety formed by polymerizing the ethylenically unsaturated monomer (r) is introduced first or later. The molecular weight and other factors may differ slightly depending on various conditions, but in theory, the same product can be produced if the raw materials and reaction conditions are the same.

It is preferable to use about 5 to 200 parts by weight of the resin-type dispersant per 100 parts by weight of the colorant, and from the viewpoint of film-forming properties, it is even more preferable to use about 5 to 100 parts by weight.

<Dye derivatives>
The coloring composition for color filters of the present invention may further contain a dye derivative. The dye derivative may be contained in an azo pigment.
The dye derivative used in the present invention may be a known dye derivative having an acidic group, a basic group, a neutral group, etc. in the organic dye residue. Examples include compounds having an acidic functional group such as a sulfo group, a carboxy group, or a phosphate group, and their amine salts, compounds having a basic functional group such as a sulfonamide group or a tertiary amino group at the terminal, and compounds having a neutral functional group such as a phenyl group or a phthalimidoalkyl group. Examples of organic dyes include diketopyrrolopyrrole pigments, phthalocyanine pigments such as copper phthalocyanine, zinc phthalocyanine, aluminum phthalocyanine, halogenated copper phthalocyanine, halogenated zinc phthalocyanine, halogenated aluminum phthalocyanine, and metal-free phthalocyanine; anthraquinone pigments such as aminoanthraquinone, diaminodianthraquinone, anthrapyrimidine, flavanthrone, anthranthrone, indanthrone, pyranthrone, and violanthrone; quinacridone pigments, dioxazine pigments, perinone pigments, perylene pigments, thiazineindigo pigments, triazine pigments, benzimidazolone pigments, indole pigments such as benzoisoindole, isoindoline pigments, isoindolinone pigments, quinophthalone pigments, naphthol pigments, threne pigments, metal complex pigments, and azo pigments such as azo, disazo, and polyazo.
More specifically, JP-A-61-246261, JP-A-63-264674, JP-A-09-272812, JP-A-10-245501, JP-A-10-265697, JP-A-11-199796, JP-A-2001-172520, JP-A-2001-220520, Japanese Patent Application Publication No. 2002-201377, Japanese Patent Application Publication No. 2003-165922, Japanese Patent Application Publication No. 2003-168208, Japanese Patent Application Publication No. 2003-171594, Japanese Patent Application Publication No. 2004-217842, Japanese Patent Application Publication No. 2005-213404, Japanese Patent Application Publication No. 2006-291194, Japanese Patent Application Publication No. 2007-079094, Japanese Patent Application Publication No. 200
No. 7-226161, JP 2007-314681 A, JP 2007-314785 A, JP 2008-31281 A, JP 2009-57478 A, WO 2009/025325 pamphlet, WO 2009/081930 pamphlet, JP 2011-162662 A, WO 2011/052617 pamphlet, JP 2012-172092 A Examples of known dye derivatives include those described in JP 2012-208329 A, JP 2012-226110 A, WO 2012/102399 A, JP 2014-5439 A, WO 2016/163351 A, JP 2017-156397 A, and Japanese Patent No. 5753266 A, and these can be used alone or in combination of two or more. In these documents, the dye derivative may be described as a derivative, pigment derivative, pigment dispersant, or simply a compound, but the compound having a functional group such as an acidic group, a basic group, or a neutral group in the organic dye residue is synonymous with the dye derivative.

Among the dye derivatives used in the present invention, dye derivatives having a basic substituent are preferred because they have a significant effect of suppressing aggregation between pigments. Furthermore, organic dye residues derived from diketopyrrolopyrrole pigments, anthraquinone pigments, quinophthalone pigments, and azo pigments are preferred from the viewpoint of hue and contrast.

It is preferable to use about 1 to 60 parts by weight of the dye derivative per 100 parts by weight of the colorant, and from the viewpoint of color characteristics, it is more preferable to use about 5 to 30 parts by weight.

<Surfactant>
Examples of the surfactant include anionic surfactants such as sodium lauryl sulfate, polyoxyethylene alkyl ether sulfate, sodium dodecylbenzene sulfonate, alkali salts of styrene-acrylic acid copolymers, sodium stearate, sodium alkyl naphthalene sulfonate, sodium alkyl diphenyl ether disulfonate, monoethanolamine lauryl sulfate, triethanolamine lauryl sulfate, ammonium lauryl sulfate, monoethanolamine stearate, monoethanolamine of styrene-acrylic acid copolymers, and polyoxyethylene alkyl ether phosphate esters; nonionic surfactants such as polyoxyethylene oleyl ether, polyoxyethylene lauryl ether, polyoxyethylene nonylphenyl ether, polyoxyethylene alkyl ether phosphate esters, polyoxyethylene sorbitan monostearate, and polyethylene glycol monolaurate; cationic surfactants such as alkyl quaternary ammonium salts and their ethylene oxide adducts; alkyl betaines such as alkyl dimethylaminoacetate betaine, and amphoteric surfactants such as alkyl imidazolines. These can be used alone or in combination of two or more, but are not necessarily limited to these.

When a surfactant is added, the amount is preferably 0.1 to 55 parts by weight, and more preferably 0.1 to 45 parts by weight, per 100 parts by weight of colorant. If the amount of surfactant is less than 0.1 parts by weight, it is difficult to obtain the effect of adding it, and if the amount is more than 55 parts by weight, the excess dispersant may affect the dispersion.

<Removal of large particles>
The coloring composition of the present invention is preferably subjected to removal of coarse particles of 5 μm or more, preferably coarse particles of 1 μm or more, more preferably coarse particles of 0.5 μm or more, and mixed dust by means of centrifugation, filtration with a sintered filter or a membrane filter, etc. In this way, it is preferable that the coloring composition does not substantially contain particles of 0.5 μm or more. More preferably, the particles are 0.3 μm or less.

<Color filter>
Next, the color filter of the present invention will be described. The color filter of the present invention comprises a red filter segment, a green filter segment, and a blue filter segment on a substrate, and may further comprise a magenta filter segment, a cyan filter segment, or a yellow filter segment, and at least one of the filter segments is formed from the coloring composition of the present invention.

<Color Filter Manufacturing Method>
The color filter of the present invention can be manufactured by a printing method or a photolithography method. The formation of filter segments by a printing method can be patterned by simply repeating printing and drying of a colored composition prepared as a printing ink, and is therefore a low-cost and mass-productive manufacturing method for color filters. Furthermore, the development of printing technology has made it possible to print fine patterns with high dimensional accuracy and smoothness. In order to perform printing, it is preferable to use a composition that does not allow the ink to dry or solidify on the printing plate or blanket. In addition, control of the fluidity of the ink on the printing machine is also important, and the ink viscosity can be adjusted by using a dispersant or an extender pigment.

When forming filter segments by photolithography, the coloring composition prepared as the above-mentioned solvent-developable or alkali-developable colored resist material is applied to a transparent substrate by a coating method such as spray coating, spin coating, slit coating, or roll coating so that the dry film thickness is 0.2 to 5 μm. If necessary, the dried film is exposed to ultraviolet light through a mask having a predetermined pattern that is in contact with or not in contact with the film. Thereafter, the uncured parts are removed by immersing the film in a solvent or alkali developing solution or spraying the developing solution by a spray or the like to form a desired pattern, and the same operation is repeated for other colors to produce a color filter. Furthermore, heating can be performed as necessary to promote polymerization of the colored resist material. According to the photolithography method, a color filter with higher accuracy than the above-mentioned printing method can be produced.

In the development, an aqueous solution of sodium carbonate, sodium hydroxide, etc. is used as an alkaline developer, and an organic alkali such as dimethylbenzylamine, triethanolamine, etc. can also be used. In addition, a defoaming agent or a surfactant can also be added to the developer.
In order to increase the sensitivity to ultraviolet light exposure, after the colored resist material is coated and dried, a water-soluble or alkaline water-soluble resin, such as polyvinyl alcohol or a water-soluble acrylic resin, may be coated and dried to form a film for preventing polymerization inhibition due to oxygen, and then ultraviolet light exposure may be performed.

The color filter of the present invention can be manufactured by the above-mentioned method, as well as by an electrodeposition method, a transfer method, an inkjet method, etc., and the coloring composition of the present invention can be used for any of these methods. The electrodeposition method is a method of manufacturing a color filter by using a transparent conductive film formed on a substrate to electrodeposit each color filter segment onto the transparent conductive film by electrophoresis of colloidal particles. The transfer method is a method in which filter segments are formed in advance on the surface of a peelable transfer base sheet, and the filter segments are then transferred to the desired substrate.

Before forming each color filter segment on a base material such as a transparent substrate or a reflective substrate, a black matrix can be formed in advance. Examples of black matrices that can be used include, but are not limited to, multilayer films of chromium or chromium/chromium oxide, inorganic films such as titanium nitride, and resin films with light-shielding agents dispersed therein. Thin film transistors (TFTs) can also be formed in advance on the transparent substrate or reflective substrate, and then each color filter segment can be formed. In addition, an overcoat film, a transparent conductive film, etc. can be formed on the color filter of the present invention as necessary.

The dry film thickness of the filter segment and black matrix is preferably 0.2 to 10 μm, and more preferably 0.2 to 5 μm. A vacuum dryer, convection oven, IR oven, hot plate, etc. may be used to dry the coating film.

The color filter is attached to the opposing substrate using a sealant, liquid crystal is injected through an injection port provided in the seal, the injection port is then sealed, and a polarizing film or retardation film is attached to the outside of the substrate as necessary to produce a liquid crystal display panel.

Such liquid crystal display panels can be used in liquid crystal display modes that use color filters such as twisted nematic (TN), super twisted nematic (STN), in-plane switching (IPS), vertical alignment (VA), and optically concentric bend (OCB).

Transparent substrates include glass plates such as soda-lime glass, low-alkali borosilicate glass, and non-alkali aluminoborosilicate glass, and resin plates such as polycarbonate, polymethylmethacrylate, and polyethylene terephthalate. Transparent electrodes made of indium oxide, tin oxide, etc. may be formed on the surface of the glass or resin plate to drive the liquid crystal after panelization.

The present invention will be described below based on examples, but the present invention is not limited thereto. In the examples, "parts" and "%" represent "parts by mass" and "% by mass", respectively.

<Weight average molecular weight (Mw) of resin>
The weight average molecular weight (Mw) of the resin is the polystyrene-equivalent weight average molecular weight (Mw) measured using a TSKgel column (manufactured by Tosoh Corporation) and a GPC (manufactured by Tosoh Corporation, HLC-8120GPC) equipped with an RI detector, using THF as a developing solvent.
<Method of identifying azo pigments>
The azo pigment of the present invention was identified using a Bruker Daltonics MALDI mass spectrometer Autoflex III (hereinafter referred to as TOF-MS) and was identified based on the agreement between the molecular ion peak of the obtained mass spectrum and the mass number obtained by calculation.

<Contrast ratio of coating film>
The light emitted from the backlight unit for liquid crystal display is polarized by passing through a polarizing plate, passes through a dried coating film of a coloring composition applied on a glass substrate, and reaches the polarizing plate. If the polarization planes of the polarizing plate and the polarizing plate are parallel, the light passes through the polarizing plate, but if the polarization planes are perpendicular, the light is blocked by the polarizing plate. However, when the light polarized by the polarizing plate passes through the dried coating film of the coloring composition, scattering by pigment particles occurs, and if a part of the polarization plane is shifted, the amount of light passing through the polarizing plate decreases when the polarizing plate is parallel, and part of the light passes through the polarizing plate when the polarizing plate is perpendicular. This transmitted light was measured as the luminance on the polarizing plate, and the ratio (contrast ratio) of the luminance when the polarizing plate is parallel to the luminance when the polarizing plate is perpendicular was calculated.
(Contrast ratio) = (Luminance when parallel) / (Luminance when perpendicular)
A color luminance meter (Topcon Corporation's "BM-5A") was used as the luminance meter, and a polarizing plate (Nitto Denko Corporation's "NPF-G1220DUN") was used as the polarizing plate. During the measurement, a black mask with a 1 cm square hole was placed over the measurement area to block unnecessary light.

First, we will explain the methods for producing the acrylic resin solution, resin-type dispersant solution, colorant, coloring composition, and photosensitive coloring composition used in the examples, production examples, and comparative examples.

<Method of producing acrylic resin solution>
(Preparation of acrylic resin solution 1)
A separable 4-neck flask was fitted with a thermometer, a cooling tube, a nitrogen gas inlet tube, a dropping tube and a stirrer. 196 parts of cyclohexanone was charged in the reaction vessel, which was heated to 80 ° C. and replaced with nitrogen in the reaction vessel. From the dropping tube, a mixture of 37.2 parts of n-butyl methacrylate, 12.9 parts of 2-hydroxyethyl methacrylate, 12.0 parts of methacrylic acid, 20.7 parts of paracumylphenol ethylene oxide modified acrylate ("Aronix M110" manufactured by Toagosei Co., Ltd.), and 1.1 parts of 2,2'-azobisisobutyronitrile was dropped over 2 hours. After the dropwise addition was completed, the reaction was continued for another 3 hours to obtain an acrylic resin solution. After cooling to room temperature, about 2 parts of the resin solution was sampled and dried by heating at 180 ° C. for 20 minutes to measure the nonvolatile content, and methoxypropyl acetate was added to the resin solution synthesized earlier so that the nonvolatile content was 20% to prepare acrylic resin solution 1. The weight average molecular weight (Mw) was 26,000.

(Preparation of acrylic resin solution 2)
A separable 4-neck flask was fitted with a thermometer, a cooling tube, a nitrogen gas inlet tube, a dropping tube and a stirrer, and 207 parts of cyclohexanone was charged into the reaction vessel, which was then heated to 80°C and substituted with nitrogen in the reaction vessel. From the dropping tube, a mixture of 20 parts of methacrylic acid, 20 parts of paracumylphenol ethylene oxide modified acrylate (Aronix M110 manufactured by Toagosei Co., Ltd.), 45 parts of methyl methacrylate, 8.5 parts of 2-hydroxyethyl methacrylate and 1.33 parts of 2,2'-azobisisobutyronitrile was added dropwise over 2 hours. After completion of the dropping, the reaction was continued for another 3 hours to obtain a copolymer resin solution. Next, the total amount of the copolymer solution obtained was stirred while stopping the nitrogen gas and injecting dry air for 1 hour, and then cooled to room temperature, and a mixture of 6.5 parts of 2-methacryloyloxyethyl isocyanate (Karenz MOI manufactured by Showa Denko K.K.), 0.08 parts of dibutyltin laurate, and 26 parts of cyclohexanone was added dropwise at 70 ° C. for 3 hours. After the end of the dropwise addition, the reaction was continued for another 1 hour to obtain an acrylic resin solution. After cooling to room temperature, about 2 parts of the resin solution was sampled and dried by heating at 180 ° C. for 20 minutes to measure the non-volatile content, and cyclohexanone was added to the resin solution previously synthesized so that the non-volatile content was 20% to prepare acrylic resin solution 2. The weight average molecular weight (Mw) was 18,000.

<Method of producing resin-type dispersant solution>
(Preparation of Resin-Type Dispersant Solution 1)
In a reaction vessel equipped with a gas inlet tube, a thermometer, a condenser, and a stirrer, 10 parts of methacrylic acid, 100 parts of methyl methacrylate, 70 parts of i-butyl methacrylate, and 20 parts of benzyl methacrylate were charged and replaced with nitrogen gas. The inside of the reaction vessel was heated to 80°C, and a solution in which 0.1 parts of 2,2'-azobisisobutyronitrile was dissolved in 10 parts of 3-mercapto-1,2-propanediol was added and reacted for 10 hours. It was confirmed that 95% had reacted by measuring the solid content. 20 parts of pyromellitic anhydride, 200.0 parts of methoxypropyl acetate, and 0.40 parts of 1,8-diazabicyclo-[5.4.0]-7-undecene as a catalyst were added, and the reaction was carried out at 120°C for 7 hours. It was confirmed by measuring the acid value that 98% or more of the acid anhydride had been half-esterified, and the reaction was terminated, and a polyester dispersant with an acid value of 77 mgKOH/g and a number average molecular weight of 8500 was obtained. Methoxypropyl acetate was added thereto so that the solid content was 40% by solid content measurement, thereby obtaining a resin-type dispersant solution 1 having an aromatic carboxyl group.

(Preparation of Resin-Type Dispersant Solution 2)
A reaction vessel equipped with a gas inlet tube, a thermometer, a condenser, and a stirrer was charged with 10 parts of methacrylic acid, 100 parts of methyl methacrylate, 70 parts of i-butyl methacrylate, and 20 parts of benzyl methacrylate, and substituted with nitrogen gas. The reaction vessel was heated to 80°C, and a solution of 0.1 parts of 2,2'-azobisisobutyronitrile dissolved in 10 parts of 3-mercapto-1,2-propanediol was added and reacted for 10 hours. It was confirmed that 95% had reacted by measuring the solid content. 36 parts of trimellitic anhydride, 200.0 parts of methoxypropyl acetate, and 0.40 parts of 1,8-diazabicyclo-[5.4.0]-7-undecene as a catalyst were added, and the reaction was carried out at 120°C for 7 hours. It was confirmed by measuring the acid value that 98% or more of the acid anhydride had been half-esterified, and the reaction was terminated, and a polyester dispersant with an acid value of 109 mgKOH/g and a number average molecular weight of 8500 was obtained. Methoxypropyl acetate was added thereto so that the solid content was 40% by solid content measurement, thereby obtaining a resin-type dispersant solution 2 having an aromatic carboxyl group.

(Preparation of Resin-Type Dispersant Solution 3)
A reaction vessel equipped with a gas inlet tube, a thermometer, a condenser, and a stirrer was charged with 6.5 parts of 3-mercapto-1,2-propanediol, 4.0 parts of pyromellitic anhydride, 0.01 parts of dimethylbenzylamine, and 41.8 parts of methoxypropyl acetate, and substituted with nitrogen gas. The reaction vessel was heated to 100 ° C. and reacted for 7 hours. After confirming that 98% or more of the acid anhydride was half-esterified by measuring the acid value, the temperature in the system was cooled to 70 ° C., 67 parts of methyl methacrylate, 5.0 parts of methacrylic acid, 16.0 parts of t-butyl acrylate, 10.0 parts of hydroxymethyl methacrylate, and 2.0 parts of ethyl acrylate were charged, and 0.10 parts of 2,2'-azobisisobutyronitrile and 60.0 parts of methoxypropyl acetate were added and reacted for 10 hours. The reaction was terminated after confirming that the polymerization had progressed to 95% by solid content measurement, yielding a polyester dispersant with an acid value of 43 mgKOH/g and a number average molecular weight of 15000. Methoxypropyl acetate was added to this solution so that the solid content was 40% by solid content measurement, yielding a resin-type dispersant solution 3 having an aromatic carboxyl group.

(Preparation of Resin-Type Dispersant Solution 4)
A reaction vessel equipped with a gas inlet tube, a thermometer, a condenser, and a stirrer was charged with 6.5 parts of 3-mercapto-1,2-propanediol, 4.0 parts of pyromellitic anhydride, 0.01 parts of dimethylbenzylamine, and 41.8 parts of methoxypropyl acetate, and substituted with nitrogen gas. The reaction vessel was heated to 100 ° C. and reacted for 7 hours. After confirming that 98% or more of the acid anhydride was half-esterified by measuring the acid value, the temperature in the system was cooled to 70 ° C., and 67 parts of methyl methacrylate, 5.0 parts of methacrylic acid, 16.0 parts of t-butyl acrylate, 10.0 parts of (3-ethyloxetan-3-yl)methyl methacrylate, and 2.0 parts of ethyl acrylate were charged, and 0.10 parts of 2,2'-azobisisobutyronitrile and 60.0 parts of methoxypropyl acetate were added and reacted for 10 hours. The reaction was terminated after confirming that the polymerization had progressed to 95% by solid content measurement, yielding a polyester dispersant with an acid value of 47 mgKOH/g and a number average molecular weight of 15000. Methoxypropyl acetate was added to this solution so that the solid content was 40% by solid content measurement, yielding resin-type dispersant solution 4 having an aromatic carboxyl group.

(Preparation of Resin-Type Dispersant Solution 5)
A flask equipped with a cooling tube and a stirrer was charged with 1.0 parts by mass of AIBN (2,2'-azobisisobutyronitrile) and 186 parts by mass of propylene glycol monomethyl ether acetate, followed by 27 parts by mass of methyl methacrylate, 27 parts by mass of butyl methacrylate, 21 parts by mass of 2-ethylhexyl methacrylate, 18 parts by mass of benzyl methacrylate and 3.6 parts by mass of cumyl dithiobenzoate, and substituted with nitrogen for 30 minutes. Thereafter, the temperature of the reaction solution was raised to 60 ° C. with gentle stirring, and this temperature was maintained for 24 hours to carry out living radical polymerization. Next, a solution of 1.0 parts by mass of AIBN and 35 parts by mass of dimethylaminoethyl methacrylate dissolved in 70 parts by mass of propylene glycol monomethyl ether acetate and substituted with nitrogen for 30 minutes was added to the reaction solution, and the solution was subjected to living radical polymerization at 60 ° C. for 24 hours to obtain a solution of a block copolymer. To the obtained block copolymer solution, 25 parts by mass of benzyl chloride and 50 parts by mass of propylene glycol monomethyl ether were added, and the reaction was carried out at 80° C. for 2 hours, and the solid content concentration was adjusted to 40%, thereby obtaining a resin-type dispersant solution 5. The resin-type dispersant 5 is a block copolymer consisting of an A block having repeating units derived from methacryloyloxyethyl benzyl dimethyl ammonium chloride and dimethylaminoethyl methacrylate, and a B block having repeating units derived from methyl methacrylate, butyl methacrylate, 2-ethylhexyl methacrylate, and benzyl methacrylate. As a result of proton NMR measurement, the copolymerization ratio of each repeating unit was methacryloyloxyethyl benzyl dimethyl ammonium chloride/dimethylaminoethyl methacrylate/methyl methacrylate/butyl methacrylate/2-ethylhexyl methacrylate/benzyl methacrylate=34/4/18/18/14/12 (mass ratio).

<Method of producing dye derivative>
The production method and structure of the dye derivative used in the present invention are shown below, but the present invention is not limited thereto.

(Production of dye derivative 1)
16 parts of 5-nitroisophthalic acid and 1.0 part of N,N-dimethylformamide (DMF) were dissolved in 110 parts of toluene. 22.6 parts of thionyl chloride were added dropwise thereto over 25 minutes, and the mixture was refluxed at 110° C. for 1 hour to synthesize 5-nitroisophthalic acid dichloride. 38.0 parts of 4-amino-N-(3-(diethylamino)propyl)benzamide were dispersed in 90 parts of toluene, and the 5-nitroisophthalic acid dichloride was added dropwise thereto at room temperature over 1 hour, followed by refluxing for 4 hours to complete the reaction. The toluene was distilled off while neutralizing with a 10% aqueous sodium carbonate solution, and the mixture was reslurried in a 3% aqueous NaOH solution, filtered, and dried to obtain 28.0 parts of a compound represented by the following formula 8.
Equation 8

Next, 25.0 parts of the compound represented by the above formula 8 was dissolved in 100 parts of N-methylpyrrolidone, and an aqueous solution of 32 parts of sodium hydrosulfide hydrate (containing 65% sodium hydrosulfide) dissolved in 55 parts of water was added thereto, followed by refluxing for 6 hours to obtain 20.0 parts of a base compound represented by the following formula 10.

Equation 9

20.0 parts of the base compound represented by the above formula 9 was dispersed in 200 parts of water, ice was added to adjust the temperature to 5°C, 20.0 parts of a 35% aqueous hydrochloric acid solution was added and stirred for 1 hour, after which an aqueous solution prepared by adding 3.60 parts of sodium nitrite to 11.0 parts of water was added and stirred for 2 hours. Next, an aqueous solution consisting of 59.0 parts of an 80% aqueous acetic acid solution, 65.0 parts of a 25% aqueous sodium hydroxide solution, and 64.0 parts of water was added to prepare an aqueous diazonium salt solution. Meanwhile, 18.7 parts of N-[2-methoxy-5-chlorophenyl]-3-hydroxy-2-naphthalenecarboxamide and 53.5 parts of a 25% aqueous sodium hydroxide solution were dissolved in 340 parts of methanol to prepare a coupler solution.

This coupler solution was poured into the above diazonium salt aqueous solution at 5°C over 30 minutes to carry out a coupling reaction. The pH at this time was 4.4. After stirring for 1 hour and confirming the disappearance of the diazonium salt, the mixture was heated to 70°C, filtered, washed with water, and dried at 90°C for 24 hours to obtain 35.8 parts of dye derivative 1 represented by formula 10.

Equation 10

(Preparation of dye derivative 2)
Dye derivative 2 represented by formula 11 was prepared with reference to Preparation Example 3 of Japanese Patent No. 1863188.
Equation 11

(Preparation of dye derivative 3)
With reference to Example 1 of Japanese Patent No. 5,316,690, dye derivative 3 represented by formula 12 was produced.
Equation 12

(Preparation of dye derivative 4)
With reference to Synthesis Example 3 of Japanese Patent No. 5748665, dye derivative 4 represented by formula 13 was produced.
Equation 13

(Preparation of dye derivative 5)
Dye derivative 5 represented by formula 14 was prepared with reference to Preparation Example 21 of Japanese Patent No. 4,396,778.
Equation 14

(Preparation of dye derivative 6)
Dye derivative 3 represented by formula 15 was prepared with reference to Preparation Example 6 of Japanese Patent No. 4,983,061.
Equation 15

(Preparation of dye derivative 7)
With reference to Example 12 of Japanese Patent No. 4,993,026, dye derivative 7 represented by formula 16 was prepared.
Equation 16

<Production of azo pigments>
[Example 1]
(Production of Azo Pigment 1)
After adding 181 parts of the base compound [B-1] represented by formula 17 to 1500 parts of N-methylpyrrolidone, 294 parts of 35% hydrochloric acid was added and cooled to -2 to 0 ° C. 208 parts of a 25% aqueous sodium nitrite solution was added to this solution, and the mixture was stirred for 30 minutes while maintaining the temperature at 0 to 5 ° C. to prepare a diazonium solution. Separately, a coupler solution consisting of 167 parts of the coupler compound [C-1] represented by formula 18, 316 parts of a 25% sodium hydroxide solution, and 1500 parts of methanol was prepared. The prepared diazonium solution and coupler solution were simultaneously added dropwise to 1000 parts of an acetate buffer solution of pH 5.4 over 10 minutes. The reaction formula at this time is represented by formula 19. After the dropwise addition, the mixture was stirred at room temperature for 30 minutes, and then further stirred while maintaining the temperature at 80 ° C. The precipitated reaction product was filtered, washed with hot water, and dried to obtain 340 parts of an azo pigment 1 represented by formula 20. As a result of mass analysis by TOF-MS, it was identified as Azo Pigment 1. The average primary particle diameter was 51 nm.

Base compound [B-1]
Equation 17

Coupler compound [C-1]
Equation 18

Reaction Scheme 19

Azo pigment 1
Equation 20

[Examples 2 to 116]
(Production of azo pigments 2 to 116)
Azo pigments 2 to 116 were obtained by carrying out the same operations as in the production of azo pigment 1, except that the base compound [B-1] and coupler compound [C-1] used in the production of azo pigment 1 were changed to the compounds represented by R, X, and A in Tables 1 to 3, respectively, and the amounts added were adjusted so that the molar numbers of the base compound and coupler compound were consistent with those in Example 1. The reaction formulas at this time are represented by Formulas 21 to 23. As a result of mass analysis by TOF-MS, the pigments were identified as azo pigments 2 to 116.
In Tables 1 to 3, Ph represents a phenyl group.

Reaction Scheme 21

Reaction Scheme 22

Reaction Scheme 23

Equations (3-1) to (3-3) in Table 3 are as follows:

Formula (3-1)

Formula (3-2)

Formula (3-3)

[Example 117]
(Preparation of Azo Pigment 117)
72 parts of Azo Pigment 1, 8 parts of Dye Derivative 1, 800 parts of sodium chloride, and 90 parts of diethylene glycol were charged into a stainless steel 1-gallon kneader (manufactured by Inoue Seisakusho Co., Ltd.), kneaded for 6 hours at 60° C., and subjected to salt milling treatment. The kneaded product obtained was poured into 3 liters of warm water, heated to 70° C. and stirred for 1 hour to obtain a slurry, which was then filtered and washed repeatedly with water to remove the sodium chloride and diethylene glycol, and then dried at 80° C. for one day to obtain 76 parts of Azo Pigment 117.

[Examples 118 to 140]
(Production of azo pigments 118 to 140)
Azo pigments 118 to 140 were obtained in the same manner as Azo pigment 117, except that the azo pigment and dye derivative used in Azo pigment 117 were replaced with the azo pigments and dye derivatives shown in Table 4 in terms of their types and ratios.

<Production of other colorants>
[Production Examples 1 to 13]
(Preparation of Red Colorant 1: PR254)
100 parts of commercially available C.I. Pigment Red 254 (PR254) (BASF "Irgazin Red D3656 HD"), 1200 parts of sodium chloride, and 120 parts of diethylene glycol were charged into a stainless steel 1 gallon kneader (Inoue Seisakusho Co., Ltd.), kneaded at 60 ° C for 6 hours, and salt milled. The kneaded product obtained was put into 3 liters of warm water, heated to 70 ° C and stirred for 1 hour to form a slurry, filtered and washed with water repeatedly to remove sodium chloride and diethylene glycol, and then dried at 80 ° C for 24 hours to obtain 98 parts of red colorant 1. The average primary particle diameter was 33 nm.

(Preparation of Red Colorant 2: PR177)
The same procedure as for the production of red colorant 1 was carried out except that C.I. Pigment Red 254 ("Irgazin Red D3656 HD" manufactured by BASF) was replaced with C.I. Pigment Red 177 (PR177) ("Sinilex Red SR3C" manufactured by Shinic) to obtain 97 parts of red colorant 2. The average primary particle diameter was 37 nm.

(Preparation of Red Colorant 3: PR242)
The same procedure as in the production of red colorant 1 was carried out except that C.I. Pigment Red 254 (BASF's "Irgazin Red D3656 HD") was replaced with C.I. Pigment Red 242 (PR242) (Clariant's "Sandorin Scarlet 4RF"), to obtain 98 parts of red colorant 3. The average primary particle diameter was 39 nm.

(Preparation of Red Colorant 4: PR269)
The same procedure as in the production of red colorant 1 was carried out except that C.I. Pigment Red 254 ("Irgazin Red D3656 HD" manufactured by BASF Corporation) was changed to C.I. Pigment Red 269 (PR269) ("Permanent Carmine 3810" manufactured by Sanyo Pigment Co., Ltd.), to obtain 98 parts of red colorant 4. The average primary particle diameter was 35 nm.

(Preparation of Red Colorant 5: PR291)
The same procedure as in the production of Red Colorant 1 was carried out except that C.I. Pigment Red 254 ("Irgazin Red D3656 HD" manufactured by BASF) was changed to C.I. Pigment Red 291 (PR291) ("Cinilex DPP MT-CF" manufactured by CINIC), to obtain 98 parts of Red Colorant 5. The average primary particle diameter was 45 nm.

(Preparation of Red Colorant 6)
The following red colorant 6 was synthesized with reference to Example 1 of Japanese Patent No. 6,368,844. The average primary particle size was 43 nm.

Red Colorant 6

(Preparation of Yellow Colorant 1: PY138)
Quinophthalone-based yellow pigment C.I. Pigment Yellow 138 (BASF "Paliotol Yellow L0962-HD") 500 parts, sodium chloride 500 parts, and diethylene glycol 250 parts were charged into a stainless steel 1-gallon kneader (Inoue Seisakusho Co., Ltd.) and kneaded at 120 ° C. for 8 hours. Next, this kneaded product was put into 5 liters of warm water, heated to 70 ° C. and stirred for 1 hour to form a slurry, filtered and washed with water repeatedly to remove sodium chloride and diethylene glycol, and then dried at 80 ° C. for 24 hours to obtain 490 parts of Yellow Colorant 1. The average primary particle diameter was 63 nm.

(Preparation of Yellow Colorant 2: PY139)
500 parts of isoindoline-based yellow pigment C.I. Pigment Yellow 139 (BASF "Paliotol Yellow L1820"), 500 parts of sodium chloride, and 250 parts of diethylene glycol were charged into a stainless steel 1-gallon kneader (Inoue Seisakusho Co., Ltd.) and kneaded at 120 ° C. for 8 hours. Next, this kneaded product was put into 5 liters of warm water, heated to 70 ° C. and stirred for 1 hour to form a slurry, filtered and washed with water repeatedly to remove sodium chloride and diethylene glycol, and then dried at 80 ° C. for 24 hours to obtain 510 parts of yellow colorant 2. The average primary particle diameter was 68 nm.

(Preparation of Yellow Colorant 3: PY150)
500 parts of azo-based yellow pigment C.I. Pigment Yellow 150 (Clariant's "Hostaperm Yellow HN4G"), 500 parts of sodium chloride, and 250 parts of diethylene glycol were charged into a stainless steel 1-gallon kneader (Inoue Seisakusho Co., Ltd.) and kneaded at 120 ° C. for 8 hours. Next, this kneaded product was put into 5 liters of warm water, heated to 70 ° C. and stirred for 1 hour to form a slurry, filtered and washed with water repeatedly to remove sodium chloride and diethylene glycol, and then dried at 80 ° C. for 24 hours to obtain 500 parts of yellow colorant 3. The average primary particle diameter was 60 nm.

(Preparation of Yellow Colorant 4: Quinophthalone Compound (b))
40 parts of 8-aminoquinaldine, 150 parts of 2,3-naphthalenedicarboxylic anhydride, and 154 parts of benzoic acid were added to 200 parts of methyl benzoate, heated to 180° C., and stirred for 4 hours. After cooling to room temperature, the reaction mixture was poured into 5,440 parts of acetone and stirred at room temperature for 1 hour. The product was filtered, washed with methanol, and dried to obtain 116 parts of quinophthalone compound (c). As a result of mass analysis by TOF-MS, it was identified as quinophthalone compound (c).

Quinophthalone Compound (c)

Furthermore, compound (c-2) was obtained using quinophthalone compound (c) as a raw material according to the synthesis method described in JP 2008-81566 A.

Compound (c-2)

100 parts of compound (c-2), 108 parts of tetrachlorophthalic anhydride, and 143 parts of benzoic acid were added to 300 parts of methyl benzoate, and the mixture was heated to 180° C. and reacted for 4 hours.
The production of quinophthalone compound (b) and the disappearance of the raw material compound (c-2) were confirmed by MS. After cooling to room temperature, the reaction mixture was added to 3,510 parts of acetone and stirred at room temperature for 1 hour. The product was filtered, washed with methanol, and dried to obtain 120 parts of quinophthalone compound (b). As a result of mass analysis by TOF-MS, the product was identified as quinophthalone compound (b).
Quinophthalone Compound (b)

500 parts of the quinophthalone compound (b) obtained above, 500 parts of sodium chloride, and 250 parts of diethylene glycol were charged into a stainless steel 1-gallon kneader (manufactured by Inoue Seisakusho Co., Ltd.) and kneaded at 120°C for 8 hours. Next, this kneaded mixture was poured into 5 liters of warm water and stirred for 1 hour while heating to 70°C to form a slurry. After repeatedly filtering and washing with water to remove the sodium chloride and diethylene glycol, the mixture was dried at 80°C for a day and night to obtain 480 parts of yellow colorant 4. The average primary particle diameter was 62 nm.

(Preparation of Green Colorant 1: PG58)
200 parts of a phthalocyanine green pigment C.I. Pigment Green 58 (DIC Corporation's "FASTOGEN GREEN A110"), 1400 parts of sodium chloride, and 360 parts of diethylene glycol were charged into a stainless steel 1-gallon kneader (Inoue Seisakusho Co., Ltd.) and kneaded at 80°C for 6 hours. Next, this kneaded mixture was added to 8000 parts of warm water, heated to 80°C and stirred for 2 hours to form a slurry, filtered and washed with water repeatedly to remove sodium chloride and diethylene glycol, and then dried at 85°C for a day and night to obtain 190 parts of green colorant 1. The average primary particle diameter was 69 nm.

(Preparation of Blue Colorant 1: PB15:6)
200 parts of phthalocyanine blue pigment C.I. Pigment Blue 15:6 ("LIONOL BLUE ES" manufactured by Toyo Color Co., Ltd.), 1400 parts of sodium chloride, and 360 parts of diethylene glycol were charged into a stainless steel 1-gallon kneader (manufactured by Inoue Seisakusho Co., Ltd.) and kneaded at 80°C for 6 hours. Next, this kneaded product was put into 8000 parts of warm water, heated to 80°C and stirred for 2 hours to form a slurry, filtered and washed with water repeatedly to remove sodium chloride and diethylene glycol, and then dried at 85°C for a day and night to obtain 190 parts of blue colorant 1. The average primary particle diameter was 74 nm.

(Preparation of Purple Colorant 1: PV23)
200 parts of a dioxazine-based purple pigment C.I. Pigment Violet 23 ("LIONOGEN VIOLET RL" manufactured by Toyo Color Co., Ltd.), 1400 parts of sodium chloride, and 360 parts of diethylene glycol were charged into a stainless steel 1-gallon kneader (manufactured by Inoue Seisakusho Co., Ltd.) and kneaded at 80°C for 6 hours. Next, the kneaded product was added to 8,000 parts of warm water and kneaded for 8 hours.
The mixture was stirred for 2 hours while heating to 0° C. to form a slurry, which was then filtered and repeatedly washed with water to remove sodium chloride and diethylene glycol, and then dried overnight at 85° C. to obtain 190 parts of Purple Colorant 1. The average primary particle size was 69 nm.

<Method of producing colored composition>
[Example 201]
(Preparation of Colored Composition (RM-1))
The mixture below was stirred and mixed to be homogeneous, and then dispersed for 3 hours in an Eiger mill ("Mini Model M-250 MKII" manufactured by Eiger Japan Co., Ltd.) using zirconia beads having a diameter of 0.5 mm. The mixture was then filtered through a filter having a pore size of 5.0 μm to prepare a colored composition (RM-1) having a non-volatile content of 20% by mass.
Colorant (azo pigment 1): 10.8 parts Dye derivative 1: 1.2 parts Acrylic resin solution 1: 19.2 parts Propylene glycol monomethyl ether acetate (PGMAc): 58.4 parts Resin-type dispersant solution 1: 10.4 parts

[Examples 202 to 376, Comparative Examples 1 to 3]
(Coloring composition (RM-2 to 177, RCM-2, RCM-4)
The following colored compositions (RM-2 to 177, RCM-2, RCM-4) were prepared in the same manner as the colored composition (RM-1), except that the composition was changed to that shown in Table 5. When a resin-type dispersant was not used, the acrylic resin solution 1 was added instead to match the solid content. When a dye derivative was not used, a colorant was added instead to match the solid content.

<Production of other coloring compositions>
(Colored composition (RCM-1): PR254)
The mixture below was stirred and mixed to be homogeneous, and then dispersed for 3 hours in an Eiger mill ("Mini Model M-250 MKII" manufactured by Eiger Japan Co., Ltd.) using zirconia beads having a diameter of 0.5 mm. The mixture was then filtered through a filter having a pore size of 5.0 μm to prepare a colored composition (RCM-1) having a non-volatile component content of 20% by mass.
Red colorant 1 (C.I. Pigment Red 254): 12.0 parts Acrylic resin solution 1: 19.2 parts Propylene glycol monomethyl ether acetate (PGMAc): 58.4 parts Resin type dispersant solution 1: 10.4 parts

(Colored composition (RCM-3): PR242)
The mixture below was stirred and mixed to be homogeneous, and then dispersed for 3 hours in an Eiger mill ("Mini Model M-250 MKII" manufactured by Eiger Japan Co., Ltd.) using zirconia beads having a diameter of 0.5 mm. The mixture was then filtered through a filter having a pore size of 5.0 μm to prepare a colored composition (RCM-3) having a non-volatile component content of 20% by mass.
Red colorant 3 (C.I. Pigment Red 242): 12.0 parts Acrylic resin solution 1: 19.2 parts Propylene glycol monomethyl ether acetate (PGMAc): 58.4 parts Resin type dispersant solution 1: 10.4 parts

(Colored composition (RCM-5): PR291)
The mixture below was stirred and mixed to be homogeneous, and then dispersed for 3 hours in an Eiger mill ("Mini Model M-250 MKII" manufactured by Eiger Japan Co., Ltd.) using zirconia beads having a diameter of 0.5 mm. The mixture was then filtered through a filter having a pore size of 5.0 μm to prepare a colored composition (RCM-5) having a non-volatile component content of 20% by mass.
Red colorant 5 (C.I. Pigment Red 291): 12.0 parts Acrylic resin solution 1: 19.2 parts Propylene glycol monomethyl ether acetate (PGMAc): 58.4 parts Resin type dispersant solution 1: 10.4 parts

(Coloring composition (YCM-1): PY138)
The mixture below was stirred and mixed to be homogeneous, and then dispersed for 3 hours in an Eiger mill ("Mini Model M-250 MKII" manufactured by Eiger Japan Co., Ltd.) using zirconia beads having a diameter of 0.5 mm. The mixture was then filtered through a filter having a pore size of 5.0 μm to prepare a colored composition (YCM-1) having a non-volatile component content of 20% by mass.
Yellow colorant 1 (C.I. Pigment Yellow 138): 12.0 parts Acrylic resin solution 1: 19.2 parts Propylene glycol monomethyl ether acetate (PGMAc): 58.4 parts Resin type dispersant solution 1: 10.4 parts

(Coloring composition (YCM-2): PY139)
The mixture below was stirred and mixed to be homogeneous, and then dispersed for 3 hours in an Eiger mill ("Mini Model M-250 MKII" manufactured by Eiger Japan Co., Ltd.) using zirconia beads having a diameter of 0.5 mm. The mixture was then filtered through a filter having a pore size of 5.0 μm to prepare a colored composition (YCM-2) having a non-volatile component content of 20% by mass.
Yellow colorant 2 (C.I. Pigment Yellow 139): 12.0 parts Acrylic resin solution 1: 19.2 parts Propylene glycol monomethyl ether acetate (PGMAc): 58.4 parts Resin type dispersant solution 1: 10.4 parts

(Coloring composition (YCM-3): PY150)
The mixture below was stirred and mixed to be homogeneous, and then dispersed for 3 hours in an Eiger mill (Eiger Japan "Mini Model M-250 MKII") using zirconia beads with a diameter of 0.5 mm. The mixture was then filtered through a filter with a pore size of 5.0 μm to prepare a coloring composition (YCM-3) with a non-volatile content of 20% by mass.
Yellow colorant 3 (C.I. Pigment Yellow 150): 12.0 parts Acrylic resin solution 1: 19.2 parts Propylene glycol monomethyl ether acetate (PGMAc): 58.4 parts Resin-type dispersant solution 1: 10.4 parts

(Coloring composition (YCM-4): Quinophthalone compound (b))
The mixture below was stirred and mixed to be homogeneous, and then dispersed for 3 hours in an Eiger mill (Eiger Japan Co., Ltd. "Mini Model M-250 MKII") using zirconia beads having a diameter of 0.5 mm. The mixture was then filtered through a filter having a pore size of 5.0 μm to prepare a colored composition (YCM-4) having a non-volatile component content of 20% by mass.
Yellow colorant 4 (quinophthalone compound (b)): 12.0 parts Acrylic resin solution 1: 19.2 parts Propylene glycol monomethyl ether acetate (PGMAc): 58.4 parts Resin-type dispersant solution 1: 10.4 parts

(Coloring composition (GCM-1): PG58)
A green colored composition (GCM-1) having a non-volatile content of 20% by mass was obtained in the same manner as in the colored composition (YCM-1), except that the yellow colorant 1 (C.I. Pigment Yellow 138) was changed to the green colorant 1 (C.I. Pigment Green 58).

(Coloring composition (BCM-1): PB15:6)
A blue colored composition (BCM-1) having a non-volatile content of 20% by mass was obtained in the same manner as in the colored composition (YCM-1), except that the yellow colorant 1 (C.I. Pigment Yellow 138) was changed to the blue colorant 1 (C.I. Pigment Blue 15:6).

(Coloring composition (VCM-1): PV23)
A purple colored composition (VCM-1) having a non-volatile content of 20% by mass was obtained in the same manner as in the colored composition (YCM-1), except that the yellow colorant 1 (C.I. Pigment Yellow 138) was changed to the purple colorant 1 (C.I. Pigment Violet 23).

(Evaluation of Colored Composition)
The heat resistance, foreign matter evaluation and storage stability of the obtained colored composition and the coating film formed using the same were performed by the following methods. The evaluation results are shown in Table 5.

(Heat resistance evaluation)
The colored composition was applied to a glass substrate of 100 mm x 100 mm and 1.1 mm thickness using a spin coater so that the dry film thickness was 2.0 μm, then dried at 70 ° C for 20 minutes, and then heated at 230 ° C for 60 minutes and allowed to cool to produce a coating film substrate (one embodiment of a color filter). The chromaticity ([L ^* (1), a ^* (1), b ^* (1)]) of the obtained coating film under C light source was measured using a microspectrophotometer (Olympus Optical Co., Ltd. "OSP-SP100"). Thereafter, as a heat resistance test, the coating film was heated at 260 ° C for 1 hour, and the chromaticity ([L ^* (2), a ^* (2), b ^* (2)]) under C light source was measured, and the color difference ΔEab ^* was calculated using the following formula and evaluated on the following four-level scale.

ΔEab ^* = √((L ^* (2)- L ^* (1)) ² + (a ^* (2)- a ^* (1)) ² +( b ^* (2)- b ^* (1)) ² )

◎: ΔEab ^* is less than 1.0 (very good)
○: ΔEab ^* is 1.0 or more and less than 2.5 (good)
△: ΔEab ^* is 2.5 or more and less than 5.0 (poor)
×: ΔEab ^* is 5.0 or more (very poor)

(Paint film foreign matter evaluation)
The colored composition was applied to a 100 mm x 100 mm, 1.1 mm thick glass substrate using a spin coater so that the dry film thickness was 2.0 μm, then dried at 70° C. for 20 minutes, and then heated at 230° C. for 60 minutes and allowed to cool to produce a coated substrate. Evaluation was performed by observing the surface using a metal microscope "BX60" manufactured by Olympus Systems Co., Ltd. The magnification was set to 500 times, and the number of particles observable in any five visual fields in transmission was counted. Evaluation was performed using the following four-level scale.

◎: The number of foreign objects is less than 5 (very good)
○: The number of foreign objects is 5 or more and less than 10 (good)
△: The number of foreign objects is 10 or more and less than 60 (defective)
×: The number of foreign objects is 60 or more (extremely poor)

(Storage stability test method)
The viscosity of the colored composition at 25° C. was measured at 20 rpm using an E-type viscometer (TUE-20L type manufactured by Toki Sangyo Co., Ltd.) The viscosity change rate (%) (= (viscosity after storage at 40° C. for 7 days−initial viscosity)/initial viscosity) was calculated from the initial viscosity on the day of preparation of the colored composition and the viscosity measured after storage for 14 days in a thermostatic chamber at 40° C., and the storage stability was evaluated according to the following criteria.

◎: Viscosity change rate is less than 10% (very good)
○: Viscosity change rate is 10% or more and less than 20% (good)
△: Viscosity change rate is 20% or more and less than 50% (bad)
×: Viscosity change rate is 50% or more (very poor)

As shown in Tables 5 to 7, the colored compositions using the colorants of the present invention showed good results in heat resistance of the coating film, foreign matter in the coating film, and storage stability. In particular, when compared with the colored composition using red colorant 6 (Comparative Example 1), it was found that the storage stability was good even under more severe test conditions.

<Method for producing photosensitive coloring composition for color filter>
[Example 401]
(Photosensitive coloring composition (RR-1))
The following mixture (total 100 parts) was stirred and mixed to be homogeneous, and then filtered through a filter having a pore size of 1.0 μm to obtain a photosensitive colored composition (RR-1).
Colored composition (RM-1): 23.0 parts Colored composition (RCM-1): 27.0 parts Acrylic resin solution 2: 7.5 parts Photopolymerizable monomer (Toagosei Co., Ltd. "Aronix M-402"): 2.0 parts Dipentaerythritol hexaacrylate Photopolymerization initiator (BASF Co., Ltd. "OXE-02"): 1.5 parts Ethanone, 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-, 1-(0-acetyloxime)
Cyclohexanone: 39.0 parts

[Examples 402 to 421, Comparative Examples 4 to 6]
(Photosensitive coloring composition (RR-2 to 24))
As shown in Table 6, photosensitive coloring compositions (RR-2 to RR-24) were obtained in the same manner as the photosensitive coloring composition (RR-1), except that the types and ratios of the coloring compositions were adjusted.
<Evaluation of Photosensitive Coloring Composition for Color Filter>
The luminance, contrast ratio, solvent resistance and dye migration of the obtained photosensitive coloring composition were evaluated by the following methods. The evaluation results are shown in Table 8.

(Brightness Evaluation)
The obtained photosensitive coloring composition was applied onto a glass substrate, dried at 70°C for 20 minutes, and then heated at 230°C for 60 minutes to obtain a coated substrate having a chromaticity of x=0.683 and y=0.313 under light source C. The luminance (Y) of the obtained substrate was measured with a microspectrophotometer (manufactured by Olympus Optical Co., Ltd., "OSP-SP200") and evaluated according to the following four stages.

◎: 13.5 or more (very good)
○: 13.0 or more, less than 13.5 (good)
△: 12.5 or more and less than 13.0 (bad)
×: Less than 12.5 (very poor)

(Evaluation of contrast ratio (CR))
The contrast ratio was measured using the substrate on which the luminance was measured, and was evaluated according to the following four levels.

◎: 8000 or more (very good)
○: 7000 or more to less than 8000 (good)
△: 6000 or more to less than 7000 (poor)
×: Less than 6000 (very poor)

(Evaluation of Solvent Resistance)
The photosensitive coloring composition for color filters was applied onto a glass substrate using a slit die coater, and then prebaked on a hot plate at 90° C. for 2 minutes to form a coating film with a thickness of 2.4 μm. The substrate on which the coating film was formed was then cooled to room temperature, and the coating film was exposed to radiation containing wavelengths of 365 nm, 405 nm, and 436 nm at an exposure dose of 1,000 J/m ² through a striped photomask using a high-pressure mercury lamp. After alkali development, the substrate was washed with ultrapure water and postbaked at 230° C. for 20 minutes to form red striped pixels on the substrate. The chromaticity ([L ^* (1), a ^* (1), b ^* (1)]) of the red striped pixels under C light source was then measured using a microspectrophotometer (Olympus Optical Co., Ltd. "OSP-SP100"). Thereafter, the sample was further immersed in N-methyl-2-pyrrolidone (NMP) for 15 minutes, and the chromaticity ([L ^* (2), a ^* (2), b ^* (2)]) after immersion was measured using Illuminant C. The color difference ΔEab ^* was calculated using the above formula and evaluated using the same criteria as for heat resistance.

(Evaluation of dye transfer)
The photosensitive coloring composition for color filters was applied onto a glass substrate using a slit die coater, and then prebaked on a hot plate at 90 ° C for 2 minutes to form a coating film with a thickness of 2.4 μm. The substrate on which the coating film was formed was then cooled to room temperature, and the coating film was exposed to radiation containing wavelengths of 365 nm, 405 nm, and 436 nm at an exposure dose of 1,000 J/m ² through a striped photomask using a high-pressure mercury lamp. After alkaline development, the substrate was washed with ultrapure water and postbaked at 230 ° C for 20 minutes to form red striped pixels on the substrate. The transmittance of 520 nm on the glass substrate 8 μm away from the red striped pixels was then measured (T1). The acrylic resin solution 2 was then applied onto the substrate using a slit die coater, and then prebaked on a hot plate at 90 ° C for 2 minutes to form a coating film with a thickness of 2.5 μm. The substrate was then postbaked at 230 ° C for 20 minutes. Next, the transmittance of the light at 520 nm on the glass substrate 8 μm away from the red stripe-shaped pixel was measured (T2). The difference between T1 and T2 was taken as ΔT (%) and evaluated using the following three-level scale. The smaller the ΔT value, the smaller the decrease in luminance due to color transfer to the adjacent filter segment of another color, and the more suppressed the color transfer.

○: ΔT is less than 1.0% (good)
△: ΔT is 1.0% or more and less than 3.0% (bad)
×: ΔT is 3.0% or more (very poor)

The results in Table 8 make it clear that the examples using the colorants of the present invention are excellent in brightness, contrast ratio, solvent resistance, and migration. In particular, a remarkable effect was confirmed by using them in place of C.I. Pigment Red 177, C.I. Pigment Red 269, or Red Colorant 6, which are conventionally used as bluish pigments.

<Method for producing green and blue photosensitive coloring compositions for color filters>
(Green photosensitive coloring composition 1: PG58/PY138)
A mixture of the following components was stirred and mixed to a uniform consistency, and then filtered through a filter having a pore size of 1.0 μm to prepare green photosensitive coloring composition 1.
Green colored composition (GCM-1): 32.0 parts Yellow colored composition (YCM-1): 18.0 parts Acrylic resin solution 2: 7.5 parts Photopolymerizable monomer (Toagosei Co., Ltd. "Aronix M-402"): 2.0 parts Dipentaerythritol hexaacrylate Photopolymerization initiator (BASF Co., Ltd. "OXE-02"): 1.5 parts Ethanone, 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-, 1-(0-acetyloxime)
Cyclohexanone: 39.0 parts

(Blue photosensitive coloring composition 1: PB15:6/PV23)
A blue-colored composition 1 was obtained in the same manner as in the green-colored composition 1, except that 32.0 parts of the green colored composition and 18.0 parts of the yellow colored composition were replaced with 46.0 parts of the blue colored composition and 4.0 parts of the purple colored composition in total of 50.0 parts.

<Production and Evaluation of Color Filters>
The red photosensitive coloring composition (RR-1) was applied onto a glass substrate on which a black matrix was formed using a slit die coater, and then prebaked on a hot plate at 90 ° C. for 2 minutes to form a coating film. Next, the substrate on which the coating film was formed was cooled to room temperature, and then the coating film was exposed to radiation containing wavelengths of 365 nm, 405 nm, and 436 nm at an exposure dose of 1,000 J / m ² through a striped photomask using a high-pressure mercury lamp. After alkali development, the substrate was washed with ultrapure water, and further postbaked at 230 ° C. for 20 minutes to form red striped pixels on the substrate.
Next, in the same manner, a green stripe-shaped pixel was formed adjacent to the red stripe-shaped pixel using the green photosensitive coloring composition 1. Furthermore, a blue stripe-shaped pixel adjacent to the red and green pixels was formed in the same manner using the blue photosensitive coloring composition 1.
Next, a protective film was formed on the pixels of three colors, red, green, and blue, using a photocurable resin composition. In this way, an RGB three-color filter having high brightness and excellent durability was produced.

Claims (9)

A colorant for color filters, comprising an azo pigment which is a compound represented by the following general formula (3), wherein the content of the azo pigment is 20 to 80 mass% in 100 mass% of the total of the colorants:

General formula (3)

[In general formula (3), R ₁₉ to R ₂₃ each independently represent a hydrogen atom, a halogen atom, an alkyl group which may have a substituent, an alkoxyl group which may have a substituent, an aryloxy group which may have a substituent, a hydroxyl group, a cyano group, a nitro group, a carboxyl group, a sulfo group, -CONR ₂₄ R ₂₅ , or -SO ₂ NR ₂₆ R _{27. R 24} to R ₂₇ each independently represent a hydrogen atom, an alkyl group which may have a substituent, or a phenyl group which may have a substituent, except for the cases where R ₁₉ , R ₂₁ , and R ₂₂ are all hydrogen atoms , or where R ₂₃ , R ₂₁ , and R ₂₀ are all hydrogen atoms .] 2. The colorant for color filters according to claim 1, wherein at least one of R ₁₉ to R ₂₃ in the general formula (3) is -CONHY or -SO ₂ NHY (wherein Y represents a phenyl group which may have a substituent). A coloring composition for color filters comprising a colorant and a binder resin, the colorant being the colorant for color filters according to claim 1 or 2. The coloring composition for color filters according to claim 3, further comprising a resin-type dispersant having an acidic substituent. The coloring composition for color filters according to claim 4, characterized in that the resin-type dispersant having an acidic substituent is a resin-type dispersant having an aromatic carboxyl group. The coloring composition for color filters according to any one of claims 3 to 5, further comprising a dye derivative, the dye derivative containing a dye derivative having a basic substituent. The colorant further comprises at least one selected from the group consisting of C.I. Pigment Red 242, C.I. Pigment Red 254, C.I. Pigment Red 291, C.I. Pigment Yellow 138, C.I. Pigment Yellow 139, C.I. Pigment Yellow 150, and a yellow pigment represented by the following general formula (4): The coloring composition for color filters according to any one of claims 3 to 6.

General formula (4)

[In general formula (4), Z ₁ to Z ₁₃ each independently represent a hydrogen atom, a halogen atom, an alkyl group which may have a substituent, an alkoxyl group which may have a substituent, an aryl group which may have a substituent, -SO ₃ H, -COOH, and monovalent to trivalent metal salts of these acidic groups, alkylammonium salts, a phthalimidomethyl group which may have a substituent, or a sulfamoyl group which may have a substituent.
Adjacent groups of Z ₁ to Z ₄ and/or Z ₁₀ to Z ₁₃ may be joined together to form an aromatic ring which may have a substituent.] The coloring composition for color filters according to any one of claims 3 to 7, further comprising a photopolymerizable monomer. A color filter comprising a filter segment formed from the coloring composition for color filters according to any one of claims 3 to 8 on a substrate.