JP6973270B2 - Color filter coating composition and color filter - Google Patents

Description

The present invention relates to a coloring composition for a color filter used for manufacturing a color filter used for manufacturing a color liquid crystal display device, a color solid-state image sensor, and the like, and a color filter formed by using the coloring composition.

In the liquid crystal display device, the liquid crystal layer sandwiched between the two polarizing plates controls the degree of polarization of the light passing through the first polarizing plate to control the amount of light passing through the second polarizing plate. This is a display device that displays with a twisted nematic (TN) type liquid crystal display, and the type that uses a twisted nematic (TN) type liquid crystal display is the mainstream. Other typical liquid crystal display methods include an in-plane switching (IPS) method in which a pair of electrodes are provided on one substrate and electrolysis is applied in a direction parallel to the substrate, and negative dielectric anisotropy. Vertical alignment (VA) method that vertically orients a nematic liquid crystal display with a Etc., and each has been put into practical use.

A liquid crystal display device can display colors by providing a color filter between two polarizing plates, and has been used in televisions, personal computer monitors, etc. in recent years. Therefore, the contrast and height of the color filters are higher and higher. The demand for brightening is increasing.

A color filter is a transparent substrate such as glass in which two or more fine striped filter segments having different hues are arranged in parallel or crossed each other, or fine filter segments are arranged in a constant vertical and horizontal direction. It consists of the ones arranged in. The filter segments are as fine as several microns to several hundreds of microns, and are arranged in a predetermined arrangement for each hue.

Generally, in a color liquid crystal display device, a transparent electrode for driving a liquid crystal is formed on a color filter by vapor deposition or sputtering, and an alignment film for orienting the liquid crystal in a certain direction is further formed on the transparent electrode. There is. In order to sufficiently obtain the performance of these transparent electrodes and alignment films, it is necessary to form them at a high temperature of generally 200 ° C. or higher, preferably 230 ° C. or higher. Therefore, as a method for manufacturing a color filter, a method called a pigment dispersion method using a pigment having excellent light resistance and heat resistance as a colorant is currently the mainstream.

The quality items required for the color filter include brightness and contrast ratio. If a color filter with a low contrast ratio is used, the degree of polarization controlled by the liquid crystal is disturbed, and when light must be blocked (OFF state), light leaks or when light must be transmitted (ON). Since the transmitted light is attenuated in the state), the screen becomes blurry. Therefore, in order to realize a high-quality liquid crystal display device, high contrast is indispensable.

Further, if a color filter having low brightness is used, the transmittance of light is low, resulting in a dark screen. In order to obtain a bright screen, it is necessary to increase the number of backlights as light sources. Therefore, from the viewpoint of suppressing the increase in power consumption, the trend is to increase the brightness of color filters. Further, as described above, color liquid crystal devices have come to be used for televisions, personal computer monitors, and the like, so that color filters are required to have high brightness, high contrast, and high reliability.

The red filter segment, which is one of the three primary colors (red, green, blue; RGB) of the color filter substrate, is a pigment having excellent light resistance and heat resistance such as diketopyrrolopyrrole pigment, anthraquinone pigment, or perylene pigment as a colorant. Is generally used alone or in combination.

Among the above pigment types, Diketopyrrolopyrrole pigment is C.I. I. Pigment Red 254 is an anthraquinone pigment from the viewpoint of contrast ratio. I. Pigment Red 177 is used as the main pigment. Among them, C.I. I. Pigment Red 177 has a spectral transmittance of C.I. I. Since it is lower than Pigment Red 254 and the spectral shape is poor, C.I. I. There was a drawback that the addition of Pigment Red 177 caused a decrease in brightness. Therefore, C.I. I. The development of an alternative material for Pigment Red 177 is desired.

In recent years, in order to realize high brightness and high coloring power, C.I. I. It has been proposed to use an azo pigment represented by Pigment Red 269 or a disazo pigment described in Patent Document 3 as a main pigment. I. Pigment Red 254 and C.I. I. Since it is different from Pigment Red 177 and the like, it has the drawbacks of being inferior in dispersibility, fluidity and storage stability, and also inferior in heat resistance and light resistance, and a practical color filter has not been obtained. In addition, C.I. I. Azo pigments such as Pigment Red 269 may have a problem of reduced brightness due to color transfer to adjacent other color filter segments, and there is a high demand for dye transferability.

In Patent Documents 1 to 3, in order to further improve the brightness of the red filter segment, C.I. I. Pigment Red 177, C.I. I. Although it has been proposed to use Pigment Red 269 and the disazo pigment described in Patent Document 3 as the main pigment, sufficient brightness could not be obtained, and further improvement was required.

Japanese Unexamined Patent Publication No. 2008-304521 Special Table 2007-533802 Gazette Japanese Unexamined Patent Publication No. 2014-160160

An object of the present invention is to provide a coloring composition for a color filter, which has a high luminance and contrast ratio and a thin film thickness when expressing the same color.

［一般式（１）中、Ｒ₁は、ハロゲン原子、置換基を有してもよいアルキル基、置換基を有してもよいアルコキシル基、置換基を有してもよいアリールオキシ基を表す。Ｒ₂およびＲ₃は、それぞれ独立に、水素原子、置換基を有してもよいアルキル基、置換基を有してもよいフェニル基を表す。
Ｘ₁〜Ｘ₄は、それぞれ独立に、水素原子、置換基を有してもよいアルキル基、置換基を有してもよいアルコキシル基、ヒドロキシル基、シアノ基、ニトロ基、カルボキシル基、スルホ基、ハロゲン原子を表す。］

一般式（２）

［一般式（２）中、Ｒ₄は、ハロゲン原子、置換基を有してもよいアルキル基、置換基を有してもよいアルコキシル基、置換基を有してもよいアリールオキシ基を表す。Ｒ₅およびＲ₆は、それぞれ独立に、水素原子、置換基を有してもよいアルキル基、置換基を有してもよいフェニル基を表す。
Ｘ₅〜Ｘ₁₂は、それぞれ独立に、水素原子、置換基を有してもよいアルキル基、置換基を有してもよいアルコキシル基、ヒドロキシル基、シアノ基、ニトロ基、ハロゲン原子を表す。Ａは、直接結合、または２価の連結基を表す。２価の連結基としては、置換基を有してもよいアルキレン基、−Ｏ−、−Ｓ−、−ＣＯ−、−ＳＯ₂−、−ＣＯＯ−、−ＣＯＮＨ−、−ＳＯ₂ＮＨ−を表す。］ The coloring composition for a color filter of the present invention comprises an azo pigment containing a compound represented by the following general formula (1) or (2), a coloring agent composed of a dye, and a binder resin.
General formula (1)

[In the general formula (1), R ₁ represents a halogen atom, an alkyl group which may have a substituent, an alkoxyl group which may have a substituent, and an aryloxy group which may have a substituent. .. R ₂ and R ₃ independently represent a hydrogen atom, an alkyl group which may have a substituent, and a phenyl group which may have a substituent.
Independently, X _{1 to} X ₄ are 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 and a sulfo group. , Represents a halogen atom. ]

General formula (2)

[In the general formula (2), R ₄ represents a halogen atom, an alkyl group which may have a substituent, an alkoxyl group which may have a substituent, and an aryloxy group which may have a substituent. .. R ₅ and R ₆ independently represent a hydrogen atom, an alkyl group which may have a substituent, and a phenyl group which may have a substituent.
X _{5 to} X ₁₂ 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, and a halogen atom. A represents a direct bond or a divalent linking group. As the divalent linking group, an alkylene group which may have a substituent, -O-, -S-, -CO-, -SO _2- , -COO-, -CONH-, and -SO ₂ NH- are used. show. ]

Further, an embodiment of the present invention is a coloring composition for a color filter composed of at least a colorant and a binder resin, wherein the colorant is a colorant for a color filter containing the azo pigment and a dye. The present invention relates to a coloring composition for a color filter.

Further, the embodiment of the present invention further relates to a coloring composition for a color filter, which further comprises a resin-type dispersant having an acidic substituent.

Further, an embodiment of the present invention relates to a coloring composition for a color filter, wherein the resin-type dispersant having an acidic substituent is a resin-type dispersant having an aromatic carboxyl group.

Further, an embodiment of the present invention further relates to a coloring composition for a color filter, which further comprises a dye derivative, wherein the dye derivative contains a dye derivative having a basic substituent.

［一般式（３）中、Ｚ₁〜Ｚ₁₃は、それぞれ独立に、水素原子、ハロゲン原子、置換基を有してもよいアルキル基、置換基を有してもよいアルコキシル基、置換基を有してもよいアリール基、−ＳＯ₃Ｈ、−ＣＯＯＨ、およびこれら酸性基の１価〜３価の金属塩、アルキルアンモニウム塩、置換基を有してもよいフタルイミドメチル基、または置換基を有してもよいスルファモイル基を示す。
Ｚ₁〜Ｚ₄、および／または、Ｚ₁₀〜Ｚ₁₃の隣接した基は、一体となって、置換基を有してもよい芳香環を形成する場合がある。］ Further, in the embodiment of the present invention, the colorant is further used, and C.I. I. Pigment Red 254, C.I. I. Pigment Red 242, C.I. I. Pigment Yellow 138, C.I. I. Pigment Yellow 139, C.I. I. The present invention relates to the coloring composition for a color filter, which comprises at least one selected from the group consisting of Pigment Yellow 150, a yellow pigment represented by the following general formula (3), and a brominated diketopyrrolopyrrole pigment.

General formula (3)

[In the general formula (3), Z _{1 to} Z ₁₃ independently have a hydrogen atom, a halogen atom, an alkyl group which may have a substituent, an alkoxyl group which may have a substituent, and a substituent. It may have an aryl group, -SO ₃ H, -COOH, and monovalent to trivalent metal salt thereof acidic groups, alkylammonium salt, an optionally substituted phthalimidomethyl group, or a substituent The sulfamoyl group which may have is shown.
Adjacent groups of Z _{1 to} Z ₄ and / or Z _{10 to} Z ₁₃ may together form an aromatic ring that may have a substituent. ]

Further, an embodiment of the present invention is characterized in that the dye is at least one selected from the group consisting of xanthene-based, dipyrromethene-based, triarylmethane-based, cyanine-based, phthalocyanine-based and anthraquinone-based dyes. For coloring compositions.

Further, the embodiment of the present invention further relates to the coloring composition for a color filter, which further comprises a photopolymerizable monomer.

Further, an embodiment of the present invention relates to a color filter comprising a filter segment formed from the coloring composition for a color filter on a substrate.

According to the present invention, a photosensitive composition is used by using a pigment having excellent fastness such as heat resistance and light resistance, few foreign substances in the coating film, and good storage stability, and a coloring composition composed of a dye and a binder resin. Therefore, there is an excellent effect that it is possible to provide a coloring composition for a color filter and a color filter having a high brightness and contrast ratio and a thin film thickness when expressing the same color.

Hereinafter, the present invention will be described in detail. In addition, in this specification, when it is described as "(meth) acryloyl", "(meth) acrylic", "(meth) acrylic acid", "(meth) acrylate", or "(meth) acrylamide", it is referred to as "(meth) acrylamide". Unless otherwise stated, "acrylloyl and / or methacrylic acid", "acrylic and / or methacrylic", "acrylic acid and / or methacrylic acid", "acrylate and / or methacrylate", or "acrylamide and / or methacrylic acid", respectively. ". Further, "CI" mentioned in the present specification means a color index (CI).

<Azo pigment>
First, the azo pigment represented by the general formula (1) or (2) of the present invention will be described. In this specification, "azo pigment represented by the general formula (1) or (2)" is abbreviated as "pigment", and "colorant for color filter" is abbreviated as "colorant". There is.

General formula (1)

In the general formula (1), R ₁ represents a halogen atom, an alkyl group which may have a substituent, an alkoxyl group which may have a substituent, and an aryloxy group which may have a substituent. R ₂ and R ₃ independently represent a hydrogen atom, an alkyl group which may have a substituent, and a phenyl group which may have a substituent.
Independently, X _{1 to} X ₄ are 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 and a sulfo group. , Represents a halogen atom.

Examples of the "halogen atom" in R ₁ include fluorine, bromine, chlorine and iodine, and among these, chlorine is preferable.

In R ₁ , the "alkyl group which may have a substituent" includes 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, and the like. 2-Ethylhexyl group, stearyl group, chloromethyl group, trichloromethyl group, trifluoromethyl group, 2-methoxyethyl group, 2-chloroethyl group, 2-nitroethyl group, cyclopentyl group, cyclohexyl group, dimethylcyclohexyl group and the like. Of these, a methyl group and a trifluoromethyl group are preferable.

In R ₁ , the "alkoxyl group which may have a substituent" includes a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, an n-octyloxy group and a 2-ethylhexyloxy group. Examples thereof include a trifluoromethoxy group, a cyclohexyloxy group, a stearyloxy group, a 2- (diethylamino) ethoxy group and the like, of which a methoxy group and a trifluoromethoxy group are preferable, and a methoxy group is particularly preferable.

In R ₁ , the "aryloxy group which may have a substituent" includes a phenoxy group, a naphthyloxy group, a 4-methylphenyloxy group, a 3,5-chlorophenyloxy group, and a 4-chloro-2-methylphenyloxy group. Groups, 4-tert-butylphenyloxy group, 4-methoxyphenyloxy group, 4-diethylaminophenyloxy group, 4-nitrophenyloxy group and the like can be mentioned, and among these, a phenoxy group is preferable.

In R ₂ and R ₃ , the "alkyl group which may have a substituent" includes 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 tert. -Amil group, 2-ethylhexyl group, stearyl group, chloromethyl group, trichloromethyl group, trifluoromethyl group, 2-methoxyethyl group, 2-hydroxyethyl group, 2-chloroethyl group, 2-nitroethyl group, cyclopentyl group, Examples thereof include a cyclohexyl group and a dimethylcyclohexyl group, and 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 are preferable.

In R ₂ and R ₃ , the substituent of the "phenyl group which may have a substituent" may have a _{halogen atom in R 1,} an alkyl group which may have a substituent, and a substituent. Examples thereof include an alkoxyl group and an aryloxy group which may have a substituent, and in addition to these, a hydroxyl group, an amino group, -NR ₇ R ₈ , a sulfo group, -SO ₂ NR ₉ R ₁₀ , -COOR ₁₁ , -CONR ₁₂ R ₁₃ , nitro group, cyano group and the like.

R _{7 to} R ₁₃ independently represent a hydrogen atom and an alkyl group which may have a substituent, and examples of the "alkyl group which may have a substituent" include an amino group and a monoalkylamino group. Alternatively, an alkyl group substituted with a dialkylamino group is preferable.

In X _{1 to} X ₄ , the "alkyl group which may have a substituent" has the same _{meaning as that in R 1} , and a methyl group, an ethyl group and a trifluoromethyl group are preferable.

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

General formula (2)

In the general formula (2), R ₄ represents a halogen atom, an alkyl group which may have a substituent, an alkoxyl group which may have a substituent, and an aryloxy group which may have a substituent. R ₅ and R ₆ independently represent a hydrogen atom, an alkyl group which may have a substituent, and a phenyl group which may have a substituent.
X _{5 to} X ₁₂ 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, and a halogen atom. A represents a direct bond or a divalent linking group. As the divalent linking group, an alkylene group which may have a substituent, -O-, -S-, -CO-, -SO _2- , -COO-, -CONH-, and -SO ₂ NH- are used. show.

In R ₄ , as "halogen atom", "alkyl group which may have a substituent", "alkoxyl group which may have a substituent", and "aryloxy group which may have a substituent". Is synonymous with that in _{R 1.}

In R ₅ and R ₆ , the "alkyl group which may have a substituent" and the "phenyl group which may have a substituent" are synonymous with those in _{R 2} and R _3.

In X _{5 to} X ₁₂ , the "alkyl group which may have a substituent" and the "alkoxyl group which may have a substituent" are synonymous with those _{in R 1.}

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. A group is mentioned, and examples of the substituent include an "alkyl group which may have a substituent" represented by _{R 1.}

The A in the general formula (2), substituents alkylene group which may have a, -O -, - S -, - CO -, - SO ₂ - is preferably, -SO ₂ among them - is Especially preferable.

<Other pigments>
The colorant used in the present invention is used in combination with a pigment other than the pigment containing the compound represented by the above general formula (1) or (2) as long as the effect of the present invention is not impaired, for the purpose of adjusting the chromaticity. You may. These pigments can be used alone or in admixture of two or more at any ratio as required.

Other pigments include, for example, C.I. 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, Red pigments such as 278, 279, 280, 281, 282, 283, 284, 285, 286, 287 or brominated diketopyrrolopyrrole pigments can be mentioned.

In addition, C.I. I. Pigment Orange 43, 71, or 73 and / or orange pigments and / or C.I. I. Pigment Yellow 1, 2, 3, 4, 5, 6, 10, 12, 13, 14, 15, 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, 94, 95, 97, 98, 100, 101, 104, 106, 108, 109, 110, 113, 114, 115, 116, 117, 118, 119, 120, 123, 126, 127, 128, 129, 138, 139, 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 the yellow pigment represented by the following general formula (3) can be used in combination.

Preferred pigments to be used in combination are azo-based, naphthol-azo-based, diketopyrrolopyrrole-based, anthraquinone-based, quinophthalone-based, and perylene-based pigments from the viewpoint of fastness such as heat resistance and light resistance and chromaticity range. Can be mentioned. Specifically, C.I. I. Pigment Red 269, 177, 254, 242, C.I. I. Pigment Yellow 138, 139, 150, 185, a yellow pigment represented by the following general formula (3), and a brominated diketopyrrolopyrrole pigment can be mentioned.
Especially from the viewpoint of brightness and coloring power, C.I. I. Pigment Red 254, 242, C.I. I. Pigment Yellow 138, 139, 150, a yellow pigment represented by the following general formula (3), and a brominated diketopyrrolopyrrole pigment are more preferable.

［一般式（３）中、Ｚ₁〜Ｚ₁₃は、それぞれ独立に、水素原子、ハロゲン原子、置換基を有してもよいアルキル基、置換基を有してもよいアルコキシル基、置換基を有してもよいアリール基、−ＳＯ₃Ｈ、−ＣＯＯＨ、およびこれら酸性基の１価〜３価の金属塩、アルキルアンモニウム塩、置換基を有してもよいフタルイミドメチル基、または置換基を有してもよいスルファモイル基を示す。
Ｚ₁〜Ｚ₄、および／または、Ｚ₁₀〜Ｚ₁₃の隣接した基は、一体となって、置換基を有してもよい芳香環を形成する場合がある。 General formula (3)

[In the general formula (3), Z _{1 to} Z ₁₃ independently have a hydrogen atom, a halogen atom, an alkyl group which may have a substituent, an alkoxyl group which may have a substituent, and a substituent. It may have an aryl group, -SO ₃ H, -COOH, and monovalent to trivalent metal salt thereof acidic groups, alkylammonium salt, an optionally substituted phthalimidomethyl group, or a substituent The sulfamoyl group which may have is shown.
Adjacent groups of Z _{1 to} Z ₄ and / or Z _{10 to} Z ₁₃ may together form an aromatic ring that may have a substituent.

Here, examples of the halogen atom include fluorine, chlorine, bromine, and iodine.

Examples of the alkyl group which may have a substituent include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert-butyl group, a neopentyl group, an n-hexyl group and an n-octyl group. In addition to a linear or branched alkyl group such as a group, a stearyl group and a 2-ethylhexyl group, a trichloromethyl group, a trifluoromethyl group, a 2,2,2-trifluoroethyl group and a 2,2-dibromoethyl group, 2,2,3,3-tetrafluoropropyl group, 2-ethoxyethyl group, 2-butoxyethyl group, 2-nitropropyl group, benzyl group, 4-methylbenzyl group, 4-tert-butylbenzyl group, 4- Examples thereof include an alkyl group having a substituent such as a methoxybenzyl group, a 4-nitrobenzyl group and a 2,4-dichlorobenzyl group.

Examples of the alkoxyl group which may have a substituent include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, an n-butoxy group, an isobutyloxy group, a tert-butyloxy group, a neopentyloxy group, a few. -In addition to linear or branched alkoxyl groups such as dimethyl-3-pentoxy, n-hexyloxy group, n-octyloxy group, stearyloxy group and 2-ethylhexyloxy group, trichloromethoxy group, trifluoromethoxy group, 2 , 2,2-Trifluoroethoxy group, 2,2,3,3-tetrafluoropropyloxy group, 2,2-ditrifluoromethylpropoxy group, 2-ethoxyethoxy group, 2-butoxyethoxy group, 2-nitropropoxy Examples thereof include an alkoxyl group having a substituent such as a group and a benzyloxy group.

The aryl group which may have a substituent includes an aryl group such as a phenyl group, a naphthyl group and an anthranyl group, as well as a p-methylphenyl group, a p-bromophenyl group, a p-nitrophenyl group and a p-. Methoxyphenyl group, 2,4-dichlorophenyl group, pentafluorophenyl group, 2-aminophenyl group, 2-methyl-4-chlorophenyl group, 4-hydroxy-1-naphthyl group, 6-methyl-2-naphthyl group, 4 , 5,8-Trichloro-2-naphthyl group, anthraquinonyl group, 2-aminoanthraquinonyl group and other aryl groups having substituents can be mentioned.

As the acidic _group, -SO 3 H, -COOH, and examples of the monovalent to trivalent metal salt thereof acidic groups, sodium salts, potassium salts, magnesium salts, calcium salts, iron salts, aluminum salts And so on. Examples of the alkylammonium salt of the acidic group include ammonium salts of long-chain monoalkylamines such as octylamine, laurylamine and stearylamine, and quaternary alkyls such as palmityltrimethylammonium, dilauryldimethylammonium and distealyldimethylammonium salts. Ammonium salt can be mentioned.

"Substituents" in the phthalimidemethyl group (C ₆ H ₄ (CO) ₂ N-CH ₂ −) which may have a substituent and the sulfamoyl group (H ₂ NSO ₂ −) which may have a substituent. Examples thereof include the above-mentioned 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 and the like.

_{Adjacent groups of Z 1 to} Z ₄ and / or Z _{10 to} Z ₁₃ of the general formula (3) may be integrated to form an aromatic ring which may have a substituent. Examples of the aromatic ring here include a hydrocarbon aromatic ring and a heteroaromatic ring. Examples of the hydrocarbon aromatic ring include a benzene ring, a naphthalene ring, an anthracene ring, and a phenanthrene ring, and the heteroaromatic ring includes pyridine. Examples thereof include a ring, a pyrazine ring, a pyrrol ring, a quinoline ring, a quinoxalin 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 the general formula (3) used in the colorant for a color filter of the present invention include the quinophthalone compounds (a) to (r) shown below, and the present invention includes these. Not limited. Further, 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 thereto.

<Dye>
The coloring composition of the present invention uses a dye as a colorant together with the azo pigment. As the dye, any of acidic dyes, direct dyes, basic dyes, salt-forming dyes, oil-soluble dyes, disperse dyes, reactive dyes, medium dyes, building dyes, sulfide dyes and the like can be used. Further, these derivatives or a lake pigment obtained by converting a dye into a lake may be used.

Further, an acidic dye having an acidic group such as sulfonic acid or carboxylic acid, or in the case of a direct dye form, an inorganic salt of the acidic dye, an acidic dye and a quaternary ammonium salt compound, a tertiary amine compound, a secondary amine compound, Alternatively, a salt-forming compound with a nitrogen-containing compound such as a primary amine compound, or chloride-forming using a resin component having these functional groups to be used as a salt-forming compound, or sulfonamide formation and use as a sulfonic acid amide compound. In order to obtain excellent resistance, a coloring composition having excellent fastness can be obtained, which is preferable.
Further, a salt-forming compound of an acid dye and a compound having an onium base is also preferable because it has excellent fastness, and more preferably, the compound having an onium base is a resin having a cationic group in the side chain.

In the case of the basic dye form, it can be used by chlorinating with an organic acid, perchloric acid or a metal salt thereof. Among them, the salt-forming compound of the basic dye is preferable because it has excellent resistance and compatibility with the pigment. Further, the basic dye and the counter component that works as a counter ion, organic sulfonic acid, organic sulfuric acid, and fluorine group-containing phosphorus are preferable. It is possible to use a salt-forming compound obtained by salting an anionic compound, a fluorine group-containing boron anionic compound, a cyano group-containing nitrogen anion compound, an anion compound having a conjugated base of an organic acid having a halogenated hydrocarbon group, or an acidic dye. It is more preferable.

Further, when the dye skeleton has a polymerizable unsaturated group, the dye can be a dye having excellent resistance, which is preferable.

The chemical structure of the dye includes, for example, azo dye, azomethin dye (Indian aniline dye, Indian phenol dye, etc.), dipyrromethene dye, quinone dye (benzoquinone dye, naphthoquinone dye, anthraquinone dye, anthra). Pyridone dyes, etc.), Carbonium dyes (diarylmethane dyes, triarylmethane dyes, xanthene dyes, acridin dyes, etc.), quinoneimine dyes (oxazine dyes, thiazine dyes, etc.), azine dyes, polymethine Dyes (oxonol dyes, merocyanine dyes, allylidene dyes, styryl dyes, cyanine dyes, squarylium dyes, croconium dyes, etc.), quinophthalone dyes, phthalocyanine dyes, subphthalocyanine dyes, perinone dyes, Examples thereof include dye structures derived from dyes selected from indigo dyes, thioindigo dyes, quinoline dyes, nitro dyes, nitroso dyes, and their metal complex dyes.

Among these dye structures, from the viewpoint of color characteristics such as hue, color separability, and color unevenness, azo dyes, xanthene dyes, cyanine dyes, triarylmethane dyes, anthraquinone dyes, dipyrromethene dyes, and squaryliums. Dye structures derived from dyes selected from dyes selected from dyes, quinophthalone dyes, phthalocyanine dyes, and subphthalocyanine dyes are preferable, and xanthene dyes, cyanine dyes, triarylmethane dyes, anthraquinone dyes, dipyrromethene dyes, and phthalocyanine dyes are preferable. A dye structure derived from a dye selected from the dyes is more preferable. For specific dye compounds that can form a dye structure, see "New Edition Dye Handbook" (Society of Synthetic Organic Chemistry; Maruzen, 1970), "Color Index" (The Society of Dyeers and colorists), "Dye Handbook" (Okawara et al.) Hen; Kodansha, 1986).

[Xanthene dyes]
The xanthene-based dye that can be preferably used in the present invention is red or purple, and preferably has any form of an oil-soluble dye, an acid dye, a direct dye, or a basic dye. Further, it may be in the form of a lake pigment obtained by converting these dyes into lakes.
Among these, it is preferable to use a xanthene-based oil-soluble dye or a xanthene-based acid dye because of its excellent hue.

The red and purple colors are defined as C.I. I. Solvent Red, C.I. I. Oil-soluble dyes such as solvent violet, C.I. I. Basic Red, C.I. I. Basic dyes such as basic violet, C.I. I. Acid Red, C.I. I. Acid dyes such as acid violet, C.I. I. Direct Red, C.I. I. Those belonging to direct dyes such as direct violet can be mentioned.
Here, the direct dye has a sulfonic acid group (-SO ₃ H, -SO ₃ Na) in the structure, and in the present invention, the direct dye is regarded as an acid dye.

Further, the xanthene-based basic dye is preferably used by chlorinating with an organic acid or perchloric acid. As the organic acid, it is preferable to use an organic sulfonic acid or an organic carboxylic acid. Above all, it is preferable to use naphthalene sulfonic acid such as tobias acid and perchloric acid in terms of resistance.
Further, the xanthene-based acidic dye is used as a salt-forming compound by chloride-forming using a quaternary ammonium salt compound, a tertiary amine compound, a secondary amine compound, a primary amine compound, and a resin component having these functional groups. In terms of resistance, it is preferable to sulfonate or use as a sulfonic acid amide compound.

Among these, salt-forming compounds of xanthene-based acidic dyes and / or sulfonic acid amide compounds of xanthene-based acidic dyes are preferable because they have excellent hue and resistance, and further, xanthene-based acidic dyes are counter components that act as counter ions. It is more preferable to use a compound obtained by chloride using the quaternary ammonium salt compound, and a sulfonic acid amide compound obtained by sulfonic amidating a xanthene-based acidic dye.

Further, among the xanthene-based dyes, the rhodamine-based dyes are preferable because they are excellent in color development and resistance.

Hereinafter, the form of the xanthene-based dye used in the present invention will be specifically described in detail.

[Xanthene-based oil-soluble dye]
Examples of xanthene-based oil-soluble dyes include CI Solvent Red 35, CI Solvent Red 36, CI Solvent Red 42, CI Solvent Red 43, CI Solvent Red 44, and C.I. I. Solvent Red 45, CI Solvent Red 46, CI Solvent Red 47, CI Solvent Red 48, CI Solvent Red 49, CI Solvent Red 72, CI. Solvent Red 73, CI Solvent Red 109, CI Solvent Red 140, CI Solvent Red 141, CI Solvent Red 237, CI Solvent Red 246, CI Solvent Violet 2. CI Solvent Violet 10 and the like can be mentioned.
Among them, CI Solvent Red 35, CI Solvent Red 36, CI Solvent Red 49, CI Solvent Red 109, and CI Solvent Red, which are rhodamine-based oil-soluble dyes with high color development. Red 237, CI Solvent Red 246 and CI Solvent Violet 2 are more preferred.

[Xanthene-based basic dye]
Examples of the xanthene-based basic dye include C.I. I. Basic Red 1 (Rhodamine 6 GCP), 8 (Rhodamine G), C.I. I. Basic Violet 10 (Rhodamine B) and the like can be mentioned. Above all, in terms of excellent color development, C.I. I. Basic Red 1, C.I. I. It is preferable to use Basic Violet 10.

[Xanthene acid dye]
Examples of the xanthene-based acid dye include C.I. I. Acid Red 51 (erythrosine (edible red No. 3)), C.I. I. Acid Red 52 (Acid Rhodamine), C.I. I. Acid Red 87 (Eosin G (Edible Red No. 103)), C.I. I. Acid Red 92 (Acid Phloxine PB (Edible Red No. 104)), C.I. I. Acid Red 289, C.I. I. Acid Red 388, Rose Bengal B (Edible Red No. 5), Acid Rhodamine G, C.I. I. It is preferable to use acid violet 9.
Among them, C.I., a xanthene-based acid dye, is a xanthene-based acid dye in terms of heat resistance and light resistance. I. Acid Red 87, C.I. I. Acid Red 92, C.I. I. Acid Red 388 or Rhodamine-based acid dye C.I. I. Acid Red 52 (Acid Rhodamine), C.I. I. Acid Red 289, Acid Rhodamine G, C.I. I. It is more preferable to use acid violet 9.
Among these, C.I., which is a rhodamine-based acid dye, is particularly excellent in color development, heat resistance, and light resistance. I. Acid Red 52, C.I. I. It is most preferable to use Acid Red 289.

Further, these acidic dyes are preferably salt-forming compounds of the acidic dyes and nitrogen-containing compounds, and are quaternary ammonium salt compounds, tertiary amine compounds, secondary amine compounds, primary amine compounds and the like, and their functionalities. It is preferable to form chloride using a resin component having a group to obtain a salt-forming compound of a xanthene-based acidic dye, because high heat resistance, light resistance, and solvent resistance can be imparted.
Further, it may be a salt-forming compound of an acid dye and a compound having an onium base, and among them, the compound having an onium base is a resin having a cationic group in the side chain, so that the lightness and resistance can be improved. It can be an excellent coloring composition.

Primary amine compounds include methylamine, ethylamine, propylamine, isopropylamine, butylamine, amylamine, hexylamine, heptylamine, octylamine, nonylamine, decylamine, undecylamine, dodecylamine (laurylamine), tridodecylamine, tetra. Examples thereof include aliphatic unsaturated primary amines such as decylamine (myristylamine), pentadecylamine, cetylamine, stearylamine, oleylamine, cocoalkylamine, beef alkylamine, hardened beef alkylamine, and allylamine, aniline, and benzylamine. ..

Examples of the secondary amine compound include aliphatic unsaturated secondary amines such as dimethylamine, diethylamine, dipropylamine, diisopropylamine, dibutylamine, diamylamine and diallylamine, methylaniline, ethylaniline, dibenzylamine, diphenylamine and dicocoalkyl. Examples include amines, di-cured beef fat alkylamines, distearylamines, etc.

Examples of the tertiary amine compound include trimethylamine, triethylamine, tripropylamine, tributylamine, triamylamine, dimethylaniline, diethylaniline, tribenzylamine and the like.

Examples of the quaternary ammonium salt compound include tetramethylammonium chloride, tetraethylammonium chloride, monostearyltrimethylammonium chloride, distearyldimethylammonium chloride, tristearylmonomethylammonium chloride, cetyltrimethylammonium chloride, trioctylmethylammonium chloride, and dioctyldimethylammonium chloride. , Monolauryltrimethylammonium chloride, Dilauryldimethylammonium chloride, Trilaurylmethylammonium chloride, Triamylbenzylammonium chloride, Trihexylbenzylammonium chloride, Trioctylbenzylammonium chloride, Trilaurylbenzylammonium chloride, benzyldimethylstearylammonium chloride, and Examples thereof include benzyldimethyloctylammonium chloride, dialkyl (alkyl is C14 to C18) and dimethylammonium chloride (hardened beef).

Specific quaternary ammonium salt compound products include, for example, Kao Corporation's Coatamine 24P, Coatamine 86P Conch, Coatamine 60W, Coatamine 86W, Coatamine D86P, Sanizol C, Sanizol B-50, etc. 80E, 2C-75, 2HT-75, 2HT flakes, 2O-75I, 2HP-75, 2HP flakes, etc. C18) Dimethylammonium chloride).

[Resin having a cationic group in the side chain]
A resin having a cationic group in the side chain will be described. The resin having a cationic group in the side chain for obtaining the salt-forming compound is not particularly limited as long as it has at least one onium base in the side chain, but is available as a suitable onium salt structure. From the viewpoint of the above, ammonium salt, iodonium salt, sulfonium salt, diazonium salt, and phosphonium salt are preferable, and in consideration of storage stability (thermal stability), ammonium salt, iodonium salt, and sulfonium salt are used. Is more preferable. More preferably, it is an ammonium salt.

The resin having a cationic group in the side chain is an alkaline resin containing a structural unit represented by the following general formula (4), and the cationic group in the general formula (4) is an anionic group of a xanthene acid dye. By forming a salt, a salt-forming compound can be obtained.

［一般式（４）中、Ｒ⁵¹は水素原子、または置換もしくは無置換のアルキル基を表す。Ｒ⁵²〜Ｒ⁵⁴は、それぞれ独立に、水素原子、置換されていてもよいアルキル基、置換されていてもよいアルケニル基、または置換されていてもよいアリール基を表し、Ｒ⁵²〜Ｒ⁵⁴のうち２つが互いに結合して環を形成しても良い。Ｑはアルキレン基、アリーレン基、−ＣＯＮＨ−Ｒ⁵⁵−、−ＣＯＯ−Ｒ⁵⁵−を表し、Ｒ⁵⁵はアルキレン基を表す。Ｙ^-は無機または有機のアニオンを表す。］

[In the general formula (4), R ⁵¹ represents a hydrogen atom or a substituted or unsubstituted alkyl group. R ^{52 to} R ⁵⁴ independently represent a hydrogen atom, an optionally substituted alkyl group, an optionally substituted alkenyl group, or an optionally substituted aryl group, respectively, of R ^{52 to} R ⁵⁴ . Two of them may be combined with each other to form a ring. Q represents an alkylene group, an arylene group, −CONH-R ⁵⁵ −, −COO − R ⁵⁵ −, and R ⁵⁵ represents an alkylene group. Y ^- is representative of an inorganic or organic anion. ]

[Salt formation]
The salt-forming compound of the acid dye and the nitrogen-containing compound or the resin having a cationic group in the side chain can be produced by a conventionally known method. A specific method is disclosed in JP-A-11-72969.
To give an example using a xanthene-based acid dye, a quaternary ammonium salt compound may be added after dissolving the xanthene-based acid dye in water, and the chloride-forming treatment may be performed while stirring. Here, the sulfonic acid group (-SO ₃ H) and sodium sulfonic acid group (-SO ₃ Na) in the xanthene-based acidic dye and the ammonium group (NH ₄ ⁺ ) in the quaternary ammonium salt compound are bonded. A salt compound is obtained. In addition, instead of water, methanol and ethanol are also solvents that can be used during chloride formation.

Further, the salt-forming compound used in the present invention is prepared by stirring or vibrating an aqueous solution prepared by dissolving a resin having a cationic group in a side chain represented by the general formula (4) and an acid dye, or using the general formula (4). ), An aqueous solution of a resin having a cationic group in the side chain and an aqueous solution of an acid dye are mixed with stirring or vibration to easily obtain the solution. In the aqueous solution, the ammonium group of the resin and the anionic group of the acid dye are ionized, and these are ionically bonded, and the ion-bonded portion becomes water-insoluble and precipitates. On the contrary, since the salt composed of the counter anion of the resin and the counter cation of the acid dye is water-soluble, it can be removed by washing with water or the like. As the resin having a cationic group in the side chain and the acid dye, only one kind may be used, or a plurality of kinds having different structures may be used.
As for other acid dyes, a nitrogen-containing compound or a salt-forming compound with a resin having a cationic group in the side chain can be obtained by the same method as that for xanthene dyes.

[Sulfonic acid amide compound]
The acid dye used in the present invention may be a sulfonic acid amide compound obtained by reacting a sulfonic acid amide compound with an anionic dye.
The sulfonic acid amide compound of the acid dye that can be preferably used for the acid dye of the present invention is obtained by chlorinating _{an acid dye having −SO 3} H and −SO ₃ Na by a conventional method to convert −SO ₃ H to −SO ₂ Cl. This compound can be produced by reacting with an amine having _{-NH 2 group.}
Specific examples of the amine compound that can be preferably used in sulfonamide formation include 2-ethylhexylamine, dodecylamine, 3-decyloxypropylamine, 3- (2-ethylhexyloxy) propylamine, and 3-ethoxypropyl. It is preferable to use amine, cyclohexylamine and the like.
To give an example using a xanthene-based acid dye, C.I. I. When a sulfonic acid amide compound obtained by modifying Acid Red 289 with 3- (2-ethylhexyloxy) propylamine is obtained, C.I. I. Acid Red 289 is sulfonyl chlorided and then reacted with a theoretical equivalent of 3- (2-ethylhexyloxy) propylamine in dioxane to give C.I. I. The sulfonic acid amide compound of Acid Red 289 may be obtained.
In addition, C.I. I. In the case of obtaining a sulfonic acid amide compound obtained by modifying Acid Red 52 with 3- (2-ethylhexyloxy) propylamine, C.I. I. Acid Red 52 is sulfonyl chlorided and then reacted with a theoretical equivalent of 3- (2-ethylhexyloxy) propylamine in dioxane to give C.I. I. The sulfonic acid amide compound of Acid Red 52 may be obtained.
Further, for other acid dyes, a sulfonic acid amide compound can be obtained by the same method as that for xanthene dyes.

Examples of such xanthene dyes include JP-A-2010-032999, JP-A-2011-13894, JP-A-2011-227313, JP-A-2011-242752, JP-A-2012-107192, and Japanese Patent Publication No. 2012-107192. Kai 2013-033194, Japanese Patent Application No. 2011-71888, Japanese Patent Application No. 2013-72263, Japanese Patent Application Laid-Open No. 2013-81209, Japanese Patent Application Laid-Open No. 2014-173064, Japanese Patent Application Laid-Open No. 2013-53028, Japanese Patent Application No. 2013 -52186, JP-A-2014-196392, JP-A-2014-196393, JP-A-2014-201714, JP-A-2014-201715, JP-A-2013-050693, JP-A-2013-178478 The publicly known techniques described in Japanese Patent Application Laid-Open No. 2013-203056, International Publication No. 2013/0116887, and the like can be used.

[Dypyrromethene dye]
The dipyrromethene dye is a dye having a partial structure derived from the dipyrromethene dye as a partial structure of the dye portion, and a dipyrromethene compound and a dipyrromethene metal complex compound obtained from a dipyrromethene compound and a metal or a metal compound are preferable. However, a metal complex compound in which the structure represented by the general formula (5) is coordinated with a metal atom or a metal compound (hereinafter, appropriately referred to as “dipyrromethene metal complex compound”) is preferable.

[Dipyrromethene metal complex compound]
A metal complex compound (dipyrromethene metal complex compound) in which the structure represented by the general formula (5) is coordinated with a metal atom or a metal compound will be described.

In the general formula (5), R ^{61 to} R ⁶⁶ each independently represent a hydrogen atom or a monovalent substituent, and R ⁶⁷ is a hydrogen atom, a halogen atom, an alkyl group, an aryl group, or a heterocyclic group. Represents.
The metal or metal compound may be any metal atom or metal compound capable of forming a complex, and may be a divalent metal atom, a divalent metal oxide, a divalent metal hydroxide, or 2 Valuable metal chloride is included. Examples of the metal or metal compound include Zn, Mg, Si, Sn, Rh, Pt, Pd, Mo, Mn, Pb, Cu, Ni, Co, Fe, B, etc., as well as AlCl ₃ , InCl ₃ , and FeCl. ₃ , _{Metal chlorides such as TiCl 2} , SnCl ₂ , SiCl ₂ and GeCl ₂ , metal oxides such as TiO and VO, and metal hydroxides such as _{Si (OH) 2 are also included.}
Among these, as the metal or the metal compound, Fe, Zn, Mg, Si, Pt, Pd, Mo, Mn, Cu, from the viewpoints of stability, spectral characteristics, heat resistance, light resistance, manufacturing suitability, etc. of the complex, Ni, Co, TiO, B, or VO is preferable, Fe, Zn, Mg, Si, Pt, Pd, Cu, Ni, Co, B, or VO is more preferable, and Fe, Zn, Cu, Co, B, or VO is most preferred.

Examples of such dipyrromethene dyes include Japanese Patent No. 5085256, Japanese Patent Application Laid-Open No. 2008-292970, Japanese Patent Application Laid-Open No. 2010-85758, Japanese Patent Application Laid-Open No. 2010-84009, Japanese Patent Application Laid-Open No. 2010-43530, and Japanese Patent Application Laid-Open No. 2013. The publicly known techniques described in Japanese Patent Application Laid-Open No. -08010, Japanese Patent Application Laid-Open No. 2013-210596, International Publication No. 2013/141156, and the like can be used.

Here, as the dipyrromethene dye in the colorant used in the present invention, a dipyrromethene dye having an absorption maximum in the vicinity of 500 to 600 nm is preferable from the viewpoint of improving the brightness and the contrast ratio of the color filter, and the dipyrromethene dye is absorbed in the vicinity of 525 to 575 nm. A dipyrromethene-based dye having a maximum is more preferable, and a dipyrromethene-based dye having an absorption maximum in the vicinity of 540 to 560 nm is particularly preferable.

Examples of such dipyrromethene dyes include Exemplified Compound I-1 (absorption maximum of 558.2 nm) and III-45 (absorption maximum of 546.7 nm) described in Japanese Patent No. 5085256.

[Triaryl methane dye]
Examples of the triarylmethane dye skeleton include a diaminotriphenylmethane dye skeleton, a triaminotriphenylmethane dye skeleton, and a rosolic acid dye skeleton having an OH group.
The triaminotriphenylmethane dye skeleton is preferable in that it has an excellent color tone and is superior in sunlight fastness to other dyes. Among them, the diphenylnaphthylmethane dye skeleton, which is a basic dye, is particularly preferable.

[Triarylmethane basic dye]
_{The triarylmethane-based basic dye develops a color when the NH 2} or OH group located at the para position with respect to the central carbon takes a quinone structure by oxidation.
It _{is classified into the following three types according to the number of NH 2} and OH groups, and among them, the form of a triaminoarylmethane-based basic dye is preferable in that it develops good blue, red, and green colors.
a) Diaminotriphenylmethane-based basic dyes b) Triaminotriphenylmethane-based basic dyes c) Rosolic acid-based basic dyes with OH groups Triaminotriphenylmethane-based basic dyes, diaminotriphenylmethane-based basic dyes Dyes have a clear color tone and are more preferable than other dyes because of their excellent sunlight-hardening and waxing properties.

Since blue-based triarylmethane-based basic dyes have spectral characteristics with high transmittance at 400 to 440 nm, they can be made to have high brightness, especially when used for forming blue filter segments. It is preferable because it can be done.

Specifically, as a triarylmethane-based basic dye, C.I. I. Basic Violet 1 (Methyl Violet), 3 (Crystal Violet), 14 (Magenta), C.I. I. Basic Blue 1 (Basic Cyanine 6G), 5 (Basic Cyanine EX), 7 (Victoria Pure Blue BO), 26 (Victoria Blue B conc.), C.I. I. Basic Green 1 (Brilliant Green GX), 4 (Malachite Green), etc.
Above all, from the point of view of brightness, C.I. I. It is preferable to use Basic Blue 7.

Further, in the case of a triarylmethane-based basic dye, it can be used by forming chloride using an organic acid, perchloric acid or a metal salt thereof. Among them, the salt-forming compound of the basic dye is preferable because it has excellent resistance and compatibility with the pigment. Further, the basic dye and the counter component that works as a counter ion, organic sulfonic acid, organic sulfuric acid, and fluorine group-containing phosphorus are preferable. It is possible to use a salt-forming compound obtained by salting an anionic compound, a fluorine group-containing boron anionic compound, a cyano group-containing nitrogen anion compound, an anion compound having a conjugated base of an organic acid having a halogenated hydrocarbon group, or an acidic dye. It is more preferable.

Specifically, heteropolyacids, organic sulfonic acids such as aliphatic sulfonic acids and aromatic sulfonic acids, organic sulfuric acids such as aliphatic sulfuric acid and aromatic sulfuric acid, organic carboxylic acids such as aromatic carboxylic acids and fatty acids, and organic acids such as fatty acids, Alternatively, it has the form of an acidic dye. Or they may be metal salts thereof. Further, a salt-forming compound with a resin having an acid group is also preferable.

[Salt formation]
Salt-forming compounds of these basic dyes and anionic counters can be synthesized by conventionally known methods. A specific method is disclosed in JP-A-2003-215850.
As an example, after dissolving a triary methane-based basic dye in water, an organic sulfonic acid or a (sodium organic sulfonic acid) solution may be added, and the chloride-forming treatment may be performed while stirring. Here, a salt-forming compound in which _{the amino group (-NHC 2} H ₅ ) portion in the triallyl methane-based basic dye and the sulfonic acid group (-SO _{3 H) portion of the organic sulfonic acid are bonded is obtained.}
Here, the organic sulfonic acid can also be dissolved in an alkaline solution such as sodium hydroxide and _{used in the form of sodium sulfonate (-SO 3 Na) before the salt-forming treatment.} Further, in the present invention, a sulfonic acid group (-SO ₃ H) and a functional group (-SO ₃ Na) which is sodium sulfonate are also synonymous.

Examples of such triarylmethane dyes include JP-A-2002-014222, JP-A-2003-246935, JP-A-2003-246935, JP-A-2008-304766, and JP-A-2010-256598. , Japanese Patent Application Laid-Open No. 2011-200560, Japanese Patent Application Laid-Open No. 2011-186043, Japanese Patent Application Laid-Open No. 2012-1733399, Japanese Patent Application Laid-Open No. 2012-23333, Japanese Patent Application Laid-Open No. 2012-098522, Japanese Patent Application Laid-Open No. 2012-288970, The publicly known techniques described in Japanese Patent Application Laid-Open No. 2012-200469, Japanese Patent Application Laid-Open No. 2014-196262, International Publication No. 2010/123071, International Publication No. 2011/162217, International Publication No. 2013/108591, etc. Can be used.

[Cyanine dye]
As the cyanine dye, any compound having a dye moiety containing a cyanine skeleton in the molecule can be used without limitation.
Examples of the cyanine dye include C.I. I. Basic Yellow 11, 12, 13, 14, 21, 22, 23, 24, 28, 29, 33, 35, 40, 43, 44, 45, 48, 49, 51, 52, 53, C.I. I. Basic Red 12, 13, 14, 15, 27, 35, 36, 37, 45, 48, 49, 52, 53, 66, 68, C.I. I. Basic Violet 7, 15, 16, 20, 21, 39, 40, C.I. I. Basic Orange 27, 42, 44, 46, C.I. I. Basic blue 62, 63 and the like can be mentioned.
In addition, cyanine dyes described in JP-A-2014-224970, JP-A-2013-261614 and the like can also be used.

[Anthraquinone dye]
Anthraquinone dyes are dyes that have an anthraquinone skeleton in the molecule.
Examples of the anthraquinone dye include C.I. I. Solvent Yellow 117, 163, 1
67, 189, C.I. I. Solvent Orange 77, 86, C.I. I. Solvent Red 111, 143, 145, 146, 150, 151, 155, 168, 169, 172, 175, 181, 207, 222, 227, 230, 245, 247, C.I. I. Solvent Violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60, C.I. I. Solvent Blue 14, 18, 35, 36, 45, 58, 59, 59: 1, 63, 68, 69, 78, 79, 83, 94, 97, 98, 100, 101, 102, 104, 105, 111, 112, 122, 128, 132, 136, 139, C.I. I. Solvent Green 3, 28, 29, 32, 33, C.I. I. Acid Red 80, C.I. I. Acid Green 25, 27, 28, 41, C.I. I. Acid Violet 34, C.I. I. Acid Blue 25, 27, 40, 45, 78, 80, 112, C.I. I. Disperse Yellow 51, C.I. I. Disperse Violet 26, 27, C.I. I. Disperse Blue 1, 14, 56, 60, C.I. I. Direct Blue 40, C.I. I. Modant Tread 3, 11, C.I. I. Modant Blue 8 and the like can be mentioned. In addition, the anthraquinone dyes described in JP-A-9-291237, International Publication No. 2003/08734, International Publication No. 2006/024617, JP-A-2011-174987, JP-A-2013-53273, etc. It can be used as a known technique. The anthraquinone dye is preferably one that dissolves in an organic solvent, and more preferably a blue, violet or red anthraquinone dye. Examples of the anthraquinone dye include C.I. I. Solvent Blue 35, C.I. I. Solvent Blue 45, C.I. I. Acid Blue 80, C.I. I. Solvent Blue 104, and C.I. I. Solvent blue 122 is preferable from the viewpoint of brightness and contrast ratio.

When used in combination with the above red pigment, yellow pigment, orange pigment, and dye, the content of the pigment containing the compound represented by the general formula (1) or (2) is 10 in 100% by mass of the total colorant. It is ~ 90% by mass, preferably 20-80% by mass. When the content of the pigment containing the compound represented by the general formula (1) or (2) is less than 10% by mass, the excellent effects of luminance and coloring power cannot be sufficiently 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 sample for measurement. Using a transmission electron microscope ("JEM-1200EX" manufactured by Nippon Denshi Co., Ltd.), this sample was photographed with 3 photographs (for 3 fields) in which the primary particles of 100 or more pigments could be confirmed, and 100 photographs were taken in order from the upper left. The size of the primary particles of was measured. Specifically, the minor axis diameter and major axis diameter of the primary particles of each pigment are measured in nm units, the average is taken as the primary particle diameter of the pigment, and a total of 300 distributions are created in 5 nm increments and 5 nm. The median value of the step (for example, 8 nm in the case of 6 nm or more and 10 nm or less) was approximated as the particle size of those particles, and the number average particle size was calculated by calculating based on each particle size and the number thereof.

<Pigment miniaturization>
The pigment used in the present invention can be miniaturized and used. It is also preferable to use the pigment containing the compound represented by the general formula (1) or (2) in a finely divided manner, but the finening method is not particularly limited, and for example, wet grinding or dry grinding is used. , Both the dissolution precipitation method can be used, and as illustrated in the present invention, the salt milling treatment by the kneader method, which is a kind of wet grinding, can be performed.

The primary particle size of the finely divided pigment is preferably 20 nm or more because the dispersion in the colorant carrier is good. Further, since it is possible to form a filter segment having a high contrast ratio, it is preferably 100 nm or less. A particularly preferable range is the range of 25 to 85 nm.

In the salt milling treatment, a mixture of a pigment, a water-soluble inorganic salt and a water-soluble organic solvent is heated using a kneader such as a kneader, a trimix, a 2-roll mill, a 3-roll mill, a ball mill, an attritor, or a sand mill. This is a treatment in which the water-soluble inorganic salt and the water-soluble organic solvent are removed by washing with water after mechanically kneading. The water-soluble inorganic salt acts as a crushing aid, and the pigment is crushed by utilizing the high hardness of the inorganic salt during salt milling. By optimizing the conditions for the salt milling treatment of the pigment, it is possible to obtain a pigment having a very fine primary particle size, a narrow distribution width, and a sharp particle size distribution.

As the water-soluble inorganic salt, sodium chloride, barium chloride, potassium chloride, sodium sulfate and the like can be used, but sodium chloride (salt) is preferably used from the viewpoint of price. From the viewpoint of both treatment efficiency and production efficiency, the water-soluble inorganic salt is preferably used in an amount of 50 to 2000 parts by mass, and most preferably 300 to 1000 parts by mass with respect to 100 parts by mass of the colorant.

The water-soluble organic solvent has a function of wetting the pigment and the water-soluble inorganic salt, and is not particularly limited as long as it dissolves (mixes) in water and does not substantially dissolve the inorganic salt used. However, since the temperature rises during salt milling and the solvent easily evaporates, a high boiling point solvent having a boiling point of 120 ° C. or higher is preferable from the viewpoint 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 and the like are used. The water-soluble organic solvent is preferably used in an amount of 5 to 1000 parts by mass, and most preferably 50 to 500 parts by mass with respect to 100 parts by mass of the colorant.

When the pigment is subjected to salt milling treatment, a resin may be added if necessary. The type of resin used is not particularly limited, and a natural resin, a modified natural resin, a synthetic resin, a synthetic resin modified with a natural resin, or the like can be used. The resin used is preferably solid at room temperature, water-insoluble, and more preferably partially soluble in the organic solvent. The amount of the resin used is preferably in the range of 5 to 200 parts by mass with respect to 100 parts by mass of the colorant.

Further, when the pigment is subjected to salt milling treatment, a dye derivative described later may be added if necessary. The structure of the dye derivative used is not particularly limited, and examples thereof include compounds in which an organic pigment, anthraquinone, acrydone, or triazine is introduced with a basic substituent, an acidic substituent, or a phthalimide methyl group which may have a substituent. Be done. These can be used alone or in combination of two or more.

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

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

<Binder resin>
The binder resin is for dispersing, dyeing, or permeating a colorant, and examples thereof include thermoplastic resins. When used in the form of an alkali-developable colored resist material, it is preferable to use an alkali-soluble vinyl-based resin obtained by copolymerizing an acidic group-containing ethylenically unsaturated monomer. Further, 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 as an alkali-development type colored resist material, the resin is three-dimensionally crosslinked when exposed to active energy rays to form a coating film. By doing so, the colorant is fixed, the heat resistance is improved, and fading (deterioration of spectral characteristics) due to the heat of the colorant can be suppressed. It also has the effect of suppressing aggregation and precipitation of colorant components in the developing process.

The binder resin is preferably a resin having a spectral transmittance of preferably 80% or more, more preferably 95% or more in the entire wavelength region 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, more preferably in the range of 10,000 to 80,000 in order to preferably disperse the colorant. 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 a color filter, a carboxyl group that acts as a colorant adsorbing group and an alkali-soluble group during development, an aliphatic group that acts as an affinity group for a colorant carrier and a solvent, and an aliphatic group. The balance of aromatic groups is important for the dispersibility, permeability, developability and durability of the colorant, and it is preferable to use a resin having an acid value of 20 to 300 mgKOH / g. If the acid value is less than 20 mgKOH / g, the solubility in a developing solution is poor and it is difficult to form a fine pattern. If it exceeds 300 mgKOH / g, no fine pattern remains.

Since the binder resin has good film forming properties and various resistances, it is preferable to use the binder resin in an amount of 20 parts by mass or more with respect to 100 parts by mass of the total mass of the colorant, and the colorant concentration is high and good color characteristics are obtained. Since it can be expressed, it is preferably used in an amount of 1000 parts by mass or less.

Examples of the thermoplastic resin used for the binder resin include acrylic resin, butyral resin, styrene-maleic acid copolymer, chlorinated polyethylene, chlorinated polypropylene, polyvinyl chloride, vinyl chloride-vinyl acetate copolymer, and polyvinyl acetate. , Polyurethane resin, polyester resin, vinyl resin, alkyd resin, polystyrene resin, polyamide resin, rubber resin, cyclized rubber resin, celluloses, polyethylene (HDPE, LDPE), polybutadiene, polyimide resin and the like. .. Above all, it is preferable to use an acrylic resin.

Examples of the vinyl-based alkali-soluble resin obtained by copolymerizing the acidic group-containing ethylenically unsaturated monomer include resins having an acidic group such as a carboxyl group and a sulfone group.
Specifically, the alkali-soluble resin includes an acrylic resin having an acidic group, an α-olefin / (anhydrous) maleic acid copolymer, a styrene / styrene sulfonic acid copolymer, an ethylene / (meth) acrylic acid copolymer, or Examples thereof include isobutylene / (anhydrous) maleic acid copolymer. Among them, an acrylic resin having an acidic group and at least one resin selected from a styrene / styrene sulfonic acid copolymer, 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 a resin in which an unsaturated ethylenically double bond is introduced by the methods (i) and (ii) shown below.

[Method (i)]
As the method (i), for example, the side chain epoxy group of the copolymer obtained by copolymerizing an unsaturated ethylenic monomer having an epoxy group with one or more other types of monomers can be used. , An unsaturated monobasic acid carboxyl group having an unsaturated ethylenic double bond is added and reacted, and a polybasic acid anhydride is reacted with the generated hydroxyl group to form an unsaturated ethylenic double bond and a carboxyl group. There is a way to introduce it.

Examples of the unsaturated ethylenic monomer having an epoxy group include glycidyl (meth) acrylate, methylglycidyl (meth) acrylate, 2-glycidoxyethyl (meth) acrylate, and 3,4 epoxybutyl (meth) acrylate. And 3,4 epoxycyclohexyl (meth) acrylates, which may be used alone or in combination of two or more. From the viewpoint of reactivity with unsaturated monobasic acid in the next step, glycidyl (meth) acrylate is preferable.

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

Examples of the polybasic acid anhydride include tetrahydrophthalic anhydride, phthalic anhydride, hexahydrophthalic anhydride, succinic anhydride, maleic anhydride and the like, and these may be used alone or in combination of two or more. It doesn't matter. If necessary, such as by increasing the number of carboxyl groups, a tricarboxylic acid anhydride such as trimellitic acid anhydride or a tetracarboxylic acid dianhydride such as pyromellitic acid dianhydride may be used to obtain the remaining anhydride. It is also possible to hydrolyze the group. Further, when etrahydrophthalic anhydride or maleic anhydride having an unsaturated ethylenically double bond is used as the polybasic acid anhydride, the unsaturated ethylenically double bond can be further increased.

As a method similar to the method (i), for example, a side chain of a copolymer obtained by copolymerizing an unsaturated ethylenic monomer having a carboxyl group with one or more other monomers. There is a method of adding an unsaturated ethylenic monomer having an epoxy group to a part of the carboxyl group to introduce an unsaturated ethylenic double bond and a carboxyl group.

[Method (ii)]
As the method (ii), an unsaturated ethylenic monomer having a hydroxyl group is used, and by copolymerizing with another unsaturated monobasic acid monomer having a carboxyl group or another monomer. There is a method of reacting the side chain hydroxyl group of the obtained copolymer with the isocyanate group of the unsaturated ethylenic monomer having an isocyanate group.

Examples of the unsaturated ethylenic monomer having a hydroxyl group include 2-hydroxyethyl (meth) acrylate, 2- or 3-hydroxypropyl (meth) acrylate, 2- or 3- or 4-hydroxybutyl (meth) acrylate, and glycerol. Examples thereof include hydroxyalkyl (meth) acrylates such as (meth) acrylate and cyclohexanedimethanol mono (meth) acrylate, and these may be used alone or in combination of two or more. Further, a polyether mono (meth) acrylate obtained by superpolymerizing the above hydroxyalkyl (meth) acrylate with ethylene oxide, propylene oxide, and / or butylene oxide, (poly) γ-valerolactone, and (poly) ε-caprolactone. , And / or (poly) ester mono (meth) acrylates to which (poly) 12-hydroxystearic acid and the like are added can also be used. 2-Hydroxyethyl (meth) acrylate or glycerol (meth) acrylate is preferable from the viewpoint of suppressing foreign matter in the coating film.

Examples of the unsaturated ethylenic monomer having an isocyanate group include 2- (meth) acryloyloxyethyl isocyanate and 1,1-bis [(meth) acryloyloxy] ethyl isocyanate, but the present invention is limited thereto. However, two or more types can be used together.

<Organic solvent>
In the coloring composition of the present invention, the coloring agent is sufficiently dispersed and permeated into the coloring agent carrier, and the filter segment is applied onto a substrate such as a glass substrate so that the dry film thickness is 0.2 to 5 μm. It contains an organic solvent to facilitate its formation. The organic solvent is selected in consideration of the solubility of each component of the coloring composition and the safety in addition to the good coatability of the coloring composition.

Examples of the organic solvent 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-cyclohexene-1-one, 3,3,5-trimethylcyclohexanone, 3-ethoxypropionic acid Ethylene, 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-butyl alcohol, 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 Monotershary Butyl Ether, Ethylene Glycol Monobutyl Ether, Ethylene Glycol Monobutyl Ether Acetate, Ethylene Glycol Monopropyl Ether, Ethylene Glycol Monohexyl Ethylene, 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, dipro Pylene Glycol Monoethyl Ether, Dipropylene Glycol Monobutyl Ether, Dipropylene Glycol Monopropyl Ether, Dipropylene 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 Examples thereof include isobutyl ketone, methylcyclohexanol, n-amyl acetate, n-butyl acetate, isoamyl acetate, isobutyl acetate, propyl acetate, dibasic acid ester and the like. These solvents can be used alone or in admixture of two or more at any ratio, if necessary.

The solvent can be used in an amount of 100 to 10000 parts by mass, preferably 500 to 5000 parts by mass with respect to 100 parts by mass of the colorant in the coloring composition.

<Photopolymerizable monomer>
The photopolymerizable monomer that may be added to the coloring composition of the present invention includes a monomer or an oligomer that is cured by ultraviolet rays, heat, or the like to produce a transparent resin.

Examples of the monomer and oligomer that cure with ultraviolet rays or heat to produce a transparent resin include methyl (meth) acrylate, ethyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, and 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 ( Meta) Acrylate, Trimethylol Propanetri (Meta) Acrylate, Pentaerythritol Tri (Meta) Acrylate, Pentaerythritol Tetra (Meta) Acrylate, 1,6-Hexanediol Diglycidyl Ether Di (Meta) Acrylate, Bisphenol A Diglycidyl Ether Di (Meta) acrylate, neopentyl glycol diglycidyl ether di (meth) acrylate, dipentaerythritol hexa (meth) acrylate, dipentaerythritol penta (meth) acrylate, tricyclodecanyl (meth) acrylate, ester acrylate, methylolated melamine (Meta) acrylic acid ester, epoxy (meth) acrylate, various acrylic acid esters such as urethane acrylate and methacrylic acid ester, (meth) acrylic acid, styrene, vinyl acetate, hydroxyethyl vinyl ether, ethylene glycol divinyl ether, pentaerythritol tri Examples thereof include, but are not limited to, vinyl ether, (meth) acrylamide, N-hydroxymethyl (meth) acrylamide, N-vinylformamide, and acrylonitrile. These photopolymerizable compounds may be used alone or in admixture of two or more at any ratio as required.

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

<Photopolymerization initiator>
A solvent-developed or alkali-developed photosensitive coloring composition is added to the coloring composition of the present invention by adding a photopolymerization initiator in order to cure the composition by irradiation with ultraviolet rays and form a filter segment by a photolithography method. Can be prepared in the form of.

Examples of the photopolymerization initiator include 4-phenoxydichloroacetophenone, 4-t-butyl-dichloroacetophenone, diethoxyacetophenone, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropane-1-one, 1-. Hydroxycyclohexylphenylketone, 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropane-1-one, 2- (dimethylamino) -2-[(4-methylphenyl) methyl] -1 -Acetophenone compounds such as [4- (4-morpholinyl) phenyl] -1-butanone or 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butane-1-one; benzoin, benzoin Benzoin compounds such as methyl ether, benzoin ethyl ether, benzoin isopropyl ether, or benzyl dimethyl ketal; benzophenone, benzoyl benzoic acid, methyl benzoyl benzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylicized benzophenone, 4-benzoyl-4' -Methyldiphenyl sulfide, or benzophenone compounds such as 3,3', 4,4'-tetra (t-butylperoxycarbonyl) benzophenone; thioxanthone, 2-chlorthioxanthone, 2-methylthioxanthone, isopropylthioxanthone, 2,4 -Thioxanthone compounds such as diisopropylthioxanthone or 2,4-diethylthioxanthone; 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-naphtho-1-yl) -4,6-bis (trichloromethyl) -s-triazine, 2,4-trichloromethyl- (piperonyl) -6-triazine, or 2,4- Triazine compounds such as trichloromethyl- (4'-methoxystyryl) -6-triazine; 1,2-octanedione, 1- [4- (phenylthio)-, 2- (O-benzoyloxime) )], Or an oxime ester compound such as O- (acetyl) -N- (1-phenyl-2-oxo-2- (4'-methoxy-naphthyl) ethylidene) hydroxylamine; bis (2,4,6- Trimethylbenzoyl) phenylphosphine oxide, or phosphine compounds such as 2,4,6-trimethylbenzoyldiphenylphosphine oxide; quinone compounds such as 9,10-phenanthrene quinone, camphorquinone, ethylanthraquinone; borate compounds; carbazole. A system compound; an imidazole system compound; or a titanosen system compound or the like is used. These photopolymerization initiators can be used alone or in admixture of two or more at any ratio as required.

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

<Sensitizer>
Further, the coloring composition for a color filter of the present invention may contain a sensitizer.
Examples of the sensitizer include unsaturated ketones represented by chalcone derivatives and dibenzalacetone, 1,2-diketone derivatives represented by benzyl and camphorquinone, benzoin derivatives, fluorene derivatives, naphthoquinone derivatives, and anthraquinone derivatives. , Xanthene derivatives, thioxanthene derivatives, xanthone derivatives, thioxanthone derivatives, coumarin derivatives, ketocoumarin derivatives, cyanine derivatives, merocyanine derivatives, oxonoal derivatives and other polymethine dyes, aclysine derivatives, azine derivatives, thiadine derivatives, oxadin derivatives, indolin derivatives, Azulene derivative, azurenium derivative, squarylium derivative, porphyrin derivative, tetraphenylporphyrin derivative, triarylmethane derivative, tetrabenzoporphyrin derivative, tetrapyrazinoporphyrazine derivative, phthalocyanine derivative, tetraazaporphyrazine derivative, tetraquinoxalyloporphyrazine derivative , Naphthalocyanine derivative, subphthalocyanine derivative, pyrylium derivative, thiopyrilium derivative, tetraphyllin derivative, anurene derivative, spiropyrane derivative, spiroxazine derivative, thiospiropyrane derivative, metal allene complex, organic ruthenium complex, Mihiler ketone derivative and the like. These sensitizers can be used alone or in admixture of two or more at any ratio as required.

More specific examples include Nobu Ogawara et al., "Dye Handbook" (1986, Kodansha), Nobu Ogawara et al., "Chemistry of Functional Dyes" (1981, CMC), Chuzaburo Ikemori et al., "Special". Examples include, but are not limited to, the sensitizers described in "Functional Materials" (1986, CMC). In addition, a sensitizer that absorbs light from the ultraviolet to the near infrared region can also be contained.
Among the above sensitizers, particularly suitable sensitizers include thioxanthone derivatives, Michler 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, 3,6-dibenzoyl- N-ethylcarbazole or the like is used.

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

<Multifunctional thiol>
The coloring composition for a color filter of the present invention can contain a polyfunctional thiol. A polyfunctional thiol is a compound having two or more thiol (SH) groups. When polyfunctional thiol is used together with the above-mentioned photopolymerization initiator, it acts as a chain transfer agent in the radical polymerization process after light irradiation, and generates chile radicals that are less susceptible to polymerization inhibition by oxygen. The composition becomes highly sensitive. In particular, polyfunctional aliphatic thiols in which the SH group is bonded to an aliphatic group such as methylene or ethylene group are preferable.

Examples of the polyfunctional thiol include hexanedithiol, decandithiol, 1,4-butanediol bisthiopropionate, 1,4-butanediol bisthioglycolate, ethylene glycol bisthioglycolate, and ethylene glycol bisthiopropio. Nate, trimethylolpropane tristhioglycolate, trimethylolpropane tristhiopropionate, trimethylolethanetris (3-mercaptobutyrate), trimethylolpropanetris (3-mercaptobutyrate), trimethylolpropanetris (3-mercaptobutyrate) Mercaptopropionate), Pentaerythritol Tetrakissthioglycolate, Pentaerythritol Tetrakissthiopropionate, Pentaerythritol Tetrakiss (3-Mercaptopropionate), Dipentaerythritol Hexakis (3-Mercaptopropionate), Trimercaptopropion Tris (2-hydroxyethyl) isocyanurate, 1,4-dimethylmercaptobenzene, 2,4,6-trimercapto-s-triazine, 2- (N, N-dibutylamino) -4,6-dimercapto-s -Triazine, etc. can be mentioned. These polyfunctional thiols can be used alone or in admixture of two or more at any ratio as required.

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

<Leveling agent>
It is preferable to add a leveling agent to the coloring composition of the present invention in order to improve the leveling property of the composition on the transparent substrate. As the leveling agent, dimethylsiloxane having a polyether structure or a polyester structure in the main chain is preferable. Specific examples of the dimethylsiloxane having a polyether structure in the main chain include FZ-2122 manufactured by Toray Dow Corning Co., Ltd., BYK-333 manufactured by Big Chemie Co., Ltd., and the like. Specific examples of dimethylsiloxane having a polyester structure in the main chain include BYK-310 and BYK-370 manufactured by Big Chemie. Didimethylsiloxane 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 with respect to 100 parts by mass of the total mass of the coloring composition.

A particularly preferable leveling agent is a kind of so-called surfactant having a hydrophobic group and a hydrophilic group in the molecule, which has a hydrophilic group but has low solubility in water, and when added to a coloring composition, the same. It is useful to have a feature of low surface tension lowering ability and good wettability to the glass plate despite low surface tension lowering ability, and the amount of addition does not cause defects in the coating film due to foaming. Those capable of sufficiently suppressing chargeability can be preferably used. As a leveling agent having such preferable properties, dimethylpolysiloxane having a polyalkylene oxide unit can be preferably used. The polyalkylene oxide unit includes a polyethylene oxide unit and a polypropylene oxide unit, and dimethylpolysiloxane may have both a polyethylene oxide unit and a polypropylene oxide unit.

The binding form of the polyalkylene oxide unit with dimethylpolysiloxane includes a pendant type in which the polyalkylene oxide unit is bonded in the repeating unit of dimethylpolysiloxane, a terminal-modified type in which the polyalkylene oxide unit is bonded to the terminal of dimethylpolysiloxane, and dimethylpolysiloxane. It may be any of the linear block copolymer types that are repeatedly bonded alternately. Didimethylpolysiloxane having a polyalkylene oxide unit is commercially available from Toray Dow Corning Co., Ltd., for example, FZ-2110, FZ-2122, FZ-2130, FZ-2166, FZ-2191, FZ-2203, FZ. 2207, but is not limited to these.

Anionic, cationic, nonionic, or amphoteric surfactants can be added as an adjunct to the leveling agent. Two or more kinds of surfactants may be mixed and used. Anionic surfactants to be added as an auxiliary to the leveling agent include polyoxyethylene alkyl ether sulfate, sodium dodecylbenzene sulfonate, alkali salt of styrene-acrylic acid copolymer, sodium alkylnaphthalline sulfonate, and alkyldiphenyl ether disulfonic acid. Sodium, monoethanolamine lauryl sulfate, triethanolamine lauryl sulfate, ammonium lauryl sulfate, monoethanolamine stearate, sodium stearate, sodium lauryl sulfate, monoethanolamine of styrene-acrylic acid copolymer, polyoxyethylene alkyl ether phosphate Examples include ester.

Examples of the chaotic surfactant added as an auxiliary to the leveling agent include alkyl quaternary ammonium salts and ethylene oxide adducts thereof. Nonionic surfactants to be added as an auxiliary to the leveling agent include polyoxyethylene oleyl ether, polyoxyethylene lauryl ether, polyoxyethylene nonylphenyl ether, polyoxyethylene alkyl ether phosphoric acid ester, and polyoxyethylene sorbitan monostearate. , Polyethylene glycol monolaurate. Examples thereof include alkyl betaines such as alkyl dimethylaminoacetic acid betaine, amphoteric surfactants such as alkyl imidazoline, and fluorine-based and silicone-based surfactants.

<Ultraviolet absorber, polymerization inhibitor>
The coloring composition for a color filter 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 the ultraviolet absorber include 2- [4-[(2-hydroxy-3- (dodecyl and tridecyl) oxypropyl) oxy] -2-hydroxyphenyl] -4,6-bis (2,4-dimethylphenyl). -1,3,5-triazine, 2- (2-hydroxy-4- [1-octyloxycarbonylethoxy] phenyl) -4,6-bis (4-phenylphenyl) -1,3,5-triazine, etc. Phenylphenyltriazine, 2- (5-methyl-2-hydroxyphenyl) benzotriazole, 2- (2H-benzotriazole-2-yl) -4,6-bis (1-methyl-1-phenylethyl) phenol, Bentriazoles such as 2- (3-t butyl-5-methyl-2-hydroxyphenyl) -5-chlorobenzotriazole, 2,4-dihydroxybenzophenone, 2-hydroxy-4-octoxybenzophenone, 2,2' , 4,4'-Benzophenone type such as tetrahydroxybenzophenone, phenylsalicylate, salicylate type such as p-tert-butylphenylsalicylate, cyanoacrylate such as ethyl-2-cyano-3,3'-diphenylacrylate. System, 2,2,6,6, -tetramethylpiperidin-1-oxyl (triacetone-amine-N-oxyl), bis (2,2,6,6-tetramethyl-4-piperidyl) -sevacate, poly [[6-[(1,1,3,3-tetrabutyl) amino] -1,3,5-triazine-2,4-diyl] [(2,2,6,6-tetramethyl-4-piperidinyl)] Imino] and other hindered amines are mentioned. These UV absorbers can be used alone or in admixture of two or more at any ratio as required.

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

The ultraviolet absorber and the polymerization inhibitor can be used in an amount of 0.01 to 20 parts by mass, preferably 0.05 to 10 parts by mass with respect to 100 parts by mass of the colorant in the coloring composition.
Better resolution can be obtained by using 0.01 part by mass or more of the ultraviolet absorber or the polymerization inhibitor.

<Antioxidant>
The coloring composition for a color filter of the present invention may contain an antioxidant in order to increase the transmittance of the coating film. The antioxidant may increase the transmittance of the coating film in order to prevent the photopolymerization initiator contained in the coloring composition for a color filter from oxidizing and yellowing due to the thermal process at the time of thermosetting or ITO annealing. can. Therefore, by containing an antioxidant, it is possible to prevent yellowing due to oxidation during the heating step and obtain a high transmittance of the coating film.

Preferred examples of the antioxidant include a hindered phenol-based antioxidant, a hindered amine-based antioxidant, a phosphorus-based antioxidant, a sulfide-based antioxidant, and the like. Further, more preferably, it is a hindered phenol-based antioxidant, a hindered amine-based antioxidant, or a phosphorus-based antioxidant. These antioxidants can be used alone or in admixture of two or more at any ratio as required.

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

For hindered amine antioxidants, 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- Piperidine) 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-) Tetramethyl-4-piperidyl) imino} Hexamethyl {(2,2,6,6-tetramethyl-4-piperidyl) imino}], poly [(6-morpholino-1,3,5-triazin-2,4-) Diyl) {(2,2,6,6-tetramethyl-4-piperidyl) imino} hexamethine {(2,2,6,6-tetramethyl-4-piperidyl) imino}]], dimethyl succinate and 1-( 2-Hydroxyethyl) -4-hydroxy-2,2,6,6-polycondensate with tetramethylpiperidine, 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-diazadecan-1,10-diamine and the like can be mentioned.

As a phosphorus-based antioxidant, tris [2-[[2,4,8,10-tetrakis (1,1-dimethylethyl) dibenzo [d, f] [1,3,2] dioxaphosphepine- 6-yl] oxy] ethyl] amine, tris [2-[(4,6,9,11-tetra-tert-butyldibenzo [d, f] [1,3,2] dioxaphosphepin-2-] Il) Oxy] ethyl] amine, ethylbis phosphite (2,4-di-tert-butyl-6-methylphenyl) can be mentioned.

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

The content of the antioxidant is preferably 0.1 to 5 parts by mass based on 100 parts by mass of the total solid content of the coloring composition for a color filter. When the amount of the antioxidant is less than 0.1 parts by mass, the effect of increasing the transmittance is small, and when the amount is more than 5 parts by mass, the hardness is greatly reduced and the sensitivity of the coloring composition for a color filter is greatly reduced.

<Other ingredients>
The coloring composition for a color filter of the present invention contains an adhesion improver such as a silane coupling agent in order to enhance the adhesion to a transparent substrate, or an amine compound having a function of reducing dissolved oxygen. Can be made to.

Examples of the silane coupling agent include vinylsilanes such as vinyltris (β-methoxyethoxy) silane, vinylethoxysilane and vinyltrimethoxysilane, (meth) acrylic silanes such as γ-methacryloxypropyltrimethoxysilane, and β- ( 3,4-Epoxycyclohexyl) ethyltrimethoxysilane, β- (3,4-epoxycyclohexyl) methyltrimethoxysilane, β- (3,4-epoxycyclohexyl) ethyltriethoxysilane, β- (3,4-epoxy) Epoxysilanes such as cyclohexyl) methyltriethoxysilane, γ-glycidoxypropyltrimethoxysilane, γ-glycidoxypropyltriethoxysilane, N-β (aminoethyl) γ-aminopropyltrimethoxysilane, N-β (Aminoethyl) γ-aminopropyltriethoxysilane, N-β (aminoethyl) γ-aminopropylmethyldiethoxysisilane, γ-aminopropyltriethoxysilane, γ-aminopropyltrimethoxysilane, N-phenyl-γ Examples thereof include aminosilanes such as −aminopropyltrimethoxysilane 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 with respect to 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, 4 -Examples include 2-ethylhexyl dimethylaminobenzoate, N, N-dimethylparatoluidine and the like.

<Manufacturing method of coloring composition for color filter>
The coloring composition for a color filter of the present invention comprises a kneader, a 2-roll mill, or a 3-roll mill in which the azo pigment of the present invention is placed in a colorant carrier such as a resin and / or a solvent, if necessary, together with a dispersion aid. , A ball mill, a horizontal sand mill, a vertical sand mill, an annular bead mill, or an attritor, and the like can be finely dispersed and produced (pigment dispersion). At this time, two or more kinds of colorants and the like may be dispersed in the colorant carrier at the same time, or those dispersed separately in the colorant carrier may be mixed. The epoxy compound may be added at the stage of preparing the pigment dispersion, or the same effect can be obtained by adding the epoxy compound to the prepared pigment dispersion later.

The dye contained in the colorant of the present invention is preferably mixed after the pigment dispersion is prepared, but the pigment is dispersed in consideration of the solubility of the dye and the possibility of deterioration due to local heating in the disperser. There is also a method of adding it when adjusting the body.

When used as a photosensitive coloring composition (resist material) for a color filter, it can be prepared as a solvent-developing type or alkali-developing type coloring composition. The solvent-developed or alkaline-developed coloring composition includes the pigment dispersion, a dye, a photopolymerizable monomer and / or a photopolymerization initiator, and if necessary, a solvent, other pigment dispersants, and addition. It can be prepared by mixing agents and the like. The photopolymerization initiator may be added at the stage of preparing the pigment dispersion, or may be added later to the prepared pigment dispersion.

<Dispersion aid>
When the colorant is dispersed in the colorant carrier, it is preferable to contain not only the resin type dispersant but also a dispersion aid such as a dye derivative and a surfactant as appropriate. Since the dispersion aid has a great effect of preventing the reaggregation of the colorant after dispersion, the coloring composition obtained by dispersing the colorant in the colorant carrier using the dispersion aid has high luminance and storage stability. Become good.

<Resin type dispersant>
The coloring composition for a color filter of the present invention preferably further contains a resin-type dispersant having an acidic substituent.
The resin-type dispersant has a colorant-affinitive moiety having a property of adsorbing to the colorant and a moiety compatible with the colorant carrier, and is adsorbed on the colorant to disperse the colorant on the colorant carrier. It works to stabilize. Specific examples of the resin-type dispersant include polycarboxylic acid esters such as polyurethane and polyacrylate, unsaturated polyamides, polycarboxylic acids, polycarboxylic acid (partial) amine salts, polycarboxylic acid ammonium salts, and polycarboxylic acid alkylamine salts. , Polysiloxane, long-chain polyaminoamidophosphate, hydroxyl group-containing polycarboxylic acid esters, modified products thereof, amides and salts thereof formed by the reaction of poly (lower alkyleneimine) with polyester having a free carboxyl group. Oil-based dispersants such as, (meth) acrylic acid-styrene copolymer, (meth) acrylic acid- (meth) acrylic acid ester copolymer, styrene-maleic acid copolymer, polyvinyl alcohol, polyvinylpyrrolidone and the like. Resins, water-soluble polymer compounds, polyesters, modified polyacrylates, ethylene oxide / propylene oxide addition compounds, phosphate esters, etc. are used, and these can be used alone or in admixture of two or more. , 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 manufactured by Big Chemie Japan. , 171, 174, 180, 181, 182, 183, 184, 185, 190, 2000, 2001, 2020, 2025, 2050, 2070, 2095, 2150, 2155, or Anti-Terra-U, 203, 204, or BYK. -P104, P104S, 220S, 6919, or Lactimon, Lactimon-WS or Bykuman, etc., SOLSPERSE-3000, 9000, 13000, 13240, 13650, 13940, 16000, 17000, 18000, 20000, 21000, 24000, manufactured by Japan Lubrizol. , 26000, 27000, 28000, 31845, 32000, 32500, 32550, 33500, 32600, 34750, 35100, 36600, 38500, 41000, 41090, 53095, 55000, 76500, etc., EFKA-46, 47, 48, manufactured by BASF. 452, 4008, 4009, 4010, 4015, 4020, 4047, 4050, 4055, 4060, 4080, 4400, 4401, 4402, 4403, 4406, 4408, 4300, 4310, 4320, 4330, 4340, 450, 451 and 453, 4540, 4550, 4560, 4800, 5010, 5065, 5066, 5070, 7500, 7554, 1101, 120, 150, 1501, 1502, 1503, etc. And so on.

Further, as the resin type dispersant used in the present invention, those having an acidic substituent are preferable, and those having an aromatic carboxyl group are particularly preferable because they have a particularly large effect of preventing reaggregation of the colorant after dispersion. .. As the resin type dispersant having an aromatic carboxyl group, those containing the following (S1) or (S2) are preferable.
(S1) A resin-type dispersant which is a reaction product of a hydroxyl group of a polymer having a hydroxyl group and an acid anhydride group of a tricarboxylic acid anhydride and / or a tetracarboxylic acid dianhydride.
(S2) A weight obtained by polymerizing an ethylenically unsaturated monomer in the presence of a reaction product of 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. A resin-type dispersant that is a coalescence.

[Resin type dispersant (S1)]
The resin-type dispersant (S1) can be produced by a known method such as WO2008 / 007776, JP-A-2008-029901, and JP-A-2009-155406. The polymer (p) having a hydroxyl group is preferably a polymer having a hydroxyl group at the terminal. For example, the ethylenically unsaturated monomer (r) is polymerized in the presence of the compound (q) having a hydroxyl group. It can be obtained as a polymer. 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 number of hydroxyl groups at the terminal is plural, the compound (q1) having two hydroxyl groups and one thiol group in the molecule is preferably used.

That is, a more preferable example, a polymer having two hydroxyl groups at one end contains a monomer (r1) in the presence of a compound (q1) having two hydroxyl groups and one thiol group in the molecule. It can be obtained as a polymer (p1) obtained by polymerizing the ethylenically unsaturated monomer (r) contained therein. The hydroxyl group of the polymer (p) having a hydroxyl group reacts with the acid anhydride group of tricarboxylic acid anhydride and / or tetracarboxylic acid dianhydride to form an ester bond, while the anhydrous ring is opened and the carboxylic acid. Produces.

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

The difference between (S1) and (S2) is whether the introduction of the polymer moiety obtained by polymerizing the ethylenically unsaturated monomer (r) is performed first or later. The molecular weight and the like may differ slightly depending on various conditions, but if the reaction conditions are the same as those of the raw material, the same can be theoretically obtained.

The resin type dispersant is preferably used in an amount of about 5 to 200 parts by mass with respect to the total amount of the colorant, and more preferably about 5 to 100 parts by mass from the viewpoint of film forming property.

<Dye derivative>
The coloring composition for a color filter of the present invention preferably further contains a dye derivative. The dye derivative may be contained in the azo pigment.
As the dye derivative used in the present invention, a known dye derivative having an acidic group, a basic group, a neutral group or the like in the organic dye residue can be used. For example, compounds having an acidic functional group such as a sulfo group, a carboxy group and a phosphoric acid group, amine salts thereof, compounds having a basic functional group such as a sulfonamide group or a tertiary amino group at the terminal, a phenyl group and a phthalimide. Examples thereof include compounds having a neutral functional group such as an alkyl group. Examples of the organic pigment include phthalocyanine pigments such as diketopyrrolopyrrole pigments, copper phthalocyanines, zinc phthalocyanines, aluminum phthalocyanines, halogenated copper phthalocyanines, halogenated zinc phthalocyanines, halogenated aluminum phthalocyanines, and metal-free phthalocyanines, aminoanthralocyanines, and diaminos. Anthraquinone pigments such as dianthraquinone, anthrapyrimidine, flavantron, antoanthron, indantron, pyrantron, biolantron, quinacridone pigments, dioxazine pigments, perinone pigments, perylene pigments, thiazineindigo pigments, triazine pigments, Benzimidazolone-based pigments, indole-based pigments such as benzoisoindole, isoindolin-based pigments, isoindolinone-based pigments, quinophthalocyan-based pigments, naphthol-based pigments, slene-based pigments, metal complex-based pigments, azo, disazo, polyazo, etc. Examples include azo pigments.
More specifically, Japanese Patent Application Laid-Open No. 61-246261, Japanese Patent Application Laid-Open No. 63-246674, Japanese Patent Application Laid-Open No. 09-272812, Japanese Patent Application Laid-Open No. 10-245501, Japanese Patent Application Laid-Open No. 10-265697, Japanese Patent Application Laid-Open No. 11-19976, 2001-172520, 2001-22520, 2002-201377, 2003-165922, 2003-168208, 2003- 171594, 2004-217842, 2005-213404, 2006-291194, 2007-079094, 2007-226161, 2007-314681. JP-A-2007-314785, JP-A-2008-31281, JP-A-2009-57478, WO2009 / 025325 pamphlet, WO2009 / 081930 pamphlet, JP-A-2011-162662, WO2011 / 052617. Pamphlet, JP2012-1722092, JP2012-208329, JP2012-226110, WO2012 / 102399, WO2012 / 102399, JP2014-5439, WO2016 / 163351, JP2017- Known dye derivatives described in Japanese Patent No. 156397, Japanese Patent No. 5753266, etc. can be mentioned, 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, a pigment derivative, a pigment dispersant, or simply a compound, but the above-mentioned organic dye residue includes an acidic group, a basic group, a neutral group, and the like. A compound having a functional group of is synonymous with a dye derivative.

Among the dye derivatives used in the present invention, a dye derivative having a basic substituent is preferable because the effect of suppressing the aggregation of the pigments is remarkable. Further, as the organic dye residue, those derived from diketopyrrolopyrrole pigments, anthraquinone pigments, quinophthalone pigments and azo pigments are preferable from the viewpoint of hue and contrast ratio.

<Surfactant>
Surfactants include sodium lauryl sulfate, polyoxyethylene alkyl ether sulfate, sodium dodecylbenzene sulfonate, alkali salt of styrene-acrylic acid copolymer, sodium stearate, sodium alkylnaphthalline sulfonate, sodium alkyldiphenyl ether disulfonate. , Monoethanolamine lauryl sulfate, Triethanolamine lauryl sulfate, Ammonium lauryl sulfate, Monoethanolamine stearate, Monoethanolamine styrene-acrylic acid copolymer, Polyoxyethylene alkyl ether phosphate and other anionic surfactants; Nonionic surfactants such as polyoxyethylene oleyl ether, polyoxyethylene lauryl ether, polyoxyethylene nonylphenyl ether, polyoxyethylene alkyl ether phosphate, polyoxyethylene sorbitan monostearate, polyethylene glycol monolaurate; alkyl Chaotic surfactants such as quaternary ammonium salts and their ethylene oxide adducts; alkyl betaines such as alkyldimethylaminoacetic acid betaine and amphoteric surfactants such as alkylimidazolin, which may be used alone or in combination of two or more. They can be mixed and used, but are not necessarily limited to these.

When the surfactant is added, it is preferably 0.1 to 55 parts by mass, more preferably 0.1 to 45 parts by mass with respect to 100 parts by mass of the colorant. If the content of the surfactant is less than 0.1 parts by mass, it is difficult to obtain the effect of addition, and if the content is more than 55 parts by mass, the dispersion may be affected by the excess dispersant. ..

<Removal of coarse particles>
The colored composition of the present invention comprises coarse particles of 5 μm or more, preferably coarse particles of 1 μm or more, more preferably 0.5 μm or more, and coarse particles of 5 μm or more, preferably coarse particles of 0.5 μm or more, by means such as centrifugation, filtration with a sintering filter or a membrane filter. It is preferable to remove the mixed dust. As described above, it is preferable that the coloring composition does not contain particles having a size of 0.5 μm or more. It is more preferably 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 includes a red filter segment, a green filter segment, and a blue filter segment on a substrate, and further includes a magenta color filter segment, a cyan color filter segment, or a yellow filter segment. The at least one filter segment may be formed from the coloring composition of the present invention.

<Manufacturing method of color filter>
The color filter of the present invention can be manufactured by a printing method or a photolithography method. Since the formation of the filter segment by the printing method can be patterned only by repeating printing and drying of the coloring composition prepared as the printing ink, it is low cost and excellent in mass productivity as a manufacturing method of the color filter. Furthermore, with the development of printing technology, it is possible to print fine patterns having high dimensional accuracy and smoothness. In order to perform printing, it is preferable that the composition is such that the ink does not dry or solidify on the printing plate or on the blanket. It is also important to control the fluidity of the ink on the printing machine, and it is possible to adjust the ink viscosity with a dispersant or an extender pigment.

When the filter segment is formed by the photolithography method, the coloring composition prepared as the solvent-developable or alkali-developable colored resist material is applied onto a transparent substrate by spray coating, spin coating, slit coating, roll coating or the like. By the method, the coating is applied so that the dry film thickness is 0.2 to 5 μm. If necessary, the dried film is exposed to ultraviolet rays through a mask having a predetermined pattern provided in contact with or without contact with the film. Then, after immersing in a solvent or an alkaline developer or spraying the developer with a spray or the like to remove the uncured portion to form a desired pattern, the same operation is repeated for other colors to manufacture a color filter. be able to. Further, in order to promote the polymerization of the colored resist material, heating can be applied as needed. According to the photolithography method, a color filter having higher accuracy than the above printing method can be manufactured.

At the time of development, an aqueous solution of sodium carbonate, sodium hydroxide or the like is used as the alkaline developer, and an organic alkali such as dimethylbenzylamine or triethanolamine can also be used. Further, an antifoaming agent or a surfactant can be added to the developing solution.
In order to increase the UV exposure sensitivity, the colored resist material is applied and dried, and then a water-soluble or alkaline water-soluble resin such as polyvinyl alcohol or a water-soluble acrylic resin is applied and dried to form a film that prevents polymerization inhibition by oxygen. After that, ultraviolet exposure can also be performed.

The color filter of the present invention can be produced by an electrodeposition method, a transfer method, an inkjet method or the like in addition to the above method, and the coloring composition of the present invention can be used in any method. The electrodeposition method is a method of manufacturing a color filter by electrodepositing each color filter segment on the transparent conductive film by electrophoresis of colloidal particles using the transparent conductive film formed on the substrate. .. Further, the transfer method is a method in which a filter segment is formed in advance on the surface of a peelable transfer base sheet, and the filter segment is transferred to a desired substrate.

A black matrix can be formed in advance before each color filter segment is formed on a substrate such as a transparent substrate or a reflective substrate. As the black matrix, a multilayer film of chromium or chromium / chromium oxide, an inorganic film such as titanium nitride, or a resin film in which a light-shielding agent is dispersed is used, but the black matrix is not limited thereto. Further, it is also possible to form a thin film transistor (TFT) in advance on the transparent substrate or the reflective substrate, and then form each color filter segment. Further, an overcoat film, a transparent conductive film, or the like is formed on the color filter of the present invention, if necessary.

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

The color filter is bonded to the facing substrate using a sealing agent, the liquid crystal is injected from the injection port provided in the sealing portion, the injection port is sealed, and a polarizing film or a retardation film is placed on the outside of the substrate as necessary. By laminating, a liquid crystal display panel is manufactured.

Such liquid crystal display panels include twisted nematic (TN), super twisted nematic (STN), in-plane switching (IPS), vertical alignment (VA), and optical convensend bend (OCB). It can be used in a liquid crystal display mode in which colorization is performed using a color filter such as.

As the transparent substrate, a glass plate such as soda-lime glass, low-alkali borosilicate glass, or non-alkali aluminoborosilicate glass, or a resin plate such as polycarbonate, polymethyl methacrylate, or polyethylene terephthalate is used. Further, a transparent electrode made of indium oxide, tin oxide or the like may be formed on the surface of the glass plate or the resin plate for driving the liquid crystal display after the panelization.

Hereinafter, the present invention will be described based on examples, but the present invention is not limited thereto. In the examples, "parts" and "%" represent "parts by mass" and "% by mass", respectively. Further, "PGMAc" means propylene glycol monomethyl ether acetate.

<Weight average molecular weight (Mw) of resin>
The weight average molecular weight (Mw) of the resin is converted to polystyrene measured by using a TSKgel column (manufactured by Tosoh Corporation) and a GPC (manufactured by Tosoh Corporation, HLC-8120GPC) equipped with an RI detector and using THF as a developing solvent. Weight average molecular weight (Mw).
<Number average molecular weight of resin>
The number average molecular weight of the resin of the present invention is measured by using HLC-8220GPC (manufactured by Tosoh Corporation) as an apparatus, TSK-GEL SUPER HZM-N as a column connected in two series, and THF as a solvent. It is the number average molecular weight in terms of polystyrene.
<Ammonium salt value of resin having a cationic group in the side chain>
The ammonium salt value of the resin having a cationic group in the side chain is a value obtained by titrating with a 0.1 N silver nitrate aqueous solution using a 5% potassium chromate aqueous solution as an indicator, and then converting it into an equivalent amount of potassium hydroxide. , Indicates the ammonium salt value of the solid content.
<Method of identifying azo pigments>
In identifying the azo pigment of the present invention, a MALDI mass spectrometer autoflex III (hereinafter referred to as TOF-MS) manufactured by Bruker Daltonics Co., Ltd. was used to obtain the molecular ion peak of the mass spectrum obtained and the mass number obtained by calculation. Further, using 2400 CHN Element Analyzer manufactured by Perkin-Elmer Co., Ltd., the identification was made based on the agreement between the ratio of each element obtained and the theoretical value.

<Contrast ratio of coating film>
The light emitted from the backlight unit for a liquid crystal display passes through a polarizing plate, is polarized, passes through a dry coating film of a colored composition coated on a glass substrate, and reaches the polarizing plate. If the polarizing plate and the polarizing planes of the polarizing plate are parallel, light passes through the polarizing plate, but if the polarizing planes are orthogonal to each other, the light is blocked by the polarizing plate. However, when the light polarized by the polarizing plate passes through the dry coating film of the coloring composition, scattering by pigment particles or the like occurs and a part of the polarizing surface is displaced. When the polarizing plates are parallel, the polarized light is polarized. The amount of light transmitted through the plate is reduced, and when the polarizing plates are orthogonal, part of the light is transmitted through the polarizing plate. This transmitted light was measured as the brightness on the polarizing plate, and the ratio (contrast ratio) between the brightness when the polarizing plates were parallel and the brightness when the polarizing plates were orthogonal was calculated.
(Contrast ratio) = (Brightness when parallel) / (Brightness when orthogonal)
A color luminance meter (“BM-5A” manufactured by Topcon Corporation) was used as the luminance meter, and a polarizing plate (“NPF-G1220DUN” manufactured by Nitto Denko Corporation) was used as the polarizing plate. At the time of measurement, a black mask having a 1 cm square hole was applied to the measurement portion in order to block unnecessary light.

First, acrylic resin solutions, resin-type dispersant solutions, dye derivatives, colorants (azo pigments / other pigments), pigment dispersions, dyes / dye solutions, and photosensitive coloring compositions used in Examples, Production Examples, and Comparative Examples. The manufacturing method of the thing will be described.
<Manufacturing method of acrylic resin solution>
(Preparation of acrylic resin solution 1)
196 parts of cyclohexanone was charged in a reaction vessel equipped with a thermometer, a cooling tube, a nitrogen gas introduction tube, a dropping tube and a stirrer in a separable 4-neck flask, the temperature was raised to 80 ° C., the inside of the reaction vessel was replaced with nitrogen, and then dropped. From the tube, 37.2 parts of n-butyl methacrylate, 12.9 parts of 2-hydroxyethyl methacrylate, 12.0 parts of methacrylic acid, paracumylphenol ethylene oxide-modified acrylate (“Aronix M110” manufactured by Toa Synthetic Co., Ltd.) 20.7 A mixture of parts 2,2'-azobisisobutyronitrile and 1.1 parts was added dropwise over 2 hours. After completion of the dropping, the reaction was continued for another 3 hours to obtain a solution of acrylic resin. After cooling to room temperature, about 2 parts of the resin solution is sampled, heated and dried at 180 ° C. for 20 minutes to measure the non-volatile content, and methoxypropyl acetate is added to the previously synthesized resin solution so that the non-volatile content is 20%. Addition was made to prepare an acrylic resin solution 1. The weight average molecular weight (Mw) was 26000.

(Preparation of acrylic resin solution 2)
207 parts of cyclohexanone was charged in a reaction vessel equipped with a thermometer, a cooling tube, a nitrogen gas introduction tube, a dropping tube and a stirrer in a separable 4-neck flask, the temperature was raised to 80 ° C., the inside of the reaction vessel was replaced with nitrogen, and then dropped. From the tube, 20 parts of methacrylic acid, 20 parts of paracumylphenol ethylene oxide modified acrylate (Aronix M110 manufactured by Toa Synthetic Co., Ltd.), 45 parts of methyl methacrylate, 8.5 parts of 2-hydroxyethyl methacrylate, and 2,2'-azobis. A mixture of 1.33 parts of isobutyronitrile 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, for the entire amount of the obtained copolymer solution, nitrogen gas was stopped, dry air was injected for 1 hour, and the mixture was stirred, cooled to room temperature, and then 2-methacryloyloxyethyl isocyanate (Showa Denko's Karenz). A mixture of 6.5 parts of MOI), 0.08 part of dibutyltin laurate and 26 parts of cyclohexanone was added dropwise at 70 ° C. over 3 hours. After completion of the dropping, the reaction was continued for another 1 hour to obtain a solution of acrylic resin. After cooling to room temperature, about 2 parts of the resin solution is sampled, heated and dried at 180 ° C. for 20 minutes to measure the non-volatile content, and cyclohexanone is added to the previously synthesized resin solution so that the non-volatile content becomes 20%. Acrylic resin solution 2 was prepared. The weight average molecular weight (Mw) was 18,000.

<Manufacturing method of resin type dispersant solution>
(Preparation of resin type dispersant solution 1)
A reaction vessel equipped with a gas introduction 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 replaced with nitrogen gas. The inside of the reaction vessel is heated to 80 ° C., and a solution prepared by dissolving 0.1 part of 2,2'-azobisisobutyronitrile in 10 parts of 3-mercapto-1,2-propanediol is added to 10 parts. Time reacted. It was confirmed by solid content measurement that 95% had reacted. Add 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, and react at 120 ° C. for 7 hours. rice field. By measuring the acid value, it was confirmed that 98% or more of the acid anhydride was half-esterified, and the reaction was terminated to obtain a polyester dispersant having an acid value of 77 mgKOH / g and a number average molecular weight of 8500. Methoxypropyl acetate was added thereto so that the solid content was 40% by solid content measurement to obtain 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 introduction 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 replaced with nitrogen gas. The inside of the reaction vessel is heated to 80 ° C., and a solution prepared by dissolving 0.1 part of 2,2'-azobisisobutyronitrile in 10 parts of 3-mercapto-1,2-propanediol is added to 10 parts. Time reacted. It was confirmed by solid content measurement that 95% had reacted. Add 36 parts of trimellitic acid anhydride, 200.0 parts of methoxypropyl acetate, and 0.40 part of 1,8-diazabicyclo- [5.4.0] -7-undecene as a catalyst, and react at 120 ° C. for 7 hours. rice field. By measuring the acid value, it was confirmed that 98% or more of the acid anhydride was half-esterified, and the reaction was terminated to obtain a polyester dispersant having an acid value of 109 mgKOH / g and a number average molecular weight of 8500. Methoxypropyl acetate was added thereto so that the solid content was 40% by solid content measurement to obtain a resin-type dispersant solution 2 having an aromatic carboxyl group.

(Preparation of resin type dispersant solution 3)
In a reaction vessel equipped with a gas introduction tube, a thermometer, a condenser, and a stirrer, 6.5 parts of 3-mercapto-1,2-propanediol, 4.0 parts of pyromellitic anhydride, 0.01 part of dimethylbenzylamine, 41.8 parts of methoxypropyl acetate was charged and replaced with nitrogen gas. The inside of 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, and t-butyl were cooled. 16.0 parts of acrylate, 10.0 parts of hydroxymethyl methacrylate and 2.0 parts of ethyl acrylate were charged, and 0.10 part of 2,2'-azobisisobutyronitrile and 60.0 parts of methoxypropyl acetate were added. It reacted for 10 hours. It was confirmed by solid content measurement that the polymerization proceeded by 95%, and the reaction was terminated to obtain a polyester dispersant having an acid value of 43 mgKOH / g and a number average molecular weight of 15,000. Methoxypropyl acetate was added thereto so that the solid content was 40% by solid content measurement to obtain a resin-type dispersant solution 3 having an aromatic carboxyl group.

(Preparation of resin type dispersant solution 4)
In a reaction vessel equipped with a gas introduction tube, a thermometer, a condenser, and a stirrer, 6.5 parts of 3-mercapto-1,2-propanediol, 4.0 parts of pyromellitic anhydride, 0.01 part of dimethylbenzylamine, 41.8 parts of methoxypropyl acetate was charged and replaced with nitrogen gas. The inside of 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, and t-butyl were cooled. 16.0 parts of acrylate, 10.0 parts of (3-ethyloxetane-3-yl) methyl methacrylate, 2.0 parts of ethyl acrylate were charged, and 2,2'-azobisisobutyronitrile 0.10 part and methoxypropyl. 60.0 parts of acetate was added and reacted for 10 hours. It was confirmed by solid content measurement that the polymerization proceeded by 95%, and the reaction was terminated to obtain a polyester dispersant having an acid value of 47 mgKOH / g and a number average molecular weight of 15,000. Methoxypropyl acetate was added thereto so that the solid content was 40% by solid content measurement to obtain a resin-type dispersant solution 4 having an aromatic carboxyl group.

<Manufacturing method of dye derivative>
The manufacturing method and structure of the dye derivative used in this invention are shown. The present invention is not limited to this.

(Manufacturing of dye derivative 1)
The dye derivative 1 represented by the formula (6) was produced with reference to Synthesis Example 3 of Japanese Patent No. 5748665.
Equation (6)

(Manufacturing of dye derivative 2)
The dye derivative 2 represented by the formula (7) was produced with reference to Production Example 21 of Japanese Patent No. 4396778.
Equation (7)

(Manufacturing of dye derivative 3)
The dye derivative 3 represented by the formula (8) was produced with reference to Production Example 6 of Japanese Patent No. 4983061.
Equation (8)

(Manufacturing of dye derivative 4)
The dye derivative 4 represented by the formula (9) was produced with reference to Example 1 of Japanese Patent No. 5316690.
Equation (9)

(Manufacturing of dye derivative 5)
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 was 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 was dispersed in 90 parts of toluene, and the above-mentioned 5-nitroisophthalic acid dichloride was added dropwise to this over 1 hour at room temperature, and then refluxed for 4 hours. And completed the reaction. Toluene was distilled off while neutralizing with a 10% aqueous sodium carbonate solution, and then resurrection, filtration and drying with a 3% aqueous NaOH solution were carried out to obtain 28.0 parts of the compound represented by the following formula (10).
Equation (10)

Next, 25.0 parts of the compound represented by the above formula (10) was dissolved in 100 parts of N-methylpyrrolidone, and 32 parts of sodium hydrosulfide hydrate (containing 65% of sodium hydrosulfide) was added to 55 parts. After adding the aqueous solution dissolved in water, the mixture was refluxed for 6 hours to obtain 20.0 parts of the base compound represented by the following formula (11).
Equation (11)

Disperse 20.0 parts of the base compound represented by the above formula (11) in 200 parts of water, add ice to adjust the temperature to 5 ° C., add 20.0 parts of a 35% aqueous hydrochloric acid solution, stir for 1 hour, and then submerge. An aqueous solution prepared by adding 3.60 parts of sodium nitrate to 11.0 parts of water was added, and the mixture was stirred for 2 hours. Subsequently, an aqueous solution consisting of 59.0 parts of an 80% acetic acid aqueous solution, 65.0 parts of a 25% sodium hydroxide aqueous solution, and 64.0 parts of water was added to prepare a diazonium salt aqueous solution. On the other hand, 18.7 parts of N- [2-methoxy-5-chlorophenyl] -3-hydroxy-2-naphthalenecarbamide and 53.5 parts of a 25% sodium hydroxide aqueous 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. for 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 the dye derivative 5 represented by the formula (12). ..

Equation (12)

(Manufacturing of dye derivative 6)
The dye derivative 6 represented by the formula (13) was produced with reference to Production Example 3 of Japanese Patent No. 1863188.
Equation (13)

<Manufacturing method of colorant (azo pigment)>
(Base compound)
The base compounds ([B-1] to [B-18]) used this time are shown in Table 1. Ph in the table represents a phenyl group.

(Manufacturing of coupler compound [C-1])

After mixing 167 parts of 3-hydroxy-2-naphthoic acid, 1500 parts of tetrahydrofuran, and 1 part of N, N-dimethylformamide, 221 parts of thionyl chloride was added, and the mixture was stirred at room temperature for 1 hour to prepare a carboxylic acid chloride solution. Obtained. Separately, a solution in which 1000 parts of N-methylpyrrolidone and 48 parts of 1,3-phenylenediamine were mixed was prepared, and a carboxylic acid chloride solution was added dropwise to this solution over 30 minutes. At this time, the dropping was performed while keeping the temperature of the reaction solution at 10 ° C. or lower. After completion of the dropping, the mixture was stirred at room temperature for 2 hours, and then the precipitated reaction product was collected by filtration to obtain the desired product. Further, the mixture was washed with 1000 parts of methanol and dried under reduced pressure to obtain 196 parts (yield 98.5%) of the coupler compound [C-1].

(Manufacturing of Coupler Compounds [C-2] to [C-70])
Instead of 48 parts of 1,3-phenylenediamine used in the production of the coupler compound [C-1], the diamines and parts by mass shown in Table 2 were changed, but the production of the coupler compound [C-1] was carried out. The same operation was carried out to produce the coupler compounds [C-2] to [C-70].

<Manufacturing of azo pigments>
[Manufacturing Example 1]
(Manufacturing of azo pigment 1)

After adding 185 parts of the base compound [B-1] to 1500 parts of N-methylpyrrolidone, 294 parts of 35% hydrochloric acid was added, and the mixture was cooled to -2 to 0 ° C. After adding 208 parts of a 25% aqueous sodium nitrite solution to this solution, 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], 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 having a pH of 5.4 in 10 minutes. After completion of the dropping, the mixture was stirred at room temperature for 30 minutes, further stirred while maintaining at 80 ° C., the precipitated reaction product was collected by filtration, washed with boiling water, and dried to add 343 parts of azo pigment 1 (yield:: 95.8%) obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as azo pigment 1.

Azo pigment 1

[Manufacturing Example 2]
(Manufacturing of azo pigment 2)
The same operation as in the production of the azo pigment 1 was performed except that 169 parts of the base compound [B-2] was used instead of 185 parts of the base compound [B-1] used in the production of the azo pigment 1. 2 was obtained in 337 parts (yield: 98.1%). As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as azo pigment 2.

Azo pigment 2

[Manufacturing Example 3]
(Manufacturing of azo pigment 3)
The same operation as in the production of the azo pigment 1 was performed except that 210 parts of the base compound [B-3] was used instead of 185 parts of the base compound [B-1] used in the production of the azo pigment 1. 3 was obtained in 371 parts (yield: 96.7%). As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as azo pigment 3.

Azo pigment 3

[Manufacturing Example 4]
(Manufacturing of azo pigment 4)
The same operation as in the production of the azo pigment 1 was performed except that 181 parts of the base compound [B-4] was used instead of 185 parts of the base compound [B-1] used in the production of the azo pigment 1. 4 was obtained in 340 parts (yield: 95.6%). As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as azo pigment 4.

Azo pigment 4

[Manufacturing Example 5]
(Manufacturing of azo pigment 5)
The same operation as in the production of the azo pigment 1 was performed except that 222 parts of the base compound [B-5] was used instead of 185 parts of the base compound [B-1] used in the production of the azo pigment 1. 5 was obtained in 384 parts (yield: 97.1%). As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 5.

Azo pigment 5

[Manufacturing Example 6]
(Manufacturing of azo pigment 6)
The same operation as in the production of the azo pigment 1 was performed except that 228 parts of the base compound [B-6] was used instead of 185 parts of the base compound [B-1] used in the production of the azo pigment 1. 6 was obtained in 393 parts (yield: 97.8%). As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 6.

Azo pigment 6

[Manufacturing Example 7]
(Manufacturing of azo pigment 7)
The same operation as in the production of the azo pigment 1 was performed except that 124 parts of the base compound [B-7] was used instead of 185 parts of the base compound [B-1] used in the production of the azo pigment 1. 7 was obtained in 287 parts (yield: 96.2%). As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 7.

Azo pigment 7

[Manufacturing Example 8]
(Manufacturing of azo pigment 8)
The same operation as in the production of the azo pigment 1 was performed except that 128 parts of the base compound [B-8] was used instead of 185 parts of the base compound [B-1] used in the production of the azo pigment 1. 8 was obtained in 296 parts (yield: 97.9%). As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 8.

Azo pigment 8

[Manufacturing Example 9]
(Manufacturing of azo pigment 9)
The same operation as in the production of the azo pigment 1 was performed except that 156 parts of the base compound [B-9] was used instead of 185 parts of the base compound [B-1] used in the production of the azo pigment 1. 322 parts (yield: 97.7%) of 9 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as azo pigment 9.

Azo pigment 9

[Manufacturing Example 10]
(Manufacturing of azo pigment 10)
The same operation as in the production of the azo pigment 1 was performed except that 187 parts of the base compound [B-10] was used instead of 185 parts of the base compound [B-1] used in the production of the azo pigment 1. 10 was obtained in 357 parts (yield: 98.9%). As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 10.

Azo pigment 10

[Manufacturing Example 11]
(Manufacturing of azo pigment 11)
The same operation as in the production of the azo pigment 1 was performed except that 190 parts of the base compound [B-11] was used instead of 185 parts of the base compound [B-1] used in the production of the azo pigment 1. 352 parts (yield: 96.6%) of 11 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 11.

Azo pigment 11

[Manufacturing Example 12]
(Manufacturing of azo pigment 12)
The same operation as in the production of the azo pigment 1 was performed except that 240 parts of the base compound [B-12] was used instead of 185 parts of the base compound [B-1] used in the production of the azo pigment 1. 12 was obtained in 399 parts (yield: 96.4%). As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 12.

Azo pigment 12

[Manufacturing Example 13]
(Manufacturing of azo pigment 13)
The same operation as in the production of the azo pigment 1 was performed except that 207 parts of the base compound [B-13] was used instead of 185 parts of the base compound [B-1] used in the production of the azo pigment 1. 13 was obtained in 373 parts (yield: 97.9%). As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 13.

Azo pigment 13

[Manufacturing Example 14]
(Manufacturing of azo pigment 14)
The same operation as in the production of the azo pigment 1 was performed except that 241 parts of the base compound [B-14] was used instead of 185 parts of the base compound [B-1] used in the production of the azo pigment 1. 14 was obtained in 394 parts (yield: 95.0%). As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 14.

Azo pigment 14

[Manufacturing Example 15]
(Manufacturing of azo pigment 15)
The same operation as in the production of the azo pigment 1 was performed except that 215 parts of the base compound [B-15] was used instead of 185 parts of the base compound [B-1] used in the production of the azo pigment 1. 372 parts (yield: 95.8%) of 15 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 15.

Azo pigment 15

[Manufacturing Example 16]
(Manufacturing of azo pigment 16)
The same operation as in the production of the azo pigment 1 was performed except that 233 parts of the base compound [B-16] was used instead of 185 parts of the base compound [B-1] used in the production of the azo pigment 1. 16 was obtained in 390 parts (yield: 96.0%). As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 16.

[Manufacturing Example 17]
(Manufacturing of azo pigment 17)
The same operation as in the production of the azo pigment 1 was performed except that 298 parts of the base compound [B-17] was used instead of 185 parts of the base compound [B-1] used in the production of the azo pigment 1. 17 was obtained in 455 parts (yield: 96.5%). As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 17.

Azo pigment 17

[Manufacturing Example 18]
(Manufacturing of azo pigment 18)
The same operation as in the production of the azo pigment 1 was performed except that 415 parts of the base compound [B-18] was used instead of 185 parts of the base compound [B-1] used in the production of the azo pigment 1. 18 was obtained in 567 parts (yield: 96.5%). As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 18.

Azo pigment 18

[Manufacturing Example 19]
(Manufacturing of azo pigment 19)
The same operation as in the production of the azo pigment 1 was performed except that 219 parts of the coupler compound [C-57] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 1. 19 was obtained in 396 parts (yield: 96.4%). As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 19.

Azo pigment 19

[Manufacturing Example 20]
(Manufacturing of azo pigment 20)
The same operation as in the production of the azo pigment 19 was performed except that 169 parts of the base compound [B-2] was used instead of 185 parts of the base compound [B-1] used in the production of the azo pigment 19. 20 was obtained in 390 parts (yield: 98.7%). As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 20.

Azo pigment 20

[Manufacturing Example 21]
(Manufacturing of azo pigment 21)
The same operation as in the production of the azo pigment 19 was performed except that 210 parts of the base compound [B-3] was used instead of 185 parts of the base compound [B-1] used in the production of the azo pigment 19. 21 was obtained in 430 parts (yield: 98.7%). As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 21.

Azo pigment 21

[Manufacturing Example 22]
(Manufacturing of azo pigment 22)
The same operation as in the production of the azo pigment 19 was performed except that 181 parts of the base compound [B-4] was used instead of 185 parts of the base compound [B-1] used in the production of the azo pigment 19. 22 was obtained in 397 parts (yield: 97.4%). As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 22.

Azo pigment 22

[Manufacturing Example 23]
(Manufacturing of azo pigment 23)
The same operation as in the production of the azo pigment 19 was performed except that 222 parts of the base compound [B-5] was used instead of 185 parts of the base compound [B-1] used in the production of the azo pigment 19. 23 was obtained in 433 parts (yield: 96.7%). As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 23.

Azo pigment 23

[Manufacturing Example 24]
(Manufacturing of azo pigment 24)
The same operation as in the production of the azo pigment 19 was performed except that 228 parts of the base compound [B-6] was used instead of 185 parts of the base compound [B-1] used in the production of the azo pigment 19. 24 was obtained in 435 parts (yield: 95.8%). As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 24.

Azo pigment 24

[Manufacturing Example 25]
(Manufacturing of azo pigment 25)
The same operation as in the production of the azo pigment 19 was performed except that 124 parts of the base compound [B-7] was used instead of 185 parts of the base compound [B-1] used in the production of the azo pigment 19. 25 was obtained in 344 parts (yield: 98.0%). As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 25.

Azo pigment 25

[Manufacturing Example 26]
(Manufacturing of azo pigment 26)
The same operation as in the production of the azo pigment 19 was performed except that 128 parts of the base compound [B-8] was used instead of 185 parts of the base compound [B-1] used in the production of the azo pigment 19. 26 was obtained in 337 parts (yield: 95.2%). As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 26.

Azo pigment 26

[Manufacturing Example 27]
(Manufacturing of azo pigment 27)
The same operation as in the production of the azo pigment 19 was performed except that 156 parts of the base compound [B-9] was used instead of 185 parts of the base compound [B-1] used in the production of the azo pigment 19. 27 was obtained in 373 parts (yield: 97.6%). As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 27.

Azo pigment 27

[Manufacturing Example 28]
(Manufacturing of azo pigment 28)
The same operation as in the production of the azo pigment 19 was performed except that 187 parts of the base compound [B-10] was used instead of 185 parts of the base compound [B-1] used in the production of the azo pigment 19. 28 was obtained in 393 parts (yield: 95.1%). As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 28.

Azo pigment 28

[Manufacturing Example 29]
(Manufacturing of azo pigment 29)
The same operation as in the production of the azo pigment 19 was performed except that 190 parts of the base compound [B-11] was used instead of 185 parts of the base compound [B-1] used in the production of the azo pigment 19. 405 parts (yield: 97.4%) of 29 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 29.

Azo pigment 29

[Manufacturing Example 30]
(Manufacturing of azo pigment 30)
The same operation as in the production of the azo pigment 19 was performed except that 240 parts of the base compound [B-12] was used instead of 185 parts of the base compound [B-1] used in the production of the azo pigment 19. 30 was obtained in 456 parts (yield: 97.8%). As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 30.

Azo pigment 30

[Manufacturing Example 31]
(Manufacturing of azo pigment 31)
The same operation as in the production of the azo pigment 19 was performed except that 207 parts of the base compound [B-13] was used instead of 185 parts of the base compound [B-1] used in the production of the azo pigment 19. 424 parts (yield: 97.8%) of 31 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 31.

Azo pigment 31

[Manufacturing Example 32]
(Manufacturing of azo pigment 32)
The same operation as in the production of the azo pigment 19 was performed except that 241 parts of the base compound [B-14] was used instead of 185 parts of the base compound [B-1] used in the production of the azo pigment 19. 32 was obtained in 457 parts (yield: 97.8%). As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 32.

Azo pigment 32

[Manufacturing Example 33]
(Manufacturing of azo pigment 33)
The same operation as in the production of the azo pigment 19 was performed except that 215 parts of the base compound [B-15] was used instead of 185 parts of the base compound [B-1] used in the production of the azo pigment 19. 428 parts (yield: 97.0%) of 33 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 33.

Azo pigment 33

[Manufacturing Example 34]
(Manufacturing of azo pigment 34)
The same operation as in the production of the azo pigment 19 was performed except that 233 parts of the base compound [B-16] was used instead of 185 parts of the base compound [B-1] used in the production of the azo pigment 19. 445 parts (yield: 97.0%) of 34 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 34.

Azo pigment 34

[Manufacturing Example 35]
(Manufacturing of azo pigment 35)
The same operation as in the production of the azo pigment 19 was performed except that 298 parts of the base compound [B-17] was used instead of 185 parts of the base compound [B-1] used in the production of the azo pigment 19. 500 parts (yield: 95.7%) of 35 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 35.

Azo pigment 35

[Manufacturing Example 36]
(Manufacturing of azo pigment 36)
The same operation as in the production of the azo pigment 19 was performed except that 415 parts of the base compound [B-18] was used instead of 185 parts of the base compound [B-1] used in the production of the azo pigment 19. 36 was obtained in 629 parts (yield: 98.4%). As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 36.

Azo pigment 36

[Manufacturing Example 37]
(Manufacturing of azo pigment 37)
The same operation as in the production of the azo pigment 4 was performed except that 172 parts of the coupler compound [C-2] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 4. 352 parts (yield: 97.6%) of 37 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 37.

Azo pigment 37

[Manufacturing Example 38]
(Manufacturing of azo pigment 38)
The same operation as in the production of the azo pigment 4 was performed except that 172 parts of the coupler compound [C-3] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 4. 38 was obtained in 357 parts (yield: 98.9%). As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 38.

Azo pigment 38

[Manufacturing Example 39]
(Manufacturing of azo pigment 39)
The same operation as in the production of the azo pigment 4 was performed except that 177 parts of the coupler compound [C-4] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 4. 354 parts (yield: 96.7%) of 39 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 39.

Azo pigment 39

[Manufacturing Example 40]
(Manufacturing of azo pigment 40)
The same operation as in the production of the azo pigment 4 was performed except that 177 parts of the coupler compound [C-5] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 4. 40 was obtained in 357 parts (yield: 97.6%). As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 40.

Azo pigment 40

[Manufacturing Example 41]
(Manufacturing of azo pigment 41)
The same operation as in the production of the azo pigment 4 was performed except that 182 parts of the coupler compound [C-6] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 4. 355 parts (yield: 95.8%) of 41 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 41.

Azo pigment 41

[Manufacturing Example 42]
(Manufacturing of azo pigment 42)
The same operation as in the production of the azo pigment 4 was performed except that 193 parts of the coupler compound [C-7] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 4. 42 was obtained in 366 parts (yield: 95.9%). As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 42.

Azo pigment 42

[Manufacturing Example 43]
(Manufacturing of azo pigment 43)
The same operation as in the production of the azo pigment 4 was performed except that 192 parts of the coupler compound [C-8] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 4. 43 was obtained in 369 parts (yield: 96.8%). As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 43.

Azo pigment 43

[Manufacturing Example 44]
(Manufacturing of azo pigment 44)
The same operation as in the production of the azo pigment 4 was performed except that 197 parts of the coupler compound [C-9] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 4. 381 parts (yield: 98.7%) of 44 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 44.

Azo pigment 44

[Manufacturing Example 45]
(Manufacturing of azo pigment 45)
The same operation as in the production of the azo pigment 4 was performed except that 178 parts of the coupler compound [C-10] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 4. 356 parts (yield: 97.0%) of 45 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 45.

Azo pigment 45

[Manufacturing Example 46]
(Manufacturing of azo pigment 46)
The same operation as in the production of the azo pigment 4 was performed except that 178 parts of the coupler compound [C-11] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 4. 355 parts (yield: 97.0%) of 46 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 46.

Azo pigment 46

[Manufacturing Example 47]
(Manufacturing of azo pigment 47)
The same operation as in the production of the azo pigment 4 was performed except that 183 parts of the coupler compound [C-12] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 4. 362 parts (yield: 97.3%) of 47 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 47.

Azo pigment 47

[Manufacturing Example 48]
(Manufacturing of azo pigment 48)
The same operation as in the production of the azo pigment 4 was performed except that 198 parts of the coupler compound [C-13] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 4. 382 parts (yield: 98.9%) of 48 were obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 48.

Azo pigment 48

[Manufacturing Example 49]
(Manufacturing of azo pigment 49)
The same operation as in the production of the azo pigment 4 was performed except that 173 parts of the coupler compound [C-14] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 4. 355 parts (yield: 98.4%) of 49 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 49.

Azo pigment 49

[Manufacturing Example 50]
(Manufacturing of azo pigment 50)
The same operation as in the production of the azo pigment 4 was performed except that 179 parts of the coupler compound [C-15] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 4. 50 was obtained in 358 parts (yield: 97.6%). As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 50.

Azo pigment 50

[Manufacturing Example 51]
(Manufacturing of azo pigment 51)
The same operation as in the production of the azo pigment 4 was performed except that 179 parts of the coupler compound [C-16] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 4. 350 parts (yield: 95.3%) of 51 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 51.

Azo pigment 51

[Manufacturing Example 52]
(Manufacturing of azo pigment 52)
The same operation as in the production of the azo pigment 4 was performed except that 176 parts of the coupler compound [C-17] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 4. 360 parts (yield: 98.7%) of 52 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 52.

Azo pigment 52

[Manufacturing Example 53]
(Manufacturing of azo pigment 53)
The same operation as in the production of the azo pigment 4 was performed except that 184 parts of the coupler compound [C-18] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 4. 367 parts (yield: 98.6%) of 53 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 53.

Azo pigment 53

[Manufacturing Example 54]
(Manufacturing of azo pigment 54)
The same operation as in the production of the azo pigment 4 was performed except that 183 parts of the coupler compound [C-19] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 4. 365 parts (yield: 98.2%) of 54 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 54.

Azo pigment 54

[Manufacturing Example 55]
(Manufacturing of azo pigment 55)
The same operation as in the production of the azo pigment 4 was performed except that 183 parts of the coupler compound [C-20] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 4. 353 parts (yield: 95.0%) of 55 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 55.

Azo pigment 55

[Manufacturing Example 56]
(Manufacturing of azo pigment 56)
The same operation as in the production of the azo pigment 4 was performed except that 183 parts of the coupler compound [C-21] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 4. 56 parts (yield: 98.3%) were obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 56.

Azo pigment 56

[Manufacturing Example 57]
(Manufacturing of azo pigment 57)
The same operation as in the production of the azo pigment 4 was performed except that 197 parts of the coupler compound [C-22] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 4. 57 was obtained in 379 parts (yield: 98.4%). As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 57.

Azo pigment 57

[Manufacturing Example 58]
(Manufacturing of azo pigment 58)
The same operation as in the production of the azo pigment 4 was performed except that 180 parts of the coupler compound [C-23] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 4. 352 parts (yield: 95.6%) of 58 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 58.

Azo pigment 58

[Manufacturing Example 59]
(Manufacturing of azo pigment 59)
The same operation as in the production of the azo pigment 4 was performed except that 196 parts of the coupler compound [C-24] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 4. 369 parts (yield: 95.9%) of 59 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 59.

Azo pigment 59

[Manufacturing Example 60]
(Manufacturing of azo pigment 60)
The same operation as in the production of the azo pigment 4 was performed except that 174 parts of the coupler compound [C-25] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 4. 60 was obtained in 353 parts (yield: 97.6%). As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 60.

Azo pigment 60

[Manufacturing Example 61]
(Manufacturing of azo pigment 61)
The same operation as in the production of the azo pigment 4 was performed except that 214 parts of the coupler compound [C-26] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 4. 392 parts (yield: 96.0%) of 61 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 61.

Azo pigment 61

[Manufacturing Example 62]
(Manufacturing of azo pigment 62)
The same operation as in the production of the azo pigment 4 was performed except that 192 parts of the coupler compound [C-27] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 4. 362 parts (yield: 95.1%) of 62 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 62.

Azo pigment 62

[Manufacturing Example 63]
(Manufacturing of azo pigment 63)
The same operation as in the production of the azo pigment 4 was performed except that 180 parts of the coupler compound [C-28] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 4. 63 parts (yield: 98.8%) were obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 63.

Azo pigment 63

[Manufacturing Example 64]
(Manufacturing of azo pigment 64)
The same operation as in the production of the azo pigment 4 was performed except that 187 parts of the coupler compound [C-29] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 4. 366 parts (yield: 97.5%) of 64 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 64.

Azo pigment 64

[Manufacturing Example 65]
(Manufacturing of azo pigment 65)
The same operation as in the production of the azo pigment 4 was performed except that 194 parts of the coupler compound [C-30] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 4. 366 parts (yield: 95.8%) of 65 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 65.

Azo pigment 65

[Manufacturing Example 66]
(Manufacturing of azo pigment 66)
The same operation as in the production of the azo pigment 4 was performed except that 196 parts of the coupler compound [C-31] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 4. 374 parts (yield: 97.3%) of 66 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 66.

Azo pigment 66

[Manufacturing Example 67]
(Manufacturing of azo pigment 67)
The same operation as in the production of the azo pigment 4 was performed except that 190 parts of the coupler compound [C-32] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 4. 368 parts (yield: 97.3%) of 67 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 67.

Azo pigment 67

[Manufacturing Example 68]
(Manufacturing of azo pigment 68)
The same operation as in the production of the azo pigment 4 was performed except that 186 parts of the coupler compound [C-33] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 4. 360 parts (yield: 96.4%) of 68 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 68.

Azo pigment 68

[Manufacturing Example 69]
(Manufacturing of azo pigment 69)
The same operation as in the production of the azo pigment 4 was performed except that 186 parts of the coupler compound [C-34] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 4. 69 parts (yield: 95.9%) were obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 69.

Azo pigment 69

[Manufacturing Example 70]
(Manufacturing of azo pigment 70)
The same operation as in the production of the azo pigment 4 was performed except that 212 parts of the coupler compound [C-35] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 4. 70 was obtained in 393 parts (yield: 98.2%). As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 70.

Azo pigment 70

[Manufacturing Example 71]
(Manufacturing of azo pigment 71)
The same operation as in the production of the azo pigment 4 was performed except that 178 parts of the coupler compound [C-36] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 4. 352 parts (yield: 95.9%) of 71 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 71.

Azo pigment 71

[Manufacturing Example 72]
(Manufacturing of azo pigment 72)
The same operation as in the production of the azo pigment 4 was performed except that 189 parts of the coupler compound [C-37] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 4. 72 was obtained in 373 parts (yield: 98.8%). As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 72.

Azo pigment 72

[Manufacturing Example 73]
(Manufacturing of azo pigment 73)
The same operation as in the production of the azo pigment 4 was performed except that 205 parts of the coupler compound [C-38] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 4. 73 parts (yield: 95.6%) were obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 73.

Azo pigment 73

[Manufacturing Example 74]
(Manufacturing of azo pigment 74)
The same operation as in the production of the azo pigment 4 was performed except that 178 parts of the coupler compound [C-39] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 4. 358 parts (yield: 97.8%) of 74 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 74.

Azo pigment 74

[Manufacturing Example 75]
(Manufacturing of azo pigment 75)
The same operation as in the production of the azo pigment 4 was performed except that 218 parts of the coupler compound [C-40] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 4. 401 parts (yield: 98.8%) of 75 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 75.

Azo pigment 75

[Manufacturing Example 76]
(Manufacturing of azo pigment 76)
The same operation as in the production of the azo pigment 4 was performed except that 183 parts of the coupler compound [C-41] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 4. 367 parts (yield: 98.7%) of 76 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 76.

Azo pigment 76

[Manufacturing Example 77]
(Manufacturing of azo pigment 77)
The same operation as in the production of the azo pigment 4 was performed except that 185 parts of the coupler compound [C-42] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 4. 356 parts (yield: 95.3%) of 77 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 77.

Azo pigment 77

[Manufacturing Example 78]
(Manufacturing of azo pigment 78)
The same operation as in the production of the azo pigment 4 was performed except that 191 parts of the coupler compound [C-43] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 4. 372 parts (yield: 98.0%) of 78 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 78.

Azo pigment 78

[Manufacturing Example 79]
(Manufacturing of azo pigment 79)
The same operation as in the production of the azo pigment 4 was performed except that 211 parts of the coupler compound [C-44] were used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 4. 388 parts (yield: 97.2%) of 79 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 79.

Azo pigment 79

[Manufacturing Example 80]
(Manufacturing of azo pigment 80)
The same operation as in the production of the azo pigment 7 was performed except that 172 parts of the coupler compound [C-2] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 7. 301 parts (yield: 98.9%) of 80 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 80.

Azo pigment 80

[Manufacturing Example 81]
(Manufacturing of azo pigment 81)
The same operation as in the production of the azo pigment 7 was performed except that 172 parts of the coupler compound [C-3] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 7. 298 parts (yield: 98.0%) of 81 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 81.

Azo pigment 81

[Manufacturing Example 82]
(Manufacturing of azo pigment 82)
The same operation as in the production of the azo pigment 7 was performed except that 192 parts of the coupler compound [C-8] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 7. 317 parts (yield: 98.0%) of 82 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 82.

Azo pigment 82

[Manufacturing Example 83]
(Manufacturing of azo pigment 83)
The same operation as in the production of the azo pigment 7 was performed except that 178 parts of the coupler compound [C-11] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 7. 300 parts (yield: 96.8%) of 83 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 83.

Azo pigment 83

[Manufacturing Example 84]
(Manufacturing of azo pigment 84)
The same operation as in the production of the azo pigment 7 was performed except that 180 parts of the coupler compound [C-23] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 7. 307 parts (yield: 98.6%) of 84 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 84.

Azo pigment 84

[Manufacturing Example 85]
(Manufacturing of azo pigment 85)
The same operation as in the production of the azo pigment 7 was performed except that 185 parts of the coupler compound [C-42] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 7. 309 parts (yield: 98.6%) of 85 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 85.

Azo pigment 85

[Manufacturing Example 86]
(Manufacturing of azo pigment 86)
The same operation as in the production of the azo pigment 7 was performed except that 191 parts of the coupler compound [C-43] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 7. 317 parts (yield: 98.4%) of 86 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 86.

Azo pigment 86

[Manufacturing Example 87]
(Manufacturing of azo pigment 87)
The same operation as in the production of the azo pigment 4 was performed except that 195 parts of the coupler compound [C-45] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 4. 375 parts (yield: 97.7%) of 87 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 87.

Azo pigment 87

[Manufacturing Example 88]
(Manufacturing of azo pigment 88)
The same operation as in the production of the azo pigment 4 was performed except that 200 parts of the coupler compound [C-46] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 4. 373 parts (yield: 96.0%) of 88 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 88.

Azo pigment 88

[Manufacturing Example 89]
(Manufacturing of azo pigment 89)
The same operation as in the production of the azo pigment 4 was performed except that 211 parts of the coupler compound [C-47] were used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 4. 388 parts of 89 (yield: 97.3%) was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 89.

Azo pigment 89

[Manufacturing Example 90]
(Manufacturing of azo pigment 90)
The same operation as in the production of the azo pigment 4 was performed except that 251 parts of the coupler compound [C-48] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 4. 422 parts (yield: 96.1%) of 90 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 90.

Azo pigment 90

[Manufacturing Example 91]
(Manufacturing of azo pigment 91)
The same operation as in the production of the azo pigment 4 was performed except that 261 parts of the coupler compound [C-49] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 4. 445 parts (yield: 98.9%) of 91 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 91.

Azo pigment 91

[Manufacturing Example 92]
(Manufacturing of azo pigment 92)
The same operation as in the production of the azo pigment 4 was performed except that 263 parts of the coupler compound [C-50] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 4. 437 parts (yield: 96.9%) of 92 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 92.

Azo pigment 92

[Manufacturing Example 93]
(Manufacturing of azo pigment 93)
The same operation as in the production of the azo pigment 4 was performed except that 223 parts of the coupler compound [C-51] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 4. 396 parts (yield: 96.2%) of 93 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 93.

Azo pigment 93

[Manufacturing Example 94]
(Manufacturing of azo pigment 94)
The same operation as in the production of the azo pigment 4 was performed except that 229 parts of the coupler compound [C-52] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 4. 409 parts (yield: 97.9%) of 94 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 94.

Azo pigment 94

[Manufacturing Example 95]
(Manufacturing of azo pigment 95)
The same operation as in the production of the azo pigment 4 was performed except that 244 parts of the coupler compound [C-53] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 4. 417 parts (yield: 96.3%) of 95 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 95.

Azo pigment 95

[Manufacturing Example 96]
(Manufacturing of azo pigment 96)
The same operation as in the production of the azo pigment 4 was performed except that 201 parts of the coupler compound [C-54] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 4. 382 parts (yield: 98.1%) of 96 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 96.

Azo pigment 96

[Manufacturing Example 97]
(Manufacturing of azo pigment 97)
The same operation as in the production of the azo pigment 4 was performed except that 207 parts of the coupler compound [C-55] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 4. 383 parts (yield: 96.9%) of 97 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 97.

Azo pigment 97

[Manufacturing Example 98]
(Manufacturing of azo pigment 98)
The same operation as in the production of the azo pigment 4 was performed except that 206 parts of the coupler compound [C-56] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 4. 383 parts (yield: 97.3%) of 98 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 98.

Azo pigment 98

[Manufacturing Example 99]
(Manufacturing of azo pigment 99)
The same operation as in the production of the azo pigment 4 was performed except that 229 parts of the coupler compound [C-58] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 4. 411 parts (yield: 98.4%) of 99 were obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 99.

Azo pigment 99

[Manufacturing Example 100]
(Manufacturing of Azo Pigment 100)
The same operation as in the production of the azo pigment 4 was performed except that 229 parts of the coupler compound [C-59] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 4. 400 parts (yield: 95.8%) of 100 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 100.

Azo pigment 100

[Manufacturing Example 101]
(Manufacturing of Azo Pigment 101)
The same operation as in the production of the azo pigment 4 was performed except that 270 parts of the coupler compound [C-60] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 4. 441 parts (yield: 96.4%) of 101 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 101.

Azo pigment 101

[Manufacturing Example 102]
(Manufacturing of azo pigment 102)
The same operation as in the production of the azo pigment 4 was performed except that 245 parts of the coupler compound [C-61] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 4. 421 parts (yield: 97.3%) of 102 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 102.

Azo pigment 102

[Manufacturing Example 103]
(Manufacturing of azo pigment 103)
The same operation as in the production of the azo pigment 4 was performed except that 232 parts of the coupler compound [C-62] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 4. 405 parts (yield: 96.3%) of 103 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 103.

Azo pigment 103

[Manufacturing Example 104]
(Manufacturing of azo pigment 104)
The same operation as in the production of the azo pigment 4 was performed except that 231 parts of the coupler compound [C-63] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 4. 399 parts (yield: 96.3%) of 104 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 104.

Azo pigment 104

[Manufacturing Example 105]
(Manufacturing of azo pigment 105)
The same operation as in the production of the azo pigment 4 was performed except that 241 parts of the coupler compound [C-64] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 4. 423 parts (yield: 98.4%) of 105 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 105.

Azo pigment 105

[Manufacturing Example 106]
(Manufacturing of Azo Pigment 106)
The same operation as in the production of the azo pigment 4 was performed except that 281 parts of the coupler compound [C-65] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 4. 456 parts (yield: 97.1%) of 106 were obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 106.

Azo pigment 106

[Manufacturing Example 107]
(Manufacturing of azo pigment 107)
The same operation as in the production of the azo pigment 4 was performed except that 212 parts of the coupler compound [C-66] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 4. 395 parts (yield: 98.7%) of 107 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 107.

Azo pigment 107

[Manufacturing Example 108]
(Manufacturing of azo pigment 108)
The same operation as in the production of the azo pigment 4 was performed except that 211 parts of the coupler compound [C-67] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 4. 390 parts (yield: 97.7%) of 108 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 108.

Azo pigment 108

[Manufacturing Example 109]
(Manufacturing of azo pigment 109)
The same operation as in the production of the azo pigment 4 was performed except that 225 parts of the coupler compound [C-68] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 4. 400 parts (yield: 96.9%) of 109 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 109.

Azo pigment 109

[Manufacturing Example 110]
(Manufacturing of azo pigment 110)
The same operation as in the production of the azo pigment 4 was performed except that 230 parts of the coupler compound [C-69] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 4. 407 parts (yield: 97.4%) of 110 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 110.

Azo pigment 110

[Manufacturing Example 111]
(Manufacturing of azo pigment 111)
The same operation as in the production of the azo pigment 4 was performed except that 237 parts of the coupler compound [C-70] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 4. 409 parts (yield: 96.0%) of 111 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 111.

Azo pigment 111

[Manufacturing Example 112]
(Manufacturing of azo pigment 112)
The same operation as in the production of the azo pigment 7 was performed except that 200 parts of the coupler compound [C-46] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 7. 320 parts (yield: 96.4%) of 112 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 112.

Azo pigment 112

[Manufacturing Example 113]
(Manufacturing of azo pigment 113)
The same operation as in the production of the azo pigment 7 was performed except that 211 parts of the coupler compound [C-47] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 7. 329 parts (yield: 96.0%) of 113 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 113.

Azo pigment 113

[Manufacturing Example 114]
(Manufacturing of azo pigment 114)
The same operation as in the production of the azo pigment 7 was performed except that 251 parts of the coupler compound [C-48] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 7. 374 parts (yield: 97.6%) of 114 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 114.

Azo pigment 114

[Manufacturing Example 115]
(Manufacturing of azo pigment 115)
The same operation as in the production of the azo pigment 7 was performed except that 201 parts of the coupler compound [C-54] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 7. 319 parts (yield: 95.7%) of 115 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 115.

Azo pigment 115

[Manufacturing Example 116]
(Manufacturing of azo pigment 116)
The same operation as in the production of the azo pigment 7 was performed except that 206 parts of the coupler compound [C-56] was used instead of 167 parts of the coupler compound [C-1] used in the production of the azo pigment 7. 330 parts (yield: 97.7%) of 116 was obtained. As a result of mass spectrometry and elemental analysis by TOF-MS, it was identified as the azo pigment 116.

Azo pigment 116

[Manufacturing Example 117]
(Manufacturing of azo pigment 117) Miniaturization process of azo pigment 4 80 parts of azo pigment 4, 800 parts of sodium chloride, and 90 parts of diethylene glycol are charged in a stainless steel 1-gallon kneader (manufactured by Inoue Seisakusho) for 6 hours at 60 ° C. It was kneaded and treated with salt milling. The obtained kneaded product was put into 3 liters of warm water, stirred for 1 hour while heating at 70 ° C. to form a slurry, filtered and washed with water repeatedly to remove sodium chloride and diethylene glycol, and then dried at 80 ° C. overnight. , 78 parts of azo pigment 117 was obtained.

[Manufacturing Example 118]
(Manufacturing of azo pigment 118) Miniaturization process of azo pigment 22 80 parts of azo pigment 22, 800 parts of sodium chloride, and 90 parts of diethylene glycol are charged in a stainless steel 1-gallon kneader (manufactured by Inoue Seisakusho) for 6 hours at 60 ° C. It was kneaded and treated with salt milling. The obtained kneaded product was put into 3 liters of warm water, stirred for 1 hour while heating at 70 ° C. to form a slurry, filtered and washed with water repeatedly to remove sodium chloride and diethylene glycol, and then dried at 80 ° C. overnight. , 78 parts of azo pigment 118 was obtained.

[Manufacturing Examples 119 to 124]
(Manufacturing of azo pigments 120 to 125)
In the production of the azo pigment 117, the azo pigments 120 to 125 were obtained in the same manner as the azo pigment 117 except that the azo pigment 4 and the dye derivative were changed to the types and ratios shown in Table 4-2 instead of the azo pigment 4. rice field.

[Manufacturing Example 125-130]
(Manufacturing of azo pigments 126 to 131)
In the production of the azo pigment 118, the azo pigments 126 to 131 were obtained in the same manner as the azo pigment 118 except that the azo pigment 22 and the dye derivative were changed to the types and ratios shown in Table 4-2 instead of the azo pigment 22. rice field.

[Manufacturing Example 801]
(Manufacturing of azo pigment 119)
The following azo pigment 119 was synthesized with reference to JP-A-2014-160160.

［製造例８０２〜８１３］
＜その他の顔料の製造＞
（赤色着色剤１（ＲＣＰ−１）の製造： ＰＲ２５４）
市販のＣ．Ｉ．ピグメントレッド２５４（ＰＲ２５４）（ＢＡＳＦ社製「イルガジンレッド Ｄ３６５６ ＨＤ」）１００部、塩化ナトリウム１２００部、及びジエチレングリコール１２０部をステンレス製１ガロンニーダー（井上製作所社製）に仕込み、６０℃で６時間混練し、ソルトミリング処理した。得られた混練物を３リットルの温水に投入し、７０℃に加熱しながら１時間撹拌してスラリー状とし、濾過、水洗を繰り返して塩化ナトリウム及びジエチレングリコールを除いた後、８０℃で一昼夜乾燥し、９８部の赤色着色剤１（ＲＣＰ−１）を得た。平均一次粒子径は３３ｎｍであった。 Azo pigment 119

[Manufacturing Example 802-813]
<Manufacturing of other pigments>
(Manufacturing of Red Colorant 1 (RCP-1): PR254)
Commercially available C.I. I. Add 100 parts of Pigment Red 254 (PR254) (BASF's "Irgazine Red D3656 HD"), 1200 parts of sodium chloride, and 120 parts of diethylene glycol to a stainless steel 1-gallon kneader (manufactured by Inoue Seisakusho) for 6 hours. It was kneaded and treated with salt milling. The obtained kneaded product was put into 3 liters of warm water, stirred for 1 hour while heating at 70 ° C. 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. , 98 parts of red colorant 1 (RCP-1) was obtained. The average primary particle size was 33 nm.

(Manufacturing of Red Colorant 2 (RCP-2): PR177)
C. I. Pigment Red 254 (BASF's "Irgazine Red D3656 HD"), C.I. I. Pigment Red 177 (PR177) (“Cinilex Red SR3C” manufactured by Sinnic Co., Ltd.) was changed in the same manner as in the production of the red colorant 1, and 97 parts of the red colorant 2 (RCP-2) was obtained. The average primary particle size was 37 nm.

(Manufacturing of Red Colorant 3 (RCP-3): PR242)
C. I. Pigment Red 254 (BASF's "Irgazine Red D3656 HD"), C.I. I. Pigment Red 242 (PR242) (“Sandorin Scarlet 4RF” manufactured by Clariant) was used in the same manner as in the production of the red colorant 1 to obtain 98 parts of the red colorant 3 (RCP-3). The average primary particle size was 39 nm.

(Manufacturing of Red Colorant 4 (RCP-4): PR269)
C. I. Pigment Red 254 (BASF's "Irgazine Red D3656 HD"), C.I. I. Pigment Red 269 (PR269) (“Permanent Carmine 3810” manufactured by Sanyo Dye Co., Ltd.) was changed in the same manner as in the production of the red colorant 1, and 98 parts of the red colorant 4 (RCP-4) were obtained. .. The average primary particle size was 35 nm.

(Production of Red Colorant 5 (RCP-5): Brominated Diketopyrrolopyrrole Pigment Formula (14))
To a stainless steel reaction vessel equipped with a reflux tube, 200 parts of molecularly dehydrated tert-amyl alcohol and 140 parts of sodium-tert-amyl alkoxide were added under a nitrogen atmosphere, and the mixture was heated to 100 ° C. with stirring to prepare an alcoholate solution. Prepared. On the other hand, 88 parts of diisopropyl succinate and 153.6 parts of 4-bromobenzonitrile were added to a glass flask and heated to 90 ° C. with stirring to dissolve them to prepare a solution of a mixture thereof. The heated solution of this mixture was slowly added dropwise to the alcoholate solution heated to 100 ° C. at a constant rate over 2 hours with vigorous stirring. After completion of the dropping, heating and stirring were continued at 90 ° C. for 2 hours to obtain an alkali metal salt of a diketopyrrolopyrrole compound. Further, 600 parts of methanol, 600 parts of water, and 304 parts of acetic acid were added to the reaction vessel with a glass jacket, and the mixture was cooled to −10 ° C. The cooled mixture was cooled to 75 ° C. using a high-speed stirring disperser while rotating a share disk having a diameter of 8 cm at 4000 rpm, and the alkali metal salt of the previously obtained diketopyrrolopyrrole compound was cooled therein. The solution was added in small portions. At this time, the rate of adding the alkali metal salt of the diketopyrrolopyrrole compound at 75 ° C. while cooling so that the temperature of the mixture consisting of methanol, acetic acid, and water is always maintained at −5 ° C. or lower. Was added in small portions over approximately 120 minutes. After the addition of the alkali metal salt, red crystals were precipitated and a red suspension was formed. Subsequently, the obtained red suspension was washed with an ultrafiltration device at 5 ° C. and then filtered off to obtain a red paste. This paste was redistributed in 3500 parts of methanol cooled to 0 ° C. to prepare a suspension having a methanol concentration of about 90%, and the mixture was stirred at 5 ° C. for 3 hours to perform particle sizing and washing with crystal transition. Subsequently, the water paste of the obtained diketopyrrolopyrrole compound was filtered off with an extraneous filter, dried at 80 ° C. for 24 hours, and pulverized to form a brominated diketo represented by the formula (14). 150.8 parts of pyrrolopyrrole pigment was obtained.

100 parts of the brominated diketopyrrolopyrrole pigment represented by the above formula (14), 1200 parts of sodium chloride, and 120 parts of diethylene glycol were charged in a stainless steel 1-gallon kneader (manufactured by Inoue Seisakusho) and 6 at 60 ° C. It was kneaded for a long time and treated with salt milling. The obtained kneaded product was put into 3 liters of warm water, stirred for 1 hour while heating at 70 ° C. 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. , 98 parts of red colorant 5 (RCP-5) was obtained. The average primary particle size was 45 nm.
Equation (14)

(Manufacturing of Yellow Colorant 1 (YCP-1): PY138)
Kinoftalone yellow pigment C.I. I. 500 parts of Pigment Yellow 138 (BASF's "Pariotor Yellow L0962-HD"), 500 parts of sodium chloride, and 250 parts of diethylene glycol were placed in a stainless steel 1-gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 120 ° C. for 8 hours. .. Next, this kneaded product was put into 5 liters of warm water, stirred for 1 hour while heating at 70 ° C. to form a slurry, filtered and washed with water repeatedly to remove sodium chloride and diethylene glycol, and then dried at 80 ° C. overnight. Then, 490 parts of yellow colorant 1 (YCP-1) was obtained. The average primary particle size was 63 nm.

(Manufacturing of Yellow Colorant 2 (YCP-2): PY139)
Isoindoline yellow pigment C.I. I. 500 parts of Pigment Yellow 139 (BASF's "Pariotor Yellow L1820"), 500 parts of sodium chloride, and 250 parts of diethylene glycol were charged in a stainless steel 1-gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 120 ° C. for 8 hours. Next, this kneaded product was put into 5 liters of warm water, stirred for 1 hour while heating at 70 ° C. to form a slurry, filtered and washed with water repeatedly to remove sodium chloride and diethylene glycol, and then dried at 80 ° C. overnight. Then, 510 parts of yellow colorant 2 (YCP-2) was obtained. The average primary particle size was 68 nm.

(Manufacturing of Yellow Colorant 3 (YCP-3): PY150)
Azo-based yellow pigment C.I. I. 500 parts of Pigment Yellow 150 (“Hosta Palm Yellow HN4G” manufactured by Clariant), 500 parts of sodium chloride, and 250 parts of diethylene glycol were charged in a stainless steel 1-gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 120 ° C. for 8 hours. Next, this kneaded product was put into 5 liters of warm water, stirred for 1 hour while heating at 70 ° C. to form a slurry, filtered and washed with water repeatedly to remove sodium chloride and diethylene glycol, and then dried at 80 ° C. overnight. Then, 500 parts of yellow colorant 3 (YCP-3) was obtained. The average primary particle size was 60 nm.

(Production of Yellow Colorant 4 (YCP-4): Kinophthalone Compound (b))
To 200 parts of methyl benzoate, 40 parts of 8-aminoquinaldine, 150 parts of 2,3-naphthalenedicarboxylic acid anhydride and 154 parts of benzoic acid were added, heated to 180 ° C., and stirred for 4 hours. Further, after cooling to room temperature, the reaction mixture was added to 5440 parts of acetone, and the mixture was stirred at room temperature for 1 hour. The product was filtered off, washed with methanol and dried to obtain 116 parts of the quinophthalone compound (c). As a result of mass spectrometry by TOF-MS, it was identified as the quinophthalone compound (c).

Kinoftalone compound (c)

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

Compound (c-2)

To 300 parts of methyl benzoate, 100 parts of compound (c-2), 108 parts of tetrachlorophthalic anhydride, and 143 parts of benzoic acid were added, heated to 180 ° C., and reacted for 4 hours. By TOF-MS, the formation of the quinophthalone compound (b) and the disappearance of the raw material compound (c-2) were confirmed. Further, after cooling to room temperature, the reaction mixture was added to 3510 parts of acetone and stirred at room temperature for 1 hour. The product was filtered off, washed with methanol and dried to obtain 120 parts of quinophthalone compound (b). As a result of mass spectrometry by TOF-MS, it was identified as the quinophthalone compound (b).
Kinoftalone compound (b)

500 parts of the quinophthalone compound (b), 500 parts of sodium chloride, and 250 parts of diethylene glycol obtained above were charged in a stainless steel 1-gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 120 ° C. for 8 hours. Next, this kneaded product was put into 5 liters of warm water, stirred for 1 hour while heating at 70 ° C. to form a slurry, filtered and washed with water repeatedly to remove sodium chloride and diethylene glycol, and then dried at 80 ° C. overnight. Then, 480 parts of yellow colorant 4 (YCP-4) was obtained. The average primary particle size was 62 nm.

(Manufacturing of green colorant 1: PG58)
Phthalocyanine-based green pigment C. I. Pigment Green 58 (“FASTOGEN GREEN A110” manufactured by DIC Corporation), 1400 parts of sodium chloride, and 360 parts of diethylene glycol were charged in a stainless steel 1-gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 80 ° C. for 6 hours. This kneaded product was put into 8000 parts of warm water, stirred for 2 hours while heating at 80 ° C. to form a slurry, filtered and washed with water repeatedly to remove sodium chloride and diethylene glycol, and then dried at 85 ° C. overnight and 190. A green colorant 1 was obtained. The average primary particle size was 69 nm.

(Preparation of blue colorant 1: PB15: 6)
Phthalocyanine blue pigment C.I. I. Add 200 parts of Pigment Blue 15: 6 (“LIONOL BLUE ES” manufactured by Toyo Color Co., Ltd.), 1400 parts of sodium chloride, and 360 parts of diethylene glycol to a stainless steel 1-gallon kneader (manufactured by Inoue Seisakusho) and knead at 80 ° C for 6 hours. bottom. Next, this kneaded product was put into 8000 parts of warm water, stirred for 2 hours while heating at 80 ° C. to form a slurry, filtered and washed with water repeatedly to remove sodium chloride and diethylene glycol, and then dried at 85 ° C. for 24 hours. , 190 parts of blue colorant 1 was obtained. The average primary particle size was 74 nm.

(Preparation of purple colorant 1: PV23)
Dioxazine-based purple pigment C.I. I. 200 parts of 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 in a stainless steel 1-gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 80 ° C. for 6 hours. Next, this kneaded product was put into 8000 parts of warm water, stirred for 2 hours while heating at 80 ° C. to form a slurry, filtered and washed with water repeatedly to remove sodium chloride and diethylene glycol, and then dried at 85 ° C. for 24 hours. , 190 parts of purple colorant 1 was obtained. The average primary particle size was 69 nm.

As described above, the results of mass spectrometry and elemental analysis of the azo pigments produced in Production Examples 1 to 116 are shown in Tables 3 and 4, respectively. Table 4 shows the evaluation results of the average primary particle size of all the produced pigments.

<Manufacturing method of pigment dispersion>
[Manufacturing Example 201]
(Preparation of Pigment Dispersion (RM-1))
The following mixture is stirred and mixed so as to be uniform, and then dispersed with an Eiger mill (“Mini Model M-250 MKII” manufactured by Eiger Japan Co., Ltd.) using zirconia beads having a diameter of 0.5 mm for 3 hours, and then the pore diameter is 5. The mixture was filtered through a 0 μm filter to prepare a pigment dispersion (RM-1) having a non-volatile component of 20% by mass.
Red colorant (RP-1): 12.0 parts Acrylic resin solution 1: 19.2 parts Propylene glycol monomethyl ether acetate (PGMAc): 60.8 parts Acid resin type dispersant solution ("Disperbyk-110" manufactured by BIC Chemie) (Solid content 52%)): 8.0 parts

[Manufacturing Examples 202 to 330, Comparative Example 1]
(Pigment dispersion (RM-2 to 131)
Hereinafter, pigment dispersions (RM-2 to 131) were prepared in the same manner as the pigment dispersion (RM-1) except that the compositions were changed to those shown in Tables 5 and 5-2.

[Manufacturing Example 331]
(Preparation of Pigment Dispersion (RM-132))
The following mixture is stirred and mixed so as to be uniform, and then dispersed with an Eiger mill (“Mini Model M-250 MKII” manufactured by Eiger Japan Co., Ltd.) using zirconia beads having a diameter of 0.5 mm for 3 hours, and then the pore diameter is 5. The mixture was filtered through a 0 μm filter to prepare a pigment dispersion (RM-132) having a non-volatile component of 20% by mass.
Red colorant (RP-4): 12.0 parts Acrylic resin solution 1: 19.2 parts Propylene glycol monomethyl ether acetate (PGMAc): 60.5 parts Acid resin type dispersant solution (SOLSPERSE-55000 manufactured by Lubrizol) (Solid content 50%)): 8.3 parts

[Manufacturing Example 332]
(Preparation of Pigment Dispersion (RM-133))
The following mixture is stirred and mixed so as to be uniform, and then dispersed with an Eiger mill (“Mini Model M-250 MKII” manufactured by Eiger Japan Co., Ltd.) using zirconia beads having a diameter of 0.5 mm for 3 hours, and then the pore diameter is 5. The mixture was filtered through a 0 μm filter to prepare a pigment dispersion (RM-133) having a non-volatile component of 20% by mass.
Red colorant (RP-4): 12.0 parts Acrylic resin solution 1: 19.2 parts Propylene glycol monomethyl ether acetate (PGMAc): 58.4 parts Basic resin type dispersant solution (Disperbyk-2000 manufactured by Big Chemie) (Solid content 40%)): 10.4 parts

[Manufacturing Example 333]
(Preparation of Pigment Dispersion (RM-134))
The following mixture is stirred and mixed so as to be uniform, and then dispersed with an Eiger mill (“Mini Model M-250 MKII” manufactured by Eiger Japan Co., Ltd.) using zirconia beads having a diameter of 0.5 mm for 3 hours, and then the pore diameter is 5. The mixture was filtered through a 0 μm filter to prepare a pigment dispersion (RM-134) having a non-volatile component of 20% by mass.
Red colorant (RP-4): 12.0 parts Acrylic resin solution 1: 40.0 parts Propylene glycol monomethyl ether acetate (PGMAc): 48.0 parts

[Manufacturing Example 334]
(Preparation of pigment dispersion (RM-135))
The following mixture is stirred and mixed so as to be uniform, and then dispersed with an Eiger mill (“Mini Model M-250 MKII” manufactured by Eiger Japan Co., Ltd.) using zirconia beads having a diameter of 0.5 mm for 3 hours, and then the pore diameter is 5. The mixture was filtered through a 0 μm filter to prepare a pigment dispersion (RM-135) having a non-volatile component of 20% by mass.
Red colorant (RP-4): 12.0 parts Acrylic resin solution 1: 19.2 parts Propylene glycol monomethyl ether acetate (PGMAc): 58.4 parts Acid resin type dispersant solution (resin type dispersant solution 1): 10.4 copies

[Manufacturing Example 335-337]
(Pigment dispersion (RM-136 to 138)
Hereinafter, a pigment dispersion (RM-136 to 138) was prepared in the same manner as the pigment dispersion (RM-135) except that the composition was changed to that shown in Table 5-3.

[Manufacturing Example 338]
(Pigment dispersion (RM-139)
A pigment dispersion (RM-139) was prepared in the same manner as the pigment dispersion (RM-132) except that the red colorant (RP-4) was changed to the red colorant (RP-22).

[Manufacturing Example 339]
(Pigment dispersion (RM-140)
A pigment dispersion (RM-140) was prepared in the same manner as the pigment dispersion (RM-133) except that the red colorant (RP-4) was changed to the red colorant (RP-22).

[Manufacturing Example 340]
(Pigment dispersion (RM-141)
A pigment dispersion (RM-141) was prepared in the same manner as the pigment dispersion (RM-134) except that the red colorant (RP-4) was changed to the red colorant (RP-22).

[Manufacturing Example 341]
(Pigment dispersion (RM-142)
A pigment dispersion (RM-142) was prepared in the same manner as the pigment dispersion (RM-135) except that the red colorant (RP-4) was changed to the red colorant (RP-22).

[Manufacturing Examples 342 to 344]
(Pigment dispersion (RM-143 to 145)
Hereinafter, pigment dispersions (RM-143 to 145) were prepared in the same manner as the pigment dispersion (RM-142) except that the composition was changed to that shown in Table 5-3.

[Manufacturing Example 345]
(Preparation of Pigment Dispersion (RM-146))
The following mixture is stirred and mixed so as to be uniform, and then dispersed with an Eiger mill (“Mini Model M-250 MKII” manufactured by Eiger Japan Co., Ltd.) using zirconia beads having a diameter of 0.5 mm for 3 hours, and then the pore diameter is 5. The mixture was filtered through a 0 μm filter to prepare a pigment dispersion (RM-146) having a non-volatile component content of 20% by mass.
Red colorant (RP-4): 10.8 parts Dye derivative 1: 1.2 parts Acrylic resin solution 1: 19.2 parts Propylene glycol monomethyl ether acetate (PGMAc): 60.8 parts Acid resin type dispersant solution ( "Disperbyk-110" manufactured by Big Chemie): 8.0 copies

[Manufacturing Examples 346 to 350, 353 to 358]
(Pigment dispersion (RM-147 to 151, 154 to 159)
Hereinafter, pigment dispersions (RM-147 to 151, 154 to 159) were prepared in the same manner as the pigment dispersion (RM-146) except that the composition was changed to that shown in Table 5-4.

[Manufacturing Example 351]
(Preparation of Pigment Dispersion (RM-152))
The following mixture is stirred and mixed so as to be uniform, and then dispersed with an Eiger mill (“Mini Model M-250 MKII” manufactured by Eiger Japan Co., Ltd.) using zirconia beads having a diameter of 0.5 mm for 3 hours, and then the pore diameter is 5. The mixture was filtered through a 0 μm filter to prepare a pigment dispersion (RM-152) having a non-volatile component of 20% by mass.
Red colorant (RP-4): 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 Acid resin type dispersant solution ( Resin type dispersant solution 1): 10.4 parts

[Manufacturing Examples 352, 359, 360]
(Pigment dispersion (RM-153, 160, 161)
Hereinafter, pigment dispersions (RM-153, 160, 161) were prepared in the same manner as the pigment dispersion (RM-152) except that the composition was changed to that shown in Table 5-4.

[Comparative Manufacturing Example 2]
(Pigment dispersion (RCM-2): PR177)
The following mixture is stirred and mixed so as to be uniform, and then dispersed with an Eiger mill (“Mini Model M-250 MKII” manufactured by Eiger Japan Co., Ltd.) using zirconia beads having a diameter of 0.5 mm for 3 hours, and then the pore diameter is 5. The mixture was filtered through a 0 μm filter to prepare a pigment dispersion (RCM-2) having a non-volatile component of 20% by mass.
Red Colorant 2 (RCP-2) (PR177): 12.0 parts Acrylic resin solution 1: 36.4 parts Propylene glycol monomethyl ether acetate (PGMAc): 50.2 parts Acid resin type dispersant solution (manufactured by BIC Chemie) Disperbyk-110 "): 1.4 copies

[Comparative Manufacturing Example 3]
(Pigment dispersion (RCM-4): PR269)
The following mixture is stirred and mixed so as to be uniform, and then dispersed with an Eiger mill (“Mini Model M-250 MKII” manufactured by Eiger Japan Co., Ltd.) using zirconia beads having a diameter of 0.5 mm for 3 hours, and then the pore diameter is 5. The mixture was filtered through a 0 μm filter to prepare a pigment dispersion (RCM-4) having a non-volatile component of 20% by mass.
Red colorant 4 (RCP-4) (PR269): 12.0 parts Acrylic resin solution 1: 36.4 parts Propylene glycol monomethyl ether acetate (PGMAc): 50.2 parts Acid resin type dispersant solution (manufactured by BIC Chemie) Disperbyk-110 "): 1.4 copies

(Pigment dispersion (RCM-1): PR254)
The following mixture is stirred and mixed so as to be uniform, and then dispersed with an Eiger mill (“Mini Model M-250 MKII” manufactured by Eiger Japan Co., Ltd.) using zirconia beads having a diameter of 0.5 mm for 3 hours, and then the pore diameter is 5. The mixture was filtered through a 0 μm filter to prepare a pigment dispersion (RCM-1) having a non-volatile component of 20% by mass.
Red colorant 1 (RCP-1) (PR254): 12.0 parts Acrylic resin solution 1: 36.4 parts Propylene glycol monomethyl ether acetate (PGMAc): 50.2 parts Acid resin type dispersant solution (manufactured by BIC Chemie) Disperbyk-110 "): 1.4 copies

(Pigment dispersion (RCM-3): PR242)
The following mixture is stirred and mixed so as to be uniform, and then dispersed with an Eiger mill (“Mini Model M-250 MKII” manufactured by Eiger Japan Co., Ltd.) using zirconia beads having a diameter of 0.5 mm for 3 hours, and then the pore diameter is 5. The mixture was filtered through a 0 μm filter to prepare a pigment dispersion (RCM-3) having a non-volatile component of 20% by mass.
Red Colorant 3 (RCP-3) (PR242): 12.0 parts Acrylic resin solution 1: 36.4 parts Propylene glycol monomethyl ether acetate (PGMAc): 50.2 parts Acid resin type dispersant solution (manufactured by BIC Chemie) Disperbyk-110 "): 1.4 copies

(Pigment dispersion (RCM-5): formula (14))
The following mixture is stirred and mixed so as to be uniform, and then dispersed with an Eiger mill (“Mini Model M-250 MKII” manufactured by Eiger Japan Co., Ltd.) using zirconia beads having a diameter of 0.5 mm for 3 hours, and then the pore diameter is 5. The mixture was filtered through a 0 μm filter to prepare a pigment dispersion (RCM-5) having a non-volatile component of 20% by mass.
Red Colorant 5 (RCP-5) (Formula (14)): 12.0 parts Acrylic resin solution 1: 36.4 parts Propylene glycol monomethyl ether acetate (PGMAc): 50.2 parts Acid resin type dispersant solution (Big Chemie) "Disperbyk-110"): 1.4 copies

(Pigment dispersion (YCM-1): PY138)
The following mixture is stirred and mixed so as to be uniform, and then dispersed with an Eiger mill (“Mini Model M-250 MKII” manufactured by Eiger Japan Co., Ltd.) using zirconia beads having a diameter of 0.5 mm for 3 hours, and then the pore diameter is 5. The mixture was filtered through a 0 μm filter to prepare a pigment dispersion (YCM-1) having a non-volatile component of 20% by mass.
Yellow colorant 1 (YCP-1) (PY138): 12.0 parts Acrylic resin solution 1: 36.4 parts Propylene glycol monomethyl ether acetate (PGMAc): 50.2 parts Acid resin type dispersant solution (manufactured by BIC Chemie) Disperbyk-110 ": 1.4 copies

(Pigment dispersion (YCM-2): PY139)
The following mixture is stirred and mixed so as to be uniform, and then dispersed with an Eiger mill (“Mini Model M-250 MKII” manufactured by Eiger Japan Co., Ltd.) using zirconia beads having a diameter of 0.5 mm for 3 hours, and then the pore diameter is 5. The mixture was filtered through a 0 μm filter to prepare a pigment dispersion (YCM-2) having a non-volatile component of 20% by mass.
Yellow colorant 2 (YCP-2) (PY139): 12.0 parts Acrylic resin solution 1: 36.4 parts Propylene glycol monomethyl ether acetate (PGMAc): 50.2 parts Acid resin type dispersant solution (manufactured by BIC Chemie) Disperbyk-110 "): 1.4 copies

(Pigment dispersion (YCM-3): PY150)
The following mixture is stirred and mixed so as to be uniform, and then dispersed with an Eiger mill (“Mini Model M-250 MKII” manufactured by Eiger Japan Co., Ltd.) using zirconia beads having a diameter of 0.5 mm for 3 hours, and then the pore diameter is 5. The mixture was filtered through a 0 μm filter to prepare a pigment dispersion (YCM-3) having a non-volatile component of 20% by mass.
Yellow Colorant 3 (YCP-3) (PY150): 12.0 parts Acrylic resin solution 1: 36.4 parts Propylene glycol monomethyl ether acetate (PGMAc): 50.2 parts Acid resin type dispersant solution (manufactured by BIC Chemie) Disperbyk-110 ": 1.4 copies

(Pigment dispersion (YCM-4): quinophthalone compound (b))
The following mixture is stirred and mixed so as to be uniform, and then dispersed with an Eiger mill (“Mini Model M-250 MKII” manufactured by Eiger Japan Co., Ltd.) using zirconia beads having a diameter of 0.5 mm for 3 hours, and then the pore diameter is 5. The mixture was filtered through a 0 μm filter to prepare a pigment dispersion (YCM-4) having a non-volatile component of 20% by mass.
Yellow colorant 4 (YCP-4) quinophthalone compound (b): 12.0 parts Acrylic resin solution 1: 36.4 parts Propylene glycol monomethyl ether acetate (PGMAc): 50.2 parts Acid resin type dispersant solution (Big Chemie) "Disperbyk-110" manufactured by the company: 1.4 copies

(Evaluation of pigment dispersion)
The heat resistance, light resistance, foreign matter evaluation and storage stability of the obtained pigment dispersion and the coating film produced using the same were carried out by the following methods. The evaluation results are shown in Table 5.

(Heat resistance evaluation)
The pigment dispersion was applied onto a 100 mm × 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 at 230 ° C. A coating film substrate (one aspect of a color filter) was produced by heating and allowing to cool for 60 minutes. ^{The chromaticity ([L *} (1), a ^* (1), b ^* (1)]) of the obtained coating film at the C light source was measured by a microspectroscopy (“OSP-SP100” manufactured by Olympus Optical Co., Ltd.). Measured using. After that, as a heat resistance test, the mixture was heated at 250 ° C. for 1 hour, the chromaticity ([L ^* (2), a ^* (2), b ^* (2)]) with a C light source was measured, and the following formula was used. , Color difference ΔEab ^* was obtained and evaluated in the following four stages.

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

⊚: ΔEab ^* is less than 1.0 (extremely good)
◯: ΔEab ^* is 1.0 or more and less than 2.5 (good)
Δ: ΔEab ^* is 2.5 or more and less than 5.0 (defective)
×: ΔEab ^* is 5.0 or more (extremely defective)

(Light resistance evaluation)
A coating substrate is prepared by the same method as in the heat resistance evaluation, and the chromaticity ([L ^* (1), a ^* (1), b ^* (1)]) at the C light source is measured by a microspectroscopy (1). The measurement was performed using "OSP-SP100" manufactured by Olympus Optical Co., Ltd.). Subsequently, an ultraviolet cut filter (“COLORED OPTICAL GLASS L38” manufactured by Hoya Co., Ltd.) was attached on the substrate, and ^{after irradiating with ultraviolet rays for 100 hours using a 470 W / m 2} xenon lamp, the chromaticity with a C light source ([ L ^* (2), a ^* (2), b ^* (2)]) were measured, and the color difference ΔEab ^* was obtained by the above formula and evaluated according to the same criteria as the heat resistance.

(Evaluation of foreign matter on the coating film)
The pigment dispersion was applied onto a 100 mm × 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 230. A coating film substrate was prepared by heating at ° C. for 60 minutes and allowing to cool. The evaluation was performed by observing the surface using a metallurgical microscope "BX60" manufactured by Olympus System Corporation. The magnification was set to 500 times, and the number of particles that could be observed in any five fields of view by transmission was counted. It was evaluated on the following four stages.

◎: The number of foreign substances is less than 5 (extremely good)
◯: The number of foreign substances is 5 or more and less than 10 (good)
Δ: The number of foreign substances is 10 or more and less than 60 (defective)
×: The number of foreign substances is 60 or more (extremely defective)

(Storage stability test method)
The viscosity of the pigment dispersion at 25 ° C. was measured at a rotation speed of 20 rpm using an E-type viscometer (TUE-20L type manufactured by Toki Sangyo Co., Ltd.). From the initial viscosity on the day of preparation of the coloring composition and the viscosity measured after storage in a constant temperature room at 40 ° C for 7 days, the viscosity change rate (%) (= (viscosity after storage at 40 ° C for 7 days-initial viscosity) / initial Viscosity x 100) was calculated and the storage stability was evaluated according to the following criteria.

⊚: Viscosity change rate is less than 10% (extremely good)
◯: Viscosity change rate is 10% or more and less than 20% (good)
Δ: Viscosity change rate is 20% or more and less than 50% (defective)
X: Viscosity change rate is 50% or more (extremely poor)

As shown in Table 5, the pigment dispersion using the colorant used in the present invention showed good results in heat resistance, light resistance, foreign matter in the coating film, and storage stability of the coating film. In particular, when compared with the coloring composition using the azo pigment 119 (Comparative Production Example 1), the dispersion was more stable due to the higher-order steric hindrance of the pigment, so that the quality was improved. Further, in particular, by using a resin-type dispersant or a dye derivative having an aromatic carboxylic acid in combination, excellent heat resistance and light resistance, foreign matter in the coating film, and good storage stability were obtained.

<Manufacturing method of resin having a cationic group in the side chain>
(Resin 1 having a cationic group in the side chain)
67.3 parts of methyl ethyl ketone was placed in a four-neck separable flask equipped with a thermometer, a stirrer, a distillation tube, and a cooler, and the temperature was raised to 75 ° C. under a nitrogen stream. Separately, 34.0 parts of methyl methacrylate, 28.0 parts of n-butyl methacrylate, 28.0 parts of 2-ethylhexyl methacrylate, 10.0 parts of dimethylaminoethyl methacrylate, 2,2'-azobis (2,4-dimethylvaleronitrile). ) Was homogenized in 6.5 parts and 25.1 parts of methyl ethyl ketone, charged in a dropping funnel, attached to a four-neck separable flask, and added dropwise over 2 hours. Two hours after the completion of the dropping, it was confirmed from the solid content that the polymerization yield was 98% or more and the weight average molecular weight (Mw) was 6830, and the mixture was cooled to 50 ° C. To this, 3.2 parts of methyl chloride and 22.0 parts of ethanol were added and reacted at 50 ° C. for 2 hours, then heated to 80 ° C. over 1 hour, and further reacted for 2 hours. In this way, a resin 1 having a cationic group in the side chain having an ammonium group having a resin component of 47% by mass was obtained. The ammonium salt value of the obtained resin was 34 mgKOH / g.

<Dye manufacturing method>
(Dye 01 (AR52-JK))
Follow the procedure below to C.I. I. Dye 01 (AR52-JK), which is a salt-forming compound composed of Acid Red 52 and a resin 1 having a cationic group in the side chain, was produced.
Resin 1 having a cationic group was added to 2000 parts of water in an amount of 30 parts in terms of solid content, and the mixture was sufficiently stirred and mixed, and then heated to 60 ° C. On the other hand, 90 parts of water and 10 parts of C.I. I. An aqueous solution in which Acid Red 52 was dissolved was prepared, and the solution was gradually added dropwise to the resin solution. After the dropping, the mixture was stirred at 60 ° C. for 120 minutes to sufficiently react. To confirm the end point of the reaction, it was judged that the salt-forming compound was obtained by dropping the reaction solution onto the filter paper and using the point where the bleeding disappeared as the end point. After allowing to cool to room temperature with stirring, suction filtration was performed, and after washing with water, the salt-forming compound remaining on the filter paper was dried by removing water with a dryer, and 32 parts of C.I. I. Dye 01 (AR52-JK), which is a salt-forming compound of Acid Red 52 and a resin 1 having a cationic group in the side chain, was obtained. At this time, C.I. I. The content of the active dye component derived from Acid Red 52 was 25% by mass.

(Dye 02 (AR289-JK))
Follow the procedure below to C.I. I. Dye 02 (AR289-JK), which is a salt-forming compound composed of Acid Red 289 and a resin 1 having a cationic group in the side chain, was produced.
Resin 1 having a cationic group was added to 2000 parts of water in an amount of 30 parts in terms of solid content, and the mixture was sufficiently stirred and mixed, and then heated to 60 ° C. On the other hand, 90 parts of water and 10 parts of C.I. I. An aqueous solution in which Acid Red 289 was dissolved was prepared, and the solution was gradually added dropwise to the resin solution. After the dropping, the mixture was stirred at 60 ° C. for 120 minutes to sufficiently react. To confirm the end point of the reaction, it was judged that the salt-forming compound was obtained by dropping the reaction solution onto the filter paper and using the point where the bleeding disappeared as the end point. After allowing to cool to room temperature with stirring, suction filtration was performed, and after washing with water, the salt-forming compound remaining on the filter paper was dried by removing water with a dryer, and 32 parts of C.I. I. Dye 02 (AR289-JK), which is a salt-forming compound of Acid Red 289 and a resin 1 having a cationic group in the side chain, was obtained. At this time, C.I. I. The content of the active dye component derived from Acid Red 289 was 27% by mass.

である。 (Dyes 03-04 (AR289-SA, AR289-DSA))
Based on the description in JP-A-2013-203056, dyes 03 to 04 (AR289-SA, AR289-DSA), which are the following xanthene-based sulfonic acid amide compounds, were obtained.
note that,

Is.

(Dyes 05-06 (DP-1, DP-2))
According to the synthetic scheme described in Japanese Patent No. 5085256, Exemplified Compound I-1 and Exemplified Compound III-45 were obtained and used as dyes 05-06 (DP-1, DP-2), respectively.

(Dye 07 (BB7-NT))
2,8-Diamino-1-naphthol-5,7-disulfonic acid (molecular weight 334) is dissolved in a 7 to 15 mol% sodium hydroxide solution, and the mixture is sufficiently mixed and stirred to obtain the sodium salt. After heating this 2,8-diamino-1-naphthol-5,7-disulfonic acid sodium salt aqueous solution to 70 to 90 ° C., Victoria Pure Blue Dye (CI Basic Blue 7) is gradually added dropwise. .. Further, the Victoria Pure Blue dye may be dissolved in water and used as an aqueous solution. After dropping the Victoria Pure Blue dye, the mixture is stirred at 70 to 90 ° C. for 40 to 60 minutes to sufficiently react. To confirm the end point of the reaction, it can be determined that the salt-forming compound was obtained by dropping the reaction solution onto the filter paper and using the point where the bleeding disappeared as the end point. After allowing to cool to room temperature with stirring, suction filtration is performed and the mixture is washed with water. After washing with water, the salt-forming compound remaining on the filter paper is dried by removing water with a dryer to form a salt of Victoria Pure Blue dye and 2,8-diamino-1-naphthol-5,7-disulfonic acid. Dye 07 (BB7-NT), which is a compound and a triarylmethane salt-forming compound, was obtained.

(Dye 08 (BV10-MA))
In a 1 L stainless steel reaction vessel with a recirculation tube, under a nitrogen atmosphere, C.I. I. Dissolve 5.0 parts of Basic Violet 10 (BV10: manufactured by Taoka Chemical Co., Ltd .: Rodamine B) and 1.6 parts of hydroxyethyl methacrylate (HEMA) in 40 ml of dichloromethane, and dissolve 1- (3-dimethylaminopropyl) -3-ethyl. 2.2 parts of carbodiimide hydrochloride and 0.25 part of dimethylaminopyridine were added, and the mixture was stirred at room temperature for 24 hours. The obtained dichloromethane solution was washed with water, dried under reduced pressure, and then purified on a silica gel column to obtain dye 08 (BV10-MA). The yield was 51.6%.

<Manufacturing method of dye solution>
(Dye solution (DS-01))
The following mixture was stirred and mixed so as to be uniform, and then filtered through a filter having a pore size of 5.0 μm to prepare a dye solution (DS-01).

Dye 01: 16.0 parts PGMAc: 84.0 parts

A dye solution (DS-02-12) was obtained in the same manner as the dye solution (DS-01) except that the dye was changed to the composition shown in Table 6.

<Manufacturing method of photosensitive coloring composition for color filter>
[Example 401]
(Photosensitive coloring composition (RR-401))
The following raw materials are mixed and stirred using the pigment dispersion (RCM-1), (RM-2), and the dye solution (DS-01) so that the solid content has the following blending amount, and PGMAc Was added to adjust the non-volatile content to 16% by mass, and the mixture was filtered through a filter having a pore size of 1.0 μm to obtain a photosensitive coloring composition (RR-401). Hereinafter, the solid content mass is shown.

Pigment Dispersion RCM-1: 12.0 parts Pigment Dispersion RM-2: 18.0 parts Dye 01 DS-01: 5.0 parts Acrylic resin solution 2: 25.0 parts Photopolymerizable monomer Aronix M- 402 (Toa Synthetic): 30.0 parts Photopolymerization initiator Irgacure 907 (BASF): 10.0 parts

[Examples 402 to 469, Comparative Examples 501 and 502]
(Photosensitive coloring compositions (RR-402 to 469, RR-501, 502))
Mix so as to have the composition shown in Table 7, adjust the non-volatile content to 16% by mass using PGMAc, and make the photosensitive coloring composition (RR-402 to RR-402) in the same manner as the photosensitive coloring composition (RR-401). 469, RR-501,502) was obtained.

<Evaluation of photosensitive coloring composition for color filters>
The brightness, contrast ratio, and film thickness of the obtained photosensitive coloring composition were measured by the following methods. Table 7 shows the evaluation results.

(Evaluation of brightness)
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. The chromaticity of the obtained substrate was x = 0. A coated substrate having 683 and y = 0.313 was obtained. The brightness (Y) of the obtained substrate was measured with a microspectroscopy (“OSP-SP200” manufactured by Olympus Optical Co., Ltd.).

(Evaluation of contrast ratio (CR))
The contrast ratio was measured using the substrate on which the brightness was measured.

(Evaluation of film thickness)
The film thickness was measured using the substrate whose brightness was measured. A surface shape measuring instrument DEKTAK150 (manufactured by ULVAC ES) was used for measuring the film thickness.

From the results in Table 7, it was clarified that the examples using the colorant of the present invention had excellent brightness and became a thin film. In particular, when used in place of the azo pigment 119, a remarkable effect was confirmed.

<Manufacturing method of green and blue photosensitive coloring composition for color filter>
(Green Photosensitive Coloring Composition 1: PG58 / PY138)
The following mixture was stirred and mixed so as to be uniform, and then dispersed with an Eiger mill (“Mini Model M-250 MKII” manufactured by Eiger Japan Co., Ltd.) using zirconia beads having a diameter of 0.5 mm for 5 hours, and then the pore diameter was 5. The mixture was filtered through a 0 μm filter to prepare a green pigment dispersion having a non-volatile content of 20% by mass.
Green Colorant 1 (CI Pigment Green 58): 12.0 parts Acrylic resin solution 1: 36.4 parts Propylene glycol monomethyl ether acetate (PGMAc): 50.2 parts Acid resin type dispersant solution (manufactured by BIC Chemie) "Disperbyk-110"): 1.4 copies

The following mixture is stirred and mixed so as to be uniform, and then dispersed with an Eiger mill (“Mini Model M-250 MKII” manufactured by Eiger Japan Co., Ltd.) using zirconia beads having a diameter of 0.5 mm for 5 hours, and then the pore diameter is 5. The mixture was filtered through a 0 μm filter to prepare a yellow pigment dispersion having a non-volatile content of 20% by mass.
Yellow Colorant 1 (CI Pigment Yellow 138): 12.0 parts Acrylic resin solution 1: 36.4 parts Propylene glycol monomethyl ether acetate (PGMAc): 50.2 parts Acid resin type dispersant solution (manufactured by BIC Chemie) "Plasterbyk-110": 1.4 copies

Subsequently, the mixture having the following composition was stirred and mixed so as to be uniform, and then filtered through a filter having a pore size of 1 μm to prepare a green photosensitive coloring composition 1.
Green pigment dispersion: 32.0 parts Yellow pigment dispersion: 18.0 parts Acrylate resin solution 2: 7.5 parts Photopolymerizable monomer ("Aronix M-402" manufactured by Toa Synthetic Co., Ltd.): 2.0 parts Dipentaerythritol hexaacrylate photopolymerization initiator (BASF "OXE-02"): 1.5 parts Etanone, 1- [9-ethyl-6- (2-methylbenzoyl) -9H-carbazole-3-yl] -, 1- (0-acetyloxime)
Cyclohexanone: 39.0 parts

(Blue Photosensitive Coloring Composition 1: PB15: 6 / PV23)
Similar to the green pigment dispersion, the non-volatile content is 20% by mass, except that the green colorant 1 (CI Pigment Green 58) is changed to the blue colorant 1 (CI Pigment Blue 15: 6). Blue pigment dispersion was obtained.

Similar to the green pigment dispersion, purple with a non-volatile content of 20% by mass, except that the green colorant 1 (CI Pigment Green 58) was changed to the purple colorant 1 (CI Pigment Violet 23). A pigment dispersion was obtained.

Subsequently, 32.0 parts of the green pigment dispersion and 18.0 parts of the yellow pigment dispersion were replaced with 46.0 parts of the blue dispersion and 4.0 parts of the purple dispersion, totaling 50.0 parts. A blue photosensitive coloring composition 1 was obtained in the same manner as the green photosensitive coloring composition 1 except for the above.

<Manufacturing and evaluation of color filters>
The red photosensitive coloring composition (RR-1) is applied onto a glass substrate on which a black matrix is formed using a slit die coater, and then prebaked on a hot plate at 90 ° C. for 2 minutes to form a coating film. Formed. Next, after cooling the substrate on which the coating film was formed to room temperature, radiation containing each wavelength of 365 nm, 405 nm, and 436 nm was applied to the coating film at 1,000 J / m via a striped photomask using a high-pressure mercury lamp. ^It was exposed with an exposure amount of 2. After alkaline development, the cells were washed with ultrapure water and post-baked at 230 ° C. for 20 minutes to form red striped pixels on the substrate.
Then, by the same method, the green photosensitive coloring composition 1 was used to form green striped pixels next to the red striped pixels. Further, using the blue photosensitive coloring composition 1, similarly, blue striped pixels adjacent to the red and green pixels were formed.
Next, a protective film was formed using the photocurable resin composition on the pixels consisting of the three colors of red, green, and blue. In this way, it was possible to create an RGB three-color color filter having high luminance and excellent resistance.

Claims (8)

A coloring composition for a color filter containing an azo pigment, a colorant composed of a dye, and a binder resin, wherein the azo pigment contains a compound represented by the following general formula (1) or (2). A coloring composition for a color filter.
General formula (1)

[In the general formula (1), R ₁ represents a halogen atom, an alkyl group which may have a substituent, an alkoxyl group which may have a substituent, and an aryloxy group which may have a substituent. .. R ₂ and R ₃ independently represent a hydrogen atom, an alkyl group which may have a substituent, and a phenyl group which may have a substituent.
Independently, X _{1 to} X ₄ are 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 and a sulfo group. , Represents a halogen atom. ]

General formula (2)

[In the general formula (2), R ₄ represents a halogen atom, an alkyl group which may have a substituent, an alkoxyl group which may have a substituent, and an aryloxy group which may have a substituent. .. R ₅ and R ₆ independently represent a hydrogen atom, an alkyl group which may have a substituent, and a phenyl group which may have a substituent.
X _{5 to} X ₁₂ 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, and a halogen atom. A represents a direct bond or a divalent linking group. As the divalent linking group, an alkylene group which may have a substituent, -O-, -S-, -CO-, -SO _2- , -COO-, -CONH-, and -SO ₂ NH- are used. show. ] The coloring composition for a color filter according to claim 1, further comprising a resin-type dispersant having an acidic substituent. The coloring composition for a color filter according to claim 2, wherein the resin-type dispersant having an acidic substituent is a resin-type dispersant having an aromatic carboxyl group. The coloring composition for a color filter according to any one of claims 1 to 3, further comprising a dye derivative, wherein the dye derivative contains a dye derivative having a basic substituent. Colorants are further described in C.I. I. Pigment Red 254, C.I. I. Pigment Red 242, C.I. I. Pigment Yellow 138, C.I. I. Pigment Yellow 139, C.I. I. The color according to any one of claims 1 to 4, which comprises at least one selected from the group consisting of Pigment Yellow 150, a yellow pigment represented by the following general formula (3), and a brominated diketopyrrolopyrrole pigment. Coloring composition for filters.

General formula (3)

[In the general formula (3), Z _{1 to} Z ₁₃ independently have a hydrogen atom, a halogen atom, an alkyl group which may have a substituent, an alkoxyl group which may have a substituent, and a substituent. It may have an aryl group, -SO ₃ H, -COOH, and monovalent to trivalent metal salt thereof acidic groups, alkylammonium salt, an optionally substituted phthalimidomethyl group, or a substituent The sulfamoyl group which may have is shown.
Adjacent groups of Z _{1 to} Z ₄ and / or Z _{10 to} Z ₁₃ may together form an aromatic ring that may have a substituent. ] The one according to any one of claims 1 to 5, wherein the dye is at least one selected from the group consisting of xanthene-based, dipyrromethene-based, triarylmethane-based, cyanine-based, phthalocyanine-based and anthraquinone-based. Coloring composition for color filters. The coloring composition for a color filter according to any one of claims 1 to 6, further comprising a photopolymerizable monomer and a photopolymerization initiator. A color filter comprising a filter segment formed from the coloring composition for a color filter according to any one of claims 1 to 7 on a substrate.