JP7476703B2 - Coloring composition, photosensitive coloring composition, color filter, liquid crystal display device, and solid-state image pickup device - Google Patents

Description

The present invention relates to a coloring composition, a photosensitive coloring composition, a color filter, a liquid crystal display device, and a solid-state imaging device.

Liquid crystal display devices are display devices in which a liquid crystal layer sandwiched between two polarizing plates controls the degree of polarization of light that passes through the first polarizing plate, thereby controlling the amount of light that passes through the second polarizing plate, and the mainstream type uses twisted nematic (TN) liquid crystals. Liquid crystal display devices are capable of color display by placing a color filter between the two polarizing plates.

Other representative LCD display systems include the in-plane switching (IPS) system, in which a pair of electrodes are placed on one of the substrates and an electric field is applied in a direction parallel to the substrate; the vertical alignment (VA) system, in which nematic liquid crystals with negative dielectric anisotropy are vertically aligned; and the optically concave bend (OCB) system, in which the optical axes of uniaxial retardation films are perpendicular to each other to provide optical compensation. All of these systems are in practical use. For this reason, LCD display devices are widely used in computer monitors, televisions, etc.

Typically, color filters are formed on the surface of a transparent substrate such as glass, and are made up of fine stripe-shaped filter segments (pixels) arranged in parallel or crosswise rows, each consisting of a red filter layer (R), a green filter layer (G), and a blue filter layer (B), or fine filter segments arranged in a fixed array vertically and horizontally. The filter segments are very fine, ranging from a few microns to a few hundred microns, and are arranged in a regular order in a predetermined array for each hue. Recently, filter segments consisting of a yellow filter layer (Y) have also been used in addition to RGB.

On the color filters used in liquid crystal display devices, transparent electrodes for driving the liquid crystal are generally formed by deposition or sputtering, and an alignment film for aligning the liquid crystal in a certain direction is formed on top of that. To obtain the full performance of these transparent electrodes and alignment films, the formation process must be carried out at high temperatures, generally above 200°C, and preferably above 230°C, so the color filters must be heat-resistant.

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

In addition, in recent years, there has been a trend to reduce the number of backlights, which serve as light sources, in order to reduce power consumption. If low-brightness color filters are used, the screen will be dark due to the low light transmittance, and it will not be possible to reduce the number of backlights, which serve as light sources. For this reason, high brightness color filters are essential.

In addition to high contrast and brightness, color filters also need to have a wide color reproduction range and high reliability.

Solid-state imaging devices such as C-MOS (Complementary Metal Oxide Semiconductor) and CCD (Charge Coupled Device) generally perform color separation by arranging color filters with additive primary color filter segments of a red filter layer (R), a green filter layer (G), and a blue filter layer (B) on the light receiving element. Color filters with filter segments of cyan (C), magenta (M), and yellow (Y), which correspond to the complementary colors of red, green, and blue, are also commonly used because they provide higher sensitivity than primary color filters.

As with liquid crystal display devices, color filters used in solid-state imaging devices also require high color characteristics and reliability.

Currently, the most common method for manufacturing color filters is the pigment dispersion method, which uses a pigment with excellent resistance to various factors such as light and heat as a colorant. In the pigment dispersion method, color filters are manufactured by the following method. First, a photosensitive coloring composition in which a pigment is dispersed is applied to a transparent substrate such as glass. After removing the solvent from the coating by drying, the coating is exposed to light in a pattern corresponding to a filter segment of a certain color. Next, the unexposed parts of the coating are removed by development, and then a process such as heating is performed as necessary. This results in a filter segment pattern of the first color. Then, similar operations are performed to form filter segment patterns of other colors, completing the color filter.

In the manufacture of green filter segments, in addition to green pigments as colorants, yellow pigments are used as colorants for adjusting color (colorants for toning), particularly C.I. Pigment Yellow 138, 139, 150, 185, etc. are used. In the manufacture of red filter segments, in addition to red pigments as colorants, yellow pigments such as C.I. Pigment Yellow 138, 139, 185, etc. are used as colorants to achieve higher brightness and a wider color reproduction range.
Among them, C.I. Pigment Yellow 138, which is a quinophthalone compound, is often used because it can provide high transmittance. However, C.I. Pigment Yellow 138, which is a quinophthalone compound, has a problem in that foreign matter is generated in the coating film when heat of 230° C. or more is applied.

Furthermore, green pixels using C.I. Pigment Green 7, 36, 58, 59, halogenated phthalocyanine pigments described in JP-A-2016-57635 and JP-A-2016-153481, which are widely used as green pigments, and C.I. Pigment Yellow 138, when incorporated into a liquid crystal display device while being shielded from oxygen, undergo phthalocyanine radical ionization when exposed to backlight in a high-temperature, high-humidity environment, resulting in a decrease in brightness and a decrease in voltage retention rate, which adversely affects the operation of the liquid crystal display device.

In order to solve the above problems, various efforts have been made. For example, Patent Document 1 discloses a green color paste containing C.I. Pigment Yellow 138 and a sulfonated derivative of C.I. Pigment Yellow 138 as a green color paste excellent in heat resistance and contrast ratio. Patent Document 2 discloses a pigment dispersion composition containing a pigment having an average primary particle size of 10 to 30 nm and a quinophthalone compound having at least one group selected from a hydroxyl group, a carboxylic acid group, a sulfonic acid group, an amino group, and salts thereof as a pigment dispersion composition with improved contrast and brightness. Patent Document 3 discloses a fluorine atom-containing quinophthalone compound excellent in brightness, contrast, and heat resistance.
However, these methods are not satisfactory in terms of brightness, contrast, and suppression of foreign matter, and do not take into consideration the decrease in brightness in a high-temperature, high-humidity, oxygen-blocking environment.

As an effort to solve the problem of brightness reduction in an oxygen-blocked environment, Patent Document 4 discloses a photosensitive coloring composition for color filters that contains a halogenated metal phthalocyanine, C.I. Pigment Yellow 138 as a quinophthalone-based yellow pigment, and a triarylsulfonium compound as an acid generator. However, although the brightness reduction in an oxygen-blocked environment is improved, contrast and brightness are deteriorated, and furthermore viscosity stability is extremely deteriorated, making it impractical. In addition, no consideration is given to the reduction in voltage holding rate.

JP 2002-179979 A JP 2011-122125 A JP 2016-145282 A JP 2019-8014 A

The problem that the present invention aims to solve is to provide a coloring composition and a photosensitive coloring composition that have excellent brightness and contrast ratio, generate little foreign matter, have an excellent voltage retention rate, and experience little decrease in brightness under high temperature and high humidity conditions, as well as a color filter, a liquid crystal display device, and a solid-state imaging device formed using the photosensitive coloring composition.

As a result of extensive research, the inventors discovered that the above problems could be solved by using a yellow colorant with a specific structure, and thus completed the present invention.

That is, the present invention relates to a yellow coloring composition comprising a yellow colorant (A), a dispersion resin (B), and an organic solvent (C), in which the yellow colorant (A) comprises a yellow colorant (A1) that is a metal salt with a compound represented by the following general formula (1), and the content of the yellow colorant (A1) is 90 mass% or more relative to the total mass of the yellow colorant (A).

General formula (1)

(In general formula (1), R ₁ to R ₁₃ each independently represent a hydrogen atom, a halogen atom, a hydroxyl group, an alkyl group which may have a substituent, an alkoxyl group which may have a substituent, or an aryl group which may have a substituent. In addition, at least one pair of adjacent groups among R 1 to R 4 and/or at least one pair of adjacent groups among R ₁₀ to R ₁₃ can be joined together to form an aromatic ring which may have a substituent.)

The present invention also relates to a yellow coloring composition in which the metal is at least one selected from the group consisting of aluminum, copper, zinc, iron, and silver.

The present invention also relates to a yellow coloring composition containing, as the dispersion resin (B), at least one of a basic dispersion resin (B1) or a dispersion resin (B2) which is a salt of the basic dispersion resin (B1) and a compound represented by the following general formula (2) or a compound represented by the following general formula (3):

General formula (2)

(In general formula (2), R ¹ and R ² each independently represent a hydrogen atom, a hydroxyl group, a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms, a vinyl group, a phenyl group or a benzyl group which may have a substituent, or -O-R ⁴ , and R ⁴ represents a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms, a vinyl group, a phenyl group or a benzyl group which may have a substituent, or a (meth)acryloyl group via an alkylene group having 1 to 4 carbon atoms; provided that at least one of R ¹ and R ² is a group containing a carbon atom.)

General formula (3)

(In the general formula (3), ^R3 represents a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms, a vinyl group, a phenyl group or a benzyl group which may have a substituent, or -O- ^R5 , and ^R5 represents a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms, a vinyl group, a phenyl group or a benzyl group which may have a substituent, or a (meth)acryloyl group via an alkylene group having 1 to 4 carbon atoms.)

The present invention also relates to a green coloring composition comprising the yellow coloring composition and a green colorant (D), in which the mass ratio of the yellow colorant (A) to the green colorant (D) is 70:30 to 10:90.

The present invention also relates to a red coloring composition containing the yellow coloring composition and a red colorant (E), in which the mass ratio of the yellow colorant (A) to the red colorant (E) is 70:30 to 10:90.

The present invention also relates to a photosensitive coloring composition comprising the coloring composition, a polymerizable compound (F), and a photopolymerization initiator (G).

The present invention also relates to a color filter having filter segments formed using the photosensitive coloring composition.

The present invention also relates to a liquid crystal display device having the above-mentioned color filter.

The present invention also relates to a solid-state imaging device having the above-mentioned color filter.

The present invention provides a coloring composition and a photosensitive coloring composition that have excellent brightness and contrast ratio, generate little foreign matter, have an excellent voltage retention rate, and experience little decrease in brightness under high temperature and high humidity conditions, as well as a color filter, a liquid crystal display device, and a solid-state imaging device formed using the photosensitive coloring composition.

FIG. 1 is a schematic cross-sectional view of a liquid crystal display device.

The following describes in detail the form for carrying out the present invention. Note that the present invention is not limited to the following embodiment, and can be carried out in various modifications within the scope of the gist of the invention.

The terms used in this specification are explained below. Unless otherwise specified, "(meth)acryloyl", "(meth)acrylic", "(meth)acrylic acid", "(meth)acrylate", or "(meth)acrylamide" respectively mean "acryloyl and/or methacryloyl", "acrylic and/or methacrylic", "acrylic acid and/or methacrylic acid", "acrylate and/or methacrylate", or "acrylamide and/or methacrylamide". In addition, "C.I." means Color Index.

<Yellow coloring composition>
The yellow coloring composition of the present invention is a yellow coloring composition comprising a yellow colorant (A), a dispersing resin (B), and an organic solvent (C), wherein the yellow colorant (A) comprises a yellow colorant (A1) which is a metal salt with a compound represented by the following general formula (1), and the content of the yellow colorant (A1) is 90 mass% or more with respect to the total mass of the yellow colorant (A):

General formula (1)

(In general formula (1), R ₁ to R ₁₃ each independently represent a hydrogen atom, a halogen atom, a hydroxyl group, an alkyl group which may have a substituent, an alkoxyl group which may have a substituent, or an aryl group which may have a substituent. In addition, at least one pair of adjacent groups among R ₁ to R ₄ and/or at least one pair of adjacent groups among R ₁₀ to R ₁₃ can be joined together to form an aromatic ring which may have a substituent.)

The following describes the components that are or may be included in the yellow coloring composition of one embodiment.

[Yellow colorant (A)]
(Yellow Colorant (A1))
The yellow colored composition of the present invention contains, as a yellow colorant (A), a yellow colorant (A1) which is a metal salt of a compound represented by the following general formula (1).
General formula (1)


(In general formula (1), R ₁ to R ₁₃ each independently represent a hydrogen atom, a halogen atom, a hydroxyl group, an alkyl group which may have a substituent, an alkoxyl group which may have a substituent, or an aryl group which may have a substituent. In addition, at least one pair of adjacent groups among R ₁ to R ₄ and/or at least one pair of adjacent groups among R ₁₀ to R ₁₃ can be joined together to form an aromatic ring which may have a substituent.)

The yellow colorant (A1) which is a metal salt of the compound represented by general formula (1) in the present invention is a salt formed between the _-SO3H (hereinafter referred to as a sulfo group) of the compound represented by general formula (1) and a metal.

Here, the substituents R ₁ to R ₁₃ in general formula (1) will be described.

Halogen atoms include fluorine, chlorine, bromine, and iodine. Of these, chlorine is preferred.

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

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

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

At least one pair of adjacent groups among R ₁ to R ₄ and/or at least one pair of adjacent groups among R ₁₀ to R ₁₃ can be joined together to form an aromatic ring which may have a substituent. The aromatic ring referred to here includes 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 examples of the heteroaromatic ring include a pyridine ring, a pyrazine ring, a pyrrole ring, a quinoline ring, a quinoxaline ring, a furan ring, a benzofuran ring, a thiophene ring, a benzothiophene ring, an oxazole ring, a thiazole ring, an imidazole ring, a pyrazole ring, an indole ring, and a carbazole ring. Among these, a benzene ring is preferable.

The yellow colorant (A1) used in the yellow colored composition of the present invention is preferably a metal salt with a compound represented by the following general formula (1-1) or the following general formula (1-2).

General formula (1-1)

(In general formula (1-1), R ₁₅ to R ₂₇ each independently represent a hydrogen atom, a halogen atom, a hydroxyl group, an alkyl group which may have a substituent, an alkoxyl group which may have a substituent, or an aryl group which may have a substituent.)

General formula (1-2)

(In general formula (1-2), R ₂₈ to R ₄₂ each independently represent a hydrogen atom, a halogen atom, a hydroxyl group, an alkyl group which may have a substituent, an alkoxyl group which may have a substituent, or an aryl group which may have a substituent.)

The halogen atoms, hydroxyl groups, alkyl groups which may have a substituent, alkoxy groups which may have a substituent, and aryl groups which may have a substituent in R ₁₅ to R ₂₇ and R ₂₈ to R ₄₂ have the same meanings as the groups explained in general formula (1).

Furthermore, in the yellow colorant (A1) used in the yellow colored composition of the present invention, R ₁₅ to R ₂₇ and R _{to R} in the general formula (1-1) or the following general formula (1-2) are more preferably hydrogen atoms or halogen atoms.

From the viewpoint of brightness and contrast ratio, the number of sulfo groups in general formula (1) is preferably 1 to 3, and more preferably 1 or 2.

Metals constituting metal salts with the compound represented by general formula (1) include sodium, potassium, magnesium, calcium, strontium, barium, chromium, manganese, iron, cobalt, nickel, copper, silver, zinc, aluminum, and gallium. Among these, aluminum, zinc, copper, and silver are preferred from the viewpoints of brightness, contrast ratio, and foreign matter, aluminum, zinc, copper, and iron are preferred from the viewpoint of voltage retention rate in the photosensitive green coloring composition described below, and copper, iron, and silver are preferred from the viewpoint of suppressing brightness reduction under high temperature and high humidity conditions.

Specific examples of the yellow colorant (A1) used in the yellow coloring composition of the present invention include metal salts with the compounds shown below, but the present invention is not limited to these.

The content of the yellow colorant (A1) used in the yellow coloring composition of the present invention is 90% by mass or more, and more preferably 95% by mass or more, based on the total mass of the yellow colorant (A). If the content of the yellow colorant (A1) is less than 90% by mass based on the total mass of the yellow colorant (A), the desired brightness and contrast ratio cannot be obtained.

In the present invention, the yellow colorant (A1) may be used alone or in combination of two or more.

In the present invention, from the viewpoints of the brightness, contrast ratio, voltage holding ratio, and suppression of brightness decrease under high temperature and high humidity in the photosensitive green coloring composition described later, it is preferable to use two or more kinds of yellow colorants (A1) in combination in which the metal is selected from the group consisting of aluminum, copper, zinc, iron, and silver, and it is more preferable to use two or more kinds of yellow colorants (A1) in combination in which the metal is selected from the group consisting of aluminum, copper, and zinc.

(Other Yellow Colorants (A2))
The yellow coloring composition of the present invention may contain, as the yellow colorant (A), other yellow colorants (A2) in addition to the yellow colorant (A1) as long as the effects of the present invention are not impaired. From the viewpoints of brightness, contrast ratio, and suppression of foreign matter, the content of the other yellow colorant (A2) is preferably less than 10 mass%, more preferably less than 5 mass%, based on the total mass of the yellow colorant (A).

Other yellow colorants (A2) that can be used in the present invention include, for example, C.I. Pigment Yellow 1, 2, 3, 4, 5, 6, 10, 11, 12, 13, 14, 15, 16, 17, 18, 20, 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, 86, 93, 94, 95, 97, 98, 100, 101, 104, 106, 108, 109, 110, 113, 114, 115, 116, 117, 118, 1 Pigments such as 19, 120, 123, 125, 126, 127, 128, 129, 137, 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;
C.I. Acid Yellow 2, 3, 4, 5, 6, 7, 8, 9, 9:1, 10, 11, 11:1, 12, 13, 14, 15, 16, 17, 17:1, 18, 20, 21, 22, 23, 25, 26, 27, 29, 30, 31, 33, 34, 36, 38, 39, 40, 40:1, 41, 42, 42:1, 43, 44, 46, 48, 51, 53, 55, 56, 60, 63, 65, 66, 67, 6 8, 69, 72, 76, 82, 83, 84, 86, 87, 90, 94, 105, 115, 117, 122, 127, 131, 132, 136, 141, 142, 143, 144, 145, 146, 149, 153, 159, 166, 168, 169, 172, 174, 175, 178, 180, 183, 187, 188, 189, 190, 191, 192, 199, C. I. Direct Yellow 1, 2, 4, 5, 12, 13, 15, 20, 24, 25, 26, 32, 33, 34, 35, 41, 42, 44, 44: 1, 45, 46, 48, 49, 50, 51, 61, 66, 67, 69, 70, 71, 72, 73, 74, 81, 84, 86, 90, 91, 92, 95, 107, 110, 117, 118, 119, 120, 121, 126, 127, 129, 132, 133, 134, C.I. Basic Yellow 1, 2, 5, 11, 13, 14, 15, 19, 21, 24, 25, 28, 29, 37, 40, 45, 49, 51, 57, 79, 87, 90, 96, 103, 105, 106, C.I. Solvent Yellow 2, 7, 28, 29, 30, 32, 33, 34, 40, 42, 43, 44, 45, 47, 48, 56, 62, 64, 68, 69, 71, 72, 73, 77, 79, 81, 82, 83, 85, 88, 89, 90, 93, 94, 98, 104, 107, 114, 116, 117, 124, 1 30, 131, 133, 135, 138, 141, 143, 145, 146, 147, 157, 160, 162, 163, 167, 172, 174, 175, 176, 177, 179, 181, 182, 183, 184, 185, 186, 187, 188, 190, 191, 192, 194, 195, C. I. Dyes such as Disperse Yellow 1, 2, 3, 5, 7, 8, 10, 11, 13, 13, 23, 27, 33, 34, 42, 45, 48, 51, 54, 56, 59, 60, 63, 64, 67, 70, 77, 79, 82, 85, 88, 93, 99, 114, 118, 119, 122, 123, 124, 126, 163, 184, 184:1, 202, 211, 229, 231, 232, 233, 241, 245, 246, 247, 248, 249, 250, and the like can be mentioned, but are not particularly limited thereto.

The yellow colorant (A) of the present invention is preferably used in a finely divided state. The method of finely dividing is not particularly limited, and for example, any of wet grinding, dry grinding, and dissolution precipitation methods can be used. As exemplified in the present invention, finely dividing can be performed by salt milling using a kneader method, which is a type of wet grinding. The average primary particle size of the colorant as determined by TEM (transmission electron microscope) is preferably in the range of 5 to 90 nm. From the viewpoints of dispersion in organic solvents and contrast ratio, the average primary particle size is more preferably in the range of 10 to 70 nm.

Salt milling is a process in which a mixture of a colorant, a water-soluble inorganic salt, and a water-soluble organic solvent is mechanically kneaded while being heated using a kneader, two-roll mill, three-roll mill, ball mill, attritor, sand mill, or other kneading machine, and then the water-soluble inorganic salt and the water-soluble organic solvent are removed by washing with water. The water-soluble inorganic salt acts as a crushing aid, and the colorant is crushed during salt milling by utilizing the high hardness of the inorganic salt. By optimizing the conditions for salt milling the colorant, a colorant can be obtained that has a very fine primary particle diameter, a narrow distribution range, and a sharp particle size distribution.

Sodium chloride, potassium chloride, sodium sulfate, etc. can be used as the water-soluble inorganic salt, but sodium chloride (table salt) is preferred from the viewpoint of cost. From the viewpoints of both processing efficiency and production efficiency, the water-soluble inorganic salt is preferably used in an amount of 50 to 2,000 mass%, and most preferably 300 to 1,000 mass%, based on the total mass of the colorant (100 mass%).

The water-soluble organic solvent is a solvent that moistens the colorant and the water-soluble inorganic salt, and is not particularly limited as long as it dissolves (is mixed) in water and does not substantially dissolve the inorganic salt used. However, since the temperature rises during salt milling and the solvent becomes prone to evaporate, a high-boiling solvent with a boiling point of 120°C or higher is preferred from the standpoint of safety. For example, 2-methoxyethanol, 2-butoxyethanol, 2-(isopentyloxy)ethanol, 2-(hexyloxy)ethanol, diethylene glycol, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, triethylene glycol, triethylene glycol monomethyl ether, liquid polyethylene glycol, 1-methoxy-2-propanol, 1-ethoxy-2-propanol, dipropylene glycol, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, liquid polypropylene glycol, etc. may be used. The water-soluble organic solvent is preferably used in an amount of 5 to 1,000% by mass, and most preferably 50 to 500% by mass, based on the total mass of the colorant (100% by mass).

When the colorant is subjected to salt milling, a resin may be added as necessary. There are no particular limitations on the type of resin used, and natural resins, modified natural resins, synthetic resins, synthetic resins modified with natural resins, etc. may be used. The resin used is preferably solid at room temperature and insoluble in water, and more preferably partially soluble in the organic solvents mentioned above. The amount of resin used is preferably in the range of 2 to 200% by mass, based on the total mass of the colorant (100% by mass).

[Dispersion Resin (B)]
The yellow colored composition of the present invention contains a dispersing resin (B). The dispersing resin (B) is not particularly limited, and any known dispersing resin can be used.

Specific examples include polyurethane, polyacrylate and other polycarboxylate esters, unsaturated polyamides, polycarboxylic acids, polycarboxylate (partial) amine salts, polycarboxylate ammonium salts, polycarboxylate alkylamine salts, polysiloxanes, long-chain polyaminoamide phosphates, hydroxyl-containing polycarboxylate esters and their modifications, oil-based dispersants such as amides formed by the reaction of poly(lower alkylene imines) with polyesters having free carboxyl groups and their salts, water-soluble resins and water-soluble polymer compounds such as (meth)acrylic acid-styrene copolymers, (meth)acrylic acid-(meth)acrylic acid ester copolymers, styrene-maleic acid copolymers, polyvinyl alcohol, and polyvinylpyrrolidone, polyesters, modified polyacrylates, ethylene oxide/propylene oxide adducts, and phosphate esters.

The structure of the dispersion resin (B) is not particularly limited, but examples include a random structure, a block structure, a comb structure, and a star structure. Among these, from the viewpoint of dispersion stability, a block structure or a comb structure is preferred.

The dispersion resin (B) may be used alone or in combination of two or more.

From the viewpoint of dispersion stability, the content of the dispersion resin (B) is preferably 3 to 200% by mass, and more preferably 5 to 100% by mass, relative to 100% by mass of the yellow colorant (A).

From the viewpoint of brightness and contrast ratio, the dispersion resin (B) used in the yellow coloring composition of the present invention preferably contains at least one of a basic dispersion resin (B1) or a dispersion resin (B2) which is a salt of the basic dispersion resin (B1) and a compound represented by the following general formula (2) or a compound represented by the following general formula (3).

General formula (2)

In general formula (2), R ¹ and R ² each independently represent a hydrogen atom, a hydroxyl group, a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms, a vinyl group, a phenyl group or a benzyl group which may have a substituent, or -O-R ⁴ , and R ⁴ represents a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms, a vinyl group, a phenyl group or a benzyl group which may have a substituent, or a (meth)acryloyl group via an alkylene group having 1 to 4 carbon atoms, with the proviso that at least one of R ¹ and R ² is a group containing a carbon atom.

General formula (3)

(In the general formula (3), ^R3 represents a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms, a vinyl group, a phenyl group or a benzyl group which may have a substituent, or -O- ^R5 , and ^R5 represents a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms, a vinyl group, a phenyl group or a benzyl group which may have a substituent, or a (meth)acryloyl group via an alkylene group having 1 to 4 carbon atoms.)

(Basic Dispersion Resin (B1))
The basic dispersion resin (B1) is, for example, a copolymer obtained by radical polymerization of ethylenically unsaturated monomers including an ethylenically unsaturated monomer having a basic group, and has an affinity site including a basic group that adsorbs to the yellow colorant (A), and functions to stabilize the dispersion by adsorbing to the yellow colorant (A).

Here, the basic group is a functional group having a nitrogen atom. Examples of the basic dispersion resin (B1) include nitrogen atom-containing graft copolymers, and nitrogen atom-containing acrylic block copolymers, random copolymers, and urethane resins having functional groups in the side chains including primary amino groups, secondary amino groups, tertiary amino groups, quaternary ammonium bases, and nitrogen-containing heterocycles.

In the present invention, it is preferable that the basic dispersion resin (B1) has at least one structural unit selected from the group represented by the following general formulas (b1-a), (b1-b), and (b1-c).

General formula (b1-a)

(In general formula (b1-a), R ⁶ to R ⁸ each independently represent a hydrogen atom or a linear or cyclic hydrocarbon group which may have a substituent, and two or more of R ⁶ to R ⁸ may be bonded to each other to form a cyclic structure. R ⁹ represents a hydrogen atom or a methyl group, X represents a divalent linking group, and Y ⁻ represents a counter anion.)

General formula (b1-b)

(In general formula (b1-b), R ¹⁰ and R ¹¹ each independently represent a hydrogen atom or a chain or cyclic hydrocarbon group which may have a substituent, and R ¹⁰ and R ¹¹ may be bonded to each other to form a cyclic structure. R ¹² represents a hydrogen atom or a methyl group, and X represents a divalent linking group.)

General formula (b1-c)

(In general formula (b1-c), R ¹³ represents a hydrogen atom, an alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 20 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, an acyl group, an oxy radical group, or OR ¹⁹ ; R ¹⁹ represents a hydrogen atom, an alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 20 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or an acyl group; R ¹⁴ to R ¹⁷ each independently represent a methyl group, an ethyl group, or a phenyl group; R ¹⁸ represents a hydrogen atom or a methyl group; and X represents a divalent linking group.)

As R ⁶ to R ⁸ in general formula (b1-a), an optionally substituted alkyl group having 1 to 4 carbon atoms and an optionally substituted aralkyl group having 7 to 16 carbon atoms are more preferable, and a methyl group, an ethyl group, a propyl group, a butyl group, and a benzyl group are particularly preferable.

In general formula (b1-b), R ¹⁰ and R ¹¹ are more preferably an alkyl group having 1 to 4 carbon atoms which may have a substituent, and a methyl group, an ethyl group, a propyl group and a butyl group are particularly preferred.

In R ¹³ in general formula (b1-c), examples of the alkyl group having 1 to 18 carbon atoms include linear, branched and cyclic alkyl groups. Specific examples thereof include a methyl group, an ethyl group, a normal propyl group, an isopropyl group, an n-butyl group, a t-butyl group, an n-hexyl group, a cyclohexyl group, an n-octyl group, and a hexadecyl group.
Examples of the aryl group having 6 to 20 carbon atoms include a phenyl group, a 1-naphthyl group, and a 2-naphthyl group.
Examples of the aralkyl group having 7 to 12 carbon atoms include a group in which an aryl group having 6 to 10 carbon atoms is bonded to an alkyl group having 1 to 8 carbon atoms. Specific examples of the aralkyl group having 7 to 12 carbon atoms include a benzyl group, a phenethyl group, an α-methylbenzyl group, and a 2-phenylpropan-2-yl group.
Examples of the acyl group include alkanoyl groups having 2 to 8 carbon atoms and aroyl groups, and specific examples thereof include an acetyl group and a benzoyl group.
Among these, a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, and an oxyradical group are particularly preferred, a hydrogen atom and a methyl group are more preferred, and a methyl group is most preferred.

In general formula (b1-a), general formula (b1-b), and general formula (b1-c), examples of the divalent linking group X include a methylene group, an alkylene group having 2 to 10 carbon atoms, an arylene group, -CONH-R ²⁰ -, -COO-R ²¹ - (wherein R ²⁰ and R ²¹ are single bonds, a methylene group, an alkylene group having 2 to 10 carbon atoms, or an ether group (alkyloxyalkyl group) having 2 to 10 carbon atoms), and preferably -CONH-R ²⁰ -, -COO-R ²¹ -. In addition, in the above formula (b1-a), examples of the counter anion Y ^- include Cl ^- , Br ^- , I ^- , ClO ₄ ^- , BF ₄ ^- , CH ₃ COO ^- , and PF ₆ ^- .

Specific examples of the ethylenically unsaturated monomer having a quaternary ammonium base, which is the precursor or partial structure of the general formula (b1-a), include alkyl (meth)acrylate-based quaternary ammonium salts such as (meth)acryloyloxyethyl trimethyl ammonium chloride, (meth)acryloyloxyethyl triethyl ammonium chloride, (meth)acryloyloxyethyl dimethyl benzyl ammonium chloride, and (meth)acryloyloxyethyl methyl morpholino ammonium chloride;
alkyl(meth)acryloylamide-based quaternary ammonium salts such as (meth)acryloylaminopropyltrimethylammonium chloride, (meth)acryloylaminoethyltriethylammonium chloride, and (meth)acryloylaminoethyldimethylbenzylammonium chloride;
Examples thereof include dimethyldiallylammonium methyl sulfate and trimethylvinylphenylammonium chloride.

Specific examples of the ethylenically unsaturated monomer having a tertiary amine group, which is the precursor or partial structure of general formula (b1-b), include (meth)acrylates having a tertiary amino group, such as N,N-dimethylaminoethyl (meth)acrylate, N,N-diethylaminoethyl (meth)acrylate, N,N-dimethylaminopropyl (meth)acrylate, and N,N-diethylaminopropyl (meth)acrylate;
Examples of the tertiary amino group-containing (meth)acrylamides include N,N-dimethylaminoethyl(meth)acrylamide, N,N-diethylaminoethyl(meth)acrylamide, N,N-dimethylaminopropyl(meth)acrylamide, and N,N-diethylaminopropyl(meth)acrylamide.

Specific examples of ethylenically unsaturated monomers that serve as precursors or partial structures of general formula (b1-c) include compounds represented by the following general formulas (b1-c-1) to (b1-c-11).

General formula (b1-c-1)

General formula (b1-c-2)

General formula (b1-c-3)

General formula (b1-c-4)

General formula (b1-c-5)

General formula (b1-c-6)

General formula (b1-c-7)

General formula (b1-c-8)

General formula (b1-c-9)

General formula (b1-c-10)

General formula (b1-c-11)

In general formulae (b1-c-1) to (b1-c-11), R ²² represents a hydrogen atom or a methyl group.

Of these, 2,2,6,6-tetramethylpiperidyl methacrylate (a compound in which R ²² in the general formula (b1-c-1) is a methyl group) and 1,2,2,6,6-pentamethylpiperidyl methacrylate (a compound in which R ²² in the general formula (b1-c-2) is a methyl group) are preferred, and 1,2,2,6,6-pentamethylpiperidyl methacrylate is particularly preferred.

The structural units represented by general formula (b1-a), general formula (b1-b), and general formula (b1-c) may be contained alone or in combination, and from the viewpoint of storage stability, it is preferable to use general formula (b1-a) and general formula (b1-b) in combination. Furthermore, each structural unit may be contained in any of the modes of random copolymerization, block copolymerization, and graft copolymerization. Among these, from the viewpoint of storage stability, it is preferable that the structural units represented by general formula (b1-a), general formula (b1-b), and general formula (b1-c) are contained in the form of block copolymerization.

The structural units other than those represented by general formula (b1-a), general formula (b1-b), and general formula (b1-c) are not particularly limited as long as they are polymer structures in which copolymerizable monomers are copolymerized, and can be appropriately selected depending on the application. The copolymerizable monomers are shown below.

For example, linear or branched alkyl (meth)acrylates such as methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, isopropyl (meth)acrylate, butyl (meth)acrylate, isobutyl (meth), tertiary butyl (meth)acrylate, isoamyl (meth)acrylate, octyl (meth)acrylate, isooctyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, cetyl (meth)acrylate, decyl (meth)acrylate, isodecyl (meth)acrylate, lauryl (meth)acrylate, tridecyl (meth)acrylate, isomyristyl (meth)acrylate, stearyl (meth)acrylate, and isostearyl (meth)acrylate;
cyclic alkyl (meth)acrylates such as cyclohexyl (meth)acrylate, tertiary butyl cyclohexyl (meth)acrylate, dicyclopentanyl (meth)acrylate, dicyclopentenyl (meth)acrylate, and isobornyl (meth)acrylate;
(meth)acrylates having a heterocycle, such as tetrahydrofurfuryl (meth)acrylate and 3-methyl-3-oxetanyl (meth)acrylate;
(Meth)acrylates having an aromatic ring, such as benzyl (meth)acrylate and phenoxyethyl (meth)acrylate; 2-methoxyethyl (meth)acrylate, 2-ethoxyethyl (meth)acrylate, 2-methoxypropyl (meth)acrylate, diethylene glycol monomethyl ether (meth)acrylate, diethylene glycol monoethyl ether (meth)acrylate, diethylene glycol mono-2-ethylhexyl ether (meth)acrylate, dipropylene glycol monomethyl ether (meth)acrylate, triethylene glycol monomethyl ether (meth)acrylate, triethylene glycol monoethyl ether (meth)acrylate, (poly)alkylene glycol monoalkyl ether (meth)acrylates such as ethyl ether (meth)acrylate, tripropylene glycol monomethyl ether (meth)acrylate, tetraethylene glycol monomethyl ether (meth)acrylate, polyethylene glycol monomethyl ether (meth)acrylate, polypropylene glycol monomethyl ether (meth)acrylate, polyethylene glycol monolauryl ether (meth)acrylate, polyethylene glycol monostearyl ether (meth)acrylate, and octoxypolyethylene glycol-polypropylene glycol (meth)acrylate;
(poly)alkylene glycol (meth)acrylates having an aromatic ring, such as phenoxyethyl (meth)acrylate, phenoxydiethylene glycol (meth)acrylate, phenoxytetraethylene glycol (meth)acrylate, phenoxyhexaethylene glycol (meth)acrylate, phenoxypolyethylene glycol (meth)acrylate, paracumylphenoxyethyl (meth)acrylate, paracumylphenoxyethylene glycol (meth)acrylate, paracumylphenoxypolyethylene glycol (meth)acrylate, nonylphenoxypolyethylene glycol (meth)acrylate, nonylphenoxypolypropylene glycol (meth)acrylate, and nonylphenoxypoly(ethylene glycol-propylene glycol) (meth)acrylate;
(meth)acrylates having an alkyloxysilyl group, such as 3-methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane, 3-methacryloxypropyltriethoxysilane, and 3-acryloxypropyltrimethoxysilane;
Fluoroalkyl (meth)acrylates such as trifluoroethyl (meth)acrylate, octafluoropentyl (meth)acrylate, perfluorooctylethyl (meth)acrylate, and tetrafluoropropyl (meth)acrylate; (meth)acryloxy-modified polydimethylsiloxanes (silicone macromers);
Examples of the compound include N-substituted (meth)acrylamides such as (meth)acrylamide, dimethyl(meth)acrylamide, N,N-diethyl(meth)acrylamide, N-isopropyl(meth)acrylamide, diacetone(meth)acrylamide, and acryloylmorpholine; and nitriles such as (meth)acrylonitrile.
Other examples include styrenes such as styrene and α-methylstyrene; vinyl ethers such as ethyl vinyl ether, n-propyl vinyl ether, isopropyl vinyl ether, n-butyl vinyl ether, and isobutyl vinyl ether; and vinyl fatty acid vinyls such as vinyl acetate and vinyl propionate.

Furthermore, a carboxyl group-containing ethylenically unsaturated monomer can also be used in combination. Examples of carboxyl group-containing ethylenically unsaturated monomers include (meth)acrylic acid, (meth)acrylic acid dimer, itaconic acid, maleic acid, fumaric acid, crotonic acid, 2-(meth)acryloyloxyethyl phthalate, 2-(meth)acryloyloxypropyl phthalate, 2-(meth)acryloyloxyethyl hexahydrophthalate, 2-(meth)acryloyloxypropyl hexahydrophthalate, β-carboxyethyl (meth)acrylate, and ω-carboxypolycaprolactone (meth)acrylate.

In addition, ethylenically unsaturated monomers containing an amino group other than the structural units represented by general formula (b1-a), general formula (b1-b), and general formula (b1-c) may be used in combination, provided that the effects of the present invention are not impaired.

From the viewpoints of storage stability and developability, the weight average molecular weight of the basic dispersion resin (B1) is preferably 1,000 to 100,000 in terms of polystyrene equivalent weight average.

(Dispersion resin (B2) which is a salt of a compound represented by general formula (2) or a compound represented by general formula (3) and a basic dispersion resin (B1))
The dispersing resin (B2) is a salt of a compound represented by the following general formula (2) or a compound represented by the following general formula (3) and the basic dispersing resin (B1).

General formula (2)

In general formula (2), R ¹ and R ² each independently represent a hydrogen atom, a hydroxyl group, a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms, a vinyl group, a phenyl group or a benzyl group which may have a substituent, or -O-R ⁴ , and R ⁴ represents a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms, a vinyl group, a phenyl group or a benzyl group which may have a substituent, or a (meth)acryloyl group via an alkylene group having 1 to 4 carbon atoms, with the proviso that at least one of R ¹ and R ² is a group containing a carbon atom.

General formula (3)

(In the general formula (3), ^R3 represents a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms, a vinyl group, a phenyl group or a benzyl group which may have a substituent, or -O- ^R5 , and ^R5 represents a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms, a vinyl group, a phenyl group or a benzyl group which may have a substituent, or a (meth)acryloyl group via an alkylene group having 1 to 4 carbon atoms.)

Examples of the compound represented by the general formula (2) include monobutyl phosphate, dibutyl phosphate, methyl phosphate, dibenzyl phosphate, diphenyl phosphate, phenylphosphinic acid, phenylphosphonic acid, and dimethacryloyloxyethyl acid phosphate.

Examples of the compound represented by the general formula (3) include benzenesulfonic acid, vinylsulfonic acid, methanesulfonic acid, p-toluenesulfonic acid, monomethylsulfuric acid, monoethylsulfuric acid, mono-n-propylsulfuric acid, etc. Hydrates such as p-toluenesulfonic acid monohydrate may also be used.

Among the compounds represented by the general formula (2) or the compounds represented by the general formula (3), the general formula (2) is preferred from the viewpoint of suppressing the generation of foreign matter.

The yellow coloring composition of the present invention may contain other dispersion resins as the dispersion resin (B) in addition to the basic dispersion resin (B1). There are no particular restrictions on the other dispersion resins, and known dispersion resins can be used. Among them, acidic dispersion resins such as phosphoric acid-based dispersion resins (B3) and carboxylic acid-based dispersion resins (B4) are preferred.

(Phosphoric acid-based dispersion resin (B3))
In the present invention, the phosphoric acid-based dispersion resin (B3) refers to a resin having a phosphoric acid bond [(-O) ₃ P=O] in the molecule. Preferred examples are phosphoric acid-based dispersion resins represented by either (B3-1) or (B3-2) below.

(Phosphoric acid-based dispersion resin (B3-1))
In the present invention, the phosphoric acid-based dispersion resin (B3-1) is represented by the following general formula (4).
General formula (4)
(HO-) _3-n -PO-(O-R ¹ ) _n
(In the general formula (4), ^R1 represents a polyester residue having a number average molecular weight of 300 to 10,000, and n represents 1 or 2.)

The phosphoric acid-based dispersion resin represented by the general formula (4) has a great effect of suppressing re-aggregation of the pigment after dispersion, and therefore produces a color filter with excellent transparency. Furthermore, due to the structure of the general formula (4), it is possible to enhance the self-solubility of the colored resin composition solidified at the tip of the coating liquid discharge port of a die-coating type coating device.

The phosphoric acid-based dispersion resin represented by general formula (4) is preferably produced, for example, by ring-opening addition of a cyclic ester to a monoalcohol as an initiator (first step), followed by phosphorylation (second step).

The monoalcohol is not particularly limited as long as it has one hydroxyl group in the molecule, and any primary, secondary, or tertiary alcohol can be used. For example, methanol, ethanol, propanol, isopropanol, butanol, sec-butanol, t-butanol, pentanol, amyl alcohol, hexanol, heptanol, octanol, 2-ethylhexyl alcohol, nonanol, decanol, lauryl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol, oleyl alcohol, hexadecyl alcohol, and mixtures thereof can be used. In particular, lauryl alcohol, N-hexanol, and hexadecyl alcohol are preferred.

Polyester residues having a hydroxyl group at one end can be obtained by ring-opening addition polymerization of ε-caprolactone or the like using a monoalcohol as an initiator. The addition reaction of ε-caprolactone can be carried out by a known method, for example, by charging a monoalcohol, ε-caprolactone, and a polymerization catalyst into a reactor connected to a dehydration tube and a condenser, and carrying out the reaction under nitrogen gas flow. When a monoalcohol with a low boiling point is used, the reaction can be carried out under pressure using an autoclave. The reaction can be carried out without solvent or with a suitable dehydrating solvent such as toluene or xylene. After completion of the reaction, the solvent used in the reaction can be removed by distillation or the like, or can be used as it is as part of the product.

The reaction temperature in the first step is in the range of 120° C. to 220° C., preferably 160° C. to 210° C. If the reaction temperature is less than 120° C., the reaction rate is extremely slow, whereas if the reaction temperature exceeds 220° C., side reactions other than the addition reaction of ε-caprolactone, such as decomposition of the ε-caprolactone adduct into ε-caprolactone monomer and production of cyclic ε-caprolactone dimer, are likely to occur.
The number of moles of ε-caprolactone added per mole of monoalcohol is 1 to 50 moles, preferably 3 to 20 moles. If the number of moles added is less than 1 mole, it becomes difficult to obtain the effect as a dispersant, whereas if it is more than 50 moles, the molecular weight of the reaction product becomes too large, which tends to lead to a decrease in dispersibility and flowability.

Examples of polymerization catalysts include quaternary ammonium salts such as tetramethylammonium chloride, tetrabutylammonium chloride, tetramethylammonium bromide, tetrabutylammonium bromide, tetramethylammonium iodide, tetrabutylammonium iodide, benzyltrimethylammonium chloride, benzyltrimethylammonium bromide, and benzyltrimethylammonium iodide; tetramethylphosphonium chloride, tetrabutylphosphonium chloride, tetramethylphosphonium bromide, tetrabutylphosphonium bromide, tetramethylphosphonium iodide, tetrabutylphosphonium iodide, and benzyl Examples of the catalyst include quaternary phosphonium salts such as benzyl trimethylphosphonium chloride, benzyl trimethylphosphonium bromide, benzyl trimethylphosphonium iodide, tetraphenylphosphonium chloride, tetraphenylphosphonium bromide, and tetraphenylphosphonium iodide, phosphorus compounds such as triphenylphosphine, organic carboxylates such as potassium acetate, sodium acetate, potassium benzoate, and sodium benzoate, alkali metal alcoholates such as sodium alcoholates and potassium alcoholates, tertiary amines, organic tin compounds, organic aluminum compounds, organic titanate compounds, and zinc compounds such as zinc chloride. The amount of catalyst used is 0.1 ppm to 3000 ppm, preferably 1 ppm to 1000 ppm. If the amount of catalyst exceeds 3000 ppm, the resin will be colored severely, which will have a negative effect on the stability of the product. Conversely, if the amount of catalyst used is less than 0.1 ppm, the ring-opening addition polymerization rate of the cyclic ester will be extremely slow, which is not preferable.

The polyester residue having a hydroxyl group at one end can be phosphorylated by reacting it with one or a combination of two or more phosphorylating agents such as phosphorus pentoxide, polyphosphoric acid, orthophosphoric acid, and phosphorus oxychloride. Of these, one or more phosphorylating agents selected from the group consisting of orthophosphoric acid, polyphosphoric acid, and phosphorus pentoxide are preferred because they do not produce by-products such as hydrochloric acid gas and do not require special equipment. Of these, polyphosphoric acid with an orthophosphoric acid content of 116% by mass is preferred.

The charge ratio of the phosphate esterification agent is preferably such that the molar ratio of phosphorus atoms in the phosphate esterification agent to the hydroxyl groups of the polyester residue having a hydroxyl group at one end is 0.5 to 1.5, more preferably 1.0 to 1.3, and most preferably 1.05 to 1.2. If the molar ratio of phosphorus atoms to epoxy groups is less than 0.5, the phosphate esterification of the hydroxyl groups tends to be insufficient and the amount of phosphoric diester by-product tends to increase, while if it exceeds 1.5, the effect of increasing the amount added tends not to be commensurate with the amount added.

The reaction temperature in the second step is not particularly limited, but is preferably 40°C to 130°C, more preferably 50°C to 110°C, and most preferably 60°C to 100°C. If the reaction temperature is lower than these ranges, the esterification reaction may be insufficient and the phosphate esterification agent may remain, while if the reaction temperature is higher than these ranges, by-products are more likely to be produced and the esterification reaction product is more likely to decompose.

In general formula (4), from the viewpoint of dispersibility, it is preferable that the molar ratio of the phosphate ester where n=1 and the phosphate ester where n=2 is 100:0 to 100:30.

In addition, in the general formula (4), it is preferable that R ¹ has a structure represented by the following general formula (4-1).
General formula (4-1)
-( ^R2 -COO-) _m - ^R3
(In the general formula (4-1), ^R2 represents a lactone residue, ^R3 represents a monoalcohol residue, and m represents an integer of 1 to 50.)
For example, when R ¹ is a polycaprolactone residue, the pigment dispersibility and dry solubility become good, which is preferable. In particular, a polycaprolactone residue having a number average molecular weight of 300 to 10,000 is more preferable.

(Phosphoric acid-based dispersion resin (B3-2))
In the present invention, the phosphoric acid-based dispersion resin (B3-2) is a dispersion resin which is a copolymer of an ethylenically unsaturated monomer having a phosphoric acid group and another ethylenically unsaturated monomer, and is described in JP-A-2003-253078 and JP-A-2008-161737.

(Carboxylic Acid-Based Dispersion Resin (B4))
In the present invention, the carboxylic acid-based dispersion resin (B4) refers to a resin having dispersibility and containing a carboxyl group (-COOH) in the molecule. Preferred examples are the carboxylic acid-based dispersion resins shown in either (B4-1) or (B4-2) below.

(Carboxylic Acid-Based Dispersion Resin (B4-1))
The carboxylic acid dispersion resin (B4-1) is a resin comprising a polyester portion having a carboxyl group, which is formed by reacting an acid anhydride group in one or more acid anhydrides selected from the group consisting of tetracarboxylic dianhydrides and tricarboxylic anhydrides with a hydroxyl group in a hydroxyl group-containing compound, and a vinyl polymer portion formed by radical polymerization of an ethylenically unsaturated monomer.

First, let us explain the polyester portion. The polyester portion has multiple ester groups that result from the reaction between an acid anhydride group and a hydroxyl group.

The tetracarboxylic dianhydride used in the present invention includes 1,2,3,4-butane tetracarboxylic dianhydride, 1,2,3,4-cyclobutane tetracarboxylic dianhydride, 1,3-dimethyl-1,2,3,4-cyclobutane tetracarboxylic dianhydride, 1,2,3,4-cyclopentane tetracarboxylic dianhydride, 2,3,5-tricarboxycyclopentyl acetic dianhydride, 3,5,6-tricarboxynorbornane-2-acetic dianhydride, 2,3,4,5-tetrahydrofuran tetracarboxylic dianhydride, 5-(2,5-dioxotetrahydrofural)-3-methyl-3-cyclohexene-1,2-dicarboxylic dianhydride, bicyclo[2.2.2]-octyl tetracarboxylic dianhydride, 5-(2,5-dioxotetrahydrofural)-3-methyl-3-cyclohexene-1,2-di ... aliphatic tetracarboxylic dianhydrides such as 2,3,5,6-phenyl-7-ene-tetracarboxylic dianhydride, pyromellitic dianhydride, ethylene glycol ditrimellitic anhydride, propylene glycol ditrimellitic anhydride, butylene glycol ditrimellitic anhydride, 3,3',4,4'-benzophenone tetracarboxylic dianhydride, 3,3',4,4'-biphenylsulfone tetracarboxylic dianhydride, 1,4,5,8-naphthalene tetracarboxylic dianhydride, 2,3,6,7-naphthalene tetracarboxylic dianhydride, 3,3',4,4'-biphenyl ether tetracarboxylic dianhydride, 3,3',4,4'-dimethyldiphenyl silane tetracarboxylic dianhydride, 3,3',4,4'-tetraphenylsilane tetracarboxylic dianhydride, 1,2,3,4-furan tetracarboxylic dianhydride, 4,4'-bis(3,4-dicarboxyphenoxy)diphenyl sulfide dianhydride, 4,4'-bis(3,4-dicarboxyphenoxy)diphenyl sulfone dianhydride, 4,4'-bis(3,4-dicarboxyphenoxy)diphenylpropane dianhydride, 3,3',4,4'-perfluoroisopropylidenediphthalic dianhydride, 3,3',4,4'-biphenyl tetracarboxylic dianhydride, bis(phthalic acid)phenylphosphine oxide dianhydride, p-phenylene-bis(triphenyl Examples of aromatic tetracarboxylic acid dianhydrides include m-phenylene-bis(triphenylphthalic acid) dianhydride, bis(triphenylphthalic acid)-4,4'-diphenyl ether dianhydride, bis(triphenylphthalic acid)-4,4'-diphenyl methane dianhydride, 9,9-bis(3,4-dicarboxyphenyl)fluorene dianhydride, 9,9-bis[4-(3,4-dicarboxyphenoxy)phenyl]fluorene dianhydride, 3,4-dicarboxy-1,2,3,4-tetrahydro-1-naphthalene succinic acid dianhydride, and 3,4-dicarboxy-1,2,3,4-tetrahydro-6-methyl-1-naphthalene succinic acid dianhydride.

The tetracarboxylic dianhydrides used in the present invention are not limited to the compounds exemplified above, and may have any structure as long as they have two carboxylic anhydride groups. These may be used alone or in combination. Tetracarboxylic dianhydrides form a dispersion resin having two carboxyl groups per tetracarboxylic dianhydride unit by reacting with a hydroxyl group-containing compound, and are therefore preferred as components of the dispersion resin from the viewpoint of pigment adsorption.

Furthermore, from the viewpoint of adsorption to pigments, aromatic tetracarboxylic dianhydrides are preferably used in the present invention.

Examples of tricarboxylic acid anhydrides include aliphatic tricarboxylic acid anhydrides and aromatic tricarboxylic acid anhydrides. Examples of aliphatic tricarboxylic acid anhydrides include 3-carboxymethylglutaric anhydride, 1,2,4-butanetricarboxylic acid-1,2-anhydride, cis-propene-1,2,3-tricarboxylic acid-1,2-anhydride, and 1,3,4-cyclopentanetricarboxylic acid anhydride. Examples of aromatic tricarboxylic acids include benzenetricarboxylic anhydrides (1,2,3-benzenetricarboxylic anhydride, trimellitic anhydride [1,2,4-benzenetricarboxylic anhydride], etc.), naphthalenetricarboxylic anhydrides (1,2,4-naphthalenetricarboxylic anhydride, 1,4,5-naphthalenetricarboxylic anhydride, 2,3,6-naphthalenetricarboxylic anhydride, 1,2,8-naphthalenetricarboxylic anhydride, etc.), 3,4,4'-benzophenonetricarboxylic anhydride, 3,4,4'-biphenylethertricarboxylic anhydride, 3,4,4'-biphenyltricarboxylic anhydride, 2,3,2'-biphenyltricarboxylic anhydride, 3,4,4'-biphenylmethanetricarboxylic anhydride, and 3,4,4'-biphenylsulfonetricarboxylic anhydride. Among the above, aromatic tricarboxylic anhydrides are preferably used in the present invention from the viewpoint of adsorption to pigments.

The molar ratio of the acid anhydride groups in one or more acid anhydrides selected from tetracarboxylic dianhydrides and tricarboxylic anhydrides to the hydroxyl groups in the hydroxyl group-containing compound is preferably 0.5 to 1.5, i.e., acid anhydride groups/hydroxyl groups. If it is less than 0.5 or more than 1.5, there will be a large amount of non-reacted portions, and the desired dispersion resin will often not be obtained.

The hydroxyl group-containing compound may have a hydroxyl group capable of reacting with an acid anhydride group, but is preferably a polyol such as a diol having a plurality of hydroxyl groups. In addition, a part or all of the polyol also serves as a bonding point with the vinyl polymer moiety.
Examples of the polyol that serves as the bond origin with the vinyl polymer portion include at least one hydroxyl group-containing compound selected from the group consisting of compounds having two hydroxyl groups and one thiol group in the molecule and vinyl polymers containing a hydroxyl group at one end, such as 1-mercapto-1,1-methanediol, 1-mercapto-1,1-ethanediol, 3-mercapto-1,2-propanediol (thioglycerin or 1-thioglycerol), 2-mercapto-1,2-propanediol, 2-mercapto-2-methyl-1,3-propanediol, 2-mercapto-2-ethyl-1,3-propanediol, 1-mercapto-2,2-propanediol, 2-mercaptoethyl-2-methyl-1,3-propanediol, and 2-mercaptoethyl-2-ethyl-1,3-propanediol.

As the carboxylic acid-based dispersion resin (B4-1), the following carboxylic acid-based dispersion resin (B4-1-1) or (B4-1-2) can be preferably used.

(Carboxylic Acid-Based Dispersion Resin (B4-1-1))
The vinyl polymer portion of the carboxylic acid-based dispersion resin (B4-1-1) is obtained by radical polymerization of (i) an ethylenically unsaturated monomer having at least one thermally crosslinkable functional group selected from the group consisting of a hydroxyl group, an oxetane group, a t-butyl group, and a blocked isocyanate group, (ii) an ethylenically unsaturated monomer having a carboxyl group, and, if necessary, (iii) other ethylenically unsaturated monomers.

(i-1) [Ethylenically unsaturated monomer having a hydroxyl group]
The ethylenically unsaturated monomer having a hydroxyl group as the thermally crosslinkable functional group may be any monomer having a hydroxyl group and an ethylenically unsaturated double bond, and specifically, a (meth)acrylate monomer having a hydroxyl group, for example, a hydroxyalkyl (meth)acrylate such as 2-hydroxyethyl (meth)acrylate, 2 (or 3)-hydroxypropyl (meth)acrylate, 2 (or 3 or 4)-hydroxybutyl (meth)acrylate, and cyclohexanedimethanol mono(meth)acrylate, and an alkyl-α-hydroxyalkyl acrylate such as ethyl-α-hydroxymethyl acrylate,
or (meth)acrylamide monomers having a hydroxyl group, for example, N-(hydroxyalkyl)(meth)acrylamides such as N-(2-hydroxyethyl)(meth)acrylamide, N-(2-hydroxypropyl)(meth)acrylamide, and N-(2-hydroxybutyl)(meth)acrylamide;
Alternatively, a vinyl ether monomer having a hydroxyl group, for example, a hydroxyalkyl vinyl ether such as 2-hydroxyethyl vinyl ether, 2-(or 3-)hydroxypropyl vinyl ether, or 2-(or 3- or 4-)hydroxybutyl vinyl ether;
Alternatively, there may be mentioned allyl ether monomers having a hydroxyl group, for example, hydroxyalkyl allyl ethers such as 2-hydroxyethyl allyl ether, 2-(or 3-)hydroxypropyl allyl ether, and 2-(or 3- or 4-)hydroxybutyl allyl ether.

In addition, ethylenically unsaturated monomers obtained by adding alkylene oxides and/or lactones to the above-mentioned hydroxyalkyl (meth)acrylates, alkyl-α-hydroxyalkyl acrylates, N-(hydroxyalkyl)(meth)acrylamides, hydroxyalkyl vinyl ethers, or hydroxyalkyl allyl ethers can also be used as ethylenically unsaturated monomers having a hydroxyl group in the method of the present invention. As the alkylene oxide to be added, ethylene oxide, propylene oxide, 1,2-, 1,4-, 2,3-, or 1,3-butylene oxide, or a combination of two or more of these can be used. When two or more alkylene oxides are used in combination, the bonding form may be either random and/or block. As the lactone to be added, δ-valerolactone, ε-caprolactone, ε-caprolactone substituted with an alkyl group having 1 to 6 carbon atoms, or a combination of two or more of these can be used. Addition of both alkylene oxides and lactones is also acceptable.

(i-2) [Ethylenically unsaturated monomer having an oxetane group]
Examples of ethylenically unsaturated monomers having an oxetane group as a thermally crosslinkable functional group include (vinyloxyalkyl)alkyloxetane, (meth)acryloyloxyalkyloxetane, and [(meth)acryloyloxyalkyl]alkyloxetane. Among these, (3-ethyloxetan-3-yl)methyl methacrylate and the like are preferable. An example of a commercially available product is ETERNACOLL OXMA ((3-ethyloxetan-3-yl)methyl methacrylate) (manufactured by Ube Industries).

(i-3) [ethylenically unsaturated monomer having a t-butyl group]
Examples of the ethylenically unsaturated monomer having a t-butyl group as a thermally crosslinkable functional group include t-butyl methacrylate and t-butyl acrylate.

(i-4) [Ethylenically unsaturated monomer having a blocked isocyanate group]
Examples of ethylenically unsaturated monomers having a blocked isocyanate group as a thermally crosslinkable functional group include 2-(0-[1'-methylpropylideneamino]carboxyamino)ethyl methacrylate, 2-[(3,5-dimethylpyrazolyl)carbonylamino]ethyl methacrylate, etc. Commercially available products include Karenz MOI-BM (2-(0-[1'-methylpropylideneamino]carboxyamino)ethyl methacrylate) (manufactured by Showa Denko), Karenz MOI-BP (2-[(3,5-dimethylpyrazolyl)carbonylamino]ethyl methacrylate) (manufactured by Showa Denko), etc.

The content of the ethylenically unsaturated monomer having an oxetane group, the ethylenically unsaturated monomer having a t-butyl group, and the ethylenically unsaturated monomer having a blocked isocyanate group is preferably 5 to 90% by mass, and more preferably 20 to 60% by mass, of the total ethylenically unsaturated monomers. If it is 5% by mass or more, it is possible to obtain a coloring composition with excellent resistance due to the crosslinking effect, and if it is 90% by mass or less, the stability of the composition is also good, which is preferable.

(ii) [Ethylenically unsaturated monomer having a carboxyl group]
Examples of the ethylenically unsaturated monomer having a carboxyl group include (meth)acrylic acid, crotonic acid, α-chloroacrylic acid, cinnamic acid, etc. Among these, (meth)acrylic acid is preferred from the viewpoints of copolymerization reactivity and easy availability.

(iii) [Other ethylenically unsaturated monomers]
The vinyl polymer portion of the carboxylic acid-based dispersion resin (B4-1-1) of the present invention may be radically polymerized with an ethylenically unsaturated monomer other than an ethylenically unsaturated monomer having a thermally crosslinkable functional group and an ethylenically unsaturated monomer having a carboxyl group.
Examples of other ethylenically unsaturated monomers include, in addition to the above-mentioned ethylenically unsaturated monomers, alkyl (meth)acrylates such as methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, isopropyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, cyclohexyl (meth)acrylate, stearyl (meth)acrylate, lauryl (meth)acrylate, trimethylcyclohexyl (meth)acrylate, and isobornyl (meth)acrylate;
Aromatic (meth)acrylates such as phenyl (meth)acrylate, benzyl (meth)acrylate, phenoxyethyl (meth)acrylate, and phenoxydiethylene glycol (meth)acrylate;
heterocyclic (meth)acrylates such as tetrahydrofurfuryl (meth)acrylate;
alkoxypolyalkylene glycol (meth)acrylates such as methoxypolypropylene glycol (meth)acrylate and ethoxypolyethylene glycol (meth)acrylate;
N-substituted (meth)acrylamides such as (meth)acrylamide, N,N-dimethyl(meth)acrylamide, N,N-diethyl(meth)acrylamide, N-isopropyl(meth)acrylamide, diacetone(meth)acrylamide, and acryloylmorpholine;
Amino group-containing (meth)acrylates such as N,N-dimethylaminoethyl (meth)acrylate and N,N-diethylaminoethyl (meth)acrylate;
and nitriles such as (meth)acrylonitrile. In this specification, (meth)acrylate refers to methacrylate or acrylate, and (meth)acrylamide refers to methacrylamide or acrylamide.

In addition, examples of monomers that can be used in combination with the above acrylates include styrenes such as styrene and α-methylstyrene, vinyl ethers such as ethyl vinyl ether, n-propyl vinyl ether, isopropyl vinyl ether, n-butyl vinyl ether, and isobutyl vinyl ether, and vinyl fatty acid vinyls such as vinyl acetate and vinyl propionate.

(Carboxylic acid-based dispersion resin (B4-1-2))
The vinyl polymer portion of the carboxylic acid-based dispersion resin (B4-1-2) is a polymer obtained by radically polymerizing an ethylenically unsaturated monomer and modifying it so as to have a (meth)acryloyl group.
Specifically, the carboxylic acid dispersion resin (B4-1-2) can be produced by reacting a compound having a (meth)acryloyl group and a functional group with a polymer obtained by polymerizing a monomer containing an ethylenically unsaturated monomer having a functional group that reacts with the functional group. For example, a combination of glycidyl methacrylate and a polymer having a hydroxyl group or a carboxyl group, a combination of methacryloyloxyethyl isocyanate and a polymer having a hydroxyl group or a carboxyl group, etc. can be mentioned.
The polymer having a hydroxyl group or a carboxyl group can be obtained by subjecting a polymer having a glycidyl group to a ring-opening reaction with an acid anhydride compound, or can be obtained by subjecting a polymer having an acid anhydride group to a ring-opening reaction.
For example, the dispersants described in JP-A-2011-157416 can be mentioned.

(Carboxylic Acid-Based Dispersion Resin (B4-2))
The carboxylic acid-based dispersion resin (B4-2) is a dispersion resin represented by the following general formula (5), and specifically, is a dispersion resin described in JP-A-2007-140487.
General formula (5)
(HOOC-) _m - ^R4 -(-COO-[-R5 ^- COO-] _n - ^R6 ) _t
(In the general formula (5), ^R4 represents a residue of a tetravalent tetracarboxylic acid compound, ^R6 represents a monoalcohol residue, ^R5 represents a lactone residue, m represents 2 or 3, n represents an integer of 1 to 50, and t represents (4-m).)

[Organic solvent (C)]
The yellow colored composition of the present invention contains an organic solvent (C) from the viewpoint of dispersibility of the yellow colorant (A). The organic solvent (C) is not particularly limited, and any known organic solvent can be used.

Specific examples of the organic solvent (C) include 1,2,3-trichloropropane, 1-methoxy-2-propanol, ethyl lactate, 1,3-butanediol, 1,3-butylene glycol, 1,3-butylene glycol diacetate, 1,4-dioxane, 2-heptanone, 2-methyl-1,3-propanediol, 3,5,5-trimethyl-2-cyclohexen-1-one, 3,3,5-trimethylcyclohexanone, ethyl 3-ethoxypropionate, 3-methyl-1,3-butanediol, 3-methoxy-3-methyl-1-butanol, 3-methoxy-3-methylbutyl acetate, 3-methoxybutanol, 3-methoxybutyl acetate, 4-heptanone, m-xylene, m-diethylbenzene, m-dichlorobenzene, N,N-dimethylacetamide, N,N-dimethylformamide, n-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 monotertiary butyl ether, ethylene glycol monobutyl ether, ethylene glycol monobutyl ether acetate, ethylene glycol monopropyl ether, ethylene glycol monohexyl Ether, ethylene glycol monomethyl ether, ethylene glycol monomethyl ether acetate, diisobutyl ketone, diethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol monoisopropyl ether, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether, diethylene glycol monobutyl ether acetate, diethylene glycol monomethyl ether, cyclohexanol, cyclohexanol acetate, cyclohexanone, dipropylene glycol dimethyl ether, dipropylene glycol methyl ether acetate, dipropylene glycol monoethyl ether, dipropylene glycol monobutyl ether, dipropylene glycol monopropyl ether, dipropylene glycol Examples of the propylene glycol monomethyl ether include diacetone alcohol, triacetin, tripropylene glycol monobutyl ether, tripropylene glycol monomethyl ether, propylene glycol diacetate, propylene glycol phenyl ether, propylene glycol monoethyl ether, propylene glycol monoethyl ether acetate, propylene glycol monobutyl ether, propylene glycol monopropyl ether, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether propionate, benzyl alcohol, methyl isobutyl ketone, methylcyclohexanol, n-amyl acetate, n-butyl acetate, isoamyl acetate, isobutyl acetate, propyl acetate, and dibasic acid esters. Among these, from the viewpoint of dispersibility of the colorant and solubility of the binder resin, glycol acetates such as ethyl lactate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, ethylene glycol monomethyl ether acetate, and ethylene glycol monoethyl ether acetate, alcohols such as benzyl alcohol and diacetone alcohol, and ketones such as cyclohexanone can be mentioned. These organic solvents (C) may be used alone or in combination of two or more in any ratio.

[Binder resin (H)]
The yellow colored composition of the present invention preferably contains a binder resin (H). The binder resin (H) is not particularly limited, and any known binder resin can be used.

The binder resin (H) preferably has a transmittance of 80% or more, more preferably 95% or more, in the entire wavelength range of 400 to 700 nm. Binder resins (H) can be classified according to their main curing method into thermoplastic resins, thermosetting resins, and active energy ray curable resins having ethylenically unsaturated double bonds, etc., and the active energy ray curable resin may be a thermoplastic resin or one that also has a thermosetting function, and from the viewpoint of developability, it is preferable that the resin is an alkali-soluble resin. In addition, a thermoplastic resin that is not active energy ray curable may be included, and it is also preferable that this is alkali-soluble. These binder resins (H) may be used alone or in combination of two or more.

From the viewpoint of film-forming properties and resistance of the coating film, the content of the binder resin (H) is preferably 20 to 400% by mass, and more preferably 50 to 250% by mass, based on the total mass of the yellow colorant (A).

(Thermoplastic resin)
Examples of thermoplastic resins that can be used as the binder resin (H) include acrylic resins, butyral resins, styrene-maleic acid copolymers, chlorinated polyethylene, chlorinated polypropylene, polyvinyl chloride, vinyl chloride-vinyl acetate copolymers, polyvinyl acetate, polyurethane resins, polyester resins, vinyl resins, alkyd resins, polystyrene resins, polyamide resins, rubber resins, cyclized rubber resins, celluloses, polyethylenes (HDPE, LDPE), polybutadiene, and polyimide resins.
The thermoplastic resin is preferably alkali-soluble, and examples thereof include resins having an acidic group such as a carboxyl group or a sulfonic group. Specific examples of the resin include an acrylic resin having an acidic group, an α-olefin/maleic acid (anhydride) copolymer, a styrene/styrene sulfonic acid copolymer, an ethylene/(meth)acrylic acid copolymer, or an isobutylene/maleic acid (anhydride) copolymer. Among these, at least one resin selected from an acrylic resin having an acidic group and a styrene/styrene sulfonic acid copolymer, particularly an alkali-soluble resin having an acidic group and/or a hydroxyl group, is preferably used because of its high developability, heat resistance, and transparency.

(Alkali-soluble resin)
From the viewpoints of developability, heat resistance, and transparency, the binder resin (H) preferably contains an alkali-soluble resin, which is used to impart solubility in development in an alkali development step during color filter production and has an acid group and/or a hydroxyl group.

(Alkali-soluble resin having an ethylenically unsaturated double bond)
From the viewpoint of coating film resistance, the binder resin (H) is preferably an alkali-soluble resin having an ethylenically unsaturated double bond. In particular, by using a resin having an ethylenically unsaturated double bond introduced therein by the following methods (i) and (ii), the resin is three-dimensionally crosslinked when exposed to active energy rays to form a coating film, thereby increasing the crosslink density and improving the coating film resistance.

(Method (i))
An example of the method (i) is a method in which an ethylenically unsaturated double bond and a carboxyl group of an unsaturated monobasic acid having an ethylenically unsaturated double bond are added to the side-chain epoxy group of a copolymer obtained by copolymerizing an ethylenically unsaturated monomer having an epoxy group with one or more other monomers, and the ethylenically unsaturated double bond and a carboxyl group are introduced by reacting a polybasic acid anhydride with the hydroxyl group thus generated.

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

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

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

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

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

Examples of ethylenically unsaturated monomers having a hydroxyl group include hydroxyalkyl methacrylates such as 2-hydroxyethyl (meth)acrylate, 2- or 3-hydroxypropyl (meth)acrylate, 2-, 3- or 4-hydroxybutyl (meth)acrylate, glycerol mono(meth)acrylate, or cyclohexanedimethanol mono(meth)acrylate, which may be used alone or in combination of two or more. In addition, polyether mono(meth)acrylates obtained by addition polymerization of ethylene oxide, propylene oxide, and/or butylene oxide to the above-mentioned hydroxyalkyl (meth)acrylates, and polyester mono(meth)acrylates obtained by addition of poly(γ-valerolactone), poly(ε-caprolactone), and/or poly(12-hydroxystearic acid) may also be used. From the viewpoint of suppressing foreign matter in the coating, 2-hydroxyethyl methacrylate or glycerol mono(meth)acrylate is preferred, and from the viewpoint of sensitivity, it is preferred to use one having 2 to 6 hydroxyl groups, with glycerol mono(meth)acrylate being even more preferred.

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

Examples of monomers that make up alkali-soluble resins include the following: methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, isopropyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, t-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, cyclohexyl (meth)acrylate, stearyl (meth)acrylate, lauryl (meth)acrylate, tetrahydrofurfuryl (meth)acrylate, isobornyl (meth)acrylate, phenyl (meth)acrylate, benzyl (meth)acrylate, phenoxyethyl (meth)acrylate, phenoxydiethylene glycol (meth)acrylate, methoxypolypropylene glycol, etc. Examples of the (meth)acrylates include (meth)acrylates such as ethoxy polyethylene glycol (meth)acrylate, (meth)acrylamide, N,N-dimethyl (meth)acrylamide, N,N-diethyl (meth)acrylamide, N-isopropyl (meth)acrylamide, diacetone (meth)acrylamide, and acryloyl morpholine; styrenes such as styrene and α-methylstyrene; vinyl ethers such as ethyl vinyl ether, n-propyl vinyl ether, isopropyl vinyl ether, n-butyl vinyl ether, and isobutyl vinyl ether; and vinyl acetate and vinyl propionate and other fatty acid vinyls.

Alternatively, cyclohexylmaleimide, phenylmaleimide, methylmaleimide, ethylmaleimide, 1,2-bismaleimideethane 1,6-bismaleimidehexane, 3-maleimidopropionic acid, 6,7-methylenedioxy-4-methyl-3-maleimidocoumarin, 4,4'-bismaleimidediphenylmethane, bis(3-ethyl-5-methyl-4-maleimidophenyl)methane, N,N'-1,3-phenylenedimaleimide, N,N'-1,4-phenylenedimaleimide, N-(1-pyrenyl)maleimide, N-(2,4,6-trichlorophenyl)maleimide, N-(4-aminophenyl)maleimide, N-(4-nitrophenyl)maleimide, N-benzylmaleimide, N-bromomethyl-2,3-dichloromaleimide, N-succinimidyl-3-maleimide Examples of such compounds include N-substituted maleimides such as imidobenzoate, N-succinimidyl-3-maleimidopropionate, N-succinimidyl-4-maleimidobutyrate, N-succinimidyl-6-maleimidohexanoate, N-[4-(2-benzimidazolyl)phenyl]maleimide, and 9-maleimidoacridine, EO-modified cresol acrylate, n-nonylphenoxy polyethylene glycol acrylate, phenoxyethyl acrylate, ethoxylated phenyl acrylate, ethylene oxide (EO)-modified (meth)acrylate of phenol, EO- or propylene oxide (PO)-modified (meth)acrylate of paracumylphenol, EO-modified (meth)acrylate of nonylphenol, and PO-modified (meth)acrylate of nonylphenol.

Carboxyl group-containing ethylenically unsaturated monomers can also be used. Examples of carboxyl group-containing ethylenically unsaturated monomers include acrylic acid, methacrylic acid, ε-caprolactone-added acrylic acid, ε-caprolactone-added methacrylic acid, itaconic acid, maleic acid, fumaric acid, and crotonic acid.

Hydroxyl-containing ethylenically unsaturated monomers can also be used. Examples of hydroxyl-containing ethylenically unsaturated monomers include hydroxyalkyl (meth)acrylates such as 2-hydroxyethyl (meth)acrylate, 2- or 3-hydroxypropyl (meth)acrylate, 2-, 3- or 4-hydroxybutyl (meth)acrylate, and cyclohexanedimethanol mono(meth)acrylate. Examples of the hydroxyalkyl (meth)acrylate include polyether mono(meth)acrylates obtained by addition polymerization of ethylene oxide, propylene oxide, and/or butylene oxide to the above-mentioned hydroxyalkyl (meth)acrylates, and (poly)ester mono(meth)acrylates obtained by addition of (poly)γ-valerolactone, (poly)ε-caprolactone, and/or (poly)12-hydroxystearic acid.

Phosphate-containing ethylenically unsaturated monomers can also be used. Examples of phosphate-containing ethylenically unsaturated monomers include monomers that can be obtained by reacting the hydroxyl group of the hydroxyl-containing ethylenically unsaturated monomer with a phosphate esterifying agent such as phosphorus pentoxide or polyphosphoric acid.

In the present invention, the binder resin (H) can be a combination of an alkali-soluble resin having an ethylenic double bond and an alkali-soluble resin having no ethylenically unsaturated double bond in order to adjust the degree of hardening of the coating film.

The weight average molecular weight (Mw) of the binder resin (H) in the present invention is from 2,000 to 40,000, preferably from 3,000 to 300,000, and more preferably from 4,000 to 20,000, from the viewpoint of solubility in alkaline development. The value of Mw/Mn is preferably 10 or less. If the weight average molecular weight (Mw) is less than 2,000, the adhesion to the substrate decreases, making it difficult to leave an exposed pattern. If it exceeds 40,000, the solubility in alkaline development decreases, residue is generated, and the linearity of the pattern deteriorates.

The acid value of the binder resin (H) in the present invention is 50 to 200 (mg KOH/g) in order to impart solubility in alkaline development, preferably in the range of 70 to 180, and more preferably in the range of 90 to 170. If the acid value is less than 50, the solubility in alkaline development decreases, residue is generated, and the linearity of the pattern deteriorates. If it exceeds 200, the adhesion to the substrate decreases, making it difficult to leave an exposed pattern.

(Thermosetting Compound (I))
The yellow coloring composition of the present invention can further contain a thermosetting compound (I) in combination with a thermoplastic resin as a binder resin (H). When a color filter is produced using the coloring composition of the present invention, the thermosetting compound reacts during baking of the filter segment to increase the crosslink density of the coating film, thereby improving the heat resistance of the filter segment, suppressing pigment aggregation during baking of the filter segment, and improving the contrast ratio.

The thermosetting compound (I) may be a low molecular weight compound or a high molecular weight compound such as a resin. Examples of the thermosetting compound include epoxy compounds, oxetane compounds, benzoguanamine compounds, rosin-modified maleic acid compounds, rosin-modified fumaric acid compounds, melamine compounds, urea compounds, and phenol compounds, but the present invention is not limited thereto. Epoxy compounds and oxetane compounds are preferably used in the coloring composition of the present invention.

[Epoxy compound (I-1)]
The epoxy compound (I-1) may be a low molecular weight compound or a high molecular weight compound such as a resin. Examples of such epoxy compounds include polycondensates of bisphenols (bisphenol A, bisphenol F, bisphenol S, biphenol, bisphenol AD, etc.), phenols (phenol, alkyl-substituted phenol, aromatic-substituted phenol, naphthol, alkyl-substituted naphthol, dihydroxybenzene, alkyl-substituted dihydroxybenzene, dihydroxynaphthalene, etc.) and various aldehydes (formaldehyde, acetaldehyde, alkyl aldehyde, benzaldehyde, alkyl-substituted benzaldehyde, hydroxybenzaldehyde, naphthaldehyde, glutaraldehyde, phthalaldehyde, crotonaldehyde, cinnamaldehyde, etc.), polycondensates of phenols and various diene compounds (dicyclopentadiene, terpenes, vinylcyclohexene, norbornadiene, vinylnorbornene, tetrahydroindene, divinylbenzene, divinylbiphenyl, diisopropyl ether ... diisopropyl ether, diisopropyl ether, diisopropyl ether, diisopropyl ether, diisopropyl ether, diisopropyl ether, diisopropyl ether, diisopropyl ether, diisopropyl ether, diisopropyl ether, diisopropyl ether, diisopropyl ether, diisopropyl ether, diisopropyl ether, diisopropyl ether, diisopropyl ether, diisopropyl ether, diisopropyl ether, diisopropyl ether, diisopropyl ether, diisopropyl ether, diisopropyl ether, Examples of the epoxy resin include polymers of phenols and ketones (acetone, methyl ethyl ketone, methyl isobutyl ketone, acetophenone, benzophenone, etc.), polycondensates of phenols and aromatic dimethanols (benzene dimethanol, α,α,α',α'-benzene dimethanol, biphenyl dimethanol, α,α,α',α'-biphenyl dimethanol, etc.), polycondensates of phenols and aromatic dichloromethyls (α,α'-dichloroxylene, bischloromethyl biphenyl, etc.), polycondensates of bisphenols and various aldehydes, glycidyl ether epoxy resins obtained by glycidylating alcohols, alicyclic epoxy resins, heterocyclic epoxy resins, aliphatic epoxy resins, glycidyl amine epoxy resins, and glycidyl ester epoxy resins, but are not limited to these, so long as they are commonly used epoxy compounds. These may be used alone, or two or more of them may be used.

Commercially available products include, for example, Epicoat 807, Epicoat 815, Epicoat 825, Epicoat 827, Epicoat 828, Epicoat 190P, Epicoat 191P (all trade names; manufactured by Yuka Shell Epoxy Co., Ltd.), Epicoat 1004, Epicoat 1256 (all trade names; manufactured by Japan Epoxy Resins Co., Ltd.), TECHMORE VG3101L (trade name; manufactured by Mitsui Chemicals, Inc.), EPPN-501H, 502H (trade names; manufactured by Nippon Kayaku Co., Ltd.), JER 1032H60 (trade name; manufactured by Japan Epoxy Resins Co., Ltd.), JER 157S65, 157S70 (product names; manufactured by Japan Epoxy Resins Co., Ltd.), EPPN-201 (product name; manufactured by Nippon Kayaku Co., Ltd.), JER152, JER154 (all of the above are product names; manufactured by Japan Epoxy Resins Co., Ltd.), EOCN-102S, EOCN-103S, EOCN-104S, EOCN-1020 (all of the above are product names; manufactured by Nippon Kayaku Co., Ltd.), Celoxide 2021, EHPE- 3150 (all trade names; manufactured by Daicel Chemical Industries, Ltd.), Denacol EX-211, 212, 252, 313, 314, 321, 411, 421, 512, 521, 611, 612, 614, 614B, 622, 711, 721 (all trade names; manufactured by Nagase ChemteX Corporation), TEPIC-L, TEPIC-H, TEPIC-S (manufactured by Nissan Chemical Industries, Ltd.), and the like.
These include, but are not limited to, the following:

The amount of the epoxy compound (I-1) is preferably 0.5 to 300 parts by mass, and more preferably 1.0 to 50 parts by mass, per 100 parts by mass of the yellow colorant (A). If it is less than 0.5 parts by mass, the effect of improving the contrast ratio and heat resistance is small, and if it is more than 300 parts by mass, problems may occur when forming filter segments by photolithography.

[Oxetane Compound (I-2)]
The oxetane compound (I-2) is not particularly limited and may be any known compound having an oxetane group. Examples of the oxetane compound include those having a monofunctional oxetane group, those having a bifunctional oxetane group, and those having an oxetane group with more than two functionalities.

Examples of those having a monofunctional oxetane group include (3-ethyloxetan-3-yl)methyl acrylate, (3-ethyloxetan-3-yl)methyl methacrylate, 3-ethyl-3-hydroxymethyloxetane, 3-ethyl-3-(2-ethylhexyloxymethyl)oxetane, 3-ethyl-3-(phenoxymethyl)oxetane, 3-ethyl-3-(2-methacryloxymethyl)oxetane, and 3-ethyl-3-{[3-(triethoxysilyl)propoxy]methyl}oxetane.
Specific examples include OXE-10 and OXE-30 manufactured by Osaka Organic Chemical Industry Ltd., and OXT-101 and OXT-212 manufactured by Toagosei Co., Ltd.

Examples of compounds having a bifunctional oxetane group include 4,4'-bis[(3-ethyl-3-oxetanyl)methoxymethyl]biphenyl), 1,4-bis[(3-ethyl-3-oxetanyl)methoxymethyl]benzene, 1,4-bis{[(3-ethyl-3-oxetanyl)methoxy]methyl}benzene, di[1-ethyl(3-oxetanyl)]methyl ether, and di[1-ethyl(3-oxetanyl)]methyl ether-3-ethyl-3-hydroxymethyloxetane. 3-ethyl-3-(2-ethylhexyloxymethyl)oxetane, 3-ethyl-3-(2-phenoxymethyl)oxetane, 3,7-bis(3-oxetanyl)-5-oxa-nonane, 1,2-bis[(3-ethyl-3-oxetanylmethoxy)methyl]ethane, 1,3-bis[(3-ethyl-3-oxetanylmethoxy)methyl]propane, ethylene glycose bis(3-ethyl-3-oxetanylmethyl)ether, dicyclopentenyl bis(3-ethyl bis(3-ethyl-3-oxetanylmethyl)ether, triethylene glycol bis(3-ethyl-3-oxetanylmethyl)ether, tetraethylene glycol bis(3-ethyl-3-oxetanylmethyl)ether, 1,4-bis(3-ethyl-3-oxetanylmethoxy)butane, 1,6-bis(3-ethyl-3-oxetanylmethoxy)hexane, polyethylene glycol bis(3-ethyl-3-oxetanylmethyl)ether, ethylene oxide (EO)-modified bisphenol A bis(3-ethyl-3-oxetanylmethyl)ether, propylene oxide (PO)-modified bisphenol A bis(3-ethyl-3-oxetanylmethyl)ether, EO-modified hydrogenated bisphenol A bis(3-ethyl-3-oxetanylmethyl)ether, PO-modified hydrogenated bisphenol A bis(3-ethyl-3-oxetanylmethyl)ether, EO-modified bisphenol F (3-ethyl-3-oxetanylmethyl)ether, and the like.
Specific examples include OXBP and OXTP manufactured by Ube Industries, Ltd., and OXT-121 and OXT-221 manufactured by Toagosei Co., Ltd.

Examples of oxetane groups with two or more functionalities include pentaerythritol tris(3-ethyl-3-oxetanylmethyl) ether, pentaerythritol tetrakis(3-ethyl-3-oxetanylmethyl) ether, dipentaerythritol hexa(3-ethyl-3-oxetanylmethyl) ether, dipentaerythritol pentakis(3-ethyl-3-oxetanylmethyl) ether, dipentaerythritol tetrakis(3-ethyl-3-oxetanylmethyl) ether, and caprolactone-modified dipentaerythritol. Examples of such polymers include taerythritol hexa(3-ethyl-3-oxetanylmethyl)ether, caprolactone-modified dipentaerythritol pentakis(3-ethyl-3-oxetanylmethyl)ether, ditrimethylolpropane tetrakis(3-ethyl-3-oxetanylmethyl)ether, resins containing oxetane groups (such as the oxetane-modified phenol novolac resin described in Japanese Patent No. 3783462), and polymers obtained by radical polymerization of (meth)acrylic monomers such as the aforementioned OXE-30. Such polymers can be obtained using known polymerization methods.

The content of the oxetane compound (I-2) used in the yellow coloring composition of the present invention is usually 0.5 to 50 mass %, preferably 1 to 40 mass %, based on 100 mass % of the solid content of the yellow coloring composition. When the content of the oxetane compound is within the above range, it is preferable because an excellent coating film with good water stain resistance and high chemical resistance can be obtained.

The melamine compound refers to a compound having a melamine ring structure. The melamine compound may be a low molecular weight compound or a high molecular weight compound such as a resin. In the present invention, melamine compounds of the methylol type or ether type, in which the number of methylol groups and/or ether groups per melamine ring is 5.0 or more on average, are preferred. If the number of methylol groups and/or ether groups per melamine ring is less than 5.0 on average, there are few reaction points, and the crosslinked structure during curing is not sufficiently dense, so that the effect of suppressing the decrease in contrast ratio due to the heat treatment process and improving NMP resistance may be reduced.

Commercially available products include, for example, Nikalac MW-30HM, MW-390, MW-100LM, MX-750LM, MW-30M, MW-30, MW-22, MS-21, MS-11, MW-24X, MS-001, MX-002, MX-730, MX-750, MX-708, MX-706, MX-042, MX-45, MX-500, MX-520, MX-43, MX-417, and MX-410 (manufactured by Sanwa Chemical Co., Ltd.), and Cymel 232, 235, 236, 238, 285, 300, 301, 303, 350, and 370 (manufactured by Nippon Cytec Industries Co., Ltd.), but are not limited to these.

Among these, Nikarak MW-30HM, MW-390, MW-100LM, MX-750LM, MW-30M, MW-30, MW-22, MS-21, MS-11, MW-24X, MX-45 (manufactured by Sanwa Chemical Co., Ltd.) and Cymel 232, 235, 236, 238, 300, 301, 303, 350 (manufactured by Nippon Cytec Industries Co., Ltd.) are preferred because they have an average of 5.0 or more methylol groups and/or ether groups per melamine ring, and they provide a dense crosslinked structure.

The yellow coloring composition of the present invention may contain a curing agent (curing accelerator) or the like as necessary to assist the curing of the thermosetting compound (I). As the curing agent, amine compounds, acid anhydrides, active esters, carboxylic acid compounds, sulfonic acid compounds, etc. are effective, but are not particularly limited to these, and any curing agent may be used as long as it can react with the thermosetting compound. As the curing agent, for example, amine compounds (e.g., dicyandiamide, benzyldimethylamine, 4-(dimethylamino)-N,N-dimethylbenzylamine, 4-methoxy-N,N-dimethylbenzylamine, 4-methyl-N,N-dimethylbenzylamine, etc.), quaternary ammonium salt compounds (e.g., triethylbenzylammonium chloride, etc.), blocked isocyanate compounds (e.g., dimethylamine, etc.), imidazole derivatives, bicyclic amidine compounds and their salts (e.g., imidazole, 2-methylimidazole, 2-ethylimidazole, 2-ethyl-4-methylimidazole, 2 -phenylimidazole, 4-phenylimidazole, 1-cyanoethyl-2-phenylimidazole, 1-(2-cyanoethyl)-2-ethyl-4-methylimidazole, etc.), phosphorus compounds (e.g., triphenylphosphine, etc.), S-triazine derivatives (e.g., 2,4-diamino-6-methacryloyloxyethyl-S-triazine, 2-vinyl-2,4-diamino-S-triazine, 2-vinyl-4,6-diamino-S-triazine-isocyanuric acid adduct, 2,4-diamino-6-methacryloyloxyethyl-S-triazine-isocyanuric acid adduct, etc.) can be used. These may be used alone or in combination of two or more. The content of the curing accelerator is preferably 0.01 to 15 parts by mass relative to 100 parts by mass of the thermosetting compound (I).

<Green Colorant Composition>
One embodiment of the present invention relates to a green coloring composition comprising the yellow coloring composition and a green colorant (D), wherein the mass ratio of the yellow colorant (A) to the green colorant (D) is 70:30 to 10:90.

The components that are or can be included in one embodiment of the green coloring composition are described below.

[Green colorant (D)]
The green coloring composition of the present invention contains a green colorant (D). The green colorant (D) is not particularly limited, and any known green colorant can be used.

Specific examples of the green colorant (D) that can be used in the present invention include C.I. Pigment Green 1, 2, 4, 7, 8, 10, 13, 14, 15, 17, 18, 19, 26, 36, 37, 45, 48, 50, 51, 54, 55, 58, 62, 63, zinc phthalocyanine pigments described in JP-A-2008-19383, JP-A-2007-320986, JP-A-2004-70342, etc., and aluminum phthalocyanine pigments described in JP-A-4893859, JP-A-2016-153481, JP-A-2017-197685, etc. Among these, phthalocyanine pigments are preferred from the viewpoints of storage stability and solvent resistance.

The phthalocyanine pigments are preferably C.I. Pigment Green 7, C.I. Pigment Green 36, C.I. Pigment Green 58, C.I. Pigment Green 62, C.I. Pigment Green 63, zinc phthalocyanine pigments described in JP-A-2008-19383, JP-A-2007-320986, JP-A-2004-70342, etc., and aluminum phthalocyanine pigments described in JP-A-4893859, JP-A-2016-153481, JP-A-2017-197685, etc.

In the present invention, the green colorant (D) may be used alone or in combination of two or more.

The content of the green colorant (D) in the green coloring composition of the present invention is such that the mass ratio of the yellow colorant (A) to the green colorant (D) is in the range of 70:30 to 10 to 90. Within the above range, a green coloring composition having excellent brightness and contrast ratio is obtained, and the photosensitive green coloring material described below has excellent voltage retention and little decrease in brightness under high temperature and high humidity conditions.

The mass ratio of the yellow colorant (A) to the green colorant (D) is preferably in the range of 70:30 to 20:80, and more preferably in the range of 70:30 to 30:70.

(Other colorants)
The green colored composition of the present invention may further contain various conventionally known pigments and dyes selected arbitrarily within the range not impairing the effects of the present invention. Other colorants that can be used in the green colored composition of the present invention are listed below.

Blue pigments that can be used in the present invention include, for example, C.I. Pigment Blue 1, 1:2, 9, 14, 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 17, 19, 25, 27, 28, 29, 33, 35, 36, 56, 56:1, 60, 61, 61:1, 62, 63, 64, 66, 67, 68, 71, 72, 73, 74, 75, 76, 78, and 79, but are not limited to these.

Examples of purple pigments that can be used in the present invention include, but are not limited to, C.I. Pigment Violet 1, 1:1, 2, 2:2, 3, 3:1, 3:3, 5, 5:1, 14, 15, 16, 19, 23, 25, 27, 29, 31, 32, 37, 39, 42, 44, 47, 49, and 50.

Dyes that can be used in the present invention include acid dyes, direct dyes, basic dyes, salt-forming dyes, oil-soluble dyes, disperse dyes, reactive dyes, mordant dyes, vat dyes, and sulfur dyes. In addition, the dyes may be in the form of derivatives of these dyes or lake pigments obtained by making the dye into a lake.

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

In the case of a basic dye, it can be used after being salted with an organic acid, perchloric acid or a metal salt thereof. Among these, a salt-forming compound of a basic dye is preferred because of its excellent resistance and compatibility with pigments, and it is even more preferred to use a salt-forming compound obtained by salting a basic dye with a counter component acting as a counter ion, such as an organic sulfonic acid, an organic sulfuric acid, a fluorine-containing phosphorus anion compound, a fluorine-containing boron anion compound, a cyano-containing nitrogen anion compound, an anion compound having a conjugate base of an organic acid having a halogenated hydrocarbon group, or an acid dye.

In addition, when the dye skeleton has a polymerizable unsaturated group, the dye has excellent resistance, which is preferable.

The chemical structure of dyes includes, for example, azo dyes, disazo dyes, azomethine dyes (indoaniline dyes, indophenol dyes, etc.), dipyrromethene dyes, quinone dyes (benzoquinone dyes, naphthoquinone dyes, anthraquinone dyes, anthrapyridone dyes, etc.), carbonium dyes (diphenylmethane dyes, triphenylmethane dyes, xanthene dyes, acridine dyes, etc.), quinoneimine dyes (oxazine dyes, thiazine dyes, etc.), azine dyes, polymer dyes, etc. Examples of dye structures derived from dyes selected from tin dyes (such as oxonol dyes, merocyanine dyes, arylidene dyes, styryl dyes, cyanine dyes, squarylium dyes, and croconium dyes), quinophthalone dyes, phthalocyanine dyes, subphthalocyanine dyes, perinone dyes, indigo dyes, thioindigo dyes, quinoline dyes, nitro dyes, nitroso dyes, rhodamine dyes, and metal complex dyes thereof, but are not limited to these.

Among these dye structures, from the viewpoint of color characteristics such as hue, color separation, and color unevenness, dye structures derived from dyes selected from azo dyes, xanthene dyes, cyanine dyes, triphenylmethane dyes, anthraquinone dyes, dipyrromethene dyes, squarylium dyes, quinophthalone dyes, phthalocyanine dyes, and subphthalocyanine dyes are preferred, and dye structures derived from dyes selected from xanthene dyes, cyanine dyes, triphenylmethane dyes, anthraquinone dyes, dipyrromethene dyes, and phthalocyanine dyes are more preferred. Specific dye compounds that can form dye structures are described in "New Dye Handbook" (edited by the Society of Organic Synthesis Chemistry; Maruzen, 1970), "Color Index" (The Society of Dyers and Colourists), "Dye Handbook" (edited by Okawara et al.; Kodansha, 1986), etc.

The coloring composition of the present invention may also use an inorganic pigment as the colorant (A). Examples include titanium oxide, barium sulfate, zinc oxide, lead sulfate, yellow lead, zinc yellow, red iron oxide (red iron (III) oxide), cadmium red, ultramarine, Prussian blue, chromium oxide green, cobalt green, amber, and synthetic iron black.

Specifically, from the viewpoint of coloring power and pattern formability, C.I. Pigment Blue 15:3, 15:4, and 15:6, which are unsubstituted phthalocyanine pigments that have a transmission region in the short wavelength region, are preferred.

<Red Colorant Composition>
One embodiment of the present invention relates to a red coloring composition comprising the yellow coloring composition and a red colorant (E), wherein the mass ratio of the yellow colorant (A) to the red colorant (E) is 70:30 to 10:90.

The components that are or can be included in the red coloring composition of one embodiment are described below.

[Red Colorant (E)]
The red coloring composition of the present invention contains a red colorant (E). The red colorant (E) is not particularly limited, and any known red colorant can be used.

The red colorant (E) that can be used in the present invention is specifically C.I. Pigment Red 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 14, 17, 22, 23, 31, 38, 41, 48:1, 48:2, 48:3, 48:4, 49, 49:1, 49:2, 57:1, 81, 81:1, 81:2, 81:3, 81:4, 83, 88, 90, 105, 112, 119, 122, 123, 144, 146, 149, 150, 155, 166, 168, 169, 170, 171, 172, 175, 176, 177, 178, 179, 184, 185, 187, 188, 190, 200, 202, 206, 207, 208, 209, 210, 216, 220, 221, 224, 226, 242, 246, 254, 255, 264, 269, 270, 272, 273, 274, 276, 277, 278, 279, 280, 281, 282, 283, 284, 285, 286, 287, 291, 295, 296, etc., but are not particularly limited to these. Among them, diketopyrrolopyrrole pigments, anthraquinone pigments, and azo pigments are preferred from the viewpoint of storage stability and solvent resistance.

The diketopyrrolopyrrole pigment is preferably C.I. Pigment Red 254, or a brominated diketopyrrolopyrrole pigment described in JP-A-2011-523433, the anthraquinone pigment is preferably C.I. Pigment Red 177, and the azo pigment is preferably C.I. Pigment Red 176, C.I. Pigment Red 242, C.I. Pigment Red 269, or an azo compound described in JP-A-2011-173971 or JP-A-2012-229344.

In the present invention, the red colorant (E) may be used alone or in combination of two or more.

The content of the red colorant (E) in the red coloring composition of the present invention is such that the mass ratio of the yellow colorant (A) to the red colorant (E) is in the range of 70:30 to 10:90. Within the above range, a red coloring composition having excellent brightness and contrast ratio can be obtained.

The mass ratio of the yellow colorant (A) to the red colorant (E) is preferably in the range of 70:30 to 20 to 80, and more preferably in the range of 70:30 to 30 to 70.

(Other colorants)
The red colored composition of the present invention may further contain various conventionally known pigments and dyes as colorants, selected arbitrarily, within the range not impairing the effects of the present invention. Other colorants that can be used in the red colored composition of the present invention include the other colorants described above.

<Photosensitive Coloring Composition>
One embodiment of the present invention relates to a photosensitive coloring composition. The photosensitive coloring composition of the present invention includes the coloring composition, a polymerizable compound (E), and a photopolymerization initiator (F).

The components that are or can be included in one embodiment of the photosensitive coloring composition are described below.

[Polymerizable compound (E)]
The photosensitive coloring composition of the present invention contains a polymerizable compound (E). The polymerizable compound (E) is not particularly limited, and any known compound can be used. The polymerizable compound (E) contains a monomer or oligomer that is cured by ultraviolet light, heat, or the like to produce a transparent resin.

Examples of monomers and oligomers that harden when exposed to ultraviolet light or heat to produce a transparent resin include methyl (meth)acrylate, ethyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, cyclohexyl (meth)acrylate, β-carboxyethyl (meth)acrylate, polyethylene glycol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, triethylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, phenoxytetraethylene glycol (meth)acrylate, phenoxyhexaethylene glycol (meth)acrylate, trimethylolpropane PO-modified tri(meth)acrylate, trimethylolpropane EO-modified tri(meth)acrylate, isocyanuric acid EO-modified di(meth)acrylate, isocyanuric acid EO-modified tri(meth)acrylate, ditrimethylolpropane tetra(meth)acrylate. acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, 1,6-hexanediol diglycidyl ether di(meth)acrylate, bisphenol A diglycidyl ether di(meth)acrylate, neopentyl glycol diglycidyl ether di(meth)acrylate, dipentaerythritol hexa(meth)acrylate, dipentaerythritol penta(meth)acrylate, tricyclodecanyl (meth)acrylate, (meth)acrylic acid ester of methylol melamine, epoxy (meth)acrylate, urethane acrylate, and various acrylic acid esters and methacrylic acid esters, (meth)acrylic acid, styrene, vinyl acetate, hydroxyethyl vinyl ether, ethylene glycol divinyl ether, pentaerythritol trivinyl ether, (meth)acrylamide, N-hydroxymethyl (meth)acrylamide, N-vinyl formamide, acrylonitrile, and the like, but are not necessarily limited thereto.

Commercially available products of these include KAYARAD R-128H, R526, PEG400DA, MAND, NPGDA, R-167, HX-220, R-551, R712, R-604, R-684, GPO-303, TMPTA, DPHA, DPEA-12, DPHA-2C, D-310, D-330, DPCA-20, DPCA-30, DPCA-60, and DPCA-120 manufactured by Nippon Kayaku Co., Ltd., and Aronix M-303, M-305, M-306, M-309, M-310, and M-32 manufactured by Toagosei Co., Ltd. 1, M-325, M-350, M-360, M-313, M-315, M-400, M-402, M-403, M-404, M-405, M-406, M-450, M-452, M-408, M-211B, M-101A, Viscoat #310HP, #335HP, #700, #295, #330, #360, #GPT, #400, #405 manufactured by Osaka Organic Chemical Co., Ltd., and NK Ester A-9300 manufactured by Shin-Nakamura Chemical Co., Ltd. can be preferably used.

(Polymerizable compound having an acid group)
The polymerizable compound (E) of the present invention may contain a polymerizable compound having an acid group. Examples of the acid group include a sulfonic acid group, a carboxyl group, and a phosphoric acid group.

Examples of polymerizable compounds having an acid group include esters of dicarboxylic acids and free hydroxyl group-containing poly(meth)acrylates of polyhydric alcohols and (meth)acrylic acid; esters of polycarboxylic acids and monohydroxyalkyl(meth)acrylates. Specific examples include free carboxyl group-containing monoesters of monohydroxy oligoacrylates or monohydroxy oligomethacrylates such as trimethylolpropane diacrylate, trimethylolpropane dimethacrylate, pentaerythritol triacrylate, pentaerythritol trimethacrylate, dipentaerythritol pentaacrylate, and dipentaerythritol pentamethacrylate, and dicarboxylic acids such as malonic acid, succinic acid, glutaric acid, and phthalic acid; Examples of the free carboxyl group-containing oligoesters include tricarboxylic acids such as butane-1,2,4-tricarboxylic acid, benzene-1,2,3-tricarboxylic acid, benzene-1,3,4-tricarboxylic acid, and benzene-1,3,5-tricarboxylic acid, and monohydroxy monoacrylates or monohydroxy monomethacrylates such as 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl acrylate, and 2-hydroxypropyl methacrylate, but are not limited to these.

As commercially available products, Viscoat #2500P manufactured by Osaka Organic Industries, and Aronix M-5300, M-5400, M-5700, M-510, M-520 manufactured by Toagosei Co., Ltd. can be suitably used.

(Polymerizable compound having a urethane bond)
The polymerizable compound (E) of the present invention may contain a polymerizable compound containing at least one ethylenically unsaturated bond and at least one urethane bond. For example, there may be mentioned a polyfunctional urethane acrylate obtained by reacting a (meth)acrylate having a hydroxyl group with a polyfunctional isocyanate, or a polyfunctional urethane acrylate obtained by reacting an alcohol with a polyfunctional isocyanate and further reacting the alcohol with a (meth)acrylate having a hydroxyl group.

Examples of (meth)acrylates having a hydroxyl group include 2-hydroxyethyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, trimethylolpropane di(meth)acrylate, pentaerythritol tri(meth)acrylate, ditrimethylolpropane tri(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol ethylene oxide modified penta(meth)acrylate, dipentaerythritol propylene oxide modified penta(meth)acrylate, dipentaerythritol caprolactone modified penta(meth)acrylate, glycerol acrylate methacrylate, glycerol dimethacrylate, 2-hydroxy-3-acryloylpropyl methacrylate, reaction product of an epoxy group-containing compound and carboxy(meth)acrylate, and hydroxyl group-containing polyol polyacrylate.

Examples of polyfunctional isocyanates include tolylene diisocyanate, hexamethylene diisocyanate, diphenylmethylene diisocyanate, isophorone diisocyanate, polyisocyanate, etc.

As commercially available products thereof, AH-600, AT-600, UA-306H, UA-306T, UA-306I, UA-510H, UF-8001G, DAUA-167 manufactured by Kyoeisha Chemical Co., Ltd., UA-160TM manufactured by Shin-Nakamura Chemical Co., Ltd., UV-4108F, UV-4117F manufactured by Osaka Organic Chemical Industry Co., Ltd., and the like can be suitably used.

The polymerizable compound (E) may be used alone or in a mixture of two or more types in any ratio as required.

From the viewpoint of photocurability and developability, the content of the polymerizable compound (E) is preferably 1 to 50 parts by mass, and more preferably 2 to 40 parts by mass, based on the total solid content of the photosensitive coloring composition (100 parts by mass).

[Photopolymerization initiator (F)]
The photosensitive coloring composition of the present invention contains a photopolymerization initiator (F). By containing the photopolymerization initiator (F), the photosensitive coloring composition can be cured by ultraviolet irradiation and a filter segment can be formed by a photolithography method. The photopolymerization initiator (F) is not particularly limited, and a known one can be used.

Examples of the photopolymerization initiator (F) include acetophenone-based compounds such as 4-phenoxydichloroacetophenone, 4-t-butyl-dichloroacetophenone, diethoxyacetophenone, 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropan-1-one, 1-hydroxycyclohexyl phenyl ketone, 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one, 2-(dimethylamino)-1-[4-(4-morpholino)phenyl]-2-(phenylmethyl)-1-butanone, and 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]-1-butanone; benzoin, benzoin methyl ether, Benzoin compounds such as benzoin ethyl ether, benzoin isopropyl ether, and benzil dimethyl ketal; benzophenone compounds such as benzophenone, benzoylbenzoic acid, methyl benzoylbenzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, and 3,3',4,4'-tetra(t-butylperoxycarbonyl)benzophenone; thioxanthone compounds such as thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, isopropylthioxanthone, 2,4-diisopropylthioxanthone, and 2,4-diethylthioxanthone; 2,4,6-trichloro-s-triazanthone; 2-phenyl-4,6-bis(trichloromethyl)-s-triazine, 2-(p-methoxyphenyl)-4,6-bis(trichloromethyl)-s-triazine, 2-(p-tolyl)-4,6-bis(trichloromethyl)-s-triazine, 2-piperonyl-4,6-bis(trichloromethyl)-s-triazine, 2,4-bis(trichloromethyl)-6-styryl-s-triazine, 2-(naphth-1-yl)-4,6-bis(trichloromethyl)-s-triazine, 2-(4-methoxy-naphth-1-yl)-4,6-bis(trichloromethyl)-s-triazine, 2,4-trichloromethyl-(piperonyl)-6-triazine, or 2,4-trichloromethyl-(4'-methoxystyryl)-6-triazine. Examples of such compounds include triazine-based compounds such as azine; oxime ester-based compounds such as 1,2-octanedione, 1-[4-(phenylthio)phenyl-, 2-(O-benzoyloxime)], or ethanone, 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-, or 1-(O-acetyloxime); phosphine-based compounds such as bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide or diphenyl-2,4,6-trimethylbenzoylphosphine oxide; quinone-based compounds such as 9,10-phenanthrenequinone, camphorquinone, and ethylanthraquinone; borate-based compounds; carbazole-based compounds; imidazole-based compounds; or titanocene-based compounds.

Commercially available products include acetophenone compounds manufactured by IGM Resins such as "Omnirad 907" (2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one), "Omnirad 369E" (2-(dimethylamino)-1-[4-(4-morpholino)phenyl]-2-(phenylmethyl)-1-butanone), and "Omnirad 379EG" (2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]-1-butanone), and phosphine compounds manufactured by IGM Resins such as "Omnirad 819" (bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide) and "Omnirad "TPO" (diphenyl-2,4,6-trimethylbenzoylphosphine oxide), etc.

In the present invention, it is preferable to contain an oxime ester compound among these.

(Oxime ester compounds)
In the oxime ester compound, the N-O bond of the oxime is cleaved by absorbing ultraviolet light, generating an iminyl radical and an alkyloxy radical. These radicals further decompose to generate highly active radicals, so that a pattern can be formed with a small amount of exposure. When the colorant concentration of the photosensitive coloring composition is high, the ultraviolet transmittance of the coating film may decrease, and the degree of curing of the coating film may decrease, but the oxime ester compound has a high quantum efficiency and is therefore preferably used.

Commercially available products of these oxime ester compounds include 1,2-octanedione, 1-[4-(phenylthio)phenyl-, 2-(O-benzoyloxime)] (IRGACURE OXE-01) from BASF, ethanone, 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-, 1-(O-acetyloxime) (IRGACURE OXE 02), N-1919 (manufactured by ADEKA), TRONLY TR-PBG-304, TRONLY TR-PBG-305, and TRONLY TR-PBG-309 (all manufactured by Changzhou Strong New Materials Co., Ltd.). In addition, it is also possible to use oxime ester-based photopolymerization initiators described in JP-A-2007-210991, JP-A-2009-179619, JP-A-2010-037223, JP-A-2010-215575, JP-A-2011-020998, etc.

The photopolymerization initiator (F) can be used alone or in a mixture of two or more types in any ratio as necessary.

The content of the photopolymerization initiator (F) is preferably 2 to 50 parts by mass, and more preferably 2 to 30 parts by mass, based on the total mass of the colorant, from the viewpoint of photocurability and developability. If it is less than 2 parts by mass, the adhesion of the formed pattern to the substrate will be poor, and if it exceeds 50 parts by mass, problems with developability may occur, and a decrease in brightness after heat treatment at 230°C may occur.

[Sensitizer (J)]
The photosensitive coloring composition of the present invention can contain a sensitizer (J). Examples of the sensitizer (J) include chalcone derivatives, unsaturated ketones such as dibenzalacetone, 1,2-diketone derivatives such as benzil and camphorquinone, benzoin derivatives, fluorene derivatives, naphthoquinone derivatives, anthraquinone derivatives, xanthene derivatives, thioxanthene derivatives, xanthone derivatives, thioxanthone derivatives, coumarin derivatives, ketocoumarin derivatives, cyanine derivatives, merocyanine derivatives, and oxonol derivatives, polymethine dyes, acridine derivatives, azine derivatives, thiazine derivatives, oxazine derivatives, indoline derivatives, azulene derivatives, azulenium derivatives, squarylium derivatives, porphyrin derivatives, tetraphenylporphyrin derivatives, triarylmethane derivatives, tetrabenzoporphyrin derivatives, tetrapyrazinoporphyra, and the like. Examples of the compound include aryl ether derivatives, phthalocyanine derivatives, tetraazaporphyrazine derivatives, tetraquinoxalylporphyrazine derivatives, naphthalocyanine derivatives, subphthalocyanine derivatives, pyrylium derivatives, thiopyrylium derivatives, tetraphylline derivatives, annulene derivatives, spiropyran derivatives, spirooxazine derivatives, thiospiropyran derivatives, metal arene complexes, organic ruthenium complexes, Michler's ketone derivatives, α-acyloxy esters, acyl oxides, methylphenyl glyoxylate, benzyl, 9,10-phenanthrenequinone, camphorquinone, ethyl anthraquinone, 4,4'-diethylisophthalophenone, 3,3' or 4,4'-tetra(t-butylperoxycarbonyl)benzophenone, and 4,4'-bis(diethylamino)benzophenone.

Among the sensitizers (J), particularly suitable sensitizers include thioxanthone derivatives, Michler's ketone derivatives, and carbazole derivatives. More specifically, 2,4-diethylthioxanthone, 2-chlorothioxanthone, 2,4-dichlorothioxanthone, 2-isopropylthioxanthone, 4-isopropylthioxanthone, 1-chloro-4-propoxythioxanthone, 4,4'-bis(dimethylamino)benzophenone, 4,4'-bis(diethylamino)benzophenone, 4,4'-bis(ethylmethylamino)benzophenone, N-ethylcarbazole, 3-benzoyl-N-ethylcarbazole, and 3,6-dibenzoyl-N-ethylcarbazole are used.

The sensitizer (J) may be used alone or in combination of two or more kinds in any ratio as required.
Commercially available products include "KAYACURE DETX-S" (2,4-diethylthioxanthone, manufactured by Nippon Kayaku Co., Ltd.) and "CHEMARK DEABP"(4,4'-bis(diethylamino)benzophenone, manufactured by Chemark Chemical Co., Ltd.).

More specifically, examples of sensitizers include those described in "Dye Handbook" edited by Okawara Makoto et al. (Kodansha, 1986), "Chemistry of Functional Dyes" edited by Okawara Makoto et al. (CMC, 1981), "Tokushu No Futon Zairyo" edited by Ikemori Chuzaburo et al., and "Tokushu No Futon Zairyo" (CMC, 1986), but are not limited to these. In addition, sensitizers that absorb light from the ultraviolet to near infrared regions can also be included.

When the sensitizer (J) is used, the content is preferably 3 to 60 parts by mass, and more preferably 5 to 50 parts by mass, per 100 parts by mass of the photopolymerization initiator (F) contained in the photosensitive coloring composition, from the viewpoints of photocurability and developability.

[Thiol-based chain transfer agent (K)]
The photosensitive coloring composition of the present invention may contain a thiol-based chain transfer agent (K) as a chain transfer agent.
By using a thiol together with a photopolymerization initiator, a thiyl radical that acts as a chain transfer agent in the radical polymerization process after irradiation with light and is resistant to polymerization inhibition by oxygen is generated, so that the obtained colored composition has high sensitivity.

In addition, polyfunctional aliphatic thiols having two or more SH groups bonded to aliphatic groups such as methylene and ethylene groups are preferred. Polyfunctional aliphatic thiols having four or more SH groups are more preferred. By increasing the number of functional groups, the polymerization initiation function is improved, and curing can be achieved from the surface of the pattern to near the substrate.

Examples of polyfunctional thiols include hexanedithiol, decanedithiol, 1,4-butanediol bisthiopropionate, 1,4-butanediol bisthioglycolate, ethylene glycol bisthioglycolate, ethylene glycol bisthiopropionate, trimethylolpropane tristhioglycolate, trimethylolpropane tristhiopropionate, trimethylolpropane tris(3-mercaptobutyrate), pentaerythritol tetrakisthioglycolate, penta Examples of such thiopropionates include erythritol tetrakisthiopropionate, trimercaptopropionic acid tris(2-hydroxyethyl)isocyanurate, 1,4-dimethylmercaptobenzene, 2,4,6-trimercapto-s-triazine, and 2-(N,N-dibutylamino)-4,6-dimercapto-s-triazine. Preferred examples include ethylene glycol bisthiopropionate, trimethylolpropane tristhiopropionate, and pentaerythritol tetrakisthiopropionate.

The thiol chain transfer agent (K) can be used alone or in a mixture of two or more.

The content of the thiol-based chain transfer agent (K) is preferably 1.0 to 10 mass % of the total solid content of the photosensitive coloring composition, and more preferably 2.0 to 8.0 mass %. In this range, the effect of the chain transfer agent becomes greater, and the sensitivity, taper shape, wrinkles, film shrinkage rate, etc. become better.

[Polymerization inhibitor (L)]
The photosensitive coloring composition of the present invention can contain a polymerization inhibitor (L) in order to prevent photosensitivity due to diffracted light from a mask during exposure. By adding the polymerization inhibitor (L), it is possible to obtain an effect of preventing curing from progressing beyond the desired pattern due to chain polymerization caused by exposure to light.

The polymerization inhibitor (L) may be, for example, alkyl catechol compounds such as catechol, resorcinol, 1,4-hydroquinone, 2-methyl catechol, 3-methyl catechol, 4-methyl catechol, 2-ethyl catechol, 3-ethyl catechol, 4-ethyl catechol, 2-propyl catechol, 3-propyl catechol, 4-propyl catechol, 2-n-butyl catechol, 3-n-butyl catechol, 4-n-butyl catechol, 2-t-butyl catechol, 3-t-butyl catechol, 4-t-butyl catechol, and 3,5-di-t-butyl catechol; 2-methyl resorcinol, 4-methyl resorcinol, 2-ethyl resorcinol, 4-ethyl resorcinol, 2-propyl resorcinol, 4-propyl resorcinol, and 2-n- Examples of the polymerization inhibitor include alkyl resorcinol compounds such as butyl resorcinol, 4-n-butyl resorcinol, 2-t-butyl resorcinol, and 4-t-butyl resorcinol, alkyl hydroquinone compounds such as methyl hydroquinone, ethyl hydroquinone, propyl hydroquinone, t-butyl hydroquinone, and 2,5-di-t-butyl hydroquinone, phosphine compounds such as tributyl phosphine, trioctyl phosphine, tricyclohexyl phosphine, triphenyl phosphine, and tribenzyl phosphine, phosphine oxide compounds such as trioctyl phosphine oxide and triphenyl phosphine oxide, phosphite compounds such as triphenyl phosphite and trisnonylphenyl phosphite, pyrogallol, and phloroglucin. The content of the polymerization inhibitor is preferably 0.01 to 0.4 parts by mass per 100 parts by mass of the photosensitive coloring composition excluding the organic solvent. In this range, the effect of the polymerization inhibitor becomes greater, and the linearity of the taper, wrinkles in the coating film, and pattern resolution become better.

[Ultraviolet absorber (M)]
The photosensitive coloring composition of the present invention can contain an ultraviolet absorber (M). The ultraviolet absorber (M) in the present invention is an organic compound having an ultraviolet absorbing function, and examples of the ultraviolet absorber (M) include benzotriazole-based organic compounds, triazine-based organic compounds, benzophenone-based organic compounds, salicylic acid ester-based organic compounds, cyanoacrylate-based organic compounds, and salicylate-based organic compounds.

The content of the ultraviolet absorber (M) is preferably 5 to 70% by mass based on the total mass % of the photopolymerization initiator (F) and the ultraviolet absorber (M). If the content of the ultraviolet absorber is less than the above, the effect of the ultraviolet absorber is small and resolution cannot be ensured, and if the content is more than the above, the sensitivity is reduced and problems such as pixel peeling and hole diameters larger than the design value may occur.

In this case, if the photosensitive coloring composition contains a sensitizer (J), the content of the photopolymerization initiator (F) includes the content of the sensitizer (J).

In addition, the total content of the photopolymerization initiator (F) and the ultraviolet absorber (M) is preferably 1 to 20% by mass in the solid content of the photosensitive coloring composition. If the total content of the photopolymerization initiator (F) and the ultraviolet absorber (M) is less than the above, adhesion may be weakened and pixel peeling may occur, and if it is more than the above, the sensitivity may be too high and the resolution may be poor.

In this case, if the photosensitive coloring composition contains a sensitizer (J), the content of the sensitizer is included in the content of the photopolymerization initiator (F).

Benzotriazole organic compounds include 2-(5-methyl-2-hydroxyphenyl)benzotriazole, 2-(2-hydroxy-5-t-butylphenyl)-2H-benzotriazole, 2-[2-hydroxy-3,5-bis(α, α-Dimethylbenzyl)phenyl]-2H-benzotriazole, 2-(3-t-butyl-5-methyl-2-hydroxyphenyl)-5-chlorobenzotriazole, 2-(2'-hydroxy-5'-t-octylphenyl)benzotriazole, 5% 2-methoxy-1-methylethyl acetate and 95% benzenepropanoic acid, 3-(2H-benzotriazol-2-yl)-(1,1-dimethylethyl)-4-hydroxy, C7-9 branched and linear alkyl ester mixture, 2-(2H-benzotriazol-2-yl)-4,6-bis(1-methyl-1-phenylethyl)phenol, 2-(2H-benzotriazol-2-yl)-6-(1-methyl-1-phenylethyl)-4-(1,1,3,3-tetramethylbutyl)phenol, methyl 3-(3-(2H-benzotriazol-2-yl)-5-t-butyl-4-hydroxyphenyl)propionate/polyethylene glycol 300 reaction products, 2-(2H-benzotriazol-2-yl)-4-(1,1,3,3-tetramethylbutyl)phenol, 2,2'-methylenebis[6-(2H-benzotriazol-2-yl)-4-(1,1,3,3-tetramethylbutyl)phenol], 2-(2H-benzotriazol-2-yl)-p-cresol, 2-(5-chloro-2H-benzotriazol-2-yl)-6 -t-butyl-4-methylphenol, 2-(3,5-di-t-amyl-2-hydroxyphenyl)benzotriazole, 2-[2-hydroxy-5-[2-(methacryloyloxy)ethyl]phenyl]-2H-benzotriazole, octyl-3-[3-t-butyl-4-hydroxy-5-(5-chloro-2H-benzotriazol-2-yl)phenyl]propionate, 2-ethylhexyl-3-[3-t-butyl-4-hydroxy-5-(5-chloro-2H-benzotriazol-2-yl)phenyl]propionate. Other oligomer and polymer type compounds having a benzotriazole structure can also be used.

More specifically, examples include TINUVIN P, PS, 234, 326, 329, 384-2, 900, 928, 99-2, and 1130 manufactured by BASF Corporation, ADK STAB LA-29, LA-31RG, LA-32, and LA-36 manufactured by ADEKA Corporation, KEMISORB 71, 73, 74, 79, and 279 manufactured by Chemipro Chemical Co., Ltd., and RUVA-93 manufactured by Otsuka Chemical Co., Ltd.

Triazine organic compounds include 2,4-bis(2,4-dimethylphenyl)-6-(2-hydroxy-4-n-octyloxyphenyl)-1,3,5-triazine, 2-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine-2-yl]-5-[3-(dodecyloxy)-2-hydroxypropoxy]phenol, and the reaction of 2-(2,4-dihydroxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine with (2-ethylhexyl)-glycidic acid ester. The product includes 2,4-bis[2-hydroxy-4-butoxyphenyl]-6-(2,4-dibutoxyphenyl)-1,3,5-triazine, 2-(4,6-diphenyl-1,3,5-triazin-2-yl)-5-(hexyloxy)phenol, 2-(4,6-diphenyl-1,3,5-triazin-2-yl)-5-[2-(2-ethylhexanoyloxy)ethoxy]phenol, 2,4,6-tris(2-hydroxy-4-hexyloxy-3-methylphenyl)-1,3,5-triazine, etc. In addition, oligomer and polymer type compounds having a triazine structure can also be used.

More specifically, examples include KEMISORB 102 manufactured by Chemipro Chemicals, TINUVIN 400, 405, 460, 477, 479, and 1577ED manufactured by BASF, Adeka STAB LA-46 and LA-F70 manufactured by ADEKA, and CYASORB UV-1164 manufactured by Sun Chemical.

Benzophenone-based organic compounds include 2,4-dihydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid-3H2O, 2-hydroxy-4-n-octoxybenzophenone, 2,2'-dihydroxy-4-methoxybenzophenone, 2,2'-dihydroxy-4,4'-dimethoxybenzophenone, 4-dodecyloxy-2-hydroxybenzophenone, 2-hydroxy-4-octadecyloxybenzophenone, 2,2'dihydroxy-4,4'-dimethoxybenzophenone, 2,2',4,4'-tetrahydroxybenzophenone, and 2-hydroxy-4-methoxy-2'-carboxybenzophenone. Other oligomer and polymer compounds having a benzophenone structure can also be used.

More specifically, examples include KEMISORB 10, 11, 11S, 12, and 111 manufactured by Chemipro Chemicals Co., Ltd., SEESORB 101 and 107 manufactured by Shipro Chemicals Co., Ltd., Adeka STAB 1413 manufactured by ADEKA Corporation, and UV-12 manufactured by Sun Chemical Co., Ltd.

Examples of salicylic acid ester organic compounds include phenyl salicylate, p-octylphenyl salicylate, and t-butylphenyl salicylate. Other oligomer and polymer type compounds having a salicylic acid ester structure can also be used.

[Antioxidant (N)]
The photosensitive coloring composition of the present invention can contain an antioxidant (N). The antioxidant (N) prevents the photopolymerization initiator or thermosetting compound contained in the photosensitive coloring composition from being oxidized and yellowed by the thermal process during heat curing or ITO annealing, so that the transmittance of the coating film can be increased. In particular, when the colorant concentration of the coloring composition is high, the amount of the coating film crosslinking component is reduced, so that a highly sensitive crosslinking component is used or the amount of the photopolymerization initiator is increased, resulting in a phenomenon in which the yellowing of the thermal process becomes stronger. Therefore, by including an antioxidant, yellowing due to oxidation during the heating process can be prevented, and a high transmittance of the coating film can be obtained.

The antioxidant (N) in the present invention may be any compound having a radical scavenging function or a peroxide decomposition function. Specific examples of the antioxidant include hindered phenol-based, hindered amine-based, phosphorus-based, sulfur-based, and hydroxylamine-based compounds, and known antioxidants can be used. In addition, the antioxidant (N) used in the present invention is preferably one that does not contain a halogen atom.

Among the antioxidants (N), preferred ones from the viewpoint of achieving both the transmittance and sensitivity of the coating film are hindered phenol-based antioxidants, hindered amine-based antioxidants, phosphorus-based antioxidants, and sulfur-based antioxidants.

Hindered phenol antioxidants include 1,3,5-tris(3,5-di-t-butyl-4-hydroxybenzyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione, 1,1,3-tris-(2'-methyl-4'-hydroxy-5'-t-butylphenyl)-butane, 4,4'-butylidene-bis-(2-t-butyl-5-methylphenol), 3-(3,5-di-t-butyl-4-hydroxyphenyl)stearyl propionate, pentaerythritol tetrakis[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate, 3,9-bis[2-[3-(3 -t-butyl-4-hydroxy-5-methylphenyl)propionyloxy]-1,1-dimethylethyl]-2,4,8,10-tetraoxaspiro[5.5]undecane, 1,3,5-tris(3,5-di-t-butyl-4-hydroxyphenylmethyl)-2,4,6-trimethylbenzene, 1,3,5-tris(3-hydroxy-4-t-butyl-2,6-dimethylbenzyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione, 2,2'-methylenebis(6-t-butyl-4-ethylphenol), 2,2'-thiodiethylbis-(3,5-di-t-butyl-4-hydroxyphenyl) N,N-hexamethylenebis(3,5-di-t-butyl-4-hydroxy-hydrocinnamamide), i-octyl-3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate, 4,6-bis(dodecylthiomethyl)-o-cresol, calcium salt of 3,5-di-t-butyl-4-hydroxybenzylphosphonic acid monoethyl ester, 4,6-bis(octylthiomethyl)-o-cresol, bis[3-(3-methyl-4-hydroxy-5-t-butylphenyl)propionic acid]ethylenebisoxybisethylene, 1,6-hexanediolbis[3-(3,5- Di-t-butyl-4-hydroxyphenyl)propionate, 2,4-bis-(n-octylthio)-6-(4-hydroxy-3,5-di-t-butylanilino)-1,3,5-triazine, 2,2'-thio-bis-(6-t-butyl-4-methylphenol), 2,5-di-t-amyl-hydroquinone, 2,6-di-t-butyl-4-nonylphenol, 2,2'-isobutylidene-bis-(4,6-dimethyl-phenol), 2,2'-methylene-bis-(6-(1-methyl-cyclohexyl)-p-cresol), 2,4-dimethyl-6-(1-methyl-cyclohexyl)-phenol, etc. In addition, oligomer type and polymer type compounds having a hindered phenol structure can also be used.

More specifically, examples include Adeka STAB AO-20, AO-30, AO-40, AO-50, AO-60, AO-80, and AO-330 manufactured by ADEKA CORPORATION, KEMINOX 101, 179, 76, and 9425 manufactured by ChemiPro Corporation, IRGANOX 1010, 1035, 1076, 1098, 1135, 1330, 1726, 1425WL, 1520L, 245, 259, 3114, 5057, and 565 manufactured by BASF Corporation, and Cyanox CY-1790 and CY-2777 manufactured by Sun Chemical Co., Ltd.

Hindered amine antioxidants include tetrakis(1,2,2,6,6-pentamethyl-4-piperidyl)-1,2,3,4-butane tetracarboxylate, tetrakis(2,2,6,6-tetramethyl-4-piperidyl)1,2,3,4-butane tetracarboxylate, bis(1,2,2,6,6-pentamethyl-4-piperidyl)sebacate, bis(2,2,6,6-tetramethyl-4-piperidyl)sebacate, bis(1-undecanoxy-2,2,6,6-tetramethylpiperidin-4-yl)carbonate, 1,2,2,6,6-pentamethyl-4-piperidyl methacrylate, 2,2 ,6,6-tetramethyl-4-piperidyl methacrylate, polycondensation product of dimethyl succinate and 1-(2-hydroxyethyl)-4-hydroxy-2,2,6,6-tetramethylpiperidine, poly[[6-[(1,1,3,3-tetramethylbutyl)amino]-s-triazine-2,4-diyl]-[(2,2,6,6-tetramethyl-4-piperidyl)imino]-hexamethylene-[(2,2,6,6-tetramethyl-4-piperidyl)imino]], ester of 4-hydroxy-2,2,6,6-tetramethyl-1-piperidineethanol and 3,5,5-trimethylhexanoic acid, N,N'-4,7-tetrakis(tetramethyl-4-piperidyl)imino, Bis[4,6-bis{N-butyl-N-(1,2,2,6,6-pentamethyl-4-piperidyl)amino}-1,3,5-triazin-2-yl]-4,7-diazadecane-1,10-diamine, decanedioic acid bis(2,2,6,6-tetramethyl-1-(octyloxy)-4-piperidinyl)ester, reaction products of 1,1-dimethylethyl hydroperoxide with octane, bis(1,2,2,6,6-pentamethyl-4-pyridyl)[[3,5-bis(1,1dimethylethyl)-4-hydroxyphenyl]methyl]butylmalonate methyl 1,2,2,6,6-pentamethyl-4-pyridylsebake ester, poly[[6-morpholino-s-triazine-2,4-diyl]-[(2,2,6,6-tetramethyl-4-piperidyl)imino]-hexamethylene-[(2,2,6,6-tetramethyl-4-piperidyl)imino]], 2,2,6,6-tetramethyl-4-piperidyl-C12-21 and C18 unsaturated fatty acid ester, N,N'-bis(2,2,6,6-tetramethyl-4-piperidyl)-1,6-hexamethylenediamine, 2-methyl-2-(2,2,6,6-tetramethyl-4-piperidyl)amino-N-(2,2,6,6-tetramethyl-4-piperidyl)propionamide, etc. In addition, oligomer type and polymer type compounds having a hindered amine structure can also be used.

More specifically, examples of such compounds include ADK STAB LA-52, LA-57, LA-63P, LA-68, LA-72, LA-77Y, LA-77G, LA-81, LA-82, LA-87, LA-402F, and LA-502XP manufactured by ADEKA CORPORATION, KAMISTAB 29, 62, 77, and 94 manufactured by Chemipro Chemicals Co., Ltd., Tinuvin 249, TINUVIN 111FDL, 123, 144, 292, and 5100 manufactured by BASF Corporation, and Cyasorb UV-3346, UV-3529, and UV-3853 manufactured by Sun Chemical Co., Ltd.

Phosphorus-based antioxidants include di(2,6-di-t-butyl-4-methylphenyl)pentaerythritol diphosphite, distearyl pentaerythritol diphosphite, 2,2'-methylenebis(4,6-di-t-butylphenyl)2-ethylhexyl phosphite, tris(2,4-di-t-butylphenyl)phosphite, tris(nonylphenyl)phosphite, tetra(C12-C15 alkyl)-4,4'-isopropylidene diphenyl diphosphite, diphenyl mono( 2-ethylhexyl) phosphite, diphenyl isodecyl phosphite, tris(isodecyl) phosphite, triphenyl phosphite, tetrakis(2,4-di-t-butylphenyl)-4,4-biphenyl diphosphonate, tris(tridecyl) phosphite, phenyl isooctyl phosphite, phenyl isodecyl phosphite, phenyl di(tridecyl) phosphite, diphenyl isooctyl phosphite, diphenyl tridecyl phosphite, 4,4'-isopropylide diphenyl alkyl phosphite, trisnonylphenyl phosphite, trisdinonylphenyl phosphite, tris(biphenyl) phosphite, di(2,4-di-t-butylphenyl)pentaerythritol diphosphite, di(nonylphenyl)pentaerythritol diphosphite, phenyl bisphenol A pentaerythritol diphosphite, tetratridecyl 4,4'-butylidenebis(3-methyl-6-t-butylphenol) diphosphite, hexatridecyl Examples include 1,1,3-tris(2-methyl-4-hydroxy-5-t-butylphenyl)butane triphosphite, 3,5-di-t-butyl-4-hydroxybenzyl phosphite diethyl ester, sodium bis(4-t-butylphenyl)phosphite, sodium-2,2-methylene-bis(4,6-di-t-butylphenyl)-phosphite, 1,3-bis(diphenoxyphosphonyloxy)-benzene, ethyl bis(2,4-di-t-butyl-6-methylphenyl) phosphite, etc. Other oligomer and polymer type compounds having a phosphite structure can also be used.

More specifically, examples include Adeka STAB PEP-36, PEP-8, HP-10, 2112, 1178, 1500, C, 135A, 3010, and TPP manufactured by ADEKA CORPORATION, IRGAFOS168 manufactured by BASF CORPORATION, and Hostanox P-EPQ manufactured by Clariant Chemicals K.K.

Examples of sulfur-based antioxidants include 2,2-bis{[3-(dodecylthio)-1-oxopropoxy]methyl}propane-1,3-diylbis[3-(dodecylthio)propionate], ditridecyl 3,3'-thiobispropionate, 2,2-thio-diethylenebis[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate], 2,4-bis[(octylthio)methyl]-o-cresol, and 2,4-bis[(laurylthio)methyl]-o-cresol. Other oligomer and polymer type compounds having a thioether structure can also be used.

More specifically, examples include Adeka STAB AO-412S and AO-503 manufactured by ADEKA CORPORATION, and KEMINOX PLS manufactured by Chemipro Chemicals Co., Ltd.

The antioxidant (N) may be used alone or in a mixture of two or more types in any ratio as required.

The content of the antioxidant (N) is preferably 0.5 to 5.0% by mass based on the solid content of the photosensitive coloring composition, since this provides good transmittance, spectral characteristics, and sensitivity.

[Leveling agent (O)]
The photosensitive coloring composition of the present invention can contain a leveling agent (O) for the purpose of improving the coating property of the composition on a transparent substrate and the drying property of the colored coating. As the leveling agent (O), various surfactants such as silicone surfactants, fluorine surfactants, nonionic surfactants, cationic surfactants, and anionic surfactants can be used.

Silicone surfactants include linear polymers consisting of siloxane bonds and modified siloxane polymers in which organic groups have been introduced into the side chains or ends.

More specifically, BYK-300, 306, 310, 313, 315N, 320, 322, 323, 330, 331, 333, 342, 345/346, 347, 348, 349, 370, 377, 378, 3455, UV3510, 3570 manufactured by BYK-Chemie Co., Ltd., and FZ-7002, 2110 manufactured by Dow Corning Toray Co., Ltd. , 2122, 2123, 2191, 5609, Shin-Etsu Chemical Co., Ltd.'s X-22-4952, X-22-4272, X-22-6266, KF-351A, KF-354L, KF-355A, KF-945, KF-640, KF-642, KF-643, X-22-4515, KF-6004, KP-341, etc.

Fluorosurfactants include surfactants or leveling agents that have a fluorocarbon chain.

More specifically, examples include Surflon S-242, S-243, S-420, S-611, S-651, and S-386 manufactured by AGC Seimi Chemical Co., Ltd., Megafac F-253, F-477, F-551, F-552, F-555, F-558, F-560, F-570, F-575, F-576, R-40-LM, R-41, RS-72-K, and DS-21 manufactured by DIC Corporation, FC-4430 and FC-4432 manufactured by Sumitomo 3M Limited, EF-PP31N09, EF-PP33G1, and EF-PP32C1 manufactured by Mitsubishi Materials Electronic Chemicals Co., Ltd., and Futergent 602A manufactured by NEOS Corporation.

Nonionic surfactants include polyoxyethylene lauryl ether, polyoxyethylene cetyl ether, polyoxyethylene stearyl ether, polyoxyethylene oleyl ether, polyoxyethylene alkyl ether, polyoxyethylene myristyl ether, polyoxyethylene octyldodecyl ether, polyoxyalkylene alkyl ether, polyoxyphenylenedistyrenated phenyl ether, polyoxyethylene tribenzyl phenyl ether, polyoxyethylene polyoxypropylene glycol, polyoxyalkylene alkenyl ether, polyoxyethylene nonyl phenyl ether, polyoxyethylene alkyl ether phosphate ester, sorbitan monolaurate, sorbitan monopalmitate, sorbitan monostearate, sorbitan distearate, sorbitan tristearate, Examples of such sorbitan monooleate, sorbitan trioleate, sorbitan sesquioleate, polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monopalmitate, polyoxyethylene sorbitan monostearate, polyoxyethylene sorbitan tristearate, polyoxyethylene sorbitan monooleate, polyoxyethylene sorbitan triisostearate, polyoxyethylene sorbitan tetraoleate, glycerol monostearate, glycerol monooleate, polyethylene glycol monolaurate, polyethylene glycol monostearate, polyethylene glycol distearate, polyethylene glycol monooleate, polyoxyethylene hydrogenated castor oil, polyoxyethylene alkylamine, alkyl alkanolamide, alkyl imidazoline, etc.

More specifically, Emulgen 103, 104P, 106, 108, 109P, 120, 123P, 130K, 147, 150, 210P, 220, 306P, 320P, 350, 404, 408, 409PV, 420, 430, 705, 707, 709, 1108, 1118S-70, 1135S-70, 1150S-60, 2020G-HA, 2025G, LS manufactured by Kao Corporation. -106, LS-110, LS-114, MS-110, A-60, A-90, B-66, PP-290, Latemul PD-420, PD-430, PD-430S, PD450, Leodor SP-L10, SP-P10, SP-S10V, SP-S20, SP-S30V, SP-O10V, SP-O30V, Super SP-L10, AS-10V, AO-10V, AO-15V, TW -L120, TW-L106, TW-P120, TW-S120V, TW-S320V, TW-O120V, TW-O106V, TW-IS399C, Super TW-L120, 430V, 440V, 460V, MS-50, MS-60, MO-60, MS-165V, Emanone 1112, 3199V, 3299V, 3299RV, 4110, CH-25, CH-40, CH-6 0(K), Amito 102, 105, 105A, 302, 320, Aminone PK-02S, L-02, Homogenol L-95, Adeka Pluronic (registered trademark) L-23, 31, 44, 61, 62, 64, 71, 72, 101, 121, TR-701, 702, 704, 913R manufactured by ADEKA CORPORATION, (meth)acrylic acid-based (co)polymer Polyflow No. 75, No. 90, No. 95 manufactured by Kyoeisha Chemical Co., Ltd., etc.

Cationic surfactants include alkylamine salts, alkyl quaternary ammonium salts such as lauryltrimethylammonium chloride, stearyltrimethylammonium chloride, and cetyltrimethylammonium chloride, and their ethylene oxide adducts.

More specifically, examples include Acetamine 24, Cortamine 24P, 60W, and 86P Conc., manufactured by Kao Corporation.

Examples of anionic surfactants include polyoxyethylene alkyl ether sulfate, sodium dodecylbenzene sulfonate, alkali salts of styrene-acrylic acid copolymers, sodium alkyl naphthalene sulfonate, sodium alkyl diphenyl ether disulfonate, monoethanolamine lauryl sulfate, triethanolamine lauryl sulfate, ammonium lauryl sulfate, monoethanolamine stearate, sodium stearate, sodium lauryl sulfate, monoethanolamine styrene-acrylic acid copolymers, polyoxyethylene alkyl ether phosphates, etc.

More specifically, examples include Futergent 100 and 150 manufactured by Neos Corporation, and Adeka Hope YES-25, Adekacol TS-230E, PS-440E, and EC-8600 manufactured by ADEKA Corporation.

Examples of amphoteric surfactants include alkyl betaines such as lauric acid amidopropyl betaine, lauryl betaine, cocamidopropyl betaine, stearyl betaine, and alkyl dimethylaminoacetate betaine, and alkyl amine oxides such as lauryl dimethylamine oxide.

More specifically, examples include Anhithol 20AB, 20BS, 24B, 55AB, 86B, 20Y-B, and 20N manufactured by Kao Corporation.

When the photosensitive coloring composition of the present invention contains a surfactant, the amount of the surfactant added is preferably 0.001 to 2.0% by mass, more preferably 0.005 to 1.0% by mass, based on the total solid content of the photosensitive coloring composition of the present invention. By being within this range, the balance between the coatability, pattern adhesion, and transmittance of the photosensitive coloring composition becomes good.
The photosensitive coloring composition of the present invention may contain only one type of surfactant, or may contain two or more types. When two or more types are contained, the total amount is preferably within the above range.

[Storage stabilizer (P)]
The photosensitive coloring composition of the present invention may contain a storage stabilizer (P) to stabilize the viscosity of the photosensitive coloring composition over time. Examples of the storage stabilizer (N) include quaternary ammonium chlorides such as benzyl trimethyl chloride and diethylhydroxyamine, organic acids such as lactic acid and oxalic acid and their methyl ethers, organic phosphines such as t-butylpyrocatechol, tetraethylphosphine and tetraphenyl, and phosphites. The storage stabilizer (P) may be used in an amount of 0.1 to 10% by mass based on the total amount of the colorant (100% by mass).

[Adhesion improver (Q)]
The photosensitive coloring composition of the present invention may contain an adhesion improver (Q) such as a silane coupling agent in order to improve adhesion to the substrate. By improving the adhesion by the adhesion improver, the reproducibility of fine lines is improved and the resolution is improved.

Examples of the adhesion improver (Q) include vinyl silanes such as vinyl trimethoxysilane and vinyl triethoxysilane, (meth)acrylic silanes such as 3-methacryloxypropyl methyl dimethoxysilane, 3-methacryloxypropyl trimethoxysilane, 3-methacryloxypropyl methyl diethoxysilane, 3-methacryloxypropyl triethoxysilane, and 3-acryloxypropyl trimethoxysilane, epoxy silanes such as 2-(3,4-epoxycyclohexyl)ethyl trimethoxysilane, 3-glycidoxypropyl methyl dimethoxysilane, 3-glycidoxypropyl trimethoxysilane, 3-glycidoxypropyl methyl diethoxysilane, and 3-glycidoxypropyl triethoxysilane, N-2-(aminoethyl)-3-aminopropyl methyl dimethoxysilane, N-2-(aminoethyl) Examples of the silane coupling agents include silane coupling agents such as 3-aminopropyltrimethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-triethoxysilyl-N-(1,3-dimethyl-butylidene)propylamine, N-phenyl-3-aminopropyltrimethoxysilane, and N-(vinylbenzyl)-2-aminoethyl-3-aminopropyltrimethoxysilane hydrochloride, mercapto compounds such as 3-mercaptopropylmethyldimethoxysilane and 3-mercaptopropyltrimethoxysilane, styryl compounds such as p-styryltrimethoxysilane, ureido compounds such as 3-ureidopropyltriethoxysilane, sulfides such as bis(triethoxysilylpropyl)tetrasulfide, and isocyanates such as 3-isocyanatepropyltriethoxysilane. The adhesion improver can be used in an amount of 0.01 to 10 parts by mass, preferably 0.05 to 5 parts by mass, relative to 100 parts by mass of the colorant in the coloring composition. This range is more effective and provides a good balance of adhesion, resolution, and sensitivity, making it more preferable.

The photosensitive coloring composition of the present invention contains the above-mentioned organic solvent (C) in order to facilitate the formation of a colored film by coating the composition on a substrate such as glass so that the dry film thickness is 0.2 to 5 μm. The organic solvent (C) is selected in consideration of the good coatability of the photosensitive coloring composition, the solubility of each component of the photosensitive coloring composition, and safety.

As the organic solvent (Q), any organic solvent commonly used in the field can be used, and the above-mentioned organic solvents can be used alone or in combination as appropriate according to the application conditions (speed, drying conditions, etc.) taking into consideration the properties such as boiling point, SP value, evaporation rate, and viscosity.

<Method of producing yellow colored composition>
The method for producing the yellow colored composition of the present invention is not particularly limited, and the composition can be produced by a known method. For example, the yellow colorant (A), the dispersion resin (B), and the organic solvent (C) are mixed, and the mixture is dispersed using various dispersing means such as a two-roll mill, a three-roll mill, a ball mill, a horizontal sand mill, a vertical sand mill, an annular bead mill, or an attritor. If necessary, the composition may contain the above-mentioned components.

The average dispersed particle diameter (secondary particle diameter) of the yellow colorant (A) in the yellow coloring composition of the present invention is preferably in the range of 30 to 200 nm, and more preferably in the range of 40 to 200 nm. Within this range, a photosensitive coloring composition with high viscosity stability and dispersion stability can be obtained even when the above-mentioned polymerizable compound (E), photopolymerization initiator (F), etc. are added, and when a color filter is produced using this, a high-quality color filter can be obtained.

The average dispersed particle size (secondary particle size) can be measured using Nikkiso's Microtrac UPA-EX150, which employs dynamic light scattering (FFT power spectrum method), with particle permeability set to absorption mode, particle shape set to non-spherical, and D50 set to the average diameter. The dilution solvent used for measurement is the same organic solvent used for dispersion, and it is preferable to measure samples treated with ultrasound immediately after sample preparation, as this tends to give results with less variation.

The green coloring composition or the red coloring composition can be produced by mixing the yellow coloring composition with a green colorant (D) or a red colorant (E) dispersed by the same method as the yellow coloring composition, or the green colorant (D) or the red colorant (E) and the yellow colorant (A) are mixed and dispersed simultaneously.

<Method for producing photosensitive coloring composition>
The photosensitive coloring composition of the present invention can be prepared by mixing the coloring composition, the polymerizable compound (E), and the photopolymerization initiator (F). If necessary, the above-mentioned components may be contained.

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

<Color filter>
One embodiment of the present invention relates to a color filter. The color filter includes a filter segment formed from the photosensitive coloring composition of the present invention on a substrate.

The color filter of one embodiment is described below.

[Color filter manufacturing method]
The color filter of the present invention can be obtained by the steps of applying the photosensitive coloring composition of the present invention onto a substrate to form a colored layer, exposing the colored layer to light in a pattern through a mask, and developing and removing the unexposed parts to form a colored pattern.
Furthermore, if necessary, a step of drying the colored layer (pre-baking step) and a step of thermally curing the colored pattern (post-baking step) may be provided.

The manufacturing method for the color filter of the present invention is described below.

(Step of forming colored layer)
In the process of forming a colored layer, the photosensitive colored composition of the present invention is applied onto a substrate by a coating method such as spin coating, roll coating, slit coating, casting coating, or inkjet coating, and dried (pre-baked) at a temperature of 50 to 120° C. for 10 to 120 seconds using an oven, a hot plate, or the like as necessary.
Before forming the colored layer on the substrate, a black matrix can be formed in advance. As the black matrix, a multilayer film of chromium or chromium/chromium oxide, an inorganic film such as titanium nitride, or a resin film with a light-shielding agent dispersed therein can be used, but is not limited thereto. In addition, a thin film transistor (TFT) can be formed in advance on the transparent substrate or reflective substrate, and then a colored layer can be formed. The substrate is not particularly limited, and a known one can be used.

(Patternwise Exposure Process)
In the exposure step, the layer formed in the step of forming the colored layer is exposed to light in a specific pattern through a mask using an exposure device such as a stepper, thereby obtaining a cured film.
As radiation that can be used for exposure, ultraviolet rays such as g-rays, h-rays, and i-rays are preferably used.

(Developing process)
By carrying out the alkaline development treatment, the colored layer in the unirradiated areas in the exposure step is dissolved in the alkaline aqueous solution, leaving only the hardened areas.
The developer is not particularly limited and may be a known developer.Specific examples of the developer include alkaline aqueous solutions in which an alkaline compound such as sodium hydroxide, potassium hydroxide, sodium carbonate, sodium silicate, sodium metasilicate, aqueous ammonia, ethylamine, diethylamine, dimethylethanolamine, tetramethylammonium hydroxide, tetraethylammonium hydroxide, choline, pyrrole, piperidine, or 1,8-diazabicyclo-[5.4.0]-7-undecene is dissolved to a concentration of 0.001 to 10% by mass, preferably 0.01 to 1% by mass.
As the alkaline developer, it is preferable to use an alkaline aqueous solution whose alkali concentration is adjusted to preferably pH 11 to 13, more preferably pH 11.5 to 12.5. When the alkali concentration is within the above range, roughening and peeling of the pattern can be more effectively suppressed, the residual film rate can be further improved, and a decrease in the development rate and the generation of development residues can be more effectively suppressed.

The development method is not particularly limited and any known method can be used. For example, there are the dip method, spray method, paddle method, etc., and the temperature is preferably 15 to 40°C. After alkaline development, it is preferable to wash with pure water.

After drying, it is preferable to perform a heat treatment (post-baking) to sufficiently harden the cured film. The heating temperature for post-baking is preferably 100 to 300°C, and more preferably 150 to 250°C. The heating time is preferably about 2 minutes to 1 hour, and more preferably about 3 minutes to 30 minutes.

<Liquid Crystal Display Device>
One embodiment of the present invention relates to a liquid crystal display device comprising the color filter of the present invention.

The following describes one embodiment of the liquid crystal display device.

The configuration of the liquid crystal display device of the present invention is not particularly limited as long as it is a configuration that includes the color filter of the present invention and functions as a liquid crystal display device. For example, the following configurations can be mentioned.

The device includes a color filter and a light source. Examples of light sources include cold cathode fluorescent lamps (CCFLs) and white LEDs, but in the present invention, it is preferable to use white LEDs because they broaden the red reproduction range. Figure 1 is a schematic cross-sectional view of a liquid crystal display device 10 equipped with the color filter of the present invention. The device 10 shown in Figure 1 includes a pair of transparent substrates 11 and 21 arranged opposite each other with a space between them, and liquid crystal LC is sealed between them.

A TFT (thin film transistor) array 12 is formed on the inner surface of the first transparent substrate 11, and a transparent electrode layer 13 made of, for example, ITO is formed thereon. An alignment layer 14 is provided on the transparent electrode layer 13. A polarizing plate 15 is formed on the outer surface of the transparent substrate 11.

On the other hand, the color filter 22 of the present invention is formed on the inner surface of the second transparent substrate 21. The red, green, and blue filter segments that make up the color filter 22 are separated by a black matrix (not shown).

A transparent protective film (not shown) is formed as necessary to cover the color filter 22, and a transparent electrode layer 23 made of, for example, ITO is formed on top of the protective film, and an alignment layer 24 is provided to cover the transparent electrode layer 23.

In addition, a polarizing plate 25 is formed on the outer surface of the transparent substrate 21. In addition, a backlight unit 30 is provided below the polarizing plate 15.

The liquid crystal LC is aligned according to the driving mode, such as TN (Twisted Nematic), STN (Super Twisted Nematic), IPS (In-Plane Switching), VA (Vertical Alignment), OCB (Opticaly Compensated Birefringence), etc. A TFT (thin film transistor) array 12 is formed on the inner surface of the first transparent substrate 11, and a transparent electrode layer 13 made of, for example, ITO is formed thereon. An alignment layer 14 is provided on the transparent electrode layer 13. A polarizing plate 15 is formed on the outer surface of the transparent substrate 11.

On the other hand, the color filter 22 of the present invention is formed on the inner surface of the second transparent substrate 21. The red, green, and blue filter segments that make up the color filter 22 are separated by a black matrix (not shown).

A transparent protective film (not shown) is formed as necessary to cover the color filter 22, and a transparent electrode layer 23 made of, for example, ITO is formed on top of the protective film, and an alignment layer 24 is provided to cover the transparent electrode layer 23.

In addition, a polarizing plate 25 is formed on the outer surface of the transparent substrate 21. In addition, a backlight unit 30 is provided below the polarizing plate 15.

White LED light sources include those in which a fluorescent filter is formed on the surface of a blue LED, and those in which a phosphor is contained in the resin package of a blue LED, and have a wavelength (λ3) in the range of 430 nm to 485 nm at which the emission intensity is maximized, a wavelength (λ4) in the range of 530 nm to 580 nm at which the emission intensity is maximized, and a wavelength (λ5) in the range of 600 nm to 650 nm at which the emission intensity is maximized, and the ratio (I4/I3) of the emission intensity I3 at wavelength λ3 to the emission intensity I4 at wavelength λ4 is 0.2 or more and 0.4 or less. , a white LED light source (LED1) having spectral characteristics in which the ratio (I5/I3) of the emission intensity I3 at wavelength λ3 to the emission intensity I5 at wavelength λ5 is 0.1 or more and 1.3 or less, a white LED light source (LED2) having a wavelength (λ1) at which the emission intensity is maximum within the range of 430 nm to 485 nm, a peak wavelength (λ2) of the second emission intensity within the range of 530 nm to 580 nm, and a ratio (I2/I1) of the emission intensity I1 at wavelength λ1 to the emission intensity I2 at wavelength λ2 is 0.2 or more and 0.7 or less is preferable.

Specific examples of LED1 include NSSW306D-HG-V1 (manufactured by Nichia Chemicals), NSSW304D-HG-V1 (manufactured by Nichia Chemicals), etc.

Specific examples of LED2 include NSSW440 (manufactured by Nichia Chemicals) and NSSW304D (manufactured by Nichia Chemicals).

<Solid-state imaging element>
An embodiment of the present invention relates to a solid-state imaging device comprising the color filter of the present invention.

The following describes one embodiment of the solid-state imaging device.

The configuration of the solid-state imaging element of the present invention is not particularly limited as long as it is a configuration that includes the color filter of the present invention and functions as a solid-state imaging element. For example, the following configurations can be mentioned.

The present invention is configured to have a substrate on which a plurality of photodiodes constituting a light receiving area of a solid-state imaging element (such as a CCD image sensor or a CMOS image sensor) and transfer electrodes made of polysilicon or the like are disposed, a light-shielding film made of tungsten or the like is disposed on the photodiodes and the transfer electrodes, with only the light receiving portions of the photodiodes being opened, a device protection film made of silicon nitride or the like formed on the light-shielding film so as to cover the entire light-shielding film and the light receiving portions of the photodiodes, and a color filter of the present invention is disposed on the device protection film.
Furthermore, the device may have a configuration in which a focusing means (e.g., a microlens, etc.; the same applies below) is provided on the device protection layer and below the color filter (on the side closer to the substrate), or the focusing means is provided on the color filter.

The present invention will be described in more detail below with reference to examples and comparative examples. However, the present invention is not limited to these. In the examples and comparative examples, "parts" and "%" respectively represent "parts by mass" and "% by mass".

Before going into the examples, we will explain each measurement method.

The weight average molecular weight (Mw), number average molecular weight (Mn), acid value (mgKOH/g), and amine value (mgKOH/g) of the resin are as follows:

(Average molecular weight of dispersing resin and binder resin)
The number average molecular weight (Mn) and weight average molecular weight (Mw) of the dispersion resin and binder resin were measured by gel permeation chromatography (GPC) equipped with an RI detector. The apparatus used was HLC-8220GPC (manufactured by Tosoh Corporation), two separation columns were connected in series, and both packings were "TSK-GEL SUPER HZM-N" connected in series. The oven temperature was 40°C, a THF solution was used as the eluent, and the flow rate was 0.35 ml/min.
The sample was dissolved in a solvent containing 1 wt % of the above eluent, and 20 microliters was injected. The molecular weights are all polystyrene equivalent values.

(Acid value of dispersion resin and binder resin)
80 ml of acetone and 10 ml of water were added to 0.5 to 1 g of the dispersion resin and binder resin solution, and the mixture was stirred to dissolve uniformly, and titrated with an automatic titrator ("COM-555" manufactured by Hiranuma Sangyo Co., Ltd.) using a 0.1 mol/L KOH aqueous solution as the titrant to measure the acid value (mgKOH/g). The acid value per solid content of the resin was calculated from the acid value of the resin solution and the solid content concentration of the resin solution.

(Amine value of basic dispersing resin)
The amine value of the basic dispersion resin is the total amine value (mg KOH/g) measured in accordance with the method of ASTM D 2074, converted into solid content.

<Production Example of Yellow Colorant (A1)>
(Finely divided yellow colorant (A1-1))
30 parts of C.I. Pigment Yellow 138 (BASF's "Paliotol Yellow K0960-HD") was dissolved in 300 parts of 101% sulfuric acid, and the mixture was stirred at 70°C for 8 hours to carry out a sulfonation reaction. The end point of the reaction was determined by measuring the spectroscopic spectrum of the sulfuric acid solution and determining the point at which no change in the spectrum was observed. Next, this reaction solution was poured into 3,000 parts of ice water, and the precipitate was filtered off, washed with water, and then dried at 80°C to obtain a compound represented by the following chemical formula (1).
Chemical Formula (1)

The obtained compound represented by chemical formula (1) was dispersed in 10,000 parts of water, and dissolved by adding an aqueous sodium hydroxide solution to adjust the pH to 11. An aqueous aluminum sulfate solution was gradually added to this solution to obtain a precipitate. The precipitate was separated by filtration, washed with water, and then dried at 80° C. to obtain a yellow colorant (A1-1) represented by the following chemical formula (2).
Chemical formula (2)

Next, 100 parts of the obtained yellow colorant (A1-1), 700 parts of sodium chloride, and 180 parts of diethylene glycol were charged into a stainless steel 1-gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 80°C for 6 hours. This mixture was poured into 2,000 parts of warm water and stirred for 1 hour while heating to 80°C to form a slurry. After repeatedly filtering and washing with water to remove the sodium chloride and diethylene glycol, the mixture was dried at 80°C for a day and night to obtain a finely divided yellow colorant (A1-1).

(Finely divided yellow colorant (A1-2))
10 g of the compound represented by chemical formula (1) was added to 500 parts of water and redispersed by stirring at 25° C. for 2 hours. Next, 4.8 parts of copper (II) sulfate pentahydrate was gradually added to this solution and reacted at 60° C. for 2 hours. The reaction product was filtered, washed with water, and dried at 80° C. to obtain a yellow colorant (A1-2) represented by the following chemical formula (3).

Chemical formula (3)

Subsequently, a finely divided yellow colorant (A1-2) was obtained in the same manner as in the production of the yellow colorant (A1-1).

(Finely divided yellow colorant (A1-3))
A yellow colorant (A1-3) represented by the following chemical formula (4) was obtained in the same manner as in the production of the yellow colorant (A1-2), except that 4.3 parts of zinc acetate dihydrate was used instead of the copper (II) sulfate pentahydrate used in the production of the yellow colorant (A1-2).

Chemical formula (4)

Subsequently, a finely divided yellow colorant (A1-3) was obtained in the same manner as in the production of the yellow colorant (A1-1).

(Finely divided yellow colorant (A1-4))
A yellow colorant (A1-4) represented by the following chemical formula (5) was obtained in the same manner as in the production of yellow colorant (A1-2), except that 5.2 parts of iron (III) chloride hexahydrate was used instead of the copper (II) sulfate pentahydrate used in the production of yellow colorant (A1-2).

Chemical formula (5)

Subsequently, a finely divided yellow colorant (A1-4) was obtained in the same manner as in the production of the yellow colorant (A1-1).

(Finely divided yellow colorant (A1-5))
A yellow colorant (A1-5) represented by the following chemical formula (6) was obtained in the same manner as in the production of yellow colorant (A1-2), except that 6.6 parts of silver nitrate (I) was used instead of the copper (II) sulfate pentahydrate used in the production of yellow colorant (A1-2).

Chemical formula (6)

Subsequently, a finely divided yellow colorant (A1-5) was obtained in the same manner as in the production of the yellow colorant (A1-1).

(Finely divided yellow colorant (A1-6))
To 200 parts of methyl benzoate, 40 parts of 8-aminoquinaldine, 90.1 parts of tetrachlorophthalic anhydride, and 183.2 parts of benzoic acid were added, and the mixture was heated to 120°C and stirred for 4 hours while distilling off water. Next, 62.4 parts of 2,3-naphthalenedicarboxylic anhydride was added, and the mixture was heated to 180°C and stirred for 4 hours while distilling off water. After cooling to room temperature, the reaction mixture was poured into 1,200 parts of ethanol and stirred at room temperature for 1 hour. The precipitate was filtered off, washed with ethanol, and then dried.
Next, 30 parts of the precipitate obtained was dissolved in 300 parts of 101% sulfuric acid and stirred at 70° C. for 8 hours to carry out a sulfonation reaction. The end point of the reaction was determined by measuring the spectroscopic spectrum of the sulfuric acid solution and determining that no change in the spectrum was observed. Next, this reaction solution was poured into 3,000 parts of ice water, and the precipitate was filtered, washed with water, and then dried at 80° C. to obtain a compound represented by the following chemical formula (7).

Chemical formula (7)

The obtained compound represented by chemical formula (7) was dispersed in 10,000 parts of water, and dissolved by adding an aqueous sodium hydroxide solution to adjust the pH to 11. An aqueous aluminum sulfate solution was gradually added to this solution to obtain a precipitate. The precipitate was separated by filtration, washed with water, and dried at 80° C. to obtain a yellow colorant (A1-6) represented by chemical formula (8).

Chemical formula (8)

Next, 100 parts of the obtained yellow colorant (A1-6), 700 parts of sodium chloride, and 180 parts of diethylene glycol were charged into a stainless steel 1-gallon kneader (manufactured by Inoue Seisakusho Co., Ltd.) and kneaded for 6 hours at 80° C. This mixture was poured into 2,000 parts of warm water, and stirred for 1 hour while heating to 80° C. to form a slurry, which was then repeatedly filtered and washed with water to remove the sodium chloride and diethylene glycol, and then dried at 80° C. for one day to obtain a finely divided yellow colorant (A1-6).

(Finely divided yellow colorant (A1-7))
A yellow colorant (A1-7) represented by chemical formula (9) was obtained in the same manner as in the production of yellow colorant (A1-6), except that 5.5 parts of copper sulfate (II) pentahydrate was used instead of the aluminum sulfate used in the production of yellow colorant (A1-6).

Chemical formula (9)

Subsequently, a finely divided yellow colorant (A1-7) was obtained in the same manner as in the production of the yellow colorant (A1-6).

<Production Example of Other Yellow Colorant (A2)>
(Finely divided C.I. Pigment Yellow 138 (A2-1))
100 parts of C.I. Pigment Yellow 138 (BASF "Paliotol Yellow K0960-HD"), 700 parts of sodium chloride, and 180 parts of diethylene glycol were charged into a stainless steel 1-gallon kneader (Inoue Seisakusho) and kneaded for 6 hours at 80 ° C. This mixture was added to 2,000 parts of hot water, heated to 80 ° C. and stirred for 1 hour to form a slurry, filtered and washed with water repeatedly to remove sodium chloride and diethylene glycol, and then dried at 80 ° C. for one day to obtain finely divided C.I. Pigment Yellow 138 (A2-1).

(Finely divided yellow colorant (A2-2))
According to Example 1 of JP2012-226110A, a finely divided yellow colorant (A2-2) represented by the following chemical formula (10) was obtained.

Chemical Formula (10)

<Production Example of Green Colorant (D)>
(Finely divided C.I. Pigment Green 36 (D-1))
200 parts of C.I. Pigment Green 6, a green colorant, 1.00 parts of sodium chloride, and 360 parts of ethylene glycol were charged into a stainless steel 1-gallon kneader (manufactured by Inoue Seisakusho) and kneaded for 6 hours at 80° C. Next, this kneaded product was put into 8 liters of warm water, heated to 80° C. and stirred for 2 hours to form a slurry, filtered and washed repeatedly to remove sodium chloride and diethylene glycol, and then dried at 85° C. for one day to obtain finely divided C.I. Pigment Green 36 (D-1).

(Finely divided C.I. Pigment Green 58 (D-2))
100 parts of a green colorant, C.I. Pigment Green 58 (DIC Corporation "FASTGEN GREEN A110"), 1,200 parts of sodium chloride, and 120 parts of diethylene glycol were charged into a stainless steel 1-gallon kneader (Inoue Manufacturing Co., Ltd.) and kneaded for 6 hours at 70 ° C. This kneaded product was added to 3,000 parts of warm water, heated to 70 ° C. and stirred for 1 hour to form a slurry, filtered and washed repeatedly to remove sodium chloride and diethylene glycol, and then dried at 80 ° C. for a day and night to obtain finely divided C.I. Pigment Green 58 (D-1).

(Finely divided green colorant (D-3))
In a 300 mL flask, 91 parts of sulfuryl chloride, 109 parts of aluminum chloride, 15 parts of sodium chloride, 30 parts of zinc phthalocyanine, and 59 parts of bromine were charged. The mixture was heated to 130°C over 40 hours, taken out in water, and then filtered to obtain a green crude pigment. 20 parts of the obtained green crude pigment, 140 parts of pulverized sodium chloride, 32 parts of diethylene glycol, and 1.8 parts of xylene were charged in a 1 L double-arm kneader and kneaded at 100°C for 6 hours. After kneading, the mixture was taken out in 2 kg of water at 80°C, stirred for 1 hour, filtered, washed with hot water, dried, and pulverized to obtain a finely divided green colorant (D-3). The obtained finely divided green colorant (D-3) had an average of 12.71 halogen atoms per molecule according to fluorescent X-ray analysis, of which the average number of bromine atoms was 10.22 and the average number of chlorine atoms was 2.49.

(Finely divided green colorant (D-4))
According to the example of JP 2017-111398 A, a finely divided green colorant (D-4) represented by the following chemical formula (11) was obtained.

Chemical Formula (11)

(Finely divided green colorant (D-5))
According to the example of JP 2017-111398 A, a finely divided green colorant (D-5) represented by the following chemical formula (12) was obtained.

Chemical Formula (12)

<Production Example of Red Colorant (E)>
(Finely divided C.I. Pigment Red 254 (E-1))
100 parts of C.I. Pigment Red 254 (BASF "Irgazin Red D3656 HD"), 1,000 parts of sodium chloride, and 120 parts of diethylene glycol were charged into a stainless steel 1 gallon kneader (Inoue Seisakusho) and kneaded for 10 hours at 60 ° C. Next, the kneaded mixture was poured into hot water, heated to about 80 ° C. and stirred for 1 hour to form a slurry, filtered and washed with water repeatedly to remove sodium chloride and diethylene glycol, then dried at 80 ° C. overnight and pulverized to obtain finely divided C.I. Pigment Red 254 (E-1).

(Micronized C.I. Pigment Red 177 (E-2))
C. I. Pigment Red 254 was replaced with C. I. Pigment Red 177 (manufactured by Shinic, "Sinilex Red SR3C"), and the resultant was pulverized in the same manner as for the finely divided C. I. Pigment Red 254 (E-1), to obtain finely divided C. I. Pigment Red 177 (E-2).

(Finely divided red colorant (E-3))
In a stainless steel reaction vessel equipped with a reflux condenser, 200 parts of tert-amyl alcohol dehydrated with a molecular sieve and 140 parts of sodium tert-amyl alkoxide were added under a nitrogen atmosphere, and the mixture was heated to 100°C while stirring to prepare an alcoholate solution. Meanwhile, 88 parts of diisopropyl succinate and 153.6 parts of 4-bromobenzonitrile were added to a glass flask, and the mixture was dissolved by heating to 90°C while stirring to prepare a solution of the mixture. The heated solution of the mixture was slowly dropped at a constant rate over 2 hours into the alcoholate solution heated to 100°C while stirring vigorously. After the dropwise addition, the mixture was heated and stirred for 2 hours at 90°C to obtain an alkali metal salt of a diketopyrrolopyrrole compound. Furthermore, 600 parts of methanol, 600 parts of water, and 304 parts of acetic acid were added to a glass jacketed reaction vessel, and the mixture was cooled to -10°C. The cooled mixture was rotated at 4000 rpm using a high-speed stirring disperser with a shear disk having a diameter of 8 cm, and the previously obtained alkali metal salt solution of the diketopyrrolopyrrole compound cooled to 75 ° C. was added in small amounts to the cooled mixture. At this time, the mixture was cooled so that the temperature of the mixture consisting of methanol, acetic acid, and water was always kept at a temperature of −5 ° C. or less, and the addition rate of the alkali metal salt of the diketopyrrolopyrrole compound at 75 ° C. was adjusted while being added in small amounts over about 120 minutes. After the addition of the alkali metal salt, red crystals were precipitated, and a red suspension was generated. Subsequently, the obtained red suspension was washed with an ultrafiltration device at 5 ° C., and then filtered to obtain a red paste. This paste was redispersed in 3500 parts of methanol cooled to 0 ° C. to obtain a suspension with a methanol concentration of about 90%, which was stirred at 5 ° C. for 3 hours, and particle sizing and washing accompanied by crystal transition were performed. Subsequently, the mixture was filtered using an ultrafilter, and the resulting aqueous paste of the diketopyrrolopyrrole compound was dried at 80° C. for 24 hours and pulverized to obtain 150.8 parts of a red colorant (E-3).
100 parts of the obtained red colorant (E-3), 1,000 parts of sodium chloride, and 120 parts of diethylene glycol were charged into a stainless steel 1-gallon kneader (manufactured by Inoue Seisakusho Co., Ltd.) and kneaded for 10 hours at 60° C. Next, the kneaded mixture was poured into warm water and stirred for 1 hour while heating to about 80° C. to form a slurry, which was then filtered and washed with water to remove the sodium chloride and diethylene glycol, and then dried overnight at 80° C. and pulverized to obtain a finely divided red colorant (E-3).

<Production Example of Dispersion Resin (B)>
(Basic Dispersion Resin (B1-1))
In a reaction apparatus equipped with a gas inlet tube, a condenser, an agitator, and a thermometer, 40 parts of methyl methacrylate, 10 parts of n-butyl methacrylate, and 13.2 parts of tetramethylethylenediamine as a catalyst were charged, and the mixture was stirred at 50° C. for 1 hour while flowing nitrogen, and the inside of the system was replaced with nitrogen. Next, 9.3 parts of ethyl bromoisobutyrate as an initiator, 5.6 parts of cuprous chloride as a catalyst, and 133 parts of propylene glycol monomethyl ether acetate (hereinafter also referred to as PGMAc) were charged, and the temperature was raised to 110° C. under a nitrogen stream to initiate polymerization of the first block (B block). After polymerization for 4 hours, the polymerization solution was sampled and the solid content was measured, and it was confirmed that the polymerization conversion rate was 98% or more based on the non-volatile content. Next, 61 parts of PGMAc, 40 parts of dimethylaminoethyl methacrylate as a second block (A block) monomer, and 10 parts of methacryloyloxyethylbenzyldimethylammonium chloride were added to the reaction apparatus, and the mixture was stirred while maintaining 110° C. under a nitrogen atmosphere to continue the reaction. Two hours after the addition, the polymerization solution was sampled and the solid content was measured, and it was confirmed that the polymerization conversion rate of the second block (A block) was 98% or more calculated from the non-volatile content, and the reaction solution was cooled to room temperature to terminate the polymerization. As a result of GPC measurement, the polymer had a mass average molecular weight of 20,000, a molecular weight distribution Mw/Mn of 1.4, and a reaction conversion rate of 98.5%. In this way, a basic dispersion resin (B1-1) having an amine value per solid content of 169.8 mgKOH/g was obtained. After cooling to room temperature, about 2 g of the resin-type dispersant solution was sampled and dried by heating at 180° C. for 20 minutes to measure the non-volatile content, and PGMAc was added so that the non-volatile content became 30% by mass to prepare a basic dispersion resin (B1-1) solution.

(Basic Dispersion Resin (B1-2))
In a reaction apparatus equipped with a gas inlet tube, a condenser, a stirring blade, and a thermometer, 30 parts of methyl methacrylate, 30 parts of n-butyl methacrylate, 20 parts of hydroxyethyl methacrylate, and 13.2 parts of tetramethylethylenediamine were charged, and the mixture was stirred at 50° C. for 1 hour while flowing nitrogen, and the inside of the system was replaced with nitrogen. Next, 9.3 parts of ethyl bromoisobutyrate, 5.6 parts of cuprous chloride, and 133 parts of PGMAc were charged, and the temperature was raised to 110° C. under a nitrogen stream to initiate polymerization of the first block (B block). After polymerization for 4 hours, the polymerization solution was sampled and the nonvolatile content was measured, and it was confirmed that the polymerization conversion rate was 98% or more based on the nonvolatile content.
Next, 61 parts of PGMAc and 20 parts of 1,2,2,6,6-pentamethylpiperidyl methacrylate (Fancryl FA-711MM, manufactured by Hitachi Chemical Co., Ltd.) as a second block (A block) monomer were added to this reaction apparatus, and the reaction was continued by stirring while maintaining a nitrogen atmosphere at 110° C. Two hours after the addition of 1,2,2,6,6-pentamethylpiperidyl methacrylate, a sample was taken from the polymerization solution and the nonvolatile content was measured. It was confirmed that the polymerization conversion rate of the second block (A block) was 98% or more calculated from the nonvolatile content, and the reaction solution was cooled to room temperature to terminate the polymerization.
In this way, a basic dispersion resin (B1-2) having a piperidyl skeleton with an amine value of 57 mgKOH/g per nonvolatile content and a number average molecular weight of 4,500 (Mn) was obtained. The basic dispersion resin (B1-1) solution was diluted in the same manner as the basic dispersion resin (B1-1) solution to prepare a basic dispersion resin (B1-2) solution having a nonvolatile content of 30% by mass.

(Basic Dispersion Resin (B1-3))
Using the method for producing pigment dispersant (1) described in Production Example 1 of Japanese Patent No. 5,513,691, [(quaternized product of 3-(N,N-dimethylamino)propylacrylamide/methoxypolyethylene glycol methacrylate copolymer (23/77 wt%); quaternization rate: 27 mol%)] was synthesized and diluted in the same manner as for the basic dispersion resin (B1-1) solution to prepare a basic dispersion resin (B1-3) solution having a nonvolatile content of 30 mass%.

(Dispersion resin (B2-1) which is a salt of phenylphosphonic acid and a basic dispersion resin having an amino group)
In a 100 mL round-bottom flask, 12.6 parts by mass of a basic dispersion resin (methyl methacrylate/dimethylaminoethyl methacrylate: composition ratio 5/3) was dissolved in 35 parts by mass of PGMAc, 2.4 parts by mass of phenylphosphonic acid, a salt-forming component (0.5 molar equivalent relative to dimethylaminoethyl methacrylate), was added, and the mixture was stirred at a reaction temperature of 40° C. for 2 hours to prepare a 30% by mass solids solution of a dispersion resin (B2-1), which is a salt of phenylphosphonic acid and a basic dispersion resin having an amino group.

(Dispersion resin (B2-2) which is a salt of phenylphosphonic acid and a basic dispersion resin having an amino group and an ammonium salt)
In a 100 mL round-bottom flask, 12.6 parts by mass of a basic dispersion resin (methyl methacrylate / dimethylaminoethyl methacrylate / dimethylaminoethyl methacrylate methyl chloride salt: composition weight ratio 3/3/2) was dissolved in 35 parts by mass of PGMAc, 2.4 parts by mass of phenylphosphonic acid, which is a salt-forming component (0.5 molar equivalent relative to dimethylaminoethyl methacrylate), was added, and the mixture was stirred at a reaction temperature of 40° C. for 2 hours to prepare a 30% by mass solids solution of a dispersion resin (B2-2), which is a salt of phenylphosphonic acid, an amino group, and a basic dispersion resin having an ammonium salt.

(Dispersion resin (B2-3) which is a salt of phenylphosphinic acid and a basic dispersion resin having an amino group)
250 parts by mass of tetrahydrofuran and 5.81 parts by mass of dimethylketene methyltrimethylsilyl acetal as an initiator were added to a 500 mL round-bottomed 4-neck separable flask equipped with a cooling tube, an addition funnel, a nitrogen inlet, a mechanical stirrer, and a digital thermometer, and nitrogen substitution was sufficiently performed. 0.5 parts by mass of a 1 mol/L acetonitrile solution of tetrabutylammonium m-chlorobenzoate as a catalyst was injected using a syringe, and 19.7 parts by mass of 2-hydroxyethyl methacrylate, 7.5 parts by mass of 2-ethylhexyl methacrylate, 12.9 parts by mass of n-butyl methacrylate, 10.7 parts by mass of benzyl methacrylate, and 30.9 parts by mass of methyl methacrylate as blocking monomers having solvent affinity were dropped using an addition funnel over 60 minutes. The temperature was kept below 40° C. by cooling the reaction flask in an ice bath. After 1 hour, 18.3 parts by mass of dimethylaminopropyl methacrylamide, a monomer for a colorant-adsorbing functional block, was added dropwise over 20 minutes. After reacting for 1 hour, 1 part by mass of methanol was added to terminate the reaction. The resulting block copolymer tetrahydrofuran solution was reprecipitated in hexane, filtered, and purified by vacuum drying.
Next, 15.0 parts by mass of the obtained block copolymer was dissolved in 35 parts by mass of PGMAc in a 100 mL round-bottom flask, and 1.1 parts by mass of phenylphosphinic acid (0.5 molar equivalent relative to dimethylaminopropyl methacrylamide), which is a salt-forming component, was added. The mixture was stirred at a reaction temperature of 30° C. for 20 hours, and PGMAc was added to adjust the mixture, thereby obtaining a dispersion resin (B2-3) solution, which is a salt of phenylphosphinic acid and a basic dispersion resin having an amino group, with a solid content of 30% by mass.

(Phosphoric acid-based dispersion resin (B3-1))
In a reaction vessel equipped with a nitrogen gas inlet tube, a condenser, and a stirrer, 186 g of lauryl alcohol, 571 g of ε-caprolactone monomer, and 0.6 g of tetrabutyl titanate were charged, and the mixture was replaced with nitrogen gas, and then heated and stirred at 120 ° C. for 3 hours. The disappearance of the caprolactone monomer was confirmed by an RI detector of GPC (gel permeation chromatography) using tetrahydrofuran as an eluent. After cooling to 40 ° C. or less, the mixture was mixed with 84.5 g of polyphosphoric acid having an orthophosphoric acid content of 116%, gradually heated, and heated at 80 ° C. for 6 hours with stirring to obtain a phosphoric acid-based resin-type dispersant (B4-1) having a number average molecular weight of R1 of 760 and an abundance ratio of n = 1 and 2 of 100:12. The solid content was adjusted with PGMAc to obtain a phosphoric acid-based dispersion resin (B3-1) solution having a solid content of 30% and an acid value of 166 mg KOH / g per nonvolatile content.

(Phosphate-based dispersion resin (B3-2))
A thermometer, a cooling tube, a nitrogen gas inlet tube, and a stirrer were attached to a separable four-neck flask, and 1500 parts of cyclohexanone were charged. The temperature was raised to 80 ° C., and the inside of the reaction vessel was replaced with nitrogen. Then, a mixture of 120 parts of methyl methacrylate, 210 parts of n-butyl methacrylate, 90 parts of 2-hydroxyethyl methacrylate, 60 parts of methacrylic acid, 120 parts of paracumylphenol ethylene oxide modified acrylate (manufactured by Toagosei Co., Ltd., "Aronix M-110"), 6 parts of acid phosphoxyethyl methacrylate, and 30 parts of 2,2'-azobisisobutyronitrile was dripped over 2 hours. After the dripping was completed, the reaction was continued for another 3 hours, and a phosphoric acid dispersion resin (B3-2) solution with a solid content of 30% and a weight average molecular weight of 24,000 was obtained.

(Carboxylic Acid-Based Dispersion Resin (B4-1))
A reaction vessel equipped with a gas inlet tube, a temperature controller, a condenser, and a stirrer was charged with 10 parts of methacrylic acid, 100 parts of methyl methacrylate, 70 parts of i-butyl methacrylate, 20 parts of benzyl methacrylate, and 50 parts of PGMAc, and substituted with nitrogen gas. The reaction vessel was heated to 50 ° C. and stirred, and 12 parts of 3-mercapto-1,2-propanediol was added. The temperature was raised to 90 ° C., and a solution of 0.1 parts of 2,2'-azobisisobutyronitrile added to 90 parts of PGMAc was added and reacted for 7 hours. It was confirmed that 95% had reacted by solid content measurement. 19 parts of pyromellitic anhydride, 50 parts of PGMAc, 50 parts of cyclohexanone, and 0.4 parts of 1,8-diazabicyclo-[5.4.0]-7-undecene as a catalyst were added, and the reaction was carried out at 100 ° C. for 7 hours. The reaction was terminated after confirming that 98% or more of the acid anhydride had been half-esterified by measuring the acid value, and the reaction solution was diluted with propylene glycol monomethyl ether acetate to a solid content of 30% by measuring the solid content, thereby obtaining a carboxylic acid-based dispersion resin (B4-1) solution having an acid value of 70 mgKOH/g and a weight average molecular weight of 8,500.

(Carboxylic acid-based dispersion resin (B4-1-1)
In a reaction vessel equipped with a gas inlet tube, a condenser, an agitator, and a thermometer, 3 parts of trimellitic anhydride, 1 part of 3-mercapto-1,2-propanediol, 50 parts of PGMAc, and 0.1 parts of dimethylbenzylamine were charged. After replacing with nitrogen gas, the inside of the reaction vessel was heated to 120°C and reacted for 4 hours, and then reacted at 80°C for 2 hours. Furthermore, 30 parts of tertiary butyl acrylate, 20 parts of ETERNACOLL OXMA (methacrylate (3-ethyloxetan-3-yl) methyl, manufactured by Ube Industries, Ltd.), 5 parts of methacrylic acid, 40 parts of ethyl acrylate, and 10 parts of PGMAc were charged, and 0.2 parts of 2,2'-azobisisobutyronitrile were added in 15 portions every 30 minutes while maintaining the inside of the reaction vessel at 80°C. The nonvolatile content was measured 1 hour after the final addition, and it was confirmed that 95% of the monomer had reacted. The solution was diluted with PGMAc so that the nonvolatile content was 30% by nonvolatile content measurement, and a carboxylic acid-based dispersion resin (B4-1-1) solution having an acid value of 51 mgKOH/g and a weight average molecular weight (Mw) of 24,000 per nonvolatile content was obtained.

(Carboxylic acid-based dispersion resin (B4-1-2)
In a reaction vessel equipped with a gas inlet tube, a thermometer, a condenser, and a stirrer, 108 parts of 1-thioglycerol, 174 parts of pyromellitic anhydride, 650 parts of PGMAc, and 0.2 parts of monobutyltin oxide as a catalyst were charged, and the mixture was replaced with nitrogen gas, and reacted at 120 ° C. for 5 hours (first step). It was confirmed that 95% or more of the acid anhydride was half-esterified by measuring the acid value. Next, 160 parts of the compound obtained in the first step in terms of solid content, 200 parts of 2-hydroxypropyl methacrylate, 200 parts of ethyl acrylate, 150 parts of t-butyl acrylate, 200 parts of 2-methoxyethyl acrylate, 200 parts of methyl acrylate, 50 parts of methacrylic acid, and 663 parts of PGMAc were charged, and the reaction vessel was heated to 80 ° C., and 1.2 parts of 2,2'-azobis (2,4-dimethylvaleronitrile) was added, and the reaction was carried out for 12 hours (second step). It was confirmed that 95% had reacted by measuring the solid content. Finally, 500 parts of a 50% PGMAc solution of the compound obtained in the second step, 27.0 parts of 2-methacryloyloxyethyl isocyanate (MOI), and 0.1 parts of hydroquinone were charged, and the reaction was carried out until the disappearance of the peak at 2270 cm-1 due to the isocyanate group was confirmed by IR (third step). After confirming the disappearance of the peak, the reaction solution was cooled and the solid content was adjusted with PGMAc to obtain a carboxylic acid dispersion resin (B4-1-2) solution with a solid content of 30%. The acid value of the obtained carboxylic acid dispersion resin (B4-1-2) was 68 mgKOH/g, the unsaturated double bond equivalent was 1,593, and the weight average molecular weight was 13,000.

(Carboxylic Acid-Based Dispersion Resin (B4-2))
In a reaction vessel equipped with a gas inlet tube, a thermometer, a condenser, and a stirrer, 62.6 parts of 1-dodecanol, 287.4 parts of ε-caprolactone, and 0.1 parts of monobutyltin (IV) oxide as a catalyst were charged, and the mixture was replaced with nitrogen gas, and then heated and stirred at 120 ° C. for 4 hours. After confirming that 98% had reacted by solid content measurement, 73.3 parts of pyromellitic anhydride were added and reacted at 120 ° C. for 2 hours. The reaction was terminated after confirming that 98% or more of the acid anhydride had been half-esterified by acid value measurement. A carboxylic acid-based dispersion resin (B4-2) solution with a solid content of 30% was obtained by adjusting the solid content with PGMAc. The acid value of the obtained carboxylic acid-based dispersion resin was 49 mg KOH / g.

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

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

(Binder Resin (H-3))
A separable 4-neck flask equipped with a thermometer, a cooling tube, a nitrogen gas inlet tube, a dropping tube and a stirrer was charged with 370 parts of cyclohexanone, and the temperature was raised to 80 ° C., and the inside of the flask was replaced with nitrogen, and then a mixture of 18 parts of paracumylphenol ethylene oxide modified acrylate (Aronix M110 manufactured by Toagosei Co., Ltd.), 10 parts of benzyl methacrylate, 18.2 parts of glycidyl methacrylate, 25 parts of methyl methacrylate, and 2.0 parts of 2,2'-azobisisobutyronitrile was dropped over 2 hours from the dropping tube. After the dropping, the mixture was further reacted at 100 ° C. for 3 hours, and then a solution of 1.0 part of azobisisobutyronitrile in 50 parts of cyclohexanone was added, and the reaction was continued at 100 ° C. for 1 hour. Next, the inside of the container was replaced with air, and 9.3 parts of acrylic acid (100% of glycidyl groups) was added to 0.5 parts of trisdimethylaminophenol and 0.1 parts of hydroquinone in the container, and the reaction was continued for 6 hours at 120 ° C., and the reaction was terminated when the solid acid value reached 0.5, to obtain an acrylic resin solution. Furthermore, 19.5 parts of tetrahydrophthalic anhydride (100% of the generated hydroxyl groups) and 0.5 parts of triethylamine were added and reacted at 120 ° C. for 3.5 hours to obtain an acrylic resin solution. After cooling to room temperature, about 2 g of the resin solution was sampled and dried at 180 ° C. for 20 minutes to measure the nonvolatile content, and PGMAc was added to the resin solution synthesized earlier so that the nonvolatile content was 20% by mass to prepare a binder resin (H-3) solution. The weight average molecular weight (Mw) was 19,000.

(Binder resin (H-4))
A separable flask equipped with a cooling tube was prepared as a reaction vessel. Meanwhile, a thoroughly stirred mixture of 40 parts of dimethyl-2,2'-[oxybis(methylene)]bis-2-propenoate, 40 parts of methacrylic acid, 120 parts of methyl methacrylate, 4 parts of t-butylperoxy-2-ethylhexanoate ("Perbutyl O" manufactured by Nippon Oil & Fats), and 40 parts of PGMAc was prepared as a monomer dropping vessel. A thoroughly stirred mixture of 8 parts of n-dodecanethiol and 32 parts of propylene glycol monomethyl ether acetate was prepared as a chain transfer agent dropping vessel.
395 parts of PGMAc was charged into the reaction vessel, and after replacing with nitrogen, the temperature of the reaction vessel was raised to 90 ° C. by heating in an oil bath while stirring. After the temperature of the reaction vessel was stabilized at 90 ° C., dropping was started from the monomer dropping vessel and the chain transfer agent dropping vessel. Dropping was carried out over 135 minutes while maintaining the temperature at 90 ° C. 60 minutes after the end of dropping, the temperature was raised to 110 ° C. After maintaining 110 ° C. for 3 hours, a gas inlet tube was attached to the separable flask, and bubbling of a mixed gas of oxygen / nitrogen = 5 / 95 (volume ratio) was started. Next, 70 parts of glycidyl methacrylate, 0.4 parts of 2,2'-methylenebis (4-methyl-6-t-butylphenol), and 0.8 parts of triethylamine were charged into the reaction vessel, and the reaction was carried out at 110 ° C. for 12 hours. Then, 150 parts of PGMAc was added and cooled to room temperature, and about 2 g of the resin solution was sampled and dried by heating at 180°C for 20 minutes to measure the non-volatile content, and PGMAc was added to the previously synthesized resin solution so that the non-volatile content was 20 mass%, to obtain a binder resin (H-4) solution. The weight average molecular weight of the resin was 18,000, and the acid value per solid content was 2 mgKOH/g.

<Production of Yellow Colored Composition>
[Example 1]
(Yellow Colored Composition (YB-1))
The following raw materials were mixed and stirred to be uniform, and then dispersed for 3 hours in an Eiger mill ("Mini Model M-250 MKII" manufactured by Eiger Japan Co., Ltd.) using zirconia beads having a diameter of 0.5 mm, and then filtered through a filter having a pore size of 1.0 μm to prepare a yellow colored composition (YB-1) having a non-volatile content of 20.0 mass %. The organic solvent (C-1) was PGMAc.
Finely divided yellow colorant (A1-1): 12 parts by weight Basic dispersion resin (B1-1) solution: 20 parts by weight Binder resin (H-1) solution: 10 parts by weight Organic solvent (C-1): 58 parts by weight

[Examples 2 to 38, Comparative Examples 1 to 4]
(Yellow Colored Compositions (YB-2 to 43))
Yellow colored compositions (YB-2 to 43) were prepared in the same manner as in Example 1, except that the material types and masses were changed as shown in Table 1.

[Comparative Example 5]
(Yellow colored composition (YB-44))
A yellow colored composition (YB-44) was prepared in the same manner as in Example 1, except that the compound represented by the above-mentioned chemical formula (1) (not in the form of a metal salt) was used as the yellow colorant (A) instead of the finely divided yellow colorant (A1-1).

<Evaluation of Yellow Colored Composition>
The obtained yellow colored compositions (YB-1 to 44) were evaluated for brightness, contrast ratio, and foreign matter by the following methods. The evaluation results are shown in Table 2.

(Lightness Evaluation)
The yellow colored composition was applied onto a glass substrate of 100 mm x 100 mm and 1.1 mm thick using a spin coater, and heated at 230°C for 20 minutes to obtain a coating film. At this time, the coating conditions (spin coater rotation speed, time) were appropriately changed so that the coating film had a thickness of x = 0.430 under C light source after heat treatment at 230°C. The lightness (Y) of the obtained coating film was measured using a microspectrophotometer (Olympus Optical Co., Ltd. "OSP-SP100"). A value of 3 or more is practical.
5: 91.0 or more 4: 89.0 or more, but less than 91.0 3: 88.0 or more, but less than 89.0 2: 87.0 or more, but less than 88.0 1: Less than 87.0

(Contrast ratio evaluation)
The light emitted from the backlight unit for liquid crystal display is polarized by passing through a polarizing plate, passes through a coating film of a coloring composition applied on a glass substrate, and reaches the other polarizing plate. In this case, if the polarization planes of the polarizing plates are parallel, the light passes through the polarizing plate, but if the polarization planes are perpendicular, the light is blocked by the polarizing plate. However, when the light polarized by the polarizing plate passes through the coating film of the coloring composition, scattering occurs due to colorant particles, and if a part of the polarization plane is shifted, the amount of light transmitted decreases when the polarizing plates are parallel, and part of the light is transmitted when the polarizing plates are perpendicular. This transmitted light was measured as the luminance on the polarizing plate, and the ratio of the luminance when the polarizing plates are parallel to the luminance when they are perpendicular was calculated as the contrast ratio.

(Contrast ratio) = (Luminance when parallel) / (Luminance when perpendicular)

Thus, scattering caused by colorants in the coating reduces the parallel luminance and increases the perpendicular luminance, resulting in a lower contrast ratio.
The same coating film as that for the evaluation of brightness was used, and a color luminance meter (Topcon Corporation's "BM-5A") was used as the luminance meter, and a polarizing plate (Nitto Denko Corporation's "NPF-G1220DUN") was used as the polarizing plate. The measurement was performed through a black mask with a 1 cm square hole in the measurement area. A value of 3 or more was considered to be a practical level.
5: 25,000 or more 4: 20,000 or more, but less than 25,000 3: 15,000 or more, but less than 20,000 2: 10,000 or more, but less than 15,000 1: Less than 10,000

(Evaluation of foreign matter)
The yellow colored composition was applied onto a transparent substrate so that the dried coating film had a thickness of about 2.0 μm, and heat-treated in an oven at 250° C. for 1 hour, and the number of foreign particles in the coating film was counted. The surface was observed using a metal microscope "BX60" (manufactured by Olympus Systems Co., Ltd.) for evaluation. The magnification was 500 times, and the number of foreign particles observable in any five visual fields in transmission was counted. Three or more was practical.
5: 0 foreign objects 4: 1 or more but less than 5 foreign objects
3: The number of foreign objects is 5 or more and less than 20
2: The number of foreign objects is 20 or more and less than 100
1: The number of foreign objects is 100 or more

<Production of Coloring Composition Not Containing a Yellow Coloring Composition>
[Production Example 1]
(Coloring composition (GB-1))
The following raw materials were mixed and stirred to be uniform, and then dispersed for 3 hours in an Eiger mill ("Mini Model M-250 MKII" manufactured by Eiger Japan Co., Ltd.) using zirconia beads having a diameter of 0.5 mm, and then filtered through a filter having a pore size of 1.0 μm to prepare a colored composition (GB-1) containing no yellow coloring composition and having a non-volatile component content of 20.0% by mass. The organic solvent (C-1) is PGMAc.
Finely divided green colorant (D-1): 12 parts by weight Basic dispersion resin (B1-1) solution: 10 parts by weight Phosphoric acid-based dispersion resin (B3-1) solution: 6 parts by weight Carboxylic acid-based dispersion resin (B4-1) solution: 4 parts by weight Binder resin (H-1) solution: 10 parts by weight Organic solvent (C-1): 58 parts by weight

[Production Examples 2 to 8]
Colored compositions (GB-2 to 5, RB-1 to 3) not containing a yellow coloring composition were prepared in the same manner as in Production Example 1, except that the material types and masses were changed as shown in Table 3.

<Production of Green Colored Composition>
[Example 39]
(Green colored composition (GYB-1)
The following components were mixed and stirred to be homogeneous, and filtered through a filter having a pore size of 1.0 μm to prepare a green colored composition (GYB-1) having a non-volatile component content of 20.0% by mass.
Yellow colored composition (YB-1): 46.5 parts by mass Green colored composition (GB-1): 37.0 parts by mass Binder resin (H-1): 16.5 parts by mass

[Examples 39 to 84, Comparative Examples 7 to 14]
(Green colorant composition (GYB-2 to 54))
Green colorant compositions (GYB-2 to 54) were prepared in the same manner as in Example 39, except that the material types and masses were changed as shown in Table 4.

<Evaluation of Green Colored Composition>
The obtained green colored compositions (GYB-1 to 54) were evaluated for brightness, contrast ratio, and foreign matter by the following methods. The evaluation results are shown in Table 5.

(Lightness Evaluation)
The green colored compositions (GYB-1 to 54) were applied onto a glass substrate of 100 mm x 100 mm and 1.1 mm thick using a spin coater, then dried at 70°C for 20 minutes, and then heated at 230°C for 30 minutes and allowed to cool to prepare a coated substrate. At this time, the coated substrate was coated to a thickness such that x = 0.297 with a C light source after heat treatment at 230°C. The brightness (Y) of the obtained coated substrate was measured with a microspectrophotometer ("OSP-SP200" manufactured by Olympus Optical Co., Ltd.) and evaluated according to the following criteria. A value of 3 or more was determined to be a practical level.
5: 66.5 or more 4: 65.9 or more, less than 66.5 3: 65.3 or more, less than 65.9 2: 64.9 or more, less than 65.3
1: Less than 64.9

(Contrast ratio evaluation)
The light emitted from the backlight unit for liquid crystal display is polarized by passing through a polarizing plate, passes through a coating film of a coloring composition applied on a glass substrate, and reaches the other polarizing plate. In this case, if the polarization planes of the polarizing plates are parallel, the light passes through the polarizing plate, but if the polarization planes are perpendicular, the light is blocked by the polarizing plate. However, when the light polarized by the polarizing plate passes through the coating film of the coloring composition, scattering occurs due to colorant particles, and if a part of the polarization plane is shifted, the amount of light transmitted decreases when the polarizing plates are parallel, and part of the light is transmitted when the polarizing plates are perpendicular. This transmitted light was measured as the luminance on the polarizing plate, and the ratio of the luminance when the polarizing plates are parallel to the luminance when they are perpendicular was calculated as the contrast ratio.

(Contrast ratio) = (Luminance when parallel) / (Luminance when perpendicular)

Thus, scattering caused by colorants in the coating reduces the parallel luminance and increases the perpendicular luminance, resulting in a lower contrast ratio.
The same coating film as that for the evaluation of brightness was used, and a color luminance meter (Topcon Corporation's "BM-5A") was used as the luminance meter, and a polarizing plate (Nitto Denko Corporation's "NPF-G1220DUN") was used as the polarizing plate. The measurement was performed through a black mask with a 1 cm square hole in the measurement area. A value of 3 or more was considered to be a practical level.
5: 20,000 or more 4: 15,000 or more, but less than 20,000 3: 10,000 or more, but less than 15,000 2: 5,000 or more, but less than 10,000 1: Less than 5,000

(Evaluation of foreign matter)
The yellow colored composition was applied onto a transparent substrate so that the dried coating film had a thickness of about 2.0 μm, and heat-treated in an oven at 230° C. for 1 hour, and the number of foreign particles in the coating film was counted. The surface was observed using a metal microscope "BX60" (manufactured by Olympus Systems Co., Ltd.) for evaluation. The magnification was 500 times, and the number of foreign particles observable in any five visual fields in transmission was counted. Three or more was practical.
5: 0 foreign objects 4: 1 or more but less than 5 foreign objects
3: The number of foreign objects is 5 or more and less than 20
2: The number of foreign objects is 20 or more and less than 100
1: The number of foreign objects is 100 or more

<Production of Red Colored Composition>
[Example 85]
(Red Composition (RYB-1)
The following components were mixed with stirring until homogeneous and filtered through a filter having a pore size of 1.0 μm to prepare a green colored composition (RYB-1) having a non-volatile component content of 20.0% by mass.
Yellow colored composition (YB-1): 19.5 parts by mass Red colored composition (RB-1): 48.5 parts by mass Binder resin (H-1): 32.0 parts by mass

[Examples 86 to 127, Comparative Examples 15 to 22]
(Red colorant composition (RYB-2 to RYB-51))
Red colorant compositions (RYB-2 to RYB-51) were prepared in the same manner as in Example 85, except that the material types and masses were changed as shown in Table 6.

<Evaluation of Red Colored Composition>
The obtained red colored compositions (RYB-1 to 51) were evaluated for brightness, contrast ratio, and foreign matter by the following methods. The evaluation results are shown in Table 7.

(Lightness Evaluation)
The red colored compositions (RYB-1 to 51) were applied onto a glass substrate of 100 mm x 100 mm and 1.1 mm thick using a spin coater, then dried at 70°C for 20 minutes, and then further heated at 230°C for 30 minutes and allowed to cool to prepare a coated substrate. At this time, the coated substrate was coated to a thickness such that x = 0.660 with a C light source after heat treatment at 230°C. The lightness (Y) of the obtained coated substrate was measured with a microspectrophotometer ("OSP-SP200" manufactured by Olympus Optical Co., Ltd.) and evaluated according to the following criteria. A value of 3 or more was determined to be a practical level.
5: 18.5 or more 4: 18.3 or more, less than 18.5 3: 18.1 or more, less than 18.3 2: 17.9 or more, less than 18.1
1: Less than 18.1

(Contrast ratio evaluation)
The light emitted from the backlight unit for liquid crystal display is polarized by passing through a polarizing plate, passes through a coating film of a coloring composition applied on a glass substrate, and reaches the other polarizing plate. In this case, if the polarization planes of the polarizing plates are parallel, the light passes through the polarizing plate, but if the polarization planes are perpendicular, the light is blocked by the polarizing plate. However, when the light polarized by the polarizing plate passes through the coating film of the coloring composition, scattering occurs due to colorant particles, and if a part of the polarization plane is shifted, the amount of light transmitted decreases when the polarizing plates are parallel, and part of the light is transmitted when the polarizing plates are perpendicular. This transmitted light was measured as the luminance on the polarizing plate, and the ratio of the luminance when the polarizing plates are parallel to the luminance when they are perpendicular was calculated as the contrast ratio.

(Contrast ratio) = (Luminance when parallel) / (Luminance when perpendicular)

Thus, scattering caused by colorants in the coating reduces the parallel luminance and increases the perpendicular lightness, resulting in a lower contrast ratio.
The same coating film as that for the evaluation of brightness was used, and a color luminance meter (Topcon Corporation's "BM-5A") was used as the luminance meter, and a polarizing plate (Nitto Denko Corporation's "NPF-G1220DUN") was used as the polarizing plate. The measurement was performed through a black mask with a 1 cm square hole in the measurement area. A value of 3 or more was considered to be a practical level.
5: 8,500 or more 4: 7,000 or more but less than 8,500 3: 5,500 or more but less than 7,000 2: 4,000 or more but less than 5,500 1: Less than 4,000

(Evaluation of foreign matter)
The yellow colored composition was applied onto a transparent substrate so that the dried coating film had a thickness of about 2.0 μm, and heat-treated in an oven at 230° C. for 1 hour, and the number of foreign particles in the coating film was counted. The surface was observed using a metal microscope "BX60" (manufactured by Olympus Systems Co., Ltd.) for evaluation. The magnification was 500 times, and the number of foreign particles observable in any five visual fields in transmission was counted. Three or more was practical.
5: 0 foreign objects 4: 1 or more but less than 5 foreign objects
3: The number of foreign objects is 5 or more and less than 20
2: The number of foreign objects is 20 or more and less than 100
1: The number of foreign objects is 100 or more

<Preparation of Photosensitive Yellow Coloring Composition>
[Example 201]
(Photosensitive Yellow Coloring Composition (YR-1))
The following raw materials were mixed, stirred, and filtered through a filter having a pore size of 1.0 μm to obtain a photosensitive yellow colored composition (YR-1).
Yellow colored composition (YB-1): 50.0 parts by mass
Binder resin (H) solution: 15.0 parts by mass Epoxy compound (I-1): 1.0 part by mass Oxetane compound (I-2): 1.0 part by mass Polymerizable compound (F): 3.0 parts by mass Photopolymerization initiator (G): 1.8 parts by mass Sensitizer (H): 0.2 parts by mass Thiol-based chain transfer agent (K): 0.4 parts by mass Polymerization inhibitor (L): 0.1 parts by mass UV absorber (M): 0.1 parts by mass Antioxidant (N): 0.1 parts by mass Leveling agent (O): 1.0 parts by mass Storage stabilizer (P): 0.1 parts by mass Adhesion improver (Q): 0.2 parts by mass Organic solvent (C): 26.0 parts by mass

[Examples 202 to 238, Comparative Examples 201 to 206]
(Photosensitive Yellow Coloring Compositions (YR-1 to 44))
Photosensitive yellow coloring compositions (YR-1 to 44) were prepared in the same manner as in Example 101, except that the type of the yellow coloring composition YB-1 in Example 201 was changed to that shown in Table 8.
The details of each raw material are as follows:

(Binder resin (H) solution)
The binder resins (H-2) to (H-4) were mixed in equal amounts to prepare a binder resin (H) solution.

(Epoxy compound (I-1))
(I-1-1) 1,2- of 2,2'-bis(hydroxymethyl)-1-butanol
Epoxy-4-(2-oxiranyl)cyclohexane adduct
[EHPE-3150 (manufactured by Daicel)],
(I-1-2) Glycidyl etherified epoxy compounds of sorbitol
[Denacol EX611 (manufactured by Nagase ChemteX Corporation)],
(I-1-3) Triglycidyl isocyanurate The above (I-1-1) to (I-1-3) were mixed in equal amounts to obtain an epoxy compound (G-1).

(Oxetane Compound (I-2))
3-Ethyl-3-[(3-ethyloxetan-3-yl)methoxymethyl]oxetane
[Aron Oxetane OXT-221 (manufactured by Toagosei Co., Ltd.)]

(Polymerizable compound (F))
(F-1) Trimethylolpropane triacrylate
[Aronix M309 (manufactured by Toagosei Co., Ltd.)]
(F-2) Dipentaerythritol penta- and hexaacrylate
[Aronix M402 (manufactured by Toagosei Co., Ltd.)]
(F-3) Polybasic acidic acrylic oligomer
[Aronix M520 (manufactured by Toagosei Co., Ltd.)]
(F-4) Caprolactone-modified dipentaerythritol hexaacrylate
[KAYARAD DPCA-30 (manufactured by Nippon Kayaku)]
The above (F-1) to (F-4) were mixed in equal amounts to obtain a polymerizable compound (F).

(Photopolymerization Initiator (G))
(G-1) 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one
[Irgacure 907 (manufactured by BASF Japan)]
(G-2) 2-(Dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]-1-butanone
[Irgacure 379 (manufactured by BASF Japan)]
(G-3) 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide
[Lucirin TPO (manufactured by Ciba Japan)]
(G-4) 2,2'-bis(o-chlorophenyl)-4,5,4',5'-tetraphenyl-1,2'-biimidazole
[Biimidazole (Kurokane Chemicals)]
(G-5) p-Dimethylaminoacetophenone
[DMA (manufactured by Daikifine)]
(G-6) Ethan-1-one, 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl], 1-(O-acetyloxime)
[Irgacure OXE02 (manufactured by BASF Japan)]
(G-7) 1-[4-(2-hydroxyethoxy)-phenyl]-2-hydroxy-2-methyl-1-propan-1-one
[Irgacure 2959 (manufactured by BASF Japan)]
(G-8) Bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide
[Irgacure 819 (manufactured by BASF Japan)]
The above (G-1) to (G-8) were mixed in equal amounts to prepare a photopolymerization initiator (F).

(Sensitizer (J))
(J-1) 2,4-diethylthioxanthone
[Kayacure DETX-S (manufactured by Nippon Kayaku)]
(J-2) 4,4'-bis(diethylamino)benzophenone
[CHEMARK DEABP (manufactured by Chemark Chemical Co.)]
The above (J-1) and (J-2) were mixed in equal amounts to prepare sensitizer (J).

(Thiol-Based Chain Transfer Agent (K))
(K-1) Trimethylolethane tris(3-mercaptobutyrate)
[TEMB (Showa Denko)]
(K-2) Trimethylolpropane tris(3-mercaptobutyrate)
[TPMB (Showa Denko)]
(K-3) Pentaerythritol tetrakis(3-mercaptopropionate)
[PEMP (manufactured by Sakai Chemical Industry Co., Ltd.)]
(K-4) Trimethylolpropane tris(3-mercaptopropionate)
[TMMP (manufactured by Sakai Chemical Industry Co., Ltd.)]
(K-5) Tris[(3-mercaptopropionyloxy)-ethyl]-isocyanurate
[TEMPIC (manufactured by Sakai Chemical Industry Co., Ltd.)]
The above (K-1) to (K-5) were mixed in equal amounts to prepare a thiol-based chain transfer agent (K).

(Polymerization Inhibitor (L))
(L-1) 3-methylcatechol (L-2) methylhydroquinone (L-3) t-butylhydroquinone The above (L-1) to (L-3) were mixed in equal amounts to prepare a polymerization inhibitor (J).

(Ultraviolet absorber (M))
(M-1) 2-[4-[(2-hydroxy-3-(dodecyl and tridecyl)oxypropyl)oxy]-2-hydroxyphenyl]-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine
[TINUVIN 400 (manufactured by BASF Japan)]
(M-2) 2-(2H-benzotriazol-2-yl)-4,6-bis(1-methyl-1-phenylethyl)phenol
[TINUVIN900 (manufactured by BASF Japan)]
The above (M-1) and (M-2) were mixed in equal amounts to prepare an ultraviolet absorber (M).

(Antioxidant (N))
(N-1) Pentaerythritol tetrakis[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate (N-2) Dioctadecyl 3,3'-thiodipropanoate (N-3) Tris[2,4-di-(t)-butylphenyl]phosphine (N-4) Bis(2,2,6,6-tetramethyl-4-piperidyl)sebacate (N-5) p-Octylphenyl salicylate The above (N-1) to (N-5) were mixed in equal amounts to give antioxidant (L).

(Leveling Agent (O))
(O-1) BYK-330 manufactured by BYK-Chemie
(O-2) "Megafac F-551" manufactured by DIC Corporation
(O-3) "Emulgen 103" manufactured by Kao Corporation
One part each of (O-1) to (O-3) above was mixed and dissolved in 97 parts of propylene glycol monomethyl ether acetate to prepare a mixed solution, which was used as a leveling agent (O).

(Storage stabilizer (P))
(P-1) 2,6-bis(1,1-dimethylethyl)-4-methylphenol ("BHT" manufactured by Honshu Chemical Industry Co., Ltd.)
(P-2) Triphenylphosphine ("TPP" manufactured by Hokko Chemical Industry Co., Ltd.)
The above (P-1) and (P-2) were mixed in equal amounts to prepare a storage stabilizer (P).

(Adhesion improver (Q))
(Q-1) 3-Glycidoxypropyltriethoxysilane
[Shin-Etsu Silicone Silane Coupling Agent KBM-403 (manufactured by Shin-Etsu Chemical Co., Ltd.)]
(Q-2) 3-Methacryloxypropyltriethoxysilane
[Shin-Etsu Silicone Silane Coupling Agent KBE-503 (manufactured by Shin-Etsu Chemical Co., Ltd.)]
(Q-3) N-2-(aminoethyl)-3-aminopropyltrimethoxysilane
[Shin-Etsu Silicone Silane Coupling Agent KBM-603 (manufactured by Shin-Etsu Chemical Co., Ltd.)]
(Q-4) 3-Mercaptopropyltrimethoxysilane
[Shin-Etsu Silicone Silane Coupling Agent KBM-803 (manufactured by Shin-Etsu Chemical Co., Ltd.)]
The above (Q-1) to (Q-4) were mixed in equal amounts to prepare a silane coupling agent (Q).

(Organic Solvent (C))
(C-1) Propylene glycol monomethyl ether acetate 30 parts (C-2) Cyclohexanone 30 parts (C-3) Ethyl 3-ethoxypropionate 10 parts (C-4) Propylene glycol monomethyl ether 10 parts (C-5) Cyclohexanol acetate 10 parts (C-6) Dipropylene glycol methyl ether acetate 10 parts The above (C-1) to (C-6) were mixed in the above parts by mass to obtain organic solvent (C).

<Evaluation of Photosensitive Yellow Coloring Composition>
The obtained photosensitive yellow colored composition was evaluated for luminance, contrast ratio, and foreign matter by the following methods. The evaluation results are shown in Table 8.

(Lightness Evaluation)
The photosensitive yellow coloring composition was applied onto a glass substrate of 100 mm x 100 mm and 1.1 mm thick using a spin coater, and heated at 230°C for 20 minutes to obtain a coating film. At this time, the coating conditions (spin coater rotation speed, time) were appropriately changed so that the coating film had a thickness of x = 0.430 under C light source after heat treatment at 230°C. The lightness (Y) of the obtained coating film was measured using a microspectrophotometer (Olympus Optical Co., Ltd. "OSP-SP100"). A value of 3 or more is practical.

5: 90.0 or more 4: 89.0 or more, but less than 90.0 3: 88.0 or more, but less than 89.0 2: 87.0 or more, but less than 88.0 1: Less than 87.0

(Contrast ratio evaluation)
The light emitted from the backlight unit for liquid crystal display is polarized by passing through a polarizing plate, passes through a coating film of a coloring composition applied on a glass substrate, and reaches the other polarizing plate. In this case, if the polarization planes of the polarizing plates are parallel, the light passes through the polarizing plate, but if the polarization planes are perpendicular, the light is blocked by the polarizing plate. However, when the light polarized by the polarizing plate passes through the coating film of the coloring composition, scattering occurs due to colorant particles, and if a part of the polarization plane is shifted, the amount of light transmitted decreases when the polarizing plates are parallel, and part of the light is transmitted when the polarizing plates are perpendicular. This transmitted light was measured as the luminance on the polarizing plate, and the ratio of the luminance when the polarizing plates are parallel to the luminance when they are perpendicular was calculated as the contrast ratio.

(Contrast ratio) = (Luminance when parallel) / (Luminance when perpendicular)

Thus, scattering caused by colorants in the coating reduces the parallel luminance and increases the perpendicular luminance, resulting in a lower contrast ratio.
The same coating film as that for the evaluation of brightness was used, and a color luminance meter (Topcon Corporation's "BM-5A") was used as the luminance meter, and a polarizing plate (Nitto Denko Corporation's "NPF-G1220DUN") was used as the polarizing plate. The measurement was performed through a black mask with a 1 cm square hole in the measurement area. A value of 3 or more was considered to be a practical level.

5: 25,000 or more 4: 20,000 or more, but less than 25,000 3: 15,000 or more, but less than 20,000 2: 10,000 or more, but less than 15,000 1: Less than 10,000

(Evaluation of foreign matter)
The photosensitive yellow coloring composition was applied onto a transparent substrate so that the dry coating film was about 2.0 μm thick, and heat-treated in an oven at 230° C. for 1 hour, and the number of foreign particles in the coating film was counted. The surface was observed using a metal microscope "BX60" (manufactured by Olympus Systems Co., Ltd.) for evaluation. The magnification was 500 times, and the number of foreign particles observable in any five visual fields in transmission was counted. Three or more is practical.

5: 0 foreign objects 4: 1 or more but less than 5 foreign objects
3: The number of foreign objects is 5 or more and less than 20
2: The number of foreign objects is 20 or more and less than 100
1: The number of foreign objects is 100 or more

<Preparation of Photosensitive Green Coloring Composition>
[Examples 239 to 284, Comparative Examples 207 to 214]
(Photosensitive Green Coloring Compositions (GYR-1 to GYR-54))
Photosensitive green colored compositions (GYR-1 to 54) were prepared in the same manner as in Example 201, except that the yellow colored composition in Example 201 was changed to the green colored composition shown in Table 9.

<Evaluation of Photosensitive Green Coloring Composition>
The obtained photosensitive green colored compositions (GYR-1 to 54) were evaluated for brightness, contrast ratio, foreign matter, voltage holding ratio, and weather resistance by the following methods. The evaluation results are shown in Table 9.

(Lightness Evaluation)
The photosensitive green coloring composition (GYR-1 to 54) was applied onto a glass substrate of 100 mm x 100 mm and 1.1 mm thick using a spin coater, then dried at 70°C for 20 minutes, and then heated at 230°C for 30 minutes and allowed to cool to prepare a coated substrate. At this time, the coated substrate was coated to a thickness such that x = 0.297 with a C light source after heat treatment at 230°C. The brightness (Y) of the obtained coated substrate was measured with a microspectrophotometer ("OSP-SP200" manufactured by Olympus Optical Co., Ltd.) and evaluated according to the following criteria. A value of 3 or more was determined to be a practical level.

5: 66.5 or more 4: 65.9 or more, but less than 66.5 3: 65.3 or more, but less than 65.9 2: 64.9 or more, but less than 65.3
1: Less than 64.9

(Contrast ratio evaluation)
The light emitted from the backlight unit for liquid crystal display is polarized by passing through a polarizing plate, passes through a coating film of a coloring composition applied on a glass substrate, and reaches the other polarizing plate. In this case, if the polarization planes of the polarizing plates are parallel, the light passes through the polarizing plate, but if the polarization planes are perpendicular, the light is blocked by the polarizing plate. However, when the light polarized by the polarizing plate passes through the coating film of the coloring composition, scattering occurs due to colorant particles, and if a part of the polarization plane is shifted, the amount of light transmitted decreases when the polarizing plates are parallel, and part of the light is transmitted when the polarizing plates are perpendicular. This transmitted light was measured as the luminance on the polarizing plate, and the ratio of the luminance when the polarizing plates are parallel to the luminance when they are perpendicular was calculated as the contrast ratio.

(Contrast ratio) = (Luminance when parallel) / (Luminance when perpendicular)

Thus, scattering caused by colorants in the coating reduces the parallel luminance and increases the perpendicular luminance, resulting in a lower contrast ratio.
The same coating film as that for the evaluation of brightness was used, and a color luminance meter (Topcon Corporation's "BM-5A") was used as the luminance meter, and a polarizing plate (Nitto Denko Corporation's "NPF-G1220DUN") was used as the polarizing plate. The measurement was performed through a black mask with a 1 cm square hole in the measurement area. A value of 3 or more was considered to be a practical level.

5: 25,000 or more 4: 20,000 or more, but less than 25,000 3: 15,000 or more, but less than 20,000 2: 10,000 or more, but less than 15,000 1: Less than 10,000

(Evaluation of foreign matter)
The photosensitive green coloring composition was applied onto a transparent substrate so that the dry coating film was about 2.0 μm thick, and heat-treated in an oven at 230° C. for 1 hour, and the number of foreign particles in the coating film was counted. The surface was observed using a metal microscope "BX60" (manufactured by Olympus Systems Co., Ltd.) for evaluation. The magnification was 500 times, and the number of foreign particles observable in any five visual fields in transmission was counted. Three or more is practical.

5: 0 foreign objects 4: 1 or more but less than 5 foreign objects
3: The number of foreign objects is 5 or more and less than 20
2: The number of foreign objects is 20 or more and less than 100
1: The number of foreign objects is 100 or more

(Evaluation of Voltage Holding Ratio Change Rate (hereinafter referred to as ΔVHR))
The photosensitive green coloring composition (GYR-1 to 54) was applied to a glass substrate having an ITO transparent electrode with an effective electrode size of 10 mm x 10 mm using a spin coater so that the thickness of the dried film was 3.2 μm, and the coating film of the electrode part was wiped off with a solvent, and then exposed to ultraviolet light with an integrated light amount of 50 mJ/cm ² and developed with an alkaline developer at 23 ° C. to obtain a coating film substrate. Then, after heating at 230 ° C. for 20 minutes and cooling, two sample-coated substrates for measurement were prepared. The two sample-coated glass substrates were arranged so that the ITO transparent electrode surfaces faced each other, and a small cell was prepared using a sealant so that the cell gap was 9 μm. A liquid crystal liquid was injected into the cell gap of this small cell, and a voltage of 5 V was applied for 60 μs at 50 ° C., and the cell voltage [V1] 16.67 ms after the voltage was released was measured using a VHR-1S manufactured by Toyo Corporation. The measured cell voltages were averaged, and the initial VHR (%) was calculated using the obtained cell voltage according to the following formula.

VHR (voltage holding ratio) (%) = ([V1] / 5) x 100

The cell sample after the initial VHR measurement was irradiated with LED lighting at 150,000 nits for 3 hours and then the VHR (%) after irradiation was measured again. ΔVHR was calculated using the following formula and evaluated according to the following criteria. A score of 3 or higher was determined as a practical level.

ΔVHR=|initial VHR−post-exposure VHR|

5: Less than 2% 4: 2% or more, less than 5% 3: 5% or more, less than 10% 2: 10% or more, less than 15% 1: 15% or more

(Weather resistance evaluation)
The photosensitive green coloring composition (GYR-1 to 54) was applied to a 10 cm x 10 cm glass substrate by spin coating, and the organic solvent was removed using a vacuum dryer. The substrate was exposed to ultraviolet light through a 1 nm thick blue plate using an ultra-high pressure mercury lamp. After that, the substrate was spray-developed using a 23°C aqueous sodium carbonate solution, washed with ion-exchanged water, air-dried, and heated in a clean oven at 230°C for 40 minutes. Next, the substrate after post-baking was again coated with an overcoat agent by the spin coat method, and then dried using a vacuum dryer. The substrate was then baked on a hot plate at 90°C for 2 minutes, and further heated in a green oven at 230°C for 60 minutes.
The obtained substrate with the overcoat agent was cut into 2 cm x 5 cm. 0.020 ml of ultraviolet curing sealant was dropped onto the cut substrate coating, and then a cover glass of 18 mm x 18 mm was placed on the substrate, and the substrate was left horizontally until the sealant spread to the edge of the cover glass. Then, the sealed portion of the cut substrate was exposed to ultraviolet light from an ultra-high pressure mercury lamp at an exposure dose of 4000 mJ/ ^cm2 to obtain a substrate for weather resistance evaluation.
The brightness of the weather resistance evaluation substrate in the XYZ color system was measured and used as the initial brightness. After the measurement, an LED backlight was placed in a high-temperature, high-humidity oven (65°C/90%RH), the film surface was placed on the backlight, the weather resistance evaluation substrate was arranged, and the LED backlight was turned on. After 72 hours, the brightness was measured at the same location as the initial brightness measurement and used as the post-irradiation brightness. The brightness change rate was calculated using the following formula.

Brightness change rate (%) = (brightness after irradiation - initial brightness) / initial brightness x 100

5: Less than 2% 4: 2% or more, less than 5% 3: 5% or more, less than 10% 2: 10% or more, less than 15% 1: 15% or more

<Preparation of Photosensitive Red Coloring Composition>
[Examples 285 to 327, Comparative Examples 215 to 222]
(Photosensitive Red Coloring Compositions (RYR-1 to RYR-51))
Photosensitive red colored compositions (RYR-1 to RYR-51) were prepared in the same manner as in Example 101, except that the yellow colored composition in Example 101 was changed to the red colored composition shown in Table 10.

<Evaluation of Photosensitive Red Coloring Composition>
The obtained photosensitive red colored compositions (RYR-1 to 51) were evaluated for brightness, contrast ratio, and foreign matter by the following methods. The evaluation results are shown in Table 10.

(Lightness Evaluation)
The photosensitive red coloring composition (RYB-1 to 51) was applied onto a glass substrate of 100 mm x 100 mm and 1.1 mm thick using a spin coater, then dried at 70°C for 20 minutes, and then heated at 230°C for 30 minutes and allowed to cool to prepare a coated substrate. At this time, the coated substrate was coated to a thickness such that x = 0.660 with a C light source after heat treatment at 230°C. The brightness (Y) of the obtained coated substrate was measured with a microspectrophotometer ("OSP-SP200" manufactured by Olympus Optical Co., Ltd.) and evaluated according to the following criteria. A value of 3 or more was determined to be a practical level.

5: 18.5 or more 4: 18.3 or more, but less than 18.5 3: 18.1 or more, but less than 18.3 2: 17.9 or more, but less than 18.1 1: Less than 17.9

(Contrast ratio evaluation)
The light emitted from the backlight unit for liquid crystal display is polarized by passing through a polarizing plate, passes through a coating film of a coloring composition applied on a glass substrate, and reaches the other polarizing plate. At this time, if the polarization planes of the polarizing plates are parallel, the light passes through the polarizing plate, but if the polarization planes are perpendicular, the light is blocked by the polarizing plate. However, when the light polarized by the polarizing plate passes through the coating film of the coloring composition, scattering occurs due to colorant particles, and if a part of the polarization plane is shifted, the amount of light transmitted decreases when the polarizing plates are parallel, and part of the light is transmitted when the polarizing plates are perpendicular. This transmitted light was measured as the luminance on the polarizing plate, and the ratio of the luminance when the polarizing plates are parallel to the luminance when they are perpendicular was calculated as the contrast ratio.

(Contrast ratio) = (Luminance when parallel) / (Luminance when perpendicular)

Thus, scattering caused by colorants in the coating reduces the parallel luminance and increases the perpendicular lightness, resulting in a lower contrast ratio.
The same coating film as that for the evaluation of brightness was used, and a color luminance meter (Topcon Corporation's "BM-5A") was used as the luminance meter, and a polarizing plate (Nitto Denko Corporation's "NPF-G1220DUN") was used as the polarizing plate. The measurement was performed through a black mask with a 1 cm square hole in the measurement area. A value of 3 or more was considered to be a practical level.

5: 10,000 or more 4: 7,000 or more but less than 8,500 3: 5,500 or more but less than 7,000 2: 4,000 or more but less than 5,500 1: Less than 4,000

(Evaluation of foreign matter)
The yellow colored composition was applied onto a transparent substrate so that the dried coating film had a thickness of about 2.0 μm, and heat-treated in an oven at 230° C. for 1 hour, and the number of foreign particles in the coating film was counted. The surface was observed using a metal microscope "BX60" (manufactured by Olympus Systems Co., Ltd.) for evaluation. The magnification was 500 times, and the number of foreign particles observable in any five visual fields in transmission was counted. Three or more was practical.

5: 0 foreign objects 4: 1 or more but less than 5 foreign objects
3: The number of foreign objects is 5 or more and less than 20
2: The number of foreign objects is 20 or more and less than 100
1: The number of foreign objects is 100 or more

REFERENCE SIGNS LIST 10 Liquid crystal display device 11 Transparent substrate 12 TFT array 13 Transparent electrode layer 14 Alignment layer 15 Polarizing plate 21 Transparent substrate 22 Color filter 23 Transparent electrode layer 24 Alignment layer 25 Polarizing plate 30 Backlight unit 31 White LED light source LC Liquid crystal

Claims (9)

A yellow coloring composition comprising a yellow colorant (A), a dispersion resin (B), and an organic solvent (C), wherein the yellow colorant (A) comprises a yellow colorant (A1) that is a metal salt of a compound represented by the following general formula (1), and the content of the yellow colorant (A1) is 90 mass% or more with respect to the total mass of the yellow colorant (A):
General formula (1)

(In general formula (1), R ₁ to R ₁₃ each independently represent a hydrogen atom, a halogen atom, a hydroxyl group, an alkyl group which may have a substituent, an alkoxyl group which may have a substituent, or an aryl group which may have a substituent. In addition, at least one pair of adjacent groups among R ₁ to R ₄ and/or at least one pair of adjacent groups among R ₅ to R ₈ can be joined together to form an aromatic ring which may have a substituent.) The yellow coloring composition according to claim 1, wherein the metal is at least one selected from the group consisting of aluminum, copper, zinc, iron, and silver. The yellow colored composition according to claim 1 or 2, wherein the dispersion resin (B) comprises at least one of a basic dispersion resin (B1) and a dispersion resin (B2) which is a salt of the basic dispersion resin (B1) and a compound represented by the following general formula (2) or a compound represented by the following general formula (3):
General formula (2)

(In general formula (2), R ¹ and R ² each independently represent a hydrogen atom, a hydroxyl group, a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms, a vinyl group, a phenyl group or a benzyl group which may have a substituent, or -O-R ⁴ , and R ⁴ represents a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms, a vinyl group, a phenyl group or a benzyl group which may have a substituent, or a (meth)acryloyl group via an alkylene group having 1 to 4 carbon atoms, with the proviso that at least one of R ¹ and R ² is a group containing a carbon atom.)
General formula (3)

(In the general formula (3), ^R3 represents a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms, a vinyl group, a phenyl group or a benzyl group which may have a substituent, or -O- ^R5 , and ^R5 represents a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms, a vinyl group, a phenyl group or a benzyl group which may have a substituent, or a (meth)acryloyl group via an alkylene group having 1 to 4 carbon atoms.) A green coloring composition comprising the yellow coloring composition according to any one of claims 1 to 3 and a green colorant (D), wherein the mass ratio of the yellow colorant (A) to the green colorant (D) is 70:30 to 10:90. A red coloring composition comprising the yellow coloring composition according to any one of claims 1 to 3 and a red colorant (E), wherein the mass ratio of the yellow colorant (A) to the red colorant (E) is 70:30 to 10:90. A photosensitive coloring composition comprising at least one of the yellow coloring composition according to any one of claims 1 to 3, the green coloring composition according to claim 4, or the red coloring composition according to claim 5, a polymerizable compound (F), and a photopolymerization initiator (G). A color filter having filter segments formed using the photosensitive coloring composition according to claim 6. A liquid crystal display device having the color filter according to claim 7. A solid-state imaging device having the color filter according to claim 7.