JP2024089368A - Photosensitive coloring composition, film using same, color filter, and image display device - Google Patents

Abstract

The present invention relates to a photosensitive coloring composition that can control the climbing property of a laminated photospacer, and can form a film with few surface defects and excellent developability, adhesion, and pattern shape.
[Solution] A photosensitive coloring composition comprising a colorant (A), a binder resin (B), a polymerizable compound (C), a polymerization initiator (D), and an organic solvent (E), wherein the organic solvent (E) comprises an organic solvent (E1) having a boiling point of 180°C or more and 220°C or less and a vapor pressure at 20°C of less than 100 Pa, in an amount of 0.1 mass% or more and less than 10 mass% based on 100 mass% of the organic solvent (E), an organic solvent (E2) having a boiling point of 160°C or more and less than 180°C and a vapor pressure at 20°C of 100 Pa or more and less than 400 Pa, in an amount of 10 mass% or more and 40 mass% or less based on 100 mass% of the organic solvent (E), and an organic solvent (E3) having a boiling point of 120°C or more and less than 160°C and a vapor pressure at 20°C of 400 Pa or more, in an amount of 55 mass% or more and 85 mass% or less based on 100 mass% of the organic solvent (E).
[Selected Figure] Figure 1

Description

The present invention relates to a photosensitive coloring composition and its uses.

Image display devices using liquid crystal display elements are used in a variety of devices because they are small, thin, lightweight, and consume little power. In such image display devices, a liquid crystal layer is disposed between a color filter substrate and a substrate on which active elements are formed (hereinafter referred to as a TFT substrate). If the distance between the color filter substrate and the TFT substrate is not maintained accurately, a difference in the thickness of the liquid crystal layer occurs, and images are not displayed correctly. For this reason, spacers are disposed between the color filter substrate and the TFT substrate to ensure a uniform cell gap. A method has been proposed for forming the spacers by forming columnar resin spacers (hereinafter referred to as photospacers) on a black matrix using a photolithography method (Patent Documents 1 and 2).

In addition, a method has been proposed in which multiple colored layers are laminated at the same time that each colored pixel such as R (red), G (green), and B (blue) is formed (Patent Documents 3 to 5). This method has the advantage of reducing the number of steps required to form a photospacer. However, the method of forming a spacer by laminating colored layers at the same time as forming colored pixels (hereinafter referred to as a laminated photospacer) has a problem in that the height of the laminated photospacer can become too low or too high (hereinafter also referred to as climbing property) during the process of applying and drying a photosensitive coloring composition to a substrate.

As a method for controlling the riding property of a laminated photospacer, for example, Patent Document 6 discloses a photosensitive coloring composition containing 1 to 30% by mass of a transparent extender pigment in the total nonvolatile content. Patent Document 7 discloses a photosensitive coloring composition containing 1 to 10% by mass of a transparent extender pigment in the total nonvolatile content, and a photopolymerizable monomer with a molecular weight in the range of 1,000 to 1,500.

JP 2001-91954 A JP 2001-92128 A Japanese Patent Application Laid-Open No. 04-18443 Japanese Patent Application Laid-Open No. 11-344700 JP 2011-209618 A JP 2011-158537 A JP 2013-097235 A

However, neither Patent Document 6 nor Patent Document 7 was sufficient to control the riding property. In addition, the surface defects, developability, adhesion, and pattern shape were not satisfactory.

The present invention aims to provide a photosensitive coloring composition that can control the climbing ability of a laminated photospacer and form a film with few surface defects and excellent developability, adhesion, and pattern shape.

The present invention relates to a photosensitive coloring composition comprising a colorant (A), a binder resin (B), a polymerizable compound (C), a polymerization initiator (D), and an organic solvent (E),
The organic solvent (E) may be
An organic solvent (E1) having a boiling point of 180° C. or more and 220° C. or less and a vapor pressure at 20° C. of less than 100 Pa is contained in an amount of 0.1% by mass or more and less than 10% by mass based on 100% by mass of the organic solvent (E);
The organic solvent (E2) has a boiling point of 160° C. or more and less than 180° C. and a vapor pressure at 20° C. of 100 Pa or more and less than 400 Pa, and the organic solvent (E2) is contained in an amount of 10 mass% or more and 40 mass% or less based on 100 mass% of the organic solvent (E);
The photosensitive coloring composition includes an organic solvent (E3) having a boiling point of 120° C. or more and less than 160° C. and a vapor pressure of 400 Pa or more at 20° C., in an amount of 55% by mass or more and 85% by mass or less based on 100% by mass of the organic solvent (E).

According to the present invention, it is possible to provide a photosensitive coloring composition that can control the climbing property of a laminated photospacer and form a film with few surface defects and excellent developability, adhesion, and pattern shape. The present invention can also provide a film, a color filter, and an image display device.

FIG. 1 is a schematic cross-sectional view showing an example of the configuration of a color filter of the present invention. FIG. 2 is a schematic cross-sectional view of an evaluation substrate used in the riding property evaluation (1) of the examples.

The following describes in detail the embodiment for implementing the photosensitive coloring composition of the present invention. Note that the present invention is not limited to the following embodiment, and can be modified within the scope of the problem that can be solved.

In this specification, unless otherwise specified, "(meth)acryloyl", "(meth)acrylic", "(meth)acrylic acid", "(meth)acrylate", or "(meth)acrylamide" respectively means "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 (C.I.; published by The Society of Dyers and Colourists). The polymerizable unsaturated group is an ethylenically unsaturated double bond.
In addition, the molecular weight of the compound in the present invention is a calculated value or a molecular weight measured by ESI-MS (electrospray ionization mass spectrometry) for a low molecular weight compound whose molecular weight can be specified, and is a polystyrene-equivalent weight average molecular weight measured by gel permeation chromatography using tetrahydrofuran as a solvent for a compound having a molecular weight distribution.
A monomer is a compound that will polymerize to form a resin. A monomer is in an unreacted state, and a monomer unit is a monomer that will polymerize to form a resin.

<Photosensitive Coloring Composition>
The photosensitive coloring composition of the present invention is a photosensitive coloring composition comprising a colorant (A), a binder resin (B), a polymerizable compound (C), a polymerization initiator (D), and an organic solvent (E),
The organic solvent (E) contains an organic solvent (E1) having a boiling point of 180° C. or more and 220° C. or less and a vapor pressure at 20° C. of less than 100 Pa in an amount of 0.1 mass% or more and less than 10 mass% based on 100 mass% of the organic solvent (E),
The organic solvent (E2) has a boiling point of 160° C. or more and less than 180° C. and a vapor pressure at 20° C. of 100 Pa or more and less than 400 Pa, and the organic solvent (E2) is contained in an amount of 10 mass% or more and 40 mass% or less based on 100 mass% of the organic solvent (E);
The organic solvent (E) contains an organic solvent (E3) having a boiling point of 120° C. or more and less than 160° C. and a vapor pressure of 400 Pa or more at 20° C. in an amount of 55% by mass or more and 85% by mass or less based on 100% by mass of the organic solvent (E).

The mechanism by which the photosensitive coloring composition having the above-mentioned configuration can solve the above problems is unclear, but it is speculated as follows.

An organic solvent (E1) having a boiling point of 180°C or more and 220°C or less and a vapor pressure at 20°C of less than 100 Pa (hereinafter also referred to as organic solvent (E1)) is difficult to evaporate in the coating and drying process and remains in the film for a long time. Therefore, it is presumed that even if the non-volatile content in the film increases in the drying process, the film has fluidity, the film is given time to spread evenly, and the riding property is good. However, if the content is high, a large amount remains in the film, and the adhesion and pattern shape are likely to deteriorate. In addition, aggregated foreign matter derived from the colorant (A) is likely to occur, and defects are likely to occur on the surface.
On the other hand, organic solvents (E3) having a boiling point of 120°C or more but less than 160°C and a vapor pressure of 400 Pa or more at 20°C (hereinafter also referred to as organic solvents (E3)) tend to evaporate during the coating and drying process. Therefore, they do not remain in the film and do not affect the adhesion or pattern shape. However, because they dry quickly, the film loses fluidity and tends to deteriorate in terms of ride-on properties. In addition, crater-like depressions and the like tend to occur on the surface of the film, and defects tend to occur on the surface.
Therefore, it is presumed that by combining organic solvent (E1), organic solvent (E3), and organic solvent (E2) (hereinafter also referred to as organic solvent (E2)) in a specific ratio, which has a boiling point of 160°C or more and less than 180°C and a vapor pressure of 100 Pa or more and less than 400 Pa at 20°C, and has a drying speed intermediate between organic solvent (E1) and organic solvent (E3), a photosensitive coloring composition can be obtained that can maintain the fluidity of the film from the coating to drying process, control the riding property, and form a film with few surface defects and excellent developability, adhesion, and pattern shape.

[Colorant (A)]
The photosensitive coloring composition of the present invention contains a colorant (A).

The colorant (A) is not particularly limited and may be either a pigment or a dye, which may be used in combination. Pigments include organic pigments and inorganic pigments, and for color filter applications, it is preferable to use a pigment in view of light resistance, heat resistance, and solvent resistance.

(Pigment)
The pigment is not particularly limited, and examples thereof include compounds classified as pigments in the Color Index.

Red pigments include, for example, C.I. Pigment Red 1, 2, 3, 4, 5, 6, 7, 8, 9, 12, 14, 15, 16, 17, 21, 22, 23, 31, 32, 37, 38, 41, 47, 48, 48:1, 48:2, 48:3, 48:4, 49, 49:1, 49:2, 50:1, 52:1, 52:2, 53, 53:1, 53:2, 53:3, 57, 57:1, 57:2, 58:4, 60, 63, 63:1, 63:2 , 64, 64:1, 68, 69, 81, 81:1, 81:2, 81:3, 81:4, 83, 88, 90:1, 101, 101:1, 104, 108, 108:1, 109, 112, 113, 114, 122, 123, 144, 146, 147, 149, 151, 166, 168, 169, 170, 172, 173, 174, 175, 176, 177, 178, 179, 181, 18 4, 185, 187, 188, 190, 193, 194, 200, 202, 206, 207, 208, 209, 210, 214, 216, 220, 221, 224, 230, 231, 232, 233, 235, 236, 237, 238, 239, 242, 243, 245, 247, 249, 250, 251, 253, 254, 255, 256, 257, 258, 259, 260, 262, 263, 264, 265, 266, 267, 268, 269, 270, 271, 272, 273, 274, 275, 276, 277, 278, 279, 280, 281, 282, 283, 284, 285, 286, 287, 291, 295, 296, pigments described in JP-A-2014-134712, and pigments described in Japanese Patent No. 6368844.

Examples of orange pigments include C.I. Pigment Orange 36, 38, 43, 64, 71, and 73.

Yellow pigments include, for example, C.I. Pigment Yellow 1, 2, 3, 4, 5, 6, 10, 12, 13, 14, 15, 16, 17, 18, 24, 31, 32, 34, 35, 35:1, 36, 36:1, 37, 37:1, 40, 42, 43, 53, 55, 60, 61, 62, 63, 65, 73, 74, 77, 81, 83, 93, 94, 95, 97, 98, 100, 101, 104, 106, 108, 109, 110, 113, 114, 115, 116, 117, 118, 119, 120, 123, 126, 1 27, 128, 129, 138, 139, 147, 150, 151, 152, 153, 154, 155, 156, 161, 162, 164, 166, 167, 168, 169, 170, 171, 172, 173, 174, 175, 176, 177, 179, 180, 181, 182, 185, 187, 188, 192, 193, 194, 196, 198, 199, 213, 214, 231, 233, and the pigments described in JP-A-2012-226110.

Yellow pigments include pigments containing at least one anion selected from the group consisting of azo compounds represented by the following general formula (1) and mono-, di-, tri-, and tetra-anions of azo compounds having tautomeric structures thereof, at least two metal ions selected from Cd, Co, Al, Cr, Sn, Pb, Zn, Fe, Ni, Cu, and Mn, and a compound represented by the following general formula (2).

General formula (1)

In general formula (1), two R _1s each independently represent -OH, -NH ₂ , -NH-CN, an acylamino group, an alkylamino group, or an arylamino group, and two R _2s each independently represent -OH or -NH ₂ .

General formula (2)

In formula (2), three _R3s each independently represent a hydrogen atom or an alkyl group.

Examples of green pigments 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, 59, 62, and 63.

Examples of blue pigments include 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, 66, 67, 68, 71, 72, 73, 74, 75, 76, 78, and 79.

Examples of purple pigments include 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.

Examples of black pigments include C.I. Pigment Black 1, 6, 7, 12, 20, and 31.

Additional inorganic pigments include silica, talc, titanium oxide, zinc oxide, barium sulfate, zinc oxide, lead sulfate, yellow lead, zinc yellow, red iron oxide (red iron (III) oxide), cadmium red, ultramarine, iron blue, chromium oxide green, cobalt green, amber, and synthetic iron black.

The pigment is preferably micronized before use. The method of micronization is not particularly limited, and for example, any of wet grinding, dry grinding, and dissolution precipitation methods can be used. Among these, salt milling treatment using a kneader method, which is a type of wet grinding, is preferred. The average primary particle size of the micronized pigment determined by TEM (transmission electron microscope) is preferably 5 to 90 nm. From the viewpoints of dispersibility and contrast ratio, the average primary particle size is more preferably 10 to 70 nm.

In the salt milling treatment, a resin may be added as necessary. By adding a resin, the pigment is coated with the resin, improving stability, light resistance, etc. The type of resin is not particularly limited, and examples include natural resins, modified natural resins, synthetic resins, and synthetic resins modified with natural resins. Among these, it is preferable that the resin is solid at room temperature, insoluble in water, and partially soluble in organic solvents. The amount of resin added is preferably 2 to 200 parts by mass per 100 parts by mass of the pigment.

(dye)
Examples of the dye include acid dyes, direct dyes, basic dyes, salt-forming dyes, oil-soluble dyes, disperse dyes, reactive dyes, mordant dyes, vat dyes, sulfur dyes, etc. Furthermore, the dye may be a derivative of these dyes or a lake pigment obtained by converting a dye into a lake.

The acid dye preferably has an acid group such as sulfonic acid or carboxylic acid. The direct dye preferably forms an inorganic salt of the acid dye, or a salt-forming compound of the acid dye and a nitrogen-containing compound such as a quaternary ammonium salt compound, a tertiary amine compound, a secondary amine compound, or a primary amine compound. In addition, a salt-forming compound that is a salt of a resin component having these functional groups and an acid dye is also preferred. In addition, the salt-forming compound is easily modified into a sulfonamide compound to obtain a photosensitive coloring composition with excellent resistance (light resistance, solvent resistance).
In addition, a salt-forming compound of an acid dye and a compound having an onium salt group is also preferable because it has excellent resistance (light resistance, solvent resistance). The compound having an onium salt group is preferably a resin having a cationic group.

Although basic dyes can be used as they are, salt-forming compounds that form salts with organic acids, perchloric acid, or metal salts thereof are preferred. Basic dye salt-forming compounds are preferred because they have excellent resistance (light resistance, solvent resistance) and affinity with pigments. In addition, in the basic dye salt-forming compounds, the anion component that acts as a counter ion is preferably an organic sulfonic acid, an organic sulfuric acid, a fluorine group-containing phosphorus anion compound, a fluorine group-containing boron anion compound, a cyano group-containing nitrogen anion compound, an anion compound having a conjugate base of an organic acid having a halogenated hydrocarbon group, or a salt-forming compound formed with an acid dye. The resistance of the salt-forming compound is further improved when the compound contains a polymerizable unsaturated group in the molecule.

The chemical structure of dyes can be, 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 properties 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.

The colorant (A) may be used alone or in combination of two or more types.

The content of colorant (A) is preferably 5% by mass or more and 70% by mass or less, and more preferably 10% by mass or more and 60% by mass or less, based on 100% by mass of the non-volatile content of the photosensitive coloring composition.

[Binder resin (B)]
The photosensitive coloring composition of the present invention contains a binder resin (B).

There are no particular limitations on the binder resin (B), and known resins can be used. Examples include (meth)acrylic resins, styrene resins, styrene/(meth)acrylic resins, epoxy resins, urethane resins, polycarbonate resins, polyester resins, polyether resins, polyimide resins, polyamide-imide resins, and cyclic olefin resins.

The weight average molecular weight of the binder resin (B) is preferably 3,000 to 50,000.

The acid value of the binder resin (B) is preferably 30 to 200 mg KOH/g, and more preferably 40 to 180 mg KOH/g.

The binder resin (B) can be used alone or in combination of two or more types.

The binder resin (B) is preferably from 1% by mass to 80% by mass, and more preferably from 3% by mass to 70% by mass, based on 100% by mass of the non-volatile content of the photosensitive coloring composition.

(Binder resin (B1) having a weight average molecular weight of 3,000 to 8,000)
From the viewpoint of riding up, the photosensitive coloring composition of the present invention preferably contains a binder resin (B1) having a weight average molecular weight of 3,000 to 8,000 (hereinafter also referred to as binder resin (B1)) as the binder resin (B). By containing a binder resin (B1) having a weight average molecular weight of 3,000 to 8,000, even if the composition becomes highly non-volatile during the drying process, a sudden increase in viscosity can be suppressed and fluidity can be maintained. Therefore, it is presumed that the film spreads easily and the riding up property is improved.

The weight average molecular weight of the binder resin (B1) is more preferably 3,000 to 7,000.

The content of binder resin (B1) is preferably 50% by mass or more and 100% by mass or less, and more preferably 60% by mass or more and 100% by mass or less, based on 100% by mass of binder resin (B).

From the viewpoint of adhesion and pattern shape, the binder resin (B1) is preferably a resin containing an alicyclic hydrocarbon-containing monomer unit (b1) and a polymerizable unsaturated group-containing monomer unit (b2). The highly hydrophobic and rigid alicyclic hydrocarbon structure can form a tough film, and furthermore, it is presumed that the presence of a polymerizable unsaturated group allows the resins to crosslink with each other upon exposure, resulting in a film with good adhesion and pattern shape.

Examples of the binder resin (B1) include a copolymer of a monomer that forms an alicyclic hydrocarbon-containing monomer unit (b1) and a monomer that forms a polymerizable unsaturated group-containing monomer unit (b2), a copolymer in which a compound having a polymerizable unsaturated group is reacted with a copolymer of a monomer that forms an alicyclic hydrocarbon-containing monomer unit (b1) and another monomer that can be copolymerized therewith to introduce a polymerizable unsaturated group-containing monomer unit (b2), and a copolymer obtained by the method described in JP-A-2008-165059.

[Alicyclic Hydrocarbon-Containing Monomer Unit (b1)]
Examples of monomers forming the alicyclic hydrocarbon-containing monomer unit (b1) include isobornyl (meth)acrylate, cyclohexyl (meth)acrylate, dicyclopentanyl (meth)acrylate, dicyclopentenyl (meth)acrylate, dicyclopentanyloxyethyl (meth)acrylate, dicyclopentenyloxyethyl (meth)acrylate, adamantyl (meth)acrylate, etc. Among these, dicyclopentanyl (meth)acrylate, dicyclopentenyl (meth)acrylate, and dicyclopentanyloxyethyl (meth)acrylate are preferred.

From the viewpoints of adhesion and pattern shape, the content of the alicyclic hydrocarbon-containing monomer unit (b1) is preferably 1 to 60 mol %, and more preferably 5 to 50 mol %, of all the constituent units of the binder resin (B1).

[Polymerizable unsaturated group-containing monomer unit (b2)]
In the binder resin (B1), the polymerizable unsaturated group-containing monomer unit (b2) can be formed, for example, by the following methods (i) to (iii).

<Method (i)>
In the method (i), for example, a polymer (precursor) of an epoxy group-containing monomer and another monomer is first polymerized, and then a carboxyl group-containing monomer (modifying compound) is added to the epoxy group of the precursor.

Examples of epoxy group-containing monomers include glycidyl (meth)acrylate, methyl glycidyl (meth)acrylate, 2-glycidoxyethyl (meth)acrylate, 3,4-epoxybutyl (meth)acrylate, and 3,4-epoxycyclohexyl (meth)acrylate. Among these, glycidyl (meth)acrylate is preferred from the viewpoint of reactivity.

Examples of carboxyl group-containing monomers include acrylic acid, methacrylic acid, crotonic acid, itaconic acid, maleic acid, and fumaric acid. Of these, acrylic acid and methacrylic acid are preferred.

From the viewpoint of developability, a portion in which an acid anhydride is reacted with a portion in which a carboxyl group of a carboxyl group-containing monomer is added to an epoxy group of an epoxy group-containing monomer unit is also preferred as the polymerizable unsaturated group-containing monomer unit (b2).

Examples of acid anhydrides include tetrahydrophthalic anhydride, phthalic anhydride, hexahydrophthalic anhydride, succinic anhydride, maleic anhydride, etc.

<Method (ii)>
In the method (ii), for example, a polymer (precursor) of a carboxyl group-containing monomer and another monomer is polymerized, and then an epoxy group-containing monomer (modifying compound) is added to the carboxyl group of the precursor.

<Method (iii)>
In the method (iii), for example, a polymer (precursor) of a hydroxyl group-containing monomer, a carboxyl group-containing monomer, and other monomers is polymerized, and then the hydroxyl group of the precursor is reacted with an isocyanate group of an isocyanate group-containing monomer (modifying compound).

Examples of hydroxyl group-containing monomers include hydroxyalkyl (meth)acrylates such as 2-hydroxyethyl (meth)acrylate, 2- or 3-hydroxypropyl (meth)acrylate, 2-, 3-, or 4-hydroxybutyl (meth)acrylate, glycerol mono(meth)acrylate, and cyclohexanedimethanol mono(meth)acrylate.

Examples of isocyanate group-containing monomers include 2-(meth)acryloylethyl isocyanate, 2-(meth)acryloyloxyethyl isocyanate, and 1,1-bis[methacryloyloxy]ethyl isocyanate.

From the viewpoints of adhesion and pattern shape, the content of the polymerizable unsaturated group-containing monomer unit (b2) is preferably 5 to 80 mol %, and more preferably 10 to 60 mol %, of all the constituent units of the binder resin (B1).

The binder resin (B1) can contain monomer units other than the alicyclic hydrocarbon-containing monomer unit (b1) and the polymerizable unsaturated group-containing monomer unit (b2). Examples include hydroxyl group-containing monomer units (b3), acidic group-containing monomer units (b4), epoxy group-containing monomer units (b5), aromatic ring-containing monomer units (b6), blocked isocyanate group-containing monomer units (b7), and other monomer units (b8). These monomer units can be contained alone or in combination of two or more types.

[Hydroxyl Group-Containing Monomer Unit (b3)]
Examples of the hydroxyl group-containing monomer include 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, 3-hydroxybutyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, 2,3-hydroxypropyl (meth)acrylate, glycerol mono(meth)acrylate, cyclohexanedimethanol mono(meth)acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-acryloyloxyethyl-2-hydroxyethyl phthalate, etc. These monomers can be used alone or in combination of two or more.

[Acidic group-containing monomer unit (b4)]
Examples of the acidic group-containing monomer include (meth)acrylic acid, crotonic acid, propiolic acid, cinnamic acid, itaconic acid, itaconic anhydride, maleic acid, monomethyl maleate, monoethyl maleate, monoisopropyl maleate, maleic anhydride, fumaric acid, 2-methacryloyloxyethyl succinic acid, 2-acryloyloxyethyl phthalic acid, 2-acryloyloxyethylhexyl hydrophthalic acid, p-styrenesulfonic acid, vinylsulfonic acid, 2-acrylamido-2-methylpropanesulfonic acid, tert-butylacrylamidosulfonic acid, 2-(meth)acryloyloxyethyl acid phosphate, etc. These monomers can be used alone or in combination of two or more.

[Epoxy group-containing monomer unit (b5)]
Examples of epoxy group-containing monomers include oxiranyl (meth)acrylate, glycidyl (meth)acrylate, 2-methylglycidyl (meth)acrylate, 2-ethylglycidyl (meth)acrylate, 2-oxiranylethyl (meth)acrylate, 2-glycidyloxyethyl (meth)acrylate, 3,4-epoxycyclohexyl (meth)acrylate, 3,4-epoxycyclohexylmethyl (meth)acrylate, 2-(3,4-epoxycyclohexyl)ethyl (meth)acrylate, 2-(3,4-epoxycyclohexylmethyloxy)ethyl (meth)acrylate, 3-(3,4-epoxycyclohexylmethyloxy)propyl (meth)acrylate, etc. These monomers can be used alone or in combination of two or more.

[Aromatic ring-containing monomer unit (b6)]
Examples of aromatic ring-containing monomers include styrene, α-methylstyrene, vinylnaphthalene, phenyl (meth)acrylate, benzyl (meth)acrylate, phenoxyethyl (meth)acrylate, paracumylphenol ethylene oxide (hereinafter also referred to as EO) or propylene oxide (hereinafter also referred to as PO) modified (meth)acrylate, phenol EO or PO modified (meth)acrylate, nonylphenol EO or PO modified (meth)acrylate, N-phenylmaleimide, N-benzylmaleimide, etc. These monomers may be used alone or in combination of two or more.

[Blocked isocyanate group-containing monomer unit (b7)]
The blocked isocyanate group-containing monomer is a monomer in which the isocyanate group of the isocyanate group-containing monomer is protected with a compound that is eliminated by heat (hereinafter, also referred to as a blocking agent). The elimination temperature of the blocking agent is preferably 60 to 160°C.

Examples of isocyanate group-containing monomers include 2-isocyanatoethyl (meth)acrylate, 2-isocyanatopropyl (meth)acrylate, 3-isocyanatopropyl (meth)acrylate, 2-isocyanato-1-methylethyl (meth)acrylate, 2-isocyanato-1,1-dimethylethyl (meth)acrylate, 4-isocyanatocyclohexyl (meth)acrylate, and methacryloyl isocyanate. In addition, equimolar reaction products of 2-hydroxyalkyl (meth)acrylate and diisocyanate compounds can also be used.

Blocking agents include oxime compounds, lactam compounds, phenol compounds, alcohol compounds, amine compounds, active methylene compounds, pyrazole compounds, mercaptan compounds, imidazole compounds, imide compounds, urea compounds, imine compounds, and bisulfite compounds.

Examples of the oxime compound include formaldoxime, acetaldoxime, acetoxime, methyl ethyl ketoxime, methyl isobutyl ketoxime, cyclohexanone oxime, benzophenone oxime, etc. Among these, methyl ethyl ketoxime is preferred.
Examples of the lactam compound include ε-caprolactam, δ-valerolactam, γ-butyrolactam, and β-propiolactam.
Examples of the phenol compound include phenol, cresol, 2,6-xylenol, 3,5-xylenol, ethylphenol, p-tert-butylphenol, nonylphenol, methyl 2-hydroxybenzoate, methyl 4-hydroxybenzoate, p-naphthol, p-nitrophenol, etc. Among these, 3,5-xylenol, methyl 2-hydroxybenzoate, and methyl 4-hydroxybenzoate are preferred.
Examples of the alcohol compound include methanol, ethanol, propanol, butanol, ethylene glycol, methyl cellosolve, butyl cellosolve, methyl carbitol, benzyl alcohol, phenyl cellosolve, and furfuryl alcohol.
Examples of the amine compound include diphenylamine, phenylnaphthylamine, aniline, and carbazole.
Examples of the active methylene compound include dimethyl malonate, diethyl malonate, methyl acetoacetate, ethyl acetoacetate, and acetylacetone, with diethyl malonate being preferred.
Examples of the pyrazole compound include pyrazole, methylpyrazole, and 3,5-dimethylpyrazole, with 3,5-dimethylpyrazole being preferred.
Examples of the mercaptan compound include butyl mercaptan, thiophenol, and tert-dodecyl mercaptan.
Examples of the imidazole compound include imidazole, 2-methylimidazole, 2-ethylimidazole, 1,2-dimethylimidazole, 2-ethyl-4-methylimidazole, and 1-benzyl-2-phenylimidazole.
Examples of the imide compound include succinimide, maleimide, maleimide, and phthalimide.
Examples of the urea compound include urea, thiourea, and ethyleneurea.
Examples of the imine compound include ethyleneimine and polyethyleneimine.
Examples of the bisulfite compound include sodium bisulfite and potassium bisulfite.

Blocking agents can be used alone or in combination of two or more types.

The blocking agent is preferably one or more selected from the group consisting of oxime compounds, lactam compounds, phenol compounds, alcohol compounds, amine compounds, active methylene compounds, pyrazole compounds, mercaptan compounds, imidazole compounds, and imide compounds, and from the viewpoint of protection reactions and deprotection reactions, it is more preferably one or more selected from the group consisting of oxime compounds, phenol compounds, active methylene compounds, and pyrazole compounds.

Examples of blocked isocyanate group-containing monomers include the following compounds. Note that the present invention is not limited to these.

Commercially available blocked isocyanate group-containing monomers include Showa Denko's Karenz MOI-DEM (blocking agent desorption temperature: 85-95°C), MOI-BP (blocking agent desorption temperature: 105-115°C), and MOI-BM (blocking agent desorption temperature: 125-135°C). These monomers can be used alone or in combination of two or more.

[Other monomer units (b8)]
Examples of other monomers include acrylic acid esters such as ethyl (meth)acrylate, n-propyl (meth)acrylate, isopropyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, tert-butyl (meth)acrylate, pentyl (meth)acrylate, hexyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, lauryl (meth)acrylate, dimethylaminoethyl (meth)acrylate, and diethylaminoethyl (meth)acrylate;
(meth)acrylamides such as (meth)acrylamide, N,N-dimethyl(meth)acrylamide, N,N-diethyl(meth)acrylamide, N-isopropyl(meth)acrylamide, diacetone(meth)acrylamide, or acryloylmorpholine;
Vinyl ethers such as ethyl vinyl ether, n-propyl vinyl ether, isopropyl vinyl ether, n-butyl vinyl ether, and isobutyl vinyl ether;
vinyl acetate, vinyl propionate, or other vinyl fatty acids;
N-substituted maleimides such as methylmaleimide, ethylmaleimide, 1,2-bismaleimidoethane, 1,6-bismaleimidohexane, 3-maleimidopropionic acid, and 6,7-methylenedioxy-4-methyl-3-maleimidocoumarin;
Examples of such monomers include dimethyl-2,2'-[oxybis(methylene)]bis-2-propenoate, diethyl-2,2'-[oxybis(methylene)]bis-2-propenoate, di(n-propyl)-2,2'-[oxybis(methylene)]bis-2-propenoate, di(isopropyl)-2,2'-[oxybis(methylene)]bis-2-propenoate, and di(2-ethylhexyl)-2,2'-[oxybis(methylene)]bis-2-propenoate. These monomers can be used alone or in combination of two or more.

(Binder Resin (B2))
The photosensitive coloring composition of the present invention may contain, as the binder resin (B), a binder resin (B2) other than the binder resin (B1) (hereinafter, also simply referred to as the binder resin (B2)).

[Polymerizable compound (C)]
The photosensitive coloring composition of the present invention contains a polymerizable compound (C).

The polymerizable compound (C) may be a monomer or oligomer having a polymerizable unsaturated group. Examples of the polymerizable unsaturated group include a vinyl group, a (meth)allyl group, a (meth)acryloyl group, and a (meth)acryloyloxy group.

Examples of the polymerizable compound (C) 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 (meth)acrylate, and other various acrylic acid esters and methacrylic acid esters, styrene, vinyl acetate, hydroxyethyl vinyl ether, ethylene glycol divinyl ether, pentaerythritol trivinyl ether, (meth)acrylamide, N-hydroxymethyl (meth)acrylamide, N-vinyl formamide, and acrylonitrile.

Commercially available products include Nippon Kayaku's KAYARAD R-128H, NPGDA, PEG400DA, FM-400, R-167, HX-220, HX-620, R-551, R712, R-604, R-684, GPO-303, PET-30, T-1420(T), RP-1040, DPHA, DPEA-12, D-310, D-330, and DCPA-20. , DCPA-30, DCPA-60, DCPA-120, FM-700, PM-2, PM-21, Aronix M-101A, M-111, M-120, M-140, M-208, M-211B, M-215, M-22-, M-225, M-240, M-303, M-305, M-306, M -309, M-310, M-321, M-325, M-350, M-360, M-313, M-315, M-400, M-402, M-403, M-404, M-405, M-406, M-408, M-450, M-452, M-460, M-471, M-510, M-520, M-521, M-5300 , M-5400, M-5700, M-920, MT-3041, 3042, Osaka Organic Viscoat #150, #155, #160, #192, #190, 2-MTA, MTG, MEDOL-10, OXE-10, OXE-30, #200, #196, #195, #230, #260, #310HP, #5 40, #802, #295, #300, #1000LT, Light Ester HOP (N), HOA (N), HOP-A (N), HOB (N), G-201P, HO-MS (N), P-1M, Epoxy Ester M-600A, 40EM, 70PA, 200PA, 80MFA, 3002M (N), 3002A (N), 3000A, Light Acrylate HOA-HH (N), HOA-MS (N), HOA-MPL (N), P-1A (N), AH-600, AT-600, UA-306H, UA-306T, UA-306I, UA-510H, UF-8001G manufactured by Kyoeisha Chemical Co., Ltd., NK Ester AM-90 manufactured by Shin-Nakamura Chemical Co., Ltd. G, AM-130G, AMP-20GY, A-LEN-10, A-SA, A-HD-N, A-NOD-N, A-DOD-N, A-NPG, 701A, A-200, A-400, APG-200, APG-400, A-DCP, ABE-300, A-BPE-4, A-BPE-10, A-TMPT, A-TM PT-9EO, A-GLY-3E, A-GLY-9E, A-GLY-20E, A-9300, A-9200YN, A-TMMT, ATM-35E, AD-TMP, A-DPH, A-9550, A-DPH-12E, UA-1100H, U-6LPA, UA-33H, U-10HA, U-15HA, Miwon Specialty Chemical Co. Miramer HR6060, 6100, 6200, SP-1106, SP-1108 manufactured by Daicel Allnex Co., Ltd.; EBECRYL40, 130, 140, 145 manufactured by Daicel Allnex Co., Ltd.; OGSOL EA-0200, 0300, GA-5060P, GA-2800 manufactured by Osaka Gas Chemicals Co., Ltd.; and Blenmar GLM, GLM-R, GMR-M, GMR-R, GAM, GAM-R, G-FA80 manufactured by NOF Corp.

The polymerizable compound (C) can be used alone or in combination of two or more types.

The content of the polymerizable compound (C) is preferably 5% by mass or more and 70% by mass or less, and more preferably 10% by mass or more and 60% by mass or less, based on 100% by mass of the non-volatile content of the photosensitive coloring composition.

(Polymerizable compound (C1) having a viscosity of 500 mPa·S or less at 25° C.)
From the viewpoint of riding up, the photosensitive coloring composition of the present invention preferably contains a polymerizable compound (C1) (hereinafter also simply referred to as polymerizable compound (C1)) having a viscosity of 500 mPa·S or less at 25 ° C. as the polymerizable compound (C). By containing a polymerizable compound (C1) having a viscosity of 500 mPa·S or less at 25 ° C., a sudden increase in viscosity of the film can be suppressed during the drying process in the process in which the non-volatile content inside the film increases due to the volatilization of the organic solvent, and fluidity can be maintained. Therefore, it is presumed that the film is easy to spread and the riding up property is improved.

Examples of the polymerizable compound (C1) include caprolactone acrylate (67-82), isobornyl acrylate (15), cyclic trimethylolpropane formal acrylate (10-20), phenoxybenzyl acrylate (12-20), benzyl acrylate (1-10), benzyl methacrylate (1-10), tetrahydrofurfuryl acrylate (2-10), 2-hydroxypropyl acrylate (3-8), 1,6-hexanediol diacrylate (5-15), 1,6-hexanediol dimethacrylate (1-10), 1,6-hexanediol EO-modified diacrylate (10-30), 1,9-nonanediol diacrylate (5-15), neopentyl glycol diacrylate (5-10), neopentyl glycol dimethacrylate (3-15 ...acrylate (5-15), 1,6-hexanediol diacrylate (5-15), 1,6-hexanediol diacrylate (5-15), 1,6-hexanediol diacrylate (5-15), 1,6-hexanediol diacrylate (5-15), 1,6-hexanediol diacrylate (5-15), 1,6-hexanediol diacrylate (5-15), 1,6-hexanediol diacrylate (5-15), 1,6-hexanediol diacrylate (5-15), 1,6-hexanediol diacrylate (5-15), Examples of the acrylates include 3-methacrylpropyl acrylate (35-55), tricyclodecane dimethanol diacrylate (125-145), tricyclodecane dimethanol dimethacrylate (100-130), tripropylene glycol diacrylate (15-20), dipropylene glycol diacrylate (5-30), triethylene glycol diacrylate (10-20), trimethylolpropane triacrylate (80-120), trimethylolpropane trimethacrylate (35-55), trimethylolpropane EO-modified triacrylate (50-90), trimethylolpropane PO-modified triacrylate (60-150), glycerin PO-modified triacrylate (80-120), pentaerythritol EO-modified tetraacrylate (300-400), etc. The numbers in parentheses indicate the viscosity (mPa·S) at 25°C. Among these, from the viewpoints of adhesion and pattern shape, di- to tetra-functional (meth)acrylates are preferred, and tri- or tetra-functional (meth)acrylates are more preferred.

From the viewpoint of ride-on property, the viscosity of the polymerizable compound (C1) at 25°C is more preferably 1 mPa·S or more and 200 mPa·S or less.

The polymerizable compound (C1) may be used alone or in combination of two or more types.

The content of the polymerizable compound (C1) is preferably 5% by mass or more and 70% by mass or less, and more preferably 15% by mass or more and 60% by mass or less, based on 100% by mass of the polymerizable compound (C).

(Polymerizable compound (C2) having a urethane bond)
From the viewpoints of surface defect suppression, adhesion, and pattern shape, the photosensitive coloring composition of the present invention preferably contains a polymerizable compound (C2) having a urethane bond as the polymerizable compound (C) (hereinafter, also simply referred to as polymerizable compound (C2)). The polymerizable compound (C2) forms a physical crosslinked structure due to intermolecular hydrogen bonds of the urethane bond part as well as a chemical crosslinked structure due to the reaction of the polymerizable unsaturated group in the film. The molecular cohesive energy of the intermolecular hydrogen bonds of the urethane bond part is larger than the cohesive energy of other organic structures such as ether bonds. Therefore, it is speculated that the film in which the photosensitive coloring composition containing the polymerizable compound (C2) is cured will be strong due to the interaction between the urethane bonds. In addition, the interaction between the urethane bonds has a weaker binding force than the chemical bond and has moderate flexibility. Therefore, it is speculated that damage to the film can be suppressed. It is also speculated that the interaction between the urethane bonds inhibits the movement of the colorant in the film, thereby suppressing aggregation and improving the surface condition.

Examples of the polymerizable compound (C2) include urethane (meth)acrylates obtained by reacting a (meth)acrylate having a hydroxyl group with a polyfunctional isocyanate, and urethane (meth)acrylates obtained by reacting a polyhydric alcohol with a polyfunctional isocyanate and then reacting the polyhydric alcohol with a (meth)acrylate having a hydroxyl group.

Examples of the (meth)acrylate 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 (EO) modified penta(meth)acrylate, dipentaerythritol propylene oxide (PO) modified penta(meth)acrylate, dipentaerythritol caprolactone modified penta(meth)acrylate, glycerol tri(meth)acrylate, glycerol di(meth)acrylate, glycerol mono(meth)acrylate, 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 the polyfunctional isocyanate include aliphatic diisocyanates such as trimethylene diisocyanate, tetramethylene diisocyanate, and hexamethylene diisocyanate, alicyclic diisocyanates such as isophorone diisocyanate, and aromatic diisocyanates such as tolylene diisocyanate, diphenylmethylene diisocyanate, and xylene diisocyanate, as well as their biuret forms, isocyanate nurate forms, and trimethylolpropane adducts.

The number of polymerizable unsaturated groups in the polymerizable compound (C2) is preferably 5 to 12 from the viewpoints of adhesion and pattern shape.

From the viewpoints of suppressing surface defects, adhesion, and pattern shape, the molecular weight (weight average molecular weight or formula weight) of the polymerizable compound (C2) is preferably 500 to 5,000, more preferably 500 to 3,000, and particularly preferably 500 to 2,000.

The polymerizable compound (C2) may be used alone or in combination of two or more types.

From the viewpoints of suppressing surface defects, adhesion, and pattern shape, the content of the polymerizable compound (C2) is preferably 30% by mass or more and 80% by mass or less, and more preferably 20% by mass or more and 70% by mass or less, based on 100% by mass of the polymerizable compound (C).

From the viewpoints of suppressing surface defects, adhesion, and pattern shape, it is preferable that the polymerizable compound (C2) contains at least one selected from the group consisting of alicyclic urethane (meth)acrylates and aromatic urethane (meth)acrylates. By having a rigid alicyclic structure or aromatic ring structure, a tougher coating film can be obtained.

[Alicyclic urethane (meth)acrylate]
The alicyclic urethane (meth)acrylate is not particularly limited, and a known compound can be used. The alicyclic urethane (meth)acrylate can be synthesized, for example, by using a polyfunctional isocyanate having an alicyclic structure as the polyfunctional isocyanate, which is a raw material of the above-mentioned polymerizable compound (C2).

Examples of the polyfunctional isocyanate having an alicyclic structure include cyclohexane-1,4-diisocyanate, isophorone diisocyanate, dimethylcyclohexyl diisocyanate, methylcyclohexyl diisocyanate, dicyclohexylmethane-4,4'-diisocyanate, 1,3-bis(isocyanatemethyl)cyclohexane, methylcyclohexane diisocyanate, norbornane diisocyanate, bis(isocyanatemethyl)cyclohexane, etc. Also included are their biuret forms, isocyanate nurate forms, trimethylolpropane adduct forms, etc.

[Aromatic urethane (meth)acrylate]
The aromatic urethane (meth)acrylate is not particularly limited, and a known compound can be used. The aromatic urethane (meth)acrylate can be obtained, for example, by changing the polyfunctional isocyanate having an alicyclic structure of the above-mentioned alicyclic urethane (meth)acrylate to a polyfunctional isocyanate having an aromatic ring structure during synthesis.

Examples of polyfunctional isocyanates having the aromatic ring structure include 1,5-naphthylene diisocyanate, 4,4'-diphenylmethane diisocyanate, 4,4'-diphenyldimethylmethane diisocyanate, 4,4'-dibenzyl isocyanate, dialkyldiphenylmethane diisocyanate, tetraalkyldiphenylmethane diisocyanate, 1,3-phenylene diisocyanate, 1,4-phenylene diisocyanate, 2,4-toluene diisocyanate, 2,6-toluene diisocyanate, xylylene diisocyanate, m-tetramethylxylylene diisocyanate, 4,4-diphenylmethane diisocyanate, tolylene diisocyanate, bischloromethyldiphenylmethane diisocyanate, 2,6-diisocyanate-benzyl chloride, bis(isocyanatomethyl)benzene, and the like. Other examples include biuret forms, isocyanate nurate forms, and trimethylolpropane adduct forms.

From the viewpoint of developability, the photosensitive coloring composition of the present invention preferably further contains a polymerizable compound (C2) having an acidic group.

Examples of the polymerizable compound (C2) having an acidic group include a compound obtained by reacting the (meth)acrylate having a hydroxyl group with the polyfunctional isocyanate and then adding a mercapto compound having a carboxyl group to the product; a compound obtained by reacting the polyhydric alcohol with the polyfunctional isocyanate, reacting the (meth)acrylate having a hydroxyl group, and then adding a mercapto compound having a carboxyl group to the product; a compound obtained by reacting the polyhydric alcohol having a carboxyl group with the polyfunctional isocyanate and then reacting the (meth)acrylate having a hydroxyl group; and a compound obtained by reacting the polyhydric alcohol having a carboxyl group with the polyfunctional isocyanate and then reacting the (meth)acrylate having a hydroxyl group.

Examples of mercapto compounds having a carboxyl group include mercaptoacetic acid, 2-mercaptopropionic acid, 3-mercaptopropionic acid, o-mercaptobenzoic acid, 2-mercaptonicotinic acid, and mercaptosuccinic acid.

Examples of the polyhydric alcohol having a carboxyl group include compounds obtained by reacting the above polyhydric alcohol with a polybasic acid or anhydride thereof (e.g., succinic acid, succinic anhydride, fumaric acid, fumaric anhydride, tetrahydrophthalic anhydride, etc.) and dimethylolpropionic acid.

In the photosensitive coloring composition of the present invention, from the viewpoints of ride-on property, suppression of surface defects, adhesion, and pattern shape, the mass ratio C1:C2 of the polymerizable compound (C1) to the polymerizable compound (C2) is preferably 80:20 to 20:80, and more preferably 70:30 to 30:70.

[Polymerization initiator (D)]
The photosensitive coloring composition of the present invention contains a polymerization initiator (D).

The polymerization initiator (D) is not particularly limited, and any known compound can be used. For example, a compound that generates radicals by the action of light or heat to initiate or promote a radical polymerization reaction can be used.
The polymerization initiator that generates radicals by light (hereinafter, also simply referred to as a photopolymerization initiator) is preferably a compound that generates radicals when exposed to light in the ultraviolet to visible light range.
The polymerization initiator that generates radicals by heat (hereinafter, also simply referred to as a thermal polymerization initiator) may be a compound that generates radicals by the action of heat and light.

Examples of the photopolymerization initiator include acetophenone-based compounds such as 4-phenoxydichloroacetophenone, 4-t-butyl-dichloroacetophenone, diethoxyacetophenone, 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropan-1-one, 1-hydroxycyclohexyl phenyl ketone, 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one, 2-(dimethylamino)-1-[4-(4-morpholino)phenyl]-2-(phenylmethyl)-1-butanone, and 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]-1-butanone;
Triazine-based compounds such as 2,4,6-trichloro-s-triazine, 2-phenyl-4,6-bis(trichloromethyl)-s-triazine, 2-(p-methoxyphenyl)-4,6-bis(trichloromethyl)-s-triazine, 2-(p-tolyl)-4,6-bis(trichloromethyl)-s-triazine, 2-piperonyl-4,6-bis(trichloromethyl)-s-triazine, 2,4-bis(trichloromethyl)-6-styryl-s-triazine, 2-(naphth-1-yl)-4,6-bis(trichloromethyl)-s-triazine, 2-(4-methoxy-naphth-1-yl)-4,6-bis(trichloromethyl)-s-triazine, 2,4-trichloromethyl-(piperonyl)-6-triazine, or 2,4-trichloromethyl-(4'-methoxystyryl)-6-triazine;
Oxime compounds such as 1,2-octanedione, 1-[4-(phenylthio)phenyl-, 2-(O-benzoyloxime)], or ethanol, 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-, 1-(O-acetyloxime);
Acylphosphine compounds such as bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide or diphenyl-2,4,6-trimethylbenzoylphosphine oxide;
Examples of the compound include quinone-based compounds such as 9,10-phenanthrenequinone, camphorquinone, and ethylanthraquinone; borate-based compounds; and carbazole-based compounds.

Commercially available products include acetophenone compounds such as Omnirad 907, 369E, 379EG, 127, 184, 1173, and 2959 manufactured by IGM Resins, acylphosphine compounds such as Omnirad 819 and TPO manufactured by IGM Resins, oxime compounds such as IRGACURE OXE-01, 02, 03, and 04 manufactured by BASF Japan, ADEKA Arcles N-1919T, NCI-730, NCI-831E, and NCI-930 manufactured by ADEKA, and TRONLY manufactured by Changzhou Strong New Materials Co., Ltd. Examples of such resins include TR-PBG-301, 304, 305, 309, 314, 345, 358, 380, 365, 610, 3054, and 3057 manufactured by IGM Resins, Omnirad 1312, 1314, and 1316 manufactured by Samyang Corporation, SPI-02, 03, 04, 05, 06, and 07 manufactured by Daito Chemistry Co., Ltd., and DFI-020, 306, and EOX-01 manufactured by Daito Chemistry Co., Ltd. Also included are compounds described in JP 2007-210991 A, JP 2009-179619 A, JP 2010-037223 A, JP 2010-215575 A, JP 2011-020998 A, WO 2015/036910 A, JP 2019-507108 A, JP 2019-528331 A, WO 2021/175855 A, etc. Among these, oxime-based compounds are preferred from the viewpoints of adhesion and pattern shape.

Specific examples of oxime compounds are shown below. Note that the present invention is not limited to these.

From the viewpoints of adhesion and pattern shape, the polymerization initiator (D) is preferably a compound having an extinction coefficient of 5.0×10 ³ L/mol·cm or more at a wavelength of 365 nm in propylene glycol monomethyl ether acetate. Specific examples thereof include the above compounds (D-1), (D-2), (D-3), (D-4), (D-5), (D-6), (D-8), (D-9), (D-10), (D-12), (D-15), and (D-16).

Examples of the thermal polymerization initiator include benzopinacol, 1,2-dimethoxy-1,1,2,2-tetraphenylethane, 1,2-dimethoxy-1,1,2,2-tetraphenylethane, 1,2-diphenoxy-1,1,2,2-tetraphenylethane, 1,2-dimethoxy-1,1,2,2-tetraphenylethane, 1,2-dimethoxy-1,1,2,2-tetra(4-methylphenyl)ethane, 1,2-diphenoxy-1,1,2,2-tetra(4-methoxyphenyl)ethane, 1,2-bis(trimethylsiloxy)-1,1,2,2-tetraphenylethane, pinacol-based compounds such as 1,2-bis(triethylsiloxy)-1,1,2,2-tetraphenylethane, 1,2-bis(tert-butyldimethylsiloxy)-1,1,2,2-tetraphenylethane, 1-hydroxy-2-trimethylsiloxy-1,1,2,2-tetraphenylethane, 1-hydroxy-2-triethylsiloxy-1,1,2,2-tetraphenylethane, and 1-hydroxy-2-tert-butyldimethylsiloxy-1,1,2,2-tetraphenylethane;
Azo compounds such as 2,2'-azobis(4-methoxy-2,4-dimethylvaleronitrile), 2,2'-azobis(2,4-dimethylvaleronitrile), dimethyl-2,2'-azobis(2-methylpropionate), 2,2'-azobis(2-methylbutyronitrile), 1,1'-azobis(cyclohexane-1-carbonitrile), 2,2'-azobis[N-(2-propenyl)2-methylpropionamide], 1-[(1-cyano-1-methylethyl)azo]formamide, 2,2'-azobis(N-butyl-2-methylpropionamide), and 2,2'-azobis(N-cyclohexyl-2-methylpropionamide);
Examples of the organic peroxide include methyl ethyl ketone peroxide, cyclohexanone peroxide, 3,3,5-trimethylcyclohexanone peroxide, methylcyclohexanone peroxide, acetylacetone peroxide, 1,1-bis(tert-butylperoxy)-3,3,5-trimethylcyclohexane, 1,1-bis(tert-butylperoxy)cyclohexane, 2,2-bis(tert-butylperoxy)butane, succinic peroxide, and benzoyl peroxide. Among these, pinacol-based compounds are preferred.

Polymerization initiator (D) can be used alone or in combination of two or more types.

The content of the polymerization initiator (D) is preferably 0.5% by mass or more and 20% by mass or less, and more preferably 1% by mass or more and 10% by mass or less, based on 100% by mass of the non-volatile content of the photosensitive coloring composition.

[Organic solvent (E)]
The photosensitive coloring composition of the present invention contains an organic solvent (E).

(Organic solvent (E1) having a boiling point of 180° C. or more and 220° C. or less and a vapor pressure at 20° C. of less than 100 Pa)
The photosensitive coloring composition of the present invention contains, as the organic solvent (E), an organic solvent (E1) having a boiling point of 180° C. or more and 220° C. or less and a vapor pressure at 20° C. of less than 100 Pa in an amount of 0.1% by mass or more and less than 10% by mass in 100% by mass of the organic solvent (E).

Specific examples of the organic solvent (E1) include diethylene glycol diethyl ether (boiling point 188°C, vapor pressure 90 Pa), dipropylene glycol monomethyl ether (boiling point 188°C, vapor pressure 55 Pa), 3-methoxy-3-methyl-1-butyl acetate (boiling point 188°C, vapor pressure 53 Pa), propylene glycol diacetate (boiling point 190°C, vapor pressure 30 Pa), ethylene glycol monobutyl ether acetate (boiling point 192°C, vapor pressure 31 Pa), diethylene glycol monomethyl ether (boiling point 194°C, vapor pressure 27 Pa), dipropylene glycol methyl ether acetate (boiling point 213°C, vapor pressure 14 Pa), propylene glycol (boiling point 188°C, vapor pressure 11 Pa), ethylene glycol (boiling point 198°C, vapor pressure 7 Pa), and ethyl octanoate (boiling point 208°C, vapor pressure 3 Pa). Note that the present invention is not limited to these.

From the viewpoints of run-on property, suppression of surface defects, adhesion, and pattern shape, it is more preferable that the organic solvent (E1) has a boiling point of 180°C or more and 210°C or less, and a vapor pressure at 20°C of 10 Pa or more and less than 80 Pa.

The organic solvent (E1) preferably contains at least one selected from dipropylene glycol monomethyl ether, propylene glycol diacetate, and ethylene glycol monobutyl ether acetate, and more preferably contains propylene glycol diacetate.

The organic solvent (E1) can be used alone or in combination of two or more types.

The content of organic solvent (E1) is more preferably 0.5% by mass or more and less than 8% by mass in 100% by mass of organic solvent (E).

(Organic solvent (E2) having a boiling point of 160° C. or more and less than 180° C. and a vapor pressure at 20° C. of 100 Pa or more and less than 400 Pa)
The photosensitive coloring composition of the present invention contains, as the organic solvent (E), an organic solvent (E2) having a boiling point of 160° C. or more and less than 180° C. and a vapor pressure at 20° C. of 100 Pa or more and less than 400 Pa, in an amount of 10% by mass or more and 40% by mass or less, based on 100% by mass of the organic solvent (E).

Specific examples of the organic solvent (E2) include 3-methoxybutyl acetate (boiling point 171°C, vapor pressure 369 Pa), diethylene glycol dimethyl ether (boiling point 162°C, vapor pressure 330 Pa), diisobutyl ketone (boiling point 168°C, vapor pressure 230 Pa), diacetone alcohol (boiling point 167°C, vapor pressure 224 Pa), 3-ethoxyethyl propionate (boiling point 170°C, vapor pressure 200 Pa), and 3-methoxy-1-butanol (boiling point 161°C, vapor pressure 160 Pa). However, the present invention is not limited to these.

From the viewpoints of run-on property, suppression of surface defects, adhesion, and pattern shape, it is more preferable that the organic solvent (E2) has a boiling point of 160°C or more and less than 180°C, and a vapor pressure at 20°C of 100 Pa or more and 300 Pa or less.

The organic solvent (E2) preferably contains at least one selected from ethyl 3-ethoxypropionate and 3-methoxy-1-butanol.

The organic solvent (E2) can be used alone or in combination of two or more types.

The content of organic solvent (E2) is more preferably 15% by mass or more and 35% by mass or less in 100% by mass of organic solvent (E).

(Organic solvent (E3) having a boiling point of 120°C or more and less than 160°C and a vapor pressure of 400 Pa or more at 20°C)
The photosensitive coloring composition of the present invention contains, as the organic solvent (E), an organic solvent (E3) having a boiling point of 120° C. or more and less than 160° C. and a vapor pressure of 400 Pa or more at 20° C., in an amount of 55% by mass or more and 85% by mass or less, based on 100% by mass of the organic solvent (E).

The organic solvent (E3) is specifically cyclopentanone (boiling point 130°C, vapor pressure 1,380 Pa), butyl acetate (boiling point 126°C, vapor pressure 1,200 Pa), propylene glycol monomethyl ether (boiling point 121°C, vapor pressure 1,150 Pa), propylene glycol monoethyl ether (boiling point 132°C, vapor pressure 900 Pa), ethylene glycol monomethyl ether (boiling point 125°C, vapor pressure 830 Pa), amyl acetate (boiling point 14 2°C, vapor pressure 747 Pa), methyl 3-methoxypropionate (boiling point 142°C, vapor pressure 707 Pa), 1-methoxy-2-propanol (boiling point 120°C, vapor pressure 670 Pa), ethylene glycol monoethyl ether (boiling point 135°C, vapor pressure 500 Pa), propylene glycol monomethyl ether acetate (boiling point 145°C, vapor pressure 500 Pa), cyclohexanone (boiling point 156°C, vapor pressure 500 Pa), etc. However, the present invention is not limited to these.

The organic solvent (E3) preferably has a boiling point of 130°C or more and less than 160°C, and a vapor pressure at 20°C of 400 Pa or more and 800 Pa or less.

The organic solvent (E3) preferably contains at least one selected from cyclohexanone, propylene glycol monomethyl ether acetate, methyl 3-methoxypropionate, and ethylene glycol monoethyl ether.

The organic solvent (E3) can be used alone or in combination of two or more types.

The content of organic solvent (E3) is more preferably 60% by mass or more and 85% by mass or less in 100% by mass of organic solvent (E).

In the photosensitive coloring composition of the present invention, the mass ratio E1:E2:E3 of organic solvent (E1), organic solvent (E2), and organic solvent (E3) is preferably 0.5-8:15-30:60-85.

(Organic solvent (E4))
The photosensitive coloring composition of the present invention may contain, as the organic solvent (E), an organic solvent (E4) other than the organic solvent (E1), the organic solvent (E2), and the organic solvent (E3), as long as the problem can be solved.

Examples of organic solvents (E4) include n-propyl acetate, toluene, 3-methoxy-3-methyl-1-butanol, ethyl lactate, ethylene glycol monoethyl ether acetate, dipropylene glycol methyl-n-butyl ether, 1,4-butanediol diacetate, and 1,6-hexanediol diacetate.

The organic solvent (E4) can be used alone or in combination of two or more types.

The content of the organic solvent (E) is preferably 60% by mass or more and 90% by mass or less in 100% by mass of the photosensitive coloring composition.
The total amount of the organic solvents (E1), (E2), and (E3) is preferably 90% by mass or more in 100% by mass of the organic solvent (E).

[Dispersion resin (F)]
The photosensitive coloring composition of the present invention preferably contains a dispersion resin (F) from the viewpoint of riding up and suppressing surface defects. This suppresses a sudden increase in viscosity even when the organic solvent (E) evaporates and becomes highly non-volatile, and maintains fluidity. Therefore, it is presumed that the film spreads easily and rides up well. In addition, the dispersion resin (F) suppresses surface defects caused by aggregation of the colorant (A). In this specification, the dispersion resin (F) is not included in the binder resin (B).

The dispersing resin (F) is not particularly limited, and known resins can be used. Examples of the dispersing resin (F) include urethane resins, polycarboxylates such as polyacrylates, unsaturated polyamides, polycarboxylic acids, polycarboxylate (partial) amine salts, polycarboxylate ammonium salts, polycarboxylate alkylamine salts, polysiloxanes, long-chain polyaminoamide phosphates, hydroxyl-containing polycarboxylates, and modified products thereof, amides formed by the reaction of poly(lower alkylene imines) with polyesters having free carboxyl groups, and salts thereof, 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 alcohols, and polyvinylpyrrolidone, polyesters, modified polyacrylates, ethylene oxide/propylene oxide adducts, and phosphates.

The molecular structure of the dispersing resin (F) may be, for example, a random structure, a block structure, a graft structure, a comb structure, or a star structure. Among these, the block structure or the comb structure is preferred from the viewpoint of dispersion stability.

Dispersion resin (F) can be used alone or in combination of two or more types.

From the viewpoint of ride-on properties and suppression of surface defects, the content of the dispersion resin (F) is preferably 3 parts by mass or more and 200 parts by mass or less, and more preferably 5 parts by mass or more and 100 parts by mass or less, per 100 parts by mass of the colorant (A).

(Dispersion resin having an acidic group (F1))
From the viewpoint of riding property and developability, the photosensitive coloring composition of the present invention more preferably contains a dispersion resin (F1) having an acidic group as the dispersion resin (F). In this specification, the dispersion resin (F1) having an acidic group refers to a dispersion resin in which the amount of acidic groups is greater than the amount of basic groups.

Examples of acidic groups include carboxyl groups, phosphate groups, and sulfonic acid groups. Among these, carboxyl groups and phosphate groups are preferred, and carboxyl groups are more preferred.

The dispersing resin (F1) having an acidic group is not particularly limited, and known resins can be used. Examples include polycarboxylates such as polyacrylates, polycarboxylates, (meth)acrylic acid-styrene copolymers, (meth)acrylic acid-(meth)acrylic acid ester copolymers, styrene-maleic acid ester copolymers, and phosphoric acid esters. Other examples include resins described in JP 2007-23195 A, WO 2008/007776 A, JP 2008-029901 A, JP 2009-155406 A, JP 2009-251481 A, JP 2010-185934 A, and JP 2011-157416 A.

Commercially available dispersing resins (F1) having acidic groups include, for example, Disperbyk-101, 102, 103, 106, 110, 111, 118, 170, 171, 174, 2096, BYK-P104, BYK-P105, BYK-220S manufactured by BYK Japan, and SOLSPERSE-3000, 21000, 26000, 36600, 41000, 41090, 43000, 45000, 53095 manufactured by Lubrizol Japan.

From the viewpoint of ride-on ability, the dispersing resin (F1) having an acidic group preferably contains a resin having a main chain based on an aromatic carboxylic acid ester moiety having an ester bond, which is a reaction product site of an aromatic compound having two or more acid anhydride groups and a compound having two or more hydroxyl groups, and a side chain based on a vinyl polymer moiety.

The aromatic carboxylic acid ester moiety in the main chain is obtained by a ring-opening reaction between an aromatic compound having two or more acid anhydride groups and a compound having two or more hydroxyl groups, and an aromatic carboxylic acid is generated at the same time as the ester bond is generated. The aromatic carboxylic acid acts as an adsorption site for the colorant (A). An aromatic carboxylic acid is a structure in which a carboxyl group and an aromatic ring are directly bonded.

The vinyl polymer moiety in the side chain acts as a steric repulsion moiety and suppresses the association and aggregation of the colorant (A). The vinyl polymer moiety in the side chain can be obtained, for example, by the following two methods.
The first method is a method of copolymerizing an ethylenically unsaturated monomer in the presence of a compound having two or more hydroxyl groups. The compound having two or more hydroxyl groups is preferably a compound having two hydroxyl groups and one thiol group in the molecule.
The second method is a method in which an ethylenically unsaturated monomer is copolymerized in the presence of a reaction product between an aromatic compound having two or more acid anhydride groups and a hydroxyl group of a compound having two or more hydroxyl groups.
The difference between the above two methods is whether the vinyl polymer moiety obtained by copolymerizing an ethylenically unsaturated monomer is introduced first or later. The molecular weight and other properties may differ slightly depending on various conditions, but in theory, the same product can be produced if the raw materials and reaction conditions are the same.

The main chain and side chains are explained in detail below.

[Main Chain]
The aromatic carboxylate moiety is obtained by a ring-opening reaction between an anhydride group of an aromatic compound having two or more acid anhydride groups and a compound having two or more hydroxyl groups.

Examples of aromatic compounds having two or more acid anhydride groups include compounds represented by the following general formula (3) and the following general formula (4).

In formula (3), n represents 1 or 2.
In general formula (4), Q represents a direct bond, —O—, —CO—, —COOCH ₂ CH ₂ OCO—, —SO ₂ —, —C(CF ₃ ) ₂ —, a group represented by the following general formula (5), or a group represented by the following general formula (6).

Specific examples of aromatic compounds having two or more acid anhydride groups include pyromellitic dianhydride, ethylene glycol ditrimellitic anhydride ester, propylene glycol ditrimellitic anhydride ester, butylene glycol ditrimellitic anhydride ester, 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, tetracarboxylic dianhydride, 3,3',4,4'-biphenyl ether tetracarboxylic dianhydride, 3,3',4,4'-dimethyldiphenylsilane 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 Anhydride, 4,4'-bis(3,4-dicarboxyphenoxy)diphenylpropane dianhydride, 3,3',4,4'-perfluoroisopropylidenediphthalic dianhydride, 3,3',4,4'-biphenyltetracarboxylic dianhydride, bis(phthalic acid)phenylphosphine oxide dianhydride, p-phenylene-bis(triphenylphthalic acid) dianhydride, m-phenylene-bis(triphenylphthalic acid) dianhydride, bis(triphenylphthalic acid)-4,4'-diphenyl ether tert-butyl phthalate dianhydride, bis(triphenylphthalic acid)-4,4'-diphenylmethane 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 dianhydride, or 3,4-dicarboxy-1,2,3,4-tetrahydro-6-methyl-1-naphthalene succinic dianhydride. Among these, aromatic tetracarboxylic acid dianhydrides are preferred, and pyromellitic dianhydride is more preferred.

As described above, compounds having two or more hydroxyl groups are preferably compounds having two hydroxyl groups and one thiol group in the molecule.

Examples of compounds having two hydroxyl groups and one thiol group in the molecule include 1-mercapto-1,1-methanediol, 1-mercapto-1,1-ethanediol, 3-mercapto-1,2-propanediol (thioglycerin), 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.

The aromatic carboxylate moiety is preferably a reaction product of 0.9 to 1.5 moles of an aromatic compound having two or more acid anhydride groups per mole of a compound having two or more hydroxyl groups. In theory, when the amount of an aromatic compound having two or more acid anhydride groups exceeds one mole, the terminal becomes an acid anhydride group.

In addition, the acid anhydride group present at the end of the aromatic carboxylic acid ester moiety may be reacted with a monoalcohol from the viewpoint of developability. That is, the acid anhydride group undergoes ring-opening with the monoalcohol to generate an alcohol ester and a carboxyl group. This improves the solubility in the developer and improves the developability.

Examples of the monoalcohol include monoalcohols such as methanol, ethanol, 1-butanol, 2-butanol, isobutanol, t-butanol, 1-pentanol, isopentyl alcohol, tert-pentyl alcohol, cyclopentanol, 1-hexanol, cyclohexanol, 1-heptanol, 1-octanol, 2-ethyl-1-hexanol, isononyl alcohol, 1-nonyl alcohol, amyl alcohol, lauryl alcohol, n-butyl alcohol, isobutyl alcohol, cyclohexanol, benzyl alcohol, and methylcyclohexanol;
Monoalcohols having an ether group, such as 3-methoxy-3-methyl-1-butanol, 3-methoxybutanol, ethylene glycol monoisopropyl ether, ethylene glycol monoethyl ether, ethylene glycol monotertiary butyl ether, ethylene glycol monobutyl ether, ethylene glycol monopropyl ether, ethylene glycol monohexyl ether, ethylene glycol monomethyl ether, diethylene glycol monoisopropyl ether, diethylene glycol monobutyl ether, diethylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol monobutyl ether, dipropylene glycol monopropyl ether, dipropylene glycol monomethyl ether, tripropylene glycol monobutyl ether, tripropylene glycol monomethyl ether, propylene glycol monophenyl ether, propylene glycol monoethyl ether, propylene glycol monobutyl ether, propylene glycol monopropyl ether, and propylene glycol monomethyl ether;
Examples of the lactate include monoalcohols having a carbonyl group, such as methyl lactate, ethyl lactate, and diacetone alcohol.
Among these, from the viewpoint of developability, compounds having an ether group or a carbonyl group are preferred, and 3-methoxybutanol, propylene glycol monomethyl ether, and diacetone alcohol are more preferred.
The monoalcohols may be used alone or in combination of two or more.

The amount of monoalcohol used relative to the acid anhydride group is preferably 1 to 30 equivalents, more preferably 1.5 to 20 equivalents, relative to 1 equivalent of the acid anhydride group in the main chain.

[Side Chain]
As described above, the vinyl polymer segment can be obtained by a method of copolymerizing an ethylenically unsaturated monomer (hereinafter also simply referred to as a monomer) in the presence of a compound having two or more hydroxyl groups, or a method of copolymerizing a monomer in the presence of a reaction product between an aromatic compound having two or more acid anhydride groups and hydroxyl groups of a compound having two or more hydroxyl groups.

Examples of the monomer include methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, isopropyl (meth)acrylate, butyl (meth)acrylate, isobutyl (meth)acrylate, 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, and the like. ) acrylate, tridecyl (meth)acrylate, isomyristyl (meth)acrylate, stearyl (meth)acrylate, or isostearyl (meth)acrylate, methoxyethyl (meth)acrylate, methoxypolyethylene glycol (meth)acrylate, methoxypolypropylene glycol (meth)acrylate, methoxypolytetramethylene glycol (meth)acrylate, or methoxypolyethylene glycol polypropylene glycol (meth)acrylate, or other linear or branched alkyl (meth)acrylates;
cyclic alkyl (meth)acrylates such as cyclohexyl (meth)acrylate, tertiary butyl cyclohexyl (meth)acrylate, dicyclopentanyl (meth)acrylate, dicyclopentanyloxyethyl (meth)acrylate, dicyclopentenyl (meth)acrylate, dicyclopentenyloxyethyl (meth)acrylate, or isobornyl (meth)acrylate;
Fluoroalkyl (meth)acrylates such as trifluoroethyl (meth)acrylate, octafluoropentyl (meth)acrylate, perfluorooctylethyl (meth)acrylate, or tetrafluoropropyl (meth)acrylate;
(Meth)acryloxy-modified polydimethylsiloxanes (silicone macromers);
(meth)acrylates having a heterocycle, such as tetrahydrofurfuryl (meth)acrylate or 3-methyl-3-oxetanyl (meth)acrylate;
(meth)acrylates having an aromatic ring, such as benzyl (meth)acrylate, phenoxyethyl (meth)acrylate, phenoxypolyethylene glycol (meth)acrylate, paracumylphenoxyethyl (meth)acrylate, paracumylphenoxypolyethylene glycol (meth)acrylate, and nonylphenoxypolyethylene glycol (meth)acrylate;
(meth)acrylates having a carboxyl group, such as (meth)acrylic acid, acrylic acid dimer, 2-(meth)acryloyloxyethyl phthalate, 2-(meth)acryloyloxypropyl phthalate, 2-(meth)acryloyloxyethyl hexahydrophthalate, 2-(meth)acryloyloxypropyl hexahydrophthalate, ethylene oxide-modified succinic acid (meth)acrylate, β-carboxyethyl (meth)acrylate, and ω-carboxypolycaprolactone (meth)acrylate;
Vinyl such as styrene, α-methylstyrene, vinyl acetate, vinyl (meth)acrylate, or allyl (meth)acrylate;
N-substituted (meth)acrylamide, N,N-dimethyl(meth)acrylamide, N,N-diethyl(meth)acrylamide, N-isopropyl(meth)acrylamide, diacetone(meth)acrylamide, or acryloylmorpholine;
Amino group-containing (meth)acrylates such as N,N-dimethylaminoethyl (meth)acrylate and N,N-diethylaminoethyl (meth)acrylate;
Nitriles such as (meth)acrylonitrile;
styrenes such as styrene and α-methylstyrene, and vinyl ethers such as ethyl vinyl ether, n-propyl vinyl ether, isopropyl vinyl ether, n-butyl vinyl ether, and isobutyl vinyl ether;
vinyl acetate, vinyl propionate, and other vinyl fatty acids;
Examples of the monomer include acidic group-containing monomers such as acrylic acid, methacrylic acid, itaconic acid, maleic acid, fumaric acid, and crotonic acid.

The vinyl polymer moiety also preferably has a thermosetting group and/or a polymerizable unsaturated group. Examples of the thermosetting group include a hydroxyl group, an epoxy group, an oxetanyl group, a tert-butyl group, and a blocked isocyanate group.
A thermosetting group can be introduced by using a monomer having a hydroxyl group, an epoxy group, an oxetanyl group, a tert-butyl group, a blocked isocyanate group, or the like.
The polymerizable unsaturated group can be introduced, for example, by reacting a hydroxyl group present in the vinyl polymer moiety with an isocyanate group of a monomer having an isocyanate group.

For example, the synthesis method involves radically polymerizing a monomer in the presence of compound (a), which is a compound having two or more hydroxyl groups and has two hydroxyl groups and one thiol group at one end, to produce a vinyl polymer having two hydroxyl groups at one end, and reacting this with tetracarboxylic dianhydride (b), which is an aromatic compound having two or more acid anhydride groups. Furthermore, if the reactant has an acid anhydride group at its end, it can be reacted with a monoalcohol to introduce a blocking site derived from the monoalcohol.

In (c), X is the reaction residue after the tetracarboxylic dianhydride (b) reacts with a hydroxyl group, Z is the reaction residue after a compound having two hydroxyl groups reacts with an acid anhydride group, and R is a residue of a monoalcohol.

The polymerization temperature of the vinyl polymer portion is preferably 40 to 150°C, more preferably 50 to 110°C. If it is 40°C or higher, the polymerization proceeds easily, and if it is 150°C or lower, it is easy to control the molecular weight.

When polymerizing the vinyl polymer portion, 0.001 to 5% by mass of a polymerization initiator can be used based on the total monomer mass of the monomers. Examples of polymerization initiators include azo compounds and organic peroxides.

Examples of the azo compound include 2,2'-azobisisobutyronitrile, 2,2'-azobis(2-methylbutyronitrile), 1,1'-azobis(cyclohexane-1-carbonitrile), 2,2'-azobis(2,4-dimethylvaleronitrile), 2,2'-azobis(2,4-dimethyl-4-methoxyvaleronitrile), dimethyl 2,2'-azobis(2-methylpropionate), 4,4'-azobis(4-cyanovaleric acid), 2,2'-azobis(2-hydroxymethylpropionitrile), and 2,2'-azobis[2-(2-imidazolin-2-yl)propane].
Examples of organic peroxides include benzoyl peroxide, tert-butyl perbenzoate, cumene hydroperoxide, diisopropyl peroxydicarbonate, di-n-propyl peroxydicarbonate, di(2-ethoxyethyl)peroxydicarbonate, t-butyl peroxyneodecanoate, t-butyl peroxypivalate, (3,5,5-trimethylhexanoyl)peroxide, dipropionyl peroxide, diacetyl peroxide, etc. These polymerization initiators can be used alone or in combination of two or more kinds.

The synthesis of the vinyl polymer portion is preferably carried out by bulk polymerization or solution polymerization. Examples of polymerization solvents for solution polymerization include, but are not limited to, ethyl acetate, n-butyl acetate, isobutyl acetate, toluene, xylene, acetone, hexane, methyl ethyl ketone, cyclohexanone, propylene glycol monomethyl ether acetate, dipropylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, ethylene glycol monobutyl ether acetate, diethylene glycol monoethyl ether acetate, and diethylene glycol monobutyl ether acetate. These polymerization solvents can be used alone or in combination of two or more.

A reaction catalyst can be used to synthesize the aromatic carboxylic acid ester moiety. The reaction catalyst is preferably a tertiary amine compound. Examples of tertiary amine compounds include triethylamine, triethylenediamine, N,N-dimethylbenzylamine, N-methylmorpholine, 1,8-diazabicyclo-[5.4.0]-7-undecene, and 1,5-diazabicyclo-[4.3.0]-5-nonene.

Solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, ethyl acetate, butyl acetate, toluene, xylene, acetonitrile, and propylene glycol monomethyl ether acetate can be used to synthesize the aromatic carboxylate moiety.

The synthesis temperature for the aromatic carboxylate moiety is preferably 50 to 180°C, more preferably 80 to 140°C.

The weight average molecular weight of the dispersing resin (F1) having an acidic group is preferably 2,000 to 40,000, and more preferably 4,000 to 30,000.

The acid value of the dispersing resin (F1) having an acidic group is preferably 20 to 250 mg KOH/g, and more preferably 30 to 200 mg KOH/g.

Dispersion resins (F1) having acidic groups can be used alone or in combination of two or more types.

(Dispersion resin having basic group (F2))
The photosensitive coloring composition of the present invention can contain a dispersion resin (F2) having a basic group as the dispersion resin (F). In this specification, the dispersion resin (F2) having a basic group refers to a dispersion resin in which the amount of basic groups is greater than the amount of acidic groups.

Examples of basic groups include primary amino groups, secondary amino groups, tertiary amino groups, quaternary ammonium bases, and groups containing nitrogen atoms such as nitrogen-containing heterocycles.

The dispersion resin (F2) having a basic group is not particularly limited, and known resins can be used. For example, salts of long-chain polyaminoamides and high molecular weight acid esters, polyester polyamines, amine salts of copolymers of unsaturated carboxylic acids such as polyacrylic acid, polyethyleneimine compounds, etc. may be mentioned. Other examples include resins described in JP 2013-119568 A, JP 2018-203795 A, JP 2019-089953 A, JP 2019-089954 A, WO 2020/031634 A, etc.

Commercially available dispersion resins having basic groups (F2) include Disperbyk-108, 109, 161, 162, 164, 167, 168, 182, 184, 185, 2000, 2008, 2013, 2022, 2050, 2055, 2150, 2155, 2163, BYK-LPN6919, 21116 manufactured by BYK Japan, and SOL manufactured by Lubrizol Japan. Examples include SPERSE-9000, 13240, 13650, 13940, 17000, 18000, 24000SC, 24000GR, 28000, 31845, 32000, 32500, 34750, 35100, 35200, 36600, 38500, and Ajisper PA111, PB711, PB821, PB822, PB824 manufactured by Ajinomoto Fine-Techno Co., Ltd.

The structure of the dispersion resin (F2) having a basic group may be, for example, a random structure, a block structure, a graft structure, a comb structure, a star structure, etc. Among these, the block structure is preferred from the viewpoint of storage stability.

The amine value of the dispersion resin (F2) having a basic group is preferably 20 to 250 mg KOH/g, and more preferably 30 to 150 mg KOH/g.

The weight average molecular weight of the dispersion resin (F2) having a basic group is preferably 2,000 to 60,000, and more preferably 4,000 to 50,000.

The dispersion resin (F2) having a basic group can be used alone or in combination of two or more types.

[Dye derivative (G)]
The photosensitive coloring composition of the present invention may contain a dye derivative (G).

The dye derivative (G) is not particularly limited, and examples thereof include dye derivatives having an acidic group, a basic group, a neutral group, etc. in the organic dye residue. Examples of the dye derivative (G) include compounds having an acidic substituent such as a sulfo group, a carboxy group, or a phosphate group, and amine salts thereof, compounds having a basic substituent such as a sulfonamide group or a tertiary amino group at the terminal, and compounds having a neutral substituent such as a phenyl group or a phthalimidoalkyl group.
Examples of organic pigments include diketopyrrolopyrrole pigments, anthraquinone pigments, quinacridone pigments, dioxazine pigments, perinone pigments, perylene pigments, thiazine indigo pigments, triazine pigments, benzimidazolone pigments, indole pigments such as benzoisoindole, isoindoline pigments, isoindolinone pigments, quinophthalone pigments, naphthol pigments, threne pigments, metal complex pigments, and azo pigments such as azo, disazo, and polyazo.

When the solubility in the polymerizable compound (C), organic solvent (E), etc. is low, the dye derivative (G) is preferably added during the micronization of the colorant (A) described above, or during the dispersion treatment of the colorant (A) described below. The average primary particle size of the dye derivative (G) is preferably 5 to 200 nm.

The dye derivative (G) can be used alone or in combination of two or more types.

The content of the dye derivative (G) is preferably 1 part by mass or more and 40 parts by mass or less, and more preferably 2 parts by mass or more and 20 parts by mass or less, per 100 parts by mass of the colorant (A).

[Sensitizer (H)]
The photosensitive coloring composition of the present invention can contain a sensitizer (H).

Examples of the sensitizer (H) include polymethine dyes such as 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, acridine derivatives, azine derivatives, thiazine derivatives, oxazine derivatives, indoline derivatives, azulene derivatives, azulenium derivatives, squarylium derivatives, porphyrin derivatives, tetraphenylporphyrin derivatives, triarylmethane derivatives, tetrabenzoporphyrin derivatives, tetrapyrazinoporphyrin derivatives, and the like. Examples of such compounds include aryl 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, or 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 (H), thioxanthone derivatives, Michler's ketone derivatives, and carbazole derivatives are preferred. Specific compounds that are preferred are 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.

The sensitizer (H) can be used alone or in combination of two or more types.

The content of the sensitizer (H) is preferably 3 parts by mass or more and 60 parts by mass or less, and more preferably 5 parts by mass or more and 50 parts by mass or less, per 100 parts by mass of the polymerization initiator (D).

[Thermosetting compound (I)]
The photosensitive coloring composition of the present invention can contain a thermosetting compound (I).

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 (I) include epoxy compounds, oxetane compounds, benzoguanamine compounds, rosin-modified maleic acid compounds, rosin-modified fumaric acid compounds, melamine compounds, urea compounds, and phenol compounds. Among these, epoxy compounds and oxetane compounds are preferred.

(Epoxy Compound)
Examples of the epoxy compound 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, 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, bischloromethylbiphenyl, 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.

Specific examples of epoxy compounds include 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, 3,4-epoxy-1-methylcyclohexyl-3,4-epoxy-1-methylhexanecarboxylate, 6-methyl-3,4-epoxycyclohexylmethyl-6-methyl-3,4-epoxycyclohexanecarboxylate, 3,4-epoxy-3-methylcyclohexylmethyl-3,4-epoxy-3-methylcyclohexanecarboxylate, 3,4-epoxy-5-methylcyclohexylmethyl-3,4-epoxy-5-methylcyclohexanecarboxylate, 2-(3,4-epoxycyclohexyl-5,5-spiro-3,4-epoxy)cyclohexane-metadioxane, bis(3,4-epoxycyclohexyl)methyl-3,4-epoxy ... Epoxycyclohexylmethyl) adipate, 3,4-epoxy-6-methylcyclohexyl carboxylate, methylene bis(3,4-epoxycyclohexane), dicyclopentadiene diepoxide, ethylene bis(3,4-epoxycyclohexane carboxylate), dioctyl epoxyhexahydrophthalate, di-2-ethylhexyl epoxyhexahydrophthalate, 1-epoxyethyl-3,4-epoxycyclohexane, 1,2-epoxy-2-epoxyethylcyclohexane, butanetetracarboxylate tetra(3,4-epoxycyclohexylmethyl) modified ε-caprolactone, 2,2-bis(hydroxymethyl)-1-butanol 1,2-epoxy-4-(2-oxiranyl)cyclohexane adduct, etc.

Commercially available epoxy compounds include, for example, Epicoat 807, 815, 825, 827, 828, 190P, and 191P manufactured by Yuka Shell Epoxy Co., Ltd., and TECHMORE manufactured by Mitsui Chemicals, Inc. VG3101L, EPPN-201, 501H, 502H, EOCN-102S, 103S, 104S, 1020 manufactured by Nippon Kayaku Co., Ltd., Epicoat 1004, 1256, JER1032H60, 157S65, 157S70, 152, 154 manufactured by Japan Epoxy Resins Co., Ltd., Celoxide 2021, EHPE-3150 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 manufactured by Nagase ChemteX Corporation, TEPIC-L, H, S manufactured by Nissan Chemical Industries, Ltd., EPICLON manufactured by DIC Corporation 830, 840, 850, 860, 1050, 3050, 4050, N-660, N-670, N-740, N-770, N865, HP-7200, HP-4700, HP-4770, HP-5000, HP-6000, HP-9500, etc.

From the viewpoint of film resistance, the epoxy compound is preferably a compound having 2 to 50 epoxy groups in the molecule, and more preferably a compound having 10 to 30 epoxy groups.

The epoxy equivalent of the epoxy compound is preferably 50 to 400 g/eq, and more preferably 100 to 200 g/eq. The epoxy equivalent is defined as the mass of the epoxy compound containing one equivalent of epoxy groups.

The epoxy compound preferably contains a compound represented by the following general formula (7):

General formula (7)

In general formula (7), R represents a group obtained by removing m hydroxyl groups from an m-hydric alcohol, where m is an integer from 1 to 6 and n is an integer from 1 to 30.

R represents a group obtained by removing m hydroxyl groups from an m-hydric alcohol.
The group obtained by removing m hydroxyl groups from an m-hydric alcohol is preferably an alkyl group having 2 to 20 carbon atoms, which may be linear, branched, or cyclic, or a combination of these. Examples of the alkyl group having 2 to 20 carbon atoms include an ethyl group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a 2,2-dimethylpropyl group, a butyl group, an isobutyl group, a tert-butyl group, a 3,3-dimethylbutyl group, a pentyl group, an isopentyl group, a hexyl group, a heptyl group, an octyl group, an isooctyl group, a 2-ethylhexyl group, a nonyl group, an isononyl group, a decyl group, an isodecyl group, an undecyl group, a dodecyl group, a hexadecyl group, a cyclopentyl group, a cyclopentylmethyl group, a cyclohexyl group, a cyclohexylmethyl group, and a cyclohexylmethyl group. Among these, a branched alkyl group having 3 to 12 carbon atoms is more preferable.

m represents an integer of 1 to 6, and n represents an integer of 1 to 30.
When m is 2 or more, n in each group in parentheses in formula (7) may be the same or different.

Specific examples of the compound represented by general formula (7) include 1,2-epoxy-4-(2-oxiranyl)cyclohexane adducts of 2,2-bis(hydroxymethyl)-1-butanol. Commercially available products include EHPE-3150 and EHPE-3150CE manufactured by Daicel Corporation.

Epoxy compounds can be used alone or in combination of two or more types.

The content of the epoxy compound is preferably 0.5% by mass or more and 50% by mass or less, and more preferably 1% by mass or more and 40% by mass or less, based on 100% by mass of the non-volatile content of the photosensitive coloring composition.

(Oxetane Compounds)
The oxetane compound is a known compound having an oxetane group. Examples of the oxetane compound include monofunctional oxetane compounds, bifunctional oxetane compounds, and trifunctional or higher oxetane compounds.

Examples of monofunctional oxetane compounds 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.

Examples of bifunctional oxetane compounds 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, di[1-ethyl(3-oxetanyl)]methyl ether 3-ethyl-3-hydroxymethyl oxetane, 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 glycol bis(3-ethyl-3-oxetanylmethyl)ether, dicyclopentenyl 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 bis(3-ethyl-3-oxetanylmethyl) ether, Examples include 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, etc.

Examples of trifunctional or higher oxetane compounds 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, ethyl) ether, caprolactone-modified dipentaerythritol hexa(3-ethyl-3-oxetanylmethyl) ether, caprolactone-modified dipentaerythritol pentakis(3-ethyl-3-oxetanylmethyl) ether, ditrimethylolpropane tetrakis(3-ethyl-3-oxetanylmethyl) ether, and resins containing oxetane groups (such as the oxetane-modified phenol novolac resin described in Japanese Patent No. 3783462).

Commercially available oxetane compounds include, for example, OXBP and OXTP manufactured by Ube Industries, OXE-10 and 30 manufactured by Osaka Organic Chemical Industry Co., Ltd., and OXT-101 and 212 manufactured by Toagosei Co., Ltd.

Oxetane compounds can be used alone or in combination of two or more types.

The content of the oxetane compound is preferably 0.5% by mass or more and 50% by mass or less, and more preferably 1% by mass or more and 40% by mass or less, based on 100% by mass of the nonvolatile content of the photosensitive coloring composition.

A melamine compound is a compound having a melamine ring structure. The melamine compound is preferably a methylol type or ether type compound, and more preferably a melamine compound having an average of 5.0 or more methylol groups and/or ether groups per melamine ring. Having an appropriate number of methylol groups or ether groups makes it easier to obtain just the right amount of heat resistance.

Commercially available melamine compounds 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.

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., which have an average of 5.0 or more methylol groups and/or ether groups per melamine ring, are preferred in terms of increasing crosslink density.

The melamine compounds can be used alone or in combination of two or more types.

The content of the melamine compound is preferably 0.01% by mass or more and 10% by mass or less, and more preferably 0.1% by mass or more and 5% by mass or less, based on 100% by mass of the non-volatile content of the photosensitive coloring composition.

The thermosetting compound (I) may be used alone or in combination of two or more types.

[Curing agent (curing accelerator)]
The photosensitive coloring composition of the present invention may contain a curing agent (curing accelerator) to assist the curing of the thermosetting compound (I).

Examples of the curing agent include amine compounds, acid anhydrides, active esters, carboxylic acid compounds, and sulfonic acid compounds. Examples of the curing agent include 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-methyl ... -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.).

The hardeners can be used alone or in combination of two or more types.

The content of the curing agent is preferably 0.01 parts by mass or more and 15 parts by mass or less per 100 parts by mass of the thermosetting compound (I).

[Thiol-based chain transfer agent (J)]
The photosensitive coloring composition of the present invention may contain a thiol-based chain transfer agent (J).

When used in combination with a polymerization initiator (D), a thiol chain transfer agent (J) generates thiyl radicals that are not easily inhibited by oxygen during radical polymerization after light irradiation, accelerating photocuring.

Examples of the thiol-based chain transfer agent (J) include monofunctional thiol compounds such as thiophenol, 2-mercaptobenzothiazole, 2-mercaptobenzimidazole, 2-mercaptobenzoxazole, 2-mercapto-5-methoxybenzothiazole, 2-mercapto-5-benzimidazole, butanethiol, octanethiol, 1-dodecanethiol, methyl 3-mercaptopropionate, ethyl 3-mercaptopropionate, octyl 3-mercaptopropionate, and 2-ethylhexyl 3-mercaptopropionate;
Monofunctional thiol compounds having a hydroxyl group or an acidic group, such as 2-mercaptoethanol, 1-thioglycerol, thioglycolic acid, 2-mercaptobenzoic acid, 3-mercaptobenzoic acid, 4-mercaptonicotinic acid, 2-mercaptopropionic acid, 3-mercaptopropionic acid, 4-mercaptobutanoic acid, octyl thioglycolate, mercaptosuccinic acid, 11-mercaptoundecanoic acid, and 2-mercaptoethanesulfonic acid;
Examples of polyfunctional thiol compounds 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 tetrakis thioglycolate, pentaerythritol tetrakis(3-mercaptopropionate), trimercaptopropionic acid tris(2-hydroxyethyl)isocyanurate, 1,4-dimethylmercaptobenzene, 2,4,6-trimercapto-s-triazine, and 2-(N,N-dibutylamino)-4,6-dimercapto-s-triazine.

The thiol chain transfer agent (J) can be used alone or in combination of two or more types.

The content of the thiol chain transfer agent (J) is preferably 0.5% by mass or more and 10% by mass or less, and more preferably 1% by mass or more and 8% by mass or less, based on 100% by mass of the nonvolatile content of the photosensitive coloring composition.

[Polymerization inhibitor (K)]
The photosensitive coloring composition of the present invention may contain a polymerization inhibitor (K).

The polymerization inhibitor (K) is, for example, an alkyl catechol compound 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, or 3,5-di-t-butyl catechol; 2-methyl resorcinol, 4-methyl resorcinol, 2-ethyl resorcinol, 4-ethyl resorcinol, 2-propyl resorcinol, 4-propyl resorcinol, or 2-n- Examples of such compounds 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 polymerization inhibitor (K) can be used alone or in combination of two or more types.

The content of the polymerization inhibitor (K) is preferably 0.01% by mass or more and 0.4% by mass or less based on 100% by mass of the non-volatile content of the photosensitive coloring composition.

[Ultraviolet absorber (L)]
The photosensitive coloring composition of the present invention may contain an ultraviolet absorber (L).

The ultraviolet absorber (L) is an organic compound having an ultraviolet absorbing function, and examples of such compounds 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.

Benzotriazole compounds include, for example, 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-methylethene, Mixture of methyl acetate and 95% benzenepropanoic acid, 3-(2H-benzotriazol-2-yl)-(1,1-dimethylethyl)-4-hydroxy, C7-9 side and straight chain alkyl esters, 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-tert-butyl-4-hydroxy-5-(5-chloro-2H-benzotriazol-2-yl)phenyl]propionate, and 2-ethylhexyl-3-[3-tert-butyl-4-hydroxy-5-(5-chloro-2H-benzotriazol-2-yl)phenyl]propionate.

Commercially available products include, for example, TINUVIN P, PS, 234, 326, 329, 384-2, 900, 928, 99-2, and 1130 manufactured by BASF Japan, ADK STAB LA-29, LA-31RG, LA-32, and LA-36 manufactured by ADEKA, KEMISORB 71, 73, 74, 79, and 279 manufactured by Chemipro Chemicals, and RUVA-93 manufactured by Otsuka Chemical.

Examples of triazine 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 product of 2-(2,4-dihydroxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine and (2-ethylhexyl)-glycidic acid ester. Examples of such compounds include 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, and 2,4,6-tris(2-hydroxy-4-hexyloxy-3-methylphenyl)-1,3,5-triazine.

Commercially available products include, for example, KEMISORB 102 manufactured by Chemipro Chemicals, TINUVIN 400, 405, 460, 477, 479, and 1577ED manufactured by BASF Japan, Adeka STAB LA-46 and LA-F70 manufactured by ADEKA, and CYASORB UV-1164 manufactured by Sun Chemical.

Examples of benzophenone compounds include 2,4-dihydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxybenzophenone 5-sulfonic acid-3-water, 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.

Commercially available products include, for example, KEMISORB10, 11, 11S, 12, and 111 manufactured by Chemipro Chemicals, SEESORB101 and 107 manufactured by Shipro Chemicals, Adeka STAB 1413 manufactured by ADEKA, and UV-12 manufactured by Sun Chemical.

Examples of salicylic acid ester compounds include phenyl salicylate, p-octylphenyl salicylate, and p-tert-butylphenyl salicylate.

The ultraviolet absorber (L) can be used alone or in combination of two or more types.

The content of the ultraviolet absorber (L) is preferably 0.1% by mass or more and 5% by mass or less based on 100% by mass of the nonvolatile content of the photosensitive composition.

[Antioxidant (M)]
The photosensitive coloring composition of the present invention may contain an antioxidant (M).

Examples of the antioxidant (M) include hindered phenol-based, hindered amine-based, phosphorus-based, sulfur-based, and hydroxylamine-based compounds. In the present invention, the antioxidant is preferably a compound that does not contain a halogen atom.

Among these, hindered phenol-based antioxidants, hindered amine-based antioxidants, phosphorus-based antioxidants, and sulfur-based antioxidants are preferred.

Examples of 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.

Commercially available products include, for example, 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 Japan, and Cyanox CY-1790 and CY-2777 manufactured by Sun Chemical Co., Ltd.

Examples of 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 esters, 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.

Examples of commercially available products include Adeka 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, Tinuvin 111FDL, 123, 144, 249, 292, and 5100 manufactured by BASF Japan, and Cyasorb UV-3346, UV-3529, and UV-3853 manufactured by Sun Chemical.

Examples of 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'-isopropylidene 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 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.

Commercially available products include, for example, Adeka STAB PEP-36, PEP-8, HP-10, 2112, 1178, 1500, C, 135A, 3010, and TPP manufactured by ADEKA CORPORATION, IRGAFOS168 manufactured by BASF Japan, and Hostanox P-EPQ manufactured by Clariant Chemicals.

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.

Commercially available products include, for example, Adeka STAB AO-412S and AO-503 manufactured by ADEKA CORPORATION, and KEMINOX PLS manufactured by Chemipro Chemicals Co., Ltd.

The antioxidant (M) can be used alone or in combination of two or more types.

The content of the antioxidant (M) is preferably 0.5% by mass or more and 5% by mass or less based on 100% by mass of the non-volatile content of the photosensitive coloring composition.

[Leveling agent (N)]
The photosensitive coloring composition of the present invention can contain a leveling agent (N).

Examples of the leveling agent (N) include silicon-based surfactants, fluorine-based surfactants, nonionic surfactants, cationic surfactants, anionic surfactants, and amphoteric surfactants.

Examples of 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.

Commercially available products include, for example, BYK-300, 306, 310, 313, 315N, 320, 322, 323, 330, 331, 333, 342, 345, 346, 347, 348, 349, 370, 377, 378, 3455, UV3510, and 3570 manufactured by BYK-Chemie, and FZ-7002 and 2110 manufactured by Dow Corning Toray. , 2122, 2123, 2191, 5609, and 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.

Fluorine-based surfactants include, for example, surfactants or leveling agents that have a fluorocarbon chain.

Examples of commercially available products include Surflon S-242, 243, 420, 611, 651, and 386 manufactured by AGC Seimi Chemical Co., Ltd., Megafac F-253, 477, 551, 552, 555, 558, 560, 570, 575, and 576, R-40-LM, R-41, RS-72-K, and DS-21 manufactured by DIC Corporation, FC-4430 and 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.

Examples of 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, and sorbitan tristearate. late, 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.

Commercially available products include, for example, 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, and 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, PD-450, 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, C Examples include H-60(K), Amit 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, and (meth)acrylic acid-based (co)polymer Polyflow No. 75, No. 90, No. 95 manufactured by Kyoeisha Chemical Co., Ltd.

Examples of cationic surfactants include alkylamine salts, alkyl quaternary ammonium salts such as lauryl trimethyl ammonium chloride, stearyl trimethyl ammonium chloride, and cetyl trimethyl ammonium chloride, and ethylene oxide adducts of these.

Commercially available products include, for example, Acetamine 24, Cortamine 24P, 60W, and 86P Conc., manufactured by Kao Corporation.

Examples of anionic surfactants include polyoxyethylene alkyl ether sulfates, sodium dodecylbenzenesulfonate, alkali salts of styrene-acrylic acid copolymers, sodium alkylnaphthalenesulfonates, sodium alkyldiphenyletherdisulfonates, 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.

Commercially available products include, for example, Futergent 100 and 150 manufactured by Neos Corporation, and Adeka Hope YES-25, Adeka Col 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.

Commercially available products include Kao Corporation's Anhithol 20AB, 20BS, 24B, 55AB, 86B, 20Y-B, and 20N.

The leveling agent (N) can be used alone or in combination of two or more types.

The content of the leveling agent (N) is preferably 0.001% by mass or more and 2% by mass or less, and more preferably 0.005% by mass or more and 1% by mass or less, based on 100% by mass of the non-volatile content of the photosensitive coloring composition.

[Storage stabilizer (O)]
The photosensitive coloring composition of the present invention may contain a storage stabilizer (O).

Examples of storage stabilizers (O) 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 tetraphenylphosphine, and phosphites.

Storage stabilizers (O) can be used alone or in combination of two or more types.

The content of the storage stabilizer (O) is preferably 0.05% by mass or more and 5% by mass or less based on 100% by mass of the nonvolatile content of the photosensitive composition.

[Adhesion improver (P)]
The photosensitive coloring composition of the present invention may contain an adhesion improver (P).

Examples of the adhesion improver (P) include vinyl silanes such as vinyl trimethoxy silane and vinyl triethoxy silane, (meth)acrylic silanes such as 3-methacryloxypropyl methyl dimethoxy silane, 3-methacryloxypropyl trimethoxy silane, 3-methacryloxypropyl methyl diethoxy silane, 3-methacryloxypropyl triethoxy silane and 3-acryloxypropyl trimethoxy silane, epoxy silanes such as 2-(3,4-epoxycyclohexyl)ethyl trimethoxy silane, 3-glycidoxypropyl methyl dimethoxy silane, 3-glycidoxypropyl trimethoxy silane, 3-glycidoxypropyl methyl diethoxy silane and 3-glycidoxypropyl triethoxy silane, N-2-(aminoethyl)-3-aminopropyl methyl Examples of such silanes include aminosilanes such as N-2-(aminoethyl)-3-aminopropyltrimethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-triethoxysilyl-N-(1,3-dimethyl-butylidene)propylamine, N-phenyl-3-aminopropyltrimethoxysilane, and hydrochloride salt of N-(vinylbenzyl)-2-aminoethyl-3-aminopropyltrimethoxysilane; mercaptosilanes such as 3-mercaptopropylmethyldimethoxysilane and 3-mercaptopropyltrimethoxysilane; styrylsilanes such as p-styryltrimethoxysilane; ureidosilanes such as 3-ureidopropyltriethoxysilane; and isocyanates such as 3-isocyanatepropyltriethoxysilane.

The adhesion improver (P) can be used alone or in combination of two or more types.

The content of the adhesion improver (P) is preferably 0.1% by mass or more and 5% by mass or less based on 100% by mass of the non-volatile content of the photosensitive coloring composition.

[Near infrared absorbing compound (Q)]
The photosensitive coloring composition of the present invention may contain a near infrared absorbing compound (Q), which makes it possible to control the transmittance of light in the near infrared region.

The near infrared absorbing compound (Q) is a compound having an absorption maximum at a wavelength of 700 to 2,000 nm, and may be a pigment (also referred to as a near infrared absorbing pigment) or a dye (also referred to as a near infrared absorbing dye). In addition, a near infrared absorbing pigment and a near infrared absorbing dye may be used in combination. From the viewpoints of heat resistance and light fastness, a near infrared absorbing pigment is preferred.
In this specification, the near infrared absorbing pigment has a solubility in 100 g of propylene glycol monomethyl ether acetate at 25° C. of preferably less than 2 g, more preferably less than 1 g, and particularly preferably 0.5 g or less.

Examples of the near-infrared absorbing compound (Q) include cyanine compounds, phthalocyanine compounds, naphthalocyanine compounds, indigo compounds, immonium compounds, anthraquinone compounds, pyrrolopyrrole compounds, squarylium compounds, croconium compounds, indium tin oxide, antimony tin oxide, zinc oxide, aluminum-doped zinc oxide, fluorine-doped tin dioxide, niobium-doped titanium dioxide, cesium tungsten oxide, and metal oxide particles or metal particles such as copper, nickel, silver, and gold.

Cyanine compounds are described in WO 2006/006573, WO 2010/073857, JP 2013-241598, JP 2016-113501, JP 2016-113504, etc.; phthalocyanine compounds are described in JP 4-23868, JP 06-192584, JP 2000-63691, WO 2014/208514, etc.; naphthalocyanines are described in WO 2006/006573, WO 2010/073857, JP 2013-241598, JP 2016-113501, JP 2016-113504, etc. Examples of the arylene compounds are disclosed in JP-A-11-152414, JP-A-2000-86919, JP-A-2009-29955, WO 2018/186490, JP-A-2022-91099, JP-A-2022-072558, etc.; examples of the indigo compounds are disclosed in JP-A-2012-224593, JP-A-2013-87233, JP-A-2013-230412, etc.; examples of the immonium compounds are disclosed in JP-A-200 Anthraquinone compounds are disclosed in JP-A-62-903 and JP-A-1-172458, and pyrrolopyrrole compounds are disclosed in JP-A-2009-263614, JP-A-2010-90313, JP-A-2011-068731, JP-A-2014-130348, WO 2015/16687, and the like. 3, etc.; squarylium compounds are described in JP 2011-132361 A, JP 2016-142891 A, WO 2017/135359 A, WO 2018/225837 A, JP 2019-001987 A, WO 2020/054718 A, WO 2021/029195 A, etc.; croconium compounds are described in WO 2019/021767 A, etc.
Among these, from the viewpoint of light resistance, it is preferable to include at least one compound selected from the group consisting of phthalocyanine compounds, naphthalocyanine compounds, indigo compounds, pyrrolopyrrole compounds, and squarylium compounds.

The near infrared absorbing compound (Q) can be used alone or in combination of two or more kinds. When two or more kinds are used in combination, it is preferable to use at least two kinds of compounds having different maximum absorption wavelengths. This broadens the waveform of the absorption spectrum compared to the case where one kind of near infrared absorbing compound (Q) is used, and near infrared rays in a wide wavelength range can be absorbed.

From the viewpoint of near-infrared absorbing properties, the content of the near-infrared absorbing compound (Q) is preferably 0.1% by mass or more and 70% by mass or less, and more preferably 0.5% by mass or more and 50% by mass or less, based on 100% by mass of the non-volatile content of the photosensitive coloring composition.

[Water content]
From the viewpoint of storage stability, the photosensitive coloring composition of the present invention preferably has a water content of 2.0% by mass or less.

The content of water in the photosensitive coloring composition is more preferably 1.5% by mass or less, and particularly preferably 1.0% by mass or less. There is no particular lower limit for the water content.

There are no particular limitations on the method for controlling the water content, and known methods can be used. For example, each of the above-mentioned components is thoroughly dried, etc., to reduce the amount of water contained in the components. Other examples include a method of producing a photosensitive coloring composition while blowing in dry air, an inert gas, or a mixture of these gases, and a method of dehydrating the composition by adding a molecular sieve after production.

The water content can be measured by known methods such as the Karl Fischer method.

[Content of specific metal elements]
From the viewpoint of storage stability, the photosensitive coloring composition of the present invention preferably has a total content of Li, Na, K, Mg, Ca, Fe, and Cr (hereinafter also referred to as specific metal elements) contained in the photosensitive coloring composition of 500 mass ppm or less.

When the total amount of the specific metal elements is within the above range, the photosensitive coloring composition has excellent dispersion stability and sensitivity even after storage over time. The content of the specific metal elements can be measured by inductively coupled plasma emission spectrometry (ICP).

[Method for producing photosensitive coloring composition]
The photosensitive coloring composition of the present invention can be prepared by stirring and mixing the above-mentioned components. In the preparation, each component may be blended at once, or each component may be dissolved or dispersed in an organic solvent and then blended successively. When a pigment with low solubility is used as the colorant (A), it is preferable to perform a dispersion treatment. For example, the colorant (A), the dispersion resin (F), and the organic solvent (E) are added to perform a dispersion treatment. Then, the binder resin (B), the polymerizable compound (C), the polymerization initiator (D), and the organic solvent (E) are blended and mixed to produce the composition. The timing of blending each material is arbitrary. The dispersion process can also be performed multiple times.

Examples of dispersing machines used for the dispersion process include 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.

The average dispersed particle size (secondary particle size) of the colorant (A) in the photosensitive coloring composition is preferably 30 to 200 nm, more preferably 40 to 200 nm. If the colorant has an appropriate particle size, it is easy to obtain a photosensitive coloring composition with high dispersion stability.

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

It is preferable to remove 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 from the photosensitive coloring composition by means of centrifugation, filtration with a sintered filter or membrane filter, etc. It is preferable that the photosensitive coloring composition of the present invention does not substantially contain particles of 0.5 μm or more, and more preferably does not contain particles of 0.3 μm or less.

The photosensitive coloring composition of the present invention is preferably used to simultaneously form colored pixels and stacked photospacers, but can also be used to form colored pixels and stacked photospacers separately.

<Membrane>
The film of the present invention is formed using the above-mentioned photosensitive coloring composition. The film is preferably a patterned film, but may also be used as a flat film without patterning.

[Membrane manufacturing method]
The method for producing the film is not particularly limited, and any known method can be used. For example, the film can be produced through a step of coating the photosensitive coloring composition of the present invention on a substrate.

The substrate may be, for example, a substrate made of a material such as glass, resin, or silicon. The glass may be colorless and transparent, or colored glass such as blue glass may be used depending on the application. An organic light-emitting layer may be formed on these substrates. An imaging element such as a CCD or CMOS may also be formed on the substrate. If necessary, an undercoat layer may be provided on the substrate to improve adhesion with the upper layer, prevent diffusion of substances, and flatten the surface. The thickness of the substrate is preferably 50 μm to 1 mm.

The coating method can be a known method. Examples include a drip method, a slit coating method, a spray method, a roll coating method, a rotary coating method, a casting coating method, an inkjet method, flexographic printing, a screen printing, a gravure printing, and an offset printing.

The thickness of the film can be adjusted as appropriate depending on the purpose. The thickness of the film is preferably 0.05 to 20.0 μm, and more preferably 0.3 to 10.0 μm.

Next, a pattern is formed. Methods for forming a pattern include photolithography and dry etching, with photolithography being preferred. If the film is to be used as a flat film, the step of forming a pattern is not necessary, and after coating, the film is dried or the entire surface is exposed to light as necessary.

The method for forming the pattern is explained in detail below.

When forming a pattern by photolithography, a layer formed by coating the photosensitive coloring composition of the present invention on a substrate is dried (pre-baked), and then exposed to light in a pattern through a mask (exposure process). The unexposed parts are removed by alkaline development (development process), and the pattern is then heat-treated (post-bake process).

[Exposure process]
In the exposure process, the layer formed by coating is exposed to a specific pattern through a mask using an exposure device such as a stepper. This allows the exposed portion to be cured. Examples of the active energy rays used for exposure include ultraviolet rays such as g-rays (wavelength 436 nm), h-rays (wavelength 405 nm), and i-rays (wavelength 365 nm). Light with a wavelength of 300 nm or less can also be used. Examples of light with a wavelength of 300 nm or less include KrF rays (wavelength 248 nm) and ArF rays (wavelength 193 nm).
In addition, the exposure may be performed by continuous irradiation with light, or by repeating irradiation and pause of light in a short cycle (for example, on the order of milliseconds or less) (pulse exposure).

[Developing process]
Next, an alkali development process is carried out, whereby the unexposed portions of the layer are dissolved in an aqueous alkali solution, and only the hardened portions remain, yielding a patterned film.
Examples of the alkaline developer include alkaline compounds such as sodium hydroxide, potassium hydroxide, sodium carbonate, sodium silicate, sodium metasilicate, aqueous ammonia, ethylamine, diethylamine, dimethylethanolamine, tetramethylammonium hydroxide, tetraethylammonium hydroxide, choline, pyrrole, piperidine, and 1,8-diazabicyclo-[5.4.0]-7-undecene.
The concentration of the alkaline developer is preferably 0.001 to 10% by mass, more preferably 0.01 to 1% by mass. The pH of the alkaline developer is preferably 11 to 13, more preferably 11.5 to 12.5. When used at an appropriate pH, it suppresses roughening and peeling of the pattern and improves the remaining film rate after development.
Examples of the developing method include a dipping method, a spraying method, a puddle method, etc. The developing temperature is preferably 15 to 40° C. After the alkaline development, it is preferable to wash with pure water.

[Post-bake process]
After development, a heat treatment (post-baking) is performed to improve the resistance of the film.
The temperature is preferably 80 to 300° C. The time is preferably about 2 minutes to 1 hour. When a material with low heat resistance is used for the substrate, or when a substrate having an organic electroluminescence element as the light-emitting layer is used, the temperature is preferably 150° C. or less, and more preferably 130° C. or less.

<Color filter>
The color filter of the present invention has colored pixels formed using the above-mentioned photosensitive coloring composition, and a laminated photospacer.

Figure 1 is a schematic cross-sectional view showing an example of the configuration of a color filter of the present invention.

The color filter (100) shown in FIG. 1 has a black matrix (120) and colored pixels (131, 132, 133) formed of the photosensitive coloring composition of the present invention on a glass substrate (110), and a laminated photospacer (140) formed by laminating one or more colors of photosensitive coloring compositions constituting the colored pixels on the black matrix (120).

The black matrix is a black layer formed between each colored pixel to increase the contrast of a pixel display device.

The colored pixels are formed using the photosensitive coloring composition of the present invention. By appropriately selecting the colorant (A), red pixels, green pixels, blue pixels, magenta pixels, cyan pixels, yellow pixels, gray pixels, etc. can be obtained. The colored pixel layer can be formed in the same manner as the above-mentioned film.

The laminated photospacer is formed simultaneously with the colored pixels using the photosensitive coloring composition of the present invention. One or more laminated photospacers are laminated on the black matrix. There is no particular limit to the number of layers as long as the cell gap required for an image display device can be obtained, but two or three layers are preferred.

The color filter of the present invention may have a transparent protective film layer formed on the colored pixels and the laminated photospacer.

<Image display device>
The image display device of the present invention has the above-mentioned color filter.

The form of the image display device is not particularly limited as long as it functions as an image display device. For example, the configuration described in "Next Generation Liquid Crystal Display Technology" (by Tatsuo Uchida, published by Kogyo Chosakai Co., Ltd. in 1994) can be mentioned.
The definition of image display devices and details of each image display device are described, for example, in "Electronic Display Devices" (written by Sasaki Akio, published by Kogyo Chosakai Co., Ltd. in 1990) and "Display Devices" (written by Ibuki Yoshiaki, published by Sangyo Tosho Co., Ltd. in 1989).

The present invention will be described in more detail below with reference to examples. However, the present invention is not limited to these examples. Note that "parts" means "parts by mass" and "%" means "% by mass". In addition, in the present invention, the non-volatile content or non-volatile content concentration refers to the mass remaining after leaving the mixture in an oven at 230°C for 30 minutes.

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

(Average molecular weight of resin)
The number average molecular weight and weight average molecular weight of the resin were measured by gel permeation chromatography (GPC) equipped with an RI detector. An HLC-8220GPC (manufactured by Tosoh Corporation) was used as the apparatus, two separation columns were connected in series, and two "TSK-GEL SUPER HZM-N" packings were used in series for both packings. The oven temperature was 40°C, a tetrahydrofuran (THF) solution was used as the eluent, and the measurement was performed at a flow rate of 0.35 ml/min. The sample was dissolved in a solvent consisting of 1% by mass of the above eluent, and 20 microliters were injected. The molecular weight is a polystyrene equivalent value.

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

(Amine value of resin)
The amine value of the resin is the total amine value (mg KOH/g) measured in accordance with the method of ASTM D 2074 and converted into non-volatile content.

<Production of Colorant (A)>
(Colorant (A-7))
According to the description of JP2014-12838A, a colorant (A-7) was obtained that contains anions of an azo compound represented by general formula (1) and an azo compound having a tautomeric structure thereof, and a compound represented by general formula (2), in which the molar ratio of Ni and Zn metal ions was 65:35.

<Production of binder resin (B)>
(Binder resin (B1-1) having a weight average molecular weight of 3,000 to 8,000)
A separable 4-neck flask was fitted with a thermometer, a cooling tube, a nitrogen gas inlet tube, and a stirrer to form a reaction vessel. 262.0 parts of propylene glycol monomethyl ether acetate (hereinafter, PGMAc) was placed in the reaction vessel, and the vessel was heated to 120°C while injecting nitrogen gas into it. At the same temperature, 16.7 parts (0.16 mol) of styrene (hereinafter, St), 76.8 parts (0.54 mol) of glycidyl methacrylate (hereinafter, GMA), 66.1 parts (0.3 mol) of dicyclopentanyl methacrylate (hereinafter, DCPMA), 19.0 parts of t-butylperoxy-2-ethylhexanoate as a polymerization initiator, and a mixture of PGMAc were added dropwise over 2.5 hours from the dropping tube.
After the dropwise addition, the mixture was stirred at 120°C for another 2 hours to obtain a precursor. The flask was then replaced with air, and 38.9 parts (0.54 moles) of acrylic acid (hereinafter, AA) as a modified compound, 0.6 parts of triphenylphosphine as a catalyst, and 0.2 parts of methylhydroquinone were added, and the mixture was reacted at 110°C for 10 hours. As a result, the epoxy group of GMA reacted with the carboxyl group of AA, and hydroxyl groups were generated by cleavage of the epoxy group of GMA, while polymerizable unsaturated groups were introduced (hereinafter, GMA + AA).
Next, 40 parts (0.4 moles) of succinic anhydride (hereinafter, SHA) was added as a modified compound, and reacted at 110° C. for 4 hours. This caused a part of the hydroxyl groups of GMA+AA to react with succinic anhydride (hereinafter, GMA+AA+SHA). Then, PGMAc was added so that the non-volatile content was 40% by mass. The acid value was 95 mg KOH/g, and the weight average molecular weight was 5,000. In Table 1, the blending amounts are expressed in mol%.

(Binder resins (B1-2) to (B1-5) having a weight average molecular weight of 3,000 to 8,000)
The type and amount of monomer and the amount of polymerization initiator were changed so as to obtain the composition and weight average molecular weight shown in Table 1, and binder resins (B1-2) to (B1-5) having a weight average molecular weight of 3,000 to 8,000 were synthesized. PGMAc was added to adjust the non-volatile content to 40 mass%.

GMA+AA+THPA in Table 1 represents a polymerizable unsaturated group-containing monomer unit (b2) obtained by reacting some of the hydroxyl groups of GMA+AA with tetrahydrophthalic anhydride (hereinafter, THPA).

(Binder resin (B2-1))
A separable 4-neck flask was equipped with a thermometer, a cooling tube, a nitrogen gas inlet tube, a dropping tube, and a stirrer. 196 parts of PGMAc 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, 25.1 parts of benzyl methacrylate (hereinafter, BzMA), 23.0 parts of n-butyl methacrylate (hereinafter, n-BMA), 14.3 parts of 2-hydroxyethyl methacrylate (hereinafter, HEMA), 13.4 parts of methacrylic acid (hereinafter, MAA), 24.1 parts of paracumylphenol EO-modified acrylate (manufactured by Toagosei Co., Ltd. "Aronix M110"), and 1.1 parts of 2,2'-azobisisobutyronitrile were added dropwise over 2 hours.
After the dropwise addition, the mixture was allowed to react for another 3 hours. After cooling to room temperature, PGMAc was added so that the non-volatile content was 40% by mass. The acid value was 87 mg KOH/g, and the weight average molecular weight was 25,000. In Table 2, the blending amounts are expressed in mol%.

(Binder Resins (B2-2) to (B2-4))
Binder resins (B2-2) to (B2-4) were synthesized by changing the type and amount of monomer and the amount of polymerization initiator so as to obtain the composition and weight average molecular weight shown in Table 2, and PGMAc was added to adjust the non-volatile content to 40 mass%.

MAA+GMA in Table 2 represents a polymerizable unsaturated group-containing monomer unit (b2) in which the epoxy group of GMA is added to the carboxyl group of methacrylic acid (hereinafter, MAA) in the precursor.

<Production of polymerizable compound (C)>
(Polymerizable compound having a urethane bond (C2-1))
A five-neck flask equipped with a stirrer, reflux condenser, nitrogen inlet tube, thermometer, and dropping tube was charged with 400 parts of dipentaerythritol pentaacrylate, 100 parts of PGMAc, and 0.5 parts of N,N-dimethylbenzylamine, and the temperature was raised to 70°C. A mixture of 66 parts of toluene diisocyanate and 66 parts of PGMAc was dropped from the dropping tube over 2 hours. After dropping, the mixture was reacted at a temperature of 50 to 70°C for 8 hours, and the disappearance of the isocyanate absorption at 2,180 cm ^-1 was confirmed by IR. Next, 35 parts of mercaptoacetic acid and 0.6 parts of 4-methoxyphenol were charged and reacted at a temperature of 50 to 60°C for 6 hours. PGMAc was added so that the non-volatile content was 50% by mass, and an aromatic urethane acrylate having an acidic group with an average number of polymerizable unsaturated groups of 9 was obtained.

(Polymerizable compound having a urethane bond (C2-2))
In a five-neck flask equipped with a stirrer, reflux condenser, nitrogen inlet tube, thermometer, and dropping tube, 400 parts of dipentaerythritol pentaacrylate, 100 parts of PGMAc, and 0.5 parts of N,N-dimethylbenzylamine were charged, and the temperature was raised to 70°C, and a mixture of 84 parts of isophorone diisocyanate and 84 parts of PGMAc was dropped from the dropping tube over 2 hours. After dropping, the mixture was reacted at a temperature of 50 to 70°C for 8 hours, and the disappearance of the isocyanate absorption at 2180 cm ^-1 was confirmed by IR. PGMAc was added so that the nonvolatile content was 50% by mass, and an alicyclic urethane acrylate having an average polymerizable unsaturated group number of 10 was obtained.

(Polymerizable compound having a urethane bond (C2-3))
A five-neck flask equipped with a stirrer, reflux condenser, nitrogen inlet tube, thermometer, and dropping tube was charged with 400 parts of dipentaerythritol pentaacrylate, 100 parts of PGMAc, and 0.5 parts of N,N-dimethylbenzylamine, and the temperature was raised to 70°C. A mixture of 64 parts of hexamethylene diisocyanate and 64 parts of PGMAc was dropped from the dropping tube over 2 hours. After dropping, the mixture was reacted at a temperature of 50 to 70°C for 8 hours, and the disappearance of the isocyanate absorption at 2,180 cm ^-1 was confirmed by IR. PGMAc was added so that the nonvolatile content was 50% by mass, and an aliphatic urethane acrylate having an average polymerizable unsaturated group number of 10 was obtained.

<Production of Dispersion Resin (F)>
(Dispersion resin having acidic group (F1-1))
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 measuring the non-volatile content. 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 PGMAc was added so that the non-volatile content was 30%, to obtain a dispersion resin (F1-1) having an acidic group. The resin had an acid value of 70 mgKOH/g and a weight average molecular weight of 8,500.

(Dispersion resin having basic group (F2-1))
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 100 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, 50 parts of PGMAc, 40 parts of dimethylaminoethyl methacrylate as a second block (A block) monomer, and 10 parts of methacryloyloxyethylbenzyldimethylammonium chloride were charged into the reaction apparatus, and the mixture was stirred while maintaining 110° C. under a nitrogen atmosphere, and the reaction was continued. Two hours after the addition, the polymerization solution was sampled and the nonvolatile 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 nonvolatile content, and the reaction solution was cooled to room temperature to stop the polymerization. After cooling to room temperature, about 2 g was sampled and dried by heating at 180°C for 20 minutes to measure the nonvolatile content, and PGMAc was added so that the nonvolatile content became 30% by mass, thereby obtaining a dispersion resin (F2-1) having a basic group. The resin had an amine value of 169.8 mgKOH/g.

<Preparation of Dispersion>
(Dispersion 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. The mixture was then filtered through a filter having a pore size of 1.0 μm to prepare Dispersion 1.
Colorant (A-1): 15.0 parts Dispersion resin (F-1): 5.0 parts Dispersion resin (F-2): 10.0 parts Organic solvent (E3-1): 70.0 parts

(Dispersions 2 to 13)
Dispersions 2 to 13 were prepared in the same manner as Dispersion 1, except that the components and amounts shown in Table 3 were changed.

The components listed in Tables 3-1 and 3-2 are as follows:

[Colorant (A)]
A-1: C.I. Pigment Green 58
A-2: C.I. Pigment Green 59
A-3: C.I. Pigment Green 63
A-4: C.I. Pigment Yellow 138
A-5: C.I. Pigment Yellow 139
A-6: C.I. Pigment Yellow 150
A-7: Synthetic colorant (A-7)
A-8: C.I. Pigment Red 254
A-9: C.I. Pigment Red 177
A-10: C.I. Pigment Blue 15:6
A-11: C.I. Pigment Violet 23

[Dye derivative (G)]

[Organic solvent (E)]
E3-1: Propylene glycol monomethyl ether acetate (boiling point 145°C, vapor pressure 500 Pa)

<Production of Photosensitive Coloring Composition>
[Example 1]
(Photosensitive Coloring Composition 1)
The following raw materials were mixed and stirred, and filtered through a filter having a pore size of 1.0 μm to obtain a photosensitive coloring composition 1.
Dispersion 1: 28.0 parts Dispersion 4: 7.0 parts Binder resin having a weight average molecular weight of 3,000 to 8,000 (B1-1): 3.25 parts
Polymerizable compound (C1-1) having a viscosity of 500 mPa·S or less at 25 ° C.: 1.5 parts Polymerizable compound having a urethane bond (C2-1): 2.0 parts Polymerizable compound having a urethane bond (C2-3): 2.0 parts Other polymerizable compounds (C3-1): 1.0 parts Polymerization initiator (D-1): 0.5 parts Organic solvent (E1-1): 2.0 parts Organic solvent (E2-1): 22.0 parts Organic solvent (E3-1): 28.95 parts Thermosetting compound (I): 0.8 parts Leveling agent (N): 1.0 parts

[Examples 2 to 56 and Comparative Examples 1 to 4]
(Photosensitive Coloring Compositions 2 to 60)
Photosensitive coloring compositions 2 to 60 were prepared in the same manner as in Example 1 using the raw materials and amounts shown in Tables 4-1 to 4-6.

The raw materials listed in Tables 4-1 to 4-6 are as follows. Note that in Tables 4-1 to 4-6, the organic solvents contained in each component are listed in addition to organic solvent (E).

[Polymerizable compound (C)]
(Polymerizable compound (C1) having a viscosity of 500 mPa·S or less at 25° C.)
C1-1: Trimethylolpropane triacrylate (80 to 120 mPa·S)
C1-2: Trimethylolpropane EO modified triacrylate (50 to 90 mPa·S)
C1-3: Pentaerythritol EO modified tetraacrylate (300 to 400 mPa·S)
C1-4: Tricyclodecane dimethanol diacrylate (125 to 145 mPa·S)

(Polymerizable Compound (C3) Other Than Polymerizable Compounds (C1) and (C2))
C3-1: Dipentaerythritol hexaacrylate (7,500 mPa·S or more)
C3-2: Aronix M-521 (manufactured by Toagosei Co., Ltd.: polyfunctional acrylate having an acidic group, 40,000 mPa·S or more)
C3-3: KAYARAD DPCA-20 (manufactured by Nippon Kayaku Co., Ltd.: lactone-modified multifunctional acrylate, 1,500 mPa·S or more)

[Polymerization initiator (D)]
D-1: The compound (D-1) described above (having an extinction coefficient of 7,051 L/mol cm for light with a wavelength of 365 nm)
D-2: The compound (D-2) described above (having an absorption coefficient of 13,410 L/mol cm for light having a wavelength of 365 nm)
D-3: The compound (D-3) described above (having an absorption coefficient of 27,257 L/mol cm for light having a wavelength of 365 nm)
D-4: The compound (D-4) described above (having an absorption coefficient of 14,214 L/mol cm for light having a wavelength of 365 nm)
D-5: The compound (D-5) described above (having an absorption coefficient of 14,127 L/mol cm for light having a wavelength of 365 nm)
D-6: The compound (D-6) described above (having an absorption coefficient of 18,334 L/mol cm for light having a wavelength of 365 nm)
D-7: The compound (D-7) described above (having an absorption coefficient of 3,884 L/mol cm for light having a wavelength of 365 nm)
D-8: The following compound (having an absorption coefficient of light with a wavelength of 365 nm of less than 5,000 L/mol cm):

[Organic solvent (E)]
(Organic solvent (E1))
E1-1: Propylene glycol diacetate (boiling point 190°C, vapor pressure 30 Pa)
E1-2: Diethylene glycol diethyl ether (boiling point 188°C, vapor pressure 90 Pa)
E1-3: Ethylene glycol (boiling point 198°C, vapor pressure 7 Pa)
E1-4: Dipropylene glycol monomethyl ether (boiling point 188°C, vapor pressure 55 Pa)
E1-5: Ethylene glycol monobutyl ether acetate (boiling point 192°C, vapor pressure 31 Pa)
E1-6: Dipropylene glycol methyl ether acetate (boiling point 213°C, vapor pressure 14 Pa)

(Organic solvent (E2))
E2-1: Ethyl 3-ethoxypropionate (boiling point 170°C, vapor pressure 200 Pa)
E2-2: Diethylene glycol dimethyl ether (boiling point 162°C, vapor pressure 330 Pa)
E2-3: 3-methoxybutyl acetate (boiling point 171°C, vapor pressure 369 Pa)
E2-4: 3-methoxy-1-butanol (boiling point 161°C, vapor pressure 160 Pa)

(Organic solvent (E3))
E3-1: Propylene glycol monomethyl ether acetate (boiling point 145°C, vapor pressure 500 Pa)
E3-2: Ethylene glycol monoethyl ether (boiling point 135°C, vapor pressure 500 Pa)
E3-3: Methyl 3-methoxypropionate (boiling point 142°C, vapor pressure 707 Pa)
E3-4: Cyclohexanone (boiling point 156°C, vapor pressure 500 Pa)
E3-5: Propylene glycol monoethyl ether (boiling point 132°C, vapor pressure 900 Pa)

(Organic solvent (E4))
E4-1: Diethylene glycol monobutyl ether (boiling point 230°C, vapor pressure 1.4 Pa)
E4-2: n-Propyl acetate (boiling point 101°C, vapor pressure 3,300 Pa)

[Thermosetting compound (I)]
EHPE-3150 (manufactured by Daicel Corporation, a compound represented by general formula (7), with approximately 15 epoxy groups and an epoxy equivalent of 170 to 190 g/eq)

[Leveling agent (N)]
A solution obtained by dissolving 1 part of BYK-330 (manufactured by BYK-Chemie) in 99 parts of PGMAc was used as a leveling agent (N).

Table 5 shows the mass percentages of organic solvents (E1) to (E4) in 100 mass% of organic solvent (E) for photosensitive coloring compositions 1 to 60, and the mass percentage of organic solvent (E) in 100 mass% of the photosensitive coloring composition.

<Evaluation of Photosensitive Coloring Composition>
The following evaluations were carried out for the obtained photosensitive coloring compositions 1 to 60. The evaluation results are shown in Table 6.

[Evaluation of developability]
The obtained photosensitive coloring composition was applied to a glass substrate (Corning Eagle 2000) having a length of 100 mm, width of 100 mm, and thickness of 0.7 mm using a spin coater so that the dry film thickness was 2.0 μm, and dried in a reduced pressure dryer until the vacuum degree reached 65 Pa. Next, using an ultra-high pressure mercury lamp, the substrate was exposed to light at an illuminance of 30 mW/cm ² and 50 mJ/cm ² through a photomask having a stripe pattern with a width of 100 μm. Thereafter, the substrate was spray-developed using an aqueous developer containing 0.12% nonionic surfactant and 0.04% potassium hydroxide at 23 ° C., washed with ion-exchanged water, air-dried, and heated in a clean oven at 230 ° C. for 30 minutes. The spray development was performed for each coating of the photosensitive coloring composition in the shortest time possible to form a pattern without residual development. Using a scanning electron microscope, the amount of residue remaining in the unexposed area was measured at a magnification of 20,000 times. The evaluation criteria are as follows, with a rating of 3 or higher being considered practical.
5: No residue was found in the unexposed areas.
4: 1 to 5 residues were observed in an area of 1.0 μm square in the unexposed area.
3: 6 to 10 residues were observed in an area of 1.0 μm square in the unexposed area.
2: 11 to 20 residues were observed in an area of 1.0 μm square in the unexposed area.
1: 21 or more residues were observed in an area of 1.0 μm square in the unexposed area.

[Adhesion evaluation]
The obtained photosensitive coloring composition was applied by spin coating to a glass substrate (Corning Eagle 2000) having a length of 100 mm x width of 100 mm and a thickness of 0.7 mm so that the film thickness after drying was 2.0 μm, and dried in a reduced pressure dryer until the degree of vacuum reached 65 Pa. Next, after cooling the substrate to room temperature, the substrate was exposed to light at an illuminance of 30 mW/cm ² and 50 mJ/cm ² through a photomask having a stripe pattern with a width of 5 μm using an ultra-high pressure mercury lamp. Thereafter, the substrate was spray-developed using an aqueous developer containing 0.12% nonionic surfactant and 0.04% potassium hydroxide at 23 ° C., washed with ion-exchanged water, air-dried, and heated in a clean oven at 230 ° C. for 30 minutes to obtain a substrate for evaluation. The spray development was performed for each coating of the photosensitive coloring composition for the shortest time possible to form a pattern without remaining development, and this was determined as the appropriate development time.
Among the patterns on the evaluation substrate, fine line patterns with widths of 5 to 25 μm were observed with an optical microscope to confirm the remaining fine line patterns. The evaluation criteria are as follows, with 3 or more being considered practical.
5: Fine lines of 10 μm or less remain.
4: Fine lines of 15 μm or more remain.
3: Fine lines of 20 μm or more remain.
2: 25 μm fine lines remain.
1: No fine lines remain.

[Pattern shape evaluation]
The obtained photosensitive coloring composition was applied by spin coating to a glass substrate (Corning Eagle 2000) having a length of 100 mm, width of 100 mm, and thickness of 0.7 mm so that the film thickness after drying was 2.0 μm, and dried in a vacuum dryer until the degree of vacuum reached 65 Pa. Then, after cooling the substrate to room temperature, the substrate was exposed through a photomask having a 100 μm wide stripe pattern at two levels of illuminance 30 mW/cm ² and exposure dose 25 mJ/cm ² and 50 mJ/cm ² using an ultra-high pressure mercury lamp. Then, the substrate was spray-developed using an aqueous developer containing 0.12% nonionic surfactant and 0.04% potassium hydroxide at 23 ° C., and then washed with ion-exchanged water and air-dried. The obtained substrate was post-baked in a clean oven at 230 ° C. for 30 minutes to obtain a substrate for evaluation.
The obtained evaluation substrate was measured for line width at an exposure dose of 25 mJ/ ^cm2 ( _CD25 ) and 50 mJ/ ^cm2 ( _CD50 ) using a Nikon Eclipse LV100POL Model optical microscope, and the line width difference (ΔCD) due to the difference in exposure dose was calculated using the following formula (1). The evaluation criteria are as follows, with 3 or more being considered practical.
Formula (1): ΔCD = CD ₅₀ - CD ₂₅
5: ΔCD is less than 2 μm 4: ΔCD is 2 μm or more and less than 3 μm 3: ΔCD is 3 μm or more and less than 5 μm 2: ΔCD is 5 μm or more and less than 6 μm 1: ΔCD is 6 μm or more

[Surface defect evaluation]
The obtained photosensitive coloring composition was applied by spin coating to a glass substrate (Corning Eagle 2000) having a length of 100 mm, width of 100 mm, and thickness of 0.7 mm so that the film thickness after drying was 2.0 μm, and dried in a vacuum dryer until the vacuum degree reached 65 Pa. Then, after cooling the substrate to room temperature, the substrate was exposed to light at an illuminance of 30 mW/cm ² and 50 mJ/cm ² through a photomask with a 25 μm wide stripe pattern using an ultra-high pressure mercury lamp. Then, the substrate was spray-developed using an aqueous developer containing 0.12% nonionic surfactant and 0.04% potassium hydroxide at 23° C., and then washed with ion-exchanged water and air-dried to obtain a substrate for evaluation.
The defect density of the obtained evaluation substrate was measured using a foreign matter inspection device (manufactured by KLA-Tencor Corporation). A defect is defined as a detection point having a size of 1 μm or more. The evaluation criteria are as follows, with a score of 3 or more being considered practical.
5: 10 pieces/ ^cm2 or less 4: More than 10 pieces/ ^cm2 and 30 pieces/ ^cm2 or less 3: More than 30 pieces/ ^cm2 and 50 pieces/ ^cm2 or less 3: More than 50 pieces/ ^cm2 and 70 pieces/ ^cm2 or less 1: More than 70 pieces/ ^cm2

[Evaluation of riding ability (1)]
The obtained photosensitive coloring composition was applied by spin coating on a glass substrate 210 on which a black matrix 220 having a thickness of 2.0 μm was formed so that the film thickness (a) of the colored pixel 230 after drying was 2.5 μm, and dried in a reduced pressure dryer until the degree of vacuum reached 65 Pa. Next, the substrate was exposed to light through a photomask at an illuminance of 30 mW/cm ² and 50 mJ/cm ² using an ultra-high pressure mercury lamp. After that, the substrate was spray-developed using an aqueous developer containing 0.12% of a nonionic surfactant and 0.04% of potassium hydroxide at 23° C., and then washed with ion-exchanged water and air-dried. The obtained substrate was post-baked in a clean oven at 230° C. for 30 minutes to prepare a substrate 200 for evaluating the riding property shown in FIG. 2.
The thickness (a) of the colored pixel 230 portion and the thickness (b) of the laminated photospacer 240 portion of the obtained substrate 200 for evaluating riding-up property were measured, and the riding-up property was evaluated by the following formula (2). The evaluation criteria are as follows, with 3 or more being considered practical.
The film thickness was measured using Dektak 3030 (manufactured by Japan Vacuum Engineering Co., Ltd.).
Formula (2): Climbing ability (%) = (B) ÷ (A) × 100
5: 75% or more, less than 80% 4: 80% or more, less than 82.5% 3: 82.5% or more, less than 85% 2: 85% or more, less than 90% 1: 90% or more

[Evaluation of riding ability (2)]
An evaluation substrate was prepared in the same manner as in the above-mentioned evaluation of riding property (1), except that the substrate was dried in a reduced pressure dryer until the degree of vacuum reached 65 Pa, and then further dried on a hot plate at 70° C. for 100 seconds. Then, the riding property was evaluated in the same manner and with the same criteria as in the above-mentioned evaluation of riding property (1).

The results in Table 6 show that Examples 1 to 56 are able to solve the problem of this application. Furthermore, the Examples with excellent results in the climbability evaluation (2) also show good climbability when the drying process includes heat drying in addition to vacuum drying.

100 Color filter 110 Glass substrate 120 Black matrix 131 Red pixel 132 Green pixel 133 Blue pixel 140 Stacked photospacer (141: red layer, 142: green layer, 143: blue layer)
200: Riding property evaluation substrate 210: Glass substrate 220: Black matrix 230: Colored pixel 240: Stacked photospacer

Claims (11)

A photosensitive coloring composition comprising a colorant (A), a binder resin (B), a polymerizable compound (C), a polymerization initiator (D), and an organic solvent (E),
The organic solvent (E) may be
An organic solvent (E1) having a boiling point of 180° C. or more and 220° C. or less and a vapor pressure at 20° C. of less than 100 Pa is contained in an amount of 0.1% by mass or more and less than 10% by mass based on 100% by mass of the organic solvent (E);
The organic solvent (E2) has a boiling point of 160° C. or more and less than 180° C. and a vapor pressure at 20° C. of 100 Pa or more and less than 400 Pa, and the organic solvent (E2) is contained in an amount of 10 mass% or more and 40 mass% or less based on 100 mass% of the organic solvent (E);
A photosensitive coloring composition comprising an organic solvent (E3) having a boiling point of 120° C. or more and less than 160° C. and a vapor pressure of 400 Pa or more at 20° C. in an amount of 55% by mass or more and 85% by mass or less based on 100% by mass of the organic solvent (E). The photosensitive coloring composition according to claim 1, wherein the content of the organic solvent (E) is 60% by mass or more and 90% by mass or less in 100% by mass of the photosensitive coloring composition. The photosensitive coloring composition according to claim 1, wherein the binder resin (B) contains a binder resin (B1) having a weight average molecular weight of 3,000 to 8,000. The photosensitive coloring composition according to claim 1, wherein the polymerizable compound (C) includes a polymerizable compound (C1) having a viscosity of 500 mPa·S or less at 25°C. The photosensitive coloring composition according to claim 4, wherein the polymerizable compound (C1) having a viscosity of 500 mPa·S or less at 25°C is contained in an amount of 5% by mass or more and 70% by mass or less based on 100% by mass of the polymerizable compound (C). The photosensitive coloring composition according to claim 1, wherein the polymerization initiator (D) contains a compound having an absorption coefficient of 5.0 x ¹⁰³ L/mol·cm or more for light having a wavelength of 365 nm in propylene glycol monomethyl ether acetate. The photosensitive coloring composition according to claim 1 further contains a dispersing resin (F). The photosensitive coloring composition according to claim 1 for simultaneously forming a colored pixel and a laminated photospacer. A film formed from the photosensitive coloring composition according to any one of claims 1 to 8. A color filter having colored pixels formed from the photosensitive coloring composition according to any one of claims 1 to 8, and a laminated photospacer. An image display device comprising the color filter according to claim 10.