Pigment dispersion composition and photosensitive coloring composition

Abstract

According to the present invention, there can be provided a pigment dispersion composition having good pigment dispersibility and storage stability, and a photosensitive coloring composition capable of obtaining a resin cured film having excellent developability, heat resistance, solvent resistance, and pattern adhesion. The pigment dispersion composition of the present invention contains a binder resin (A-1), a pigment (B), a polymer dispersant (C), and a solvent (D-1). The binder resin (A-1) is composed of a resin (A-1a) or a resin (A-1b). The resin (A-1a) is a resin obtained by adding a part of the carboxyl groups of a copolymer (P) of a monomer (M) containing a polymerizable monomer (m-1) composed of a polymerizable monomer (m-1a) having a bridged cyclic hydrocarbon group or a polymerizable monomer (m-1b) represented by the following formula (1), acrylic acid (m-2), and a polymerizable monomer (m-3) containing an aromatic ring, and an ethylenically unsaturated group-containing compound (m-4) having a group reactive with the carboxyl group.

Description

Technical Field

[0001] The present invention relates to a pigment dispersion composition and a photosensitive coloring composition.

[0002] This application claims priority based on Japanese Patent Application No. 2020-189475 filed in Japan on November 13, 2020, and incorporates its content herein. Background Art

[0003] From the viewpoints of resource saving and energy saving, photosensitive resin compositions that can be cured by active energy rays such as ultraviolet rays and electron beams are now widely used in various fields such as coating, printing, paints, and adhesives. In the field of electronic materials such as printed wiring boards, photosensitive resin compositions have been used for solder resistants, resists for color filters, and the like.

[0004] A color filter generally consists of: a transparent substrate such as a glass substrate; red, green, and blue pixels formed on the transparent substrate; a black matrix formed at the pixel boundaries; and a protective film formed on the pixels and the black matrix. A color filter having such a configuration is usually manufactured by sequentially forming a so-called black matrix or a colored pattern of pixels, or a so-called pattern of the protective film on the transparent substrate. As methods for forming various patterns, various methods have been proposed. Among them, the pigment / dye dispersion method, which uses a photosensitive resin composition as a resist and is produced by a lithography process of repeated coating, exposure, development, and baking, has become the mainstream today because it can provide a colored pattern with excellent durability and few defects such as pinholes.

[0005] Generally, the photosensitive resin composition used in the lithography process contains an alkali-soluble resin, a reactive diluent, a photoinitiator, a pigment / dye dispersion composition (also referred to as a colorant), and a solvent. Although the pigment / dye dispersion method has the above advantages, on the contrary, due to the repeated formation of black matrix, red, green, and blue patterns, heat resistance capable of withstanding high baking temperatures or resistance to various solvents exposed in the manufacturing steps is required.

[0006] Generally, negative resist characteristics are required for the photosensitive resin composition used in the lithography process. For example, Patent Document 1 discloses the use of a polymer (A) having an acid group and a bridged cyclic hydrocarbon group with 10 to 20 carbon atoms.

[0007] In addition, in recent years, high image quality and high definition have been required for displays such as liquid crystals or organic ELs, and for color filters, designs that achieve high brightness and an expanded color reproduction range have also been required. In order to achieve high brightness or an expanded color reproduction range, there are examples of using only dyes instead of pigments as colorants for color materials. However, since the heat resistance or solvent resistance of dyes is poor compared to pigments, and the usage ratio or types are limited, in most cases, the color materials contain pigments.

[0008] When using pigments to form a color filter, uniform micronization of the pigments is essential. By micronizing the pigments, it is possible to reduce the scattering of light transmitted through the color filter caused by the pigment particles, which contributes highly to the transmittance and achieves high brightness.

[0009] Furthermore, in order to expand the color reproduction range, efforts are also being made to increase the concentration of the colorant for the color material.

[0010] [Prior Art Documents]

[0011] [Patent Documents]

[0012] [Patent Document 1] Japanese Patent Application Laid-Open No. 2019-112494 Summary of the Invention

[0013] [Problems to be Solved by the Invention]

[0014] However, the micronized pigment particles are prone to aggregation, and there is a problem that the pigment dispersibility or the storage stability of the pigment dispersion composition is likely to decrease.

[0015] In addition, as the concentration of the "color material" increases, the concentration of the dispersant or the binder resin decreases. Therefore, it is required to exhibit various resist characteristics such as pigment dispersibility, storage stability, heat resistance, solvent resistance, and pattern adhesion with a smaller amount of dispersant or binder resin and other compositions.

[0016] The present invention is an invention for solving the above-mentioned problems, and the object is to provide a pigment dispersion composition that can obtain sufficient pigment dispersibility and storage stability even when the concentration of the dispersant or the binder resin decreases due to the high concentration of the pigment.

[0017] In addition, the object is to provide a photosensitive coloring composition that can obtain a resin cured film with excellent developability, heat resistance, solvent resistance, and pattern adhesion by using the pigment dispersion composition; a color filter having a cured product of the composition; and an image display component including the filter.

[0018] [Means for Solving the Problems]

[0019] The present invention includes the following solutions.

[0020] [1]. A pigment dispersion composition, characterized by containing a binder resin (A-1), a pigment (B), a polymer dispersant (C), and a solvent (D-1).

[0021] The binder resin (A-1) is at least one resin selected from resin (A-1a) and resin (A-1b).

[0022] The resin (A-1a) is a resin obtained by adding a part of the carboxyl groups of a copolymer (P) of a monomer (M) containing at least one polymerizable monomer (m-1) selected from polymerizable monomers (m-1a) having a bridged cyclic hydrocarbon group with 10 to 20 carbon atoms and a polymerizable monomer (m-1b) represented by the following formula (1), acrylic acid (m-2), and a polymerizable monomer (m-3) containing an aromatic ring, to a compound (m-4) containing an ethylenically unsaturated group having a group reactive with a carboxyl group. In the formula, the polymerizable monomer (m-1a) does not include the polymerizable monomer (m-1b).

[0023] The resin (A-1b) is a resin obtained by adding a part of the hydroxyl groups in the resin (A-1a) to one or more selected from a compound (m-5) containing an ethylenically unsaturated group having an isocyanate group and a polyanhydride (m-6). The hydroxyl group is a hydroxyl group generated by ring-opening addition of a monomer having an epoxy group or an oxetanyl group as the compound (m-4) containing an ethylenically unsaturated group in the resin (A-1a).

[0024]

[0025] In formula (1), R1 and R2 each independently represent a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms, and R1 and R2 may also be bonded to form a cyclic structure. R3 and R4 each independently represent a hydrogen atom, or a linear or branched hydrocarbon group having 1 to 4 carbon atoms.

[0026] [2]. The pigment dispersion composition according to [1], wherein the pigment (B) contains a pigment having a halogenated phthalocyanine skeleton.

[0027] [3]. The pigment dispersion composition according to [1] or [2], wherein the polymer dispersant (C) has at least one group selected from a tertiary amino group and a quaternary ammonium cationic group.

[0028] [4]. The pigment dispersion composition according to any one of [1] to [3], characterized in that the polymer dispersant (C) is

[0029] At least one monomer selected from monomers having a tertiary amino group and an ethylenically unsaturated group, and monomers having a quaternary ammonium cation group and an ethylenically unsaturated group, and

[0030] other monomers having an ethylenically unsaturated group

[0031] block polymer.

[0032] [5]. The pigment dispersion composition according to any one of [1] to [4], wherein the group reactive with a carboxyl group in the ethylenically unsaturated group-containing compound (m-4) is an epoxy group or an oxetanyl group.

[0033] [6]. The pigment dispersion composition according to any one of [1] to [5], wherein when the total of the polymerizable monomer (m-1), the acrylic acid (m-2), and the aromatic ring-containing polymerizable monomer (m-3) of the copolymer (P) is 100 mol%, the proportion of the aromatic ring-containing polymerizable monomer (m-3) is 9 to 70 mol%.

[0034] [7]. The pigment dispersion composition according to any one of [1] to [6], wherein the binder resin (A-1) is the resin (A-1b).

[0035] [8]. The pigment dispersion composition according to any one of [1] to [7], per 100 parts by mass of the pigment (B),

[0036] containing 10 to 50 parts by mass of the binder resin (A-1), and

[0037] containing 10 to 80 parts by mass of the polymer dispersant (C).

[0038] [9]. A photosensitive coloring composition, characterized by containing the pigment dispersion composition according to any one of [1] to [8], a binder resin (A-2), a reactive diluent (E), and a photopolymerization initiator (F).

[0039]

[10] . The photosensitive coloring composition according to [9], per 100 parts by mass of the pigment (B),

[0040] containing a total of 50 to 280 parts by mass of the binder resins (A-1) and (A-2),

[0041] containing 10 to 80 parts by mass of the polymer dispersant (C),

[0042] containing 40 to 200 parts by mass of the reactive diluent (E), and

[0043] containing 0.1 to 10 parts by mass of the photopolymerization initiator (F).

[0044]

[11] . A resin cured film is formed by curing the photosensitive coloring composition described in [9] or

[10] .

[0045]

[12] . A color filter has a cured product of the photosensitive coloring composition described in [9] or

[10] .

[0046]

[13] . An image display component includes the color filter described in

[12] .

[0047] Advantages of the Invention

[0048] According to the present invention, a pigment dispersion composition with good pigment dispersibility and storage stability can be provided. In addition, by using this pigment dispersion composition, a photosensitive coloring composition capable of obtaining a resin cured film with excellent developability, heat resistance, solvent resistance, and pattern adhesion can be provided. Further, a color filter having a cured product of this photosensitive coloring composition and an image display component including this color filter can be provided. Detailed Embodiments

[0049] The embodiments of the present invention will be described in detail below. However, the present invention is not limited to the embodiments described below.

[0050] The embodiments of the present invention will be described in detail below. However, the present invention is not limited to the embodiments described below. It should be noted that in this specification, the so-called “(meth)acryloyloxy” means one or more selected from methacryloyloxy and acryloyloxy. The same applies to “(meth)acrylic acid” and “(meth)acrylate”.

[0051] <Pigment Dispersion Composition>

[0052] The pigment dispersion composition of this embodiment contains: binder resin (A-1), pigment (B), polymer dispersant (C), and solvent (D-1).

[0053] [Binder Resin (A-1)]

[0054] Binder resin (A-1) is at least one resin selected from the following resin (A-1a) and resin (A-1b).

[0055] The resin (A-1a) is a resin obtained by adding a part of the carboxyl groups of the copolymer (P) to a compound (m-4) containing an ethylenically unsaturated group. The compound (m-4) containing an ethylenically unsaturated group has a group reactive with a carboxyl group. The copolymer (P) is a copolymer of monomers (M), and the monomers (M) include at least one polymerizable monomer (m-1) selected from polymerizable monomers (m-1a) having a bridged cyclic hydrocarbon group with 10 to 20 carbon atoms (excluding polymerizable monomer (m-1b)) and polymerizable monomer (m-1b) represented by the following formula (1), acrylic acid (m-2), and a polymerizable monomer (m-3) containing an aromatic ring.

[0056] The resin (A-1b) is a resin obtained by adding the aforementioned resin (A-1a) to one or more selected from a compound (m-5) containing an ethylenically unsaturated group and a polyanhydride (m-6). The compound (m-5) containing an ethylenically unsaturated group has an isocyanato group. The resin (A-1a) is a resin obtained by adding a part of the carboxyl groups of the copolymer (P) to the compound (m-4) containing an ethylenically unsaturated group having an epoxy group or an oxetanyl group. The resin (A-1a) has a plurality of hydroxyl groups generated by ring-opening addition thereof. A part of the plurality of hydroxyl groups has been added to one or more selected from the compound (m-5) containing an ethylenically unsaturated group and the polyanhydride (m-6).

[0057] One form of the adhesive resin (A-1) of the present embodiment is a resin (A-1a) obtained by adding a part of the carboxyl groups of a copolymer (P) having a carboxyl group to a compound (m-4) containing an ethylenically unsaturated group having a reactive group. The copolymer (P) is a copolymer of monomers (M), and the monomers (M) include at least one polymerizable monomer (m-1) selected from polymerizable monomers (m-1a) having a bridged cyclic hydrocarbon group with 10 to 20 carbon atoms (excluding polymerizable monomer (m-1b)) and polymerizable monomer (m-1b) represented by the following formula (1), acrylic acid (m-2), and a polymerizable monomer (m-3) containing an aromatic ring.

[0058]

[0059] (In formula (1), R1 and R2 each independently represent a hydrogen atom or a hydrocarbon group with 1 to 20 carbon atoms, and R1 and R2 may also be bonded to form a cyclic structure. R3 and R4 each independently represent a hydrogen atom, or a linear or branched hydrocarbon group with 1 to 4 carbon atoms).

[0060] In addition, another form of the adhesive resin (A-1) of the present embodiment is a resin (A-1b) obtained by further adding one or more selected from a compound (m-5) having an ethylenically unsaturated group containing an isocyanate group and a polyanhydride (m-6) to the above resin (A-1a).

[0061] First, a copolymer (P) which is a precursor of the adhesive resin (A-1) of the present embodiment will be described.

[0062] "Copolymer (P)"

[0063] The copolymer (P) used in the present embodiment contains, as constituent monomers (M): at least one polymerizable monomer (m-1) selected from a polymerizable monomer (m-1a) having a bridged cyclic hydrocarbon group with 10 to 20 carbon atoms and a polymerizable monomer (m-1b) represented by the following formula (1), acrylic acid (m-2), and a polymerizable monomer (m-3) containing an aromatic ring. Regarding the "polymerizable monomer (m-1a) having a bridged cyclic hydrocarbon group with 10 to 20 carbon atoms", the "polymerizable monomer (m-1b) represented by the following formula (1)", the "polymerizable monomer (m-1)", the "acrylic acid (m-2)", and the "polymerizable monomer (m-3) containing an aromatic ring", there are cases where they are respectively referred to as "monomer (m-1a)", "monomer (m-1b)", "monomer (m-1)", "monomer (m-2)", and "monomer (m-3)".

[0064] "Monomer (m-1)"

[0065] Monomer (m-1) is at least one selected from monomer (m-1a) and monomer (m-1b).

[0066] Monomer (m-1a) has a bridged cyclic hydrocarbon group with 10 to 20 carbon atoms. Here, the so-called bridged cyclic hydrocarbon preferably has a structure represented by the following formula (3) or (4). Examples of the bridged cyclic hydrocarbon include adamantane and norbornane. The so-called bridged cyclic hydrocarbon group refers to the remaining part after removing a part of the hydrogen atoms in this structure. In addition, monomer (m-1a) is defined not to include monomer (m-1b) described later.

[0067]

[0068] In formula (3), A and B each independently represent a linear or branched alkylene group (including cyclic) with 1 to 10 carbon atoms, A and B may be the same or different, and the branches of A and B may be bonded to each other to form a cyclic structure, and R5 represents a hydrogen atom or a methyl group.

[0069]

[0070] In formula (4), A', B' and D each independently represent a linear or branched alkylene group having 1 to 10 carbon atoms (including cyclic), A', B' and D may be the same or different, and the branches of A', B' and D may be bonded to each other to form a cyclic structure, and R6 represents a hydrogen atom or a methyl group.

[0071] As the monomer (m-1a), a (meth)acrylate having a bridged cyclic hydrocarbon group having 10 to 20 carbon atoms is preferred, and an adamantyl (meth)acrylate or a (meth)acrylate having a structure represented by the following formula (5) is more preferred.

[0072]

[0073] In formula (5), R7 to R9 each independently represent a hydrogen atom or a methyl group, R10 and R11 represent a hydrogen atom or a methyl group, or may be bonded to form a saturated or unsaturated ring, and the ring is preferably a 5-membered ring or a 6-membered ring, and * represents a bonding bond connected to the (meth)acryloyloxy group.

[0074] Specific examples of the (meth)acrylate having the structure represented by the above formula (5) include dicyclopenteny (meth)acrylate (also known as: hexahydro-4,7-methano-1H-indenyl (meth)acrylate), dicyclopentyl (meth)acrylate (also known as: tricyclo[5.2.1.02,6]dec-8-yl (meth)acrylate), isobornyl (meth)acrylate, etc. These can be used alone or in combination of two or more.

[0075] The monomer (m-1b) is the polymerizable monomer represented by the above formula (1). In the above formula (1), examples of the substituent in the hydrocarbon group having 1 to 20 carbon atoms which may have a substituent represented by R1 and R2 include an alkoxy group, an aryl group, etc. Specific examples of the hydrocarbon group having 1 to 20 carbon atoms which may have a substituent include linear or branched alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, tert-pentyl, stearyl, lauryl, 2-ethylhexyl; alicyclic groups such as cyclohexyl, tert-butylcyclohexyl, dicyclopentadienyl, tricyclodecyl, isobornyl, adamantyl, 2-methyl-2-adamantyl; alkoxy-substituted alkyl groups such as 1-methoxyethyl, 1-ethoxyethyl; aryl-substituted alkyl groups such as phenylalkyl, etc. In addition, specific examples of the linear or branched hydrocarbon group having 1 to 4 carbon atoms represented by R3 and R4 include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc.

[0076] Specific examples of the monomer (m-1b) include norbornene (bicyclo[2.2.1]hept-2-ene), 5-methylbicyclo[2.2.1]hept-2-ene, tetracyclo[4.4.0.1 2,5 .17,10 dodec-3-ene, 8-ethyltetracyclo[4.4.0.1 2,5 .1 7,10 dodec-3-ene, dicyclopentadiene, tricyclo[5.2.1.0 2,6 dec-8-ene, tricyclo[4.4.0.1 2,5 undec-3-ene, tricyclo[6.2.1.0 1 ,8 undec-9-ene, tetracyclo[4.4.0.1 2,5 .1 7,10 .0 1,6 dodec-3-ene, 8-ethylidene tetracyclo[4.4.0.1 2,5 .1 7,12 dodec-3-ene, pentacyclo[6.5.1.1 3,6 .0 2,7 .0 9,13 pentadec-4-ene etc. These can be used alone or in combination of two or more kinds.

[0077] By including monomer (m-1a) and / or monomer (m-1b), a color filter having high surface hardness and capable of suppressing bleeding of a colorant can be provided. At the same time, it can have high thermal decomposition resistance and high heat yellowing resistance, and can make the color change of the baked color filter small.

[0078] It should be noted that either monomer (m-1a) or monomer (m-1b) can be used alone, or both can be used. In particular, from the viewpoint of hardness, as monomer (m-1), adamantyl (meth)acrylate or the (meth)acrylate having the structure represented by the above formula (5) is preferred, and dicyclopentyl (meth)acrylate is more preferred.

[0079] "Monomer (m-2)"

[0080] The copolymer (P) of the present embodiment contains monomer (m-2) as a constituent monomer (M). Monomer (m-2) is acrylic acid. The binder resin (A-1) has a higher affinity for the alkali developer due to the carboxyl group derived from monomer (m-2), and a colored photosensitive composition with excellent developability can be obtained, and a high-precision color filter with strict dimensional accuracy can be provided. In particular, by using monomer (m-2) as the copolymer (P), a pigment dispersion composition with excellent pigment dispersibility and storage stability can be obtained compared to other polymerizable monomers containing acid groups such as carboxyl group, sulfo group, and phospho group. Therefore, an increase in the brightness or transmittance of the color filter with the improvement of pigment dispersibility can be expected. In addition, with the improvement of pigment dispersibility, scattering caused by pigment particles during exposure can also be reduced, which also contributes to the improvement of the developability of the photosensitive coloring composition.

[0081] The copolymer (P) of the present embodiment may be used in combination with a polymerizable monomer containing an acid group other than monomer (m-2) as a constituent monomer within the range that does not impair the effects of the present invention, but for the above reasons, it is preferably not used.

[0082] "Monomer (m-3)"

[0083] Monomer (m-3) is a monomer other than monomer (m-1a), monomer (m-1b), and monomer (m-2), and there is no particular limitation as long as it is a polymerizable monomer containing an aromatic ring. By including monomer (m-3), the affinity with pigment (B) can be improved, and a pigment dispersion composition with excellent pigment dispersibility and storage stability can be obtained. Along with this, even in the case where the concentration of the dispersant or binder resin is reduced due to the high concentration of the pigment, a pigment dispersion composition capable of obtaining sufficient pigment dispersibility and storage stability can be provided.

[0084] Specific examples of monomer (m-3) include benzyl (meth)acrylate, phenyl (meth)acrylate, triphenylmethyl (meth)acrylate, isopropylphenyl (meth)acrylate, rosin (meth)acrylate, naphthyl (meth)acrylate, anthryl (meth)acrylate, 4-hydroxyphenyl (meth)acrylate, styrene, α-, o-, m-, p-alkyl, nitro, cyano, amide derivatives of styrene, N-phenylmaleimide, N-(4-hydroxyphenyl)maleimide, etc. In particular, from the viewpoints of copolymerization ease or availability, benzyl (meth)acrylate, phenyl (meth)acrylate, styrene, and α-, o-, m-, p-alkyl derivatives of styrene are preferably used. These compounds can be used alone or in combination of two or more.

[0085] "Mixing ratio of each monomer in copolymer (P)"

[0086] There is no particular limitation on the blending ratio (molar ratio of each monomer) of each monomer in the copolymer (P) of the present embodiment. When the total of monomers (m-1), (m-2), and (m-3) is set to 100 mol%, the proportion of monomer (m-1) is preferably 1 to 40 mol%, more preferably 2 to 20 mol%, and still more preferably 5 to 15 mol%. It should be noted that there is no limitation on the ratio of monomer (m-1a) and / or (m-1b) in monomer (m-1), and any blending ratio can be adopted. When the blending ratio of monomer (m-1) is 1 mol% or more, the desired properties derived from monomer (m-1) can be obtained. When the blending ratio is 40 mol% or less, other polymerizable monomers can be sufficiently blended, and other properties can be attempted to be combined.

[0087] When the total of monomers (m-1), (m-2), and (m-3) is set to 100 mol%, the proportion of monomer (m-2) is preferably 10 to 90 mol%, more preferably 20 to 85 mol%, and still more preferably 30 to 70 mol%. When the blending ratio of monomer (m-2) is 10 mol% or more, good developability of the pigment dispersion composition can be obtained, and a sufficient amount of ethylenically unsaturated groups can be introduced into the side chain of copolymer (P). On the other hand, when the blending ratio is 90 mol% or less, other polymerizable monomers can be sufficiently blended, and other properties can be attempted to be combined.

[0088] When the total of monomers (m-1), (m-2), and (m-3) is set to 100 mol%, the proportion of monomer (m-3) is preferably 9 to 70 mol%, more preferably 13 to 60 mol%, and still more preferably 20 to 55 mol%. When the blending ratio is 9 mol% or more, the desired properties derived from the monomer containing an aromatic group can be obtained. When the blending ratio is 70 mol% or less, other polymerizable monomers can be sufficiently blended, and other properties can be attempted to be combined.

[0089] "Other polymerizable monomers"

[0090] The copolymer (P) of the present embodiment may also contain structural units derived from other polymerizable monomers within a range that does not interfere with the desired properties derived from the aforementioned monomers (m-1), (m-2), and (m-3). That is, it may contain copolymerizable other polymerizable monomers other than the aforementioned monomers (m-1a), (m-1b), (m-2), and (m-3). The other polymerizable monomers are generally free-radically polymerizable compounds having an ethylenically unsaturated group, and specific examples thereof include: dienes such as butadiene; non-reactive (meth)acrylates such as methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, isopropyl (meth)acrylate, n-butyl (meth)acrylate, sec-butyl (meth)acrylate, isobutyl (meth)acrylate, tert-butyl (meth)acrylate, pentyl (meth)acrylate, neopentyl (meth)acrylate, isopentyl (meth)acrylate, hexyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, lauryl (meth)acrylate, dodecyl (meth)acrylate, cyclopentyl (meth)acrylate, cyclohexyl (meth)acrylate, methylcyclohexyl (meth)acrylate, ethylcyclohexyl (meth)acrylate, allyl (meth)acrylate, tetrahydrofurfuryl (meth)acrylate, 3-(N,N-dimethylamino)propyl (meth)acrylate; reactive (meth)acrylates such as 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 3-hydroxybutyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, 3-hydroxypentyl (meth)acrylate, 4-hydroxypentyl (meth)acrylate, 5-hydroxypentyl (meth)acrylate, 4-hydroxyhexyl (meth)acrylate, 5-hydroxyhexyl (meth)acrylate, 6-hydroxyhexyl (meth)acrylate, 5-hydroxy-3-methyl-pentyl (meth)acrylate, cyclohexane-1,4-dimethanol mono(meth)acrylate, 2-(2-hydroxyethyloxy)ethyl (meth)acrylate, 2,3-dihydroxy (meth)acrylate, butanetriol mono(meth)acrylate, pentaerythritol mono(meth)acrylate, glycidyl (meth)acrylate, glycidyl ether of 4-hydroxybutyl (meth)acrylate, 3,4-epoxycyclohexylmethyl (meth)acrylate, (3-ethyloxetane-3-yl)methyl (meth)acrylate, 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, 1,1-(bisacryloxymethyl)ethyl isocyanate, and compounds having a blocked isocyanate group obtained by blocking the isocyanate group of the aforementioned ethylenically unsaturated compound having an isocyanate group with a blocking agent.(Meth)acrylamide, (meth)acrylic acid N,N-dimethylamide, (meth)acrylic acid N,N-diethylamide, (meth)acrylic acid N,N-dipropylamide, (meth)acrylic acid N,N-di-isopropylamide, (meth)acrylic acid anthracenylamide and other (meth)acrylamides; vinyl compounds such as (meth)acrylamide benzene, (meth)acrylonitrile, acrolein, vinyl chloride, vinylidene chloride, vinyl fluoride, vinylidene fluoride, N-vinylpyrrolidone, vinylpyridine, vinyl acetate, vinyltoluene, etc.; maleimides such as N-cyclohexylmaleimide, N-laurylmaleimide, etc.; unsaturated dicarboxylic acid diesters such as diethyl citraconate, diethyl maleate, diethyl fumarate, diethyl itaconate, etc. These can be used alone as needed, or two or more of them can be used in combination.

[0091] "Ratio of other polymerizable monomers"

[0092] Regarding the ratio of other polymerizable monomers in the copolymer (P) of the present embodiment, when the total of the monomers (m-1), (m-2), (m-3), and other polymerizable monomers is set to 100 mol%, it is preferably 10 mol% or less, more preferably 5 mol% or less.

[0093] "Compound added to the copolymer (P) etc."

[0094] Next, an adhesive resin (A-1) obtained by adding the copolymer (P), a compound (m-4) having an ethylenically unsaturated group having a group reactive with a carboxyl group, and further one or more selected from a compound (m-5) having an ethylenically unsaturated group having an isocyanate group and a polyanhydride (m-6) as optional compounds will be described.

[0095] Regarding the "compound (m-4) having an ethylenically unsaturated group having a group reactive with a carboxyl group", the "compound (m-5) having an ethylenically unsaturated group having an isocyanate group", and the "polyanhydride (m-6)", there are cases where they are respectively referred to as the "compound (m-4)", the "compound (m-5)", and the "compound (m-6)".

[0096] "Compound (m-4)"

[0097] The compound (m-4) has a "group reactive with a carboxyl group" and an "ethylenically unsaturated group". Examples of the group reactive with a carboxyl group include an epoxy group, an oxetanyl group, an isocyanate group, a hydroxyl group, and an amino group.

[0098] By adding the carboxyl group of the monomer (m-2) from the aforementioned copolymer (P) to the group reactive with the carboxyl group in the compound (m-4), an ethylenically unsaturated group can be introduced into the side chain of the aforementioned copolymer (P). The binder resin (A-1) has an ethylenically unsaturated group from the compound (m-4), inhibits the bleeding of the pigment (B), and can provide a pigment dispersion composition exhibiting excellent resist properties such as heat resistance, solvent resistance, pattern adhesion, and developability.

[0099] Specific examples of the compound (m-4) include glycidyl (meth)acrylate, glycidyl 4-hydroxybutyl (meth)acrylate, 3,4-epoxycyclohexylmethyl (meth)acrylate, (3-ethyloxetane-3-yl)methyl (meth)acrylate, 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, 1,1-bis(acryloxymethyl)ethyl isocyanate, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 3-hydroxybutyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, 3-hydroxypentyl (meth)acrylate, 4-hydroxypentyl (meth)acrylate, 5-hydroxypentyl (meth)acrylate, 4-hydroxyhexyl (meth)acrylate, 5-hydroxyhexyl (meth)acrylate, 6-hydroxyhexyl (meth)acrylate, 5-hydroxy-3-methylpentyl (meth)acrylate, cyclohexane-1,4-dimethanol mono(meth)acrylate, 2-(2-hydroxyethyloxy)ethyl (meth)acrylate, 2,3-dihydroxy (meth)acrylate, butanetriol mono(meth)acrylate, pentaerythritol mono(meth)acrylate, 2-aminoethyl (meth)acrylate, 2-dimethylaminoethyl (meth)acrylate, and 2-monomethylaminoethyl (meth)acrylate. These can be used alone or in combination of two or more. Among them, from the viewpoints of easy availability, reactivity with the copolymer (P), and further addition of the following compound (m-5) or compound (m-6) as optional monomers, those having an epoxy group or an oxetanyl group are preferred, and glycidyl (meth)acrylate, glycidyl 4-hydroxybutyl (meth)acrylate, 3,4-epoxycyclohexylmethyl (meth)acrylate, and (3-ethyloxetane-3-yl)methyl (meth)acrylate are more preferred, and glycidyl (meth)acrylate is even more preferred.

[0100] "Compound (m-5)"

[0101] When using a compound having an epoxy group or an oxetanyl group as the compound (m-4), the compound (m-5) may be further used as needed. The compound (m-5) is a monomer having an isocyanate group and an ethylenically unsaturated group, and does not have a carboxyl group, an epoxy group, or an oxetanyl group. By adding a part of the plurality of hydroxyl groups of the resin (A-1a) to the compound (m-5), the resin (A-1b) can be obtained. As a result, an ethylenically unsaturated group is further introduced into the resin (A-1a). By using the resin (A-1b), various resist characteristics such as heat resistance, solvent resistance, pattern adhesion, and developability can be further improved. The plurality of hydroxyl groups of the resin (A-1a) are formed by ring-opening addition of the carboxyl group of the monomer (m-2) from the copolymer (P) to the epoxy group or oxetanyl group of the compound (m-4). The resin (A-1a) is a form of the binder resin (A-1), and the resin (A-1b) is another form of the binder resin (A-1).

[0102] Specific examples of the compound (m-5) 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, 1,1-bis(acryloxymethyl)ethyl isocyanate, etc. These can be used alone or in combination of two or more. Among them, from the viewpoint of easy availability, 2-isocyanatoethyl (meth)acrylate is preferred.

[0103] "Compound (m-6)"

[0104] The compound (m-6) is a polyanhydride. When using a compound having an epoxy group or an oxetanyl group as the compound (m-4), the compound (m-6) may be further used as needed. As long as it has an anhydride structure, the compound (m-6) is not particularly limited, and those having a ring structure that does not produce by-products after the reaction are preferred. By adding a part of the plurality of hydroxyl groups of the resin (A-1a) to the compound (m-6), the resin (A-1b) can be obtained. As a result, a carboxyl group can be introduced into the resin (A-1a). By using the resin (A-1b), it will contribute to the improvement of the developability of the photosensitive coloring composition. The plurality of hydroxyl groups of the resin (A-1a) are formed by ring-opening addition of the carboxyl group of the monomer (m-2) from the copolymer (P) to the epoxy group or oxetanyl group of the compound (m-4). The resin (A-1a) is a form of the binder resin (A-1), and the resin (A-1b) is another form of the binder resin (A-1).

[0105] As the compound (m-6), 1,2,3,6-tetrahydrophthalic anhydride, hexahydrophthalic anhydride, 4-methylhexahydrophthalic anhydride, bicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride, methylbicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride, succinic anhydride, octenyl succinic anhydride, etc. can be specifically cited. These can be used alone or two or more thereof can be used. Among them, from the viewpoint of ease of availability, succinic anhydride is preferred.

[0106] "Import ratio of compound (m-4)"

[0107] Regarding the import ratio of compound (m-4) relative to the aforementioned copolymer (P), when the total of monomers (m-1) to (m-3) is set to 100 mol%, it is preferably 5 to 90 mol%, more preferably 10 to 70 mol%, and still more preferably 10 to 40 mol%. In addition, when acrylic acid (m-2) is set to 100 mol%, it is preferably 5 to 90 mol%, more preferably 10 to 70 mol%, and still more preferably 20 to 50 mol%.

[0108] By making the blending ratio of compound (m-4) fall within the aforementioned range, the effects brought about by the introduction of the ethylenically unsaturated group can be exerted, and furthermore, the residue of unreacted compound (m-4) can also be reduced.

[0109] "Total import ratio of compound (m-5) and compound (m-6)"

[0110] Regarding the total import ratio of compound (m-5) and compound (m-6) relative to the aforementioned copolymer (P), when the total of monomers (m-1) to (m-3) is set to 100 mol%, it is preferably 3 to 70 mol%, more preferably 5 to 50 mol%, and still more preferably 5 to 25 mol%. In addition, when compound (m-4) is set to 100 mol%, it is preferably 5 to 90 mol%, more preferably 20 to 80 mol%, and still more preferably 40 to 70 mol%.

[0111] By making the total import ratio of the ethylenically unsaturated group-containing compound (m-5) and the polyanhydride (m-6) fall within the aforementioned range, the effects brought about by the introduction can be exerted, and furthermore, the residue of unreacted monomers can also be reduced.

[0112] It should be noted that there is no limitation on the incorporation ratio in the case of using the compound (m-5) and the compound (m-6) in combination, and any incorporation ratio can be selected according to the desired performance. That is, when improving heat resistance, solvent resistance, and pattern adhesion, the ratio of the compound (m-5) can be increased; when improving developability, the ratio of the compound (m-6) can be increased. When all properties are desired to be improved, the compound (m-5) and the compound (m-6) can be increased in the same ratio.

[0113] By adjusting the incorporation ratio of (m-5) and the compound (m-6) as described above, the added value of the desired performance can be obtained.

[0114] "Physical properties of the binder resin (A-1)"

[0115] The acid value of the binder resin (A-1) in the present embodiment (the value measured according to the regulations shown in JIS K6901 5.3, etc.) includes the carboxylic acid from acrylic acid (m-2), and there is no particular limitation as long as it is 0 mgKOH / g or more, preferably 10 to 400 mgKOH / g, more preferably 30 to 300 mgKOH / g, and most preferably 50 to 200 mgKOH / g. If the acid value of the binder resin (A-1) is 10 mgKOH / g or more, the developability of the photosensitive coloring composition is good. On the other hand, if the acid value of the binder resin (A-1) is 400 mgKOH / g or less, a uniform composition can be provided without impairing the affinity with the pigment dispersion composition and other components contained in the photosensitive coloring composition.

[0116] The molecular weight of the binder resin (A-1) in the present embodiment (weight average molecular weight in terms of polystyrene) is not particularly limited, preferably 1000 to 50000, more preferably 3000 to 40000, and most preferably 5000 to 30000. If the molecular weight of the binder resin (A-1) is 1000 or more, excellent heat resistance, solvent resistance, and pattern adhesion can be ensured. On the other hand, if the molecular weight of the binder resin (A-1) is 50000 or less, the molecular weight and viscosity during the production of the binder resin (A-1) can be controlled within an appropriate range, and a practical pigment dispersion composition and photosensitive coloring composition can be provided.

[0117] The alkenyl unsaturated group equivalent of the binder resin (A-1) in the present embodiment is not particularly limited as long as it has an alkenyl unsaturated group in the side chain of the copolymer (P), and is preferably 200 to 5000 g / mol, more preferably 300 to 2500 g / mol, and most preferably 500 to 2000 g / mol. If the alkenyl unsaturated group equivalent of the binder resin (A-1) is 5000 g / mol or less, excellent heat resistance, solvent resistance, and pattern adhesion can be ensured. On the other hand, if the alkenyl unsaturated group equivalent during the production of the binder resin (A-1) is 200 g / mol or more, a practical pigment dispersion composition and a photosensitive coloring composition that can ensure the stability during the production of the binder resin (A-1) can be provided.

[0118] "Method for Producing Binder Resin (A-1)"

[0119] The copolymer (P) as a precursor of the binder resin (A-1) can be obtained by carrying out a copolymerization reaction according to a well-known radical polymerization method in the art. For example, after dissolving the monomers used for copolymerization in a solvent, a polymerization initiator is added to the solution, and the reaction is carried out at 50 to 130°C for 1 to 20 hours. In addition, the monomers used for copolymerization and the polymerization initiator can be added dropwise to a solvent adjusted to 50 to 130°C while the reaction proceeds.

[0120] As the solvent that can be used in this copolymerization reaction, as long as it is inert to radical polymerization, it is not particularly limited, and commonly used organic solvents can be used. Specific examples include ethylene glycol ether solvents such as propylene glycol monomethyl ether and propylene glycol monomethyl ether acetate; aromatic solvents such as toluene and xylene, and ester solvents such as ethyl acetate, isopropyl acetate, and ethyl lactate. These can be used alone or in combination of two or more. In particular, among these, ethylene glycol ether solvents are preferably used.

[0121] The amount of the solvent used in this copolymerization reaction is not particularly limited. When the total amount of the monomers used for copolymerization is set to 100 parts by mass, it is generally 30 to 1000 parts by mass, preferably 50 to 800 parts by mass. In particular, by setting the amount of the solvent used to 1000 parts by mass or less, a decrease in the molecular weight of the copolymer (P) due to chain transfer can be suppressed, and the viscosity of the copolymer (P) can be controlled within an appropriate range. In addition, by setting the amount of the solvent used to 30 parts by mass or more, abnormal polymerization reactions can be prevented, and the polymerization reaction can be carried out stably while preventing the coloring or gelation of the copolymer (P).

[0122] As the polymerization initiator that can be used in this copolymerization reaction, any initiator that can initiate free radical polymerization can be used without particular limitation, and commonly used organic peroxide catalysts or azo compounds can be used. Specific examples include azobisisobutyronitrile, azodiisovaleronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), dimethyl azobis(2-methylpropionate), benzoyl peroxide, dicumyl peroxide, diisopropyl peroxide, di-tert-butyl peroxide, tert-butyl peroxybenzoate, tert-hexyl peroxybenzoate, tert-butyl peroxy-2-ethylhexanoate, tert-hexyl peroxy-2-ethylhexanoate, 1,1,3,3-tetramethylbutyl peroxy-2-ethylhexanoate, etc. These can be used alone or in combination of two or more, and it is advisable to select a free radical polymerization initiator with an appropriate half-life according to the polymerization temperature.

[0123] The blending amount of the polymerization initiator used in this copolymerization reaction is not particularly limited. When the total amount of the monomers used in the copolymerization is set to 100 parts by mass, it is generally 0.5 to 20 parts by mass, preferably 1.0 to 10 parts by mass.

[0124] As a method for adding a part of the carboxyl group of the aforementioned copolymer (P) to the compound (m-4), well-known addition reactions can be used. For example, after adding a polymerization inhibitor and a catalyst to the solution of the aforementioned copolymer (P), the compound (m-4) is added, and the addition reaction or dehydration reaction is carried out under the conditions of room temperature to 150 °C (preferably 50 to 120 °C). Here, the polymerization inhibitor is added to prevent side reactions of the introduced unsaturated groups. Specific examples of the polymerization inhibitor include hydroquinone, methylhydroquinone, hydroquinone monomethyl ether, dibutylhydroxytoluene, etc. In addition, specific examples of the catalyst include tertiary amines such as triethylamine, quaternary ammonium salts such as triethylbenzylammonium chloride, phosphorus compounds such as triphenylphosphine, and organometallic compounds such as chromium or tin.

[0125] A part of the carboxyl group of the aforementioned copolymer (P) is subjected to ring-opening addition with the epoxy group and oxetanyl group of the compound (m-4) to generate multiple hydroxyl groups. If a part of the aforementioned multiple hydroxyl groups is further added with one or more selected from the compound (m-5) containing an ethylenically unsaturated group and the polyanhydride (m-6), as a method for the addition reaction, the compound (m-5) and the compound (m-6) can be continuously added after the addition reaction of the aforementioned compound (m-4). If necessary, the reaction temperature can be adjusted, or the aforementioned catalyst can be added additionally.

[0126] [Pigment (B)]

[0127] The pigment (B) in this embodiment is not particularly limited as long as it can be uniformly dispersed in the composition to form the pixels of the color filter. Pigments of the three primary colors of light, namely red, green, and blue, can be used, and various pigments such as yellow, orange, and purple that can be used as complementary colors, and pigments such as black and brown that can be used as black matrices can also be used. In addition, as the chemical structure of the pigment (B), all organic pigments such as isoindolinone, isoindoline, methineimine, anthraquinone, anthrone, xanthene, diketopyrrolopyrrole, perylene, violanthrone, quinacridone, indigo, dioxazine, indigo, phthalocyanine, anthocyanin, and azo can be cited, or inorganic pigments such as carbon black, titanium black, and titanium dioxide can be used.

[0128] Among them, the pigment (B) in this embodiment is preferably a green pigment having a halogenated phthalocyanine skeleton represented by the following formula (6).

[0129]

[0130] In formula (6), M represents a divalent or tetravalent metal atom. From the viewpoint of color reproducibility, zinc or copper is preferred, and zinc is particularly preferred. X represents any one of a hydrogen atom, a chlorine atom, and a bromine atom, and at least one chlorine atom or bromine atom is included. The addition ratio of the chlorine atom and the bromine atom changes accordingly corresponding to the luminance or color reproducibility. When the chlorine atom is more and the bromine atom is less, it becomes high luminance. On the contrary, when the bromine atom is more and the chlorine atom is less, the color reproducibility tends to be good. The chlorine atom is preferably 1 or more and 10 or less, more preferably 1.5 or more and 8 or less. The bromine atom is preferably 5 or more and 15 or less, more preferably 7 or more and 14 or less.

[0131] By using the above-mentioned pigment (B) together with the binder resin (A-1) and the polymer dispersant (C) described later, a pigment dispersion composition excellent in pigment dispersibility and storage stability can be obtained, and a color filter with high luminance and a wide color reproduction range can be provided. At the same time, heat resistance, solvent resistance, and pattern adhesion of the colored pattern can be imparted.

[0132] Commercially available products can be used as the halogenated phthalocyanine pigment, or it can be prepared by oneself. Examples of commercially available products include C.I. Pigment Green 7, 36, 58, 59, etc. Among them, for high luminance or high color reproducibility, it is preferred to use C.I. Pigment Green 58, 59.

[0133] In the case of self-preparation, well-known manufacturing methods are used. For example, there can be mentioned: a method of forming a phthalocyanine skeleton using phthalic acid or phthalonitrile in which part or all of the hydrogen atoms of the aromatic ring are substituted by halogen atoms as a starting material in the presence of a catalyst such as ammonium molybdate; or a method of halogenating phthalocyanine with chlorine gas or bromine gas. The crude pigment obtained by these methods is dry-ground in a crusher such as a ball mill or a vibration mill and treated by a well-known solvent grinding method or the like to obtain the desired green pigment.

[0134] It should be noted that as long as it contains at least a halogenated phthalocyanine skeleton and can be uniformly dispersed with other compositions to form pixels of a color filter, other pigments can also be used in combination. There is no particular limitation. Starting with the pigments of the three primary colors of light, namely red, green, and blue, various colored pigments such as yellow, orange, and purple that can be used as complementary colors, and black, brown, etc. that can be used as black matrix pigments can be used. In addition, as the chemical structures of these pigments, all organic pigments such as isoindolinone, isoindoline, methineimine, anthraquinone, anthrone, xanthene, diketopyrrolopyrrole, perylene, violanthrone, quinacridone, indigo, dioxazine, indigo, anthocyanin, azo, etc., or inorganic pigments such as carbon black, titanium black, titanium dioxide, etc. can be mentioned.

[0135] As specific examples of other pigments, there can be mentioned yellow pigments such as C.I. Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 194, 214, etc.; orange pigments such as C.I. Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73, etc.; red pigments such as C.I. Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 180, 192, 209, 215, 216, 224, 242, 254, 255, 264, 265, etc.; blue pigments such as C.I. Pigment Blue 15, 15:3, 15:4, 15:6, 60, etc.; purple pigments such as C.I. Pigment Violet 1, 19, 23, 29, 32, 36, 38, etc.; brown pigments such as C.I. Pigment Brown 23, 25, etc.; black pigments such as C.I. Pigment Black 1, 7, carbon black, titanium black, iron oxide, etc. Depending on the color of the pixel as the purpose, these pigments can be used alone or in combination of two or more.

[0136] Furthermore, as the colorant in the present embodiment, not only the pigment (B) but also a dye can be used in combination. When a dye is used in combination, compared with the case of using a pigment, it is possible to expect higher brightness, an expanded color reproduction range, and good developability. On the other hand, when a pigment is used in combination, it has excellent heat resistance compared with a dye, and there is little color change after the formation of the colored pattern. Depending on the color of the pixel as the required performance or purpose, a dye and a pigment can also be used in combination.

[0137] As the dye, from the viewpoints of solubility in the solvent (D-1) or alkali developer described later, interaction with other components in the resin composition, heat resistance, etc., it is preferable to use an acidic dye having an acidic group such as a carboxyl group, a salt of an acidic dye and a nitrogen compound, a sulfonamide body of an acidic dye, etc. Specific examples of such dyes include acid alizarin violet N; acid black 1, 2, 24, 48; acid blue 1, 7, 9, 25, 29, 40, 45, 62, 70, 74, 80, 83, 90, 92, 112, 113, 120, 129, 147; acid chromeviolet K; acid Fuchsin; acid green 1, 3, 5, 25, 27, 50; acid orange 6, 7, 8, 10, 12, 50, 51, 52, 56, 63, 74, 95; acid red 1, 4, 8, 14, 17, 18, 26, 27, 29, 31, 34, 35, 37, 42, 44, 50, 51, 52, 57, 69, 73, 80, 87, 88, 91, 92, 94, 97, 103, 111, 114, 129, 133, 134, 138, 143, 145, 150, 151, 158, 176, 183, 198, 211, 215, 216, 217, 249, 252, 257, 260, 266, 274; acid violet 6B, 7, 9, 17, 19; acid yellow 1, 3, 9, 11, 17, 23, 25, 29, 34, 36, 42, 54, 72, 73, 76, 79, 98, 99, 111, 112, 114, 116; food yellow 3 and derivatives thereof, etc. Among these, acidic dyes of the azo type, xanthene type, anthraquinone type, or phthalocyanine type are preferable. These dyes can be used alone or in combination of two or more.

[0138] [Polymeric dispersant (C)]

[0139] The polymer dispersant (C) is not particularly limited as long as it can disperse the pigment (B). From the viewpoints of pigment dispersibility and storage stability, a polymer compound having at least one substituent selected from a tertiary amino group and a quaternary ammonium cation group is preferred. Examples thereof include polyamines (or polyammonium cation salts) obtained by homopolymerizing or copolymerizing a monomer having a tertiary amino group and an ethylenically unsaturated group or a monomer having a quaternary ammonium cation group and an ethylenically unsaturated group, or polyamines (or polyammonium cation salts) obtained by copolymerizing these monomers with other monomers having an ethylenically unsaturated group, compounds obtained by alkylating a polymer compound containing one or more primary amino groups and / or secondary amino groups to form a tertiary amino group, or compounds obtained by further reacting the tertiary amino group with an acidic compound or an alkyl halide compound to form a quaternary ammonium cation salt, etc.

[0140] The aforementioned polymer dispersant (C) is preferably a block polymer of at least one monomer selected from a monomer having a tertiary amino group and an ethylenically unsaturated group and a monomer having a quaternary ammonium cation group and an ethylenically unsaturated group, and other monomers having an ethylenically unsaturated group. Examples of the aforementioned other monomers having an ethylenically unsaturated group include (meth)acrylates having an alkyl group, an aryl group, an aralkyl group, a cycloalkyl group, an alkylene glycol group, etc.

[0141] In particular, a polyamine (or polyammonium cation salt) obtained by block polymerizing a monomer having a tertiary amino group and an ethylenically unsaturated group and / or a monomer having a quaternary ammonium cation group and an ethylenically unsaturated group, and other monomers having an ethylenically unsaturated group is preferably used as the polymer dispersant (C). By using the polyamine (or polyammonium cation salt) obtained by block polymerization as the polymer dispersant (C), the tertiary amino group and / or the quaternary ammonium cation group will be locally present in the single terminal region, thereby improving the affinity with the pigment (B). In addition, the affinity of the other single terminal region with other pigment dispersion compositions (specifically, such as the binder resin (A-1) or the solvent (D-1) described later) will be high, whereby the pigment dispersibility or the storage stability of the pigment dispersion composition can be remarkably improved.

[0142] It should be noted that examples of the other monomers having an ethylenically unsaturated group for improving the affinity with other pigment dispersion compositions include (meth)acrylates having an alkyl group, an aryl group, an aralkyl group, a cycloalkyl group, an alkylene glycol group, etc.

[0143] The amine content of the polymer dispersant (C) can be quantitatively determined by measuring the amine value (a value measured according to the specifications shown in JIS K7237, etc.). The amine content of the polymer dispersant (C) in the present embodiment is not particularly limited, preferably 10 mgKOH / g to 200 mgKOH / g, more preferably 30 mgKOH / g to 160 mgKOH / g. When the amine value is 10 mgKOH / g or more, the affinity with the aforementioned pigment (B) can be improved, and sufficient pigment dispersibility or storage stability of the pigment dispersion composition can be obtained. On the other hand, when the amine value is 200 mgKOH / g or less, yellowing of the coloring pattern caused by the amine can be suppressed.

[0144] In addition, the molecular weight (weight-average molecular weight in terms of polystyrene) of the polymer dispersant (C) in the present embodiment is not particularly limited, preferably 1000 to 50000, more preferably 3000 to 30000. Furthermore, the molecular weight distribution of the polymer dispersant (C) (the value obtained by dividing the weight-average molecular weight in terms of polystyrene by the number-average molecular weight) is preferably in the range of 1.0 to 2.0, more preferably 1.0 to 1.7, and further preferably 1.0 to 1.5. When the molecular weight or molecular weight distribution of the polymer dispersant (C) is within the above range, the viscosity of the pigment dispersion composition can be controlled within an appropriate range, and sufficient pigment dispersibility or storage stability of the pigment dispersion composition can be obtained. In particular, when the molecular weight distribution is narrower, pigment dispersibility or storage stability of the pigment dispersion composition can be effectively obtained with a smaller amount of the dispersant.

[0145] As the polymer dispersant (C), commercially available products can be used, or it can be prepared by oneself. In addition, commercially available products and polyamines obtained by well-known block polymer production methods can be arbitrarily modified and subjected to functional group modification. When using commercially available products, examples of suitable polymer compounds include the DISPERBYK series manufactured by BYK, the Solsperse series manufactured by Lubrizol, and the EFKA-PX series manufactured by BASF. These polymer dispersants (C) can be used alone or in combination of two or more as needed.

[0146] When preparing the polymer dispersant (C) by oneself, the polyamine shown above is synthesized by a well-known block polymer production method. As specific examples of the monomer having a tertiary amino group and an ethylenically unsaturated group, there may be mentioned (meth)acrylic acid dimethylaminoethyl ester, (meth)acrylic acid dimethylaminopropyl ester, (meth)acrylic acid dimethylaminobutyl ester, (meth)acrylic acid diethylaminoethyl ester, (meth)acrylic acid diethylaminopropyl ester, (meth)acrylic acid diethylaminobutyl ester, (meth)acrylic acid pentamethylpiperidyl ester, (meth)acrylic acid tetramethylpiperidyl ester, N,N-dimethyl(meth)acrylamide, N,N-diethyl(meth)acrylamide, N-isopropyl(meth)acrylamide, dimethylaminoethyl (meth)acrylamide, dimethylaminopropyl (meth)acrylamide, diacetone (meth)acrylamide, or (meth)acrylamide compounds such as acryloylmorpholine. These monomers may be used alone or two or more thereof may be used.

[0147] As specific examples of the monomer having a quaternary ammonium cation group and an ethylenically unsaturated group, there may be mentioned organic halide salts of the monomer having a tertiary amino group. The organic halide salt is not particularly limited, and from the viewpoint of ease of acquisition, specific examples thereof may include chloromethane, chloroethane, chloropropane, chlorobutane, benzyl chloride, chloroethyl alcohol, bromomethane, bromoethane, bromopropane, bromobutane, benzyl bromide, bromoethyl alcohol, iodomethane, iodoethane, iodopropane, iodobutane, benzyl iodide, iodoethyl alcohol, etc. It should be noted that for the introduction of the quaternary ammonium cation group, instead of using the above monomers, a monomer having a tertiary amino group and another monomer having an ethylenically unsaturated group may be subjected to block polymerization, and then an organic halide salt may be added to the tertiary amine in the presence of an arbitrary temperature and a catalyst, and the introduction may be carried out by substituting a part or all of the tertiary amine with a quaternary ammonium cation group.

[0148] On the other hand, as other monomers having an ethylenically unsaturated group for improving the affinity with other pigment dispersion compositions, examples include (meth)acrylates having an alkyl, aryl, aralkyl, cycloalkyl, (poly)oxyalkylene skeleton, etc., as long as they do not impair the affinity with other pigment dispersion compositions, and there is no particular limitation. Specific examples include methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, isopropyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, tert-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, cyclohexyl (meth)acrylate, stearyl (meth)acrylate, lauryl (meth)acrylate, tetrahydrofurfuryl (meth)acrylate, isobornyl (meth)acrylate, phenyl (meth)acrylate, benzyl (meth)acrylate, phenoxyethyl (meth)acrylate, phenoxydiethylene glycol (meth)acrylate, methoxypolypropylene glycol (meth)acrylate, or ethoxypolyethylene glycol (meth)acrylate, etc. (meth)acrylate esters; styrenes such as styrene or α-methylstyrene; vinyl ethers such as ethyl vinyl ether, n-propyl vinyl ether, isopropyl vinyl ether, n-butyl vinyl ether, or isobutyl vinyl ether; fatty vinyl esters such as vinyl acetate or vinyl propionate. These monomers can be used alone or in combination of two or more.

[0149] [Solvent (D-1)]

[0150] The solvent (D-1) is not particularly limited as long as it does not react with the components contained in the pigment dispersion composition or the photosensitive coloring composition of the present embodiment and can dissolve or disperse these. As the solvent (D-1), the same solvent as that used in the production of the adhesive resin (A-1) or the polymer dispersant (C) can be used, and the solvent contained after the reaction can also be directly used, or a solvent can be further added. In addition, when adding other components, the solvent can also coexist with other components.

[0151] Specific examples of the solvent (D-1) include propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, dipropylene glycol monomethyl ether acetate, ethyl acetate, butyl acetate, isopropyl acetate, propylene glycol monomethyl ether, dipropylene glycol monomethyl ether, tripropylene glycol monomethyl ether, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, ethylene glycol monoethyl ether acetate, diethylene glycol ethyl ether acetate, etc. These can be used alone or in combination of two or more. Among these, ethylene glycol ether solvents such as propylene glycol monomethyl ether and propylene glycol monomethyl ether acetate, which are preferably used in the production of color filters, are preferred.

[0152] [Composition of Pigment Dispersion Composition]

[0153] The suitable blending amounts of the respective components in the pigment dispersion composition of the present embodiment are as follows.

[0154] The content of the binder resin (A-1) is preferably 10 to 50 parts by mass, more preferably 15 to 40 parts by mass, and still more preferably 20 to 30 parts by mass with respect to 100 parts by mass of the pigment (B). When the content of the binder resin (A-1) is 10 parts by mass or more, a photosensitive coloring composition having good developability can be obtained, and a resin cured film excellent in heat resistance, solvent resistance, and pattern adhesion can be obtained. When the content of the binder resin (A-1) is 50 parts by mass or less, the content of the pigment (B) can be sufficiently ensured, and a resin cured film excellent in color reproducibility can be obtained.

[0155] The content of the polymer dispersant (C) is preferably 10 to 50 parts by mass, more preferably 15 to 40 parts, and still more preferably 20 to 30 parts with respect to 100 parts by mass of the pigment (B). When the content of the polymer dispersant (C) is 10 parts by mass or more, a pigment dispersion composition excellent in pigment dispersibility and storage stability can be obtained. When the content of the polymer dispersant (C) is 50 parts by mass or less, the sufficient content of the pigment (B) can be ensured, and a photosensitive coloring composition excellent in color reproducibility can be obtained.

[0156] When the total amount of the components of the pigment dispersion composition other than the solvent (D-1) is set to 100 parts by mass, the blending amount of the solvent (D-1) is preferably 100 to 900 parts, more preferably 120 to 600 parts, and still more preferably 150 to 400 parts. As long as the content of the solvent (D-1) is within the above range, a pigment dispersion composition having an appropriate viscosity can be obtained.

[0157] [Method for producing pigment dispersion composition]

[0158] The pigment dispersion composition of the present embodiment is prepared by weighing specified amounts of a binder resin (A-1), a pigment (B), a polymeric dispersant (C), and a solvent (D-1), and subjecting the pigment (B) to micronization and dispersion using well-known dispersion treatment steps. In this dispersion treatment step, apparatuses such as a paint shaker, a bead mill, a ball mill, a roll mill, a stone mill, a jet mill, a homogenizer, a planetary mixer, and a rotation-revolution mixer are mostly used. Further, in this dispersion treatment step, when beads having a diameter of 0.01 to 10 mm are used, uniform micronization of the pigment (B) can be efficiently performed. The material of the beads is not limited, and glass beads or zirconia beads are preferably used in consideration of hardness or contamination of the pigment dispersion composition. Regarding the suitable time, temperature, bead diameter, and usage amount for the dispersion treatment, appropriate conditions vary depending on the composition of the pigment dispersion composition or the size of the apparatus, and can be appropriately adjusted as long as they are adjusted properly.

[0159] Finally, for the purpose of removing fine impurities and coarse particles or aggregates of the pigment (B) in the pigment dispersion composition, it is preferable to filter the pigment dispersion composition using a glass filter or the like.

[0160] <Photosensitive Coloring Composition>

[0161] The photosensitive coloring composition of the present embodiment contains: the above-mentioned pigment dispersion composition, a binder resin (A-2), a reactive diluent (E), and a photopolymerization initiator (F). The photosensitive coloring composition of the present embodiment may also contain a solvent (D-2). In the photosensitive coloring composition of the present embodiment, preferably, relative to 100 parts by mass of the pigment (B), the total binder resin (A) of the aforementioned binder resin (A-1) and binder resin (A-2) is 50 to 280 parts by mass, the aforementioned reactive diluent (E) is 40 to 200 parts by mass, and the aforementioned photopolymerization initiator (F) is 0.1 to 10 parts by mass.

[0162] As the solvent (D-2), the same solvent as the solvent (D-1) contained in the above-mentioned pigment dispersion composition can be used, or different solvents can be added.

[0163] [Binder Resin (A-2)]

[0164] The binder resin (A-2) used in the photosensitive coloring composition is not particularly limited, and resins such as (meth)acrylic resins, epoxy (meth)acrylic resins, and vinyl ester resins generally used in negative resists are preferred. As a specific backbone, a resin containing an ethylenically unsaturated double bond such as a vinyl group or a (meth)acryloyl group and a substituent contributing to alkali solubility such as a carboxylic acid, phosphoric acid, or sulfonic acid is preferred. By using these resins, a photosensitive coloring composition having excellent pattern adhesion or developability can be provided.

[0165] Among these resins, particularly from the viewpoint of easily providing resins with a wide range of properties, (meth)acrylic resins having a (meth)acryloxy group and a carboxyl group are preferred. This resin can be a commercially available product or prepared independently. When preparing independently, the same one as the binder resin (A-1) can also be used. It should be noted that in the synthesis, in order to control the molecular weight within an appropriate range, and in addition, in order to adjust the viscosity after synthesis to an appropriate range, a solvent (D-2) can also be added.

[0166] There are no particular restrictions on the physical properties of the binder resin (A-2). From the viewpoints of the ease of manufacturing the photosensitive coloring composition or the compatibility with other compositions, the weight-average molecular weight is preferably in the range of 1000 to 50000, the solid content acid value is preferably 10 to 200 mgKOH / mg, the double bond equivalent is preferably 100 to 3000 g / mol, and the viscosity of the binder resin (A-2) solution is preferably in the range of 0.1 to 1000 dPa·s.

[0167] The total content of the binder resin (A) of the aforementioned binder resin (A-1) and binder resin (A-2) is preferably 50 to 280 parts by mass, more preferably 75 to 230 parts by mass, and still more preferably 100 to 200 parts by mass with respect to 100 parts by mass of the pigment (B).

[0168] [Reactive diluent (E)]

[0169] The reactive diluent (E) is not particularly limited as long as it is a low molecular compound containing an ethylenically unsaturated double bond such as vinyl, (meth)acryloyloxy, etc. Specific examples of the reactive diluent (E) include aromatic vinyl monomers such as styrene, α-methylstyrene, α-chloromethylstyrene, vinyltoluene, divinylbenzene, diallyl phthalate, and diallyl phenylphosphonate; polycarboxylic acid monomers such as vinyl acetate and vinyl adipate; (meth)acrylic acid monomers such as (meth)methyl acrylate, (meth)ethyl acrylate, (meth)propyl acrylate, (meth)butyl acrylate, (meth)β-hydroxyethyl acrylate, (meth)hydroxypropyl acrylate, ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, ethylene glycol di(meth)acrylate, trimethylolpropane di(meth)acrylate, trimethylolpropane tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol hexa(meth)acrylate, and tri(meth)acrylate of tri(2-hydroxyethyl)isocyanurate; and triallyl cyanurate. These can be used alone or in combination of two or more. Among these, compounds having a plurality of (meth)acryloyloxy groups are preferred, and compounds having 3 or more (meth)acryloyloxy groups such as trimethylolpropane tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol hexa(meth)acrylate, and tri(meth)acrylate of tri(2-hydroxyethyl)isocyanurate are more preferred.

[0170] The content of the reactive diluent (E) is preferably 40 to 200 parts by mass, more preferably 60 to 180 parts by mass, and still more preferably 80 to 160 parts by mass, based on 100 parts by mass of the pigment (B).

[0171] [Photoinitiator (F)]

[0172] The photoinitiator (F), preferably a photo-radical generator, as a specific example, may include benzoin and its alkyl ethers such as benzoin methyl ether and benzoin ethyl ether; acetophenones such as acetophenone, 2,2-dimethoxy-2-phenylacetophenone, 1,1-dichloroacetophenone, 4-(1-tert-butyldioxy-1-methylethyl)acetophenone; anthraquinones such as 2-methylanthraquinone, 2-pentylanthraquinone, 2-tert-butylanthraquinone, 1-chloroanthraquinone; thioxanthones such as 2,4-dimethylthioxanthone, 2,4-diisopropylthioxanthone, 2-chlorothioxanthone; ketals such as acetophenone dimethyl ketal and benzyl dimethyl ketal; benzophenones such as benzophenone, 4-(1-tert-butyldioxy-1-methylethyl)benzophenone, 3,3’,4,4’-tetra(tert-butyldioxycarbonyl)benzophenone; 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one; 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)butan-1-one; acylphosphine oxides; and thioxanthones, etc. These can be used alone or in combination of two or more.

[0173] The content of the photoinitiator (F) is preferably 0.02 to 11 parts by mass, more preferably 0.24 to 6.7 parts by mass, and still more preferably 0.56 to 4.4 parts by mass, based on 100 parts by mass of the total amount of the binder resins (A-1), binder resins (A-2), and reactive diluent (E).

[0174] In addition to the above components, in order to impart specified properties, the photosensitive coloring composition of the present embodiment may also be formulated with well-known additives such as photoacid generators, photobase generators, coupling agents, leveling agents, fillers, etc. The blending amounts of these components are not particularly limited within the range that does not impair the effects of the present invention.

[0175] [Method for manufacturing the photosensitive coloring composition]

[0176] The photosensitive coloring composition of the present embodiment can be manufactured by mixing the above-mentioned respective components using a well-known mixing device. For example, after adjusting the pigment dispersion composition, the binder resin (A-2), reactive diluent (E), photoinitiator (F), etc. are sequentially mixed, whereby it can be manufactured. In addition, as needed, in addition to the solvent (D-1) contained in the pigment dispersion composition, a solvent (D-2) can also be added. In this case, the solvent (D) contained in the photosensitive coloring composition will include the solvent (D-1) and the solvent (D-2). It should be noted that the solvent (D-2) can be the same as the solvent (D-1) or different.

[0177] The photosensitive coloring composition obtained by operating as described above can achieve sufficient pigment dispersibility or storage stability of the pigment dispersion composition even when the colorant of the coloring agent is made highly concentrated and the concentration of the dispersant or binder resin is reduced, and can achieve high brightness and exhibit various resist characteristics such as heat resistance, solvent resistance, pattern adhesion, and developability. As a result, a coloring pattern with excellent reliability can be formed. That is, by using the aforementioned photosensitive coloring composition, a color filter with excellent reliability can be provided.

[0178] <Color Filter>

[0179] Next, a color filter having a coloring pattern composed of a cured product of the photosensitive coloring composition of the present invention will be described. The color filter of the present invention has a coloring pattern formed by using the above-described photosensitive coloring composition. Generally, a color filter is composed of the following components: a substrate; RGB pixels formed on the substrate; a black matrix formed at the boundary of each pixel; and a protective film formed on the pixels and the black matrix. In this configuration, except for the pixels and the black matrix (coloring pattern) being formed using the above-described photosensitive coloring composition, other configurations can be those well-known.

[0180] Next, an embodiment of a method for manufacturing a color filter will be described. First, a coloring pattern is formed on a substrate. Specifically, a black matrix and RGB pixels are sequentially formed on the substrate. The material of the substrate is not particularly limited, and a glass substrate, a silicon substrate, a polycarbonate substrate, a polyester substrate, a polyamide substrate, a polyamideimide substrate, a polyimide substrate, an aluminum substrate, a printed wiring board, an array substrate, etc. can be appropriately used.

[0181] The coloring pattern can be formed by a photolithography method. Specifically, after the above-described photosensitive coloring composition is coated on the substrate to form a coating film, the coating film is exposed through a photomask with a specified pattern, and the exposed portion is photocured. Next, the unexposed portion is developed with an alkaline aqueous solution and then baked, whereby a specified coloring pattern can be formed.

[0182] The coating method of the photosensitive coloring composition is not particularly limited, and a screen printing method, a roll coating method, a curtain coating method, a spraying method, a spin coating method, etc. can be used. In addition, after the photosensitive coloring composition is coated, if necessary, heating means such as a circulating oven, an infrared heater, a hot plate, etc. can be used to heat to volatilize the solvent (D-1) or the solvent (D-2). The heating conditions are not particularly limited and can be appropriately set according to the type of the photosensitive coloring composition used. Generally, heating at a temperature of 50°C to 120°C for 30 seconds to 30 minutes is sufficient.

[0183] Next, through a negative mask, actinic energy rays such as ultraviolet rays and excimer lasers are irradiated onto the formed coating film to perform partial exposure. The amount of the irradiated energy rays can be appropriately selected according to the composition of the photosensitive coloring composition. For example, it is preferably 30 to 2000 mJ / cm 2 . The light source used for exposure is not particularly limited, and a low-pressure mercury lamp, a medium-pressure mercury lamp, a high-pressure mercury lamp, a xenon lamp, a metal halide lamp, etc. can be used.

[0184] The alkaline aqueous solution used for development is not particularly limited, and an aqueous solution of sodium carbonate, potassium carbonate, calcium carbonate, sodium hydroxide, potassium hydroxide, etc.; an aqueous solution of an amine compound such as ethylamine, diethylamine, dimethylethanolamine, etc.; an aqueous solution of a p-phenylenediamine compound such as tetramethylammonium, 3-methyl-4-amino-N,N-diethylaniline, 3-methyl-4-amino-N-ethyl-N-β-hydroxyethylaniline, 3-methyl-4-amino-N-ethyl-N-β-methanesulfonamidoethylaniline, 3-methyl-4-amino-N-ethyl-N-β-methoxyethylaniline and sulfates, hydrochlorides or p-toluenesulfonates thereof can be used. It should be noted that, in these aqueous solutions, an antifoaming agent or a surfactant can be added as needed. In addition, after development with the above alkaline aqueous solution, it is preferably washed with water and dried.

[0185] In addition, the baking conditions are not particularly limited, and heat treatment can be performed according to the type of the photosensitive coloring composition used. Generally, heating at 130 to 250 °C for 10 to 60 minutes is sufficient.

[0186] By sequentially repeating coating, exposure, development, and baking as described above using the photosensitive coloring composition for the black matrix and the photosensitive coloring compositions for red, green, and blue pixels, a desired colored pattern can be formed. Thereafter, a protective film is formed on the colored pattern (each pixel of RGB and the black matrix). The protective film is not particularly limited, and a well-known one can be used for formation.

[0187] The color filter manufactured by operating in such a manner has excellent pigment dispersibility due to the uniform micronization of the pigment, and achieves various resist characteristics such as high brightness, excellent heat resistance, solvent resistance, adhesion, and developability, and is of high fineness.

[0188] <Image display component>

[0189] The image display component of the present embodiment includes the above-described color filter. As a specific example, solid-state imaging components such as liquid crystal display components, organic EL display components, CCD components, or CMOS components can be cited. The manufacturing of the image display component of the present embodiment can be carried out according to a conventional method except for using the above-described color filter. For example, when manufacturing a liquid crystal display component, the above-described color filter is formed on a substrate, and then electrodes, spacers, etc. are formed in sequence. Then, after forming electrodes, etc. on another substrate, the two substrates are bonded together, a specified amount of liquid crystal is injected, and sealing is performed.

[0190] [Examples]

[0191] Hereinafter, the present invention will be described in detail with reference to examples, but the present invention is not limited by these examples. It should be noted that unless otherwise specified, parts and % in this example are based on mass.

[0192] <Method for Measuring Weight-Average Molecular Weight>

[0193] The weight-average molecular weight described below means the standard polystyrene-converted weight-average molecular weight measured under the following conditions using gel permeation chromatography (GPC).

[0194] Column: Shodex (registered trademark) LF-804 + LF-804 (manufactured by Showa Denko K.K.)

[0195] Column temperature: 40 °C

[0196] Sample: 0.2% tetrahydrofuran solution of adhesive resin (A-1)

[0197] Developing solvent: Tetrahydrofuran

[0198] Detector: Differential refractometer (Shodex RI-71S) (manufactured by Showa Denko K.K.)

[0199] Flow rate: 1 mL / min

[0200] <Method for Measuring Acid Value>

[0201] According to JIS K6901 5.3.2, the number of mg of potassium hydroxide required to neutralize the acidic components contained in 1 g of the solid content of the adhesive resin (A-1) is measured.

[0202] Measuring instrument: 776Dosimat (Metrohm)

[0203] Mixed indicator: Mixed indicator of bromothymol blue and phenol red

[0204] <Method for Measuring Unsaturated Group Equivalent>

[0205] The mass of the binder resin (A-1) per mole number of the ethylenically unsaturated group, and is a calculated value based on the usage amount of the monomer.

[0206] <Method for measuring amine value>

[0207] The mass of the polymer dispersant (C) per mole number of the tertiary amino group and the quaternary ammonium cation group, and is a calculated value based on the usage amount of the monomer. The calculation is based on the definition of the amine value (a value measured according to the specifications shown in JIS K7237, etc.), and represents the number of mg of potassium hydroxide required to neutralize the amine component contained in 1 g of the solid component of the polymer dispersant (C).

[0208] Synthesis examples and comparative synthesis examples of the binder resin (A-1) are as follows.

[0209] <Synthesis Example 1>

[0210] In a flask equipped with a stirring device, a dropping funnel, a condenser, a thermometer, and a gas inlet tube, 67.2 g of propylene glycol monomethyl ether acetate (50.0 parts by mass relative to 100 parts by mass of the total of the monomers (m-1a), (m-2), and (m-3)) was placed. Then, while purging with nitrogen, stirring was carried out and the temperature was raised to 120 °C. Next, a mixed solution obtained by adding 8.0 g of tert-butyl peroxy-2-ethylhexanoate (8.4 parts by mass relative to 100 parts by mass of the total of the monomers (m-1a), (m-2), and (m-3)) as a polymerization initiator to a monomer mixture composed of 16.2 g of dicyclopentanyl methacrylate (m-1a), 26.5 g of acrylic acid (m-2), and 51.8 g of benzyl methacrylate (m-3) was added dropwise from the dropping funnel into the aforementioned flask. After the dropwise addition was completed, copolymerization reaction was carried out by stirring at 120 °C for 2 hours to obtain a copolymer (P).

[0211] Next, after replacing the inside of the aforementioned flask with dry air, 15.7 g of glycidyl methacrylate (m-4), 0.3 g of triphenylphosphine as a catalyst (0.3 parts by mass relative to 100 parts by mass of the total of the monomers (m-1a), (m-2), (m-3), and (m-4)), and 0.2 g of hydroquinone monomethyl ether as a polymerization inhibitor (0.2 parts by mass relative to 100 parts by mass of the total of the monomers (m-1a), (m-2), (m-3), and (m-4)) were added, and addition reaction to the copolymer (P) was carried out by stirring at 120 °C for 5 hours. Then, propylene glycol monomethyl ether acetate was added as a solvent so that the solid content became 40.0%, and a solution of the binder resin (A-1) having an ethylenically unsaturated double bond and a carboxyl group as an alkali-soluble group was obtained, and it was used as Sample No. 1.

[0212] When converting the total of monomers (m-1a), (m-2), and (m-3) to 100 mol%, the blending ratios of the respective monomers, the weight-average molecular weight, acid value, and unsaturated group equivalent of the binder resin (A-1) are shown in Table 1.

[0213] <Synthesis Examples 2, 5, 6, Comparative Synthesis Examples 1 to 4>

[0214] Except for setting the blending ratios of the monomers described in Table 1, the rest are obtained in the same manner as in Synthesis Example 1 to obtain the binder resin (A-1), and these are used as Sample No. 2, Sample No. 5 to 10. The blending ratios of the respective monomers, and the weight-average molecular weight, acid value, and unsaturated group equivalent of the binder resin (A-1) are shown in Table 1.

[0215] <Synthesis Example 3>

[0216] The copolymer (P) is obtained in the same manner as in Synthesis Example 1.

[0217] Next, after replacing the inside of the aforementioned flask with dry air, 15.7 g of glycidyl methacrylate (m-4), 0.3 g of triphenylphosphine as a catalyst (0.3 parts by mass relative to 100 parts by mass of the total of monomers (m-1a), (m-2), (m-3), and (m-4)), and 0.2 g of hydroquinone monomethyl ether as a polymerization inhibitor (0.2 parts by mass relative to 100 parts by mass of the total of monomers (m-1a), (m-2), (m-3), and (m-4)) are added, and the addition reaction to the copolymer (P) is carried out by stirring at 120 °C for 5 hours. Further, 10.4 g of 2-isocyanatoethyl acrylate (m-5) is added, and the addition reaction to the copolymer (P) is carried out by stirring at 100 °C for 1 hour. Then, propylene glycol monomethyl ether acetate as a solvent is added so that the solid content becomes 40.0%, and a solution of the binder resin (A-1) having an ethylenic unsaturated double bond and a carboxyl group as an alkali-soluble group is obtained, and this is used as Sample No. 3.

[0218] When converting the total of monomers (m-1a), (m-2), and (m-3) to 100 mol%, the blending ratios of the respective monomers, the weight-average molecular weight, acid value, and unsaturated group equivalent of the binder resin (A-1) are shown in Table 1.

[0219] <Synthesis Example 4>

[0220] The copolymer (P) is obtained in the same manner as in Synthesis Example 1.

[0221] Next, after replacing the inside of the aforementioned flask with dry air, 15.7 g of glycidyl methacrylate (m-4), 0.3 g of triphenylphosphine as a catalyst (0.3 parts by mass with respect to 100 parts by mass in total of monomers (m-1a), (m-2), (m-3) and (m-4)), and 0.2 g of hydroquinone monomethyl ether as a polymerization inhibitor (0.2 parts by mass with respect to 100 parts by mass in total of monomers (m-1a), (m-2), (m-3) and (m-4)) were added, and the addition reaction for the copolymer (P) was carried out by stirring at 120°C for 5 hours. Further, 7.4 g of succinic anhydride (m-6) was added, and the addition reaction for the copolymer (P) was carried out by stirring at 120°C for 1 hour. Thereafter, propylene glycol monomethyl ether acetate as a solvent was added so that the solid content became 40.0%, and a solution of the binder resin (A-1) having an ethylenically unsaturated double bond and a carboxyl group as an alkali-soluble group was obtained, and this was designated as Sample No. 4.

[0222] The blending ratios of the respective monomers, the weight-average molecular weight, acid value, and unsaturated group equivalent of the binder resin (A-1) when converting the total of the monomers (m-1a), (m-2) and (m-3) to 100 mol% are shown in Table 1.

[0223] Table 1

[0224]

[0225] A production example of the polymer dispersant (C) is as follows.

[0226] <Synthesis Example 7>

[0227] In a flask equipped with a stirring device, a dropping funnel, a condenser, a thermometer, and a gas inlet tube, 133 g of propylene glycol monomethyl ether acetate, 80.5 g of isobornyl methacrylate, and 13.2 g of tetramethylethylenediamine as a catalyst were placed. While replacing the inside of the flask with nitrogen, it was stirred at 50 °C for 1 hour. Then, 9.3 g of ethyl 2-bromoisobutyrate and 5.6 g of copper(I) chloride as catalysts were added, and after raising the temperature of the flask to 110 °C, a polymerization reaction was carried out for 4 hours. After the reaction, a sample solution was taken to measure the non-volatile components. After confirming that the polymerization conversion rate converted from the non-volatile components was 98% or more, 61 g of propylene glycol monomethyl ether acetate and 19.5 g of dimethylaminoethyl methacrylate as a monomer having a tertiary amino group were added, and further reacted at 110 °C for 2 hours. After the reaction, a sample solution was taken again to measure the non-volatile components. After confirming that the polymerization conversion rate converted from the non-volatile components was 98% or more, the solution was cooled. Finally, propylene glycol monomethyl ether acetate as a solvent was added so that the solid content became 40.0%, and sample No. 11 (amine value 70 mg KOH / g, weight average molecular weight 5500) of a solution of a polymer dispersant (C) having a tertiary amino group was obtained.

[0228] <Synthesis Example 8>

[0229] In a flask equipped with a stirring device, a dropping funnel, a condenser, a thermometer, and a gas inlet tube, 133 g of propylene glycol monomethyl ether acetate, 70.0 g of isobornyl methacrylate, and 13.2 g of tetramethylethylenediamine as a catalyst were placed. While replacing the inside of the flask with nitrogen, it was stirred at 50 °C for 1 hour. Then, 9.3 g of ethyl 2-bromoisobutyrate and 5.6 g of copper(I) chloride as catalysts were added, and after raising the temperature of the flask to 110 °C, a polymerization reaction was carried out for 4 hours. After the reaction, a sample solution was taken to measure the non-volatile components. After confirming that the polymerization conversion rate converted from the non-volatile components was 98% or more, 61 g of propylene glycol monomethyl ether acetate and 30.0 g of methacryloyloxyethylbenzyldimethylammonium chloride as a monomer having a quaternary ammonium cation group were added, and further reacted at 110 °C for 2 hours. After the reaction, a sample solution was taken again to measure the non-volatile components. After confirming that the polymerization conversion rate converted from the non-volatile components was 98% or more, the solution was cooled. Finally, propylene glycol monomethyl ether acetate as a solvent was added so that the solid content became 40.0%, and sample No. 12 (amine value 60 mg KOH / g, weight average molecular weight 5000) of a solution of a polymer dispersant (C) having a quaternary ammonium cation group was obtained.

[0230] The production examples of the pigment dispersion composition are shown below.

[0231] <Examples 1 to 7, Comparative Examples 1 to 4>

[0232] In a SUS container (inner diameter 50 mm × height 100 mm) filled with 200 g of zirconia beads (YTZ beads manufactured by NIKKATO) with a diameter of 0.1 mm, the following components were mixed according to the composition shown in Table 2: 7.5 g of C.I. Pigment Green 58 (Fastogen Green A110 manufactured by DIC Corporation) as the pigment (B), either Sample No. 11 having a tertiary amino group or Sample No. 12 having a quaternary ammonium cation group as the polymer dispersant (C), any one of the aforementioned Samples No. 1 to No. 10 as the binder resin (A-1), and propylene glycol monomethyl ether acetate was added as the solvent (D-1) such that the solid content excluding the zirconia beads was 24%. The mixture was then dispersed by mixing at room temperature for 2 hours using a paint shaker (Red Devil 5400 manufactured by Red Devil Equipment). Thereafter, the content was suction filtered through a glass filter to obtain Pigment Dispersion Compositions No. 1 to 7, 10 to 13.

[0233] <Examples 8 - 9, Comparative Example 5>

[0234] Except that the following components were mixed according to the composition shown in Table 2: 9.4 g of C.I. Pigment Green 58 as the pigment (B), EFKA-PX4300 as the polymer dispersant (C), and any one of the aforementioned Samples No. 1, No. 6, or No. 10 as the binder resin (A-1), the rest was carried out in the same manner as in Example 1 to obtain Pigment Dispersion Compositions No. 8 - 9 and 14.

[0235] <Evaluation of Pigment Dispersion>

[0236] The viscosity of the freshly prepared pigment dispersion composition was measured using an E-type viscometer (RE-80L manufactured by Toki Sangyo Co., Ltd., measurement temperature 25°C, cone No. 3, rotation speed 20 rpm) for evaluation. In addition, based on the measurement results of the viscosity, the pigment dispersion and the storage stability of the pigment dispersion composition were evaluated in three grades of ◎, ○, and × according to the following criteria, and ◎ and ○ were considered qualified. The evaluation results are shown in Table 2.

[0237] ◎: Less than 6.0 mPa·s

[0238] ○: 6.0 mPa·s or more and less than 10.0 mPa·s

[0239] ×: 10.0 mPa·s or more

[0240] <Evaluation of Storage Stability of Pigment Dispersion Composition>

[0241] Evaluation was carried out by measuring the viscosity of the prepared pigment dispersion composition after storage at room temperature for 2 weeks using an E-type viscometer. The increase rate of the viscosity of the pigment dispersion composition after storage at room temperature for 2 weeks was compared with that of the freshly prepared one, and evaluation was carried out in three stages of ○, △, and × according to the following criteria, and ○ and △ were regarded as qualified. The evaluation results are shown in Table 2.

[0242] ○: Less than 10%

[0243] △: 10% or more (less than 10% after storage at room temperature for 1 week)

[0244] ×: 10% or more (already 10% or more after storage at room temperature for 1 week)

[0245] Table 2

[0246]

[0247] The production examples of the binder resin (A-2) are shown below.

[0248] <Synthesis Example 9>

[0249] In the above Synthesis Example 1, except that 11.9 g of dicyclopentanyl methacrylate was used instead of 16.2 g of dicyclopentanyl methacrylate (m-1a); 42.7 g of benzyl methacrylate was used instead of 51.8 g of benzyl methacrylate (m-3); 20.9 g of methacrylic acid was used instead of 26.5 g of acrylic acid (m-2); as a polymerization initiator, 1.6 g of tert-butyl peroxy-2-ethylhexanoate was used instead of 8.0 g of tert-butyl peroxy-2-ethylhexanoate; 11.5 g of glycidyl methacrylate was used instead of 15.7 g of glycidyl methacrylate (m-4), according to the same method as in Synthesis Example 1, a sample No. 13 (molecular weight 32000, solid content acid value 104 mgKOH / g, ethylenically unsaturated group equivalent 1100 g / mol) as a solution of the binder resin (A-2) was obtained.

[0250] The production examples of the photosensitive coloring composition are shown below.

[0251] <Examples 10 to 18, Comparative Examples 6 to 10>

[0252] When the solid components of the aforementioned pigment dispersion compositions Nos. 1 to 13 are set to 100 parts by mass, the following are mixed: 80 parts by mass of the aforementioned sample No. 13 as the binder resin (A-2) with a solid component of 80 parts by mass, 80 parts by mass of dipentaerythritol hexaacrylate as the reactive diluent (E), 4 parts by mass of 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-,-1-(O-acetoxime) as the photopolymerization initiator (F), and as the solvent (D-2), propylene glycol monomethyl ether acetate is added so that the total solid component becomes 30%, thereby preparing photosensitive coloring compositions Nos. 1 to 14. It should be noted that, as the blending amounts of each component relative to 100 parts by mass of the pigment (B), in photosensitive coloring compositions Nos. 1 to 7, Nos. 10 to 13, the binder resin (A-2) is 120 parts by mass, the reactive diluent (E) is 120 parts by mass, and the photopolymerization initiator (F) is 6 parts by mass. In addition, in photosensitive coloring compositions Nos. 8, No. 9 and No. 14, the binder resin (A-2) is 112 parts by mass, the reactive diluent (E) is 112 parts by mass, and the photopolymerization initiator (F) is 5.6 parts by mass.

[0253] <Evaluation of the storage stability of the photosensitive coloring composition>

[0254] The evaluation is carried out by measuring the viscosities of the prepared photosensitive coloring composition and the photosensitive coloring composition after being stored at room temperature for 2 weeks after adjustment, using an E-type viscometer (RE-80L manufactured by Toki Sangyo Co., Ltd., measurement temperature 25 °C, cone No. 3, rotation speed 20 rpm). The increase rate of the viscosity of the photosensitive coloring composition after being stored at room temperature for 2 weeks is compared with that of the freshly prepared one, and the evaluation is carried out in two stages of ○ (qualified) and × (unqualified) according to the following criteria. The evaluation results are shown in Tables 3 and 4.

[0255] ○: Less than 10%

[0256] ×: 10% or more

[0257] <Production of the green color resist (1)>

[0258] The photosensitive coloring compositions Nos. 1 to 7, Nos. 10 to 13 are spin-coated on a glass substrate (non-alkali glass substrate) with a side length of 5 cm so that the average thickness of the final cured film becomes 2.0 μm, and then heated at 100 °C for 3 minutes to volatilize the solvent. Next, after exposing the entire surface of the film (using USH-250BY manufactured by Ushio Electric Co., Ltd. as the lamp, the exposure amount is 40 mJ / cm 2 ), and then baking at 230 °C for 30 minutes, thereby obtaining the green color resist (1) as the cured film.

[0259] <Fabrication of Green Color Resist (2)>

[0260] Photocurable coloring compositions Nos. 1 to 7, Nos. 10 to 13 were spin-coated on a 5 cm square glass substrate (non-alkali glass substrate) so that the average thickness of the final cured film became 2.0 μm, and then heated at 100 °C for 3 minutes to volatilize the solvent. Next, a photomask with a line and space or dot pattern was set on the substrate, and the film was exposed (as the lamp, USH-250BY manufactured by Ushio Denki Kabushiki Kaisha, exposure amount: 40 mJ / cm 2 ) for photocuring. After that, development was carried out using a 0.2 mass% aqueous potassium hydroxide solution. Furthermore, by baking at 230 °C for 30 minutes, green color resist (2) as a cured film was obtained.

[0261] <Fabrication of Green Color Resist (3)>

[0262] Except that photocurable coloring compositions Nos. 1, Nos. 7 to 9, and No. 14 were adjusted to the average thickness described below and placed on a 5 cm square glass substrate (non-alkali glass substrate), the rest was carried out in the same manner as the fabrication method of green color resist (1), and thus green color resist (3) as a cured film was obtained. The above average thickness was such that the color coordinates of the final cured film were x = 0.26 ± 0.005 and y = 0.45 ± 0.005 using a spectrophotometer UV-1650PC manufactured by Shimadzu Corporation.

[0263] <Color Strength Test>

[0264] The film thickness of the above green color resist (3) was measured using a step gauge (ET4000M manufactured by Kosaka Laboratory Ltd.). The film thickness was evaluated in three grades of ◎, ○, and × according to the following criteria, and ◎ and ○ were regarded as qualified. The evaluation results are shown in Table 4.

[0265] ◎: Film thickness is less than 1.9 μm

[0266] ○: Film thickness is 1.9 to 2.1 μm

[0267] ×: Film thickness is 2.1 μm or more

[0268] <Transmittance Test>

[0269] Using a spectrophotometer UV-1650PC manufactured by Shimadzu Corporation, the transmittances of the above green color resists (1) and (3) at 525 nm were measured. Transmittance of 95.0% or more was regarded as ○ (qualified), and 94.9% or less was regarded as × (unqualified), and the measurement results are shown in Tables 3 and 4.

[0270] <Solvent resistance test>

[0271] Immerse the entire surface of the above green color resist (1) in N-methylpyrrolidone at 60 °C or 80 °C for 3 minutes. Then, take out the green color resist and conduct air drying. By visually confirming the degree of peeling of the entire surface of the green color resist, the solvent resistance of the photosensitive coloring composition is evaluated in three grades of ⊙, ○, and × according to the following criteria, and ⊙ and ○ are regarded as qualified. The evaluation results are shown in Table 3.

[0272] ⊙: No peeling at 60 °C and 80 °C

[0273] ○: More than one peeling is observed at 80 °C, but no peeling is observed at 60 °C

[0274] ×: More than one peeling is observed at 60 °C and 80 °C

[0275] <Developability test>

[0276] The developability test evaluates two aspects: development speed and pattern shape.

[0277] Regarding the development speed, in the development step of the above green color resist (2), measure the time required until the pattern is no longer visible during development with a 0.2% by mass aqueous potassium hydroxide solution, and evaluate it in three grades of ⊙, ○, and × according to the following criteria, and ⊙ and ○ are regarded as qualified. The evaluation results are shown in Table 3.

[0278] ⊙: Less than 40 seconds

[0279] ○: 40 seconds or more and less than 80 seconds

[0280] ×: 80 seconds or more

[0281] Regarding the pattern shape, it is carried out under the condition that the development speed is qualified. Use a scanning electron microscope (S-3400N manufactured by Hitachi-High Technologies Corporation) to confirm the shape of the pattern end face of the cured coating film of the above green color resist (2). Evaluate it in two grades of ○ (qualified) and × (unqualified) according to the following criteria. The evaluation results are shown in Table 3.

[0282] ○: Good end face shape (not inverted cone)

[0283] ×: The end face becomes an inverted cone

[0284]

[0285] Table 4

[0286] ※When the solid content of the pigment dispersion composition is set to

[0287] 100 parts by mass, the solid content of the binder resin (A-2),

[0288] the parts by mass of the reactive diluent (E) and the photoinitiator (F).

[0289] Reactive diluent (E): Dipentaerythritol hexaacrylate

[0290] Photoinitiator (F):

[0291] 1-[9-Ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-, -1-(0-acetoxime)

[0292] Solvent (D-2): Propylene glycol monomethyl ether acetate

[0293] As can be seen from the results of Tables 2 and 3, in Examples 1 to 16, excellent pigment dispersibility and storage stability of the pigment dispersion composition can be obtained, and excellent transmittance and solvent resistance of the photosensitive coloring composition can be obtained, and it is confirmed that a pigment dispersion composition with high brightness and suppression of bleeding of the colorant can be provided. Furthermore, excellent development speed and pattern shape are exhibited, and it is shown that a color filter with excellent processability can be provided.

[0294] In particular, in Examples 4 and 13, compared with Examples 1 and 10, a binder resin (A-1) having more ethylenically unsaturated groups introduced into the side chain is used, so that excellent solvent resistance of the photosensitive coloring composition can be obtained. However, on the other hand, in Examples 5 and 14, compared with Examples 1 and 10, a binder resin (A-1) having more carboxylic acids introduced into the side chain is used, so that excellent developability of the photosensitive coloring composition can be obtained.

[0295] Furthermore, from the results of Tables 2 and 4, it can be seen that in Examples 8 and 17, compared with Examples 1 and 10, even for a pigment dispersion composition in which the concentration of the dispersant or the binder resin is reduced due to the high concentration of the pigment, sufficient pigment dispersibility and storage stability can be exhibited. Along with this, it can be known that the photosensitive coloring composition has sufficient coloring power even in a thin film state due to the high concentration of the pigment, and the bleeding of the colorant is suppressed due to the reduction of the concentration of the dispersant or the binder resin, and excellent solvent resistance is exhibited.

[0296] In contrast, comparing Comparative Examples 1 and 6, the pigment dispersibility and storage stability of the pigment dispersion composition are good. However, on the other hand, since the binder resin (A-1) does not have a structural unit derived from the compound (m-4) containing an ethylenically unsaturated group, the curability of the photosensitive coloring composition is poor. As a result, it was confirmed that the green color resist peeled off in the solvent resistance test or the developed pattern had an inverted conical shape.

[0297] Furthermore, comparing Comparative Examples 2 and 7, the pigment dispersibility and storage stability of the pigment dispersion composition are good. However, on the other hand, since the binder resin (A-1) does not have a structural unit derived from the polymerizable monomer (m-1), the transmittance and solvent resistance of the photosensitive coloring composition are poor. As a result, high brightness cannot be achieved and the bleeding of the colorant cannot be suppressed.

[0298] Furthermore, comparing Comparative Examples 3-4 and 8-9, since the binder resin (A-1) does not have a structural unit derived from acrylic acid (m-2) and the polymerizable monomer (m-3) containing an aromatic ring, the pigment dispersibility and storage stability of the pigment dispersion composition are significantly poor. As a result, the storage stability of the photosensitive coloring composition is also poor, the transmittance and developability are also poor, and it becomes a composition that is difficult to actually use.

[0299] In addition, from the results of Tables 2 and 4, the following is known. Comparing Comparative Examples 5 and 10, since the binder resin (A-1) does not contain a structural unit derived from the polymerizable monomer (m-3) containing an aromatic ring, similar to Comparative Examples 4 and 9, even in the pigment dispersion composition with a high pigment concentration, the pigment dispersibility is insufficient, and the storage stability or transmittance is also poor, so it is difficult to actually use. The aforementioned polymerizable monomer (m-3) containing an aromatic ring has a high affinity for the pigment (B). When considering the results of Examples 8 and 17 and Examples 9 and 18 together, the following is shown. The binder resin (A-1) with a low content ratio of the structural unit derived from the polymerizable monomer (m-3) containing an aromatic ring, as in Examples 7 and 16, can be applied to the pigment dispersion composition with a low pigment concentration, but when the pigment concentration is high, the storage stability tends to decrease.

[0300] Based on the above, it can be known that according to the present invention, a pigment dispersion composition can be provided, which can achieve high brightness due to sufficient pigment dispersibility or storage stability of the pigment dispersion composition, and can suppress the bleeding of the colorant, and has excellent heat resistance, solvent resistance, pattern adhesion and excellent reliability. In addition, a photosensitive coloring composition containing the pigment dispersion composition and a color filter containing the photosensitive coloring composition can be provided.

[0301] Industrial Applicability

[0302] According to the present invention, a pigment dispersion composition having good pigment dispersibility and storage stability can be provided. Further, by using the pigment dispersion composition, a photosensitive coloring composition capable of obtaining a cured product having excellent solvent resistance can be provided. Furthermore, a color filter having a cured product of the photosensitive coloring composition and an image display component including the color filter can be provided.

Claims

1. A pigment dispersion composition, characterized in that it contains a binder resin (A-1), a pigment (B), a polymeric dispersant (C) and a solvent (D-1), the binder resin (A-1) is at least one resin selected from resin (A-1a) and resin (A-1b), the resin (A-1a) is a resin obtained by adding a part of the carboxyl groups of a copolymer (P) of a monomer (M) containing a polymerizable monomer (m-1a) having a bridged cyclic hydrocarbon group with 10 to 20 carbon atoms, acrylic acid (m-2) and a polymerizable monomer (m-3) containing an aromatic ring, to a compound (m-4) containing an ethylenically unsaturated group having a group reactive with a carboxyl group. Among them, the polymerizable monomer (m-1a) is a (meth)acrylate having a structure represented by the following formula (5) and does not include the polymerizable monomer (m-1b) represented by the following formula (1), the resin (A-1b) is a resin obtained by adding a part of the hydroxyl groups in the resin (A-1a) to one or more selected from a compound (m-5) containing an ethylenically unsaturated group having an isocyanate group and a polyanhydride (m-6). Among them, the hydroxyl group is a hydroxyl group generated by ring-opening addition of the compound (m-4) containing an ethylenically unsaturated group in the resin (A-1a) with a monomer having an epoxy group or an oxetanyl group, In formula (1), R1 and R2 each independently represent a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms, and R1 and R2 may also be bonded to form a cyclic structure. R3 and R4 each independently represent a hydrogen atom, or a linear or branched hydrocarbon group having 1 to 4 carbon atoms, In formula (5), R7 to R9 each independently represent a hydrogen atom or a methyl group, R10 and R11 represent a hydrogen atom or a methyl group, or may also be bonded to form a saturated or unsaturated ring, which is a 5-membered ring or a 6-membered ring, and * represents a bonding bond connected to the (meth)acryloyloxy group, the polymerizable monomer (m-3) containing an aromatic ring is at least one selected from benzyl (meth)acrylate, phenyl (meth)acrylate, styrene, and α-, o-, m-, p-alkyl derivatives of styrene, relative to 100 parts by mass of the pigment (B), 10 to 50 parts by mass of the binder resin (A-1) is contained, the content of the polymeric dispersant (C) is 10 to 50 parts by mass relative to 100 parts by mass of the pigment (B).

2. The pigment dispersion composition according to claim 1, wherein the pigment (B) contains a pigment having a halogenated phthalocyanine skeleton.

3. The pigment dispersion composition according to claim 1 or 2, wherein the polymeric dispersant (C) has at least one group selected from a tertiary amino group and a quaternary ammonium cationic group.

4. The pigment dispersion composition according to claim 1 or 2, characterized in that the polymeric dispersant (C) is at least one monomer selected from a monomer having a tertiary amino group and an ethylenically unsaturated group, and a monomer having a quaternary ammonium cationic group and an ethylenically unsaturated group, and a block polymer of other monomers having an ethylenically unsaturated group.

5. The pigment dispersion composition according to claim 1 or 2, wherein the group reactive with a carboxyl group in the compound (m-4) having an ethylenically unsaturated group is an epoxy group or an oxetanyl group.

6. The pigment dispersion composition according to claim 1 or 2, when the total of the polymerizable monomer (m-1a), the acrylic acid (m-2) and the polymerizable monomer (m-3) having an aromatic ring of the copolymer (P) is set to 100 mol%, the proportion of the polymerizable monomer (m-3) having an aromatic ring is 9 to 70 mol%.

7. The pigment dispersion composition according to claim 1 or 2, wherein the binder resin (A-1) is the resin (A-1b).

8. A photosensitive coloring composition characterized in that it contains the pigment dispersion composition according to any one of claims 1 to 7, a binder resin (A-2), a reactive diluent (E) and a photopolymerization initiator (F).

9. The photosensitive coloring composition according to claim 8, relative to 100 parts by mass of the pigment (B) contains a total of 50 to 280 parts by mass of the binder resins (A-1) and (A-2), contains 40 to 200 parts by mass of the reactive diluent (E), and contains 0.1 to 10 parts by mass of the photopolymerization initiator (F).

10. A resin cured film obtained by curing the photosensitive coloring composition according to claim 8 or 9.

11. A color filter having a cured product of the photosensitive coloring composition according to claim 8 or 9.

12. An image display component including the color filter according to claim 11.

Images