Pigment dispersion composition, photosensitive colored composition, and color filter

Abstract

To provide a pigment dispersion composition with superior pigment dispersibility and storage stability, which is used in a photosensitive coloring composition, yielding a cured product that has superior developability, undergoes a curing process at low temperatures, and has superior solvent resistance.SOLUTION: A pigment dispersion composition contains a binder resin (A-1), a polymer dispersant (B), a pigment (C), and a solvent (D-1). The binder resin (A-1) includes a first binder resin (A-1a). The first binder resin (A-1a) is an adduct of an epoxy group-containing resin precursor (PA-1a) with an ethylenically unsaturated group-containing compound (a-1) with a functional group reactable with an epoxy group. The polymer dispersant (B) has a quaternary ammonium cation group (g-1) with at least one selected from the group consisting of ethylenically unsaturated groups and groups with carbon-carbon triple bonds.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a pigment dispersion composition, a photosensitive colored composition, and a color filter. [Background technology]

[0002] Currently, from the perspective of resource and energy conservation, photosensitive resin compositions that can be cured by active energy rays such as ultraviolet rays and electron beams are widely used in fields such as various coatings, printing, paints, and adhesives. In the field of electronic materials, photosensitive resin compositions are used as solder resists for printed circuit boards, and as resists for color filters in displays such as liquid crystal and organic EL displays.

[0003] 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 black matrix. Color filters with this configuration are usually manufactured by sequentially forming color patterns such as black matrices and pixels, and patterns such as protective films, on a transparent substrate. Various methods have been proposed for forming these patterns. Among them, color filters manufactured using photolithography, which involves repeatedly coating, exposing, developing, and baking a photosensitive resin composition in which pigments / dyes are dispersed as a resist, are currently the mainstream because they offer excellent durability and provide a color pattern with few defects such as pinholes.

[0004] Generally, photosensitive resin compositions used in photolithography contain an alkali-soluble binder resin, a reactive diluent, a photopolymerization initiator, a pigment / dye (also called a colorant), and a solvent. In the method of producing color filters using this photosensitive resin composition, patterns of black matrix, red, green, and blue are repeatedly formed, so the cured product of the photosensitive resin composition is required to be resistant to various solvents to which it is exposed during the manufacturing process. In addition, the light-emitting layer of organic EL displays often uses heat-sensitive materials, creating a demand for color filters that can be cured at low curing temperatures.

[0005] In recent years, there has been a demand for higher image quality and resolution in displays such as LCDs and OLEDs, and color filters are also required to be designed to achieve higher brightness and a wider color reproduction range. In order to achieve higher brightness and a wider color reproduction range, there are examples where only dyes are used as colorants, but dyes have inferior heat resistance and solvent resistance compared to pigments, and their usage ratio and types are limited, so in most cases pigments are included in the colorant. When forming a color filter using pigments, uniform miniaturization of the pigment is essential. By miniaturizing the pigment, scattering of light transmitted through the color filter by pigment particles is reduced, which contributes more to the transmittance and achieves higher brightness. However, finely milled pigment particles tend to aggregate, leading to problems such as reduced dispersibility of the pigment and decreased storage stability of the pigment dispersion composition. Using a pigment and a dispersant in combination is an effective method for improving the dispersibility of finely milled pigments in a pigment dispersion composition.

[0006] Furthermore, efforts are being made to incorporate high concentrations of colorants in order to expand the color reproduction range. As the concentration of colorants increases, the concentrations of dispersants and other compositions are relatively reduced. Therefore, it is necessary for various resist properties such as pigment dispersibility, storage stability of the pigment dispersion composition, heat resistance, solvent resistance, and pattern adhesion to be exhibited even with a smaller amount of dispersant.

[0007] Generally, dispersants have both a site that adsorbs to pigments and a site that has high affinity for solvents or other resin compositions. The optimal structure of the site that adsorbs to pigments changes depending on the surface condition of the pigment. For example, for pigments with acidic surfaces, dispersants with basic adsorption sites are used, and in many cases, as in Patent Document 1, amino groups are used for the basic adsorption sites. Furthermore, in recent years, as described in Patent Documents 1 to 3, dispersants have been developed that incorporate ethylenically unsaturated groups, which are photosensitive groups, to impart curing functionality, resulting in dispersants that are more photocurable and have excellent solvent resistance.

Prior Art Documents

Patent Documents

[0008]

Patent Document 1

Patent Document 2

Patent Document 3

Summary of the Invention

Problems to be Solved by the Invention

[0009] However, when the dispersants disclosed in Patent Documents 1 to 3 are used, a cured product with good solvent resistance can be obtained. However, there are cases where the pigment dispersibility is insufficient and it is difficult to use alone, and the storage stability of the pigment dispersion composition also needs to be improved. In addition, in order for the crosslinking by the addition reaction of the ethylenically unsaturated group, which is a curable group, to proceed, a high curing temperature or strong ultraviolet irradiation is required. However, when using heat-sensitive materials such as organic ELs, whose demand has been expanding in recent years, a cured product must be produced under limited temperature conditions (about 90 to 130°C). Under these conditions, a cured product with insufficient solvent resistance is obtained, and improvement has been demanded.

[0010] The present invention has been made to solve the above problems, and an object thereof is to provide a pigment dispersion composition having good pigment dispersibility and storage stability. When the present pigment dispersion composition is used, a photosensitive coloring composition having good developability, sufficiently cured even at low temperatures, and a cured product having excellent solvent resistance is obtained, and an object thereof is to provide a color filter having the cured product and an image display element including the same.

Means for Solving the Problems

[0011] [[ID=4​​​​​Pigment (C) and Solvent (D-1), A pigment dispersion composition containing, The binder resin (A-1) contains at least one selected from the first binder resin (A-1a) and the second binder resin (A-1aa), The first binder resin (A-1a) is an addition reaction product of an epoxy group-containing resin precursor (PA-1a) and an ethylenically unsaturated group-containing compound (a-1) having a functional group that is reactive with epoxy groups. The second binder resin (A-1aa) is an addition product of the first binder resin (A-1a) and one or more compounds (a-2) selected from polybasic acids and polybasic acid anhydrides. The epoxy group-containing resin precursor (PA-1a) is a copolymer of a polymerizable monomer (M) containing an epoxy group-containing (meth)acrylate (m-1), A pigment dispersion composition characterized in that the polymer dispersant (B) has a quaternary ammonium cation group (g-1) having one or more selected from the group consisting of an ethylenically unsaturated group and a group having a carbon-carbon triple bond. [2] The pigment dispersion composition according to [1], wherein the amount of ethylenically unsaturated groups in the first binder resin (A-1a) and the second binder resin (A-1aa) is 1600 to 8000 μmol / g. [3] The pigment dispersion composition according to [1] or [2], wherein the amount of ethylenically unsaturated groups in the polymer dispersant (B) is 50 to 1600 μmol / g. [4] The pigment dispersion composition according to any one of [1] to [3], wherein the polymerizable monomer (M) contains 40 to 100 mol% of the epoxy group-containing (meth)acrylate (m-1). [5] The polymerizable monomer (M) further comprises a polymerizable monomer (m-2) having a crosslinked cyclic hydrocarbon group having 7 to 20 carbon atoms, The pigment dispersion composition according to any one of [1] to [4], wherein the polymerizable monomer (M) contains 0.5 to 25 mol% of the polymerizable monomer (m-2) having a crosslinked cyclic hydrocarbon group having 7 to 20 carbon atoms. [6] In the first binder resin (A-1a), the addition rate of the ethylenically unsaturated group-containing compound (a-1) having a functional group reactive with the epoxy group is 10 to 100 mol% with respect to 100 mol% of the epoxy groups of the epoxy group-containing resin precursor (PA-1a). The pigment dispersion composition according to any one of [1] to [5]. [7] The pigment dispersion composition according to any one of [1] to [6], wherein the binder resin (A-1) contains the second binder resin (A-1aa). [8] The pigment dispersion composition according to any one of [1] to [7], wherein the quaternary ammonium cation group (g-1) contained in the polymer dispersant (B) is one or more selected from the group consisting of the groups represented by the following formula (4), the following formula (5), the following formula (6), and the following formula (7). -(CH2) m -O-(CO)-(NH)-(CH2) n -O-(CO)-CR 1 =CH2(4) -(CH2) m -O-(CO)-CR 1 =CH2(5) -(CH2) m -CR 1 =CH2(6) -(CH2) m -C≡CH (7) (In formulas (4) to (7), m and n are each independently an integer of 1 to 20, and R 1 represents a hydrogen atom or a methyl group.) [9] The pigment dispersion composition according to any one of [1] to [8], wherein the polymer dispersant (B) further has an amino group.

[10] The binder resin (A-1) further contains a third binder resin (A-1b), The third binder resin (A-1b) is an addition reaction product of a carboxy group-containing resin precursor (PA-1b) and an ethylenically unsaturated group-containing compound (a-3) having a functional group reactive with the carboxy group, A pigment dispersion composition according to any one of [1] to [9] wherein the acid value of the third binder resin (A-1b) is greater than that of the first binder resin (A-1a) and the second binder resin (A-1aa).

[11] A pigment dispersion composition according to any one of [1] to

[10] , wherein the pigment (C) comprises a pigment having a halogenated phthalocyanine skeleton.

[12] With respect to 100 parts by mass of the pigment (C), The aforementioned binder resin (A-1) is contained in an amount of 10 to 80 parts by mass. A pigment dispersion composition according to any one of [1] to

[11] , containing 5 to 80 parts by mass of the polymer dispersant (B).

[13] A pigment dispersion composition according to any one of [1] to

[12] , Binder resin (A-2), Reactive diluent (E), Photopolymerization initiator (F) and A photosensitive coloring composition characterized by containing [a certain substance].

[14] With respect to 100 parts by mass of the pigment (C), The total amount of the binder resin (A-1) and the binder resin (A-2) is 30 to 280 parts by mass. The above polymer dispersant (B) is contained in 5 to 80 parts by mass, The reactive diluent (E) is contained in 20 to 200 parts by mass, The photosensitive coloring composition according to

[13] , comprising 0.1 to 20 parts by mass of the photopolymerization initiator (F). A resin-cured film obtained by curing the photosensitive coloring composition described in

[15]

[13] or

[14] . A color filter having a cured product of the photosensitive coloring composition described in

[16]

[13] or

[14] .

[17] An image display element comprising the color filter described in

[16] . [Effects of the Invention]

[0012] According to the present invention, a pigment dispersion composition with good pigment dispersibility and storage stability can be provided. Furthermore, by using this pigment dispersion composition in a photosensitive coloring composition, a cured product can be obtained that has good developability, hardens at low temperatures, and has excellent solvent resistance. In addition, a color filter having a cured product of this photosensitive coloring composition and an image display element equipped therewith can be provided. [Modes for carrying out the invention]

[0013] Embodiments of the present invention will be described in detail below. However, the present invention is not limited to the embodiments shown below. In this specification, "(meth)acryloyloxy group" refers to one or more selected from methacryloyloxy groups and acryloyloxy groups. The same applies to "(meth)acrylic acid" and "(meth)acrylate".

[0014] <Pigment dispersion composition> A pigment dispersion composition according to one embodiment of the present invention (sometimes referred to as "the pigment dispersion composition of this embodiment") contains a binder resin (A-1), a polymer dispersant (B), a pigment (C), and a solvent (D-1).

[0015] [Binder resin (A-1)] The binder resin (A-1) according to this embodiment contains at least one selected from a first binder resin (A-1a) and a second binder resin (A-1aa). The binder resin (A-1) may further contain a third binder resin (A-1b) as needed.

[0016] <First Binder Resin (A-1a)> The first binder resin (A-1a) according to this embodiment is an addition product of an epoxy group-containing resin precursor (PA-1a) and an ethylenically unsaturated group-containing compound (a-1) (hereinafter also simply referred to as "compound (a-1)") having a functional group that is reactive with epoxy groups. The pigment dispersion composition of this embodiment, by containing the first binder resin (A-1a), exhibits affinity with the polymer dispersant (B) and pigment (C) described later, making it possible to obtain a pigment dispersion composition with excellent pigment dispersibility and storage stability. Furthermore, in the synthesis method of the first binder resin (A-1a), the process of introducing the ethylenically unsaturated group, which is a curable group, involves minimal side reactions. Therefore, because the basic physical properties of the resin, such as the acid value and molecular weight, are easily controlled, there is less risk of runaway reactions such as gelation, and it is possible to provide a binder resin with a high amount of introduced ethylenically unsaturated group, which was difficult with conventional resins. In other words, in the process of curing a photosensitive colored composition to obtain a resin-cured film, even under limited temperature conditions for thermal curing, the inclusion of the first binder resin (A-1a) makes it possible to provide a cured product with excellent solvent resistance.

[0017] The amount of ethylenically unsaturated groups in the first binder resin (A-1a) according to this embodiment is preferably 1600 to 8000 μmol / g, more preferably 3100 to 7000 μmol / g, and even more preferably 3800 to 6000 μmol / g. When the amount of ethylenically unsaturated groups is 1600 μmol / g or more, sufficient low-temperature curability is obtained, and the resin cured film cured at low temperatures exhibits sufficient solvent resistance. When the amount of ethylenically unsaturated groups is 8000 μmol / g or less, the storage stability of the pigment dispersion composition is good.

[0018] The acid value of the first binder resin (A-1a) according to this embodiment is preferably 200 mg KOH / g or less, more preferably 160 mg KOH / g or less, and even more preferably 120 mg KOH / g or less. When the acid value is 200 mg KOH / g or less, the storage stability of the pigment dispersion composition is good.

[0019] The weight-average molecular weight of the first binder resin (A-1a) in this embodiment is preferably 3,000 to 50,000, more preferably 5,000 to 30,000, and even more preferably 7,000 to 20,000. When the weight-average molecular weight is 3,000 or more and 50,000 or less, particularly good dispersion stability is obtained when it is made into a pigment dispersion.

[0020] In this embodiment, the content of the first binder resin (A-1a) is preferably 10% by mass or more, more preferably 30% by mass or more, and even more preferably 50% by mass or more, in the total amount of binder resin (A-1). A content of 10% by mass or more of the first binder resin (A-1a) allows for the formation of a strong coating film due to the crosslinking of ethylenically unsaturated groups abundantly present in the first binder resin (A-1a), resulting in good low-temperature curing properties and solvent resistance of the low-temperature cured resin film. On the other hand, in some cases, by using binder resins with higher acid values, such as the second binder resin (A-1aa) and the third binder resin (A-1b) described later, it becomes possible to adjust the alkaline development speed while exhibiting sufficient low-temperature curing properties as a photosensitive colored composition. From this viewpoint, the content of the first binder resin (A-1a) may be 100% by mass or less, or 90% by mass or less, 70% by mass or less, or 50% by mass or less.

[0021] The epoxy group-containing resin precursor (PA-1a) according to this embodiment is a copolymer of a polymerizable monomer (M) containing an epoxy group-containing (meth)acrylate (m-1). As the polymerizable monomer (M) for obtaining the epoxy group-containing resin precursor (PA-1a), a polymerizable monomer (m-2) having a crosslinked cyclic hydrocarbon group with 7 to 20 carbon atoms (hereinafter also simply referred to as "polymerizable monomer (m-2)") and other monomers (m-3) can be used in combination as needed. By using an epoxy group-containing resin precursor (PA-1a) in the production of the first binder resin (A-1a), it is expected that the addition reaction to introduce ethylenically unsaturated groups into the copolymer in a later process will proceed with high selectivity and reaction rate. Therefore, the possibility of residual unreacted monomers is reduced, and a high-quality binder resin (A-1) can be obtained.

[0022] The epoxy group-containing (meth)acrylate (m-1) according to this embodiment is not particularly limited as long as it is a compound having an epoxy group and a (meth)acryloyloxy group. Specifically, examples include glycidyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate glycidyl ether, 3,4-epoxycyclohexylmethyl (meth)acrylate, and (3-ethyloxetan-3-yl)methyl (meth)acrylate. Among these, glycidyl (meth)acrylate is preferred from the viewpoint of ease of availability and the further addition of compound (a-1) described later.

[0023] The content of the epoxy group-containing (meth)acrylate (m-1) in this embodiment is preferably 40 to 100 mol%, more preferably 50 to 98 mol%, and even more preferably 80 to 96 mol%, based on 100 mol% of the polymerizable monomer (M). A content of 40 mol% or more provides sufficient reaction sites and thus reactivity for the compound (a-1) described later.

[0024] The polymerizable monomer (m-2) according to this embodiment does not have an epoxy group and is a polymerizable monomer having a cross-linked cyclic hydrocarbon group with 7 to 20 carbon atoms and an ethylenically unsaturated double bond. By including the polymerizable monomer (m-2), a color filter can be provided that has high surface hardness and can suppress pigment (C) bleed-out. At the same time, it has high heat decomposition resistance and high heat yellowing resistance, and the color change of the color filter after baking can be reduced. Specifically, (meth)acrylates having cyclic hydrocarbon groups such as adamantyl (meth)acrylate, dicyclopentenyl (meth)acrylate, dicyclopentanyl (meth)acrylate, isobornyl (meth)acrylate, norbornene (bicyclo[2.2.1]hept-2-ene), 5-methylbicyclo[2.2.1]hept-2-ene, tetracyclo[4.4.0.1 2,5 .1 7,10 ] Dodeca-3-ene, 8-ethyltetracyclo[4.4.0.1 2,5 .1 7,10 ] Dodeca-3-ene, dicyclopentadiene, tricyclo[5.2.1.02,6 Deca-8-en, tricyclo[4.4.0.1 2,5 ]Undeca-3-ene, tricyclo[6.2.1.0 1,8 ]Undeka-9-ene, tetracyclo[4.4.0.1 2,5 .1 7,10 .0 1,6 ] Dodeca-3-ene, 8-ethylidenetetracyclo[4.4.0.1 2,5 .1 7,12 ] Dodeca-3-ene, pentacyclo[6.5.1.1 3,6 .0 2,7 .0 9,13 Examples include pentadeca-4-ene. These may be used individually or in combination of two or more.

[0025] In particular, from the viewpoint of surface hardness, (meth)acrylates having a cross-linked cyclic hydrocarbon group with 7 to 20 carbon atoms are preferred, and dicyclopentanyl (meth)acrylate is more preferred.

[0026] The content of polymerizable monomer (m-2) is preferably 0.5 to 25 mol%, more preferably 1 to 20 mol%, and even more preferably 2 to 15 mol%, based on 100 mol% of polymerizable monomer (M). By having a content of 0.5 mol% or more, the high heat decomposition resistance and high heat yellowing resistance of the polymerizable monomer (m-2) can be imparted to the binder resin (A-1). On the other hand, by setting the content to 25 mol% or less, an excessive increase in the glass transition temperature of the binder resin (A-1) can be prevented, the crosslinking reaction by ethylenically unsaturated groups during ultraviolet exposure of the photosensitive colored composition can not be hindered, and a color filter with high surface hardness can be provided.

[0027] The other monomer (m-3) in this embodiment is a polymerizable monomer other than the epoxy group-containing (meth)acrylate (m-1) and polymerizable monomer (m-2). That is, the epoxy group-containing resin precursor (PA-1a) may contain other polymerizable monomers copolymerizable with the epoxy group-containing (meth)acrylate (m-1) and polymerizable monomer (m-2). The other monomer (m-3) is generally a radical polymerizable compound having an ethylenically unsaturated group, and may contain one or more polymerizable monomers as constituent units, including the following specific examples, as long as they do not interfere with the desired properties derived from the epoxy group-containing (meth)acrylate (m-1) and polymerizable monomer (m-2) in the epoxy group-containing resin precursor (PA-1a). Other specific examples of monomers (m-3) include dienes such as butadiene; methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, iso-propyl (meth)acrylate, n-butyl (meth)acrylate, sec-butyl (meth)acrylate, iso-butyl (meth)acrylate, tert-butyl (meth)acrylate, pentyl (meth)acrylate, neopentyl (meth)acrylate, isoamyl (meth)acrylate, hexyl ( (meth)acrylic acid esters such as 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; Isocyanato group-containing (meth)acrylic acid esters such as 2-isocyanatoethyl (meth)acrylate, 2-isocyanatopropyl (meth)acrylate, 3-isocyanatopropyl (meth)acrylate, 2-isocyanato-1-methylethyl (meth)acrylate, 2-isocyanato-1,1-dimethylethyl (meth)acrylate, 4-isocyanatocyclohexyl (meth)acrylate, and 1,1-(bisacryloyloxymethyl)ethyl isocyanate; and blocked isocyanato group-containing (meth)acrylic acid esters obtained by blocking the isocyanato groups of the said isocyanato group-containing (meth)acrylic acid esters using a blocking agent; (meth)acrylamides such as (meth)acrylamide, (meth)acrylamide N,N-dimethylamide, (meth)acrylamide N,N-diethylamide, (meth)acrylamide N,N-dipropylamide, (meth)acrylamide N,N-diisopropylamide, and (meth)acrylamide anthracenylamide; (meth) anilide acrylate, (meth) acryloyl nitrile, acrolein; Vinyl compounds such as vinyl chloride, vinylidene chloride, vinyl fluoride, vinylidene fluoride, N-vinylpyrrolidone, vinylpyridine, vinyl acetate, and vinyltoluene; Examples include maleimides such as N-cyclohexylmaleimide and N-laurylmaleimide; and unsaturated dicarboxylic acid diesters such as diethyl citraconate, diethyl maleate, diethyl fumarate, and diethyl itaconate. These may be used individually or in combination of two or more, as needed. Among the other monomers (m-3), polymerizable monomers containing aromatic rings are preferred, other than epoxy group-containing (meth)acrylates (m-1) and polymerizable monomers (m-2). Specific examples include benzyl (meth)acrylate, phenyl (meth)acrylate, triphenylmethyl (meth)acrylate, cumyl (meth)acrylate, rosin (meth)acrylate, naphthalene (meth)acrylate, anthracene (meth)acrylate, 4-hydroxyphenyl (meth)acrylate, styrene, α-, o-, m-, p-alkyl, nitro, cyano, and amide derivatives of styrene, N-phenylmaleimide, and N-(4-hydroxyphenyl)maleimide. When monomer (m-3) is a polymerizable monomer containing aromatic rings as shown in the specific examples, the affinity of the binder resin (A-1) with the pigment (C) is improved, resulting in a pigment dispersion composition with excellent pigment dispersibility and storage stability. Accordingly, by increasing the concentration of the pigment, it is possible to provide a pigment dispersion composition that can obtain sufficient pigment dispersibility and storage stability even when the concentrations of the polymer dispersant (B) and binder resin (A-1) are reduced.

[0028] The content of other monomers (m-3) according to this embodiment is preferably 0.5 to 40 mol%, more preferably 1 to 30 mol%, and even more preferably 2 to 20 mol%, based on 100 mol% of polymerizable monomer (M).

[0029] The ethylenically unsaturated group-containing compound (a-1) having a functional group reactive with an epoxy group according to this embodiment is not particularly limited as long as it has a functional group reactive with an epoxy group and an ethylenically unsaturated group. Examples of functional groups reactive with an epoxy group include carboxyl groups, amino groups, hydroxyl groups, and mercapto groups, but carboxyl groups are preferred from the viewpoint of availability and reactivity, and (meth)acrylic acid is particularly preferred.

[0030] The addition ratio of compound (a-1) according to this embodiment is preferably 10 to 100 mol%, more preferably 50 to 100 mol%, even more preferably 60 to 100 mol%, and particularly preferably 80 to 100 mol%, relative to 100 mol% of the epoxy groups in the epoxy group-containing resin precursor (PA-1a). An addition ratio of 10% or more allows the pigment dispersion composition to exhibit photosensitivity, and an addition ratio of 50% or more reduces the number of remaining epoxy groups, thereby reducing the possibility of unwanted side reactions such as crosslinking. Furthermore, an addition ratio of 60 mol% or more provides a photosensitive colored composition that has good storage stability while possessing solvent resistance that far surpasses conventional pigment dispersions.

[0031] <Second Binder Resin (A-1aa)> The second binder resin (A-1aa) according to this embodiment is an addition product of the first binder resin (A-1a) and one or more compounds (a-2) selected from polybasic acids and polybasic acid anhydrides (hereinafter also simply referred to as "compound (a-2)"). The compound (a-2) according to this embodiment is not particularly limited as long as it is a compound having a polybasic acid structure or an acid anhydride of a compound having a polybasic acid structure. By adding compound (a-2) to a portion of the hydroxyl groups of the first binder resin (A-1a), carboxyl groups are introduced to the first binder resin (A-1a). The hydroxyl groups of the first binder resin (A-1a) are formed during the ring-opening addition reaction between the epoxy group derived from the epoxy group-containing (meth)acrylate (m-1) of the epoxy group-containing resin precursor (PA-1a) and compound (a-1).

[0032] The amount of ethylenically unsaturated groups in the second binder resin (A-1aa) according to this embodiment is preferably 1600 to 8000 μmol / g, more preferably 3100 to 7000 μmol / g, and even more preferably 3800 to 6000 μmol / g. When the amount of ethylenically unsaturated groups is 1600 μmol / g or more, sufficient low-temperature curability is obtained, and the resin cured film cured at low temperatures exhibits sufficient solvent resistance. When the amount of ethylenically unsaturated groups is 8000 μmol / g or less, the storage stability of the pigment dispersion composition is good.

[0033] The acid value of the second binder resin (A-1aa) according to this embodiment is preferably 1 to 200 mg KOH / g, more preferably 5 to 160 mg KOH / g, and even more preferably 10 to 120 mg KOH / g. When the acid value is 200 mg KOH / g or less, the storage stability of the pigment dispersion composition is good.

[0034] The weight-average molecular weight of the second binder resin (A-1aa) in this embodiment is preferably 3,000 to 50,000, more preferably 5,000 to 30,000, and even more preferably 7,000 to 20,000. When the weight-average molecular weight is 3,000 or more and 50,000 or less, particularly good dispersion stability is obtained when it is made into a pigment dispersion.

[0035] In this embodiment, the content of the second binder resin (A-1aa) is preferably 10% by mass or more, more preferably 30% by mass or more, and even more preferably 50% by mass or more, in the total amount of binder resin (A-1). A content of 10% by mass or more of the second binder resin (A-1aa) is expected to facilitate the formation of a strong coating film due to the crosslinking of ethylenically unsaturated groups abundantly present in the second binder resin (A-1aa), resulting in good low-temperature curing properties and solvent resistance of the low-temperature cured resin film. On the other hand, in some cases, by using a binder resin with a higher acid value, such as the third binder resin (A-1b) described later, it becomes possible to adjust the alkaline development speed while exhibiting sufficient low-temperature curing properties as a photosensitive colored composition. From this viewpoint, the content of the second binder resin (A-1aa) may be 100% by mass or less, or 90% by mass or less, 70% by mass or less, or 50% by mass or less.

[0036] Examples of compound (a-2) according to this embodiment include 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, and the like. These may be used individually or in combination of two or more.

[0037] The addition ratio of compound (a-2) according to this embodiment is preferably 0.5 to 50 mol%, more preferably 3 to 45 mol%, and even more preferably 7 to 35 mol%, relative to 100 mol% of the hydroxyl groups present in the first binder resin (A-1a). By keeping the addition ratio of compound (a-2) within the above range, the effect of improving developability by introducing carboxyl groups to the first binder resin (A-1a) can be imparted while reducing the remaining unreacted monomers.

[0038] <Third Binder Resin (A-1b)> The third binder resin (A-1b) according to this embodiment is an addition reaction product of a carboxyl group-containing resin precursor (PA-1b) and an ethylenically unsaturated group-containing compound (a-3) having a functional group reactive with a carboxyl group (hereinafter also simply referred to as "compound (a-3)"), and is a resin having a higher acid value than the first binder resin (A-1a) and the second binder resin (A-1aa). Furthermore, compound (a-2) may be added in any proportion as needed. By using the third binder resin (A-1b), the developability of the photosensitive colored composition can be improved.

[0039] The amount of ethylenically unsaturated groups in the third binder resin (A-1b) according to this embodiment is preferably 500 to 6000 μmol / g, more preferably 700 to 5000 μmol / g, and even more preferably 900 to 4000 μmol / g. If the amount of ethylenically unsaturated groups is 500 μmol / g or more, the low-temperature curability as a photosensitive colored composition is good. If the amount of ethylenically unsaturated groups is 6000 μmol / g or less, a sufficient amount of acid value can be secured for the third binder resin (A-1b), and the developability as a photosensitive colored composition is good.

[0040] The acid value of the third binder resin (A-1b) according to this embodiment is preferably 10 to 300 mg KOH / g, more preferably 20 to 250 mg KOH / g, and even more preferably 50 to 230 mg KOH / g. By setting the acid value of the third binder resin (A-1b) within the above range, the developability as a photosensitive colored composition can be improved, and the storage stability of the pigment dispersion composition is good.

[0041] The weight-average molecular weight of the third binder resin (A-1b) according to this embodiment is preferably 3,000 to 50,000, and more preferably 5,000 to 30,000.

[0042] The carboxyl group-containing resin precursor (PA-1b) is a copolymer of a polymerizable monomer (M') containing a carboxyl group-containing monomer (m-4). The polymerizable monomer (M') used to obtain the carboxyl group-containing resin precursor (PA-1b) may optionally include the polymerizable monomer (m-2) and the other monomer (m-3). The carboxyl group-containing monomer (m-4) is not particularly limited as long as it is a monomer having a carboxyl group and an ethylenically unsaturated group. Specifically, examples include (meth)acrylic acid, itaconic acid, crotonic acid, vinylbenzoic acid, and unsaturated monobasic acids such as α-haloalkyl, alkoxyl, halogen, nitro, and cyano-substituted derivatives of (meth)acrylic acid. Among these, (meth)acrylic acid is preferred from the viewpoint of reactivity for obtaining the carboxyl group-containing resin precursor (PA-1b). The ethylenically unsaturated group-containing compound (a-3) having a functional group reactive with a carboxyl group according to this embodiment is not particularly limited as long as it is a compound having both a functional group reactive with a carboxyl group and an ethylenically unsaturated group. Examples of functional groups reactive with a carboxyl group include hydroxyl groups, mercapto groups, blocked isocyanate groups, and epoxy groups. Among these, compounds having an epoxy group are preferred from the viewpoint of reactivity with a carboxyl group, and in that sense, compounds similar to the epoxy group-containing (meth)acrylate (m-1) are particularly preferred. Furthermore, glycidyl (meth)acrylate is extremely preferred from the viewpoint of availability.

[0043] The content of the third binder resin (A-1b) in this embodiment is preferably 90% by mass or less, more preferably 70% by mass or less, and even more preferably 50% by mass or less, in the binder resin (A-1). By making it 90% by mass or less, the excellent low-temperature curability of the first binder resin (A-1a) or the second binder resin (A-1aa) can be expected. On the other hand, by incorporating a third binder resin (A-1b) having a higher acid value than the first binder resin (A-1a) and the second binder resin (A-1aa) within the above range, it becomes possible to freely adjust the alkali development speed as a photosensitive colored composition.

[0044] In the pigment dispersion composition of this embodiment, the content of binder resin (A-1) is preferably 10 to 80 parts by mass, more preferably 15 to 75 parts by mass, and even more preferably 20 to 65 parts by mass, per 100 parts by mass of pigment (C). When the content of binder resin (A-1) is 10 parts by mass or more, a photosensitive colored composition with good developability can be obtained, as well as a resin cured film with excellent heat resistance, solvent resistance, and pattern adhesion. When the content of binder resin (A-1) is 80 parts by mass or less, a sufficient content of pigment (C) can be secured, and a resin cured film with excellent color reproducibility can be obtained.

[0045] <Polymer dispersant (B)> The polymer dispersant (B) according to this embodiment is not particularly limited as long as it has a quaternary ammonium cation group (g-1) (hereinafter also simply referred to as "quaternary ammonium cation group (g-1)") having one or more selected from the group consisting of ethylenically unsaturated groups and groups having a carbon-carbon triple bond. By having one or more selected from the group consisting of ethylenically unsaturated groups and groups having a carbon-carbon triple bond, the polymer dispersant (B) can react with the ethylenically unsaturated groups of the binder resin (A-1) and the reactive diluent (E) described later to crosslink them. Therefore, even when the photosensitive colored composition is heat-treated at a low temperature (90-130°C), a resin cured film with excellent solvent resistance can be obtained. In this specification, a quaternary ammonium cation group refers to a group in which four carbon atoms are bonded to a nitrogen atom, and does not include amide bonds or urea bonds.

[0046] Furthermore, the polymer dispersant (B) may also have an amino group in addition to the quaternary ammonium cation group (g-1). The amino groups that the polymer dispersant (B) according to this embodiment may have include primary, secondary, and tertiary amino groups. A primary amino group is a group in which one carbon atom is bonded to a nitrogen atom, a secondary amino group is a group in which two carbon atoms are bonded to a nitrogen atom, and a tertiary amino group is a group in which three carbon atoms are bonded to a nitrogen atom. In particular, when the polymer dispersant (B) has a tertiary amino group and a quaternary ammonium cation group (g-1), it has good dispersibility for pigments in the pigment dispersion composition, good storage stability, and good developability when used as a photosensitive colored composition.

[0047] The quaternary ammonium cation group (g-1) contained in the polymer dispersant (B) is preferably an ethylenically unsaturated group or a group having a carbon-carbon triple bond, selected from the group consisting of the groups represented by the following formulas (1), (2), and (3), from the viewpoint of having affinity with the pigment (B) described later. That is, it is preferable that the quaternary ammonium cation group (g-1) contained in the polymer dispersant (B) has one or more groups selected from the group consisting of the groups represented by the following formulas (1), (2), and (3).

[0048] -(CH2) m -OX-(CO)-CR 1 =CH2(1) -(CH2) m -X-CR 1 =CH2(2) -(CH2) m -XC≡CH (3)

[0049] (In formulas (1) to (3), m is an integer from 1 to 20, X is a single bond or a divalent linking group with 1 to 20 carbon atoms, R 1 (This represents a hydrogen atom or a methyl group.) In formulas (1) to (3), m is 1 to 20, preferably 1 to 10, and more preferably 1 to 6. The divalent linking group represented by X has 1 to 20 carbon atoms, preferably 1 to 10, and more preferably 1 to 6 carbon atoms. The divalent linking group represented by X may include ether bonds, ester bonds, amide bonds, etc. Specifically, examples include alkylene groups such as methylene groups and ethylene groups, and (poly)alkylene oxides such as methylene oxide, ethylene oxide, and diethylene oxide.

[0050] From the viewpoint of the ease of synthesis of the polymer dispersant (B), the availability of raw materials, and the affinity with the pigment (C) described later, it is more preferable that the ethylenically unsaturated group and the group having a carbon-carbon triple bond are ethylenically unsaturated groups or groups having a carbon-carbon triple bond selected from the group consisting of the groups represented by the following formulas (4), (5), (6), and (7). In other words, it is more preferable that the quaternary ammonium cation group (g-1) contained in the polymer dispersant (B) has one or more selected from the group consisting of the groups represented by the following formulas (4), (5), (6), and (7).

[0051] -(CH2) m -O-(CO)-(NH)-(CH2) n -O-(CO)-CR 1 =CH2(4) -(CH2) m -O-(CO)-CR 1 =CH2(5) -(CH2) m -CR 1 =CH2(6) -(CH2) m -C≡CH (7)

[0052] (In equations (4) to (7), m and n are independent integers from 1 to 20, and R 1 (This represents a hydrogen atom or a methyl group.) In equations (4) to (7), m and R 1The definition and preferred range of n are the same as those shown in formulas (1) to (3). n is 1 to 19, preferably 1 to 9, and more preferably 1 to 5.

[0053] In this embodiment, the polymer dispersant (B) is preferably an addition product of an addition reaction product of a tertiary amino group-containing polymer compound (b-0) and a functional group-containing halogen compound (b-1), and a compound (b-2) (hereinafter also simply referred to as "compound (b-2)") having one or more selected from the group consisting of a group reactive with the functional group, an ethylenically unsaturated group, and a group having a carbon-carbon triple bond, or an addition product of an addition reaction product of a tertiary amino group-containing polymer compound (b-0) and a halogen compound (b-3) (hereinafter also simply referred to as "halogen compound (b-3)") containing one or more selected from the group consisting of an ethylenically unsaturated group and a group having a carbon-carbon triple bond. A halogen compound refers to an organic chemical substance to which halogen atoms such as chlorine, bromine, and iodine are bonded. When a tertiary amino group-containing polymer compound (b-0) reacts with the functional group-containing halogen compound (b-1), the residue from which the halogen atom of the functional group-containing halogen compound (b-1) has been removed coordinates to the tertiary amino group of the tertiary amino group-containing polymer compound (b-0), forming a quaternary ammonium cation group. Next, compound (b-2) reacts with the functional group derived from the functional group-containing halogen compound (b-1), introducing one or more groups selected from the group consisting of ethylenically unsaturated groups and groups having a carbon-carbon triple bond to the quaternary ammonium cation group, resulting in a quaternary ammonium cation group (g-1). Alternatively, by reacting the tertiary amino group-containing polymer compound (b-0) with the halogen compound (b-3), the conversion of the tertiary amino group to a quaternary ammonium cation group and the introduction of one or more groups selected from the group consisting of ethylenically unsaturated groups and groups having a carbon-carbon triple bond can be carried out simultaneously, allowing a quaternary ammonium cation group (g-1) to be obtained from a tertiary amino group in a single reaction.

[0054] <Tertiary amino group-containing polymer compound (b-0)> Examples of the tertiary amino group-containing polymer compound (b-0) according to this embodiment include polyamines obtained by homopolymerizing a monomer having a tertiary amino group and an ethylenically unsaturated group, or copolymerizing it with another monomer having an ethylenically unsaturated group. Examples of such polymer compounds include polytertiary amines, which are polymers of vinyl tertiary amines or allyl tertiary amines; polytertiary amines obtained by copolymerizing vinyl tertiary amines or allyl tertiary amines with other monomers having an ethylenically unsaturated group; polymers obtained by ring-opening polymerization of 1-substituted aziridines or 2-oxazolines; and polyalkyleneimines obtained by polycondensation of polyfunctional amine compounds such as ethylenediamine or hexamethylenediamine with haloalkanes. The aforementioned tertiary amino group-containing polymer compound (b-0) may also contain primary amino groups, secondary amino groups, quaternary ammonium cationic groups without unsaturated groups, amides, imides, ureas, urethanes, etc., in addition to tertiary amino groups, to the extent that it does not impair the effect, and this does not prevent the addition of the functional group-containing halogen compound (b-1) to these as well. As mentioned above, since the amine structure contributes greatly to pigment dispersibility, it is preferable that it substantially omits amides, imides, ureas, and urethane bonds. Among these, polytertiary amines obtained by block polymerization of a monomer having a tertiary amino group and an ethylenically unsaturated group with another monomer having an ethylenically unsaturated group are preferred. By using a block-polymerized polytertiary amine, the tertiary amino group is unevenly distributed in one terminal region, and when this is converted to a quaternary ammonium cationic group (g-1) to form a polymer dispersant (B), the affinity with the pigment (C) is improved. Furthermore, the other end region has increased affinity with other pigment dispersion compositions, specifically the binder resin (A-1) and the solvent (D-1) described later, which dramatically improves the pigment dispersibility and storage stability of the pigment dispersion composition.

[0055] Specific examples of monomers having a tertiary amino group and an ethylenically unsaturated group include dimethylaminoethyl (meth)acrylate, dimethylaminopropyl (meth)acrylate, dimethylaminobutyl (meth)acrylate, diethylaminoethyl (meth)acrylate, diethylaminopropyl (meth)acrylate, diethylaminobutyl (meth)acrylate, pentamethylpiperidyl (meth)acrylate, tetramethylpiperidyl (meth)acrylate, 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)acrylamides such as acryloylmorpholine. These monomers may be used individually or in combination of two or more. Among these, dimethylaminoethyl (meth)acrylate is more preferred because it greatly contributes to improving the dispersibility and storage stability of the pigment dispersion composition.

[0056] Other monomers having ethylenically unsaturated groups include, for example, (meth)acrylates having alkyl groups, aryl groups, aralkyl groups, cycloalkyl groups, (poly)oxyalkylene skeletons, etc., but there are no particular restrictions as long as they do not impair affinity with other pigment dispersion compositions. Specific examples include methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, isopropyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, t-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, cyclohexyl (meth)acrylate, stearyl (meth)acrylate, lauryl (meth)acrylate, tetrahydrofurfuryl (meth)acrylate, isobornyl (meth)acrylate, phenyl (meth)acrylate, and benzyl (meth)acrylate. Examples include (meth)acrylates such as rilate, phenoxyethyl (meth)acrylate, phenoxydiethylene glycol (meth)acrylate, methoxypolypropylene glycol (meth)acrylate, or ethoxypolyethylene glycol (meth)acrylate; 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; and vinyl fatty acid compounds such as vinyl acetate or vinyl propionate. These monomers may be used individually or in combination of two or more.

[0057] The tertiary amino group-containing polymer compound (b-0) according to this embodiment may be a commercially available product or may be prepared in-house. When using a commercially available product, suitable examples of tertiary amino group-containing polymer compounds (b-0) include the DISPERBYK series from Bic Chemie, the Solspers series from Lubrizol, and the EFKA-PX series from BASF. When preparing it in-house, known polymer manufacturing methods can be used. These tertiary amino group-containing polymer compounds (b-0) may be used individually or in combination of two or more, as needed.

[0058] <Functional group-containing halogen compound (b-1)> The functional group-containing halogen compound (b-1) in this embodiment is not particularly limited as long as it is a monohalogen compound having a functional group, and the number of functional groups is not particularly limited. For example, brominated, chlorinated, or iodized compounds of compounds having one or more selected from the group consisting of a blocked isocyanate group, an alkyl ester group, an epoxy group, an oxetanyl group, a hydroxyl group, a mercapto group, and a carboxyl group are examples. Specifically, examples include 2-bromoethanol and epibromohydrin. These compounds may be used individually or in combination of two or more. Among these, brominated compounds are preferred from the viewpoint of reactivity.

[0059] <A compound having one or more groups selected from the group consisting of a group that is reactive with a functional group, an ethylenically unsaturated group, and a group having a carbon-carbon triple bond (b-2)> The compound (b-2) according to this embodiment is not particularly limited as long as it has both a group that is reactive with the functional group of the functional group-containing halogen compound (b-1) and an ethylenically unsaturated group within its molecule. Examples of reactive functional groups corresponding to the functional group of the functional group-containing halogen compound (b-1) include blocked isocyanate groups, alkyl ester groups, epoxy groups, oxetanyl groups, hydroxyl groups, mercapto groups, and carboxyl groups. Specifically, examples include 2-(meth)acryloyloxyethyl isocyanate and (meth)acrylate glycidyl. These compounds may be used individually or in combination of two or more. Among these, 2-(meth)acryloyloxyethyl isocyanate is preferred from the viewpoint of reactivity.

[0060] <Halogen compounds (b-3) containing one or more selected from the group consisting of ethylenically unsaturated groups and groups having a carbon-carbon triple bond> The compound (b-3) according to this embodiment is not particularly limited as long as it is a monohalogen compound having an ethylenically unsaturated group and / or a carbon-carbon triple bond, and the number of unsaturated groups per molecule is not particularly limited. Examples of halogen compounds include brominated compounds, chlorinated compounds, and iodinated compounds, but among these, brominated compounds are preferred from the viewpoint of reactivity. Specifically, examples include 3-bromo-1-propene, 4-bromo-1-butene, 5-bromo-1-pentene, 6-bromo-1-hexene, 7-bromo-1-heptene, 8-bromo-1-octene, 9-bromo-1-nonene, 10-bromo-1-decene, 5-bromo-1-pentine, 3-bromo-1-propyne, 4-bromo-1-butine, 5-bromo-1-pentine, 6-bromo-1-hexyne, 7-bromo-1-heptine, 8-bromo-1-octin, 9-bromo-1-nonine, and 10-bromo-1-decene. Among these, 3-bromo-1-propene and 3-bromo-1-propyne are preferred from the viewpoint of improving reactivity due to increased activity of the halogen atom.

[0061] The addition rate of the functional group-containing halogen compound (b-1) to the total amount of amino groups in the tertiary amino group-containing polymer compound (b-0) according to this embodiment is preferably 5 to 95%, more preferably 10 to 90%, and even more preferably 30 to 80%. When the addition rate of the functional group-containing halogen compound (b-1), and consequently compound (b-2), is 5% or more, a sufficient amount of ethylenically unsaturated groups is introduced into the polymer dispersant (B), ensuring sufficient crosslinking with the ethylenically unsaturated groups in the binder resin (A-1) and the reactive diluent (E) described later, resulting in a resin cured film with good low-temperature curability as a photosensitive colored composition and excellent solvent resistance. When the addition rate of the functional group-containing halogen compound (b-1) is 95% or less, the polymer dispersant (B) can be easily manufactured without gelation during synthesis, the pigment dispersibility is not impaired during the preparation of the pigment dispersion composition, and storage stability is sufficient.

[0062] The amount of amino groups (primary amines, secondary amines, tertiary amines) and quaternary ammonium cation groups (g-1) in the polymer dispersant (B) according to this embodiment can be quantitatively determined by measuring the amine value (a value measured in accordance with standards such as JIS K7237). The amine content of the tertiary amino group-containing polymer compound (b-0) in this embodiment is not particularly limited, but is preferably 10 mg KOH / g to 400 mg KOH / g, more preferably 15 mg KOH / g to 300 mg KOH / g, and even more preferably 25 mg KOH / g to 200 mg KOH / g. When the amine value is 10 mg KOH / g or higher, sufficient dispersibility and storage stability of the pigment dispersion composition can be obtained.

[0063] The proportion of quaternary ammonium cationic groups (g-1) in the polymer dispersant (B) according to this embodiment is preferably 5 to 95 mol%, more preferably 10 to 90 mol%, and even more preferably 30 to 80 mol%, relative to the total amount of amino groups and quaternary ammonium cationic groups (g-1). If it is 5 mol% or more, a sufficient amount of ethylenically unsaturated groups or carbon-carbon triple bonds can be ensured, improving the solvent resistance of the photosensitive colored composition. If it is 95 mol% or less, sufficient dispersibility and storage stability of the pigment dispersion composition can be obtained by ensuring a sufficient amount of amino groups. When the polymer dispersant (B) according to this embodiment contains amino groups, the tertiary amino groups, in particular, contribute significantly to improving the dispersibility and storage stability of the pigment dispersion composition. Therefore, it is preferable to ensure a sufficient tertiary amine content in the polymer dispersant (B). From this viewpoint, the tertiary amine value of the polymer dispersant (B) is preferably 10 mg KOH / g to 400 mg KOH / g, more preferably 15 mg KOH / g to 300 mg KOH / g, and even more preferably 25 mg KOH / g to 200 mg KOH / g. The tertiary amine value is calculated based on the amount of amino group-containing monomer and functional group-containing halogen compound (b-1) used, with respect to the amine value V0 (a value measured in accordance with standards such as JIS K7237).

[0064] The total amount of ethylenically unsaturated groups and carbon-carbon triple bonds contained in 1 g of polymer dispersant (B) according to this embodiment is preferably 50 to 1600 μmol / g, more preferably 150 to 1500 μmol / g, and even more preferably 400 to 1400 μmol / g. When the total amount of the unsaturated groups is 50 μmol / g or more, an increase in solvent resistance is observed due to crosslinking with the ethylenically unsaturated groups of the binder resin (A-1) and the reactive diluent (E) described later, and when the total amount of the unsaturated groups is 1600 μmol / g or less, good dispersion stability is obtained when it is used as a pigment dispersion composition.

[0065] The weight-average molecular weight of the polymer dispersant (B) according to this embodiment is preferably 1,000 to 40,000, more preferably 1,000 to 30,000. Furthermore, the molecular weight distribution of the polymer dispersant (B) (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 3.0, more preferably 1.0 to 2.0. When the molecular weight and molecular weight distribution of the polymer dispersant (B) are within the above range, the viscosity of the pigment dispersion composition can be controlled within an appropriate range, ensuring sufficient pigment dispersibility and storage stability of the pigment dispersion composition, as well as excellent heat resistance, solvent resistance, pattern adhesion, developability, etc.

[0066] The content of the polymer dispersant (B) according to this embodiment is preferably 5 to 80 parts by mass, more preferably 10 to 60 parts by mass, and even more preferably 15 to 40 parts by mass, per 100 parts by mass of pigment (C). If the content of polymer dispersant (B) is 5 parts by mass or more, good pigment dispersibility can be obtained. If the content of polymer dispersant (B) is 80 parts by mass or less, a sufficient pigment (C) content can be ensured, a cured film with good color characteristics can be obtained, and a photosensitive colored composition with good low-temperature curability can be obtained.

[0067] <Pigment (C)> The pigment (C) according to this embodiment is not particularly limited as long as it can be uniformly dispersed with other compositions to form pixels of a color filter. Pigments of various colors can be used, including pigments of the three primary colors of light such as red, green, and blue, pigments of yellow, orange, and purple that can be used as complementary colors, and pigments of black and brown used in the black matrix. Furthermore, examples of the chemical structure of pigment (C) include all organic pigments such as isoindolinone, isoindoline, azomethine, anthraquinone, anthrone, xanthene, diketopyrrolopyrrole, perylene, perinone, quinacridone, indigoid, dioxazine, indigoid, phthalocyanine, anthocyanin, and azo pigments, as well as inorganic pigments such as carbon black, titanium black, and titanium dioxide.

[0068] In particular, the pigment (C) according to this embodiment preferably includes a green pigment having a halogenated phthalocyanine skeleton represented by the following formula (8).

[0069] [ka]

[0070] In formula (8), M represents a divalent or tetravalent metal atom. Zinc or copper is preferred from the viewpoint of color reproducibility, and zinc is particularly preferred. X represents one of hydrogen atoms, chlorine atoms, or bromine atoms, and contains at least one chlorine atom or bromine atom. The ratio of chlorine atoms to bromine atoms changes depending on the brightness and color reproducibility, with higher brightness resulting from more chlorine atoms and fewer bromine atoms, and conversely, better color reproducibility tending to occur from more bromine atoms and fewer chlorine atoms. The number of chlorine atoms is preferably 1 to 10, and more preferably 1.5 to 8. The number of bromine atoms is preferably 5 to 15, and more preferably 7 to 14.

[0071] By using a green pigment having a halogenated phthalocyanine skeleton and the polymer dispersant (B), sufficient pigment dispersibility and storage stability of the pigment dispersion composition can be obtained, providing a color filter with high brightness and a wide color reproduction range, as well as imparting heat resistance, solvent resistance, and pattern adhesion to the colored pattern.

[0072] As the halogenated phthalocyanine pigment, commercially available products may be used, or one may be prepared in-house. Examples of commercially available products include CI Pigment Green 7, 36, 58, and 59, among which CI Pigment Green 58 and 59 are preferred due to their high brightness and excellent color reproduction. If preparing the pigment oneself, known manufacturing methods can be used. For example, methods include using phthaloic acid or phthalonitrile, in which some or all of the hydrogen atoms of the aromatic ring are substituted with halogen atoms, as a starting material to form a phthalocyanine skeleton under a catalyst such as ammonium molybdate, or halogenating phthalocyanine with chlorine gas or bromine gas. The crude pigment obtained by these methods can be dry-ground in a pulverizer such as a ball mill or vibratory mill, and then processed by a known solvent-salt milling method to obtain the desired green pigment.

[0073] Regarding the pigment (C) according to this embodiment, the green pigment having a halogenated phthalocyanine skeleton may be used alone or in combination of two or more types. Furthermore, other pigments that do not have a halogenated phthalocyanine skeleton may be used in combination. Other specific examples of pigments include yellow pigments such as CI 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; orange pigments such as CI Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73; and CI Pigment Red 9, 97, 105, 12 Examples of pigments include red pigments such as 2, 123, 144, 149, 166, 168, 176, 177, 180, 192, 209, 215, 216, 224, 242, 254, 255, 264, and 265; blue pigments such as CI Pigment Blue 15, 15:3, 15:4, 15:6, and 60; purple pigments such as CI Pigment Violet 1, 19, 23, 29, 32, 36, and 38; brown pigments such as CI Pigment Brown 23 and 25; and black pigments such as CI Pigment Black 1, 7, carbon black, titanium black, and iron oxide. These pigments may be used individually or in combination of two or more, depending on the desired pixel color.

[0074] Furthermore, in this embodiment, the pigment (C) may be used in combination with a dye. When a dye is used in combination with a pigment, higher brightness, a wider color reproduction range, and better developability can be expected compared to when only a pigment is used. On the other hand, when a pigment is used in combination with a dye, it has better heat resistance and less color change after the formation of the colored pattern. Depending on the required performance and the desired pixel color, dyes and pigments may be used in combination.

[0075] In this embodiment, it is preferable to use acid dyes having acidic groups such as carboxyl groups, salts of acid dyes with nitrogen compounds, or sulfonamide forms of acid dyes, from the viewpoint of solubility in solvents (D-1) and alkaline developers, interaction with other components in the resin composition, and heat resistance. 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 chrome violet 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 red1, 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, 11 4,129,133,134,138,143,145,150,151,158,176,183,198,211,215,216,217,249,252,257,260,266,274;acid violet 6B, 7, 9, 17, 19;acid Examples include 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 its derivatives. Among these, azo, xanthene, anthraquinone, or phthalocyanine acid dyes are preferred. These dyes may be used individually or in combination of two or more. When using dyes, 20 to 80 parts by mass are preferred per 100 parts by mass of pigment (C).

[0076] <Solvent (D-1)> The solvent (D-1) according to this embodiment is not particularly limited as long as it does not react with the components contained in the pigment dispersion composition or photosensitive coloring composition according to this embodiment, and is capable of dissolving or dispersing them. The solvent (D-1) can be the same solvent used when manufacturing the binder resin (A-1) or polymer dispersant (B), the solvent contained after the reaction can be used as is, or additional solvent can be added. It may also be a solvent that is present when other components are added.

[0077] Specific examples of the solvent (D-1) according to this embodiment 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, and diethylene glycol ethyl ether acetate. These may be used individually or in combination of two or more. Among these, glycol ether solvents such as propylene glycol monomethyl ether and propylene glycol monomethyl ether acetate, which are preferably used in the manufacture of color filters, are preferred.

[0078] <Method for producing the first binder resin (A-1a)> The epoxy group-containing resin precursor (PA-1a), which is a precursor of the first binder resin (A-1a), is obtained by copolymerizing according to a radical polymerization method known in the art. For example, the monomer to be used for copolymerization may be dissolved in a solvent, a polymerization initiator may be added to the solution, and the reaction may be carried out at 50-130°C for 1-20 hours. Alternatively, the monomer to be used for copolymerization and the polymerization initiator may be reacted dropwise into a solvent adjusted to 50-130°C.

[0079] The solvents that can be used in this copolymerization reaction are not particularly limited as long as they are inert to radical polymerization, and commonly used organic solvents can be used. Specifically, examples include 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 individually or in combination of two or more. Among these, the use of glycol ether solvents is particularly preferred.

[0080] The amount of solvent used in this copolymerization reaction is not particularly limited, but generally it is 30 to 1000 parts by mass, preferably 50 to 800 parts by mass, when the total amount of monomers used in copolymerization is 100 parts by mass. In particular, by limiting the amount of solvent to 1000 parts by mass or less, the decrease in molecular weight of the epoxy group-containing resin precursor (PA-1a) due to chain transfer can be suppressed, and the viscosity of the epoxy group-containing resin precursor (PA-1a) can be controlled within an appropriate range. Furthermore, by limiting the amount of solvent to 30 parts by mass or more, abnormal polymerization reactions can be prevented, the polymerization reaction can be carried out stably, and discoloration and gelation of the epoxy group-containing resin precursor (PA-1a) can also be prevented.

[0081] The polymerization initiators that can be used in this copolymerization reaction are not particularly limited as long as they can initiate radical polymerization, and commonly used organic peroxide catalysts and azo compounds can be used. Specifically, examples include azobisisobutyronitrile, azobisisovaleronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), azobis(2-methylpropionic acid)dimethyl, benzoyl peroxide, dicumyl peroxide, diisopropyl peroxide, di-t-butyl peroxide, t-butyl peroxybenzoate, t-hexyl peroxybenzoate, t-butyl peroxy-2-ethylhexanoate, t-hexyl peroxy-2-ethylhexanoate, and 1,1,3,3-tetramethylbutyl peroxy-2-ethylhexanoate. These can be used individually or in combination of two or more, and it is desirable to select a radical polymerization initiator with an appropriate half-life depending on the polymerization temperature.

[0082] The amount of polymerization initiator used in this copolymerization reaction is not particularly limited, but is generally 0.5 to 20 parts by mass, preferably 1.0 to 10 parts by mass, when the total amount of monomers used in copolymerization is 100 parts by mass.

[0083] As a method for adding compound (a-1) to some of the epoxy groups of the epoxy group-containing resin precursor (PA-1a), known addition reactions can be used. For example, after adding a polymerization inhibitor and a catalyst to a solution of the epoxy group-containing resin precursor (PA-1a), compound (a-1) is added, and an addition reaction or dehydration reaction is carried out under 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 polymerization inhibitors include hydroquinone, methylhydroquinone, hydroquinone monomethyl ether, and dibutylhydroxytoluene. Specific examples of catalysts include tertiary amino groups such as triethylamine, quaternary ammonium salts such as triethylbenzylammonium chloride, phosphorus compounds such as triphenylphosphine, and organometallic compounds such as chromium and tin.

[0084] <Manufacturing method for the second binder resin (A-1aa)> In the production of the first binder resin (A-1a) according to this embodiment, a portion of the epoxy groups of the epoxy group-containing resin precursor (PA-1a) is subjected to ring-opening addition of functional groups such as carboxyl groups, amino groups, and hydroxyl groups of compound (a-1), thereby generating a plurality of hydroxyl groups. When compound (a-2) is to be further added to a portion of the plurality of hydroxyl groups of the first binder resin (A-1a), the addition reaction can be carried out by adding compound (a-2) immediately following the addition reaction of compound (a-1) during the production of the first binder resin (A-1a), and the reaction temperature may be adjusted or the catalyst added as necessary.

[0085] <Method for producing the third binder resin (A-1b)> The method for producing the first binder resin (A-1a) according to this embodiment can also be applied to the production of the third binder resin (A-1b) by changing the type and amount of polymerizable monomer (M) used. When producing the third binder resin (A-1b), the reaction temperature may be adjusted or the catalyst may be changed as needed.

[0086] <Method for producing polymer dispersant (B)> The polymer dispersant (B) according to this embodiment can be produced, for example, by the following method. That is, it can be produced by adding a functional group-containing halogen compound (b-1) to the amino group of a tertiary amino group-containing polymer compound (b-0) and then performing an addition reaction with compound (b-2). Alternatively, it can also be produced by adding a halogen compound (b-3) to the amino group of a tertiary amino group-containing polymer compound (b-0). As a method for adding the functional group-containing halogen compound (b-1) to the amino group of the tertiary amino group-containing polymer compound (b-0), it is preferable to use a bromo-chlorination reaction. Specifically, the tertiary amino group-containing polymer compound (b-0), the functional group-containing halogen compound (b-1), and a solvent in any proportion are added and mixed, and the mixture is reacted under conditions of room temperature to 150°C, preferably 30°C to 130°C, to obtain an addition reaction product of the tertiary amino group-containing polymer compound (b-0) and the functional group-containing halogen compound (b-1). Further, compound (b-2) is added, and the reaction is carried out under conditions of room temperature to 150°C, preferably 30°C to 130°C, to obtain polymer dispersant (B).

[0087] <Method for producing a pigment dispersion composition> The pigment dispersion composition of this embodiment is prepared by weighing a predetermined amount of at least one selected from a first binder resin (A-1a) and a second binder resin (A-1aa), a polymer dispersant (B), a pigment (C), a solvent (D-1), and optionally a third binder resin (A-1b), and then micronizing and dispersing the pigment (C) using a known dispersion process. In this dispersion process, equipment such as paint shakers, bead mills, ball mills, roll mills, stone mills, jet mills, homogenizers, planetary mixers, and revolving mixers are frequently used. Furthermore, using beads with a diameter of 0.01 to 10 mm in this dispersion process allows for efficient and uniform micronization of the pigment (C). There are no restrictions on the material of the beads, but considering hardness and contamination of the pigment dispersion composition, the use of glass beads or zirconia beads is preferred. The optimal time, temperature, bead diameter, and amount used for the dispersion process will vary depending on the composition of the pigment dispersion composition and the size of the apparatus, so these should be adjusted as appropriate. Finally, it is preferable to filter the pigment dispersion composition using a glass filter or the like in order to remove fine dust and coarse particles or aggregates of pigment (C).

[0088] <Photosensitive coloring composition> The photosensitive colored composition of this embodiment contains the above-mentioned pigment dispersion composition, a binder resin (A-2), a reactive diluent (E), and a photopolymerization initiator (F). The photosensitive colored composition of this embodiment may also contain a solvent (D-2). In the photosensitive colored composition of this embodiment, it is preferable that, per 100 parts by mass of pigment (C), the total binder resin (A), consisting of the binder resin (A-1) and binder resin (A-2), is 30 to 280 parts by mass, the reactive diluent (E) is 20 to 200 parts by mass, and the photopolymerization initiator (F) is 0.1 to 20 parts by mass. The solvent (D-2) may be the same as the solvent (D-1) contained in the above pigment dispersion composition, or a different solvent may be added.

[0089] <Binder resin (A-2)> The binder resin (A-2) used in the photosensitive colored composition of this embodiment is not particularly limited, but resins commonly used in negative-type resists, such as (meth)acrylic resins, epoxy (meth)acrylic resins, and vinyl ester resins, are preferred. Specifically, resins containing ethylenically unsaturated double bonds such as vinyl groups and (meth)acryloyl groups, and substituents that contribute to alkali solubility, such as carboxylic acids, phosphoric acid, and sulfonic acid, are preferred as the backbone. By using these resins, a photosensitive colored composition with excellent pattern adhesion and developability can be provided.

[0090] Among these resins, the use of (meth)acrylic resins having (meth)acryloyloxy groups and carboxyl groups is preferred, particularly from the viewpoint of easily providing resins with a wide range of properties. This resin may be a commercially available product or prepared in-house. If prepared in-house, the same type as the binder resin (A-1) can be used. In addition, a solvent (D-2) may be added to appropriately control the molecular weight during synthesis and to appropriately adjust the viscosity after synthesis.

[0091] There are no particular restrictions on the physical properties of the binder resin (A-2), but from the viewpoint of ease of manufacturing the photosensitive colored composition and compatibility with other compositions, it is preferable that the weight-average molecular weight is in the range of 1000 to 50000, the acid value is in the range of 10 to 200 mgKOH / mg, the double bond equivalent is in the range of 100 to 3000 g / mol, and the viscosity of the binder resin (A-2) solution is in the range of 0.1 to 1000 dPa·s.

[0092] The total binder resin (A) content of binder resin (A-1) and binder resin (A-2) is preferably 30 to 280 parts by mass, more preferably 40 to 200 parts by mass, and even more preferably 50 to 130 parts by mass, per 100 parts by mass of pigment (B).

[0093] <Reactive Diluent (E)> The reactive diluent (E) according to this embodiment is not particularly limited as long as it is a low molecular weight compound containing an ethylenically unsaturated double bond such as a vinyl group or a (meth)acryloyloxy group. Specific examples of the reactive diluent (E) include aromatic vinyl monomers such as styrene, α-methylstyrene, α-chloromethylstyrene, vinyltoluene, divinylbenzene, diallyl phthalate, and diallylbenzenephosphonate; polycarboxylic acid monomers such as vinyl acetate and vinyl adipate; methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, butyl (meth)acrylate, β-hydroxyethyl (meth)acrylate, hydroxypropyl (meth)acrylate, ethylene glycol di( Examples include (meth)acrylic monomers such as 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 tris(hydroxyethyl) isocyanurate; triallyl cyanurate, etc. These may be used individually or in combination of two or more. Among these, compounds having multiple (meth)acryloyloxy groups are preferred, and compounds having three or more (meth)acryloyloxy groups, such as trimethylolpropane tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol hexa(meth)acrylate, and tris(hydroxyethyl)isocyanurate tri(meth)acrylate, are more preferred.

[0094] The content of the reactive diluent (E) according to this embodiment is preferably 20 to 200 parts by mass, more preferably 30 to 150 parts by mass, and even more preferably 40 to 100 parts by mass, per 100 parts by mass of pigment (C).

[0095] <Photopolymerization initiator (F)> The photopolymerization initiator (F) in this embodiment is preferably a photoradical generator, and specific examples include benzoin, benzoin methyl ether and its alkyl ethers such as benzoin, benzoin ethyl ether; acetophenones such as acetophenone, 2,2-dimethoxy-2-phenylacetophenone, 1,1-dichloroacetophenone, and 4-(1-t-butyldioxy-1-methylethyl)acetophenone; anthraquinones such as 2-methylanthraquinone, 2-amylanthraquinone, 2-t-butylanthraquinone, and 1-chloroanthraquinone; and 2,4-dimethylthioxanthone and 2,4-diisopropyl alcohol. Examples include thioxanthones such as ropylthioxanthone and 2-chlorothioxanthone; ketals such as acetophenone dimethyl ketal and benzyl dimethyl ketal; benzophenones such as benzophenone, 4-(1-t-butyldioxy-1-methylethyl)benzophenone, and 3,3',4,4'-tetrakis(t-butyldioxycarbonyl)benzophenone; 2-methyl-1-[4-(methylthio)phenyl]-2-morpholino-propan-1-one; 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)butanone-1; acylphosphine oxides; and xanthones. These may be used individually or in combination of two or more.

[0096] The content of the photopolymerization initiator (F) according to this embodiment is preferably 0.1 to 20 parts by mass, more preferably 1 to 15 parts by mass, and even more preferably 2 to 10 parts by mass, per 100 parts by mass of pigment (C).

[0097] In addition to the components described above, the photosensitive colored composition of this embodiment may also contain known additives such as photoacid generators, photobase generators, coupling agents, leveling agents, fillers, etc., to impart predetermined properties. The amounts of these components are not particularly limited, as long as they do not hinder the effects of the present invention.

[0098] <Method for producing a photosensitive colored composition> The photosensitive colored composition of this embodiment can be manufactured by mixing the above components using a known mixing apparatus. For example, it can be manufactured by first preparing the pigment dispersion composition and then sequentially mixing the binder resin (A-2), reactive diluent (E), photopolymerization initiator (F), etc. In addition, if necessary, a solvent (D-2) may be added in addition to the solvent (D-1) contained in the pigment dispersion composition. Note that the solvent (D-2) may be the same as the solvent (D-1), or it may be a different solvent.

[0099] <Color Filter> Next, a color filter having a colored pattern made of a cured product of the photosensitive colored composition according to this embodiment will be described. The color filter according to this embodiment has a colored pattern formed using the above-mentioned photosensitive colored composition. A color filter typically consists of a substrate, RGB pixels formed thereon, 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 that the pixels and the black matrix (colored pattern) are formed using the above-mentioned photosensitive colored composition, other components can be those of known origin.

[0100] Next, an embodiment of a method for manufacturing a color filter will be described. First, a color 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 glass substrates, silicon substrates, polycarbonate substrates, polyester substrates, polyamide substrates, polyamide-imide substrates, polyimide substrates, aluminum substrates, printed circuit boards, array substrates, etc., can be used as appropriate.

[0101] The colored pattern can be formed by photolithography. Specifically, the above-mentioned photosensitive colored composition is applied to a substrate to form a coating film, and then the coating film is exposed to light through a photomask of a predetermined pattern to photocure the exposed areas. After developing the unexposed areas with an alkaline aqueous solution and then baking, the predetermined colored pattern can be formed.

[0102] The method for applying the photosensitive colored composition of this embodiment is not particularly limited, but methods such as screen printing, roll coating, curtain coating, spray coating, and spin coating can be used. Furthermore, after applying the photosensitive colored composition, the solvent (D-1) or solvent (D-2) may be volatilized by heating using a heating means such as a circulating oven, infrared heater, or hot plate, if necessary. The heating conditions are not particularly limited and should be set appropriately according to the type of photosensitive colored composition used. Generally, heating at a temperature of 50°C to 120°C for 30 seconds to 30 minutes is sufficient.

[0103] Next, the formed coating film is partially exposed by irradiating it with active energy rays such as ultraviolet light or excimer laser light through a negative-type mask. The amount of energy irradiated can be appropriately selected according to the composition of the photosensitive coloring composition, and is preferably, for example, 30 to 2000 mJ / cm2. The light source used for exposure is not particularly limited, but low-pressure mercury lamps, medium-pressure mercury lamps, high-pressure mercury lamps, xenon lamps, metal halide lamps, etc., can be used.

[0104] The alkaline aqueous solution used for developing is not particularly limited, but can be an aqueous solution of sodium carbonate, potassium carbonate, calcium carbonate, sodium hydroxide, potassium hydroxide, etc.; an aqueous solution of amino group compounds such as ethylamino group, diethylamino group, dimethylethanolamino group, etc.; or an aqueous solution of p-phenylenediamino group compounds 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-methanesulfonamideethylaniline, 3-methyl-4-amino-N-ethyl-N-β-methoxyethylaniline, and their sulfates, hydrochlorides, or p-toluenesulfonates. Antifoaming agents and surfactants may be added to these aqueous solutions as needed. Furthermore, after developing with the above alkaline aqueous solution, it is preferable to wash with water and dry.

[0105] Furthermore, the baking conditions are not particularly limited, and the heat treatment should be performed according to the type of photosensitive coloring composition used. Generally, heating at 130-250°C for 10-60 minutes is sufficient. However, the light-emitting layer of organic EL displays, for which demand has been expanding in recent years, often uses heat-sensitive materials, and in such cases, it may be treated by heating at 90-130°C for 10-50 minutes.

[0106] A desired coloring pattern can be formed by sequentially repeating the above-described coating, exposure, development, and baking processes using a photosensitive coloring composition for the black matrix and photosensitive coloring compositions for the red, green, and blue pixels. Subsequently, a protective film is formed on the coloring pattern (each RGB pixel and the black matrix). The protective film is not particularly limited and can be formed using known materials.

[0107] The color filters manufactured in this way achieve excellent pigment dispersibility by uniformly miniaturizing the pigments, resulting in high brightness, and possess various resist properties such as excellent heat resistance, solvent resistance, adhesion, and developability, resulting in high resolution.

[0108] <Image display element> The image display element of this embodiment is an image display element equipped with the above-mentioned color filter, and specific examples include liquid crystal display elements, organic EL display elements, solid-state image sensors such as CCD elements and CMOS elements. The manufacturing of the image display element of this embodiment can be carried out in accordance with conventional methods, except for the use of the above-mentioned color filter. For example, when manufacturing a liquid crystal display element, the above-mentioned color filter is formed on a substrate, and then electrodes, spacers, etc. are formed sequentially. Then, electrodes etc. are formed on another substrate, the two are bonded together, a predetermined amount of liquid crystal is injected and sealed. [Examples]

[0109] The present invention will be described in more detail below with reference to examples and comparative examples, but the present invention is not limited to the following examples. In this embodiment, unless otherwise specified, parts and percentages all refer to mass.

[0110] <Content of ethylenically unsaturated groups in binder resin (A)> This is the number of moles of ethylenically unsaturated groups per unit mass of the first binder resin (A-1a), second binder resin (A-1aa), third binder resin (A-1b), or binder resin (A-2), and is a calculated value based on the amount of raw material monomer used.

[0111] <Methods for measuring weight-average molecular weight and number-average molecular weight> The weight-average molecular weight and number-average molecular weight refer to the weight-average molecular weight and number-average molecular weight on a standard polystyrene basis, measured using gel permeation chromatography (GPC) under the following conditions. Column: SHODEX (registered trademark) LF-804 + LF-804 (manufactured by Showa Denko Corporation) Column temperature: 40℃ Sample: 0.2% tetrahydrofuran solution of the substance to be measured. Developing solvent: tetrahydrofuran Detector: Differential refractometer (Showdex RI-71S) (manufactured by Showa Denko Corporation) Flow rate: 1mL / min

[0112] <Acid value of binder resin (A)> The acid values ​​of the first binder resin (A-1a), second binder resin (A-1aa), third binder resin (A-1b), or binder resin (A-2) were measured using a mixed indicator of bromothymol blue and phenol red in accordance with JIS K6901 5.3.

[0113] <Amine value of polymer dispersant (B)> The amine value of polymer dispersant (B) was measured according to the method described above (JIS K7237). The total amine value, including quaternary ammonium cations, is a calculated value based on the amounts used of tertiary amino group-containing polymer compound (b-0), functional group-containing halogen compound (b-1), compound (b-2), and halogen compound (b-3) in each synthesis example and comparative synthesis example.

[0114] <Amount of ethylenically unsaturated groups or carbon-carbon triple bonds in polymer dispersant (B)> This represents the number of moles of ethylenically unsaturated groups or carbon-carbon triple bonds per unit mass of polymer dispersant (B), and is a calculated value based on the amounts used of tertiary amino group-containing polymer compound (b-0), functional group-containing halogen compound (b-1), compound (b-2), and halogen compound (b-3) in each synthesis example and comparative synthesis example.

[0115] An example of the production of the first binder resin (A-1a) is shown below.

[0116] <Example of resin synthesis a1> 158.67 g of propylene glycol monomethyl ether acetate was placed in a flask equipped with a stirrer, dropping funnel, condenser, thermometer, and gas inlet tube. The flask was then stirred while purging with nitrogen gas and heated to 120°C. Next, a monomer mixture consisting of 4.40 g of dicyclopentanyl methacrylate, 3.12 g of styrene, and 134.90 g of glycidyl methacrylate was mixed with 6.41 g of t-butyl peroxy-2-ethylhexanoate as a polymerization initiator, and this mixture was added dropwise to the flask from the dropping funnel. After the addition was complete, the copolymerization reaction was carried out by stirring at 120°C for 2 hours. Next, after replacing the contents of the flask with dry air, 68.40 g of acrylic acid, 0.632 g of triphenylphosphine as a catalyst, and 0.632 g of dibutylhydroxytoluene as a polymerization inhibitor were added, and the addition reaction was carried out at 120°C for 5 hours. Binder resin No. A1 was obtained. For resin synthesis examples a2-a4 and a7-a9, the monomers listed in Tables 1-1 and 1-2 were used, and the synthesis was carried out according to the same method as for resin synthesis example a1, except for the monomer ratio. Binder resins No. A2-A4 and A7-A9 were obtained, respectively.

[0117] An example of the production of the second binder resin (A-1aa) is shown below.

[0118] <Resin synthesis examples a5, a6, a10> In the flask obtained by the above method, 1,2,3,6-tetrahydrophthalic anhydride or maleic anhydride by weight corresponding to the ratio of each synthesis example was added, and an addition reaction was carried out at 115°C for 2 hours to obtain binder resins No. A5, A6, and A10.

[0119] <Comparative synthesis examples ca1, ca2, ca3> 54.49 g of propylene glycol monomethyl ether acetate was placed in a flask equipped with a stirrer, dropping funnel, condenser, thermometer, and gas inlet tube. The flask was then stirred while purging with nitrogen gas and heated to 120°C. Next, a monomer mixture consisting of 3.96 g of dicyclopentanyl methacrylate, 4.75 g of styrene, and 61.52 g of acrylic acid was mixed with 7.02 g of t-butyl peroxy-2-ethylhexanoate as a polymerization initiator, and this mixture was added dropwise to the flask from the dropping funnel. After the addition was complete, the copolymerization reaction was carried out by stirring at 120°C for 2 hours. Next, after replacing the inside of the flask with dry air, 121.34 g of glycidyl methacrylate, 0.570 g of triphenylphosphine as a catalyst, and 0.570 g of methyl hydroquinone as a polymerization inhibitor were added, and the addition reaction was carried out at 120°C for 5 hours. Comparative synthesis examples ca1, ca2, and ca3 were also synthesized using the monomers listed in Tables 1-1 and 1-2, and were synthesized in the same manner as resin synthesis example a1, except for the monomer ratio. Binder resin No. cA3 was obtained. However, in the case of binder resins No. cA1 and cA2, crosslinking due to side reactions progressed during the addition reaction, and the molecular weight increased significantly, resulting in gelation.

[0120] [Table 1-1]

[0121] [Table 1-2]

[0122] An example of the production of the third binder resin (A-1b) is shown below.

[0123] 257.17 g of propylene glycol monomethyl ether acetate was placed in a flask equipped with a stirrer, dropping funnel, condenser, thermometer, and gas inlet tube. The mixture was then stirred while purging with nitrogen gas and heated to 120°C. Next, a monomer mixture consisting of 22.0 g of dicyclopentanyl methacrylate, 46.8 g of styrene, and 38.7 g of methacrylic acid was mixed with 1.96 g of t-butyl peroxy-2-ethylhexanoate as a polymerization initiator, and this mixture was added dropwise to the flask from the dropping funnel. After the addition was complete, the copolymerization reaction was carried out by stirring at 120°C for 2 hours. Next, after replacing the contents of the flask with dry air, 21.3 g of glycidyl methacrylate, 0.48 g of triphenylphosphine as a catalyst, and 0.48 g of dibutylhydroxytoluene as a polymerization inhibitor were added, and the addition reaction was carried out at 120°C for 5 hours to obtain the sample (molecular weight 22000, acid value 119 mg KOH / g, ethylenically unsaturated group equivalent 1100 μmol / g).

[0124] An example of the production of polymer dispersant (B) is shown below.

[0125] <Synthesis of Sample Dispersant 1> In a flask equipped with a stirrer, dropping funnel, condenser, thermometer, and gas inlet tube, 133.0 g of propylene glycol monomethyl ether acetate, 55.0 g of isobornyl methacrylate, and 13.2 g of tetramethylethylenediamine as a catalyst were added, and the mixture was stirred at 50°C for 1 hour while purging the flask with nitrogen. Then, 9.3 g of ethyl bromoisobutyrate and 5.6 g of cuprous chloride were added as catalysts, and the flask was heated to 110°C for 4 hours to carry out the polymerization reaction. After the reaction, the solution was sampled and the non-volatile content was measured. Based on the non-volatile content, it was confirmed that the polymerization conversion rate was 98% or higher. Then, 61 g of propylene glycol monomethyl ether acetate and 45.0 g of dimethylaminoethyl methacrylate as a monomer having a tertiary amino group were added, and the reaction was carried out for a further 2 hours at 110°C. After the reaction, the solution was sampled again and the non-volatile content was measured. Based on the non-volatile content, it was confirmed that the polymerization conversion rate was 98% or higher, and then the solution was cooled. Finally, propylene glycol monomethyl ether acetate was added as a solvent so that the total amount of components excluding the solvent was 40.0%, to obtain sample dispersant 1 containing a tertiary amino group (amine value 160 mg KOH / g, weight-average molecular weight 5500).

[0126] <Synthesis example b1> In a flask equipped with a stirrer, dropping funnel, condenser, thermometer, and gas inlet tube, 35 g of sample dispersant 1 (total components excluding solvent) as a tertiary amino group-containing polymer compound (b-0), 6.27 g of ethylene bromohydrin (50 mol%) of functional group-containing halogen compound (b-1) relative to the total amount of amino groups in the tertiary amino group-containing polymer compound (b-0), and propylene glycol monomethyl ether acetate as a solvent to a theoretical non-volatile content of 30% were added. The mixture was stirred while replacing the inside of the flask with nitrogen gas, and the temperature was raised from room temperature to 100°C. After stirring until a peak shift of ethylene bromohydrin was confirmed by NMR spectroscopy, the temperature was lowered to room temperature. 7.07 g of 2-acryloyloxyethyl isocyanate was added, and the temperature was raised to 60°C for 2 hours to obtain polymer dispersant No. B1.

[0127] For synthesis examples b2-b7 and comparative synthesis examples cb1-cb7, the compounds listed in Tables 2-1 and 2-2 were used, and the synthesis was carried out in the same manner as for dispersant synthesis example b1, except for the compound addition ratio. Polymer dispersants No. B2-B7 and No. cB1-cB7 were obtained, respectively. The following compounds were used for the tertiary amino group-containing polymer compound (b-0). EFKA-PX4300: Manufactured by BASF, contains tertiary amino groups, does not contain primary or secondary amino groups, solids content 80%, amine value 57 mgKOH / g, weight-average molecular weight 25000 • Polyment NK-100PM: Manufactured by Nippon Shokubai Co., Ltd., solids content 49%, amine value 143 mg KOH / g, weight-average molecular weight 20000, contains primary and secondary amino groups, does not contain tertiary amino groups, dispersant.

[0128] [Table 2-1]

[0129] [Table 2-2]

[0130] An example of the production of a pigment dispersion composition is shown below.

[0131] <Pigment dispersion composition examples a1-a17> In a SUS container (inner diameter 50 mm x height 100 mm) filled with 200 g of 0.1 mm diameter zirconia beads (Nikkatoh YTZ balls), 7.5 g (100 parts by mass) of CI Pigment Green 58 (DIC Fastogen Green A110) as pigment (C), one of the samples obtained in resin synthesis examples a1 to a10 as the first binder resin (A-1a) or second binder resin (A-1aa), one of the samples obtained in dispersant synthesis examples b1 to b7 as the polymer dispersant (B), and in example a17 only, a third binder resin (A-1b) is also added, and mixed to the composition shown in Tables 3-1 to 3-2, and propylene glycol monomethyl ether acetate as solvent (D-1) to prepare the mixture so that the total component content after removing the solvent is 24% by mass, and then mixed in a paint shaker (Red Devil Equipment Red Devil The pigment dispersion compositions No. E1 to E17 were obtained by mixing and dispersing the components at room temperature for 2 hours using 5400, and then filtering the contents by suction using a glass filter. The values ​​shown in Tables 3-1 to 3-2 represent the parts by mass of each component excluding the solvent, when the pigment (C) is 100 parts by mass.

[0132] <Comparative Examples of Pigment Dispersion Compositions ca1~ca8> In a SUS container (inner diameter 50 mm x height 100 mm) filled with 200 g of 0.1 mm diameter zirconia beads (Nikkatoh YTZ balls), 7.5 g (100 parts by mass) of CI Pigment Green 58 (DIC Fastogen Green A110) as pigment (C), either the first binder resin (A-1a) or the second binder resin (A-1aa) obtained from resin synthesis example a9 or resin comparative synthesis example ca3, and either the polymer dispersant (B) obtained from dispersant synthesis example b1 or dispersant comparative synthesis examples cb1 to cb7 were added and mixed to the composition shown in Table 3-3, and propylene glycol monomethyl ether acetate was added as solvent (D-1) to prepare the mixture so that the total component content after removing the solvent was 24% by mass, and then mixed in a paint shaker (Red Devil Equipment Red Devil The pigment dispersion compositions No. cE1 to cE8 were obtained by mixing and dispersing the components at room temperature for 2 hours using 5400, and then filtering the contents by suction through a glass filter. The values ​​shown in Table 3-3 represent the parts by mass of each component excluding the solvent, when the pigment (C) is 100 parts by mass.

[0133] [Table 3-1]

[0134] [Table 3-2]

[0135] [Table 3-3]

[0136] <Evaluation of pigment dispersibility> The viscosity of the pigment dispersion composition immediately after preparation was evaluated by measuring it with an E-type viscometer (RE-80L, manufactured by Toki Sangyo Co., Ltd., cone size 4.8 cm, rotation speed 20 rpm, measurement temperature 25°C). In addition, the pigment dispersibility was evaluated on a four-point scale (◎, ○, △, ×) based on the viscosity measurement results, with ○ or higher being considered a pass. The evaluation results are shown in Tables 3-1 to 3-3 above. "◎": Less than 6.0 mPa·s "〇": 6.0 mPa·s or more and less than 10.0 mPa·s "△": 10.0 mPa·s or more and less than 15.0 mPa·s "×": 10.0mPa·s or more

[0137] <Evaluation of storage stability of pigment dispersion compositions> The viscosity of the prepared pigment dispersion composition after storage at room temperature was evaluated by measuring it with an E-type viscometer (RE-80L, manufactured by Toki Sangyo Co., Ltd., measurement temperature 25°C). The viscosity of the pigment dispersion composition was measured after storage for one week or two weeks, and the viscosity increase rate ((viscosity after storage - viscosity after adjustment) × 100 / viscosity after adjustment) was evaluated in three stages (○, △, ×) according to the following criteria, with ○ or higher being considered a pass. The evaluation results are shown in Tables 3-1 to 3-3 above. "〇": Less than 10%, Less than 10% (after 1 week and 2 weeks, respectively) "△": Less than 10%, 10% or more "×": 10% or more, 10% or more

[0138] An example of the production of a photosensitive colored composition (CR) is shown below.

[0139] <Photosensitive colored compositions: Examples b1-b17, Comparative Examples cb1-cb8> When the pigment (C) of the pigment dispersion compositions No. E1 to E17 obtained in the above example and the pigment dispersion compositions No. cE1 to cE8 obtained in the above comparative example is 100 parts by mass, 28.8 parts by mass of ca3 obtained in the resin comparative synthesis example is used as the binder resin (A-2) as the total amount of components other than the solvent, 56 parts by mass of dipentaerythritol hexaacrylate is used as the reactive diluent (E), and 6.4 parts by mass of 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl-]-,-1-(O-acetyloxime) is used as the photopolymerization initiator (F). Propylene glycol monomethyl ether acetate is added as the solvent (D-2) and mixed so that the proportion of components other than the solvent is 30%, thereby preparing photosensitive colored compositions No. F1 to F17 and photosensitive colored compositions No. cF1 to cF8. Tables 4-1 to 4-3 show the combinations of various materials used in Examples b1 to b17 and Comparative Examples cb1 to cb8, as well as the quantities used.

[0140] [Table 4-1]

[0141] [Table 4-2]

[0142] [Table 4-3]

[0143] <Preparation of green resist (1) for solvent resistance testing> The obtained photosensitive colored compositions No. F1 to F17 and No. cF1 to cF8 were spin-coated onto a 5 cm square glass substrate (alkali-free glass substrate) so that the average thickness of the final cured coating film was 1.5 μm. The substrate was then heated at 100°C for 3 minutes to evaporate the solvent. Next, the entire surface of the coating film was exposed to light (using a USH-250BY lamp manufactured by Ushio Inc., with an exposure dose of 40 mJ / cm2), and then baked at 100°C for 30 minutes to obtain a cured coating film, which is a green resist (1).

[0144] <Preparation of green resist (2) for developability testing> The obtained photosensitive colored compositions No. F1 to F17 and No. cF1 to cF8 were spin-coated onto a 5cm square glass substrate (alkali-free glass substrate) so that the average thickness of the final cured coating film was 1.5 μm. The substrate was then heated at 100°C for 3 minutes to evaporate the solvent. Next, a photomask with a line and space or dot pattern was placed on the substrate to expose the coating film (a USH-250BY lamp manufactured by Ushio Inc. was used, with an exposure dose of 40 mJ / cm²). 2 After photocuring, the film was developed with a 0.2% by mass potassium hydroxide aqueous solution and then baked at 100°C for 30 minutes to obtain a cured coating film, which is a green color resist (2).

[0145] <Transmittance Test> The transmittance of the above green resist (1) at 525 nm was measured using a Shimadzu UV-1650PC spectrophotometer. Based on the measurement results, the transmittance of the photosensitive colored composition was evaluated in three stages according to the following criteria, with ○ being considered a pass. The evaluation results are shown in Tables 4-1 to 4-3 above. "〇": Transmittance 95% or more "△": Transmittance between 90% and 95% "×": Transmittance less than 90%

[0146] <Solvent resistance test> The entire surface of the above green resist was immersed in propylene glycol monomethyl ether acetate at 25°C for 15 minutes. After that, the green resist was removed and air-dried. The solvent resistance of the photosensitive colored composition was evaluated by checking the residual film percentage of the green resist. Based on the measurement results, the solvent resistance of the photosensitive colored composition was evaluated on a 5-point scale from 1 to 5 according to the following criteria, with a score of 3 or higher being considered a pass. The evaluation results are shown in Tables 4-1 to 4-3 above. "5": Remaining film rate 93% or more "4": Residual film percentage 85% or more and less than 93% "3": Residual film rate 80% or more but less than 85% "2": Residual film rate less than 80% "1": Peeling visible to the naked eye occurs on the paint film.

[0147] <Developability Test> The developability test evaluated the development speed. For the development speed, during the development process of the green color resist (2) described above, the time taken for the pattern to become visible during development with a 0.2% by mass potassium hydroxide aqueous solution was measured and evaluated on a 5-point scale from 1 to 5 according to the following criteria, with a score of 3 or higher being considered a pass. The evaluation results are shown in Tables 4-1 to 4-3 above. "5": Less than 40 seconds "4": 40 seconds or more but less than 50 seconds "3": 50 seconds or more but less than 65 seconds "2": 65 seconds or more but less than 80 seconds "1": 80 seconds or more

[0148] As can be seen from the results in Tables 3-1 to 3-3, excellent pigment dispersibility and storage stability were obtained in pigment dispersion composition examples a1 to a17. Furthermore, as can be seen from the results in Tables 4-1 to 4-3, transmittance, developability, and solvent resistance were simultaneously achieved in photosensitive colored composition examples b1 to b17. This is because, in the present invention, by combining the binder resin (A-1) and the polymer dispersant (B), an abundance of ethylenically unsaturated groups and / or carbon-carbon triple bonds that serve as crosslinking points can be provided, thus increasing the crosslinking density even under the limited curing conditions of 100°C. In contrast, comparative examples ca2 to ca8 of the pigment dispersion compositions did not achieve sufficient solvent resistance. This is thought to be because dispersants No. cB1 to cB7 contained fewer ethylenically unsaturated groups compared to the examples of the present invention, and therefore, sufficient crosslinking reactions did not proceed under limited exposure and low-temperature conditions. Furthermore, while comparative example ca2, which used binder resin ca3, achieved usable solvent resistance, its storage stability was not good. This is because, compared to the present invention where an epoxy group-containing polymerizable monomer is copolymerized and then an unsaturated carboxylic acid is added, binder resin ca3 involves copolymerizing an unsaturated carboxylic acid before adding the epoxy group-containing monomer, requiring a large amount of carboxylic acid to obtain sufficient addition reaction sites. However, excessively high acid values ​​impair the stability of the pigment dispersion, which is thought to have resulted in the low storage stability shown in Tables 4-1 to 4-3.

[0149] Based on the above, the present invention provides a pigment dispersion composition with excellent pigment dispersibility and storage stability, a photosensitive colored composition containing the pigment dispersion composition with excellent low-temperature curability, and a color filter containing the photosensitive colored composition that has excellent solvent resistance and developability, and is expected to suppress the elution and bleed-out of dispersants and pigments. [Industrial applicability]

[0150] According to the present invention, it is possible to provide a pigment dispersion composition with good pigment dispersibility and storage stability. Furthermore, by using the pigment dispersion composition, it is possible to provide a photosensitive colored composition that yields a cured product with excellent solvent resistance and developability. In addition, it is possible to provide a color filter having a cured product of the photosensitive colored composition, and an image display element equipped therewith.

Claims

1. Binder resin (A-1), Polymer dispersant (B), Pigment (C) and Solvent (D-1), A pigment dispersion composition containing, The binder resin (A-1) contains at least one selected from the first binder resin (A-1a) and the second binder resin (A-1aa), The first binder resin (A-1a) is an addition reaction product of an epoxy group-containing resin precursor (PA-1a) and an ethylenically unsaturated group-containing compound (a-1) having a functional group that is reactive with epoxy groups. The second binder resin (A-1aa) is an addition reaction product of the first binder resin (A-1a) and one or more compounds (a-2) selected from polybasic acids and polybasic acid anhydrides. The epoxy group-containing resin precursor (PA-1a) is a copolymer of a polymerizable monomer (M) containing an epoxy group-containing (meth)acrylate (m-1), A pigment dispersion composition characterized in that the polymer dispersant (B) has a quaternary ammonium cation group (g-1) having one or more selected from the group consisting of an ethylenically unsaturated group and a group having a carbon-carbon triple bond.

2. The pigment dispersion composition according to claim 1, wherein the amount of ethylenically unsaturated groups in the first binder resin (A-1a) and the second binder resin (A-1aa) is 1600 to 8000 μmol / g.

3. The pigment dispersion composition according to claim 1, wherein the total amount of ethylenically unsaturated groups and carbon-carbon triple bonds in the polymer dispersant (B) is 50 to 1600 μmol / g.

4. The pigment dispersion composition according to any one of claims 1 to 3, wherein the polymerizable monomer (M) contains 40 to 100 mol% of the epoxy group-containing (meth)acrylate (m-1).

5. The polymerizable monomer (M) further comprises a polymerizable monomer (m-2) having a crosslinked cyclic hydrocarbon group with 7 to 20 carbon atoms. The pigment dispersion composition according to any one of claims 1 to 3, wherein the polymerizable monomer (M) contains 0.5 to 25 mol% of the polymerizable monomer (m-2) having a crosslinked cyclic hydrocarbon group having 7 to 20 carbon atoms.

6. The pigment dispersion composition according to any one of claims 1 to 3, wherein in the first binder resin (A-1a), the addition rate of an ethylenically unsaturated group-containing compound (a-1) having a functional group reactive with the epoxy group is 10 to 100 mol% with respect to 100 mol% of the epoxy group-containing resin precursor (PA-1a).

7. The pigment dispersion composition according to any one of claims 1 to 3, wherein the binder resin (A-1) contains the second binder resin (A-1aa).

8. The pigment dispersion composition according to any one of claims 1 to 3, wherein the quaternary ammonium cation group (g-1) contained in the polymer dispersant (B) is selected from the group consisting of the groups represented by the following formulas (4), (5), (6), and (7). -(CH) ２ ) ｍ -O-(CO)-(NH)-(CH ２ ) ｎ -O-(CO)-CR １ =CH ２ (4) -(CH) ２ ) ｍ -O-(CO)-CR １ =CH ２ (5) -(CH ２ ) ｍ -CR １ =CH ２ (6) -(CH ２ ) ｍ -C≡CH (7) (In equations (4) to (7), m and n are each independent integers from 1 to 20, and R １ (This represents a hydrogen atom or a methyl group.)

9. The pigment dispersion composition according to any one of claims 1 to 3, wherein the polymer dispersant (B) further has an amino group.

10. The binder resin (A-1) further contains a third binder resin (A-1b), The third binder resin (A-1b) is an addition reaction product of a carboxyl group-containing resin precursor (PA-1b) and an ethylenically unsaturated group-containing compound (a-3) having a functional group that is reactive with a carboxyl group. The pigment dispersion composition according to any one of claims 1 to 3, wherein the acid value of the third binder resin (A-1b) is greater than that of the first binder resin (A-1a) and the second binder resin (A-1aa).

11. The pigment dispersion composition according to any one of claims 1 to 3, wherein the pigment (C) comprises a pigment having a halogenated phthalocyanine skeleton.

12. With respect to 100 parts by mass of the pigment (C), The aforementioned binder resin (A-1) is contained in an amount of 10 to 80 parts by mass. The pigment dispersion composition according to any one of claims 1 to 3, comprising 5 to 80 parts by mass of the polymer dispersant (B).

13. A pigment dispersion composition according to any one of claims 1 to 3, Binder resin (A-2), Reactive diluent (E), Photopolymerization initiator (F) and A photosensitive coloring composition characterized by containing [a certain substance].

14. With respect to 100 parts by mass of the pigment (C), The total amount of the binder resin (A-1) and the binder resin (A-2) is 30 to 280 parts by mass. The above polymer dispersant (B) is contained in 5 to 80 parts by mass, The reactive diluent (E) is contained in parts 20 to 200 parts by mass, The photosensitive coloring composition according to claim 13, comprising 0.1 to 20 parts by mass of the photopolymerization initiator (F).

15. A resin-cured film obtained by curing the photosensitive coloring composition according to claim 13.

16. A color filter having a cured product of the photosensitive coloring composition described in claim 13.

17. An image display element comprising the color filter described in claim 16.

Images