Dispersants and their uses

Abstract

This invention provides a dispersant that offers excellent dispersibility and compatibility, while also achieving both alkaline developability and substrate adhesion after alkaline development. [Solution] A dispersant for an AB block polymer having a substructure represented by the following general formula (1) at one end and a carboxyl group at the other end, wherein the A block has structural units having a carboxyl group bonded to an aromatic ring and hydroxyl group-containing monomer units, and the B block has (meth)acrylic acid ester units. General formula (1) TIFF2026052200000018.tif30170 [In general formula (1), Z represents an alkyl group having 1 to 18 carbon atoms, an alkenyl group having 2 to 18 carbon atoms, a monovalent aromatic hydrocarbon group having 6 to 18 carbon atoms, or a monovalent heterocyclic group having 3 to 18 atoms, or a -SR1 group; R1 represents an alkyl group having 1 to 18 carbon atoms; and * represents the bonding site with the polymer.]

Description

Technical Field

[0001] The present invention relates to a dispersant and a dispersion.

Background Art

[0002] In recent years, in order to obtain good color reproducibility and high contrast of color filters, increasing the concentration of pigments in photosensitive coloring compositions has been studied. When increasing the concentration of pigments, the proportion of the dispersant relatively decreases, so the dispersant is required to have high dispersibility. In addition, various additives such as binder resins, surfactants, and photocurable monomers are used in photosensitive coloring compositions for imparting functions. However, if the compatibility with these additives is insufficient, minute foreign matters are generated, and there is a problem that the quality of color filters deteriorates. Therefore, a dispersant excellent in dispersibility and compatibility, or a living radical copolymer as an alkali-soluble resin has been proposed (Patent Documents 1 to 3). Patent Document 1 discloses a carboxyl group-containing alkali-soluble resin obtained by living radical polymerization in the presence of a disulfide compound. Patent Documents 2 to 3 disclose an AB block polymer dispersant obtained by living radical polymerization of an aromatic carboxylic acid-containing methacrylate.

Prior Art Documents

Patent Documents

[0003]

Patent Document 1

Patent Document 2

Patent Document 3

Summary of the Invention

Problems to be Solved by the Invention

[0004] However, conventional living radical copolymers required further improvements in dispersibility and compatibility. Furthermore, achieving both alkali developability and substrate adhesion after alkali development was difficult. In addition, conventional living radical copolymers had limitations on the monomers that could be used because their synthesis relied on organometallic catalysts and iodine compounds. Moreover, these catalysts were expensive, and the need to remove them after synthesis resulted in low productivity.

[0005] The present invention aims to provide a dispersant that exhibits excellent dispersibility and compatibility, and can achieve both alkaline developability and substrate adhesion after alkaline development. [Means for solving the problem]

[0006] The dispersant of the present invention is a dispersant for AB block polymers having a substructure represented by the following general formula (1) at one end and a carboxyl group at the other end, The aforementioned Block A has a structural unit having a carboxyl group bonded to an aromatic ring and a hydroxyl group-containing monomer unit, The aforementioned Block B is a dispersant having (meth)acrylic acid ester units. General formula (1) [ka]

[0007] [In general formula (1), Z represents an alkyl group having 1 to 18 carbon atoms, an alkenyl group having 2 to 18 carbon atoms, a monovalent aromatic hydrocarbon group having 6 to 18 carbon atoms, or a monovalent heterocyclic group having 3 to 18 atoms, or a -SR1 group; R1 represents an alkyl group having 1 to 18 carbon atoms; and * represents the bonding site with the polymer.] [Effects of the Invention]

[0008] The present invention provides a dispersant that exhibits excellent dispersibility and compatibility, and can achieve both alkaline developability and substrate adhesion after alkaline development. Furthermore, the present invention can provide a photosensitive colored composition, a film, an optical filter, an image display device, and a solid-state image sensor. [Modes for carrying out the invention]

[0009] The following definitions are used in this specification. When "(meth)acryloyl," "(meth)acrylic," "(meth)acrylic acid," "(meth)acrylate," or "(meth)acrylamide" are used, unless otherwise specified, they refer to "acryloyl and / or methacryloyl," "acrylic and / or methacrylic," "acrylic acid and / or methacrylic acid," "acrylate and / or methacrylate," or "acrylamide and / or methacrylamide," respectively. In this specification, "CI" means color index (CI). A monomer is an ethylenically unsaturated monomer. A monomer is the form before polymerization, and a monomer unit is the form that constitutes part of the polymer after polymerization.

[0010] In this specification, the dispersant is an AB block polymer having a substructure represented by the following general formula (1) at one end and a carboxyl group at the other end, The aforementioned Block A has a structural unit having a carboxyl group bonded to an aromatic ring and a hydroxyl group-containing monomer unit, The aforementioned Block B is a dispersant having (meth)acrylic acid ester units. General formula (1) [ka]

[0011] In general formula (1), Z represents an alkyl group having 1 to 18 carbon atoms, an alkenyl group having 2 to 18 carbon atoms, a monovalent aromatic hydrocarbon group having 6 to 18 carbon atoms, or a monovalent heterocyclic group having 3 to 18 atoms, or a -SR1 group; R1 represents an alkyl group having 1 to 18 carbon atoms; and * represents a bonding site with the polymer.

[0012] The dispersant of the present invention is preferably used for dispersing colorants such as pigments and dyes in applications such as inks, paints, molded articles, color filters, etc., and for dispersing dispersed substances such as metal particles. Among these applications, the color filter application is preferred. Note that the dispersed substance is preferably particles.

[0013] The mechanism by which the dispersant of the present invention can solve the problems can be speculated as follows. Since the dispersant of the present invention has a carboxy group at one polymer terminal, it has high mobility and can be adsorbed well to the dispersed substance, so a dispersion excellent in dispersibility and viscosity stability can be obtained. Also, since it has a partial structure represented by the general formula (1) with high hydrophobicity at the other terminal, it has high affinity for the dispersion solvent etc. and the dispersion stability is improved. The dispersant of the present invention can achieve both dispersibility and compatibility by having these polymer terminal structures. Furthermore, the dispersant of the present invention is an A-B block polymer, and by having a structural unit having a carboxy group bonded to an aromatic ring with strong acidity in the A block, it strongly adsorbs to the dispersed substance, so the dispersibility is improved. Furthermore, since the A block has a hydroxyl group-containing monomer unit, the adhesion to the substrate by hydrogen bonding during film formation is improved. Thereby, the adhesion to the substrate especially after alkali development can be improved without impairing the dispersibility and alkali developability. Also, the hydroxyl group, for example, during heat treatment, since the condensation reaction with the carboxy group proceeds, the heat resistance and chemical resistance of the film are improved. Furthermore, by making it an A-B block polymer having the partial structure represented by the general formula (1), the B block, the A block, and the carboxy group in this order, the adsorption force to the dispersed substance by the A block and the terminal carboxy group is improved, and both improvement of dispersibility and suppression of foreign substances can be achieved.

[0014] <Dispersant> The dispersant of the present invention has a partial structure represented by the following general formula (1) at one terminal and a carboxy group at the other terminal. In this specification, the dispersant only needs to have both of these terminals, and the synthesis method is not limited. Note that in this specification, the dispersant is preferably a polymer synthesized by living radical polymerization using a reversible addition-fragmentation chain transfer agent (hereinafter, RAFT agent). General formula (1) [Chemical]

[0015] In general formula (1), Z represents an alkyl group having 1 to 18 carbon atoms, an alkenyl group having 2 to 18 carbon atoms, a monovalent aromatic hydrocarbon group having 6 to 18 carbon atoms or a monovalent heterocyclic group having 3 to 18 atoms, or a -SR1 group, R1 represents an alkyl group having 1 to 18 carbon atoms, and * represents a bonding site with the polymer.

[0016] [RAFT agent] The RAFT agent preferably has a partial structure represented by general formula (1) and a carboxy group. Examples of the RAFT agent include 2-[(dodecylsulfanylthiocarbonyl)sulfanyl]propanoic acid, 4-cyano-4-[(thiobenzoyl)sulfanyl]pentanoic acid, 3-[[[(1-cyano-1-methylethyl)thio]thioxomethyl]thio]propanoic acid, and the like Among these, 2-[(dodecylsulfanylthiocarbonyl)sulfanyl]propanoic acid is preferable because it is excellent in molecular weight control and can obtain a polymer with a sharp molecular weight distribution.

[0017] The amount of the RAFT agent used is preferably 0.1 to 10 parts by mass, more preferably 1 to 10 parts by mass, based on 100 parts by mass of the monomer used for the synthesis of the dispersant.

[0018] [A block] The A block of the dispersant in this specification has a structural unit having a carboxy group bonded to an aromatic ring and a monomer unit containing a hydroxyl group By having a carboxy group bonded to an aromatic ring with a high acidity in the A block, the adsorptivity to the dispersed material is improved and the dispersibility is improved Also, by including a monomer containing a hydroxyl group in the A block, for example, after film formation, the dispersibility and alkali developability are not impaired, and the adhesion to the substrate after alkali development is improved.

[0019] [Structural unit having a carboxy group bonded to an aromatic ring] Structural units having a carboxyl group bonded to an aromatic ring are units derived from monomers having a carboxyl group bonded to an aromatic ring. Examples of monomers having a carboxyl group bonded to an aromatic ring include monohydroxyethyl acrylate phthalate, 4-methacryloxyethyl trimellitic acid, 4-acrylooxyethyl trimellitic acid, 4-methacrylooxypropyl trimellitic acid, 4-acrylooxypropyl trimellitic acid, 4-methacryloxybutyl trimellitic acid, or 4-acrylooxybutyl trimellitic acid. Among these, monohydroxyethyl (meth)acrylate phthalate is preferred from the viewpoint of adsorption to the dispersed material and solubility of the raw material.

[0020] Monomers having a carboxyl group bonded to an aromatic ring can be used alone or in combination of two or more types.

[0021] The content of structural units having a carboxyl group bonded to the aromatic ring is preferably 80 to 99.5% by mass, more preferably 85 to 99.5% by mass, and even more preferably 90 to 99.5% by mass, of the monomer units in Block A. Including an appropriate amount further improves the balance between dispersibility and alkali developability.

[0022] <Hydroxyl group-containing monomer unit> Hydroxyl group-containing monomer units are units derived from hydroxyl group-containing monomers. Examples of hydroxyl group-containing monomers include hydroxyl group-containing (meth)acrylates such as 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, diethylene glycol mono(meth)acrylate, dipropylene glycol mono(meth)acrylate, polyethylene glycol mono(meth)acrylate, propylene glycol mono(meth)acrylate, polypropylene glycol mono(meth)acrylate, polytetramethylene glycol mono(meth)acrylate, poly(ethylene glycol-propylene glycol) mono(meth)acrylate, poly(propylene glycol-tetramethylene glycol) mono(meth)acrylate, or glycerol (meth)acrylate. Among these, 2-hydroxyethyl (meth)acrylate and 4-hydroxybutyl (meth)acrylate are preferred, and 2-hydroxyethyl acrylate and 4-hydroxybutyl acrylate are more preferred. Using hydroxyl group-containing monomers can improve adhesion to the substrate.

[0023] Hydroxyl group-containing monomers can be used alone or in combination of two or more types.

[0024] The content of hydroxyl group-containing monomer units is preferably 0.05 to 5% by mass, more preferably 0.1 to 3% by mass, and even more preferably 0.1 to 2% by mass, out of the total monomer units of block A. When the hydroxyl group-containing monomer content is 0.05% by mass or more, substrate adhesion after alkaline development is improved. When the hydroxyl group-containing monomer content is 5% by mass or less, the adsorption of carboxyl group blocks bonded to the aromatic ring is further improved, resulting in improved dispersibility. By including an appropriate amount, a higher level of balance between dispersibility and substrate adhesion after alkaline development can be achieved.

[0025] Block A may contain (meth)acrylic acid ester units other than structural units having a carboxyl group bonded to an aromatic ring and hydroxyl group-containing monomer units, or other monomer units. (Meth)acrylic acid ester units and other monomer units will be described later.

[0026] <Bブロック> Block B of the dispersant of the present invention has (meth)acrylic acid ester units. By appropriately selecting the type of (meth)acrylic acid ester unit, the affinity with resin species and dispersion solvents can be controlled. Examples of (meth)acrylic acid ester units include (meth)acrylic acid alkyl ester units, (meth)acrylic acid ester units containing a thermal crosslinking group, (meth)acrylic acid ester units containing an aliphatic ring, (meth)acrylic acid ester units containing an aromatic ring, (meth)acrylic acid ester units containing a carboxyl group, and other (meth)acrylic acid ester units.

[0027] Block B may contain amide monomer units, other monomer units, etc., in addition to (meth)acrylic acid ester units.

[0028] <(meth)acrylate alkyl ester unit> Examples of alkyl (meth)acrylates include methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, isopropyl (meth)acrylate, butyl (meth)acrylate, isobutyl (meth)acrylate, isoamyl (meth)acrylate, octyl (meth)acrylate, isooctyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, cetyl (meth)acrylate, decyl (meth)acrylate, isodecyl (meth)acrylate, lauryl (meth)acrylate, tridecyl (meth)acrylate, isomiristyl (meth)acrylate, stearyl (meth)acrylate, or isostearyl (meth)acrylate.

[0029] The content of alkyl (meth)acrylate units is preferably 0 to 80% by mass, and more preferably 5 to 70% by mass, of the total monomer units in block B. By setting it within this range, both dispersibility and compatibility can be achieved, and the generation of foreign matter can be suppressed.

[0030] <(meth)acrylic acid ester units containing thermal crosslinking groups> Examples of (meth)acrylic acid ester units containing a thermal crosslinking group include monomers having a tert-butyl group, monomers having an oxetane group, and monomers having a blocked isocyanate group. Examples of monomers having a tert-butyl group include tert-butyl (meth)acrylate and tert-butylcyclohexyl (meth)acrylate. Examples of monomers having an oxetane group include 3-ethyl-3-methacryloyloxymethyl oxetane and 3-ethyl-3-acryloyloxymethyl oxetane. Examples of monomers having a blocked isocyanate group include 2-[(3,5-dimethylpyrazolyl)carbonylamino]ethyl (meth)acrylate and 2-[0-(1'-methylpropyleneneamino)carboxyamino]ethyl (meth)acrylate.

[0031] The content of (meth)acrylic acid ester units containing thermal crosslinking groups is preferably 5 to 50% by mass, and more preferably 10 to 45% by mass, of the total monomer units in block B. This range allows for both dispersibility and resistance to be achieved.

[0032] <Aliphatic ring-containing (meth)acrylate ester units> Examples of aliphatic ring-containing (meth)acrylic acid ester units include cyclohexyl (meth)acrylate, dicyclopentanyl (meth)acrylate, dicyclopentanyloxyethyl (meth)acrylate, dicyclopentenyl (meth)acrylate, or isobornyl (meth)acrylate.

[0033] <Aromatic ring-containing (meth)acrylic acid ester units> Examples of aromatic ring-containing (meth)acrylic acid ester units include benzyl (meth)acrylate, phenoxyethyl (meth)acrylate, phenoxypolyethylene glycol (meth)acrylate, paracumyl phenoxyethyl (meth)acrylate, or nonylphenoxypolyethylene glycol (meth)acrylate.

[0034] <Carboxyl group-containing (meth)acrylic acid ester units> Examples of carboxyl group-containing (meth)acrylic acid ester units include 2-(meth)acryloyloxyethyl phthalate, 2-(meth)acryloyloxypropyl phthalate, 2-(meth)acryloyloxyethyl hexahydrophthalate, 2-(meth)acryloyloxypropyl hexahydrophthalate, β-carboxyethyl (meth)acrylate, or ω-carboxypolycaprolactone (meth)acrylate.

[0035] <Other (meth)acrylic acid ester units> Other (meth)acrylic acid ester units include, for example, the aforementioned hydroxyl group-containing (meth)acrylic acid esters, or fluoroalkyl (meth)acrylates such as trifluoroethyl (meth)acrylate, octafluoropentyl (meth)acrylate, perfluorooctylethyl (meth)acrylate, or tetrafluoropropyl (meth)acrylate, (meth)acryloxy-modified polydimethylsiloxane (silicone macromer), or amino group-containing (meth)acrylates such as N,N-dimethylaminoethyl (meth)acrylate or N,N-diethylaminoethyl (meth)acrylate.

[0036] <Amide monomer units> Examples of amide monomer units include (meth)acrylamide, N,N-dimethyl(meth)acrylamide, N,N-diethyl(meth)acrylamide, N-isopropyl(meth)acrylamide, diacetone(meth)acrylamide, or N-substituted (meth)acrylamides such as acryloylmorpholine.

[0037] <Other monomer units> Examples include (meth)acrylic acid, (meth)acrylonitrile, styrene, α-methylstyrene, vinyl acetate, vinyl (meth)acrylate, or allyl (meth)acrylate. Among these, (meth)acrylic acid is preferred. The content of (meth)acrylic acid units is preferably greater than 0% by mass and 20% by mass or less, and more preferably 1 to 10% by mass, of the total monomer units in block B. By keeping it within this range, both dispersibility and developability can be achieved.

[0038] The dispersant of the present invention is preferably synthesized by living radical polymerization (RAFT polymerization) of Block A and Block B using the aforementioned RAFT agent. By performing RAFT polymerization, the end structure of the polymer, the molecular weight of the polymer, and the molecular weight distribution can be precisely controlled.

[0039] For living radical polymerization, azo compounds are preferred as radical polymerization initiators. Examples of azo compounds include 2,2'-azobisisobutyronitrile, 2,2'-azobis(2-methylbutyronitrile), 2,2'-azobis(methyl isobutyrate), 1,1'-azobis(cyclohexane1-carbonnitrile), 2,2'-azobis(2,4-dimethylvaleronitrile), 2,2'-azobis(2,4-dimethyl-4-methoxyvaleronitrile), dimethyl2,2'-azobis(2-methylpropionate), 4,4'-azobis(4-cyanovaleric acid), 2,2'-azobis(2-hydroxymethylpropionitrile), or 2,2'-azobis[2-(2-imidazolin-2-yl)propane].

[0040] Radical polymerization initiators can be used alone or in combination of two or more types.

[0041] The polymerization reaction temperature is preferably 40 to 150°C, and more preferably 50 to 110°C. The reaction time is preferably 3 to 30 hours, and more preferably 5 to 20 hours.

[0042] In the synthesis of the dispersant of the present invention, it is preferable to first form block A using a RAFT agent, and then form block B. This yields a dispersant having, in that order, a substructure represented by general formula (1), block B, block A, and a carboxyl group. Because there is a carboxyl group at the polymer end of block A, adsorption to the dispersed material is enhanced, and dispersibility is particularly improved.

[0043] The dispersant of the present invention can be synthesized using an organic solvent. Examples of organic solvents include ethyl acetate, n-butyl acetate, isobutyl acetate, toluene, xylene, acetone, hexane, methyl ethyl ketone, cyclohexanone, propylene glycol monomethyl ether acetate, dipropylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, ethylene glycol monobutyl ether acetate, diethylene glycol monoethyl ether acetate, or diethylene glycol monobutyl ether acetate. The organic solvents can be used individually or in combination of two or more types.

[0044] [Molecular weight] The weight-average molecular weight of the dispersant of the present invention is preferably 5,000 to 50,000, more preferably 5,000 to 30,000, and even more preferably 6,000 to 20,000. When the molecular weight is 5,000 or more, the aggregation of the dispersed material is further suppressed due to the steric repulsion effect of block B, thus improving dispersibility. When the molecular weight is 50,000 or less, the solubility in organic solvents is improved, which improves adsorption to the dispersed material and further improves dispersibility. When the molecular weight is within the above range, the compatibility with additives such as binder resins, surfactants, and photocurable monomers is also further improved. The weight-average molecular weight is a value measured by gel permeation chromatography (GPC).

[0045] The dispersant of the present invention preferably contains 0% to 2% by mass of components with a weight-average molecular weight of 1,000 or less in the entire dispersant. This improves dispersibility and foreign matter suppression when the dispersion described herein is used. Furthermore, the molecular weight distribution (Mw / Mn) is preferably 1.8 or less. Dispersibility is further improved when the molecular weight distribution is 1.8 or less. Note that Mn is the number-average molecular weight.

[0046] The method for reducing the weight-average molecular weight of components with a molecular weight of 1,000 or less to 2% by mass or less in the entire dispersant can be controlled, for example, by adding a radical polymerization initiator in the later stages of the polymerization reaction. This suppresses unreacted raw materials and oligomer components. It goes without saying that the method for reducing the weight-average molecular weight of polymers with a molecular weight of 1,000 or less to 2% by mass or less in the entire dispersant as described herein is not limited to the method described above.

[0047] [Acid value] The acid value of the dispersant of the present invention is preferably 10 to 200 mg KOH / g, more preferably 20 to 150 mg KOH / g, and even more preferably 30 to 110 mg KOH / g. When the acid value is 10 mg KOH / g or higher, the adsorption capacity to the dispersed material is improved, and the dispersibility is further improved. On the other hand, when the acid value is 200 mg KOH / g or lower, the interaction between dispersants can be suppressed, so the viscosity of the dispersion can be kept low.

[0048] In the dispersant of the present invention, the content of monomer units of block A is preferably 10 to 40% by mass, more preferably 15 to 40% by mass, and even more preferably 15 to 35% by mass, of the total monomer units of the block AB polymer. Being within this range provides an excellent balance between the adsorption properties of block A and block B to the dispersed material and the steric repulsion effect, resulting in a dispersion with low viscosity and high viscosity stability.

[0049] In the dispersant of the present invention, it is preferable that the total monomer units of the AB block polymer contain 35 to 80% by mass of (meth)acrylic acid ester units, and more preferably 40 to 70% by mass. Being within this range improves the balance between alkali solubility and heat resistance.

[0050] <Dispersion> The dispersion of the present invention preferably comprises the above-mentioned dispersant, the material to be dispersed, and a solvent. The material to be dispersed is dispersible particles, including organic particles such as colorants and inorganic particles such as metals.

[0051] The dispersant content in the dispersion is preferably 0.01 to 100 parts by mass, more preferably 0.01 to 60 parts by mass, and even more preferably 5 to 40 parts by mass, per 100 parts by mass of the material to be dispersed. An appropriate amount provides a good dispersion effect and suppresses the viscosity of the dispersion.

[0052] The dispersion of the present invention can be suitably used in applications that utilize pigment dispersions, such as color filters, offset inks, and inkjet inks. The following explanation will use color filter applications as an example.

[0053] <Coloring agent> For color filter applications, the dispersed material is preferably a colorant. Colorants include pigments. Examples of pigments include organic pigments and inorganic pigments. Organic pigments are preferred because they have high color development and high resistance to heat degradation. Specific examples of organic pigments are shown below, indicated by their color index numbers.

[0054] Red pigments include, for example, CI Pigment Red 1, 2, 3, 4, 5, 6, 7, 8, 9, 12, 14, 15, 16, 17, 21, 22, 23, 31, 32, 37, 38, 41, 47, 48, 48:1, 48:2, 48:3, 48:4, 49, 49:1, 49:2, 50:1, 52:1, 52:2, 53, 53:1, 53:2, 53:3, 57, 57:1, 57:2 , 58:4, 60, 63, 63:1, 63:2, 64, 64:1, 68, 69, 81, 81:1, 81:2, 81:3, 81:4, 83, 88, 90:1, 101, 101:1, 104, 108, 108:1, 109, 112, 113, 114, 122, 123, 144, 146, 147, 149, 151, 166, 168, 169, 170, 172, 173, 174, 175, 176, 177, 178, 179, 181, 184, 185, 187, 188, 190, 193, 194, 200, 202, 206, 207, 208, 209, 210, 214, 216, 220, 221, 224, 230, 231, 232, 233, 235, 236, 237, 238, 239, 242, 243, 245, 247, 249, 2 Examples include 50, 251, 253, 254, 255, 256, 257, 258, 259, 260, 262, 263, 264, 265, 266, 267, 268, 269, 270, 271, 272, 273, 274, 275, 276, 277, 278, 279, 280, 281, 282, 283, 284, 285, 286, 287, 291, 295, 296, etc. Among these, CI pigment red 48:1, 122, 177, 224, 242, 269, 254, 291, 295, and 296 are preferred from the viewpoint of heat resistance, light resistance, and transmittance of the filter segment, and CI pigment red 177, 254, 291, 295, and 296 are more preferred.

[0055] Examples of orange pigments include CI Pigment Orange 36, 38, 43, 51, 55, 59, 61, 71, or 73.

[0056] Examples of blue pigments include CI Pigment Blue 1, 1:2, 9, 14, 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 17, 19, 25, 27, 28, 29, 33, 35, 36, 56, 56:1, 60, 61, 61:1, 62, 63, 66, 67, 68, 71, 72, 73, 74, 75, 76, 78, and 79. Among these, CI Pigment Blue 15, 15:1, 15:2, 15:3, 15:4, or 15:6 are preferred from the viewpoint of heat resistance, light resistance, and transmittance of the filter segment, and CI Pigment Blue 15:6 is more preferred.

[0057] Examples of purple pigments include CI Pigment Violet 1, 1:1, 2, 2:2, 3, 3:1, 3:3, 5, 5:1, 14, 15, 16, 19, 23, 25, 27, 29, 31, 32, 37, 39, 42, 44, 47, 49, and 50. Among these, CI Pigment Violet 19 or 23 is preferred, and CI Pigment Violet 23 is more preferred, from the viewpoint of heat resistance, light resistance, and transmittance of the filter segment.

[0058] Examples of green pigments include CI Pigment Green 1, 2, 4, 7, 8, 10, 13, 14, 15, 17, 18, 19, 26, 36, 37, 45, 48, 50, 51, 54, 55, 58, 59, 62, and 63. Among these, CI Pigment Green 36, 58, 59, 62, and 63 are preferred from the viewpoint of transmittance.

[0059] Yellow pigments include, for example, CI Pigment Yellow 1, 2, 3, 4, 5, 6, 10, 12, 13, 14, 15, 16, 17, 18, 24, 31, 32, 34, 35, 35:1, 36, 36:1, 37, 37:1, 40, 42, 43, 53, 55, 60, 61, 62, 63, 65, 73, 74, 77, 81, 83, 93, 94, 95, 97, 98, 100, 101, 104, 106, 108, 109, 110, 113, 114, 115, 116, 117, 118 Examples include 119, 120, 123, 126, 127, 128, 129, 138, 139, 147, 150, 151, 152, 153, 154, 155, 156, 161, 162, 164, 166, 167, 168, 169, 170, 171, 172, 173, 174, 175, 176, 177, 179, 180, 181, 182, 185, 187, 188, 192, 193, 194, 196, 198, 199, 213, 214, 231, and 233. Among these, CI Pigment Yellow 138, 139, 150, 185, 231, and 233 are preferred.

[0060] Examples of blue pigments include CI Pigment Blue 15:1, 15:2, 15:4, 15:3, 15:6, 16, and 81.

[0061] Examples of purple pigments include CI Pigment Violet 1, 19, CI Pigment Red 144, 146, 177, 169, and 81.

[0062] Examples of inorganic pigments include metal oxide powders, metal sulfide powders, or metal powders such as barium sulfate, zinc oxide, lead sulfate, lead yellow, zinc yellow, red iron oxide (red iron(III) oxide), cadmium red, ultramarine, Prussian blue, chromium oxide green, cobalt green, amber, titanium black, synthetic iron black, titanium dioxide, and iron tetroxide. Inorganic pigments are used in combination with organic pigments to ensure good coating properties, sensitivity, and developability while maintaining a balance between saturation and brightness.

[0063] In this specification, the dispersion may contain a dye within a range that does not reduce its heat resistance.

[0064] <Solvent> The dispersion of the present invention contains a solvent. The solvents include, for example, 1,2,3-trichloropropane, 1,3-butanediol, 1,3-butylene glycol, 1,3-butylene glycol diacetate, 1,4-dioxane, 2-heptanone, 2-methyl-1,3-propanediol, 3,5,5-trimethyl-2-cyclohexen-1-one, 3,3,5-trimethylcyclohexanone, 3-ethoxypropionate ethyl, 3-methyl-1,3-butanediol, 3-methoxy-3-methyl-1-butanol, 3-methoxy-3-methylbutyl acetate, 3-methoxybutanol, 3-methoxy Butyl acetate, 4-heptanone, m-xylene, m-diethylbenzene, m-dichlorobenzene, N,N-dimethylacetamide, N,N-dimethylformamide, n-butyl alcohol, n-butylbenzene, n-propyl acetate, N-methylpyrrolidone, o-xylene, o-chlorotoluene, o-diethylbenzene, o-dichlorobenzene, p-chlorotoluene, p-diethylbenzene, sec-butylbenzene, tert-butylbenzene, γ-butyrolactone, isobutyl alcohol, isophorone, ethylene glycol diethyl ether Ethylene glycol dibutyl ether, ethylene glycol monoisopropyl ether, ethylene glycol monoethyl ether, ethylene glycol monoethyl ether acetate, ethylene glycol monotertiary butyl ether, ethylene glycol monobutyl ether, ethylene glycol monobutyl ether acetate, ethylene glycol monopropyl ether, ethylene glycol monohexyl ether, ethylene glycol monomethyl ether, ethylene glycol monomethyl ether acetate, diisobutyl ketone, diethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol monoisopropyl ether, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether, diethylene glycol monobutyl ether acetate, diethylene glycol monomethyl ether, cyclohexanol, cyclohexanol acetate, cyclohexanone, dipropylene glycol dimethyl ether, dipropylene glycol methyl ether acetate, dipropylene glycol monoethyl ether,Examples include dipropylene glycol monobutyl ether, dipropylene glycol monopropyl ether, dipropylene glycol monomethyl ether, diacetone alcohol, triacetin, tripropylene glycol monobutyl ether, tripropylene glycol monomethyl ether, propylene glycol diacetate, propylene glycol phenyl ether, propylene glycol monoethyl ether, propylene glycol monoethyl ether acetate, propylene glycol monobutyl ether, propylene glycol monopropyl ether, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether propionate, benzyl alcohol, methyl isobutyl ketone, methylcyclohexanol, n-amyl acetate, n-butyl acetate, isoamyl acetate, isobutyl acetate, propyl acetate, or dibasic acid esters. The solvent can be used alone or in mixtures of two or more types.

[0065] The dispersion of the present invention may contain a binder resin or the like, in addition to a dispersant, a colorant, and a solvent.

[0066] <Binder resin> The binder resin is a resin that, when forming a 1.5 μm thick film, has a transmittance of preferably 80% or more, more preferably 95% or more, across the entire wavelength range of 400 to 700 nm in the visible light region. Examples of resins include thermoplastic resins and photosensitive resins.

[0067] Examples of thermoplastic resins include butyral resin, styrene-maleic acid copolymer, chlorinated polyethylene, chlorinated polypropylene, polyvinyl chloride, vinyl chloride-vinyl acetate copolymer, polyvinyl acetate, polyurethane resin, polyester resin, acrylic resin, alkyd resin, polystyrene, polyamide resin, rubber resin, cycloadhesive rubber resin, cellulose, polyethylene, polybutadiene, or polyimide resin. Examples of thermosetting resins include epoxy resins, benzoguanamine resins, rosin-modified maleic acid resins, rosin-modified fumaric acid resins, melamine resins, urea resins, or phenolic resins.

[0068] The photosensitive resin is preferably a resin obtained by reacting a resin having a reactive substituent such as a hydroxyl group, carboxyl group, or amino group with a (meth)acrylic compound having a reactive substituent such as an isocyanate group, aldehyde group, or epoxy group, or with cinnamic acid, to introduce a photocrosslinkable group such as a (meth)acryloyl group or styryl group into the polymer. Also preferred are resins in which a polymer containing an acid anhydride such as a styrene-maleic anhydride copolymer or an α-olefin-maleic anhydride copolymer is half-esterified with a (meth)acrylic compound having a hydroxyl group such as a hydroxyalkyl (meth)acrylate.

[0069] When considering pattern formation by photolithography, an alkali-soluble resin is preferred for the binder resin. An alkali-soluble resin is a resin that dissolves in an alkaline aqueous solution, and is, for example, a resin having an acidic functional group such as a carboxyl group or a sulfone group, with a weight-average molecular weight of 1,000 to 500,000, preferably 5,000 to 100,000. Examples of alkali-soluble resins include acrylic resins having acidic functional groups, α-olefin / (anhydride) maleic acid copolymers, styrene / (anhydride) maleic acid copolymers, styrene / styrene sulfonic acid copolymers, ethylene / (meth)acrylic acid copolymers, or isobutylene / (anhydride) maleic acid copolymers. Among these, acrylic resins having acidic functional groups, α-olefin / (anhydride) maleic acid copolymers, styrene / (anhydride) maleic acid copolymers, and styrene / styrene sulfonic acid copolymers are preferred.

[0070] The binder resin content is preferably 20 to 400 parts by mass, and more preferably 50 to 250 parts by mass, per 100 parts by mass of the dispersed material. Including an appropriate amount allows for easy film formation and facilitates obtaining good color characteristics.

[0071] The dispersion of the present invention can be prepared by, for example, performing a dispersion treatment using a material to be dispersed, a dispersant, and a solvent. When the material to be dispersed is an organic pigment, using a dispersion aid such as a dye derivative during the dispersion treatment allows for finer dispersion of the organic pigment. Furthermore, if the pigment has high solubility in the solvent, dispersion treatment may not be necessary. When two or more pigments are used in combination, dispersions can be prepared for each pigment separately and then mixed. Alternatively, a dispersion can be prepared all at once using multiple pigments. Subsequently, a photosensitive dispersion can be obtained by further adding a polymerizable compound and a photopolymerization initiator and mixing. It goes without saying that the timing of adding each material is arbitrary.

[0072] The aforementioned dispersion process can be carried out using a dispersion device such as a kneader, a two-roll mill, a three-roll mill, a ball mill, a horizontal sand mill, a vertical sand mill, an annular bead mill, or an attritor.

[0073] After preparing the dispersion, it is preferable to remove coarse particles of 5 μm or larger, preferably 1 μm or larger, and more preferably 0.5 μm or larger, as well as any mixed dust, by means of centrifugation, sintering filters, membrane filters, etc.

[0074] <Other dispersants> In this specification, other dispersants may be used in combination with the dispersant of the present invention. Examples of other dispersants include resin-type dispersants other than the dispersant of the present invention, surfactants, and the like.

[0075] The aforementioned resin-type dispersants include, for example, styrene-maleic anhydride copolymer, olefin-maleic anhydride copolymer, poly(meth)acrylate, styrene-(meth)acrylic acid copolymer, (meth)acrylic acid-(meth)acrylic acid ester copolymer, (meth)acrylic acid-polyvinyl macromer copolymer, phosphate ester group-containing acrylic resin, aromatic carboxyl group-containing acrylic resin, polystyrene sulfonate, acrylamide-(meth)acrylic acid copolymer, carboxymethylcellulose, polyurethane having a carboxyl group, formalin condensate of naphthalene sulfonate, or anionic resin-type pigment dispersants such as sodium alginate; Nonionic resin-type pigment dispersants such as polyvinyl alcohol, polyalkylene polyamine, polyacrylamide, or polymer starch; or, Examples include polyethyleneimines, aminoalkyl (meth)acrylate copolymers, polyvinylimidazolines, polyurethanes having amino groups, reaction products of poly(lower alkyleneimines) and polyesters having free carboxyl groups, or cationic resin-type pigment dispersants such as satkinsan.

[0076] Commercial resin-type dispersants include Disperbyk-101, 103, 107, 108, 110, 111, 116, 130, 140, 154, 161, 162, 163, 164, 165, 166, 170, 171, 174, 180, 181, 182, 183, 184, 185, 190, 2000, 2001, 2020, 2025, 2050, 2070, 2095, 2150, 2155, or manufactured by BIC Chemie Japan. Anti-Terra-U, 203, 204, or BYK-P104, P104S, 220S, 6919, or Lactimon, Lactimon-WS, or Bykumen, etc., manufactured by Lubrizol Japan, SOLSPERSE-3000, 9000, 13000, 13240, 13650, 13940, 16000, 17000, 18000, 20000, 21000, 24000, 26000, 27000, 28000, 31845, 32000, 32500, 32550, 33500, 32600, 34750, 35100, 36600, 38500, 41000, 41090, 53095, 55000, 76500 etc., and BASF Japan's EFKA-46, 47, 48, 452, 4008, 4009, 4010, 4015, 4020, 4047, 4050, 4055, 4060, 4080, 4400, 4401, 44 Examples include 02, 4403, 4406, 4408, 4300, 4310, 4320, 4330, 4340, 450, 451, 453, 4540, 4550, 4560, 4800, 5010, 5065, 5066, 5070, 7500, 7554, 1101, 120, 150, 1501, 1502, 1503, etc., as well as Ajisper PA111, PB711, PB821, PB822, PB824, etc., manufactured by Ajinomoto Fine Techno Co., Ltd.

[0077] Surfactants include anionic surfactants such as polyoxyethylene alkyl ether sulfate, sodium dodecylbenzenesulfonate, alkali salts of styrene-acrylic acid copolymer, sodium alkylnaphthalenesulfonate, sodium alkyldiphenyl ether disulfonate, monoethanolamine lauryl sulfate, triethanolamine lauryl sulfate, ammonium lauryl sulfate, monoethanolamine stearate, sodium stearate, sodium lauryl sulfate, monoethanolamine of styrene-acrylic acid copolymer, or polyoxyethylene alkyl ether phosphate esters; Nonionic surfactants such as polyoxyethylene oleyl ether, polyoxyethylene lauryl ether, polyoxyethylene nonylphenyl ether, polyoxyethylene alkyl ether phosphate, polyoxyethylene sorbitan monostearate, or polyethylene glycol monolaurate; Cationic surfactants such as alkyl quaternary ammonium salts and their ethylene oxide adducts; or, Examples include alkyl betaines such as alkyldimethylaminoacetic acid betaine, or amphoteric surfactants such as alkylimidazolines. Other dispersants can be used individually or in combination of two or more.

[0078] The amount of other dispersants used is preferably 0.1 to 40 parts by mass, and more preferably 0.1 to 30 parts by mass, per 100 parts by mass of the material to be dispersed. Using an appropriate amount of other dispersants further improves dispersibility.

[0079] <Dye derivatives> Dye derivatives can be used in the dispersion as needed. This further improves the dispersibility of the dispersed material (e.g., colorant). Dye derivatives are compounds having acidic groups, basic groups, neutral groups, etc., on organic dye residues. Examples of dye derivatives include compounds having acidic substituents such as sulfo groups, carboxyl groups, or phosphate groups (hereinafter referred to as acidic derivatives), as well as compounds having basic substituents such as amine salts, sulfonamide groups, or tertiary amino groups at the terminal (hereinafter referred to as basic derivatives), and compounds having neutral substituents such as phenyl groups or phthalimidoalkyl groups. Examples of pigment skeletons in pigment derivatives include diketopyrrolopyrrole pigments, anthraquinone pigments, quinacridone pigments, dioxazine pigments, perinone pigments, perylene pigments, thiaidine indigo pigments, triazine pigments, benzimidazolone pigments, indole pigments such as benzoisoindole, isoindoline pigments, isoindolinone pigments, quinophthalone pigments, naphthol pigments, surene pigments, metal complex pigments, and azo pigments such as azo, disazo, and polyazo.

[0080] In the dispersion of the present invention, the amount of dye derivative is preferably 1 to 50 parts by mass, more preferably 3 to 30 parts by mass, and even more preferably 5 to 25 parts by mass, per 100 parts by mass of the dispersed material. When the amount of dye derivative is 1% by mass or more, the effect of the addition is obtained and the pigment dispersibility is improved, and when it is 50% by mass or less, the heat resistance and light resistance are less likely to be adversely affected.

[0081] Specific examples of dye derivatives having a basic group used in the present invention are shown below. However, the invention is not limited to these examples.

[0082] • Dye derivative 1 [ka]

[0083] • Dye derivative 2 [ka]

[0084] • Dye derivative 3 [ka]

[0085] • Dye derivative 4 [ka]

[0086] • Dye derivative 5 [ka]

[0087] The photosensitive compositions described herein may contain a dispersant, a colorant, a polymerizable compound, and a polymerization initiator. Furthermore, the photosensitive compositions described herein may further contain a binder resin, which is described above.

[0088] The coloring agent can be any of the coloring agents described above for the dispersed material. The coloring agent content is preferably 1 to 90% by mass, and more preferably 10 to 80% by mass, of the nonvolatile content of the photosensitive coloring composition. When the colorant content is within the aforementioned range, the color density when used as a color filter is sufficient, and the necessary amount of binder and additives can be included in the photosensitive colored composition, which is preferable because it allows for the formation of a pattern with sufficient mechanical strength.

[0089] <Polymerizable compound> Polymerizable compounds are monomers and oligomers having polymerizable unsaturated groups. Examples of polymerizable unsaturated groups include vinyl groups, (meth)acryloyl groups, and (meth)allyl groups. The number of polymerizable unsaturated groups in a polymerizable compound is one or more, and preferably two to twenty.

[0090] Polymerizable compounds are compounds that harden when exposed to ultraviolet light or heat, and include monomers and oligomers. Examples include polyethylene glycol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, triethylene glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, 1,6-hexanediol diglycidyl ether di(meth)acrylate, bisphenol A diglycidyl ether di(meth)acrylate, neopentyl glycol diglycidyl ether di(meth)acrylate, dipentaerythritol hexa(meth)acrylate, dipentaerythritol penta(meth)acrylate, and tricyclodecanyl(meth)acrylate.

[0091] Polymerizable compounds can be used individually or in combination of two or more types.

[0092] The polymerizable compound content is preferably 2 to 50 parts by mass, and more preferably 2 to 30 parts by mass, per 100 parts by mass of colorant. Adding an appropriate amount further improves photocurability and developability.

[0093] <Photopolymerization initiator> Examples of photopolymerization initiators include acetophenone-based photopolymerization initiators such as 4-phenoxydichloroacetophenone, 4-tert-butyl-dichloroacetophenone, diethoxyacetophenone, 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropan-1-one, 1-hydroxycyclohexylphenyl ketone, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1-one, or 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one; Benzoin-based photopolymerization initiators such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, or benzyl dimethyl ketal; Benzophenone-based photopolymerization initiators such as benzophenone, benzoylbenzoic acid, methyl benzoylbenzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylic benzophenone, or 4-benzoyl-4'-methyldiphenyl sulfide; Thioxanthone-based photopolymerization initiators such as thioxanthone, 2-chlorthioxanthone, 2-methylthioxanthone, isopropylthioxanthone, or 2,4-diisopropylthioxanthone; Triazine-based photopolymerization initiators such as 2,4,6-trichloro-s-triazine, 2-phenyl-4,6-bis(trichloromethyl)-s-triazine, 2-(p-methoxyphenyl)-4,6-bis(trichloromethyl)-s-triazine, 2-(p-tolyl)-4,6-bis(trichloromethyl)-s-triazine, 2-piperonyl-4,6-bis(trichloromethyl)-s-triazine, 2,4-bis(trichloromethyl)-6-styryl-s-triazine, 2-(naphtho-1-yl)-4,6-bis(trichloromethyl)-s-triazine, 2-(4-methoxy-naphtho-1-yl)-4,6-bis(trichloromethyl)-s-triazine, 2,4-trichloromethyl-(piperonyl)-6-triazine, or 2,4-trichloromethyl(4'-methoxystyryl)-6-triazine; Examples include borate-based photopolymerization initiators, carbazole-based photopolymerization initiators, and imidazole-based photopolymerization initiators. Photopolymerization initiators can be used alone or in combination of two or more types.

[0094] The amount of photopolymerization initiator is preferably 5 to 200 parts by mass, and more preferably 10 to 150 parts by mass, per 100 parts by mass of colorant.

[0095] The photosensitive colored composition of the present invention can be used in combination with a photopolymerization initiator and a sensitizer. This improves the photoreactivity. Examples of sensitizers include α-acyloxyesters, acylphosphine oxides, methylphenylglyoxylates, benzyl, 9,10-phenanthrenequinone, camphorquinone, ethylanthraquinone, 4,4'-diethylisophthalophenone, 3,3',4,4'-tetra(tert-butylperoxycarbonyl)benzophenone, or 4,4'-diethylaminobenzophenone.

[0096] The sensitizer content is preferably 0.1 to 60 parts by mass per 100 parts by mass of the photopolymerization initiator.

[0097] The binder resin content is preferably 1 to 60% by mass, and more preferably 5 to 50% by mass, of the nonvolatile content of the photosensitive colored composition.

[0098] The photosensitive coloring compositions of this specification may further contain additives. Examples of additives include chain transfer agents, plasticizers, surface modifiers, UV inhibitors, light stabilizers, antioxidants, antistatic agents, antiblocking agents, defoamers, viscosity modifiers, and waxes.

[0099] The photosensitive colored compositions described herein can be prepared, for example, by dispersing a mixture containing a dispersant, a colorant, and a solvent to produce a dispersion. The dispersion can then be mixed with a polymerizable compound and a polymerization initiator, etc. The timing of adding each ingredient is arbitrary. Furthermore, the dispersion process can be performed multiple times.

[0100] <Membranes, optical filters> The film of the present invention is formed from a photosensitive colored composition. The film is preferably used for optical filter applications. Examples of optical filters include color filters, near-infrared transmission filters, and near-infrared blocking filters.

[0101] <Color Filter> The color filter preferably has a filter segment formed from the above-mentioned dispersion on a substrate (also called a substrate). The color filter preferably has a red filter segment, a green filter segment, and a blue filter segment, depending on the type of colorant used. Alternatively, the color filter may have a magenta filter segment, a cyan filter segment, and a yellow filter segment in addition to or instead of the aforementioned color filter segments. The substrate can be either a transparent substrate or a reflective substrate. A transparent substrate is, for example, a glass substrate. A reflective substrate is, for example, a substrate that uses aluminum electrodes or a thin metal film as the reflective surface.

[0102] In color filters, it is preferable to first form a black matrix on the substrate, and then form the filter segments. Alternatively, thin-film transistors (TFTs) can be formed on the substrate beforehand, and then the black matrix can be formed. Examples of black matrices include multilayer films of chromium or chromium / chromium oxide, inorganic films such as titanium nitride, and resin films in which light-shielding agents are dispersed.

[0103] Filter segments can be fabricated by methods such as printing, electrodeposition, transfer, inkjet, and photolithography. This specification describes the most preferred method: photolithography.

[0104] Examples of substrates include glass plates with high transmittance to visible light, and resin plates such as polycarbonate, polymethyl methacrylate, and polyethylene terephthalate.

[0105] Photolithography involves, for example, coating a transparent substrate with a colored composition containing a coloring agent of a certain hue to form a film with a dry film thickness of approximately 0.2 to 5 μm. The resulting film (hereinafter referred to as the first film) is exposed (irradiated with light) through a mask having a predetermined pattern. Next, development is performed by immersion in a solvent or alkaline developer or by spraying the developer, removing uncured portions and obtaining the desired pattern. By performing this process similarly with photosensitive colored compositions containing coloring agents of other hues, color filters with filter segments of each color can be manufactured. Furthermore, a second film (oxygen barrier film) can be formed on the first film before exposure using polyvinyl alcohol or water-soluble acrylic resin. This prevents the first film from coming into contact with oxygen, thus improving its exposure sensitivity. Additionally, the color filter can be heated (post-paved) to cure any uncured polymerizable compounds in the filter segments.

[0106] Coating equipment includes, for example, spray coating, spin coating, slit coating, and roll coating. A drying process can be performed during coating. Drying equipment includes, for example, a hot air oven and an infrared heater.

[0107] The developer can be an alkaline developer, for example, an inorganic alkali such as sodium carbonate or sodium hydroxide; or an organic alkali such as dimethylbenzylamine or triethanolamine. Furthermore, the developer may contain defoaming agents or surfactants.

[0108] The post-bake temperature is preferably around 80-230°C. In recent years, low-temperature curing below 150°C has become more preferable to address environmental concerns. The low-temperature curing post-baking time is approximately 30 minutes to 1 hour.

[0109] <Image display device> The image display device of the present invention has an optical filter. The optical filter is preferably a color filter, for example. The manufacturing of an image display device involves bonding a counter substrate to a substrate using a sealant, injecting liquid crystal through an injection port provided in the sealed area, sealing the injection port, and, if necessary, bonding a polarizing film or phase difference film to the outside of the substrate to obtain a liquid crystal display device, which is a type of image display device. This liquid crystal display device can be used in liquid crystal display modes that perform colorization using color filters such as twisted nematic (TN), super-twisted nematic (STN), in-plane switching (IPS), vertically aligned (VA), and optically convened bend (OCB).

[0110] The above-mentioned image display device can be used for applications other than liquid crystal displays, such as organic EL displays, quantum dot displays, electronic paper, and head-mounted displays.

[0111] <Solid-state image sensor> The solid-state image sensor of the present invention has an optical filter. The optical filter is preferably a color filter, for example. The solid-state image sensor of the present invention is equipped with the optical filter of the present invention. The optical filter is preferably a color filter. The configuration of the solid-state image sensor of the present invention is a configuration that includes a color filter for the solid-state image sensor of the present invention, and is not particularly limited as long as it functions as a solid-state image sensor, but for example, the following configuration can be given. The solid-state image sensor color filter of the present invention is provided on a substrate, comprising a plurality of photodiodes constituting the light-receiving area of ​​a solid-state image sensor (CCD sensor, CMOS sensor, or organic CMOS sensor, etc.) and transfer electrodes made of polysilicon or the like, a light-shielding film made of tungsten or the like with an opening only for the light-receiving portion of the photodiodes on the photodiodes and the transfer electrodes, a device protection film made of silicon nitride or the like formed on the light-shielding film so as to cover the entire surface of the light-shielding film and the light-receiving portion of the photodiodes, and the color filter for solid-state image sensors of the present invention on the device protection film. Furthermore, the configuration may include a configuration in which a light-gathering means (for example, a microlens, etc.; the same applies hereinafter) is provided on the device protection layer and below the color filter (on the side closer to the substrate), or a configuration in which the light-gathering means is provided on the color filter. The organic CMOS sensor is composed of a thin panchromatic photosensitive organic photoelectric conversion film as the photoelectric conversion layer and a CMOS signal readout substrate. It has a two-layer hybrid structure in which the organic material is responsible for capturing light and converting it into an electrical signal, and the inorganic material is responsible for extracting the electrical signal to the outside. In principle, it is possible to achieve a 100% aperture ratio for incident light. The organic photoelectric conversion film is a structure-free continuous film that can be laid on the CMOS signal readout substrate, so it does not require expensive microfabrication processes and is suitable for miniaturizing filter segments. There are no particular restrictions on the arrangement of color filter segments, and known methods can be used.

[0112] [Example of an embodiment] Examples of embodiments of the present invention are given below. The present invention is not limited to the following.

[0113] <1> The dispersant described herein is a dispersant for AB block polymers having a substructure represented by the following general formula (1) at one end and a carboxyl group at the other end, The aforementioned Block A has a structural unit having a carboxyl group bonded to an aromatic ring and a hydroxyl group-containing monomer unit, The aforementioned Block B is a dispersant having (meth)acrylic acid ester units. General formula (1) [ka] [In general formula (1), Z represents an alkyl group having 1 to 18 carbon atoms, an alkenyl group having 2 to 18 carbon atoms, a monovalent aromatic hydrocarbon group having 6 to 18 carbon atoms, or a monovalent heterocyclic group having 3 to 18 atoms, or a -SR1 group; R1 represents an alkyl group having 1 to 18 carbon atoms; and * represents the bonding site with the polymer.] <2> The acid value is 10-200 mgKOH / g. <1> A dispersant. <3> The monomer unit content of block A is 10 to 40% by weight of the total monomer units of the AB block polymer. <1> or <2> A dispersant. <4> The monomer units of block A contain 80 to 100% by mass of structural units having a carboxyl group bonded to the aromatic ring. <1> ~ <3> Any dispersant. <5> The monomer units of block A contain 0.05 to 5% by mass of pre-hydroxyl group-containing monomer units. <1> ~ <4> Any dispersant. <6> The weight-average molecular weight is 5,000 to 50,000, and in the AB block polymer, the amount of polymer with a weight-average molecular weight of 1,000 or less is 0% by mass or more and 2% by mass or less. <1> ~ <5> Any dispersant. <7> The substructure shown in general formula (1), the B block, the A block, and the carboxyl group are in that order. <1> ~ <6> Any dispersant. <8> <1> ~ <7> A dispersion comprising any of the following: a dispersant, a substance to be dispersed, and a solvent. <9> 1>~ <7> A photosensitive colored composition comprising any of the following: a dispersant, a colorant, a polymerizable compound, and a polymerization initiator. <10> <9> A film formed from a photosensitive coloring composition. <11> Substrate and <10> An optical filter having a film. <12> <11> An image display device having an optical filter. <13> <11> A solid-state image sensor having an optical filter. [Examples]

[0114] The present invention will be described below based on examples. However, the present invention is not limited to these examples. Note that "parts" refers to "parts by mass" and "%" refers to "percentage by mass".

[0115] (Polymerization average molecular weight (Mw)) The weight-average molecular weight (Mw) was measured using gel permeation chromatography (GPC) equipped with an RI detector. An HLC-8320GPC (Tosoh Corporation) was used, with two separation columns connected in series. Both columns were packed with two TSK-GEL SUPER HZM-N columns. The oven temperature was 40°C, THF solution was used as the eluent, and the measurement was performed at a flow rate of 0.35 ml / min. The sample was dissolved in a 0.1% solvent of the above eluent and injected in 20 microliters. All molecular weights are polystyrene equivalents. The amount of components with a weight-average molecular weight of 1,000 or less was calculated based on a weight-average molecular weight chart obtained by measuring the dispersant using GPC. A result of "○" was given when the polymer with a weight-average molecular weight of 1,000 or less was between 0% and 2%, and a result of "×" was given when it exceeded 2%.

[0116] (Acid value) 0.5 to 1.0 g of the sample was mixed with 40 ml of pyridine and 5 ml of water and stirred to dissolve uniformly. The sample was then titrated with a 0.1 mol / L potassium hydroxide-ethanol aqueous solution using an automatic titrator ("COM-555," manufactured by Hiranuma Sangyo Co., Ltd.) to measure the acid value. The acid value per unit of non-volatile content of the sample was then calculated from the calculated acid value and the non-volatile content concentration of the sample.

[0117] The acid value (mgKOH / g) of the dry sample was calculated using the following formula. Acid value (mgKOH / g) = {(5.611 × α × F) / S} / (non-volatile content concentration / 100) However, S: Sample volume (g) α: Consumption volume (ml) of 0.1 mol / L potassium hydroxide-ethanol solution F: Potency of 0.1 mol / L potassium hydroxide-ethanol solution

[0118] (Non-volatile content) The non-volatile content was calculated by weighing 1.0 g of the sample into an aluminum container and drying it in an electric oven at 200°C for 10 minutes, then comparing the weight before and after drying. Non-volatile content % = (Weight of sample after drying) / (Weight of sample before drying) × 100

[0119] <Example 1> (Manufacturing of Dispersant 1) In a reaction vessel equipped with a gas inlet tube, thermometer, condenser, and stirrer, 7.2 parts of 4-cyano-4-[(dodecylsulfanylthiocarbonyl)sulfanyl]pentanoic acid, 10.0 parts of monohydroxyethyl acrylate phthalate, 1.0 part of 4-hydroxybutyl acrylate, and 28.0 parts of propylene glycol monomethyl ether acetate were charged. After purging with nitrogen gas, the mixture was heated to 80°C while stirring. Next, 0.05 parts of 2,2'-azobis(2-methylpropionic acid)dimethyl was dissolved in 3.0 parts of propylene glycol monomethyl ether acetate and added to initiate the reaction. After 4 hours, another 0.05 parts of 2,2'-azobis(2-methylpropionic acid)dimethyl was dissolved in 3.0 parts of propylene glycol monomethyl ether acetate and added, and the reaction was continued for another 4 hours. Finally, after confirming that more than 95% had reacted by measuring the non-volatile content, Block A was synthesized. Subsequently, the temperature in the reaction vessel was cooled to below 40°C, and 30.0 parts methyl methacrylate, 15.0 parts tert-butyl methacrylate, 40.0 parts 2-methoxyethyl acrylate, 4.0 parts methacrylic acid, and 38.2 parts propylene glycol monomethyl ether acetate were charged. After purging with nitrogen gas, the temperature was raised to 80°C while stirring. Next, 0.05 parts 2,2'-azobis(2-methylpropionic acid)dimethyl was dissolved in 3.0 parts propylene glycol monomethyl ether acetate and added to start the reaction. After 4 hours, another 0.05 parts 2,2'-azobis(2-methylpropionic acid)dimethyl was dissolved in 3.0 parts propylene glycol monomethyl ether acetate and added, and the reaction was continued for another 4 hours. Finally, after confirming that more than 95% had reacted by measuring the non-volatile content, the reaction was terminated. After the reaction was complete, propylene glycol monomethyl ether acetate was added to adjust the non-volatile content to 40% by mass, and a solution of AB block polymer dispersant 1 with an acid value of 61 mg KOH / g and a weight-average molecular weight of 8,000 was obtained.

[0120] [Table 1]

[0121] [Table 2]

[0122] [Table 3]

[0123] <Examples 2-12, Comparative Examples 1-3> (Manufacturing of dispersants 2-12 and 15-17) The dispersants 2-12 and 15-17 were synthesized in the same manner as the production example for dispersant 1, except that the raw materials and quantities listed in Tables 1 and 2 were used, and solutions were obtained.

[0124] <Example 13> (Manufacturing of dispersant 13) In a reaction vessel equipped with a gas inlet tube, thermometer, condenser, and stirrer, 7.2 parts of 4-cyano-4-[(dodecylsulfanylthiocarbonyl)sulfanyl]pentanoic acid, 36.0 parts of methyl methacrylate, 23.5 parts of tert-butyl acrylate, 16.0 parts of ethyl acrylate, 4.0 parts of methacrylic acid, and 79.5 parts of propylene glycol monomethyl ether acetate were charged. After purging with nitrogen gas, the mixture was heated to 80°C while stirring. Next, 0.05 parts of 2,2'-azobis(2-methylpropionic acid)dimethyl was dissolved in 3.0 parts of propylene glycol monomethyl ether acetate and added to start the reaction. After 4 hours, another 0.05 parts of 2,2'-azobis(2-methylpropionic acid)dimethyl was dissolved in 3.0 parts of propylene glycol monomethyl ether acetate and added, and the reaction was continued for another 4 hours. Then, after confirming that more than 95% had reacted by measuring the non-volatile content, Block B was synthesized. Subsequently, the temperature in the reaction vessel was cooled to below 40°C, and 20.0 parts monohydroxyethyl acrylate phthalate, 0.5 parts 2-hydroxyethyl acrylate, and 27.7 parts propylene glycol monomethyl ether acetate were charged. After purging with nitrogen gas, the temperature was raised to 80°C while stirring. Next, 0.05 parts 2,2'-azobis(2-methylpropionic acid)dimethyl was dissolved in 3.0 parts propylene glycol monomethyl ether acetate and added to start the reaction. After 4 hours, another 0.05 parts 2,2'-azobis(2-methylpropionic acid)dimethyl was dissolved in 3.0 parts propylene glycol monomethyl ether acetate and added, and the reaction was continued for another 4 hours. Finally, after confirming that more than 95% had reacted by measuring the non-volatile content, the reaction was terminated. After the reaction was complete, propylene glycol monomethyl ether acetate was added to adjust the non-volatile content to 40% by mass, and a solution of AB block polymer dispersant 13 with an acid value of 83 mg KOH / g and a weight-average molecular weight of 8,000 was obtained.

[0125] <Example 14> (Manufacturing of dispersant 14) In a reaction vessel equipped with a gas inlet tube, thermometer, condenser, and stirrer, 7.2 parts of 4-cyano-4-[(dodecylsulfanylthiocarbonyl)sulfanyl]pentanoic acid, 10.0 parts of monohydroxyethyl phthalate, 1.0 part of 4-hydroxybutyl acrylate, and 28.0 parts of propylene glycol monomethyl ether acetate were charged. After purging with nitrogen gas, the mixture was heated to 80°C while stirring. Next, 0.05 parts of 2,2'-azobis(2-methylpropionic acid)dimethyl was dissolved in 3.0 parts of propylene glycol monomethyl ether acetate and added to initiate the reaction. After 4 hours, the reaction was continued for another 4 hours without adding an initiator. Finally, after confirming that more than 95% had reacted by measuring the non-volatile content, Block A was synthesized. Subsequently, the temperature in the system was cooled to below 40°C, and 30.0 parts of methyl methacrylate, 15.0 parts of tert-butyl methacrylate, 40.0 parts of 2-methoxyethyl acrylate, 4.0 parts of methacrylic acid, and 38.2 parts of propylene glycol monomethyl ether acetate were charged. After purging with nitrogen gas, the temperature was raised to 80°C while stirring. Next, 0.05 parts of 2,2'-azobis(2-methylpropionic acid)dimethyl was dissolved in 3.0 parts of propylene glycol monomethyl ether acetate and added to start the reaction. After 4 hours, the reaction was continued for another 4 hours without adding an initiator. The reaction was terminated after confirming that more than 95% had reacted by measuring the non-volatile content. After the reaction was complete, propylene glycol monomethyl ether acetate was added to prepare a solution of AB block polymer dispersant 14 with an acid value of 61 mg KOH / g and a weight-average molecular weight of 7,500.

[0126] The abbreviations used in the table are as follows: [Monomers having carboxyl groups bonded to aromatic compounds] • Aromatic carboxylic acid monomer 1: Monohydroxyethyl acrylate phthalate • Aromatic carboxylic acid monomer 2: Monohydroxyethyl methacrylate phthalate • Aromatic carboxylic acid monomer 3:4-methacryloxyethyl trimellitic acid [Monomers having a carboxyl group attached to an aliphatic group] • Aliphatic carboxylic acid monomer 1: mono(2-acryloyloxyethyl) succinate [Hydroxyl group-containing monomers] • 2HEA: 2-hydroxyethyl acrylate · 4HBA: 4-hydroxybutyl acrylate [(meth)acrylic acid ester] <(meth)acrylate alkyl ester unit> • MMA: Methyl methacrylate • EA: Ethyl acrylate <(meth)acrylic acid ester units containing thermal crosslinking groups> TBMA: tert-butyl methacrylate TBA: tert-butyl acrylate • OXMA: Methyl 3-ethyloxetane-3-yl methacrylate <Other (meth)acrylic acid ester units> • 2MTA: 2-methoxyethyl acrylate [Other monomers] • MAA: Methacrylic acid [RAFT agent] • RAFT agent 1: 4-cyano-4-[(dodecylsulfanylthiocarbonyl)sulfanyl]pentanoic acid (In the synthesized AB block polymer, Z in the part corresponding to general formula (1) is substituent (2) below) • RAFT agent 2: 4-cyano-4-[(phenylcarbonothioyl)thio]pentanoic acid (In the synthesized AB block polymer, Z in the part corresponding to general formula (1) is substituent (3) below) • RAFT agent 3: 4-cyano-4-[(dodecylsulfanylthiocarbonyl)sulfanyl]methyl pentanoate (In the synthesized AB block polymer, Z in the part corresponding to general formula (1) is the substituent (2) below)

[0127] [ka]

[0128] <Method for manufacturing binder resin> (Preparation of acrylic resin solution 1) A reaction vessel was prepared by fitting a thermometer, condenser, nitrogen gas inlet tube, and stirrer into a separable four-neck flask. 70.0 parts of propylene glycol monomethyl ether acetate were charged into the vessel, and the temperature was raised to 80°C. After purging the reaction vessel with nitrogen, a mixture of 13.3 parts n-butyl methacrylate, 4.6 parts 2-hydroxyethyl methacrylate, 4.3 parts methacrylic acid, 7.4 parts paracumylphenol ethylene oxide modified acrylate (Toagosei Co., Ltd. "Aronics M110"), and 0.4 parts 2,2'-azobisisobutyronitrile was added dropwise over 2 hours using a dropping tube. After the dropwise addition was complete, the reaction was continued for another 3 hours to obtain a solution of acrylic resin with a weight-average molecular weight (Mw) of 26,000. After cooling to room temperature, approximately 2 g of the resin solution was sampled and heated and dried at 180°C for 20 minutes. The non-volatile content was measured, and propylene glycol monoethyl ether acetate was added to prepare acrylic resin solution 1 so that the non-volatile content was 20% by mass.

[0129] <Example 15> (Preparation of Pigment Dispersion 1) After stirring and mixing the following mixture until homogeneous, it was dispersed for 3 hours using 0.5 mm diameter zirconia beads in an Eiger mill (Eiger Japan's "Mini Model M-250MKII"), and then filtered through a 5.0 μm pore size filter to prepare pigment dispersion 1 with 20% by mass of nonvolatile components. Dispersant 1:15.3 parts PR254 (CIPigment Red 254, manufactured by BASF Japan, "Irgafore Red B-CF"): 12.4 parts Dye derivative 1:1.7 parts Propylene glycol monomethyl ether acetate (PGMAc): 70.6 parts

[0130] [Table 4]

[0131] <Examples 16-28, Comparative Examples 4-6> (Manufacturing of pigment dispersions 2-17) Pigment dispersions 2 to 17 were obtained in the same manner as the production example for pigment dispersion 1, except that the raw materials and preparation amounts listed in Table 4 were used.

[0132] Dye derivative 1: [ka]

[0133] <Example 29> (Photosensitive coloring composition 1) A mixture of the following compositions was stirred and mixed until homogeneous, and then filtered through a 1 μm pore size filter to prepare a photosensitive colored composition 1 with 15% non-volatile content. Pigment dispersion 1:50.0 parts Acrylic resin solution 1:7.5 parts Photopolymerizable compound (Arronix M-402, manufactured by Toagosei Co., Ltd.): 2.0 parts Photopolymerization initiator (BASF Japan "Irgacure OXE02"): 1.2 parts Sensitizer (EAB-F, manufactured by Hodogaya Chemical Co., Ltd.): 0.3 parts Propylene glycol monomethyl ether acetate (PGMAc): 39.0 parts

[0134] [Photopolymerizable compound] • M-402; Arronix M-402: A mixture of dipentaerythritol pentaacrylate and dipentaerythritol hexaacrylate (manufactured by Toagosei Chemical Co., Ltd.)

[0135] [Photopolymerization initiator] • Irgacure OXE02: Ethane-1-one, 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl], 1-(O-acetyloxime) (manufactured by BASF Japan)

[0136] [Sensitizer] • EAB-F: 4,4'-bis(diethylamino)benzophenone (manufactured by Hodogaya Chemical Co., Ltd.)

[0137] <Examples 30-42, Comparative Examples 7-9> (Manufacturing of photosensitive colored compositions 2-17) The procedure was the same as in the production example of photosensitive colored composition 1, except that the pigment dispersions listed in Table 5 were used instead of pigment dispersion 1 in Example 29, to obtain photosensitive colored compositions 2 to 17.

[0138] (viscosity stability) The viscosity stability of the obtained photosensitive colored composition was evaluated by the following method. The initial viscosity the day after the preparation of the photosensitive colored composition and the viscosity after accelerating the process over one week at 40°C were measured using an E-type viscometer (ELD-type viscometer manufactured by Toki Sangyo Co., Ltd.) at 25°C and a rotation speed of 50 rpm. From these initial and viscosity values, the rate of change in viscosity over time was calculated using the following formula, and the viscosity stability was evaluated in three stages. A low rate of change in viscosity indicates good dispersibility of the dispersant. [Percentage change in viscosity over time] = |([Initial viscosity] - [Viscosity over time]) / [Initial viscosity]| × 100 ○: Viscosity change rate less than 5% (good) △: Viscosity change rate of 5% or more but less than 10% (practical) ×: Viscosity change rate of 10% or more (not practical)

[0139] (Developability) The obtained photosensitive colored composition was coated onto a 10 cm x 10 cm square glass substrate using a spin coater, and then dried in an 80°C oven for 5 minutes to form a coating with a thickness of 1.5 μm. After the substrate was cooled to room temperature, a high-pressure mercury lamp was used to apply 100 mJ / cm² of heat. 2 The substrate was exposed to light through a photomask at the specified exposure level. Then, the substrate was immersed in a developer solution consisting of a 5% sodium carbonate aqueous solution at 25°C for 30 seconds and 1 minute, washed with pure water, and air-dried. The amount of developer residue remaining was observed. ○ indicated no residue after 30 seconds of immersion in the developer solution, △ indicated no residue after 1 minute of immersion, and × indicated residue was observed even after 1 minute of immersion. ○ and △ represent practical levels.

[0140] (Foreign object detection) The obtained photosensitive colored composition was coated onto a glass substrate with a pre-formed black matrix by spin coating, and then dried in a clean oven at 70°C for 20 minutes to form a coating with a thickness of 1.5 μm. Next, the substrate was cooled to room temperature and exposed to ultraviolet light through a photomask using an ultra-high pressure mercury lamp. After that, the substrate was spray-developed in a 0.2 mass% sodium carbonate aqueous solution at 23°C for 30 seconds, washed with deionized water, and dried. Furthermore, it was heat-treated in a clean oven at 230°C for 30 minutes to form a stripe-like pattern on the substrate. The fabricated pattern was formed to have a thickness of 2.0 μm after heat treatment at 230°C. The number of foreign particles in the colored pixels was measured using the obtained substrate. Evaluation was performed by surface observation using an Olympus Systems BX60 metal microscope. The magnification was set to 500x, and the number of foreign particles observable in any five fields of view was measured using transmission. High compatibility is indicated when the number of foreign particles can be suppressed. ◎: Fewer than 3 foreign objects (Excellent) ○: Number of foreign objects is 3 or more but less than 20 (good) △: Number of foreign objects is 21 or more but less than 100 (practical) ×: More than 100 foreign objects (not practical)

[0141] (Evaluation of adhesion) The obtained photosensitive colored composition was coated onto a 10 cm x 10 cm square glass substrate using a spin coater, and then dried in an 80°C oven for 5 minutes to form a coating with a thickness of 1.5 μm. After the substrate was cooled to room temperature, a high-pressure mercury lamp was used to apply 100 mJ / cm² of heat. 2The substrate was exposed to light through a photomask at the specified exposure level. Then, the substrate was developed by immersing it in a developer solution consisting of a 5% by mass sodium carbonate aqueous solution at 25°C for 1 minute. It was then washed with pure water, air-dried, and baked in an oven at 240°C for 40 minutes. This prepared the substrate for adhesion testing. Next, in accordance with JIS 5400, a grid test was performed on the coating film on the sample substrate, using 100 1mm square grids. The peeling state was observed using cellophane tape. The number of adhered grids (the number of grids that remained unpeeled) was counted to evaluate glass adhesion. Considering practical required physical properties, scores of 90 or higher were judged as ○, 80-89 as △, and 79 or lower as ×. ○ and △ represent practical levels.

[0142] (Chemical resistance evaluation) The obtained photosensitive colored composition was coated onto a 10 cm x 10 cm square glass substrate using a spin coater, and then dried in an 80°C oven for 5 minutes to form a coating with a thickness of 1.5 μm. After the substrate was cooled to room temperature, a high-pressure mercury lamp was used to apply 100 mJ / cm² of heat. 2 The substrate was exposed to light through a photomask at the specified exposure level. Then, it was heated at 230°C for 20 minutes and allowed to cool to produce an evaluation substrate. This substrate was then immersed in NMP (N-methylpyrrolidone) for 10 minutes, and its appearance was visually evaluated. ○ and △ indicate a practical level. ○: No particular changes are observed in the appearance (good) △: Slight changes are visible in the appearance (still usable). ×: Significant changes in appearance are visible, such as loss of surface gloss (unusable).

[0143] [Table 5]

[0144] The results in Table 5 show that the colored composition obtained using the dispersant of the present invention can solve all the problems. On the other hand, the comparative example could not satisfy all the requirements for dispersibility, compatibility, developability, and substrate adhesion.

Claims

1. A dispersant for an A-B block polymer having a substructure represented by the following general formula (1) at one end and a carboxyl group at the other end, The aforementioned Block A has a structural unit having a carboxyl group bonded to an aromatic ring and a hydroxyl group-containing monomer unit, The aforementioned block B is a dispersant having (meth)acrylic acid ester units. General formula (1) 【Chemistry 1】 [In general formula (1), Z is an alkyl group having 1 to 18 carbon atoms, an alkenyl group having 2 to 18 carbon atoms, a monovalent aromatic hydrocarbon group having 6 to 18 carbon atoms, or a monovalent heterocyclic group having 3 to 18 atoms, or -SR １ The base is indicated by R １ * indicates an alkyl group having 1 to 18 carbon atoms, and * indicates the bonding site with the polymer.

2. The dispersant according to claim 1, wherein the acid value is 10 to 200 mg KOH / g.

3. The dispersant according to claim 1, wherein the content of monomer units in block A is 10 to 40% by weight of the total monomer units of the A-B block polymer.

4. The dispersant according to claim 1, wherein the dispersant contains 80 to 100% by mass of structural units having a carboxyl group bonded to the aromatic ring in the monomer units of block A.

5. The dispersant according to claim 1, wherein the hydroxyl group-containing monomer units are contained in 0.05 to 5% by mass of the monomer units of block A.

6. The dispersant according to claim 1, wherein the weight-average molecular weight is 5,000 to 50,000, and the A-B block polymer contains 0% to 2% by mass of a polymer with a weight-average molecular weight of 1,000 or less.

7. The dispersant according to claim 1, having in order a substructure represented by general formula (1), a B block, an A block, and a carboxyl group.

8. A dispersion comprising a dispersant, a substance to be dispersed, and a solvent according to any one of claims 1 to 7.

9. A photosensitive colored composition comprising a dispersant, a colorant, a polymerizable compound, and a polymerization initiator according to any one of claims 1 to 7.

10. A film formed from the photosensitive coloring composition according to claim 9.

11. An optical filter having a substrate and the film described in claim 10.

12. An image display device having the optical filter of claim 11.

13. A solid-state image sensor having the optical filter of claim 11.

Images