Colorant dispersion, dispersant, colored curable composition, color filter, display device

Abstract

To provide a color material liquid dispersion, and a dispersing agent, capable of forming a curable coloring composition excelling in all of dispersion stability, brightness, contrast, adhesion to base material, and re-solubility in solvent.SOLUTION: Provided is a color material liquid dispersion containing a color material, a dispersing agent, and a solvent, where the dispersing agent includes: a salt polymer obtained by forming a salt from at least some of the acidic groups that, of a polymer having the constituent unit represented by general formula (I), are included in general formula (I); and at least one compound (B) selected from the group consisting of tertiary amines and basic heterocyclic compounds. (In general formula (I), R1 represents a hydrogen atom or a methyl group, A represents a direct bond or a divalent linking group, and Q is an acidic group).SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a colorant dispersion, a dispersant, a colored curable composition, a color filter, and a display device. [Background technology]

[0002] In recent years, the demand for liquid crystal displays has increased with the development of personal computers, especially portable personal computers. The penetration rate of mobile displays (mobile phones, smartphones, tablet PCs) is also increasing, and the market for liquid crystal displays is expanding further. Recently, organic light-emitting display devices such as organic EL displays, which have high visibility due to their self-luminescence, have also been attracting attention as next-generation image display devices. In terms of the performance of these image display devices, there is a strong demand for further improvement in image quality, such as improved contrast, brightness, and color reproducibility, as well as reduced power consumption.

[0003] Color filters are used in these liquid crystal display devices and organic light-emitting display devices. For example, when a color image is formed in a liquid crystal display device, the light passing through the color filter is colored as it is with the color of each pixel that constitutes the color filter, and the light of these colors is combined to form a color image. In addition to conventional cold cathode fluorescent lamps, organic light-emitting elements that emit white light or inorganic light-emitting elements that emit white light may be used as the light source in this case. In addition, organic light-emitting display devices use color filters for color adjustment and the like. Under these circumstances, there is an increasing demand for color filters with higher brightness, higher contrast, and improved color reproducibility.

[0004] Here, a color filter generally has a transparent substrate, a colored layer formed on the transparent substrate and consisting of colored patterns of the three primary colors, red, green, and blue, and a light-shielding portion formed on the transparent substrate so as to partition each colored pattern.

[0005] Among the methods for forming pixels in color filters, the pigment dispersion method is the most widely used because it has excellent characteristics on average in terms of spectral characteristics, durability, pattern shape and accuracy, and the like. In color filters having pixels formed by using a pigment dispersion method, miniaturization of pigments has been studied to realize high brightness and high contrast. It is believed that miniaturization of pigments reduces the scattering of light passing through the color filter by pigment particles, thereby achieving high brightness and high contrast. However, since finely divided pigment particles tend to aggregate, there is a problem in that dispersibility and dispersion stability are reduced.

[0006] It is known that the use of a dispersant is effective as a method for improving the dispersibility of finely divided pigments. For example, Patent Document 1 discloses a block copolymer that can provide a dispersion composition with excellent dispersion stability when used as a dispersant, the block copolymer having an A block containing a structural unit derived from a vinyl monomer having two or more carboxyl groups, at least two of which are bonded to adjacent carbon atoms on an aromatic ring, and a B block containing a structural unit derived from a (meth)acrylic acid alkyl ester, and having an acid value of 30 to 250 mgKOH / g.

[0007] On the other hand, Patent Document 2 describes a color filter color composition that has excellent dispersibility, contrast ratio, brightness, and heat resistance, and further has excellent developability in an alkaline aqueous solution and achieves high resolution. The color filter color composition contains a pigment, a basic dispersant, an acidic dispersant (X), a binder resin, and a solvent, and is characterized in that the acidic dispersant has a main chain that is a polyester having a carboxyl group derived from a tricarboxylic acid anhydride and / or a tetracarboxylic acid dianhydride, and a side chain that is a vinyl polymer having a specific structure, and the basic dispersant is a graft copolymer and / or a block copolymer having an amino group, and has an amine value of 10 to 350 mgKOH / g. [Prior art documents] [Patent documents]

[0008] [Patent Document 1] JP 2016-204529 A [Patent Document 2] JP 2016-191909 A Summary of the Invention [Problem to be solved by the invention]

[0009] As described above, in recent color filters, the particle size of the pigment used has been reduced due to the demand for high brightness and high contrast. Since fine pigments tend to aggregate due to the increase in specific surface area, dispersants with higher dispersibility are required. In addition, the demand for a high color gamut and thin film has increased the demand for a high concentration of coloring material in the colored curable composition. When the coloring material ratio in the colored curable composition increases, the binder component decreases relatively. When the binder components, such as polyfunctional monomers and photoinitiators, that are involved in the curing properties of the coating film, are reduced, the crosslink density of the coating film decreases due to insufficient curing, and the substrate adhesion of the coating film decreases. Similarly, when the ratio of coloring material that is difficult to dissolve in a solvent in the colored curable composition increases and the binder component that is easily soluble in a solvent is relatively reduced, the solvent resolubility deteriorates. Therefore, in order to achieve the demand for a high concentration of coloring material in the colored curable composition, a technology is required that simultaneously solves the problems caused by the shortage of these binder components. The substrate adhesion is an index of the adhesion of the formed colored coating film (cured product of the colored curable composition) to the substrate, and if the substrate adhesion is poor, the colored coating film peels off due to physical impact in the process after the colored coating film is formed, resulting in a problem of display defects. In addition, the solvent resolubility refers to the property of the solid content of the colored curable composition once dried dissolving in a solvent again. For example, when the colored curable composition adheres to the tip of the die lip during coating with a die coater, a solidified material is generated by drying. If the solidified material is not easily dissolved in the colored curable composition when coating is resumed, the solidified material on the die lip is partially peeled off and easily adheres to, for example, the colored layer of a color filter, causing a foreign matter defect. In particular, when the colorant concentration of the colored curable composition is increased, the solvent resolubility is easily insufficient, and the reduction in yield due to the generation of the above-mentioned foreign matter in the manufacturing process of the color filter has been a problem.

[0010] The present invention has been made in view of the above circumstances, and aims to provide a colorant dispersion liquid and a dispersant capable of producing a colored curable composition that simultaneously satisfies excellent dispersion stability, brightness, contrast, substrate adhesion, and solvent resolubility. Another object of the present invention is to provide a colored curable composition that simultaneously satisfies excellent dispersion stability, brightness, contrast, substrate adhesion, and solvent resolubility. Another object of the present invention is to provide a color filter and a display device formed using the colored curable composition. [Means for solving the problem]

[0011] The colorant dispersion according to the present invention is a colorant dispersion containing a colorant, a dispersant, and a solvent, The dispersant contains a salt-type polymer in which at least a portion of the acidic groups contained in a polymer having a structural unit represented by the following general formula (I) forms a salt with one or more compounds (B) selected from the group consisting of tertiary amino group-containing basic compounds and basic heterocyclic compounds:

[0012] [ka] (In general formula (I), R 1 represents a hydrogen atom or a methyl group, A represents a direct bond or a divalent linking group, and Q is an acidic group.

[0013] The dispersant according to the present invention is a salt-type polymer in which at least a portion of the acidic groups contained in a polymer having a structural unit represented by general formula (I) forms a salt with one or more compounds (B) selected from the group consisting of tertiary amino group-containing basic compounds and basic heterocyclic compounds.

[0014] The colored curable composition according to the present invention contains a colorant, the dispersant according to the present invention, a polymerizable compound, an initiator, and a solvent.

[0015] The color filter according to the present invention is a color filter comprising at least a substrate and colored layers provided on the substrate, and at least one of the colored layers is a cured product of the colored curable composition according to the present invention.

[0016] A display device according to the present invention has the color filter according to the present invention. Effect of the Invention

[0017] According to the present invention, it is possible to provide a colorant dispersion liquid and a dispersant capable of preparing a colored curable composition that simultaneously satisfies excellent dispersion stability, brightness, contrast, substrate adhesion, and solvent resolubility. Also, according to the present invention, it is possible to provide a colored curable composition that simultaneously satisfies excellent dispersion stability, brightness, contrast, substrate adhesion, and solvent resolubility. Also, according to the present invention, it is possible to provide a color filter and a display device formed using the colored curable composition. [Brief description of the drawings]

[0018] [Figure 1] FIG. 1 is a schematic diagram showing an example of the color filter of the present invention. [Diagram 2] FIG. 2 is a schematic diagram showing an example of the liquid crystal display device of the present invention. [Diagram 3] FIG. 3 is a schematic diagram showing an example of an organic light-emitting display device of the present invention. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0019] The colorant dispersion, the dispersant, the colored curable composition, the color filter, and the display device according to the present invention will be described in detail below. In the present invention, light includes electromagnetic waves with wavelengths in the visible and invisible regions, as well as radiation, and radiation includes, for example, microwaves and electron beams. Specifically, it refers to electromagnetic waves with wavelengths of 5 μm or less and electron beams. In the present invention, (meth)acryloyl refers to each of acryloyl and methacryloyl, (meth)acrylic refers to each of acrylic and methacrylic, and (meth)acrylate refers to each of acrylate and methacrylate. In this specification, unless otherwise specified, chromaticity coordinates x, y are those in the XYZ color system of JIS Z8701:1999 measured using a C light source. In addition, in this specification, the use of "to" indicating a numerical range is used to mean that the numerical values ​​before and after it are included as the lower limit and upper limit.

[0020] I. Colorant dispersion liquid The colorant dispersion according to the present invention is a colorant dispersion containing a colorant, a dispersant, and a solvent, The dispersant contains a salt-type polymer in which at least a portion of the acidic groups contained in a polymer having a structural unit represented by the following general formula (I) forms a salt with one or more compounds (B) selected from the group consisting of tertiary amino group-containing basic compounds and basic heterocyclic compounds:

[0021] [ka] (In general formula (I), R 1 represents a hydrogen atom or a methyl group, A represents a direct bond or a divalent linking group, and Q is an acidic group.

[0022] The colorant dispersion liquid according to the present invention uses, as a dispersant, at least a salt-type polymer in which at least a part of the acidic groups contained in the general formula (I) forms a salt with one or more compounds (B) selected from the group consisting of tertiary amino group-containing basic compounds and basic heterocyclic compounds. In the salt type polymer used as a dispersant in the present invention, at least a part of the acidic groups, which are colorant-adsorptive groups, forms a salt with a specific basic compound, thereby increasing the polarity of the colorant-adsorptive groups and enhancing the colorant-adsorptive properties, thereby improving the dispersibility and dispersion stability of the colorant, thereby improving contrast and brightness. In addition, it is presumed that the increased colorant-adsorptive properties of the dispersant result in the colorant being appropriately coated with the dispersant, thereby improving the solvent resolubility. In addition, in the salt type polymer used as a dispersant in the present invention, at least a part of the acidic groups, which are colorant-adsorptive groups, forms a salt with a specific basic compound, and this increases the polarity of the dispersant and enhances the interaction with the substrate surface, which is presumably why adhesion to the substrate is improved.

[0023] The colorant dispersion liquid according to the present invention contains at least a colorant, a dispersant, and a solvent, and may further contain other components within a range that does not impair the effects of the present invention. Hereinafter, each component of the colorant dispersion liquid according to the present invention will be described in detail, starting with the dispersant of the present invention.

[0024] <Dispersant> In the present invention, at least one salt-type polymer is used as the dispersant, in which at least a portion of the acidic groups contained in a polymer having a structural unit represented by the general formula (I) forms a salt with one or more compounds (B) selected from the group consisting of tertiary amino group-containing basic compounds and basic heterocyclic compounds.

[0025] [Polymer having a structural unit represented by the above general formula (I)] (Structural unit represented by general formula (I)) In general formula (I), R 1 represents a hydrogen atom or a methyl group, A represents a direct bond or a divalent linking group, and Q is an acidic group. In A, examples of the divalent linking group include linear, branched or cyclic, saturated or unsaturated aliphatic hydrocarbon groups, linear, branched or cyclic, saturated or unsaturated aliphatic hydrocarbon groups having a hydroxyl group, aromatic hydrocarbon groups, -CONH-, -COO-, -NHCOO-, ether groups (-O-), thioether groups (-S-), and combinations thereof. In the present invention, the direction of the bond of the divalent linking group is arbitrary. That is, when the divalent linking group contains -CONH-, -CO may be on the carbon atom side of the main chain and -NH may be on the nitrogen atom side of the side chain, or conversely, -NH may be on the carbon atom side of the main chain and -CO may be on the nitrogen atom side of the side chain.

[0026] Specific examples of the aliphatic hydrocarbon group include linear alkylene groups such as a methylene group, a dimethylene group (ethylene group), a trimethylene group, a tetramethylene group, a pentamethylene group, a hexamethylene group, an octamethylene group, and a decamethylene group; branched alkylene groups such as a methylmethylene group, a methylethylene group, a 1-methylpentylene group, and a 1,4-dimethylbutylene group; and cyclic alkylene groups such as a cyclopentylene group and a cyclohexylene group. The aliphatic hydrocarbon group may have 1 to 20 carbon atoms, and from the viewpoint of dispersion stability, it is preferably 1 to 16, more preferably 1 to 12, and even more preferably 2 to 8 carbon atoms. Specific examples of the aromatic hydrocarbon group include a phenylene group and a naphthylene group.

[0027] Among these, from the viewpoint of dispersibility, A in general formula (I) is preferably a divalent linking group containing at least one of a -CONH- group and a -COO- group, and more preferably a divalent linking group containing at least one of a -CONH- group and a -COO- group, and an aliphatic hydrocarbon group having 1 to 12 carbon atoms which may contain an oxygen atom.

[0028] Examples of the acidic group represented by Q include a carboxy group (-COOH), a sulfonic acid group (SO3H), a phosphonic acid group (-P(=O)(OH)2), and a phosphoric acid group (-OP(=O)(OH)2). From the viewpoint of dispersion stability, the acidic group represented by Q is preferably at least one selected from the group consisting of a carboxy group (-COOH), a sulfonic acid group (SO3H), and a phosphoric acid group (-OP(=O)(OH)2). Examples of the phosphoric acid group-containing ethylenically unsaturated monomer include 2-(meth)acryloyloxyethyl acid phosphate, acid phosphooxy polyoxyethylene glycol mono(meth)acrylate, and the like. Examples of the sulfonic acid group-containing ethylenically unsaturated monomer include (meth)acryloyloxyethylsulfonic acid and 2-(meth)acrylamide-2-methylpropanesulfonic acid. Of the acidic groups represented by Q, a carboxy group is preferred from the standpoint of brightness, and the constitutional unit represented by the general formula (I) above preferably contains a constitutional unit represented by the following general formula (II).

[0029] [ka] (In general formula (II), R 1 represents a hydrogen atom or a methyl group, and A represents a direct bond or a divalent linking group.

[0030] R in the general formula (II) 1 and A may be the same as in general formula (I). Examples of the constituent unit represented by the general formula (II) include a constituent unit derived from (meth)acrylic acid, a constituent unit derived from vinylbenzoic acid, and a constituent unit derived from a (meth)acrylic acid ester. As the structural unit of the general formula (II), from the viewpoint of dispersibility and dispersion stability, at least one selected from the group consisting of a structural unit represented by the following general formula (II-1) and a structural unit represented by the following general formula (II-2) is preferable.

[0031] [ka] (In general formula (II-1), R 1represents a hydrogen atom or a methyl group, In general formula (II-2), R 1 represents a hydrogen atom or a methyl group, R 2 represents an aliphatic hydrocarbon group which may contain an oxygen atom, R 3 represents a hydrocarbon group.

[0032] The structural unit represented by the general formula (II-1) is a structural unit derived from (meth)acrylic acid. In the structural unit represented by the general formula (II-2), R 2 represents an aliphatic hydrocarbon group which may contain an oxygen atom. R 2 The aliphatic hydrocarbon group in may be the same as described above. R 2 The aliphatic hydrocarbon group containing an oxygen atom in the above formula (I) has a structure in which a carbon atom in the aliphatic hydrocarbon group is replaced with an oxygen atom, or a hydrogen atom in the aliphatic hydrocarbon group is replaced with a substituent containing an oxygen atom. Examples of the aliphatic hydrocarbon group that may contain an oxygen atom include a structure in which a linking group such as -O-, -COO-, -OCO-, etc. is contained in the carbon chain of the hydrocarbon group. Specific examples of the aliphatic hydrocarbon group containing an oxygen atom include -R 20 -(OR 21 )s-(where R 20 and R 21 each independently represents an aliphatic hydrocarbon group, and s represents a number from 1 to 80), -R 22 -(OCO-R 23 )t-(where R 22 and R 23 each independently represents an aliphatic hydrocarbon group, and t represents a number from 1 to 40. 20 , R 21 , R 22 and R 23 The aliphatic hydrocarbon group of R may be the same as the aliphatic hydrocarbon group described above. 20 is preferably an alkylene group having 1 to 20 carbon atoms, 21is preferably an alkylene group having 1 to 20 carbon atoms, and s is preferably a number of 1 to 40, more preferably 2 to 25, and even more preferably 2 to 10. From the viewpoint of dispersion stability, the R 22 is preferably an alkylene group having 1 to 20 carbon atoms, 23 is preferably an alkylene group having 1 to 20 carbon atoms, and t is preferably a number of 1 to 30, more preferably 1 to 20, and even more preferably 1 to 10. R 20 and the above R 22 are each independently preferably an alkylene group having 1 to 12 carbon atoms, and more preferably an alkylene group having 2 to 8 carbon atoms. R 21 is preferably an alkylene group having 2 to 8 carbon atoms, and more preferably an ethylene group or a propylene group. R 23 is preferably an alkylene group having 2 to 8 carbon atoms, and more preferably an alkylene group having 3 to 7 carbon atoms. Examples of the substituent containing an oxygen atom include a hydroxyl group and an alkoxy group. In the structural unit represented by the general formula (II-2), R 2 In particular, from the viewpoint of re-solubility in a solvent, the alkyl group may be an aliphatic hydrocarbon group, and may be an aliphatic hydrocarbon group having 1 to 20 carbon atoms.

[0033] In the structural unit represented by the general formula (II-2), R 3 R represents a hydrocarbon group. 3 Examples of the hydrocarbon group in include an aliphatic hydrocarbon group, an aromatic hydrocarbon group, and a combination thereof. The aliphatic hydrocarbon group and the aromatic hydrocarbon group may be the same as those described above. R 3 The hydrocarbon group may have 1 to 20 carbon atoms, and from the viewpoint of dispersion stability, it is preferably 1 to 16, more preferably 2 to 12, and even more preferably 2 to 6.

[0034] The structural unit represented by general formula (II-2) can be derived, for example, from a monomer which is an addition reaction product between a (meth)acrylate having a hydroxyl group and a dicarboxylic acid or dicarboxylic acid anhydride. Examples of (meth)acrylates having a hydroxyl group include 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, 6-hydroxyhexyl (meth)acrylate, (poly)ethylene glycol mono(meth)acrylate, (poly)propylene glycol mono(meth)acrylate, and unsaturated fatty acid hydroxyalkyl ester-modified ε-caprolactone. Examples of the aliphatic dicarboxylic acid or the aliphatic dicarboxylic anhydride include malonic acid, succinic acid, glutaric acid, adipic acid, 1,6-hexanedicarboxylic acid, hexahydrophthalic acid, succinic anhydride, adipic anhydride, hexahydrophthalic anhydride, maleic anhydride, etc. Examples of the aromatic dicarboxylic acid or the aromatic dicarboxylic anhydride include terephthalic acid, isophthalic acid, phthalic acid, 2,6-naphthalenedicarboxylic acid, 2,7-naphthalenedicarboxylic acid, diphenyldicarboxylic acid, 4,4'-dicarboxydiphenyl ether, phthalic anhydride, naphthalic anhydride, etc.

[0035] In the polymer, the constitutional unit represented by general formula (I) may be composed of one type, or may contain two or more types of constitutional units.

[0036] From the viewpoints of dispersibility and dispersion stability, the polymer having a structural unit represented by the general formula (I) is preferably a copolymer, and is more preferably at least one of a graft copolymer having a structural unit represented by the general formula (I) and a block copolymer having an A block containing a structural unit represented by the general formula (I).

[0037] {Graft copolymer} The graft copolymer used in the present invention is preferably a copolymer having a constitutional unit represented by the above general formula (I) in the main chain, which functions as an adsorption site for a colorant, and a graft polymer chain in the side chain, which functions as a solvent affinity site.

[0038] (Structural unit having a graft polymer chain) The graft copolymer has, in its side chain, a graft polymer chain that functions as a solvent affinity site. As a guideline, the polymer chain preferably has a solubility at 23° C. of 20 (g / 100 g solvent) or more in the organic solvent used in combination. The solubility of the polymer chain can be determined by the fact that the raw material into which the polymer chain is introduced when preparing the graft copolymer has the above solubility. For example, when a polymerizable oligomer (macromonomer) containing a polymer chain and a group having an ethylenically unsaturated double bond at its end is used to introduce a polymer chain into the graft copolymer, the polymerizable oligomer should have the above solubility. In addition, when a polymer chain is introduced using a polymer chain containing a reactive group capable of reacting with a reactive group contained in the copolymer after a copolymer is formed by a monomer containing a group having an ethylenically unsaturated double bond, the polymer chain containing the reactive group should have the above solubility.

[0039] The graft copolymer used in the present invention preferably has, in its main chain, a constitutional unit represented by the above general formula (I) that functions as an adsorption site for a colorant, and further has, in its side chain, a constitutional unit represented by the following general formula (III) that has a polymer chain that functions as a solvent affinity site.

[0040] [ka] (In general formula (III), R 1” is a hydrogen atom or a methyl group, A 1 represents a direct bond or a divalent linking group, and Polymer represents a polymer chain.

[0041] In the general formula (III), A 1 is a direct bond or a divalent linking group. 1 The divalent linking group in is not particularly limited as long as it can link the carbon atom derived from the ethylenically unsaturated double bond to the polymer chain. The divalent linking group may be the same as A in general formula (I). Among these, from the viewpoint of dispersibility and dispersion stability, A in the general formula (III) is 1 is preferably a divalent linking group containing a -CONH- group or a -COO- group, and more preferably a divalent linking group containing a -CONH- group or a -COO- group and an aliphatic hydrocarbon group having 1 to 12 carbon atoms which may contain an oxygen atom.

[0042] The polymer chain preferably contains at least one type of constitutional unit represented by the following general formula (IV) from the viewpoint of dispersibility and dispersion stability of the colorant.

[0043] [ka] (In general formula (IV), R 11 is a hydrogen atom or a methyl group, A 2 is a divalent linking group, R 4 is a hydrocarbon group which may have a substituent and may contain a heteroatom.

[0044] In the general formula (IV), A 2 is a divalent linking group. 2 Examples of the divalent linking group in A include 1 The divalent linking group may be the same as the divalent linking group in the above formula. Among these, from the viewpoint of dispersibility and dispersion stability of the colorant, A in general formula (IV) is 2 is preferably a divalent linking group containing a -CONH- group or a -COO- group, and more preferably a -CONH- group or a -COO- group.

[0045] R 4Examples of the hydrocarbon group in the hydrocarbon group which may contain a heteroatom include an alkyl group having 1 to 18 carbon atoms, an alkenyl group having 2 to 18 carbon atoms, an aryl group, and combinations thereof such as an aralkyl group or an alkyl-substituted aryl group. The alkyl group having 1 to 18 carbon atoms may be linear, branched, or cyclic, and examples thereof include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an n-nonyl group, an n-lauryl group, an n-stearyl group, a cyclopentyl group, a cyclohexyl group, a bornyl group, an isobornyl group, a dicyclopentanyl group, an adamantyl group, a lower alkyl group-substituted adamantyl group, etc. The number of carbon atoms in the alkyl group is preferably 1 to 12, and more preferably 1 to 6. The alkenyl group having 2 to 18 carbon atoms may be linear, branched, or cyclic. Examples of such alkenyl groups include vinyl, allyl, and propenyl groups. There is no limitation on the position of the double bond in the alkenyl group, but from the viewpoint of the reactivity of the obtained polymer, it is preferable that the double bond is located at the terminal of the alkenyl group. The number of carbon atoms in the alkenyl group is preferably 2 to 12, and more preferably 2 to 8. Examples of the aryl group include a phenyl group, a biphenyl group, a naphthyl group, a tolyl group, a xylyl group, etc. The number of carbon atoms in the aryl group is preferably 6 to 24, and more preferably 6 to 12. Examples of the aralkyl group include a benzyl group, a phenethyl group, a naphthylmethyl group, and a biphenylmethyl group, which may further have a substituent. The number of carbon atoms in the aralkyl group is preferably 7 to 20, and more preferably 7 to 14. Furthermore, the aromatic ring of the aryl group, aralkyl group, or the like may have a linear or branched alkyl group having 1 to 30 carbon atoms bonded thereto as a substituent.

[0046] R 4In terms of dispersibility and dispersion stability, the hydrocarbon group in is preferably at least one selected from the group consisting of an alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 12 carbon atoms which may be substituted with an alkyl group, and an aralkyl group having 7 to 14 carbon atoms which may be substituted with an alkyl group, and is preferably at least one selected from the group consisting of a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an n-nonyl group, an n-lauryl group, an n-stearyl group, a phenyl group which may be substituted with an alkyl group, and a benzyl group.

[0047] R 4 The hydrocarbon group containing a heteroatom in the above means a structure in which a carbon atom in the above hydrocarbon group is replaced with a heteroatom, or a hydrogen atom in the above hydrocarbon group is replaced with a substituent containing a heteroatom. Examples of the heteroatom that may be contained in the hydrocarbon group include an oxygen atom, a nitrogen atom, a sulfur atom, and a silicon atom. Examples of the hydrocarbon group that may contain a heteroatom include a structure in which a linking group such as -CO-, -COO-, -OCO-, -O-, -S-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -OCO-NH-, -NH-COO-, -NH-CO-NH-, -NH-O-, and -O-NH- are contained in the carbon chain of the hydrocarbon group. In addition, the hydrocarbon group may have a substituent within the range that does not impair the dispersion performance, etc. of the graft copolymer. Examples of the substituent include a halogen atom, a hydroxyl group, a carboxy group, an alkoxy group, a nitro group, a cyano group, an epoxy group, an isocyanate group, and a thiol group.

[0048] Also, R 4 The hydrocarbon group which may contain a heteroatom in may have a structure in which a polymerizable group such as an alkenyl group is added to the end of the hydrocarbon group via a linking group containing a heteroatom. For example, the structural unit represented by general formula (IV) may have a structure in which a structural unit derived from (meth)acrylic acid is reacted with glycidyl (meth)acrylate. That is, -A in general formula (IV) may have a structure in which a polymerizable group such as an alkenyl group is added to the end of the hydrocarbon group via a linking group containing a heteroatom. 2 -R4 The structure of may be represented by -COO-CH2CH(OH)CH2-OCO-CR=CH2 (where R is a hydrogen atom or a methyl group). The structural unit represented by general formula (IV) may be a structure obtained by reacting a structural unit derived from a hydroxyalkyl (meth)acrylate with a 2-isocyanatoalkyl (meth)acrylate. That is, R in general formula (IV) 4 However, it may have a structure represented by -R'-OCONH-R"-OCO-CR=CH2 (wherein R' and R" each independently represent an alkylene group, and R represents a hydrogen atom or a methyl group).

[0049] Examples of monomers that derive the structural unit represented by formula (IV) include methyl (meth)acrylate, ethyl (meth)acrylate, isopropyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, tert-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, 2-ethoxyethyl (meth)acrylate, cyclohexyl (meth)acrylate, benzyl (meth)acrylate, phenyl (meth)acrylate, isobornyl (meth)acrylate, dicyclopentanyl (meth)acrylate, adamantyl (meth)acrylate, and (meth)acrylic acid. Preferred are those having structural units derived from 2-methacryloyloxyethyl succinate, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, 2-hydroxy-3-phenoxypropyl (meth)acrylate, phenoxyethyl (meth)acrylate, methoxypolyethylene glycol (meth)acrylate and polyethylene glycol (meth)acrylate, phenoxyethylene glycol (meth)acrylate, unsaturated fatty acid hydroxyalkyl ester modified ε-caprolactone, etc. However, the present invention is not limited to these.

[0050] In the present invention, the R 4As the organic solvent, it is preferable to use one having excellent solubility in the organic solvent described later, and it may be appropriately selected according to the organic solvent used in the colorant dispersion liquid. Specifically, for example, when the organic solvent is an ether alcohol acetate type, an ether type, an ester type, an alcohol type, or the like, which is generally used as an organic solvent for the colorant dispersion liquid, a methyl group, an ethyl group, an isobutyl group, an n-butyl group, a 2-ethylhexyl group, a benzyl group, a cyclohexyl group, a dicyclopentanyl group, a hydroxyethyl group, a phenoxyethyl group, an adamantyl group, a methoxypolyethylene glycol group, a methoxypolypropylene glycol group, a polyethylene glycol group, or the like is preferable.

[0051] In the polymer chain, the constitutional unit represented by the general formula (IV) may be of one type alone or may be of two or more types mixed together. From the viewpoint of dispersibility and dispersion stability of the colorant, the total proportion of the structural units represented by the general formula (IV) in the polymer chain may be 100% by mass relative to all structural units of the polymer chain (100% by mass). From the viewpoint of dispersibility and dispersion stability of the colorant, the total proportion of the structural units represented by the general formula (IV) in the polymer chain is preferably 40% by mass or more, more preferably 70% by mass or more, relative to all structural units of the polymer chain.

[0052] Furthermore, it is preferable that the polymer chain of the macromonomer contains at least one type of constituent unit selected from the group consisting of constituent units represented by the following general formula (V) and constituent units represented by the following general formula (V'), among the constituent units represented by the general formula (IV), in terms of improving adhesion to the substrate and shortening the development time.

[0053] [ka] (In general formula (V), R 11’ is a hydrogen atom or a methyl group, A 2’ is a divalent linking group, R 5 is an ethylene group or a propylene group, R 6is a hydrogen atom or a hydrocarbon group, and m is a number of 2 or more and 80 or less. In general formula (V'), R 11” is a hydrogen atom or a methyl group, A 2” is a divalent linking group, R 7 is an alkylene group having 1 to 10 carbon atoms, R 8 is an alkylene group having 3 to 7 carbon atoms, R 9 is a hydrogen atom or a hydrocarbon group, and n is a number between 1 and 40.

[0054] In the constitutional unit represented by the general formula (V) and the constitutional unit represented by the general formula (V'), A 2’ , and A 2” are each independently a divalent linking group. 2’ and A 2” Examples of the divalent linking group in A include 2 The divalent linking group may be the same as the divalent linking group in the above formula. Among them, A is the most suitable for color filters because of its solubility in organic solvents. 2’ , and A 2” are each independently preferably a divalent linking group containing a -CONH- group or a -COO- group, and more preferably a -CONH- group or a -COO- group.

[0055] In the general formula (V), m represents the number of repeating units of an ethylene oxide chain or a propylene oxide chain and is a number of 2 or more. From the viewpoint of adhesion to a substrate, m is preferably 3 or more, and more preferably 4 or more. On the other hand, the upper limit of m is 80 or less, but is preferably 50 or less from the viewpoint of solubility in organic solvents used in color filters.

[0056] R 6 is a hydrogen atom or a hydrocarbon group, 6 Examples of the hydrocarbon group in include an alkyl group having 1 to 18 carbon atoms, an alkenyl group having 2 to 18 carbon atoms, an aryl group, and combinations thereof such as an aralkyl group or an alkyl-substituted aryl group. R6 The hydrocarbon group in R 4 The hydrocarbon groups are the same as those in the above. R 6 In particular, from the viewpoint of dispersion stability, the hydrocarbon group in is preferably at least one selected from the group consisting of an alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 12 carbon atoms which may be substituted with an alkyl group, and an aralkyl group having 7 to 14 carbon atoms which may be substituted with an alkyl group, and is preferably at least one selected from the group consisting of a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an n-nonyl group, an n-lauryl group, an n-stearyl group, a phenyl group which may be substituted with an alkyl group, and a benzyl group.

[0057] In the general formula (V'), R 7 is an alkylene group having 1 to 10 carbon atoms, An alkylene group having 2 to 8 carbon atoms is preferred from the viewpoint of re-solubility in a solvent. R 8 is an alkylene group having 3 to 7 carbon atoms, of which an alkylene group having 3 to 5 carbon atoms, and more preferably an alkylene group having 5 carbon atoms, is preferred from the standpoint of adhesion to substrates. R 9 is a hydrogen atom or a hydrocarbon group, 9 The hydrocarbon group in R 6 may be the same as the hydrocarbon group in

[0058] In the general formula (V'), n represents the number of repeating units of the lactone chain and is a number of 1 or more, preferably 2 or more, and more preferably 3 or more, from the viewpoint of adhesion to the substrate. On the other hand, the upper limit of n is 40 or less, but is preferably 20 or less from the viewpoint of solubility in organic solvents used in color filters.

[0059] In the polymer chain, the constitutional unit represented by the general formula (V) and beforeThe at least one structural unit selected from the group consisting of structural units represented by the general formula (V') may be of one type alone or a mixture of two or more types. In order to improve the adhesion to the substrate and shorten the development time, the macromonomer of the graft copolymer preferably contains a constitutional unit represented by the general formula (V) and before The total proportion of at least one type of structural unit selected from the group consisting of structural units represented by the general formula (V') is preferably 5% by mass or more, more preferably 10% by mass or more, and even more preferably 15% by mass or more. before From the viewpoint of solvent resolubility, the total proportion of at least one type of structural unit selected from the group consisting of structural units represented by the general formula (V') is preferably 90 mass% or less, more preferably 80 mass% or less, and even more preferably 70 mass% or less, relative to all structural units of the polymer chain.

[0060] The structural units of the polymer chain in the structural unit represented by the general formula (III) of the graft copolymer include a structural unit represented by the general formula (V) and before In addition to the structural unit represented by the general formula (IV) which includes at least one type of structural unit selected from the group consisting of structural units represented by the general formula (V'), other structural units may be included. Examples of other structural units include structural units derived from ethylenically unsaturated monomers that are copolymerizable with the ethylenically unsaturated monomers that derive the structural unit represented by the general formula (IV) above. Examples of monomers from which other structural units are derived include styrenes such as styrene and α-methylstyrene, and vinyl ethers such as phenyl vinyl ether.

[0061] In the polymer chain of the structural unit represented by the general formula (III) of the graft copolymer, the total proportion of other structural units is preferably 30 mass% or less, and more preferably 10 mass% or less, based on all structural units of the polymer chain, in terms of the effects of the present invention.

[0062] In addition, from the viewpoint of dispersibility and dispersion stability of the colorant, the mass average molecular weight Mw of the polymer chain is preferably 2000 or more, more preferably 3000 or more, even more preferably 4000 or more, and more preferably 15000 or less, even more preferably 12000 or less. Within the above range, a sufficient steric repulsion effect as a dispersant can be maintained, and the above-mentioned action due to the increase in the specific surface area of ​​the solvent-compatible portion of the dispersant can be improved. The mass average molecular weight Mw of the polymer chain can be measured for the polymerizable oligomer or the polymer chain containing a reactive group in the same manner as for the dispersant described later.

[0063] In addition, the polymer chain has an acid value of 10 mgKOH / g or less, and more preferably has an acid value of 0 mgKOH / g or less. in From the viewpoint of dispersion stability, the acid value can be measured for the polymerizable oligomer or the polymer chain containing the reactive group in the same manner as the acid value of the dispersant described below. The polymer chain may contain a structural unit represented by general formula (I) as long as the effects of the present invention are not impaired. From the viewpoint of dispersion stability, however, the total proportion of structural units containing an acidic group relative to all structural units of the polymer chain is preferably 5% by mass or less, and more preferably 0% by mass.

[0064] In addition, the polymer chain has an amine value of 10 mgKOH / g or less, and more preferably has an amine value of 0 mgKOH / g or less. inIn terms of dispersibility and dispersion stability, it is preferable that the amine value of the polymer chain is equal to the mass (mg) of potassium hydroxide equivalent to the amount of hydrochloric acid required to neutralize 1 g of the solid content of the polymerizable oligomer or the polymer chain containing the reactive group, and is a value measured by the method described in JIS K 7237:1995. The polymer chain may contain a nitrogen atom-containing structural unit as long as the effects of the present invention are not impaired. From the viewpoint of dispersion stability, however, the total proportion of the nitrogen atom-containing structural units relative to all structural units of the polymer chain is preferably 5 mass% or less, and more preferably 0 mass%.

[0065] In the graft copolymer, the content of the structural unit represented by the general formula (I) is preferably 3% by mass or more and 60% by mass or less, more preferably 6% by mass or more and 45% by mass or less, and even more preferably 9% by mass or more and 35% by mass or less, based on the total structural units of the main chain of the graft copolymer. If the content of the structural unit represented by the general formula (I) in the graft copolymer is within the above range, the proportion of the part having affinity with the coloring material in the graft copolymer becomes appropriate, and the decrease in solubility in organic solvents can be suppressed, so that the adsorption to the coloring material becomes good, and excellent dispersibility, dispersion stability, and solvent resolubility can be obtained. On the other hand, in the graft copolymer, the total content of the structural unit containing the graft polymer chain and the structural unit represented by the general formula (III) is preferably 40% by mass or more and 97% by mass or less, more preferably 55% by mass or more and 94% by mass or less, and even more preferably 65% ​​by mass or more and 91% by mass or less, based on the total structural units of the main chain of the graft copolymer. If the total content of the structural unit containing the graft polymer chain and the structural unit represented by the general formula (III) in the graft copolymer is within the above range, the proportion of the solvent-compatible portion in the graft copolymer becomes appropriate, and the steric repulsion effect as a dispersant can be sufficiently maintained, and the specific surface area of ​​the solvent-compatible portion of the dispersant can be increased to improve the effect of the above effect. The content ratio of the structural unit is calculated from the amount of monomers that derive the structural unit represented by the general formula (I) and the structural unit represented by the general formula (III) when synthesizing the graft copolymer.

[0066] The graft copolymer used in the present invention may further have other structural units in addition to the structural unit represented by the general formula (I) and the structural unit represented by the general formula (III) within the range in which the effects of the present invention are not impaired. As the other structural units, ethylenically unsaturated monomers copolymerizable with the ethylenically unsaturated monomers from which the structural units represented by the general formula (I) and the like are derived can be appropriately selected and copolymerized to introduce the other structural units. Examples of other structural units copolymerized in the main chain with the structural unit represented by general formula (I) include structural units represented by general formula (IV) and structural units containing an acidic group different from the structural unit represented by general formula (I). Examples of monomers that derive a structural unit containing an acidic group different from the structural unit represented by the general formula (I) include maleic acid, maleic acid monoalkyl esters, fumaric acid, itaconic acid, crotonic acid, and cinnamic acid. In the graft copolymer, the total content of other structural units copolymerized in the main chain is preferably 40 mass% or less, more preferably 20 mass% or less, and may be 0 mass% based on all structural units in the main chain of the graft copolymer.

[0067] (Method for producing graft copolymer) In the present invention, the method for producing the graft copolymer is not particularly limited as long as it can produce a graft copolymer having a structural unit represented by the general formula (I).When producing a graft copolymer having a structural unit represented by the general formula (I), for example, a method for producing a graft copolymer by copolymerizing a monomer represented by the following general formula (Ia) and a polymerizable oligomer (macromonomer) consisting of the polymer chain and a group having an ethylenically unsaturated double bond at its terminal as copolymerization components is included. If necessary, other monomers may also be used to produce the graft copolymer by known polymerization means.

[0068] [ka] (In general formula (Ia), R 1 , A and Q are the same as in general formula (I).

[0069] In addition, when producing a graft copolymer having a constitutional unit represented by the general formula (I), a polymer chain may be introduced by using a polymer chain containing a reactive group capable of reacting with a reactive group contained in the copolymer after a copolymer is formed by addition polymerization of a monomer represented by the general formula (Ia) and other ethylenically unsaturated monomers.Specifically, for example, a copolymer having a substituent such as an alkoxy group, a hydroxyl group, a carboxyl group, an amino group, an epoxy group, an isocyanate group, or a hydrogen bond forming group may be synthesized, and then a polymer chain containing a functional group reactive with the substituent may be reacted to introduce the polymer chain. For example, a polymer chain can be introduced by reacting a polymer chain having a carboxyl group at its terminal with a copolymer having a glycidyl group in its side chain, or by reacting a polymer chain having a hydroxyl group at its terminal with a copolymer having an isocyanate group in its side chain. In the polymerization, additives generally used in polymerization, such as a polymerization initiator, a dispersion stabilizer, and a chain transfer agent, may be used.

[0070] {Block copolymer} The block copolymer used in the present invention has an A block that contains a constitutional unit represented by the above general formula (I), which functions as an adsorption site for a colorant. The block copolymer used in the present invention preferably further has a B block that functions as a solvent affinity site.

[0071] (A Block) In the A block, the constitutional unit represented by the general formula (I) is the same as described above, and therefore the explanation thereof will be omitted here. In the A block, the constitutional unit represented by general formula (I) may be composed of one type, or may contain two or more types of constitutional units.

[0072] In the A block, other structural units may be contained in addition to the structural unit represented by the general formula (I) as long as the effect of the present invention is not impaired. As the other structural units, ethylenically unsaturated monomers copolymerizable with the ethylenically unsaturated monomers from which the structural units represented by the general formula (I) are derived can be appropriately selected and copolymerized to introduce the other structural units. Examples of other structural units that may be included in the A block within a range that does not impair the effects of the present invention include structural units represented by general formula (IV) and structural units containing an acidic group different from the structural unit represented by general formula (I). The structural unit represented by the general formula (IV) and the structural unit containing an acidic group different from the structural unit represented by the general formula (I) may be the same as those described in the graft copolymer, and therefore the description thereof will be omitted here. The total content of other structural units contained in the A block is not particularly limited as long as it is within a range in which the effects of the present invention are not impaired. From the standpoint of dispersibility and dispersion stability, however, it is preferably 40 mass % or less, more preferably 20 mass % or less, and may be 0 mass % with respect to all structural units of the A block.

[0073] In other words, from the standpoints of dispersibility and dispersion stability, the content of the structural unit represented by general formula (I) contained in the A block is preferably 60 mass% or more, more preferably 80 mass% or more, and may be 100 mass%, relative to all the structural units of the A block.

[0074] (Block B) In the block copolymer used in the present invention, the B block is a block that functions as a solvent-affinity site. The B block is preferably selected from ethylenically unsaturated monomers copolymerizable with the ethylenically unsaturated monomer that derives the structural unit represented by the general formula (I) according to the solvent so as to have solvent affinity. As a guideline, it is preferable to introduce the B block so that the solubility of the block copolymer at 23°C is 20 (g / 100g solvent) or more in the solvent used in combination.

[0075] In the block copolymer used in the present invention, the B block functioning as a solvent affinity site preferably contains at least one constitutional unit represented by the general formula (IV) above, in order to improve the solvent affinity and the dispersibility and dispersion stability of the colorant. The structural unit represented by the general formula (IV) contained in the B block may be the same as that described in the graft copolymer, and therefore a description thereof will be omitted here.

[0076] In the B block, the constitutional unit represented by the general formula (IV) may be of one type alone or may be of two or more types mixed together. From the viewpoint of dispersibility and dispersion stability of the colorant, the total proportion of the structural units represented by the general formula (IV) in the B block may be 100% by mass relative to all the structural units in the B block. From the viewpoint of dispersibility and dispersion stability of the colorant, the total proportion of the structural units represented by the general formula (IV) in the B block is preferably 40% by mass or more, more preferably 70% by mass or more, relative to all the structural units in the B block.

[0077] Furthermore, it is preferable that the B block contains at least one type of structural unit selected from the group consisting of structural units represented by general formula (V) and structural units represented by general formula (V'), among the structural units represented by general formula (IV), in terms of improving adhesion to the substrate and shortening the development time. The at least one type of structural unit selected from the group consisting of the structural unit represented by general formula (V) and the structural unit represented by general formula (V') contained in the B block may be the same as those described in the graft copolymer, and therefore description thereof will be omitted here.

[0078] In the B block, the structural unit represented by the general formula (V) and before The at least one structural unit selected from the group consisting of structural units represented by the general formula (V') may be of one type alone or a mixture of two or more types. From the viewpoints of improving the adhesion to the substrate and shortening the development time, the structural unit represented by the general formula (V) and before The total proportion of at least one type of structural unit selected from the group consisting of structural units represented by the general formula (V') is preferably 5% by mass or more, more preferably 10% by mass or more, and even more preferably 15% by mass or more, based on all structural units of the B block. before From the viewpoint of solvent resolubility, the total proportion of at least one type of structural unit selected from the group consisting of structural units represented by the general formula (V') is preferably 90 mass % or less, more preferably 80 mass % or less, and even more preferably 70 mass % or less, relative to all structural units of the B block.

[0079] The B block contains a structural unit represented by the general formula (V) and before In addition to the structural unit represented by the general formula (IV) which includes at least one type of structural unit selected from the group consisting of structural units represented by the general formula (V'), other structural units may be included. Examples of other structural units include structural units derived from ethylenically unsaturated monomers that are copolymerizable with the ethylenically unsaturated monomers that derive the structural unit represented by the general formula (IV) above. Examples of monomers from which other structural units are derived include styrenes such as styrene and α-methylstyrene, and vinyl ethers such as phenyl vinyl ether.

[0080] In the B block, the total proportion of the other structural units is preferably 30% by mass or less, and more preferably 10% by mass or less, based on all the structural units of the B block, in terms of the effects of the present invention.

[0081] From the viewpoint of dispersibility and dispersion stability of the colorant, the mass average molecular weight Mw of the B block is preferably 2000 or more, more preferably 3000 or more, even more preferably 4000 or more, and more preferably 15000 or less, even more preferably 12000 or less. Within the above range, a sufficient steric repulsion effect as a dispersant can be maintained, and the above-mentioned action due to the increase in the specific surface area of ​​the solvent-compatible portion of the dispersant can be improved. The mass average molecular weight Mw of only the B block can be measured for a polymer of only the B block in the same manner as for a dispersant described later.

[0082] From the viewpoint of dispersion stability, the acid value of the B block is preferably 10 mgKOH / g or less, more preferably 0 mgKOH / g. The acid value can be measured for a polymer consisting of only the B block in the same manner as the acid value of a dispersant described later. The B block may contain a structural unit containing an acidic group, such as at least one structural unit selected from the group consisting of the structural unit represented by general formula (I) and the structural unit represented by general formula (II), as long as the effects of the present invention are not impaired. From the viewpoint of dispersion stability, however, the total proportion of the structural units containing an acidic group relative to all the structural units of the B block is preferably 5 mass% or less, and more preferably 0 mass%.

[0083] From the viewpoint of dispersion stability, the amine value of the B block is preferably 10 mgKOH / g or less, more preferably 0 mgKOH / g. The amine value of the B block can be measured for a polymer consisting of only the B block in the same manner as the amine value of the polymer chain described above. The B block may contain nitrogen atom-containing structural units as long as the effects of the present invention are not impaired. From the viewpoint of dispersion stability, however, the total proportion of the nitrogen atom-containing structural units relative to all structural units of the B block is preferably 5 mass % or less, and more preferably 0 mass %.

[0084] The B block may be selected so as to function as a solvent affinity site, and may be composed of one type of structural unit or may be composed of two or more types of structural units. When the B block contains two or more types of structural units, the two or more types of structural units may be randomly copolymerized within the B block.

[0085] The bonding order of the block copolymer is not particularly limited as long as it can stably disperse the colorant, but it is preferable that the A block is bonded to one end of the block copolymer from the viewpoints of excellent interaction with the colorant and effective suppression of aggregation between dispersants. An AB type block copolymer, an ABA type block copolymer, or a BAB type block copolymer is preferable, and an AB type block copolymer or a BAB type block copolymer is particularly preferable.

[0086] In the block copolymer, the total content of the A blocks is preferably 3% by mass to 60% by mass, more preferably 6% by mass to 45% by mass, and even more preferably 9% by mass to 35% by mass, based on all structural units of the main chain of the block copolymer. If the total content of the A blocks in the block copolymer is within the above range, the proportion of the portion with affinity for the colorant in the block copolymer becomes appropriate and a decrease in solubility in organic solvents can be suppressed, resulting in good adsorption to the colorant and excellent dispersibility, dispersion stability, and solvent resolubility. In the block copolymer, the content of the constitutional unit represented by the general formula (I) is preferably 3% by mass to 60% by mass, more preferably 6% by mass to 45% by mass, and even more preferably 9% by mass to 35% by mass, based on the total constitutional units of the main chain of the block copolymer. If the content of the constitutional unit represented by the general formula (I) in the block copolymer is within the above range, the proportion of the part with affinity for the colorant in the block copolymer becomes appropriate, and the decrease in solubility in organic solvents can be suppressed, so that the adsorption to the colorant becomes good, and excellent dispersibility, dispersion stability, and solvent resolubility can be obtained.

[0087] On the other hand, in the block copolymer, the total content of the B blocks is preferably 40% by mass or more and 97% by mass or less, more preferably 55% by mass or more and 94% by mass or less, and even more preferably 65% ​​by mass or more and 91% by mass or less, based on all the structural units of the main chain of the block copolymer. If the total content of the B blocks in the block copolymer is within the above range, the proportion of the solvent-compatible portion in the block copolymer becomes appropriate, and a sufficient steric repulsion effect as a dispersant can be maintained, and the effect of the solvent-compatible portion of the dispersant being increased in specific surface area can be improved. The content ratio of the structural unit is calculated from the amount of monomers that derive the structural unit represented by the general formula (I) and the structural unit represented by the general formula (IV) when synthesizing the block copolymer.

[0088] (Method of Producing Block Copolymer) The method for producing the block copolymer is not particularly limited. The block copolymer can be produced by a known method, but among them, it is preferable to produce it by a living polymerization method. This is because chain transfer and deactivation are unlikely to occur, a copolymer with a uniform molecular weight can be produced, and dispersibility and the like can be improved. Examples of living polymerization methods include living anionic polymerization methods such as living radical polymerization and group transfer polymerization, and living cationic polymerization methods. A copolymer can be produced by sequentially polymerizing monomers using these methods. For example, a block A can be produced first, and a structural unit constituting a block B can be polymerized to the block A to produce a block copolymer. In the above production method, the order of polymerization of the block A and the block B can also be reversed. In addition, the block A and the block B can be produced separately, and then the block A and the block B can be coupled.

[0089] {Characteristics of the polymer having a structural unit represented by formula (I)} The mass average molecular weight Mw of the polymer having the constitutional unit represented by the general formula (I) before salt formation is preferably 4000 or more, more preferably 5000 or more, and even more preferably 6000 or more, from the viewpoint of dispersibility and dispersion stability, while being preferably 50000 or less, more preferably 30000 or less, from the viewpoint of solvent resolubility. In addition, the ratio of the mass average molecular weight Mw to the number average molecular weight Mn (Mw / Mn) of the graft copolymer dispersant is preferably 4.0 or less, more preferably 3.5 or less, and even more preferably 3.0 or less, from the viewpoint of dispersion stability. In addition, the ratio of the mass average molecular weight Mw to the number average molecular weight Mn (Mw / Mn) of the block copolymer dispersant is preferably 1.8 or less, more preferably 1.6 or less, and even more preferably 1.4 or less, from the viewpoint of dispersion stability. In the present invention, the mass average molecular weight Mw and the number average molecular weight Mn are values ​​measured by GPC (gel permeation chromatography). The measurements were performed using HLC-8120GPC manufactured by Tosoh Corporation, N-methylpyrrolidone containing 0.01 mol / L lithium bromide as the elution solvent, polystyrene standards for calibration curve Mw 377400, 210500, 96000, 50400, 20650, 10850, 5460, 2930, 1300, 580 (all of which are Easi PS-2 series manufactured by Polymer Laboratories) and Mw 1090000 (manufactured by Tosoh Corporation), and two TSK-GEL ALPHA-M columns (manufactured by Tosoh Corporation).

[0090] From the viewpoint of dispersion stability, the acid value of the polymer having a structural unit represented by the general formula (I) before salt formation is preferably 20 mgKOH / g or more, more preferably 30 mgKOH / g or more, even more preferably 40 mgKOH / g or more, and even more preferably 60 mgKOH / g or more. On the other hand, from the viewpoint of solvent re-solubility, the acid value of at least one of the graft copolymer and the block copolymer is preferably 250 mgKOH / g or less, more preferably 180 mgKOH / g or less, even more preferably 160 mgKOH / g or less, and even more preferably 120 mgKOH / g or less. The acid value of the dispersant represents the mass (mg) of potassium hydroxide required to neutralize the acidic components contained in 1 g of the solid content of the copolymer, and is a value measured by the method described in JIS K 0070:1992.

[0091] [Salt-type polymer] The salt type polymer used as a dispersant in the present invention is a salt type polymer in which at least a part of the acidic groups contained in a polymer having a structural unit represented by the general formula (I) forms a salt with one or more compounds (B) selected from the group consisting of tertiary amino group-containing basic compounds and basic heterocyclic compounds.

[0092] (Compound (B)) The compound (B) used as a modifier for forming a salt with at least a portion of the acidic groups contained in the general formula (I) is at least one selected from the group consisting of tertiary amino group-containing basic compounds and basic heterocyclic compounds. Compound (B) is a basic compound because it forms a salt with an acidic group, and the first stage acid dissociation constant (pKa) of compound (B) is 7.5 or more, preferably 8.5 or more, more preferably 9.5 or more, and even more preferably 10.5 or more from the viewpoints of dispersibility, dispersion stability, and solvent resolubility. On the other hand, the upper limit of the acid dissociation constant is not particularly limited as long as the effect of the present invention is not impaired, but may be 30 or less. Here, pKa is the value of the acid dissociation constant in water at 25°C. In the present invention, the acid dissociation constant can be measured by the alkali titration method described in pages 215 to 217 of Jikken Kagaku Koza (Experimental Chemistry Course), 2nd Edition, published by Maruzen Co., Ltd.

[0093] Among the compounds (B), the tertiary amino group-containing basic compound contains a tertiary amino group, and may further have other functional groups as long as it is a basic compound. Examples of the other functional groups include a hydroxyl group, a (meth)acryloyloxy group, a (meth)acrylamide group, an amide group, and an ether group. Examples of the tertiary amino group-containing basic compound include dimethylbenzylamine (pKa: 9), triethylamine (pKa: 10.8), tributylamine (pKa: 10), bis(2-dimethylaminoethyl)ether (pKa: 9.1), N,N,N',N'-tetramethylpropanediamine (pKa: 9.9), N,N,N',N'-tetramethyl-1,6-hexanediamine (pKa: 10.1), N,N,N',N",N"-pentamethyldiethyl ... triamine (pKa: 8.8), 2-(dimethylamino)ethanol (pKa: 9.3), tetramethylethylenediamine (pKa: 8.3), N,N,N',N',N"-pentamethyldipropylenetriamine (pKa: 9.9), N,N-dimethylcyclohexylamine (pKa: 10.7), N-[3-(dimethylamino)propyl]acrylamide (pKa: 10.4), and dimethylaminoethyl methacrylate (pKa: 8.2). Examples of basic heterocyclic compounds include 1,8-diazabicyclo[5.4.0]undecene-7 (pKa: 12.5), 1,5-diazabicyclo[4.3.0]nonene-5 (pKa: 12.7), 1,5,7-triazabicyclo[4.4.0]dec-5-ene (pKa: 14.7), 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene (pKa: 14.4), 2-methylimidazole (pKa: 7.8), 1-isobutyl-2-methylimidazole (pKa: 7.8), and triethylenediamine (pKa: 8.8). From the viewpoints of dispersion stability, brightness, contrast, and solvent re-dissolubility, it is preferable to use one or more selected from the group consisting of 1,8-diazabicyclo[5.4.0]undecene-7 (pKa: 12.5), 1,5-diazabicyclo[4.3.0]nonene-5 (pKa: 12.7), 1,5,7-triazabicyclo[4.4.0]dec-5-ene (pKa: 14.7), and 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene (pKa: 14.4). In addition, from the viewpoint of improving the curability of the coating film and improving the chipping resistance of the resist coating film during alkaline development, tertiary amino group-containing basic compounds and basic heterocyclic compounds having a polymerizable functional group such as an ethylenically unsaturated double bond, such as N-[3-(dimethylamino)propyl]acrylamide and dimethylaminoethyl methacrylate, are also preferred.

[0094] From the viewpoints of dispersibility and dispersion stability, the compound (B) preferably has a molecular weight of 800 or less, more preferably 650 or less, even more preferably 500 or less, and even more preferably 350 or less. On the other hand, from the viewpoint of heat resistance, the compound (B) preferably has a molecular weight of 60 or more.

[0095] In the salt-type polymer, the content of the compound (B) is a salt formed with the terminal acidic group of the structural unit represented by the general formula (I), so that the total of at least one selected from the compounds (B) is preferably 0.01 molar equivalents or more, more preferably 0.05 molar equivalents or more, even more preferably 0.1 molar equivalents or more, and particularly preferably 0.2 molar equivalents or more, relative to the terminal acidic group of the structural unit represented by the general formula (I). When the content is equal to or more than the above lower limit, the effect of improving the colorant dispersibility, contrast, substrate adhesion, and brightness due to salt formation is easily obtained. Similarly, it is preferably 1 molar equivalent or less, more preferably 0.8 molar equivalents or less, even more preferably 0.7 molar equivalents or less, and particularly preferably 0.6 molar equivalents or less. When the content is equal to or less than the above upper limit, it can be excellent in alkali developability and solvent resolubility. The at least one selected from the group consisting of the compounds (B) may be used alone or in combination of two or more. When two or more types are combined, the total content is preferably within the above range.

[0096] Examples of a method for preparing the salt-type polymer include a method in which at least one kind selected from the group consisting of the compounds (B) is added to a solvent in which a polymer having a structural unit represented by the general formula (I) before salt formation is dissolved or dispersed, followed by stirring and, if necessary, heating. The fact that the terminal acidic group of the structural unit of the polymer represented by the general formula (I) forms a salt with at least one selected from the group consisting of the compounds (B) and the ratio thereof can be confirmed by a known method such as NMR.

[0097] In the present invention, the content ratio and structure of each constituent unit of the dispersant can be determined using various mass analyses, NMR, etc. In addition, the dispersant can be decomposed by pyrolysis or the like as necessary, and the obtained decomposition product can be determined using high performance liquid chromatography, a gas chromatograph mass spectrometer, NMR, elemental analysis, XPS / ESCA, TOF-SIMS, etc.

[0098] The dispersant according to the present invention is a salt-type polymer in which at least a portion of the acidic groups contained in a polymer having a structural unit represented by general formula (I) forms a salt with one or more compounds (B) selected from the group consisting of tertiary amino group-containing basic compounds and basic heterocyclic compounds. In the colorant dispersion liquid according to the present invention, the dispersant contains at least a salt-type polymer in which at least a part of the acidic groups contained in the general formula (I) of the polymer having a structural unit represented by the general formula (I) forms a salt with one or more compounds (B) selected from the group consisting of tertiary amino group-containing basic compounds and basic heterocyclic compounds, but may contain other dispersants as long as the effects of the present invention are not impaired. For example, known dispersants can be appropriately selected and used as the other dispersants. In the dispersant used in the colorant dispersion liquid according to the present invention, the content of the salt type copolymer is preferably 60% by mass or more, more preferably 70% by mass or more, even more preferably 80% by mass or more, even more preferably 90% by mass or more, and may be 100% by mass.

[0099] In the colorant dispersion liquid according to the present invention, at least the salt type copolymer is used as a dispersant, and the content of the dispersant is appropriately selected depending on the type of colorant used and further the solid content concentration in the colored curable composition described later. The content of the dispersant is preferably 3% by mass or more and 60% by mass or less, more preferably 5% by mass or more and 45% by mass or less, based on the total solid content in the colorant dispersion liquid. If it is equal to or more than the lower limit, the dispersibility and dispersion stability of the colorant are excellent, and the storage stability of the colored curable composition is excellent. If it is equal to or less than the upper limit, the development residue is good. In the present invention, the solid content refers to everything other than the above-mentioned solvent, including monomers dissolved in the solvent.

[0100] <Coloring material> In the present invention, the coloring material is not particularly limited as long as it can produce a desired color when a colored layer of a color filter is formed, and various organic pigments, inorganic pigments, dispersible dyes, dye salt compounds, etc. can be used alone or in combination of two or more kinds. Among them, organic pigments are preferably used because they have high color development and high heat resistance. Examples of organic pigments include compounds classified as pigments in the Color Index (CI; published by The Society of Dyers and Colourists), specifically, those assigned the following Color Index (CI) numbers.

[0101] CI Pigment Yellow 1, 1:1, 2, 3, 4, 5, 6, 9, 10, 12, 13, 14, 15, 16, 17, 20, 24, 31, 32, 34, 35, 35:1, 36, 36:1, 37, 37:1, 40, 41, 42, 43, 48, 53, 55, 60, 61, 62, 62:1, 63, 65, 71, 73, 74, 75, 81, 83, 87, 93, 94, 95, 97, 98, 100, 101, 104, 105, 106, 108, 109, 110, 111, 113 , 114, 116, 117, 119, 120, 126, 127, 127:1, 128, 129, 133, 134, 136, 138, 139, 142, 147, 148, 150, 151, 152, 153, 154, 155, 156, 157, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 168, 173, 175, 185, 194, 211, 214, 215, 231, and pigments derived from CI Pigment Yellow 150; CI Pigment Orange 1, 5, 13, 14, 16, 17, 24, 34, 36, 38, 40, 43, 46, 49, 51, 61, 63, 64, 71, 73; CI Pigment Violet 1, 19, 23, 29, 32, 36, 38; CI Pigment Red 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 14, 15, 16, 17, 18, 19, 21, 22, 23, 30, 31, 32, 37, 38, 40, 41, 42, 47, 48, 48:1, 48:2, 48:3, 48:4, 49, 49:1, 49:2, 50:1, 52:1, 53:1, 57, 57 :1, 57:2, 58:2, 58:4, 60, 60:1, 63, 63:1, 63:2, 64, 64:1, 68, 69, 81:1, 83, 88, 90:1, 97, 101, 102, 104, 105, 106, 108, 109, 112, 113, 114, 122, 123, 144, 146, 147, 149, 150, 151, 166, 168, 170, 171, 172, 173, 174, 175, 176, 177, 178, 179, 180, 181, 184, 185, 187, 188, 190, 193, 194, 200, 202, 206, 207, 208, 209, 210, 214, 215, 216, 220, 221, 224, 226, 230, 231, 232, 233, 235, 236, 237, 238, 239, 242, 243, 245, 247, 249, 250, 251, 253, 254, 255, 256, 257, 258, 259, 260, 262, 263, 264, 265, 266, 267, 268, 269, 270, 271, 272, 273, 274, 275, 276, 291; CI Pigment Blue 1, 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 60, 61, 79, 80; CI Pigment Green 1, 2, 4, 7, 8, 10, 13, 14, 15, 17, 18, 19, 26, 36, 45, 48, 50, 51, 54, 55, 58, 59, 62, 63; CI Pigment Brown 23, 25; CI Pigment Black 1, 7.

[0102] Specific examples of the inorganic pigment include titanium oxide, barium sulfate, calcium carbonate, zinc oxide, lead sulfate, yellow lead, zinc yellow, red iron oxide (red iron (III)), cadmium red, ultramarine, Prussian blue, chromium oxide green, cobalt green, amber, titanium black, synthetic iron black, and carbon black.

[0103] For example, when the colorant dispersion according to the present invention is used as a colored curable composition to be described later to form a light-shielding layer pattern on a color filter substrate, a black pigment having high light-shielding properties is blended into the ink. Examples of the black pigment having high light-shielding properties that can be used include inorganic pigments such as carbon black and iron oxide, and organic pigments such as cyanine black.

[0104] The dispersible dyes include dyes which have become dispersible by being given various substituents or by being used in combination with a solvent having low solubility. The dye salt-forming compound refers to a compound in which a dye forms a salt with a counter ion, and examples of such compounds include a salt-forming compound between a basic dye and an acid, and a salt-forming compound between an acidic dye and a base. It also includes lake pigments in which a solvent-soluble dye is made insoluble in a solvent using a known lake (salting) technique. In the present invention, by using a colorant containing at least one selected from the group consisting of dyes and dye salt-forming compounds in combination with the dispersant of the present invention, the dispersibility and dispersion stability of the colorant can be improved.

[0105] The dye can be appropriately selected from conventionally known dyes, such as azo dyes, metal complex azo dyes, anthraquinone dyes, triphenylmethane dyes, xanthene dyes, coumarin dyes, cyanine dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, and phthalocyanine dyes. As a guideline, if the amount of dye dissolved in 10 g of a solvent (or mixed solvent) is 10 mg or less, it can be determined that the dye is dispersible in the solvent (or mixed solvent).

[0106] Among them, when the coloring material contains at least one selected from the group consisting of diketopyrrolopyrrole pigment, anthraquinone pigment, quinophthalone pigment, copper phthalocyanine pigment, zinc phthalocyanine pigment, aluminum phthalocyanine pigment, dioxazine pigment, azomethine pigment, zinc phthalocyanine dye, triarylmethane dye, quinophthalone dye, coumarin dye, phthalocyanine dye, and salt-forming compounds of these dyes, it is preferable because the use of the dispersant makes it possible to form a colored layer with high brightness. Also, among them, the coloring material preferably contains at least one selected from the group consisting of diketopyrrolopyrrole pigment, quinophthalone pigment, copper phthalocyanine pigment, zinc phthalocyanine pigment, dioxazine pigment, zinc phthalocyanine dye, triarylmethane dye, quinophthalone dye, and salt-forming compounds of these dyes.

[0107] Examples of the diketopyrrolopyrrole pigment include CI Pigment Red 254, 255, 264, 272, and 291, and diketopyrrolopyrrole pigments represented by the following general formula (i). Among them, CI Pigment Red 254, 272, and 291, and diketopyrrolopyrrole pigments represented by the following general formula (i) are preferably used. 21 and R 22 and each of which is a 4-bromophenyl group is preferable.

[0108] [ka] (In general formula (i), R 21 and R 22 are each independently a 4-chlorophenyl group or a 4-bromophenyl group.

[0109] An example of an anthraquinone pigment is CI Pigment Red 177. Examples of quinophthalone pigments include CI Pigment Yellow 138 and 231. Examples of copper phthalocyanine pigments include CI Pigment Blue 15, 15:1, 15:2, 15:3, 15:4, 15:5, 15:6, CI Pigment Green 7, and 36, and among these, CI Pigment Blue 15:6 is preferred. Examples of zinc phthalocyanine pigments include CI Pigment Green 58 and 59. Examples of aluminum phthalocyanine pigments include CI Pigment Green 62 and 63. Dioxazine pigments include CI Pigment Violet 23 and the like. Examples of azomethine pigments include CI Pigment Yellow 150. Examples of quinophthalone dyes include CI Disperse Yellow 54, 64, 67, 134, 149, and 160, and CI Solvent Yellow 114 and 157. Of these, CI Disperse Yellow 54 is preferred. Triarylmethane dyes include CI Basic Red 9, CI Basic Blue 1, 7, and the like. Examples of the phthalocyanine dye include CI Basic Blue 140 and zinc phthalocyanine dyes in which the central metal of CI Basic Blue 140 is replaced with zinc. Furthermore, a coloring material represented by the following general formula (1) is also preferably used in combination with the dispersant of the present invention from the viewpoint of luminance.

[0110] [ka] (In the general formula (1), A represents an a-valent organic group in which the carbon atom directly bonded to N does not have a π bond, and the organic group represents an aliphatic hydrocarbon group having a saturated aliphatic hydrocarbon group at least at the end directly bonded to N, or an aromatic group having the aliphatic hydrocarbon group, and may contain a heteroatom in the carbon chain. c- R represents a polyacid anion having a valence of c. i ~R veach independently represents a hydrogen atom, an optionally substituted alkyl group, or an optionally substituted aryl group; R ii and R iii , R iv and R v may be bonded to form a ring structure. vi and R vii each independently represents an alkyl group which may have a substituent, an alkoxy group which may have a substituent, a halogen atom or a cyano group. 1 represents a divalent aromatic group which may have a substituent. i ~R vii and Ar 1 may be the same or different. a and c represent integers of 2 or more, and b and d represent integers of 1 or more. e is 0 or 1, and when e is 0, no bond exists. f and g represent integers of 0 or more and 4 or less, and f+e and g+e are 0 or more and 4 or less. Multiple e, f, and g may be the same or different.

[0111] For the explanation of each symbol of the coloring material represented by the general formula (1), the explanation of the symbols in the corresponding parts of the general formula (I) described in WO 2018 / 003706 can be referred to. Examples of partial structures and other structures of the coloring material represented by the general formula (1) include structures described in WO 2018 / 003706, WO 2012 / 144521, etc.

[0112] The colorant used in the present invention is preferably at least one selected from the group consisting of CI Pigment Red 177, 254, 291, CI Pigment Yellow 138, 150, 231, CI Pigment Blue 15:6, CI Pigment Green 58, 59, 62, 63, CI Pigment Violet 23, and the colorant represented by the general formula (1), in that it is possible to form a colored layer with high brightness and a wide color gamut.

[0113] The average primary particle size of the colorant used in the present invention is not particularly limited as long as it can produce a desired color when used as a colored layer of a color filter, and although it varies depending on the type of colorant used, it is preferably within the range of 10 to 100 nm, and more preferably 15 to 60 nm. By having the average primary particle size of the colorant within the above range, a display device equipped with a color filter manufactured using the colorant dispersion liquid of the present invention can be made to have high brightness, high contrast, and high quality.

[0114] The average dispersed particle size of the colorant in the colorant dispersion liquid differs depending on the type of colorant used, but is preferably within the range of 10 to 100 nm, and more preferably within the range of 15 to 60 nm. The average dispersed particle size of the colorant in the colorant dispersion is the dispersed particle size of the colorant particles dispersed in a dispersion medium containing at least a solvent, and is measured by a laser light scattering particle size distribution meter. The particle size can be measured by diluting the colorant dispersion with the solvent used in the colorant dispersion to a concentration that can be measured by the laser light scattering particle size distribution meter (for example, 1000 times), and measuring the particle size at 23°C by dynamic light scattering using a laser light scattering particle size distribution meter (for example, Nanotrack particle size distribution measuring device UPA-EX150 manufactured by Nikkiso Co., Ltd.). The average dispersed particle size here is the volume average particle size.

[0115] The coloring material used in the present invention can be produced by a known method such as a recrystallization method, a solvent salt milling method, etc. Also, commercially available coloring materials may be used after being subjected to a micronization treatment.

[0116] In the colorant dispersion liquid according to the present invention, the content of the colorant is not particularly limited. From the viewpoint of dispersibility and dispersion stability, the content of the colorant is preferably 5% by mass or more and 80% by mass or less, more preferably 8% by mass or more and 70% by mass or less, based on the total amount of solids in the colorant dispersion liquid. In particular, when forming a coating film or a colored layer having a high colorant concentration, it is preferable to mix the colorant in an amount of 30% by mass or more and 80% by mass or less, more preferably 40% by mass or more and 75% by mass or less, based on the total solid content in the colorant dispersion.

[0117] <Solvent> The solvent used in the present invention is not particularly limited as long as it is an organic solvent that does not react with each component in the colorant dispersion liquid and can dissolve or disperse them. The solvent can be used alone or in combination of two or more kinds. Specific examples of the solvent include alcohol-based solvents such as methyl alcohol, ethyl alcohol, n-propyl alcohol, i-propyl alcohol, methoxy alcohol, and ethoxy alcohol; carbitol-based solvents such as methoxyethoxyethanol and ethoxyethoxyethanol; ethyl acetate, butyl acetate, methyl methoxypropionate, ethyl methoxypropionate, ethyl ethoxypropionate, ethyl lactate, methyl hydroxypropionate, ethyl hydroxypropionate, n-butyl acetate, and isobutyl acetate. ester solvents such as butyl acetate, isobutyl butyrate, n-butyl butyrate, ethyl lactate, and cyclohexanol acetate; ketone solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, and 2-heptanone; glycol ether acetate solvents such as methoxyethyl acetate, propylene glycol monomethyl ether acetate, 3-methoxy-3-methyl-1-butyl acetate, 3-methoxybutyl acetate, and ethoxyethyl acetate; and methoxyethoxyethyl acetate. carbitol acetate solvents such as ethoxyethoxyethyl acetate and butyl carbitol acetate (BCA); diacetates such as propylene glycol diacetate and 1,3-butylene glycol diacetate; glycol ether solvents such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, diethylene glycol monoethyl ether, diethylene glycol diethyl ether, propylene glycol monomethyl ether and dipropylene glycol dimethyl ether; aprotic amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide and N-methylpyrrolidone; lactone solvents such as γ-butyrolactone; cyclic ether solvents such as tetrahydrofuran; unsaturated hydrocarbon solvents such as benzene, toluene, xylene and naphthalene; saturated hydrocarbon solvents such as n-heptane, n-hexane and n-octane; and aromatic hydrocarbons such as toluene and xylene.Among these solvents, glycol ether acetate solvents, carbitol acetate solvents, glycol ether solvents, and ester solvents are preferably used in terms of the solubility of other components.Among these, the solvent used in the present invention is preferably one or more selected from the group consisting of propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, butyl carbitol acetate (BCA), 3-methoxy-3-methyl-1-butyl acetate, ethyl ethoxypropionate, ethyl lactate, and 3-methoxybutyl acetate in terms of the solubility of other components and coating suitability.

[0118] In the colorant dispersion liquid according to the present invention, the above-mentioned solvent is preferably in the range of 55% by mass to 95% by mass, more preferably in the range of 65% by mass to 90% by mass, and more preferably in the range of 70% by mass to 88% by mass, based on the total amount of the colorant dispersion liquid including the solvent. If the amount of the solvent is too small, the viscosity increases and the dispersibility tends to decrease. If the amount of the solvent is too large, the colorant concentration decreases, and it may be difficult to achieve the target chromaticity coordinates.

[0119] <Other ingredients> The colorant dispersion liquid according to the present invention may further contain a dispersion-assisting resin and other components, if necessary, so long as the effects of the present invention are not impaired. Examples of the dispersion-assisting resin include alkali-soluble resins exemplified in the colored curable composition described below. The steric hindrance of the alkali-soluble resin makes it difficult for colorant particles to come into contact with each other, thereby stabilizing the dispersion, and the dispersion stabilizing effect may have the effect of reducing the amount of dispersant. Examples of other components include surfactants for improving wettability, silane coupling agents for improving adhesion, defoamers, anti-cision agents, antioxidants, anti-aggregation agents, and ultraviolet absorbers.

[0120] The colorant dispersion according to the present invention is used as a preparatory product for preparing a colored curable composition described later. That is, the colorant dispersion is a colorant dispersion having a high ratio of (mass of colorant components in the composition) / (mass of solids other than colorant components in the composition) that is preparatoryly prepared in a stage prior to the preparation of a colored curable composition described later. Specifically, the ratio of (mass of colorant components in the composition) / (mass of solids other than colorant components in the composition) is usually 1.0 or more. By mixing the colorant dispersion with each of the components described later, a colored curable composition having excellent dispersibility can be prepared.

[0121] <Method of manufacturing colorant dispersion liquid> In the present invention, the method for producing the colorant dispersion liquid is not particularly limited as long as it is a method that can obtain a colorant dispersion liquid in which the colorant is dispersed in the solvent by the dispersant. In view of excellent dispersibility and dispersion stability of the colorant, the method for producing the colorant dispersion liquid according to the present invention includes a step of preparing the dispersant, and a step of dispersing the colorant in a solvent in the presence of the dispersant.

[0122] In the above-mentioned production method, the coloring material can be dispersed using a conventionally known dispersing machine. Specific examples of the dispersing machine include roll mills such as two-roll and three-roll, ball mills such as ball mills and vibration ball mills, paint conditioners, and bead mills such as continuous disk bead mills and continuous annular bead mills. As a preferred dispersion condition for the bead mill, the diameter of the beads used is preferably 0.03 to 3.0 mm, more preferably 0.05 to 2.0 mm.

[0123] Specifically, preliminary dispersion is performed using zirconia beads having a relatively large bead diameter of 2.0 mm, and then main dispersion is performed using zirconia beads having a relatively small bead diameter of 0.1 mm. After dispersion, it is preferable to filter the mixture through a 0.5 to 2 μm filter.

[0124] <Application> The colorant dispersion liquid and the dispersant according to the present invention can prepare a colored curable composition that simultaneously satisfies excellent dispersion stability, brightness, contrast, substrate adhesion, and solvent resolubility, and therefore can be suitably used, among others, for color filter applications. Moreover, the colorant dispersion liquid and the dispersant according to the present invention can also be used in a colored resin composition that does not require a photosensitive component, or in a thermosetting colored resin composition. The colorant dispersion and dispersant according to the present invention are used in various applications requiring excellent dispersion stability of fine colorant, including inkjet inks, printing inks, writing instruments, cosmetics, etc.

[0125] II. Colored curable composition The colored curable composition according to the present invention is characterized by containing a colorant, the dispersant according to the present invention, a polymerizable compound, an initiator, and a solvent. The colored curable composition of the present invention can simultaneously satisfy excellent dispersion stability, brightness, contrast, substrate adhesion, and solvent resolubility by using the dispersant of the present invention.

[0126] The colored curable composition of the present invention contains at least a colorant, a dispersant, a polymerizable compound, an initiator, and a solvent, and may further contain other components within a range that does not impair the effects of the present invention. Hereinafter, each component contained in the colored curable composition of the present invention will be described, but the dispersant, colorant, and solvent are the same as those described in the colorant dispersion liquid according to the present invention, so that the description here will be omitted.

[0127] <Polymerizable compound> The polymerizable compound is not particularly limited as long as it can be polymerized by the initiator described later, and for example, a photopolymerizable compound or a thermally polymerizable compound can be used. As the thermally polymerizable compound, a compound having a thermally polymerizable functional group such as a carboxyl group, an amino group, an epoxy group, a hydroxyl group, a glycidyl group, an isocyanate group, and an alkoxyl group in the molecule can be used. In addition, a compound having an ethylenically unsaturated group can be used as a thermally polymerizable compound by combining it with a thermal radical polymerization initiator. As the polymerizable compound, a photopolymerizable compound that can be polymerized by a photoinitiator described later is preferable, since a pattern can be easily formed by the photolithography method using an existing process.

[0128] The photopolymerizable compound used in the colored curable composition is not particularly limited as long as it is polymerizable by a photoinitiator described later. Usually, a compound having two or more ethylenically unsaturated double bonds is used, and in particular, a polyfunctional (meth)acrylate having two or more acryloyl groups or methacryloyl groups is preferably used. Such a polyfunctional (meth)acrylate may be appropriately selected from conventionally known ones, and specific examples thereof include those described in JP-A-2013-029832.

[0129] These photopolymerizable compounds may be used alone or in combination of two or more. In addition, when the colored curable composition of the present invention is required to have excellent photocurability (high sensitivity), the photopolymerizable compound is preferably one having three (trifunctional) or more polymerizable double bonds, and poly(meth)acrylates of polyhydric alcohols having a valence of three or more and dicarboxylic acid modified products thereof are preferable, and specifically, trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, succinic acid modified product of pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, succinic acid modified product of dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, etc. are preferable.

[0130] The content of the polymerizable compound in the colored curable composition is preferably 5% by mass or more and 60% by mass or less, more preferably 10% by mass or more and 50% by mass or less, and even more preferably 20% by mass or more and 40% by mass or less, based on the total solid content of the colored curable composition. When the content of the polymerizable compound is equal to or more than the lower limit, poor curing can be suppressed, so that the exposed part can be suppressed from dissolving during development, and when the content of the polymerizable compound is equal to or less than the upper limit, poor development can be suppressed and heat shrinkage can be suppressed, so that micro-wrinkles are unlikely to occur on the entire surface of the colored layer.

[0131] <Initiator> The initiator used in the colored curable composition of the present invention is not particularly limited, and one or a combination of two or more of various conventionally known initiators can be used. Examples of the initiator include polymerization initiators such as thermal polymerization initiators and photopolymerization initiators, and specific examples include those described in JP2013-029832A.

[0132] Examples of the photoinitiator include aromatic ketones, benzoin ethers, halomethyloxadiazole compounds, α-aminoketones, biimidazoles, N,N-dimethylaminobenzophenone, halomethyl-S-triazine compounds, and thioxanthone.Specific examples of the photoinitiator include aromatic ketones such as benzophenone, 4,4'-bisdiethylaminobenzophenone, and 4-methoxy-4'-dimethylaminobenzophenone, benzoin ethers such as benzoin methyl ether, benzoin such as ethylbenzoin, biimidazoles such as 2-(o-chlorophenyl)-4,5-phenylimidazole dimer, halomethyloxadiazole compounds such as 2-trichloromethyl-5-(p-methoxystyryl)-1,3,4-oxadiazole, and 2-(4-butoxynaphthalene)-2-methylphenyl ether. Halomethyl-S-triazine compounds such as 4,6-bis-trichloromethyl-S-triazine, 2,2-dimethoxy-1,2-diphenylethan-1-one, 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropanone, 1,2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butanone, 1-hydroxy-cyclohexyl-phenyl ketone, benzyl, benzoylbenzoic acid, methyl benzoylbenzoate, 4-benzoyl-4'-methyldiphenyl sulfide, benzyl methyl ketal, dimethylaminobenzoate, p-dimethylaminobenzoic acid isoamyl, 2-n-butoxyethyl-4-dimethylaminobenzoate, 2-chlorothioxanthone, 2,4-diethylthioxanthone, 2,4-dimethylthioxanthone, isopropylthioxanthone, 4-benzoyl-methyldiphenyl sulfide, 1-hydroxy-cyclohexyl-phenyl ketone, 2-benzyl-2-(dimethylamino)-1-[4-(4-morpholinyl)phenyl]-1-butoxyethyl butanone, 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]-1-butanone, α-dimethoxy-α-phenylacetophenone, phenylbis(2,4,6-trimethylbenzoyl)phosphine oxide, 2-methyl-1-[4-(methylthio)phenyl]-2-(4-morpholinyl)-1-propanone, 1-(9,9-dibutyl-9H-fluoren-2-yl)-2-methyl-2-(4-morpholinyl)-1-propanone, and the like. Among them, 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one, 2-benzyl-2-(dimethylamino)-1-(4-morpholinophenyl)-1-butanone, 4,4'-bis(diethylamino)benzophenone, and diethylthioxanthone are preferably used.Furthermore, it is preferable to combine an α-aminoacetophenone initiator such as 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one with a thioxanthone initiator such as diethylthioxanthone, in terms of adjusting sensitivity, suppressing water stains, and improving development resistance. When an α-aminoacetophenone initiator and a thioxanthone initiator are used, the total content of these initiators is 5% by mass based on the total solid content of the colored curable composition. % more than 15 mass %below It is preferable that the amount of the initiator is 15% by mass or less, since the amount of sublimation during the manufacturing process is reduced. If the amount of the initiator is 5% by mass or more, water stains, etc. Suppress , and the development resistance is improved.

[0133] In the present invention, the photoinitiator preferably contains an oxime ester photoinitiator, because it can improve the sensitivity. In addition, by using an oxime ester photoinitiator, the variation in the line width in the plane is easily suppressed when forming a fine line pattern. Furthermore, by using an oxime ester photoinitiator, the residual film rate is improved, and the effect of suppressing the occurrence of water stains tends to be enhanced. As the oxime ester-based photoinitiator, from the viewpoint of reducing contamination of the colored curable composition and contamination of the device due to decomposition products, among them, those having an aromatic ring are preferable, those having a condensed ring containing an aromatic ring are more preferable, and those having a condensed ring containing a benzene ring and a heterocycle are further preferable. The oxime ester photoinitiator can be appropriately selected from 1,2-octadione-1-[4-(phenylthio)-, 2-(o-benzoyloxime)], ethanone, 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-, 1-(o-acetyloxime), and the oxime ester photoinitiators described in JP-A Nos. 2000-80068, 2001-233842, JP-T Nos. 2010-527339, 2010-527338, and 2013-041153. Commercially available products include Irgacure OXE-01, Adeka Arcles NCI-930, TR-PBG-345, TR-PBG-304 with a carbazole skeleton, Irgacure OXE-02, Adeka Arcles NCI-831, TR-PBG-365, and TR-PBG-3057 with a diphenyl sulfide skeleton (all manufactured by Changzhou Strong Electronic New Materials Co., Ltd.). In particular, it is preferable to use an oxime ester photoinitiator with a diphenyl sulfide skeleton or a fluorene skeleton from the viewpoint of brightness. In addition, it is preferable to use an oxime ester photoinitiator with a carbazole skeleton from the viewpoint of high sensitivity.

[0134] In addition, it is preferable to use a photoinitiator having a tertiary amine structure in combination with an oxime ester photoinitiator in terms of suppressing water stains and improving sensitivity. The photoinitiator having a tertiary amine structure has a tertiary amine structure that is an oxygen quencher in the molecule, so that the radical generated from the initiator is less likely to be deactivated by oxygen, and sensitivity can be improved. Examples of commercially available photoinitiators having the above-mentioned tertiary amine structure include 2-methyl-1-(4-methylthiophenyl)-2-morpholinopropan-1-one (e.g., Irgacure 907, manufactured by BASF), 2-benzyl-2-(dimethylamino)-1-(4-morpholinophenyl)-1-butanone (e.g., Irgacure 369, manufactured by BASF), and 4,4'-bis(diethylamino)benzophenone (e.g., Hi-Cure ABP, manufactured by Kawaguchi Yakuhin). In addition, combining an oxime ester photoinitiator with a thioxanthone photoinitiator is preferable from the viewpoints of adjusting sensitivity, suppressing water stains, and improving development resistance, and combining two or more types of oxime ester photoinitiators with a thioxanthone photoinitiator is preferable from the viewpoints of improving brightness and film remaining rate, making it easier to adjust sensitivity, having a high effect of suppressing the occurrence of water stains, and improving development resistance.

[0135] The content of the initiator in the colored curable composition is preferably 0.1% by mass or more and 15% by mass or less, more preferably 1% by mass or more and 10% by mass or less, based on the total solid content of the colored curable composition. When the content of the initiator is equal to or more than the lower limit, curing proceeds sufficiently, and when the content of the initiator is equal to or less than the upper limit, side reactions can be suppressed and stability over time can be maintained.

[0136] <Other ingredients> The colored curable composition of the present invention may contain a polymer such as an alkali-soluble resin, an antioxidant, and further various additives, if necessary.

[0137] (polymer) As the polymer, when a photolithography process is used to form the colored layer, an alkali-soluble resin that is soluble in an alkali developer is preferably used. In the present invention, since the dispersant has an acidic group, it can also function as an alkali-soluble resin, so that an alkali-soluble resin different from the dispersant is not an essential component even when a photolithography process is used. In the photosensitive color resin composition of the present invention, it is preferable to further contain an alkali-soluble resin different from the dispersant, in order to easily adjust the alkali solubility. The alkali-soluble resin has an acidic group, and can be appropriately selected and used as long as it acts as a binder resin and is soluble in the alkali developer used in forming the pattern. In the present invention, an alkali-soluble resin can be defined as one having an acid value of 30 mgKOH / g or more.

[0138] As the alkali-soluble resin, any conventionally known alkali-soluble resin can be appropriately selected and used. For example, the alkali-soluble resins described in WO2016 / 104493 can be appropriately selected and used. The preferred alkali-soluble resin in the present invention is a resin having an acidic group, usually a carboxy group, and specifically includes acrylic resins such as acrylic copolymers having a carboxy group and styrene-acrylic copolymers having a carboxy group, and epoxy (meth)acrylate resins having a carboxy group. Among these, particularly preferred are those having a carboxy group in the side chain and further having a photopolymerizable functional group such as an ethylenically unsaturated group in the side chain. This is because the film strength of the cured film formed is improved by containing the photopolymerizable functional group. In addition, these acrylic resins such as acrylic copolymers and styrene-acrylic copolymers, and epoxy acrylate resins may be used in a mixture of two or more kinds.

[0139] The content of the alkali-soluble resin used in the colored curable composition is not particularly limited, but is preferably in the range of 1% by mass to 60% by mass, more preferably 5% by mass to 40% by mass, based on the total solid content of the colored curable composition. When the content of the alkali-soluble resin is equal to or more than the lower limit, sufficient alkali developability is easily obtained, and when the content of the alkali-soluble resin is equal to or less than the upper limit, film roughness and pattern chipping during development are easily suppressed. In the present invention, the solid content refers to everything other than the solvent, including monomers dissolved in the solvent.

[0140] In addition, the colored curable composition according to the present invention may contain, as the polymer, a thermosetting polymer such as a phenol resin, a urea resin, a diallyl phthalate resin, a melamine resin, a guanamine resin, an unsaturated polyester resin, a polyurethane resin, an epoxy resin, an aminoalkyd resin, a melamine-urea co-condensation resin, a silicon resin, or a polysiloxane resin.

[0141] The polymers may be used alone or in combination of two or more. The content of the polymer in the colored curable composition is not particularly limited, but is preferably 1% by mass or more and 60% by mass or less, and more preferably 5% by mass or more and 50% by mass or less, based on the total solid content of the colored curable composition. When the content of the polymer is equal to or more than the lower limit, the decrease in film strength can be suppressed, and when the content of the polymer is equal to or less than the upper limit, components other than the polymer can be sufficiently contained.

[0142] (Antioxidants) The colored curable composition of the present invention preferably further contains an antioxidant, since it improves heat resistance, inhibits fading of the coloring material, and improves brightness. The antioxidant may be appropriately selected from conventionally known antioxidants. Specific examples of the antioxidant include hindered phenol-based antioxidants, amine-based antioxidants, phosphorus-based antioxidants, sulfur-based antioxidants, and hydrazine-based antioxidants, and it is preferable to use a hindered phenol-based antioxidant from the viewpoint of heat resistance. A latent antioxidant such as that described in International Publication No. 2014 / 021023 may also be used.

[0143] Examples of the hindered phenol-based antioxidant include pentaerythritol tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate] (trade name :Examples of such compounds include 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)isocyanurate (trade name: Irganox 3114, manufactured by BASF), 2,4,6-tris(4-hydroxy-3,5-di-tert-butylbenzyl)mesitylene (trade name: Irganox 1330, manufactured by BASF), 2,2'-methylenebis(6-tert-butyl-4-methylphenol) (trade name: Sumilizer MDP-S, manufactured by Sumitomo Chemical), 6,6'-thiobis(2-tert-butyl-4-methylphenol) (trade name: Irganox 1081, manufactured by BASF), and 3,5-di-tert-butyl-4-hydroxybenzylphosphonic acid diethyl ester (trade name: Irgamod 195, manufactured by BASF). Among these, pentaerythritol tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate] (trade name) is preferred from the viewpoint of heat resistance and light resistance. : IRGANOX1010, manufactured by BASF) is preferred.

[0144] The colored curable composition of the present invention preferably contains a combination of the oxime ester-based photoinitiator and an antioxidant, since this improves brightness due to a synergistic effect and improves the ability to form a fine line pattern according to the designed mask line width.

[0145] The amount of the antioxidant is preferably 0.1% by mass or more and 10.0% by mass or less, more preferably 0.5% by mass or more and 5.0% by mass or less, based on the total amount of solids in the colored curable composition. If the amount is more than the lower limit, the heat resistance and light resistance are excellent. On the other hand, if the amount is less than the upper limit, the colored curable composition of the present invention can be a highly sensitive photosensitive resin composition.

[0146] When the antioxidant is used in combination with the oxime ester photoinitiator, the amount of the antioxidant is preferably 1 part by mass or more and 250 parts by mass or less, more preferably 3 parts by mass or more and 80 parts by mass or less, and even more preferably 5 parts by mass or more and 45 parts by mass or less, relative to 100 parts by mass of the total amount of the oxime ester photoinitiator. If it is within the above range, the effect of the combination is excellent.

[0147] (Various additives) The colored curable composition of the present invention may contain various additives. Examples of the additives include a polymerization terminator, a chain transfer agent, a leveling agent, a plasticizer, a surfactant, an antifoaming agent, a silane coupling agent, an ultraviolet absorbing agent, and an adhesion promoter. Specific examples of the surfactant and plasticizer include those described in JP2013-029832A.

[0148] Examples of the silane coupling agent include KBM-502, KBM-503, KBE-502, KBE-503, KBM-5103, KBM-903, KBE-903, KBM573, KBM-403, KBE-402, KBE-403, KBM-303, KBM-802, KBM-803, KBE-9007, and X-12-967C (manufactured by Shin-Etsu Silicones Co., Ltd.). Among these, KBM-502, KBM-503, KBE-502, KBE-503, and KBM-5103 having a methacryl group or an acrylic group are preferred from the viewpoint of adhesion to the SiN substrate.

[0149] The content of the silane coupling agent is preferably 0.05% by mass or more and 10.0% by mass or less, and more preferably 0.1% by mass or more and 5.0% by mass or less, based on the total solid content in the colored curable composition. If the content is more than the lower limit and less than the upper limit, the adhesion to the substrate is excellent.

[0150] <Mixing ratio of each component in the colored curable composition> The total content of the coloring materials is preferably 3% by mass or more and 65% by mass or less, more preferably 4% by mass or more and 60% by mass or less, based on the total solid content of the coloring curable composition. If it is equal to or more than the lower limit, the coloring layer when the coloring curable composition is applied to a predetermined film thickness (usually 1.0 to 5.0 μm) has sufficient color density. If it is equal to or less than the upper limit, a coloring layer having excellent storage stability, sufficient hardness, and adhesion to the substrate can be obtained. In particular, when a coloring layer having a high coloring material concentration is formed, the content of the coloring materials is preferably 15% by mass or more and 75% by mass or less, more preferably 25% by mass or more and 70% by mass or less, based on the total solid content of the coloring curable composition. The content of the dispersant is not particularly limited as long as it can uniformly disperse the colorant, but can be used, for example, at a ratio of 1% by mass to 40% by mass with respect to the total solid content of the colored curable composition. Furthermore, it is preferable to mix it at a ratio of 2% by mass to 30% by mass with respect to the total solid content of the colored curable composition, and particularly preferably at a ratio of 3% by mass to 25% by mass with respect to the total solid content of the colored curable composition. If it is equal to or more than the above lower limit, the dispersibility and dispersion stability of the colorant are excellent, and the storage stability of the colored curable composition is more excellent. If it is equal to or less than the above upper limit, the alkali developability is good. In particular, when forming a colored layer with a high colorant concentration, the content of the dispersant is preferably mixed at a ratio of 2% by mass to 25% by mass with respect to the total solid content of the colored curable composition, more preferably 3% by mass to 20% by mass with respect to the total solid content of the colored curable composition. The content of the solvent may be appropriately set within a range that allows the colored layer to be formed with good accuracy. The content of the solvent is preferably within a range of 55% by mass or more and 95% by mass or less, and more preferably within a range of 65% by mass or more and 88% by mass or less, based on the total amount of the colored curable composition including the solvent. By having the content of the solvent within the above range, it is possible to obtain excellent coating properties.

[0151] <Method for producing colored curable composition> The method for producing the colored curable composition of the present invention is not particularly limited, and for example, the colored curable composition can be obtained by adding a polyfunctional monomer, a photoinitiator, and optionally an alkali-soluble resin and other components to the colorant dispersion liquid of the present invention, and mixing them using a known mixing means. Alternatively, the colored curable composition can be obtained by adding a colorant, the dispersant of the present invention, a polyfunctional monomer, a photoinitiator, a solvent, and optionally an alkali-soluble resin and other components, and mixing them using a known mixing means.

[0152] <Application> The colored curable composition according to the present invention can simultaneously satisfy excellent dispersion stability, brightness, contrast, substrate adhesion, and solvent resolubility, and therefore can be suitably used, among others, for color filter applications. The colored curable composition according to the present invention is used in various applications requiring excellent dispersion stability of fine color materials, and is also used as an inkjet ink or a printing ink.

[0153] III. Color Filters The color filter according to the present invention is a color filter comprising at least a substrate and colored layers provided on the substrate, and at least one of the colored layers is a cured product of the colored curable composition according to the present invention.

[0154] The color filter according to the present invention will be described with reference to the drawings. Fig. 1 is a schematic cross-sectional view showing an example of the color filter according to the present invention. According to Fig. 1, the color filter 10 according to the present invention has a substrate 1, a light-shielding portion 2, and a colored layer 3.

[0155] <Colored layer> At least one of the colored layers used in the color filter of the present invention is a colored layer which is a cured product of the colored curable composition of the present invention. The colored layer is usually formed in the opening of the light-shielding part on the substrate, which will be described later, and usually consists of a colored pattern of three or more colors. The arrangement of the colored layers is not particularly limited, and may be, for example, a common arrangement such as a stripe type, a mosaic type, a triangle type, a four-pixel arrangement type, etc. The width, area, etc. of the colored layers may be set arbitrarily. The thickness of the colored layer is appropriately controlled by adjusting the coating method, the solid content concentration and the viscosity of the colored curable composition, etc., but is usually preferably in the range of 1 to 5 μm.

[0156] The colored layer can be formed, for example, by the following method. First, the colored curable composition of the present invention described above is applied onto a substrate described below using a coating method such as spray coating, dip coating, bar coating, roll coating, spin coating, die coating, etc., to form a wet coating film. Among these, the spin coating and die coating methods are preferably used. Next, the wet coating film is dried using a hot plate or oven, and then exposed to light through a mask having a predetermined pattern to photopolymerize the alkali-soluble resin and the polyfunctional monomer, etc., to form a cured coating film. Examples of light sources used for exposure include ultraviolet light from a low-pressure mercury lamp, a high-pressure mercury lamp, a metal halide lamp, etc., and electron beams. The amount of exposure is appropriately adjusted depending on the light source used and the thickness of the coating film. In order to promote the polymerization reaction after the exposure, a heat treatment may be carried out. The heating conditions are appropriately selected depending on the blending ratio of each component in the colored curable composition used, the thickness of the coating film, and the like.

[0157] Next, the coating is developed using a developer to dissolve and remove the unexposed parts, forming a coating film in a desired pattern. As the developer, a solution in which an alkali is dissolved in water or a water-soluble solvent is usually used. A suitable amount of a surfactant or the like may be added to this alkaline solution. A general method may be used as the development method. After the development process, the developer is usually washed away and the cured coating film of the colored curable composition is dried to form a colored layer. After the development process, a heat treatment may be performed to sufficiently cure the coating film. The heating conditions are not particularly limited and are appropriately selected depending on the application of the coating film.

[0158] <Light shielding part> The light-shielding portion in the color filter of the present invention is formed in a pattern on a substrate described later, and can be the same as that used as a light-shielding portion in a general color filter. The pattern shape of the light-shielding part is not particularly limited, and examples thereof include stripe-like and matrix-like shapes. The light-shielding part may be a thin metal film such as chromium formed by a sputtering method, a vacuum deposition method, or the like. Alternatively, the light-shielding part may be a resin layer containing light-shielding particles such as carbon fine particles, metal oxides, inorganic pigments, and organic pigments in a resin binder. In the case of a resin layer containing light-shielding particles, there are a method of patterning by development using a photosensitive resist, a method of patterning using an inkjet ink containing light-shielding particles, a method of thermally transferring a photosensitive resist, and the like.

[0159] The film thickness of the light-shielding portion is set to about 0.2 to 0.4 μm in the case of a metal thin film, and is set to about 0.5 to 2 μm in the case of a black pigment dispersed or dissolved in a binder resin.

[0160] <Substrate> The substrate may be a transparent substrate, a silicon substrate, or a transparent or silicon substrate on which an aluminum, silver, or silver / copper / palladium alloy thin film is formed, as described below. On these substrates, other color filter layers, resin layers, transistors such as TFTs, circuits, etc. may be formed. The transparent substrate in the color filter of the present invention is not particularly limited as long as it is a base material transparent to visible light, and a transparent substrate used in general color filters can be used. Specifically, examples of the transparent substrate include transparent rigid materials with no flexibility, such as quartz glass, non-alkali glass, and synthetic quartz plate, and transparent flexible materials with flexibility, such as transparent resin films, optical resin plates, and flexible glass. The thickness of the transparent substrate is not particularly limited, but may be, for example, about 100 μm to 1 mm depending on the application of the color filter of the present invention. The color filter of the present invention may further include, in addition to the substrate, the light-shielding portion, and the colored layer, an overcoat layer, a transparent electrode layer, an alignment film, a columnar spacer, and the like.

[0161] IV.Display device The display device according to the present invention is characterized by having the color filter according to the present invention. The configuration of the display device according to the present invention is not particularly limited, and can be appropriately selected from conventionally known display devices, for example, liquid crystal display devices and organic light-emitting display devices.

[0162] [Liquid crystal display device] An example of the liquid crystal display device of the present invention is a liquid crystal display device having the above-mentioned color filter according to the present invention, a counter substrate, and a liquid crystal layer formed between the color filter and the counter substrate. Such a liquid crystal display device of the present invention will be described with reference to the drawings. Fig. 2 is a schematic diagram showing an example of a liquid crystal display device of the present invention. As shown in Fig. 2, a liquid crystal display device 40 of the present invention has a color filter 10, a counter substrate 20 having a TFT array substrate or the like, and a liquid crystal layer 30 formed between the color filter 10 and the counter substrate 20. The liquid crystal display device of the present invention is not limited to the configuration shown in FIG. 2, but may have any known configuration as a liquid crystal display device that generally uses color filters.

[0163] The driving method of the liquid crystal display device of the present invention is not particularly limited, and any driving method generally used for liquid crystal display devices can be adopted. Examples of such driving methods include the TN method, the IPS method, the OCB method, and the MVA method. Any of these methods can be suitably used in the present invention. The counter substrate can be appropriately selected depending on the driving method of the liquid crystal display device of the present invention. Furthermore, as the liquid crystal constituting the liquid crystal layer, various liquid crystals having different dielectric anisotropy and mixtures thereof can be used depending on the driving method of the liquid crystal display device of the present invention.

[0164] The liquid crystal layer can be formed by a method generally used for producing liquid crystal cells, such as a vacuum injection method, a liquid crystal dropping method, etc. After the liquid crystal layer is formed by the above method, the liquid crystal cell is gradually cooled to room temperature, whereby the enclosed liquid crystal can be aligned.

[0165] [Organic light-emitting display device] An example of the organic light-emitting display device of the present invention is an organic light-emitting display device having the color filter according to the present invention and an organic light-emitting body. Such an organic light-emitting display device of the present invention will be described with reference to the drawings. Fig. 3 is a schematic diagram showing an example of an organic light-emitting display device of the present invention. As illustrated in Fig. 3, an organic light-emitting display device 100 of the present invention has a color filter 10 and an organic light-emitting body 80. An organic protective layer 50 and an inorganic oxide film 60 may be provided between the color filter 10 and the organic light-emitting body 80.

[0166] Examples of the method for laminating the organic light-emitting body 80 include a method for sequentially forming a transparent anode 71, a hole injection layer 72, a hole transport layer 73, a light-emitting layer 74, an electron injection layer 75, and a cathode 76 on the upper surface of a color filter, and a method for bonding an organic light-emitting body 80 formed on a separate substrate onto an inorganic oxide film 60. The transparent anode 71, the hole injection layer 72, the hole transport layer 73, the light-emitting layer 74, the electron injection layer 75, the cathode 76, and other components of the organic light-emitting body 80 may be appropriately selected from known components. The organic light-emitting display device 100 thus fabricated can be applied to, for example, a passive-drive organic EL display and an active-drive organic EL display. The organic light-emitting display device of the present invention is not limited to the configuration shown in FIG. 3, but may have any known configuration as an organic light-emitting display device that generally uses color filters. EXAMPLES

[0167] The present invention will be described in detail below with reference to examples, but the present invention is not limited to these examples. The acid value of the graft copolymer and the block copolymer was determined according to the measurement method described in the above specification of the present invention. The weight average molecular weight (Mw) and Mw / Mn of the graft copolymer and block copolymer were determined as values ​​converted into standard polystyrene by GPC (gel permeation chromatography) according to the measurement method described in the above specification of the present invention. In the following, Production Examples 6 and 8, and Examples 6, 36, and 66 are referred to as Reference Examples.

[0168] (Synthesis Example 1: Production of Macromonomer m1) A reactor equipped with a cooling tube, an addition funnel, a nitrogen inlet, a mechanical stirrer, and a digital thermometer was charged with 30.0 parts by mass of propylene glycol methyl ether acetate (PGMEA), and heated to a temperature of 90 ° C. while stirring under a nitrogen stream. A mixed solution of 45.0 parts by mass of methyl methacrylate (MMA), 10.0 parts by mass of butyl methacrylate (BMA), 10.0 parts by mass of benzyl methacrylate (BzMA), 35.0 parts by mass of unsaturated fatty acid hydroxyalkyl ester modified ε-caprolactone (PCL-FM5) (trade name; Plaxel FM5, manufactured by Daicel Corporation, caprolactone chain repeat number = 5), 7.0 parts by mass of mercaptopropionic acid, and 1.0 parts by mass of α,α'-azobisisobutyronitrile (AIBN) was added dropwise over 1.5 hours and reacted for another 3 hours. After cooling, the reaction solution was diluted with 200 parts by mass of tetrahydrofuran (THF) and reprecipitated with 3000 parts by mass of hexane to obtain 106.0 parts by mass of white powder. Next, 50.0 parts by mass of PGMEA, 7.4 parts by mass of glycidyl methacrylate (GMA), 0.30 parts by mass of N,N-dimethyldodecylamine, and 0.2 parts by mass of p-methoxyphenol were added to 100.0 parts by mass of this white powder, and the mixture was stirred at 110° C. for 24 hours while air bubbling. After cooling, the reaction solution was reprecipitated with 3000 parts by mass of hexane to obtain 106.0 parts by mass of macromonomer m1. The obtained macromonomer m1 was analyzed by gel permeation chromatography (GPC) using N-methylpyrrolidone, 0.01 mol / L lithium bromide added, and polystyrene standard. The weight average molecular weight (Mw) was 4,500 and the molecular weight distribution (Mw / Mn) was 1.6.

[0169] (Synthesis Example 2: Production of Macromonomer m2) In the production of macromonomer m1 in Synthesis Example 1, instead of using 45.0 parts by mass of MMA, 10.0 parts by mass of BMA, 10.0 parts by mass of BzMA, and 35.0 parts by mass of unsaturated fatty acid hydroxyalkyl ester modified ε-caprolactone (PCL-FM5), as shown in Table 1, 60.0 parts by mass of MMA, 10.0 parts by mass of BMA, and 30.0 parts by mass of methoxypolyethylene glycol monomethacrylate (manufactured by NOF Corporation, product name: Blenmer PME-200, ethyleneoxy group repeat number = 4) (PME-200) were used, except that the macromonomer m2 was produced in the same manner as in Synthesis Example 1. The obtained macromonomer m2 had a weight average molecular weight (Mw) of 6000 and a molecular weight distribution (Mw / Mn) of 1.7.

[0170] (Synthesis Example 3: Production of Graft Copolymer A) A reactor equipped with a cooling tube, an addition funnel, a nitrogen inlet, a mechanical stirrer, and a digital thermometer was charged with 100.0 parts by mass of PGMEA, and heated to a temperature of 85° C. while stirring under a nitrogen stream. A mixed solution of 94.6 parts by mass of macromonomer m1 of Synthesis Example 1, 5.4 parts by mass of methacrylic acid (MAA), 1.3 parts by mass of n-dodecyl mercaptan, 50.0 parts by mass of PGMEA, and 1.0 parts by mass of AIBN was dropped over 1.5 hours, and the mixture was heated and stirred for 3 hours, after which a mixed solution of 0.10 parts by mass of AIBN and 6.0 parts by mass of PGMEA was dropped over 10 minutes, and the mixture was further aged at the same temperature for 1 hour. After cooling, the reaction solution was reprecipitated with 3000 parts by mass of hexane to obtain 99.0 parts by mass of graft copolymer A. The resulting graft copolymer A had a weight average molecular weight (Mw) of 11,200, an Mw / Mn ratio of 2.6, and an acid value of 35 mgKOH / g.

[0171] (Synthesis Examples 4 to 8: Production of Graft Copolymers BF) Graft copolymers B to F were produced in the same manner as in Synthesis Example 1, except that instead of using 94.6 parts by mass of macromonomer m1 and 5.4 parts by mass of MAA in Synthesis Example 1, at least one of the types of macromonomer, the types of monomers deriving the structural unit represented by general formula (I), and the mass ratio of the macromonomer and the monomers deriving the structural unit represented by general formula (I) was changed as shown in Table 1, and the amount of n-dodecyl mercaptan was arbitrarily changed to adjust the molecular weight. The weight average molecular weight (Mw), Mw / Mn, and acid value of the obtained graft copolymers B to F are shown in Table 1. In the table, 2-MOES represents 2-methacryloyloxyethylsuccinic acid from which the structural unit represented by the general formula (II-2) is derived. ATBS represents 2-acrylamido-2-methylpropanesulfonic acid (manufactured by Toa Gosei Co., Ltd., product name ATBS). P-1M represents 2-methacryloyloxyethylsuccinic acid. R Represents royloxyethyl acid phosphate (Kyoeisha Chemical Industry, product name Light Ester P-1M).

[0172] [Table 1]

[0173] (Synthesis Example 9: Production of Block Copolymer G) A reactor equipped with a cooling tube, an addition funnel, a nitrogen inlet, a mechanical stirrer, and a digital thermometer was charged with 150.0 parts by mass of PGMEA, 3.0 parts of iodine, 2,2'-azobis(4-methoxy-2,4-dimethylvaleronitrile) (trade name: V-70, manufactured by Wako Pure Chemical Industries, Ltd.), 26.3 parts by mass of MMA, 17.5 parts by mass of BMA, 43.9 parts by mass of methoxypolyethylene glycol monomethacrylate (manufactured by NOF Corporation, trade name: Blenmer PME-200, number of ethyleneoxy group repeats = 4) (PME-200), and 0.04 parts by mass of succinimide, and the mixture was stirred at 40°C for 5 hours with stirring under a nitrogen stream to produce a B block copolymer. Subsequently, 12.3 parts by mass of MAA was added and stirred at 40° C. for 5 hours. The solid content was measured and calculated from the non-volatile content, and the polymerization conversion rate was 99%. The reaction solution was reprecipitated with 3,000 parts by mass of hexane to obtain 99.0 parts by mass of AB block copolymer G. The block copolymer thus obtained G The weight average molecular weight (Mw) was 8100, Mw / Mn was 1.2, and the acid value was 80 mgKOH / g.

[0174] (Synthesis Example 10: Production of Block Copolymer H) Block copolymer H was produced in the same manner as in Synthesis Example 9, except that 70.2 parts by mass of MMA and 17.5 parts by mass of BMA were used instead of 26.3 parts by mass of MMA, 17.5 parts by mass of BMA, and 43.9 parts by mass of methoxypolyethylene glycol monomethacrylate in Synthesis Example 9. The weight average molecular weight (Mw), Mw / Mn, and acid value of the obtained block copolymer H are shown in Table 2.

[0175] [Table 2]

[0176] (Production Example 1: Production of Salt-Type Graft Copolymer A) To 25.0 parts by mass of PGMEA, 25.52 parts by mass of graft copolymer A and 0.48 parts by mass of 1,8-diazabicyclo[5.4.0]undecene-7 (manufactured by San-Apro, "DBU") of compound (B) (0.2 molar equivalent to the MAA constituent unit of graft copolymer A) were added, and the mixture was stirred at room temperature for 6 hours to prepare a salt-type graft copolymer A solution. The obtained salt-type graft copolymer A solution was adjusted to a solid content of 35% with PGMEA.

[0177] (Production Examples 2 to 8: Production of Salt-Type Graft or Block Copolymers B to H) In Production Example 1, graft copolymer A of Instead, graft copolymers B to F also are block copolymers G and H ofThe salt-type graft copolymers B to F solutions and the salt-type block copolymers G and H solutions were each produced in the same manner as in Production Example 1, except that DBU was used in an amount of 0.2 molar equivalent relative to the constitutional units represented by general formula (I) of graft copolymers B to F or block copolymers G and H.

[0178] (Production Examples 9 to 11: Production of Salt-Type Graft Copolymers I to K) The salt-type graft copolymer I to K solutions were each produced in the same manner as in Production Example 1, except that in Production Example 1, graft copolymer B was used instead of graft copolymer A, and the amount of compound (B) (molar equivalent relative to the MAA constituent unit of the graft copolymer) was changed as shown in Table 4.

[0179] (Production Examples 12 to 30: Production of Salt-Type Graft Copolymers L to AD) In Production Example 1, graft copolymer A of Instead, graft copolymer B of The salt-type graft copolymers L to AD solutions were prepared in the same manner as in Production Example 1, except that the type of compound (B) was changed as shown in Table 4 or Table 5.

[0180] (Preparation Example 1: Preparation of alkali-soluble resin α) A reactor equipped with a cooling tube, an addition funnel, a nitrogen inlet, a mechanical stirrer, and a digital thermometer was charged with 300 parts by mass of PGMEA, and the temperature was raised to 100°C under a nitrogen atmosphere, after which 90 parts by mass of 2-phenoxyethyl methacrylate (PhEMA), 54 parts by mass of MMA, 36 parts by mass of methacrylic acid (MAA), 6 parts by mass of Perbutyl O (manufactured by NOF Corp.), and 2 parts by mass of a chain transfer agent (n-dodecyl mercaptan) were continuously added dropwise over 1.5 hours. The reaction was then continued while maintaining the temperature at 100°C, and 2 hours after the end of the dropwise addition of the main chain forming mixture, 0.1 parts by mass of p-methoxyphenol was added as a polymerization inhibitor to terminate the polymerization. Next, while blowing in air, 20 parts by mass of glycidyl methacrylate (GMA) was added as an epoxy group-containing compound, and the temperature was raised to 110°C. After that, 0.8 parts by mass of triethylamine was added and an addition reaction was carried out at 110°C for 15 hours to obtain an alkali-soluble resin α solution (weight average molecular weight (Mw) 8,500, acid value 75 mgKOH / g, solid content 40% by mass).

[0181] Example 1 (1) Manufacture of colorant dispersion G-1 14.9 parts by weight of the salt-type graft copolymer A solution from Production Example 1 as dispersant A, 11.7 parts by weight of CI Pigment Green 58 (PG58), 1.3 parts by weight of CI Pigment Yellow 138 (PY138), 72.1 parts by weight of PGMEA, and 100 parts by weight of zirconia beads with a particle size of 2.0 mm were placed in a mayonnaise bottle and shaken for 1 hour with a paint shaker (manufactured by Asada Iron Works Co., Ltd.) as pre-crushing, then the zirconia beads with a particle size of 2.0 mm were removed and 200 parts by weight of zirconia beads with a particle size of 0.1 mm were added, and similarly dispersed for 4 hours with the paint shaker as main crushing, to obtain colorant dispersion liquid G-1.

[0182] (2) Preparation of Colored Curable Composition G-1 9.80 parts by mass of the colorant dispersion G-1 obtained in (1) above, 0.36 parts by mass of the alkali-soluble resin α solution obtained in Preparation Example 1, 1.31 parts by mass of a polyfunctional monomer (product name Aronix M-403, manufactured by Toagosei Co., Ltd.), 0.06 parts by mass of 2-methyl-1-(4-methylthiophenyl)-2-morpholinopropan-1-one (photoinitiator: product name Irgacure 907, manufactured by BASF Japan Ltd.), 0.06 parts by mass of 2-benzyl-2-dimethylamino-1-(4-morpholino To the mixture were added 0.06 parts by mass of 1,2-octanedione,1-[4-(phenylthio)-,2-(O-benzoyloxime)] (photoinitiator: trade name Irgacure OXE01, manufactured by BASF Japan Co., Ltd.), 0.03 parts by mass of 1,2-octanedione,1-[4-(phenylthio)-,2-(O-benzoyloxime)] (photoinitiator: trade name Irgacure OXE01, manufactured by BASF Japan Co., Ltd.), 0.07 parts by mass of a fluorine-based surfactant (trade name Megafac R-08MH, manufactured by DIC Corporation), and 8.30 parts by mass of PGMEA, to obtain a colored curable composition G-1.

[0183] (Examples 2 to 30) (1) Production of colorant dispersions G-2 to G-30 Colorant dispersions G-2 to G-30 were produced in the same manner as in Example 1, except that in (1) of Example 1, salt-type graft copolymer B to AD solutions were used, as shown in Tables 3 to 5, instead of the salt-type graft copolymer A solution. (2) Preparation of Colored Curable Compositions G-2 to G-30 Colored curable compositions G-2 to G-30 were obtained in the same manner as in Example 1(2), except that the colorant dispersion liquid G-1 was replaced with the colorant dispersion liquid G-2 to G-30, respectively.

[0184] (Comparative Examples 1 to 3) (1) Preparation of Comparative Colorant Dispersions CG-1 to CG-3 Comparative colorant dispersions CG-1 to CG-3 were obtained in the same manner as in Example 1, except that in (1) of Example 1, instead of dispersant A, which is a salt-type graft copolymer, graft copolymers B, E, and F, which are not salt-formed with compound (B), were used, as shown in Table 5. (2) Preparation of Comparative Colored Curable Compositions CG-1 to CG-3 Comparative colored curable compositions CG-1 to CG-3 were obtained in the same manner as in Example 1(2), except that the comparative colorant dispersions CG-1 to CG-3 were used instead of the colorant dispersion G-1 in Example 1(2).

[0185] (Example 31) (1) Manufacture of colorant dispersion R-1 14.9 parts by weight of the salt-type graft copolymer A solution of Production Example 1 as dispersant A, 3.9 parts by weight of CI Pigment Red 177 (PR177), 9.1 parts by weight of CI Pigment Red 291 (PR291), 72.1 parts by weight of PGMEA, and 100 parts by weight of zirconia beads with a particle size of 2.0 mm were placed in a mayonnaise bottle and shaken for 1 hour with a paint shaker (manufactured by Asada Iron Works Co., Ltd.) as pre-crushing, then the zirconia beads with a particle size of 2.0 mm were removed and 200 parts by weight of zirconia beads with a particle size of 0.1 mm were added, and similarly dispersed for 4 hours with a paint shaker as main crushing, to obtain colorant dispersion liquid R-1.

[0186] (2) Preparation of Colored Curable Composition R-1 9.80 parts by mass of the colorant dispersion liquid R-1 obtained in (1) above, 0.36 parts by mass of the alkali-soluble resin α solution obtained in Preparation Example 1, 1.31 parts by mass of a polyfunctional monomer (product name Aronix M-403, manufactured by Toagosei Co., Ltd.), 0.06 parts by mass of 2-methyl-1-(4-methylthiophenyl)-2-morpholinopropan-1-one (photoinitiator: product name Irgacure 907, manufactured by BASF Japan Ltd.), 0.06 parts by mass of 2-benzyl-2-dimethylamino-1-(4-morpholino To the mixture were added 0.06 parts by mass of 1,2-octanedione,1-[4-(phenylthio)-,2-(O-benzoyloxime)] (photoinitiator: trade name Irgacure OXE01, manufactured by BASF Japan Co., Ltd.), 0.03 parts by mass of 1,2-octanedione,1-[4-(phenylthio)-,2-(O-benzoyloxime)] (photoinitiator: trade name Irgacure OXE01, manufactured by BASF Japan Co., Ltd.), 0.07 parts by mass of a fluorine-based surfactant (trade name Megafac R-08MH, manufactured by DIC Corporation), and 8.30 parts by mass of PGMEA, to obtain a colored curable composition R-1.

[0187] (Examples 32 to 60) (1) Production of colorant dispersions R-2 to R-30 Colorant dispersions R-2 to R-30 were produced in the same manner as in Example 31, except that in (1) of Example 31, salt-type graft copolymer B to AD solutions were used, as shown in Tables 6 to 8, instead of the salt-type graft copolymer A solution, respectively. (2) Production of Colored Curable Compositions R-2 to R-30 Colored curable compositions R-2 to R-30 were obtained in the same manner as in Example 31(2), except that the colorant dispersion liquid R-1 was replaced with the colorant dispersion liquids R-2 to R-30, respectively.

[0188] (Comparative Examples 4 to 6) (1) Preparation of Comparative Colorant Dispersions CR-1 to CR-3 Comparative colorant dispersions CR-1 to CR-3 were obtained in the same manner as in Example 31, except that in (1) of Example 31, instead of dispersant A, which is a salt-type graft copolymer, graft copolymers B, E, and F, which are not salt-formed with compound (B), were used, as shown in Table 8. (2) Preparation of Comparative Colored Curable Compositions CR-1 to CR-3 Comparative colored curable compositions CR-1 to CR-3 were obtained in the same manner as in Example 31(2), except that the comparative colorant dispersions CR-1 to CR-3 were used instead of the colorant dispersion R-1 in Example 31(2).

[0189] (Example 61) (1) Preparation of colorant dispersion B-1 14.9 parts by weight of the salt-type graft copolymer A solution from Production Example 1 as dispersant A, 10.4 parts by weight of CI Pigment Blue 15:6 (PB15:6) as colorants, 2.6 parts by weight of CI Pigment Violet 23 (PV23), 72.1 parts by weight of PGMEA, and 100 parts by weight of zirconia beads with a particle size of 2.0 mm were placed in a mayonnaise bottle and shaken for 1 hour with a paint shaker (manufactured by Asada Iron Works Co., Ltd.) as pre-crushing, then the 2.0 mm zirconia beads were removed and 200 parts by weight of zirconia beads with a particle size of 0.1 mm were added, and similarly dispersed for 4 hours with a paint shaker as main crushing, to obtain colorant dispersion liquid B-1.

[0190] (2) Preparation of Colored Curable Composition B-1 The colorant dispersion B-1 obtained in (1) above was used in an amount of 6.78 parts by mass, the alkali-soluble resin α solution obtained in Preparation Example 1 was used in an amount of 1.46 parts by mass, a polyfunctional monomer (product name: Aronix M-403, manufactured by Toagosei Co., Ltd.) was used in an amount of 1.36 parts by mass, 2-methyl-1-(4-methylthiophenyl)-2-morpholinopropan-1-one (photoinitiator: product name: Irgacure 907, manufactured by BASF Japan Ltd.) was used in an amount of 0.09 parts by mass, and 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-2-propan-1-one was used in an amount of 0.09 parts by mass. To the mixture were added 0.09 parts by mass of 1,2-octanedione,1-[4-(phenylthio)-,2-(O-benzoyloxime)] (photoinitiator: trade name Irgacure OXE01, manufactured by BASF Japan Co., Ltd.), 0.04 parts by mass of 1,2-octanedione,1-[4-(phenylthio)-,2-(O-benzoyloxime)] (photoinitiator: trade name Irgacure OXE01, manufactured by BASF Japan Co., Ltd.), 0.07 parts by mass of a fluorine-based surfactant (trade name Megafac R-08MH, manufactured by DIC Corporation), and 10.11 parts by mass of PGMEA, to obtain a colored curable composition B-1.

[0191] (Examples 62 to 90) (1) Preparation of colorant dispersions B-2 to B-30 Colorant dispersions B-2 to B-30 were produced in the same manner as in Example 61, except that in (1) of Example 61, salt-type graft copolymer B to AD solutions were used, as shown in Tables 9 to 11, instead of the salt-type graft copolymer A solution. (2) Preparation of Colored Curable Compositions B-2 to B-30 Colored curable compositions B-2 to B-30 were obtained in the same manner as in Example 61(2), except that in Example 61(2), the colorant dispersion liquid B-1 was replaced with the colorant dispersion liquid B-2 to B-30, respectively.

[0192] (Comparative Examples 7 to 9) (1) Preparation of Comparative Colorant Dispersions CB-1 to CB-3 Comparative colorant dispersions CB-1 to CB-3 were obtained in the same manner as in Example 61, except that in (1) of Example 61, instead of dispersant A, which is a salt-type graft copolymer, graft copolymers B, E, and F, which are not salt-formed with compound (B), were used, as shown in Table 11. (2) Preparation of Comparative Colored Curable Compositions CB-1 to CB-3 Comparative colored curable compositions CB-1 to CB-3 were obtained in the same manner as in Example 61(2), except that the comparative colorant dispersions CB-1 to CB-3 were used instead of the colorant dispersion B-1 in Example 61(2).

[0193] [Evaluation method] <Evaluation of dispersibility and stability of colorant dispersion liquid> The viscosity of each of the colorant dispersions obtained in the Examples and Comparative Examples was measured immediately after preparation and after storage at 25°C for 30 days, and the viscosity stability was evaluated by calculating the viscosity change rate from the viscosity before and after storage. A vibration viscometer was used to measure the viscosity at 25.0±0.5°C. (Dispersion Stability Evaluation Criteria) A: The change in viscosity before and after storage is less than 10%. B: The change in viscosity before and after storage is 10% or more but less than 20%. C: Viscosity change rate before and after storage is 20% or more but less than 40% D: Viscosity change rate before and after storage is 40% or more E: Gelation during dispersion or storage However, this is the value when the colorant is 13 mass % with respect to the total mass of the colorant dispersion liquid including the solvent. If the evaluation result is C, the dispersion stability is relatively good, if the evaluation result is B, the dispersion stability is good, and if the evaluation result is A, the colorant dispersion liquid has excellent dispersion stability.

[0194] <Optical performance, contrast> The colored curable compositions obtained in the examples and comparative examples were applied to a glass substrate (manufactured by NH Technoglass Co., Ltd., "NA35") using a spin coater to a thickness that would form a colored layer with y=0.520 for Green, x=0.655 for Red, and y=0.082 for Blue after post-baking, and then dried at 80°C for 3 minutes using a hot plate to form a colored layer on the glass substrate. This colored layer was irradiated with ultraviolet light at 60mJ / cm2 using an ultra-high pressure mercury lamp. Next, the colored substrate was post-baked for 30 minutes in a clean oven at 230°C to produce a colored substrate. The contrast, chromaticity (x, y), and luminance (Y) of the obtained colored substrate were measured using a contrast measuring device CT-1B manufactured by Tsubosaka Electric and a microspectrophotometer OSP-SP200 manufactured by Olympus. The brightness was calculated when y = 0.520 for Green, x = 0.655 for Red, and y = 0.082 for Blue. The higher the value, the higher the brightness. (Contrast Evaluation Criteria) A: Green and Blue are over 7000, Red is over 6000, B: Green and Blue are 6000~7000, Red is 5000~6000 C: Green and Blue are 5000~6000, Red is 4000~5000 D: Green and Blue are 4000~5000, Red is 3000~4000 E: Green and Blue are less than 4000, Red is less than 3000 Green is the contrast at y=0.520, Red is the contrast at x=0.655, and Blue is the contrast at y=0.082. If the evaluation result is C, the contrast is relatively good, if the evaluation result is B, the contrast is good, and if the evaluation result is A, the contrast is excellent.

[0195] <Adhesion evaluation to substrate> The colored curable compositions obtained in the examples and comparative examples were each applied to a glass substrate (NH Technoglass Co., Ltd., "NA35") using a spin coater in a thickness that would form a colored layer of 2.0 μm after post-baking, and then dried on a hot plate at 80° C. for 3 minutes to form a colored layer on the glass substrate. This colored layer was irradiated with ultraviolet light of 60 mJ / cm2 using an ultra-high pressure mercury lamp. Next, the colored substrate was post-baked in a clean oven at 230°C for 30 minutes to prepare a colored substrate. The obtained colored substrate was cut into 100 squares in the same manner as in JIS K5400, and then cellophane adhesive tape was attached and then instantly peeled off. The change in state of the 100 squares was observed using an optical microscope before and after the test with the cellophane adhesive tape. (Substrate Adhesion Evaluation Criteria) A: 100 squares were checked after the test, and there was no change in the condition of the cut area before and after the test. B: 100 squares were confirmed after the test, and the width of the cut part changed widely before and after the test. C: 70 to 100 squares confirmed after testing D: 30 to 70 squares confirmed after testing E: Less than 30 squares are found after the test, or the entire colored layer peels off. If the evaluation result is C, the adhesion to the substrate is relatively good, if the evaluation result is B, the adhesion to the substrate is good, and if the evaluation result is A, the adhesion to the substrate is excellent.

[0196] <Solvent re-dissolution> The tip of a glass substrate having a width of 0.5 cm and a length of 10 cm was immersed in the colored curable composition obtained in the Examples and Comparative Examples, and the composition was applied to a 1 cm long portion of the glass substrate. The glass substrate was then placed in a thermohygrostat so that the glass surface was horizontal, and dried for 30 minutes at a temperature of 23°C and a humidity of 80% RH. Next, the glass substrate with the dried coating film attached thereto was immersed in PGMEA for 15 seconds. At this time, the redissolution state of the dried coating film was visually determined and evaluated. (Solvent re-dissolvability evaluation criteria) A: The dried coating film was completely dissolved. B: Thin flakes of the dried coating film appear in the solvent, and the flakes eventually dissolve. C: Dried coating flakes appear in the solvent and the solution becomes colored. D: Dried coating flakes appeared in the solvent, and the solution did not color. E: No flakes of dried coating were formed in the solvent and the solution was not colored. If the evaluation result is C, the solvent resolubility is relatively good, if the evaluation result is B, the solvent resolubility is good, and if the evaluation result is A, the solvent resolubility is excellent.

[0197] <Development time evaluation> The colored curable compositions obtained in the Examples and Comparative Examples were each applied onto a glass substrate (NH Technoglass Co., Ltd., "NA35") using a spin coater in a thickness that would form a colored layer having a thickness of 2.0 μm after post-baking, and then dried at 80° C. for 3 minutes using a hot plate to form a colored layer on the glass substrate. This colored layer was then exposed to 60 mJ / cm 2 of light using an ultra-high pressure mercury lamp through a photomask. 2 Thereafter, the glass substrate on which the colored layer was formed was shower-developed for 60 seconds using a 0.05% by mass aqueous solution of potassium hydroxide as an alkaline developer, and the time until the colored layer was completely dissolved and the glass surface of the area on which the colored layer was formed appeared was measured as the development time. (Evaluation Criteria) A: The time it took for the glass surface to appear was less than 15 seconds. B: The time it took for the glass surface to appear was more than 15 seconds but less than 30 seconds. C: The time it took for the glass surface to appear was more than 30 seconds but less than 45 seconds. D: The time it took for the glass surface to appear was more than 45 seconds but less than 60 seconds. E: The glass surface did not appear. If the evaluation result is C, the developability is relatively good, if the evaluation result is B, the developability is good, and if the evaluation result is A, the developability is excellent.

[0198] The colorant dispersions and colored curable compositions obtained in the above-mentioned Examples and Comparative Examples were evaluated as described above. The evaluation results are shown in Tables 3 to 11.

[0199] [Table 3]

[0200] [Table 4]

[0201] [Table 5]

[0202] [Table 6]

[0203] [Table 7]

[0204] [Table 8]

[0205] [Table 9]

[0206] [Table 10]

[0207] [Table 11]

[0208] [Summary of results] Comparison between the Examples and Comparative Examples reveals that in Examples 1 to 90, in which a salt-type polymer in which at least a part of the acidic group contained in the general formula (I) forms a salt with one or more compounds (B) selected from the group consisting of a tertiary amino group-containing basic compound and a basic heterocyclic compound is used as a dispersant, a colored curable composition that simultaneously satisfies excellent dispersion stability, brightness, contrast, substrate adhesion, and solvent resolubility can be obtained. In contrast, the comparative colored curable compositions of Comparative Examples 1 to 9, which used an acidic group-containing polymer that was not salted with the compound (B), had poor dispersion stability, and were also inferior in brightness and contrast, as well as in adhesion to substrates and resolubility in solvents. In comparison among the examples, it was shown that when the acid value of the dispersant is within a certain range, the dispersion stability, brightness, contrast, and solvent resolubility tend to be more excellent, and when the acid group of the dispersant is a sulfonic acid group or a carboxy group, especially a carboxy group, the dispersion stability, brightness, contrast, and solvent resolubility tend to be more excellent. In addition, when the molar equivalent of the salt formed by the acid group of the dispersant and the compound (B) is within a certain range, the dispersion stability, brightness, contrast, substrate adhesion, and solvent resolubility tend to be more excellent, and when the pKa of the compound (B) is larger, the dispersion stability, brightness, contrast, and solvent resolubility tend to be more excellent. In the dispersant, the polymer having the constitutional unit represented by the general formula (I) is before When at least one structural unit selected from the group consisting of structural units represented by the following general formula (V') is contained, there is a tendency for the adhesion to the substrate to be further improved. [Explanation of symbols]

[0209] 1 Board 2 Light shielding section 3 Colored layer 10 Color Filters 20 Opposing substrate 30 Liquid crystal layer 40 LCD display device 50 Organic protective layer 60 Inorganic oxide film 71 Transparent anode 72 Hole injection layer 73 Hole transport layer 74 Light-emitting layer 75 Electron injection layer 76 Cathode 80 Organic Light Emitting Materials 100 Organic light-emitting display device

Claims

1. A colorant dispersion liquid containing a colorant, a dispersant, and a solvent, the dispersant comprises a salt-type polymer in which at least a portion of acidic groups contained in a polymer having a structural unit represented by the following general formula (I) forms a salt with one or more compounds (B) selected from the group consisting of tertiary amines and basic heterocyclic compounds, The polymer having a constitutional unit represented by the following general formula (I) is at least one of a graft copolymer having a constitutional unit represented by the following general formula (I) and a block copolymer having an A block containing a constitutional unit represented by the following general formula (I): A colorant dispersion liquid (excluding cases where the water content exceeds 2 mass%), wherein the solvent is at least one selected from the group consisting of glycol ether acetate solvents, carbitol acetate solvents, glycol ether solvents, and ester solvents. 【Chemistry 1】 (In general formula (I), R １ represents a hydrogen atom or a methyl group, A represents a direct bond or at least one of a -CONH- group and a -COO- group, and an aliphatic hydrocarbon group having 1 to 12 carbon atoms which may contain an oxygen atom, Q represents a carboxy group (-COOH) and a sulfonic acid group (-SO ３ H) is at least one acidic group selected from the group consisting of

2. The colorant dispersion liquid according to claim 1 , wherein the compound (B) has a molecular weight of 800 or less.

3. 3. The colorant dispersion liquid according to claim 1, wherein in the dispersant, the polymer having the constitutional unit represented by the general formula (I) before salt formation has an acid value of 20 to 250 mgKOH / g.

4. The colorant dispersion liquid according to any one of claims 1 to 3, wherein the constitutional unit represented by the general formula (I) includes a constitutional unit represented by the following general formula (II): 【Chemistry 2】 (In general formula (II), R １ represents a hydrogen atom or a methyl group, and A represents a direct bond or an aliphatic hydrocarbon group having 1 to 12 carbon atoms which may contain at least one of a -CONH- group and a -COO- group, and an oxygen atom.

5. The polymer having a structural unit represented by the general formula (I) is A graft copolymer having a constitutional unit represented by the above general formula (I) and a constitutional unit represented by the following general formula (III), wherein the polymer chain in the general formula (III) contains at least one constitutional unit selected from the group consisting of a constitutional unit represented by the following general formula (V) and a constitutional unit represented by the following general formula (V'), and A block copolymer having an A block containing a constitutional unit represented by the above general formula (I) and a B block containing a constitutional unit represented by the following general formula (IV), wherein the B block contains at least one constitutional unit selected from the group consisting of a constitutional unit represented by the following general formula (V) and a constitutional unit represented by the following general formula (V'): The colorant dispersion liquid according to any one of claims 1 to 4, which is at least one of the following: 【Chemistry 3】 (In general formula (III), R １” is a hydrogen atom or a methyl group, A １ represents a direct bond or a divalent linking group selected from a linear, branched or cyclic, saturated or unsaturated aliphatic hydrocarbon group, a linear, branched or cyclic, saturated or unsaturated aliphatic hydrocarbon group having a hydroxyl group, an aromatic hydrocarbon group, a -CONH- group, a -COO- group, a -NHCOO- group, a -O- group, a -S- group, and combinations thereof; and Polymer represents a polymer chain. 【Chemistry 4】 (In general formula (IV), R １１ is a hydrogen atom or a methyl group, A ２ is a -CONH- group or a -COO- group, R ４ is a hydrocarbon group which may have a substituent and may contain a heteroatom. 【Chemistry 5】 (In general formula (V), R １１’ is a hydrogen atom or a methyl group, A ２’ is a -CONH- group or a -COO- group, R ５ is an ethylene group or a propylene group, R ６ represents a hydrogen atom or a hydrocarbon group, and m represents a number of 2 or more and 80 or less. In general formula (V'), R １１” is a hydrogen atom or a methyl group, A ２” is a -CONH- group or a -COO- group, R ７ is an alkylene group having 1 to 10 carbon atoms, R ８ is an alkylene group having 3 to 7 carbon atoms, R ９ is a hydrogen atom or a hydrocarbon group, and n is a number of 1 to 40.

6. A salt-type polymer in which at least a part of the acidic groups contained in a polymer having a structural unit represented by the following general formula (I) forms a salt with one or more compounds (B) selected from the group consisting of tertiary amines and basic heterocyclic compounds: A polymer having a structural unit represented by the following general formula (I): A graft copolymer having a constitutional unit represented by the following general formula (I) and a constitutional unit represented by the following general formula (III), wherein the polymer chain in the general formula (III) contains at least one constitutional unit selected from the group consisting of a constitutional unit represented by the following general formula (V) and a constitutional unit represented by the following general formula (V'), and A block copolymer having an A block containing a constitutional unit represented by the following general formula (I) and a B block containing a constitutional unit represented by the following general formula (IV), wherein the B block contains at least one constitutional unit selected from the group consisting of a constitutional unit represented by the following general formula (V) and a constitutional unit represented by the following general formula (V'): A dispersant, which is at least one of 【Chemistry 6】 (In general formula (I), R １ represents a hydrogen atom or a methyl group, A represents a direct bond or at least one of a -CONH- group and a -COO- group, and an aliphatic hydrocarbon group having 1 to 12 carbon atoms which may contain an oxygen atom, Q represents a carboxy group (-COOH) and a sulfonic acid group (-SO ３ H) is at least one acidic group selected from the group consisting of 【Chemistry 7】 (In general formula (III), R １” is a hydrogen atom or a methyl group, A １ represents a direct bond or a divalent linking group selected from a linear, branched or cyclic, saturated or unsaturated aliphatic hydrocarbon group, a linear, branched or cyclic, saturated or unsaturated aliphatic hydrocarbon group having a hydroxyl group, an aromatic hydrocarbon group, a -CONH- group, a -COO- group, a -NHCOO- group, a -O- group, a -S- group, and combinations thereof; and Polymer represents a polymer chain. 【Chemistry 8】 (In general formula (IV), R １１ is a hydrogen atom or a methyl group, A ２ is a -CONH- group or a -COO- group, R ４ is a hydrocarbon group which may have a substituent and may contain a heteroatom. 【Chemistry 9】 (In general formula (V), R １１’ is a hydrogen atom or a methyl group, A ２’ is a -CONH- group or a -COO- group, R ５ is an ethylene group or a propylene group, R ６ represents a hydrogen atom or a hydrocarbon group, and m represents a number of 2 or more and 80 or less. In general formula (V'), R １１” is a hydrogen atom or a methyl group, A ２” is a -CONH- group or a -COO- group, R ７ is an alkylene group having 1 to 10 carbon atoms, R ８ is an alkylene group having 3 to 7 carbon atoms, R ９ is a hydrogen atom or a hydrocarbon group, and n is a number of 1 to 40.

7. The dispersant according to claim 6 , wherein the compound (B) has a molecular weight of 800 or less.

8. The dispersant according to claim 6 or 7, wherein the acid value of the polymer having a structural unit represented by the general formula (I) before salt formation is 20 to 250 mgKOH / g.

9. The dispersant according to any one of claims 6 to 8, wherein the constitutional unit represented by the general formula (I) includes a constitutional unit represented by the following general formula (II): 【Chemistry 10】 (In general formula (II), R １ represents a hydrogen atom or a methyl group, and A represents a direct bond or an aliphatic hydrocarbon group having 1 to 12 carbon atoms which may contain at least one of a -CONH- group and a -COO- group, and an oxygen atom.

10. A colored curable composition comprising a dispersant, a colorant, a polymerizable compound, an initiator, and a solvent, the dispersant comprises a salt-type polymer in which at least a portion of acidic groups contained in a polymer having a structural unit represented by the following general formula (I) forms a salt with one or more compounds (B) selected from the group consisting of tertiary amines and basic heterocyclic compounds, The polymer having a constitutional unit represented by the following general formula (I) is at least one of a graft copolymer having a constitutional unit represented by the following general formula (I) and a block copolymer having an A block containing a constitutional unit represented by the following general formula (I): The colored curable composition, wherein the solvent is at least one selected from the group consisting of glycol ether acetate solvents, carbitol acetate solvents, glycol ether solvents, and ester solvents (excluding the case where the water content exceeds 2 mass%). 【Chemistry 11】 (In general formula (I), R １ represents a hydrogen atom or a methyl group, A represents a direct bond or at least one of a -CONH- group and a -COO- group, and an aliphatic hydrocarbon group having 1 to 12 carbon atoms which may contain an oxygen atom, Q represents a carboxy group (-COOH) and a sulfonic acid group (-SO ３ H) is at least one acidic group selected from the group consisting of

11. The colored curable composition according to claim 10 , wherein the compound (B) has a molecular weight of 800 or less.

12. The colored curable composition according to claim 10 or 11, wherein in the dispersant, the acid value of the polymer having the structural unit represented by the general formula (I) before salt formation is 20 to 250 mgKOH / g.

13. The colored curable composition according to any one of claims 10 to 12, wherein the structural unit represented by general formula (I) includes a structural unit represented by the following general formula (II): 【Chemistry 12】 (In general formula (II), R １ represents a hydrogen atom or a methyl group, and A represents a direct bond or an aliphatic hydrocarbon group having 1 to 12 carbon atoms which may contain at least one of a -CONH- group and a -COO- group, and an oxygen atom.

14. The polymer having a structural unit represented by the general formula (I) is A graft copolymer having a constitutional unit represented by the above general formula (I) and a constitutional unit represented by the following general formula (III), wherein the polymer chain in the general formula (III) contains at least one constitutional unit selected from the group consisting of a constitutional unit represented by the following general formula (V) and a constitutional unit represented by the following general formula (V'), and A block copolymer having an A block containing a constitutional unit represented by the above general formula (I) and a B block containing a constitutional unit represented by the following general formula (IV), wherein the B block contains at least one constitutional unit selected from the group consisting of a constitutional unit represented by the following general formula (V) and a constitutional unit represented by the following general formula (V'): The colored curable composition according to any one of claims 10 to 13, which is at least one of the following: 【Chemistry 13】 (In general formula (III), R １” is a hydrogen atom or a methyl group, A １ represents a direct bond or a divalent linking group selected from a linear, branched or cyclic, saturated or unsaturated aliphatic hydrocarbon group, a linear, branched or cyclic, saturated or unsaturated aliphatic hydrocarbon group having a hydroxyl group, an aromatic hydrocarbon group, a -CONH- group, a -COO- group, a -NHCOO- group, a -O- group, a -S- group, and combinations thereof; and Polymer represents a polymer chain. 【Chemistry 14】 (In general formula (IV), R １１ is a hydrogen atom or a methyl group, A ２ is a -CONH- group or a -COO- group, R ４ is a hydrocarbon group which may have a substituent and may contain a heteroatom. 【Chemistry 15】 (In general formula (V), R １１’ is a hydrogen atom or a methyl group, A ２’ is a -CONH- group or a -COO- group, R ５ is an ethylene group or a propylene group, R ６ represents a hydrogen atom or a hydrocarbon group, and m represents a number of 2 or more and 80 or less. In general formula (V'), R １１” is a hydrogen atom or a methyl group, A ２” is a -CONH- group or a -COO- group, R ７ is an alkylene group having 1 to 10 carbon atoms, R ８ is an alkylene group having 3 to 7 carbon atoms, R ９ is a hydrogen atom or a hydrocarbon group, and n is a number of 1 to 40.

15. A color filter comprising at least a substrate and colored layers provided on the substrate, wherein at least one of the colored layers is a cured product of the colored curable composition according to any one of claims 10 to 14.

16. A display device comprising the color filter according to claim 15.

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