WO2020031633A1

WO2020031633A1 - Dispersant composition, coloring composition and color filter

Info

Publication number: WO2020031633A1
Application number: PCT/JP2019/028051
Authority: WO
Inventors: 清水達彦
Original assignee: 大塚化学株式会社
Priority date: 2018-08-07
Filing date: 2019-07-17
Publication date: 2020-02-13
Also published as: TWI818051B; JPWO2020031633A1; CN112334504B; JP7299894B2; KR20210040933A; CN112334504A; TW202019995A

Abstract

[Problem] To provide a dispersant composition which exhibits little generation of formaldehyde over time. [Solution] A dispersant composition characterized by containing a polymer which has a structure represented by general formula (5) in a sidechain thereof. (5): *-Y¹-N-R¹¹R¹² [In general formula (5), R¹¹ represents a hydrogen atom or a chain-shaped or ring-shaped hydrocarbon group which has a carbon number of two or higher and may have a substituent group. R¹² represents a chain-shaped or ring-shaped hydrocarbon group which has a carbon number of two or higher and may have a substituent group. R¹¹ and R¹² may form a ring-shaped structure by bonding with one another. Y¹ is a divalent hydrocarbon group. * represents atomic bonding.]

Description

Dispersant composition, coloring composition, and color filter

(4) The present invention relates to a dispersant composition containing a polymer.

Conventionally, in the production of a color filter used for a liquid crystal display or the like, as a method of applying a coloring material to a substrate, a dyeing method, a printing method, an ink jet method, an electrodeposition method, a pigment dispersion method and the like are known. Among them, the pigment dispersion method is mainly used from the viewpoints of spectral characteristics, durability, pattern shape and accuracy. In this pigment dispersion method, a coating film made of a coloring composition in which a pigment, a dispersant, a dispersion medium (solvent), a binder resin, and the like are mixed is formed on a substrate, and radiation is applied through a photomask having a desired pattern shape. Irradiation cures and alkali development is performed.

In recent years, in order to obtain good color reproducibility and high contrast of a color filter, increasing the concentration of a pigment in a coloring composition has been studied. When the concentration of the pigment is increased, the proportion of the dispersant relatively decreases, so that the dispersant is required to have high dispersibility (for example, see Patent Document 1 (paragraph 0004)). In alkali development, a binder resin having alkali solubility plays a large role. However, in the case of a pigment dispersion composition having a high pigment concentration, the ratio of the binder resin as a developing component decreases, and the alkali developability decreases. For this reason, the alkali developability originally required for the binder resin is also required for the dispersant. As such a dispersant, Patent Document 2 discloses, as a pigment dispersion, an AB block copolymer comprising an A block having a polylactone chain in a side chain and a B block having a tertiary amino group in a side chain. It is described to be used (see Patent Document 2 (paragraphs 0023 to 0045)).

JP 2009-265515 A JP 2013-119568 A

In a resin-type dispersant, it has been proposed to introduce a tertiary amino group into a side chain in order to enhance the dispersibility of a coloring material (see Patent Document 2). However, it is considered that the resin-type dispersant having a tertiary amino group generates formaldehyde over time due to the tertiary amino group. Therefore, when such a resin-type dispersant is used in a coloring composition, formaldehyde is contained in the coloring composition. In recent years, environmental standards have become stricter, so that when a conventional resin-type dispersant is used, the amount of formaldehyde in the coloring composition does not meet the environmental standards.

The present invention has been made in view of the above circumstances, and it is an object of the present invention to provide a dispersant composition that generates a small amount of formaldehyde over time.

The dispersant composition of the present invention that has solved the above-mentioned problems is characterized by containing a polymer having a structure represented by the general formula (5) in a side chain.
* -Y ¹ -NR ¹¹ R ¹² (5)
[In the general formula (5), R ¹¹ represents a hydrogen atom, an optionally substituted linear or cyclic hydrocarbon group having 2 or more carbon atoms. R ¹² represents a linear or cyclic hydrocarbon group having 2 or more carbon atoms which may have a substituent. R ¹¹ and R ¹² may combine with each other to form a cyclic structure. Y ¹ represents a divalent hydrocarbon group. * Represents a bond. ]

When a polymer having an amino group is used as a dispersant, it is considered that formaldehyde is generated over time due to the amino group. In the present invention, surprisingly, by forming the amino group into a specific structure (structure represented by the general formula (5)), generation of formaldehyde over time is suppressed, and formaldehyde in the dispersant composition is reduced. it can. Further excellent dispersion performance of the coloring material can be obtained.

The present invention also includes a coloring composition comprising the dispersant composition, a coloring material, a binder resin and a dispersion medium. The present invention also includes a color filter comprising a coloring layer formed using the coloring composition.

According to the present invention, a dispersant composition having a small amount of formaldehyde generated over time can be obtained.

Hereinafter, an example of a preferred embodiment of the present invention will be described. However, the following embodiments are merely examples. The present invention is not limited to the following embodiments.

において In the present invention, “(meth) acryl” means “at least one of acryl and methacryl”. “(Meth) acrylic monomer” refers to a monomer having a “(meth) acryloyl group” in the molecule. “(Meth) acryloyl” refers to “at least one of acryloyl and methacryloyl”. “Vinyl monomer” refers to a monomer having a radically polymerizable carbon-carbon double bond in the molecule. “Structural unit derived from (meth) acrylic monomer” refers to a structural unit in which a radically polymerizable carbon-carbon double bond of a (meth) acrylic monomer is polymerized into a carbon-carbon single bond. The “structural unit derived from a vinyl monomer” refers to a structural unit in which a radically polymerizable carbon-carbon double bond of a vinyl monomer is polymerized into a carbon-carbon single bond.

<Dispersant composition>
The dispersant composition of the present invention is characterized in that the side chain contains a polymer having a structure represented by the general formula (5).
* -Y ¹ -NR ¹¹ R ¹² (5)
[In the general formula (5), R ¹¹ represents a hydrogen atom, an optionally substituted linear or cyclic hydrocarbon group having 2 or more carbon atoms. R ¹² represents a linear or cyclic hydrocarbon group having 2 or more carbon atoms which may have a substituent. R ¹¹ and R ¹² may combine with each other to form a cyclic structure. Y ¹ represents a divalent hydrocarbon group. * Represents a bond. ]

Examples of the chain hydrocarbon group represented by R ¹¹ and R ¹² include a linear alkyl group and a branched chain alkyl group. The linear alkyl group preferably has 2 to 20 carbon atoms, more preferably has 2 to 10 carbon atoms, and still more preferably has 2 to 5 carbon atoms. Examples of the linear alkyl group include an ethyl group, an n-propyl group, an n-butyl group, an n-hexyl group, an n-octyl group, an n-nonyl group, an n-decyl group and an n-lauryl group. . The branched chain alkyl group preferably has 3 to 20 carbon atoms, more preferably 3 to 10 carbon atoms, and still more preferably 3 to 5 carbon atoms. Examples of the branched alkyl group include an isopropyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a 2-ethylhexyl group, a neopentyl group, and an isooctyl group.

Examples of the substituent of the chain hydrocarbon group represented by R ¹¹ and R ¹² include a halogen group, an alkoxy group, a benzoyl group (—COC ₆ H ₅ ), and a hydroxy group.

Examples of the cyclic hydrocarbon group represented by R ¹¹ and R ¹² include a cyclic alkyl group and an aromatic group, and the cyclic alkyl group and the aromatic group may have a chain portion. The cyclic alkyl group preferably has 4 to 18 carbon atoms, more preferably has 6 to 12 carbon atoms, and still more preferably has 6 to 10 carbon atoms. Examples of the cyclic alkyl group include a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and the like. The aromatic group preferably has 6 to 18 carbon atoms, more preferably 6 to 12 carbon atoms, and even more preferably 6 to 8 carbon atoms. Examples of the aromatic group include a phenyl group, a tolyl group, a xylyl group, and a mesityl group. Examples of the cyclic alkyl group having a chain portion and the chain portion of the aromatic group having a chain portion include an alkylene group having 1 to 12 carbon atoms, preferably an alkylene group having 1 to 6 carbon atoms, and more preferably Examples include alkylene groups of formulas 1 to 3.

Examples of the substituent of the cyclic hydrocarbon group represented by R ¹¹ and R ¹² include a halogen group, an alkoxy group, a chain alkyl group, and a hydroxy group.

Examples of the cyclic structure formed by combining R ¹¹ and R ¹² with each other include a 5- to 7-membered nitrogen-containing heterocycle or a condensed ring formed by condensing two of them. The nitrogen-containing hetero ring preferably has no aromaticity, and is more preferably a saturated ring.

Examples of the divalent hydrocarbon group represented by Y ¹ include an alkylene group having 1 to 10 carbon atoms, an alkenylene group having 1 to 10 carbon atoms, and an arenediyl group having 6 to 10 carbon atoms. Among these, an alkylene group having 1 to 10 carbon atoms is preferable. The alkylene group may be linear or branched, but is preferably linear. Y ¹ is preferably an alkylene group having 1 to 5 carbon atoms.

The —NR ¹¹ R ¹² moiety of the structure represented by the general formula (5) includes a monoalkylamino group such as an ethylamino group, a propylamino group, and a tert-butylamino group; a diethylamino group, a dipropylamino group And a dialkylamino group such as a bis (2-hydroxyethyl) amino group.

Examples of the polymer having a structure represented by the general formula (5) in the side chain include a (meth) acrylic polymer, a polyurethane polymer, a polyester polymer, a polyallylamine polymer, and a carbodiimide polymer. Can be mentioned.

The amine value of the polymer having a structure represented by the general formula (5) in the side chain is preferably 10 mgKOH / g or more, more preferably 50 mgKOH / g, from the viewpoints of adsorbability to the colorant and dispersibility of the colorant. g or more, more preferably 80 mgKOH / g or more, preferably 200 mgKOH / g or less, more preferably 150 mgKOH / g or less, even more preferably 120 mgKOH / g or less.

分子 The molecular weight of the polymer having a structure represented by the general formula (5) in the side chain is measured by gel permeation chromatography. The weight average molecular weight (Mw) of the polymer is preferably 3,000 or more, more preferably 4,000 or more, still more preferably 5,000 or more, particularly preferably 6,000 or more, and 40,000 or less. Is more preferably 30,000 or less, further preferably 25,000 or less, and particularly preferably 20,000 or less. When the weight average molecular weight is within the above range, the dispersing performance when used as a dispersant becomes better.

(Block copolymer)
From the viewpoint of dispersibility, the polymer preferably has a block copolymer having an A block having a structural unit derived from a (meth) acrylic monomer and a B block having a structural unit represented by the general formula (1). Coalescence is preferred.

[In the general formula (1), R ¹¹ represents a hydrogen atom, a linear or cyclic hydrocarbon group having 2 or more carbon atoms which may have a substituent. R ¹² represents a linear or cyclic hydrocarbon group having 2 or more carbon atoms which may have a substituent. R ¹¹ and R ¹² may combine with each other to form a cyclic structure. R ¹³ represents a hydrogen atom or a methyl group. X ¹ represents an amide group, an ester group, or a single bond. Y ¹ represents a divalent hydrocarbon group. ]

各種 Various constituent components of the block copolymer will be described below.

(A block)
The A block is a polymer block containing a structural unit derived from a (meth) acrylic monomer. The structural unit derived from the (meth) acrylic monomer in the A block may be only one type, or may have two or more types. By having a structural unit derived from a (meth) acrylic monomer, high affinity with a dispersion medium (solvent) and a binder resin blended in the coloring composition can be maintained.

The content of the structural unit derived from the (meth) acrylic monomer is preferably 80% by mass or more, more preferably 90% by mass or more, still more preferably 95% by mass or more, particularly preferably 100% by mass of the A block. Is 100% by mass.

The (meth) acrylic monomer includes a (meth) acrylate having a chain alkyl group (a linear alkyl group or a branched chain alkyl group), a (meth) acrylate having a cyclic alkyl group, and a (meth) acrylate having a polycyclic structure. (Meth) acrylate having an aromatic group, (meth) acrylate having a polyalkylene glycol structural unit, (meth) acrylate having a hydroxy group, (meth) acrylate having a lactone-modified hydroxy group, and (meth) having an alkoxy group Acrylates, (meth) acrylates having an oxygen-containing heterocyclic group, (meth) acrylates having an acidic group, (meth) acrylic acid, and the like can be used, and one or more of these can be used in combination. Can be.

The (meth) acrylate having a straight-chain alkyl group is preferably a (meth) acrylate having a straight-chain alkyl group having 1 to 20 carbon atoms, and a straight-chain alkyl group having 1 to 20 carbon atoms. A (meth) acrylate having a linear alkyl group of 10 is more preferred. Examples of the (meth) acrylate having a linear alkyl group include methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, n-butyl (meth) acrylate, n-hexyl (meth) acrylate, Examples include n-octyl (meth) acrylate, n-nonyl (meth) acrylate, decyl (meth) acrylate, n-lauryl (meth) acrylate, and n-stearyl (meth) acrylate.

The (meth) acrylate having a branched alkyl group is preferably a (meth) acrylate having a branched alkyl group having 3 to 20 carbon atoms, and a branched alkyl group having 3 to 20 carbon atoms. A (meth) acrylate having a branched alkyl group of 10 is preferred. Examples of the (meth) acrylate having a branched alkyl group include isopropyl (meth) acrylate, isobutyl (meth) acrylate, sec-butyl (meth) acrylate, tert-butyl (meth) acrylate, isooctyl (meth) acrylate, 2- Examples include ethylhexyl (meth) acrylate, isononyl (meth) acrylate, and isodecyl (meth) acrylate.

The (meth) acrylate having a cyclic alkyl group is preferably a (meth) acrylate having a cyclic alkyl group having 6 to 12 carbon atoms. Examples of the cyclic alkyl group include a cyclic alkyl group having a single ring structure (for example, a cycloalkyl group). Specific examples of (meth) acrylates having a monocyclic cyclic alkyl group include cyclohexyl (meth) acrylate, methylcyclohexyl (meth) acrylate, and cyclododecyl (meth) acrylate.

The (meth) acrylate having a polycyclic structure is preferably a (meth) acrylate having a polycyclic structure having 6 to 12 carbon atoms. Examples of the polycyclic structure include a cyclic alkyl group having a bridged ring structure (for example, an adamantyl group, a norbornyl group, and an isobornyl group). Specific examples of the (meth) acrylate having a polycyclic structure include isobornyl (meth) acrylate, dicyclopentenyloxyethyl (meth) acrylate, dicyclopentanyloxyethyl (meth) acrylate, and 2-methyl-2-adamantyl. (Meth) acrylate, 2-ethyl-2-adamantyl (meth) acrylate, and the like.

The (meth) acrylate having an aromatic group is preferably a (meth) acrylate having an aromatic group having 6 to 12 carbon atoms. Examples of the aromatic group include an aryl group and the like, and may have a chain portion such as an alkylaryl group, an aralkyl group, and an aryloxyalkyl group. Specific examples of the (meth) acrylate having an aromatic group include benzyl (meth) acrylate, phenyl (meth) acrylate, and phenoxyethyl (meth) acrylate.

Examples of the (meth) acrylate having a polyalkylene glycol structural unit include polyethylene glycol (degree of polymerization = 2 to 10) methyl ether (meth) acrylate, polyethylene glycol (degree of polymerization = 2 to 10) ethyl ether (meth) acrylate, polyethylene (Meth) acrylates having a polyethylene glycol structural unit such as glycol (degree of polymerization = 2 to 10) propyl ether (meth) acrylate, polyethylene glycol (degree of polymerization = 2 to 10) phenyl ether (meth) acrylate; polypropylene glycol (degree of polymerization = 2 to 10) methyl ether (meth) acrylate, polypropylene glycol (degree of polymerization = 2 to 10) ethyl ether (meth) acrylate, polypropylene glycol (degree of polymerization = 2 to 10) propyl Ether (meth) acrylate, polypropylene glycol (polymerization degree = 2-10) with polypropylene glycol structural units such as phenyl ether (meth) acrylate (meth) acrylate.

Examples of the (meth) acrylate having a hydroxy group include 2-hydroxyethyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, and 6- Examples include hydroxyhexyl (meth) acrylate, 8-hydroxyoctyl (meth) acrylate, 10-hydroxydecyl (meth) acrylate, and 12-hydroxylauryl (meth) acrylate. Among these, a (meth) acrylate having a hydroxyalkyl group having 1 to 5 carbon atoms is more preferable.

（Examples of the (meth) acrylate having a lactone-modified hydroxy group include those obtained by adding a lactone to the (meth) acrylate having a hydroxy group, and those obtained by adding caprolactone are preferable. The added amount of caprolactone is preferably 1 mol to 10 mol, more preferably 1 mol to 5 mol. Examples of the (meth) acrylate having a lactone-modified hydroxy group include 2-hydroxyethyl (meth) acrylate adduct of 1 mol of caprolactone, 2-hydroxyethyl (meth) acrylate adduct of 2 mol of caprolactone, and 2-hydroxyethyl (meth) acrylate Are preferably 3 mol adduct of caprolactone, 4 mol adduct of caprolactone of 2-hydroxyethyl (meth) acrylate, 5 mol adduct of caprolactone of 2-hydroxyethyl (meth) acrylate, and 10 mol adduct of caprolactone of 2-hydroxyethyl (meth) acrylate. .

（Examples of the (meth) acrylate having an alkoxy group include methoxyethyl (meth) acrylate and ethoxyethyl (meth) acrylate.

として As the (meth) acrylate having an oxygen-containing heterocyclic group, a (meth) acrylate having a 4- to 6-membered oxygen-containing heterocyclic group is preferable. Specific examples of the (meth) acrylate having an oxygen-containing heterocyclic group include glycidyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, (3-ethyloxetane-3-yl) methyl (meth) acrylate, and (2- Methyl-2-ethyl-1,3-dioxolan-4-yl) methyl (meth) acrylate, cyclic trimethylolpropaneformal (meth) acrylate, 2-[(2-tetrahydropyranyl) oxy] ethyl (meth) acrylate, 1,3-dioxane- (meth) acrylate and the like.

Examples of the acidic group include a carboxy group (—COOH), a sulfonic acid group (—SO ₃ H), a phosphoric acid group (—OPO ₃ H ₂ ), a phosphonic acid group (—PO ₃ H ₂ ), and a phosphinic acid group (— PO ₂ H ₂ ). Examples of the (meth) acrylate having an acidic group include (meth) acrylate having a carboxy group, (meth) acrylate having a phosphoric acid group, and (meth) acrylate having a sulfonic acid group.

Examples of the (meth) acrylate having a carboxy group include carboxyethyl (meth) acrylate, carboxypentyl (meth) acrylate, 2- (meth) acryloyloxyethyl succinate, 2- (meth) acryloyloxyethyl maleate, Examples include monomers obtained by reacting a (meth) acrylate having a hydroxy group such as (meth) acryloyloxyethyl phthalate with an acid anhydride such as maleic anhydride, succinic anhydride, or phthalic anhydride. Examples of the (meth) acrylate having a sulfonic acid group include ethyl sulfonic acid (meth) acrylate. Examples of the (meth) acrylate having a phosphate group include 2- (phosphonooxy) ethyl (meth) acrylate.

The A block may have a structural unit other than the structural unit derived from the (meth) acrylic monomer. Other structural units that can be included in the A block are not particularly limited as long as they are formed of a vinyl monomer that can be copolymerized with both a (meth) acrylic monomer and a vinyl monomer that forms a B block described below. Vinyl monomers capable of forming other structural units of the A block may be used alone or in combination of two or more.

Specific examples of vinyl monomers that can form other structural units of the A block include α-olefins, aromatic vinyl monomers, heterocyclic-containing vinyl monomers, vinylamides, vinyl carboxylate, and dienes. These vinyl monomers may have a hydroxy group or an epoxy group.

Examples of the α-olefin include 1-hexene, 1-octene, 1-decene and the like.
Examples of the aromatic vinyl monomer include styrene, α-methylstyrene, 4-methylstyrene, 2-methylstyrene, 3-methylstyrene, 4-methoxystyrene, 2-hydroxymethylstyrene, 1-vinylnaphthalene, and the like.
Examples of the vinyl monomer containing a hetero ring include 2-vinylthiophene, N-methyl-2-vinylpyrrole, 1-vinyl-2-pyrrolidone, 2-vinylpyridine, 4-vinylpyridine, N-phenylmaleimide, and N-benzyl Maleimide, N-cyclohexylmaleimide and the like.
Examples of vinylamide include N-vinylformamide, N-vinylacetamide, N-vinyl-ε-caprolactam, and the like.
Examples of the vinyl carboxylate include vinyl acetate, vinyl pivalate, vinyl benzoate and the like.
Examples of dienes include butadiene, isoprene, 4-methyl-1,4-hexadiene, 7-methyl-1,6-octadiene and the like.

The A block preferably contains a structural unit represented by the general formula (10), that is, a structural unit derived from the (meth) acrylate having a lactone-modified hydroxy group. Since the structural unit represented by the general formula (10) has an ester bond portion and a terminal hydroxy group in a side chain, it has high affinity for a dispersion medium and a binder resin, and has an alkali developability of a block copolymer. Enhance.

[In the general formula (10), n1 represents an integer of 1 to 10. R ¹ represents a hydrogen atom or a methyl group. R ² represents an alkylene group having 1 to 10 carbon atoms. R ³ represents an alkylene group having 1 to 10 carbon atoms. ]

Ｎn1 in the above formula (10) is preferably an integer of 1 to 7, more preferably an integer of 1 to 5.

The alkylene group having 1 to 10 carbon atoms represented by R ² may be linear or branched, but is preferably linear. Specific examples of the alkylene group having 1 to 10 carbon atoms represented by R ² include a methylene group, an ethylene group, a trimethylene group, a tetramethylene group, a pentamethylene group, a hexamethylene group, a heptamethylene group, an octamethylene group, Examples include a nonamethylene group, a decamethylene group, and a 1-methylethylene group. R ² is preferably an alkylene group having 1 to 5 carbon atoms.

The alkylene group having 1 to 10 carbon atoms represented by R ³ may be linear or branched, but is preferably linear. Specific examples of the alkylene group having 1 to 10 carbon atoms represented by R ³ include a methylene group, an ethylene group, a trimethylene group, a tetramethylene group, a pentamethylene group, a hexamethylene group, a heptamethylene group, an octamethylene group, Examples include a nonamethylene group and a decamethylene group. R ³ is preferably an alkylene group having 1 to 8 carbon atoms, and more preferably an alkylene group having 3 to 8 carbon atoms.

When the A block contains a structural unit represented by the general formula (10), the content is preferably 10% by mass or more, more preferably 20% by mass or more, and still more preferably 100% by mass of the A block. Is 30% by mass or more, particularly preferably 60% by mass or more, preferably 95% by mass or less, more preferably 90% by mass or less, and still more preferably 85% by mass or less. By adjusting the content of the structural unit derived from the (meth) acrylate having a lactone-modified hydroxy group within the above range, the alkali developability of the block copolymer can be increased.

The A block preferably has a structural unit derived from a vinyl monomer having an acidic group (preferably, (meth) acrylate or (meth) acrylic acid having an acidic group). By having a structural unit derived from a vinyl monomer having an acidic group, the solubility in an alkali developer is increased, and alkali developability can be improved. However, when the ratio increases, the affinity with the solvent and the alkali-soluble resin may be reduced. Therefore, it is preferable that the ratio of the structural unit derived from the vinyl monomer having an acidic group be a ratio at which the overall acid value of the block copolymer is lower than the amine value.

(4) When a structural unit derived from a vinyl monomer having an acidic group is contained, the content is preferably 2% by mass or more and 100% by mass or less in 100% by mass of the A block. When the content of the structural unit derived from the vinyl monomer having an acidic group is 2% by mass or more, the dissolution rate upon neutralization with an alkali increases in alkali development, and when the content is 20% by mass or less, the hydrophilicity is high. This makes it possible to prevent the formed pixels from being cluttered.

In the A block, the content of the structural unit represented by the general formula (1) described below is less than 10% by mass, preferably 3% by mass or less, more preferably 1% by mass or less, and further preferably 0.1% by mass or less. Most preferably, it does not contain the structural unit represented by the general formula (1) by mass% or less. As the content of the structural unit represented by the general formula (1) in the A block is lower, the dispersibility of the coloring material is improved.

The 好ましい A block preferably has no amino group. That is, it is preferable that the vinyl monomer constituting the A block does not contain a vinyl monomer having an amino group. When a large amount of amino group is present in the A block, when used as a dispersant, the coloring material is adsorbed on both the A block and the B block, and the dispersing performance of the coloring material is reduced. The content of the structural unit derived from the vinyl monomer having an amino group in the A block (including a quaternized amino group) is preferably 3% by mass or less, more preferably 1% by mass or less, The content is more preferably 0.1% by mass or less, and most preferably 0% by mass.

When two or more structural units are contained in the A block, the various structural units contained in the A block may be contained in the A block in any mode such as random copolymerization and block copolymerization. From the viewpoint of uniformity, it is preferable that the compound is contained in a mode of random copolymerization. For example, the A block may be formed of a copolymer of a structural unit composed of an a1 block and a structural unit composed of an a2 block.

(B block)
The B block is a polymer block containing a structural unit represented by the following general formula (1).

(Structural unit represented by general formula (1))
The structural unit represented by the general formula (1) may be only one type, or may have two or more types. By having the structural unit represented by the general formula (1), the adsorptivity to a coloring material is high, and generation of formaldehyde over time can be suppressed. In the structural unit represented by the general formula (1), -Y ¹ -NR ¹¹ R ¹² bonded to X ¹ is a structure represented by the general formula (5).

R ¹¹ and R ¹² in the general formula (1) has the same meaning as R ¹¹ and R ¹² in the general formula (5). Examples of the chain hydrocarbon group and the cyclic hydrocarbon group represented by R ¹¹ and R ¹² in the general formula (1) include those exemplified as R ¹¹ and R ¹² in the general formula (5). The carbon number of the linear alkyl group represented by R ¹¹ and R ¹² in the general formula (1) is preferably 2 to 20 carbon atoms, more preferably 2 to 10 carbon atoms, and further preferably 2 to 5 carbon atoms. Preferably, the number of carbon atoms in the branched alkyl group is preferably from 3 to 20, more preferably from 3 to 10, and even more preferably from 3 to 5.

Examples of the cyclic structure formed by combining R ¹¹ and R ¹² with each other include a 5- to 7-membered nitrogen-containing heterocycle or a condensed ring formed by condensing two of them. The nitrogen-containing hetero ring preferably has no aromaticity, and is more preferably a saturated ring. Specific examples include structures represented by the following formulas (1-1), (1-2), and (1-3).

[In the general formulas (1-1), (1-2) and (1-3), R ¹⁴ represents an alkyl group having 1 to 6 carbon atoms. l represents an integer of 0 to 5. m represents an integer of 0 to 4. n represents an integer of 0 to 4. * Represents a bond. When 1 is 2 to 5, m is 2 to 4, and n is 2 to 4, a plurality of R ¹⁴ may be the same or different. ]

X ¹ represents an amide group (—CO—NH—), an ester group (—CO—O—), or a single bond. In addition, the bonding direction of the amide group and the ester group is not particularly limited. Examples of the bonding mode of the amide group include C-CO-NH-Y ¹ and C-NH-CO-Y ¹ , and C-CO-NH-Y ¹ is preferable. Examples of the bonding mode of the ester group include C—CO—O—Y ¹ and C—O—CO—Y ¹ , with C—CO—O—Y ¹ being preferred.

Y ¹ in the general formula (1) has the same meaning as Y ¹ in the general formula (5). Y ¹ is preferably an alkylene group having 1 to 10 carbon atoms. The alkylene group may be linear or branched, but is preferably linear. Y ¹ is preferably an alkylene group having 1 to 5 carbon atoms.

Specific examples of the vinyl monomer forming the structural unit represented by the general formula (1) include ethylaminoethyl (meth) acrylate, ethylaminopropyl (meth) acrylate, ethylaminobutyl (meth) acrylate, and diethylaminoethyl (meth). ) Acrylate, diethylaminopropyl (meth) acrylate, diethylaminobutyl (meth) acrylate, propylaminoethyl (meth) acrylate, propylaminopropyl (meth) acrylate, propylaminobutyl (meth) acrylate, dipropylaminoethyl (meth) acrylate, Examples thereof include dipropylaminopropyl (meth) acrylate, dipropylaminobutyl (meth) acrylate, and tert-butylaminoethyl (meth) acrylate.

The content of the structural unit represented by the general formula (1) is preferably 10% by mass or more, more preferably 30% by mass or more, even more preferably 50% by mass or more in 100% by mass of the B block, and 98% by mass. % Or less, more preferably 80% by mass or less, and even more preferably 70% by mass or less. By setting the content of the structural unit represented by the general formula (1) in this range, it is considered that the colorant has high affinity.

The B block may have a structural unit represented by the general formula (2). The structural unit represented by the general formula (2) in the B block may be only one type, or may have two or more types. When the B block has the structural unit represented by the general formula (2), strong adsorption to the colorant surface can be maintained for a long time, and storage stability is further improved.

[In the general formula (2), R ²¹ represents a hydrogen atom, a linear or cyclic hydrocarbon group which may have a substituent. R ²² and R ²³ each independently represent a linear or cyclic hydrocarbon group which may have a substituent. R ²² and R ²³ may combine with each other to form a cyclic structure. R ²⁴ represents a hydrogen atom or a methyl group. X ² represents an amide group, an ester group, or a single bond. Y ² represents a divalent hydrocarbon group. ]

Examples of the chain hydrocarbon group represented by R ²¹ to R ²³ include a linear alkyl group and a branched alkyl group. The linear alkyl group preferably has 1 to 20 carbon atoms, more preferably has 2 to 20 carbon atoms, further preferably has 2 to 10 carbon atoms, and particularly preferably has 2 to 5 carbon atoms. Examples of the linear alkyl group include an ethyl group, an n-propyl group, an n-butyl group, an n-hexyl group, an n-octyl group, an n-nonyl group, an n-decyl group and an n-lauryl group. . The branched chain alkyl group preferably has 3 to 20 carbon atoms, more preferably 3 to 10 carbon atoms, and still more preferably 3 to 5 carbon atoms. Examples of the branched alkyl group include an isopropyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a 2-ethylhexyl group, a neopentyl group, and an isooctyl group.

Examples of the substituent on the chain hydrocarbon group represented by R ²¹ to R ²³ include a halogen group, an alkoxy group, a benzoyl group (—COC ₆ H ₅ ), and a hydroxy group.

Examples of the cyclic hydrocarbon group represented by R ²¹ to R ²³ include a cyclic alkyl group and an aromatic group, and the cyclic alkyl group and the aromatic group may have a chain portion. The cyclic alkyl group preferably has 4 to 18 carbon atoms, more preferably has 6 to 12 carbon atoms, and still more preferably has 6 to 10 carbon atoms. Examples of the cyclic alkyl group include a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and the like. The aromatic group preferably has 6 to 18 carbon atoms, more preferably 6 to 12 carbon atoms, and even more preferably 6 to 8 carbon atoms. Examples of the aromatic group include a phenyl group, a tolyl group, a xylyl group, and a mesityl group. Examples of the cyclic alkyl group having a chain portion and the chain portion of the aromatic group having a chain portion include an alkylene group having 1 to 12 carbon atoms, preferably an alkylene group having 1 to 6 carbon atoms, and more preferably Examples include alkylene groups of formulas 1 to 3.

Examples of the substituent on the cyclic hydrocarbon group represented by R ²¹ to R ²³ include a halogen group, an alkoxy group, a chain alkyl group, and a hydroxy group.

Examples of the cyclic structure formed by combining R ²² and R ²³ with each other include a 5- to 7-membered nitrogen-containing heterocycle or a condensed ring formed by condensing two of them. The nitrogen-containing hetero ring preferably has no aromaticity, and is more preferably a saturated ring. Specific examples include structures represented by the following formulas (2-1), (2-2), and (2-3).

[In the general formulas (2-1), (2-2) and (2-3), R ²⁵ is R ²¹ . R ²⁶ represents an alkyl group having 1 to 6 carbon atoms. l represents an integer of 0 to 5. m represents an integer of 0 to 4. n represents an integer of 0 to 4. * Represents a bond. When 1 is 2 to 5, m is 2 to 4, and n is 2 to 4, a plurality of R ²⁶ may be the same or different. ]

X ² represents an amide group (—CO—NH—), an ester group (—CO—O—), or a single bond. In addition, the bonding direction of the amide group and the ester group is not particularly limited. Examples of the bonding mode of the amide group include C-CO-NH-Y ² and C-NH-CO-Y ² , and C-CO-NH-Y ² is preferable. Examples of the bonding mode of the ester group include C—CO—O—Y ² and C—O—CO—Y ² , with C—CO—O—Y ² being preferred.

Examples of the divalent hydrocarbon group represented by Y ² include an alkylene group having 1 to 10 carbon atoms, an alkenylene group having 1 to 10 carbon atoms, and an areendiyl group having 6 to 10 carbon atoms. Among these, an alkylene group having 1 to 10 carbon atoms is preferable. The alkylene group may be linear or branched, but is preferably linear. Y ² is preferably an alkylene group having 1 to 5 carbon atoms.

Examples of Z ^- include a halogen anion, a carboxylate anion, a sulfate anion, a sulfonate anion, a phosphate anion, and a nitroxide anion.
Examples of the halogen anion include a fluoro anion, a chloro anion, a bromo anion and an iodo anion.
Examples of the carboxylate anion include an alkyl carboxylate anion such as an acetate anion and a propionate anion; and an aromatic carboxylate anion such as a benzoate anion.
Examples of the sulfate anion include an alkyl sulfate anion such as a methyl sulfate anion and an ethyl sulfate anion; and an aromatic sulfate anion such as a phenyl sulfate anion and a benzyl sulfate anion.
Examples of the sulfonate anion include alkyl sulfonate anions such as methanesulfonic acid anion and ethanesulfonic acid anion; and aromatic sulfonate anions such as benzenesulfonic acid anion and toluenesulfonic acid anion.
Examples of the phosphate anion include alkyl phosphate anions such as methyl phosphonate anion and ethyl phosphonate anion; and aromatic phosphate anions such as phenyl phosphonate anion and benzyl phosphonate anion.

Specific examples of the vinyl monomer forming the structural unit represented by the formula (2) include (meth) acryloyloxyethylbenzyldiethylammonium chloride, (meth) acryloyloxypropylbenzyldiethylammonium chloride, and (meth) acryloyloxybutylbenzyl. Diethyl ammonium chloride, (meth) acryloyloxyethylbenzyl diethylammonium bromide, (meth) acryloyloxypropylbenzyldiethylammonium bromide, (meth) acryloyloxybutylbenzyldiethylammonium bromide, (meth) acryloyloxyethylbenzyldiethylammonium iodide, (Meth) acryloyloxypropylbenzyldiethylammonium iodide, (meth) acryloyloxy Chill benzyl diethyl ammonium iodide, (meth) acryloyloxyethyl benzyl diethyl ammonium fluoride, (meth) acryloyloxy propyl benzyl diethyl ammonium fluoride, and (meth) acryloyloxy butyl benzyl diethyl ammonium fluoride and the like.

When a structural unit represented by the general formula (2) is contained, the content is preferably 2% by mass or more, more preferably 20% by mass or more, and 90% by mass or less in 100% by mass of the B block. Preferably, it is 70% by mass or less. By setting the content of the structural unit represented by the general formula (2) in this range, it is considered that the composition has high affinity with the coloring material.

The B block may include only the structural unit represented by the general formula (1) and the structural unit represented by the general formula (2), or may include another structural unit. From the viewpoint of maintaining the affinity with the coloring material, the total content of the structural unit represented by the general formula (1) and the structural unit represented by the general formula (2) in the B block is 100 mass of the B block. %, Preferably at least 80% by mass, more preferably at least 90% by mass, even more preferably at least 95% by mass. Further, the B block preferably does not substantially contain a structural unit derived from a vinyl monomer having an acidic group. That is, the content of the structural unit derived from the vinyl monomer having an acidic group is preferably 5% by mass or less, more preferably 2% by mass or less in 100% by mass of the B block.

Specific examples of the vinyl monomer capable of forming the other structural unit of the block B include the same as those exemplified as specific examples of the vinyl monomer capable of forming the other structural unit of the block A.

When two or more structural units are contained in the B block, various structural units contained in the B block may be contained in the B block in any mode such as random copolymerization and block copolymerization. From the viewpoint of uniformity, it is preferable that the compound is contained in a mode of random copolymerization. For example, the B block may be formed of a copolymer of a structural unit composed of a b1 block and a structural unit composed of a b2 block.

(Block copolymer)
The structure of the block copolymer is preferably a linear block copolymer. Further, the linear block copolymer may have any structure (arrangement), but from the viewpoint of the physical properties of the linear block copolymer or the physical properties of the composition, A block is A and B block is B. Group represented by (AB) _m type, (AB) _m -A type, (BA) _m -B type (m is an integer of 1 or more, for example, an integer of 1 to 3) It is preferable that the copolymer has at least one structure selected from the group consisting of: Among these, an AB type diblock copolymer is preferred from the viewpoint of handleability during processing and physical properties of the composition. By constituting the AB type diblock copolymer, the structural unit derived from the (meth) acrylic monomer in the A block and the structural unit represented by the general formula (1) in the B block are localized. It is considered that the colorant, the dispersing medium (solvent), and the binder resin (alkali-soluble resin) can efficiently act suitably. The block copolymer may have other blocks other than the A block and the B block.

The content of the A block is preferably 35% by mass or more, more preferably 40% by mass or more, still more preferably 45% by mass or more, and preferably 85% by mass or less, based on 100% by mass of the entire block copolymer. It is more preferably at most 80% by mass, further preferably at most 75% by mass. The content of the B block is preferably 15% by mass or more, more preferably 20% by mass or more, even more preferably 25% by mass or more, and preferably 65% by mass or less, based on 100% by mass of the whole block copolymer. The content is more preferably 60% by mass or less, and further preferably 55% by mass or less. By adjusting the content of the A block and the B block within the above range, the dispersing performance when used as a dispersant is further improved.

The mass ratio between the A block and the B block (A block / B block) in the block copolymer is preferably 50/50 or more, more preferably 55/45 or more, further more preferably 60/40 or more. / 5 or less, more preferably 90/10 or less, and even more preferably 80/20 or less. When the mass ratio of the A block and the B block is within the above range, the dispersing performance when used as a dispersant is further improved.

When the block copolymer contains a structural unit having an acidic group, the content of the structural unit derived from a vinyl monomer having an acidic group in the block copolymer is preferably 1% by mass or more, and more preferably 10% by mass or less. Is preferred.

The total content of the structural unit represented by the general formula (1) and the structural unit represented by the general formula (2) in the block copolymer is preferably 5% by mass or more, more preferably 10% by mass. As described above, the content is more preferably 20% by mass or more, preferably 50% by mass or less, more preferably 45% by mass or less, and still more preferably 40% by mass or less.

分子 The molecular weight of the block copolymer is measured by gel permeation chromatography (hereinafter referred to as “GPC”). The weight average molecular weight (Mw) of the block copolymer is preferably 3,000 or more, more preferably 4,000 or more, still more preferably 5,000 or more, and particularly preferably 6,000 or more. It is preferably at most 000, more preferably at most 30,000, further preferably at most 25,000, particularly preferably at most 20,000. When the weight average molecular weight is within the above range, the dispersing performance when used as a dispersant becomes better.

分子 The molecular weight distribution (PDI) of the block copolymer is preferably 2.5 or less, more preferably 2.0 or less, and even more preferably 1.6 or less. In the present invention, the molecular weight distribution (PDI) is determined by (weight average molecular weight of block copolymer (Mw)) / (number average molecular weight of block copolymer (Mn)). The smaller the PDI, the narrower the width of the molecular weight distribution, and the resulting copolymer becomes uniform in molecular weight. When the value is 1.0, the width of the molecular weight distribution is the narrowest. That is, the lower limit of PDI is 1.0. When the molecular weight distribution (PDI) of the block copolymer exceeds 2.5, those having a small molecular weight and those having a large molecular weight are included.

The amine value of the block copolymer is preferably 10 mgKOH / g or more, more preferably 50 mgKOH / g or more, further more preferably 80 mgKOH / g or more, from the viewpoints of adsorbability to the colorant and dispersibility of the colorant. It is preferably at most 200 mgKOH / g, more preferably at most 150 mgKOH / g, even more preferably at most 120 mgKOH / g.

場合 When the block copolymer contains a structural unit having an acidic group, the acid value of the block copolymer is preferably 5 mgKOH / g or more, and more preferably 50 mgKOH / g or less. By setting the acid value within this range, the block copolymer can suitably act on the binder resin (alkali-soluble resin) without impairing the affinity for the colorant.

(Method for producing block copolymer)
As a method for producing the block copolymer, a method in which an A block is first produced by a polymerization reaction of a vinyl monomer, and a monomer of a B block is polymerized in an A block; A method of polymerizing the monomer of the block; a method of separately producing the A block and the B block, and then coupling the A block and the B block.

The polymerization method is not particularly limited, but living radical polymerization is preferred. That is, the block copolymer is preferably a polymer obtained by living radical polymerization. In the conventional radical polymerization method, not only the initiation reaction and the growth reaction, but also the termination reaction and the chain transfer reaction cause the deactivation of the growth terminal, which tends to easily produce a mixture of polymers having various molecular weights and heterogeneous compositions. In contrast, the living radical polymerization method, while maintaining the simplicity and versatility of the conventional radical polymerization method, is unlikely to cause a termination reaction or chain transfer and grows without deactivating the growth terminal, so that the molecular weight distribution This is preferred because it is easy to produce a polymer having a precise composition and a uniform composition.

In the living radical polymerization method, a method using a transition metal catalyst (ATRP method); a method using a sulfur-based reversible chain transfer agent (RAFT method); There is a method such as a method used (TERP method). Since the ATRP method uses an amine-based complex, it cannot be used without protecting the acidic group of the vinyl monomer having an acidic group. In the RAFT method, when various types of monomers are used, a low molecular weight distribution is unlikely to occur, and there may be a problem such as a sulfur odor or coloring. Among these methods, it is preferable to use the TERP method from the viewpoints of diversity of usable monomers, control of molecular weight in a polymer region, uniform composition, and coloring.

The TERP method is a method of polymerizing a radical polymerizable compound (vinyl monomer) using an organic tellurium compound as a chain transfer agent. For example, WO2004 / 14848, WO2004 / 14962, WO No. 2004/072126 and WO 2004/096870.

Specific polymerization methods of the TERP method include the following (a) to (d).
(A) A vinyl monomer is polymerized using an organic tellurium compound represented by the general formula (3).
(B) A vinyl monomer is polymerized using a mixture of an organic tellurium compound represented by the general formula (3) and an azo-based polymerization initiator.
(C) A vinyl monomer is polymerized using a mixture of an organic telluride compound represented by the general formula (3) and an organic ditelluride compound represented by the general formula (4).
(D) A vinyl monomer is polymerized using a mixture of an organic telluride compound represented by the general formula (3), an azo-based polymerization initiator, and an organic ditelluride compound represented by the general formula (4).

[In the general formula (3), R ³¹ represents an alkyl group having 1 to 8 carbon atoms, an aryl group, or an aromatic heterocyclic group. R ³² and R ³³ each independently represent a hydrogen atom or an alkyl group having 1 to 8 carbon atoms. R ³⁴ represents an alkyl group having 1 to 8 carbon atoms, an aryl group, a substituted aryl group, an aromatic heterocyclic group, an alkoxy group, an acyl group, an amide group, an oxycarbonyl group, a cyano group, an allyl group or a propargyl group.
In the general formula (4), R ³¹ represents an alkyl group having 1 to 8 carbon atoms, an aryl group or an aromatic heterocyclic group. ]

The group represented by R ³¹ is an alkyl group having 1 to 8 carbon atoms, an aryl group or an aromatic heterocyclic group, and is specifically as follows.
Examples of the alkyl group having 1 to 8 carbon atoms include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, and heptyl. And a straight-chain or branched-chain alkyl group such as an octyl group, and a cyclic alkyl group such as a cyclohexyl group. It is preferably a linear or branched alkyl group having 1 to 4 carbon atoms, and more preferably a methyl group or an ethyl group.
Examples of the aryl group include a phenyl group and a naphthyl group.
Examples of the aromatic heterocyclic group include a pyridyl group, a furyl group, and a thienyl group.

The groups represented by R ³² and R ³³ are each independently a hydrogen atom or an alkyl group having 1 to 8 carbon atoms, and each group is specifically as follows.
Examples of the alkyl group having 1 to 8 carbon atoms include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, and heptyl. And a straight-chain or branched-chain alkyl group such as an octyl group, and a cyclic alkyl group such as a cyclohexyl group. It is preferably a linear or branched alkyl group having 1 to 4 carbon atoms, and more preferably a methyl group or an ethyl group.

The group represented by R ³⁴ is an alkyl group having 1 to 8 carbon atoms, an aryl group, a substituted aryl group, an aromatic heterocyclic group, an alkoxy group, an acyl group, an amide group, an oxycarbonyl group, a cyano group, an allyl group, It is a propargyl group, which is specifically as follows.
Examples of the alkyl group having 1 to 8 carbon atoms include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, and heptyl. And a linear or branched alkyl group such as a octyl group, and a cyclic alkyl group such as a cyclohexyl group. It is preferably a linear or branched alkyl group having 1 to 4 carbon atoms, and more preferably a methyl group or an ethyl group.
Examples of the aryl group include a phenyl group and a naphthyl group. Preferably it is a phenyl group.
Examples of the substituted aryl group include a phenyl group having a substituent and a naphthyl group having a substituent. Examples of the substituent of the aryl group having a substituent include a halogen atom, a hydroxy group, an alkoxy group, an amino group, a nitro group, a cyano group, and a carbonyl-containing group represented by —COR ³⁴¹ (where R ³⁴¹ is carbon Examples thereof include an alkyl group having 1 to 8 carbon atoms, an aryl group, an alkoxy group having 1 to 8 carbon atoms or an aryloxy group), a sulfonyl group, and a trifluoromethyl group. Further, these substituents are preferably substituted one or two times.
Examples of the aromatic heterocyclic group include a pyridyl group, a furyl group, and a thienyl group.
As the alkoxy group, a group in which an alkyl group having 1 to 8 carbon atoms is bonded to an oxygen atom is preferable. For example, a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, an n-butoxy group, a sec-butoxy group, a tert- Butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy and the like.
Examples of the acyl group include an acetyl group, a propionyl group, and a benzoyl group.
Examples of the amide group include —CONR ³⁴²¹ R ³⁴²² (R ³⁴²¹ and R ³⁴²² are each independently a hydrogen atom, an alkyl group or an aryl group having 1 to 8 carbon atoms).
As the oxycarbonyl group, a group represented by —COOR ³⁴³¹ (R ³⁴³¹ is a hydrogen atom, an alkyl group or an aryl group having 1 to 8 carbon atoms) is preferable, and examples thereof include a carboxy group, a methoxycarbonyl group, an ethoxycarbonyl group, and a propoxycarbonyl group. Groups, n-butoxycarbonyl group, sec-butoxycarbonyl group, tert-butoxycarbonyl group, n-pentyloxycarbonyl group, phenoxycarbonyl group and the like. Preferred oxycarbonyl groups include a methoxycarbonyl group and an ethoxycarbonyl group.
^{Examples of the} allyl group include -CR ³⁴⁴¹ R ³⁴⁴² -CR ³⁴⁴³ = CR ³⁴⁴⁴ R ³⁴⁴⁵ (R ³⁴⁴¹ and R ³⁴⁴² each independently represent a hydrogen atom or an alkyl group having 1 to 8 carbon atoms, and R ³⁴⁴³ , R ³⁴⁴⁴ and R ³⁴⁴⁵ represent And each independently is a hydrogen atom, an alkyl group or an aryl group having 1 to 8 carbon atoms, and the respective substituents may be connected by a cyclic structure).
Examples of the propargyl group include —CR ³⁴⁵¹ R ³⁴⁵² —C≡CR ³⁴⁵³ (R ³⁴⁵¹ and R ³⁴⁵² are a hydrogen atom or an alkyl group having 1 to 8 carbon atoms, and R ³⁴⁵³ is a hydrogen atom or an alkyl group having 1 to 8 carbon atoms. , An aryl group or a silyl group).

Specific examples of the organic tellurium compound represented by the general formula (3) include (methylteranylmethyl) benzene, (methylteranylmethyl) naphthalene, ethyl-2-methyl-2-methylteranyl-propionate, and ethyl-2-yl. Methyl-2-n-butylteranyl-propionate, (2-trimethylsiloxyethyl) -2-methyl-2-methylterranyl-propionate, (2-hydroxyethyl) -2-methyl-2-methylterranyl-propionate or (3-trimethylsilylpropargyl) ) -2-Methyl-2-methylterranyl-propionate and the like organic compounds described in WO 2004/14848, WO 2004/14962, WO 2004/072126, and WO 2004/096870. All of tellurium compounds It can be exemplified.

Specific examples of the organic ditelluride compound represented by the general formula (4) include dimethyl ditelluride, diethyl ditelluride, di-n-propyl ditelluride, diisopropyl ditelluride, dicyclopropyl ditelluride, -N-butyl ditelluride, di-s-butyl ditelluride, di-t-butyl ditelluride, dicyclobutyl ditelluride, diphenyl ditelluride, bis- (p-methoxyphenyl) ditelluride, bis- (p-aminophenyl) ditelluride, bis Examples include-(p-nitrophenyl) ditelluride, bis- (p-cyanophenyl) ditelluride, bis- (p-sulfonylphenyl) ditelluride, dinaphthyl ditelluride, dipyridyl ditelluride, and the like.

The azo polymerization initiator can be used without any particular limitation as long as it is an azo polymerization initiator used in ordinary radical polymerization. For example, 2,2′-azobis (isobutyronitrile) (AIBN), 2,2′-azobis (2-methylbutyronitrile) (AMBN), 2,2′-azobis (2,4-dimethylvaleronitrile) ) (ADVN), 1,1′-azobis (1-cyclohexanecarbonitrile) (ACHN), dimethyl-2,2′-azobisisobutyrate (MAIB), 4,4′-azobis (4-cyanovaleric acid) ) (ACVA), 1,1′-azobis (1-acetoxy-1-phenylethane), 2,2′-azobis (2-methylbutylamide), 2,2′-azobis (4-methoxy-2,4 -Dimethylvaleronitrile) (V-70), 2,2'-azobis (2-methylamidinopropane) dihydrochloride, 2,2'-azobis [2- (2-imidazolin-2-yl) Lopan], 2,2′-azobis [2-methyl-N- (2-hydroxyethyl) propionamide], 2,2′-azobis (2,4,4-trimethylpentane), 2-cyano-2-propyl Examples include azoformamide, 2,2′-azobis (N-butyl-2-methylpropionamide), and 2,2′-azobis (N-cyclohexyl-2-methylpropionamide).

In the polymerization step, the vinyl monomer and the organic tellurium compound of the general formula (3) are further substituted with an inert gas for the purpose of accelerating the reaction and controlling the molecular weight and the molecular weight distribution according to the type of the vinyl monomer. A system polymerization initiator and / or an organic ditelluride compound of the general formula (4) are mixed. At this time, examples of the inert gas include nitrogen, argon, and helium. Preferably, argon and nitrogen are good.

ビニル The amount of the vinyl monomer used in (a), (b), (c) and (d) may be appropriately adjusted depending on the physical properties of the desired copolymer. It is preferable that the vinyl monomer is 5 mol to 10000 mol per 1 mol of the organic tellurium compound of the general formula (3).

When the organic tellurium compound of the general formula (3) and the azo-based polymerization initiator (b) are used in combination, the azo-based polymerization initiator is used in an amount of 0.01 mol to 10 mol per 1 mol of the organic tellurium compound of the general formula (3). It is preferable that

When the organic telluride compound represented by the general formula (3) and the organic ditelluride compound represented by the general formula (4) are used in combination, 1 mol of the organic tellurium compound represented by the general formula (3) is added to the organic tellurium compound represented by the general formula (4). It is preferable that the ditelluride compound be 0.01 mol to 100 mol.

In the case where the organic telluride compound of the general formula (3), the organic ditelluride compound of the general formula (4) and the azo-based polymerization initiator are used in combination with each other, 1 mol of the organic tellurium compound of the general formula (3) is generally used. The amount of the organic ditelluride compound of the formula (4) is preferably from 0.01 mol to 100 mol, and the amount of the azo-based polymerization initiator is preferably from 0.01 mol to 10 mol per 1 mol of the organic telluride compound of the general formula (3).

The polymerization reaction can be carried out without a solvent, but may be carried out by using an aprotic solvent or a protic solvent generally used in radical polymerization and stirring the mixture. Examples of usable aprotic solvents include anisole, benzene, toluene, N, N-dimethylformamide (DMF), dimethyl sulfoxide (DMSO), acetone, 2-butanone (methyl ethyl ketone), dioxane, propylene glycol monomethyl ether acetate, and chloroform. , Carbon tetrachloride, tetrahydrofuran (THF), ethyl acetate or trifluoromethylbenzene. Examples of the protic solvent include water, methanol, ethanol, isopropanol, n-butanol, ethyl cellosolve, butyl cellosolve, 1-methoxy-2-propanol, hexafluoroisopropanol and diacetone alcohol.

The amount of the solvent to be used may be appropriately adjusted. For example, the amount is preferably 0.01 ml or more, more preferably 0.05 ml or more, still more preferably 0.1 ml or more, and 50 ml or less, per 1 g of the vinyl monomer. It is preferably 10 ml or less, more preferably 1 ml or less.

The reaction temperature and the reaction time may be appropriately adjusted depending on the molecular weight or molecular weight distribution of the obtained copolymer. Usually, the mixture is stirred at 0 ° C. to 150 ° C. for 1 minute to 100 hours. The TERP method can obtain a high yield and a precise molecular weight distribution even at a low polymerization temperature and a short polymerization time. At this time, the pressure is usually set at normal pressure, but may be increased or decreased.

(4) After the completion of the polymerization reaction, the target copolymer can be separated from the obtained reaction mixture by removing the solvent used, residual vinyl monomer, and the like by ordinary separation and purification means.

The growth terminal of the copolymer obtained by the polymerization reaction is in the form of -TeR ³¹ derived from a tellurium compound (where R ³¹ is the same as above), and is deactivated by the operation in the air after the completion of the polymerization reaction. However, tellurium atoms may remain. Since the copolymer having a tellurium atom at the terminal is colored or has poor thermal stability, it is preferable to remove the tellurium atom.

As a method for removing tellurium atoms, a radical reduction method using tributylstannane or a thiol compound; a method of adsorbing with activated carbon, silica gel, activated alumina, activated clay, molecular sieves, a polymer adsorbent, etc .; A method for adsorbing a metal: a peroxide such as hydrogen peroxide or benzoyl peroxide is added, or air or oxygen is blown into the system to oxidize and decompose the tellurium atom at the terminal of the copolymer, and to wash with water or an appropriate solution. A liquid-liquid extraction method or solid-liquid extraction method for removing residual tellurium compounds by combining solvents; a purification method in a solution state such as ultrafiltration for extracting and removing only those having a specific molecular weight or less can be used. Also, these methods can be used in combination.

The other end of the copolymer obtained by the polymerization reaction (the end opposite to the growth end) is -CR ³² R ³³ R ³⁴ derived from the tellurium compound (where R ³² , R ³³ and R ³⁴ are represented by the formula: (The same as R ³² , R ³³ and R ^{34 in} (3).)

When the tertiary amine group of the structural unit represented by the formula (1) is quaternized, quaternizing agents include alkyl halides such as methyl chloride, ethyl chloride, methyl bromide, and methyl iodide; benzyl chloride Aralkyl halides such as benzyl bromide and benzyl iodide; dimethyl sulfate; and dialkyl sulfates such as diethyl sulfate and di-n-propyl sulfate. Of these, aralkyl halides such as benzyl chloride, benzyl bromide and benzyl iodide are preferred, and benzyl chloride is more preferred. An alkyl group and an aralkyl group derived from a quaternizing agent are introduced into the quaternized structure. Therefore, by measuring the amount of the alkyl group and the aralkyl group introduced by the quaternization, the amount of the structural unit represented by the formula (2) can be estimated.

方法 As a method of quaternizing a part of the tertiary amine structure of the structural unit represented by the formula (1) in the polymer, a method of contacting the polymer with a quaternizing agent may be mentioned. Specifically, after polymerizing a monomer composition containing a vinyl monomer capable of forming a structural unit represented by the formula (1), a quaternizing agent is added to the reaction solution, followed by stirring. . The temperature of the reaction solution to which the quaternizing agent is added is preferably 55 ° C. to 65 ° C., and the stirring time is preferably 5 hours to 20 hours. When adding the quaternizing agent, it is also preferable to dilute the reaction solution after polymerization. Examples of the solvent to be added for dilution include a solvent that can be used for a polymerization reaction, a protic solvent is preferable, and methanol is more preferable.

(Polymerization product)
The dispersant composition may use a polymerization product containing the block copolymer as a dispersant component. The polymerization product refers to a product obtained by performing a polymerization operation (a quaternization treatment as necessary) to obtain the block copolymer. The polymerization product contains a desired block copolymer and a polymer impurity by-produced when synthesizing the block copolymer.

The polymer impurities are other polymers that are inevitably produced as by-products when synthesizing a desired block copolymer. For example, as a polymer impurity by-produced when synthesizing the AB diblock copolymer, a random polymer having the same composition as the A block and a random polymer having the same composition as the B block can be given. The polymer impurity is a polymer by-produced when synthesizing a desired block copolymer, and does not include a polymer added separately.

含有 The content of the block copolymer in the polymerization product is preferably 50% by mass or more based on 100% by mass of the polymerization product. When the content of the block copolymer in the polymerization product is 50% by mass or more, the dispersing performance is improved when the polymerization product is used as a dispersant.

(Dispersion medium)
The dispersant composition may contain a dispersion medium. The dispersing medium can be appropriately selected and used as long as it disperses or dissolves the block copolymer, does not react with these components, and has an appropriate volatility. For example, conventionally known organic solvents can be used, for example, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene Glycol mono-n-butyl ether, propylene glycol-t-butyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol mono-n-butyl ether, methoxymethyl pentanol, methoxypropanol, propylene glycol monoethyl ether, dipropylene glycol monoethyl ether , Dipropylene glycol monomethyl Glycol monoalkyl ethers such as ether, 3-methyl-3-methoxybutanol, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, tripropylene glycol methyl ether; ethylene glycol dimethyl ether, ethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol Glycol dialkyl ethers such as diethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether and dipropylene glycol dimethyl ether; ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, ethylene glycol mono-n-butyl ether acetate, propylene Glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, propylene glycol monobutyl ether acetate, methoxybutyl acetate, 3-methoxybutyl acetate, methoxypentyl acetate, diethylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, Glycol alkyl ether acetates such as diethylene glycol mono-n-butyl ether acetate, dipropylene glycol monomethyl ether acetate, triethylene glycol monomethyl ether acetate, triethylene glycol monoethyl ether acetate, 3-methyl-3-methoxybutyl acetate Glycol diacetates such as ethylene glycol diacetate, 1,3-butylene glycol diacetate and 1,6-hexanediol diacetate; alkyl acetates such as cyclohexanol acetate; amyl ether, propyl ether, diethyl ether; Ethers such as dipropyl ether, diisopropyl ether, butyl ether, diamyl ether, ethyl isobutyl ether, dihexyl ether; acetone, methyl ethyl ketone, methyl amyl ketone, methyl isopropyl ketone, methyl isoamyl ketone, diisopropyl ketone, diisobutyl ketone, methyl isobutyl ketone, Cyclohexanone, ethyl amyl ketone, methyl butyl ketone, methyl hexyl ketone, methyl nonyl ketone, methoxy methyl Ketones such as pentanone; monohydric or polyhydric alcohols such as ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, butanediol, diethylene glycol, dipropylene glycol, triethylene glycol, glycerin and benzyl alcohol; Aliphatic hydrocarbons such as n-pentane, n-octane, diisobutylene, n-hexane, hexene, isoprene, dipentene, dodecane; alicyclic hydrocarbons such as cyclohexane, methylcyclohexane, methylcyclohexene, bicyclohexyl; benzene , Toluene, xylene, cumene and other aromatic hydrocarbons; amyl formate, ethyl formate, ethyl acetate, butyl acetate, propyl acetate, amyl acetate, methyl isobutyrate , Ethylene glycol acetate, ethyl propionate, propyl propionate, butyl butyrate, isobutyl butyrate, methyl isobutyrate, ethyl caprylate, butyl stearate, ethyl benzoate, methyl 3-ethoxypropionate, 3-ethoxypropionic acid Linear or cyclic esters such as ethyl, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, propyl 3-methoxypropionate, butyl 3-methoxypropionate, and γ-butyrolactone; 3-methoxypropionic acid, Alkoxycarboxylic acids such as ethoxypropionic acid; halogenated hydrocarbons such as butyl chloride and amyl chloride; ether ketones such as methoxymethylpentanone; nitriles such as acetonitrile and benzonitrile. That.

含有 The content of the dispersion medium in the dispersant composition is not particularly limited, and can be appropriately adjusted. The upper limit of the content of the dispersion medium in the dispersant composition is usually 99% by mass. In addition, the lower limit of the content of the dispersion medium in the dispersant composition is usually 10% by mass, and preferably 30% by mass, in consideration of a viscosity suitable for producing a coloring composition described later.

<Coloring composition>
The coloring composition of the present invention contains the dispersant composition, a coloring material, a binder resin and a dispersion medium.

(Coloring material)
The type of the coloring material may be appropriately selected according to its use, and examples thereof include pigments and dyes. It is preferable that the coloring composition contains a pigment as a coloring material from the viewpoint of light resistance and heat resistance. The pigment may be either an organic pigment or an inorganic pigment, but an organic pigment containing an organic compound as a main component is particularly preferable. Examples of the pigment include pigments of each color such as a red pigment, a yellow pigment, an orange pigment, a blue pigment, a green pigment, and a violet pigment. Pigment structures include azo pigments such as monoazo pigments, diazo pigments, and condensed diazo pigments, diketopyrrolopyrrole pigments, phthalocyanine pigments, isoindolinone pigments, isoindoline pigments, quinacridone pigments, indigo And polycyclic pigments such as thioindigo pigments, quinophthalone pigments, dioxazine pigments, anthraquinone pigments, perylene pigments, and perinone pigments. The pigment contained in the coloring composition may be only one type or a plurality of types.

具体 Specific examples of pigments include C.I. I. Pigment Red 7, 9, 14, 41, 48: 1, 48: 2, 48: 3, 48: 4, 81: 1, 81: 2, 81: 3, 122, 123, 146, 149, 166, 168, Red pigments such as 177, 178, 179, 187, 200, 202, 208, 210, 215, 224, 254, 255, 264, 269; I. Pigment Yellow 1, 3, 5, 6, 14, 55, 60, 61, 62, 63, 65, 73, 74, 77, 81, 93, 97, 98, 104, 108, 110, 138, 139, 147, Yellow pigments such as 150, 151, 154, 155, 166, 167, 168, 170, 180, 185, 188, 193, 194, 213; I. Orange pigments such as CI Pigment Orange 36, 38, 43; I. Blue pigments such as C.I. Pigment Blue 15, 15: 2, 15: 3, 15: 4, 15: 6, 16, 22, 60; I. Pigment Green 7, 36, 58, 59, 62, 63, aluminum phthalocyanine, polyhalogenated aluminum phthalocyanine, aluminum phthalocyanine hydroxide, diphenoxyphosphinyloxyaluminum phthalocyanine, diphenylphosphinyloxyaluminum phthalocyanine, polyhalogenated diphenoxy Green pigments such as phosphinyloxyaluminum phthalocyanine and polyhalogenated diphenylphosphinyloxyaluminum phthalocyanine; I. Pigment Violet 23, 32, 50, and the like. Pigments are, among these, C.I. I. Pigment Red 254, C.I. I. Pigment Red 255, C.I. I. Pigment Red 264, C.I. I. Pigment Blue 15, C.I. I. Pigment Blue 15: 2, C.I. I. Pigment Blue 15: 3, C.I. I. Pigment Blue 15: 4, C.I. I. Pigment Blue 15: 6, C.I. I. Pigment Blue 16, C.I. I. Pigment Green 7, C.I. I. Pigment Green 36, C.I. I. Pigment Green 58, C.I. I. Pigment Green 59 or the like is preferable.

黒色 When forming a light-shielding material such as a black matrix of a color filter using the coloring composition of the present invention, a black pigment can be used. The black pigment may be used alone, or the red pigment, the green pigment, the blue pigment, and the like may be mixed and used. Examples of the black pigment include carbon black, acetylene black, lamp black, bone black, graphite, iron black, and titanium black. Among these, carbon black and titanium black are preferable from the viewpoint of light blocking ratio and image characteristics.

平均 The average particle size of the colorant may be appropriately selected according to the application, and is not particularly limited. It is preferable that the coloring composition contains a coloring material having an average particle diameter of 10 nm to 150 nm from the viewpoint of high transparency and high contrast.

The coloring material may contain a pigment derivative as a dispersing aid. The dye derivative preferably contains an acidic dye derivative having an acidic group so as to be ionically bonded to and adsorbed to an amino group in the polymer contained in the dispersant composition. This dye derivative has an acidic functional group introduced into the dye skeleton. As the dye skeleton, a skeleton that is the same or similar to the coloring material constituting the coloring composition, or a skeleton that is the same or similar to the compound that is a raw material of the pigment is preferable. Specific examples of the dye skeleton include an azo dye skeleton, a phthalocyanine dye skeleton, an anthraquinone dye skeleton, a triazine dye skeleton, an acridine dye skeleton, and a perylene dye skeleton. As the acidic group introduced into the dye skeleton, a carboxy group, a phosphoric acid group, and a sulfonic acid group are preferable. In addition, a sulfonic acid group is preferable on account of the synthesis and the strength of the acidity. The acidic group may be directly bonded to the dye skeleton, or may be bonded to the dye skeleton via a hydrocarbon group such as an alkyl group or an aryl group; an ester, an ether, a sulfonamide, or a urethane bond. The amount of the dye derivative used is not particularly limited, but is preferably, for example, 4 to 17 parts by mass with respect to 100 parts by mass of the coloring material.

From the viewpoint of luminance, the upper limit of the content of the coloring material in the coloring composition is usually 80% by mass, preferably 70% by mass, and more preferably 60% by mass in the total solid content of the coloring composition. Is more preferable. In addition, the lower limit of the content of the coloring material in the coloring composition is usually 10% by mass, preferably 20% by mass, and more preferably 30% by mass in the total solid content of the coloring composition. preferable. Here, the solid content is a component other than the dispersion medium described below.

The content of the dispersant component (block copolymer and polymerization product) with respect to the coloring material in the coloring composition is preferably 5 parts by mass to 200 parts by mass, and more preferably 10 parts by mass to 100 parts by mass of the coloring material. It is preferably 100 parts by mass, more preferably 10 parts by mass to 80 parts by mass.

(Binder resin)
The coloring composition contains a binder resin (however, a polymer having a structure represented by the general formula (5) in the side chain is excluded). Thereby, the alkali developability of the coloring composition and the binding property to the substrate can be improved. Such a binder resin is not particularly limited, but is preferably a resin having an acidic group such as a carboxy group and a phenolic hydroxy group.

ランダム As the binder resin, a random copolymer containing a structural unit derived from a carboxy group-containing vinyl monomer and a structural unit derived from (meth) acrylate is preferable. As the carboxy group-containing vinyl monomer, (meth) acrylic acid is preferable. Examples of the (meth) acrylate include methyl (meth) acrylate, butyl (meth) acrylate, and benzyl (meth) acrylate.

In the binder resin, the total content of structural units derived from a carboxy group-containing vinyl monomer and structural units derived from (meth) acrylate is preferably 50% by mass or more, more preferably 60% by mass or more, and still more preferably 70% by mass or more. The binder resin has a content of a structure derived from a carboxy group-containing vinyl monomer of preferably 5% by mass or more, more preferably 10% by mass or more, further preferably 20% by mass or more, and 90% by mass or less. And more preferably 70% by mass or less.

の Among these, a random copolymer of a carboxy group-containing vinyl monomer and (meth) acrylate is preferable. Specific examples of such a copolymer include a random copolymer of (meth) acrylic acid and butyl (meth) acrylate, a random copolymer of (meth) acrylic acid and benzyl (meth) acrylate, ) A random copolymer of acrylic acid, butyl (meth) acrylate, and benzyl (meth) acrylate. From the viewpoint of the affinity between the binder resin and the coloring material, the binder resin is particularly preferably a random copolymer of (meth) acrylic acid and benzyl (meth) acrylate.

In the copolymer of a carboxy group-containing vinyl monomer and (meth) acrylate, the content of (meth) acrylic acid is usually from 5% by mass to 90% by mass, and preferably from 10% by mass to 70% by mass of all monomer components. Is more preferable, and more preferably 20% by mass to 70% by mass.

The binder resin may have a radically polymerizable carbon-carbon double bond in a side chain. By having a double bond in the side chain, the photocurability of the coloring composition according to the present invention is increased, so that the resolution and adhesion can be further improved. Examples of a method of introducing a radically polymerizable carbon-carbon double bond into a side chain include, for example, glycidyl (meth) acrylate, 3,4-epoxycyclohexylmethyl (meth) acrylate, o- (or m-, or p- A) a method of reacting a compound such as vinylbenzyl glycidyl ether with an acidic group of the binder resin.

ＭMw of the binder resin is preferably from 3,000 to 100,000, more preferably from 5,000 to 50,000, even more preferably from 5,000 to 20,000. When the Mw of the binder resin is 3,000 or more, the heat resistance and the film strength of the colored layer formed from the colored composition are improved, and when the Mw is 100,000 or less, the alkali developability of the coating film is improved. Is further improved.

The acid value of the binder resin is preferably from 20 mgKOH / g to 170 mgKOH / g, more preferably from 50 mgKOH / g to 150 mgKOH / g, and still more preferably from 90 mgKOH / g to 150 mgKOH / g. When the acid value of the binder resin is 20 mgKOH / g or more / g, the alkali developability of the colored composition as a colored layer is further improved, and when it is 170 mgKOH / g or less, the heat resistance becomes good.

は The binder resin contained in the coloring composition may be only one kind or plural kinds. In the coloring composition, the content of the binder resin is preferably 3 parts by mass to 200 parts by mass, more preferably 10 parts by mass to 100 parts by mass, and more preferably 20 parts by mass with respect to 100 parts by mass of the coloring material. More preferably, the amount is from 80 parts by mass to 80 parts by mass.

(Crosslinking agent)
The coloring composition may contain a crosslinking agent as necessary. A crosslinking agent refers to a compound having two or more polymerizable groups. Examples of the polymerizable group include an ethylenically unsaturated group, an oxiranyl group, an oxetanyl group, and an N-alkoxymethylamino group. As the crosslinking agent, a compound having two or more (meth) acryloyl groups or a compound having two or more N-alkoxymethylamino groups is preferable.

Specific examples of the compound having two or more (meth) acryloyl groups include polyfunctional (meth) acrylates obtained by reacting an aliphatic polyhydroxy compound with (meth) acrylic acid, and caprolactone-modified polyfunctional ( (Meth) acrylate, polyfunctional (meth) acrylate modified with alkylene oxide, polyfunctional urethane (meth) acrylate obtained by reacting (meth) acrylate having a hydroxy group with polyfunctional isocyanate, (meth) acrylate having a hydroxy group And a polyfunctional (meth) acrylate having a carboxy group obtained by reacting an acid anhydride with an acid anhydride.

Examples of the aliphatic polyhydroxy compound include divalent aliphatic polyhydroxy compounds such as ethylene glycol, propylene glycol, polyethylene glycol, and polypropylene glycol; and trivalent or higher valent compounds such as glycerin, trimethylolpropane, pentaerythritol, and dipentaerythritol. Aliphatic polyhydroxy compounds. Examples of the (meth) acrylate having a hydroxy group include 2-hydroxyethyl (meth) acrylate, trimethylolpropane di (meth) acrylate, pentaerythritol tri (meth) acrylate, dipentaerythritol penta (meth) acrylate, Pentaerythritol hexa (meth) acrylate, glycerol di (meth) acrylate and the like can be mentioned. Examples of the polyfunctional isocyanate include tolylene diisocyanate, hexamethylene diisocyanate, diphenylmethylene diisocyanate, and isophorone diisocyanate. Examples of the acid anhydride include dibasic acid anhydrides such as succinic anhydride, maleic anhydride, glutaric anhydride, itaconic anhydride, phthalic anhydride, and hexahydrophthalic anhydride; pyromellitic anhydride, biphenyltetracarboxylic acid Tetrabasic dianhydrides such as acid dianhydride and benzophenonetetracarboxylic dianhydride are exemplified.

において In the coloring composition, the content of the crosslinking agent is preferably from 10 to 1,000 parts by mass, particularly preferably from 20 to 500 parts by mass, per 100 parts by mass of the coloring material. If the content of the crosslinking agent is too small, sufficient curability may not be obtained. On the other hand, if the amount of the cross-linking agent is too large, the alkali developability of the coloring composition of the present invention is reduced, and background contamination on the unexposed portion of the substrate or the light-shielding layer, a film residue, and the like tend to be easily generated. .

(Photopolymerization initiator)
The coloring composition may contain a photopolymerization initiator as needed. Thereby, radiation sensitivity can be imparted to the coloring composition. The photopolymerization initiator is a compound that generates an active species capable of initiating polymerization of a crosslinking agent upon exposure to radiation such as visible light, ultraviolet light, far infrared light, electron beam, and X-ray.

Examples of the photopolymerization initiator include thioxanthone compounds, acetophenone compounds, biimidazole compounds, triazine compounds, O-acyl oxime compounds, onium salt compounds, benzoin compounds, benzophenone compounds, α-diketones Compounds, polynuclear quinone compounds, diazo compounds, imidosulfonate compounds, aminoketone compounds and the like. The photopolymerization initiators can be used alone or in combination of two or more.

、 In the coloring composition of the present invention, the content of the photopolymerization initiator is preferably from 0.01 to 120 parts by mass, particularly preferably from 1 to 100 parts by mass, per 100 parts by mass of the crosslinking agent. In this case, if the content of the photopolymerization initiator is too small, curing may be insufficient due to exposure, while if it is too large, the formed colored layer tends to easily fall off the substrate during development.

(Dispersion medium)
The coloring composition contains a dispersion medium. The dispersing medium can be appropriately selected and used as long as it disperses or dissolves other components constituting the coloring composition, does not react with these components, and has an appropriate volatility. For example, a conventionally known organic solvent can be used, and examples thereof include an organic solvent (dispersion medium) that can be used in the dispersant composition. The organic solvent is preferably a glycol alkyl ether acetate, a monohydric or polyhydric alcohol from the viewpoints of dispersibility of the pigment and the like, solubility of the dispersant, and applicability of the pigment dispersion composition. The solvent contained in the pigment dispersion composition may be only one type or a plurality of types.

(4) When forming pixels of a color filter by photolithography, the boiling point of the dispersion medium (under a pressure of 1013.25 hPa; hereinafter, the same applies to all boiling points) is preferably 100 ° C. to 200 ° C. Among the above-mentioned dispersion media, glycol alkyl ether acetates are preferable because they have a good balance of coatability, surface tension, and the like, and relatively high solubility of the components in the coloring composition. It is also preferable to use a dispersion medium having a boiling point of 150 ° C. or higher. By using a dispersion medium having a high boiling point, it is possible to suppress the mutual destruction of the coloring composition due to rapid drying of the coloring composition. The dispersion medium having a boiling point of 150 ° C. or higher may be glycol alkyl ether acetates. The content of the dispersion medium having a boiling point of 150 ° C. or higher is preferably 3 to 50% by mass based on 100% by mass of the entire dispersion medium.

含有 The content of the dispersion medium in the coloring composition is not particularly limited, and can be appropriately adjusted. The upper limit of the content of the dispersion medium in the coloring composition is usually 99% by mass. Further, the lower limit of the content of the dispersion medium in the coloring composition is usually 70% by mass, and preferably 80% by mass, in consideration of the viscosity suitable for applying the coloring composition. The dispersion medium can be used as a solvent for dissolving and removing the precipitate formed from the coloring composition.

(Other compounding agents)
The coloring composition may contain other compounding agents in addition to the compounding agents as long as the preferable physical properties of the present invention are not impaired. Other compounding agents include a sensitizing dye, a thermal polymerization inhibitor, a nonionic surfactant, an anionic surfactant, a cationic surfactant, an amphoteric surfactant, a plasticizer, an organic carboxylic acid compound, and an organic carboxylic acid. Acid anhydrides, pH adjusters, antioxidants, ultraviolet absorbers, light stabilizers, preservatives, fungicides, surfactants, anti-agglomeration agents, adhesion improvers, development improvers, storage stabilizers, etc. be able to.

Examples of the sensitizing dye include 4,4′-dimethylaminobenzophenone, 4,4′-diethylaminobenzophenone, 2-aminobenzophenone, 4-aminobenzophenone, 4,4′-diaminobenzophenone, 3,3′-diaminobenzophenone, and , 4-Diaminobenzophenone, 2- (p-dimethylaminophenyl) benzoxazole, 2- (p-diethylaminophenyl) benzoxazole, 2- (p-dimethylaminophenyl) benzo [4,5] benzoxazole, 2- ( p-dimethylaminophenyl) benzo [6,7] benzoxazole, 2,5-bis (p-diethylaminophenyl) 1,3,4-oxazole, 2- (p-dimethylaminophenyl) benzothiazole, 2- (p -Diethylaminophenyl) benzothiazo 2- (p-dimethylaminophenyl) benzimidazole, 2- (p-diethylaminophenyl) benzimidazole, 2,5-bis (p-diethylaminophenyl) 1,3,4-thiadiazole, (p-dimethylaminophenyl ) Pyridine, (p-diethylaminophenyl) pyridine, (p-dimethylaminophenyl) quinoline, (p-diethylaminophenyl) quinoline, (p-dimethylaminophenyl) pyrimidine, (p-diethylaminophenyl) pyrimidine and the like.

Examples of the thermal polymerization inhibitor include hydroquinone, p-methoxyphenol, pyrogallol, catechol, 2,6-t-butyl-p-cresol, β-naphthol and the like.

Examples of the nonionic surfactant include a fluorine-based surfactant, a silicone-based surfactant, and a polyoxyethylene-based surfactant.
Examples of anionic surfactants include alkyl sulfonates, alkyl benzene sulfonates, alkyl naphthalene sulfonates, polyoxyethylene alkyl ether sulfonates, alkyl sulfates, alkyl sulfate salts, higher alcohol sulfate salts, and aliphatic alcohols. Alcohol sulfates, polyoxyethylene alkyl ether sulfates, polyoxyethylene alkyl phenyl ether sulfates, alkyl phosphates, polyoxyethylene alkyl ether phosphates, polyoxyethylene alkyl phenyl ether phosphates, special polymer surfactants Agents and the like.
Examples of the cationic surfactant include quaternary ammonium salts, imidazoline derivatives, and alkylamine salts.
Examples of the amphoteric surfactant include betaine-type compounds, imidazolium salts, imidazolines, and amino acids.

Plasticizers include dioctyl phthalate, didodecyl phthalate, triethylene glycol dicaprylate, dimethyl glycol phthalate, tricresyl phosphate, dioctyl adipate, dibutyl sebacate, triacetyl glycerin and the like.

Examples of the organic carboxylic acid compound include a monocarboxylic acid, a carboxylic acid in which a carboxy group is directly bonded to a phenyl group, and a carboxylic acid in which a carboxy group is bonded to a phenyl group via a carbon bond.

Organic carboxylic anhydrides include acetic anhydride, trichloroacetic anhydride, trifluoroacetic anhydride, tetrahydrophthalic anhydride, succinic anhydride, maleic anhydride, citraconic anhydride, itaconic anhydride, glutaric anhydride, 1,2- Examples include cyclohexene dicarboxylic acid, n-octadecyl succinic anhydride, 5-norbornene-2,3-dicarboxylic anhydride, phthalic anhydride, trimellitic anhydride, pyromellitic anhydride, naphthalic anhydride and the like.

<Production method of coloring composition>
The coloring composition can be prepared by mixing a coloring material, a dispersant composition, a binder resin, a dispersion medium, and, if necessary, a crosslinking agent, a photopolymerization initiator, and other compounding agents. For mixing, for example, a mixing and dispersing machine such as a paint shaker, a bead mill, a ball mill, a dissolver, and a kneader can be used. It is preferable that the coloring composition is filtered after mixing. Since the coloring composition has alkali developability, it can be suitably used for color filters.

着色 As the coloring material, those which have been surface-treated with the dispersant composition of the present invention in advance can be used. Surface treatment methods include a dry method in which a dispersant is added and mixed while stirring a coloring material using a Henschel mixer, a ball mill, an atomizer colloid mill, and a Banbury mixer, and a wet method in which the solvent is removed after treatment in a solvent. Can be used. By performing the surface treatment with the dispersant composition of the present invention as described above, the dispersibility of the colorant can be improved and aggregation can be prevented.

<Color filter>
The color filter of the present invention includes a coloring layer formed using the coloring composition.

方法 As a method of manufacturing a color filter, for example, the following method can be mentioned. First, thermoplastic resin sheets such as polyester resin, polyolefin resin, polycarbonate resin, and polymethyl methacrylate resin; thermosetting resin sheets such as epoxy resin, unsaturated polyester resin, and poly (meth) acrylic resin; Having a color pixel that transmits light of three primary colors of red (R), green (G) and blue (B) on a transparent substrate, and preferably having a black matrix formed from the coloring composition. It is. As a method of manufacturing a color filter, a black colored composition is applied, and then prebaked to evaporate a solvent (dispersion medium) to form a coating film. Next, the coating film is exposed through a photomask, and then developed using an alkaline developer (an aqueous solution containing an organic solvent or a surfactant and an alkaline compound) to dissolve and remove unexposed portions of the coating film. Then, a black pattern (black matrix) is formed. Thereafter, post-baking is performed as necessary, and the same operation is sequentially repeated for red (R), green (G), and blue (B), so that pixel arrays of three primary colors of red, green, and blue are arranged on the substrate. The obtained color filter is obtained. However, in the present invention, the order of forming pixels of each color is not limited to the above.

When applying the coloring composition to the substrate, an appropriate coating method such as a spray method, a roll coating method, a spin coating method (spin coating method), a slit die coating method, and a bar coating method can be used. In particular, it is preferable to employ a spin coating method or a slit die coating method.

(4) After forming a protective film, if necessary, on the pixel pattern thus obtained, a transparent conductive film (such as indium tin oxide (ITO)) is formed by sputtering. After the formation of the transparent conductive film, a spacer may be further formed to form a color filter.

The color filter of the present invention has high dimensional accuracy and the like, and can be suitably used for a color liquid crystal display device, a color image pickup tube device, a color sensor, an organic EL display device, electronic paper, and the like.

In addition, since the coloring composition has a low viscosity and excellent dispersibility of a coloring material, it is suitable as a coloring column spacer to be supported on a thin film transistor (TFT) substrate and a color filter substrate which are positioned with a liquid crystal layer interposed therebetween. Can be used for For example, a composition having a high optical density (Optical @ Depth: OD) described in JP-A-2015-191234 can be mentioned.

Hereinafter, the present invention will be described in more detail based on specific examples. The present invention is not limited to the following embodiments at all, and can be implemented with appropriate changes within a scope that does not change the gist of the present invention. The polymerization rate, weight average molecular weight (Mw), molecular weight distribution (PDI) and amine value of the block copolymer and the binder resin, the formaldehyde amount of the dispersant composition, and the dispersibility (viscosity and particle diameter) of the coloring composition Was evaluated according to the following method.

The meanings of the abbreviations are as follows.
BMA: butyl methacrylate PCL5: 5-mol caprolactone adduct of 2-hydroxyethyl methacrylate (Placel (registered trademark) FM5, manufactured by Daicel Chemical Industries, Ltd.)
DMAEMA: dimethylaminoethyl methacrylate DEAEMA: diethylaminoethyl methacrylate TBAEMA: tert-butylaminoethyl methacrylate BTEE: ethyl-2-methyl-2-n-butylteranyl-propionate DBDT: dibutyl ditelluride AIBN: 2,2′-azobis (iso Butyronitrile)
PMA: Propylene glycol monomethyl ether acetate

(Polymerization rate)
¹ H-NMR was measured (solvent: CDCl ₃ , internal standard: TMS) using a nuclear magnetic resonance (NMR) measuring apparatus (manufactured by Bruker BioSpin, model: AVANCE 500 (frequency: 500 MHz)). With respect to the obtained NMR spectrum, the integral ratio between the peak of the vinyl group derived from the monomer and the peak of the ester side chain derived from the polymer was determined, and the conversion of the monomer was calculated.

(Weight average molecular weight (Mw) and molecular weight distribution (PDI))
It was determined by gel permeation chromatography (GPC) using a high performance liquid chromatograph (Model: HLC-8320, manufactured by Tosoh Corporation). The column was one SHOdex KF-603 (φ6 mm × 150 mm) (manufactured by SHOdex), 10 mmol / L lithium bromide / 10 mmol / L acetic acid / N-methyl-2-pyrrolidone solution in the mobile phase, and a differential refractometer in the detector. It was used. The measurement conditions were a column temperature of 40 ° C., a sample concentration of 20 mg / mL, a sample injection amount of 10 μm, and a flow rate of 0.2 mL / min. A calibration curve (calibration curve) was prepared using polystyrene (molecular weight: 427,000, 190,000, 96,400, 37,400, 10,200, 2,630, 906) as a standard substance, and the weight average molecular weight ( Mw) and number average molecular weight (Mn). The molecular weight distribution (PDI = Mw / Mn) was calculated from the measured values.

(Amine value)
The amine value represents the mass of potassium hydroxide (KOH) equivalent to the basic component per 1 g of solid content. The measurement sample was dissolved in tetrahydrofuran, and the obtained solution was subjected to neutralization titration with a 0.1 mol / L hydrochloric acid / 2-propanol solution using a potentiometric titrator (trade name: GT-06, manufactured by Mitsubishi Chemical Corporation). The amine value (B) was calculated by the following equation using the inflection point of the titration pH curve as the end point of the titration.
B = 56.11 × Vs × 0.1 × f / w
B: amine value (mgKOH / g)
Vs: amount of 0.1 mol / L hydrochloric acid / 2-propanol solution required for titration (mL)
f: titer of 0.1 mol / L hydrochloric acid (2-propanol property) w: mass (g) of a measurement sample (in terms of solid content)

(viscosity)
Using an E-type viscometer (trade name: TVE-22L, manufactured by Toki Sangyo Co., Ltd.), the viscosity was measured at 25 ° C. at a rotor rotation speed of 60 rpm using a cone rotor (1 ° 34 ′ × R24). The measurement was performed on the colored composition stored at 25 ° C. for 2 hours after preparation.

(Particle size)
The particle size was measured at 25 ° C. using a concentrated particle size analyzer (trade name: FPAR-1000, manufactured by Otsuka Electronics Co., Ltd.). The measurement was performed on the colored composition stored at 25 ° C. for 2 hours after the adjustment. The sample was diluted with propylene glycol monomethyl ether acetate (PGMEA) as needed.

(Amount of formaldehyde)
A cartridge (Sep Pak (registered trademark) DNPH silica plus cartridge (product number: WAT037500, manufactured by Waters)) filled with 0.5 g of the dispersant composition and silica gel impregnated with DNPH (2,4-dinitrophenylhydrazine) was used. The mixture was injected and allowed to stand at room temperature for 2 hours.
After washing with 4 mL of acetonitrile, the volume was increased to 5 mL. Liquid chromatograph (manufactured by Shimadzu Corporation, trade name: LC-10AD, column: Pro C18 RS (4.6 × 250 mm, 5 μm (manufactured by YMC)), mobile phase: acetonitrile / ultrapure water = 65: 35 solution, column temperature : 40 ° C., flow rate: 1.0 mL / min, detection wavelength: 360 nm), and measurement using a standard mixture of two aldehydes-DNPH (0.1 μg aldehyde / μL acetonitrile, manufactured by Wako Pure Chemical Industries) as a standard substance The amount of formaldehyde was calculated from the measurement results.

<Production of block copolymer>
(Block copolymer No. 1)
PCL5 (275.8 g), BMA (45.3 g), AIBN (1.64 g), and PMA (80.3 g) were charged into a flask equipped with an argon gas inlet tube and a stirrer, and after purging with argon, BTEE (14. 99g) and DBDT (18.47g) were added and reacted at 60 ° C for 7 hours. The polymerization rate was 98.3%.

(4) To the obtained solution, a mixed solution of DEAEMA (191.4 g) and PMA (47.9 g), which had been previously purged with argon, was added, and reacted at 60 ° C. for 13.5 hours. The polymerization rate was 99.4%.

終了 After the reaction was completed, the reaction solution was poured into n-heptane being stirred. The precipitated polymer was filtered by suction and dried to obtain a block copolymer No. 1 was obtained. The obtained block copolymer No. In No. 1, Mw was 16,301, PDI was 1.44, and amine value was 108 mgKOH / g. Table 2 shows the block copolymer No. The composition of No. 1 was shown. The content of each structural unit in the copolymer was calculated from the ratio of charged monomers used in the polymerization reaction and the conversion.

(Block copolymer Nos. 2, 3)
Block copolymer No. In the same manner as in the production method of block copolymer No. 1, A few were made. Table 1 shows the used monomers, organic tellurium compounds, organic ditelluride compounds, azo-based polymerization initiators, solvents, reaction conditions, and polymerization rates. Table 2 shows the composition, Mw, PDI, and amine value of each block copolymer. The content of each structural unit in the copolymer was calculated from the charged ratio and the conversion of the monomers used in the polymerization reaction.

<Dispersant composition>
0.325 g of each block copolymer was dissolved in 0.675 g of PMA to prepare a dispersant composition. The amount of formaldehyde was measured for this dispersant composition and is shown in Table 2.

Dispersant composition No. 3 is a structural unit derived from dimethylaminoethyl methacrylate in which the B block of the block copolymer as a dispersant does not have the structural unit of the general formula (1) (in the general formula (1), R ¹¹ and R ¹² has a methyl group). This dispersant composition No. Sample No. 3 had a high formaldehyde content of 1.7 ppm. On the other hand, the dispersant composition No. In Nos. 1 and 2, the B block of the block copolymer as a dispersant has a structural unit represented by the general formula (1). These dispersant compositions No. In Examples 1 and 2, the amount of formaldehyde was 0.1 ppm and 0.0 ppm, which was extremely reduced.

<Synthesis of alkali-soluble resin (binder resin)>
A flask equipped with an argon gas inlet tube and a stirrer was charged with methacrylic acid (MAA) (40.0 g), benzyl methacrylate (BzMA) (160.0 g), and propylene glycol monomethyl ether acetate (PMA) (580.0 g). After purging with argon, 2,2′-azobis (isobutyronitrile) (AIBN) (4.0 g), n-dodecanethiol (6.0 g) and PMA (20.0 g) were added, and the temperature was raised to 90 ° C. While maintaining the solution at 90 ° C., MAA (80.0 g), BzMA (320.0 g), AIBN (8.0 g), n-dodecanethiol (12.0 g), and PMA (50.0 g) were added to the solution. It was added dropwise over 1.5 hours. After 60 minutes from the completion of the dropwise addition, the temperature was raised to 110 ° C., AIBN (0.8 g) and PMA (10.0 g) were added, and the mixture was reacted for 1 hour. Further, AIBN (0.8 g) and PMA ( 10.0 g) was added and reacted for 1 hour, and AIBN (0.8 g) and PMA (10.0 g) were further added and reacted for 1 hour.

(4) The obtained reaction solution was cooled to room temperature, PMA (240.0 g) was added, and a solution of an alkali-soluble resin having a nonvolatile content of 39.5% was obtained. The weight average molecular weight (Mw) of the alkali-soluble resin was 9,150, the molecular weight distribution (PDI) was 1.92, and the acid value was 128 mgKOH / g.

<Preparation of coloring composition>
Coloring composition No. 1
Pigment 8 parts by mass, block copolymer No. A mixing composition was prepared so as to be 16 parts by mass, 6 parts by mass of an alkali-soluble resin, and 80 parts by mass of PMA, and 555 parts by mass of 0.3 mm zirconia beads were added, and a bead mill (trade name: DISPERMAT CA, manufactured by VMA-GETZMANN GmbH) ) For 3 hours and sufficiently dispersed. After completion of the dispersion, the beads were filtered off to obtain a colored composition. Pigments include C.I. I. Pigment Red 254 (trade name: BKCF, manufactured by Ciba Specialty Chemicals) was used. The dispersibility of the obtained coloring composition was evaluated. Table 3 shows the evaluation results.

Coloring composition No. Two, three
Except that the block copolymer was changed, the coloring composition No. In the same manner as in the preparation method of Colored Composition No. 1, A few were prepared. Table 3 shows the evaluation results.

Coloring composition No. Each of 1 to 3 has good pigment dispersibility. Therefore, it can be understood that the block copolymer in which the B block has the structural unit of the general formula (1) can be used as a dispersant. Further, in particular, the coloring composition No. B using a block copolymer in which the B block has a structural unit derived from diethylaminoethyl methacrylate. No. 1 is excellent in pigment dispersibility. Therefore, by using a block copolymer in which the B block has a structural unit derived from diethylaminoethyl methacrylate, the amount of formaldehyde can be reduced, and a colored composition having excellent pigment dispersibility can be obtained. Understand.

The present invention includes the following embodiments.
(Embodiment 1)
A dispersant composition comprising a polymer having a structure represented by the general formula (5) in a side chain.
* -Y ¹ -NR ¹¹ R ¹² (5)
[In the general formula (5), R ¹¹ represents a hydrogen atom, an optionally substituted linear or cyclic hydrocarbon group having 2 or more carbon atoms. R ¹² represents a linear or cyclic hydrocarbon group having 2 or more carbon atoms which may have a substituent. R ¹¹ and R ¹² may combine with each other to form a cyclic structure. Y ¹ represents a divalent hydrocarbon group. * Represents a bond. ]

(Embodiment 2)
The dispersant composition according to embodiment 1, wherein the polymer has an amine value of 10 mgKOH / g to 200 mgKOH / g.

(Embodiment 3)
Embodiment 1 or 2 in which the polymer is a block copolymer having an A block having a structural unit derived from a (meth) acrylic monomer and a B block having a structural unit represented by the general formula (1) The dispersant composition according to any one of the preceding claims.

(Embodiment 4)
The dispersant composition according to aspect 3, wherein the A block has a structural unit represented by a general formula (10).

(Embodiment 5)
The dispersant composition according to aspect 3 or 4, wherein the molecular weight distribution (PDI) of the block copolymer is 2.5 or less.

(Embodiment 6)
The dispersant composition according to any one of aspects 3 to 5, wherein the block copolymer is obtained by polymerization by living radical polymerization.

(Embodiment 7)
A coloring composition comprising the dispersant composition according to any one of aspects 1 to 6, a coloring material, a binder resin and a dispersion medium.

(Embodiment 8)
The coloring composition according to aspect 7, which is used for a color filter.

(Embodiment 9)
A color filter comprising a coloring layer formed using the coloring composition according to aspect 8.

Claims

A dispersant composition comprising a polymer having a structure represented by the general formula (5) in a side chain.
* -Y 1 -NR 11 R 12 (5)
[In the general formula (5), R 11 represents a hydrogen atom, an optionally substituted linear or cyclic hydrocarbon group having 2 or more carbon atoms. R 12 represents a linear or cyclic hydrocarbon group having 2 or more carbon atoms which may have a substituent. R 11 and R 12 may combine with each other to form a cyclic structure. Y 1 represents a divalent hydrocarbon group. * Represents a bond. ]
分散 The dispersant composition according to claim 1, wherein the polymer has an amine value of 10 mgKOH / g to 200 mgKOH / g.
The polymer is a block copolymer having an A block having a structural unit derived from a (meth) acrylic monomer and a B block having a structural unit represented by the general formula (1). 3. The dispersant composition according to item 1.

[In the general formula (1), R 11 represents a hydrogen atom, a linear or cyclic hydrocarbon group having 2 or more carbon atoms which may have a substituent. R 12 represents a linear or cyclic hydrocarbon group having 2 or more carbon atoms which may have a substituent. R 11 and R 12 may combine with each other to form a cyclic structure. R 13 represents a hydrogen atom or a methyl group. X 1 represents an amide group, an ester group, or a single bond. Y 1 represents a divalent hydrocarbon group. ]
The dispersant composition according to claim 3, wherein the A block has a structural unit represented by the general formula (10).

[In the general formula (10), n1 represents an integer of 1 to 10. R 1 represents a hydrogen atom or a methyl group. R 2 represents an alkylene group having 1 to 10 carbon atoms. R 3 represents an alkylene group having 1 to 10 carbon atoms. ]
The dispersant composition according to claim 3 or 4, wherein the molecular weight distribution (PDI) of the block copolymer is 2.5 or less.
(6) The dispersant composition according to any one of (3) to (5), wherein the block copolymer is polymerized by living radical polymerization.
A coloring composition comprising the dispersant composition according to any one of claims 1 to 6, a coloring material, a binder resin, and a dispersion medium.
The coloring composition according to claim 7, which is used for a color filter.
A color filter comprising a coloring layer formed using the coloring composition according to claim 8.