KR20210040933A - Dispersant composition, coloring composition, and color filter - Google Patents

Abstract

[Problem] To provide a dispersant composition with a small amount of formaldehyde over time.
[Solution means] The dispersant composition is characterized by containing a polymer having a structure represented by the general formula (5) in the side chain.
*-Y ¹ -NR ¹¹ R ¹² (5)
[In General Formula (5), R ¹¹ represents a hydrogen atom or a chain or cyclic hydrocarbon group having 2 or more carbon atoms which may have a substituent. R ¹² represents a chain or cyclic hydrocarbon group having 2 or more carbon atoms which may have a substituent. R ¹¹ and R ¹² may be bonded to each other to form a cyclic structure. Y ¹ represents a divalent hydrocarbon group. * Represents a binding hand.]

Description

Dispersant composition, coloring composition, and color filter

The present invention relates to a dispersant composition containing a polymer.

Conventionally, in manufacturing a color filter used in a liquid crystal display or the like, as a method of imparting a colorant to a substrate, a dyeing method, a printing method, an inkjet method, an electrodeposition method, a pigment dispersion method, and the like are known. Among these, from the viewpoint of spectral characteristics, durability, pattern shape, and precision, the pigment dispersion method has become mainstream. In this pigment dispersion method, a coating film made of a colored composition in which a pigment, a dispersant, a dispersion medium (solvent), a binder resin, etc. is mixed is formed on a substrate, irradiated with radiation through a photomask having a desired pattern shape, and cured, and alkali The phenomenon takes place.

In recent years, in order to obtain satisfactory color reproducibility and high contrast of color filters, high concentration of pigments in colored compositions has been studied. In the case of high concentration of the pigment, since the proportion of the dispersant decreases relatively, high dispersibility is required for the dispersant (for example, see Patent Document 1 (paragraph 0004)). In addition, in alkali development, a binder resin having alkali solubility plays a large role. However, in the case of the pigment dispersion composition in which the pigment is made high, the proportion of the binder resin as a developing component decreases, and the alkali developability decreases. Therefore, the alkali developability, which has originally been required for the binder resin, is also required for the dispersant. As such a dispersant, Patent Literature 2 describes using an AB block copolymer as a pigment dispersant, consisting of an A block having a polylactone chain in the side chain and a B block having a tertiary amino group in the side chain (Patent Literature 2 (See paragraphs 0023 to 0045).

Japanese Patent Laid-Open No. 2009-265515 Japanese Patent Laid-Open No. 2013-119568

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

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

The dispersant composition of the present invention capable of solving the above problems is characterized by containing a polymer having a structure represented by the general formula (5) in the side chain.

*-Y ¹ -NR ¹¹ R ¹² (5)

[In General Formula (5), R ¹¹ represents a hydrogen atom or a chain or cyclic hydrocarbon group having 2 or more carbon atoms which may have a substituent. R ¹² represents a chain or cyclic hydrocarbon group having 2 or more carbon atoms which may have a substituent. R ¹¹ and R ¹² may be bonded to each other to form a cyclic structure. Y ¹ represents a divalent hydrocarbon group. * Represents a binding hand.]

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

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

According to the present invention, it is possible to obtain a dispersant composition with a small amount of formaldehyde generation over time.

Hereinafter, an example of a preferred embodiment of the present invention will be described. However, the following embodiment is a mere illustration. It is not limited at all to the following embodiment.

In the present invention, "(meth)acrylic" refers to "at least one of acrylic and methacrylic". "(Meth)acrylic monomer" refers to a monomer having a "(meth)acryloyl group" in a molecule. "(Meth)acryloyl" means "at least one of acryloyl and methacryloyl". "Vinyl monomer" refers to a monomer having a radically polymerizable carbon-carbon double bond in a molecule. "Structural unit derived from a (meth)acrylic monomer" refers to a structural unit in which a radically polymerizable carbon-carbon double bond of a (meth)acrylic monomer is polymerized to form a single carbon-carbon bond. "Structural unit derived from a vinyl monomer" refers to a structural unit in which a carbon-carbon double bond capable of radical polymerization of a vinyl monomer is polymerized to form a single carbon-carbon bond.

<Dispersant composition>

The dispersant composition of the present invention is characterized by containing a polymer having a structure represented by the general formula (5) in the side chain.

*-Y ¹ -NR ¹¹ R ¹² (5)

[In General Formula (5), R ¹¹ represents a hydrogen atom or a chain or cyclic hydrocarbon group having 2 or more carbon atoms which may have a substituent. R ¹² represents a chain or cyclic hydrocarbon group having 2 or more carbon atoms which may have a substituent. R ¹¹ and R ¹² may be bonded to each other to form a cyclic structure. Y ¹ represents a divalent hydrocarbon group. * Represents a binding hand.]

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

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 carbon number of the linear alkyl group is preferably 2 to 20 carbon atoms, more preferably 2 to 10 carbon atoms, and still more preferably 2 to 5 carbon atoms. Examples of the linear alkyl group include ethyl group, n-propyl group, n-butyl group, n-hexyl group, n-octyl group, n-nonyl group, n-decyl group, n-lauryl group, and the like. As carbon number of the said branched chain alkyl group, C3-C20 is preferable, C3-C10 is more preferable, and C3-C5 is still more preferable. Examples of the branched chain alkyl group include isopropyl group, isobutyl group, sec-butyl group, tert-butyl group, 2-ethylhexyl group, neopentyl group, and isooctyl group.

Examples of ^{the substituents 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 moiety. As the carbon number of the cyclic alkyl group, 4 to 18 carbon atoms are preferable, 6 to 12 carbon atoms are more preferable, and 6 to 10 carbon atoms are still more preferable. Examples of the cyclic alkyl group include a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group. As carbon number of the said aromatic group, C6-C18 is preferable, C6-C12 is more preferable, and C6-C8 is more preferable. Examples of the aromatic group include a phenyl group, a tolyl group, a xylyl group, and a mesityl group. Examples of the chain moiety of a cyclic alkyl group having a chain moiety and an aromatic group having a chain moiety include an alkylene group having 1 to 12 carbon atoms, preferably an alkylene group having 1 to 6 carbon atoms, and more preferably an alkylene group having 1 to 3 carbon atoms. Can be lifted.

Examples of ^{the substituents 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 bonding of R 11} and R ¹² to each other include a 5- to 7-membered nitrogen-containing heterocycle or a condensed ring formed by condensing two of them. It is preferable that the nitrogen-containing heterocycle does not have aromaticity, and a saturated ring is more preferable.

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. Although either linear or branched chain may be sufficient as the said alkylene group, linear is preferable. Y ¹ is preferably an alkylene group having 1 to 5 carbon atoms.

^{As the -NR 11} R ¹² moiety of the structure represented by the general formula (5), monoalkylamino groups such as ethylamino group, propylamino group, and tert-butylamino group; diethylamino group, dipropylamino group, bis(2-hydroxyethyl) ) Dialkylamino groups such as amino groups, and the like.

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

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 or more, further preferably from the viewpoint of adsorption to a coloring material and dispersibility of a coloring material. Preferably, it is 80 mgKOH/g or more, 200 mgKOH/g or less is preferable, more preferably 150 mgKOH/g or less, and still more preferably 120 mgKOH/g or less.

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, more preferably 5,000 or more, particularly preferably 6,000 or more, preferably 40,000 or less, and more preferably 30,000 Below, it is more preferably 25,000 or less, and particularly preferably 20,000 or less. When the weight average molecular weight is within the above range, the dispersion performance when used as a dispersant becomes more favorable.

(Block copolymer)

The polymer is preferably a block copolymer having a block A having a structural unit derived from a (meth)acrylic monomer and a block B having a structural unit represented by the general formula (1) from the viewpoint of dispersibility. .

[In General Formula (1), R ¹¹ represents a hydrogen atom or a chain or cyclic hydrocarbon group having 2 or more carbon atoms which may have a substituent. R ¹² represents a chain or cyclic hydrocarbon group having 2 or more carbon atoms which may have a substituent. R ¹¹ and R ¹² may be bonded to 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.]

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

(A block)

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

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

The (meth)acrylic monomer is a (meth)acrylate having a chain alkyl group (straight chain alkyl group or branched chain alkyl group), (meth)acrylate having a cyclic alkyl group, (meth)acrylate having a polycyclic structure, and having an aromatic group. (Meth)acrylate, (meth)acrylate having a polyalkylene glycol structural unit, (meth)acrylate having a hydroxy group, (meth)acrylate having a lactone-modified hydroxy group, (meth)acrylate having an alkoxy group, and (Meth)acrylate having an oxygen heterocyclic group, (meth)acrylate having an acidic group, (meth)acrylic acid, and the like can be exemplified, and one type or a combination of two or more of them may be used.

As the (meth)acrylate having a straight-chain alkyl group, a (meth)acrylate having a straight-chain alkyl group having 1 to 20 carbon atoms in the straight-chain alkyl group is preferable, and (meth) having a straight-chain alkyl group having 1 to 10 carbon atoms in the straight-chain alkyl group Acrylate is more preferred. As the (meth)acrylate having a linear alkyl group, methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, n-butyl (meth)acrylate, n-hexyl (meth) Acrylate, n-octyl (meth)acrylate, n-nonyl (meth)acrylate, decyl (meth)acrylate, n-lauryl (meth)acrylate, n-stearyl (meth)acrylate, etc. I can.

As the (meth)acrylate having a branched chain alkyl group, a (meth)acrylate having a branched chain alkyl group having 3 to 20 carbon atoms in the branched chain alkyl group is preferable, and a branched chain alkyl group having 3 to 10 carbon atoms in the branched chain alkyl group (Meth)acrylate having a is preferred. As the (meth)acrylate having a branched chain alkyl group, isopropyl (meth)acrylate, isobutyl (meth)acrylate, sec-butyl (meth)acrylate, tert-butyl (meth)acrylate, isooctyl ( Meth)acrylate, 2-ethylhexyl (meth)acrylate, isononyl (meth)acrylate, isodecyl (meth)acrylate, and the like.

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

As the (meth)acrylate having a polycyclic structure, it is preferable that it is a (meth)acrylate having a polycyclic structure having 6 to 12 carbon atoms in the polycyclic structure. Examples of the polycyclic structure include a cyclic alkyl group having a crosslinked 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, etc. are mentioned.

The (meth)acrylate having an aromatic group is preferably a (meth)acrylate having an aromatic group having 6 to 12 carbon atoms in the aromatic group. Examples of the aromatic group include an aryl group and the like, and may have a chain moiety 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.

As the (meth)acrylate having the polyalkylene glycol structural unit, 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 glycol (degree of polymerization = 2 to 10) propyl ether (meth) acrylate, polyethylene glycol (degree of polymerization = 2 to 10) phenyl ether (meth) acrylate having polyethylene glycol structural units such as (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 And (meth)acrylates having a polypropylene glycol structural unit such as polypropylene glycol (polymerization degree = 2 to 10) phenyl ether (meth)acrylate.

Examples of the (meth)acrylate having a hydroxy group include 2-hydroxyethyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, and 4-hydroxybutyl ( Meth)acrylate, 6-hydroxyhexyl (meth)acrylate, 8-hydroxyoctyl (meth)acrylate, 10-hydroxydecyl (meth)acrylate, 12-hydroxylauryl (meth)acrylate, etc. Can be mentioned. 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 lactone to the (meth)acrylate having a hydroxy group, and caprolactone is preferably added. The amount of caprolactone added is preferably 1 mol to 10 mol, more preferably 1 mol to 5 mol. Examples of the lactone-modified hydroxy group-containing (meth)acrylate, 2-hydroxyethyl (meth)acrylate with 1 mol of caprolactone adduct, 2-hydroxyethyl (meth)acrylate with 2 mol of caprolactone adduct, 2-hydroxy Caprolactone 3 mol adduct of oxyethyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate caprolactone 4 mol adduct, 2-hydroxyethyl (meth)acrylate caprolactone 5 mol adduct, 2- A 10 mol addition product of caprolactone of hydroxyethyl (meth)acrylate and the like is preferred.

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

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. As specific examples of the (meth)acrylate having an oxygen-containing heterocyclic group, glycidyl (meth)acrylate, tetrahydrofurfuryl (meth)acrylate, (3-ethyloxetan-3-yl)methyl (meth)acrylic Rate, (2-methyl-2-ethyl-1,3-dioxoran-4-yl)methyl (meth)acrylate, cyclic trimethylolpropane formal (meth)acrylate, 2-[(2-tetrahydro Pyranyl)oxy]ethyl (meth)acrylate, 1,3-dioxane-(meth)acrylate, and the like.

Examples of the acidic group include a carboxyl 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 ). Can be mentioned. 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 carboxyl group include carboxyethyl (meth)acrylate, carboxypentyl (meth)acrylate, 2-(meth)acryloyloxyethylsuccinate, and 2-(meth)acryloyloxy. A monomer obtained by reacting an acid anhydride such as maleic anhydride, succinic anhydride and phthalic anhydride with (meth)acrylate having a hydroxy group such as ethyl maleate and 2-(meth)acryloyloxyethylphthalate, etc. are mentioned. Examples of the (meth)acrylate having a sulfonic acid group include ethyl sulfonic acid (meth)acrylate. Examples of the (meth)acrylate having a phosphoric acid group include 2-(phosphonooxy)ethyl (meth)acrylate.

The A block may have a structural unit other than the structural unit derived from a (meth)acrylic monomer. Other structural units that may be included in the A block are not particularly limited as long as it is formed of a vinyl monomer that can be copolymerized with both a (meth)acrylic monomer and a vinyl monomer forming the B block described later. The 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 the vinyl monomers capable of forming other structural units of the A block include α-olefins, aromatic vinyl monomers, vinyl monomers containing heterocycles, vinylamides, vinyl carboxates, dienes, and the like. These vinyl monomers may have a hydroxy group and an epoxy group.

Examples of the α-olefin include 1-hexene, 1-octene, and 1-decene.

Examples of the aromatic vinyl monomer include styrene, α-methylstyrene, 4-methylstyrene, 2-methylstyrene, 3-methylstyrene, 4-methoxystyrene, 2-hydroxymethylstyrene, and 1-vinylnaphthalene.

As a vinyl monomer containing a heterocycle, 2-vinylthiophene, N-methyl-2-vinylpyrrole, 1-vinyl-2-pyrrolidone, 2-vinylpyridine, 4-vinylpyridine, N-phenylmaleimide, N-benzyl maleimide, N-cyclohexyl maleimide, etc. are mentioned.

Examples of vinylamides include N-vinylformamide, N-vinylacetamide, and N-vinyl-ε-caprolactam.

As vinyl carboxylate, vinyl acetate, vinyl pivalate, vinyl benzoate, etc. are mentioned.

Examples of dienes include butadiene, isoprene, 4-methyl-1,4-hexadiene, and 7-methyl-1,6-octadiene.

It is preferable that the A block contains a structural unit represented by the general formula (10), that is, a structural unit derived from the (meth)acrylate having the lactone-modified hydroxy group. Since the structural unit represented by the general formula (10) has an ester bonding moiety and a terminal hydroxy group in the side chain, it has high affinity with a dispersion medium and a binder resin, thereby enhancing the alkali developability of the block copolymer.

[In General Formula (10), n1 represents the integer of 1-10. 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.]

It is preferable that n1 of said formula (10) is an integer of 1-7, and it is more preferable that it is an integer of 1-5.

The ^{alkylene group having 1 to 10 carbon atoms represented by R 2} may be linear or branched, but linear is preferable. Specific examples of the alkylene group having 1 to 10 carbon atoms represented by R ² are methylene group, ethylene group, trimethylene group, tetramethylene group, pentamethylene group, hexamethylene group, heptamethylene group, octamethylene group, 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 linear is preferable. 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, and 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 the structural unit represented by the general formula (10), the content rate is preferably 10% by mass or more, more preferably 20% by mass or more, further preferably, in 100% by mass of the A block. It is preferably 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. The alkali developability of the block copolymer can be improved by making the content of the structural unit derived from the (meth)acrylate having a lactone-modified hydroxy group within the above range.

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

When a structural unit derived from a vinyl monomer having an acidic group is contained, the content rate is preferably 2% by mass or more and preferably 20% by mass or less in 100% by mass of the A block. If the content of the structural unit derived from the vinyl monomer having an acidic group is 2% by mass or more, the dissolution rate when neutralized with alkali is accelerated in the alkali phenomenon, and if it is 20% by mass or less, the hydrophilicity is not too high, resulting in messy pixels to be formed. You can suppress the loss.

In the A block, the content of the structural unit represented by the general formula (1) described later is less than 10% by mass, preferably 3% by mass or less, more preferably 1% by mass or less, and still more preferably 0.1% by mass. Hereinafter, it is most preferable not to contain the structural unit represented by general formula (1). The lower the content rate of the structural unit represented by the general formula (1) in the A block, the better the dispersion performance of the coloring material.

It is preferable that the A block does not have an 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 groups are present in the A block, when used as a dispersant, the coloring material is adsorbed to both the A block and B block, and the dispersing performance of the coloring material is deteriorated. The content rate of the structural unit derived from a vinyl monomer having an amino group in the A block (including those in which the amino group is quaternized) is preferably 3% by mass or less, more preferably 1% by mass or less, further preferably It is 0.1 mass% or less, Most preferably, it is 0 mass %.

When two or more types of structural units are contained in the A block, the various structural units contained in the A block may be contained in any of random copolymerization, block copolymerization, etc. in the A block, and random copolymerization from the viewpoint of uniformity. It is preferably contained in the form of. 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 one type or may have two or more types. By having the structural unit represented by the general formula (1), the adsorption property with the coloring material is high, and the generation of formaldehyde with time can be suppressed. In addition, in the structural unit represented by general formula (1), ^{-Y 1} -NR ¹¹ R ¹² bonded to ^{X 1} is a structure represented by general formula (5).

[In General Formula (1), R ¹¹ represents a hydrogen atom or a chain or cyclic hydrocarbon group having 2 or more carbon atoms which may have a substituent. R ¹² represents a chain or cyclic hydrocarbon group having 2 or more carbon atoms which may have a substituent. R ¹¹ and R ¹² may be bonded to 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.]

In the formula (1) R ¹¹ and R ¹² is an R ¹¹ and R ¹² and agreement in the general formula (5). Examples of the chain hydrocarbon group and cyclic hydrocarbon group represented by ^{R 11} and R ¹² in the general formula (1) include those exemplified by ^{R 11} and R ^{12 in the general formula (5). As the carbon number of the linear alkyl group represented by R 11} and R ¹² in the general formula (1), 2 to 20 carbon atoms are preferable, 2 to 10 carbon atoms are more preferable, 2 to 5 carbon atoms are more preferable, and branched As the carbon number of the chain alkyl group, 3 to 20 carbon atoms are preferable, 3 to 10 carbon atoms are more preferable, and 3 to 5 carbon atoms are still more preferable.

Examples of ^{the cyclic structure formed by bonding of R 11} and R ¹² to each other include a 5- to 7-membered nitrogen-containing heterocycle or a condensed ring formed by condensing two of them. It is preferable that the nitrogen-containing heterocycle does not have aromaticity, and a saturated ring is more preferable. Specifically, structures represented by the following formulas (1-1), (1-2), and (1-3) are exemplified.

[In General Formulas (1-1), (1-2), and (1-3), R ¹⁴ represents an alkyl group having 1 to 6 carbon atoms. l represents the integer of 0-5. m represents the integer of 0-4. n represents the integer of 0-4. * Represents a binding hand. When l 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, respectively.]

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 aspect of the amide group include C-CO-NH-Y ¹ or C-NH-CO-Y ¹ , and C-CO-NH-Y ¹ is preferable. As a bonding aspect of an ester group, C-CO-OY ¹ or CO-CO-Y ¹ can be mentioned, and C-CO-OY ¹ is preferable.

^{Y 1} in General Formula (1) is synonymous with ^{Y 1} in General Formula (5). The Y ¹ is preferably an alkylene group having 1 to 10 carbon atoms. Although either linear or branched chain may be sufficient as the said alkylene group, linear is preferable. 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, dipropylaminopropyl (meth)acrylate, dipropylaminobutyl (meth)acrylate, tert-butylaminoethyl (meth)acrylate, and the like.

The content rate of the structural unit represented by the general formula (1) is preferably 10% by mass or more, more preferably 30% by mass or more, further preferably 50% by mass or more, and 98% by mass in 100% by mass of the B block. % Or less is preferable, more preferably 80% by mass or less, and still more preferably 70% by mass or less. It is thought that it has high affinity with a coloring material by making the content rate of the structural unit represented by General formula (1) into this range.

The B block may have a structural unit represented by 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. If the B block has the structural unit represented by the general formula (2), strong adsorption to the surface of the coloring material can be maintained for a long time, and storage stability is further improved.

[In General Formula (2), R ²¹ represents a hydrogen atom or a chain or cyclic hydrocarbon group which may have a substituent. R ²² and R ²³ each independently represent a chain or cyclic hydrocarbon group which may have a substituent. R ²² and R ²³ may be bonded to 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 chain alkyl group. As carbon number of the said linear alkyl group, C1-C20 is preferable, C2-C20 is more preferable, C2-C10 is still more preferable, and C2-C5 is especially preferable. Examples of the linear alkyl group include ethyl group, n-propyl group, n-butyl group, n-hexyl group, n-octyl group, n-nonyl group, n-decyl group, n-lauryl group, and the like. As carbon number of the said branched chain alkyl group, C3-C20 is preferable, C3-C10 is more preferable, and C3-C5 is still more preferable. Examples of the branched chain alkyl group include isopropyl group, isobutyl group, sec-butyl group, tert-butyl group, 2-ethylhexyl group, neopentyl group, and isooctyl group.

Examples of ^{the substituents of 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 ), a hydroxy group, and the like.

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 moiety. As the carbon number of the cyclic alkyl group, 4 to 18 carbon atoms are preferable, 6 to 12 carbon atoms are more preferable, and 6 to 10 carbon atoms are still more preferable. Examples of the cyclic alkyl group include a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group. As carbon number of the said aromatic group, C6-C18 is preferable, C6-C12 is more preferable, and C6-C8 is more preferable. Examples of the aromatic group include a phenyl group, a tolyl group, a xylyl group, and a mesityl group. Examples of the chain moiety of a cyclic alkyl group having a chain moiety and an aromatic group having a chain moiety include an alkylene group having 1 to 12 carbon atoms, preferably an alkylene group having 1 to 6 carbon atoms, and more preferably an alkylene group having 1 to 3 carbon atoms. Can be lifted.

Examples of ^{the substituents of 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 bonding of R 22} and R ²³ to each other include a 5- to 7-membered nitrogen-containing heterocycle or a condensed ring formed by condensing two of them. It is preferable that the nitrogen-containing heterocycle does not have aromaticity, and a saturated ring is more preferable. Specifically, structures represented by the following formulas (2-1), (2-2), and (2-3) are exemplified.

[In General Formulas (2-1), (2-2), and (2-3), R ²⁵ is R ²¹ . R ²⁶ represents a C1-C6 alkyl group. l represents the integer of 0-5. m represents the integer of 0-4. n represents the integer of 0-4. * Represents a binding hand. When l 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, respectively.]

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 aspect of the amide group include C-CO-NH-Y ² or C-NH-CO-Y ² , and C-CO-NH-Y ² is preferable. Examples of the bonding aspect of the ester group include C-CO-OY ² or CO-CO-Y ² , and C-CO-OY ² is preferable.

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 arenediyl group having 6 to 10 carbon atoms. Among these, an alkylene group having 1 to 10 carbon atoms is preferable. Although either linear or branched chain may be sufficient as the said alkylene group, linear is preferable. It is preferable that Y ² is a C1-C5 alkylene group.

Examples of Z ⁻ include halogen anion, carboxylate anion, sulfate anion, sulfonate anion, phosphate anion, nitroxide anion, and the like.

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 alkyl carboxylate anions such as acetate anion and propionic acid anion; aromatic carboxylate anions such as benzoate anions.

Examples of the sulfate anion include alkyl sulfate anions such as methyl sulfate anion and ethyl sulfate anion; aromatic sulfate anions such as phenyl sulfate anion and benzyl sulfate anion.

Examples of the sulfonate anions include alkyl sulfonate anions such as methanesulfonic acid anions and ethanesulfonic acid anions; aromatic sulfonate anions such as benzenesulfonic acid anions and toluenesulfonic acid anions.

Examples of the phosphate anion include alkyl phosphate anions such as methylphosphonic acid anion and ethylphosphonic acid anion; aromatic phosphate anions such as phenylphosphonic acid anion and benzylphosphonic acid anion.

Specific examples of the vinyl monomer forming the structural unit represented by the above formula (2) include (meth)acryloyloxyethylbenzyldiethylammonium chloride, (meth)acryloyloxypropylbenzyldiethylammonium chloride, (meth) Acryloyloxybutylbenzyldiethylammonium chloride, (meth)acryloyloxyethylbenzyldiethylammonium bromide, (meth)acryloyloxypropylbenzyldiethylammonium bromide, (meth)acryloyloxybutylbenzyldiethyl Ammonium bromide, (meth)acryloyloxyethylbenzyldiethylammonium iodide, (meth)acryloyloxypropylbenzyldiethylammonium iodide, (meth)acryloyloxybutylbenzyldiethylammonium iodide, (meth) ) Acryloyloxyethylbenzyldiethylammonium fluoride, (meth)acryloyloxypropylbenzyldiethylammonium fluoride, (meth)acryloyloxybutylbenzyldiethylammonium fluoride, and the like.

In the case of containing the structural unit represented by the general formula (2), the content rate is preferably 2% by mass or more, more preferably 20% by mass or more, and preferably 90% by mass or less in 100% by mass of the B block. And more preferably 70% by mass or less. It is thought that it has high affinity with a coloring material by making the content rate of the structural unit represented by General formula (2) into this range.

The B block may be only a structural unit represented by general formula (1) and a structural unit represented by general formula (2), or may contain other structural units. From the viewpoint of maintaining the affinity of 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 80% by mass or more in 100% by mass of the B block. This is preferable, more preferably 90% by mass or more, and still more preferably 95% by mass or more. In addition, it is preferable that the B block does not substantially contain a structural unit derived from a vinyl monomer having an acidic group. That is, the content rate of the structural unit derived from the vinyl monomer having an acidic group is preferably 5% by mass or less, and 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 units of the B block include the same ones exemplified as the specific examples of the vinyl monomer capable of forming the other structural units of the A block.

When two or more types of structural units are contained in the B block, various structural units contained in the B block may be contained in any of random copolymerization, block copolymerization, etc. in the B block, and random copolymerization from the viewpoint of uniformity. It is preferably contained in the form of. 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)

It is preferable that the structure of the block copolymer is a linear block copolymer. In addition, 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, when the A block is expressed as A and the B block is B, (AB) _m- type , (AB) _m -A type, (BA) _m -B type (m is an integer greater than or equal to 1, for example, an integer of 1 to 3) It is preferably a copolymer having at least one structure selected from the group consisting of . Among these, it is preferable that it is an AB-type diblock copolymer from the viewpoint of handling properties 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, thereby effectively producing a coloring material and , It is thought that it can act suitably with a dispersion medium (solvent), and a binder resin (alkali-soluble resin). The block copolymer may have blocks other than the A block and the B block.

The content rate of the block A 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 in the total 100% by mass of the block copolymer. , More preferably, it is 80 mass% or less, More preferably, it is 75 mass% or less. The content rate of the B block is preferably 15% by mass or more, more preferably 20% by mass or more, further preferably 25% by mass or more, and 65% by mass or less in the total 100% by mass of the block copolymer. , More preferably, it is 60 mass% or less, More preferably, it is 55 mass% or less. By adjusting the content rates of the A block and B block within the above range, the dispersion performance when used as a dispersant is further improved.

The mass ratio of the A block and the B block in the block copolymer (A block/B block) is preferably 50/50 or more, more preferably 55/45 or more, still more preferably 60/40 or more, and 95/5 The following are preferable, more preferably 90/10 or less, and still more preferably 80/20 or less. When the mass ratio of the A block and the B block is within the above range, the dispersion 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 preferably 10% by mass or less. Do.

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, and more preferably 10% by mass. More preferably, it is 20 mass% or more, 50 mass% or less is preferable, More preferably, it is 45 mass% or less, More preferably, it is 40 mass% or less.

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, more preferably 5,000 or more, particularly preferably 6,000 or more, and 40,000 or less is preferred, and more preferably Is 30,000 or less, more preferably 25,000 or less, and particularly preferably 20,000 or less. When the weight average molecular weight is within the above range, the dispersion performance when used as a dispersant becomes more favorable.

The molecular weight distribution (PDI) of the block copolymer is preferably 2.5 or less, more preferably 2.0 or less, and still more preferably 1.6 or less. In addition, in this invention, molecular weight distribution (PDI) is what is calculated|required by (weight average molecular weight (Mw) of a block copolymer)/(number average molecular weight (Mn) of a block copolymer). The smaller the PDI, the narrower the molecular weight distribution and the homogeneous molecular weight copolymer becomes, and when the value is 1.0, the width of the molecular weight distribution is 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 or a large molecular weight will be included.

The amine value of the block copolymer is preferably 10 mgKOH/g or more, more preferably 50 mgKOH/g or more, further preferably 80 mgKOH/g or more, 200 mgKOH/ It is preferably not more than g, more preferably not more than 150 mgKOH/g, and still more preferably not more than 120 mgKOH/g.

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 preferably 50 mgKOH/g or less. By setting the acid value in this range, it is possible to work suitably with a binder resin (alkali-soluble resin) without impairing the affinity of the coloring material of the block copolymer.

(Method for producing block copolymer)

As a method for producing the block copolymer, a method of first preparing a block A by polymerization of a vinyl monomer, and then polymerizing a monomer of a block B to a block A; a method of preparing a block B first, and then a monomer of a block A to the block B A method of polymerizing; A method of coupling A block and B block after separately preparing A block and B block, etc. are mentioned.

Although the polymerization method is not particularly limited, living radical polymerization is preferred. That is, as the block copolymer, it is preferable that the block copolymer is polymerized by living radical polymerization. In the conventional radical polymerization method, not only the initiation reaction and the growth reaction, but also the stop reaction and the chain transfer reaction cause loss of activity at the growth end, which tends to become a mixture of polymers having various molecular weights and non-uniform composition. On the other hand, the living radical polymerization method maintains the simplicity and versatility of the conventional radical polymerization method, while the stop reaction or chain transfer is difficult to occur, and the growth end grows without loss of activity, so precise control of the molecular weight distribution and uniform It is preferable because it is easy to manufacture the polymer of the 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); a method using an organic tellurium compound according to the difference in the method of stabilizing the polymerization growth terminal. There are methods such as (TERP method). Since the ATRP method uses an amine-based complex, there are cases where 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, it is difficult to obtain a low molecular weight distribution, and there may be problems such as sulfur odor and coloring. Among these methods, it is preferable to use the TERP method from the viewpoint of diversity of monomers that can be used, molecular weight control in the polymer region, uniform composition, or coloring.

The TERP method is a method of polymerizing a radically polymerizable compound (vinyl monomer) by using an organic tellurium compound as a chain transfer agent. For example, International Publication No. 2004/14848, International Publication No. 2004/14962, International Publication It is a method described in 2004/072126 and International Publication No. 2004/096870.

As a specific polymerization method of the TERP method, the following (a) to (d) can be mentioned.

(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 polymerization initiator.

(c) A vinyl monomer is polymerized using a mixture of an organic tellurium 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 tellurium compound represented by the general formula (3), an azo polymerization initiator, and an organic ditelluride compound represented by the general formula (4).

[In 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 General Formula (4), R ³¹ represents a C 1 to C 8 alkyl group, an aryl group, or an aromatic heterocyclic group.]

The ^{group represented by R 31} is an alkyl group, an aryl group or an aromatic heterocyclic group having 1 to 8 carbon atoms, and is specifically as follows.

Examples of the alkyl group having 1 to 8 carbon atoms include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, hexyl group, heptyl group, oxy Linear or branched chain alkyl groups, such as a yl group, and cyclic alkyl groups, such as a cyclohexyl group, etc. are mentioned. Preferably, it is a C1-C4 linear or branched chain alkyl group, More preferably, it is 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 group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, hexyl group, heptyl group, oxy Linear or branched chain alkyl groups, such as a yl group, and cyclic alkyl groups, such as a cyclohexyl group, etc. are mentioned. Preferably, it is a C1-C4 linear or branched chain alkyl group, More preferably, it is 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 or a propargyl group, and specifically Is as follows.

Examples of the alkyl group having 1 to 8 carbon atoms include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, hexyl group, heptyl group, oxy Linear or branched chain alkyl groups such as a tyl group, and cyclic alkyl groups such as a cyclohexyl group, etc. are mentioned. Preferably, it is a C1-C4 linear or branched chain alkyl group, More preferably, it is 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. As the substituent of the aryl group having the above substituent, for example, a halogen atom, a hydroxy group, an alkoxy group, an amino group, a nitro group, a cyano group, a carbonyl-containing group represented by ^{-COR 341 (R 341} is 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. Moreover, it is good that 1 or 2 of these substituents are substituted.

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, ethoxy group, propoxy group, isopropoxy group, n-butoxy group, sec-butoxy group, tert- Butoxy group, pentyloxy group, hexyloxy group, heptyloxy group, octyloxy group, etc. are mentioned.

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 having 1 to 8 carbon atoms, or an aryl group).

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. For example, a carboxyl group, a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, n- Butoxycarbonyl group, sec-butoxycarbonyl group, tert-butoxycarbonyl group, n-pentyloxycarbonyl group, phenoxycarbonyl group, and the like. As a preferable oxycarbonyl group, a methoxycarbonyl group and an ethoxycarbonyl group are mentioned.

As the allyl group, -CR ³⁴⁴¹ R ³⁴⁴² -CR ³⁴⁴³ =CR ³⁴⁴⁴ R ³⁴⁴⁵ (R ³⁴⁴¹ , R ³⁴⁴² are each independently a hydrogen atom or an alkyl group having 1 to 8 carbon atoms, R ³⁴⁴³ , R ³⁴⁴⁴ , R ³⁴⁴⁵ are each independently Examples thereof include a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or an aryl group, and each substituent may be connected in a cyclic structure).

Examples of pro Parr ^{long, -CR 3451 R 3452 -C≡CR 3453 (} R 3451, R 3452 is a hydrogen atom or an alkyl group having 1 to 8 carbon atoms, R ³⁴⁵³ is a hydrogen atom, alkyl group having 1 to 8 carbon atoms, an aryl group, or Silyl group), etc. are mentioned.

The organic tellurium compound represented by the general formula (3) is specifically, (methyltelanylmethyl)benzene, (methyltelanylmethyl)naphthalene, ethyl-2-methyl-2-methyltelanyl-propionate, ethyl -2-Methyl-2-n-butyltelanyl-propionate, (2-trimethylsiloxyethyl)-2-methyl-2-methyltelanyl-propionate, (2-hydroxyethyl)-2- Methyl-2-methyltellanyl-propionate or (3-trimethylsilylpropargyl)-2-methyl-2-methyltellanyl-propionate, etc., International Publication No. 2004/14848, International Publication No. 2004/ All of the organic tellurium compounds described in 14962, International Publication No. 2004/072126, and International Publication No. 2004/096870 can be illustrated.

Specific examples of the organic ditelluride compound represented by the general formula (4) include dimethylditelluride, diethylditelluride, di-n-propylditelluride, diisopropylditelluride, and dicyclopropylditelluride. , Di-n-butylditelluride, di-s-butylditelluride, di-t-butylditelluride, dicyclobutylditelluride, diphenylditelluride, bis-(p-methoxyphenyl) Ditelluride, bis-(p-aminophenyl)ditelluride, bis-(p-nitrophenyl)ditelluride, bis-(p-cyanophenyl)ditelluride, bis-(p-sulfonylphenyl) Ditelluride, dinaphthylditelluride, dipyridylditelluride, and the like can be exemplified.

The azo-based polymerization initiator can be used without particular limitation, as long as it is an azo-based polymerization initiator used by 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)propane], 2,2'-azobis[2-methyl-N-(2-hydroxyethyl)propionamide], 2,2'-azo Bis(2,4,4-trimethylpentane), 2-cyano-2-propylazoformamide, 2,2'-azobis(N-butyl-2-methylpropionamide), or 2,2'-azo Bis(N-cyclohexyl-2-methylpropionamide) etc. can be illustrated.

The polymerization process is carried out in a container substituted with an inert gas, for the purpose of accelerating the reaction, controlling molecular weight and molecular weight distribution, etc., depending on the type of vinyl monomer and the organic tellurium compound of the general formula (3), and further The polymerization initiator and/or the organic ditelluride compound of the general formula (4) are mixed. In this case, nitrogen, argon, helium, etc. are mentioned as an inert gas. Preferably, argon and nitrogen are good.

The amount of the vinyl monomer used in the above (a), (b), (c) and (d) may be appropriately adjusted according to the properties of the target copolymer. It is preferable to set the vinyl monomer to 5 mol-10000 mol with respect to 1 mol of the organic tellurium compound of general formula (3).

When the organic tellurium compound of the general formula (3) and an azo polymerization initiator are used in combination, the azo polymerization initiator is 0.01 mol to 10 mol per 1 mol of the organic tellurium compound of the general formula (3). desirable.

When using the organic tellurium compound of the general formula (3) of the above (c) and the organic ditelluride compound of the general formula (4) in combination, the general formula (4) with respect to 1 mol of the organic tellurium compound of the general formula (3) It is preferable to set the organic ditelluride compound of 0.01 mol to 100 mol.

When using the organic tellurium compound of the general formula (3) of the above (d), the organic ditelluride compound of the general formula (4), and an azo polymerization initiator in combination, with respect to 1 mol of the organic tellurium compound of the general formula (3) It is preferable that the organic ditelluride compound of the general formula (4) is 0.01 mol to 100 mol, and the azo-based polymerization initiator is preferably 0.01 mol to 10 mol with respect to 1 mol of the organic tellurium compound of the general formula (3).

The polymerization reaction can be carried out even without a solvent, but may be carried out by stirring the mixture using an aprotic solvent or a protic solvent generally used in radical polymerization. Aprotic solvents that can be used include, for example, anisole, benzene, toluene, N,N-dimethylformamide (DMF), dimethyl sulfoxide (DMSO), acetone, 2-butanone (methylethylketone), Dioxane, propylene glycol monomethyl ether acetate, chloroform, carbon tetrachloride, tetrahydrofuran (THF), ethyl acetate, trifluoromethylbenzene, etc. can be illustrated. In addition, as a protic solvent, for example, water, methanol, ethanol, isopropanol, n-butanol, ethyl cellosolve, butyl cellosolve, 1-methoxy-2-propanol, hexafluoroisopropanol or diacetone alcohol And the like can be illustrated.

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

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

After completion of the polymerization reaction, the target copolymer can be separated from the obtained reaction mixture by removing the solvent to be used and the remaining vinyl monomer by a conventional separation and purification means.

The growth end of the copolymer obtained by the polymerization reaction is in the form of -TeR ³¹ derived from a tellurium compound (in the formula, R ³¹ is the same as above), and the activity is lost by operation in air after the polymerization reaction is completed. There are cases where tellurium atoms remain. Since the copolymer in which the tellurium atom remains at the terminal is colored or has poor thermal stability, it is preferable to remove the tellurium atom.

As a method of removing the tellurium atom, a radical reduction method using tributyl stannane or a thiol compound, etc.; a method of adsorbing with activated carbon, silica gel, activated alumina, activated clay, molecular sieve, and a polymer adsorbent; Method of adsorbing metal with ion exchange resin, etc.; adding hydrogen peroxide water or peroxide such as benzoyl peroxide, or by blowing air or oxygen into the system to oxidatively decompose the tellurium atom at the end of the copolymer, washing with water or using an appropriate solvent. A liquid-liquid extraction method or a solid-liquid extraction method in which residual tellurium compounds are removed by combining; a purification method in a solution state such as ultrafiltration, which extracts and removes only those with a specific molecular weight or less, can be used, and a combination of these methods It can also be used.

In addition, 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 a tellurium compound (in the formula, R ³² , R ³³ and R ³⁴ are the formulas It is the same as ^{R 32} , R ³³ and R ³⁴ in (3)).

In the case of quaternizing the tertiary amine group of the structural unit represented by formula (1), examples of the quaternizing agent include alkyl halides such as methyl chloride, ethyl chloride, methyl bromide, and methyl iodide; benzyl chloride, benzyl bromide, benzyl iodide, etc. And dialkyl sulfates such as aralkyl halide; dimethyl sulfate; diethyl sulfate and di-n-propyl sulfate. Among these, aralkyl halide, such as benzyl chloride, benzyl bromide, and benzyl iodide, is preferable, and benzyl chloride is more preferable. As the structure after quaternization, an alkyl group and an aralkyl group derived from a quaternizing agent are introduced. Therefore, by measuring the amount of the alkyl group and the aralkyl group introduced by quaternization, the amount of the structural unit represented by the formula (2) can be estimated.

As a method of quaternizing the tertiary amine structure of a part of the structural unit represented by formula (1) in the polymer, a method of bringing the polymer and a quaternizing agent into contact can be mentioned. Specifically, after polymerization of a monomer composition containing a vinyl monomer capable of forming the 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 a quaternizing agent, it is also preferable to dilute the reaction liquid after polymerization. As a solvent added for dilution, a solvent that can be used in the polymerization reaction is exemplified, a protic solvent is preferable, and methanol is more preferable.

(Polymerization product)

As the dispersant composition, as a dispersant component, a polymerization product containing the block copolymer may be used. The polymerization product refers to a product obtained when a polymerization operation (quaternization treatment as necessary) is performed in order to obtain the block copolymer. The polymerization product contains a desired block copolymer and a polymer impurity produced by synthesizing the block copolymer.

The polymer impurities are other polymers that are inevitably produced when synthesizing a desired block copolymer. For example, as polymer impurities produced by-products when synthesizing an A-B 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 exemplified. In addition, polymer impurities are polymers that are by-products when synthesizing a desired block copolymer, and do not include polymers added separately.

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

(Dispersion medium)

The dispersant composition may contain a dispersion medium. As the dispersion medium, as long as it disperses or dissolves the block copolymer, does not react with these components, and has adequate volatility, it can be appropriately selected and used. 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, methoxymethylpentanol , Methoxypropanol, propylene glycol monoethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol monomethyl ether, 3-methyl-3-methoxybutanol, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, tri Glycol monoalkyl ethers such as propylene glycol methyl ether; ethylene glycol dimethyl ether, ethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, Glycol dialkyl ethers such as 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, diethylene Glycol alkyl ether acetates such as glycol mono-n-butyl ether acetate, dipropylene glycol monomethyl ether acetate, triethylene glycol monomethyl ether acetate, triethylene glycol monoethyl ether acetate, and 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 , Dipropyl ether, diisopropyl ether, butyl ether, diamyl ether, ethyl isobutyl ether, dihex Ethers such as silether; acetone, methyl ethyl ketone, methyl amyl ketone, methyl isopropyl ketone, methyl isoamyl ketone, diisopropyl ketone, diisobutyl ketone, methyl isobutyl ketone, cyclohexanone, ethyl amyl ketone , Methylbutyl ketone, methylhexyl ketone, methylnonyl ketone, methoxymethylpentanone, and other ketones; ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, butanediol, diethylene glycol, dipropylene glycol , Monohydric or polyhydric alcohols such as triethylene glycol, glycerin, and benzyl alcohol; aliphatic hydrocarbons such as n-pentane, n-octane, diisobutylene, n-hexane, hexene, isoprene, dipentene, and dodecane; Alicyclic hydrocarbons such as cyclohexane, methylcyclohexane, methylcyclohexene, and bicyclohexyl; aromatic hydrocarbons such as benzene, toluene, xylene, and cumene; 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, 3-ethoxy Chain or cyclic esters such as methyl propionate, ethyl 3-ethoxypropionate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, propyl 3-methoxypropionate, butyl 3-methoxypropionate, and γ-butyrolactone ; Alkoxycarboxylic acids such as 3-methoxypropionic acid and 3-ethoxypropionic acid; Halogenated hydrocarbons such as butyl chloride and amyl chloride; Ether ketones such as methoxymethylpentanone; Nitriles such as acetonitrile and benzonitrile, etc. Can be mentioned.

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, preferably 30% by mass in consideration of a viscosity suitable for production of a colored composition described later.

<Coloring composition>

The coloring composition of this invention contains the said dispersing agent composition, a coloring material, a binder resin, and a dispersion medium.

(Coloring material)

The kind of the coloring material may be appropriately selected depending on the application, and examples thereof include pigments and dyes. It is preferable that the said coloring composition contains a pigment as a coloring material from a viewpoint of light resistance and heat resistance. As the pigment, any of an organic pigment and an inorganic pigment may be used, but an organic pigment containing an organic compound as a main component is particularly preferable. As a pigment, each color pigment, such as a red pigment, a yellow pigment, an orange pigment, a blue pigment, a green pigment, and a purple pigment, is mentioned, for example. The structure of the pigment is azo pigments such as monoazo pigments, diazo pigments and condensed diazo pigments, diketopyrrolopyrrole pigments, phthalocyanine pigments, isoindolinone pigments, isoindoline pigments, quinacridone pigments And polycyclic pigments such as pigments, indigo pigments, thioindigo pigments, quinophthalone pigments, dioxazine pigments, anthraquinone pigments, perylene pigments, and perinone pigments. The number of pigments contained in the coloring composition may be only one type or may be plural types.

As a specific example of a pigment, C.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; CI 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; CI Orange pigments such as Pigment Orange 36, 38, 43; C.I. Blue pigments such as Pigment Blue 15, 15:2, 15:3, 15:4, 15:6, 16, 22, 60; C.I. Pigment Green 7, 36, 58, 59, 62, 63, aluminum phthalocyanine, polyhalogenated aluminum phthalocyanine, aluminum phthalocyanine hydroxide, diphenoxyphosphinyloxy aluminum phthalocyanine, diphenylphosphinyloxy aluminum phthalocyanine, polyhalogenated diphenoxyphosphi Green pigments such as niloxy aluminum phthalocyanine and polyhalogenated diphenylphosphinyloxy aluminum phthalocyanine; CI Purple pigments, such as Pigment Violet 23, 32, 50, etc. are mentioned. Among these pigments, C.I. Pigment Red 254, C.I. Pigment Red 255, C.I. Pigment Red 264, C.I. Pigment Blue 15, C.I. Pigment Blue 15:2, C.I. Pigment Blue 15:3, C.I. Pigment Blue 15:4, C.I. Pigment Blue 15：6, C.I. Pigment Blue 16, C.I. Pigment Green 7, C.I. Pigment Green 36, C.I. Pigment Green 58, C.I. Pigment Green 59 and the like are preferred.

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, and the blue pigment 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 the light-shielding rate and image characteristics.

The average particle diameter of the coloring material may be appropriately selected depending on the application, and there is no particular limitation. From the viewpoint of high transparency and high contrast, the colored composition preferably contains a coloring material having an average particle diameter of 10 nm to 150 nm.

The coloring material may contain a dye derivative as a dispersing aid. As the dye derivative, it is preferable to contain an acidic dye derivative having an acidic group since it is adsorbed by ion bonding with 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 identical or similar to the coloring material constituting the coloring composition, and a skeleton identical or similar to the compound used as a raw material for the pigment is preferable. Specific examples of the dye skeleton include an azo dye skeleton, a phthalocyanine dye skeleton, an anthraquinone pigment skeleton, a triazine pigment skeleton, an acridine pigment skeleton, and a perylene pigment skeleton. As the acidic group introduced into the dye skeleton, a carboxyl group, a phosphoric acid group, and a sulfonic acid group are preferable. In addition, a sulfonic acid group is preferred for the convenience of synthesis and in terms of the intensity of acidity. Further, the acidic group may be directly bonded to the dye skeleton, but may be bonded to the dye skeleton through a hydrocarbon group such as an alkyl group or an aryl group; an ester, ether, sulfonamide, or urethane bond. Although the amount of the dye derivative is not particularly limited, it is preferably 4 parts by mass to 17 parts by mass, for example, based on 100 parts by mass of the coloring material.

The upper limit of the content of the coloring material in the coloring composition is usually 80 mass%, preferably 70 mass%, and more preferably 60 mass% in the total solid content of the coloring composition from the viewpoint of luminance. Moreover, 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. Here, the solid content is a component other than the dispersion medium described later.

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 preferably 10 parts by mass to 100 parts by mass with respect to 100 parts by mass of the coloring material. And, it is more preferable that it is 10 mass parts-80 mass parts.

(Binder resin)

The colored composition contains a binder resin (however, except for a polymer having a structure represented by the general formula (5) in the side chain). Thereby, alkali developability of a colored composition and binding property to a board|substrate can be improved. Although it does not specifically limit as such a binder resin, It is preferable that it is a resin which has acidic groups, such as a carboxy group and a phenolic hydroxy group.

As the binder resin, a random copolymer containing a structural unit derived from a carboxyl group-containing vinyl monomer and a structural unit derived from (meth)acrylate is preferable. As said 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 the structural unit derived from a carboxyl group-containing vinyl monomer and the structural unit derived from (meth)acrylate is preferably 50% by mass or more, more preferably 60% by mass or more, and more preferably Is 70% by mass or more. In addition, the binder resin has a content rate of a structure derived from a carboxyl group-containing vinyl monomer is preferably 5% by mass or more, more preferably 10% by mass or more, still more preferably 20% by mass or more, and 90% by mass or less. Is preferably, more preferably 70% by mass or less.

Among these, it is preferable that it is a random copolymer of a carboxyl group-containing vinyl monomer and (meth)acrylate. 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, and (meth)acrylic acid and butyl (meth)acrylic. And a random copolymer of benzyl (meth)acrylate and the like. 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 carboxyl group-containing vinyl monomer and (meth)acrylate, the content of (meth)acrylic acid is usually 5% by mass to 90% by mass, preferably 10% by mass to 70% by mass, among all monomer components. , It is more preferable that it is 20 mass%-70 mass %.

The binder resin may have a carbon-carbon double bond capable of radical polymerization in the side chain. By having a double bond in the side chain, since the photocurability of the colored composition according to the present invention increases, resolution and adhesion can be further improved. As a method of introducing a radically polymerizable carbon-carbon double bond into the side chain, for example, glycidyl (meth)acrylate, 3,4-epoxycyclohexylmethyl (meth)acrylate, o- (or m-, Alternatively, a method of reacting a compound such as p-) vinylbenzyl glycidyl ether to the acidic group of the binder resin is exemplified.

It is preferable that it is 3,000-100,000, as for Mw of a binder resin, it is more preferable that it is 5,000-50,000, and it is still more preferable that it is 5,000-20,000. When Mw of the binder resin is 3,000 or more, the heat resistance, film strength, etc. of the colored layer formed of the colored composition become good, and when Mw is 100,000 or less, the alkali developability of this coating film 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, the alkali developability when the colored composition is used as a colored layer becomes more favorable, and when it is 170 mgKOH/g or less, the heat resistance becomes good.

Only one type may be sufficient as the binder resin contained in a colored composition, and multiple types may be sufficient as it. 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 20 parts by mass to 80 parts by mass per 100 parts by mass of the coloring material. More preferable.

(Crosslinking agent)

If necessary, the colored composition may contain a crosslinking agent. The 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.

As a specific example of the compound having two or more (meth)acryloyl groups, polyfunctional (meth)acrylate obtained by reacting an aliphatic polyhydroxy compound with (meth)acrylic acid, and caprolactone-modified polyfunctional (meth)acrylate , Alkylene oxide-modified polyfunctional (meth)acrylate, polyfunctional urethane (meth)acrylate obtained by reacting a (meth)acrylate having a hydroxyl group with a polyfunctional isocyanate, (meth)acrylate having a hydroxyl group and an acid anhydride The polyfunctional (meth)acrylate etc. which have a carboxy group obtained by reacting are mentioned.

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

In the above colored composition, the content of the crosslinking agent is preferably 10 parts by mass to 1,000 parts by mass, and particularly preferably 20 parts by mass to 500 parts by mass with respect to 100 parts by mass of the coloring material. If the content of the crosslinking agent is too small, there is a fear that sufficient curability may not be obtained. On the other hand, when the amount of the crosslinking agent is too large, alkali developability is lowered in the colored composition of the present invention, and scuming, film residues, etc. tend to occur easily on the substrate or the light-shielding layer of the unexposed portion.

(Photopolymerization initiator)

The said colored composition may contain a photoinitiator as needed. Thereby, radiation-sensitive property can be imparted to the colored composition. The photopolymerization initiator is a compound that generates an active species capable of initiating polymerization of a crosslinking agent by exposure to radiation such as visible light, ultraviolet rays, far infrared rays, electron rays, and X-rays.

Examples of the photopolymerization initiator include thioxanthone compounds, acetophenone compounds, biimidazole compounds, triazine compounds, O-acyloxime compounds, onium salt compounds, benzoin compounds, benzophenone compounds, α-diketone compounds, polynuclear quinone compounds, diazo compounds, imide sulfonate compounds, amino ketone compounds, and the like. Photoinitiators can be used individually or in mixture of 2 or more types.

In the colored composition of the present invention, the content of the photopolymerization initiator is preferably 0.01 parts by mass to 120 parts by mass, and particularly preferably 1 part by mass to 100 parts by mass, based on 100 parts by mass of the crosslinking agent. In this case, if the content of the photopolymerization initiator is too small, there is a concern that curing may be insufficient due to exposure, while if it is too large, the formed colored layer tends to be easily detached from the substrate during development.

(Dispersion medium)

The coloring composition contains a dispersion medium. As the dispersion medium, as long as it disperses or dissolves other components constituting the colored composition, does not react with these components, and has adequate volatility, it can be appropriately selected and used. For example, a conventionally known organic solvent can be used, for example, an organic solvent (dispersion medium) that can be used in the dispersant composition. The organic solvent is preferably glycol alkyl ether acetates, monohydric or polyhydric alcohols from the viewpoints of dispersibility of pigments, the solubility of dispersants, and coating properties of the pigment dispersion composition. The number of solvents contained in the pigment dispersion composition may be only one type or may be plural types.

When forming pixels of a color filter by a photolithography method, the boiling point of the dispersion medium (under a pressure of 1013.25 hPa. Hereinafter, all of the boiling points are the same) is preferably 100°C to 200°C. Among the above dispersion media, glycol alkyl ether acetates are preferred because the balance of coating properties and surface tension is good, and the solubility of the constituent components in the colored composition is relatively high. Further, 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 destruction of the mutual relationship of the colored composition due to the rapid drying of the colored composition. Further, the dispersion medium having a boiling point of 150°C or higher may be glycol alkyl ether acetates. The content ratio of the dispersion medium having a boiling point of 150°C or higher is preferably 3 to 50% by mass in the total 100% by mass of the dispersion medium.

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. In addition, the lower limit of the content of the dispersion medium in the colored composition is usually 70% by mass, preferably 80% by mass in consideration of a viscosity suitable for application of the colored composition. The dispersion medium can be used as a solvent for dissolving and removing precipitates formed from the colored composition.

(Other formulations)

In addition to the above compounding agent, other compounding agents may be compounded in the colored composition as long as the range does not impair the desirable physical properties of the present invention. Other compounding agents include sensitizing dyes, thermal polymerization inhibitors, nonionic surfactants, anionic surfactants, cationic surfactants, amphoteric surfactants, plasticizers, organic carboxylic acid compounds, organic carboxylic anhydrides, pH adjusters, antioxidants, UV absorbers, light stabilizers, preservatives, mold inhibitors, surfactants, anti-aggregation agents, adhesion improvers, development improvers, storage stabilizers, and the like.

As a sensitizing dye, 4,4'-dimethylaminobenzophenone, 4,4'-diethylaminobenzophenone, 2-aminobenzophenone, 4-aminobenzophenone, 4,4'-diaminobenzophenone, 3, 3 '-Diaminobenzophenone, 3,4-diaminobenzophenone, 2-(p-dimethylaminophenyl)benzoxazole, 2-(p-diethylaminophenyl)benzoxazole, 2-(p-dimethylamino Phenyl)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)benzothiazole, 2-(p-dimethylaminophenyl)benzimidazole, 2-(p-diethyl Aminophenyl)benzoimidazole, 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, and β-naphthol.

Examples of the nonionic surfactant include a fluorine surfactant, a silicone surfactant, and a polyoxyethylene surfactant.

As anionic surfactants, alkyl sulfonates, alkylbenzene sulfonates, alkyl naphthalene sulfonates, polyoxyethylene alkyl ether sulfonates, alkyl sulfates, alkyl sulfuric acid ester salts, higher alcohol sulfuric acid ester salts, aliphatic alcohol sulfuric acid Ester salts, polyoxyethylene alkyl ether sulfates, polyoxyethylene alkylphenyl ether sulfates, alkyl phosphoric acid ester salts, polyoxyethylene alkyl ether phosphates, polyoxyethylene alkylphenyl ether phosphates, special polymer surfactants, etc. I can.

Examples of the cationic surfactant include quaternary ammonium salts, imidazoline derivatives, and alkylamine salts.

Examples of amphoteric surfactants include betaine compounds, imidazolium salts, imidazolines, amino acids, and the like.

Examples of the plasticizer include dioctyl phthalate, didodecyl phthalate, triethylene glycol dicaprylate, dimethyl glycol phthalate, tricresyl phosphate, dioctyl adipate, dibutyl sebacate, and triacetyl glycerin.

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

As organic carboxylic anhydride, acetic anhydride, trichloroacetic anhydride, trifluoroacetic anhydride, tetrahydrophthalic anhydride, succinic anhydride, maleic anhydride, citraconic anhydride, itaconic anhydride, glutaric anhydride, 1,2 -Cyclohexenedicarboxylic acid, n-octadecylsuccinic anhydride, 5-norbornene-2,3-dicarboxylic anhydride, phthalic anhydride, trimellitic anhydride, pyromellitic anhydride, naphthalic anhydride, and the like.

<Production method of colored composition>

The said colored composition can be prepared by mixing a coloring material, a dispersant composition, a binder resin, a dispersion medium, and a crosslinking agent, a photoinitiator, and another compounding agent as needed. Mixing can be performed using a mixing and dispersing machine such as a paint shaker, a bead mill, a ball mill, a dissolve bar, or a kneader. It is preferable to filter the colored composition after mixing. Since the said colored composition has alkali developability, it can be used suitably as a color filter use.

Moreover, as a coloring material, what was previously surface-treated with the dispersing agent composition of this invention can also be used. As the surface treatment method, a dry method in which a dispersant is added and mixed while stirring the coloring material using a Henschel mixer, a ball mill, an atomizer colloid mill, a Benbury mixer, etc., or a wet method in which the solvent is removed after treatment in a solvent can be used. . Thus, by performing the surface treatment with the dispersant composition of the present invention, the dispersibility of the coloring material can be improved and aggregation can be prevented.

<Color filter>

The color filter of the present invention is provided with a colored layer formed using the colored composition.

As a method of manufacturing a color filter, the following method is mentioned, for example. First, thermoplastic resin sheets such as polyester resins, polyolefin resins, polycarbonate resins, and polymethyl methacrylate resins; thermosetting resin sheets such as epoxy resins, unsaturated polyester resins, and poly(meth)acrylic resins; various glasses, etc. On the transparent substrate of, a color pixel that transmits light of three primary colors of red (R), green (G) and blue (B) is provided, and a black matrix formed of the above colored composition is preferably provided. As a method of manufacturing a color filter, after applying a black colored composition, prebaking is performed to evaporate a solvent (dispersion medium) to form a coating film. Next, after exposure to the coating film through a photomask, it is developed using an alkali developer (such as an organic solvent or an aqueous solution containing a surfactant and an alkaline compound), dissolving and removing the unexposed part of the coating film, and removing a black pattern ( Black matrix). After that, post-baking as necessary, and then repeating the same operation sequentially for red (R), green (G), and blue (B), a pixel array of three primary colors of red, green and blue is placed on the substrate. Color filters can be obtained. However, in the present invention, the order of forming each color pixel is not limited to the above.

When applying the colored composition to the substrate, an appropriate coating method such as a spray method, a roll coating method, a rotation coating method (spin coating method), a slit die coating method, and a bar coating method may be employed. In particular, a spin coating method, It is preferable to employ a slit die coating method.

After forming a protective film as necessary on the pixel pattern thus obtained, a transparent conductive film (such as indium tin oxide (ITO)) is formed by sputtering. After the transparent conductive film is formed, 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 element, a color imaging tube element, a color sensor, an organic EL display element, electronic paper, or the like.

In addition, since the colored composition has a low viscosity and excellent dispersibility of a coloring material, it can be suitably used as a colored column spacer supporting a color filter substrate and a thin film transistor (TFT) substrate positioned between the liquid crystal layer. . For example, the composition of high optical density (Optical Depth: OD) described in Japanese Unexamined Patent Application Publication No. 2015-191234 is mentioned.

[Example]

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

In addition, the meaning of the abbreviation is as follows.

BMA: Butyl methacrylate

PCL5: 5-mol caprolactone adduct of 2-hydroxyethyl methacrylate (manufactured by Daicel Corporation, PLACCEL (registered trademark) FM5)

DMAEMA: Dimethylaminoethyl methacrylate

DEAEMA: Diethylaminoethyl methacrylate

TBAEMA: tert-butylaminoethyl methacrylate

BTEE: Ethyl-2-methyl-2-n-butyltelanyl-propionate

DBDT: Dibutylditelluride

AIBN: 2,2'-azobis (isobutyronitrile)

PMA: Propylene glycol monomethyl ether acetate

(Polymerization rate)

Nuclear magnetic resonance (NMR) measuring device (Bruker BioSpin Co., Ltd., model: AVANCE500 (frequency 500MHz)) using a measuring a ¹ H-NMR were (solvent:: CDCl _3, internal standard TMS). For the obtained NMR spectrum, the integral ratio of the peak of the vinyl group derived from the monomer and the peak of the ester side chain derived from the polymer was calculated, and the polymerization rate 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 chromatography (manufactured by Tosoh Corporation, model HLC-8320). 1 column SHODEX KF-603 (φ6mm×150mm) (manufactured by SHODEX), a 10mmol/L lithium bromide/10mmol/L acetic acid/N-methyl-2-pyrrolidone solution as a mobile phase, and a differential refractometer as a detector. did. 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) were measured. The molecular weight distribution (PDI = Mw/Mn) was calculated from this measured value.

(Amine number)

The amine value represents the mass of the basic component and the equivalent of potassium hydroxide (KOH) 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 appropriate pH curve as the appropriate end point.

B=56.11×Vs×0.1×f/w

B: Amine number (mgKOH/g)

Vs: The amount of 0.1 mol/L hydrochloric acid/2-propanol solution required for titration (mL)

f: 0.1 mol/L hydrochloric acid (2-propanol) titer

w: Mass of the measurement sample (g) (converted to 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 controller rotor (1° 34'×R24). Measurement was performed about the colored composition stored at 25 degreeC for 2 hours after preparation.

(Particle diameter)

Using a thick particle size analyzer (trade name: FPAR-1000, manufactured by Otsuka Electronics Co., Ltd.), the particle size was measured at 25°C. Measurement was performed about the colored composition stored at 25 degreeC for 2 hours after adjustment. If necessary, the sample was diluted with propylene glycol monomethyl ether acetate (PGMEA).

(Formaldehyde amount)

0.5 g of the dispersant composition was injected into a cartridge filled with silica gel impregnated with DNPH (2,4-dinitrophenylhydrazine) (manufactured by Waters Corporation, Sep Pak (registered trademark) DNPH silica plus cartridge (product number: WAT037500)). And left to stand at room temperature for 2 hours.

Washed with 4 mL of acetonitrile and adjusted to 5 mL. Liquid chromatograph (manufactured by Shimadzu Corporation, trade name: LC-10AD, column: Pro C18 RS (4.6×250mm, 5μm (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), as a standard substance, two aldehyde-DNPH mixed standard solutions (0.1 μg aldehyde/μL acetonitrile, manufactured by Wako Pure Chemical Industries, Ltd.) were used to measure. The amount of formaldehyde was calculated from the measurement results.

<Production of block copolymer>

(Block copolymer No.1)

PCL5 (275.8g), BMA (45.3g), AIBN (1.64g), and PMA (80.3g) were injected into a flask equipped with an argon gas inlet tube and a stirrer, and after argon substitution, BTEE (14.99g), DBDT ( 18.47 g) was added and reacted at 60°C for 7 hours. The polymerization rate was 98.3%.

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

After completion of the reaction, the reaction solution was poured into stirring n-heptane. Block copolymer No. 1 was obtained by suction filtration and drying the precipitated polymer. The obtained block copolymer No. 1 had an Mw of 16,301, a PDI of 1.44, and an amine value of 108 mgKOH/g. Moreover, the composition of the block copolymer No. 1 was shown in Table 2. In addition, the content rate of each structural unit in the copolymer was calculated from the injection rate and the polymerization rate of the monomer used in the polymerization reaction.

(Block copolymer No. 2, 3)

Block copolymer Nos. 2 and 3 were produced in the same manner as in the production method of block copolymer No. 1. In Table 1, the used monomer, organic tellurium compound, organic ditelluride compound, azo polymerization initiator, solvent, reaction conditions, and polymerization rate are shown. Moreover, in Table 2, the composition, Mw, PDI, and amine value of each block copolymer were shown. In addition, the content rate of each structural unit in the copolymer was calculated from the injection rate and the polymerization rate of the monomer 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 it is shown in Table 2.

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

<Synthesis of alkali-soluble resin (binder resin)>

Into a flask equipped with an argon gas inlet and a stirrer, methacrylic acid (MAA) (40.0 g), benzyl methacrylate (BzMA) (160.0 g), and propylene glycol monomethyl ether acetate (PMA) (580.0 g) were injected. , After argon substitution, 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 over 1.5 hours. It was loaded. 60 minutes after the dropping was completed, the temperature was raised to 110° C., AIBN (0.8 g) and PMA (10.0 g) were added to react for 1 hour, and AIBN (0.8 g) and PMA (10.0 g) were added. Then, the mixture was reacted for 1 hour, further added AIBN (0.8 g) and PMA (10.0 g), followed by reaction for 1 hour.

The obtained reaction solution was cooled to room temperature, and PMA (240.0 g) was added to obtain a solution of an alkali-soluble resin having a nonvolatile content of 39.5%. 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 colored composition>

Coloring composition No.1

The blending composition was adjusted so that 8 parts by mass of pigment, 6 parts by mass of block copolymer No. 1, 6 parts by mass of alkali-soluble resin, and 80 parts by mass of PMA were added, and 555 parts by mass of 0.3 mm zirconia beads were added, and a bead mill (trade name: DISPERMAT CA, VMA-GETZMANN GmbH (manufactured by VMA-GETZMANN GmbH) was mixed for 3 hours and sufficiently dispersed. After completion of the dispersion, the beads were separated by filtration to obtain a colored composition. Pigments include C.I. Pigment Red 254 (brand name: BKCF, manufactured by Ciba Specialty Chemicals Inc.) was used. The dispersibility of the obtained colored composition was evaluated. Table 3 shows the evaluation results.

Coloring composition No.2, 3

Except having changed the block copolymer, it carried out similarly to the preparation method of coloring composition No. 1, and prepared coloring compositions No. 2 and 3. Table 3 shows the evaluation results.

All of the coloring compositions No. 1 to 3 have good dispersibility of the pigment. Therefore, it is 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. In particular, the coloring composition No. 1 using a block copolymer in which the B block has a structural unit derived from diethylaminoethyl methacrylate is excellent in dispersibility of the pigment. Therefore, it can be seen that the use of a block copolymer in which the B block has a structural unit derived from diethylaminoethyl methacrylate can reduce the amount of formaldehyde, and a colored composition having excellent pigment dispersibility can be obtained.

The following embodiments are included in the present invention.

(Embodiment 1)

A dispersant composition comprising a polymer having a structure represented by the general formula (5) in the side chain.

*-Y ¹ -NR ¹¹ R ¹² (5)

[In General Formula (5), R ¹¹ represents a hydrogen atom or a chain or cyclic hydrocarbon group having 2 or more carbon atoms which may have a substituent. R ¹² represents a chain or cyclic hydrocarbon group having 2 or more carbon atoms which may have a substituent. R ¹¹ and R ¹² may be bonded to each other to form a cyclic structure. Y ¹ represents a divalent hydrocarbon group. * Represents a binding hand.]

(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)

The dispersant composition according to Embodiment 1 or 2, wherein the polymer is a block copolymer having a block A having a structural unit derived from a (meth)acrylic monomer and a block B having a structural unit represented by the general formula (1).

[In General Formula (1), R ¹¹ represents a hydrogen atom or a chain or cyclic hydrocarbon group having 2 or more carbon atoms which may have a substituent. R ¹² represents a chain or cyclic hydrocarbon group having 2 or more carbon atoms which may have a substituent. R ¹¹ and R ¹² may be bonded to 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.]

(Embodiment 4)

The dispersant composition according to Embodiment 3, wherein the A block has a structural unit represented by General Formula (10).

[In General Formula (10), n1 represents the integer of 1-10. 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.]

(Embodiment 5)

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

(Embodiment 6)

The dispersant composition according to any one of Embodiments 3 to 5, wherein the block copolymer is polymerized by living radical polymerization.

(Embodiment 7)

A coloring composition comprising the dispersant composition, a coloring material, a binder resin, and a dispersion medium according to any one of Embodiments 1 to 6.

(Embodiment 8)

The coloring composition according to Embodiment 7 for use in color filters.

(Embodiment 9)

A color filter comprising a colored layer formed using the colored composition according to the eighth embodiment.

Claims (9)

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

[In General Formula (1), R ¹¹ represents a hydrogen atom or a chain or cyclic hydrocarbon group having 2 or more carbon atoms which may have a substituent. R ¹² represents a chain or cyclic hydrocarbon group having 2 or more carbon atoms which may have a substituent. R ¹¹ and R ¹² may be bonded to 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 method of claim 3,
The dispersant composition, wherein the A block has a structural unit represented by General Formula (10).

[In General Formula (10), n1 represents the integer of 1-10. 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 method according to claim 3 or 4,
The molecular weight distribution (PDI) of the block copolymer is 2.5 or less, a dispersant composition. The method according to any one of claims 3 to 5,
The dispersant composition, wherein the block copolymer is polymerized by living radical polymerization. A coloring composition comprising the dispersant composition, a coloring material, a binder resin, and a dispersion medium according to any one of claims 1 to 6. The method of claim 7,
A coloring composition for a color filter. A color filter comprising a colored layer formed using the colored composition according to claim 8.