Dispersants, colored compositions, color filters, solid-state imaging devices, and display devices.

Abstract

To provide a dispersant capable of producing a dispersion which has good stability during storage at low temperature and excellent dispersibility even in an ink in which a pigment is incorporated in a high concentration.SOLUTION: There is provided a dispersant represented by the following general formula. In the general formula, A1 to A4 are a combination selected from the group consisting of the following A, B and C, A) two moieties of A1 to A4 are monovalent polymer moieties (P) which are identical or different from each other and the other two moieties are -C(=O)OH or CH2C(=O)OH, which are identical or different from each other, B) one moiety of A1 to A4 is a monovalent polymer moiety (P) and the other 3 moieties are mutually identical or different -C(=O)OH or CH2C(=O)OH and C) one moiety of A1 to A4 is a monovalent polymer moiety (P), two moieties are mutually identical or different -C(=O)OH or CH2C(=O)OH and another moiety is -C(=O)-Xa-Ra.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a dispersant and its use. [Background technology]

[0002] It is generally known that it is difficult to stably disperse a pigment at a high concentration when producing ink, etc. For example, a dispersion containing a pigment consisting of fine particles exhibits high viscosity, making it difficult to remove from a disperser or transport, and if the dispersibility is poor, gelation may occur during storage, making it difficult to use.

[0003] Therefore, dispersants are generally used to maintain a good dispersion state. Dispersants have a structure with a site that adsorbs to the pigment and a site that has high affinity for the solvent, which is the dispersion medium, and the performance of the dispersant is determined by the balance between these two sites. Various dispersants are used depending on the surface condition of the pigment to be dispersed, but acidic dispersants are generally used for pigments with a surface that is biased toward basicity. In this case, the acidic functional group becomes the site of adsorption for the pigment. As such, various dispersants having carboxylic acid as the acidic functional group have been proposed (for example, Patent Document 1). [Prior art documents] [Patent documents]

[0004] [Patent Document 1] Japanese Patent Application Laid-Open No. 2008-029901 Summary of the Invention [Problem to be solved by the invention]

[0005] However, although conventional dispersants provided good dispersibility, fluidity, and storage stability for pigment dispersions, there was room for improvement in dispersion stability during low-temperature storage and in the somewhat high viscosity of inks containing high concentrations of pigment.

[0006] An object of the present invention is to provide a dispersant that has good stability during low-temperature storage and that can be used to produce a dispersion that has excellent dispersibility even in inks containing pigments at high concentrations. [Means for solving the problem]

[0007] The present invention is a dispersant represented by the following general formula (1). General formula (1) [ka]

[0008] In general formula (1), A 1 ~A 4 is a combination selected from the group consisting of A, B, and C below, A)A 1 ~A 4 two of the moieties are monovalent polymer moieties (P) which may be the same or different from each other, and the other two moieties are —C(═O)OH or —CHC(═O)OH which may be the same or different from each other; B)A 1 ~A 4 one moiety is a monovalent polymer moiety (P), and the other three moieties are the same or different -C(=O)OH or CHC(=O)OH; C)A 1 ~A 4 One of the moieties is a monovalent polymer moiety (P), the other two moieties are the same or different -C(=O)OH or CH2C(=O)OH, and the other moiety is -C(=O)-Xa-Ra (wherein Xa is -O- or N(Ra 2 )-, Ra is a group selected from the group consisting of alkyl groups having 1 to 18 carbon atoms, alkenyl groups having 2 to 18 carbon atoms, cycloalkyl groups having 3 to 18 carbon atoms, and aryl groups having 6 to 18 carbon atoms, and Ra 2 is a hydrogen atom or a group selected from the group consisting of alkyl groups having 1 to 18 carbon atoms, alkenyl groups having 2 to 18 carbon atoms, cycloalkyl groups having 3 to 18 carbon atoms, and aryl groups having 6 to 18 carbon atoms), X1 is a tetravalent group represented by the following general formula (2), general formula (3), or general formula (4): [ka]

[0009] [In the general formula (2), k represents 1 or 2. The * represents a bond.] [In general formula (3), R 2 is a direct bond, -CH2-, -O-, -C(=O)-, -C(=O)OCH2CH2OC(=O)-, -C(=O)OCH(OC(=O)CH3)CH2OC(=O)-, -SO2-, -C(CF3)2-, formula: [ka] [The total number of carbon atoms in the group represented by general formula (4) is 4 to 20, and in general formula (4), R 3 is a direct bond, -O-, or a divalent or trivalent hydrocarbon group having 1 to 8 carbon atoms, and R 4 , R 5 , R 6 , and R 9 are each independently a hydrogen atom or a hydrocarbon group having 1 to 8 carbon atoms, or R 4 and R 6 and / or R 5 and R 9 may be directly bonded to form an unsaturated double bond, and R 7 and R 8 are each independently a hydrogen atom or a hydrocarbon group having 1 to 8 carbon atoms, or R 7 and R 8 and form a direct bond or a divalent hydrocarbon group having 1 to 8 carbon atoms to form a cyclic group X 1 or R 3 and R 7 and or R 3 and R 8 and form a trivalent hydrocarbon group having 1 to 8 carbon atoms, and a cyclic group X 1 or R 3 and R 7 and R 8and form a tetravalent hydrocarbon group having 1 to 8 carbon atoms, and a polycyclic group X 1 may be formed.] The monovalent polymer moiety (P) is a cyclic ester polymer moiety having a terminal moiety A, which is a structure derived from a monoalcohol or monoamine having a molecular weight of 300 or less and containing an aromatic ring or an alkyleneoxy unit. [Effects of the Invention]

[0010] The present invention provides a dispersant that has good stability during low-temperature storage and that can be used to produce a dispersion that exhibits excellent dispersibility even in inks containing high concentrations of pigment. The present invention also provides a coloring composition, a color filter, a solid-state imaging device, and a display device that contain the dispersant. DETAILED DESCRIPTION OF THE INVENTION

[0011] The terms used in this specification are defined below. Unless otherwise specified, the terms "(meth)acryloyl," "(meth)acrylic," "(meth)acrylic acid," "(meth)acrylate," or "(meth)acrylamide" respectively mean "acryloyl and / or methacryloyl," "acrylic and / or methacrylic," "acrylic acid and / or methacrylic acid," "acrylate and / or methacrylate," or "acrylamide and / or methacrylamide." Furthermore, in this specification, "CI" refers to the Color Index (CI). Generally, pigment dispersants have a site that adsorbs to the pigment and an affinity to the pigment carrier and the solvent that is the dispersion medium. The dispersant's performance is determined by the balance between these two parts. In other words, in order to achieve dispersibility, both the dispersant's ability to adsorb to the pigment and its affinity with the pigment carrier and the solvent, which is the dispersion medium, are extremely important. The pigment carrier referred to here consists of resin, its precursor, or a mixture of these, excluding the pigment component and dispersant from the non-volatile components.

[0012] <Dispersant> The dispersant of the present invention is a dispersant represented by the general formula (1), and is a tetravalent group X1 and its four substituents, group A 1 ~A 4 and a tetravalent group X 1 is represented by the general formula (2), general formula (3) or general formula (4).

[0013] Substituent A 1 ~A 4 The combination of two is preferably a combination of monovalent polymer moieties (P) and the other two are -C(=O)OH or -CHC(=O)OH, and more preferably a combination of two is monovalent polymer moieties (P) and the other two are -C(=O)OH.

[0014] In the general formula (1), the substituent A 1 ~A 4 The one or two monovalent polymer moieties (P) contained as the copolymer function as moieties that have affinity for the solvent, which is the dispersion medium, and can suppress aggregation of the pigment through steric repulsion.

[0015] <Polymer part (P)> The polymer portion (P) of the present invention is a cyclic ester polymer portion having a terminal portion A, and the terminal portion A has a structure derived from a monoalcohol containing an aromatic ring or an alkyleneoxy unit and having a molecular weight of 300 or less, or a monoamine containing an aromatic ring or an alkyleneoxy unit and having a molecular weight of 300 or less. Because the terminal portion A has an aromatic ring or an alkyleneoxy unit, it is possible to control the affinity to the solvent and the crystallinity of the polymer portion (P). As a result, a dispersion using the dispersant of the present invention exhibits stability during low-temperature storage and stability over time when dispersing pigments at high concentrations.

[0016] The weight-average molecular weight of the monovalent polymer moiety (P) is preferably 400 to 10,000, more preferably 600 to 8,000, and most preferably 800 to 4,000. When the molecular weight is 400 or more, the steric repulsion effect of the solvent-affinitive moiety can prevent pigment aggregation. When the molecular weight is 10,000 or less, solvent solubility is ensured and a sufficient steric repulsion effect can be maintained. When the molecular weight is within the above range, the pigment aggregation suppression effect due to the steric repulsion effect is better.

[0017] Here, the polymer portion (P) is a cyclic ester polymer portion. The molecular weight of these polymers can be easily adjusted to the above range, and they also have good affinity for solvents. More preferably, the polymer portion (P) is substantially free of hydroxyl groups, primary amino groups, secondary amino groups, and thiol groups, in order to prevent adverse effects on dispersibility.

[0018] The tetravalent group X of the dispersant of the present invention 1 is represented by the general formula (2), general formula (3) or general formula (4).

[0019] The tetravalent group X represented by the general formula (4) 1 Preferred embodiments of the group include, for example, the following groups:

[0020] [ka] [ka] [ka]

[0021] [The above structure is represented by the general formula (4) where R 3 and R 7 and R 8 and form a tetravalent hydrocarbon group [>CH-CH2-CH<] to form a polycyclic group X 1 In the formula, * represents a bond.

[0022] [ka]

[0023] [ka]

[0024] [The above structure is represented by the general formula (4) where R3 is a trivalent hydrocarbon radical [>CH-CH2-], and R 8 represents a structure in which the divalent hydrocarbon group [-CH=C(CH3)-] is

[0025] [ka]

[0026] [The above structure is represented by the general formula (4) where R 3 and R 7 and R 8 and form a tetravalent hydrocarbon group [>CH-CH2-CH2-CH<] to form a polycyclic group X 1 This is the case when the following is formed.]

[0027] [ka]

[0028] [The above structure is represented by the general formula (4) where R 3 and R 7 and R 8 and form a tetravalent hydrocarbon group [>CH-CH=CH-CH<] to form a polycyclic group X 1 This is the case when the following is formed.]

[0029] [ka] [ka]

[0030] [The above structure is represented by the general formula (4) where R 3 and R 7 and R 8 and form a tetravalent hydrocarbon group [(-CH2-)2CH-CH(-CH2-)2] to form a polycyclic group X 1 In the general formula (1), from the viewpoint of reducing the viscosity and preservation stability of the pigment dispersion or ink, 1Preferably, the group X represented by the general formula (2) or (3) contains an aromatic ring. 1 Furthermore, in the general formula (2), it is preferable that k is 1, and in the general formula (3), R 2 is a direct bond, -C(=O)-, -C(=O)OCH2CH2OC(=O)-, -SO2-, or the formula:

[0031] [ka] It is preferable that the group is a group represented by the following formula:

[0032] The dispersant of the present invention represented by the general formula (1) contains, as shown in the structural formula, a tetravalent group X 1 The four substituents are group A 1 ~A 4 and having a group A 1 ~A 4 It has two or three carboxyl groups [-C(=O)OH or -CH2C(=O)OH].

[0033] Next, a method for producing the dispersant of the present invention will be described, although it goes without saying that the production method is not limited to the following.

[0034] The dispersant is preferably synthesized, for example, by the following first and second steps. (First step) Method (1) Method for producing "a cyclic ester polymer moiety (APOH) having a terminal moiety A and a hydroxyl group at the other terminal" Method (2) Method for producing "a cyclic ester polymer moiety (APNH2) having a terminal moiety A and an amino group at the other terminal"

[0035] (Second step) A step of reacting the polymer (APOH) or (APNH2) obtained in the first step with a tetracarboxylic dianhydride. Here, the site obtained by removing one hydrogen atom of a hydroxyl group or one hydrogen atom of a primary amino group from the polymer (APOH) or (APNH2) corresponds to A in the dispersant represented by the general formula (1). 1 ~A 4 The tetracarboxylic acid dianhydride constitutes one or two of the monovalent polymer moieties (P) in the general formula (1). 1 Configure.

[0036] First, the first step, method (1), will be described in detail. In the production method of the present invention, in the first step, A "cyclic ester polymer moiety (APOH) having a terminal moiety A and a hydroxyl group at the other terminal" is obtained by ring-opening polymerization of a cyclic compound using a compound selected from the group consisting of monoalcohols or monoamines containing an aromatic ring or an alkyleneoxy unit as an initiator.

[0037] Examples of aromatic ring-containing monoalcohols having a molecular weight of 300 or less include primary hydroxyl group-containing monoalcohols such as benzyl alcohol, phenoxyethanol, paracumylphenoxyethyl alcohol, piperonyl alcohol, and 1-naphthalenemethanol, and secondary hydroxyl group-containing monoalcohols such as 1-hydroxyindane and 1-phenyl-1-propanol. Of these, benzyl alcohol and phenoxyethanol are preferred.

[0038] Examples of alkyleneoxy unit-containing monoalcohols having a molecular weight of 300 or less include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, ethylene glycol monohexyl ether, ethylene glycol mono-2-ethylhexyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, propylene glycol monohexyl ether, propylene glycol mono-2-ethylhexyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monopropyl ether, diethylene glycol monobutyl ether, diethylene glycol monohexyl ether, diethylene glycol mono-2-ethylhexyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol monopropyl ether, and dipropylene glycol monobutyl ether. ether, dipropylene glycol monohexyl ether, dipropylene glycol mono-2-ethylhexyl ether, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, triethylene glycol monopropyl ether, triethylene glycol monobutyl ether, triethylene glycol monohexyl ether, triethylene glycol mono-2-ethylhexyl ether, tripropylene glycol monomethyl ether, tripropylene glycol monoethyl ether, tripropylene glycol monopropyl ether, tripropylene glycol monobutyl ether, tripropylene glycol monohexyl ether, tripropylene glycol mono-2-ethylhexyl ether, tetraethylene glycol monomethyl ether, tetraethylene glycol monoethyl ether, tetraethylene glycol monopropyl ether, tetraethylene glycol monobutyl ether, tetraethylene glycol monohexyl ether, tetraethylene glycol mono-2-ethylhexyl ether, tetrapropylene glycol monomethyl ether,Examples of the alkylene glycol monoalkyl ether include tetrapropylene glycol monoethyl ether, tetrapropylene glycol monopropyl ether, tetrapropylene glycol monobutyl ether, tetrapropylene glycol monohexyl ether, tetrapropylene glycol mono-2-ethylhexyl ether, and tetradiethylene glycol monomethyl ether. Of these, diethylene glycol monomethyl ether, diethylene glycol monopropyl ether, and diethylene glycol monobutyl ether are preferred.

[0039] Aromatic ring-containing monoamines with a molecular weight of 300 or less include, for example: Examples include benzylamine, α-methylbenzylamine, 2-methylbenzylamine, 3-methyl-6 benzylamine, 4-methylbenzylamine, 4-(aminomethyl)phenol, 4-fluorobenzylamine, 2-(benzyloxy)ethanamine, and 1-aminoindan. Of these, benzylamine is preferred.

[0040] The alkyleneoxy unit-containing monoamine having a molecular weight of 300 or less is, for example, Examples include 3,6,9,12-tetraoxadecanamine and tert-butyl 3-[2-(2-aminoethoxy)ethoxy]propanoate. Of these, 3,6,9,12-tetraoxadecanamine is preferred.

[0041] The monoalcohols and monoamines used in the present invention are preferably monoalcohols. The monoalcohols and monoamines can be used either alone or in combination of two or more.

[0042] Cyclic compounds include alkylene oxides, lactones, lactides, dicarboxylic acid anhydrides, and epoxides.

[0043] Examples of alkylene oxides that can be used include ethylene oxide, propylene oxide, 1,2-, 1,4-, 2,3-, or 1,3-butylene oxide, and combinations of two or more of these. When two or more alkylene oxides are used in combination, the bonding form may be random and / or block. The number of polymerization moles of alkylene oxide per mole of initiator is preferably 0 to 100.

[0044] The polymerization of alkylene oxide can be carried out, for example, in the presence of an alkali catalyst at a temperature of 100 to 200° C. under pressure. Polymers (PeOH) obtained by polymerizing alkylene oxide with the hydroxyl group of a monoalcohol are commercially available, such as the Uniox series manufactured by NOF Corporation and the Blemmer series manufactured by NOF Corporation, and can be used as the polymer (PeOH) in the production method of the present invention. Commercially available products include, for example, Uniox M-400, M-550, M-2000, Blenmar PE-90, PE-200, PE-350, AE-90, AE-200, AE-400, PP-1000, PP-500, PP-800, AP-150, AP-400, AP-550, AP-800, 50PEP-300, 70PEP-350B, AEP series, 55PET-400, 30PET-800, 55PET-800, AET series, 30PPT-800, 50PPT-800, 70PPT-800, APT series, 10PPB-500B, 10APB-500B, etc. In the present specification, the first step may be omitted by using these commercially available products.

[0045] Lactones include, for example, β-butyrolactone, γ-butyrolactone, γ-valerolactone, Lactone, δ-valerolactone, δ-caprolactone, ε-caprolactone, alkyl groups Among these, δ-valerolactone, ε-caprolactone, and alkyl-substituted ε-caprolactone are preferred in terms of ring-opening polymerizability.

[0046] In the production method of the present invention, the lactones that can be used are not limited to the above examples. They may be used alone or in combination of two or more.

[0047] As the lactide, one represented by the following general formula (5) is preferred (including glycolide).

[0048] General formula (5): [ka] [In general formula (5), R 31 and R 32 are each independently a hydrogen atom or a saturated or unsaturated, linear or branched alkyl group having 1 to 20 carbon atoms; R 33 and R 34 are each independently a hydrogen atom, a halogen atom, or a saturated or unsaturated, straight-chain or branched lower alkyl group having 1 to 9 carbon atoms. In this specification, lactide refers to lactide (3,6-dimethyl-1,4-dioxane-2,5-dione) and glycolide (1,4-dioxane-2,5-dione). Of the lactones and lactides, lactones are preferred.

[0049] The ring-opening polymerization of lactone and / or lactide can be carried out, for example, by charging an initiator, lactone and / or lactide, and a polymerization catalyst into a reactor connected to a dehydration tube and a condenser, and carrying out the reaction under a nitrogen stream. When a low-boiling monoalcohol is used, the reaction can be carried out under pressure using an autoclave. When a monoalcohol having an ethylenically unsaturated double bond is used, it is preferable to add a polymerization inhibitor and carry out the reaction under a dry air stream.

[0050] The number of moles of lactone and / or lactide polymerized per mole of initiator is preferably in the range of 1 to 60 moles, more preferably 2 to 20 moles, and most preferably 3 to 15 moles.

[0051] Examples of the polymerization catalyst include quaternary ammonium salts such as tetramethylammonium chloride, tetrabutylammonium chloride, tetramethylammonium bromide, tetrabutylammonium bromide, tetramethylammonium iodide, tetrabutylammonium iodide, benzyltrimethylammonium chloride, benzyltrimethylammonium bromide, and benzyltrimethylammonium iodide; tetramethylphosphonium chloride, tetrabutylphosphonium chloride, tetramethylphosphonium bromide, tetrabutylphosphonium bromide, tetramethylphosphonium iodide, tetrabutylphosphonium iodide; Examples of catalysts include quaternary phosphonium salts such as trimethylphosphonium chloride, benzyltrimethylphosphonium bromide, benzyltrimethylphosphonium iodide, tetraphenylphosphonium chloride, tetraphenylphosphonium bromide, and tetraphenylphosphonium iodide, as well as phosphorus compounds such as triphenylphosphine, organic carboxylates such as potassium acetate, sodium acetate, potassium benzoate, and sodium benzoate, alkali metal alcoholates such as sodium alcoholate and potassium alcoholate, as well as tertiary amines, organotin compounds, organoaluminum compounds, organotitanate compounds, and zinc compounds such as zinc chloride. The amount of catalyst used is 0.1 ppm to 3,000 ppm, and preferably 1 ppm to 1,000 ppm, based on the mass of the lactone and / or lactide. When the above range is satisfied, a colorless polymer can be easily obtained at a polymerization rate suitable for production.

[0052] The polymerization temperature of lactone and / or lactide is in the range of 100° C. to 220° C., preferably 110° C. to 210° C. If the temperature is within this range, a polymer with few by-products can be easily obtained at a polymerization rate suitable for production.

[0053] Examples of dicarboxylic acid anhydrides include succinic anhydride, maleic anhydride, phthalic anhydride, itaconic anhydride, glutaric anhydride, dodecenylsuccinic anhydride, and chlorendec anhydride.

[0054] Examples of epoxides include methyl glycidyl ether, ethyl glycidyl ether, butyl glycidyl ether, 2-ethylhexyl glycidyl ether, dodecyl glycidyl ether, phenyl glycidyl ether, p-tertiary butylphenyl glycidyl ether, 2,4-dibromophenyl glycidyl ether, 3-methyl-dibromophenyl glycidyl ether (however, the substitution position of the bromo is optional), allyl glycidyl ether, ethoxyphenyl glycidyl ether, glycidyl (meth)acrylate, glycidyl phthalimide, and styrene oxide.

[0055] The order of reaction of the cyclic compounds is arbitrary. For example, alkylene oxide can be polymerized with the initiator in the first step, followed by lactone in the second step, and then alternatingly polymerizing dicarboxylic acid anhydride and epoxide in the third step. In this example, the initiator used to polymerize lactone in the second step is the alkylene oxide polymer having a hydroxyl group at one end polymerized in the first step. Furthermore, the initiator used to alternately polymerize dicarboxylic acid anhydride and epoxide in the third step is a block copolymer of the alkylene oxide polymer having a hydroxyl group at one end polymerized up to the second step and the lactone polymer. In the production method of the present invention, such a polymer having a hydroxyl group at one end is also included as an initiator when producing the polymer (APOH) described below. Similarly, the polymer (APNH2) described below may also function as an initiator.

[0056] The reaction order of the cyclic compounds is not limited to the combination of alkylene oxide in the first step, lactone in the second step, and dicarboxylic acid anhydride and epoxide in the third step, and the combinations of alkylene oxide, lactone (and / or lactide), and dicarboxylic acid anhydride and epoxide can be carried out in any order, one or more times each. Alternatively, instead of carrying out ring-opening polymerization for all combinations of alkylene oxide, lactone (and / or lactide), and dicarboxylic acid anhydride and epoxide, any cyclic compound can be selected from them and subjected to ring-opening polymerization.

[0057] In the synthesis of the present invention, a dicarboxylic anhydride and an epoxide are simultaneously used with an initiator and react alternately. At this time, the acid anhydride group of the dicarboxylic anhydride first reacts with a hydroxyl group, a primary amino group, a secondary amino group, or a thiol group of the initiator to generate a carboxyl group, and then the epoxy group of the epoxide reacts with this carboxyl group to generate a hydroxyl group. The acid anhydride group of the dicarboxylic anhydride then reacts with this hydroxyl group, and so on, allowing the same reactions to proceed sequentially. The polymerization mole numbers of the dicarboxylic anhydride and the epoxide per mole of the initiator are preferably 0 to 30 moles each. The reaction ratio ([D] / [E]) of the dicarboxylic anhydride and the epoxide is: 0.8≦[D] / [E]≦1.0 (where [D] is the number of moles of dicarboxylic acid anhydride, and [E] is the number of moles of epoxide.) When the above range is satisfied, it is easy to obtain a polymer having a hydroxyl group at one end while reducing the amount of remaining epoxide raw material.

[0058] The alternating polymerization of dicarboxylic acid anhydride and epoxide is preferably carried out at a temperature of 50 to 180°C, more preferably Preferably, the reaction temperature is in the range of 60 to 150°C. If the temperature exceeds 100°C, the reaction rate is extremely slow.

[0059] Next, the first step of producing "a cyclic ester polymer moiety (APNH2) having a terminal moiety A and an amino group at the other terminal" will be described. In the production method of the present invention, the polymer (APNH2) can be synthesized by ring-opening polymerization of a cyclic compound using a monoalcohol as an initiator to produce a cyclic ester polymer moiety having a hydroxyl group at one end, and then reductively amminating the hydroxyl group.

[0060] The "cyclic ester polymer moiety (APOH) having a terminal moiety A and a hydroxyl group at the other terminal" as a precursor of the "cyclic ester polymer moiety (APNH2) having a terminal moiety A and an amino group at the other terminal" is already synthesized in the same manner as in the synthesis of the polymer (APOH). The synthesis conditions and raw materials are also the same as those described above. This "cyclic ester polymer moiety (APOH) having a terminal moiety A and a hydroxyl group at the other terminal" can be obtained, for example, by reacting it in the presence of ammonia, hydrogen, and a catalyst under high-temperature conditions of 170 to 250°C under a pressure of 5 to 30 MPa for 0.15 to 2 hours. In this way, the hydroxyl group is reductively aminated to obtain the "cyclic ester polymer moiety (APNH2) having a terminal moiety A and an amino group at the other terminal." As a catalyst for reductive amination, a Raney nickel / aluminum catalyst is preferred.

[0061] The "cyclic ester polymer moiety (APNH2) having a terminal moiety A and an amino group at the other terminal" is commercially available, for example, from Mitsui Fine Chemicals, Inc. or Huntsman Corporation under the trade name Jeffamine or Surfonamin. In the production method of the present invention, such commercially available products can be used as the polyether (ANH2) having an amino group at one terminal, and the first step can be omitted. Specific examples of commercially available products include Jeffamine XTJ-475, XTJ-436, XTJ-505, XTJ-506, XTJ-507, M-2070, Surfonamin B-60, L-100, B-200, L-207, L-300, B-30, and B-100.

[0062] As described above, the monovalent polymer moiety (P) herein is composed of a moiety obtained by removing one hydrogen atom of a hydroxyl group or one hydrogen atom of a primary amino group from the polymer (APOH)" or the polymer (APNH)" respectively. In this specification, from the viewpoint of the simplicity of the synthesis process, which does not require reductive amination, the polymer moiety (P) is preferably a cyclic ester polymer moiety (APOH) having a terminal moiety A and a hydroxyl group at the other terminal.

[0063] The cyclic ester polymer moiety (APOH) is preferably lactone or lactide in terms of the ease of the production process, ease of molecular weight control, and high reactivity.

[0064] A solvent can be used in the first step of producing the polymer (APOH) or polymer (APNH2). Examples of the solvent include acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, ethyl acetate, butyl acetate, toluene, xylene, acetonitrile, and propylene glycol monomethyl ether acetate. Two or more of these solvents may be mixed and used. After the reaction is complete, the solvent used can be removed by distillation or the like, or it can be used as is as part of the dispersant product.

[0065] Next, the second step of reacting "a cyclic ester polymer moiety (APOH) having a terminal moiety A and a hydroxyl group at the other terminal, or a cyclic ester polymer moiety (APNH2) having a terminal moiety A and an amino group at the other terminal" with a tetracarboxylic dianhydride will be described.

[0066] In the present invention, the hydroxyl group of the "cyclic ester polymer moiety (APOH) having a terminal moiety A and a hydroxyl group at the other terminal" obtained in the first step, or the primary amino group of the "cyclic ester polymer moiety (APNH2) having a terminal moiety A and an amino group at the other terminal" is reacted with the anhydride group of a tetracarboxylic dianhydride. In this second step, for example, a dispersant represented by the general formula (1) according to the present invention can be obtained.

[0067] Examples of the tetracarboxylic dianhydride include aliphatic tetracarboxylic dianhydrides, aromatic tetracarboxylic dianhydrides, and polycyclic tetracarboxylic dianhydrides.

[0068] Examples of the aliphatic tetracarboxylic dianhydride include 1,2,3,4-butanetetracarboxylic dianhydride, 1,2,3,4-cyclobutanetetracarboxylic dianhydride, 1,3-dimethyl-1,2,3,4-cyclobutanetetracarboxylic dianhydride, 1,2,3,4-cyclopentanetetracarboxylic dianhydride, 2,3,5-tricarboxycyclopentylacetic dianhydride, 2,3,5,6-tetracarboxycyclohexane dianhydride, 2,3,5,6-tetracarboxynorbornane dianhydride, 3,5,6-tricarboxynorbornane-2-acetic dianhydride, 2,3,4,5-tetrahydrofurantetracarboxylic dianhydride, 5-(2,5-dioxotetrahydrofuryl)-3-methyl-3-cyclohexene-1,2-dicarboxylic dianhydride, and bicyclo[2,2,2]-oct-7-ene-2,3,5,6-tetracarboxylic dianhydride.

[0069] Examples of aromatic tetracarboxylic acid anhydrides include pyromellitic dianhydride, ethylene glycol ditrimellitic anhydride, propylene glycol ditrimellitic anhydride, butylene glycol ditrimellitic anhydride, 3,3',4,4'-benzophenone tetracarboxylic acid dianhydride, 2,2',3,3'-benzophenone tetracarboxylic acid dianhydride, 3,3',4,4'-biphenylsulfone tetracarboxylic acid dianhydride, 2,2',3,3'-biphenylsulfone tetracarboxylic acid dianhydride, 1,4,5,8-naphthalene tetracarboxylic acid dianhydride, 2,3,6,7-naphthalene tetracarboxylic acid dianhydride, 3,3',4,4'-biphenyl ether tetracarboxylic acid dianhydride, 3,3',4,4'-dimethyldiphenylsilane tetracarboxylic acid dianhydride, 3,3',4,4'-tetraphenylsilane tetracarboxylic acid dianhydride, and 1,2,3,4-furan tetracarboxylic acid dianhydride. , 4,4'-bis(3,4-dicarboxyphenoxy)diphenyl sulfide dianhydride, 4,4'-bis(3,4-dicarboxyphenoxy)diphenyl sulfone dianhydride, 4,4'-bis(3,4-dicarboxyphenoxy)diphenylpropane dianhydride, 3,3',4,4'-perfluoroisopropylidenediphthalic dianhydride, 3,3',4,4'-biphenyltetracarboxylic dianhydride, bis(phthalic acid)phenylphosphine oxide dianhydride Examples of suitable dianhydrides include fluorene dianhydride, p-phenylene-bis(triphenylphthalic) dianhydride, M-phenylene-bis(triphenylphthalic) dianhydride, bis(triphenylphthalic)-4,4'-diphenyl ether dianhydride, bis(triphenylphthalic)-4,4'-diphenylmethane dianhydride, 9,9-bis(3,4-dicarboxyphenyl)fluorene dianhydride, and 9,9-bis[4-(3,4-dicarboxyphenoxy)phenyl]fluorene dianhydride.

[0070] Examples of polycyclic tetracarboxylic acid anhydrides include 3,4-dicarboxy-1,2,3,4-tetrahydro-1-naphthalene succinic dianhydride and 3,4-dicarboxy-1,2,3,4-tetrahydro-6-methyl-1-naphthalene succinic dianhydride.

[0071] The tetracarboxylic acid dianhydride used in the production method of the present invention is not limited to the compounds exemplified above, and any structure may be used as long as it has two carboxylic acid anhydride groups. These compounds may be used alone or in combination. Aromatic tetracarboxylic acid dianhydrides are preferred for use in the present invention, from the viewpoint of reducing the viscosity of pigment dispersions or various inks. Preferred aromatic tetracarboxylic acid dianhydrides include pyromellitic dianhydride, 3,3',4,4'-benzophenone tetracarboxylic acid dianhydride, ethylene glycol ditrimellitic anhydride, 3,3',4,4'-benzophenone tetracarboxylic acid dianhydride, 9,9-bis(3,4-dicarboxyphenyl)fluorene dianhydride, 3,3',4,4'-biphenylsulfone tetracarboxylic acid dianhydride, 2,3,6,7-naphthalene tetracarboxylic acid dianhydride, and 3,3',4,4'-biphenyl tetracarboxylic acid dianhydride.

[0072] The reaction ratio in the second step is determined by the moles of the hydroxyl groups of the polymer (APOH) or the primary amino groups of the polymer (APNH2). <h>, the number of moles of carboxylic acid anhydride groups of tetracarboxylic acid dianhydride <n>When this is the case, 0.5< <h> / <n><1.2 is preferable, and 0.7< <h> / <n><1.1, most preferably <h> / <n>=1. <h> / <n>When the reaction is carried out at <1, the remaining acid anhydride may be hydrolyzed with a required amount of water before use.

[0073] A catalyst may be used in the second step, such as a tertiary amine compound, including triethylamine, triethylenediamine, N,N-dimethylbenzylamine, N-methylmorpholine, 1,8-diazabicyclo-[5.4.0]-7-undecene, and 1,5-diazabicyclo-[4.3.0]-5-nonene.

[0074] The second step may be carried out without a solvent or with the use of an appropriate dehydrated organic solvent. After the reaction is completed, the solvent used can be removed by distillation or the like, or it can be used as it is as part of the dispersant product.

[0075] The reaction temperature in the second step is preferably in the range of 80°C to 180°C, more preferably 90°C to 160°C, when a "polymer having a hydroxyl group at one end (POH)" is used. If the reaction temperature is below 80°C, the reaction rate is slow, and if it exceeds 180°C, the acid anhydride that has been reacted and opened to form a cyclic anhydride again, which may make it difficult to complete the reaction. Furthermore, if a "polymer having a primary amino group at one end (PNH2)" is used, the reaction temperature is preferably in the range of 0°C to 150°C, more preferably 10°C to 100°C. If the reaction temperature satisfies the above range, it becomes easier to carry out synthesis at a reaction rate suitable for production while suppressing the rate of side reactions such as imidization.

[0076] Here, the portion excluding the group generated by the reaction of two acid anhydride groups in the tetracarboxylic dianhydride with the reactive functional group is X in the general formula (1). 1 Configure.

[0077] The colored composition of the present invention refers to a paste or chip-like product obtained by dispersing a colorant using the dispersant of the present invention. A pigment dispersion can be obtained using only the dispersant of the present invention and the colorant. Alternatively, a colored composition can be obtained by using the dispersant of the present invention to disperse a colorant in a pigment carrier (a resin, its precursor, or a mixture thereof) other than the dispersant, a solvent, a varnish, or the like.

[0078] The coloring composition of the present invention may further contain, as other additives, a photopolymerization initiator, a chain transfer agent, a polymerizable compound, a terpolymerization initiator ... Plasticizer, surface conditioner, UV inhibitor, light stabilizer, antioxidant, antistatic agent, antiblock Addition of blocking agents, defoamers, viscosity modifiers, waxes, surfactants, leveling agents, etc. can.

[0079] Examples of the apparatus used for dispersion in this specification include a horizontal sand mill, a vertical sand mill, an annular bead mill, an attritor, a kneader, a two-roll mill, a three-roll mill, a high-speed mixer, a homomixer, a ball mill, a roll mill, a stone mill, and an ultrasonic disperser.

[0080] Furthermore, a coloring composition in chip form can also be obtained by dispersing the nonvolatile components using a milling mixer such as a kneader, a two-roll mill, a three-roll mill, etc. Note that the solid dispersion refers to a pigment dispersion that does not use a solvent.

[0081] When each dispersing device has a viscosity range suitable for dispersion, the viscosity can be adjusted by changing the ratio of various colorant carriers to pigments.

[0082] The coloring composition of the present invention preferably contains a dispersant and a colorant (A). The coloring composition of the present invention preferably further contains a polymerizable compound (B) and a photopolymerization initiator (C). The coloring composition of the present invention can be used for color filters, offset inks, inkjet inks, and the like. The coloring composition for color filters will be described below.

[0083] <Colorant (A)> Examples of the colorant (A) include organic pigments, inorganic pigments, and dyes. Among these, pigments with high color development and high heat resistance, particularly pigments with high thermal decomposition resistance, are preferred, and organic pigments are usually used.

[0084] Specific examples of organic pigments are shown below by color index numbers.

[0085] Red pigments include, for example, CI Pigment Red 1, 2, 3, 4, 5, 6, 7, 8, 9, 12, 14, 15, 16, 17, 21, 22, 23, 31, 32, 37, 38, 41, 47, 48, 48:1, 48:2, 48:3, 48:4, 49, 49:1, 49:2, 50:1, 52:1, 52:2, 53, 53:1, 53:2, 53:3, 57, 57:1, 57:2, 58:4, 60, 63, 63:1, 63:2, 64, 64:1, 68, 69, 81, 81:1, 81:2, 81:3, 81:4, 83, 88, 90:1, 101, 101:1, 104, 108, 108:1, 109, 112, 113, 114, 122, 123, 144, 146, 147, 149, 151, 166, 168, 169, 170, 172, 173, 174, 175, 176, 177, 178, 179 ,181,184,185,187,188,190,193,194,200,202,206,207,208,209,210,214,216,220,221,224,230,231,232,233,235,236,237,238,239,242,243,245,247,249,250,251,253,254,255,256,257,258,259, 260, 262, 263, 264, 265, 266, 267, 268, 269, 270, 271, 272, 273, 274, 275, 276, 277, 278, 279, 280, 281, 282, 283, 284, 285, 286, 287, 291, 295, 296, JP 2014-134712 A, and the pigments described in Japanese Patent No. 6368844. Among these, from the viewpoints of heat resistance, light fastness, and transmittance, CI Pigment Red 48:1,122,177,224,242,269,254,291,295,296, the pigments described in JP-A-2014-134712, and the pigments described in Japanese Patent No. 6368844 are preferred, and CI Pigment Red 177,254,291,295,296, the pigments described in JP-A-2014-134712, and the pigments described in Japanese Patent No. 6368844 are particularly preferred.

[0086] Examples of orange pigments include CI Pigment Orange 36, 38, 43, 64, 71, and 73.

[0087] Yellow pigments include, for example, CI Pigment Yellow 1, 2, 3, 4, 5, 6, 10, 12, 13, 14, 15, 16, 17, 18, 24, 31, 32, 34, 35, 35:1, 36, 36:1, 37, 37:1, 40, 42, 43, 53, 55, 60, 61, 62, 63, 65, 73, 74, 77, 81, 83, 93, 94, 95, 97, 98, 100, 101, 104, 106, 108, 109, 110, 113, 114, 115, 116, 117, 118, 119, 120, and 123. , 126,127,128,129,138,139,147,150,151,152, 153,154,155,156,161,162,164,166,167,168,169,170,171,172,173,174,175,176,177,179,180,181,182,185,187,188,192,193,194,196,198,199,213,214,231,233, and the pigments described in JP-A-2012-226110. Among these, CI Pigment Yellows 138, 139, 150, 185, 231, and 233, and the pigments described in JP-A-2012-226110 are preferred.

[0088] Examples of green pigments include CI Pigment Green 1, 2, 4, 7, 8, 10, 13, 14, 15, 17, 18, 19, 26, 36, 37, 45, 48, 50, 51, 54, 55, 58, 59, 62, and 63. Among these, CI Pigment Green 36, 58, 59, 62, and 63 are preferred.

[0089] Examples of blue pigments include CI Pigment Blue 1, 1:2, 9, 14, 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 17, 19, 25, 27, 28, 29, 33, 35, 36, 56, 56:1, 60, 61, 61:1, 62, 63, 66, 67, 68, 71, 72, 73, 74, 75, 76, 78, and 79. Among these, CI Pigment Blue 15, 15:1, 15:2, 15:3, 15:4, and 15:6 are preferred.

[0090] Examples of purple pigments include CI Pigment Violet 1, 1:1, 2, 2:2, 3, 3:1, 3:3, 5, 5:1, 14, 15, 16, 19, 23, 25, 27, 29, 31, 32, 37, 39, 42, 44, 47, 49, and 50. Among these, CI Pigment Violet 19 and 23 are preferred.

[0091] Examples of black pigments include CI Pigment Black 1, 6, 7, 12, 20, and 31. The black pigment includes inorganic pigments.

[0092] Examples of inorganic pigments include titanium oxide, barium sulfate, zinc oxide, lead sulfate, yellow lead, zinc yellow, red iron oxide (red iron (III) oxide), cadmium red, ultramarine, iron blue, chromium oxide green, cobalt green, umber, and synthetic iron black.

[0093] <dye> Examples of dyes include acid dyes, direct dyes, basic dyes, salt-forming dyes, oil-soluble dyes, disperse dyes, reactive dyes, mordant dyes, vat dyes, sulfur dyes, etc. Furthermore, as the dye, derivatives of these dyes or lake pigments obtained by lake-forming dyes can also be used.

[0094] The acid dye preferably has an acidic group such as a sulfonic acid or carboxylic acid. The direct dye preferably forms an inorganic salt of the acid dye, or a salt-forming compound between the acid dye and a nitrogen-containing compound such as a quaternary ammonium salt compound, a tertiary amine compound, a secondary amine compound, or a primary amine compound. Also preferred are salt-forming compounds that are salts of the acid dye and a resin component having these functional groups. Furthermore, the salt-forming compound can be sulfonamidated to modify it into a sulfonic acid amide compound, which makes it easy to obtain a photosensitive coloring composition with excellent resistance (light resistance, solvent resistance). In addition, a salt-forming compound of an acid dye and a compound having an onium salt group is also preferred because it has excellent resistance (light resistance, solvent resistance). The compound having an onium salt group is preferably a resin having a cationic group.

[0095] Although basic dyes can be used as they are, salt-forming compounds that form salts with organic acids, perchloric acid, or metal salts thereof are preferred. Salt-forming compounds of basic dyes are preferred because they have excellent resistance (lightfastness, solvent resistance) and affinity with pigments. Furthermore, in the salt-forming compounds of basic dyes, the anion component that acts as a counter ion is preferably an organic sulfonic acid, organic sulfuric acid, a fluorine-containing phosphorus anion compound, a fluorine-containing boron anion compound, a cyano-containing nitrogen anion compound, an anion compound having a conjugate base of an organic acid with a halogenated hydrocarbon group, or a salt-forming compound formed with an acid dye. Furthermore, the resistance of salt-forming compounds is further improved when the salt-forming compound contains a polymerizable unsaturated group in the molecule.

[0096] Examples of dyes include azo dyes, disazo dyes, azomethine dyes (indoaniline dyes, indophenol dyes, etc.), dipyrromethene dyes, quinone dyes (benzoquinone dyes, naphthoquinone dyes, anthraquinone dyes, anthrapyridone dyes, etc.), carbonium dyes (diphenylmethane dyes, triphenylmethane dyes, xanthene dyes, acridine dyes, etc.), and quinoneimine dyes (oxazine dyes, thiazine dyes, etc.). azine dyes, polymethine dyes (oxonol dyes, merocyanine dyes, arylidene dyes, styryl dyes, cyanine dyes, squarylium dyes, croconium dyes, etc.), quinophthalone dyes, phthalocyanine dyes, subphthalocyanine dyes, perinone dyes, indigo dyes, thioindigo dyes, quinoline dyes, nitro dyes, nitroso dyes, rhodamine dyes, and metal complex dyes thereof. Among these, from the viewpoint of color properties such as hue, difficulty in color separation, and color unevenness, azo dyes, xanthene dyes, cyanine dyes, triphenylmethane dyes, anthraquinone dyes, dipyrromethene dyes, squarylium dyes, quinophthalone dyes, phthalocyanine dyes, and subphthalocyanine dyes are preferred, and xanthene dyes, cyanine dyes, triphenylmethane dyes, anthraquinone dyes, dipyrromethene dyes, and phthalocyanine dyes are more preferred.

[0097] <Binder resin> The coloring composition for color filter of the present invention may contain a binder resin, and the binder resin is a resin that has a transmittance of preferably 80% or more, more preferably 95% or more, in the entire wavelength range of 400 to 700 nm in the visible light region in a film having a thickness of 2 μm. Examples of the resin include thermoplastic resins and photosensitive resins.

[0098] Examples of thermoplastic resins include butyral resins, styrene-maleic acid copolymers, chlorinated polyethylene, chlorinated polypropylene, polyvinyl chloride, vinyl chloride-vinyl acetate copolymers, polyvinyl acetate, polyurethane resins, polyester resins, acrylic resins, alkyd resins, polystyrene, polyamide resins, rubber resins, cyclized rubber resins, celluloses, polyethylene, polybutadiene, and polyimide resins. Examples of the thermosetting resin include epoxy resin, benzoguanamine resin, rosin-modified maleic acid resin, rosin-modified fumaric acid resin, melamine resin, urea resin, and phenol resin.

[0099] As the photosensitive resin, a resin in which a photocrosslinkable group such as a (meth)acryloyl group or a styryl group is introduced into a polymer having a reactive substituent such as a hydroxyl group, a carboxyl group, or an amino group by reacting the polymer with a (meth)acrylic compound having a reactive substituent such as an isocyanate group, an aldehyde group, or an epoxy group or cinnamic acid is used. Also used is a resin in which a polymer containing an acid anhydride such as a styrene-maleic anhydride copolymer or an α-olefin-maleic anhydride copolymer is half-esterified with a (meth)acrylic compound having a hydroxyl group such as a hydroxyalkyl (meth)acrylate.

[0100] Furthermore, when a filter segment is formed by alkaline development using the coloring composition of the present invention, it is preferable for the binder resin to contain an alkali-soluble non-photosensitive resin. The alkali-soluble non-photosensitive resin is a resin that dissolves in an alkaline aqueous solution and does not crosslink with radicals, and examples thereof include resins having an acidic functional group such as a carboxyl group or a sulfonic group and a weight-average molecular weight of 1,000 to 500,000, preferably 5,000 to 100,000. Examples of alkali-soluble non-photosensitive resins include acrylic resins having an acidic functional group, α-olefin / maleic acid (anhydride) copolymers, styrene / maleic acid (anhydride) copolymers, styrene / styrene sulfonic acid copolymers, ethylene / (meth)acrylic acid copolymers, and isobutylene / maleic acid (anhydride) copolymers. Among these, at least one resin selected from the group consisting of an acrylic resin having an acidic functional group, an α-olefin / maleic acid (anhydride) copolymer, a styrene / maleic acid (anhydride) copolymer, and a styrene / styrene sulfonic acid copolymer, and in particular an acrylic resin having an acidic functional group, is preferably used because of its high heat resistance and transparency.

[0101] <Polymerizable compound (B)> The polymerizable compound (B) is a monomer or oligomer having a polymerizable unsaturated group. The oligomer is a compound having a molecular weight of 1000 or more. Examples of the polymerizable unsaturated group include a vinyl group, a (meth)acryloyl group, and a (meth)allyl group.

[0102] Examples of the polymerizable compound (B) include photopolymerizable compounds having an acid group, photopolymerizable compounds having a urethane bond, and other monomers.

[0103] (Photopolymerizable compound having an acid group) Examples of the acid group of the photopolymerizable compound having an acid group include a sulfonic acid group, a carboxyl group, and a phosphoric acid group.

[0104] Examples of photopolymerizable compounds having an acid group include esters of dicarboxylic acids and poly(meth)acrylates containing free hydroxyl groups, which are polyhydric alcohols and (meth)acrylic acid; and esters of polycarboxylic acids and monohydroxyalkyl(meth)acrylates. Examples of the photopolymerizable compound having an acid group include free carboxyl group-containing monoesters of monohydroxy oligoacrylates or monohydroxy oligomethacrylates such as trimethylolpropane diacrylate, trimethylolpropane dimethacrylate, pentaerythritol triacrylate, pentaerythritol trimethacrylate, dipentaerythritol pentaacrylate, and dipentaerythritol pentamethacrylate with dicarboxylic acids such as malonic acid, succinic acid, glutaric acid, and terephthalic acid; propane-1,2,3 and free carboxyl group-containing oligoesters of tricarboxylic acids such as 1,2,4-tricarboxylic acid (tricarboxylic acid), butane-1,2,4-tricarboxylic acid, benzene-1,2,3-tricarboxylic acid, benzene-1,3,4-tricarboxylic acid, and benzene-1,3,5-tricarboxylic acid with monohydroxymonoacrylates or monohydroxymonomethacrylates such as 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl acrylate, and 2-hydroxypropyl methacrylate.

[0105] Examples of commercially available photopolymerizable compounds having an acid group include Viscoat #2500P manufactured by Osaka Organic Industries, and M-5300, M-5400, M-5700, M-510, and M-520 manufactured by Toagosei Co., Ltd.

[0106] (Photopolymerizable compound having a urethane bond) The photopolymerizable compound may contain a photopolymerizable compound containing at least one ethylenically unsaturated bond and one urethane bond (hereinafter referred to as a polymerizable compound having a urethane bond). Examples of the polymerizable compound having a urethane bond include a polyfunctional urethane acrylate obtained by reacting a (meth)acrylate having a hydroxyl group with a polyfunctional isocyanate, and a polyfunctional urethane acrylate obtained by reacting an alcohol with a polyfunctional isocyanate and further reacting the resulting alcohol with a (meth)acrylate having a hydroxyl group.

[0107] Examples of the (meth)acrylate having a hydroxyl group include 2-hydroxyethyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, trimethylolpropane di(meth)acrylate, pentaerythritol tri(meth)acrylate, ditrimethylolpropane tri(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol ethylene oxide-modified penta(meth)acrylate, dipentaerythritol propylene oxide-modified penta(meth)acrylate, dipentaerythritol caprolactone-modified penta(meth)acrylate, glycerol acrylate methacrylate, glycerol dimethacrylate, 2-hydroxy-3-acryloylpropyl methacrylate, a reaction product of an epoxy group-containing compound and a carboxy(meth)acrylate, and a hydroxyl group-containing polyol polyacrylate.

[0108] Examples of polyfunctional isocyanates include tolylene diisocyanate, hexamethylene diisocyanate, diphenylmethylene diisocyanate, isophorone diisocyanate, and polyisocyanate.

[0109] Although there are no limitations on the structure of the alcohol, the use of a polyhydric alcohol is preferred because it increases the degree of crosslinking of the cured coating film and improves solvent resistance. Examples of polyhydric alcohols include propylene glycol, ethylene glycol, glycerin, trimethylolpropane, and pentaerythritol.

[0110] Examples of commercially available polymerizable compounds having a urethane bond include AH-600, AT-600, UA-306H, UA-306T, UA-306I, UA-510H, UF-8001G, and DAUA167 manufactured by Kyoeisha Chemical Co., Ltd., UA160™ manufactured by Shin-Nakamura Chemical Co., Ltd., and UV-4108F and UV-4117F manufactured by Osaka Organic Chemical Industry Ltd.

[0111] Other monomers include, for example, methyl (meth)acrylate, ethyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, cyclohexyl (meth)acrylate, β-carboxyethyl (meth)acrylate, polyethylene glycol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, triethylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, phenoxytetraethylene glycol (meth)acrylate, phenoxyhexaethylene glycol (meth)acrylate, trimethylolpropane PO-modified tri(meth)acrylate, trimethylolpropane EO-modified tri(meth)acrylate, isocyanuric acid EO-modified di(meth)acrylate, isocyanuric acid EO-modified tri(meth)acrylate, ditrimethylolpropane tetra(meth)acrylate, pentaerythritol Examples of suitable acrylic acid esters and methacrylic acid esters include butyl acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, 1,6-hexanediol diglycidyl ether di(meth)acrylate, bisphenol A diglycidyl ether di(meth)acrylate, neopentyl glycol diglycidyl ether di(meth)acrylate, dipentaerythritol hexa(meth)acrylate, dipentaerythritol penta(meth)acrylate, tricyclodecanyl (meth)acrylate, ester acrylate, (meth)acrylic acid ester of methylolated melamine, epoxy (meth)acrylate, and urethane acrylate; (meth)acrylic acid, styrene, vinyl acetate, hydroxyethyl vinyl ether, ethylene glycol divinyl ether, pentaerythritol trivinyl ether, (meth)acrylamide, N-hydroxymethyl (meth)acrylamide, N-vinylformamide, and acrylonitrile.

[0112] Commercially available photopolymerizable compounds include, for example, KAYARAD R-128H, KAYARAD R526, KAYARAD PEG400DA, KAYARAD MAND, KAYARD NPGDA, KAYARAD R-167, KAYARAD HX-220, KAYARAD R-551, KAYARAD R712, KAYARAD R-604, KAYARAD R-684, KAYARAD GPO-303, KAYARAD TMPTA, KAYARAD DPHA, KAYARAD DPEA12, KAYARAD DPHA-2C, KAYARAD D-310, KAYARAD D-330, KAYARAD DPCA-20, KAYARAD DPCA-30, KAYARAD DPCA-60, and KAYARAD Examples of such a coating include DPCA120, and M-303, M-305, M-306, M-309, M-310, M-321, M-325, M-350, M-360, M-313, M-315, M-400, M-402, M-403, M-404, M-405, M-406, M-450, M-452, M-408, M-211B, and M-101A manufactured by Toagosei Co., Ltd., Viscoat #310HP, Viscoat #335HP, Viscoat #700, Viscoat #295, Viscoat #330, Viscoat #360, Viscoat #GPT, Viscoat #400, and Viscoat #405 manufactured by Osaka Organic Chemical Co., Ltd., and A-9300 manufactured by Shin-Nakamura Chemical Co., Ltd.

[0113] <Photopolymerization initiator (C)> The photopolymerization initiator (C) is an acetophenone-based photopolymerization initiator such as 4-phenoxydichloroacetophenone, 4-t-butyl-dichloroacetophenone, diethoxyacetophenone, 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropan-1-one, 1-hydroxycyclohexyl phenyl ketone, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1-one, or 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one; benzoin-based photopolymerization initiators such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, or benzil dimethyl ketal; benzophenone-based photopolymerization initiators such as benzophenone, benzoylbenzoic acid, methyl benzoylbenzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone, or 4-benzoyl-4'-methyldiphenyl sulfide; thioxanthone-based photopolymerization initiators such as thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, isopropylthioxanthone, and 2,4-diisopropylthioxanthone; triazine-based photopolymerization initiators such as 2,4,6-trichloro-s-triazine, 2-phenyl-4,6-bis(trichloromethyl)-s-triazine, 2-(p-methoxyphenyl)-4,6-bis(trichloromethyl)-s-triazine, 2-(p-tolyl)-4,6-bis(trichloromethyl)-s-triazine, 2-piperonyl-4,6-bis(trichloromethyl)-s-triazine, 2,4-bis(trichloromethyl)-6-styryl-s-triazine, 2-(naphth-1-yl)-4,6-bis(trichloromethyl)-s-triazine, 2-(4-methoxy-naphth-1-yl)-4,6-bis(trichloromethyl)-s-triazine, 2,4-trichloromethyl-(piperonyl)-6-triazine, or 2,4-trichloromethyl(4'-methoxystyryl)-6-triazine; Borate-based photoinitiators; a carbazole-based photoinitiator; or Examples include imidazole-based photopolymerization initiators.

[0114] The content of the photopolymerization initiator (C) is preferably from 5 to 200% by mass, more preferably from 10 to 150% by mass, relative to 100% by mass of the colorant.

[0115] The coloring composition may contain a sensitizer, such as an α-acyloxy ester, acylphosphine oxide, methylphenyl glyoxylate, benzyl, 9,10-phenanthrenequinone, camphorquinone, ethylanthraquinone, 4,4′-diethylisophthalophenone, 3,3′,4,4′-tetra(t-butylperoxycarbonyl)benzophenone, or 4,4′-diethylaminobenzophenone.

[0116] The content of the sensitizer is preferably from 0.1 to 60% by mass based on the mass of the photopolymerization initiator (C) in the colored composition.

[0117] <Solvent> The coloring composition of the present invention may contain a solvent to adjust the viscosity and flowability.

[0118] Examples of the solvent include 1,2,3-trichloropropane, 1,3-butanediol, 1,3-butylene glycol, 1,3-butylene glycol diacetate, 1,4-dioxane, 2-heptanone, 2-methyl-1,3-propanediol, 3,5,5-trimethyl-2-cyclohexen-1-one, 3,3,5-trimethylcyclohexanone, ethyl 3-ethoxypropionate, 3-methyl-1,3-butanediol, 3-methoxy-3-methyl-1-butanol, 3-methoxy-3-methylbutyl acetate, 3-methoxybutanol, and 3-methoxymethyl-2-methyl-1-propanediol. Butyl acetate, 4-heptanone, m-xylene, m-diethylbenzene, m-dichlorobenzene, N,N-dimethylacetamide, N,N-dimethylformamide, n-butyl alcohol, n-butylbenzene, n-propyl acetate, N-methylpyrrolidone, o-xylene, o-chlorotoluene, o-diethylbenzene, o-dichlorobenzene, p-chlorotoluene, p-diethylbenzene, sec-butylbenzene, tert-butylbenzene, γ-butyrolactone, isobutyl alcohol, isophorone, ethylene glycol diethyl ether ethanol, ethylene glycol dibutyl ether, ethylene glycol monoisopropyl ether, ethylene glycol monoethyl ether, ethylene glycol monoethyl ether acetate, ethylene glycol monotertiary butyl ether, ethylene glycol monobutyl ether, ethylene glycol monobutyl ether acetate, ethylene glycol monopropyl ether, ethylene glycol monohexyl ether, ethylene glycol monomethyl ether, ethylene glycol monomethyl ether acetate, diisobutyl ketone, diethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol monoisopropyl ether, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether, diethylene glycol monobutyl ether acetate, diethylene glycol monomethyl ether, cyclohexanol, cyclohexanol acetate, cyclohexanone, dipropylene glycol dimethyl ether, dipropylene glycol methyl ether acetate, dipropylene glycol monoethyl ether,Examples of the alkyl ester include dipropylene glycol monobutyl ether, dipropylene glycol monopropyl ether, dipropylene glycol monomethyl ether, diacetone alcohol, triacetin, tripropylene glycol monobutyl ether, tripropylene glycol monomethyl ether, propylene glycol diacetate, propylene glycol phenyl ether, propylene glycol monoethyl ether, propylene glycol monoethyl ether acetate, propylene glycol monobutyl ether, propylene glycol monopropyl ether, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether propionate, benzyl alcohol, methyl isobutyl ketone, methylcyclohexanol, n-amyl acetate, n-butyl acetate, isoamyl acetate, isobutyl acetate, propyl acetate, and dibasic acid esters. Among these, monoalcohols having an ether group or a carbonyl group are preferred, and 3-methoxybutanol and diacetone alcohol are more preferred. When a monoalcohol having an ether group or a carbonyl group is contained, the dispersion stability of the present invention during low-temperature storage is improved.

[0119] The colored composition of the present invention can be produced by, for example, adding a colorant, a dispersant, a dye derivative, a solvent, etc., and carrying out a dispersion treatment to produce a dispersion. Then, the binder resin (A), a polymerizable compound, a photopolymerization initiator, etc. are blended and mixed with the dispersion. The materials to be blended and the timing of blending are optional. The dispersion process can also be carried out multiple times.

[0120] Examples of dispersing machines for carrying out the dispersion treatment include a two-roll mill, a three-roll mill, a ball mill, a horizontal sand mill, a vertical sand mill, an annular bead mill, and an attritor.

[0121] Dye derivatives are compounds having an acidic group, a basic group, a neutral group, etc. in an organic dye residue. Examples of dye derivatives include compounds having an acidic substituent such as a sulfo group, a carboxy group, or a phosphate group, and amine salts thereof; compounds having a basic substituent such as a sulfonamide group or a terminal tertiary amino group; and compounds having a neutral substituent such as a phenyl group or a phthalimidoalkyl group. Examples of organic pigments include diketopyrrolopyrrole pigments, anthraquinone pigments, quinacridone pigments, dioxazine pigments, perinone pigments, perylene pigments, thiazine indigo pigments, triazine pigments, benzimidazolone pigments, indole pigments such as benzoisoindole, isoindoline pigments, isoindolinone pigments, quinophthalone pigments, naphthol pigments, threne pigments, metal complex pigments, and azo pigments such as azo, disazo, and polyazo.

[0122] It is preferable to remove coarse particles of 5 μm or more, preferably coarse particles of 1 μm or more, more preferably coarse particles of 0.5 μm or more, and mixed dust from the colored composition of the present invention by means of centrifugation, a sintered filter, a membrane filter, or the like.

[0123] <Color filter> In this specification, a color filter comprises a base material (also referred to as a transparent substrate) and filter segments formed from a photosensitive coloring composition. By appropriately selecting the type of colorant used, the color filter can have red filter segments, green filter segments, and blue filter segments. Furthermore, instead of these filter segments, magenta filter segments, cyan filter segments, and yellow filter segments can also be used. Note that a reflective substrate can be used instead of the transparent substrate. Examples of the transparent substrate include a glass substrate. Examples of the reflective substrate include a substrate that uses an aluminum electrode or a metal thin film as a reflective surface. A transparent electrode such as an ITO film can also be formed on the substrate.

[0124] <Color filter manufacturing method> It is preferable to form a color filter by first forming a black matrix on a substrate and then forming filter segments. Alternatively, thin film transistors (TFTs) can be formed on the substrate before forming the black matrix. Examples of the black matrix include a multilayer film of chromium or chromium / chromium oxide, an inorganic film such as titanium nitride, and a resin film in which a light-blocking agent is dispersed.

[0125] The filter segments can be formed by, for example, a printing method, an electrodeposition method, a transfer method, an inkjet method, a photolithography method, etc. In this specification, the most preferred method is the photolithography method.

[0126] In the photolithography method, for example, a photosensitive coloring composition containing a colorant of a certain color tone is applied to a transparent substrate so that the dry film thickness is approximately 0.2 to 5 μm to form a coating. The resulting coating (hereinafter referred to as the first coating) is exposed (irradiated with light) through a mask having a predetermined pattern. The coating is then developed by immersing in a solvent or alkaline developer or by spraying the developer onto the substrate, and the uncured portions are removed to obtain the desired pattern. This process can be similarly performed using photosensitive coloring compositions containing colorants of other colors to produce color filters having filter segments of each color. Furthermore, a second coating (oxygen barrier film) can be formed on the first coating before exposure using polyvinyl alcohol or a water-soluble acrylic resin. This prevents the first coating from coming into contact with oxygen, thereby further improving exposure sensitivity. Furthermore, the color filter can be heated to cure any uncured photopolymerizable compound in the filter segments.

[0127] Examples of the coating device include a spray coater, a spin coater, a slit coater, and a roll coater. A drying step can be carried out during coating. Examples of the drying device include a hot air oven and an infrared heater.

[0128] The developer may be an alkaline developer, such as an inorganic alkali such as sodium carbonate or sodium hydroxide, or an organic alkali such as dimethylbenzylamine or triethanolamine. The developer may also contain an antifoaming agent or a surfactant.

[0129] A color liquid crystal display device is manufactured by laminating the color filter of the present invention to an opposing substrate using a sealant, injecting liquid crystal through an injection port provided in the seal, sealing the injection port, and laminating a polarizing film or a retardation film to the outside of the substrate as needed. This color liquid crystal display device can be used in liquid crystal display modes that use color filters such as twisted nematic (TN), super twisted nematic (STN), in-plane switching (IPS), vertically aligned (VA), and optically convencive bend (OCB).

[0130] <Solid-state imaging element> The solid-state imaging device of the present invention includes the color filter of the present invention. The configuration of the solid-state imaging device of the present invention is not particularly limited as long as it is a configuration including the color filter for the solid-state imaging device of the present invention and functions as a solid-state imaging device, but examples thereof include the following configurations. The solid-state imaging device has a substrate on which a plurality of photodiodes constituting the light receiving area of ​​the solid-state imaging element (CCD sensor, CMOS sensor, organic CMOS sensor, etc.) and transfer electrodes made of polysilicon or the like; a light-shielding film made of tungsten or the like with only the light-receiving portion of the photodiodes exposed on the photodiodes and the transfer electrodes; a device protection film made of silicon nitride or the like formed on the light-shielding film so as to cover the entire light-shielding film and the light-receiving portion of the photodiodes; and a color filter for the solid-state imaging element of the present invention on the device protection film. Furthermore, the device may have a light-collecting means (for example, a microlens, etc.; the same applies below) on the device protection layer and below the color filter (on the side closer to the substrate), or may have a light-collecting means on the color filter. The organic CMOS sensor is composed of a thin-film panchromatic organic photoelectric conversion film as the photoelectric conversion layer and a CMOS signal readout substrate. It has a two-layer hybrid structure in which the organic material captures light and converts it into an electrical signal, while the inorganic material extracts the electrical signal from the sensor. In principle, the aperture ratio for incident light can be made 100%. The organic photoelectric conversion film is a structure-free continuous film that can be laid on the CMOS signal readout substrate, so it does not require expensive microfabrication processes and is suitable for miniaturizing filter segments. The arrangement of the color filter segments is not particularly limited, and any known method can be used. [Example]

[0131] The present invention will be described below based on examples, but is not limited to these. In the examples, "parts" means "parts by mass" and "%" means "% by mass."

[0132] (resin weight average molecular weight (Mw)) Measurements were performed using gel permeation chromatography (GPC) equipped with an RI detector. The instrument used was an HLC-8220GPC (Tosoh Corporation), with two separation columns connected in series, both packed with "TSK-GELSUPERHZM-N" in series. Measurements were performed at an oven temperature of 40°C, a THF solution as the eluent, and a flow rate of 0.35 ml / min. The sample was dissolved in a solvent consisting of 1 wt% of the above eluent, and 20 microliters were injected. All molecular weights are expressed in terms of polystyrene.

[0133] (resin acid value) Approximately 1 g of the object to be measured for acid value was weighed out, 30 g of pyridine and 1 g of water were added, and the mixture was stirred for 10 minutes. Then, using a 0.1 N potassium hydroxide ethanol solution as a titrant, the mixture was titrated using a potentiometric measuring device (manufactured by Kyoto Electronics Manufacturing Co., Ltd., device name "potentiometric automatic titrator AT-710M") to measure the acid value of the resin and calculate the acid value per non-volatile content.

[0134] Example 1: Synthesis of Dispersant 1 A reaction vessel equipped with a gas inlet tube, thermometer, condenser, and stirrer was charged with 22.4 parts of benzyl alcohol, 177.6 parts of ε-caprolactone, and 0.1 parts of monobutyltin(IV) oxide as a catalyst, and after purging with nitrogen gas, the mixture was heated and stirred at 120°C for 4 hours. Measurement of the nonvolatile content confirmed that 98% had reacted, completing the first step ("Production Process 1" in the tables below).

[0135] 22.6 parts of pyromellitic dianhydride and 0.1 parts of DBU (1,8-diazabicyclo-[5.4.0]-7-undecene) were added to the reaction product and reacted at 100°C for 5 hours. Measurement of the acid value confirmed that 97% or more of the acid anhydride had been half-esterified, and the second step ("Production Step 2" in the tables below) was completed. The resulting dispersant had a weight-average molecular weight of 3,460 and an acid value of 49 mgKOH / g.

[0136] (Examples 2 to 21, Comparative Examples 1 and 2) Synthesis of Dispersants 2 to 21 and Comparative Dispersants 1 and 2 Dispersants 2 to 21 were obtained by synthesis in the same manner as in the production example of Dispersant 1, except that the raw materials and amounts charged as shown in Table 1 were used.

[0137] [Table 1]

[0138] [Table 2]

[0139] [Table 3]

[0140] Abbreviations in Tables 1-3: Methoxy PEG400: One-terminated methoxylated polyethylene glycol (number average molecular weight 3 95, hydroxyl value: 142mgKOH / g) PMA···Pyromellitic dianhydride BTDA 3,3,4,4-benzophenonetetracarboxylic dianhydride DSDA: 3,3,4,4-biphenylsulfonetetracarboxylic dianhydride TMEG: Ethylene glycol ditrimellitic anhydride ester (manufactured by New Japan Chemical Co., Ltd.: trade name: Rikacid TMEG-100) BPAF···9,9-bis(3,4-dicarboxyphenyl)fluorene dianhydride BTA 1,2,3,4-Butanetetracarboxylic acid dianhydride BPDA···3,3',4,4'-biphenyltetracarboxylic dianhydride NPDA: 2,3,6,7-naphthalenetetracarboxylic dianhydride

[0141] <Dispersant affinity to low-temperature solvents> In order to confirm the solvent affinity of the obtained dispersant at low temperatures, the following test was carried out. To a 30 ml screw tube, 10 parts of each dispersant obtained in Examples 1 to 21 and 10 parts of propylene glycol monomethyl ether acetate were added, heated to 40°C, and the dispersant was dissolved over 1 hour. The screw tube was then stored in a 5°C refrigerator. After 72 hours, the contents of the screw tube were suction filtered using a Kiriyama funnel and filter paper, dried under reduced pressure, and the weight percentage of the precipitated dispersant added was measured, and this was used to evaluate solvent affinity at low temperatures according to the following criteria. The results are shown in Tables 1 to 3. ◎: 0% (no precipitation) Good 〇: More than 0% and less than 5% Practical use possible △: 5% to less than 25% Not practical ×: 25% or more, not practical

[0142] (Example 22) Preparation of Coloring Composition P-1 The mixture below was stirred and mixed until uniform, and then dispersed for 3 hours in an Eiger mill (Eiger Japan Co., Ltd., "Mini Model M-250MKII") using zirconia beads with a diameter of 0.5 mm. The mixture was then filtered through a filter with a pore size of 5.0 μm to produce coloring composition P-1 with a non-volatile content of 20% by mass. PR254 (CI Pigment Red 254 (diketopyrrolopyrrole red pigment): 15.2 parts Basic derivative 1:0.8 parts Dispersant 1: 5.3 parts Propylene glycol monomethyl ether acetate (PGMAc): 70.8 parts Diacetone alcohol (DAA): 7.9 parts

[0143] (Examples 23 to 47, Comparative Examples 3 to 4) Colored compositions P-2 to P-28 were obtained in the same manner as in the production example for colored composition P-1, except that the raw materials and amounts thereof shown in Table 4 were used.

[0144] Basic derivative 1:

[0145] [ka]

[0146] Abbreviations in Table 4: PGMAc: Propylene glycol monomethyl ether acetate PGME: Propylene glycol monomethyl ether DAA: Diacetone alcohol

[0147] (Low temperature stability) The colored compositions obtained in the examples and comparative examples were evaluated for low-temperature stability by the following method. The initial viscosity on the day after preparation of the colored composition for color filters and the viscosity over time after accelerated aging at 5°C for one week were measured using an E-type viscometer ("ELD-type viscometer" manufactured by Toki Sangyo Co., Ltd.) at 25°C and a rotation speed of 50 rpm. From the values ​​of the initial viscosity and the viscosity over time, the rate of change in viscosity over time was calculated using the following formula, and the viscosity stability was evaluated on a four-point scale. [Change in viscosity over time] = |([Initial viscosity] - [Viscosity over time]) / [Initial viscosity]| x 100 ◎: Change rate less than 5% Good 〇: Change rate 5% to 10% Practical △: Change rate 10% or more, not practical ×: Settling or gelation, not practical

[0148] [Table 4]

[0149] As shown in Table 4, the colored composition using the dispersant of the present invention had good low-temperature stability over time.

[0150] (Examples 48 to 70, Comparative Examples 5 to 6) High-concentration colored compositions P-29 to P-56 were obtained in the same manner as in the production example for colored composition P-1, except that the raw materials and amounts charged were used as shown in Table 5.

[0151] (High concentration dispersibility) The obtained colored composition was measured using an E-type viscometer ("ELD type viscometer" manufactured by Toki Sangyo Co., Ltd.) at 25° C. and a rotation speed of 50 rpm, and the dispersibility was evaluated using the following four-point scale. ◎: Less than 50 mPa·s Good 〇: 50 mPa·s or more but less than 200 mPa·s, suitable for practical use △: 200 mPa·s or more, not practical ×: gelation, sedimentation or separation, not practical

[0152] [Table 5]

[0153] As shown in Table 5, the coloring composition using the dispersant of the present invention had good dispersibility even when the pigment was contained at a high concentration. Comparative Dispersants 1 and 2 shown in Comparative Examples 5 and 6 were relatively good under low concentration conditions, but did not reach a practical level under the high concentration conditions shown in Table 5.

[0154] <Method for producing binder resin> (Preparation of acrylic resin solution 1) A separable four-necked flask equipped with a thermometer, condenser, nitrogen gas inlet, and stirrer was charged with 70.0 parts of propylene glycol monoethyl ether acetate, heated to 80°C, and the atmosphere inside the reaction vessel was replaced with nitrogen. A mixture of 13.3 parts of n-butyl methacrylate, 4.6 parts of 2-hydroxyethyl methacrylate, 4.3 parts of methacrylic acid, 7.4 parts of paracumylphenol ethylene oxide-modified acrylate (Toagosei Co., Ltd.'s "Aronix M110"), and 0.4 parts of 2,2'-azobisisobutyronitrile was added dropwise over 2 hours. After the addition was completed, the reaction was continued for another 3 hours, yielding a solution of acrylic resin with a weight average molecular weight (Mw) of 26,000. After cooling to room temperature, approximately 2 g of the resin solution was sampled and dried by heating at 180°C for 20 minutes to measure the non-volatile content. Propylene glycol monoethyl ether acetate was added to the resin solution synthesized earlier so that the non-volatile content was 20 mass % to prepare acrylic resin solution 1.

[0155] (Example 74) Preparation of coloring composition RP-1 A mixture of the following composition was stirred and mixed to become uniform, and then filtered through a filter with a pore size of 1 μm to prepare a colored composition RP-1 containing a polymerizable compound (B) and a photopolymerization initiator (C). Coloring composition 1:50.0 parts Acrylic resin solution 1:7.5 parts Photopolymerizable monomer (Toagosei "Aronix M-402"): 2.0 parts Photopolymerization initiator (BASF Japan "Irgacure OXE02"): 1.2 parts Sensitizer (Chemark Chemical "CHEMARK DEABP"): 0.3 parts Propylene glycol monomethyl ether acetate (PGMAc): 39.0 parts

[0156] [Photopolymerizable compound] M-402; Aronix M-402: Dipentererythritol pentaacrylate / Dipentaerythritol hexaacrylate (manufactured by Toagosei Co., Ltd.)

[0157] [Photopolymerization initiator] Irgacure OXE02: Ethan-1-one, 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl], 1-(O-acetyloxime) (BASF Japan)

[0158] [Sensitizer] CHEMARK DEABP: 4,4'-bis(diethylamino)benzophenone (Chemark Chemical Co.)

[0159] (Examples 75 to 99, Comparative Examples 7 to 8) Preparation of Colored Compositions RP-2 to RP-28 The same procedure as in the production example of colored composition P-1 was carried out except that the raw materials and amounts thereof listed in Table 6 were used, and colored compositions RP-2 to P-28 containing a polymerizable compound (B) and a photopolymerization initiator (C) were obtained.

[0160] [Table 6]

[0161] The low-temperature stability over time of colored compositions RP-1 to RP-28 containing the polymerizable compound (B) and the photopolymerization initiator (C) was evaluated under the same evaluation conditions as those for colored compositions P-1 to P-28. As the results are shown in Table 6, the colored composition using the dispersant of the present invention had good low-temperature stability over time.< / n> < / h> < / n> < / h> < / n> < / h> < / n> < / h> < / n> < / h>

Claims

1. A dispersant represented by the following general formula (1): General formula (1) 【Chemical 1】 In general formula (1), A １ ~A ４ is a combination selected from the group consisting of A, B, and C below, A) A １ ~A ４ Two of the moieties are monovalent polymer moieties (P) which may be the same or different from each other, and the other two moieties are —C(═O)OH or CH ２ C(═O)OH, B) A １ ~A ４ One of the moieties is a monovalent polymer moiety (P), and the other three moieties are the same or different -C(=O)OH or CH ２ C(═O)OH, C) A １ ~A ４ One of the moieties is a monovalent polymer moiety (P), and the other two moieties are the same or different -C(=O)OH or CH ２ C(=O)OH, and another site is -C(=O)-Xa-Ra (wherein Xa is -O- or -N(Ra ２ )-, Ra is a group selected from the group consisting of an alkyl group having 1 to 18 carbon atoms, an alkenyl group having 2 to 18 carbon atoms, a cycloalkyl group having 3 to 18 carbon atoms, and an aryl group having 6 to 18 carbon atoms, and Ra ２ is a hydrogen atom or a group selected from the group consisting of alkyl groups having 1 to 18 carbon atoms, alkenyl groups having 2 to 18 carbon atoms, cycloalkyl groups having 3 to 18 carbon atoms, and aryl groups having 6 to 18 carbon atoms; X １ is a tetravalent group represented by the following general formula (2), general formula (3), or general formula (4): 【Chemistry 2】 [In the general formula (2), k represents 1 or 2. The * represents a bond.] [In general formula (3), R ２ is a direct bond, -CH ２ -, -O-, -C(=O)-, -C(=O)OCH ２ CH ２ OC(=O)-, -C(=O)OCH(OC(=O)CH ３ ) CH ２ OC(=O)-,-SO ２ -, -C(CF ３ ) ２ -,formula: 【Chemistry 3】 and a group represented by the following formula: [The total number of carbon atoms in the group represented by general formula (4) is 4 to 20, and in general formula (4), R ３ is a direct bond, —O—, or a divalent or trivalent hydrocarbon group having 1 to 8 carbon atoms, and R ４ , R ５ , R ６ , and R ９ are each independently a hydrogen atom or a hydrocarbon group having 1 to 8 carbon atoms, or R ４ and R ６ and / or R ５ and R ９ may be directly bonded to form an unsaturated double bond, and R ７ and R ８ are each independently a hydrogen atom or a hydrocarbon group having 1 to 8 carbon atoms, or R ７ and R ８ and a cyclic group X by forming a direct bond or a divalent hydrocarbon group having 1 to 8 carbon atoms. １ or R ３ and R ７ and R ３ and R ８ and form a trivalent hydrocarbon group having 1 to 8 carbon atoms, and a cyclic group X １ or R ３ and R ７ and R ８ and may form a tetravalent hydrocarbon group having 1 to 8 carbon atoms to form the polycyclic group X1.] The monovalent polymer moiety (P) is a cyclic ester polymer moiety having a terminal moiety A, and the terminal moiety A has a structure derived from a monoalcohol or monoamine having a molecular weight of 300 or less and containing an aromatic ring or an alkyleneoxy unit.

2. A coloring composition comprising the dispersant according to claim 1 and a colorant (A).

3. The colored composition according to claim 2 , further comprising a polymerizable compound (B) and a photopolymerization initiator (C).

4. A color filter comprising a substrate and filter segments formed from the colored composition according to claim 2 or 3.

5. A solid-state imaging device comprising the color filter according to claim 4 .

6. A display device comprising the color filter according to claim 4.

Images