Colored resin composition, color filter, and display device

Abstract

To provide a colored resin composition capable of forming a color filter that exhibits excellent brightness and contrast.SOLUTION: The colored resin composition comprises: a phenylphosphonic acid which may have a substituent; a colorant containing a compound represented by the formula (I); a dispersant having an amine value of less than 70 mgKOH / g; and a resin.SELECTED DRAWING: None

Description

Technical Field

[0001] The present invention relates to a colored resin composition, a color filter, and a display device.

Background Art

[0002] Color filters used in display devices such as liquid crystal display devices, electroluminescence display devices, and plasma displays, and solid-state imaging devices such as CCDs and CMOS sensors are manufactured from colored resin compositions. As the colored resin composition for forming the color filter, various colorants are used, and as the colorant, for example, an example (Patent Document 1) of using a compound represented by the following formula (I-5a-2) is known.

[0003]

Chemical Formula

Prior Art Documents

Patent Documents

[0004]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0005] However, the color filter formed from the colored resin composition containing the above compound may not sufficiently satisfy the brightness and contrast. Therefore, an object of the present invention is to provide a colored resin composition capable of forming a color filter excellent in brightness and contrast.

Means for Solving the Problems

[0006] That is, the gist of the present invention is as follows. [1] A colored resin composition containing a phenylphosphonic acid which may have a substituent, a colorant, a dispersant having an amine value of less than 70 mg KOH / g, and a resin, wherein the colorant contains a compound represented by the following formula (I). [Chemical formula] [In formula (I), R 1 ~R 4 and R 13 each independently represent a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent. R 5 ~R 12 each independently represent a hydrogen atom, a halogen atom or a hydrocarbon group having 1 to 5 carbon atoms which may have a substituent. T 1 represents a divalent aromatic hydrocarbon group which may have a substituent. T 2 represents a divalent aromatic hydrocarbon group which may have a substituent or a divalent aromatic heterocyclic group which may have a substituent. L 1 represents an a-valent aliphatic hydrocarbon group having 1 to 12 carbon atoms which may have a substituent or a group represented by formula (i). a represents an integer of 2 or more. b and c each independently represent an integer of 1 or more. d represents an integer of 0 or more. X c- represents a c-valent anion.] [Chemical formula] [In formula (i), T 3 represents an a-valent aromatic hydrocarbon group which may have a substituent or an a-valent aromatic heterocyclic group which may have a substituent. L 2 represents a divalent aliphatic hydrocarbon group having 1 to 5 carbon atoms which may have a substituent. a represents an integer of 2 or more. * is T2 represents a bonding hand with [.] [2]R 1 and R 3 each independently represent a phenyl group which may have a substituent, said R 1 and R 3 The phenyl group of has an alkyl group having 1 to 4 carbon atoms at at least one of the two bonding positions that are ortho to the N to which the phenyl group is bonded. The colored resin composition according to [1]. [3] The colored resin composition according to [1] or [2], wherein the amine value of the dispersant is 0 mgKOH / g or more and 65 mgKOH / g or less. [4] The colored resin composition according to any one of [1] to [3], further containing a polymerizable compound and a polymerization initiator. [5] A color filter formed from the colored resin composition according to any one of [1] to [4]. [6] A display device including the color filter according to [5]. [Effects of the Invention]

[0007] According to the present invention, it is possible to provide a colored resin composition capable of forming a color filter excellent in lightness and contrast. [Embodiments for Carrying Out the Invention]

[0008] The colored resin composition of the present invention includes phenylphosphonic acid which may have a substituent, a colorant (hereinafter sometimes referred to as colorant (A)), a dispersant (hereinafter sometimes referred to as dispersant (P)), and a resin (hereinafter sometimes referred to as resin (B)). The colored resin composition of the present invention may further contain a polymerizable compound (hereinafter sometimes referred to as polymerizable compound (C)). The colored resin composition of the present invention may further contain a polymerization initiator (hereinafter sometimes referred to as polymerization initiator (D)). The colored resin composition of the present invention may further contain a solvent (hereinafter sometimes referred to as solvent (E)). The colored resin composition of the present invention may further contain a polymerization initiation aid (hereinafter sometimes referred to as polymerization initiation aid (D1)). The colored resin composition of the present invention may further contain a leveling agent (hereinafter sometimes referred to as leveling agent (F)). In the present specification, the compounds exemplified as each component can be used alone or in combination of a plurality of kinds unless otherwise specified.

[0009] <Colorant (A)> The colorant (A) contains a compound represented by the following formula (I) (hereinafter sometimes referred to as compound (I)). Hereinafter, the present invention will be described in detail using formula (I), but compound (I) also includes tautomers of formula (I).

[0010]

Chemical formula

[0011] R 1 ~R 4 and R 13 Examples of the hydrocarbon group having 1 to 10 carbon atoms represented by include an aliphatic hydrocarbon group and an aromatic hydrocarbon group. The aliphatic hydrocarbon group may be saturated or unsaturated, and may be linear or alicyclic.

[0012] Examples of the saturated or unsaturated chain hydrocarbon group include linear alkyl groups such as methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, and n-decyl group; branched alkyl groups such as isopropyl group, (1-ethyl)propyl group, isobutyl group, sec-butyl group, tert-butyl group, (1-ethyl)butyl group, (2-ethyl)butyl group, (1-propyl)butyl group, isopentyl group, neopentyl group, tert-pentyl group, (2-methyl)pentyl group, (1-ethyl)pentyl group, (3-ethyl)pentyl group, (1-propyl)pentyl group, (1-butyl)pentyl group, isohexyl group, (2-methyl)hexyl group, (5-methyl)hexyl group, (2-ethyl)hexyl group, (1-butyl)hexyl group, (2-methyl)heptyl group, (2-ethyl)heptyl group, (3-ethyl)heptyl group, (2-methyl)octyl group, and (2-ethyl)octyl group; alkenyl groups such as vinyl group, 1-propenyl group, 2-propenyl group (allyl group), (1-methyl)ethenyl group, 2-butenyl group, 3-butenyl group, 1,3-butadienyl group, (1-(2-propenyl))ethenyl group, (1,2-dimethyl)propenyl group, and 2-pentenyl group; and the like.

[0013] Examples of the saturated or unsaturated alicyclic hydrocarbon group include cycloalkyl groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, and cyclooctyl group; cycloalkenyl groups such as cyclohexenyl group (e.g., cyclohex-2-ene, cyclohex-3-ene), cycloheptenyl group, and cyclooctenyl group; norbornyl group, adamantyl group, bicyclo[2.2.2]octyl group; and the like.

[0014] Examples of the aromatic hydrocarbon group include aryl groups such as phenyl group, 1-naphthyl group, 2-naphthyl group; alkylaryl groups such as o-tolyl group, m-tolyl group, p-tolyl group, 2-ethylphenyl group, 3-ethylphenyl group, 4-ethylphenyl group, 2,3-dimethylphenyl group, 2,4-dimethylphenyl group, 2,5-dimethylphenyl group, 2,6-dimethylphenyl group, 3,4-dimethylphenyl group, 3,5-dimethylphenyl group, 2,4,6-trimethylphenyl group, 2-methyl-6-ethylphenyl group, 2,6-diethylphenyl group, o-isopropylphenyl group, m-isopropylphenyl group, p-isopropylphenyl group, 2-methyl-6-isopropylphenyl group, 4-butylphenyl group, o-tert-butylphenyl group, m-tert-butylphenyl group, p-tert-butylphenyl group; alkenylaryl groups such as 4-vinylphenyl group; and the like.

[0015] The hydrocarbon group having 1 to 10 carbon atoms may be a group formed by combining two or more of the linear hydrocarbon groups, alicyclic hydrocarbon groups, and aromatic hydrocarbon groups listed above, as long as the upper limit of the number of carbon atoms is 10. Such groups include, for example, aralkyl groups such as benzyl group, phenethyl group, 1-methyl-1-phenylethyl group; arylalkenyl groups such as phenylethenyl group (phenylvinyl group); arylalkynyl groups such as phenylethynyl group; 1-methylcyclopropyl group, 1-methylcyclohexyl group, 2-methylcyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 1,2-dimethylcyclohexyl group, 1,3-dimethylcyclohexyl group, 1,4-dimethylcyclohexyl group, 2,3-dimethylcyclohexyl group, 2,4-dimethylcyclohexyl group, 2,5-dimethylcyclohexyl group, 2,6-dimethylcyclohexyl group, 3,4-dimethylcyclohexyl group, 3,5-dimethylcyclohexyl group, 2,2-dimethylcyclohexyl group, 3,3-dimethylcyclohexyl group, 4,4-dimethylcyclohexyl group, 2,4,6-trimethylcyclohexyl group, 2,2,6,6-tetramethylcyclohexyl group, 3,3,5,5-tetramethylcyclohexyl group, etc., which are alicyclic hydrocarbon groups to which one or more alkyl groups or alicyclic hydrocarbon groups are bonded; alkyl groups to which one or more alicyclic hydrocarbon groups such as cyclopropylmethyl group, cyclopropylethyl group, cyclobutylmethyl group, cyclobutylethyl group, cyclopentylmethyl group, cyclopentylethyl group, cyclohexylmethyl group, 2-methylcyclohexylmethyl group, cyclohexylethyl group, etc. are bonded; and the like.

[0016] Examples of the substituent that the hydrocarbon group having 1 to 10 carbon atoms may have (hereinafter sometimes referred to as substituent A) include a halogen atom, a hydroxy group, an alkoxy group, a formyl group, a substituted or unsubstituted amino group, a nitro group, a cyano group, -SO3 - , and at least one or more selected from the group consisting of -SO3M, where M represents a hydrogen atom or an alkali metal atom.

[0017] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Examples of the alkoxy group include alkoxy groups having 1 to 4 carbon atoms such as methoxy group, ethoxy group, propoxy group, and butoxy group. Examples of the substituted amino group include amino groups having one or two hydrocarbon groups, and examples of the hydrocarbon group include the groups exemplified as the hydrocarbon groups having 1 to 10 carbon atoms described above. Examples of the substituted amino group include, for example, N-methylamino group, N,N-dimethylamino group, N-ethylamino group, N,N-diethylamino group, N-propylamino group, N,N-dipropylamino group, N-isopropylamino group, N,N-diisopropylamino group, N-phenylamino group, N,N-diphenylamino group, N,N-ethylmethylamino group, N,N-methylphenylamino group, N,N-ethylphenylamino group, and the like.

[0018] Examples of the alkali metal atom include sodium and potassium.

[0019] R 5 ~R 12 Examples of the halogen atom represented by R 5 ~R 12 include fluorine atom, chlorine atom, bromine atom, and iodine atom.

[0020] R 5 ~R 12 Examples of the hydrocarbon group having 1 to 5 carbon atoms represented by R 5 ~R 12 include aliphatic hydrocarbon groups having 1 to 5 carbon atoms. Specifically, among the groups exemplified as the aliphatic hydrocarbon groups for R 1 ~R 4 and R 13 , groups having 1 to 5 carbon atoms are included. 1 ~R 4 and R 13 Examples of the substituent that the hydrocarbon group having 1 to 5 carbon atoms may have include the groups exemplified as substituent A.

[0021] Examples of the substituent that the hydrocarbon group having 1 to 5 carbon atoms may have include the groups exemplified as substituent A.

[0022] T 1 and T 2The divalent aromatic hydrocarbon group represented by [description] is a group in which two hydrogen atoms directly bonded to carbon atoms constituting the aromatic hydrocarbon ring are replaced by bonds. The aromatic hydrocarbon ring constituting the divalent aromatic hydrocarbon group may be either a monocyclic ring or a condensed ring. Examples include a benzene ring, a naphthalene ring, an anthracene ring, and structures in which at least one hydrogen atom of these aromatic hydrocarbon rings is replaced by a hydrocarbon group. Examples of the hydrocarbon group include the groups exemplified as the hydrocarbon group having 1 to 10 carbon atoms represented by R 1 ~R 4 and R 13 preferably a saturated chain hydrocarbon group, an aryl group, or an alkylaryl group, and more preferably a saturated chain hydrocarbon group having 1 to 4 carbon atoms. The number of hydrocarbon groups bonded to the aromatic hydrocarbon ring is preferably 0 to 4, more preferably 0 to 3, and even more preferably 0 to 2. Specific examples of the divalent aromatic hydrocarbon group include groups represented by the following formulas (Ta-1) to (Ta-8).

[0023] [Chemical formula]

[0024] T 2 The divalent aromatic heterocyclic group represented by [description] is a group in which two hydrogen atoms directly bonded to atoms constituting the aromatic heterocyclic ring are replaced by bonds. The aromatic heterocyclic ring constituting the divalent aromatic heterocyclic group may be either a monocyclic ring or a condensed ring. Examples include a pyrrole ring, an oxazole ring, a pyrazole ring, an imidazole ring, a thiazole ring, a furan ring, a thiophene ring, a pyridine ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, an indole ring, a benzimidazole ring, a benzothiazole ring, a quinoline ring, a benzofuran ring, and structures in which at least one hydrogen atom of these aromatic heterocyclic rings is replaced by a hydrocarbon group. Examples of the hydrocarbon group include the groups exemplified as the hydrocarbon group having 1 to 10 carbon atoms represented by R 1 ~R 4 and R 13Examples of the hydrocarbon group having 1 to 10 carbon atoms represented by [description] include groups exemplified as the substituent A, and preferably a saturated chain hydrocarbon group, an aryl group, or an alkylaryl group. The number of hydrocarbon groups bonded to the aromatic heterocyclic ring is preferably 0 to 4, more preferably 0 to 3, and even more preferably 0 to 2.

[0025] Examples of the substituent that the divalent aromatic hydrocarbon group and the divalent aromatic heterocyclic group may have include the groups exemplified as the substituent A.

[0026] L 1 The a-valent aliphatic hydrocarbon group having 1 to 12 carbon atoms represented by [description] is a group in which a hydrogen atoms constituting the aliphatic hydrocarbon are replaced by bonds. When a is 2 or more, it is preferable that the a bonds are present on different carbon atoms. Examples of the a-valent aliphatic hydrocarbon group include an a-valent chain hydrocarbon group, an a-valent alicyclic hydrocarbon group, an a-valent group combining a chain hydrocarbon group and an alicyclic hydrocarbon group, and the like.

[0027] The a-valent chain hydrocarbon group may be saturated or unsaturated, but is preferably an a-valent saturated chain hydrocarbon group. Examples of the a-valent saturated chain hydrocarbon group include alkane diyl groups such as methylene group, ethylene group, propane-1,2-diyl group, propane-1,3-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group, hexane-1,6-diyl group; alkane triyl groups such as the groups represented by the following formulas (a-1) to (a-2); alkane tetrayl groups such as the group represented by the following formula (a-3); and the like. The number of carbon atoms of the a-valent chain hydrocarbon group is preferably 1 to 8, and more preferably 1 to 6.

[0028]

Chemical formula

[0029] The alicyclic hydrocarbon group of a-valence may be saturated or unsaturated, but is preferably an alicyclic hydrocarbon group of a-valence that is saturated. Examples of the alicyclic hydrocarbon group of a-valence that is saturated include divalent saturated alicyclic hydrocarbon groups such as cyclohexane-1,2-diyl group, cyclohexane-1,4-diyl group, norbornane-2,5-diyl group; trivalent saturated alicyclic hydrocarbon groups such as cyclohexane-1,3,5-triyl group; tetravalent saturated alicyclic hydrocarbon groups such as cyclohexane-1,2,4,5-tetrayl group; and the like. The number of carbon atoms in the alicyclic hydrocarbon group of a-valence is preferably 3 to 10, more preferably 3 to 6.

[0030] As the a-valent group combining a chain hydrocarbon group and an alicyclic hydrocarbon group, it is preferably an a-valent group combining at least one chain hydrocarbon group and at least one saturated alicyclic hydrocarbon group, and examples thereof include groups represented by the following formulas (a-4) to (a-7).

[0031]

Chemical formula

[0032] Examples of the substituent that the a-valent aliphatic hydrocarbon group having 1 to 12 carbon atoms may have include the groups exemplified as Substituent A.

[0033] L 1 may be a group represented by formula (i).

[0034] In formula (i), T 3 The a-valent aromatic hydrocarbon group represented by is a group in which a hydrogen atoms directly bonded to the carbon atoms constituting the ring in the aromatic hydrocarbon ring are replaced by bonds. Examples of the aromatic hydrocarbon ring constituting the a-valent aromatic hydrocarbon group include the structures described as the aromatic hydrocarbon rings constituting the above-mentioned divalent aromatic hydrocarbon groups.

[0035] In formula (i), T 3The a-valent aromatic heterocyclic group represented by [a certain formula] is a group in which a hydrogen atoms directly bonded to the atoms constituting the aromatic heterocyclic ring are replaced by bonds. Examples of the aromatic heterocyclic ring constituting the a-valent aromatic heterocyclic group include the structures described as the aromatic heterocyclic ring constituting the aforementioned divalent aromatic heterocyclic group.

[0036] Examples of the substituent that the a-valent aromatic hydrocarbon group and the a-valent aromatic heterocyclic group may have include the groups exemplified as Substituent A.

[0037] In formula (i), L 2 Examples of the divalent aliphatic hydrocarbon group having 1 to 5 carbon atoms represented by [a certain formula] include a divalent chain hydrocarbon group having 1 to 5 carbon atoms and a divalent alicyclic hydrocarbon group having 1 to 5 carbon atoms.

[0038] The divalent chain hydrocarbon group may be saturated or unsaturated, but is preferably a divalent saturated chain hydrocarbon group. Examples of the divalent saturated chain hydrocarbon group include alkane diyl groups such as methylene group, ethylene group, propane-1,2-diyl group, propane-1,3-diyl group, butane-1,4-diyl group, and pentane-1,5-diyl group.

[0039] The divalent alicyclic hydrocarbon group may be saturated or unsaturated, but is preferably a divalent saturated alicyclic hydrocarbon group. Examples of the divalent saturated alicyclic hydrocarbon group include cyclopropyl-1,2-diyl group and cyclobutyl-1,3-diyl group.

[0040] Examples of the substituent that the divalent aliphatic hydrocarbon group having 1 to 5 carbon atoms may have include the groups exemplified as Substituent A.

[0041] Specific examples of the group represented by formula (i) include the groups represented by the following formula (i1) or (i2).

[0042]

Chemical formula

[0043] Examples of the divalent saturated chain hydrocarbon group having 1 to 5 carbon atoms include a methylene group, an ethylene group, a propane-1,2-diyl group, a propane-1,3-diyl group, a butane-1,4-diyl group, and a pentane-1,5-diyl group.

[0044] In formulas (i1) to (i2), L i1 and L i2 , and L i3 ~L i5 may be the same or different from each other, but are preferably the same.

[0045] Examples of the c-valent anion represented by X c- include known anions. Specifically, they include halide ions such as fluoride ion, chloride ion, bromide ion, and iodide ion, boron-containing anions, aluminum-containing anions, fluorine-containing anions, and anions containing at least one element selected from the group consisting of tungsten, molybdenum, silicon, and phosphorus and oxygen as essential elements.

[0046] Examples of the boron-containing anion and the aluminum-containing anion include, for example, an anion represented by the following formula (4).

[0047] [Chemical formula]

[0048] [In formula (4), W 1 , W 2 each independently represents a group having two substituents that release protons from monovalent proton-donating substituents. M A represents boron or aluminum.]

[0049] Examples of the group having two substituents that release protons from monovalent proton-donating substituents include groups formed by releasing protons from two proton-donating substituents respectively from a compound having at least two monovalent proton-donating substituents (such as a hydroxy group, a carboxylic acid group, etc.). Examples of such compounds preferably include catechol which may have a substituent, 2,3-dihydroxynaphthalene which may have a substituent, 2,2'-biphenol which may have a substituent, 3-hydroxy-2-naphthoic acid which may have a substituent, 2-hydroxy-1-naphthoic acid which may have a substituent, 1-hydroxy-2-naphthoic acid which may have a substituent, binaphthol which may have a substituent, salicylic acid which may have a substituent, benzoic acid which may have a substituent, or mandelic acid which may have a substituent.

[0050] In the exemplified compounds, examples of the substituent include a saturated hydrocarbon group (such as an alkyl group, a cycloalkyl group, etc.), a halogen atom, a haloalkyl group, a hydroxy group, an amino group, a nitro group, an alkoxy group, etc.

[0051] Examples of salicylic acids which may have a substituent include salicylic acid, 3-methylsalicylic acid, 3-tert-butylsalicylic acid, 3-methoxysalicylic acid, 3-nitrosalicylic acid, 4-trifluoromethylsalicylic acid, 3,5-di-tert-butylsalicylic acid, 3-aminosalicylic acid, 4-aminosalicylic acid, 5-aminosalicylic acid, 6-aminosalicylic acid and other monoaminosalicylic acids; 3-hydroxysalicylic acid (2,3-dihydroxybenzoic acid), 4-hydroxysalicylic acid (2,4-dihydroxybenzoic acid), 5-hydroxysalicylic acid (2,5-dihydroxybenzoic acid), 6-hydroxysalicylic acid (2,6-dihydroxybenzoic acid) and other monohydroxysalicylic acids; 4,5-dihydroxysalicylic acid, 4,6-dihydroxysalicylic acid and other dihydroxysalicylic acids; 3-chlorosalicylic acid, 4-chlorosalicylic acid, 5-chlorosalicylic acid, 6-chlorosalicylic acid, 3-bromosalicylic acid, 4-bromosalicylic acid, 5-bromosalicylic acid, 6-bromosalicylic acid and other monohalosalicylic acids; 3,5-dichlorosalicylic acid, 3,5-dibromosalicylic acid, 3,5-diiodosalicylic acid and other dihalosalicylic acids; 3,5,6-trichlorosalicylic acid and other trihalosalicylic acids; and the like.

[0052] Examples of benzoic acids which may have a substituent include

[0053]

Chemical formula

[0054] Examples of mandelic acids which may have a substituent include

[0055]

Chemical formula

[0056] Among the anions represented by formula (4), preferred anions are anions represented by the following formulae, anions (BC-1) to anions (BC-24) having the substituents described in Table 1, and anions (BC-25) to anions (BC-28) represented by formula (BC-25), formula (BC-26), formula (BC-27) and formula (BC-28), respectively.

[0057]

Chemical formula

[0058]

Table 1

[0059]

Chemical formula

[0060]

Chemical formula

[0061]

Chemical formula

[0062]

Chemical formula

[0063] M shown in anions (BC-1) to anions (BC-24) and anions (BC-25) to anions (BC-28) represented by formula (BC-25), formula (BC-26), formula (BC-27) and formula (BC-28), respectively A represents boron or aluminum.

[0064] From the viewpoint of solubility in organic solvents, as the anion represented by the formula (4), anion (BC-1), anion (BC-2), anion (BC-3), anion (BC-25), anion (BC-26), and anion (BC-27) are preferable, anion (BC-1), anion (BC-2), and anion (BC-25) are more preferable, and anion (BC-1) and anion (BC-2) are even more preferable.

[0065] Examples of the fluorine-containing anion include groups represented by the following formulas (6), (7), (8), and (9).

[0066]

Chemical formula

[0067] [In formula (6), W 3 and W 4 each independently represent a fluorine atom or a fluorinated alkyl group having 1 to 4 carbon atoms, or W 3 and W 4 together represent a fluorinated alkanediyl group having 1 to 4 carbon atoms.]

[0068]

Chemical formula

[0069] [In formula (7), W 5 to W 7 each independently represent a fluorine atom or a fluorinated alkyl group having 1 to 4 carbon atoms.]

[0070]

Chemical formula

[0071] [In formula (8), Y 1 represents a fluorinated alkanediyl group having 1 to 4 carbon atoms.]

[0072]

Chemical formula

[0073] [In formula (9), Y 2 represents an alkyl fluoride group having 1 to 4 carbon atoms.]

[0074] In formulas (6), (7) and (9), as the alkyl fluoride group having 1 to 4 carbon atoms, a perfluoroalkyl group is preferable. Examples of the perfluoroalkyl group include -CF3, -CF2CF3, -CF2CF2CF3, -CF(CF3)2, -CF2CF2CF2CF3, -CF2CF(CF3)2, -C(CF3)3 and the like.

[0075] In formulas (6) and (8), as the alkanediyl fluoride group having 1 to 4 carbon atoms, a perfluoroalkanediyl group is preferable. Examples of the perfluoroalkanediyl group include -CF2-, -CF2CF2-, -CF2CF2CF2-, -C(CF3)2-, -CF2CF2CF2CF2- and the like.

[0076] Examples of the anion represented by formula (6) (hereinafter sometimes referred to as "anion (6)") include anions represented by formulas (6-1) to (6-6) (hereinafter sometimes referred to as "anion (6-1)" to "anion (6-6)").

[0077] [Chemical formula]

[0078] Examples of the anion represented by formula (7) (hereinafter sometimes referred to as "anion (7)") include anion (7-1) represented by the following formula.

[0079] [Chemical formula]

[0080] Examples of the anion represented by formula (8) (hereinafter sometimes referred to as "anion (8)") include anions represented by formulas (8-1) to (8-4) (hereinafter sometimes referred to as "anion (8-1)" to "anion (8-4)").

[0081] [Chemical formula]

[0082] Examples of the anion represented by formula (9) (hereinafter sometimes referred to as "anion (9)") include anions represented by formulas (9-1) to (9-4) (hereinafter sometimes referred to as "anion (9-1)" to "anion (9-4)").

[0083] [Chemical formula]

[0084] X c- The c-valent anion represented by is at least one anion selected from the group consisting of anion (6), anion (7), anion (8) and anion (9) (i.e., a fluorine-containing anion), whereby the solubility of compound (I) in an organic solvent can be improved. Among them, anion (6-1), anion (6-2) and anion (7-1) are preferred, and anion (6-2) is particularly preferred.

[0085] X c- Examples of the c-valent anion represented by include anions containing at least one element selected from the group consisting of tungsten, molybdenum, silicon and phosphorus and oxygen as essential elements, and anions of heteropolyacids or isopolyacids containing tungsten as an essential element are preferred, and anions of phosphotungstic acid, silicotungstic acid and tungsten-based isopolyacids are more preferred.

[0086] Examples of anions of heteropolyacids or isopolyacids containing such tungsten as an essential element include, for example, Keggin-type phosphotungstate ion α-[PW 12 O 40 3- Dawson-type phosphotungstate ion α-[P2W 18 O 62 6- β-[P2W 18 O 62 6- Keggin-type silicotungstate ion α-[SiW 12 O 40 4- β-[SiW 12 O 40 4- γ-[SiW 12 O 40 4- Furthermore, as other examples, [P2W 17 O 61 10- [P2W 15 O 56 12- [H2P2W 12 O 48 12- [NaP5W 30 O 110 14- α-[SiW9O 34 10- γ-[SiW 10 O 36 8- α-[SiW 11 O 39 8- β-[SiW 11 O 39 8- [W6O 19 2- [W 10 O 32 4- WO4 2- etc. can be mentioned.

[0087] ​​​​​​​​​​​​​​​​Among anions other than anions of heteropolyacids or isopolyacids containing tungsten as an essential element, anions composed of at least one element selected from the group consisting of silicon and phosphorus and oxygen are preferred. Examples of such anions composed of at least one element selected from the group consisting of silicon and phosphorus and oxygen include SiO3 2- , PO4 3- .

[0088] In particular, from the viewpoints of ease of synthesis and post-treatment, heteropolyacid anions such as keggin-type phosphotungstic acid ions, dawson-type phosphotungstic acid ions, keggin-type silicotungstic acid ions, [W 10 O 32 4- and other isopolyacid anions are preferred.

[0089] In formula (I), the plurality of R 1 ~R 13 , T 1 , T 2 , and L 1 may be the same or different from each other, but are preferably the same.

[0090] R 1 ~R 4 are each independently preferably a saturated chain hydrocarbon group having 1 to 10 carbon atoms which may have a substituent, an aryl group having 6 to 10 carbon atoms which may have a substituent, or an alkylaryl group having 7 to 10 carbon atoms which may have a substituent.

[0091] In particular, R 1 and R 3 are each independently preferably an aryl group having 6 to 10 carbon atoms which may have a substituent, or an alkylaryl group having 7 to 10 carbon atoms which may have a substituent, and R 2 and R 4 are each independently preferably a saturated chain hydrocarbon group having 1 to 10 carbon atoms which may have a substituent. R 1 and R 3 ​is, independently of each other, a phenyl group which may have a substituent, and R 2 and R 4 are, independently of each other, more preferably a saturated linear hydrocarbon group having 1 to 10 carbon atoms which may have a substituent, R 1 and R 3 are, independently of each other, a phenyl group which may have a substituent, and is a group having an alkyl group having 1 to 4 carbon atoms at at least one of two bonding positions ortho to N bonded to the phenyl group, and R 2 and R 4 are, independently of each other, more preferably a saturated linear hydrocarbon group having 1 to 6 carbon atoms which may have a substituent, R 1 and R 3 are, independently of each other, a phenyl group which may have a substituent, and is a group having an alkyl group having 1 to 4 carbon atoms at at least one of two bonding positions ortho to N bonded to the phenyl group, and R 2 and R 4 are, independently of each other, even more preferably a saturated linear hydrocarbon group having 2 to 6 carbon atoms which may have a substituent, R 1 and R 3 are, independently of each other, a phenyl group which may have a substituent, and is a group having an alkyl group having 1 to 3 carbon atoms at each of two bonding positions ortho to N bonded to the phenyl group, and R 2 and R 4 are, independently of each other, particularly preferably a saturated linear hydrocarbon group having 2 to 6 carbon atoms which may have a substituent. Here, examples of the substituent which the phenyl group may have include at least one selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, a halogen atom, a hydroxy group, an alkoxy group, a formyl group, a substituted or unsubstituted amino group, a nitro group, a cyano group, -SO3 - and -SO3M (M is the same as above), and among them, an alkyl group having 1 to 4 carbon atoms, a halogen atom, an alkoxy group, and -SO3 -At least one selected from the group consisting of is preferable, and an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, and -SO3 - At least one selected from the group consisting of is more preferable. In particular, when the phenyl group has no substituent or has, as a substituent, an alkyl group having 1 to 4 carbon atoms, a halogen atom, a hydroxy group, a formyl group, a substituted or unsubstituted amino group, a nitro group, a cyano group, -SO3 - , and at least one substituent selected from the group consisting of -SO3M only (preferably at least one substituent selected from the group consisting of an alkyl group having 1 to 4 carbon atoms and -SO3 - only), the brightness of the obtained color filter can be further increased. Also, when the phenyl group has an alkoxy group (preferably a methoxy group) as a substituent, the light resistance can be improved. The substitution position of the alkoxy group (preferably a methoxy group) is not particularly limited, but by bonding to the position para to N bonded to the phenyl group, the light resistance improving effect can be further enhanced.

[0092] The aforementioned R 1 ~R 4 In a preferred embodiment, R 1 and R 3 are each independently particularly preferably any of the groups represented by formulas (r1) to (r3). Note that any one or more of the hydrogen atoms of the groups represented by formulas (r1) to (r3) may be substituted with -SO3 - .

[0093] [Chemical formula] [In the formula, R r1 ~R r4 each independently represent an alkyl group having 1 to 4 carbon atoms. * represents a bond.]

[0094] R r1 ~R r4is preferably a methyl group, an ethyl group, or a propyl group, more preferably a methyl group or an ethyl group, and even more preferably a methyl group.

[0095] R 5 ~R 12 is preferably a hydrogen atom.

[0096] R 13 is preferably a hydrogen atom or a hydrocarbon group having 1 to 6 carbon atoms which may have a substituent, more preferably a hydrogen atom or a saturated chain hydrocarbon group having 1 to 6 carbon atoms which may have a substituent, still more preferably a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, or an isopropyl group, and even more preferably a hydrogen atom.

[0097] T 1 As the aromatic hydrocarbon ring constituting the divalent aromatic hydrocarbon group represented by T, a benzene ring, a naphthalene ring, or a structure in which at least one hydrogen atom of these rings is replaced by a saturated chain hydrocarbon group having 1 to 10 (preferably 1 to 4) carbon atoms is preferable. T 1 is more preferably any of the groups represented by the above formulas (Ta-1) to (Ta-8), and particularly preferably the group represented by the above formula (Ta-8).

[0098] T 2 is preferably a divalent aromatic hydrocarbon group which may have a substituent. As the aromatic hydrocarbon ring constituting the divalent aromatic hydrocarbon group, a benzene ring, a naphthalene ring, or a structure in which at least one hydrogen atom of these rings is replaced by a saturated chain hydrocarbon group having 1 to 10 (preferably 1 to 4) carbon atoms is preferable, and a benzene ring or a structure in which at least one hydrogen atom of the benzene ring is replaced by a saturated chain hydrocarbon group having 1 to 4 carbon atoms is more preferable. T 2It is more preferably any of the groups represented by the following formulas (Tb-1) to (Tb-10), still more preferably any of the groups represented by the following formulas (Tb-3), (Tb-5), (Tb-6), (Tb-9), and (Tb-10), and particularly preferably any of the groups represented by the following formulas (Tb-5), (Tb-6), (Tb-9), and (Tb-10).

[0099]

Chemical formula

[0100] L 1 is an a-valent aliphatic hydrocarbon group having 1 to 8 carbon atoms which may have a substituent, or in the group represented by the formula (i), T 3 is an a-valent aromatic hydrocarbon group which may have a substituent, and L 2 is preferably a divalent saturated chain hydrocarbon group having 1 to 5 carbon atoms, more preferably an alkanediyl group having 1 to 6 carbon atoms which may have a substituent, a divalent saturated alicyclic hydrocarbon group having 3 to 10 carbon atoms which may have a substituent, or a group represented by the above formula (i1) or (i2), and still more preferably an alkanediyl group having 1 to 6 carbon atoms which may have a substituent, a divalent saturated alicyclic hydrocarbon group having 3 to 10 carbon atoms which may have a substituent, or any of the groups represented by the following formulas (i-1) to (i-4).

[0101]

Chemical formula

[0102] X c-The c-valent anion represented by [the formula] is preferably a halide ion or an anion containing, as essential elements, at least one element selected from the group consisting of tungsten, molybdenum, silicon and phosphorus and oxygen, more preferably a halide ion or an anion of a heteropolyacid or isopolyacid containing tungsten as an essential element, and still more preferably a halide ion, a keggin-type phosphotungstic acid ion, or a dawson-type phosphotungstic acid ion.

[0103] The substituent (i.e., substituent A) that the compound (I) has is preferably at least one selected from the group consisting of a halogen atom, a hydroxy group, an alkoxy group, a substituted or unsubstituted amino group, -SO3 - and -SO3M, more preferably at least one selected from the group consisting of a halogen atom, an alkoxy group, -SO3 - and -SO3M.

[0104] a is preferably an integer of 2 or more and 6 or less, more preferably an integer of 2 or more and 4 or less, and still more preferably 2 or 3. Note that a in formula (I) and a in formula (i) are the same.

[0105] c is usually 1 to 14, preferably 1 to 12, more preferably 1 to 10, still more preferably 1 to 6, and particularly preferably 1 to 4.

[0106] b and d are determined according to a, c, and the number of -SO3 - that the compound (I) has as a substituent (hereinafter sometimes referred to as e), and generally, they are adjusted so that the overall charge of formula (I) becomes 0. Therefore, usually, a to d in formula (I) satisfy the relationship of the following formula (z). a × b = (c × d) + e ···(z) [In the above formula, a to d have the same meanings as described above. e represents the number of -SO3 - that the compound (I) has as a substituent.]

[0107] e is an integer of 0 or more, preferably 0 or more and (a + 1) or less, more preferably 0 or more and a or less, still more preferably 0 or a. In particular, when d is 1 or more, e is 0, that is, the compound (I) does not have -SO3 - and when d is 0, it is preferable that e = a.

[0108] From the viewpoints of heat resistance and solvent resistance, X c- is an anion containing, as essential elements, at least one element selected from the group consisting of tungsten, molybdenum, silicon and phosphorus and oxygen, and a compound in which d is 1 or more and e is 0 is preferable.

[0109] The compound (I) is preferably a compound represented by the formula (I-1) or the formula (I-2).

[0110]

Chemical formula

Chemical formula

[0111]

Chemical formula

[0112] R 101 , R 103 , R 201 and R 203 The substituents that the phenyl groups represented by may have include at least one or more selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, a halogen atom, a hydroxy group, an alkoxy group, a formyl group, a substituted or unsubstituted amino group, a nitro group, a cyano group, and -SO3M (M is a hydrogen atom or an alkali metal atom). Among them, at least one or more selected from the group consisting of an alkyl group having 1 to 4 carbon atoms and an alkoxy group having 1 to 4 carbon atoms are preferable. The halogen atom, alkoxy group, substituted amino group, and alkali metal atom are the same as those described for substituent A.

[0113] R 101 , R 103 , R 201 and R 203is each independently a phenyl group which may have a substituent, and is preferably a group having an alkyl group with 1 to 4 carbon atoms at at least one (preferably both) of the two bonding positions ortho to the N bonded to the phenyl group. In particular, R 101 、R 103 、R 201 and R 203 are each independently preferably any of the groups represented by the above formulas (r1) to (r3), more preferably a group represented by the above formula (r1) or (r2) from the viewpoint of better lightness, and more preferably a group represented by the above formula (r3) from the viewpoint of better light resistance.

[0114] R 102 、R 104 、R 202 and R 204 are each independently preferably a saturated chain hydrocarbon group with 1 to 6 carbon atoms which may have a substituent, more preferably a saturated chain hydrocarbon group with 2 to 6 carbon atoms, and even more preferably a saturated chain hydrocarbon group with 2 to 4 carbon atoms. As the substituent (hereinafter referred to as substituent B) which the saturated chain hydrocarbon group represented by R 102 、R 104 、R 202 and R 204 may have, at least one or more selected from the group consisting of a halogen atom, a hydroxy group, an alkoxy group, a formyl group, a substituted or unsubstituted amino group, a nitro group, a cyano group, and -SO3M (M is a hydrogen atom or an alkali metal atom) can be mentioned. The halogen atom, alkoxy group, substituted amino group, and alkali metal atom are the same as those described for substituent A.

[0115] R 113 and R 213 As the substituent which the saturated chain hydrocarbon group with 1 to 6 carbon atoms may have, the groups described for substituent B can be mentioned. R 113 、R 213 are preferably hydrogen atoms.

[0116] T101 and T 201 Examples of the substituent that the divalent aromatic hydrocarbon group represented by T may have include the groups described as substituent B. T 101 and T 201 is preferably any of the groups represented by the above formulas (Ta-1) to (Ta-8), and more preferably the group represented by formula (Ta-8).

[0117] T 102 and T 202 Examples of the substituent that the divalent aromatic hydrocarbon group represented by T may have include the groups described as substituent B. Among them, at least one selected from the group consisting of a halogen atom and an alkoxy group is preferable. T 102 and T 202 is a divalent aromatic hydrocarbon group which may have a substituent, and the aromatic hydrocarbon ring constituting the divalent aromatic hydrocarbon group preferably has a structure in which at least one hydrogen atom of the benzene ring is replaced by a saturated chain hydrocarbon group having 1 to 4 carbon atoms. More preferably, it is any of the groups represented by the above formulas (Tb-1) to (Tb-10), still more preferably any of the groups represented by formulas (Tb-5), (Tb-6), (Tb-9), (Tb-10), and particularly preferably any of the groups represented by formulas (Tb-5) and (Tb-6).

[0118] L 101 and L 201 Examples of the a-valent saturated chain hydrocarbon group having 1 to 8 carbon atoms represented by T, 3 the a-valent aromatic hydrocarbon group represented by T, 103 the a101-valent aromatic hydrocarbon group represented by T, 203 the a201-valent aromatic hydrocarbon group represented by T, and L 2 Examples of the substituent of the aliphatic hydrocarbon group represented by T include the groups described as substituent B. L 101 and L 201It is preferably any one of an alkanediyl group having 1 to 6 carbon atoms which may have a substituent, a divalent saturated alicyclic hydrocarbon group having 3 to 10 carbon atoms which may have a substituent, or a group represented by the above formula (i1) or (i2). In formula (i-1), T 103 The a101-valent aromatic hydrocarbon group represented by is a group in which a101 hydrogen atoms directly bonded to the carbon atoms constituting the ring are replaced by bonds in the aromatic hydrocarbon ring. Examples of the aromatic hydrocarbon ring constituting the a101-valent aromatic hydrocarbon group include the structures described for the aromatic hydrocarbon ring constituting the above-mentioned divalent aromatic hydrocarbon group. In formula (i-2), T 203 The a201-valent aromatic hydrocarbon group represented by is a group in which a201 hydrogen atoms directly bonded to the carbon atoms constituting the ring are replaced by bonds in the aromatic hydrocarbon ring. Examples of the aromatic hydrocarbon ring constituting the a201-valent aromatic hydrocarbon group include the structures described for the aromatic hydrocarbon ring constituting the above-mentioned divalent aromatic hydrocarbon group. L 102 and L 202 are preferably an alkanediyl group having 1 to 5 carbon atoms, more preferably a methylene group, an ethylene group, a propane-1,2-diyl group, a propane-1,3-diyl group, a butane-1,4-diyl group, or a pentane-1,5-diyl group.

[0119] a201 and e201 are preferably the same. a101 in formula (I-1) and a101 in formula (i-1) are preferably the same. a201 in formula (I-2) and a201 in formula (i-2) are preferably the same.

[0120] The compounds represented by formula (I-1) and formula (I-2) preferably have a charge of 0.

[0121] From the viewpoints of heat resistance and solvent resistance, the compound represented by formula (I-1) is preferred.

[0122] Examples of the compound (I) include compounds (I-1a-1) to (I-108a-1) and compounds (I-1a-2) to (I-108a-2) represented by the following formula (I-a), and compounds (I-1b) to (I-108b) represented by the following formula (I-b). Note that the compound represented by the formula (I-b) indicates a compound in which b is 1 and d is 0 among the compounds (I). The compound represented by the formula (I-b) has two hydrogen atoms out of the hydrogen atoms of R 1b ~R 13b 、T 1b 、T 2b 、and L 1b substituted with -SO3 - .

[0123]

Chemical formula

[0124]

Table 2

[0125]

Table 3

[0126]

Table 4

[0127]

Table 5

[0128]

Table 6

[0129]

Chemical formula

[0130]

Table 7

[0131]

Table 8

[0132]

Table 9

[0133] In Tables 2 to 9, H represents a hydrogen atom, Et represents an ethyl group, Pr represents an n-propyl group, r-1 to r-3 represent groups represented by the following formulas (r-1) to (r-3), Ta-8 represents a group represented by the following formula (Ta-8), Tb-5 to Tb-6 and Tb-9 to Tb-10 represent groups represented by the following formulas (Tb-5) to (Tb-6) and (Tb-9) to (Tb-10), l-1 represents a group represented by the following formula (l-1), and i-2 and i-4 represent groups represented by the following formulas (i-2) and (i-4).

[0134]

Chemical formula

[0135]

Chemical formula

[0136]

Chemical formula

[0137]

Chemical formula

[0138] As the compound (I), compounds (I-1a-1) to (I-36a-1), compounds (I-1a-2) to (I-36a-2), compounds (I-55a-1) to (I-90a-1), compounds (I-55a-2) to (I-90a-2), compounds (I-1b) to (I-36b), and compounds (I-55b) to (I-90b) are preferable, compounds (I-1a-1) to (I-18a-1), compounds (I-55a-1) to (I-72a-1), compounds (I-1a-2) to (I-18a-2), compounds (I-55a-2) to (I-72a-2), compounds (I-1b) to (I-18b), and compounds (I-55b) to (I-72b) are more preferable, and compounds (I-1a-2) to (I-18a-2), compounds (I-55a-2) to (I-72a-2), compounds (I-1b) to (I-18b), and compounds (I-55b) to (I-72b) are even more preferable. From the viewpoint of better lightness, R 1a , R 3a , R 1b , R 3b is preferably a compound represented by the formula (r-1) or (r-2), and from the viewpoint of better light fastness, R 1a , R 3a , R 1b , R 3b is preferably a compound represented by the formula (r-3). Further, from the viewpoints of heat resistance and solvent resistance, compounds (I-1a-2) to (I-108a-2) are preferable, compounds (I-1a-2) to (I-18a-2) and compounds (I-55a-2) to (I-72a-2) are more preferable, compounds (I-1a-2) to (I-6a-2) and compounds (I-55a-2) to (I-60a-2) are even more preferable, and compounds (I-1a-2) to (I-6a-2) are even more preferably.

[0139] The compound (I) can be produced, for example, by the following methods (1) to (3), etc.

[0140] (1) Xc- Process for producing compound (I) in which X is a halide ion (hereinafter sometimes referred to as compound (I')). Compound (I') can be produced, for example, by reacting a compound represented by formula (B-I) with a compound represented by formula (C-I).

[0141] [Chemical formula] [In formulas (B-I) and (C-I), R 1 ~R 13 , T 2 , L 1 , and a represent the same meanings as described above. T 1B represents a group in which a bond different from the bond bonded to the nitrogen atom in the above T 1 is replaced by a hydrogen atom.]

[0142] The amount of the compound represented by formula (C-I) used is preferably 0.5 mol or more and 10 mol or less, more preferably 1 mol or more and 4 mol or less, per 1 mol of the compound represented by formula (B-I).

[0143] The reaction temperature is preferably 30°C to 180°C, more preferably 80°C to 130°C. The reaction time is preferably 1 hour to 12 hours, more preferably 1 hour to 8 hours.

[0144] The above reaction may be carried out in the presence of an organic solvent or without a solvent, but from the viewpoint of yield, it is preferably carried out in an organic solvent. Examples of the organic solvent include hydrocarbon solvents such as toluene and xylene; halogenated hydrocarbon solvents such as chlorobenzene, dichlorobenzene, and chloroform; alcohol solvents such as methanol, ethanol, isopropanol, and butanol; nitrohydrocarbon solvents such as nitrobenzene; ketone solvents such as methyl isobutyl ketone; amide solvents such as 1-methyl-2-pyrrolidone; and the like. The amount of the organic solvent used is preferably 1 part by mass or more and 20 parts by mass or less, more preferably 2 parts by mass or more and 10 parts by mass or less, per 1 part by mass of the compound represented by formula (B-I).

[0145] From the perspective of yield, the above reaction is preferably carried out in the presence of a condensing agent. Examples of the condensing agent include phosphorus oxychloride such as phosphoric acid, polyphosphoric acid, phosphorus oxychloride, thionyl halides such as sulfuric acid and thionyl chloride, etc. When using phosphorus oxychloride, thionyl halide, etc. as the condensing agent and satisfying the relationship of formula (z1), X c- a compound (I’) in which is a halide ion can be obtained. a×b - e > 0 ···(z1) [In the above formula, a and b have the same meanings as a and b in formula (I). e represents the number of -SO3 - contained as a substituent in the compound (I’).] The amount of the condensing agent used is preferably 0.1 part by mass or more and 20 parts by mass or less, more preferably 0.2 part by mass or more and 10 parts by mass or less, based on 1 part by mass of the compound represented by formula (B-I).

[0146] The method for obtaining the compound (I’) from the reaction mixture is not particularly limited, and various known methods can be adopted. After extraction, the obtained residue may be purified by column chromatography, recrystallization, or the like.

[0147] As the method for producing the compound (B-I), various known methods, for example, the method described in German Patent Application P3928243.0 can be used. Further purification may be carried out by known methods such as recrystallization and preparative chromatography as necessary.

[0148] As the method for producing the compound (C-I), various known methods can be mentioned. Further purification may be carried out by known methods such as recrystallization and preparative chromatography as necessary.

[0149] (2) X c- is an anion other than a halide ion (hereinafter, anion X 1 ), and the method for producing the compound (I) (hereinafter, sometimes referred to as compound (I’’)) Compound (I'') can be produced by mixing compound (I') with an alkali metal salt or a protonic acid of anion X 1 Examples of the alkali metal include lithium, sodium, potassium and the like.

[0150] The amount of the alkali metal salt or the protonic acid of anion X 1 used with respect to compound (I') may be added in a stoichiometric ratio such that the charges of the cation in compound (I') and anion X 1 are balanced. Preferably, it is 0.5 mol or more and 8 mol or less, more preferably 1 mol or more and 3 mol or less, per 1 mol of compound (I').

[0151] Compound (I') and anion X 1 may be mixed by dissolving both in the following solvent or without dissolving.

[0152] Examples of the solvent include N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide, acetonitrile, ethyl acetate, toluene, methanol, ethanol, isopropanol, acetone, tetrahydrofuran, dioxane, water and chloroform. Among them, from the viewpoint of solubility, at least one solvent selected from the group consisting of N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide, methanol, ethanol, isopropanol and water is preferable. The amount of the solvent used is preferably 1 part by mass or more and 30 parts by mass or less, more preferably 2 parts by mass or more and 20 parts by mass or less, per 1 part by mass of compound (I'). When the solvent is water, an acid such as acetic acid or hydrochloric acid may be added.

[0153] Compound (I') and anion X 1The mixing temperature with an alkali metal salt or a protonic acid is preferably from 0°C to 150°C, more preferably from 10°C to 120°C, still more preferably from 20°C to 100°C. The mixing time is preferably from 1 hour to 72 hours, more preferably from 2 hours to 24 hours, still more preferably from 3 hours to 12 hours.

[0154] When a solvent miscible with water is used, the solutions are mixed and, if necessary, stirred for an additional 1 to 3 hours, and then the solvent is removed to obtain compound (I''). Optionally, the obtained compound (I'') may be washed with ion-exchanged water, methanol, or the like.

[0155] When a solvent immiscible with water is used, the reaction mixture is mixed with ion-exchanged water and, if necessary, stirred for an additional 1 to 3 hours, and then the organic layer is obtained by liquid separation to obtain a solution containing compound (I''). Optionally, the solution may be washed with ion-exchanged water. Compound (I'') can be obtained by removing the solvent from the solution containing compound (I'').

[0156] (3) X c- A method for producing a compound in which X is absent (i.e., d = 0) (hereinafter sometimes referred to as compound (I''')). Compound (I''') can be produced by mixing compound (I') and sulfuric acid.

[0157] The amount of sulfuric acid used relative to compound (I') may be added in a stoichiometric ratio such that the charge of the cation in compound (I') and -SO3 - are balanced. For example, it is 0.5 mol or more and 8 mol or less, preferably 1 mol or more and 3 mol or less, per 1 mol of compound (I'). Further, the sulfuric acid may be used as a reaction solvent. When sulfuric acid is used as a solvent, the amount of sulfuric acid used is, for example, 20 mol or more, preferably 25 mol or more, per 1 mol of compound (I'). The upper limit of the amount of sulfuric acid used when sulfuric acid is used as a solvent is not particularly limited, but is, for example, 100 parts by mass or less, preferably 50 parts by mass or less, per 1 part by mass of compound (I').

[0158] The mixing temperature of compound (I') and sulfuric acid is preferably 0°C to 150°C, more preferably 10°C to 120°C, and even more preferably 20°C to 100°C. The mixing time is preferably 1 hour to 72 hours, more preferably 2 hours to 24 hours, and even more preferably 3 hours to 12 hours.

[0159] The mixture obtained by mixing compound (I') and sulfuric acid can be added to ice water to form a suspension, and then filtered to obtain compound (I'''). If necessary, it may be further purified by known methods such as recrystallization or preparative chromatography.

[0160] The content of compound (I) is preferably 70% by mass or more, more preferably 80% by mass or more, even more preferably 90% by mass or more, and even more preferably 95% by mass or more, and may be 100% by mass, in 100% by mass of colorant (A). Colorant (A) may contain one or more compounds (I).

[0161] Colorant (A) may contain dyes other than compound (I) (hereinafter sometimes referred to as dye (A1-1)) and / or pigments (hereinafter sometimes referred to as pigment (A1-2)). Hereinafter, dye (A1-1) and pigment (A1-2) may be collectively referred to as colorant (A1). These may be used alone or in combination of two or more.

[0162] The dye (A1-1) is not particularly limited as long as it does not contain the compound (I), and known dyes can be used. For example, solvent dyes, acid dyes, direct dyes, mordant dyes, etc. can be mentioned. Examples of the dye include compounds classified as dyes in the Color Index (published by The Society of Dyers and Colourists) and known dyes described in the Dyeing Notes (Color Dyeing Co., Ltd.). Also, according to the chemical structure, azo dyes, cyanine dyes, triphenylmethane dyes, xanthene dyes, anthraquinone dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, azomethine dyes, squarylium dyes, acridine dyes, styryl dyes, coumarin dyes, quinoline dyes, nitro dyes, and phthalocyanine dyes, etc. can be mentioned. Among these, organic solvent-soluble dyes are preferred.

[0163] Specifically, as the dye (A1-1), C.I. Solvent Yellow 4, 14, 15, 23, 24, 25, 38, 62, 63, 68, 79, 81, 82, 83, 89, 94, 98, 99, 117, 162, 163, 167, 189; C.I. Solvent Red 24, 45, 49, 90, 91, 111, 118, 119, 122, 124, 125, 127, 130, 132, 143, 145, 146, 150, 151, 155, 160, 168, 169, 172, 175, 181, 207, 218, 222, 227, 230, 245, 247; C.I. Solvent Orange 2, 7, 11, 15, 26, 41, 54, 56, 77, 86, 99; C.I. Solvent Violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60; C.I. Solvent Blue 4, 5, 14, 18, 35, 36, 37, 38, 44, 45, 58, 59, 59:1, 63, 67, 68, 69, 70, 78, 79, 83, 90, 94, 97, 98, 100, 101, 102, 104, 105, 111, 112, 122, 128, 132, 136, 139; C.I. Solvent Green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35; etc. C.I. Solvent Dyes, C.I. Acid Yellow 1, 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112, 113, 114, 116, 119, 123, 128, 134, 135, 138, 139, 140, 144, 150, 155, 157, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251; C.I. Acid Red 1, 4, 8, 14, 17, 18, 26, 27, 29, 31, 33, 34, 35, 37, 40, 42, 44, 50, 51, 52, 57, 66, 73, 76, 80, 87, 88, 91, 92, 94, 95, 97, 98, 103, 106, 111, 114, 129, 133, 134, 138, 143, 145, 150, 151, 155, 158, 160, 172, 176, 182, 183, 195, 198, 206, 211, 215, 216, 217, 227, 228, 249, 252, 257, 258, 260, 261, 266, 268, 270, 274, 277, 280, 281, 289, 308, 312, 315, 316, 339, 341, 345, 346, 349, 382, 383, 388, 394, 401, 412, 417, 418, 422, 426; C.I. Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 149, 162, 169, 173; C.I. Acid Violet 6B, 7, 9, 15, 16, 17, 19, 21, 23, 24, 25, 30, 34, 38, 49, 72, 102; C.I. Acid Blue 1, 3, 5, 7, 9, 11, 13, 15, 17, 18, 22, 23, 24, 25, 26, 27, 29, 34, 38, 40, 41, 42, 43, 45, 48, 51, 54, 59, 60, 62, 70, 72, 74, 75, 78, 80, 82, 83, 86, 87, 88, 90, 90:1, 91, 92, 93, 93:1, 96, 99, 100, 102, 103, 104, 108, 109, 110, 112, 113, 117, 119, 120, 123, 126, 127, 129, 130, 131, 138, 140, 142, 143, 147, 150, 151, 154, 158, 161, 166, 167, 168, 170, 171, 175, 182, 183, 184, 187, 192, 199, 203, 204, 205, 210, 213, 229, 234, 236, 242, 243, 249, 256, 259, 267, 269, 278, 280, 285, 290, 296, 315, 324:1, 335, 340; C.I. Acid Green 1, 3, 5, 6, 7, 8, 9, 11, 13, 14, 15, 16, 22, 25, 27, 28, 41, 50, 50:1, 58, 63, 65, 80, 104, 105, 106, 109; and other C.I. acid dyes, C.I. Direct Yellow 2, 4, 28, 33, 34, 35, 38, 39, 43, 44, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129, 132, 136, 138, 141; C.I. Direct Red 79, 82, 83, 84, 91, 92, 96, 97, 98, 99, 105, 106, 107, 172, 173, 176, 177, 179, 181, 182, 184, 204, 207, 211, 213, 218, 220, 221, 222, 232, 233, 234, 241, 243, 246, 250; C.I. Direct Orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107; C.I. Direct Violet 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104; C.I. Direct Blue 1, 2, 3, 6, 8, 15, 22, 25, 28, 29, 40, 41, 42, 47, 52, 55, 57, 71, 76, 77, 78, 80, 81, 84, 85, 86, 87, 90, 93, 94, 95, 97, 98, 99, 100, 101, 106, 107, 108, 109, 113, 114, 115, 117, 119, 120, 137, 149, 150, 153, 155, 156, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 168, 170, 171, 172, 173, 188, 189, 190, 192, 193, 194, 195, 196, 198, 199, 200, 201, 202, 203, 207, 209, 210, 212, 213, 214, 222, 225, 226, 228, 229, 236, 237, 238, 242, 243, 244, 245, 246, 247, 248, 249, 250, 251, 252, 256, 257, 259, 260, 268, 274, 275, 293; C.I. Direct Green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 79, 82; and other C.I. Direct dyes, C.I. Disperse Yellow 51, 54, 76; C.I. Disperse Violet 26, 27; C.I. Disperse Blue 1, 14, 56, 60; and other C.I. Disperse dyes, C.I. Basic Red 1, 9, 10; C.I. Basic Blue 1, 3, 5, 7, 9, 19, 21, 22, 24, 25, 26, 28, 29, 40, 41, 45, 47, 54, 58, 59, 60, 64, 65, 66, 67, 68, 81, 83, 88, 89; C.I. Basic Violet 2; C.I. Basic Green 1; and other C.I. Basic dyes, C.I. Reactive Yellow 2, 76, 116; C.I. Reactive Orange 16; C.I. Reactive Red 36; and other C.I. Reactive dyes, C.I. Mordant Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65; C.I. Mordant Red 1, 2, 3, 4, 9, 11, 12, 14, 17, 18, 19, 22, 23, 24, 25, 26, 27, 29, 30, 32, 33, 36, 37, 38, 39, 41, 42, 43, 45, 46, 48, 52, 53, 56, 62, 63, 71, 74, 76, 78, 85, 86, 88, 90, 94, 95; C.I. Mordant Orange 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47, 48; C.I. Mordant Violet 1, 1:1, 2, 3, 4, 5, 6, 7, 8, 10, 11, 14, 15, 16, 17, 18, 19, 21, 22, 23, 24, 27, 28, 30, 31, 32, 33, 36, 37, 39, 40, 41, 44, 45, 47, 48, 49, 53, 58; C.I. Mordant Blue 1, 2, 3, 7, 8, 9, 12, 13, 15, 16, 19, 20, 21, 22, 23, 24, 26, 30, 31, 32, 39, 40, 41, 43, 44, 48, 49, 53, 61, 74, 77, 83, 84; C.I. Mordant Green 1, 3, 4, 5, 10, 13, 15, 19, 21, 23, 26, 29, 31, 33, 34, 35, 41, 43, 53; etc. C.I. Mordant dyes, C.I. Vat Green 1; etc. C.I. Vat dyes and other dyes with Color Index (C.I.) numbers may be mentioned.

[0164] As the pigment (A1-2), as long as it does not include the compound (I), it is not particularly limited and known pigments can be used. For example, pigments classified as pigments in the Color Index (published by The Society of Dyers and Colourists) can be mentioned. Examples of pigments classified as pigments include, for example, yellow pigments such as C.I. Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 129, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 185, 194, 214, 231, etc.; Orange pigments such as C.I. Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73, etc.; Red pigments such as C.I. Pigment Red 9, 97, 105, 122, 144, 166, 168, 176, 177, 180, 190, 192, 209, 215, 216, 224, 242, 254, 255, 264, 265, 266, 268, 269, 273, etc.; Blue pigments such as C.I. Pigment Blue 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 60, etc.; Violet pigments such as C.I. Pigment Violet 1, 19, 23, 32, 36, 38, etc.; Green pigments such as C.I. Pigment Green 7, 36, 58, 59, 62, 63, etc.; Brown pigments such as C.I. Pigment Brown 23, 25, etc.; Black pigments such as C.I. Pigment Black 1, 7, etc. can be mentioned.

[0165] As the colorant (A1), yellow, red or green dyes and / or pigments are preferred.

[0166] The colorant (A1) may, if necessary, be subjected to surface treatment using rosin treatment, derivatives with acidic or basic groups introduced, etc., graft treatment of the surface of the colorant (A1) with a polymer compound, etc., micronization treatment by the sulfuric acid micronization method, etc., washing treatment with an organic solvent, water, etc. for removing impurities, removal treatment by an ion exchange method for ionic impurities, etc. The particle size of the colorant (A1) is preferably substantially uniform.

[0167] When the colorant (A) further contains the colorant (A1), the content of the compound (I) is, for example, 1% by mass or more, preferably 2% by mass or more, more preferably 10% by mass or more, still more preferably 25% by mass or more, and particularly preferably 50% by mass or more with respect to the total amount of the colorant (A). Further, when the colorant (A) further contains the colorant (A1), the content of the compound (I) is, for example, less than 100% by mass with respect to the total amount of the colorant (A).

[0168] When the colored resin composition contains the solvent (E), a colorant-containing liquid containing the colorant (A) and the solvent (E) may be prepared in advance, and then the colored resin composition may be prepared using the colorant-containing liquid. When the colorant (A) is not soluble in the solvent (E), for example, when the colorant (A) contains the pigment (A1-2), the colorant-containing liquid can be prepared by dispersing and mixing the colorant (A) in the solvent (E). The colorant-containing liquid may contain part or all of the solvent (E) contained in the colored resin composition.

[0169] The content of the solid content in the colorant-containing liquid is preferably 0.01% by mass or more and 99.99% by mass or less, more preferably 0.1% by mass or more and 99.9% by mass or less, still more preferably 0.1% by mass or more and 99% by mass or less, even more preferably 0.5% by mass or more and 90% by mass or less, and particularly preferably 1% by mass or more and 50% by mass or less with respect to the total amount of the colorant-containing liquid.

[0170] The colorant (A) may be in a state where the colorant (A) is uniformly dispersed in the solution by performing a dispersion treatment by containing a dispersant. When two or more kinds of the colorant (A) are used in combination, each may be dispersed separately, or a plurality of kinds may be mixed and dispersed.

[0171] Dispersant (P) Examples of the dispersant (P) include surfactants, and any of cationic, anionic, nonionic, and amphoteric surfactants may be used. Specifically, surfactants such as polyester-based, polyamine-based, urethane-based, and acrylic-based surfactants can be mentioned. These dispersants may be used alone or in combination of two or more. When represented by trade names, examples of the dispersant (P) include KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Floren (manufactured by Kyoeisha Chemical Co., Ltd.), Solsperse (registered trademark) (manufactured by DuPont Tate & Lyle Bio Products Company), EFKA (registered trademark) (manufactured by BASF), Ajisper (registered trademark) (manufactured by Ajinomoto Fine-Techno Co., Inc.), Disperbyk (registered trademark) (manufactured by BYK Chemie GmbH), BYK (registered trademark) (manufactured by BYK Chemie GmbH), etc. As the dispersant, the resin (B) described later may be used.

[0172] The dispersant (P) may or may not have an amino group. From the viewpoint of improving lightness and contrast, the amine value of the dispersant (P) is less than 70 mgKOH / g, preferably 0 mgKOH / g or more and 65 mgKOH / g or less, more preferably 1 mgKOH / g or more and 65 mgKOH / g or less, still more preferably 2 mgKOH / g or more and 63 mgKOH / g or less, even more preferably 3 mgKOH / g or more and 61 mgKOH / g or less, particularly preferably 5 mgKOH / g or more and 61 mgKOH / g or less, and most preferably 7 mgKOH / g or more and 59 mgKOH / g or less. When the amine value of the dispersant is 70 mgKOH / g or more, there is a risk of lowering lightness and contrast. In one aspect, from the viewpoint of further improving contrast, the amine value of the dispersant (P) is preferably 30 mgKOH / g or more and 60 mgKOH / g or less, more preferably 40 mgKOH / g or more, and still more preferably 50 mgKOH / g or more. The amine value represents the number of milligrams of potassium hydroxide equivalent to perchloric acid required to neutralize the amine component contained in 1 g of the sample, and can be measured, for example, according to JIS K7237.

[0173] When using the dispersant (P), the amount of the dispersant (solid content) used is usually 1 part by mass or more and 10,000 parts by mass or less, preferably 5 parts by mass or more and 5,000 parts by mass or less, more preferably 10 parts by mass or more and 1,000 parts by mass or less, and still more preferably 15 parts by mass or more and 800 parts by mass or less, based on 100 parts by mass of the colorant (A). When the amount of the dispersant used is within the above range, a colorant-containing liquid with a more uniform dispersion state tends to be obtained. The content rate of the dispersant (P) is preferably 1 to 30% by mass, more preferably 2 to 25% by mass, still more preferably 3 to 20% by mass, and even more preferably 5 to 20% by mass, based on the total amount of the solid content of the colored resin composition.

[0174] The content rate of the colorant (A) is preferably 0.1% by mass or more and 50% by mass or less, more preferably 0.5% by mass or more and 40% by mass or less, and still more preferably 1% by mass or more and 30% by mass or less, based on the total amount of the solid content of the colored resin composition. When the content rate of the colorant (A) is within the above range, the color density when used as a color filter is sufficient, and since the resin (B) can be contained in a necessary amount in the composition, it is possible to form a pattern with sufficient mechanical strength, which is preferable. Here, the "total amount of solid content" in this specification refers to the amount obtained by removing the content of the solvent from the total amount of the colored resin composition. The total amount of solid content and the content of each component relative thereto can be measured by known analytical means such as liquid chromatography or gas chromatography.

[0175] Phenylphosphonic acid which may have a substituent The colored resin composition of the present invention contains phenylphosphonic acid which may have a substituent. Such phenylphosphonic acid may form a salt with the dispersant and may stabilize the salt structure of the compound of formula (I), and as a result, the lightness and contrast can be improved. One kind or two or more kinds of phenylphosphonic acid which may have a substituent may be used.

[0176] The phenylphosphonic acid which may have a substituent is preferably a compound represented by the formula (X).

[0177] [Chemical formula]

[0178] [In the formula (X), R x is selected from the group consisting of a halogen atom, a hydroxy group, a substituted or unsubstituted amino group, R A , OR A , COOR B , P(O)(OR B )2, a nitro group, and a cyano group. R A represents a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent. R B represents a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent. R y represents a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent. p is 0 to 5. When p is 2 or more, R x may be the same or different.]

[0179] Examples of the hydrocarbon group having 1 to 10 carbon atoms represented by R A , R B and R y include an aliphatic hydrocarbon group and an aromatic hydrocarbon group. The aliphatic hydrocarbon group may be saturated or unsaturated, and may be linear or alicyclic.

[0180] Examples of the saturated or unsaturated chain hydrocarbon group include linear alkyl groups such as methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, and n-decyl group; branched alkyl groups such as isopropyl group, (1-ethyl)propyl group, isobutyl group, sec-butyl group, tert-butyl group, (1-ethyl)butyl group, (2-ethyl)butyl group, (1-propyl)butyl group, isopentyl group, neopentyl group, tert-pentyl group, (2-methyl)pentyl group, (1-ethyl)pentyl group, (3-ethyl)pentyl group, (1-propyl)pentyl group, (1-butyl)pentyl group, isohexyl group, (2-methyl)hexyl group, (5-methyl)hexyl group, (2-ethyl)hexyl group, (1-butyl)hexyl group, (2-methyl)heptyl group, (2-ethyl)heptyl group, (3-ethyl)heptyl group, (2-methyl)octyl group, and (2-ethyl)octyl group; alkenyl groups such as vinyl group, 1-propenyl group, 2-propenyl group (allyl group), (1-methyl)ethenyl group, 2-butenyl group, 3-butenyl group, 1,3-butadienyl group, (1-(2-propenyl))ethenyl group, (1,2-dimethyl)propenyl group, and 2-pentenyl group; etc.

[0181] Examples of the saturated or unsaturated alicyclic hydrocarbon group include cycloalkyl groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, and cyclooctyl group; cycloalkenyl groups such as cyclohexenyl group (e.g., cyclohexa-2-ene, cyclohexa-3-ene), cycloheptenyl group, and cyclooctenyl group; norbornyl group, adamantyl group, bicyclo[2.2.2]octyl group; etc.

[0182] Examples of the aromatic hydrocarbon group include aryl groups such as phenyl group, 1-naphthyl group, 2-naphthyl group; alkylaryl groups such as o-tolyl group, m-tolyl group, p-tolyl group, 2-ethylphenyl group, 3-ethylphenyl group, 4-ethylphenyl group, 2,3-dimethylphenyl group, 2,4-dimethylphenyl group, 2,5-dimethylphenyl group, 2,6-dimethylphenyl group, 3,4-dimethylphenyl group, 3,5-dimethylphenyl group, 2,4,6-trimethylphenyl group, 2-methyl-6-ethylphenyl group, 2,6-diethylphenyl group, o-isopropylphenyl group, m-isopropylphenyl group, p-isopropylphenyl group, 2-methyl-6-isopropylphenyl group, 4-butylphenyl group, o-tert-butylphenyl group, m-tert-butylphenyl group, p-tert-butylphenyl group; alkenylaryl groups such as 4-vinylphenyl group; and the like.

[0183] As long as the upper limit of the number of carbon atoms is 10, the hydrocarbon group having 1 to 10 carbon atoms may be a group formed by combining two or more of the chain hydrocarbon groups, alicyclic hydrocarbon groups, and aromatic hydrocarbon groups listed above. Such groups include, for example, aralkyl groups such as benzyl group, phenethyl group, 1-methyl-1-phenylethyl group; arylalkenyl groups such as phenylethenyl group (phenylvinyl group); arylalkynyl groups such as phenylethynyl group; 1-methylcyclopropyl group, 1-methylcyclohexyl group, 2-methylcyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 1,2-dimethylcyclohexyl group, 1,3-dimethylcyclohexyl group, 1,4-dimethylcyclohexyl group, 2,3-dimethylcyclohexyl group, 2,4-dimethylcyclohexyl group, 2,5-dimethylcyclohexyl group, 2,6-dimethylcyclohexyl group, 3,4-dimethylcyclohexyl group, 3,5-dimethylcyclohexyl group, 2,2-dimethylcyclohexyl group, 3,3-dimethylcyclohexyl group, 4,4-dimethylcyclohexyl group, 2,4,6-trimethylcyclohexyl group, 2,2,6,6-tetramethylcyclohexyl group, 3,3,5,5-tetramethylcyclohexyl group, etc., which are alicyclic hydrocarbon groups to which one or more alkyl groups or alicyclic hydrocarbon groups are bonded; alkyl groups to which one or more alicyclic hydrocarbon groups such as cyclopropylmethyl group, cyclopropylethyl group, cyclobutylmethyl group, cyclobutylethyl group, cyclopentylmethyl group, cyclopentylethyl group, cyclohexylmethyl group, 2-methylcyclohexylmethyl group, cyclohexylethyl group are bonded; and the like.

[0184] Examples of the substituted amino group include amino groups having one or two hydrocarbon groups, and examples of the hydrocarbon group include the groups exemplified as the hydrocarbon groups having 1 to 10 carbon atoms described above. Examples of the substituted amino group include, for example, N-methylamino group, N,N-dimethylamino group, N-ethylamino group, N,N-diethylamino group, N-propylamino group, N,N-dipropylamino group, N-isopropylamino group, N,N-diisopropylamino group, N-phenylamino group, N,N-diphenylamino group, N,N-ethylmethylamino group, N,N-methylphenylamino group, N,N-ethylphenylamino group, and the like.

[0185] R x The halogen atom represented by x is, for example, a bromine atom, a chlorine atom, a fluorine atom, or an iodine atom, preferably a bromine atom, a chlorine atom, or a fluorine atom, more preferably a bromine atom or a chlorine atom, and even more preferably a bromine atom.

[0186] Examples of the substituent that the hydrocarbon group having 1 to 10 carbon atoms may have include at least one or more selected from the group consisting of a halogen atom, a hydroxy group, a carboxyl group, an alkoxy group, a formyl group, a substituted or unsubstituted amino group, a nitro group, and a cyano group.

[0187] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Examples of the alkoxy group include alkoxy groups having 1 to 4 carbon atoms such as a methoxy group, an ethoxy group, a propoxy group, and a butoxy group. Examples of the substituted amino group include those similar to those exemplified as the substituted amino group of R x x .

[0188] R A R B R y The number of carbon atoms of the hydrocarbon group represented by A , B , and y is preferably 1 to 8, more preferably 1 to 6, even more preferably 1 to 4, and even more preferably 1 or 2.

[0189] Among them, RA and R B is preferably an aliphatic hydrocarbon group having 1 to 8 carbon atoms, more preferably an aliphatic hydrocarbon group having 1 to 4 carbon atoms, and even more preferably a methyl group or an ethyl group. R y is preferably a hydrogen atom.

[0190] R x is a halogen atom, a hydroxy group, a substituted or unsubstituted amino group, OR A , COOR B , and P(O)(OR B )2, and is preferably selected from the group consisting of a halogen atom, a substituted or unsubstituted amino group, OR A , COOR B , and P(O)(OR B )2. COOR B and P(O)(OR B )2, R B is preferably a hydrogen atom. R x is preferably a halogen atom from the viewpoint of higher brightness, and is preferably P(O)(OR B )2 from the viewpoints of higher brightness and contrast. R x When there is one, the substitution position of R x may be any of the ortho position, para position, and meta position with respect to -P(O)(OH)(OR y ) bonded to the phenyl ring, and the para position and meta position are preferred.

[0191] p is preferably 0 to 4, more preferably 0 to 3, even more preferably 0, 1 or 2, and even more preferably 0 or 1.

[0192] Examples of the compound represented by the formula (X) include compounds represented by the following formula (X-1) to formula (X-22).

[0193]

Chemical formula

[0194] Among the compounds represented by Formula (X-1) to Formula (X-22), the compound represented by Formula (X-1), the compound represented by Formula (X-4), the compound represented by Formula (X-6), the compound represented by Formula (X-11), the compound represented by Formula (X-12), and the compound represented by Formula (X-13) are particularly preferred.

[0195] The content of phenylphosphonic acid which may have a substituent is preferably 1 to 100 parts by mass, more preferably 2 to 80 parts by mass, still more preferably 3 to 60 parts by mass, and even more preferably 4 to 40 parts by mass with respect to 100 parts by mass of the colorant. The content of phenylphosphonic acid which may have a substituent is preferably 1 to 50 parts by mass, more preferably 2 to 40 parts by mass, still more preferably 3 to 30 parts by mass, and even more preferably 4 to 25 parts by mass with respect to 100 parts by mass of the dispersant.

[0196] The content ratio of phenylphosphonic acid which may have a substituent is preferably 0.1 to 10% by mass, more preferably 0.2 to 8% by mass, still more preferably 0.3 to 6% by mass, and even more preferably 0.4 to 4% by mass with respect to the solid content of the colored resin composition.

[0197] <Resin (B)> Resin (B) is not particularly limited, but is preferably an alkali-soluble resin. Examples of Resin (B) include the following resins [K1] to [K6] and the like. Resin [K1]; a copolymer having a structural unit derived from at least one monomer (a) (hereinafter sometimes referred to as "(a)") selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic acid anhydrides, and a structural unit derived from a monomer (b) (hereinafter sometimes referred to as "(b)") having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond; Resin [K2]; a copolymer having a structural unit derived from (a), a structural unit derived from (b), and a structural unit derived from a monomer (c) copolymerizable with (a) (where (c) is different from (a) and (b), hereinafter sometimes referred to as "(c)"); Resin [K3]; a copolymer having a structural unit derived from (a) and a structural unit derived from (c); Resin [K4]; a copolymer having a structural unit obtained by adding (b) to a structural unit derived from (a) and a structural unit derived from (c); Resin [K5]; a copolymer having a structural unit obtained by adding (a) to a structural unit derived from (b) and a structural unit derived from (c); Resin [K6]; a copolymer having a structural unit obtained by adding (a) to a structural unit derived from (b) and further adding a carboxylic anhydride and a structural unit derived from (c).

[0198] Examples of the monomer (a) include unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, and o-, m-, p-vinylbenzoic acid; unsaturated dicarboxylic acids such as maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyltetrahydrophthalic acid, and 1,4-cyclohexenedicarboxylic acid; bicyclic unsaturated compounds containing a carboxy group such as methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo[2.2.1]hept-2-ene, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene, 5-carboxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-carboxy-6-methylbicyclo[2.2.1]hept-2-ene, and 5-carboxy-6-ethylbicyclo[2.2.1]hept-2-ene; carboxylic anhydrides such as anhydrides of the above unsaturated dicarboxylic acids excluding fumaric acid and mesaconic acid; Unsaturated mono[(meth)acryloyloxyalkyl] esters of polyvalent carboxylic acids having two or more valences, such as monosuccinate [2-(meth)acryloyloxyethyl] and monophthalate [2-(meth)acryloyloxyethyl]; Unsaturated acrylates containing a hydroxy group and a carboxy group in the same molecule, such as α-(hydroxymethyl)acrylic acid; etc. may be mentioned. Among these, from the viewpoints of copolymerization reactivity and solubility of the resulting resin in an aqueous alkali solution, acrylic acid, methacrylic acid, maleic anhydride, etc. are preferable. In this specification, “(meth)acrylic acid” represents at least one selected from the group consisting of acrylic acid and methacrylic acid. Expressions such as “(meth)acryloyl” and “(meth)acrylate” also have the same meaning.

[0199] Monomer (b) refers to a polymerizable compound having a cyclic ether structure having 2 to 4 carbon atoms (for example, at least one selected from the group consisting of an oxirane ring, an oxetane ring, and a tetrahydrofuran ring (oxolane ring)) and an ethylenically unsaturated bond. Monomer (b) is preferably a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth)acryloyloxy group.

[0200] Examples of monomer (b) include monomers having an oxiranyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as “monomer (b1)”), monomers having an oxetanyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as “monomer (b2)”), monomers having a tetrahydrofuryl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as “monomer (b3)”), and the like.

[0201] Examples of monomer (b1) include monomers having a structure obtained by epoxidizing an unsaturated aliphatic hydrocarbon (hereinafter sometimes referred to as “monomer (b1-1)”), and monomers having a structure obtained by epoxidizing an unsaturated alicyclic hydrocarbon (hereinafter sometimes referred to as “monomer (b1-2)”).

[0202] As the monomer (b1-1), a monomer having a glycidyl group and an ethylenically unsaturated bond is preferable. Specific examples of the monomer (b1-1) include glycidyl (meth) acrylate, β-methyl glycidyl (meth) acrylate, β-ethyl glycidyl (meth) acrylate, glycidyl vinyl ether, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether, α-methyl-o-vinylbenzyl glycidyl ether, α-methyl-m-vinylbenzyl glycidyl ether, α-methyl-p-vinylbenzyl glycidyl ether, 2,3-bis(glycidyloxymethyl)styrene, 2,4-bis(glycidyloxymethyl)styrene, 2,5-bis(glycidyloxymethyl)styrene, 2,6-bis(glycidyloxymethyl)styrene, 2,3,4-tris(glycidyloxymethyl)styrene, 2,3,5-tris(glycidyloxymethyl)styrene, 2,3,6-tris(glycidyloxymethyl)styrene, 3,4,5-tris(glycidyloxymethyl)styrene, 2,4,6-tris(glycidyloxymethyl)styrene, and the like.

[0203] Examples of the monomer (b1-2) include vinylcyclohexene monooxide, 1,2-epoxy-4-vinylcyclohexane (e.g., Celoxide (registered trademark) 2000; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth) acrylate (e.g., Cyclomer (registered trademark) A400; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth) acrylate (e.g., Cyclomer (registered trademark) M100; manufactured by Daicel Corporation), a compound represented by formula (BI), and a compound represented by formula (BII).

[0204] [Chemical formula]

[0205] [In formula (BI) and formula (BII), R a and R bEach independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the hydrogen atom contained in the alkyl group may be substituted with a hydroxy group. X a and X b Each independently represents a single bond, *-R c -, *-R c -O-, *-R c -S- or *-R c -NH-. R c represents an alkanediyl group having 1 to 6 carbon atoms. * represents a bond to O.

[0206] Examples of the alkyl group having 1 to 4 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, a tert-butyl group, and the like.

[0207] Examples of the alkyl group in which the hydrogen atom is substituted with a hydroxy group include a hydroxymethyl group, a 1-hydroxyethyl group, a 2-hydroxyethyl group, a 1-hydroxypropyl group, a 2-hydroxypropyl group, a 3-hydroxypropyl group, a 1-hydroxy-1-methylethyl group, a 2-hydroxy-1-methylethyl group, a 1-hydroxybutyl group, a 2-hydroxybutyl group, a 3-hydroxybutyl group, a 4-hydroxybutyl group, and the like.

[0208] R a and R b Preferably include a hydrogen atom, a methyl group, a hydroxymethyl group, a 1-hydroxyethyl group, a 2-hydroxyethyl group, more preferably a hydrogen atom, a methyl group.

[0209] Examples of the alkanediyl group include a methylene group, an ethylene group, a propane-1,2-diyl group, a propane-1,3-diyl group, a butane-1,4-diyl group, a pentane-1,5-diyl group, a hexane-1,6-diyl group, and the like.

[0210] X a and X bExamples thereof preferably include a single bond, a methylene group, an ethylene group, a *-CH2-O-* group (where * represents a bond to O), and a *-CH2CH2-O-* group, and more preferably include a single bond and a *-CH2CH2-O-* group (where * represents a bond to O).

[0211] Examples of the compound represented by formula (BI) include compounds represented by any of formula (BI-1) to formula (BI-15). Among them, compounds represented by formula (BI-1), formula (BI-3), formula (BI-5), formula (BI-7), formula (BI-9), and formula (BI-11) to formula (BI-15) are preferred, and compounds represented by formula (BI-1), formula (BI-7), formula (BI-9), and formula (BI-15) are more preferred.

[0212]

Chemical formula

[0213] Examples of the compound represented by formula (BII) include compounds represented by any of formula (BII-1) to formula (BII-15). Among them, compounds represented by formula (BII-1), formula (BII-3), formula (BII-5), formula (BII-7), formula (BII-9), and formula (BII-11) to formula (BII-15) are preferred, and compounds represented by formula (BII-1), formula (BII-7), formula (BII-9), and formula (BII-15) are more preferred.

[0214]

Chemical formula

[0215] The compound represented by formula (BI) and the compound represented by formula (BII) may be used alone or in combination. When used in combination, the content ratio of the compound represented by formula (BI) and the compound represented by formula (BII) is preferably 5:95 to 95:5, more preferably 10:90 to 90:10, and still more preferably 20:80 to 80:20 on a molar basis.

[0216] As the monomer (b2) having an oxetanyl group and an ethylenically unsaturated bond, a monomer having an oxetanyl group and a (meth)acryloyloxy group is more preferable. Examples of the monomer (b2) include 3-methyl-3-((meth)acryloyloxymethyl)oxetane, 3-ethyl-3-((meth)acryloyloxymethyl)oxetane, 3-methyl-3-((meth)acryloyloxyethyl)oxetane, 3-ethyl-3-((meth)acryloyloxyethyl)oxetane, and the like.

[0217] As the monomer (b3) having a tetrahydrofuryl group and an ethylenically unsaturated bond, a monomer having a tetrahydrofuryl group and a (meth)acryloyloxy group is more preferable. Examples of the monomer (b3) include tetrahydrofurfuryl acrylate (for example, Biscoat V#150, manufactured by Osaka Organic Chemical Industry Co., Ltd.), tetrahydrofurfuryl methacrylate, and the like.

[0218] Examples of the monomer (c) include methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, sec-butyl (meth)acrylate, tert-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, dodecyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, cyclopentyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, tricyclo[5.2.1.0 2,6 dec-8-yl (meth)acrylate (in the art, it is commonly referred to as "dicyclopentanyl (meth)acrylate". It may also be referred to as "tricyclodecyl (meth)acrylate"), tricyclo[5.2.1.0 2,6 dec-9-yl (meth)acrylate, tricyclo[5.2.1.0 2,6 dec-8-en-8-yl (meth)acrylate (in the art, it is commonly referred to as "dicyclopentenyl (meth)acrylate"), tricyclo[5.2.1.0 2,6(Meth)acrylic acid esters such as decen-9-yl (meth)acrylate, dicyclopentanyloxyethyl (meth)acrylate, isobornyl (meth)acrylate, adamantyl (meth)acrylate, allyl (meth)acrylate, propargyl (meth)acrylate, phenyl (meth)acrylate, naphthyl (meth)acrylate, and benzyl (meth)acrylate; Hydroxy group-containing (meth)acrylic acid esters such as 2-hydroxyethyl (meth)acrylate and 2-hydroxypropyl (meth)acrylate; Dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate, and diethyl itaconate; Bicyclic unsaturated compounds such as bicyclo[2.2.1]hept-2-ene, 5-methylbicyclo[2.2.1]hept-2-ene, 5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxybicyclo[2.2.1]hept-2-ene, 5-hydroxymethylbicyclo[2.2.1]hept-2-ene, 5-(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5-methoxybicyclo[2.2.1]hept-2-ene, 5-ethoxybicyclo[2.2.1]hept-2-ene, 5,6-dihydroxybicyclo[2.2.1]hept-2-ene, 5,6-di(hydroxymethyl)bicyclo[2.2.1]hept-2-ene, 5,6-di(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5,6-dimethoxybicyclo[2.2.1]hept-2-ene, 5,6-diethoxybicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxymethyl-5-methylbicyclo[2.2.1]hept-2-ene, 5-tert-butoxycarbonylbicyclo[2.2.1]hept-2-ene, 5-cyclohexyloxycarbonylbicyclo[2.2.1]hept-2-ene, 5-phenoxycarbonylbicyclo[2.2.1]hept-2-ene, 5,6-bis(tert-butoxycarbonyl)bicyclo[2.2.1]hept-2-ene, and 5,6-bis(cyclohexyloxycarbonyl)bicyclo[2.2.1]hept-2-ene; Dicarbonylimide derivatives such as N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl 3-maleimidobenzoate, N-succinimidyl 4-maleimidobutyrate, N-succinimidyl 6-maleimidocaproate, N-succinimidyl 3-maleimidopropionate, and N-(9-acridinyl)maleimide; Vinyl group-containing aromatic compounds such as styrene, o-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, and p-methoxystyrene; vinyl group-containing nitriles such as (meth)acrylonitrile; halogenated hydrocarbons such as vinyl chloride and vinylidene chloride; vinyl group-containing amides such as (meth)acrylamide; esters such as vinyl acetate; dienes such as 1,3-butadiene, isoprene, and 2,3-dimethyl-1,3-butadiene; and the like. Among these, from the viewpoints of copolymerization reactivity and heat resistance, styrene, vinyltoluene, tricyclo[5.2.1.0 2,6 decane-8-yl (meth)acrylate, tricyclo[5.2.1.0 2,6 decane-9-yl (meth)acrylate, tricyclo[5.2.1.0 2,6 decene-8-yl (meth)acrylate, tricyclo[5.2.1.0 2,6 decene-9-yl (meth)acrylate, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo[2.2.1]hept-2-ene, 2-hydroxyethyl (meth)acrylate, and benzyl (meth)acrylate, it is preferable to use at least one selected from the group consisting of them.

[0219] In resin [K1], the ratio of the structural units derived therefrom is among all the structural units constituting resin [K1], Structural units derived from (a); 2 to 60 mol% Structural units derived from (b); 40 to 98 mol% It is preferably such that, Structural units derived from (a); 10 to 50 mol% The structural unit derived from (b); 50 to 90 mol% is more preferably. When the ratio of the structural unit of the resin [K1] is within the above range, the storage stability of the colored resin composition, the developability when forming a colored pattern, and the solvent resistance of the resulting color filter tend to be excellent.

[0220] The resin [K1] can be produced, for example, with reference to the methods described in the literature "Experimental Methods of Polymer Synthesis" (written by Takayuki Otsu, published by Kagaku Dojin Publishing Co., Ltd., 1st edition, 1st printing, issued on March 1, 1972) and the cited references described in the literature.

[0221] Specifically, a method of putting predetermined amounts of (a) and (b), a polymerization initiator, a solvent, etc. into a reaction vessel, replacing oxygen with nitrogen, for example, to create a deoxygenated atmosphere, and heating and keeping warm while stirring can be mentioned. The polymerization initiator, solvent, etc. used here are not particularly limited, and those commonly used in the art can be used. For example, as the polymerization initiator, azo compounds (2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), etc.) and organic peroxides (benzoyl peroxide, etc.) can be mentioned, and as the solvent, any one that can dissolve each monomer may be used, and solvents such as those described later as the solvent (E) of the colored resin composition of the present invention can be mentioned.

[0222] The obtained copolymer may be used as the reaction solution as it is, or a concentrated or diluted solution may be used, or a solid (powder) taken out by a method such as reprecipitation may be used. In particular, by using the solvent contained in the colored resin composition of the present invention as the solvent during this polymerization, the reaction solution can be used as it is for the preparation of the colored resin composition of the present invention, so the manufacturing process of the colored resin composition of the present invention can be simplified.

[0223] In the resin [K2], the ratio of the structural unit derived from each is among all the structural units constituting the resin [K2], The structural unit derived from (a); 2 to 45 mol% Structural units derived from (b); 2 to 95 mol% Structural units derived from (c); 1 to 65 mol% It is preferably Structural units derived from (a); 5 to 40 mol% Structural units derived from (b); 5 to 80 mol% Structural units derived from (c); 5 to 60 mol% more preferably When the ratio of the structural units of resin [K2] is within the above range, the storage stability of the colored resin composition, the developability when forming a colored pattern, and the solvent resistance, heat resistance, and mechanical strength of the resulting color filter tend to be excellent.

[0224] Resin [K2] can be produced, for example, in the same manner as the method described for the production method of resin [K1].

[0225] In resin [K3], the ratio of the structural units derived therefrom is among all the structural units constituting resin [K3], Structural units derived from (a); 2 to 60 mol% Structural units derived from (c); 40 to 98 mol% It is preferably Structural units derived from (a); 10 to 50 mol% Structural units derived from (c); 50 to 90 mol% more preferably Resin [K3] can be produced, for example, in the same manner as the method described for the production method of resin [K1].

[0226] Resin [K4] can be produced by obtaining a copolymer of (a) and (c) and adding the cyclic ether having 2 to 4 carbon atoms that (b) has to the carboxylic acid and / or carboxylic anhydride that (a) has. First, a copolymer of (a) and (c) is produced in the same manner as the method described for the production method of resin [K1]. In this case, the ratio of the structural units derived therefrom is preferably the same ratio as that mentioned for resin [K3].

[0227] Next, a cyclic ether having 2 to 4 carbon atoms in (b) is reacted with a part of the carboxylic acid and / or carboxylic anhydride derived from (a) in the copolymer. Subsequent to the production of the copolymer of (a) and (c), the atmosphere in the flask is replaced from nitrogen to air, and (b), a reaction catalyst for the reaction between the carboxylic acid or carboxylic anhydride and the cyclic ether (for example, tris(dimethylaminomethyl)phenol, etc.) and a polymerization inhibitor (for example, hydroquinone, etc.) are put into the flask, and then, for example, reacted at 60 to 130 °C for 1 to 10 hours to produce resin [K4]. The amount of (b) used is preferably 5 to 80 moles, more preferably 10 to 75 moles, per 100 moles of (a). By setting it within this range, the storage stability of the colored resin composition, the developability when forming a pattern, and the balance of the solvent resistance, heat resistance, mechanical strength, and sensitivity of the obtained pattern tend to be good. Since the reactivity of the cyclic ether is high and unreacted (b) hardly remains, (b1) is preferable as (b) used for resin [K4], and (b1-1) is more preferable. The amount of the reaction catalyst used is preferably 0.001 to 5 parts by mass with respect to 100 parts by mass of the total amount of (a), (b), and (c). The amount of the polymerization inhibitor used is preferably 0.001 to 5 parts by mass with respect to 100 parts by mass of the total amount of (a), (b), and (c). Reaction conditions such as the charging method, reaction temperature, and time can be appropriately adjusted in consideration of the production equipment, the heat generation amount due to polymerization, etc. Similar to the polymerization conditions, the charging method and reaction temperature can be appropriately adjusted in consideration of the production equipment, the heat generation amount due to polymerization, etc.

[0228] As a first step, resin [K5] is obtained in the same manner as the production method of resin [K1] described above to obtain a copolymer of (b) and (c). Similar to the above, the obtained copolymer may be used as the reaction solution as it is, or a concentrated or diluted solution may be used, or a solid (powder) taken out by a method such as reprecipitation may be used. (b) and (c) the ratio of the structural units derived from, with respect to the total number of moles of all structural units constituting the copolymer, respectively, Structural units derived from (b); 5 to 95 mol% Structural units derived from (c); 5 to 95 mol% It is preferably that, Structural units derived from (b); 10 to 90 mol% Structural units derived from (c); 10 to 90 mol% It is more preferably that.

[0229] Furthermore, under the same conditions as the production method of resin [K4], by reacting the carboxylic acid or carboxylic anhydride of (a) with the cyclic ether derived from (b) in the copolymer of (b) and (c), resin [K5] can be obtained. The amount of (a) used for reacting with the copolymer is preferably 5 to 80 moles with respect to 100 moles of (b). Since the cyclic ether has high reactivity and unreacted (b) hardly remains, (b1) is preferable as (b) used for resin [K5], and (b1-1) is more preferable.

[0230] Resin [K6] is a resin obtained by further reacting a carboxylic anhydride with resin [K5]. The carboxylic anhydride is reacted with the hydroxy group generated by the reaction of the cyclic ether and the carboxylic acid or carboxylic anhydride. Examples of the carboxylic anhydride include maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride and the like. The amount of the carboxylic anhydride used is preferably 0.5 to 1 mole with respect to 1 mole of the amount of (a) used.

[0231] Specific examples of resin (B) include 3,4-epoxycyclohexylmethyl (meth)acrylate / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.02,6 Resins such as decyl acrylate / (meth)acrylic acid copolymer [K1]; glycidyl (meth)acrylate / benzyl (meth)acrylate / (meth)acrylic acid copolymer, glycidyl (meth)acrylate / styrene / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 decyl acrylate / (meth)acrylic acid / N-cyclohexylmaleimide copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 Resins such as decyl acrylate / (meth)acrylic acid / N-cyclohexylmaleimide / 2-hydroxyethyl (meth)acrylate copolymer, 3-methyl-3-(meth)acryloyloxymethyloxetane / (meth)acrylic acid / styrene copolymer [K2]; resins such as benzyl (meth)acrylate / (meth)acrylic acid copolymer, styrene / (meth)acrylic acid copolymer [K3]; resins such as resins obtained by adding glycidyl (meth)acrylate to benzyl (meth)acrylate / (meth)acrylic acid copolymer, resins obtained by adding glycidyl (meth)acrylate to tricyclodecyl (meth)acrylate / styrene / (meth)acrylic acid copolymer, resins obtained by adding glycidyl (meth)acrylate to tricyclodecyl (meth)acrylate / benzyl (meth)acrylate / (meth)acrylic acid copolymer [K4]; resins such as resins obtained by reacting (meth)acrylic acid with a copolymer of tricyclodecyl (meth)acrylate / glycidyl (meth)acrylate, resins obtained by reacting (meth)acrylic acid with a copolymer of tricyclodecyl (meth)acrylate / styrene / glycidyl (meth)acrylate [K5]; resins such as resins obtained by further reacting tetrahydrophthalic anhydride with a resin obtained by reacting (meth)acrylic acid with a copolymer of tricyclodecyl (meth)acrylate / glycidyl (meth)acrylate [K6], etc. are mentioned.

[0232] It is more preferable that the resin (B) is at least one selected from the group consisting of the resin [K1] and the resin [K2], and particularly preferably the resin [K2].

[0233] The weight average molecular weight (Mw) of the resin (B) in terms of polystyrene is preferably 1,000 or more and 100,000 or less, more preferably 2,000 or more and 50,000 or less, and still more preferably 3,000 or more and 30,000 or less. When the weight average molecular weight is within the above range, the solubility of the unexposed portion in the developer is high, and the remaining film ratio and hardness of the resulting pattern tend to be high. The dispersity [weight average molecular weight (Mw) / number average molecular weight (Mn)] of the resin (B) is preferably 1 or more and 6 or less, more preferably 1.001 or more and 4 or less, and still more preferably 1.01 or more and 4 or less.

[0234] The acid value (value in terms of solid content) of the resin (B) is preferably 10 mg-KOH / g or more and 300 mg-KOH / g or less, more preferably 20 mg-KOH / g or more and 250 mg-KOH / g or less, still more preferably 25 mg-KOH / g or more and 200 mg-KOH / g or less, even more preferably 30 mg-KOH / g or more and 150 mg-KOH / g or less, and particularly preferably 60 mg-KOH / g or more and 135 mg-KOH / g or less. Here, the acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of the resin, and can be determined, for example, by titration using an aqueous potassium hydroxide solution.

[0235] The content of the resin (B) is preferably 5 to 50% by mass, more preferably 10 to 40% by mass, and still more preferably 15 to 30% by mass in 100% by mass of the solid content of the colored resin composition. When the content of the resin (B) is within the above range, the solubility of the unexposed portion in the developer tends to be high.

[0236] <Polymerizable compound (C)> The polymerizable compound (C) is a compound that can be polymerized by active radicals and / or acids generated from the polymerization initiator (D), and examples thereof include compounds having a polymerizable ethylenically unsaturated bond, and preferably (meth)acrylic acid ester compounds.

[0237] Examples of the polymerizable compound having one ethylenically unsaturated bond include nonylphenyl carbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexyl carbitol acrylate, 2-hydroxyethyl acrylate, N-vinylpyrrolidone, etc., and the above-mentioned monomer (a), monomer (b) and monomer (c).

[0238] Examples of the polymerizable compound having two ethylenically unsaturated bonds include 1,6-hexanediol di(meth)acrylate, ethylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, bis(acryloyloxyethyl) ether of bisphenol A, and 3-methylpentanediol di(meth)acrylate, etc.

[0239] The polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds. Examples of such polymerizable compounds include trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, tripentaerythritol octa(meth)acrylate, tripentaerythritol hepta(meth)acrylate, tetrapentaerythritol deca(meth)acrylate, tetrapentaerythritol nona(meth)acrylate, tris(2-(meth)acryloyloxyethyl) isocyanurate, ethylene glycol-modified pentaerythritol tetra(meth)acrylate, ethylene glycol-modified dipentaerythritol hexa(meth)acrylate, propylene glycol-modified pentaerythritol tetra(meth)acrylate, propylene glycol-modified dipentaerythritol hexa(meth)acrylate, caprolactone-modified pentaerythritol tetra(meth)acrylate, and caprolactone-modified dipentaerythritol hexa(meth)acrylate. Preferably, at least one selected from the group consisting of dipentaerythritol penta(meth)acrylate and dipentaerythritol hexa(meth)acrylate is included.

[0240] The weight average molecular weight of the polymerizable compound (C) is preferably 50 or more and 4,000 or less, more preferably 70 or more and 3,500 or less, still more preferably 100 or more and 3,000 or less, even more preferably 150 or more and 2,900 or less, and particularly preferably 250 or more and 1,500 or less.

[0241] The content of the polymerizable compound (C) may be, for example, 1% by mass or more and 99% by mass or less, preferably 5% by mass or more and 90% by mass or less, more preferably 10% by mass or more and 80% by mass or less, and still more preferably 12% by mass or more and 70% by mass or less, based on the total solid content of the colored resin composition.

[0242] <Coinitiator (D)> The coinitiator (D) is not particularly limited as long as it is a compound that can generate active radicals, acids, etc. by the action of light or heat and initiate polymerization, and known polymerization initiators can be used.

[0243] Examples of the coinitiator (D) include O-acyl oxime compounds, alkylphenone compounds, biimidazole compounds, triazine compounds, and acylphosphine oxide compounds.

[0244] Examples of the O-acyl oxime compound include N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine, N-acetoxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine, N-acetoxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethan-1-imine, N-acetoxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethyl-2,4-dioxacyclopentanylmethyloxy)benzoyl}-9H-carbazol-3-yl]ethan-1-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropan-1-imine, and N-benzoyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropan-1-one-2-imine. Further, as the O-acyl oxime compound, commercially available products such as Irgacure (registered trademark) OXE01, OXE02 (both manufactured by BASF), N-1919 (manufactured by ADEKA Corporation), and TR-PBG327 (manufactured by Changzhou Qiangli Electronic New Materials Co., Ltd.) may be used.Among them, as the O-acyl oxime compound, at least one selected from the group consisting of N-benzoyloxy-1-(4-phenylsulfanylphenyl)butane-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octane-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropane-1-one-2-imine, and TR-PBG327 (N-acetoxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropane-1-one-2-imine) is preferable, and at least one selected from the group consisting of N-benzoyloxy-1-(4-phenylsulfanylphenyl)octane-1-one-2-imine and TR-PBG327 (N-acetoxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropane-1-one-2-imine) is more preferable.

[0245] Examples of the alkylphenone compound include 2-methyl-2-morpholino-1-(4-methylsulfanylphenyl)propan-1-one, 2-dimethylamino-1-(4-morpholinophenyl)-2-benzylbutan-1-one, and 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]butan-1-one. As the alkylphenone compound, commercially available products such as Irgacure (registered trademark) 369, 907, 379 (manufactured by BASF) may be used. Examples of the alkylphenone compound also include 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy)phenyl]propan-1-one, 1-hydroxycyclohexyl phenyl ketone, an oligomer of 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propan-1-one, α,α-diethoxyacetophenone, and benzyl dimethyl ketal.

[0246] Examples of the biimidazole compounds include 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3-dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole (see, for example, JP-A-6-75372 and JP-A-6-75373), 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(alkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(dialkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(trialkoxyphenyl)biimidazole (see, for example, JP-B-48-38403 and JP-A-62-174204), and biimidazole compounds in which the phenyl groups at the 4,4',5,5'-positions are substituted with carboxyalkoxy groups (see, for example, JP-A-7-10913), etc.

[0247] Examples of the triazine compounds include 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxynaphthyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxystyryl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(5-methylfuran-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl)ethenyl]-1,3,5-triazine, and 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)ethenyl]-1,3,5-triazine, etc.

[0248] Examples of the acylphosphine oxide compound include 2,4,6-trimethylbenzoyldiphenylphosphine oxide. Commercially available products such as Irgacure (registered trademark) 819 (manufactured by BASF) may also be used.

[0249] Furthermore, examples of the polymerization initiator (D) include benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether; benzophenone compounds such as benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, 3,3',4,4'-tetra(tert-butylperoxycarbonyl)benzophenone, and 2,4,6-trimethylbenzophenone; quinone compounds such as 9,10-phenanthrenequinone, 2-ethylanthraquinone, and camphorquinone; 10-butyl-2-chloroacridone, benzyl, methyl phenylglyoxylate, and titanocene compounds. These are preferably used in combination with the polymerization initiation aid (D1) (particularly an amine compound) described below.

[0250] The polymerization initiator (D) is preferably a polymerization initiator containing at least one selected from the group consisting of an alkylphenone compound, a triazine compound, an acylphosphine oxide compound, an O-acyl oxime compound, and a biimidazole compound, and more preferably a polymerization initiator containing an O-acyl oxime compound.

[0251] The content of the polymerization initiator (D) is preferably 0.1 part by mass or more and 30 parts by mass or less, more preferably 1 part by mass or more and 20 parts by mass or less, based on 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C) contained in the colored resin composition. When the content of the polymerization initiator (D) is within the above range, the sensitivity tends to increase and the exposure time tends to be shortened, so the productivity of the color filter is improved.

[0252] <Polymerization initiation aid (D1)> The colored resin composition of the present invention may contain a polymerization initiation aid (D1). The polymerization initiation aid (D1) is a compound or a sensitizer used to promote the polymerization of a polymerizable compound (C) whose polymerization has been initiated by a polymerization initiator (D). When the polymerization initiation aid (D1) is included, it is usually used in combination with the polymerization initiator (D).

[0253] Examples of the polymerization initiation aid (D1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds, carboxylic acid compounds, and the like.

[0254] Examples of the amine compound include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 2-ethylhexyl 4-dimethylaminobenzoate, N,N-dimethyl-p-toluidine, 4,4'-bis(dimethylamino)benzophenone (commonly known as Michler's ketone), 4,4'-bis(diethylamino)benzophenone, and 4,4'-bis(ethylmethylamino)benzophenone. Preferably, 4,4'-bis(diethylamino)benzophenone is mentioned. Further, as the amine compound, commercially available products such as EAB-F (manufactured by Hodogaya Chemical Co., Ltd.) may be used.

[0255] Examples of the alkoxyanthracene compound include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene, 9,10-dibutoxyanthracene, and 2-ethyl-9,10-dibutoxyanthracene.

[0256] Examples of the thioxanthone compound include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, and 1-chloro-4-propoxythioxanthone.

[0257] Examples of the carboxylic acid compound include phenylsulfanylacetic acid, methylphenylsulfanylacetic acid, ethylphenylsulfanylacetic acid, methylethylphenylsulfanylacetic acid, dimethylphenylsulfanylacetic acid, methoxyphenylsulfanylacetic acid, dimethoxyphenylsulfanylacetic acid, chlorophenylsulfanylacetic acid, dichlorophenylsulfanylacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, and naphthoxyacetic acid.

[0258] When using these polymerization initiation aids (D1), the content is preferably 0.1 part by mass or more and 30 parts by mass or less, more preferably 1 part by mass or more and 20 parts by mass or less, based on 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C) contained in the colored resin composition.

[0259] <Solvent (E)> The solvent (E) is not particularly limited, and solvents commonly used in the art can be used. Examples of the solvent (E) include ester solvents (solvents containing -COO- in the molecule and not containing -O-), ether solvents (solvents containing -O- in the molecule and not containing -COO-), ether ester solvents (solvents containing -COO- and -O- in the molecule), ketone solvents (solvents containing -CO- in the molecule and not containing -COO-), alcohol solvents (solvents containing OH in the molecule and not containing -O-, -CO-, and -COO-), aromatic hydrocarbon solvents, amide solvents, dimethyl sulfoxide, and the like. These solvents may be used in combination of two or more.

[0260] Examples of the ester solvent include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutyrate, ethyl acetate, n-butyl acetate, isobutyl acetate, pentyl formate, isopentyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexanol acetate, and γ-butyrolactone.

[0261] Examples of ether solvents include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenetole, methyl anisole, and the like.

[0262] Examples of ether ester solvents include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, ethyl 2-ethoxy-2-methylpropionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, and dipropylene glycol methyl ether acetate, and the like.

[0263] Examples of the ketone solvent include 4-hydroxy-4-methyl-2-pentanone (diacetone alcohol), acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone, and isophorone.

[0264] Examples of the alcohol solvent include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerin.

[0265] Examples of the aromatic hydrocarbon solvent include benzene, toluene, xylene, and mesitylene.

[0266] Examples of the amide solvent include N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.

[0267] The solvent (E) is preferably a solvent containing at least one selected from propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate, diacetone alcohol, and cyclohexanone.

[0268] The content of the solvent (E) is usually 99.99% by mass or less, preferably 40% by mass or more and 99% by mass or less, more preferably 50% by mass or more and 95% by mass or less, still more preferably 70% by mass or more and 95% by mass or less, and even more preferably 75% by mass or more and 90% by mass or less, based on the total amount of the colored resin composition. In other words, the total amount of the solid content of the colored resin composition is usually 0.01% by mass or more, preferably 1% by mass or more and 60% by mass or less, more preferably 5% by mass or more and 50% by mass or less, still more preferably 5% by mass or more and 30% by mass or less, and even more preferably 10% by mass or more and 25% by mass or less. When the content of the solvent (E) is within the above range, the flatness during coating is improved, and the display characteristics tend to be good because the color density is not insufficient when forming a color filter.

[0269] <Leveling agent (F)> Examples of the leveling agent (F) include silicone surfactants, fluorosurfactants, and silicone surfactants having fluorine atoms. These may have a polymerizable group in the side chain.

[0270] Examples of the silicone surfactant include surfactants having a siloxane bond in the molecule. Specifically, Toray Silicone DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, SH29PA, SH30PA, SH8400 (trade name: manufactured by Toray Dow Corning Co., Ltd.), KP321, KP322, KP323, KP324, KP326, KP340, KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452, and TSF4460 (manufactured by Momentive Performance Materials Japan LLC) etc. are included.

[0271] Examples of the fluorosurfactant include surfactants having a fluorocarbon chain in the molecule. Specifically, Fluorad (registered trademark) FC430, FC431 (manufactured by Sumitomo 3M Limited), Megafac (registered trademark) F142D, F171, F172, F173, F177, F183, F554, R30, RS-718-K (manufactured by DIC Corporation), F-Top (registered trademark) EF301, EF303, EF351, EF352 (manufactured by Mitsubishi Materials Electronic Chemicals Co., Ltd.), Surflon (registered trademark) S381, S382, SC101, SC105 (manufactured by AGC Inc.), and E5844 (manufactured by Daikin Fine Chemical Research Institute Co., Ltd.) etc. are included.

[0272] Examples of the silicone surfactant having fluorine atoms include surfactants having a siloxane bond and a fluorocarbon chain in the molecule. Specifically, Megafac (registered trademark) R08, BL20, F475, F477, and F443 (manufactured by DIC Corporation) etc. are included.

[0273] When the leveling agent (F) is contained, the content of the leveling agent (F) is preferably 0.0005% by mass or more and 1% by mass or less, more preferably 0.001% by mass or more and 0.5% by mass or less, and still more preferably 0.005% by mass or more and 0.1% by mass or less with respect to the total amount of the colored resin composition. Note that the content of the dispersant described above is not included in this content. When the content of the leveling agent (F) is within the above range, the flatness of the color filter can be improved.

[0274] <Other components> The colored resin composition may contain, if necessary, fillers, other polymer compounds, adhesion promoters, quenchers, antioxidants, light stabilizers, chain transfer agents, and other additives known in the art.

[0275] <Method for producing colored resin composition> The colored resin composition can be prepared by mixing phenylphosphonic acid which may have a substituent, a colorant (A), a dispersant (P), a resin (B), and optionally a polymerizable compound (C), a polymerization initiator (D), a polymerization initiation aid (D1), a solvent (E), a leveling agent (F), and other components. The mixing can be carried out by known or conventional devices and conditions. The colorant (A) may be used as a colorant-containing liquid obtained by mixing in advance with a part or all of the solvent (E) and dispersing it using a bead mill or the like until the average particle diameter becomes about 0.2 μm or less, and it is preferably used as a colorant-containing liquid. At this time, a part or all of the dispersant (P) and the resin (B) may be blended as necessary. Further, the colorant (A) may be used as a colorant-containing liquid obtained by dissolving it in a part or all of the solvent (E) in advance. The target colored resin composition can be prepared by mixing the remaining components into the colorant-containing liquid thus obtained so as to have a predetermined concentration.

[0276] <Method for producing color filter> A color filter, which may be a color conversion layer, can be formed from the colored resin composition of the present invention. Examples of the method for forming a colored pattern include a photolithography method, an inkjet method, a printing method, etc. Among them, the photolithography method is preferred. The photolithography method is a method in which the colored resin composition is applied to a substrate, dried to form a colored resin composition layer, and the colored resin composition layer is exposed and developed through a photomask. In the photolithography method, a colored coating film, which is a cured product of the colored resin composition layer, can be formed by not using a photomask and / or not developing during exposure. The colored pattern and the colored coating film thus formed are the color filter of the present invention.

[0277] The film thickness of the color filter to be produced is not particularly limited and can be appropriately adjusted according to the purpose, application, etc. For example, it is 0.1 μm or more and 30 μm or less, preferably 0.1 μm or more and 20 μm or less, more preferably 0.5 μm or more and 6 μm or less, and even more preferably 0.8 μm or more and 4.5 μm or less.

[0278] As the substrate, a glass plate such as quartz glass, borosilicate glass, aluminosilicate glass, and soda lime glass with a silica-coated surface, a resin plate such as polycarbonate, polymethyl methacrylate, and polyethylene terephthalate, silicon, or a substrate with an aluminum, silver, silver / copper / palladium alloy thin film, etc. formed thereon is used. Another color filter layer, resin layer, transistor, circuit, etc. may be formed on these substrates.

[0279] The formation of each color pixel by the photolithography method can be performed with known or conventional devices and conditions. For example, it can be produced as follows. First, the colored resin composition is applied onto a substrate, and volatile components such as a solvent are removed by heating and drying (pre-baking) and / or drying under reduced pressure to obtain a smooth colored resin composition layer. Examples of the coating method include a spin coating method, a slit coating method, a slit and spin coating method, etc. When performing heat drying, the temperature is preferably 30°C or higher and 120°C or lower, more preferably 50°C or higher and 110°C or lower. Also, the heating time is preferably 10 seconds or longer and 60 minutes or shorter, more preferably 30 seconds or longer and 30 minutes or shorter. When performing reduced-pressure drying, it is preferably performed under a pressure of 50 Pa or higher and 150 Pa or lower and in a temperature range of 20°C or higher and 25°C or lower. The film thickness of the colored resin composition layer is not particularly limited and may be appropriately selected according to the film thickness of the target color filter.

[0280] Next, the colored resin composition layer is exposed through a photomask for forming the target colored pattern. The pattern on the photomask is not particularly limited, and a pattern corresponding to the target application is used. Also, since it is possible to irradiate the entire exposure surface with parallel light rays uniformly and to perform accurate alignment between the photomask and the substrate on which the colored resin composition layer is formed, it is preferable to use an exposure apparatus such as a mask aligner and a stepper. When forming a colored coating film, exposure may be performed without using a photomask.

[0281] As the light source used for exposure, a light source that generates light with a wavelength of 250 nm or longer and 450 nm or shorter is preferable. For example, light with a wavelength of less than 350 nm may be cut using a filter that cuts this wavelength range, or light near 436 nm, near 408 nm, or near 365 nm may be selectively extracted using a band-pass filter that extracts these wavelength ranges. Specifically, a mercury lamp, a light-emitting diode, a metal halide lamp, a halogen lamp, etc. may be mentioned.

[0282] By bringing the exposed colored resin composition layer into contact with a developer for development, a colored pattern is formed on the substrate. By development, the unexposed portion of the colored resin composition layer is dissolved and removed by the developer. As the developer, for example, an aqueous solution of an alkaline compound such as potassium hydroxide, sodium hydrogen carbonate, sodium carbonate, or tetramethylammonium hydroxide is preferable. The concentration in the aqueous solution of these alkaline compounds is preferably 0.01% by mass or more and 10% by mass or less, more preferably 0.03% by mass or more and 5% by mass or less. Further, the developer may contain a surfactant. The developing method may be any of a paddle method, a dipping method, a spray method, etc. Further, the substrate may be tilted at an arbitrary angle during development. The substrate after development is preferably washed with water.

[0283] Furthermore, it is preferable to perform post-baking on the obtained colored pattern or colored coating film. The post-baking temperature is preferably 150°C or higher and 250°C or lower, more preferably 160°C or higher and 240°C or lower. The post-baking time is preferably 1 minute or more and 120 minutes or less, more preferably 10 minutes or more and 60 minutes or less.

[0284] <Display device> The color filter is useful as a color filter used in a display device (for example, a liquid crystal display device, an organic EL device, an electronic paper, etc.) and a solid-state imaging device.

Examples

[0285] Next, the present invention will be described more specifically with reference to synthesis examples. In the examples, % and parts representing content or usage amount are based on mass unless otherwise specified.

[0286] In the following synthesis examples, the structure of the compound was confirmed by mass spectrometry (LC; Agilent 1200 type, MASS; Agilent LC / MSD6130 type).

[0287] <Synthesis of dye> [Synthesis example of dye 1: Synthesis of compound (B-I-1)] The following reaction was carried out under a nitrogen atmosphere. 0.48 part of palladium acetate (manufactured by Tokyo Chemical Industry Co., Ltd.), 1.74 parts of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (manufactured by Tokyo Chemical Industry Co., Ltd.), 7.50 parts of sodium tert-butoxide (manufactured by Tokyo Chemical Industry Co., Ltd.) and 14.58 parts of 1-bromonaphthalene (manufactured by Tokyo Chemical Industry Co., Ltd.) were charged into a flask equipped with a condenser tube and a stirrer. Then, a mixed solution of 9 parts of 4,4′-methylenebis(2,6-dimethylaniline) (manufactured by Sigma-Aldrich Co., LLC) and 63 parts of toluene was added dropwise to the flask. The reaction solution was stirred for 2 hours while heating to 110 °C in an oil bath. After allowing the reaction solution to cool, it was filtered through celite to obtain a filtrate. 180 parts of ethyl acetate and 180 parts of ion-exchanged water were added thereto, and the mixture was vigorously mixed and then separated to obtain an organic layer. The obtained organic layer was dried over 48 parts of sodium sulfate, and the solid was removed by filtration. The obtained organic layer was concentrated to obtain a crude product. The obtained crude product was purified by silica gel column chromatography (solvent: chloroform / methanol 100 / 1 to 20 / 1), and the obtained fraction was concentrated under reduced pressure and dried under reduced pressure at 60 °C to obtain 11.6 parts of the compound represented by the formula (B-I-1).

[0288] [Chemical formula]

[0289] Identification of the compound represented by the formula (B-I-1) (Mass spectrometry) Ionization mode = ESI+: m / z = 506.5

[0290] [Example of pigment synthesis 2: Synthesis of compound (C-I-1)] The following reaction was carried out under a nitrogen atmosphere. 0.27 part of bis(dibenzylideneacetone)palladium(0) (manufactured by Tokyo Chemical Industry Co., Ltd.), 0.57 part of 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (manufactured by Sigma-Aldrich), 42.1 parts of sodium tert-butoxide (manufactured by Tokyo Chemical Industry Co., Ltd.), and 50 parts of 4,4′-dichlorobenzophenone (manufactured by Tokyo Chemical Industry Co., Ltd.) were charged into a flask equipped with a condenser tube and a stirrer. Then, a mixed solution of 48.3 parts of 2,6-dimethylaniline (manufactured by Tokyo Chemical Industry Co., Ltd.) and 432 parts of toluene was added dropwise to the flask. The reaction solution was stirred for 2 hours while heating to 80 °C in an oil bath. After cooling the reaction solution in an ice bath, filtration was performed to obtain a solid and a filtrate. This solid was designated as crude product A1, and the filtrate was designated as filtrate A1. The obtained crude product A1 was washed with 50 parts of toluene and then washed twice with 250 parts of ion-exchanged water to obtain a solid. This solid was designated as crude product B1. Filtrate A1, 50 parts of toluene, 229 parts of ion-exchanged water, and 20.8 parts of 35% hydrochloric acid were charged into a bottom-discharge flask, stirred for 1 hour, and then liquid-separated to obtain an organic layer. The obtained organic layer was liquid-separated and washed with a mixed solution of 238 parts of ion-exchanged water and 12.5 parts of sodium carbonate, dried over 150 parts of magnesium sulfate, and the solid was removed by filtration. The obtained organic layer was concentrated to obtain a solid. This solid was designated as crude product C1. Crude product B1 and crude product C1 were charged into a flask equipped with a stirrer, 4 times the mass of acetonitrile with respect to the total mass of crude product B1 and crude product C1 was added, and the mixture was stirred for 1 hour. The solid obtained by filtering the mixture was washed with 1 time the mass of acetonitrile with respect to the total mass of crude product B1 and crude product C1. The washed solid was dried under reduced pressure at 60 °C to obtain 75.9 parts of the compound represented by the formula (C-I-1). The yield was 90.6%.

[0291] [Chemical formula]

[0292] [Example of Dye Synthesis 3: Synthesis of Compound (C-I-2)] The following reaction was carried out under a nitrogen atmosphere. 50 parts of the compound represented by the formula (C-I-1) and 188 parts of N,N-dimethylformamide were charged into a flask equipped with a condenser tube and a stirrer, and the mixture was stirred for 30 minutes while cooling in an ice bath. 40 parts of potassium tert-butoxide (manufactured by Tokyo Chemical Industry Co., Ltd.) was charged into the flask, and the mixture was further stirred for 1 hour while cooling in an ice bath. While keeping the reaction solution ice-cooled, 55.6 parts of iodoethane (manufactured by Tokyo Chemical Industry Co., Ltd.) was added dropwise. After the reaction solution was heated to 35 °C using an oil bath and stirred for 5 hours, it was allowed to cool to room temperature. 1000 parts of a 10% aqueous sodium chloride solution was charged into another flask equipped with a stirrer, and the above reaction solution was added dropwise while stirring. After stirring for 30 minutes, filtration was carried out to obtain a solid. The obtained solid was washed three times with 500 parts of ion-exchanged water and dried at 60 °C under reduced pressure to obtain 53.0 parts of the compound represented by the formula (C-I-2). The yield was 93.5%.

[0293]

Chemical formula

[0294] [Example of pigment synthesis 4: Synthesis of compound (I-5a-1)] The following reaction was carried out under a nitrogen atmosphere. After charging 1 part of the compound represented by the formula (B-I-1), 11.28 parts of the compound represented by the formula (C-I-2) and 42 parts of toluene into a flask equipped with a condenser tube and a stirrer, 5.4 parts of phosphorus oxychloride (manufactured by FUJIFILM Wako Pure Chemical Corporation) was then added, and the mixture was stirred at 110 °C for 7.5 hours. Next, after cooling the reaction mixture to room temperature, 450 parts of ethyl acetate and saturated brine were added and filtered to obtain a crude product. This was purified by silica gel column chromatography (solvent: chloroform / methanol 100 / 1 to 10 / 1), and the obtained fraction was concentrated under reduced pressure and dried under reduced pressure at 60 °C to obtain 9.90 parts of the compound represented by the formula (I-5a-1).

[0295]

Chemical formula

[0296] Identification of the compound represented by the formula (I-5a-1) (Mass spectrometry) Ionization mode = ESI+: m / z = 712.6, divalent

[0297] [Example of pigment synthesis 5: Synthesis of compound (I-5a-2)] The following reaction was carried out under a nitrogen atmosphere. 4 parts of the compound represented by the formula (I-5a-1) and 26.7 parts of methanol were charged into a flask equipped with a condenser tube and a stirrer, and then stirred at room temperature for 30 minutes to prepare a blue solution. 17.8 parts of water was charged into a flask equipped with a condenser tube and a stirrer, and further, 6.2 parts of phosphotungstic acid hydrate (Keggin type phosphotungstic acid; manufactured by Sigma-Aldrich Co., Ltd.) was charged into the water, and mixed at room temperature under an air atmosphere to prepare a phosphotungstic acid solution. To the obtained phosphotungstic acid solution, 53.4 parts of the previously prepared blue solution and washing methanol were added dropwise. After stirring for 4 hours while heating to 55 °C in an oil bath, it was cooled to room temperature. The reaction mixture was concentrated to obtain a crude product. 40 parts of ion-exchanged water was added to the obtained crude product to form a suspension, and it was filtered and washed successively with 50 parts of ion-exchanged water and 10 parts of methanol. The obtained crude product was charged into 80 parts of methanol and dispersed for 1 hour, and then filtered and washed with 50 parts of methanol. The blue solid obtained by this operation was dried under reduced pressure at 60 °C to obtain 7.51 parts of the compound represented by the formula (I-5a-2).

[0298] [Chemical formula]

[0299] Identification of the compound represented by the formula (I-5a-2) (Mass spectrometry) Ionization mode = MALDI+: m / z = 1423.7 Ionization mode = MALDI-: m / z = 2902.5

[0300] [Synthesis of resin] [Resin synthesis example 1] An appropriate amount of nitrogen was flowed into a flask equipped with a reflux condenser, a dropping funnel, and a stirrer, and the atmosphere was replaced with nitrogen. 371 parts of propylene glycol monomethyl ether acetate were placed, and the mixture was heated to 85 °C while stirring. Next, 54 parts of acrylic acid, 225 parts of a mixture of 3,4-epoxytricyclo[5.2.1.0 2,6 decane-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 2,6 decane-9-yl acrylate (the content ratio was 1:1 in molar ratio), and 81 parts of vinyltoluene (isomer mixture) were added dropwise into the flask over 4 hours as a mixed solution of 80 parts of propylene glycol monomethyl ether acetate. On the other hand, a solution prepared by dissolving 30 parts of a polymerization initiator 2,2-azobis(2,4-dimethylvaleronitrile) in 160 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. After the dropping of the initiator solution was completed, the mixture was held at 85 °C for 4 hours and then cooled to room temperature to obtain a copolymer (resin B-1) solution with a solid content of 37.5% and a viscosity of 246 mPa·s measured with a B-type viscometer (23 °C). The weight-average molecular weight of the produced copolymer was 1.06×10 4 , the dispersity was 2.01, and the acid value in terms of solid content was 115 mg-KOH / g. Resin B-1 has the following structural units.

[0301]

Chemical formula

[0302] Regarding the measurement of the weight-average molecular weight (Mw) and number-average molecular weight (Mn) of the above resin, the GPC method was used and carried out under the following conditions. Apparatus; K2479 (manufactured by Shimadzu Corporation) Column; SHIMADZU Shim-pack GPC-80M Column temperature; 40 °C Solvent; tetrahydrofuran (THF) Concentration of test solution; 25 mg / mL (solvent; THF) Flow rate; 1.0 mL / min Detector; RI Standard substance for calibration; TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Corporation) The ratio of the weight average molecular weight and the number average molecular weight in terms of polystyrene obtained above was defined as the dispersity (Mw / Mn).

[0303] [Resin Synthesis Example 2] An appropriate amount of nitrogen was flowed into a flask equipped with a reflux condenser, a dropping funnel, and a stirrer and replaced with a nitrogen atmosphere. 141 parts of ethyl lactate and 178 parts of propylene glycol monomethyl ether acetate were placed, and the mixture was heated to 85°C while stirring. Next, a mixed solution of 38 parts of acrylic acid, 25 parts of a mixture of 3,4-epoxytricyclo[5.2.1.0 2,6 decane-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 2,6 decane-9-yl acrylate (molar ratio 1:1), 137 parts of N-cyclohexylmaleimide, 50 parts of 2-hydroxyethyl methacrylate, and 338 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. On the other hand, a solution prepared by dissolving 5 parts of 2,2-azobisisobutyronitrile in 88 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After completion of the addition, the mixture was held at 85°C for 4 hours and then cooled to room temperature to obtain a copolymer (resin B-2) solution having a viscosity of 23 mPa·s measured with a B-type viscometer (23°C) and a solid content of 25.6%. The weight average molecular weight Mw of the produced copolymer was 8.0×10 3 , the dispersity was 2.1, and the acid value in terms of solid content was 109 mg-KOH / g. Resin B-2 has the following structural units.

[0304] [Chemical formula]

[0305] [Preparation Example 1] [Preparation of Colorant Dispersion (A-1) Containing Compound (I-5a-2)] 5.0 parts of compound (I-5a-2), 0.25 part of phenylphosphonic acid (manufactured by Tokyo Chemical Industry Co., Ltd.), 3.0 parts of dispersant P-1 (manufactured by BYK-Chemie, DISPERBYK-161, amine value 11 mg KOH / g), 2.0 parts of resin B-1 (in terms of solid content), 80 parts of propylene glycol monomethyl ether acetate, 10 parts of diacetone alcohol and 300 parts of 0.2 mm zirconia beads were mixed, and the resulting mixture was shaken for 3 hours using a paint conditioner (manufactured by LAU). Then, the zirconia beads were removed by filtration to obtain a colorant dispersion (A-1).

[0306] [Preparation Example 2] [Preparation of Colorant Dispersion (A-2)] 5.0 parts of compound (I-5a-2), 0.5 part of phenylphosphonic acid (manufactured by Tokyo Chemical Industry Co., Ltd.), 3.0 parts of dispersant P-1 (manufactured by BYK-Chemie, DISPERBYK-161, amine value 11 mg KOH / g), 2.0 parts of resin B-1 (in terms of solid content), 80 parts of propylene glycol monomethyl ether acetate, 10 parts of diacetone alcohol and 300 parts of 0.2 mm zirconia beads were mixed, and the resulting mixture was shaken for 3 hours using a paint conditioner (manufactured by LAU). Then, the zirconia beads were removed by filtration to obtain a colorant dispersion (A-2).

[0307] [Preparation Examples 3 to 5] [Preparation of Colorant Dispersions (A-3) to (A-5)] Colorant dispersions (A-3) to (A-5) were obtained in the same manner as in Preparation Example 1, except that the dispersant in Preparation Example 1 was changed to P-2 to P-4, respectively. P-2: BYK-LP N 21324 (manufactured by BYK-Chemie, amine value 0 mg KOH / g) P-3: DISPERBYK-2001 (manufactured by BYK-Chemie, amine value 29 mg KOH / g, acid value 19 mg KOH / g) P-4: DISPERBYK-2150 (manufactured by BYK-Chemie, amine value 57 mg KOH / g)

[0308] [Preparation Examples 6 to 10] <Preparation of Colorant Dispersion (A-6) to (A-10)> Colorant dispersions (A-6) to (A-10) were obtained in the same manner as in Preparation Example 1, except that the phenylphosphonic acid in Preparation Example 1 was changed to each of the following X-b to X-f. X-b: 1,4-Phenylenediphosphonic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) X-c: 4-Bromophenylphosphonic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) X-d: 3-Carboxylphenylphosphonic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) X-e: 4-Methoxyphenylphosphonic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) X-f: 4-Aminophenylphosphonic acid (manufactured by Tokyo Chemical Industry Co., Ltd.)

[0309] [Comparative Preparation Example 1] <Preparation of Colorant Dispersion (A-11)> 5.0 parts of Compound (I-5a-2), 3.0 parts of Dispersant P-1 (manufactured by BYK Chemie GmbH, DISPERBYK-161, amine value 11 mg KOH / g), 2.0 parts of Resin B-1 (in terms of solid content), 80 parts of propylene glycol monomethyl ether acetate, 10 parts of diacetone alcohol, and 300 parts of 0.2 mm zirconia beads were mixed, and the resulting mixture was shaken for 3 hours using a paint conditioner (manufactured by LAU). Thereafter, the zirconia beads were removed by filtration to obtain Colorant Dispersion (A-11).

[0310] [Comparative Preparation Example 2] <Preparation of Colorant Dispersion (A-12)> Colorant Dispersion (A-12) was obtained in the same manner as in Preparation Example 1, except that the dispersant in Preparation Example 1 was changed to P-5. P-5: DISPERBYK-108 (manufactured by BYK Chemie GmbH, amine value 71 mg KOH / g)

[0311] Example 1 <Preparation of Colored Resin Composition 1> (A) Colorant: 880 parts of Colorant Dispersion (A-1) (B) Resin: 75 parts of Resin (B-2) (in terms of solid content) (C) Polymerizable compound: dipentaerythritol hexaacrylate (Kayarad (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 50 parts (D) Polymerization initiator: TR-PBG327 (manufactured by Changzhou Strong Electronics New Materials Co., Ltd.) 4.3 parts (F) Surfactant: Polyether modified silicone oil (product name: Toray Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.) 0.18 parts (E) Solvent: Propylene glycol monomethyl ether acetate (E-1) 410 copies (E) Solvent: Ethyl lactate (E-2) 44 parts The above ingredients were mixed to obtain a colored resin composition 1.

[0312] Example 2 <Preparation of Colored Resin Composition 2> (A) Colorant: Colorant dispersion (A-2) 890 parts (B) Resin: Resin (B-2) (solid content equivalent) 75 parts (C) Polymerizable compound: dipentaerythritol hexaacrylate (Kayarad (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 50 parts (D) Polymerization initiator: TR-PBG327 (manufactured by Changzhou Strong Electronics New Materials Co., Ltd.) 4.3 parts (F) Surfactant: Polyether modified silicone oil (Product name: Toray Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.) 0.18 parts (E) Solvent: Propylene glycol monomethyl ether acetate (E-1) 420 copies (E) Solvent: Ethyl lactate (E-2) 44 parts The above were mixed to obtain a colored resin composition 2.

[0313] Examples 3 to 10 <Preparation of Colored Resin Compositions 3 to 10> Colored resin compositions 3 to 10 were obtained in the same manner as in Example 1, except that the colorant dispersion (A-1) in Example 1 was changed to colorant dispersions (A-3) to (A-10), respectively.

[0314] Comparative Example 1 <Preparation of Comparative Colored Resin Composition 1> (A) Colorant: 870 parts of colorant dispersion (A-11) (B) Resin: 76 parts of resin (B-2) (in terms of solid content) (C) Polymerizable compound: Dipentaerythritol hexaacrylate (Kayarad (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 50 parts (D) Polymerization initiator: TR-PBG327 (manufactured by Changzhou Qiangli Electronic New Materials Co., Ltd.) 4.3 parts (F) Surfactant: Polyether-modified silicone oil (Trade name: Toray Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.) 0.17 part (E) Solvent: Propylene glycol monomethyl ether acetate (E-1) 403 parts (E) Solvent: Ethyl lactate (E-2) 44 parts These were mixed to obtain Comparative Colored Resin Composition 1.

[0315] Comparative Example 2 <Preparation of Comparative Colored Resin Composition 2> Comparative Colored Resin Composition 2 was obtained in the same manner as in Example 1, except that the colorant dispersion (A-1) in Example 1 was changed to colorant dispersion (A-12).

[0316] <Formation of Colored Coating Film (Color Filter)> On a 2-inch square glass substrate (Eagle 2000; manufactured by Corning Inc.), the colored resin compositions 1 to 10 obtained in Examples 1 to 10 and the comparative colored resin compositions 1 to 2 obtained in Comparative Examples 1 to 2 were each applied by spin coating, and then pre-baked at 100°C for 3 minutes to form a composition layer. After cooling, using an exposure machine (TME-150RSK; manufactured by Topcon Corporation), the composition layer was irradiated with light at an exposure amount of 60 mJ / cm 2 (based on 365 nm) in an air atmosphere, and then post-baked in an oven at 230°C for 20 minutes to obtain a colored coating film.

[0317] <Evaluation of Contrast> Regarding the obtained colored coating film, using a contrast meter (CT-1; manufactured by Kozaka Electric Co., Ltd., color difference meter BM-5A; manufactured by Topcon Corporation, light source; F-10, polarizing film; manufactured by Kozaka Electric Co., Ltd.), with a blank value of 50000, the contrast was measured.

[0318] <Evaluation of Lightness> Regarding the obtained colored coating film, using a colorimeter (OSP-SP-200; manufactured by Olympus Corporation), spectroscopy was measured, and using the characteristic function of the C light source, the xy chromaticity coordinates (x, y) and the stimulus value Y in the CIE XYZ color system were measured. Y represents lightness, and regarding the values of Y at the same y coordinate, a comparative evaluation was performed. The larger the Y value, the higher the lightness.

[0319] Table 10 shows the film thickness, lightness, and contrast results of the colored coating films obtained in Examples 1 to 10 and Comparative Examples 1 to 2.

[0320]

Table 10

[0321] When the amine value of the dispersant is 70 mgKOH / g or more, the lightness and contrast significantly decrease (Comparative Example 2). Even when the amine value of the dispersant is less than 70 mgKOH / g, without adding phenylphosphonic acid, although the lightness and contrast are improved, it is not sufficient (Comparative Example 1). It can be seen that Examples 1 to 10, in which the amine value of the dispersant is less than 70 mgKOH / g and unsubstituted or substituted phenylphosphonic acid is added, show a higher contrast and higher lightness compared to Comparative Examples 1 to 2.

Claims

Claim 1 A colored resin composition containing a phenylphosphonic acid which may have a substituent, a colorant, a dispersant having an amine value of less than 70 mg KOH / g, and a resin, wherein the colorant contains a compound represented by the following formula (I). 【Chemical Formula 1】 [In formula (I), R 1 to R 4 and R 13 each independently represents a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent. R 5 to R 12 each independently represents a hydrogen atom, a halogen atom, or a hydrocarbon group having 1 to 5 carbon atoms which may have a substituent. T 1 represents a divalent aromatic hydrocarbon group which may have a substituent. T 2 represents a divalent aromatic hydrocarbon group which may have a substituent or a divalent aromatic heterocyclic group which may have a substituent. L 1 represents an a-valent aliphatic hydrocarbon group having 1 to 12 carbon atoms which may have a substituent or a group represented by the formula (i). a represents an integer of 2 or more. b and c each independently represent an integer of 1 or more. d represents an integer of 0 or more. X c- represents an anion with a c valence.] 【Chemical 2】 [In formula (i), T 3 represents an a-valent aromatic hydrocarbon group which may have a substituent or an a-valent aromatic heterocyclic group which may have a substituent. L 2 represents a divalent aliphatic hydrocarbon group having 1 to 5 carbon atoms which may have a substituent. a represents an integer of 2 or more. * represents a bond with T 2 represents a bond with.] Claim 2 R 1 and R 3 each independently represents a phenyl group which may have a substituent, said R 1 and R 3 The colored resin composition according to claim 1, wherein the phenyl groups of R and R each have an alkyl group having 1 to 4 carbon atoms at at least one of two bonding positions that are ortho positions with respect to the N bonded to the phenyl group. Claim 3 The colored resin composition according to claim 1, wherein the amine value of the dispersant is 0 mg KOH / g or more and 65 mg KOH / g or less. Claim 4 The colored resin composition according to any one of claims 1 to 3, further containing a polymerizable compound and a polymerization initiator. Claim 5 A color filter formed from the colored resin composition according to any one of claims 1 to 3. Claim 6 A display device including the color filter according to claim 5.

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