Colored resin composition, color filter and display device

Abstract

The present invention addresses the problem of providing a colored resin composition capable of forming a color filter having excellent brightness and contrast. The present invention relates to a colored resin composition containing one or more acids selected from the group consisting of phenyl phosphonic acids that may have a substituent and diphenyl phosphonic acids that may have a substituent, a colorant, a dispersant, and a resin, the colorant containing a compound represented by formula (I), and the dispersant having an amine value of 0-65 mgKOH / g. # imgabs0 #

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, electroluminescent display devices, and plasma display panels, and solid-state imaging elements such as CCDs or CMOS sensors are manufactured from colored resin compositions. As the colored resin composition for forming the color filter, various colorants are used. As such a colorant, for example, there is an example of using a compound represented by the following formula (I-5a-2) (Patent Document 1), and an example of using a compound represented by the following chemical formula (3) (Patent Document 2).

[0003]

[0004] Prior Art Documents

[0005] Patent Documents

[0006] Patent Document 1: International Publication No. 2022 / 234774

[0007] Patent Document 2: International Publication No. 2016 / 024596 Summary of the Invention

[0008] However, there are cases where the brightness and contrast of a color filter formed from a colored resin composition containing the above compound are not sufficiently satisfactory. Therefore, an object of the present invention is to provide a colored resin composition capable of forming a color filter having excellent brightness and contrast.

[0009] That is, the gist of the present invention is as follows.

[0010] [1] A colored resin composition containing one or more acids selected from phenylphosphoric acid which may have a substituent and diphenylphosphoric acid which may have a substituent, a colorant, a dispersant, and a resin, wherein the colorant contains a compound represented by the following formula (I), and the amine value of the dispersant is 0 mgKOH / g to 65 mgKOH / g.

[0011]

[0012] [In formula (I),

[0013] R 1 ~R 4 and R 13 independently of each other represent a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent.

[0014] R 5 ~R 12Each independently represents a hydrogen atom, a halogen atom, or a hydrocarbon group having 1 to 5 carbon atoms which may have substituents.

[0015] T 1 Represents a divalent aromatic ring which may have substituents. a represents an integer of 1 or more.

[0016] i) When a is 1

[0017] T 2 Represents a hydrocarbon group having 1 to 10 carbon atoms which may have substituents.

[0018] ii) When a is an integer of 2 or more

[0019] T 2 Represents an a-valent group which may have substituents, and the -CH2- contained in the a-valent group may be substituted by -O-, -CO-, -S-, -SO-, -SO2-, or -NR 1a -.

[0020] R 1a Represents a hydrogen atom or an aliphatic hydrocarbon group having 1 to 8 carbon atoms.

[0021] b and c each independently represent an integer of 1 or more.

[0022] d represents an integer of 0 or more.

[0023] X c- Represents a c-valent anion.

[0024] [2] The colored resin composition according to [1], wherein in formula (I), a is an integer of 2 or more, and T 2 Represents the group represented by formula (i).

[0025]

[0026] [In formula (i),

[0027] T 3 Represents an a-valent cyclic hydrocarbon group, and L 2 Represents a divalent aliphatic hydrocarbon group having 1 to 5 carbon atoms which may have substituents, or

[0028] T 3 Represents a divalent aliphatic hydrocarbon group having 1 to 5 carbon atoms which may have substituents, and L 2 Represents an a-valent cyclic hydrocarbon group.

[0029] * represents the bonding site to the nitrogen atom.

[0030] [3] The colored resin composition according to [1] or [2], further comprising a polymerizable compound and a polymerization initiator.

[0031] [4] A color filter formed from the coloring resin composition according to any one of [1] to [3].

[0032] [5] A display device including the color filter according to [4].

[0033] According to the present invention, a coloring resin composition capable of forming a color filter having excellent brightness and contrast can be provided. Detailed Description of the Invention

[0034] The coloring resin composition of the present invention contains one or more acids selected from phenylphosphoric acid which may have substituents and diphenylphosphoric acid which may have substituents (hereinafter, sometimes referred to as acid), 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)).

[0035] The coloring resin composition of the present invention may further contain a polymerizable compound (hereinafter, sometimes referred to as polymerizable compound (C)).

[0036] The coloring resin composition of the present invention may further contain a polymerization initiator (hereinafter, sometimes referred to as polymerization initiator (D)).

[0037] The coloring resin composition of the present invention may further contain a solvent (hereinafter, sometimes referred to as solvent (E)).

[0038] The coloring resin composition of the present invention may further contain a polymerization initiator assistant (hereinafter, sometimes referred to as polymerization initiator assistant (D1)).

[0039] The coloring resin composition of the present invention may further contain a leveling agent (hereinafter, sometimes referred to as leveling agent (F)).

[0040] It should be noted that, in this specification, the compounds exemplified as each component may be used alone or in combination of a plurality of them as long as there is no particular description.

[0041] <Colorant (A)>

[0042] 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 the tautomer of formula (I) is also included in compound (I).

[0043]

[0044] [In formula (I),

[0045] R 1 ~R 4 and R13 Each independently represents a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms which may have substituents.

[0046] R 5 ~R 12 Each independently represents a hydrogen atom, a halogen atom or a hydrocarbon group having 1 to 5 carbon atoms which may have substituents.

[0047] T 1 Represents a divalent aromatic ring which may have substituents. a represents an integer of 1 or more.

[0048] i) When a is 1

[0049] T 2 Represents a hydrocarbon group having 1 to 10 carbon atoms which may have substituents.

[0050] ii) When a is an integer of 2 or more

[0051] T 2 Represents an a-valent group which may have substituents, and the —CH2— contained in the a-valent group may be substituted by —O—, —CO—, —S—, —SO—, —SO2— or —NR 1a —.

[0052] R 1a Represents a hydrogen atom or an aliphatic hydrocarbon group having 1 to 8 carbon atoms.

[0053] b and c each independently represent an integer of 1 or more.

[0054] d represents an integer of 0 or more.

[0055] X c- Represents a c-valent anion.

[0056] As the hydrocarbon group having 1 to 10 carbon atoms represented by R 1 ~R 4 and R 13 Examples of the hydrocarbon group having 1 to 10 carbon atoms include aliphatic hydrocarbon groups and aromatic hydrocarbon groups. The aliphatic hydrocarbon group may be saturated or unsaturated, and may be linear or alicyclic.

[0057] Examples of the above-mentioned saturated or unsaturated chain hydrocarbon groups include linear alkyl groups such as methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, and n-decyl; branched alkyl groups such as isopropyl, (1-ethyl)propyl, isobutyl, sec-butyl, tert-butyl, (1-ethyl)butyl, (2-ethyl)butyl, (1-propyl)butyl, isopentyl, neopentyl, tert-pentyl, (2-methyl)pentyl, (1-ethyl)pentyl, (3-ethyl)pentyl, (1-propyl)pentyl, (1-butyl)pentyl, isohexyl, (2-methyl)hexyl, (5-methyl)hexyl, (2-ethyl)hexyl, (1-butyl)hexyl, (2-methyl)heptyl, (2-ethyl)heptyl, (3-ethyl)heptyl, (2-methyl)octyl, and (2-ethyl)octyl; and alkenyl groups such as vinyl, 1-propenyl, 2-propenyl (allyl), (1-methyl)vinyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, (1-(2-propenyl))vinyl, (1,2-dimethyl)propenyl, and 2-pentenyl.

[0058] Examples of the above-mentioned saturated or unsaturated alicyclic hydrocarbon groups include cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl; cycloalkenyl groups such as cyclohexenyl (e.g., cyclohex-2-ene, cyclohex-3-ene), cycloheptenyl, and cyclooctenyl; and norbornyl, adamantyl, bicyclo[2.2.2]octyl, etc.

[0059] Examples of the aromatic hydrocarbon groups include aryl groups such as phenyl, 1-naphthyl, and 2-naphthyl; alkylaryl groups such as o-tolyl, m-tolyl, p-tolyl, 2-ethylphenyl, 3-ethylphenyl, 4-ethylphenyl, 2,3-dimethylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, 3,4-dimethylphenyl, 3,5-dimethylphenyl, 2,4,6-trimethylphenyl, 2-methyl-6-ethylphenyl, 2,6-diethylphenyl, o-isopropylphenyl, m-isopropylphenyl, p-isopropylphenyl, 2-methyl-6-isopropylphenyl, 4-butylphenyl, o-tert-butylphenyl, m-tert-butylphenyl, and p-tert-butylphenyl; and alkenylaryl groups such as 4-vinylphenyl.

[0060] When the upper limit of the number of carbon atoms of the above-mentioned hydrocarbon group having 1 to 10 carbon atoms is 10, it may also be a group formed by combining two or more of the above-mentioned linear hydrocarbon group, alicyclic hydrocarbon group and aromatic hydrocarbon group. As such a group, for example, aralkyl groups such as benzyl, phenethyl, 1-methyl-1-phenylethyl, etc.; arylalkenyl groups such as phenylvinyl (phenylvinyl); arylalkynyl groups such as phenyl ethynyl; 1-methylcyclopropyl, 1-methylcyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 1,2-dimethylcyclohexyl, 1,3-dimethylcyclohexyl, 1,4-dimethylcyclohexyl, 2,3-dimethylcyclohexyl, 2,4-dimethylcyclohexyl, 2,5-dimethylcyclohexyl, 2,6-dimethylcyclohexyl, 3,4-dimethylcyclohexyl, 3,5-dimethylcyclohexyl, 2,2-dimethylcyclohexyl, 3,3-dimethylcyclohexyl, 4,4-dimethylcyclohexyl, 2,4,6-trimethylcyclohexyl, 2,2,6,6-tetramethylcyclohexyl, 3,3,5,5-tetramethylcyclohexyl and other alicyclic hydrocarbon groups bonded with one or more alkyl groups or alicyclic hydrocarbon groups; alkyl groups such as cyclopropylmethyl, cyclopropylethyl, cyclobutylmethyl, cyclobutylethyl, cyclopentylmethyl, cyclopentylethyl, cyclohexylmethyl, 2-methylcyclohexylmethyl, cyclohexylethyl and other alkyl groups bonded with one or more alicyclic hydrocarbon groups.

[0061] As the substituents that the above-mentioned hydrocarbon group having 1 to 10 carbon atoms may have (hereinafter sometimes referred to as substituent A), examples include at least one selected from halogen atoms, hydroxyl groups, alkoxy groups, formyl groups, substituted or unsubstituted amino groups, nitro groups, cyano groups, -SO3 - and -SO3M, where M represents a hydrogen atom or an alkali metal atom.

[0062] As the above-mentioned halogen atom, examples include fluorine atom, chlorine atom, bromine atom, iodine atom.

[0063] As the above-mentioned alkoxy group, examples include alkoxy groups having 1 to 4 carbon atoms such as methoxy group, ethoxy group, propoxy group, butoxy group.

[0064] As the above-mentioned substituted amino group, examples include amino groups having one or two hydrocarbon groups. As the above-mentioned hydrocarbon group, examples include the groups exemplified as the above-mentioned hydrocarbon group having 1 to 10 carbon atoms. As the substituted amino group, for example, N-methylamino, N,N-dimethylamino, N-ethylamino, N,N-diethylamino, N-propylamino, N,N-dipropylamino, N-isopropylamino, N,N-diisopropylamino, N-phenylamino, N,N-diphenylamino, N,N-ethylmethylamino, N,N-methylphenylamino, N,N-ethylphenylamino, etc.

[0065] As the above-mentioned alkali metal atom, examples include sodium, potassium, etc.

[0066] As R5 ~R 12 The halogen atom represented by 12 may be a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

[0067] As R 5 ~R 12 The hydrocarbon group having 1 to 5 carbon atoms represented by 12 may be an aliphatic hydrocarbon group having 1 to 5 carbon atoms. Specifically, as the above R 1 ~R 4 and R 13 The group having 1 to 5 carbon atoms among the groups exemplified as the aliphatic hydrocarbon groups of 13 .

[0068] As the substituent that the hydrocarbon group having 1 to 5 carbon atoms as described above may have, the groups exemplified as substituent A may be mentioned.

[0069] T 1 The divalent aromatic ring represented by 1 includes a divalent aromatic hydrocarbon group and a divalent aromatic heterocyclic group.

[0070] The divalent aromatic hydrocarbon group means a group formed by substituting two hydrogen atoms directly bonded to the carbon atoms constituting the aromatic hydrocarbon ring with bonding sites. The aromatic hydrocarbon ring constituting the divalent aromatic hydrocarbon group may be either a monocyclic ring or a fused ring. For example, a benzene ring, a naphthalene ring, an anthracene ring, and a structure obtained by substituting at least one hydrogen atom of these aromatic hydrocarbon rings with a hydrocarbon group that may have a substituent, etc. may be mentioned. As the above hydrocarbon group, the groups exemplified as the above R 1 ~R 4 and R 13 The groups exemplified as the hydrocarbon group having 1 to 10 carbon atoms represented by 13 are preferably a saturated chain hydrocarbon group, an aryl group, or an alkylaryl group, 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 further preferably 0 to 2. Specifically, as the divalent aromatic hydrocarbon group, groups represented by the following formulas (Ta-1) to (Ta-8) etc. may be mentioned.

[0071]

[0072] The divalent aromatic heterocyclic group means a group obtained by substituting two hydrogen atoms directly bonded to the atoms constituting the aromatic heterocyclic ring with bonding sites. The aromatic heterocyclic ring constituting the divalent aromatic heterocyclic group may be either a monocyclic ring or a fused ring. For example, 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 a structure obtained by substituting at least one hydrogen atom of these aromatic heterocyclic rings with a hydrocarbon group that may have a substituent, etc. may be mentioned. As the above hydrocarbon group, the groups exemplified as the above R1 ~R 4 and R 13 The groups exemplified by hydrocarbon groups having 1 to 10 carbon atoms represented are preferably saturated chain hydrocarbon groups, aryl groups, or alkylaryl groups. The number of hydrocarbon groups bonded to the aromatic heterocycle is preferably 0 to 4, more preferably 0 to 3, and still more preferably 0 to 2.

[0073] As substituents that the above divalent aromatic hydrocarbon group, the above divalent aromatic heterocyclic group, and the hydrocarbon group bonded to these groups may have, the groups exemplified as substituent A can be mentioned.

[0074] Hereinafter, T will be described separately for the case where a is 1 and the case where a is an integer of 2 or more. 2 Explanation will be given.

[0075] <Case where a is 1>

[0076] T 2 represents a hydrocarbon group having 1 to 10 carbon atoms which may have substituents.

[0077] For the hydrocarbon group having 1 to 10 carbon atoms represented by T 2 hydrocarbon groups the same as those described for R 1 ~R 4 and R 13 can be mentioned, and for the substituents that this hydrocarbon group may have, substituents the same as the above substituent A can be mentioned.

[0078] T 2 The hydrocarbon group having 1 to 10 carbon atoms represented is preferably an aromatic hydrocarbon group, more preferably an aryl group such as phenyl, 1-naphthyl, 2-naphthyl; alkylaryl groups such as o-tolyl, m-tolyl, p-tolyl, 2-ethylphenyl, 3-ethylphenyl, 4-ethylphenyl, 2,3-dimethylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, 3,4-dimethylphenyl, 3,5-dimethylphenyl, 2,4,6-trimethylphenyl, and still more preferably an aryl group such as phenyl; alkylaryl groups such as o-tolyl, m-tolyl, p-tolyl, 2-ethylphenyl, 3-ethylphenyl, 4-ethylphenyl.

[0079] The number of carbon atoms of the hydrocarbon group is preferably 6 to 10, more preferably 6 to 9, and still more preferably 6 to 8.

[0080] <Case where a is an integer of 2 or more>

[0081] T 2 represents an a-valent group which may have substituents, and the —CH2— contained in this a-valent group may be substituted by —O—, —CO—, —S—, —SO—, —SO2— or —NR 1a —.

[0082] R 1a represents a hydrogen atom or an aliphatic hydrocarbon group having 1 to 8 carbon atoms.

[0083] The number of carbon atoms of the a-valent group is preferably 2 to 30, more preferably 3 to 25, still more preferably 5 to 20, and even more preferably 6 to 18.

[0084] T represented by the a-valent group 2 is preferably an a-valent hydrocarbon group which may have substituents, more preferably one or more selected from an a-valent aliphatic hydrocarbon group which may have substituents, an a-valent aromatic hydrocarbon group which may have substituents, and an a-valent aromatic heterocyclic group which may have substituents.

[0085] For the a-valent aliphatic hydrocarbon group, the a-valent aliphatic hydrocarbon group means a group obtained by substituting a hydrogen atoms constituting an aliphatic hydrocarbon for the bonding sites. When a is 2 or more, it is preferred that the a bonding sites are respectively 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, and an a-valent group formed by combining a chain hydrocarbon group and an alicyclic hydrocarbon group.

[0086] The a-valent chain hydrocarbon group may be saturated or unsaturated, and is preferably an a-valent saturated chain hydrocarbon group. Examples of the a-valent saturated chain hydrocarbon group include alkane diyls such as methylene, ethylene, propane-1,2-diyl, propane-1,3-diyl, butane-1,4-diyl, pentane-1,5-diyl, hexane-1,6-diyl; alkane triyls such as the groups represented by the following formulas (a-1) to (a-2); alkane tetrayls such as the group represented by the following formula (a-3). The number of carbon atoms of the a-valent chain hydrocarbon group is preferably 1 to 8, more preferably 1 to 6.

[0087]

[0088] The a-valent alicyclic hydrocarbon group may be saturated or unsaturated, and is preferably an a-valent saturated alicyclic hydrocarbon group. Examples of the a-valent saturated alicyclic hydrocarbon group include divalent saturated alicyclic hydrocarbon groups such as cyclohexane-1,2-diyl, cyclohexane-1,4-diyl, methylcyclohexane-1,2-diyl, methylcyclohexane-1,4-diyl, ethylcyclohexane-1,2-diyl, ethylcyclohexane-1,4-diyl, norbornane-2,5-diyl; trivalent saturated alicyclic hydrocarbon groups such as cyclohexane-1,3,5-triyl; tetravalent saturated alicyclic hydrocarbon groups such as cyclohexane-1,2,4,5-tetrayl. The number of carbon atoms of the a-valent alicyclic hydrocarbon group is preferably 3 to 10, more preferably 3 to 6.

[0089] As an a-valent group formed by combining an acyclic hydrocarbon group and an alicyclic hydrocarbon group, an a-valent group formed by combining at least one acyclic hydrocarbon group and at least one saturated alicyclic hydrocarbon group is preferred. For example, groups represented by the following formulas (a-4) to (a-7) and groups represented by the following formulas (a-8) to (a-13) can be cited.

[0090]

[0091] As substituents that the a-valent aliphatic hydrocarbon group having 1 to 12 carbon atoms can have, groups exemplified as substituent A can be cited.

[0092] The a-valent aromatic hydrocarbon group is a group obtained by substituting a hydrogen atoms directly bonded to carbon atoms constituting the ring in an aromatic hydrocarbon ring with bonding sites. As the aromatic hydrocarbon ring constituting the a-valent aromatic hydrocarbon group, the structures described as the aromatic hydrocarbon ring constituting the above aromatic hydrocarbon group can be cited.

[0093] The a-valent aromatic heterocyclic group is a group obtained by substituting a hydrogen atoms directly bonded to atoms constituting the ring in an aromatic heterocycle with bonding sites. As the aromatic heterocycle constituting the a-valent aromatic heterocyclic group, the structures described as the aromatic heterocycle constituting the above aromatic heterocyclic group can be cited.

[0094] As a group in which -CH2- contained in the a-valent group can be substituted by -O-, -CO-, -S-, -SO-, -SO2- or -NR 1a -, the following groups can be cited (* represents a bonding site).

[0095]

[0096] For R 1a The aliphatic hydrocarbon group represented can be cited as the same aliphatic hydrocarbon group as the aliphatic hydrocarbon group in the hydrocarbon group having 1 to 10 carbon atoms represented by R 1 ~R 4 And R 13 The preferred aliphatic hydrocarbon groups are methyl, ethyl, propyl, and butyl.

[0097] T 2 Preferably represents the group represented by formula (i).

[0098]

[0099] [In formula (i),

[0100] T 3 Represents an a-valent cyclic hydrocarbon group, and L 2 Represents a divalent aliphatic hydrocarbon group having 1 to 5 carbon atoms that can have substituents, or

[0101] T3 represents a divalent aliphatic hydrocarbon group having 1 to 5 carbon atoms which may have substituents, and L 2 represents an a-valent cyclic hydrocarbon group.

[0102] a represents an integer of 1 or more.

[0103] * represents the bonding site to the nitrogen atom.]

[0104] T 3 or L 2 The a-valent cyclic hydrocarbon group represented is preferably 1 or more selected from an a-valent aromatic hydrocarbon group, an a-valent aromatic heterocyclic group, and an a-valent alicyclic hydrocarbon group, as described later.

[0105] For the above a-valent aromatic hydrocarbon group, the above a-valent aromatic heterocyclic group, and the above a-valent alicyclic hydrocarbon group, the same examples as described above can be cited.

[0106] In formula (i), as T 3 or L 2 the divalent aliphatic hydrocarbon group having 1 to 5 carbon atoms represented, there can be cited a divalent chain hydrocarbon group having 1 to 5 carbon atoms and a divalent alicyclic hydrocarbon group having 1 to 5 carbon atoms.

[0107] The divalent chain hydrocarbon group may be saturated or unsaturated, and is preferably a divalent saturated chain hydrocarbon group. As the divalent saturated chain hydrocarbon group, there can be cited alkane diyls such as methylene, ethylene, propane-1,2-diyl, propane-1,3-diyl, butane-1,4-diyl, pentane-1,5-diyl, etc.

[0108] The divalent alicyclic hydrocarbon group may be saturated or unsaturated, and is preferably a divalent saturated alicyclic hydrocarbon group. As the divalent saturated alicyclic hydrocarbon group, there can be cited cyclopropyl-1,2-diyl, cyclobutyl-1,3-diyl, etc.

[0109] As the substituents that the above divalent aliphatic hydrocarbon group having 1 to 5 carbon atoms may have, there can be cited the groups exemplified as substituent A.

[0110] As the group represented by formula (i), specifically, there can be cited the groups represented by the following formula (i1) or (i2).

[0111]

[0112] [In the formula, L i1 ~L i5 each independently represents a divalent saturated chain hydrocarbon group having 1 to 5 carbon atoms.]

[0113] Examples of the divalent saturated chain hydrocarbon group having 1 to 5 carbon atoms include methylene, ethylene, propane-1,2-diyl, propane-1,3-diyl, butane-1,4-diyl, and pentane-1,5-diyl.

[0114] In formulas (i1) to (i2), L i1 and L i2 and L i3 to L i5 may be the same or different, and are preferably the same.

[0115] Specific examples of the group represented by formula (i) also include the groups represented by the following formulas (i3) to (i5).

[0116]

[0117] [In the formula, L i6 represents a divalent saturated chain hydrocarbon group having 1 to 5 carbon atoms.]

[0118] Among them, in the group represented by formula (i), preferably, T 3 represents a divalent aliphatic hydrocarbon group having 1 to 5 carbon atoms that may have a substituent, and L 2 represents an a-valent cyclic hydrocarbon group.

[0119] The group represented by formula (i) is preferably the group represented by formula (i3) or (i4), and more preferably the group represented by formula (i4).

[0120] In one embodiment, T 2 may be the group represented by formula (r).

[0121]

[0122] [In formula (r), L 1 represents an a-valent aliphatic hydrocarbon group having 1 to 12 carbon atoms that may have a substituent or the group represented by formula (ii). T 2 represents a divalent aromatic hydrocarbon group that may have a substituent or a divalent aromatic heterocyclic group that may have a substituent. a represents an integer of 2 or more. * represents the bonding site to the nitrogen atom.]

[0123] Examples of the a-valent aliphatic hydrocarbon group having 1 to 12 carbon atoms represented by L 1 are the same as those described above. 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 formed by combining a chain hydrocarbon group and an alicyclic hydrocarbon group, and the like.

[0124] For T 2The divalent aromatic hydrocarbon group which may have substituents or the divalent aromatic heterocyclic group which may have substituents may be the same groups as those described above, and the preferred ranges may also be the same ranges as those described above.

[0125]

[0126] [In formula (ii),

[0127] T 33 represents an a-valent aromatic hydrocarbon group which may have substituents or an a-valent aromatic heterocyclic group which may have substituents.

[0128] L 22 represents a divalent aliphatic hydrocarbon group having 1 to 5 carbon atoms which may have substituents.

[0129] a represents an integer of 2 or more.

[0130] * represents the bonding site with T 2 .]

[0131] T 33 The a-valent aromatic hydrocarbon group or a-valent aromatic heterocyclic group represented by may be the same examples as those described above, and the preferred ranges may also be the same ranges as those described above.

[0132] L 22 The divalent aliphatic hydrocarbon group having 1 to 5 carbon atoms represented by may be the same examples as those described above, and the preferred ranges may also be the same ranges as those described above.

[0133] As the substituents that the above aromatic hydrocarbon group, the above aromatic heterocyclic group, and the above aliphatic hydrocarbon group may have, the groups exemplified as substituent A can be mentioned.

[0134] As the c-valent anion represented by X c- , known anions can be mentioned. Specifically, 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 tungsten, molybdenum, silicon, and phosphorus and oxygen as essential elements can be mentioned.

[0135] As the boron-containing anions and aluminum-containing anions, for example, the anions represented by the following formula (4) can be mentioned.

[0136]

[0137] [In formula (4), W 1 , W 2 each independently represents a group having two substituents formed by releasing protons from monovalent proton-donating substituents. M A represents boron or aluminum.]

[0138] As a group having two substituents each formed by releasing a proton from a monovalent proton-donating substituent, a group formed by releasing a proton from each of two proton-donating substituents of a compound having at least two monovalent proton-donating substituents (such as a hydroxyl group, a carboxylic acid group, etc.) can be cited. As such a compound, 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, benzilic acid which may have a substituent, or mandelic acid which may have a substituent is preferred.

[0139] Among the compounds exemplified above, as the substituent, a saturated hydrocarbon group (such as an alkyl group, a cycloalkyl group, etc.), a halogen atom, a halogenated alkyl group, a hydroxyl group, an amino group, a nitro group, an alkoxy group, etc. can be cited.

[0140] As salicylic acid which may have a substituent, monoamino salicylic acids such as 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, etc. can be cited; monohydroxy salicylic acids such as 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), etc.; dihydroxy salicylic acids such as 4,5-dihydroxysalicylic acid, 4,6-dihydroxysalicylic acid, etc.; monohalogenated salicylic acids such as 3-chlorosalicylic acid, 4-chlorosalicylic acid, 5-chlorosalicylic acid, 6-chlorosalicylic acid, 3-bromosalicylic acid, 4-bromosalicylic acid, 5-bromosalicylic acid, 6-bromosalicylic acid, etc.; dihalogenated salicylic acids such as 3,5-dichlorosalicylic acid, 3,5-dibromosalicylic acid, 3,5-diiodosalicylic acid, etc.; trihalogenated salicylic acids such as 3,5,6-trichlorosalicylic acid, etc.

[0141] As benzilic acid which may have a substituent, the following can be cited:

[0142]

[0143] As mandelic acid which may have a substituent, the following can be cited:

[0144]

[0145] etc.

[0146] As the preferred anions among the anions represented by formula (4), anions represented by the following formulas and having substituents described in Table 1, i.e., 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, etc. can be mentioned.

[0147]

[0148] [Table 1]

[0149] Anion <![CDATA[R 61 > <![CDATA[R 62 > <![CDATA[R 63 > <![CDATA[R 64 > Anion (BC-1) H H H H Anion (BC-2) OH H H H Anion (BC-3) H OH H H Anion (BC-4) H H OH H Anion (BC-5) H H H OH Anion (BC-6) Cl H H H Anion (BC-7) H Cl H H Anion (BC-8) H H Cl H Anion (BC-9) H H H Cl Anion (BC-10) Br H H H Anion (BC-11) H Br H H Anion (BC-12) H H Br H Anion (BC-13) H H H Br Anion (BC-14) <![CDATA[NH2]]> H H H Anion (BC-15) H <![CDATA[NH2]]> H H Anion (BC-16) H H <![CDATA[NH2]]> H Anion (BC-17) H H H <![CDATA[NH2]]> Anion (BC-18) H tBu H tBu Anion (BC-19) H Cl H Cl Anion (BC-20) H Br H Br Anion (BC-21) H I H I Anion (BC-22) H OH OH H Anion (BC-23) OH H OH H Anion (BC-24) Cl Cl H Cl

[0150]

[0151]

[0152] 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.

[0153] From the viewpoint of solubility in an organic solvent, as the anion represented by formula (4), anions (BC-1), anion (BC-2), anion (BC-3), anion (BC-25), anion (BC-26), anion (BC-27) are preferred, anions (BC-1), anion (BC-2), anion (BC-25) are more preferred, and anions (BC-1), anion (BC-2) are further preferred.

[0154] As the fluorine-containing anions, for example, groups represented by the following formulas (6), (7), (8), and (9) can be mentioned.

[0155]

[0156] [In formula (6), W 3 and W 4 each independently represents a fluorine atom or a fluorinated alkyl group having 1 to 4 carbon atoms, or W 3 and W 4 together represent a fluorinated alkylene group having 1 to 4 carbon atoms.]

[0157]

[0158] [In formula (7), W 5 to W 7Each independently represents a fluorine atom or a fluoroalkyl group having 1 to 4 carbon atoms.

[0159]

[0160] [In formula (8), Y 1 represents a fluoroalkanediyl group having 1 to 4 carbon atoms.

[0161]

[0162] [In formula (9), Y 2 represents a fluoroalkyl group having 1 to 4 carbon atoms.

[0163] In formulas (6), (7) and (9), as the fluoroalkyl group having 1 to 4 carbon atoms, a perfluoroalkyl group is preferred. Examples of the perfluoroalkyl group include -CF3, -CF2CF3, -CF2CF2CF3, -CF(CF3)2, -CF2CF2CF2CF3, -CF2CF(CF3)2, -C(CF3)3 and the like.

[0164] In formulas (6) and (8), as the fluoroalkanediyl group having 1 to 4 carbon atoms, a perfluoroalkanediyl group is preferred. Examples of the perfluoroalkanediyl group include -CF2-, -CF2CF2-, -CF2CF2CF2-, -C(CF3)2-, -CF2CF2CF2CF2- and the like.

[0165] As the anion represented by formula (6) (hereinafter sometimes referred to as "anion (6)"), anions represented by formulas (6-1) to (6-6) (hereinafter sometimes referred to as "anion (6-1)" to "anion (6-6)") can be respectively cited.

[0166]

[0167] As the anion represented by formula (7) (hereinafter sometimes referred to as "anion (7)"), an anion represented by the following formula (7-1) can be cited.

[0168]

[0169] As the anion represented by formula (8) (hereinafter sometimes referred to as "anion (8)"), anions represented by formulas (8-1) to (8-4) (hereinafter sometimes referred to as "anion (8-1)" to "anion (8-4)") can be respectively cited.

[0170]

[0171] As the anion represented by formula (9) (hereinafter sometimes referred to as "anion (9)"), anions represented by formula (9-1) to formula (9-4) (hereinafter sometimes referred to as "anion (9-1)" to "anion (9-4)") can be cited respectively.

[0172]

[0173] By making the c-valent anion represented by X c- be at least one anion selected from anion (6), anion (7), anion (8) and anion (9) (i.e., a fluorine-containing anion), 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.

[0174] As the c-valent anion represented by X c- an anion containing at least one element selected from tungsten, molybdenum, silicon and phosphorus and oxygen as essential elements can be cited. An anion of a heteropolyacid or isopolyacid containing tungsten as an essential element is preferred, and anions of phosphotungstic acid, silicotungstic acid and tungsten-based isopolyacids are more preferred.

[0175] As such an anion of a heteropolyacid or isopolyacid containing tungsten as an essential element, 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- , and 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.

[0176] In addition, among anions other than anions of heteropolyacids or isopolyacids containing tungsten as an essential element, anions composed of at least one element selected from silicon and phosphorus and oxygen are preferred.

[0177] As such anions composed of at least one element selected from silicon and phosphorus and oxygen, SiO3 2- , PO4 3- can be cited.

[0178] Particularly from the viewpoints of ease of synthesis and post-treatment, heteropolyacid anions such as Keggin-type phosphotungstate ions, Dawson-type phosphotungstate ions, Keggin-type silicotungstate ions, and [W 10 O 32 4- and other isopolyacid anions are preferred.

[0179] In formula (I), a plurality of R 1 ~R 13 , T 1 and T 2 can be the same or different respectively, and are preferably the same.

[0180] 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.

[0181] In particular, it is preferred that R 1 and R 3 are each independently 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, and R 2 and R 4 ​​​​​​​Each independently is a saturated acyclic hydrocarbon group having 1 to 10 carbon atoms which may have substituents,

[0182] More preferably, R 1 and R 3 Each independently is a saturated acyclic hydrocarbon group having 1 to 10 carbon atoms which may have substituents, or a phenyl group which may have substituents, and R 2 and R 4 Each independently is a saturated acyclic hydrocarbon group having 1 to 10 carbon atoms which may have substituents,

[0183] Even more preferably, R 1 and R 3 Each independently is a saturated acyclic hydrocarbon group having 1 to 8 carbon atoms which may have substituents, or a phenyl group which may have substituents and has an alkyl group having 1 to 4 carbon atoms at at least one of two bonding positions ortho to the N bonded to the phenyl group, and R 2 and R 4 Each independently is a saturated acyclic hydrocarbon group having 1 to 6 carbon atoms which may have substituents,

[0184] Even further preferably, R 1 and R 3 Each independently is a saturated acyclic hydrocarbon group having 1 to 6 carbon atoms which may have substituents, or a phenyl group which may have substituents and has an alkyl group having 1 to 4 carbon atoms at at least one of two bonding positions ortho to the N bonded to the phenyl group, and R 2 and R 4 Each independently is a saturated acyclic hydrocarbon group having 2 to 6 carbon atoms which may have substituents,

[0185] Particularly preferably, R 1 and R 3 Each independently is an alkyl group having 1 to 6 carbon atoms, or a phenyl group which may have substituents and has alkyl groups having 1 to 3 carbon atoms at the two bonding positions ortho to the N bonded to the phenyl group, and R 2 and R 4 Each independently is a saturated acyclic hydrocarbon group having 2 to 6 carbon atoms which may have substituents.

[0186] Here, as the substituents which the above phenyl group may have, examples include at least one or more selected from alkyl groups having 1 to 4 carbon atoms, halogen atoms, hydroxy groups, alkoxy groups, formyl groups, substituted or unsubstituted amino groups, nitro groups, cyano groups, -SO3 - and -SO3M (M is the same as above), and among them, preferably selected from alkyl groups having 1 to 4 carbon atoms, halogen atoms, alkoxy groups and -SO3 -at least one or more, more preferably selected from alkyl groups having 1 to 4 carbon atoms, alkoxy groups having 1 to 4 carbon atoms, and -SO3 - at least one or more thereof.

[0187] In particular, the above phenyl group has no substituent, or has only a substituent selected from alkyl groups having 1 to 4 carbon atoms, halogen atoms, hydroxyl groups, formyl groups, substituted or unsubstituted amino groups, nitro groups, cyano groups, -SO3 - , and at least one or more substituents of -SO3M (preferably only substituents selected from alkyl groups having 1 to 4 carbon atoms and -SO3 - ), the brightness of the obtained color filter can be further improved.

[0188] In addition, when the above phenyl group has an alkoxy group (preferably a methoxy group) as a substituent, the light resistance can be improved. The substitution position of the above alkoxy group (preferably a methoxy group) is not particularly limited, and by bonding to the position para to N bonded to the phenyl group, the above light resistance improvement effect can be further improved.

[0189] The above R 1 ~R 4 In the preferred mode, it is particularly preferred that R 1 and R 3 are each independently methyl, ethyl, or any one of the groups represented by formulas (r1) to (r3). It should be noted that any one or more of the hydrogen atoms of the groups represented by formulas (r1) to (r3) may be substituted by -SO3 - .

[0190]

[0191] [In the formula, R r1 ~R r4 each independently represent an alkyl group having 1 to 4 carbon atoms. * represents the bonding site.]

[0192] R r1 ~R r4 are preferably methyl, ethyl, propyl, more preferably methyl, ethyl, and further preferably methyl.

[0193] R 5 ~R 12 are preferably hydrogen atoms.

[0194] 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, further preferably a hydrogen atom, methyl, ethyl, n-propyl, or isopropyl, and even more preferably a hydrogen atom, methyl, or ethyl.

[0195] As T 1 The divalent aromatic ring represented is preferably a benzene ring, a naphthalene ring, or a structure obtained by substituting at least one hydrogen atom of these rings with a saturated chain hydrocarbon group having 1 to 10 carbon atoms (preferably 1 to 4 carbon atoms). As T 1 , more preferably any one 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).

[0196] In addition, as T 1 The divalent aromatic ring represented is preferably An oxazole ring, a pyrazole ring, an imidazole ring, a thiazole ring, or a structure obtained by substituting at least one hydrogen atom of these rings with a hydrocarbon group having 1 to 10 carbon atoms (preferably a saturated chain hydrocarbon group having 1 to 4 carbon atoms or an aromatic hydrocarbon group having 6 to 10 carbon atoms) which may have substituents.

[0197] When a is 1, T 2 is preferably an aromatic hydrocarbon group which may have substituents. As the aromatic hydrocarbon ring constituting the above aromatic hydrocarbon group, a benzene ring, a naphthalene ring, or a structure obtained by substituting at least one hydrogen atom of these rings with a saturated chain hydrocarbon group having 1 to 10 carbon atoms (preferably 1 to 4 carbon atoms) is preferred, and a benzene ring or a structure obtained by substituting at least one hydrogen atom of a benzene ring with a saturated chain hydrocarbon group having 1 to 4 carbon atoms is more preferred.

[0198] When a is 2, T 2 is preferably a divalent aliphatic hydrocarbon group having 1 to 5 carbon atoms which may have substituents - a divalent cyclic hydrocarbon group which may have substituents - a divalent aliphatic hydrocarbon group having 1 to 5 carbon atoms which may have substituents, more preferably a divalent aliphatic hydrocarbon group having 1 to 5 carbon atoms which may have substituents - a divalent alicyclic hydrocarbon group which may have substituents - a divalent aliphatic hydrocarbon group having 1 to 5 carbon atoms which may have substituents, and further preferably a divalent aliphatic hydrocarbon group having 1 to 3 carbon atoms which may have substituents - a divalent alicyclic hydrocarbon group which may have substituents - a divalent aliphatic hydrocarbon group having 1 to 3 carbon atoms which may have substituents.

[0199] When a is 2, T 2 is preferably a divalent cyclic hydrocarbon group which may have substituents - a divalent aliphatic hydrocarbon group having 1 to 5 carbon atoms which may have substituents - a divalent cyclic hydrocarbon group which may have substituents.

[0200] More preferably, it is a divalent alicyclic hydrocarbon group which may have substituents - a divalent aliphatic hydrocarbon group having 1 to 5 carbon atoms which may have substituents - a divalent alicyclic hydrocarbon group which may have substituents, and more preferably a divalent aromatic hydrocarbon group which may have substituents - a divalent aliphatic hydrocarbon group having 1 to 5 carbon atoms which may have substituents - a divalent aromatic hydrocarbon group which may have substituents.

[0201] Even more preferably, it is a divalent alicyclic hydrocarbon group which may have substituents - a divalent aliphatic hydrocarbon group having 1 to 3 carbon atoms which may have substituents - a divalent alicyclic hydrocarbon group which may have substituents, and even more preferably a divalent aromatic hydrocarbon group which may have substituents - a divalent aliphatic hydrocarbon group having 1 to 3 carbon atoms which may have substituents - a divalent aromatic hydrocarbon group which may have substituents.

[0202] T 2 When a is 2 and in the formula (r), it is preferably a divalent aromatic hydrocarbon group which may have substituents. As the aromatic hydrocarbon ring constituting the above divalent aromatic hydrocarbon group, it is preferably a benzene ring, a naphthalene ring, or a structure obtained by substituting at least 1 hydrogen atom of these rings with a saturated chain hydrocarbon group having 1 to 10 (preferably 1 to 4) carbon atoms, and more preferably a benzene ring or a structure obtained by substituting at least 1 hydrogen atom of the benzene ring with a saturated chain hydrocarbon group having 1 to 4 carbon atoms. As T 2 , it is even more preferably any one of the groups represented by the following formulas (Tb-1) to (Tb-10), and even more preferably any one of the groups represented by the following formulas (Tb-3), (Tb-5), (Tb-6), (Tb-9), (Tb-10), and particularly preferably any one of the groups represented by the following formulas (Tb-5), (Tb-6), (Tb-9), (Tb-10).

[0203]

[0204] [In the formula, * represents the bonding site with L 1 , and ** represents the bonding site with the nitrogen atom.]

[0205] L 1 is preferably a valence aliphatic hydrocarbon group having 1 to 8 carbon atoms which may have substituents, or in the group represented by the formula (ii), T 33 is a valence aromatic hydrocarbon group which may have substituents, L 22A group which is a divalent saturated chain hydrocarbon group having 1 to 5 carbon atoms, more preferably an alkylene 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 further preferably an alkylene 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 one of the groups represented by the following formulas (i-1) to (i-4).

[0206]

[0207] As X c- represents a c-valent anion, preferably a halide ion or an anion containing at least one element selected from tungsten, molybdenum, silicon and phosphorus and oxygen as essential elements, more preferably a halide ion or an anion of a heteropolyacid or isopolyacid containing tungsten as an essential element, and further preferably a halide ion, a Keggin-type phosphotungstate ion or a Dawson-type phosphotungstate ion.

[0208] As the substituent (i.e., substituent A) possessed by the compound (I), it is preferably at least one or more selected from a halogen atom, a hydroxyl group, an alkoxy group, a substituted or unsubstituted amino group, -SO3 - and -SO3M, more preferably at least one or more selected from a halogen atom, an alkoxy group, -SO3 - and -SO3M.

[0209] a is preferably an integer of 2 to 6, more preferably an integer of 2 to 4, and further preferably 2 or 3.

[0210] c is usually 1 to 14, preferably 1 to 12, more preferably 1 to 10, further preferably 1 to 6, and particularly preferably 1 to 4.

[0211] b and d are determined according to a, c and the number of -SO3 - possessed by the compound (I) in the form of a substituent (hereinafter sometimes referred to as e). Generally, the overall charge of the formula (I) is adjusted to 0. Therefore, usually, a to d in the formula (I) satisfy the relationship of the following formula (z).

[0212] a × b = (c × d) + e ··· (z)

[0213] [In the above formula, a to d represent the same meanings as described above. e represents the number of -SO3 - possessed by the compound (I) in the form of a substituent.]

[0214] e is an integer of 0 or more, preferably 0 to (a + 1), more preferably 0 to a, and still more preferably 0 or a. In particular, when d is 1 or more, it is preferable that e is 0, that is, the compound (I) does not have -SO3 - , and when d is 0, it is preferably e = a.

[0215] It should be noted that from the viewpoints of heat resistance and solvent resistance, it is preferable that X c- is an anion containing at least one element selected from tungsten, molybdenum, silicon, and phosphorus and oxygen as essential elements, d is 1 or more, and e is 0.

[0216] The compound (I) in which a is 1 is preferably the compound represented by the formula (I-0).

[0217]

[0218] [In the formula (I-0),

[0219] R 51 and R 53 are each independently a phenyl group which may have a substituent,

[0220] R 52 and R 54 are each independently a saturated chain hydrocarbon group having 1 to 10 carbon atoms which may have a substituent,

[0221] R 55 to R 62 are hydrogen atoms,

[0222] R 63 is a hydrogen atom or a saturated chain hydrocarbon group having 1 to 6 carbon atoms which may have a substituent,

[0223] T 51 represents a divalent aromatic heterocyclic group which may have a substituent,

[0224] T 52 represents an aromatic hydrocarbon group which may have a substituent,

[0225] a51 is 1,

[0226] d51 represents an integer of 1 or more,

[0227] b, c, and X c- represent the same meanings as described above.]

[0228] For the above-mentioned saturated chain hydrocarbon groups, the above-mentioned aromatic heterocyclic groups, the above-mentioned aromatic hydrocarbon groups, and the substituents of these groups, the same examples as described above can be cited.

[0229] R 52 and R 54Each is independently preferably a saturated chain hydrocarbon group having 1 to 8 carbon atoms which may have substituents, more preferably a saturated chain hydrocarbon group having 1 to 6 carbon atoms which may have substituents, still more preferably a saturated chain hydrocarbon group having 1 to 4 carbon atoms which may have substituents, even more preferably an alkyl group having 1 to 3 carbon atoms which may have substituents, and particularly preferably a methyl group, an ethyl group or a propyl group.

[0230] R 63 It is preferably a saturated chain hydrocarbon group having 1 to 5 carbon atoms, more preferably a saturated chain hydrocarbon group having 1 to 4 carbon atoms, still more preferably a saturated chain hydrocarbon group having 1 to 3 carbon atoms, even more preferably an alkyl group having 1 to 3 carbon atoms, and particularly preferably a methyl group or an ethyl group.

[0231] T 52 It is preferably an aryl group or an alkylaryl group which may have substituents, more preferably a phenyl group, a 1-naphthyl group, a 2-naphthyl group, an o-tolyl group, an m-tolyl group, a p-tolyl group, a 2-ethylphenyl group, a 3-ethylphenyl group, a 4-ethylphenyl group, a 2,3-dimethylphenyl group, a 2,4-dimethylphenyl group, a 2,5-dimethylphenyl group, a 2,6-dimethylphenyl group, a 3,4-dimethylphenyl group, a 3,5-dimethylphenyl group, or a 2,4,6-trimethylphenyl group, and still more preferably an o-tolyl group, an m-tolyl group, or a p-tolyl group.

[0232] T 51 It is preferably a group represented by the formula (T 51 -1).

[0233]

[0234] [In the formula (T 51 -1), R 100 represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an aromatic hydrocarbon group having 6 to 10 carbon atoms which may be substituted.

[0235] X2 represents an oxygen atom or a sulfur atom.

[0236] * represents the bonding site to a carbon atom, and ** represents the bonding site to a nitrogen atom.]

[0237] R 100Preferably an alkyl group having 1 to 10 carbon atoms, or an aromatic hydrocarbon group having 6 to 10 carbon atoms which may be substituted, more preferably an alkyl group having 1 to 8 carbon atoms, a halogen atom, a haloalkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a hydroxyl group, an alkyl group having 1 to 4 carbon atoms, or an aromatic hydrocarbon group having 6 to 10 carbon atoms which may be substituted by a methylsulfonyl group, and still more preferably a phenyl group, an o-tolyl group, an m-tolyl group, a p-tolyl group, or a phenyl group having at least one of a fluorine atom, a chlorine atom, a bromine atom, a trifluoromethyl group or a methanesulfonyl group bonded thereto at the ortho-position, para-position or para-position relative to the bonding site.

[0238] b and c are each independently preferably an integer of 1 to 4, more preferably an integer of 1 to 3.

[0239] d51 is preferably 1.

[0240] For the compound (I) in which a is an integer of 2 or more, the compound is preferably a compound represented by formula (I-1) or formula (I-2).

[0241]

[0242] [In formula (I-1),

[0243] R 101 and R 103 are each independently a phenyl group which may have a substituent,

[0244] R 102 and R 104 are each independently a saturated chain hydrocarbon group having 1 to 10 carbon atoms which may have a substituent,

[0245] R 105 ~R 112 are hydrogen atoms,

[0246] R 113 is a hydrogen atom or a saturated chain hydrocarbon group having 1 to 6 carbon atoms which may have a substituent,

[0247] T 101 and T 102 are a divalent aromatic hydrocarbon group which may have a substituent, and the aromatic hydrocarbon ring constituting the divalent aromatic hydrocarbon group is a benzene ring, a naphthalene ring, or a structure in which at least one hydrogen atom of these rings is substituted by a saturated chain hydrocarbon group having 1 to 4 carbon atoms,

[0248] L 101 is a C1-8 a101-valent aliphatic hydrocarbon group which may have a substituent, or represents a group represented by the following formula (i-1),

[0249] a101 is 2 or 3,

[0250] d101 represents an integer of 1 or more.

[0251] b, c, and X c- represent the same meaning as described above.

[0252]

[0253] [In formula (i - 1),

[0254] T 103 represents an a101-valent aromatic hydrocarbon group which may have substituents.

[0255] L 102 represents a divalent aliphatic hydrocarbon group having 1 to 5 carbon atoms.

[0256] a101 is 2 or 3.

[0257] * represents the bonding site with T 102 .

[0258]

[0259] [In formula (I - 2),

[0260] R 201 and R 203 are each independently a phenyl group which may have substituents,

[0261] R 202 and R 204 are each independently a saturated chain hydrocarbon group having 1 to 10 carbon atoms which may have substituents,

[0262] R 205 to R 212 are hydrogen atoms,

[0263] R 213 is a hydrogen atom or a saturated chain hydrocarbon group having 1 to 6 carbon atoms which may have substituents,

[0264] T 201 and T 202 are divalent aromatic hydrocarbon groups which may have substituents, and the aromatic hydrocarbon ring constituting the divalent aromatic hydrocarbon group is a benzene ring, a naphthalene ring, or a structure in which at least 1 hydrogen atom of these rings is substituted with a saturated chain hydrocarbon group having 1 to 4 carbon atoms,

[0265] L 201 is an a201-valent aliphatic hydrocarbon group having 1 to 8 carbon atoms which may have substituents, or represents a group represented by the following formula (i - 2),

[0266] a201 and e201 are 2 or 3,

[0267] The R of the compound represented by formula (I-2) 201 ~R 213 、T 201 、T 202 and L 201 Any e201 of the hydrogen atoms possessed are replaced by -SO3 - .]

[0268]

[0269] [In formula (i-2),

[0270] T 203 represents an a201-valent aromatic hydrocarbon group which may have substituents.

[0271] L 202 represents a divalent saturated chain hydrocarbon group having 1 to 5 carbon atoms.

[0272] a201 is 2 or 3.

[0273] * represents the bonding site to T 202 .]

[0274] As the substituents that the phenyl groups represented by R 101 、R 103 、R 201 、R 203 、the R to be described later 301 、R 303 may have, there may be mentioned at least one or more selected from alkyl groups having 1 to 4 carbon atoms, halogen atoms, hydroxyl groups, alkoxy groups, formyl groups, substituted or unsubstituted amino groups, nitro groups, cyano groups, and -SO3M (M is a hydrogen atom or an alkali metal atom). Among them, it is preferably at least one or more selected from alkyl groups having 1 to 4 carbon atoms and alkoxy groups having 1 to 4 carbon atoms. As the halogen atom, alkoxy group, substituted amino group, and alkali metal atom, they are the same as the halogen atom, alkoxy group, substituted amino group, and alkali metal atom described as substituent A.

[0275] R 101 、R 103 、R 201 、R 203 、the R to be described later 301 、R 303 are each independently preferably a phenyl group which may have substituents, and is a group having an alkyl group having 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 、R 203 、the R to be described later 301 、R 303Each is independently preferably any one of the groups represented by the above formulas (r1) to (r3), more preferably the group represented by the above formula (r1) or (r2) from the viewpoint of better brightness, and more preferably the group represented by the above formula (r3) from the viewpoint of better light resistance.

[0276] R 102 、R 104 、R 202 、R 204 、R hereinafter described 302 、R 304 Each is independently preferably a saturated chain hydrocarbon group having 1 to 6 carbon atoms which may have a substituent, more preferably a saturated chain hydrocarbon group having 2 to 6 carbon atoms, and further preferably a saturated chain hydrocarbon group having 2 to 4 carbon atoms. As the saturated chain hydrocarbon group represented by R 102 、R 104 、R 202 、R 204 、R hereinafter described 302 、R 304 The substituent (hereinafter referred to as substituent B) that the saturated chain hydrocarbon group represented by can have includes at least one selected from a halogen atom, a hydroxyl 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). As the halogen atom, alkoxy group, substituted amino group, and alkali metal atom, they are the same as the halogen atom, alkoxy group, substituted amino group, and alkali metal atom described as substituent A.

[0277] As the substituent that the saturated chain hydrocarbon group having 1 to 6 carbon atoms represented by R 113 、R 213 、R hereinafter described 313 can have, the groups described as substituent B can be cited.

[0278] R 113 、R 213 、R hereinafter described 313 is preferably a hydrogen atom.

[0279] As the substituent that the divalent aromatic hydrocarbon group represented by T 101 、T 201 、T hereinafter described 301 can have, the groups described as substituent B can be cited. As T 101 、T 201 、T hereinafter described 301 is preferably any one of the groups represented by the above formulas (Ta-1) to (Ta-8), and more preferably the group represented by the formula (Ta-8).

[0280] As T 102 and T 202The substituents that the divalent aromatic hydrocarbon group represented can have include the groups described as substituent B, among which at least one or more selected from a halogen atom and an alkoxy group are preferred. As T 102 and T 202 , it is preferably a divalent aromatic hydrocarbon group that can have substituents, and the aromatic hydrocarbon ring constituting the divalent aromatic hydrocarbon group is a benzene ring or a structure obtained by substituting at least one hydrogen atom of the benzene ring with a saturated chain hydrocarbon group having 1 to 4 carbon atoms. More preferably, it is any one of the groups represented by the above formulas (Tb-1) to (Tb-10), still more preferably any one of the groups represented by formulas (Tb-5), (Tb-6), (Tb-9), and (Tb-10), and particularly preferably any one of the groups represented by formulas (Tb-5) and (Tb-6).

[0281] As the a-valent saturated chain hydrocarbon group having 1 to 8 carbon atoms represented by L 101 and L 201 , the a-valent aromatic hydrocarbon group represented by T 3 , the a101-valent aromatic hydrocarbon group represented by T 103 , the a201-valent aromatic hydrocarbon group represented by T 203 , and the substituents of the aliphatic hydrocarbon group represented by L 2 , the groups described as substituent B can be cited. As L 101 and L 201 , it is preferably an alkylene group having 1 to 6 carbon atoms that can have substituents, a divalent saturated alicyclic hydrocarbon group having 3 to 10 carbon atoms that can have substituents, or any one of the groups represented by the above formulas (i1) or (i2).

[0282] In formula (i-1), the a101-valent aromatic hydrocarbon group represented by T 103 refers to a group in which a101 hydrogen atoms directly bonded to the carbon atoms constituting the ring in the aromatic hydrocarbon ring are substituted with bonding sites. As the aromatic hydrocarbon ring constituting the a101-valent aromatic hydrocarbon group, the structures described above as the aromatic hydrocarbon ring constituting the divalent aromatic hydrocarbon group can be cited.

[0283] In formula (i-2), the a201-valent aromatic hydrocarbon group represented by T 203 refers to a group in which a201 hydrogen atoms directly bonded to the carbon atoms constituting the ring in the aromatic hydrocarbon ring are substituted with bonding sites. As the aromatic hydrocarbon ring constituting the a201-valent aromatic hydrocarbon group, the structures described above as the aromatic hydrocarbon ring constituting the divalent aromatic hydrocarbon group can be cited.

[0284] L 102 and L 202An alkane diyl group having 1 to 5 carbon atoms is preferred, and 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 is more preferred.

[0285] a201 and e201 are preferably the same. a101 in formula (I-1) is preferably the same as a101 in formula (i-1). a201 in formula (I-2) is preferably the same as a201 in formula (i-2).

[0286] The compounds represented by formula (I-0), formula (I-1) and formula (I-2) preferably have a charge of zero.

[0287] In addition, from the viewpoint of heat resistance and solvent resistance, the compound represented by formula (I-1) is preferred.

[0288] Specific examples of 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). The compound represented by formula (I-b) is a compound in which b is 1 and d is 0 in compound (I). R of the compound represented by formula (I-b) is 1b ~R 13b 、T 1b 、T 2b and L 1b Any e2 of the hydrogen atoms contained in -SO3 - replace.

[0289]

[0290] [Table 2]

[0291] <![CDATA[R 1a ,R 3a > <![CDATA[R 2a , R 4a > <![CDATA[R 5a ~R 12a > <![CDATA[R 13a > <![CDATA[T 1a > <![CDATA[T 2a > <![CDATA[L 1a > a1 b1 <![CDATA[X c1- > d1 I-1a-1 r-1 Et H H Ta-8 Tb-5 l-1 2 1 <![CDATA[Cl - > 2 I-2a-1 r-2 Et H H Ta-8 Tb-5 l-1 2 1 <![CDATA[Cl - > 2 I-3a-1 r-3 Et H H Ta-8 Tb-5 l-1 2 1 <![CDATA[Cl - > 2 I-4a-1 r-1 Et H H Ta-8 Tb-6 l-1 2 1 <![CDATA[Cl - > 2 I-5a-1 r-2 Et H H Ta-8 Tb-6 l-1 2 1 <![CDATA[Cl - > 2 I-6a-1 r-3 Et H H Ta-8 Tb-6 l-1 2 1 <![CDATA[Cl - > 2 I-7a-1 r-1 Et H Et Ta-8 Tb-5 l-1 2 1 <![CDATA[Cl - > 2 I-8a-1 r-2 Et H Et Ta-8 Tb-5 l-1 2 1 <![CDATA[Cl - > 2 I-9a-1 r-3 Et H Et Ta-8 Tb-5 l-1 2 1 <![CDATA[Cl - > 2 I-10a-1 r-1 Et H Et Ta-8 Tb-6 l-1 2 1 <![CDATA[Cl - > 2 I-11a-1 r-2 Et H Et Ta-8 Tb-6 l-1 2 1 <![CDATA[Cl - > 2 I-12a-1 r-3 Et H Et Ta-8 Tb-6 l-1 2 1 <![CDATA[Cl - > 2 I-13a-1 r-1 Et H Pr Ta-8 Tb-5 l-1 2 1 <![CDATA[Cl - > 2 I-14a-1 r-2 Et H Pr Ta-8 Tb-5 l-1 2 1 <![CDATA[Cl - > 2 I-15a-1 r-3 Et H Pr Ta-8 Tb-5 l-1 2 1 <![CDATA[Cl - > 2 I-16a-1 r-1 Et H Pr Ta-8 Tb-6 l-1 2 1 <![CDATA[Cl - > 2 I-17a-1 r-2 Et H Pr Ta-8 Tb-6 l-1 2 1 <![CDATA[Cl - > 2 I-18a-1 r-3 Et H Pr Ta-8 Tb-6 l-1 2 1 <![CDATA[Cl - > 2 I-19a-1 r-1 Et H H Ta-8 Tb-5 i-2 2 1 <![CDATA[Cl - > 2 I-20a-1 r-2 Et H H Ta-8 Tb-5 i-2 2 1 <![CDATA[Cl - > 2 I-21a-1 r-3 Et H H Ta-8 Tb-5 i-2 2 1 <![CDATA[Cl - > 2 I-22a-1 r-1 Et H H Ta-8 Tb-6 i-2 2 1 <![CDATA[Cl - > 2 I-23a-1 r-2 Et H H Ta-8 Tb-6 i-2 2 1 <![CDATA[Cl - > 2 I-24a-1 r-3 Et H H Ta-8 Tb-6 i-2 2 1 <![CDATA[Cl - > 2 I-25a-1 r-1 Et H Et Ta-8 Tb-5 i-2 2 1 <![CDATA[Cl - > 2 I-26a-1 r-2 Et H Et Ta-8 Tb-5 i-2 2 1 <![CDATA[Cl - > 2 I-27a-1 r-3 Et H Et Ta-8 Tb-5 i-2 2 1 <![CDATA[Cl - > 2 I-28a-1 r-1 Et H Et Ta-8 Tb-6 i-2 2 1 <![CDATA[Cl - > 2 I-29a-1 r-2 Et H Et Ta-8 Tb-6 i-2 2 1 <![CDATA[Cl - > 2 I-30a-1 r-3 Et H Et Ta-8 Tb-6 i-2 2 1 <![CDATA[Cl - > 2 I-31a-1 r-1 Et H Pr Ta-8 Tb-5 i-2 2 1 <![CDATA[Cl - > 2 I-32a-1 r-2 Et H Pr Ta-8 Tb-5 i-2 2 1 <![CDATA[Cl - > 2 I-33a-1 r-3 Et H Pr Ta-8 Tb-5 i-2 2 1 <![CDATA[Cl - > 2 I-34a-1 r-1 Et H Pr Ta-8 Tb-6 i-2 2 1 <![CDATA[Cl - > 2 I-35a-1 r-2 Et H Pr Ta-8 Tb-6 i-2 2 1 <![CDATA[Cl - > 2 I-36a-1 r-3 Et H Pr Ta-8 Tb-6 i-2 2 1 <![CDATA[Cl - > 2 I-37a-1 r-1 Et H H Ta-8 Tb-5 i-4 3 1 <![CDATA[Cl - > 3 I-38a-1 r-2 Et H H Ta-8 Tb-5 i-4 3 1 <![CDATA[Cl - > 3 I-39a-1 r-3 Et H H Ta-8 Tb-5 i-4 3 1 <![CDATA[Cl - > 3 I-40a-1 r-1 Et H H Ta-8 Tb-6 i-4 3 1 <![CDATA[Cl - > 3 I-41a-1 r-2 Et H H Ta-8 Tb-6 i-4 3 1 <![CDATA[Cl - > 3 I-42a-1 r-3 Et H H Ta-8 Tb-6 i-4 3 1 <![CDATA[Cl - > 3 I-43a-1 r-1 Et H Et Ta-8 Tb-5 i-4 3 1 <![CDATA[Cl - > 3 I-44a-1 r-2 Et H Et Ta-8 Tb-5 i-4 3 1 <![CDATA[Cl - > 3 I-45a-1 r-3 Et H Et Ta-8 Tb-5 i-4 3 1 <![CDATA[Cl - > 3

[0292] [Table 3]

[0293] <![CDATA[R 1a ,R 3a > <![CDATA[R 2a ,R 4a > <![CDATA[R 5a ~R 12a > <![CDATA[R 13a > <![CDATA[T 1a > <![CDATA[T 2a > <![CDATA[L 1a > a1 b1 <![CDATA[X c1- > d1 I-46a-1 r-1 Et H Et Ta-8 Tb-6 i-4 3 1 <![CDATA[Cl - > 3 I-47a-1 r-2 Et H Et Ta-8 Tb-6 i-4 3 1 <![CDATA[Cl - > 3 I-48a-1 r-3 Et H Et Ta-8 Tb-6 i-4 3 1 <![CDATA[Cl - > 3 I-49a-1 r-1 Et H Pr Ta-8 Tb-5 i-4 3 1 <![CDATA[Cl - > 3 I-50a-1 r-2 Et H Pr Ta-8 Tb-5 i-4 3 1 <![CDATA[Cl - > 3 I-51a-1 r-3 Et H Pr Ta-8 Tb-5 i-4 3 1 <![CDATA[Cl - > 3 I-52a-1 r-1 Et H Pr Ta-8 Tb-6 i-4 3 1 <![CDATA[Cl - > 3 I-53a-1 r-2 Et H Pr Ta-8 Tb-6 i-4 3 1 <![CDATA[Cl - > 3 I-54a-1 r-3 Et H Pr Ta-8 Tb-6 i-4 3 1 <![CDATA[Cl - > 3 I-55a-1 r-1 Et H H Ta-8 Tb-9 l-1 2 1 <![CDATA[Cl - > 2 I-56a-1 r-2 Et H H Ta-8 Tb-9 l-1 2 1 <![CDATA[Cl - > 2 I-57a-1 r-3 Et H H Ta-8 Tb-9 l-1 2 1 <![CDATA[Cl - > 2 I-58a-1 r-1 Et H H Ta-8 Tb-10 l-1 2 1 <![CDATA[Cl - > 2 I-59a-1 r-2 Et H H Ta-8 Tb-10 l-1 2 1 <![CDATA[Cl - > 2 I-60a-1 r-3 Et H H Ta-8 Tb-10 l-1 2 1 <![CDATA[Cl - > 2 I-61a-1 r-1 Et H Et Ta-8 Tb-9 l-1 2 1 <![CDATA[Cl - > 2 I-62a-1 r-2 Et H Et Ta-8 Tb-9 l-1 2 1 <![CDATA[Cl - > 2 I-63a-1 r-3 Et H Et Ta-8 Tb-9 l-1 2 1 <![CDATA[Cl - > 2 I-64a-1 r-1 Et H Et Ta-8 Tb-10 l-1 2 1 <![CDATA[Cl - > 2 I-65a-1 r-2 Et H Et Ta-8 Tb-10 l-1 2 1 <![CDATA[Cl - > 2 I-66a-1 r-3 Et H Et Ta-8 Tb-10 l-1 2 1 <![CDATA[Cl - > 2 I-67a-1 r-1 Et H Pr Ta-8 Tb-9 l-1 2 1 <![CDATA[Cl - > 2 I-68a-1 r-2 Et H Pr Ta-8 Tb-9 l-1 2 1 <![CDATA[Cl - > 2 I-69a-1 r-3 Et H Pr Ta-8 Tb-9 l-1 2 1 <![CDATA[Cl - > 2 I-70a-1 r-1 Et H Pr Ta-8 Tb-10 l-1 2 1 <![CDATA[Cl - > 2 I-71a-1 r-2 Et H Pr Ta-8 Tb-10 l-1 2 1 <![CDATA[Cl - > 2 I-72a-1 r-3 Et H Pr Ta-8 Tb-10 l-1 2 1 <![CDATA[Cl - > 2 I-73a-1 r-1 Et H H Ta-8 Tb-9 i-2 2 1 <![CDATA[Cl - > 2 I-74a-1 r-2 Et H H Ta-8 Tb-9 i-2 2 1 <![CDATA[Cl - > 2 I-75a-1 r-3 Et H H Ta-8 Tb-9 i-2 2 1 <![CDATA[Cl - > 2 I-76a-1 r-1 Et H H Ta-8 Tb-10 i-2 2 1 <![CDATA[Cl - > 2 I-77a-1 r-2 Et H H Ta-8 Tb-10 i-2 2 1 <![CDATA[Cl - > 2 I-78a-1 r-3 Et H H Ta-8 Tb-10 i-2 2 1 <![CDATA[Cl - > 2 I-79a-1 r-1 Et H Et Ta-8 Tb-9 i-2 2 1 <![CDATA[Cl - > 2 I-80a-1 r-2 Et H Et Ta-8 Tb-9 i-2 2 1 <![CDATA[Cl - > 2 I-81a-1 r-3 Et H Et Ta-8 Tb-9 i-2 2 1 <![CDATA[Cl - > 2 I-82a-1 r-1 Et H Et Ta-8 Tb-10 i-2 2 1 <![CDATA[Cl - > 2 I-83a-1 r-2 Et H Et Ta-8 Tb-10 i-2 2 1 <![CDATA[Cl - > 2 I-84a-1 r-3 Et H Et Ta-8 Tb-10 i-2 2 1 <![CDATA[Cl - > 2 I-85a-1 r-1 Et H Pr Ta-8 Tb-9 i-2 2 1 <![CDATA[Cl - > 2 I-86a-1 r-2 Et H Pr Ta-8 Tb-9 i-2 2 1 <![CDATA[Cl - > 2 I-87a-1 r-3 Et H Pr Ta-8 Tb-9 i-2 2 1 <![CDATA[Cl - > 2 I-88a-1 r-1 Et H Pr Ta-8 Tb-10 i-2 2 1 <![CDATA[Cl - > 2 I-89a-1 r-2 Et H Pr Ta-8 Tb-10 i-2 2 1 <![CDATA[Cl - > 2 I-90a-1 r-3 Et H Pr Ta-8 Tb-10 i-2 2 1 <![CDATA[Cl - > 2

[0294] [Table 4]

[0295] <![CDATA[R 1a ,R 3a > <![CDATA[R 2a ,R 4a > <![CDATA[R 5a ~R 12a > <![CDATA[R 13a > <![CDATA[T 1a > <![CDATA[T 2a > <![CDATA[L 1a > a1 b1 <![CDATA[X c1- > d1 I-91a-1 r-1 Et H H Ta-8 Tb-9 i-4 3 1 <![CDATA[Cl - > 3 I-92a-1 r-2 Et H H Ta-8 Tb-9 i-4 3 1 <![CDATA[Cl - > 3 I-93a-1 r-3 Et H H Ta-8 Tb-9 i-4 3 1 <![CDATA[Cl - > 3 I-94a-1 r-1 Et H H Ta-8 Tb-10 i-4 3 1 <![CDATA[Cl - > 3 I-95a-1 r-2 Et H H Ta-8 Tb-10 i-4 3 1 <![CDATA[Cl - > 3 I-96a-1 r-3 Et H H Ta-8 Tb-10 i-4 3 1 <![CDATA[Cl - > 3 I-97a-1 r-1 Et H Et Ta-8 Tb-9 i-4 3 1 <![CDATA[Cl - > 3 I-98a-1 r-2 Et H Et Ta-8 Tb-9 i-4 3 1 <![CDATA[Cl - > 3 I-99a-1 r-3 Et H Et Ta-8 Tb-9 i-4 3 1 <![CDATA[Cl - > 3 I-100a-1 r-1 Et H Et Ta-8 Tb-10 i-4 3 1 <![CDATA[Cl - > 3 I-101a-1 r-2 Et H Et Ta-8 Tb-10 i-4 3 1 <![CDATA[Cl - > 3 I-102a-1 r-3 Et H Et Ta-8 Tb-10 i-4 3 1 <![CDATA[Cl - > 3 I-103a-1 r-1 Et H Pr Ta-8 Tb-9 i-4 3 1 <![CDATA[Cl - > 3 I-104a-1 r-2 Et H Pr Ta-8 Tb-9 i-4 3 1 <![CDATA[Cl - > 3 I-105a-1 r-3 Et H Pr Ta-8 Tb-9 i-4 3 1 <![CDATA[Cl - > 3 I-106a-1 r-1 Et H Pr Ta-8 Tb-10 i-4 3 1 <![CDATA[Cl - > 3 I-107a-1 r-2 Et H Pr Ta-8 Tb-10 i-4 3 1 <![CDATA[Cl - > 3 I-108a-1 r-3 Et H Pr Ta-8 Tb-10 i-4 3 1 <![CDATA[Cl - > 3 I-1a-2 r-1 Et H H Ta-8 Tb-5 l-1 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-2a-2 r-2 Et H H Ta-8 Tb-5 l-1 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-3a-2 r-3 Et H H Ta-8 Tb-5 l-1 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-4a-2 r-1 Et H H Ta-8 Tb-6 l-1 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-5aa-2 r-2 Et H H Ta-8 Tb-6 l-1 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-6aa-2 r-3 Et H H Ta-8 Tb-6 l-1 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-7a-2 r-1 Et H Et Ta-8 Tb-5 l-1 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-8a-2 r-2 Et H Et Ta-8 Tb-5 l-1 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-9a-2 r-3 Et H Et Ta-8 Tb-5 l-1 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-10a-2 r-1 Et H Et Ta-8 Tb-6 l-1 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-11a-2 r-2 Et H Et Ta-8 Tb-6 l-1 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-12a-2 r-3 Et H Et Ta-8 Tb-6 l-1 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-13a-2 r-1 Et H Pr Ta-8 Tb-5 l-1 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-14a-2 r-2 Et H Pr Ta-8 Tb-5 l-1 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-15a-2 r-3 Et H Pr Ta-8 Tb-5 l-1 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-16a-2 r-1 Et H Pr Ta-8 Tb-6 l-1 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-17a-2 r-2 Et H Pr Ta-8 Tb-6 l-1 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-18a-2 r-3 Et H Pr Ta-8 Tb-6 l-1 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-19a-2 r-1 Et H H Ta-8 Tb-5 i-2 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-20a-2 r-2 Et H H Ta-8 Tb-5 i-2 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-21a-2 r-3 Et H H Ta-8 Tb-5 i-2 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-22a-2 r-1 Et H H Ta-8 Tb-6 i-2 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-23a-2 r-2 Et H H Ta-8 Tb-6 i-2 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-24a-2 r-3 Et H H Ta-8 Tb-6 i-2 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-25a-2 r-1 Et H Et Ta-8 Tb-5 i-2 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-26a-2 r-2 Et H Et Ta-8 Tb-5 i-2 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-27a-2 r-3 Et H Et Ta-8 Tb-5 i-2 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2

[0296] [Table 5]

[0297] <![CDATA[R 1a ,R 3a > <![CDATA[R 2a , R 4a > <![CDATA[R 5a ~R 12a > <![CDATA[R 13a > <![CDATA[T 1a > <![CDATA[T 2a > <![CDATA[L 1a > a1 b1 <![CDATA[X c1- > d1 I-28a-2 r-1 Et H Et Ta-8 Tb-6 i-2 2 3 <![CDATA[[PW 12 O 40 30 > ​ 2 I-29a-2 r-2 Et H Et Ta-8 Tb-6 i-2 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-30a-2 r-3 Et H Et Ta-8 Tb-6 i-2 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-31a-2 r-1 Et H Pr Ta-8 Tb-5 i-2 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-32a-2 r-2 Et H Pr Ta-8 Tb-5 i-2 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-33a-2 r-3 Et H Pr Ta-8 Tb-5 i-2 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-34a-2 r-1 Et H Pr Ta-8 Tb-6 i-2 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-35a-2 r-2 Et H Pr Ta-8 Tb-6 i-2 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-36a-2 r-3 Et H Pr Ta-8 Tb-6 i-2 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-37a-2 r-1 Et H H Ta-8 Tb-5 i-4 3 1 <![CDATA[[PW 12 O 40 3- > ​ 1 I-38a-2 r-2 Et H H Ta-8 Tb-5 i-4 3 1 <![CDATA[[PW 12 O 40 3- > ​ 1 I-39a-2 r-3 Et H H Ta-8 Tb-5 i-4 3 1 <![CDATA[[PW 12 O 40 3- > ​ 1 I-40a-2 r-1 Et H H Ta-8 Tb-6 i-4 3 1 <![CDATA[[PW 12 O 40 3- > ​ 1 I-41a-2 r-2 Et H H Ta-8 Tb-6 i-4 3 1 <![CDATA[[PW 12 O 40 3- > ​ 1 I-42a-2 r-3 Et H H Ta-8 Tb-6 i-4 3 1 <![CDATA[[PW 12 O 40 3- > ​ 1 I-43a-2 r-1 Et H Et Ta-8 Tb-5 i-4 3 1 <![CDATA[[PW 12 O 40 3- > ​ 1 I-44a-2 r-2 Et H Et Ta-8 Tb-5 i-4 3 1 <![CDATA[[PW 12 O 40 3- > ​ 1 I-45a-2 r-3 Et H Et Ta-8 Tb-5 i-4 3 1 <![CDATA[[PW 12 O 40 3- > ​ 1 I-46a-2 r-1 Et H Et Ta-8 Tb-6 i-4 3 1 <![CDATA[[PW 12 O 40 3- > ​ 1 I-47a-2 r-2 Et H Et Ta-8 Tb-6 i-4 3 1 <![CDATA[[PW 12 O 40 3- > ​ 1 I-48a-2 r-3 Et H Et Ta-8 Tb-6 i-4 3 1 <![CDATA[[PW 12 O 40 3- > ​ 1 I-49a-2 r-1 Et H Pr Ta-8 Tb-5 i-4 3 1 <![CDATA[[PW 12 O 40 3- > ​ 1 I-50a-2 r-2 Et H Pr Ta-8 Tb-5 i-4 3 1 <![CDATA[[PW 12 O 40 3- > ​ 1 I-51a-2 r-3 Et H Pr Ta-8 Tb-5 i-4 3 1 <![CDATA[[PW 12 O 40 3- > ​ 1 I-52a-2 r-1 Et H Pr Ta-8 Tb-6 i-4 3 1 <![CDATA[[PW 12 O 40 3- > ​ 1 I-53a-2 r-2 Et H Pr Ta-8 Tb-6 i-4 3 1 <![CDATA[[PW 12 O 40 3- > ​ 1 I-54a-2 r-3 Et H Pr Ta-8 Tb-6 i-4 3 1 <![CDATA[[PW 12 O 40 3- > ​ 1 I-55a-2 r-1 Et H H Ta-8 Tb-9 l-1 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-56a-2 r-2 Et H H Ta-8 Tb-9 l-1 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-57a-2 r-3 Et H H Ta-8 Tb-9 l-1 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-58a-2 r-1 Et H H Ta-8 Tb-10 l-1 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-59a-2 r-2 Et H H Ta-8 Tb-10 l-1 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-60a-2 r-3 Et H H Ta-8 Tb-10 l-1 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-61a-2 r-1 Et H Et Ta-8 Tb-9 l-1 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-62a-2 r-2 Et H Et Ta-8 Tb-9 l-1 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-63a-2 r-3 Et H Et Ta-8 Tb-9 l-1 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-64a-2 r-1 Et H Et Ta-8 Tb-10 l-1 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-65a-2 r-2 Et H Et Ta-8 Tb-10 l-1 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-66a-2 r-3 Et H Et Ta-8 Tb-10 l-1 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-67a-2 r-1 Et H Pr Ta-8 Tb-9 l-1 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-68a-2 r-2 Et H Pr Ta-8 Tb-9 l-1 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-69a-2 r-3 Et H Pr Ta-8 Tb-9 l-1 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-70a-2 r-1 Et H Pr Ta-8 Tb-10 l-1 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-71a-2 r-2 Et H Pr Ta-8 Tb-10 l-1 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-72a-2 r-3 Et H Pr Ta-8 Tb-10 l-1 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2

[0298] [Table 6]

[0299] <![CDATA[R 1a ,R 3a > <![CDATA[R 2a ,R 4a > <![CDATA[R 5a ~R 12a > <![CDATA[R 13a > <![CDATA[T 1a > <![CDATA[T 2a > <![CDATA[L 1a > a1 b1 <![CDATA[X c1- > d1 I-73a-2 r-1 Et H H Ta-8 Tb-9 i-2 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-74a-2 r-2 Et H H Ta-8 Tb-9 i-2 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-75a-2 r-3 Et H H Ta-8 Tb-9 i-2 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-76a-2 r-1 Et H H Ta-8 Tb-10 i-2 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-77a-2 r-2 Et H H Ta-8 Tb-10 i-2 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-78a-2 r-3 Et H H Ta-8 Tb-10 i-2 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-79a-2 r-1 Et H Et Ta-8 Tb-9 i-2 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-80a-2 r-2 Et H Et Ta-8 Tb-9 i-2 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-81a-2 r-3 Et H Et Ta-8 Tb-9 i-2 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-82a-2 r-1 Et H Et Ta-8 Tb-10 i-2 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-83a-2 r-2 Et H Et Ta-8 Tb-10 i-2 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-84a-2 r-3 Et H Et Ta-8 Tb-10 i-2 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-85a-2 r-1 Et H Pr Ta-8 Tb-9 i-2 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-86a-2 r-2 Et H Pr Ta-8 Tb-9 i-2 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-87a-2 r-3 Et H Pr Ta-8 Tb-9 i-2 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-88a-2 r-1 Et H Pr Ta-8 Tb-10 i-2 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-89a-2 r-2 Et H Pr Ta-8 Tb-10 i-2 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-90a-2 r-3 Et H Pr Ta-8 Tb-10 i-2 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-91a-2 r-1 Et H H Ta-8 Tb-9 i-4 3 1 <![CDATA[[PW 12 O 40 3- > ​ 1 I-92a-2 r-2 Et H H Ta-8 Tb-9 i-4 3 1 <![CDATA[[PW 12 O 40 3- > ​ 1 I-93a-2 r-3 Et H H Ta-8 Tb-9 i-4 3 1 <![CDATA[[PW12O 4a 3- > ​ 1 I-94a-2 r-1 Et H H Ta-8 Tb-10 i-4 3 1 <![CDATA[[PW 12 O 40 3- > ​ 1 I-95a-2 r-2 Et H H Ta-8 Tb-10 i-4 3 1 <![CDATA[[PW 12 O 40 3- > ​ 1 I-96a-2 r-3 Et H H Ta-8 Tb-10 i-4 3 1 <![CDATA[[PW 12 O 40 3- > ​ 1 I-97a-2 r-1 Et H Et Ta-8 Tb-9 i-4 3 1 <![CDATA[[PW 12 O 40 3- > ​ 1 I-98a-2 r-2 Et H Et Ta-8 Tb-9 i-4 3 1 <![CDATA[[PW 12 o 4o 3- > ​ 1 I-49a-2 r-3 Et H Et Ta-8 Tb-9 i-4 3 1 <![CDATA[[PW 12 O 40 3- > ​ 1 I-100a-2 r-1 Et H Et Ta-8 Tb-10 i-4 3 1 <![CDATA[[PW 12 O 40 3- > ​ 1 I-101a-2 r-2 Et H Et Ta-8 Tb-10 i-4 3 1 <![CDATA[[PW 12 O 40 3- > ​ 1 I-102a-2 r-3 Et H Et Ta-8 Tb-10 i-4 3 1 <![CDATA[[PW 12 O 40 3- > ​ 1 I-103a-2 r-1 Et H Pr Ta-8 Tb-9 i-4 3 1 <![CDATA[[PW 12 O 40 3- > ​ 1 I-104a-2 r-2 Et H Pr Ta-8 Tb-9 i-4 3 1 <![CDATA[[PW 12 O 40 3- > ​ 1 I-105a-2 r-3 Et H Pr Ta-8 Tb-9 i-4 3 1 <![CDATA[[PW 12 O 40 3- > ​ 1 I-106a-2 r-1 Et H Pr Ta-8 Tb-10 i-4 3 1 <![CDATA[[PW 12 O 40 3- > ​ 1 I-107a-2 r-2 Et H Pr Ta-8 Tb-10 i-4 3 1 <![CDATA[[PW 12 O 40 2- > ​ 1 I-108a-2 r-3 Et H Pr Ta-8 Tb-10 i-4 3 1 <![CDATA[[PW 12 O 40 3- > ​ 1

[0300]

[0301] [Table 7]

[0302] <![CDATA[R 1b ,R 3b > <![CDATA[R 2b ,R 4b > <![CDATA[R 5b ~R 12b > <![CDATA[R 13b > <![CDATA[T 1b > <![CDATA[T 2b > <![CDATA[L 1b > a2 e2 I-1b r-1 Et H H Ta-8 Tb-5 l-1 2 2 I-2b r-2 Et H H Ta-8 Tb-5 l-1 2 2 I-3b r-3 Et H H Ta-8 Tb-5 l-1 2 2 I-4b r-1 Et H H Ta-8 Tb-6 l-1 2 2 I-5b r-2 Et H H Ta-8 Tb-6 l-1 2 2 I-6b r-3 Et H H Ta-8 Tb-6 l-1 2 2 I-7b r-1 Et H Et Ta-8 Tb-5 l-1 2 2 I-8b r-2 Et H Et Ta-8 Tb-5 l-1 2 2 I-9b r-3 Et H Et Ta-8 Tb-5 l-1 2 2 I-10b r-1 Et H Et Ta-8 Tb-6 l-1 2 2 I-11b r-2 Et H Et Ta-8 Tb-6 l-1 2 2 I-12b r-3 Et H Et Ta-8 Tb-6 l-1 2 2 I-13b r-1 Et H Pr Ta-8 Tb-5 l-1 2 2 I-14b r-2 Et H Pr Ta-8 Tb-5 l-1 2 2 I-15b r-3 Et H Pr Ta-8 Tb-5 l-1 2 2 I-16b r-1 Et H Pr Ta-8 Tb-6 l-1 2 2 I-17b r-2 Et H Pr Ta-8 Tb-6 l-1 2 2 I-18b r-3 Et H Pr Ta-8 Tb-6 l-1 2 2 I-19b r-1 Et H H Ta-8 Tb-5 i-2 2 2 I-20b r-2 Et H H Ta-8 Tb-5 i-2 2 2 I-21b r-3 Et H H Ta-8 Tb-5 i-2 2 2 I-22b r-1 Et H H Ta-8 Tb-6 i-2 2 2 I-23b r-2 Et H H Ta-8 Tb-6 i-2 2 2 I-24b r-3 Et H H Ta-8 Tb-6 i-2 2 2 I-25b r-1 Et H Et Ta-8 Tb-5 i-2 2 2 I-26b r-2 Et H Et Ta-8 Tb-5 i-2 2 2 I-27b r-3 Et H Et Ta-8 Tb-5 i-2 2 2 I-28b r-1 Et H Et Ta-8 Tb-6 i-2 2 2 I-29b r-2 Et H Et Ta-8 Tb-6 i-2 2 2 I-30b r-3 Et H Et Ta-8 Tb-6 i-2 2 2 I-31b r-1 Et H Pr Ta-8 Tb-5 i-2 2 2 I-32b r-2 Et H Pr Ta-8 Tb-5 i-2 2 2 I-33b r-3 Et H Pr Ta-8 Tb-5 i-2 2 2 I-34b r-1 Et H Pr Ta-8 Tb-6 i-2 2 2 I-35b r-2 Et H Pr Ta-8 Tb-6 i-2 2 2 I-36b r-3 Et H Pr Ta-8 Tb-6 i-2 2 2 I-37b r-1 Et H H Ta-8 Tb-5 i-4 3 3 I-38b r-2 Et H H Ta-8 Tb-5 i-4 3 3 I-39b r-3 Et H H Ta-8 Tb-5 i-4 3 3 I-40b r-1 Et H H Ta-8 Tb-6 i-4 3 3 I-41b r-2 Et H H Ta-8 Tb-6 i-4 3 3 I-42b r-3 Et H H Ta-8 Tb-6 i-4 3 3 I-43b r-1 Et H Et Ta-8 Tb-5 i-4 3 3 I-44b r-2 Et H Et Ta-8 Tb-5 i-4 3 3 I-45b r-3 Et H Et Ta-8 Tb-5 i-4 3 3

[0303] [Table 8]

[0304] <![CDATA[R 1b ,R 3b > <![CDATA[R 2b ,R 4b > <![CDATA[R 5b ~R 12b > <![CDATA[R 13b > <![CDATA[T 1b > <![CDATA[T 2b > <![CDATA[L 1b > a2 e2 I-46b r-1 Et H Et Ta-8 Tb-6 i-4 3 3 I-47b r-2 Et H Et Ta-8 Tb-6 i-4 3 3 I-48b r-3 Et H Et Ta-8 Tb-6 i-4 3 3 I-49b r-1 Et H Pr Ta-8 Tb-5 i-4 3 3 I-50b r-2 Et H Pr Ta-8 Tb-5 i-4 3 3 I-51b r-3 Et H Pr Ta-8 Tb-5 i-4 3 3 I-52b r-1 Et H Pr Ta-8 Tb-6 i-4 3 3 I-53b r-2 Et H Pr Ta-8 Tb-6 i-4 3 3 I-54b r-3 Et H Pr Ta-8 Tb-6 i-4 3 3 I-55b r-1 Et H H Ta-8 Tb-9 l-1 2 2 I-56b r-2 Et H H Ta-8 Tb-9 l-1 2 2 I-57b r-3 Et H H Ta-8 Tb-9 l-1 2 2 I-58b r-1 Et H H Ta-8 Tb-10 l-1 2 2 I-59b r-2 Et H H Ta-8 Tb-10 l-1 2 2 I-60b r-3 Et H H Ta-8 Tb-10 l-1 2 2 I-61b r-1 Et H Et Ta-8 Tb-9 l-1 2 2 I-62b r-2 Et H Et Ta-8 Tb-9 l-1 2 2 I-63b r-3 Et H Et Ta-8 Tb-9 l-1 2 2 I-64b r-1 Et H Et Ta-8 Tb-10 l-1 2 2 I-65b r-2 Et H Et Ta-8 Tb-10 l-1 2 2 I-66b r-3 Et H Et Ta-8 Tb-10 l-1 2 2 I-67b r-1 Et H Pr Ta-8 Tb-9 l-1 2 2 I-68b r-2 Et H Pr Ta-8 Tb-9 l-1 2 2 I-69b r-3 Et H Pr Ta-8 Tb-9 l-1 2 2 I-70b r-1 Et H Pr Ta-8 Tb-10 l-1 2 2 I-71b r-2 Et H Pr Ta-8 Tb-10 l-1 2 2 I-72b r-3 Et H Pr Ta-8 Tb-10 l-1 2 2 I-73b r-1 Et H H Ta-8 Tb-9 i-2 2 2 I-74b r-2 Et H H Ta-8 Tb-9 i-2 2 2 I-75b r-3 Et H H Ta-8 Tb-9 i-2 2 2 I-76b r-1 Et H H Ta-8 Tb-10 i-2 2 2 I-77b r-2 Et H H Ta-8 Tb-10 i-2 2 2 I-78b r-3 Et H H Ta-8 Tb-10 i-2 2 2 I-79b r-1 Et H Et Ta-8 Tb-9 i-2 2 2 I-80b r-2 Et H Et Ta-8 Tb-9 i-2 2 2 I-81b r-3 Et H Et Ta-8 Tb-9 i-2 2 2 I-82b r-1 Et H Et Ta-8 Tb-10 i-2 2 2 I-83b r-2 Et H Et Ta-8 Tb-10 i-2 2 2 I-84b r-3 Et H Et Ta-8 Tb-10 i-2 2 2 I-85b r-1 Et H Pr Ta-8 Tb-9 i-2 2 2 I-86b r-2 Et H Pr Ta-8 Tb-9 i-2 2 2 I-87b r-3 Et H Pr Ta-8 Tb-9 i-2 2 2 I-88b r-1 Et H Pr Ta-8 Tb-10 i-2 2 2 I-89b r-2 Et H Pr Ta-8 Tb-10 i-2 2 2 I-90b r-3 Et H Pr Ta-8 Tb-10 i-2 2 2

[0305] [Table 9]

[0306] <![CDATA[R 1b ,R 3b > <![CDATA[R 2b ,R 4b > <![CDATA[R 5b ~R 12b > <![CDATA[R 13b > <![CDATA[T 1b > <![CDATA[T 2b > <![CDATA[L 1b > a2 e2 I-91b r-1 Et H H Ta-8 Tb-9 i-4 3 3 I-92b r-2 Et H H Ta-8 Tb-9 i-4 3 3 I-93b r-3 Et H H Ta-8 Tb-9 i-4 3 3 I-94b r-1 Et H H Ta-8 Tb-10 i-4 3 3 I-95b r-2 Et H H Ta-8 Tb-10 i-4 3 3 I-96b r-3 Et H H Ta-8 Tb-10 i-4 3 3 I-97b r-1 Et H Et Ta-8 Tb-9 i-4 3 3 I-98b r-2 Et H Et Ta-8 Tb-9 i-4 3 3 I-99b r-3 Et H Et Ta-8 Tb-9 i-4 3 3 I-100b r-1 Et H Et Ta-8 Tb-10 i-4 3 3 I-101b r-2 Et H Et Ta-8 Tb-10 i-4 3 3 I-102b r-3 Et H Et Ta-8 Tb-10 i-4 3 3 I-103b r-1 Et H Pr Ta-8 Tb-9 i-4 3 3 I-104b r-2 Et H Pr Ta-8 Tb-9 i-4 3 3 I-105b r-3 Et H Pr Ta-8 Tb-9 i-4 3 3 I-106b r-1 Et H Pr Ta-8 Tb-10 i-4 3 3 I-107b r-2 Et H Pr Ta-8 Tb-10 i-4 3 3 I-108b r-3 Et H Pr Ta-8 Tb-10 i-4 3 3

[0307] In Tables 2 to 9, H represents a hydrogen atom, Et represents an ethyl group, Pr represents a 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).

[0308]

[0309] [In the formula, * represents the bonding site to the nitrogen atom.]

[0310]

[0311] [In the formula, * represents the bonding site.]

[0312]

[0313] [In the formula, * represents the bonding site to L 1a or L 1b and ** represents the bonding site to the nitrogen atom.]

[0314]

[0315] [In the formula, * represents the bonding site to T 2a or T 2b .]

[0316] As the compound (I), the compounds (I-1a-1) to (I-36a-1), the compounds (I-1a-2) to (I-36a-2), the compounds (I-55a-1) to (I-90a-1), the compounds (I-55a-2) to (I-90a-2), the compounds (I-1b) to (I-36b) and the compounds (I-55b) to (I-90b) are preferred, the compounds (I-1a-1) to (I-18a-1), the compounds (I-55a-1) to (I-72a-1), the compounds (I-1a-2) to (I-18a-2), the compounds (I-55a-2) to (I-72a-2), the compounds (I-1b) to (I-18b) and the compounds (I-55b) to (I-72b) are more preferred, and the compounds (I-1a-2) to (I-18a-2), the compounds (I-55a-2) to (I-72a-2), the compounds (I-1b) to (I-18b), and the compounds (I-55b) to (I-72b) are further preferred. From the viewpoint of better brightness, R 1a 、R 3a 、R 1b 、R 3b The compound represented by the formula (r-1) or (r-2) is preferred. From the viewpoint of better light resistance, R 1a 、R 3a 、R 1b 、R 3b The compound represented by the formula (r-3) is preferred. In addition, from the viewpoints of heat resistance and solvent resistance, the compounds (I-1a-2) to (I-108a-2) are preferred, the compounds (I-1a-2) to (I-18a-2) and the compounds (I-55a-2) to (I-72a-2) are more preferred, the compounds (I-1a-2) to (I-6a-2) and the compounds (I-55a-2) to (I-60a-2) are further preferred, and the compounds (I-1a-2) to (I-6a-2) are still further preferred.

[0317] The compound (I) is also preferably the compound represented by the following formula (I-3).

[0318]

[0319] [In the formula (I-3),

[0320] R 301 and R 303 are each independently a phenyl group which may have a substituent,

[0321] R 302 and R 304 are each independently a saturated chain hydrocarbon group having 1 to 10 carbon atoms which may have a substituent,

[0322] R 305 ~R 312 is a hydrogen atom,

[0323] R 313 is a hydrogen atom or a saturated chain hydrocarbon group having 1 to 6 carbon atoms which may have substituents,

[0324] T 301 represents a divalent aromatic hydrocarbon group which may have substituents, T 302 represents a a301-valent cyclic hydrocarbon group which may have substituents,

[0325] L 301 represents a divalent aliphatic hydrocarbon group having 1 to 5 carbon atoms which may have substituents,

[0326] a301 is 2 or 3,

[0327] d301 represents an integer of 1 or more,

[0328] b, c and X c- represent the same meanings as described above.]

[0329] R 301 ~R 313 and T 301 are the same as described above.

[0330] As the substituent of the cyclic hydrocarbon group represented by T 302 and the substituent of the aliphatic hydrocarbon group represented by L 301 groups described as substituent B can be mentioned.

[0331] T 302 is preferably a divalent alicyclic hydrocarbon group which may have substituents, more preferably a divalent alicyclic hydrocarbon group having 1 to 18 carbon atoms which may have substituents, and still more preferably a divalent alicyclic hydrocarbon group having 1 to 8 carbon atoms which may have substituents.

[0332] L 301 is preferably a divalent aliphatic hydrocarbon group having 1 to 5 carbon atoms, more preferably a divalent aliphatic hydrocarbon group having 1 to 3 carbon atoms, and still more preferably a divalent aliphatic hydrocarbon group having 1 to 2 carbon atoms.

[0333] a 301 is preferably 2.

[0334] d 301 is preferably 1 to 4, more preferably 1 to 3, still more preferably 1 or 2, and even more preferably 2.

[0335] b and c are independently preferably 1 to 4, more preferably 1 to 3, still more preferably 2 to 3, and even more preferably 3.

[0336] X c- Preferably, it contains an anion of a heteropolyacid or isopolyacid containing tungsten as an essential element, more preferably an anion of phosphotungstic acid, silicotungstic acid, and tungsten-based isopolyacid.

[0337] As the compound represented by the formula (I-3), as shown in Table 10, compounds represented by the formula (I-c-1) to the formula (I-c-20) etc. can be cited.

[0338] [Table 10]

[0339] <![CDATA[R 301 ,R 303 > <![CDATA[R 302 ,R 304 > <![CDATA[R 305～ R 312 > <![CDATA[R 313 > <![CDATA[T 301 > <![CDATA[T 302 > <![CDATA[L 301 > a301 b <![CDATA[X c1- > d301 I-c-1 r-1 Met H H Ta-8 Tb-11 l-1 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-c-2 r-2 Met H H Ta-8 Tb-11 l-1 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-c-3 r-3 Met H H Ta-8 Tb-11 l-1 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-c-4 r-4 Met H H Ta-8 Tb-11 l-1 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-c-5 r-5 Met H H Ta-8 Tb-11 l-1 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-c-6 r-1 Met H H Ta-8 Tb-12 l-1 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-c-7 r-2 Met H H Ta-8 Tb-12 l-1 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-c-8 r-3 Met H H Ta-8 Tb-12 l-1 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-c-9 r-4 Met H H Ta-8 Tb-12 l-1 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-c-10 r-5 Met H H Ta-8 Tb-12 l-1 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-c-11 r-1 Et H H Ta-8 Tb-11 l-1 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-c-12 r-2 Et H H Ta-8 Tb-11 l-1 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-c-13 r-3 Et H H Ta-8 Tb-11 l-1 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-c-14 r-4 Et H H Ta-8 Tb-11 l-1 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-c-15 r-5 Et H H Ta-8 Tb-11 l-1 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-c-16 r-1 Et H H Ta-8 Tb-12 l-1 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-c-17 r-2 Et H H Ta-8 Tb-12 l-1 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-c-18 r-3 Et H H Ta-8 Tb-12 l-1 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-c-19 r-4 Et H H Ta-8 Tb-12 l-1 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2 I-c-20 r-5 Et H H Ta-8 Tb-12 l-1 2 3 <![CDATA[[PW 12 O 40 3- > ​ 2

[0340] In Table 10, Met represents methyl, Et represents ethyl, r-1 to r-5 represent groups represented by the following formula (r-1) to (r-5), Ta-8 represents a group represented by the following formula (Ta-8), Tb-11 to Tb-12 represent groups represented by the following formula (Tb-11) to (Tb-12), and l-1 represents a group represented by the following formula (l-1).

[0341]

[0342] [In the formula, * represents the bonding site with the nitrogen atom.]

[0343]

[0344] [In the formula, * represents the bonding site.]

[0345]

[0346] [In the formula, * represents the bonding site with L 301 and ** represents the bonding site with the nitrogen atom.]

[0347]

[0348] [In the formula, * represents the bonding site with T 302 .]

[0349] Compound (I) can be produced by methods such as the following (1) to (3) etc.

[0350] (1) X c- Production method of compound (I) (hereinafter, sometimes referred to as compound (I')) where X is a halide ion

[0351] Compound (I') can be produced, for example, by reacting a compound represented by the formula (B-I) with a compound represented by the formula (C-I).

[0352]

[0353] [In formulas (B-I) and (C-I), R 1 ~R 13 , T 2 , L 1 and a respectively represent the same meanings as described above. T 1B represents a group obtained by substituting a hydrogen atom for a bonding site different from the bonding site bonded to the nitrogen atom in the above-mentioned T 1 .]

[0354] The usage amount of the compound represented by formula (C-I) is preferably 0.5 mol to 10 mol, more preferably 1 mol to 4 mol, relative to 1 mol of the compound represented by formula (B-I).

[0355] 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.

[0356] The above reaction can be carried out in the presence of an organic solvent or without a solvent. From the perspective 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, etc. The usage amount of the organic solvent is preferably 1 part by mass to 20 parts by mass, more preferably 2 parts by mass to 10 parts by mass, relative to 1 part by mass of the compound represented by formula (B-I).

[0357] 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 phosphoryl halides such as phosphoric acid, polyphosphoric acid, and phosphoryl chloride, sulfuric acid, thionyl halides such as thionyl chloride, etc. When using phosphoryl halides, thionyl halides, etc. as the condensing agent and satisfying the relationship of formula (z1), a compound (I') in which X c- is a halide ion is obtained.

[0358] a×b - e > 0 ··· (z1)

[0359] [In the above formula, a and b have the same meanings as a and b in formula (I). e represents the number of -SO3 - possessed by the compound (I') as a substituent.]

[0360] The usage amount of the condensing agent is preferably 0.1 part by mass to 20 parts by mass, more preferably 0.2 part by mass to 10 parts by mass, relative to 1 part by mass of the compound represented by formula (B-I).

[0361] 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 can be purified by column chromatography, recrystallization, or the like.

[0362] As the method for producing the compound (B-I), various known methods can be used, such as the method described in German Patent Application No. P3928243.0. Additionally, further purification can be carried out by known methods such as separation by recrystallization and chromatography according to needs.

[0363] As the method for producing the compound (C-I), various known methods can be cited. Additionally, further purification can be carried out by known methods such as separation by recrystallization and chromatography according to needs.

[0364] (2) X c- is an anion other than a halide ion (hereinafter referred to as anion X 1 ) of the compound (I) (hereinafter sometimes referred to as compound (I''))

[0365] The compound (I'') can be produced by mixing the compound (I') with a metal salt or protonic acid of anion X 1 . As the alkali metal, lithium, sodium, potassium, etc. can be cited.

[0366] The amount of the metal salt or protonic acid of anion X 1 relative to the compound (I') is added in a stoichiometric ratio that balances the charge of the cation in the compound (I') with that of anion X 1 . For example, per 1 mole of the compound (I'), it is preferably 0.5 mole to 8 moles, more preferably 1 mole to 3 moles.

[0367] The mixing of the compound (I') and the metal salt or protonic acid of anion X 1 can be carried out by dissolving both in the following solvents, or can also be carried out without dissolution.

[0368] As the solvent, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide, acetonitrile, ethyl acetate, toluene, methanol, ethanol, isopropanol, acetone, tetrahydrofuran, di ane, water, and chloroform can be cited.

[0369] Among them, from the viewpoint of solubility, at least one solvent selected from N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide, methanol, ethanol, isopropanol, and water is preferred.

[0370] The amount of the solvent used is preferably 1 to 30 parts by mass, more preferably 2 to 20 parts by mass, relative to 1 part by mass of the compound (I').

[0371] When the solvent is water, an acid such as acetic acid or hydrochloric acid can be added.

[0372] The compound (I') and the anion X 1 The mixing temperature of the alkali metal salt or the protonic acid is preferably 0°C to 150°C, more preferably 10°C to 120°C, and further preferably 20°C to 100°C. The mixing time is preferably 1 to 72 hours, more preferably 2 to 24 hours, and further preferably 3 to 12 hours.

[0373] When using a solvent soluble in water, the solution is mixed and, if necessary, further stirred for 1 to 3 hours, and then the solvent is removed, whereby the compound (I'') can be obtained. The obtained compound (I'') can be washed with ion-exchanged water, methanol, etc. as needed.

[0374] When using a solvent immiscible with water, the reaction mixture and ion-exchanged water are mixed and, if necessary, further stirred for 1 to 3 hours, and then the organic layer is obtained by liquid separation, whereby a solution containing the compound (I'') can be obtained. This solution can also be washed with ion-exchanged water as needed. The solvent is removed from the solution containing the compound (I''), and the compound (I'') can be obtained.

[0375] (3) Method for producing a compound (hereinafter sometimes referred to as compound (I''')) in which X c- (i.e., d = 0) does not exist

[0376] The compound (I''') can be produced by mixing the compound (I') with sulfuric acid.

[0377] The amount of sulfuric acid used relative to the compound (I') is added in a stoichiometric ratio that balances the charge of the cation in the compound (I') with that of -SO3 - , for example, 0.5 to 8 moles, preferably 1 to 3 moles, per 1 mole of the compound (I'). In addition, the above sulfuric acid can be used as a reaction solvent. When using sulfuric acid as a solvent, the amount of sulfuric acid used is, for example, 20 moles or more, preferably 25 moles or more, per 1 mole of the compound (I'). In addition, when using sulfuric acid as a solvent, the upper limit of the amount of sulfuric acid used is not particularly limited, and is, for example, 100 parts by mass or less, preferably 50 parts by mass or less, relative to 1 part by mass of the compound (I').

[0378] The mixing temperature of compound (I') and sulfuric acid is preferably 0°C to 150°C, more preferably 10°C to 120°C, and further preferably 20°C to 100°C. The mixing time is preferably 1 hour to 72 hours, more preferably 2 hours to 24 hours, and further preferably 3 hours to 12 hours.

[0379] The mixture obtained by mixing compound (I') and sulfuric acid can be made into a suspension by adding it to ice water and then filtered to obtain compound (I'''). Additionally, it can be further purified by known methods such as recrystallization and separation by chromatography as needed.

[0380] In 100% by mass of colorant (A), the content of compound (I) is preferably 70% by mass or more, more preferably 80% by mass or more, further preferably 90% by mass or more, still more preferably 95% by mass or more, and may also be 100% by mass. Colorant (A) may contain one or more than two kinds of compound (I).

[0381] Colorant (A) may contain dyes (hereinafter sometimes referred to as dye (A1-1)) and / or pigments (hereinafter sometimes referred to as pigment (A1-2)) other than compound (I). Hereinafter, dye (A1-1) and pigment (A1-2) are sometimes collectively referred to as colorant (A1). These can be used alone or in combination of two or more.

[0382] As long as dye (A1-1) does not contain compound (I), known dyes can be used without particular limitation. For example, solvent dyes, acid dyes, direct dyes, mordant dyes, etc. can be cited. As dyes, for example, those classified as dye compounds in The Society of Dyers and Colourists' Colour Index and known dyes described in the Dyeing Guide (Color Dyeing Company) can be cited. Additionally, according to chemical structure, azo dyes, cyanine dyes, triphenylmethane dyes, xanthene dyes, anthraquinone dyes, naphthoquinone dyes, quinoneimine dyes, methylene dyes, azomethine dyes, squaric dyes, acridine dyes, styrene dyes, coumarin dyes, quinoline dyes, nitro dyes, and phthalocyanine dyes, etc. can be cited. Among them, organic solvent-soluble dyes are preferred.

[0383] Specifically, as dye (A1-1), examples include

[0384] 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;

[0385] 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;

[0386] C.I. Solvent Orange 2, 7, 11, 15, 26, 41, 54, 56, 77, 86, 99;

[0387] C.I. Solvent Violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60;

[0388] 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;

[0389] C.I. Solvent Green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35; etc. C.I. Solvent Dyes,

[0390] 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;

[0391] 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;

[0392] 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;

[0393] C.I. Acid Violet 6B, 7, 9, 15, 16, 17, 19, 21, 23, 24, 25, 30, 34, 38, 49, 72, 102;

[0394] 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;

[0395] 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; etc. C.I. Acid Dyes,

[0396] 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;

[0397] 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;

[0398] C.I. Direct Orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107;

[0399] C.I. Direct Violet 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104;

[0400] 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;

[0401] C.I. Direct Green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 79, 82; etc. C.I. direct dyes,

[0402] C.I. Disperse Yellow 51, 54, 76;

[0403] C.I. Disperse Violet 26, 27;

[0404] C.I. Disperse Blue 1, 14, 56, 60; etc. C.I. disperse dyes,

[0405] C.I. Basic Red 1, 9, 10;

[0406] 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;

[0407] C.I. Basic Violet 2;

[0408] C.I. Basic Green 1; etc. C.I. basic dyes,

[0409] C.I. Reactive Yellow 2, 76, 116;

[0410] C.I. Reactive Orange 16;

[0411] C.I. Reactive Red 36; etc. C.I. reactive dyes,

[0412] C.I. Mordant Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65;

[0413] 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;

[0414] 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;

[0415] 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;

[0416] 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;

[0417] 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,

[0418] C.I. Vat Green 1; etc. C.I. vat dyes and dyes with Color Index (C.I.) numbers.

[0419] As the pigment (A1 - 2), as long as it does not contain the compound (I), known pigments can be used without particular limitation. For example, pigments classified as pigments in the Color Index (published by The Society of Dyers and Colourists) can be cited.

[0420] As pigments classified as pigments, 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.;

[0421] Orange pigments such as C.I. Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73, etc.;

[0422] 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.;

[0423] Blue pigments such as C.I. Pigment Blue 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 60, etc.;

[0424] Purple pigments such as C.I. Pigment Violet 1, 19, 23, 32, 36, 38, etc.;

[0425] Green pigments such as C.I. Pigment Green 7, 36, 58, 59, 62, 63, etc.;

[0426] Brown pigments such as C.I. Pigment Brown 23, 25, etc.;

[0427] Black pigments such as C.I. Pigment Black 1, 7, etc.

[0428] As the colorant (A1), dyes and / or pigments that are yellow, red, or green are preferred.

[0429] The colorant (A1) can be subjected to rosin treatment as needed, surface treatment using derivatives into which acidic groups or basic groups are introduced, graft treatment of the surface of the colorant (A1) using a polymer compound, etc., micronization treatment based on the sulfuric acid micronization method, etc., cleaning treatment based on an organic solvent, water, etc. for removing impurities, removal treatment of ionic impurities based on the ion exchange method, etc. The particle size of the colorant (A1) is preferably substantially uniform.

[0430] When the colorant (A) further contains a colorant (A1), the content rate 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, relative to the total amount of the colorant (A). In addition, when the colorant (A) further contains a colorant (A1), the content rate of the compound (I) is, for example, less than 100% by mass relative to the total amount of the colorant (A).

[0431] When the colored resin composition contains a solvent (E), a colorant-containing solution containing the colorant (A) and the solvent (E) can be prepared in advance, and then the colored resin composition can be prepared using the colorant-containing solution. When the colorant (A) is insoluble in the solvent (E), for example, when the colorant (A) contains a pigment (A1-2) or the like, the colorant-containing solution can be prepared by dispersing and mixing the colorant (A) in the solvent (E). The colorant-containing solution may contain a part or all of the solvent (E) contained in the colored resin composition.

[0432] The content rate of the solid component in the colorant-containing solution is preferably 0.01% by mass to 99.99% by mass, more preferably 0.1% by mass to 99.9% by mass, still more preferably 0.1% by mass to 99% by mass, even more preferably 0.5% by mass to 90% by mass, and particularly preferably 1% by mass to 50% by mass, relative to the total amount of the colorant-containing solution.

[0433] The colorant (A) can be dispersed by containing a dispersant so that the colorant (A) is in a state of being uniformly dispersed in the solution. When two or more kinds are used in combination as the colorant (A), they can be dispersed separately or a plurality of them can be mixed and dispersed.

[0434] Dispersant (P)

[0435] As the dispersant (P), for example, surfactants and the like can be cited, and it can be any of cationic, anionic, nonionic, and amphoteric surfactants. Specifically, surfactants such as polyester-based, polyamine-based, polyurethane-based, and acrylic-based surfactants can be cited. These dispersants (P) can be used alone or in combination of two or more. When represented by a trade name as the dispersant (P), examples include KP (manufactured by Shin-Etsu Chemical Co., Ltd.), FLOWLEN (manufactured by Kyoeisha Chemical Co., Ltd.), Solsperse (registered trademark) (manufactured by ZENECA Co., Ltd.), 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 (P), the resin (B) described later can be used.

[0436] The above-mentioned dispersant (P) may have an amino group or may not have an amino group.

[0437] From the viewpoint of improving brightness and contrast, the amine value of the above-mentioned dispersant (P) is 0 mgKOH / g to 65 mgKOH / g, more preferably 1 mgKOH / g to 65 mgKOH / g, further preferably 2 mgKOH / g to 63 mgKOH / g, still further preferably 3 mgKOH / g to 61 mgKOH / g, particularly preferably 5 mgKOH / g to 61 mgKOH / g, and most preferably 7 mgKOH / g to 59 mgKOH / g. If the amine value of the dispersant (P) exceeds 65 mgKOH / g, there is a concern that the brightness and contrast may decrease.

[0438] In one aspect, from the viewpoint of further improving the contrast, the amine value of the above-mentioned dispersant (P) is preferably 15 mgKOH / g to 45 mgKOH / g, more preferably 20 mgKOH / g to 40 mgKOH / g, and further preferably 25 mgKOH / g to 35 mgKOH / g.

[0439] The amine value represents the number of milligrams of potassium hydroxide equivalent to the 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.

[0440] When using the dispersant (P), the amount of use of the dispersant (solid content) is usually 1 part by mass to 10,000 parts by mass, preferably 5 parts by mass to 5,000 parts by mass, more preferably 10 parts by mass to 1,000 parts by mass, and further preferably 15 parts by mass to 800 parts by mass with respect to 100 parts by mass of the colorant (A). If the amount of use of the dispersant is within the above range, there is a tendency to obtain a more uniform dispersion state of the colorant-containing solution.

[0441] The content rate of the dispersant (P) is preferably 1% by mass to 30% by mass, more preferably 2% by mass to 25% by mass, still more preferably 3% by mass to 20% by mass, and even more preferably 5% by mass to 20% by mass with respect to the total amount of the solid components of the colored resin composition.

[0442] The content rate of the colorant (A) is preferably 0.1% by mass to 50% by mass, more preferably 0.5% by mass to 40% by mass, and still more preferably 1% by mass to 30% by mass with respect to the total amount of the solid components of the colored resin composition. When the content rate of the colorant (A) is within the above range, the color density is sufficient when a color filter is formed, and the composition can contain a required amount of the resin (B), so that a pattern with sufficient mechanical strength can be formed, which is thus preferred.

[0443] Here, the "total amount of solid components" in the present 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 the solid components and the content of each component relative to the total amount can be measured by known analytical means such as liquid chromatography or gas chromatography, for example.

[0444] <Acid>

[0445] The colored resin composition of the present invention contains one or more acids selected from phenylphosphonic acid which may have a substituent and diphenylphosphonic acid which may have a substituent. The above acids can also form salts with the dispersant, and can stabilize the salt structure of the compound of formula (I). As a result, the brightness and contrast can be improved.

[0446] One or more of the above phenylphosphonic acid and the above diphenylphosphonic acid can be used respectively in one kind or two or more kinds.

[0447] One or more acids selected from phenylphosphonic acid which may have a substituent and diphenylphosphonic acid which may have a substituent are preferably one or more selected from the compounds represented by formula (Y) and the compounds represented by formula (Z).

[0448]

[0449] [In formula (Y), R y1 represents a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent. R y2 is selected from a halogen atom, a hydroxyl 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 Brepresents a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms which may have substituents. p is 0 to 5. When p is 2 or more, R y2 may be the same or different.]

[0450]

[0451] [In formula (Z), R z1 and R z2 are each independently selected from a halogen atom, a hydroxyl 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 substituents. R B represents a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms which may have substituents. R z1 and R z2 may each independently bond to the benzene ring to form a ring. p and q are each independently 0 to 5. When p and q are 2 or more, R z1 and R z2 may be the same or different.]

[0452] As the hydrocarbon group having 1 to 10 carbon atoms represented by R A , R B and R y1 , there may be mentioned an aliphatic hydrocarbon group and an aromatic hydrocarbon group. The aliphatic hydrocarbon group may be saturated or unsaturated, and may be linear or alicyclic.

[0453] As the above-mentioned saturated or unsaturated linear hydrocarbon group, there may be mentioned linear alkyl groups such as methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl; branched alkyl groups such as isopropyl, (1-ethyl)propyl, isobutyl, sec-butyl, tert-butyl, (1-ethyl)butyl, (2-ethyl)butyl, (1-propyl)butyl, isopentyl, neopentyl, tert-pentyl, (2-methyl)pentyl, (1-ethyl)pentyl, (3-ethyl)pentyl, (1-propyl)pentyl, (1-butyl)pentyl, isohexyl, (2-methyl)hexyl, (5-methyl)hexyl, (2-ethyl)hexyl, (1-butyl)hexyl, (2-methyl)heptyl, (2-ethyl)heptyl, (3-ethyl)heptyl, (2-methyl)octyl, (2-ethyl)octyl; alkenyl groups such as vinyl, 1-propenyl, 2-propenyl (allyl), (1-methyl)vinyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, (1-(2-propenyl))vinyl, (1,2-dimethyl)propenyl, 2-pentenyl, etc.

[0454] Examples of the above-mentioned saturated or unsaturated alicyclic hydrocarbon groups include cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl; cycloalkenyl groups such as cyclohexenyl (e.g., cyclohex-2-ene, cyclohex-3-ene), cycloheptenyl, cyclooctenyl; norbornyl, adamantyl, bicyclo[2.2.2]octyl, etc.

[0455] Examples of the aromatic hydrocarbon groups include aryl groups such as phenyl, 1-naphthyl, 2-naphthyl; alkylaryl groups such as o-tolyl, m-tolyl, p-tolyl, 2-ethylphenyl, 3-ethylphenyl, 4-ethylphenyl, 2,3-dimethylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, 3,4-dimethylphenyl, 3,5-dimethylphenyl, 2,4,6-trimethylphenyl, 2-methyl-6-ethylphenyl, 2,6-diethylphenyl, o-isopropylphenyl, m-isopropylphenyl, p-isopropylphenyl, 2-methyl-6-isopropylphenyl, 4-butylphenyl, o-tert-butylphenyl, m-tert-butylphenyl, p-tert-butylphenyl; alkenylaryl groups such as 4-vinylphenyl, etc.

[0456] As long as the upper limit of the number of carbon atoms is 10, the hydrocarbon group having 1 to 10 carbon atoms may also be a group formed by combining two or more of the above-mentioned linear hydrocarbon groups, alicyclic hydrocarbon groups, and aromatic hydrocarbon groups. Examples of such groups include aralkyl groups such as benzyl, phenethyl, 1-methyl-1-phenylethyl; arylalkenyl groups such as phenylvinyl (phenylvinyl); arylalkynyl groups such as phenylacetylenyl; alicyclic hydrocarbon groups bonded with one or more alkyl or alicyclic hydrocarbon groups such as 1-methylcyclopropyl, 1-methylcyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 1,2-dimethylcyclohexyl, 1,3-dimethylcyclohexyl, 1,4-dimethylcyclohexyl, 2,3-dimethylcyclohexyl, 2,4-dimethylcyclohexyl, 2,5-dimethylcyclohexyl, 2,6-dimethylcyclohexyl, 3,4-dimethylcyclohexyl, 3,5-dimethylcyclohexyl, 2,2-dimethylcyclohexyl, 3,3-dimethylcyclohexyl, 4,4-dimethylcyclohexyl, 2,4,6-trimethylcyclohexyl, 2,2,6,6-tetramethylcyclohexyl, 3,3,5,5-tetramethylcyclohexyl; alkyl groups bonded with one or more alicyclic hydrocarbon groups such as cyclopropylmethyl, cyclopropylethyl, cyclobutylmethyl, cyclobutylethyl, cyclopentylmethyl, cyclopentylethyl, cyclohexylmethyl, 2-methylcyclohexylmethyl, cyclohexylethyl, etc.

[0457] As the above-mentioned substituted amino group, an amino group having one or two hydrocarbon groups can be mentioned. As the above-mentioned hydrocarbon group, the groups exemplified as the hydrocarbon group having 1 to 10 carbon atoms described above can be mentioned. As the substituted amino group, for example, N-methylamino, N,N-dimethylamino, N-ethylamino, N,N-diethylamino, N-propylamino, N,N-dipropylamino, N-isopropylamino, N,N-diisopropylamino, N-phenylamino, N,N-diphenylamino, N,N-ethylmethylamino, N,N-methylphenylamino, N,N-ethylphenylamino, etc. can be mentioned.

[0458] R x The halogen atom represented, for example, is a bromine atom, a chlorine atom, a fluorine atom, or an iodine atom, preferably a bromine atom, a chlorine atom, or a fluorine atom, and more preferably a bromine atom or a chlorine atom.

[0459] As the substituent that the hydrocarbon group having 1 to 10 carbon atoms described above can have, at least one or more selected from a halogen atom, a hydroxyl group, an alkoxy group, a formyl group, a substituted or unsubstituted amino group, a nitro group, and a cyano group can be mentioned.

[0460] As the above-mentioned halogen atom, a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom can be mentioned.

[0461] As the above-mentioned alkoxy group, an alkoxy group having 1 to 4 carbon atoms such as a methoxy group, an ethoxy group, a propoxy group, or a butoxy group can be mentioned.

[0462] As the above-mentioned substituted amino group, the same examples as the substituted amino group mentioned as the substituted amino group of R y2 can be mentioned.

[0463] R A 、R B and R y1 The number of carbon atoms of the hydrocarbon group represented is preferably 1 to 8, more preferably 1 to 6, further preferably 1 to 4, and even more preferably 1 or 2.

[0464] Among them, R A 、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 further preferably a methyl group or an ethyl group. R y1 is preferably a hydrogen atom.

[0465] R y2 、R z1 and R z2 When there is one, the substitution position of R y2 、R z1 and R z2 can be relative to -O-P(O)(OH)(OR y1) and -O-P(O)(OH)O- can be any of ortho, para, and meta.

[0466] p and q are preferably from 0 to 4, more preferably from 0 to 3, still more preferably 0, 1, or 2.

[0467] The compound represented by formula (Y) is preferably a compound represented by formula (Y-1) to formula (Y-23).

[0468]

[0469] Among the compounds represented by formula (Y-1) to formula (Y-23), the compound represented by formula (Y-1) is particularly preferred.

[0470] The compound represented by formula (Z) is preferably a compound represented by formula (Z-1) to formula (Z-13).

[0471]

[0472] Among the compounds represented by formula (Z-1) to formula (Z-13), the compound represented by formula (Z-1) is particularly preferred.

[0473] The content (total content) of the above acid 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.

[0474] The content (total content) of the above acid 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.

[0475] The content ratio (total content ratio) of the above acid with respect to the solid content of the colored resin composition 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.

[0476] <Resin (B)>

[0477] Resin (B) is not particularly limited and is preferably an alkali-soluble resin. Examples of resin (B) include the following resins [K1] to [K6], etc.

[0478] Resin [K1]: A copolymer having a structural unit derived from at least one monomer (a) selected from unsaturated carboxylic acids and unsaturated carboxylic anhydrides (hereinafter sometimes referred to as "(a)"), and a structural unit derived from a monomer (b) having a cyclic ether structure and an ethylenic unsaturated bond with 2 to 4 carbon atoms (hereinafter sometimes referred to as "(b)");

[0479] 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) (but different from (a) and (b)) (hereinafter sometimes referred to as "(c)");

[0480] Resin [K3]: A copolymer having a structural unit derived from (a) and a structural unit derived from (c);

[0481] 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);

[0482] 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);

[0483] Resin [K6]: A copolymer having a structural unit obtained by adding a structural unit derived from (b) to (a) and then adding an acid anhydride, and a structural unit derived from (c).

[0484] As the monomer (a), for example, unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, and o-, m-, p-vinylbenzoic acid can be cited;

[0485] 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;

[0486] Bicyclic unsaturated compounds containing a carboxyl 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;

[0487] Acid anhydrides such as acid anhydrides of the above unsaturated dicarboxylic acids other than fumaric acid and mesaconic acid;

[0488] Unsaturated mono[(meth)acryloyloxyalkyl] esters of polycarboxylic acids having 2 or more carboxylic acid groups such as succinic acid mono[2-(meth)acryloyloxyethyl] ester and phthalic acid mono[2-(meth)acryloyloxyethyl] ester;

[0489] Unsaturated acrylate esters containing a hydroxyl group and a carboxyl group in the same molecule such as α-(hydroxymethyl)acrylic acid; etc.

[0490] Among them, from the aspects of copolymerization reactivity and the solubility of the obtained resin in an aqueous alkali solution, acrylic acid, methacrylic acid, maleic anhydride, etc. are preferred.

[0491] It should be noted that in this specification, “(meth)acrylic acid” means at least one selected from acrylic acid and methacrylic acid. Expressions such as “(meth)acryloyl” and “(meth)acrylate” have the same meaning.

[0492] Monomer (b) is a polymerizable compound having a cyclic ether structure with 2 to 4 carbon atoms (for example, at least one selected from 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 with 2 to 4 carbon atoms and a (meth)acryloyloxy group.

[0493] 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 tetrahydrofuranyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as “monomer (b3)”), etc.

[0494] Examples of monomer (b1) include monomers having a structure obtained by epoxidizing an unsaturated aliphatic hydrocarbon (hereinafter sometimes referred to as “monomer (b1-1)”), monomers having a structure obtained by epoxidizing an unsaturated alicyclic hydrocarbon (hereinafter sometimes referred to as “monomer (b1-2)”).

[0495] As monomer (b1-1), monomers having a glycidyl group and an ethylenically unsaturated bond are preferred. Specifically, examples of 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, etc.

[0496] Examples of the monomer (b1-2) include vinylcyclohexene monooxide, 1,2-epoxy-4-vinylcyclohexane (e.g., Celloxide 2000; manufactured by Daicel Corporation), methyl 3,4-epoxycyclohexyl (meth)acrylate (e.g., Cyclomer A400; manufactured by Daicel Corporation), methyl 3,4-epoxycyclohexyl (meth)acrylate (e.g., Cyclomer M100; manufactured by Daicel Corporation), the compound represented by formula (BI), and the compound represented by formula (BII).

[0497]

[0498] [In formula (BI) and formula (BII), R a and R b each independently represent 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 hydroxyl group.

[0499] X a and X b each independently represent a single bond, *-R c -, *-R c -O-, *-R c -S-, or *-R c -NH-.

[0500] R c represents an alkylene group having 1 to 6 carbon atoms.

[0501] * represents the bonding site to O.]

[0502] Examples of the alkyl group having 1 to 4 carbon atoms include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, and tert-butyl.

[0503] Examples of the alkyl group in which the hydrogen atom is substituted with a hydroxyl group include hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 1-hydroxypropyl, 2-hydroxypropyl, 3-hydroxypropyl, 1-hydroxy-1-methylethyl, 2-hydroxy-1-methylethyl, 1-hydroxybutyl, 2-hydroxybutyl, 3-hydroxybutyl, and 4-hydroxybutyl.

[0504] As R a and R b , hydrogen atom, methyl, hydroxymethyl, 1-hydroxyethyl, and 2-hydroxyethyl are preferably selected, and hydrogen atom and methyl are more preferably selected.

[0505] Examples of the alkylene group include methylene, ethylene, propane-1,2-diyl, propane-1,3-diyl, butane-1,4-diyl, pentane-1,5-diyl, and hexane-1,6-diyl.

[0506] As X a and X b A single bond, methylene, ethylene, *-CH2-O- (* represents the bonding site to O) group, *-CH2CH2-O- group can be preferably selected, and a single bond, *-CH2CH2-O- group (* represents the bonding site to O) can be more preferably selected.

[0507] As the compound represented by formula (BI), compounds represented by any one of formula (BI-1) to formula (BI-15) etc. can be cited. 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.

[0508]

[0509] As the compound represented by formula (BII), compounds represented by any one of formula (BII-1) to formula (BII-15) etc. can be cited. 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.

[0510]

[0511] The compound represented by formula (BI) and the compound represented by formula (BII) can be used separately alone, or the compound represented by formula (BI) and the compound represented by formula (BII) can be used in combination. When they are 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 in terms of molar basis, more preferably 10:90 to 90:10, and further preferably 20:80 to 80:20.

[0512] 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 preferred. As the monomer (b2), for example, 3-methyl-3-(meth)acryloxymethyl oxetane, 3-ethyl-3-(meth)acryloxymethyl oxetane, 3-methyl-3-(meth)acryloxyethyl oxetane, 3-ethyl-3-(meth)acryloxyethyl oxetane etc. can be cited.

[0513] As the monomer (b3) having a tetrahydrofuranyl group and an ethylenically unsaturated bond, a monomer having a tetrahydrofuranyl group and a (meth)acryloyloxy group is more preferable. Examples of the monomer (b3) include tetrahydrofurfuryl acrylate (e.g., Viscoat V#150, manufactured by Osaka Organic Chemical Industry Co., Ltd.), tetrahydrofurfuryl methacrylate, and the like.

[0514] Examples of the monomer (c) include (meth)acrylic acid methyl ester, (meth)acrylic acid ethyl ester, (meth)acrylic acid n-butyl ester, (meth)acrylic acid sec-butyl ester, (meth)acrylic acid tert-butyl ester, (meth)acrylic acid 2-ethylhexyl ester, (meth)acrylic acid dodecyl ester, (meth)acrylic acid lauryl ester, (meth)acrylic acid stearyl ester, (meth)acrylic acid cyclopentyl ester, (meth)acrylic acid cyclohexyl ester, (meth)acrylic acid 2-methylcyclohexyl ester, (meth)acrylic acid tricyclo[5.2.1.0 2,6 decane-8-yl ester (in this technical field, it is commonly called “(meth)acrylic acid dicyclopentyl ester”. In addition, it is sometimes called “(meth)acrylic acid tricyclodecyl ester”), (meth)acrylic acid tricyclo[5.2.1.0 2,6 decane-9-yl ester, (meth)acrylic acid tricyclo[5.2.1.0 2,6 decene-8-yl ester (in this technical field, it is commonly called “(meth)acrylic acid dicyclopentenyl ester”), (meth)acrylic acid tricyclo[5.2.1.0 2,6 decene-9-yl ester, (meth)acrylic acid dicyclopentyloxyethyl ester, (meth)acrylic acid isobornyl ester, (meth)acrylic acid adamantyl ester, (meth)acrylic acid allyl ester, (meth)acrylic acid propargyl ester, (meth)acrylic acid phenyl ester, (meth)acrylic acid naphthyl ester, and (meth)acrylic acid benzyl ester and other (meth)acrylic acid esters;

[0515] (meth)acrylic acid 2-hydroxyethyl ester and (meth)acrylic acid 2-hydroxypropyl ester and other (meth)acrylic acid esters containing a hydroxyl group;

[0516] Diethyl maleate, diethyl fumarate, diethyl itaconate and other dicarboxylic acid diesters;

[0517] 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-bis(hydroxymethyl)bicyclo[2.2.1]hept-2-ene, 5,6-bis(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;

[0518] Dicarbonylimide derivatives such as N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl 3-maleimidobenzoate, N-succinimidyl 4-maleimidobutyrate, N-succinimidyl 6-maleimidohexanoate, N-succinimidyl 3-maleimidopropionate, and N-(9-acridinyl)maleimide;

[0519] Aromatic compounds containing vinyl such as styrene, o-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, and p-methoxystyrene; Nitriles containing vinyl such as (meth)acrylonitrile; Halohydrocarbons such as vinyl chloride and vinylidene chloride; Amides containing vinyl such as (meth)acrylamide; Esters such as vinyl acetate; Dienes such as 1,3-butadiene, isoprene, and 2,3-dimethyl-1,3-butadiene.

[0520] Among them, from the aspects of copolymerization reactivity and heat resistance, it is preferable to use those selected from styrene, vinyltoluene, (meth)acrylic acid tricyclo[5.2.1.0 2,6 decane-8-yl ester, (meth)acrylic acid tricyclo[5.2.1.0 2,6 decane-9-yl ester, (meth)acrylic acid tricyclo[5.2.1.0 2,6Dec-8-enyl ester, tricyclo[5.2.1.0 2,6 Dec-9-enyl ester, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo[2.2.1]hept-2-ene, 2-hydroxyethyl (meth)acrylate, and benzyl (meth)acrylate, and at least one or more thereof.

[0521] In the resin [K1], the ratio of the structural units from each unit among all the structural units constituting the resin [K1] is preferably 2 to 60 mol% for the structural units from (a) and 40 to 98 mol% for the structural units from (b), and more preferably 10 to 50 mol% for the structural units from (a) and 50 to 90 mol% for the structural units from (b).

[0522] When the ratio of the structural units of the resin [K1] is within the above range, there is a tendency that the storage stability of the colored resin composition, the developability when forming a colored pattern, and the solvent resistance of the obtained color filter are excellent.

[0523] 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, March 1, 1972) and the cited references in this literature.

[0524] Specifically, the following method can be mentioned: A predetermined amount of (a) and (b), a polymerization initiator, a solvent, etc. are charged into a reaction vessel, and an oxygen-free atmosphere is formed, for example, by replacing oxygen with nitrogen, and while stirring, heating and heat preservation are carried out. It should be noted that the polymerization initiator, solvent, etc. used here are not particularly limited, and the polymerization initiator and solvent commonly used in this field can be used. For example, as the polymerization initiator, azo compounds (2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), etc.), organic peroxides (benzoyl peroxide, etc.) can be mentioned, and as the solvent, any solvent that can dissolve each monomer can 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.

[0525] It should be noted that for the obtained copolymer, the reaction solution can be used directly, or a concentrated or diluted solution can be used, or a substance taken out in the form of a solid (powder) by methods such as reprecipitation can 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 directly used for preparing the colored resin composition of the present invention, so that the manufacturing process of the colored resin composition of the present invention can be simplified.

[0526] In the resin [K2], the ratio of the structural units derived from each unit among all the structural units constituting the resin [K2] is preferably such that the structural units derived from (a) are 2 to 45 mol%, the structural units derived from (b) are 2 to 95 mol%, and the structural units derived from (c) are 1 to 65 mol%. More preferably, the structural units derived from (a) are 5 to 40 mol%, the structural units derived from (b) are 5 to 80 mol%, and the structural units derived from (c) are 5 to 60 mol%.

[0527] When the ratio of the structural units of the resin [K2] is within the above range, there is a tendency that 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 obtained color filter are excellent.

[0528] The resin [K2] can be produced, for example, in the same manner as the method described for the production method of the resin [K1].

[0529] In the resin [K3], the ratio of the structural units derived from each unit among all the structural units constituting the resin [K3] is preferably such that the structural units derived from (a) are 2 to 60 mol% and the structural units derived from (c) are 40 to 98 mol%. More preferably, the structural units derived from (a) are 10 to 50 mol% and the structural units derived from (c) are 50 to 90 mol%.

[0530] The resin [K3] can be produced, for example, in the same manner as the method described for the production method of the resin [K1].

[0531] The resin [K4] can be produced by obtaining a copolymer of (a) and (c) and adding a cyclic ether having 2 to 4 carbon atoms possessed by (b) to the carboxylic acid and / or carboxylic anhydride possessed by (a).

[0532] First, a copolymer of (a) and (c) is produced in the same manner as the method described for the production method of the resin [K1]. In this case, the ratio of the structural units derived from each unit is preferably the same as the ratio cited for the resin [K3].

[0533] Next, a cyclic ether having 2 to 4 carbon atoms possessed by (b) is reacted with a part of the carboxylic acid and / or carboxylic anhydride derived from (a) in the above copolymer.

[0534] After 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 carboxylic acid or carboxylic anhydride and the cyclic ether (such as tris(dimethylaminomethyl)phenol, etc.) and a polymerization inhibitor (such as hydroquinone, etc.) are put into the flask. For example, it is reacted at 60 to 130 °C for 1 to 10 hours, whereby the resin [K4] can be produced.

[0535] (b) is preferably used in an amount of 5 to 80 moles, more preferably 10 to 75 moles, relative to 100 moles of (a). By being in this range, there is a tendency for good balance among the storage stability of the colored resin composition, the developability during pattern formation, and the solvent resistance, heat resistance, mechanical strength, and sensitivity of the resulting pattern. Since the cyclic ether has high reactivity and it is not easy to leave unreacted (b), (b1) is preferably used as (b) used in resin [K4], and (b1-1) is more preferably used.

[0536] The amount of the above reaction catalyst used is preferably 0.001 to 5 parts by mass relative to 100 parts by mass of the total amount of (a), (b), and (c). The amount of the above polymerization inhibitor used is preferably 0.001 to 5 parts by mass relative to 100 parts by mass of the total amount of (a), (b), and (c).

[0537] Reaction conditions such as the feeding method, reaction temperature, and time can be appropriately adjusted in consideration of the manufacturing equipment, the heat generation based on polymerization, etc. It should be noted that the feeding method and reaction temperature can be appropriately adjusted in consideration of the manufacturing equipment, the heat generation based on polymerization, etc. in the same way as the polymerization conditions.

[0538] For resin [K5], as the first stage, it is carried out in the same manner as the manufacturing method of the above resin [K1] to obtain a copolymer of (b) and (c). Similarly to the above, for the obtained copolymer, the reaction solution after the reaction can be directly used, or a solution after concentration or dilution can be used, or a substance taken out in the form of a solid (powder) by methods such as reprecipitation can be used.

[0539] The ratio of the structural units from (b) and (c) relative to the total number of moles of all the structural units constituting the above copolymer is preferably 5 to 95 mol% for the structural units from (b) and 5 to 95 mol% for the structural units from (c), and more preferably 10 to 90 mol% for the structural units from (b) and 10 to 90 mol% for the structural units from (c).

[0540] Furthermore, under the same conditions as the manufacturing method of resin [K4], the carboxylic acid or carboxylic anhydride of (a) is reacted with the cyclic ether from (b) in the copolymer of (b) and (c), whereby resin [K5] can be obtained.

[0541] The amount of (a) used for reacting with the above copolymer is preferably 5 to 80 moles relative to 100 moles of (b). Since the cyclic ether has high reactivity and it is not easy to leave unreacted (b), (b1) is preferably used as (b) used in resin [K5], and (b1-1) is more preferably used.

[0542] The resin [K6] is obtained by further reacting the resin [K5] with a carboxylic anhydride. The carboxylic anhydride is made to react with the hydroxyl groups generated by the reaction of a cyclic ether with a carboxylic acid or a carboxylic anhydride.

[0543] 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 relative to 1 mole of the amount of (a) used.

[0544] As the specific resin (B), examples include (meth)acrylic acid 3,4-epoxycyclohexylmethyl ester / (meth)acrylic acid copolymer, acrylic acid 3,4-epoxytricyclo[5.2.1.0 2,6 decyl ester / (meth)acrylic acid copolymer and other resins [K1]; (meth)acrylic acid glycidyl ester / (meth)acrylic acid benzyl ester / (meth)acrylic acid copolymer, (meth)acrylic acid glycidyl ester / styrene / (meth)acrylic acid copolymer, acrylic acid 3,4-epoxytricyclo[5.2.1.0 2,6 decyl ester / (meth)acrylic acid / N-cyclohexylmaleimide copolymer, acrylic acid 3,4-epoxytricyclo[5.2.1.0 2,6 decyl ester / (meth)acrylic acid / N-cyclohexylmaleimide / (meth)acrylic acid 2-hydroxyethyl ester copolymer, 3-methyl-3-(meth)acryloxymethyloxetane / (meth)acrylic acid / styrene copolymer and other resins [K2]; (meth)acrylic acid benzyl ester / (meth)acrylic acid copolymer, styrene / (meth)acrylic acid copolymer and other resins [K3]; the resin obtained by adding (meth)acrylic acid glycidyl ester to (meth)acrylic acid benzyl ester / (meth)acrylic acid copolymer, the resin obtained by adding (meth)acrylic acid glycidyl ester to (meth)acrylic acid tricyclodecyl ester / styrene / (meth)acrylic acid copolymer, the resin obtained by adding (meth)acrylic acid glycidyl ester to (meth)acrylic acid tricyclodecyl ester / (meth)acrylic acid benzyl ester / (meth)acrylic acid copolymer and other resins [K4]; the resin obtained by reacting the copolymer of (meth)acrylic acid tricyclodecyl ester / (meth)acrylic acid glycidyl ester with (meth)acrylic acid, the resin obtained by reacting the copolymer of (meth)acrylic acid tricyclodecyl ester / styrene / (meth)acrylic acid glycidyl ester with (meth)acrylic acid and other resins [K5]; the resin obtained by further reacting the resin obtained by reacting the copolymer of (meth)acrylic acid tricyclodecyl ester / (meth)acrylic acid glycidyl ester with (meth)acrylic acid with tetrahydrophthalic anhydride and other resins [K6], etc.

[0545] Resin (B) is more preferably at least one selected from Resin [K1] and Resin [K2], and particularly preferably Resin [K2].

[0546] The polystyrene-reduced weight-average molecular weight (Mw) of Resin (B) is preferably from 1,000 to 100,000, more preferably from 2,000 to 50,000, and still more preferably from 3,000 to 30,000. When the weight-average molecular weight is within the above range, there is a tendency that the solubility of the unexposed portion in the developer is high, and the residual film rate and hardness of the resulting pattern are also high.

[0547] The dispersity [weight-average molecular weight (Mw) / number-average molecular weight (Mn)] of Resin (B) is preferably from 1 to 6, more preferably from 1.001 to 4, and still more preferably from 1.01 to 4.

[0548] The acid value (in terms of solid content) of Resin (B) is preferably from 10 mg-KOH / g to 300 mg-KOH / g, more preferably from 20 mg-KOH / g to 250 mg-KOH / g, still more preferably from 25 mg-KOH / g to 200 mg-KOH / g, even more preferably from 30 mg-KOH / g to 150 mg-KOH / g, and particularly preferably from 60 mg-KOH / g to 135 mg-KOH / g. 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 with an aqueous potassium hydroxide solution.

[0549] The content of Resin (B) in 100% by mass of the solid content of the colored resin composition is preferably from 5 to 50% by mass, more preferably from 10 to 40% by mass, and still more preferably from 15 to 30% by mass. When the content of Resin (B) is within the above range, there is a tendency that the solubility of the unexposed portion in the developer is high.

[0550] <Polymerizable Compound (C)>

[0551] The polymerizable compound (C) is a compound that can be polymerized by active radicals and / or an acid generated from a polymerization initiator (D). For example, compounds having a polymerizable ethylenically unsaturated bond can be mentioned, and (meth)acrylate compounds are preferred.

[0552] 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 monomers (a), (b), and (c).

[0553] As a polymerizable compound having two ethylenically unsaturated bonds, for example, 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, 3 - methylpentane diol di(meth)acrylate, etc. can be cited.

[0554] The polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds. As such polymerizable compounds, for example, 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, caprolactone - modified dipentaerythritol hexa(meth)acrylate, etc. can be cited. At least one selected from dipentaerythritol penta(meth)acrylate and dipentaerythritol hexa(meth)acrylate can be preferably selected.

[0555] The weight - average molecular weight of the polymerizable compound (C) is preferably 50 to 4000, more preferably 70 to 3500, further preferably 100 to 3000, still further preferably 150 to 2900, and particularly preferably 250 to 1500.

[0556] The content rate of the polymerizable compound (C) relative to the total amount of the solid components of the colored resin composition can be, for example, 1 mass% to 99 mass%, preferably 5 mass% to 90 mass%, more preferably 10 mass% to 80 mass%, and further preferably 12 mass% to 70 mass%.

[0557] <Polymerization initiator (D)>

[0558] The polymerization initiator (D) is not particularly limited as long as it is a compound that can generate active radicals, acids, etc. under the action of light or heat and initiate polymerization, and known polymerization initiators can be used.

[0559] As the polymerization initiator (D), O - acyl oxime compounds, alkyl phenyl ketone compounds, biimidazole compounds, triazine compounds, acyl phosphine oxide compounds, etc. can be cited.

[0560] As the O-acyl oxime compound, for example, N-benzoyloxy-1-(4-phenylthiophenyl)butane-1-one-2-imine, N-benzoyloxy-1-(4-phenylthiophenyl)octane-1-one-2-imine, N-benzoyloxy-1-(4-phenylthiophenyl)-3-cyclopentylpropane-1-one-2-imine, N-acetoxy-1-(4-phenylthiophenyl)-3-cyclopentylpropane-1-one-2-imine, N-acetoxy-1-(4-phenylthiophenyl)-3-cyclohexylpropane-1-one-2-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethane-1-imine, N-acetoxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethyl-2,4-dioxolanylmethoxy)benzoyl}-9H-carbazol-3-yl]ethane-1-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropane-1-imine, and N-benzoyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropane-1-one-2-imine, etc. can be cited. In addition, as the O-acyl oxime compound, commercially available products such as Irgacure (registered trademark) OXE01, OXE02 (both are manufactured by BASF), N-1919 (manufactured by ADEKA Corporation), and TR-PBG327 (manufactured by Changzhou Qiangli Electronic New Materials Company) can also be used. Among them, as the O-acyl oxime compound, it is preferably at least one selected from N-benzoyloxy-1-(4-phenylthiophenyl)butane-1-one-2-imine, N-benzoyloxy-1-(4-phenylthiophenyl)octane-1-one-2-imine, N-benzoyloxy-1-(4-phenylthiophenyl)-3-cyclopentylpropane-1-one-2-imine, and TR-PBG327 (N-acetoxy-1-(4-phenylthiophenyl)-3-cyclohexylpropane-1-one-2-imine), and more preferably at least one selected from N-benzoyloxy-1-(4-phenylthiophenyl)octane-1-one-2-imine and TR-PBG327 (N-acetoxy-1-(4-phenylthiophenyl)-3-cyclohexylpropane-1-one-2-imine).

[0561] As the alkyl phenyl ketone compound, 2-methyl-2-morpholino-1-(4-methylthiophenyl)propane-1-one, 2-dimethylamino-1-(4-morpholinophenyl)-2-benzylbutane-1-one, and 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]butane-1-one, etc. can be cited. As the alkyl phenyl ketone compound, commercially available products such as Irgacure (registered trademark) 369, 907, 379 (all are manufactured by BASF) can be used.

[0562] As alkyl phenyl ketone compounds, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy)phenyl]propan-1-one, 1-hydroxycyclohexyl phenyl ketone, oligomers of 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propan-1-one, α,α-diethoxyacetophenone, and benzil dimethyl ketal can also be mentioned.

[0563] As bisimidazole compounds, for example, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenyl bisimidazole, 2,2'-bis(2,3-dichlorophenyl)-4,4',5,5'-tetraphenyl bisimidazole (for example, refer to Japanese Patent Laid-Open No. 6-75372, Japanese Patent Laid-Open No. 6-75373, etc.), 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(alkoxyphenyl) bisimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(dialkoxyphenyl) bisimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(trialkoxyphenyl) bisimidazole (for example, refer to Japanese Patent Publication No. 48-38403, Japanese Patent Laid-Open No. 62-174204, etc.), bisimidazole compounds in which the phenyl groups at the 4,4',5,5'-positions are substituted with carbalkoxy groups (for example, refer to Japanese Patent Laid-Open No. 7-10913, etc.), etc.

[0564] As triazine compounds, 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-methoxystyrene)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(5-methylfuran-2-yl)vinyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)vinyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl)vinyl]-1,3,5-triazine, and 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)vinyl]-1,3,5-triazine, etc. can be mentioned.

[0565] As acylphosphine oxide compounds, 2,4,6-trimethylbenzoyl diphenylphosphine oxide, etc. can be mentioned. Commercially available products such as Irgacure (registered trademark) 819 (manufactured by BASF Corporation) can be used.

[0566] In addition, 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, benzil, methyl benzoylformate, and metallocene compounds, etc.

[0567] They are preferably used in combination with a polymerization initiator assistant (D1) (particularly an amine compound) described later.

[0568] The polymerization initiator (D) is preferably a polymerization initiator containing at least one selected from the group consisting of alkylbenzene ketone compounds, triazine compounds, acylphosphine oxide compounds, O-acyl oxime compounds, and biimidazole compounds, and more preferably a polymerization initiator containing an O-acyl oxime compound.

[0569] The content of the polymerization initiator (D) is preferably 0.1 to 30 parts by mass, and more preferably 1 to 20 parts by mass, based on 100 parts by mass in total 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, there is a tendency to increase the sensitivity and shorten the exposure time, and thus the productivity of the color filter is improved.

[0570] <Polymerization initiator assistant (D1)>

[0571] The colored resin composition of the present invention may contain a polymerization initiator assistant (D1). The polymerization initiator assistant (D1) is a compound or a sensitizer for promoting the polymerization of the polymerizable compound (C) initiated by the polymerization initiator (D). When the polymerization initiator assistant (D1) is contained, it is usually used in combination with the polymerization initiator (D).

[0572] Examples of the polymerization initiator assistant (D1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds, and carboxylic acid compounds, etc.

[0573] Examples of the amine compound include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isopentyl 4-dimethylaminobenzoate, 2-(dimethylamino)ethyl 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. Among them, 4,4'-bis(diethylamino)benzophenone is preferably selected. In addition, as the amine compound, commercially available products such as EAB-F (manufactured by Hodogaya Chemical Co., Ltd.) can be used.

[0574] 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.

[0575] Examples of the thioxanthone compound include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, and 1-chloro-4-propoxythioxanthone.

[0576] Examples of the carboxylic acid compound include phenylthioacetic acid, methylphenylthioacetic acid, ethylphenylthioacetic acid, methylethylphenylthioacetic acid, dimethylphenylthioacetic acid, methoxyphenylthioacetic acid, dimethoxyphenylthioacetic acid, chlorophenylthioacetic acid, dichlorophenylthioacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, and naphthoxyacetic acid.

[0577] When using these polymerization initiator aids (D1), its content is preferably 0.1 part by mass to 30 parts by mass, more preferably 1 part by mass to 20 parts by mass, 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.

[0578] <Solvent (E)>

[0579] The solvent (E) is not particularly limited, and solvents commonly used in the art can be employed.

[0580] For the solvent (E), for example, an ester solvent (a solvent containing -COO- in the molecule and not containing -O-), an ether solvent (a solvent containing -O- in the molecule and not containing -COO-), an ether ester solvent (a solvent containing -COO- and -O- in the molecule), a ketone solvent (a solvent containing -CO- in the molecule and not containing -COO-), an alcohol solvent (a solvent containing OH in the molecule and not containing -O-, -CO-, and -COO-), an aromatic hydrocarbon solvent, an amide solvent, dimethyl sulfoxide, etc. Two or more of these solvents can be used in combination.

[0581] Examples of the ester solvent include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutyrate, ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, isoamyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexyl acetate, and γ-butyrolactone.

[0582] Examples of the ether solvent 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, and methylanisole.

[0583] Examples of the ether ester solvent 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.

[0584] 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.

[0585] Examples of the alcohol solvent include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerin.

[0586] Examples of the aromatic hydrocarbon solvent include benzene, toluene, xylene, and mesitylene.

[0587] Examples of the amide solvent include N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.

[0588] As the solvent (E), a solvent containing at least one selected from propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate, diacetone alcohol, and cyclohexanone is preferred.

[0589] The content rate of the solvent (E) is usually 99.99% by mass or less, preferably 40% to 99% by mass, more preferably 50% to 95% by mass, further preferably 70% to 95% by mass, and even more preferably 75% to 90% by mass with respect to the total amount of the colored resin composition. In other words, the total amount of the solid components of the colored resin composition is usually 0.01% by mass or more, preferably 1% to 60% by mass, more preferably 5% to 50% by mass, further preferably 5% to 30% by mass, and even more preferably 10% to 25% by mass. When the content rate of the solvent (E) is within the above range, the flatness during coating becomes good, and the color density is not insufficient when forming a color filter, so there is a tendency for the display characteristics to become good.

[0590] <Leveling agent (F)>

[0591] Examples of the leveling agent (F) include silicone-based surfactants, fluorine-based surfactants, and silicone-based surfactants having fluorine atoms. They may have a polymerizable group in the side chain.

[0592] Examples of the silicone-based surfactant include surfactants having a siloxane bond in the molecule. Specifically, examples include Toray Silicone DC3PA, Toray Silicone SH7PA, Toray Silicone DC11PA, Toray Silicone SH21PA, Toray Silicone SH28PA, Toray Silicone SH29PA, Toray Silicone SH30PA, Toray Silicone SH8400 (trade name: manufactured by Dow Corning Toray 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.

[0593] Examples of the fluorine-based surfactant include surfactants having a fluorocarbon chain in the molecule. Specifically, examples include FLUORAD (registered trademark) FC430, FLUORAD FC431 (manufactured by Sumitomo 3M Limited), MEGAFAC (registered trademark) F142D, MEGAFAC F171, MEGAFAC F172, MEGAFAC F173, MEGAFAC F177, MEGAFAC F183, MEGAFAC F554, MEGAFAC R30, MEGAFAC RS-718-K (manufactured by DIC Corporation), F-top (registered trademark) EF301, F-top EF303, F-top EF351, F-top EF352 (manufactured by Mitsubishi Materials Electronic Chemicals Co., Ltd.), Surflon (registered trademark) S381, Surflon S382, Surflon SC101, Surflon SC105 (manufactured by Asahi Glass Co., Ltd.), and E5844 (manufactured by Daikin Fine Chemical Research Institute Co., Ltd.), etc.

[0594] Examples of the silicone-based surfactant having a fluorine atom include surfactants having a siloxane bond and a fluorocarbon chain in the molecule. Specifically, examples include MEGAFAC (registered trademark) R08, MEGAFAC BL20, MEGAFAC F475, MEGAFAC F477, and MEGAFAC F443 (manufactured by DIC Corporation), etc.

[0595] When a leveling agent (F) is contained, the content rate of the leveling agent (F) is preferably 0.0005% by mass to 1% by mass, more preferably 0.001% by mass to 0.5% by mass, and still more preferably 0.005% by mass to 0.1% by mass, relative to the total amount of the colored resin composition. It should be noted that the content does not include the content of the above-mentioned dispersant. When the content rate of the leveling agent (F) is within the above range, the flatness of the color filter can be improved.

[0596] <Other components>

[0597] The colored resin composition may contain, as needed, additives well-known in the art such as fillers, other polymer compounds, adhesion promoters, quenchers, antioxidants, light stabilizers, and chain transfer agents.

[0598] <Method for producing colored resin composition>

[0599] The colored resin composition can be prepared by mixing phenylphosphoric acid and diphenylphosphoric acid which may have substituents, a colorant (A), a dispersant (P), a resin (B), and, as needed, a polymerizable compound (C), a polymerization initiator (D), a polymerization initiator assistant (D1), a solvent (E), a leveling agent (F), and other components. The mixing can be carried out using well-known or conventional devices and conditions.

[0600] The colorant (A) can be used in the form of a colorant-containing solution obtained by previously mixing with a part or all of the solvent (E) and dispersing it with a bead mill to an average particle size of about 0.2 μm or less, and is preferably used in the form of a colorant-containing solution. At this time, a part or all of the above-mentioned dispersant (P) and resin (B) can be blended as needed. In addition, the colorant (A) can also be used in the form of a colorant-containing solution obtained by previously dissolving it in a part or all of the solvent (E). By mixing the remaining components in the colorant-containing solution thus obtained to a specified concentration, the target colored resin composition can be prepared.

[0601] <Method for producing color filter>

[0602] A color filter that can serve as a color conversion layer can be formed from the colored resin composition of the present invention. As a method for forming a colored pattern, there can be mentioned a photolithography method, an inkjet method, a printing method, etc. Among them, the photolithography method is preferred. The photolithography method is a method of coating the above-mentioned colored resin composition on a substrate, drying it to form a colored resin composition layer, exposing the colored resin composition layer through a photomask, and developing it. In the photolithography method, a colored coating film, which is a cured product of the above-mentioned colored resin composition layer, can be formed by not using a photomask and / or not performing development during exposure. The colored pattern and colored coating film thus formed are the color filters of the present invention.

[0603] The film thickness of the produced color filter is not particularly limited and can be appropriately adjusted according to the purpose, use, etc. For example, it is 0.1 μm to 30 μm, preferably 0.1 μm to 20 μm, more preferably 0.5 μm to 6 μm, and still more preferably 0.8 μm to 4.5 μm.

[0604] As the substrate, glass plates such as quartz glass, borosilicate glass, aluminosilicate glass, and soda-lime glass with a silica coating on the surface, resin plates such as polycarbonate, polymethyl methacrylate, and polyethylene terephthalate, silicon, and substrates with aluminum, silver, silver / copper / palladium alloy thin films, etc. formed on the above substrates can be used. Other color filter layers, resin layers, transistors, circuits, etc. can be formed on these substrates.

[0605] The formation of each color pixel based on photolithography can be carried out using known or conventional devices and conditions. For example, it can be produced as described below.

[0606] First, the colored resin composition is coated on the substrate and heated and dried (pre-baked) and / or dried under reduced pressure to remove volatile components such as solvents and make it dry, obtaining a smooth colored resin composition layer.

[0607] As the coating method, spin coating method, slit coating method, slit and spin coating method, etc. can be cited.

[0608] When heating and drying, the temperature is preferably 30 to 120 °C, more preferably 50 °C to 110 °C. In addition, as the heating time, it is preferably 10 seconds to 60 minutes, more preferably 30 seconds to 30 minutes.

[0609] When drying under reduced pressure, it is preferably carried out at a pressure of 50 to 150 Pa in a temperature range of 20 to 25 °C.

[0610] The film thickness of the colored resin composition layer is not particularly limited and can be appropriately selected as long as it is based on the film thickness of the target color filter.

[0611] Next, the colored resin composition layer is exposed through a photomask for forming the target colored pattern. The pattern on this photomask is not particularly limited, and a pattern corresponding to the target use is used. In addition, in order to be able to uniformly irradiate parallel light on the entire exposure surface and accurately align the photomask with the substrate on which the colored resin composition layer is formed, exposure devices such as mask aligners and steppers are preferably used. In the case of forming a colored coating film, it is only necessary to expose without using a photomask.

[0612] As the light source used for exposure, a light source that preferably generates light with a wavelength of 250 to 450 nm is used. For example, light with a wavelength less than 350 nm can be cut off using a filter that cuts off this wavelength region, or light near 436 nm, near 408 nm, or near 365 nm can be selectively extracted using a band-pass filter that extracts these wavelength regions. Specifically, a mercury lamp, a light-emitting diode, a metal halide lamp, a halogen lamp, etc. can be mentioned.

[0613] The exposed colored resin composition layer is brought into contact with a developer to perform development, thereby forming a colored pattern on the substrate. By development, the unexposed portion of the colored resin composition layer dissolves in the developer and is removed. As the developer, for example, an aqueous solution of an alkaline compound such as potassium hydroxide, sodium bicarbonate, sodium carbonate, or tetramethylammonium hydroxide is preferably used. The concentration of these alkaline compounds in the aqueous solution is preferably 0.01% by mass to 10% by mass, more preferably 0.03% by mass to 5% by mass. In addition, the developer may contain a surfactant.

[0614] The development method can be any one of a paddle method, an immersion method, a spray method, etc. Further, the substrate can be tilted at an arbitrary angle during development.

[0615] The developed substrate is preferably washed with water.

[0616] In addition, it is preferable to perform post-baking on the obtained colored pattern or colored coating film. The post-baking temperature is preferably 150°C to 250°C, more preferably 160°C to 240°C. The post-baking time is preferably 1 to 120 minutes, more preferably 10 to 60 minutes.

[0617] <Display device>

[0618] The above-described 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 element.

[0619] Examples

[0620] Hereinafter, synthesis examples are given to illustrate the present invention more specifically. In the examples, % and parts indicating content or usage amount are based on mass unless otherwise specified.

[0621] In the following synthesis examples, the structure of the compound was confirmed by a mass spectrometer (LC; Agilent 1200 type, MASS; Agilent LC / MSD6130 type).

[0622] <Synthesis of pigment>

[0623] [Pigment synthesis example I-1: Synthesis of compound (B-I-1)]

[0624] The following reaction was carried out under a nitrogen atmosphere. 0.48 parts 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 placed in a flask equipped with a condenser and a stirrer. Then, a mixed solution of 9 parts of 4,4'-methylenebis(2,6-dimethylaniline) (manufactured by Sigma-Aldrich) and 63 parts of toluene was added dropwise to the flask. The reaction solution was heated to 110 °C with an oil bath and stirred for 2 hours. After allowing the reaction solution to cool, it was filtered through diatomaceous earth to obtain a filtrate. 180 parts of ethyl acetate and 180 parts of ion-exchanged water were added thereto, and after vigorous mixing, liquid separation was performed to obtain an organic layer. The obtained organic layer was dried with 48 parts of sodium sulfate, and the solid was filtered off and removed. 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).

[0625]

[0626] Identification of the compound represented by the formula (B-I-1)

[0627] (Mass spectrometry) Ionization mode = ESI+: m / z = 506.5

[0628] [Example of pigment synthesis I-2: Synthesis of compound (C-I-1)]

[0629] 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 placed in a flask equipped with a condenser tube and a stirring device. 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 with an oil bath. After cooling the reaction solution with an ice bath, filtration was carried out to obtain a solid and a filtrate. This solid was designated as crude product A1, and this 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 placed in a flask equipped with a bottom drain port and stirred for 1 hour, followed by liquid separation to obtain an organic layer. The obtained organic layer was subjected to liquid separation and washing with a mixed solution of 238 parts of ion-exchanged water and 12.5 parts of sodium carbonate, and then dried with 150 parts of magnesium sulfate, and the solid was filtered off and removed. 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 placed in a flask equipped with a stirring device, and 4 times the mass of acetonitrile was added based on the total mass of crude product B1 and crude product C1, and the mixture was stirred for 1 hour. The solid obtained by filtering this mixed solution was washed with acetonitrile in an amount of 1 time the mass of 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 formula (C-I-1). The yield was 90.6%.

[0630]

[0631] [Synthesis Example of Pigment I-3: Synthesis of Compound (C-I-2)]

[0632] The following reaction is carried out under a nitrogen atmosphere. 50 parts of the compound represented by formula (C-I-1) and 188 parts of N,N-dimethylformamide are charged into a flask equipped with a condenser and a stirrer, and stirred for 30 minutes while cooling with an ice bath. 40 parts of potassium tert-butoxide (manufactured by Tokyo Chemical Industry Co., Ltd.) is charged into this flask, and stirred for another 1 hour while cooling with an ice bath. 55.6 parts of iodoethane (manufactured by Tokyo Chemical Industry Co., Ltd.) is added dropwise to the reaction solution while it is kept ice-cold. After the reaction solution is heated to 35 °C using an oil bath and stirred for 5 hours, it is cooled to room temperature. 1000 parts of 10% aqueous sodium chloride solution is charged into another flask equipped with a stirrer, and the above reaction solution is added dropwise while stirring. After stirring for 30 minutes, filtration is carried out to obtain a solid. The obtained solid is washed 3 times with 500 parts of ion-exchanged water and dried under reduced pressure at 60 °C to obtain 53.0 parts of the compound represented by formula (C-I-2). The yield is 93.5%.

[0633]

[0634] [Pigment Synthesis Example I-4: Synthesis of Compound (I-5a-1)]

[0635] The following reaction is carried out under a nitrogen atmosphere. 1 part of the compound represented by formula (B-I-1), 11.28 parts of the compound represented by formula (C-I-2) and 42 parts of toluene are charged into a flask equipped with a condenser and a stirrer, and then 5.4 parts of phosphoryl chloride (manufactured by Fujifilm Wako Pure Chemical Corporation) is added, and the mixture is stirred at 110 °C for 7.5 hours. Then, after the reaction mixture is cooled to room temperature, 450 parts of ethyl acetate and saturated brine are added and filtered to obtain a crude product. It is purified by silica gel column chromatography (solvent: chloroform / methanol 100 / 1 to 10 / 1), the obtained fraction is concentrated under reduced pressure, and dried under reduced pressure at 60 °C to obtain 9.90 parts of the compound represented by formula (I-5a-1).

[0636]

[0637] Identification of the compound represented by formula (I-5a-1)

[0638] (Mass spectrometry) Ionization mode = ESI+: m / z = 712.6, divalent

[0639] [Pigment Synthesis Example I-5: Synthesis of Compound (I-5a-2)]

[0640] The following reaction is carried out under a nitrogen atmosphere. 4 parts of the compound represented by formula (I-5a-1) and 26.7 parts of methanol are charged into a flask equipped with a condenser and a stirrer, and stirred at room temperature for 30 minutes to prepare a blue solution.

[0641] 17.8 parts of water was put into a flask equipped with a cooling tube and a stirring device, and then 6.2 parts of phosphotungstic acid hydrate (Keggin type phosphotungstic acid; manufactured by Sigma-Aldrich Co., Ltd.) was put into the water. Under an air atmosphere, mixing was carried out at room temperature to prepare a phosphotungstic acid solution.

[0642] 53.4 parts of the previously prepared blue solution and washed methanol were added dropwise to the obtained phosphotungstic acid solution. After heating to 55 °C with an oil bath and stirring for 4 hours, 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, which was filtered, and washed successively with 50 parts of ion-exchanged water and 10 parts of methanol. The obtained crude product was put into 80 parts of methanol and dispersed for 1 hour, 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 formula (I-5a-2).

[0643]

[0644] Identification of the compound represented by formula (I-5a-2)

[0645] (Mass spectrometry) Ionization mode = MALDI+: m / z = 1423.7

[0646] Ionization mode = MALDI−: m / z = 2902.5

[0647] [Pigment synthesis example 2]

[0648] The following reaction was carried out under a nitrogen atmosphere. 8.0 parts of the compound represented by formula (TA-II-1) and 396.0 parts of methanol were put into a flask equipped with a cooling tube and a stirring device, and then stirred at room temperature for 30 minutes to prepare a blue solution. Then, 396.0 parts of tap water was put into the blue solution, and then stirred at room temperature for 30 minutes to obtain a reaction solution.

[0649] 53 parts of tap water was put into a beaker, and further 11.8 parts of Keggin type phosphotungstic acid (manufactured by Aldrich) and 53 parts of methanol were put into the tap water. Under an air atmosphere, mixing was carried out at room temperature to prepare a phosphotungstic acid solution.

[0650] The obtained phosphotungstic acid solution was added dropwise to the previously prepared reaction solution over 1 hour. Subsequently, after stirring at room temperature for 30 minutes, filtration was carried out to obtain a blue solid. The obtained blue solid was put into 200.0 parts of methanol to disperse for 1 hour, followed by filtration, and the above operation was repeated 2 times. The blue solid obtained through this operation was put into 200.0 parts of tap water to disperse for 1 hour, followed by filtration, and the above operation was repeated 2 times. The blue solid obtained through this operation was dried under reduced pressure at 60 °C to obtain 17.1 parts of the compound represented by the formula (TA-I-1) (hereinafter, referred to as compound (TA-I-1)). The yield was 94%.

[0651]

[0652] [Example of pigment synthesis 3]

[0653] According to the description of Example 2-3 of Japanese Patent Laid-Open No. 2018-138678, the compound represented by the following formula (II-3) (sometimes referred to as compound (II-3)) was manufactured.

[0654]

[0655] <Synthesis of resin>

[0656] [Example of resin synthesis 1]

[0657] An appropriate amount of nitrogen was introduced into a flask equipped with a reflux condenser, a dropping funnel, and a stirrer and replaced with a nitrogen atmosphere. 371 parts of propylene glycol monomethyl ether acetate was charged, and it was heated to 85 °C while stirring. Subsequently, a mixed solution of 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 (containing a molar ratio of 1:1), 81 parts of vinyltoluene (isomer mixture), and 80 parts of propylene glycol monomethyl ether acetate was added dropwise to the flask over 4 hours. On the other hand, a solution obtained by dissolving 30 parts of the 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 addition of the initiator solution was completed, it was maintained 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 using a B-type viscometer (23 °C). The weight-average molecular weight of the generated 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.

[0658]

[0659] The weight-average molecular weight (Mw) and number-average molecular weight (Mn) of the above resin were measured by the GPC method under the following conditions.

[0660] Apparatus: K2479 (manufactured by Shimadzu Corporation)

[0661] Column: SHIMADZU Shim-pack GPC-80M

[0662] Column temperature: 40 °C

[0663] Solvent: Tetrahydrofuran (THF)

[0664] Concentration of the test solution; 25 mg / mL (solvent; THF)

[0665] Flow rate: 1.0 mL / min

[0666] Detector: RI

[0667] Standard substance for calibration: TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Corporation)

[0668] The ratio of the weight-average molecular weight to the number-average molecular weight of the polystyrene obtained above was taken as the dispersity (Mw / Mn).

[0669] [Resin synthesis example 2]

[0670] An appropriate amount of nitrogen was introduced into a flask equipped with a reflux condenser, a dropping funnel, and a stirrer, and the atmosphere was replaced with nitrogen. 141 parts of ethyl lactate and 178 parts of propylene glycol monomethyl ether acetate were charged, and the mixture was heated to 85 °C while stirring. Then, a mixed solution of 25 parts of a mixture of 3,4-epoxytricyclo[5.2.1.0]decane-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0]decane-9-yl acrylate (containing a molar ratio of 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 obtained by dissolving 5 parts of 2,2-azobisisobutyronitrile in 88 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After the addition was completed, the mixture was maintained 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 mPas measured by a B-type viscometer (23 °C) and a solid content of 25.6%. The weight-average molecular weight Mw of the resulting copolymer was 8.0×10 2,6 decane-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 2,6 decane-9-yl acrylate (containing a molar ratio of 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 obtained by dissolving 5 parts of 2,2-azobisisobutyronitrile in 88 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After the addition was completed, the mixture was maintained 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 mPas measured by a B-type viscometer (23 °C) and a solid content of 25.6%. The weight-average molecular weight Mw of the resulting copolymer was 8.0×10 3, the degree of dispersion is 2.1, and the acid value in terms of solid content is 109 mg-KOH / g. Resin B-2 has the following structural units.

[0671]

[0672] [Preparation Example 1]

[0673] <Preparation of Colorant Dispersion (A-1) Containing Compound (I-5a-2)>

[0674] Mix 5.0 parts of compound (I-5a-2), 0.25 parts of phenylphosphoric 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. Use a paint conditioner (manufactured by LAU Co., Ltd.) to shake the resulting mixture for 3 hours. Then, remove the zirconia beads by filtration to obtain colorant dispersion (A-1).

[0675] [Preparation Examples 2 to 4]

[0676] <Preparation of Colorant Dispersions (A-2) to (A-4)>

[0677] Change the dispersants in Preparation Example 1 to P-2 to P-4 respectively. Otherwise, obtain colorant dispersions (A-2) to (A-4) by the same method as in Preparation Example 1.

[0678] P-2: BYK-LP N 21324 (manufactured by BYK-Chemie, amine value 0 mg KOH / g)

[0679] P-3: DISPERBYK-2001 (manufactured by BYK-Chemie, amine value 29 mg KOH / g, acid value 19 mg KOH / g)

[0680] P-4: DISPERBYK-2150 (manufactured by BYK-Chemie, amine value 57 mg KOH / g)

[0681] [Preparation Example 5]

[0682] <Preparation of Colorant Dispersion (A-5)>

[0683] Change the phenylphosphoric acid in Preparation Example 4 to diphenylphosphoric acid (manufactured by Tokyo Chemical Industry Co., Ltd.). Otherwise, obtain colorant dispersion (A-5) in the same manner as in Preparation Example 4.

[0684] [Preparation Example 6]

[0685] <Preparation of Colorant Dispersion (A-6)>

[0686] Mix 5.0 parts of compound (TA-I-1), 0.5 part of diphenylphosphoric 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. Use a paint conditioner (manufactured by LAU Co., Ltd.) to shake the resulting mixture for 3 hours. Then, remove the zirconia beads by filtration to obtain colorant dispersion (A-6).

[0687] [Preparation Example 7]

[0688] <Preparation of Colorant Dispersion (A-7) Containing Compound (II-3)>

[0689] Mix 5.0 parts of compound (II-3), 0.25 part of phenylphosphoric acid (manufactured by Tokyo Chemical Industry Co., Ltd.), 3.0 parts of dispersant P-3 (manufactured by BYK-Chemie, DISPERBYK-2001, amine value 29 mg KOH / g, acid value 19 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. Use a paint conditioner (Paint Conditioner, manufactured by LAU Co., Ltd.) to shake the resulting mixture for 3 hours. Then, remove the zirconia beads by filtration to obtain colorant dispersion (A-7).

[0690] [Comparative Preparation Example 1]

[0691] <Preparation of Colorant Dispersion (A-8)>

[0692] Mix 5.0 parts of compound (I-5a-2), 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. Use a paint conditioner (manufactured by LAU Co., Ltd.) to shake the resulting mixture for 3 hours. Then, remove the zirconia beads by filtration to obtain colorant dispersion (A-8).

[0693] [Comparative Preparation Example 2]

[0694] <Preparation of Colorant Dispersion (A-9)>

[0695] The dispersant in Preparation Example 1 was changed to P-5, and a colorant dispersion (A-9) was obtained in the same manner as in Preparation Example 1 except for this change.

[0696] P-5: DISPERBYK-108 (manufactured by BYK-Chemie, amine value 71 mg KOH / g)

[0697] [Comparative Preparation Example 3]

[0698] <Preparation of Colorant Dispersion (A-10)>

[0699] The compound (I-5a-2) in Comparative Preparation Example 1 was changed to the compound (TA-I-1), and a colorant dispersion (A-10) was obtained in the same manner as in Comparative Preparation Example 1 except for this change.

[0700] [Comparative Preparation Example 4]

[0701] <Preparation of Colorant Dispersion (A-11)>

[0702] Phenylphosphoric acid in Preparation Example 7 was not added, and a colorant dispersion (A-11) was obtained in the same manner as in Preparation Example 7 except for this change.

[0703] Example 1

[0704] <Preparation of Colored Resin Composition 1>

[0705] The following components were mixed to obtain Colored Resin Composition 1.

[0706]

[0707] Examples 2 to 5

[0708] <Preparation of Colored Resin Compositions 2 to 5>

[0709] The colorant dispersions (A-1) in Preparation Example 1 were respectively changed to colorant dispersions (A-2) to (A-5), and Colored Resin Compositions 2 to 5 were obtained in the same manner as in Preparation Example 1 except for this change.

[0710] Example 6

[0711] <Preparation of Colored Resin Composition 6>

[0712] The following components were mixed to obtain Colored Resin Composition 6.

[0713]

[0714]

[0715] Example 7

[0716] <Preparation of Colored Resin Composition 7>

[0717] The following components were mixed to obtain Colored Resin Composition 7.

[0718]

[0719] Comparative Example 1

[0720] <Preparation of Comparative Colored Resin Composition 1>

[0721] The following components were mixed to obtain Comparative Colored Resin Composition 1.

[0722]

[0723] Comparative Example 2

[0724] <Preparation of Comparative Colored Resin Composition 2>

[0725] The following components were mixed to obtain Comparative Colored Resin Composition 2.

[0726]

[0727] Comparative Example 3

[0728] <Preparation of Comparative Colored Resin Composition 3>

[0729] The following components were mixed to obtain Comparative Colored Resin Composition 3.

[0730]

[0731] Comparative Example 4

[0732] <Preparation of Comparative Colored Resin Composition 4>

[0733] The following components were mixed to obtain Comparative Colored Resin Composition 4.

[0734]

[0735] <Formation of Colored Coating Film (Color Filter)>

[0736] The colored resin compositions 1 to 7 obtained in Examples 1 to 7 and the comparative colored resin compositions 1 to 4 obtained in Comparative Examples 1 to 4 were respectively coated on a 2-inch square glass substrate (EAGLE 2000; manufactured by CORNING) by spin coating, pre-baked at 100 °C for 3 minutes to form a composition layer. After cooling, an exposure machine (TME-150RSK; manufactured by TOPCON) was used, and in an atmospheric atmosphere, at 60 mJ / cm 2After irradiating the composition layer with an exposure amount (based on 365 nm), it was baked in an oven at 230 °C for 20 minutes to obtain a colored coating film.

[0737] <Evaluation of contrast>

[0738] For the obtained colored coating film, a contrast meter (CT-1; manufactured by Kamban Electric Co., Ltd., color difference meter BM-5A; manufactured by TOPCON Corporation, light source; F-10, polarizing film; manufactured by Kamban Electric Co., Ltd.) was used, and the blank value was set to 50000 to measure the contrast.

[0739] <Evaluation of brightness>

[0740] For the obtained colored coating film, a colorimeter (OSP-SP-200; manufactured by Olympus Corporation) was used to measure the spectral reflectance, and the characteristic function of the C light source was used to measure the xy chromaticity coordinates (x, y) and the stimulus value Y in the CIE XYZ colorimetric system. Y represents brightness, and the Y values at the same y coordinate were compared and evaluated. The larger Y is, the higher the brightness.

[0741] The results of the film thickness, brightness, and contrast of the colored coating films obtained in Examples 1 to 5 and Comparative Examples 1 to 2 are shown in Table 11.

[0742] [Table 11]

[0743]

[0744] The results of the film thickness, brightness, and contrast of the colored coating films obtained in Example 6 and Comparative Example 3 are shown in Table 12.

[0745] [Table 12]

[0746]

[0747] The results of the film thickness, brightness, and contrast of the colored coating films obtained in Example 7 and Comparative Example 4 are shown in Table 13.

[0748] [Table 13]

[0749]

[0750] When the amine value of the dispersant exceeds 65 mgKOH / g, the brightness and contrast are greatly reduced (Comparative Example 2). Even when the amine value of the dispersant is 65 mgKOH / g or less, but phenylphosphoric acid is not added, although the brightness and contrast are improved, they are not sufficient (Comparative Example 1).

[0751] Comparing Examples 1 to 5, in which the amine value of the dispersant is 65 mgKOH / g or less and phenylphosphoric acid is added, with Comparative Examples 1 to 2, it can be seen that they exhibit high contrast and high brightness.

[0752] In Example 6 where the amine value of the dispersant is 65 mgKOH / g or less and diphenylphosphoric acid is added, it can be seen that a high contrast is exhibited and the brightness is also increased compared to Comparative Example 3.

[0753] In Example 7 where the amine value of the dispersant is 65 mgKOH / g or less and phenylphosphoric acid and colorant (II-3) are added, it can be seen that a high contrast is exhibited and the brightness is also increased compared to Comparative Example 4.

Claims

1. A colored resin composition comprising one or more acids selected from phenylphosphoric acid which may have a substituent and diphenylphosphoric acid which may have a substituent, a colorant, a dispersant, and a resin, wherein the colorant comprises a compound represented by the following formula (I), and the dispersant has an amine value of 0 mgKOH / g to 65 mgKOH / g. In formula (I), R 1 ~R 4 and R 13 each independently represents a hydrogen atom or an optionally substituted hydrocarbon group having 1 to 10 carbon atoms, R 5 ~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 ring which may have a substituent, a represents an integer greater than 1, i) When a is 1, T 2 represents a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent, ii) When a is an integer greater than or equal to 2, T 2 It represents an a-valent group which may have a substituent, and the -CH2- contained in the a-valent group may be replaced by -O-, -CO-, -S-, -SO-, -SO2- or -NR 1a -replace, R 1a represents a hydrogen atom or an aliphatic hydrocarbon group having 1 to 8 carbon atoms, b and c independently represent an integer greater than 1, d represents an integer greater than 0, X c- It represents a c-valent anion.

2. The colored resin composition according to claim 1, wherein In formula (I), a is an integer greater than 2, T 2 represents a group represented by formula (i), In formula (i), T 3 represents an a-valent cyclic hydrocarbon group, and L 2 represents a divalent aliphatic hydrocarbon group having 1 to 5 carbon atoms which may have a substituent, or T 3 represents a divalent aliphatic hydrocarbon group having 1 to 5 carbon atoms which may have a substituent, and L 2 represents an a-valent cyclic hydrocarbon group, * indicates the bonding site to the nitrogen atom.

3. The colored resin composition according to claim 1 or 2, wherein It further contains a polymerizable compound and a polymerization initiator. 4 . A color filter formed from the colored resin composition according to claim 3 .

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

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