compound

Abstract

The present invention addresses the problem of providing a compound with which it is possible to form a color filter having exceptional brightness. The aforementioned problem is solved by a compound represented by formula (I). (I) [In formula (I), T1 and T2 each independently represent a divalent aromatic hydrocarbon group optionally having a substituent or a divalent aromatic heterocyclic group optionally having a substituent, L1 represents a C1-12 a-valent aliphatic hydrocarbon group optionally having a substituent or a group represented by formula (i), at least one of the methylene groups included in the aliphatic hydrocarbon group is substituted by -O-, and a represents an integer equal to or greater than 2.] (i) [In formula (i), T3 represents an a-valent aromatic hydrocarbon group optionally having a substituent or an a-valent aromatic heterocyclic group optionally having a substituent, L2 represents a C1-5 divalent aliphatic hydrocarbon group optionally having a substituent, and at least one of the methylene groups included in the aliphatic hydrocarbon group is substituted by -O-.]

Description

[Technical Field]

[0001] The present invention relates to compounds, colored resin compositions, color filters, and display devices. [Background technology]

[0002] Color filters used in display devices such as liquid crystal displays, electroluminescent displays, and plasma displays, as well as solid-state image sensors such as CCDs and CMOS sensors, are manufactured from colored resin compositions. Various colorants are used as colored resin compositions for forming these color filters, and examples of compounds represented by the following formulas (x1) and (x2) are known to be used as colorants (Patent Document 1).

[0003] [ka] [Prior art documents] [Patent Documents]

[0004] [Patent Document 1] Japanese Patent Publication No. 2014-108975 [Overview of the project] [Problems that the invention aims to solve]

[0005] However, color filters formed from colored resin compositions containing the above-mentioned compounds sometimes did not have sufficiently satisfactory brightness. Therefore, the object of the present invention is to provide a compound capable of forming color filters with excellent brightness. [Means for solving the problem]

[0006] The gist of this invention is as follows: [1] A compound represented by formula (I). [ka] [In formula (I), R , , , 2 , , 3 , , , , , 2 , ~R 4 and R 13 each independently represent a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent. R 5 ~R 12 each independently represent a hydrogen atom, a halogen atom or a hydrocarbon group having 1 to 5 carbon atoms which may have a substituent. T 1 and T 2 each independently represent a divalent aromatic hydrocarbon group which may have a substituent or a divalent aromatic heterocyclic group which may have a substituent. L 1 represents an a-valent aliphatic hydrocarbon group having 1 to 12 carbon atoms which may have a substituent or a group represented by formula (i), and at least one of the methylene groups contained in the aliphatic hydrocarbon group is replaced by -O-. a represents an integer of 2 or more. b and c each independently represent an integer of 1 or more. d represents an integer of 0 or more. X c- represents a c-valent anion.] [Chemical formula] <00003​​​​​​​​​​​​​​​​​​​ [4] A color filter formed from the colored resin composition described in [2] or [3]. A display device including the color filter described in [5] [4]. [Effects of the Invention]

[0007] According to the present invention, it is possible to provide a compound capable of forming a color filter with excellent brightness. [Modes for carrying out the invention]

[0008] <Compound> The compound of the present invention is a compound represented by formula (I) (hereinafter sometimes referred to as compound (I)). The present invention will be described in detail below using formula (I), but compound (I) also includes tautomers of formula (I).

[0009] [ka] [In formula (I), R 1 ~R 4 and R 13 Each of these independently represents a hydrocarbon group having 1 to 10 carbon atoms, which may have a hydrogen atom or a substituent. R 5 ~R 12 Each of these independently represents a hydrogen atom, a halogen atom, or a C1-C5 hydrocarbon group which may have substituents. T 1 and T 2 These independently represent a optionally substituted divalent aromatic hydrocarbon group or an optionally substituted divalent aromatic heterocyclic group. L 1 represents an α-valent aliphatic hydrocarbon group having 1 to 12 carbon atoms, which may have substituents, or a group represented by formula (i), wherein at least one methylene group contained in the aliphatic hydrocarbon group is replaced by -O-. 'a' represents an integer greater than or equal to 2. b and c represent independent integers greater than or equal to 1. d represents a non-negative integer. X c- This represents a c-valent anion. [ka] [In formula (i), T 3 This represents an α-valent aromatic hydrocarbon group or an α-valent aromatic heterocyclic group that may have substituents. L 2 This represents a divalent aliphatic hydrocarbon group having 1 to 5 carbon atoms, which may have substituents, and at least one of the methylene groups contained in the aliphatic hydrocarbon group is replaced by -O-. 'a' has the same meaning as above. * is T 2 This represents a combination of two elements.

[0010] R 1 ~R 4 and R 13 Examples of hydrocarbon groups having 1 to 10 carbon atoms represented by include aliphatic hydrocarbon groups and aromatic hydrocarbon groups. Aliphatic hydrocarbon groups may be saturated or unsaturated, and may be linear or alicyclic.

[0011] The saturated or unsaturated linear 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 groups; 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, and (1-butyl) Examples include branched alkyl groups such as pentyl group, isohexyl group, (2-methyl)hexyl group, (5-methyl)hexyl group, (2-ethyl)hexyl group, (1-butyl)hexyl group, (2-methyl)heptyl group, (2-ethyl)heptyl group, (3-ethyl)heptyl group, (2-methyl)octyl group, and (2-ethyl)octyl group; and alkenyl groups such as vinyl group, 1-propenyl group, 2-propenyl group (allyl group), (1-methyl)ethenyl group, 2-butenyl group, 3-butenyl group, 1,3-butadienyl group, (1-(2-propenyl))ethenyl group, (1,2-dimethyl)propenyl group, and 2-pentenyl group.

[0012] Examples of the saturated or unsaturated alicyclic hydrocarbon groups include cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl groups; cycloalkenyl groups such as cyclohexenyl (e.g., cyclohexa-2-ene, cyclohexa-3-ene), cycloheptenyl, and cyclooctenyl groups; and norbornyl, adamantyl, and bicyclo[2.2.2]octyl groups.

[0013] Examples of aromatic hydrocarbon groups include aryl groups such as phenyl, 1-naphthyl, and 2-naphthyl groups; 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.

[0014] The aforementioned hydrocarbon groups having 1 to 10 carbon atoms may be groups formed by combining two or more of the chain-like hydrocarbon groups, alicyclic hydrocarbon groups, and aromatic hydrocarbon groups listed above, as long as the upper limit of the number of carbon atoms is 10. Such groups include, for example, aralkyl groups such as benzyl group, phenethyl group, and 1-methyl-1-phenylethyl group; arylalkenyl groups such as phenylethenyl group (phenylvinyl group); arylalkynyl groups such as phenylethynyl group; 1-methylcyclopropyl group, 1-methylcyclohexyl group, 2-methylcyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 1,2-dimethylcyclohexyl group, 1,3-dimethylcyclohexyl group, 1,4-dimethylcyclohexyl group, 2,3-dimethylcyclohexyl group, 2,4-dimethylcyclohexyl group, 2,5-dimethylcyclohexyl group, 2,6-dimethylcyclohexyl group, and 3,4-dimethylcyclohexyl group. Examples include alicyclic hydrocarbon groups to which one or more alkyl groups or alicyclic hydrocarbon groups are bonded, such as 3,5-dimethylcyclohexyl group, 2,2-dimethylcyclohexyl group, 3,3-dimethylcyclohexyl group, 4,4-dimethylcyclohexyl group, 2,4,6-trimethylcyclohexyl group, 2,2,6,6-tetramethylcyclohexyl group, and 3,3,5,5-tetramethylcyclohexyl group; alkyl groups to which one or more alicyclic hydrocarbon groups are bonded, such as cyclopropylmethyl group, cyclopropylethyl group, cyclobutylmethyl group, cyclobutylethyl group, cyclopentylmethyl group, cyclopentylethyl group, cyclohexylmethyl group, 2-methylcyclohexylmethyl group, and cyclohexylethyl group; and so on.

[0015] The substituents that the C1-C10 hydrocarbon group may have (hereinafter sometimes referred to as substituent A) include halogen atoms, hydroxyl groups, alkoxy groups, formyl groups, substituted or unsubstituted amino groups, nitro groups, cyano groups, and -SO3 - At least one selected from the group consisting of , and -SO3M, where M represents a hydrogen atom or an alkali metal atom.

[0016] Examples of the halogen atoms include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms. Examples of the alkoxy group include alkoxy groups having 1 to 4 carbon atoms, such as methoxy, ethoxy, propoxy, and butoxy groups. Examples of the substituted amino group include an amino group having one or two hydrocarbon groups, and examples of the hydrocarbon group include the groups exemplified above as hydrocarbon groups having 1 to 10 carbon atoms. Examples of the substituted amino group include N-methylamino group, N,N-dimethylamino group, N-ethylamino group, N,N-diethylamino group, N-propylamino group, N,N-dipropylamino group, N-isopropylamino group, N,N-diisopropylamino group, N-phenylamino group, N,N-diphenylamino group, N,N-ethylmethylamino group, N,N-methylphenylamino group, N,N-ethylphenylamino group, and the like.

[0017] Examples of the alkali metal atoms mentioned above include sodium and potassium.

[0018] R 5 ~R 12 Examples of halogen atoms represented by this formula include fluorine, chlorine, bromine, and iodine.

[0019] R 5 ~R 12 Examples of hydrocarbon groups having 1 to 5 carbon atoms represented by include aliphatic hydrocarbon groups having 1 to 5 carbon atoms, specifically the aforementioned R 1 ~R 4 and R 13 Among the aliphatic hydrocarbon groups exemplified above, those with 1 to 5 carbon atoms are particularly noteworthy.

[0020] Examples of substituents that the hydrocarbon group having 1 to 5 carbon atoms may have include the group exemplified as substituent A.

[0021] T 1 and T 2A divalent aromatic hydrocarbon group represented by R is a group in which two hydrogen atoms directly bonded to carbon atoms constituting an aromatic hydrocarbon ring are replaced by a bonding site. The aromatic hydrocarbon ring constituting the divalent aromatic hydrocarbon group may be a monocyclic or fused ring, and examples include a benzene ring, a naphthalene ring, anthracene ring, and structures in which at least one hydrogen atom of these aromatic hydrocarbon rings is replaced by a hydrocarbon group. The hydrocarbon group is as described above. 1 ~R 4 and R 13 Examples of hydrocarbon groups having 1 to 10 carbon atoms represented by the formulas (Ta-1) to (Ta-8) are those exemplified above, preferably saturated chain hydrocarbon groups, aryl groups, or alkylaryl groups, and more preferably saturated chain hydrocarbon groups having 1 to 4 carbon atoms. The number of hydrocarbon groups bonded to the aromatic hydrocarbon ring is preferably 0 to 4, and more preferably 0 to 3. Specific examples of divalent aromatic hydrocarbon groups include those represented by the following formulas (Ta-1) to (Ta-8).

[0022] [ka]

[0023] T 1 and T 2 A divalent aromatic heterocyclic group represented by R is a group in which two hydrogen atoms directly bonded to the atoms constituting the ring are replaced by bonding bonds in an aromatic heterocyclic ring. The aromatic heterocyclic ring constituting the divalent aromatic heterocyclic group may be either a monocyclic or a fused ring, and examples include a pyrrole ring, oxazole ring, pyrazole ring, imidazole ring, thiazole ring, furan ring, thiophene ring, pyridine ring, pyrimidine ring, pyridazine ring, pyrazine ring, indole ring, benzimidazole ring, benzothiazole ring, quinoline ring, benzofuran ring, and structures in which at least one hydrogen atom of these aromatic heterocyclic rings is replaced by a hydrocarbon group. The hydrocarbon group is as described above R 1 ~R 4 and R 13Examples of hydrocarbon groups having 1 to 10 carbon atoms, as represented by , include the groups exemplified above, 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, and more preferably 0 to 3.

[0024] Examples of substituents that the divalent aromatic hydrocarbon group and the divalent aromatic heterocyclic group may have include the group exemplified as substituent A.

[0025] L 1 An α-valent aliphatic hydrocarbon group having 1 to 12 carbon atoms, represented by , is a group in which a hydrogen atoms constituting an aliphatic hydrocarbon are replaced by a bonding site. Preferably, the a hydrogen atoms are located on different carbon atoms. Examples of α-valent aliphatic hydrocarbon groups include α-valent linear hydrocarbon groups, α-valent alicyclic hydrocarbon groups, and α-valent groups that combine linear and alicyclic hydrocarbon groups.

[0026] The α-valent linear hydrocarbon group may be saturated or unsaturated, but it is preferable that it be an α-valent saturated linear hydrocarbon group. Examples of α-valent saturated linear hydrocarbon groups include alkanediyl groups such as methylene group, ethylene group, propane-1,2-diyl group, propane-1,3-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group, and hexane-1,6-diyl group; alkanetriyl groups such as the group represented by the following formulas (a-1) to (a-2); and alkanetetrayl groups such as the group represented by the following formula (a-3). The number of carbon atoms in the α-valent linear hydrocarbon group is preferably 1 to 8, and more preferably 2 to 6.

[0027] [ka]

[0028] The α-valent alicyclic hydrocarbon group may be saturated or unsaturated, but it is preferable that it be an α-valent saturated alicyclic hydrocarbon group. Examples of α-valent saturated alicyclic hydrocarbon groups include divalent saturated alicyclic hydrocarbon groups such as cyclohexyl-1,2-diyl, cyclohexyl-1,4-diyl, and norbornane-2,5-diyl; trivalent saturated alicyclic hydrocarbon groups such as cyclohexyl-1,3,5-triyl; and tetravalent saturated alicyclic hydrocarbon groups such as cyclohexyl-1,2,4,5-tetrayl. The number of carbon atoms in the α-valent alicyclic hydrocarbon group is preferably 3 to 10, and more preferably 3 to 6.

[0029] Examples of α-valent groups that combine a chain-like hydrocarbon group and an alicyclic hydrocarbon group include the groups represented by the following formulas (a-5) to (a-7).

[0030] [ka]

[0031] L 1 At least one of the methylene groups in the α-valent aliphatic hydrocarbon group having 1 to 12 carbon atoms, represented by , is replaced by -O-. However, not both adjacent methylene groups are replaced by -O-. The number of methylene groups replaced by -O- is, for example, 1 to 6, but preferably 1 or more and a or less, more preferably a. The position of the methylene group replaced by -O- is not particularly limited, but it is preferable that at least one of the methylene groups adjacent to the bond of the α-valent aliphatic hydrocarbon group is replaced by -O-, and it is more preferable that all of the methylene groups adjacent to the bond of the α-valent aliphatic hydrocarbon group are replaced by -O-.

[0032] Specifically, groups in which at least one methylene group in an α-valent aliphatic hydrocarbon group is replaced by -O- include the groups represented by the following formulas (l-1a) to (l-24a), with groups represented by formulas (l-1a) to (l-16a), (l-18a) to (l-19a), and (l-22a) to (l-24a) being preferred, groups represented by formulas (l-1a), (l-10a) to (l-16a), (l-18a) to (l-19a), and (l-22a) to (l-24a) being more preferred, and groups represented by formulas (l-10a) to (l-16a) being even more preferred.

[0033] [ka]

[0034] Examples of substituents that the aliphatic hydrocarbon group having 1 to 12 carbon atoms may have include the group exemplified as substituent A.

[0035] L 1 The base may be represented by equation (i).

[0036] In equation (i), T 3 An α-valent aromatic hydrocarbon group, represented by α, is a group in which, in an aromatic hydrocarbon ring, the α hydrogen atoms directly bonded to the carbon atoms constituting the ring are replaced by bond bonds. An example of an aromatic hydrocarbon ring constituting an α-valent aromatic hydrocarbon group is the structure described above as an aromatic hydrocarbon ring constituting a divalent aromatic hydrocarbon group.

[0037] In equation (i), T 3 An α-valent aromatic heterocyclic group, represented by α, is a group in which, in an aromatic heterocyclic ring, the α hydrogen atoms directly bonded to the atoms constituting the ring are replaced by bond bonds. Examples of aromatic heterocyclic rings that constitute an α-valent aromatic heterocyclic group include the structures described above as aromatic heterocyclic rings that constitute a divalent aromatic heterocyclic group.

[0038] Examples of substituents that the α-valent aromatic hydrocarbon group and the α-valent aromatic heterocyclic group may have include the group exemplified as substituent A.

[0039] In equation (i), L 2 Examples of divalent aliphatic hydrocarbon groups having 1 to 5 carbon atoms, represented by , include divalent chain hydrocarbon groups having 1 to 5 carbon atoms and divalent alicyclic hydrocarbon groups having 1 to 5 carbon atoms.

[0040] The divalent linear hydrocarbon group may be saturated or unsaturated, but it is preferable that it be a divalent saturated linear hydrocarbon group. Examples of divalent saturated linear hydrocarbon groups include methylene group, ethylene group, propane-1,2-diyl group, propane-1,3-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group, and other alkanediyl groups.

[0041] The divalent alicyclic hydrocarbon group may be saturated or unsaturated, but a divalent saturated alicyclic hydrocarbon group is preferred. Examples of divalent saturated alicyclic hydrocarbon groups include cyclopropyl-1,2-diyl group and cyclobutyl-1,3-diyl group.

[0042] L 2 At least one methylene group in a divalent aliphatic hydrocarbon group having 1 to 5 carbon atoms, represented by , is replaced by -O-. However, not both adjacent methylene groups are replaced by -O-. The number of methylene groups replaced by -O- is, for example, 1 to 3, preferably 1 to 2. The position of the methylene group replaced by -O- is not particularly limited, but T 2 It is preferable that the methylene group adjacent to the bond with is replaced by -O-.

[0043] Specifically, groups in which at least one methylene group in a divalent aliphatic hydrocarbon group having 1 to 5 carbon atoms is replaced by -O- include the groups represented by the following formulas (l-1b) to (l-12b), and among these, the groups represented by the formulas (l-2b) to (l-5b) are preferred.

[0044] [ka] [In the formula, * is T 2 This shows a coupling with T, where ** is T 3 This shows the combination.

[0045] Examples of substituents that the C1-C5 divalent aliphatic hydrocarbon group may have include the group exemplified as substituent A.

[0046] The base represented by formula (i) specifically includes the bases represented by the following formulas (i1) to (i8). [ka] [In formulas (i1) to (i8), L i1 ~L i8 Each of these independently represents an alkanediyl group having 1 to 5 carbon atoms, in which one of the methylene groups contained in the alkanediyl group is replaced by -O-. * represents T 2 This represents a combination of two elements.

[0047] The position of the methylene group that replaces -O- is not particularly limited, but T 2 It is preferable that the methylene group adjacent to the bond with is replaced by -O-.

[0048] Multiple L i1 ~L i8 These may be the same or different, but it is preferable that they be the same.

[0049] X c- Examples of c-valent anions represented by include known anions, specifically, halide ions such as fluoride ions, chloride ions, bromide ions, and iodide ions, boron-containing anions, aluminum-containing anions, fluorine-containing anions, and anions containing at least one element selected from the group consisting of tungsten, molybdenum, silicon, and phosphorus, and oxygen as essential elements.

[0050] Examples of boron-containing anions and aluminum-containing anions include the anions represented by the following formula (4).

[0051] [ka]

[0052] [In formula (4), W 1 , W 2 Each of these independently represents a group having two substituents, each consisting of a monovalent proton-donating substituent that releases a proton. M represents boron or aluminum.

[0053] A group having two substituents formed by releasing a proton from a monovalent proton-donating substituent can be described as a group formed by releasing a proton from each of two proton-donating substituents from a compound having at least two monovalent proton-donating substituents (e.g., a hydroxyl group, a carboxylic acid group, etc.). Preferably, such compounds are optionally substituted catechol, optionally substituted 2,3-dihydroxynaphthalene, optionally substituted 2,2'-biphenol, optionally substituted 3-hydroxy-2-naphthoic acid, optionally substituted 2-hydroxy-1-naphthoic acid, optionally substituted 1-hydroxy-2-naphthoic acid, optionally substituted binaphthol, optionally substituted salicylic acid, optionally substituted benzyl acid, or optionally substituted mandelic acid.

[0054] In the above-mentioned example compounds, examples of substituents include saturated hydrocarbon groups (e.g., alkyl groups, cycloalkyl groups, etc.), halogen atoms, haloalkyl groups, hydroxyl groups, amino groups, nitro groups, alkoxy groups, and the like.

[0055] Salicylic acids that may have substituents include monoaminosalicylic 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, and 6-aminosalicylic acid; 3-hydroxysalicylic acid (2,3-dihydroxybenzoic acid), 4-hydroxysalicylic acid (2,4-dihydroxybenzoic acid), 5-hydroxysalicylic acid (2,5-dihydroxybenzoic acid), and 6-hydroxysalicylic acid. Examples include monohydroxysalicylic acids such as 2,6-dihydroxybenzoic acid; dihydroxysalicylic acids such as 4,5-dihydroxysalicylic acid and 4,6-dihydroxysalicylic acid; monohalosalicylic acids such as 3-chlorosalicylic acid, 4-chlorosalicylic acid, 5-chlorosalicylic acid, 6-chlorosalicylic acid, 3-bromosalicylic acid, 4-bromosalicylic acid, 5-bromosalicylic acid, and 6-bromosalicylic acid; dihalosalicylic acids such as 3,5-dichlorosalicylic acid, 3,5-dibromosalicylic acid, and 3,5-diiodosalic acid; and trihalosalicylic acids such as 3,5,6-trichlorosalicylic acid.

[0056] Benzyl acids that may have substituents include:

[0057] [ka]

[0058] Mandelic acid which may have substituents includes:

[0059] [ka]

[0060] These are some examples.

[0061] Preferred anions among those represented by formula (4) include anions represented by the following formulas, having substituents listed in the table, from anion (BC-1) to anion (BC-24), and anions represented by formulas (BC-25), (BC-26), (BC-27), and (BC-28), respectively, from anion (BC-25) to anion (BC-28).

[0062] [ka]

[0063] [Table 1]

[0064] [ka]

[0065] [ka]

[0066] [ka]

[0067] [ka]

[0068] From the viewpoint of solubility in organic solvents, the anions represented by formula (4) are preferably anion (BC-1), anion (BC-2), anion (BC-3), anion (BC-25), anion (BC-26), and anion (BC-27), more preferably anion (BC-1), anion (BC-2), and anion (BC-25), and even more preferably anion (BC-1) and anion (BC-2).

[0069] Examples of fluorine-containing anions include the groups represented by the following formulas (6), (7), (8), and (9).

[0070] [ka]

[0071] [In formula (6), W 3 and W 4 Each of these independently represents a fluorine atom or a fluorinated alkyl group having 1 to 4 carbon atoms, or W 3 and W 4 Together, these represent a fluoride alkanediyl group with 1 to 4 carbon atoms.

[0072] [ka]

[0073] [In formula (7), W 5 ~W 7 Each of these independently represents either a fluorine atom or a fluorinated alkyl group having 1 to 4 carbon atoms.

[0074] [ka]

[0075] [In formula (8), Y 1 This represents an alkanediyl fluoride group with 1 to 4 carbon atoms.

[0076] [ka]

[0077] [In formula (9), Y 2 This represents an alkyl fluoride with 1 to 4 carbon atoms.

[0078] In formulas (6), (7), and (9), perfluoroalkyl groups are preferred as the fluoride alkyl group having 1 to 4 carbon atoms. Examples of such perfluoroalkyl groups include -CF3, -CF2CF3, -CF2CF2CF3, -CF(CF3)2, -CF2CF2CF2CF3, -CF2CF(CF3)2, and -C(CF3)3.

[0079] In formulas (6) and (8), perfluoroalkanediyl groups are preferred as fluoride alkanediyl groups having 1 to 4 carbon atoms. Examples of perfluoroalkanediyl groups include -CF2-, -CF2CF2-, -CF2CF2CF2-, -C(CF3)2-, and -CF2CF2CF2CF2-.

[0080] Anions represented by formula (6) (hereinafter sometimes referred to as "anion (6)") include the anions shown by formulas (6-1) to (6-6), respectively (hereinafter sometimes referred to as "anion (6-1)" to "anion (6-6)".

[0081] [ka]

[0082] An anion represented by formula (7) (hereinafter sometimes referred to as "anion (7)") is anion (7-1) shown in the following formula.

[0083] [ka]

[0084] Anions represented by formula (8) (hereinafter sometimes referred to as "anion (8)") include the anions shown by formulas (8-1) to (8-4) (hereinafter sometimes referred to as "anion (8-1)" to "anion (8-4)").

[0085] [ka]

[0086] Anions represented by formula (9) (hereinafter sometimes referred to as "anion (9)") include the anions shown by formulas (9-1) to (9-4) (hereinafter sometimes referred to as "anion (9-1)" to "anion (9-4)").

[0087] [ka]

[0088] X c- The solubility of compound (I) in organic solvents can be improved by having the c-valent anion represented as being at least one anion selected from the group consisting of anion (6), anion (7), anion (8), and anion (9) (i.e., a fluorine-containing anion). Among these, anion (6-1), anion (6-2), and anion (7-1) are preferred, and anion (6-2) is particularly preferred.

[0089] X c- Examples of c-valent anions represented by include anions containing at least one element selected from the group consisting of tungsten, molybdenum, silicon, and phosphorus, and oxygen as essential elements. Anions of heteropoly acids or isopoly acids containing tungsten as an essential element are preferred, and anions of phosphotungstic acid, silicatungstic acid, and tungsten-based isopoly acids are more preferred.

[0090] Anions of heteropoly acids or isopoly acids containing tungsten as an essential element include, for example, the 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 silicatungstate ion α-[SiW 12 O40 4- , β-[SiW 12 O 40 4- , γ-[SiW 12 O 40 4- 、Furthermore, as other examples, [P2W 17 O 61 10- , [P2W 15 O 56 12- , [H2P2W 12 O 48 12- , [NaP5W 30 O 110 14- , α-[SiW9O 34 10- , γ-[SiW 10 O 36 8- , α-[SiW 11 O 39 8- , β-[SiW 11 O 39 8- , [W6O​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​4- Isopolyate anions such as the above are preferred.

[0093] In equation (I), multiple R 1 ~R 13 , T 1 , T 2 , and L 1 These may be the same or different, but it is preferable that they be the same. Also, in formula (i), multiple L 2 These may be the same or different, but it is preferable that they be the same.

[0094] R 1 ~R 4 Preferably, each of these is independently a saturated chain hydrocarbon group having 1 to 10 carbon atoms, which may have substituents, an aryl group having 6 to 10 carbon atoms, which may have substituents, or an alkylaryl group having 7 to 10 carbon atoms, which may have substituents.

[0095] In particular, R 1 and R 3 However, each is independently an aryl group having 6 to 10 carbon atoms which may have substituents, or an alkylaryl group having 7 to 10 carbon atoms which may have substituents, and R 2 and R 4 However, each is preferably independently a saturated chain hydrocarbon group having 1 to 10 carbon atoms, which may have substituents. R 1 and R 3 However, each is independently a phenyl group which may have substituents, and R 2 and R 4 However, each is more preferably a saturated chain hydrocarbon group having 1 to 10 carbon atoms, which may have substituents. R 1 and R 3 However, each is independently a phenyl group which may have substituents, and at least one of the two bond positions which are ortho relative to the N bonded to the phenyl group has an alkyl group having 1 to 4 carbon atoms, and R 2 and R 4However, each is more preferably a saturated chain hydrocarbon group having 1 to 6 carbon atoms, which may have substituents. R 1 and R 3 However, each is independently a phenyl group which may have substituents, and at least one of the two bond positions which are ortho relative to the N bonded to the phenyl group has an alkyl group having 1 to 4 carbon atoms, and R 2 and R 4 However, each is more preferably independently a saturated chain hydrocarbon group having 2 to 6 carbon atoms, which may have substituents. R 1 and R 3 However, each is independently a phenyl group which may have substituents, and each of the two bonding positions that are ortho relative to the N bonded to the phenyl group has an alkyl group having 1 to 3 carbon atoms, and R 2 and R 4 However, it is particularly preferable that each of them be a saturated chain hydrocarbon group having 2 to 6 carbon atoms, which may have substituents. Here, the substituents that the phenyl group may have include C1-C4 alkyl groups, halogen atoms, hydroxyl groups, alkoxy groups, formyl groups, substituted or unsubstituted amino groups, nitro groups, cyano groups, and -SO3 - At least one selected from the group consisting of , and -SO3M (where M is the same as above), among which are alkyl groups having 1 to 4 carbon atoms, halogen atoms, alkoxy groups, and -SO3 - Preferably, at least one selected from the group consisting of C1-C4 alkyl groups, C1-C4 alkoxy groups, and -SO3 - It is more preferable to select at least one from the group consisting of the following:

[0096] In particular, when the phenyl group has an alkoxy group (preferably a methoxy group) as a substituent, the brightness of the resulting color filter can be further increased. The substitution position of the alkoxy group (preferably a methoxy group) is not particularly limited, but the effect can be further enhanced by bonding it at a position para with respect to the nitrogen bonded to the phenyl group.

[0097] The aforementioned R 1 ~R 4 In a preferred embodiment, R 1 and R 3 Each of these groups is preferably one of the groups represented by formulas (r1) to (r3). Furthermore, it is particularly preferable that one or more hydrogen atoms in the groups represented by formulas (r1) to (r3) are -SO3 - It may be replaced with .

[0098] [ka] [In the formula, R r1 ~R r4 Each of these independently represents an alkyl group having 1 to 4 carbon atoms. * indicates a bond.

[0099] R r1 ~R r4 It is preferable that it be a methyl group.

[0100] R 5 ~R 12 It is preferable that it be a hydrogen atom.

[0101] R 13 It is preferably a C1-C6 hydrocarbon group which may have a hydrogen atom or substituents, more preferably a C1-C6 saturated chain hydrocarbon group which may have a hydrogen atom or substituents, and even more preferably a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, or an isopropyl group.

[0102] T 1It is preferably a divalent aromatic hydrocarbon group which may have substituents, and the aromatic hydrocarbon ring constituting the divalent aromatic hydrocarbon group is preferably a benzene ring, a naphthalene ring, or a structure in which at least one hydrogen atom of such a ring is replaced by a saturated chain hydrocarbon group having 1 to 10 (preferably 1 to 4) carbon atoms. 1 It is more preferable that the group is one of the groups represented by the above formulas (Ta-1) to (Ta-8), and the group represented by the above formula (Ta-8) is particularly preferred.

[0103] T 2 It is preferably a divalent aromatic hydrocarbon group which may have substituents, and the aromatic hydrocarbon ring constituting the divalent aromatic hydrocarbon group is preferably a benzene ring, a naphthalene ring, or a structure in which at least one hydrogen atom of such a ring is replaced by a saturated chain hydrocarbon group having 1 to 10 (preferably 1 to 4) carbon atoms, and more preferably a benzene ring or a structure in which at least one hydrogen atom of a benzene ring is replaced by a saturated chain hydrocarbon group having 1 to 4 carbon atoms. 2 It is more preferably one of the groups represented by the following formulas (Tb-1) to (Tb-10), even more preferably one of the groups represented by the following formulas (Tb-3), (Tb-5), (Tb-6), (Tb-9), and (Tb-10), and particularly preferably one of the groups represented by the following formulas (Tb-5), (Tb-6), (Tb-9), and (Tb-10).

[0104] [ka] [In the formula, * represents L 1 This represents a bond with the nitrogen atom, and ** represents a bond with the nitrogen atom.

[0105] As for equation (i), T 3 L is an α-valent aromatic hydrocarbon group which may have substituents, 2The group is preferably a divalent saturated chain hydrocarbon group having 1 to 5 carbon atoms, wherein at least one methylene group contained in the saturated chain hydrocarbon group is replaced by -O-, any of the groups represented by formulas (i1) to (i8) above is more preferred, the group represented by formula (i2) or formula (i3) above is even more preferred, and any of the groups represented by the following formulas (i-1) to (i-6) is particularly preferred.

[0106] [ka] [In the formula, * is T 2 This represents a combination of two elements.

[0107] L 1 Preferably, the aliphatic hydrocarbon group is a C1-C8 α-valent aliphatic hydrocarbon group which may have substituents, and in which at least one methylene group contained in the aliphatic hydrocarbon group is replaced by -O-, or it is one of the groups represented by the above formulas (i1) to (i8). A saturated chain hydrocarbon group having 1 to 8 carbon atoms, which may have substituents, wherein at least one methylene group contained in the aliphatic hydrocarbon group is replaced by -O-, or more preferably a group represented by the above formula (i2) or formula (i3). It is more preferably a saturated chain hydrocarbon group having 1 to 8 carbon atoms, which may have substituents, in which at least one methylene group contained in the aliphatic hydrocarbon group is replaced by -O-, or a group represented by the above formulas (i-1) to (i-6). It is particularly preferable that the group be one of the groups represented by the above formulas (l-10a) to (l-16a) or formulas (i-1) to (i-6).

[0108] X c-The c-valent anion represented by is preferably a halide ion or an anion containing at least one element selected from the group consisting of tungsten, molybdenum, silicon, and phosphorus, and oxygen as essential elements; more preferably a halide ion or an anion of a heteropoly acid or isopoly acid containing tungsten as an essential element; and even more preferably a halide ion, a Keggin-type phosphotungstate ion, or a Dawson-type phosphotungstate ion.

[0109] The substituents (i.e., substituent A) of compound (I) include halogen atoms, hydroxyl groups, alkoxy groups, substituted or unsubstituted amino groups, and -SO3 - Preferably, at least one selected from the group consisting of , and -SO3M, and more preferably a halogen atom, an alkoxy group, and -SO3 - It is at least one selected from the group consisting of , and -SO3M.

[0110] a is preferably an integer between 2 and 6, more preferably between 2 and 4, and even more preferably 2 or 3.

[0111] c is usually 1 to 14, preferably 1 to 12, more preferably 1 to 10, even more preferably 1 to 6, and particularly preferably 1 to 4.

[0112] b and d are the -SO3 substituents that a, c, and compound (I) have. - The number of (hereinafter sometimes referred to as e) determines the value, and is generally adjusted so that the total charge of equation (I) becomes 0. Therefore, a to d in equation (I) usually satisfy the relationship shown in equation (z) below. a × b = (c × d) + e ... (z) [In the above formula, a to d have the same meaning as above. e is the -SO3 substituent that compound (I) has. - [Indicates the number of.]

[0113] e is an integer greater than or equal to 0, preferably 0 or greater than or equal to (a+1), more preferably 0 or greater than or equal to a, and even more preferably 0 or a. In particular, when d is 1 or greater, e is 0, i.e., compound (I) is -SO3 - It is preferable that it does not have, and when d is 0, it is preferable that e = a.

[0114] In particular, from the viewpoint of heat resistance and solvent resistance, X c- A compound is preferred in which the anion contains at least one element selected from the group consisting of tungsten, molybdenum, silicon, and phosphorus, and oxygen as essential elements, and in which d is 1 or more and e is 0.

[0115] Compound (I) is preferably a compound represented by formula (I-1) or formula (I-2).

[0116] [ka] [In formula (I-1), R 101 and R 103 However, each is independently a phenyl group which may have substituents, R 102 and R 104 However, each is independently a saturated chain hydrocarbon group having 1 to 10 carbon atoms, which may have substituents. R 105 ~R 112 It is a hydrogen atom, R 113 This is a saturated chain hydrocarbon group having 1 to 6 carbon atoms, which may have hydrogen atoms or substituents. T 101 and T 102 This is a divalent aromatic hydrocarbon group which may have substituents, wherein the aromatic hydrocarbon ring constituting the divalent aromatic hydrocarbon group has a structure in which at least one hydrogen atom of such ring is replaced by a saturated chain hydrocarbon group having 1 to 4 carbon atoms. L 101This is a saturated chain hydrocarbon group having 1 to 8 carbon atoms and having an a101 valency, which may have substituents, wherein at least one methylene group contained in the aliphatic hydrocarbon group is replaced by -O-, or in a group represented by formula (i), T 3 A substituted a101 valent aromatic hydrocarbon group, L 2 This is a divalent saturated chain hydrocarbon group having 1 to 5 carbon atoms, wherein at least one methylene group contained in the saturated chain hydrocarbon group is replaced by -O-. a101 is 2 or 3, d101 represents an integer greater than or equal to 1, b, c, and X c- This has the same meaning as above.

[0117] [ka] [In formula (I-2), R 201 and R 203 However, each is independently a phenyl group which may have substituents, R 202 and R 204 However, each is independently a saturated chain hydrocarbon group having 1 to 10 carbon atoms, which may have substituents. R 205 ~R 212 It is a hydrogen atom, R 213 This is a saturated chain hydrocarbon group having 1 to 6 carbon atoms, which may have hydrogen atoms or substituents. T 201 and T 202 This is a divalent aromatic hydrocarbon group which may have substituents, wherein the aromatic hydrocarbon ring constituting the divalent aromatic hydrocarbon group has a structure in which at least one hydrogen atom of such ring is replaced by a saturated chain hydrocarbon group having 1 to 4 carbon atoms. L 201This is a saturated chain hydrocarbon group having 1 to 8 carbon atoms and having an a2O1 valency, which may have substituents, wherein at least one methylene group contained in the aliphatic hydrocarbon group is replaced by -O-, or in a group represented by formula (i), T 3 A 201 valent aromatic hydrocarbon group which may have substituents, L 2 This is a divalent saturated chain hydrocarbon group having 1 to 5 carbon atoms, wherein at least one methylene group contained in the saturated chain hydrocarbon group is replaced by -O-. a201 and e201 are 2 or 3. The compound represented by formula (I-2) is R 201 ~R 213 , T 201 , T 202 , and L 201 Any of the hydrogen atoms e201 in -SO3 - It has been replaced with [this].

[0118] R 101 , R 103 , R 201 and R 203 The substituents that the phenyl group represented by may have include at least one selected from the group consisting of C1-C4 alkyl groups, halogen atoms, hydroxyl groups, alkoxy groups, formyl groups, substituted or unsubstituted amino groups, nitro groups, cyano groups, and -SO3M (where M is a hydrogen atom or an alkali metal atom). Among these, at least one selected from the group consisting of C1-C4 alkyl groups and C1-C4 alkoxy groups is preferred. The halogen atoms, alkoxy groups, substituted amino groups, and alkali metal atoms are the same as those described as substituent A.

[0119] R 101 , R 103 , R 201 and R 203 It is preferably a phenyl group which may have substituents, and which has a C1-C4 alkyl group at at least one (preferably both) of the two bond positions that are ortho relative to the N bonded to the phenyl group. In particular, R 101 , R 103, R 201 and R 203 are each independently preferably any of the groups represented by the above formulas (r1) to (r3).

[0120] R 102 , R 104 , R 202 and R 204 are preferably saturated chain hydrocarbon groups having 1 to 6 carbon atoms which may have substituents, and more preferably saturated chain hydrocarbon groups having 2 to 6 carbon atoms. As the substituents which the saturated chain hydrocarbon groups represented by R 102 , R 104 , R 202 explanationand R 204 may have (hereinafter referred to as substituent B), examples include at least one or more selected from the group consisting of a halogen atom, a hydroxy group, an alkoxy group, a formyl group, a substituted or unsubstituted amino group, a nitro group, a cyano group, and -SO3M (M is a hydrogen atom or an alkali metal atom). The halogen atom, alkoxy group, substituted amino group, and alkali metal atom are the same as those described as substituent A.

[0121] R 113 and R 213 Examples of the substituents which the saturated chain hydrocarbon groups having 1 to 6 carbon atoms represented by may have include the groups described as substituent B.

[0122] [[ID=3V]] T 101 and T 201 Examples of the substituents which the divalent aromatic hydrocarbon group represented by may have include the groups described as substituent B. As T 101 and T<00002I2>is preferably any of the groups represented by the above formulas (Ta-1) to (Ta-8), and more preferably the group represented by the formula (Ta-8). [[ID=q6]]

[0123] Ted 102 and T 202Examples of the substituent that the divalent aromatic hydrocarbon group represented by may have include the groups described as substituent B. Among them, at least one selected from the group consisting of a halogen atom and an alkoxy group is preferable. T 102 and T 202 Examples of include a divalent aromatic hydrocarbon group that may have a substituent. The aromatic hydrocarbon ring constituting the divalent aromatic hydrocarbon group is preferably a benzene ring or a structure in which at least one hydrogen atom of the benzene ring is replaced by a saturated chain hydrocarbon group having 1 to 4 carbon atoms, more preferably any of the groups represented by the above formulas (Tb-1) to (Tb-10), and particularly preferably any of the groups represented by the formulas (Tb-5), (Tb-6), (Tb-9), and (Tb-10).

[0124] In formulas (I-1) and (I-2), L 101 and L 201 Examples of the saturated chain hydrocarbon group having a carbon number of 1 to 8 and an a-valence represented by , T 3 Examples of the aromatic hydrocarbon group having an a-valence represented by , and the substituent that L in formula (i) may have include the groups described as substituent B. 2 Examples of include a saturated chain hydrocarbon group having a carbon number of 1 to 8 and an a-valence that may have a substituent, and at least one of the methylene groups contained in the aliphatic hydrocarbon group is replaced by -O-, or it is preferably any of the groups represented by the above formulas (i1) to (i8). L 101 and L 201 Examples of include a saturated chain hydrocarbon group having a carbon number of 1 to 8 and an a-valence that may have a substituent, and at least one of the methylene groups contained in the aliphatic hydrocarbon group is replaced by -O-, or it is more preferably the group represented by the above formula (i2) or formula (i3). Examples of include a saturated chain hydrocarbon group having a carbon number of 1 to 8 and an a-valence that may have a substituent, and at least one of the methylene groups contained in the aliphatic hydrocarbon group is replaced by -O-, or it is more preferably the group represented by the above formula (i2) or formula (i3). It is particularly preferable that it is any of the groups represented by the above formulas (l-10a) to (l-16a) or formulas (i-1) to (i-6).

[0125] a201 and e201 are preferably the same.

[0126] The compounds represented by formulas (I-1) and (I-2) preferably have a charge of 0.

[0127] Furthermore, from the viewpoint of heat resistance and solvent resistance, the compound represented by formula (I-1) is preferred.

[0128] Compound (I) specifically includes compounds (I-1a-1) to (I-108a-1) and compounds (I-1a-2) to (I-108a-2) represented by the following formula (Ia), and compounds (I-1b) to (I-108b) represented by the following formula (Ib). Note that the compound represented by formula (Ib) refers to a compound (I) in which b is 1 and d is 0. The compound represented by formula (Ib) is R 1b ~R 13b , T 1b , T 2b , and L 1b Any two of the hydrogen atoms in -SO3 - It has been replaced with.

[0129] [ka]

[0130] [Table 2]

[0131] [Table 3]

[0132] [Table 4]

[0133] [Table 5]

[0134] [Table 6]

[0135] [Chemistry]

[0136] [Table 7]

[0137] [Table 8]

[0138] [Table 9]

[0139] In Tables 2 to 9, H represents a hydrogen atom, Et represents an ethyl group, Pr represents an n-propyl group, r-1 to r-3 represent groups represented by the following formulas (r-1) to (r-3), Ta-8 represents a group represented by the following formula (Ta-8), Tb-5 to Tb-6 and Tb-9 to Tb-10 represent groups represented by the following formulas (Tb-5) to (Tb-6) and (Tb-9) to (Tb-10), i-1 and i-4 represent groups represented by the following formulas (i-1) and (i-4), and l-13a represents a group represented by the following formula (l-13a).

[0140] [Chemistry] [In the formula, * indicates a bond to a nitrogen atom.]

[0141] [Chemistry] [In the formula, * indicates a bond.]

[0142] [Chemistry] [In the formula, * represents L 1a or L 1b This represents a bond with the nitrogen atom, and ** represents a bond with the nitrogen atom.

[0143] [ka] [In the formula, * is T 2a or T 2b This shows the combination.

[0144] As compound (I), compounds (I-1a-1) to (I-108a-1) and compounds (I-1a-2) to (I-108a-2) are preferred, compounds (I-1a-2) to (I-108a-2) are more preferred, and compounds (I-1a-2) to (I-36a-2), compounds (I-39a-2), compounds (I-42a-2), compounds (I-45a-2), compounds (I-48a-2), compounds (I-51a-2), and compounds (I-54a-2) are even more preferred.

[0145] Compound (I) can be produced, for example, by the following methods (1) to (3).

[0146] (1)X c- Method for producing compound (I) (hereinafter sometimes referred to as compound (I')), in which the compound is a halide ion. Compound (I') can be produced, for example, by reacting a compound represented by formula (BI) with a compound represented by formula (CI).

[0147] [ka] [In formulas (BI) and (CI), R 1 ~R 13 , T 2 , L 1 , and a represent the same meanings as described above. 1B The above T 1This represents a group in which a bond different from the one bonding to the nitrogen atom is replaced by a hydrogen atom.

[0148] The amount of compound represented by formula (CI) used is preferably 0.5 moles to 10 moles, and more preferably 1 mole to 4 moles, per mole of compound represented by formula (BI).

[0149] The reaction temperature is preferably 30°C to 180°C, and more preferably 80°C to 130°C. The reaction time is preferably 1 hour to 12 hours, and more preferably 1 hour to 8 hours.

[0150] The above reaction may be carried out in the presence of an organic solvent or without a solvent, but from the viewpoint of yield, it is preferable to carry it out in an organic solvent. Examples of organic solvents 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; nitro hydrocarbon solvents such as nitrobenzene; ketone solvents such as methyl isobutyl ketone; and amide solvents such as 1-methyl-2-pyrrolidone. The amount of organic solvent used is preferably 1 to 20 parts by mass, and more preferably 2 to 10 parts by mass, per 1 part by mass of the compound represented by formula (BI).

[0151] The above reaction is preferably carried out in the presence of a condensing agent from the viewpoint of yield. Examples of condensing agents include phosphoric acid, polyphosphate, oxyhalogenated phosphorus such as phosphorus oxychloride, sulfuric acid, and thionyl halogens such as thionyl chloride. When phosphorus oxyhalogenated phosphorus, thionyl halogen, etc. are used as the condensing agent, and the relationship of formula (z1) is satisfied, X c- Compound (I') is obtained, in which the ion is a halide ion. a × be > 0 ···(z1) [In the above formula, a and b have the same meanings as a and b in formula (I). e is the -SO3 substituent that compound (I') has. - [Indicates the number of.] The amount of condensing agent used is preferably 0.1 parts by mass to 20 parts by mass, and more preferably 0.2 parts by mass to 10 parts by mass, per 1 part by mass of the compound represented by formula (BI).

[0152] The method for obtaining compound (I') from the reaction mixture is not particularly limited, and various known methods can be employed. After extraction, the resulting residue may be purified by column chromatography or recrystallization.

[0153] Various known methods can be used to produce the compound (BI), such as the method described in West German Patent Application P3928243.0. Further purification may be performed by known methods such as recrystallization or chromatographic separation, if necessary.

[0154] Various known methods can be used to produce the compound (CI). Furthermore, if necessary, it may be further purified by known methods such as recrystallization or chromatography.

[0155] (2)X c- anions other than halide ions (hereinafter referred to as anion X) 1 A method for manufacturing compound (I) (hereinafter sometimes referred to as compound (I'')). Compound (I'') is composed of compound (I') and anion X 1 It can be produced by mixing an alkali metal salt or protonic acid. Examples of alkali metals include lithium, sodium, and potassium.

[0156] Anion X against compound (I') 1 The amount of alkali metal salt or protic acid used depends on the cation in compound (I') and the anion X 1 It is preferable to add the compound in a stoichiometric ratio that balances the charge, but for example, for 1 mole of compound (I'), it is preferably 0.5 moles to 8 moles, and more preferably 1 mole to 3 moles.

[0157] Compound (I') and anion X 1 The mixing of alkali metal salts or protic acids may be carried out by dissolving both in the following solvents, or without dissolving them.

[0158] Examples of solvents include N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide, acetonitrile, ethyl acetate, toluene, methanol, ethanol, isopropanol, acetone, tetrahydrofuran, dioxane, water, and chloroform. In particular, from the viewpoint of solubility, at least one solvent selected from the group consisting of N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide, methanol, ethanol, isopropanol, and water is preferred. The amount of solvent used is preferably 1 to 30 parts by mass, and more preferably 2 to 20 parts by mass, per 1 part by mass of compound (I'). If the solvent is water, an acid such as acetic acid or hydrochloric acid may be added.

[0159] Compound (I') and anion X 1 The mixing temperature with the alkali metal salt or protic acid is preferably 0°C to 150°C, more preferably 10°C to 120°C, and even more preferably 20°C to 100°C. The mixing time is preferably 1 hour to 72 hours, more preferably 2 hours to 24 hours, and even more preferably 3 hours to 12 hours.

[0160] If a solvent compatible with water is used, the solution can be mixed and stirred for a further 1 to 3 hours as needed, and then the solvent can be removed to obtain compound (I''). If necessary, the obtained compound (I'') may be washed with deionized water or methanol.

[0161] If a solvent immiscible with water is used, the reaction mixture can be mixed with deionized water, stirred for a further 1 to 3 hours as needed, and then the organic layer can be obtained by liquid-liquid separation to obtain a solution containing compound (I''). If necessary, the solution may be washed with deionized water. Compound (I'') can be obtained by removing the solvent from the solution containing compound (I'').

[0162] (3)X c- Method for producing a compound in which d does not exist (i.e., d=0) (hereinafter sometimes referred to as compound (I''')) Compound (I''') can be produced by mixing compound (I') with sulfuric acid.

[0163] The amount of sulfuric acid used for compound (I') depends on the cation in compound (I') and -SO3 - It is preferable to add sulfuric acid in a stoichiometric ratio that balances the charge, for example, 0.5 moles to 8 moles, preferably 1 mole to 3 moles, per mole of compound (I'). The sulfuric acid may also be used as a reaction solvent. When sulfuric acid is used as a solvent, the amount of sulfuric acid used is, for example, 20 moles or more, preferably 25 moles or more, per mole of compound (I'). There is no particular upper limit to the amount of sulfuric acid used when sulfuric acid is used as a solvent, but it is, for example, 100 parts by mass or less, preferably 50 parts by mass or less, per part by mass of compound (I').

[0164] The mixing temperature of compound (I') and sulfuric acid is preferably 0°C to 150°C, more preferably 10°C to 120°C, and even more preferably 20°C to 100°C. The mixing time is preferably 1 hour to 72 hours, more preferably 2 hours to 24 hours, and even more preferably 3 hours to 12 hours.

[0165] The mixture obtained by mixing compound (I') with sulfuric acid can be added to ice water to form a suspension, and then filtered to obtain compound (I'''). If necessary, further purification may be performed by known methods such as recrystallization or preparative chromatography.

[0166] <Colored resin composition> The colored resin composition of the present invention contains a coloring agent (hereinafter sometimes referred to as coloring agent (A)) and a resin (hereinafter sometimes referred to as resin (B)), wherein the coloring agent contains compound (I). The colored resin composition of the present invention preferably further contains a polymerizable compound (hereinafter sometimes referred to as polymerizable compound (C)) and a polymerization initiator (hereinafter sometimes referred to as polymerization initiator (D)). The colored resin composition of the present invention preferably further contains a solvent (hereinafter sometimes referred to as solvent (E)). The colored resin composition of the present invention may further contain a leveling agent (hereinafter sometimes referred to as leveling agent (F)). In this specification, the compounds exemplified as components may be used individually or in combination, unless otherwise specified.

[0167] <Coloring agent (A)> The coloring agent (A) contains compound (I). This results in good brightness of the resulting color filter, and preferably allows for thinning of the resulting color filter. Furthermore, the inclusion of compound (I) in the coloring agent (A) preferably improves the heat resistance and / or solvent resistance of the resulting color filter. Examples of compound (I) include the compound (I) described above, and the preferred embodiments thereof are also as described above.

[0168] The coloring agent (A) may contain dyes other than compound (I) (hereinafter sometimes referred to as dye (A1-1)) and / or pigments (hereinafter sometimes referred to as pigment (A1-2)). Hereinafter, dye (A1-1) and pigment (A1-2) together may be referred to as coloring agent (A1). These may be used individually or in combination of two or more types.

[0169] The dye (A1-1) is not particularly limited and any known dye can be used, as long as it does not include compound (I). Examples include solvent dyes, acid dyes, direct dyes, mordant dyes, etc. Examples of dyes include compounds classified as dyes in the Color Index (published by The Society of Dyers and Colourists) and known dyes listed in the Dyeing Notes (Irozome-sha). In addition, based on chemical structure, examples include azo dyes, cyanine dyes, triphenylmethane dyes, xanthene dyes, anthraquinone dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, azomethine dyes, squarylium dyes, acridine dyes, styryl dyes, coumarin dyes, quinoline dyes, nitro dyes, and phthalocyanine dyes. Of these, organic solvent-soluble dyes are preferred.

[0170] Specifically, as a dye (A1-1), CI 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; CI 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; CI Solvent Orange 2, 7, 11, 15, 26, 41, 54, 56, 77, 86, 99; CI Solvent Violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60; CI 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; CI Solvent Green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35; and other CI solvent dyes. CI 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; CI 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, 1 82, 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; CI 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; CI Acid Violet 6B, 7, 9, 15, 16, 17, 19, 21, 23, 24, 25, 30, 34, 38, 49, 72, 102; CI 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; CI Acid Green 1, 3, 5, 6, 7, 8, 9, 11, 13, 14, 15, 16, 22, 25, 27, 28, 41, 50, 50:1, 58, 63, 65, 80, 104, 105, 106, 109; and other CI Acid dyes. CI 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; CI 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; CI Direct Orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107; CI Direct Violet 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104; CI 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, 16 6, 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; CI Direct Green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 79, 82; and other CI Direct dyes. CI Disperse Yellow 51, 54, 76; CI Disperse Violet 26, 27; CI Disperse Blue 1, 14, 56, 60; and other CI disperse dyes. CI Basic Red 1, 9, 10; CI 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; CI Basic Violet 2; CI Basic Green 1; and other CI Basic dyes, CI Reactive Yellow 2, 76, 116; CI Reactive Orange 16; CI Reactive Red 36; and other CI reactive dyes, CI Mordant Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65; CI Modant 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; CI Modern Orange 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47, 48; CI 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; CI Modern 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; CI Modant Green 1, 3, 4, 5, 10, 13, 15, 19, 21, 23, 26, 29, 31, 33, 34, 35, 41, 43, 53; and other CI Modant dyes. Examples include dyes with color index (CI) numbers, such as CI Bat Green 1 and other CI Bat dyes.

[0171] The pigment (A1-2) is not particularly limited and any known pigment can be used, as long as it does not contain compound (I). Examples include pigments classified as pigments in the Color Index (published by The Society of Dyers and Colourists). Examples of pigments classified as pigments include yellow pigments such as CI 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, and 231; CI Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73, and other orange pigments; CI 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, and other red pigments; CI Pigment Blue 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 60, and other blue pigments; Violet pigments such as CI Pigment Violet 1, 19, 23, 32, 36, 38; Green pigments such as CI Pigment Green 7, 36, 58, 59, 62, 63; CI Pigment Brown 23, 25, and other brown pigments; Examples include black pigments such as CI Pigment Black 1 and 7.

[0172] As the coloring agent (A1), yellow, red, or green dyes and / or pigments are preferred.

[0173] The coloring agent (A1) may be subjected to rosin treatment, surface treatment using derivatives into which acidic or basic groups have been introduced, graft treatment of the surface of the coloring agent (A1) with polymer compounds, atomization treatment by sulfuric acid atomization method, washing treatment with organic solvents or water to remove impurities, removal treatment of ionic impurities by ion exchange method, etc. The particle size of the coloring agent (A1) is preferably substantially uniform.

[0174] If colorant (A) further contains colorant (A1), the content of compound (I) is, for example, 1% by mass or more, preferably 2% by mass or more, more preferably 10% by mass or more, even more preferably 25% by mass or more, and particularly preferably 50% by mass or more, relative to the total amount of colorant (A). Also, if colorant (A) further contains colorant (A1), the content of compound (I) is, for example, less than 100% by mass, relative to the total amount of colorant (A).

[0175] If the colored resin composition contains a solvent (E), a colorant-containing solution containing the colorant (A) and solvent (E) may be prepared in advance, and then the colored resin composition may be prepared using the colorant-containing solution. If the colorant (A) does not dissolve in the solvent (E), for example, if the colorant (A) contains pigments (A1-2), the colorant-containing solution can be prepared by dispersing the colorant (A) in the solvent (E) and mixing it. The colorant-containing solution may contain some or all of the solvent (E) contained in the colored resin composition.

[0176] The solid content in the coloring agent-containing liquid is preferably 0.01% by mass or more and 99.99% by mass or less, more preferably 0.1% by mass or more and 99.9% by mass or less, even more preferably 0.1% by mass or more and 99% by mass or less, even more preferably 0.5% by mass or more and 90% by mass or less, and particularly preferably 1% by mass or more and 50% by mass or less, relative to the total amount of the coloring agent-containing liquid.

[0177] The coloring agent (A) may be uniformly dispersed in the solution by dispersing it with a dispersant. When using two or more types of coloring agents (A) in combination, each may be dispersed individually, or multiple types may be mixed and dispersed.

[0178] Examples of dispersants include surfactants, which may be cationic, anionic, nonionic, or amphoteric. Specifically, examples include polyester-based, polyamine-based, and acrylic-based surfactants. These dispersants may be used alone or in combination of two or more. Examples of dispersants, by trade name, include KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Floren (manufactured by Kyoeisha Chemical Co., Ltd.), Solspers® (registered trademark) (manufactured by Zeneca Co., Ltd.), EFKA® (registered trademark) (manufactured by BASF Ltd.), Azisper® (registered trademark) (manufactured by Ajinomoto Fine Techno Co., Ltd.), and Disperbyk® (registered trademark) (manufactured by BIC Chemie Co., Ltd.), BYK® (registered trademark) (manufactured by BIC Chemie Co., Ltd.). A resin (B) described later may also be used as a dispersant.

[0179] When a dispersant is used, the amount of dispersant (solid content) used is usually 1 to 10,000 parts by mass, preferably 5 to 5,000 parts by mass, more preferably 10 to 1,000 parts by mass, and even more preferably 15 to 800 parts by mass, per 100 parts by mass of colorant (A). When the amount of dispersant used is within the above range, a colorant-containing liquid with a more uniform dispersion state tends to be obtained.

[0180] The content of the coloring agent (A) is preferably 0.1% to 50% by mass, more preferably 0.5% to 40% by mass, and even more preferably 1% to 30% by mass, relative to the total amount of solids in the colored resin composition. When the content of the coloring agent (A) is within the above range, the color density when used as a color filter is sufficient, and the required amount of resin (B) can be included in the composition, so it is preferable that a pattern with sufficient mechanical strength can be formed. Herein, "total amount of solids" as used herein refers to the amount obtained by subtracting the solvent content from the total amount of the colored resin composition. The total amount of solids and the content of each component therein can be measured by known analytical means such as liquid chromatography or gas chromatography.

[0181] <Resin (B)> The resin (B) is not particularly limited, but is preferably an alkali-soluble resin. Examples of resin (B) include the following resins [K1] to [K6]. Resin [K1]; a copolymer having structural units derived from at least one monomer (a) (hereinafter sometimes referred to as "(a)") selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic acid anhydrides, and structural units derived from monomer (b) (hereinafter sometimes referred to as "(b)") having a cyclic ether structure with 2 to 4 carbon atoms and an ethylenically unsaturated bond; Resin [K2]; a copolymer having structural units derived from (a) and structural units derived from (b) and a monomer (c) copolymerizable with (a) (however different from (a) and (b)) (hereinafter sometimes referred to as "(c)"); Resin [K3]; a copolymer having structural units derived from (a) and structural units derived from (c); Resin [K4]; a copolymer having structural units derived from (a) to which (b) is added and structural units derived from (c); Resin [K5]; a copolymer having structural units derived from (b) to which (a) is added and structural units derived from (c); A copolymer having a structural unit obtained by adding (a) to a resin [K6] and further adding a carboxylic acid anhydride, and a structural unit obtained by adding (c).

[0182] Examples of monomers (a) include unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, and o-, m-, p-vinylbenzoic acid; Unsaturated dicarboxylic acids such as maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyltetrahydrophthalic acid, and 1,4-cyclohexenedicarboxylic acid; Bicyclounsaturated compounds containing carboxyl groups, such as methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo[2.2.1]hept-2-ene, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene, 5-carboxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-carboxy-6-methylbicyclo[2.2.1]hept-2-ene, and 5-carboxy-6-ethylbicyclo[2.2.1]hept-2-ene; Carboxylic acid anhydrides such as the anhydrides of the above unsaturated dicarboxylic acids, excluding fumaric acid and mesaconic acid; Unsaturated mono(meth)acryloyloxyalkyl) esters of divalent or higher polycarboxylic acids such as mono(2-(meth)acryloyloxyethyl) succinate and mono(2-(meth)acryloyloxyethyl) phthalate; Examples include unsaturated acrylates containing both a hydroxyl group and a carboxyl group in the same molecule, such as α-(hydroxymethyl)acrylic acid. Of these, acrylic acid, methacrylic acid, and maleic anhydride are preferred in terms of copolymerization reactivity and the solubility of the resulting resin in alkaline aqueous solutions. In this specification, "(meth)acrylic acid" refers to at least one selected from the group consisting of acrylic acid and methacrylic acid. The terms "(meth)acryloyl" and "(meth)acrylate" have the same meaning.

[0183] Monomer (b) refers to a polymerizable compound having a cyclic ether structure with 2 to 4 carbon atoms (for example, at least one selected from the group consisting of an oxirane ring, an oxetane ring, and a tetrahydrofuran ring (oxolane ring)) and an ethylenically unsaturated bond. Preferably, monomer (b) is a monomer having a cyclic ether with 2 to 4 carbon atoms and a (meth)acryloyloxy group.

[0184] Examples of monomer (b) include monomers having an oxyranyl 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)"), and monomers having a tetrahydrofuryl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "monomer (b3)").

[0185] Examples of monomers (b1) include monomers having a structure in which unsaturated aliphatic hydrocarbons are epoxidized (hereinafter sometimes referred to as "monomer (b1-1)") and monomers having a structure in which unsaturated alicyclic hydrocarbons are epoxidized (hereinafter sometimes referred to as "monomer (b1-2)").

[0186] As monomer (b1-1), monomers having a glycidyl group and an ethylenically unsaturated bond are preferred. Specifically as monomer (b1-1), glycidyl (meth)acrylate, β-methylglycidyl (meth)acrylate, β-ethylglycidyl (meth)acrylate, glycidyl vinyl ether, o-vinylbenzylglycidyl ether, m-vinylbenzylglycidyl ether, p-vinylbenzylglycidyl ether, α-methyl-o-vinylbenzylglycidyl ether, α-methyl-m-vinylbenzylglycidyl ether, α-methyl-p-vinylbenzylglycidyl ether, 2,3-bis( Examples include 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, and 2,4,6-tris(glycidyloxymethyl)styrene.

[0187] Examples of monomers (b1-2) include vinylcyclohexene monooxide, 1,2-epoxy-4-vinylcyclohexane (e.g., Celoxide® 2000; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., Cyclomer® A400; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., Cyclomer® M100; manufactured by Daicel Corporation), compounds represented by formula (BI), and compounds represented by formula (BII).

[0188] [ka]

[0189] [In formulas (BI) and (BII), R a and R b Each of these independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the hydrogen atom contained in the alkyl group may be substituted with a hydroxyl group. X a and X b These are independent of each other, single bonds, *-R c -, *-R c -O-, *-R c -S- or *-R c Represents -NH- R c This represents an alkanediyl group with 1 to 6 carbon atoms. * represents a bond with O.

[0190] Examples of alkyl groups having 1 to 4 carbon atoms include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, and tert-butyl groups.

[0191] Examples of alkyl groups in which a hydrogen atom is substituted with hydroxyl include hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 1-hydroxypropyl group, 2-hydroxypropyl group, 3-hydroxypropyl group, 1-hydroxy-1-methylethyl group, 2-hydroxy-1-methylethyl group, 1-hydroxybutyl group, 2-hydroxybutyl group, 3-hydroxybutyl group, and 4-hydroxybutyl group.

[0192] R a and R b Preferably, the group can be a hydrogen atom, a methyl group, a hydroxymethyl group, a 1-hydroxyethyl group, or a 2-hydroxyethyl group, and more preferably a hydrogen atom or a methyl group.

[0193] Examples of alkanediyl groups include methylene, ethylene, propane-1,2-diyl, propane-1,3-diyl, butane-1,4-diyl, pentane-1,5-diyl, and hexane-1,6-diyl.

[0194] X a and X b Preferably, the bonds include single bonds, methylene groups, ethylene groups, *-CH2-O- (* represents a bond with O) groups, and *-CH2CH2-O- groups, and more preferably, single bonds and *-CH2CH2-O- groups (* represents a bond with O).

[0195] Compounds represented by formula (BI) include those represented by any of formulas (BI-1) to (BI-15). Among these, compounds represented by formulas (BI-1), (BI-3), (BI-5), (BI-7), (BI-9), and (BI-11) to (BI-15) are preferred, and compounds represented by formulas (BI-1), (BI-7), (BI-9), and (BI-15) are more preferred.

[0196] [ka]

[0197] Compounds represented by formula (BII) include those represented by any of formulas (BII-1) to (BII-15), among which compounds represented by formulas (BII-1), (BII-3), (BII-5), (BII-7), (BII-9), and (BII-11) to (BII-15) are preferred, and compounds represented by formulas (BII-1), (BII-7), (BII-9), and (BII-15) are more preferred.

[0198] [ka]

[0199] The compound represented by formula (BI) and the compound represented by formula (BII) may be used individually, or the compound represented by formula (BI) and the compound represented by formula (BII) may be used in combination. When used in combination, the content ratio of the compound represented by formula (BI) and the compound represented by formula (BII) is preferably 5:95 to 95:5 on a molar basis, more preferably 10:90 to 90:10, and even more preferably 20:80 to 80:20.

[0200] 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. Examples of monomer (b2) include 3-methyl-3-(meth)acryloyloxymethyl oxetane, 3-ethyl-3-(meth)acryloyloxymethyl oxetane, 3-methyl-3-(meth)acryloyloxyethyl oxetane, and 3-ethyl-3-(meth)acryloyloxyethyl oxetane.

[0201] As the monomer (b3) having a tetrahydrofuryl group and an ethylenically unsaturated bond, a monomer having a tetrahydrofuryl group and a (meth)acryloyloxy group is more preferred. Examples of monomer (b3) include tetrahydrofuryl acrylate (e.g., Viscoat V#150, manufactured by Osaka Organic Chemical Industry Co., Ltd.) and tetrahydrofuryl methacrylate.

[0202] Examples of monomers (c) include methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, sec-butyl (meth)acrylate, tert-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, dodecyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, cyclopentyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, tricyclo[5.2.1.0 2,6 ] Decane-8-yl(meth)acrylate (in the relevant technical field, it is commonly called "dicyclopentanyl(meth)acrylate". It is also sometimes called "tricyclodecyl(meth)acrylate"), tricyclo[5.2.1.0 2,6 Decane-9-yl (meth)acrylate, tricyclo[5.2.1.0 2,6 ] Decen-8-yl(meth)acrylate (commonly known as "dicyclopentenyl(meth)acrylate" in the relevant art), tricyclo[5.2.1.0 2,6 (meth)acrylic acid esters such as decen-9-yl (meth)acrylate, dicyclopentanyloxyethyl (meth)acrylate, isobornyl (meth)acrylate, adamantyl (meth)acrylate, allyl (meth)acrylate, propargyl (meth)acrylate, phenyl (meth)acrylate, naphthyl (meth)acrylate, and benzyl (meth)acrylate; Hydroxy group-containing (meth)acrylic acid esters such as 2-hydroxyethyl (meth)acrylate and 2-hydroxypropyl (meth)acrylate; Dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate, and diethyl itaconate; 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-methoxybic Chlo[2.2.1]hept-2-ene, 5-ethoxybicyclo[2.2.1]hept-2-ene, 5,6-dihydroxybicyclo[2.2.1]hept-2-ene, 5,6-di(hydroxymethyl)bicyclo[2.2.1]hept-2-ene, 5,6-di(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5,6-dimethoxybicyclo[2.2.1]hept Bicyclounsaturated compounds such as -2-ene, 5,6-diethoxybicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxymethyl-5-methylbicyclo[2.2.1]hept-2-ene, 5-tert-butoxycarbonylbicyclo[2.2.1]hept-2-ene, 5-cyclohexyloxycarbonylbicyclo[2.2.1]hept-2-ene, 5-phenoxycarbonylbicyclo[2.2.1]hept-2-ene, 5,6-bis(tert-butoxycarbonyl)bicyclo[2.2.1]hept-2-ene, and 5,6-bis(cyclohexyloxycarbonyl)bicyclo[2.2.1]hept-2-ene; Dicarbonylimide derivatives such as N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimide benzoate, N-succinimidyl-4-maleimide butyrate, N-succinimidyl-6-maleimide caproate, N-succinimidyl-3-maleimide propionate, and N-(9-acridinyl)maleimide; Examples include vinyl group-containing aromatic compounds such as styrene, o-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, and p-methoxystyrene; vinyl group-containing nitriles such as (meth)acrylonitrile; halogenated hydrocarbons such as vinyl chloride and vinylidene chloride; vinyl group-containing amides such as (meth)acrylamide; esters such as vinyl acetate; and dienes such as 1,3-butadiene, isoprene, and 2,3-dimethyl-1,3-butadiene. Of these, styrene, vinyltoluene, and tricyclotoluene were selected based on their copolymerization reactivity and heat resistance. [5.2.1.0 2,6 Decane-8-yl(meth)acrylate, tricyclo[5.2.1.0 2,6 Decane-9-yl (meth)acrylate, tricyclo[5.2.1.0 2,6 ] Decen-8-yl (meth)acrylate, tricyclo[5.2.1.0 2,6 It is preferable to use at least one selected from the group consisting of decen-9-yl (meth)acrylate, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo[2.2.1]hept-2-ene, 2-hydroxyethyl (meth)acrylate, and benzyl (meth)acrylate.

[0203] In resin [K1], the ratio of structural units derived from each is, among all structural units constituting resin [K1], (a) Structural units derived from (a); 2-60 mol% (b) Structural units derived from (b); 40-98 mol% It is preferable that this be the case. (a) Structural units derived from (a); 10-50 mol% (b) Structural units derived from (b); 50-90 mol% It is preferable that it be so. When the ratio of structural units of resin [K1] falls within the above range, the storage stability of the colored resin composition, the developability when forming a colored pattern, and the solvent resistance of the resulting color filter tend to be excellent.

[0204] The resin [K1] can be manufactured, for example, by referring to the method described in the literature "Experimental Methods for Polymer Synthesis" (by Takayuki Otsu, published by Kagaku Dojin Co., Ltd., 1st edition, 1st printing, March 1, 1972) and the cited literature.

[0205] Specifically, a method involves placing predetermined amounts of (a) and (b), a polymerization initiator, and a solvent into a reaction vessel, creating a deoxygenated atmosphere by, for example, replacing oxygen with nitrogen, and heating and maintaining the temperature while stirring. The polymerization initiator and solvent used here are not particularly limited and can be those commonly used in the field. For example, examples of polymerization initiators include azo compounds (2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), etc.) and organic peroxides (benzoyl peroxide, etc.), and the solvent can be any solvent that dissolves each monomer. Examples of solvents include the solvent (E) of the colored resin composition of the present invention, as described later.

[0206] The resulting copolymer may be used as is after the reaction, or after being concentrated or diluted, or after being extracted as a solid (powder) by methods such as reprecipitation. In particular, by using the solvent contained in the colored resin composition of the present invention as the solvent during polymerization, the solution after the reaction can be used directly in the preparation of the colored resin composition of the present invention, thereby simplifying the manufacturing process of the colored resin composition of the present invention.

[0207] In resin [K2], the ratio of structural units derived from each is, among all structural units constituting resin [K2], (a) Structural units derived from (a); 2-45 mol% (b) Structural units derived from (b); 2-95 mol% (c) Structural units derived from (c); 1-65 mol% It is preferable that this be the case. (a) Structural units derived from (a); 5-40 mol% (b) Structural units derived from (b); 5-80 mol% (c) Structural units derived from (c); 5-60 mol% It is preferable that it be so. When the ratio of structural units of resin [K2] falls within the above range, the colored resin composition tends to exhibit excellent storage stability, developability when forming colored patterns, and solvent resistance, heat resistance, and mechanical strength of the resulting color filter.

[0208] Resin [K2] can be manufactured, for example, in the same manner as described as the method for manufacturing resin [K1].

[0209] In resin [K3], the ratio of structural units derived from each is, out of the total structural units constituting resin [K3], (a) Structural units derived from (a); 2-60 mol% (c) Structural units derived from this structure; 40-98 mol% It is preferable that this be the case. (a) Structural units derived from (a); 10-50 mol% (c) Structural units derived from (c); 50-90 mol% It is preferable that it be so. Resin [K3] can be manufactured, for example, in the same manner as described as the method for manufacturing resin [K1].

[0210] The resin [K4] can be produced by obtaining a copolymer of (a) and (c), and adding the cyclic ether having 2 to 4 carbon atoms of (b) to the carboxylic acid and / or carboxylic acid anhydride of (a). First, a copolymer of (a) and (c) is produced in the same manner as described for the production of resin [K1]. In this case, it is preferable that the ratio of structural units derived from each is the same as that given for resin [K3].

[0211] Next, a portion of the carboxylic acid and / or carboxylic acid anhydride derived from (a) in the copolymer is reacted with a cyclic ether having 2 to 4 carbon atoms that (b) possesses. Following the production of the copolymer of (a) and (c), the atmosphere inside the flask is replaced from nitrogen to air, and (b), a reaction catalyst for the reaction between a carboxylic acid or carboxylic acid anhydride and a cyclic ether (e.g., tris(dimethylaminomethyl)phenol) and a polymerization inhibitor (e.g., hydroquinone) are added to the flask and the mixture is reacted at, for example, 60 to 130°C for 1 to 10 hours to produce resin [K4]. The amount of (b) used is preferably 5 to 80 moles, more preferably 10 to 75 moles, per 100 moles of (a). This range tends to result in a good balance of storage stability of the colored resin composition, developability when forming patterns, and solvent resistance, heat resistance, mechanical strength, and sensitivity of the resulting patterns. Since the cyclic ether is highly reactive and unreacted (b) is less likely to remain, (b1) is preferred as the (b) used in the resin [K4], and (b1-1) is even more preferred. The amount of the reaction catalyst used is preferably 0.001 to 5 parts by mass per 100 parts by mass of the total amount of (a), (b), and (c). The amount of the polymerization inhibitor used is preferably 0.001 to 5 parts by mass per 100 parts by mass of the total amount of (a), (b), and (c). The reaction conditions, such as the preparation method, reaction temperature, and time, can be adjusted as appropriate, taking into account the manufacturing equipment and the amount of heat generated by polymerization. Similarly, the preparation method and reaction temperature can be adjusted as appropriate, taking into account the manufacturing equipment and the amount of heat generated by polymerization.

[0212] As a first step, resin [K5] is produced in the same manner as the production method for resin [K1] described above to obtain a copolymer of (b) and (c). As described above, the obtained copolymer may be used as is after the reaction, or a concentrated or diluted solution may be used, or it may be used after being extracted as a solid (powder) by methods such as reprecipitation. The ratio of structural units derived from (b) and (c) is such that, relative to the total number of moles of all structural units constituting the copolymer, the structural units derived from (b) are 5 to 95 mol%. (c) Structural units derived from (c); 5-95 mol% It is preferable that this be the case. (b) Structural units derived from (b); 10-90 mol% (c) Structural units derived from (c); 10-90 mol% It is preferable that it be so.

[0213] Furthermore, resin [K5] can be obtained by reacting the cyclic ether derived from (b) in the copolymer of (b) and (c) with the carboxylic acid or carboxylic acid anhydride of (a) under the same conditions as for the production of resin [K4]. The amount of (a) used to react with the copolymer is preferably 5 to 80 moles per 100 moles of (b). Since the cyclic ether is highly reactive and unreacted (b) is less likely to remain, (b1) is preferred as the (b) used in the resin [K5], and (b1-1) is even more preferred.

[0214] Resin [K6] is a resin obtained by further reacting resin [K5] with a carboxylic acid anhydride. The hydroxyl group generated by the reaction of a cyclic ether with a carboxylic acid or carboxylic acid anhydride is reacted with the carboxylic acid anhydride. Examples of carboxylic acid anhydrides 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, and 5,6-dicarboxybicyclo[2.2.1]hepto-2-ene anhydride. The amount of carboxylic acid anhydride used is preferably 0.5 to 1 mole per mole of (a).

[0215] Specific resins (B) include 3,4-epoxycyclohexylmethyl(meth)acrylate / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] Resins such as decyl acrylate / (meth)acrylic acid copolymer [K1]; glycidyl (meth)acrylate / benzyl (meth)acrylate / (meth)acrylic acid copolymer, glycidyl (meth)acrylate / styrene / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6Decyl acrylate / (meth)acrylic acid / N-cyclohexyl maleimide copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 Resins such as decyl acrylate / (meth)acrylic acid / N-cyclohexyl maleimide / 2-hydroxyethyl (meth)acrylate copolymer, 3-methyl-3-(meth)acryloyloxymethyl oxetane / (meth)acrylic acid / styrene copolymer [K2]; resins such as benzyl (meth)acrylate / (meth)acrylic acid copolymer, styrene / (meth)acrylic acid copolymer [K3]; resins obtained by adding glycidyl (meth)acrylate to benzyl (meth)acrylate / (meth)acrylic acid copolymer, resins obtained by adding glycidyl (meth)acrylate to tricyclodecyl (meth)acrylate / styrene / (meth)acrylic acid copolymer, tricyclodecyl Examples of resins include those obtained by adding glycidyl(meth)acrylate to a (meth)acrylate / benzyl(meth)acrylate / (meth)acrylic acid copolymer [K4]; resins obtained by reacting (meth)acrylic acid with a copolymer of tricyclodecyl(meth)acrylate / glycidyl(meth)acrylate, resins obtained by reacting (meth)acrylic acid with a copolymer of tricyclodecyl(meth)acrylate / styrene / glycidyl(meth)acrylate [K5]; and resins obtained by reacting tetrahydrophthalic anhydride with a resin obtained by reacting (meth)acrylic acid with a copolymer of tricyclodecyl(meth)acrylate / glycidyl(meth)acrylate [K6].

[0216] Resin (B) is more preferably at least one selected from the group consisting of resin [K1] and resin [K2], and is particularly preferably resin [K2].

[0217] The weight-average molecular weight (Mw) of resin (B) in terms of polystyrene is preferably 1,000 to 100,000, more preferably 2,000 to 50,000, and even more preferably 3,000 to 30,000. When the weight-average molecular weight is within the above range, the solubility of the unexposed areas in the developer is high, and the residual film rate and hardness of the resulting pattern tend to be high. The degree of dispersion of resin (B) [weight-average molecular weight (Mw) / number-average molecular weight (Mn)] is preferably 1 or more and 6 or less, more preferably 1.001 or more and 4 or less, and even more preferably 1.01 or more and 4 or less.

[0218] The acid value (solid content equivalent) of resin (B) is preferably 10 mg-KOH / g or more and 300 mg-KOH / g or less, more preferably 20 mg-KOH / g or more and 250 mg-KOH / g or less, even more preferably 25 mg-KOH / g or more and 200 mg-KOH / g or less, even more preferably 30 mg-KOH / g or more and 150 mg-KOH / g or less, and particularly preferably 60 mg-KOH / g or more and 135 mg-KOH / g or less. Here, the acid value is measured as the amount of potassium hydroxide (mg) required to neutralize 1 g of resin, and can be determined, for example, by titration using an aqueous potassium hydroxide solution.

[0219] The content of resin (B) is preferably 5 to 50% by mass, more preferably 10 to 40% by mass, and even more preferably 15 to 30% by mass, based on 100% by mass of the solid content of the colored resin composition. When the content of resin (B) is within the above range, the solubility of the unexposed areas in the developer tends to be high.

[0220] <Polymerizable compound (C)> The polymerizable compound (C) is a compound that can be polymerized by active radicals and / or acids generated from the polymerization initiator (D), and examples include compounds having polymerizable ethylenically unsaturated bonds, and is preferably a (meth)acrylic acid ester compound.

[0221] Examples of polymerizable compounds having one ethylenically unsaturated bond include nonylphenylcarbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexylcarbitol acrylate, 2-hydroxyethyl acrylate, N-vinylpyrrolidone, and monomers (a), (b), and (c) mentioned above.

[0222] Examples of polymerizable compounds having two ethylenically unsaturated bonds include 1,6-hexanediol di(meth)acrylate, ethylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, bis(acryloyloxyethyl) ether of bisphenol A, and 3-methylpentanediol di(meth)acrylate.

[0223] The polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds. Examples of such polymerizable compounds include trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, tripentaerythritol octa(meth)acrylate, tripentaerythritol hepta(meth)acrylate, tetrapentaerythritol deca(meth)acrylate, tetrapentaerythritol nona(meth)acrylate, tris(2-(meth)acryloyloxyethyl) isocyanurate, and ethylene glycol modified. Examples include pentaerythritol tetra(meth)acrylate, ethylene glycol-modified dipentaerythritol hexa(meth)acrylate, propylene glycol-modified pentaerythritol tetra(meth)acrylate, propylene glycol-modified dipentaerythritol hexa(meth)acrylate, caprolactone-modified pentaerythritol tetra(meth)acrylate, and caprolactone-modified dipentaerythritol hexa(meth)acrylate, and preferably at least one selected from the group consisting of dipentaerythritol penta(meth)acrylate and dipentaerythritol hexa(meth)acrylate.

[0224] The weight-average molecular weight of the polymerizable compound (C) is preferably 50 to 4,000, more preferably 70 to 3,500, even more preferably 100 to 3,000, even more preferably 150 to 2,900, and particularly preferably 250 to 1,500.

[0225] The content of polymerizable compound (C) may be, for example, 1% by mass or more and 99% by mass or less, preferably 5% by mass or more and 90% by mass or less, more preferably 10% by mass or more and 80% by mass or less, and even more preferably 12% by mass or more and 70% by mass or less, based on the total amount of solids in the colored resin composition.

[0226] <Polymerization initiator (D)> The polymerization initiator (D) is not particularly limited as long as it is a compound that generates active radicals, acids, etc., upon the action of light or heat and can initiate polymerization; any known polymerization initiator can be used.

[0227] Examples of polymerization initiators (D) include O-acyloxime compounds, alkylphenone compounds, biimidazole compounds, triazine compounds, and acylphosphine oxide compounds.

[0228] Examples of O-acyloxime compounds include N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropane-1-one-2-imine, N-acetoxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropane-1-one-2-imine, N-acetoxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropane-1-one-2-imine, N-acetoxy-1-[ Examples include 9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]ethane-1-imine, N-acetoxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethyl-2,4-dioxacyclopentanylmethyloxy)benzoyl}-9H-carbazole-3-yl]ethane-1-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]-3-cyclopentylpropane-1-imine, and N-benzoyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]-3-cyclopentylpropane-1-one-2-imine. Furthermore, commercially available O-acyloxime compounds such as Irgacure® OXE01, OXE02 (both manufactured by BASF), N-1919 (manufactured by ADEKA Corporation), and TR-PBG327 (manufactured by Changzhou Strong Electronic New Materials Co., Ltd.) may also be used.In particular, as the O-acyloxime compound, at least one selected from the group consisting of N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropane-1-one-2-imine, and TR-PBG327(N-acetoxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropane-1-one-2-imine) is preferred, and at least one selected from the group consisting of N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine and TR-PBG327(N-acetoxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropane-1-one-2-imine) is more preferred.

[0229] Examples of alkylphenone compounds include 2-methyl-2-morpholino-1-(4-methylsulfanylphenyl)propan-1-one, 2-dimethylamino-1-(4-morpholinophenyl)-2-benzylbutan-1-one, and 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]butan-1-one. Commercial alkylphenone compounds such as Irgacure® 369, 907, and 379 (all manufactured by BASF) may also be used. Examples of alkylphenone compounds include 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy)phenyl]propan-1-one, 1-hydroxycyclohexylphenyl ketone, oligomers of 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propan-1-one, α,α-diethoxyacetophenone, and benzyldimethyl ketal.

[0230] Examples of biimidazole compounds include 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3-dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole (see, for example, Japanese Patent Publication No. 6-75372, Japanese Patent Publication No. 6-75373, etc.), 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(alkoxyphenyl)biimidazole, and 2,2'-bis(2-chlorophenyl) Examples include (-4,4',5,5'-tetra(dialkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(trialkoxyphenyl)biimidazole (see, for example, Japanese Patent Publication No. 48-38403, Japanese Patent Application Publication No. 62-174204, etc.), and biimidazole compounds in which the phenyl group at the 4,4',5,5'-position is substituted with a carboalkoxy group (see, for example, Japanese Patent Application Publication No. 7-10913, etc.).

[0231] Examples of triazine compounds include 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxynaphthyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxystyryl)-1,3,5-triazine, and 2,4-bis(trichloromethyl)-6-[2-( Examples include 5-methylfuran-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl)ethenyl]-1,3,5-triazine, and 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)ethenyl]-1,3,5-triazine.

[0232] Examples of acylphosphine oxide compounds include 2,4,6-trimethylbenzoyldiphenylphosphine oxide. Commercially available products such as Irgacure® 819 (manufactured by BASF) may also be used.

[0233] Furthermore, examples of polymerization initiators (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, o-benzoyl methyl benzoate, 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; and 10-butyl-2-chloroacridone, benzyl, methyl phenylglyoxylate, and titanocene compounds. These are preferably used in combination with polymerization initiators (D1) (especially amine compounds) as described later.

[0234] The polymerization initiator (D) is preferably a polymerization initiator comprising at least one selected from the group consisting of alkylphenone compounds, triazine compounds, acylphosphine oxide compounds, O-acyloxime compounds, and biimidazole compounds, and more preferably a polymerization initiator comprising an O-acyloxime compound.

[0235] The content of the polymerization initiator (D) is preferably 0.1 parts by mass to 30 parts by mass, and more preferably 1 part by mass to 20 parts by mass, based on 100 parts by mass of the total amount of resin (B) and polymerizable compound (C) contained in the colored resin composition. When the content of the polymerization initiator (D) is within the above range, sensitivity tends to increase and exposure time is shortened, thus improving the productivity of color filters.

[0236] <Polymerization initiator (D1)> The colored resin composition of the present invention may contain a polymerization initiator (D1). The polymerization initiator (D1) is a compound or sensitizer used to promote the polymerization of a polymerizable compound (C) whose polymerization has been initiated by a polymerization initiator (D). When the polymerization initiator (D1) is included, it is usually used in combination with the polymerization initiator (D).

[0237] Examples of polymerization initiators (D1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds, and carboxylic acid compounds.

[0238] Examples of amine compounds include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 2-ethylhexyl 4-dimethylaminobenzoate, N,N-dimethylparatoluidine, 4,4'-bis(dimethylamino)benzophenone (commonly known as Michla's ketone), 4,4'-bis(diethylamino)benzophenone, and 4,4'-bis(ethylmethylamino)benzophenone, with 4,4'-bis(diethylamino)benzophenone being preferred. Alternatively, commercially available amine compounds such as EAB-F (manufactured by Hodogaya Chemical Co., Ltd.) may be used.

[0239] Examples of alkoxyanthracene compounds 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.

[0240] Examples of thioxanthone compounds include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, and 1-chloro-4-propoxythioxanthone.

[0241] Examples of carboxylic acid compounds include phenylsulfanylacetic acid, methylphenylsulfanylacetic acid, ethylphenylsulfanylacetic acid, methylethylphenylsulfanylacetic acid, dimethylphenylsulfanylacetic acid, methoxyphenylsulfanylacetic acid, dimethoxyphenylsulfanylacetic acid, chlorophenylsulfanylacetic acid, dichlorophenylsulfanylacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, and naphthoxyacetic acid.

[0242] When these polymerization initiators (D1) are used, their content is preferably 0.1 parts by mass or more and 30 parts by mass or less, and more preferably 1 part by mass or more and 20 parts by mass or less, based on 100 parts by mass of the total amount of resin (B) and polymerizable compound (C) contained in the colored resin composition.

[0243] <Solvent (E)> The solvent (E) is not particularly limited, and any solvent commonly used in the art may be used. Examples of solvent (E) include ester solvents (solvents containing -COO- but not -O- in the molecule), ether solvents (solvents containing -O- but not -COO- in the molecule), ether ester solvents (solvents containing both -COO- and -O- in the molecule), ketone solvents (solvents containing -CO- but not -COO- in the molecule), alcohol solvents (solvents containing OH in the molecule but not -O-, -CO-, and -COO- in the molecule), aromatic hydrocarbon solvents, amide solvents, dimethyl sulfoxides, etc. Two or more of these solvents may be used in combination.

[0244] Examples of ester solvents include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutanoate, ethyl acetate, n-butyl acetate, isobutyl acetate, pentyl formate, isopentyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexanol acetate, and γ-butyrolactone.

[0245] Examples of ether solvents include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenethole, and methylanisole.

[0246] Examples of ether ester solvents include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, methyl 2-ethoxy-2-methylpropionate Examples include ethyl acetate, 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.

[0247] Examples of ketone solvents 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.

[0248] Examples of alcoholic solvents include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerin.

[0249] Examples of aromatic hydrocarbon solvents include benzene, toluene, xylene, and mesitylene.

[0250] Examples of amide solvents include N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.

[0251] The solvent (E) is preferably a solvent containing at least one selected from propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate, diacetone alcohol, and cyclohexanone.

[0252] The solvent (E) content is usually 99.99% by mass or less, preferably 40% to 99% by mass, more preferably 50% to 95% by mass, even more preferably 70% to 95% by mass, and even more preferably 75% to 90% by mass, relative to the total amount of the colored resin composition. In other words, the total amount of solids in 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, even more preferably 5% to 30% by mass, and even more preferably 10% to 25% by mass. When the solvent (E) content is within the above range, the flatness during coating tends to be good, and the display characteristics tend to be good because there is no shortage of color density when a color filter is formed.

[0253] <Leveling agent (F)> Examples of leveling agents (F) include silicone-based surfactants, fluorine-based surfactants, and silicone-based surfactants containing fluorine atoms. These may have polymerizable groups in their side chains.

[0254] Examples of silicone-based surfactants include surfactants that have siloxane bonds in their molecules. Specifically, examples include Toray Silicone DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, SH29PA, SH30PA, SH8400 (product name: manufactured by Toray Dow Corning Co., Ltd.), KP321, KP322, KP323, KP324, KP326, KP340, KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452, and TSF4460 (manufactured by Momentive Performance Materials Japan LLC).

[0255] Examples of fluorine-based surfactants include surfactants having fluorocarbon chains in their molecules. Specifically, these include Florard® FC430, FC431 (manufactured by Sumitomo 3M Co., Ltd.), Megafac® F142D, F171, F172, F173, F177, F183, F554, R30, RS-718-K (manufactured by DIC Corporation), F-Top® EF301, EF303, EF351, EF352 (manufactured by Mitsubishi Materials Electronic Chemicals Co., Ltd.), Surflon® S381, S382, SC101, SC105 (manufactured by AGC Inc.), and E5844 (manufactured by Daikin Fine Chemical Laboratories, Inc.).

[0256] Examples of silicone-based surfactants containing fluorine atoms include surfactants having siloxane bonds and fluorocarbon chains in their molecules. Specifically, examples include Megafac® R08, BL20, F475, F477, and F443 (manufactured by DIC Corporation).

[0257] When a leveling agent (F) is included, the content of the leveling agent (F) is preferably 0.0005% by mass or more and 1% by mass or less, more preferably 0.001% by mass or more and 0.5% by mass or less, and even more preferably 0.005% by mass or more and 0.1% by mass or less, relative to the total amount of the colored resin composition. This content does not include the content of the dispersant mentioned above. When the content of the leveling agent (F) is within the above range, the flatness of the color filter can be improved.

[0258] <Other ingredients> The colored resin composition may optionally contain additives known in the art, such as fillers, other polymer compounds, adhesion promoters, quenchers, antioxidants, light stabilizers, and chain transfer agents.

[0259] <Method for producing colored resin composition> A colored resin composition can be prepared by mixing a colorant (A), a resin (B), and, if necessary, a polymerizable compound (C), a polymerization initiator (D), a polymerization initiator aid (D1), a solvent (E), a leveling agent (F), and other components. Mixing can be carried out using known or conventional equipment and conditions. The coloring agent (A) may be used as a coloring agent-containing liquid obtained by pre-mixing part or all of the solvent (E) and dispersing it using a bead mill or the like until the average particle size is about 0.2 μm or less, and it is preferable to use it as a coloring agent-containing liquid. In this case, part or all of the dispersant and resin (B) may be added as needed. Alternatively, the coloring agent (A) may be used as a coloring agent-containing liquid obtained by pre-dissolving part or all of the solvent (E). The desired colored resin composition can be prepared by mixing the remaining components to the coloring agent-containing liquid obtained in this way to a predetermined concentration.

[0260] <How to manufacture color filters> A color filter, which may be a color conversion layer, can be formed from the colored resin composition of the present invention. Methods for forming the colored pattern include photolithography, inkjet printing, and printing. Among these, photolithography is preferred. Photolithography is a method in which the colored resin composition is applied to a substrate, dried to form a colored resin composition layer, and then exposed to light through a photomask for development. In photolithography, by not using a photomask during exposure and / or by not developing, a colored coating film, which is a cured product of the colored resin composition layer, can be formed. The colored pattern or colored coating film formed in this way is the color filter of the present invention.

[0261] The film thickness of the color filter to be manufactured is not particularly limited and can be adjusted as appropriate depending on the purpose and application. 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 even more preferably 0.8 μm to 4.5 μm.

[0262] As substrates, glass plates such as quartz glass, borosilicate glass, aluminasilate glass, and soda-lime glass with a silica coating on the surface are used; resin plates such as polycarbonate, polymethyl methacrylate, and polyethylene terephthalate are used; silicon is used; and aluminum, silver, silver / copper / palladium alloy thin films are formed on the substrate. Other color filter layers, resin layers, transistors, circuits, etc. may be formed on these substrates.

[0263] The formation of each color pixel by photolithography can be carried out using known or conventional equipment and conditions. For example, it can be manufactured as follows. First, a colored resin composition is applied to a substrate, and volatile components such as solvents are removed by heat drying (pre-baking) and / or vacuum drying, and then dried to obtain a smooth colored resin composition layer. Coating methods include spin coating, slit coating, and slit and spin coating. When performing heat drying, the temperature is preferably between 30°C and 120°C, and more preferably between 50°C and 110°C. The heating time is preferably between 10 seconds and 60 minutes, and more preferably between 30 seconds and 30 minutes. When performing vacuum drying, it is preferable to do so under a pressure of 50 Pa to 150 Pa and at a temperature range of 20°C to 25°C. The thickness of the colored resin composition layer is not particularly limited and can be appropriately selected according to the desired thickness of the color filter.

[0264] Next, the colored resin composition layer is exposed via a photomask to form the desired colored pattern. The pattern on the photomask is not particularly limited, and a pattern appropriate to the intended application is used. Furthermore, it is preferable to use an exposure apparatus such as a mask aligner and a stepper, as this allows for uniform irradiation of the entire exposure surface with parallel light and precise alignment between the photomask and the substrate on which the colored resin composition layer is formed. When forming a colored coating film, exposure can be performed without using a photomask.

[0265] For exposure, a light source that generates light with a wavelength between 250 nm and 450 nm is preferred. For example, light below 350 nm can be filtered out using a filter that cuts out this wavelength range, or light around 436 nm, 408 nm, and 365 nm can be selectively extracted using a bandpass filter that extracts these wavelength ranges. Specific examples include mercury lamps, light-emitting diodes, metal halide lamps, and halogen lamps.

[0266] A colored pattern is formed on the substrate by developing the colored resin composition layer after exposure by contacting it with a developer. During development, the unexposed parts of the colored resin composition layer are dissolved and removed by the developer. As the developer, aqueous solutions of alkaline compounds such as potassium hydroxide, sodium bicarbonate, sodium carbonate, and tetramethylammonium hydroxide are preferred. The concentration of these alkaline compounds in the aqueous solution is preferably 0.01% by mass or more and 10% by mass or less, and more preferably 0.03% by mass or more and 5% by mass or less. Furthermore, the developer may also contain a surfactant. The development method can be any of the following: paddle method, dipping method, or spray method. Furthermore, the substrate may be tilted to any angle during development. It is preferable to wash the substrate with water after development.

[0267] Furthermore, it is preferable to perform post-baking on the obtained colored pattern or colored coating. The post-baking temperature is preferably 150°C to 250°C, and more preferably 160°C to 240°C. The post-baking time is preferably 1 minute to 120 minutes, and more preferably 10 minutes to 60 minutes.

[0268] <Display device> The aforementioned color filter is useful as a color filter for display devices (e.g., liquid crystal display devices, organic EL devices, electronic paper, etc.) and solid-state image sensors.

[0269] This application claims the benefit of priority based on Japanese Patent Application No. 2021-078791, filed on 6 May 2021. The entire specification of Japanese Patent Application No. 2021-078791, filed on 6 May 2021, is incorporated herein by reference. [Examples]

[0270] The present invention will be described in more detail below with reference to examples. In the examples, percentages and parts representing content or usage are based on mass unless otherwise specified.

[0271] In the following synthesis examples, the structure of the compounds was confirmed by mass spectrometry (LC: Agilent 1200; MASS: Agilent LC / MSD6130).

[0272] The weight-average molecular weight (Mw) and number-average molecular weight (Mn) of the resin, calculated on a polystyrene basis, were measured using the GPC method under the following conditions. Equipment: HLC-8120GPC (manufactured by Tosoh Corporation) Column: TSK-GELG2000HXL Column temperature: 40℃ Solvent: Tetrahydrofuran Flow rate: 1.0mL / min Solid content concentration of the analytical sample: 0.001~0.01% by mass Injection volume: 50μL Detector: RI Calibration standards: TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Corporation) The ratio of the weight-average molecular weight to the number-average molecular weight (Mw / Mn) obtained above in polystyrene terms was defined as the degree of dispersion.

[0273] <Synthesis of pigments> [Dye Synthesis Example 1: Synthesis of Compound (BI-1a)] 14.8 parts of 4-bromo-3,5-dimethylphenol (manufactured by Tokyo Chemical Industry Co., Ltd.) and 134 parts of N,N-dimethylformamide (manufactured by Kanto Chemical Co., Ltd.) were mixed, and 3.2 parts of 60% sodium hydride (manufactured by Kanto Chemical Co., Ltd.) were slowly added, and the mixture was heated to 40°C. 8.0 parts of 1,3,5-tris(bromomethyl)benzene (manufactured by Tokyo Chemical Industry Co., Ltd.) and 34 parts of N,N-dimethylformamide (manufactured by Kanto Chemical Co., Ltd.) were added dropwise, and the mixture was stirred for 5 hours. After cooling to 10°C, 168 parts of water were added. After heating to 25°C, 168 parts of ethyl acetate (manufactured by Kanto Chemical Co., Ltd.) were added, the ethyl acetate layer was extracted, concentrated, and dried under reduced pressure at 60°C to obtain 13.4 parts of the compound represented by formula (BI-1a) (yield 83%).

[0274] [ka]

[0275] Identification of the compound represented by formula (BI-1a) (Mass Spectrometry) Ionization Mode = ESI+: m / z = 715.2

[0276] [Dye Synthesis Example 2: Synthesis of Compound (BI-1)] Ten parts of the compound (BI-1a) obtained in Dye Synthesis Example 1, 7.0 parts of 1-naphthylamine (manufactured by Tokyo Chemical Industry Co., Ltd.), 0.38 parts of palladium acetate (manufactured by Tokyo Chemical Industry Co., Ltd.), 1.7 parts of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (manufactured by Tokyo Chemical Industry Co., Ltd.), 6.4 parts of tert-butoxysodium (manufactured by Tokyo Chemical Industry Co., Ltd.), and 200 parts of dehydrated 1,2-dimethoxyethane (manufactured by Kanto Chemical Co., Ltd.) were mixed and stirred at 93°C for 10 hours. After cooling to 25°C, the resulting mixture was filtered through Celite and the filtrate was concentrated. The obtained residue was purified by silica gel column (solvent: chloroform) and dried under reduced pressure at 60°C to obtain 8.2 parts of the compound represented by formula (BI-1) (yield 65%).

[0277] [ka]

[0278] Identification of the compound represented by formula (BI-1) (Mass Spectrometry) Ionization Mode = ESI+: m / z = 904.6

[0279] [Dye Synthesis Example 3: Synthesis of Compound (CI-1a)] The following reaction was carried out under a nitrogen atmosphere. In a flask equipped with a condenser and a stirrer, 0.27 parts of bis(dibenzylideneacetone)palladium(0) (manufactured by Tokyo Chemical Industry Co., Ltd.), 0.57 parts 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 added. 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 mixture was heated to 80°C in an oil bath and stirred for 2 hours. After cooling the reaction mixture in an ice bath, it was filtered to obtain a solid and a filtrate. The solid was designated as crude A1, and the filtrate as filtrate A1. The obtained crude A1 was washed with 50 parts of toluene, then washed twice with 250 parts of deionized water to obtain a solid. This solid was designated as crude B1. Filtrate A1, 50 parts of toluene, 229 parts of deionized water, and 20.8 parts of 35% hydrochloric acid were placed in a bottom-drain flask and stirred for 1 hour. The mixture was then separated to obtain the organic layer. The obtained organic layer was separated and washed with a mixture of 238 parts of deionized water and 12.5 parts of sodium carbonate, then dried with 150 parts of magnesium sulfate, and the solid was removed by filtration. The obtained organic layer was distilled to obtain a solid. This solid was designated as crude C1. Crude B1 and crude C1 were placed in a flask equipped with a stirring device, and acetonitrile four times the total mass of crude B1 and crude C1 was added. The mixture was stirred for 1 hour. The mixture was filtered to obtain a solid, which was then washed with acetonitrile one time the total mass of crude B1 and crude C1. The washed solid was dried under reduced pressure at 60°C to obtain 75.9 parts of the compound represented by formula (CI-1a). Yield: 90.6%.

[0280] [ka]

[0281] [Dye Synthesis Example 4: Synthesis of Compound (CI-1)] The following reaction was carried out under a nitrogen atmosphere. 50 parts of the compound represented by formula (CI-1a) and 188 parts of N,N-dimethylformamide were placed in a flask equipped with a condenser and a stirrer, and stirred for 30 minutes while cooling in an ice bath. 40 parts of potassium tert-butoxide (manufactured by Tokyo Chemical Industry Co., Ltd.) were placed in the flask, and stirred for a further 1 hour while cooling in an ice bath. 55.6 parts of iodoethane (manufactured by Tokyo Chemical Industry Co., Ltd.) were added dropwise to the reaction mixture while it was still ice-cooled. The reaction mixture was heated to 35°C using an oil bath and stirred for 5 hours, then allowed to cool to room temperature. 1000 parts of a 10% sodium chloride aqueous solution were placed in another flask equipped with a stirrer, and the reaction mixture was added dropwise while stirring. After stirring for 30 minutes, the mixture was filtered to obtain a solid. The obtained solid was washed three times with 500 parts of deionized water, dried under reduced pressure at 60°C, and 53.0 parts of the compound represented by formula (CI-1) were obtained. Yield 93.5%.

[0282] [ka]

[0283] [Dye Synthesis Example 5: Synthesis of Compound (I-23a-1)] The following reaction was carried out under a nitrogen atmosphere. In a flask equipped with a condenser and a stirrer, 6.8 parts of the compound represented by formula (BI-1) obtained in dye synthesis example 2, 11 parts of the compound represented by formula (CI-1) obtained in dye synthesis example 4, and 48 parts of toluene were added. Then, 4.6 parts of phosphorus oxychloride (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) were added and the mixture was stirred at 110°C for 8 hours. After the reaction mixture was cooled to room temperature, 200 parts of chloroform and 200 parts of saturated brine were added, and the aqueous layer was removed by liquid-liquid extraction. After the solvent was removed from the organic layer using an evaporator, the resulting blue-violet solid was purified by column chromatography. Furthermore, the obtained blue-violet solid was washed with 100 parts of chloroform and 500 parts of toluene, and then dried under reduced pressure at 60°C to obtain 7.5 parts of the compound represented by formula (I-23a-1) (yield 39%).

[0284] [ka]

[0285] Identification of the compound represented by formula (I-23a-1) (Mass Spectrometry) Ionization Mode = ESI+: m / z = 760.6, trivalent

[0286] [Dye Synthesis Example 6: Synthesis of Compound (I-23a-2)] The following reaction was carried out under a nitrogen atmosphere. In a flask equipped with a condenser and a stirrer, 4.3 parts of phosphotungstic acid hydrate (Kegin-type phosphotungstic acid; manufactured by Sigma-Aldrich Co., Ltd.), 12 parts of methanol, and 7.9 parts of water were added and mixed at 55°C to prepare a phosphotungstic acid solution. 3.0 parts of the compound represented by formula (I-23a-1) obtained in dye synthesis example 5 were added to the flask and stirred at 55°C for 4 hours. After concentrating the reaction solution, 200 parts of water were added and dispersed for 1 hour, then filtered to obtain a blue solid. Furthermore, 800 parts of methanol were added to the blue solid and dispersed for 1 hour, then filtered and dried under reduced pressure at 60°C to obtain 4.7 parts of the compound represented by formula (I-23a-2) (yield 72%).

[0287] [ka]

[0288] Identification of the compound represented by formula (I-23a-2) (Mass Spectrometry) Ionization Mode = MALDI+: m / z = 2280.0 Ionization mode = MALDI-: m / z = 2902.5

[0289] [Dye Synthesis Example 7: Synthesis of Compound (BI-2a)] 7.4 parts of 4-bromo-3,5-dimethylphenol (manufactured by Tokyo Chemical Industry Co., Ltd.) and 71 parts of N,N-dimethylformamide (manufactured by Kanto Chemical Co., Ltd.) were mixed, and 1.6 parts of 60% sodium hydride (manufactured by Kanto Chemical Co., Ltd.) were slowly added, and the mixture was heated to 40°C. 4.4 parts of 1,4-bis(bromomethyl)benzene (manufactured by Tokyo Chemical Industry Co., Ltd.) and 18 parts of N,N-dimethylformamide (manufactured by Kanto Chemical Co., Ltd.) were added dropwise, and the mixture was stirred for 5 hours. After cooling to 10°C, 93 parts of water were added. After heating to 25°C, 93 parts of ethyl acetate (manufactured by Kanto Chemical Co., Ltd.) were added, the ethyl acetate layer was extracted and concentrated, and dried under reduced pressure at 60°C to obtain 5.1 parts of the compound represented by formula (BI-2a) (yield 45%).

[0290] [ka]

[0291] Identification of the compound represented by formula (BI-2a) (Mass Spectrometry) Ionization Mode = ESI+: m / z = 503.2

[0292] [Dye Synthesis Example 8: Synthesis of Compound (BI-2)] 9.5 parts of the compound represented by formula (BI-2a) obtained in dye synthesis example 7, 7.0 parts of 1-naphthylamine (manufactured by Tokyo Chemical Industry Co., Ltd.), 0.89 parts of palladium acetate (manufactured by Tokyo Chemical Industry Co., Ltd.), 4.1 parts of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (manufactured by Tokyo Chemical Industry Co., Ltd.), 5.8 parts of tert-butoxysodium (manufactured by Tokyo Chemical Industry Co., Ltd.), and 190 parts of dehydrated 1,2-dimethoxyethane (manufactured by Kanto Chemical Co., Ltd.) were mixed and stirred at 93°C for 10 hours. After cooling to 25°C, the resulting mixture was filtered by Celite and the filtrate was concentrated. The obtained residue was purified by silica gel column (solvent: chloroform) and dried under reduced pressure at 60°C to obtain 7.3 parts of the compound represented by formula (BI-2) (yield 61%).

[0293] [ka]

[0294] Identification of the compound represented by formula (BI-2) (Mass Spectrometry) Ionization Mode = ESI+: m / z = 629.5

[0295] [Dye Synthesis Example 9: Synthesis of Compound (I-5a-1)] The following reaction was carried out under a nitrogen atmosphere. In a flask equipped with a condenser and a stirrer, 4.0 parts of the compound represented by formula (BI-2) obtained in dye synthesis example 8, 22 parts of the compound represented by formula (CI-1) obtained in dye synthesis example 4, and 112 parts of toluene were added. Then, 5.9 parts of phosphorus oxychloride (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) were added and the mixture was stirred at 90°C for 6.5 hours. After the reaction mixture was cooled to room temperature, 300 parts of chloroform were added to the resulting solution, which was then poured into 3300 parts of ethyl acetate. The wet solid obtained by filtration was washed with ethyl acetate. The obtained solid was dried under reduced pressure at 60°C and purified by column chromatography. When dried under reduced pressure at 60°C, 1.0 part of the compound represented by formula (I-5a-1) was obtained (yield 10%).

[0296] [ka]

[0297] Identification of the compound represented by formula (I-5a-1) (Mass Spectrometry) Ionization mode = ESI+: m / z = 774.6, divalent

[0298] [Dye Synthesis Example 10: Synthesis of Compound (I-5a-2)] The following reaction was carried out under a nitrogen atmosphere. In a flask equipped with a condenser and a stirrer, 2.0 parts of phosphotungstic acid hydrate (manufactured by Sigma-Aldrich Co., Ltd.), 20 parts of dimethyl sulfoxide, and 0.6 parts of the compound represented by formula (I-5a-1) obtained in dye synthesis example 9 were added and stirred at 45°C for 6 hours. After cooling to 25°C, 80 parts of distilled water were added to the reaction mixture and dispersed for 1 hour, then filtered to obtain a blue solid. Furthermore, 60 parts of methanol were added to the blue solid and dispersed for 1 hour, then filtered and dried under reduced pressure at 60°C to obtain 1.8 parts (quantitatively) of the compound represented by formula (I-5a-2).

[0299] [ka]

[0300] Identification of the compound represented by formula (I-5a-2) (Mass Spectrometry) Ionization Mode = MALDI+: m / z = 1545.7 Ionization mode = MALDI-: m / z = 2902.5

[0301] [Dye Synthesis Example 11: Synthesis of Compound (BI-3a)] 4.0 parts of the compound represented by formula (BI-2a) obtained in dye synthesis example 7, 4.4 parts of 1-propylamine (manufactured by Tokyo Chemical Industries, Ltd.), 0.72 parts of tris(dibenzylideneacetone)dipalladium(0) (manufactured by Fujifilm Wako Pure Chemical Corporation), 0.92 parts of 2-dicyclohexylphosphino-2'-(dimethylamino)biphenyl (manufactured by Fujifilm Wako Pure Chemical Corporation), 2.44 parts of tert-butoxysodium (manufactured by Tokyo Chemical Industries, Ltd.), and 80 parts of dehydrated 1,2-dimethoxyethane (manufactured by Kanto Chemical Co., Ltd.) were mixed and stirred at 40°C for 2 hours. After cooling to 25°C, the resulting mixture was filtered by Celite and the filtrate was concentrated. The obtained residue was purified by silica gel column (solvent: chloroform) and dried under reduced pressure at 60°C to obtain 3.24 parts of the compound represented by formula (BI-3a) (yield 89%).

[0302] [ka]

[0303] Identification of the compound represented by formula (BI-3a) (Mass Spectrometry) Ionization Mode = ESI+: m / z = 461.5

[0304] [Dye Synthesis Example 12: Synthesis of Compound (BI-3)] Three parts of the compound represented by formula (BI-3a) obtained in dye synthesis example 11, two parts of 1-bromonaphthalene (manufactured by Tokyo Chemical Industry Co., Ltd.), zero parts of palladium acetate (manufactured by Tokyo Chemical Industry Co., Ltd.), zero parts of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (manufactured by Tokyo Chemical Industry Co., Ltd.), zero parts of tert-butoxysodium (manufactured by Tokyo Chemical Industry Co., Ltd.), and sixty parts of dehydrated 1,2-dimethoxyethane (manufactured by Kanto Chemical Co., Ltd.) were mixed and stirred at 93°C for 10 hours. After cooling to 25°C, the resulting mixture was filtered through Celite and the filtrate was concentrated. The obtained residue was purified by silica gel column (solvent: chloroform) and dried under reduced pressure at 60°C to obtain three parts of the compound represented by formula (BI-3) (yield 74%).

[0305] [ka]

[0306] Identification of the compound represented by formula (BI-3) (Mass Spectrometry) Ionization Mode = ESI+: m / z = 713.6

[0307] [Dye Synthesis Example 13: Synthesis of Compound (I-17a-1)] 2.01 parts of the compound represented by formula (CI-1) obtained in dye synthesis example 4, 1.35 parts of the compound represented by formula (BI-3) obtained in dye synthesis example 12, 0.75 parts of phosphorus oxychloride (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.), and 9.9 parts of dehydrated toluene (manufactured by Kanto Chemical Co., Ltd.) were mixed and stirred at 100°C for 3 hours. After cooling to 25°C, the resulting mixture was concentrated. The obtained residue was purified by silica gel column (solvent: chloroform) and dried under reduced pressure at 60°C to obtain 2.31 parts of the compound represented by formula (I-17a-1) (yield 68%).

[0308] [ka]

[0309] Identification of the compound represented by formula (I-17a-1) (Mass Spectrometry) Ionization Mode = ESI+: m / z = 815.7, divalent

[0310] [Dye Synthesis Example 14: Synthesis of Compound (I-17a-2)] 1.95 parts of the compound represented by formula (I-17a-1) obtained in dye synthesis example 13, 2.91 parts of phosphotungstic acid hydrate (manufactured by Sigma-Aldrich Co., Ltd.), and 10.2 parts of dehydrated dimethyl sulfoxide (manufactured by Kanto Chemical Co., Ltd.) were mixed and stirred at 45°C for 6 hours. After cooling to 25°C, 78 parts of water were added, and the resulting blue precipitate was filtered. The resulting residue was dried under reduced pressure at 60°C to obtain 3.3 parts of the compound represented by formula (I-17a-2) (yield 84%).

[0311] [ka]

[0312] Identification of the compound represented by formula (I-17a-2) (Mass Spectrometry) Ionization Mode = MALDI+: m / z = 1629.6 Ionization mode = MALDI-: m / z = 2902.5

[0313] [Dye Synthesis Example 15: Synthesis of Compound (BI-4a)] 2.76 parts of the compound represented by formula (BI-1a) obtained in dye synthesis example 1, 3.3 parts of 1-propylamine (manufactured by Tokyo Chemical Industries, Ltd.), 0.528 parts of tris(dibenzylideneacetone)dipalladium(0) (manufactured by Fujifilm Wako Pure Chemical Corporation), 0.69 parts of 2-dicyclohexylphosphino-2'-(dimethylamino)biphenyl (manufactured by Fujifilm Wako Pure Chemical Corporation), 1.77 parts of tert-butoxysodium (manufactured by Tokyo Chemical Industries, Ltd.), and 54 parts of dehydrated 1,2-dimethoxyethane (manufactured by Kanto Chemical Co., Ltd.) were mixed and stirred at 40°C for 2 hours. After cooling to 25°C, the resulting mixture was filtered by Celite and the filtrate was concentrated. The obtained residue was purified by silica gel column (solvent: chloroform) and dried under reduced pressure at 60°C to obtain 1.68 parts of the compound represented by formula (BI-4a) (yield 67%).

[0314] [ka]

[0315] Identification of the compound represented by formula (BI-4a) (Mass Spectrometry) Ionization Mode = ESI+: m / z = 652.6

[0316] [Dye Synthesis Example 16: Synthesis of Compound (BI-4)] 0.82 parts of the compound represented by formula (BI-4a) obtained in dye synthesis example 15, 0.91 parts of 1-bromonaphthalene (manufactured by Tokyo Chemical Industry Co., Ltd.), 0.052 parts of palladium acetate (manufactured by Tokyo Chemical Industry Co., Ltd.), 0.24 parts of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (manufactured by Tokyo Chemical Industry Co., Ltd.), 0.59 parts of tert-butoxysodium (manufactured by Tokyo Chemical Industry Co., Ltd.), and 16 parts of dehydrated 1,2-dimethoxyethane (manufactured by Kanto Chemical Co., Ltd.) were mixed and stirred at 93°C for 10 hours. After cooling to 25°C, the resulting mixture was filtered by Celite and the filtrate was concentrated. The obtained residue was purified by silica gel column (solvent: chloroform) and dried under reduced pressure at 60°C to obtain 1.2 parts of the compound represented by formula (BI-4) (yield 87%).

[0317] [ka]

[0318] Identification of the compound represented by formula (BI-4) (Mass Spectrometry) Ionization Mode = ESI+: m / z = 1030.8

[0319] [Dye Synthesis Example 17: Synthesis of Compound (I-35a-1)] 1.36 parts of the compound represented by formula (CI-1) obtained in dye synthesis example 4, 0.90 parts of the compound represented by formula (BI-4) obtained in dye synthesis example 16, 0.52 parts of phosphorus oxychloride (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.), and 6.8 parts of dehydrated toluene (manufactured by Kanto Chemical Co., Ltd.) were mixed and stirred at 100°C for 3 hours. After cooling to 25°C, the resulting mixture was concentrated. The obtained residue was purified by silica gel column (solvent: chloroform) and dried under reduced pressure at 60°C to obtain 1.36 parts of the compound represented by formula (I-35a-1) (yield 62%).

[0320] [ka]

[0321] Identification of the compound represented by formula (I-35a-1) (Mass Spectrometry) Ionization Mode = ESI+: m / z = 802.7, trivalent

[0322] [Dye Synthesis Example 18: Synthesis of Compound (I-35a-2)] 0.69 parts of the compound represented by formula (I-35a-1) obtained in dye synthesis example 17, 1.18 parts of phosphotungstic acid hydrate (manufactured by Sigma-Aldrich Co., Ltd.), and 3.6 parts of dehydrated dimethyl sulfoxide (manufactured by Kanto Chemical Co., Ltd.) were mixed and stirred at 45°C for 6 hours. After cooling to 25°C, 28 parts of water were added, and the resulting blue precipitate was filtered. The resulting residue was dried under reduced pressure at 60°C to obtain 1.3 parts of the compound represented by formula (I-35a-2) (yield 89%).

[0323] [ka]

[0324] Identification of the compound represented by formula (I-35a-2) (Mass Spectrometry) Ionization Mode = MALDI+: m / z = 2405.9 Ionization mode = MALDI-: m / z = 2902.5

[0325] [Dye Synthesis Example 19: Synthesis of Compound (BI-5a)] The following reaction was carried out under a nitrogen atmosphere. 4.6 parts of 4-bromo-3,5-dimethylphenol (manufactured by Tokyo Chemical Industry Co., Ltd.), 4.0 parts of potassium carbonate, and 17.4 parts of N,N-dimethylformamide were added to a flask equipped with a condenser and a stirrer, and the mixture was stirred at 25°C for 20 minutes. Then, 2.5 parts of 1,4-dibromobutane (manufactured by Tokyo Chemical Industry Co., Ltd.) were added, and the mixture was stirred at 60°C for 5 hours. After the reaction mixture was allowed to cool, 200 parts of distilled water and 200 parts of ethyl acetate were added, and the mixture was separated. The aqueous layer was washed twice with 200 parts of ethyl acetate. The resulting organic layers were dried together over excess Na2SO4 and concentrated under reduced pressure to obtain the crude product. This was purified by silica gel column chromatography (developing phase: xane / toluene 3 / 1). After drying under reduced pressure at 60°C, 3.7 parts of the compound represented by formula (BI-5a) were obtained (yield 69%).

[0326] [ka]

[0327] Identification of the compound represented by formula (BI-5a) (Mass Spectrometry) Ionization Mode = ESI+: m / z = 455.2

[0328] [Dye Synthesis Example 20: Synthesis of Compound (BI-5)] 3.95 parts of the compound represented by formula (BI-5a) obtained in dye synthesis example 19, 2.48 parts of 1-aminonaphthalene (manufactured by Tokyo Chemical Industry Co., Ltd.), 1.00 part of tris(dibenzylideneacetone)dipalladium(0), 0.71 parts of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (manufactured by Tokyo Chemical Industry Co., Ltd.), 3.74 parts of tert-butoxysodium (manufactured by Tokyo Chemical Industry Co., Ltd.), and 40 parts of toluene were mixed and stirred at 110°C for 3 hours. After cooling to 25°C, the resulting mixture was filtered through Celite and the filtrate was concentrated. The obtained residue was purified by silica gel column (solvent: chloroform) and dried under reduced pressure at 60°C to obtain 3.5 parts of the compound represented by formula (BI-5) (yield 70%).

[0329] [ka]

[0330] Identification of the compound represented by formula (BI-5) (Mass Spectrometry) Ionization Mode = ESI+: m / z = 581.5

[0331] [Dye Synthesis Example 21: Synthesis of Compound (CI-5a)] The compound represented by formula (CI-5a) was obtained in the same manner as in dye synthesis example 3, except that 2,4,6-trimethylaniline (manufactured by Tokyo Chemical Industry Co., Ltd.) was used instead of 2,6-dimethylaniline (manufactured by Tokyo Chemical Industry Co., Ltd.).

[0332] [ka]

[0333] [Dye Synthesis Example 22: Synthesis of Compound (CI-5)] The compound represented by formula (CI-5) was obtained in the same manner as in dye synthesis example 4, except that the compound represented by formula (CI-5a) was used instead of the compound represented by formula (CI-1a).

[0334] [ka]

[0335] [Dye Synthesis Example 23: Synthesis of Compound (I-40a-1)] 16.5 parts of the compound represented by formula (CI-5) obtained in dye synthesis example 22, 7.5 parts of the compound represented by formula (BI-5) obtained in dye synthesis example 20, 5.9 parts of phosphorus oxychloride (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.), and 98 parts of dehydrated toluene (manufactured by Kanto Chemical Co., Ltd.) were mixed and stirred at 80°C for 3 hours. After cooling to 25°C, the resulting mixture was concentrated. The obtained residue was purified by silica gel column (solvent: chloroform) and dried under reduced pressure at 60°C to obtain 1.0 part of the compound represented by formula (I-40a-1) (yield 5%).

[0336] [ka]

[0337] Identification of the compound represented by formula (I-40a-1) (Mass Spectrometry) Ionization Mode = ESI+: m / z = 777.7, divalent

[0338] [Dye Synthesis Example 24: Synthesis of Compound (I-40a-2)] 1.3 parts of the compound represented by formula (I-40a-1) obtained in dye synthesis example 23, 3.8 parts of phosphotungstic acid hydrate (manufactured by Sigma-Aldrich Co., Ltd.), and 6.6 parts of dehydrated dimethyl sulfoxide (manufactured by Kanto Chemical Co., Ltd.) were mixed and stirred at 45°C for 6 hours. After cooling to 25°C, 80 parts of water were added, and the resulting blue precipitate was filtered. The resulting residue was dried under reduced pressure at 60°C to obtain 1.4 parts of the compound represented by formula (I-40a-2) (yield 61%).

[0339] [ka]

[0340] Identification of the compound represented by formula (I-40a-2) (Mass Spectrometry) Ionization Mode = MALDI+: m / z = 1553.7 Ionization mode = MALDI-: m / z = 2902.5

[0341] [Dye Synthesis Example 25: Synthesis of Compound (CI-6a)] The compound represented by formula (CI-6a) was obtained in the same manner as in dye synthesis example 3, except that 2,6-dimethyl-4-methoxyaniline was used instead of 2,6-dimethylaniline (manufactured by Tokyo Chemical Industry Co., Ltd.).

[0342] [ka]

[0343] [Dye Synthesis Example 26: Synthesis of Compound (CI-6)] The compound represented by formula (CI-6) was obtained in the same manner as in dye synthesis example 4, except that the compound represented by formula (CI-6a) was used instead of the compound represented by formula (CI-1a).

[0344] [ka]

[0345] [Dye Synthesis Example 27: Synthesis of Compound (I-42a-1)] 4.7 parts of the compound represented by formula (CI-6) obtained in dye synthesis example 26, 2.0 parts of the compound represented by formula (BI-5) obtained in dye synthesis example 20, 1.6 parts of phosphorus oxychloride (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.), and 6.0 parts of dehydrated toluene (manufactured by Kanto Chemical Co., Ltd.) were mixed and stirred at 80°C for 4 hours. After cooling to 25°C, the resulting mixture was concentrated. The obtained residue was purified by silica gel column (solvent: chloroform) and dried under reduced pressure at 60°C to obtain 0.7 parts of the compound represented by formula (I-42a-1) (yield 10%).

[0346] [ka]

[0347] Identification of the compound represented by formula (I-42a-1) (Mass Spectrometry) Ionization Mode = ESI+: m / z = 809.7, divalent

[0348] [Dye Synthesis Example 28: Synthesis of Compound (I-42a-2)] 0.7 parts of the compound represented by formula (I-42a-1) obtained in dye synthesis example 27, 1.8 parts of phosphotungstic acid hydrate (manufactured by Sigma-Aldrich Co., Ltd.), and 210 parts of dehydrated dimethyl sulfoxide (manufactured by Kanto Chemical Co., Ltd.) were mixed and stirred at 45°C for 6 hours. After cooling to 25°C, 300 parts of water were added, and the resulting blue precipitate was filtered. The resulting residue was dried under reduced pressure at 60°C to obtain 0.7 parts of the compound represented by formula (I-42a-2) (yield 57%).

[0349] [ka]

[0350] Identification of the compound represented by formula (I-42a-2) (Mass Spectrometry) Ionization Mode = MALDI+: m / z = 1617.7 Ionization mode = MALDI-: m / z = 2902.5

[0351] [Dye Synthesis Example 29: Synthesis of Compound (I-4a-1)] The compound represented by formula (I-4a-1) was obtained in the same manner as in dye synthesis example 9, except that the compound represented by formula (CI-5) was used instead of the compound represented by formula (CI-1).

[0352] [ka]

[0353] Identification of the compound represented by formula (I-4a-1) (Mass Spectrometry) Ionization Mode = MALDI+: m / z = 1601.9

[0354] [Dye Synthesis Example 30: Synthesis of Compound (I-4a-2)] The compound represented by formula (I-4a-2) was obtained in the same manner as in dye synthesis example 10, except that the compound represented by formula (I-4a-1) was used instead of the compound represented by formula (I-5a-1).

[0355] [ka]

[0356] Identification of the compound represented by formula (I-4a-2) (Mass Spectrometry) Ionization Mode = MALDI+: m / z = 1601.9 Ionization mode = MALDI-: m / z = 2902.5

[0357] [Dye Synthesis Example 31: Synthesis of Compound (x1)] In accordance with the contents described in Japanese Patent Publication No. 2014-108975, a compound represented by the following formula (x1) was synthesized.

[0358] [ka]

[0359] [Dye Synthesis Example 32: Synthesis of Compound (x2)] In accordance with the contents described in Japanese Patent Publication No. 2014-108975, a compound represented by the following formula (x2) was synthesized.

[0360] [ka]

[0361] <Synthesis of resins> Resin synthesis example 1 A suitable amount of nitrogen was flowed into a flask equipped with a reflux condenser, dropping funnel, and stirrer to replace the atmosphere with nitrogen. 141 parts of ethyl lactate and 178 parts of propylene glycol monomethyl ether acetate were added, and the mixture was heated to 85°C while stirring. Then, 38 parts of acrylic acid and 3,4-epoxytricyclo[5.2.1.02,6 ] Decane-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 2,6 A mixed solution of 25 parts of decane-9-yl acrylate (with 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. Meanwhile, a solution of 5 parts of 2,2-azobisisobutyronitrile dissolved in 88 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After the addition was complete, the mixture was held at 85°C for 4 hours, then cooled to room temperature to obtain a copolymer (resin B-1) solution with a viscosity of 23 mPas and a solid content of 25.6%, as measured by a B-type viscometer (23°C). The weight-average molecular weight Mw of the resulting copolymer was 8.0 × 10⁻⁶. 3 The dispersion was 2.1, and the acid value on a solid content basis was 109 mg-KOH / g. Resin B-1 has the following structural units.

[0362] [ka]

[0363] [Example 1] <Preparation of a colorant dispersion (A-1) containing compound (I-23a-2)> Five parts of compound (I-23a-2), three parts of acrylic dispersant, two parts of resin B-1 (based on solid content), seventy-nine parts of propylene glycol monomethyl ether acetate, ten parts of diacetone alcohol, one part of ethyl lactate, and three hundred parts of 0.2 mm zirconia beads were mixed and the resulting mixture was shaken for one hour using paint conditioner (LAU). The zirconia beads were then removed by filtration to obtain a colorant dispersion (A-1).

[0364] <Preparation of colored resin composition> (A) Coloring agent: Coloring agent dispersion (A-1) 245 parts (B) Resin: Resin (B-1) (solid content equivalent) 45 parts (C) Polymerizable compound: Dipentaerythritol hexaacrylate (Kayalad® DPHA; manufactured by Nippon Kayaku Co., Ltd.) 50 copies (D) Polymerization initiator: TR-PBG327 (manufactured by Changzhou Strong Electronics New Materials Co., Ltd.) 3 parts (F) Surfactant: Fluorine-based surfactant (Megafac® F554; manufactured by DIC Corporation, 0.09 parts) (E) Solvent: Propylene glycol monomethyl ether acetate (E-1) 506 parts (E) Solvent: Ethyl lactate (E-2) 27 parts A colored resin composition was obtained by mixing these ingredients.

[0365] [Examples 2-7, Comparative Examples 1-2] Each colored resin composition was obtained in the same manner as in Example 1, except that compound (I-23a-2) was replaced with the following compound. Example 2: Compound (I-5a-2) Example 3: Compound (I-17a-2) Example 4: Compound (I-35a-2) Example 5: Compound (I-40a-2) Example 6: Compound (I-42a-2) Example 7: Compound (I-4a-2) Comparative Example 1: Compound (x1) Comparative example 2: Compound (x2)

[0366] <Example 1> (Preparation of red resin composition) (A) Coloring agent: Acid Red 52 (manufactured by Tokyo Chemical Industry Co., Ltd.) 8 parts (B) Resin: Resin (B-1) (solid content equivalent) 50 parts (C) Polymerizable compound: Dipentaerythritol hexaacrylate (Kayalad® DPHA; manufactured by Nippon Kayaku Co., Ltd.) 50 copies (D) Polymerization initiator: 3 parts TR-PBG327 (manufactured by Changzhou Strong Electronics New Materials Co., Ltd.) (F) Surfactant: Fluorine-based surfactant (Megafac® F554; manufactured by DIC Corporation) 0.09 parts (E) Solvent: Propylene glycol monomethyl ether acetate (E-1) 127 parts (E) Solvent: Ethyl lactate (E-2) 30 parts (E) Solvent: 4-Hydroxy-4-methyl-2-pentanone (E-3) 472 parts A red resin composition was obtained by mixing these ingredients.

[0367] <Formation of a colored coating (color filter)> On a 2-inch square glass substrate (Eagle 2000; Corning), the colored resin compositions obtained in Examples 1-7 and Comparative Examples 1-2, as well as the red resin composition obtained in Fabrication Example 1, were applied by spin coating. The substrates were then pre-baked at 100°C for 3 minutes to form the composition layers. After cooling, the substrates were exposed to air at 60 mJ / cm² using an exposure machine (TME-150RSK; Topcon) under atmospheric conditions. 2 After irradiating the composition layer with light at an exposure level (based on 365 nm), a colored coating film was obtained by post-baking in an oven at 230°C for 20 minutes.

[0368] <Measurement of transmission spectrum> Using an Olympus colorimeter (OSP-SP-200), the transmission spectra of the colored coating films obtained from Examples 1-7, Comparative Examples 1-2, and Fabrication Example 1 were measured.

[0369] <Calculation of brightness> The CIE chromaticity coordinates and lightness Y were determined when the colored resin compositions of Examples 1-7 or Comparative Examples 1-2 were mixed with the red resin composition of Production Example 1 in the ratios shown in Table 10. The CIE chromaticity coordinates and lightness Y were calculated using the transmission spectra obtained from the colored coating films of Examples 1-7 and Comparative Examples 1-2, the transmission spectrum obtained from the colored coating film of Production Example 1, and the characteristic function of the C light source. All of the mixing ratios in Table 10 were combinations that resulted in a CIE chromaticity coordinate (x,y) = (0.150, 0.060). The values ​​of lightness Y are shown in Table 10. A larger value of Y indicates higher lightness.

[0370] [Table 10]

[0371] In Table 10, each notation indicates the following coloring agent. I-23a-2: Compound (I-23a-2) I-5a-2: Compound (I-5a-2) I-17a-2: Compound (I-17a-2) I-35a-2: Compound (I-35a-2) I-40a-2: Compound (I-40a-2) I-42a-2: Compound (I-42a-2) I-4a-2: Compound (I-4a-2) x1 : Compound (x1) x2 : Compound (x2) AR52: Acid Red 52

Claims

1. A compound represented by formula (I). 【Chemistry 1】 [In formula (I), R 1 ~R 4 and R 13 Each of these independently represents a hydrocarbon group having 1 to 10 carbon atoms, which may have a hydrogen atom or a substituent. R 5 ~R 12 Each of these independently represents a hydrogen atom, a halogen atom, or a C1-C5 hydrocarbon group which may have substituents. T 1 and T 2 These independently represent a optionally substituted divalent aromatic hydrocarbon group or an optionally substituted divalent aromatic heterocyclic group. L 1 This represents an avalence aliphatic hydrocarbon group having 1 to 12 carbon atoms or a group represented by formula (i), wherein at least one methylene group contained in the aliphatic hydrocarbon group is replaced by -O-. 'a' represents either 2 or 3. b and c represent integers greater than or equal to 1, independently of each other. d represents a non-negative integer. X c- represents an anion with a valence of c.] 【Chemistry 2】 [In formula (i), T 3 This represents an α-valent aromatic hydrocarbon group or an α-valent aromatic heterocyclic group, which may have substituents. L 2 This represents a divalent aliphatic hydrocarbon group having 1 to 5 carbon atoms, in which at least one methylene group contained in the aliphatic hydrocarbon group is replaced by -O-. a is the same as described above. * is T 2 This represents a combination of [ ].

2. A colored resin composition comprising a coloring agent and a resin, wherein the coloring agent comprises the compound described in claim 1.

3. The colored resin composition according to claim 2, further comprising a polymerizable compound and a polymerization initiator.

4. A color filter formed from the colored resin composition according to claim 2 or 3.

5. A display device comprising the color filter described in claim 4.

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