Compound, resin composition, cured product of resin composition, color filter, display device, solid-state imaging element, and method for producing compound

Abstract

Provided is a compound having optical characteristics suitable for a color filter, having high solubility in an organic solvent, and having high heat resistance. A compound represented by formula (I). [In formula (I), each of R1-R10 independently represents a hydrogen atom, an optionally substituted hydrocarbon group having 1-20 carbon atoms, a halogen atom, a hydroxyl group, or a carboxyl group, a methylene group contained in the hydrocarbon group may be substituted with-O-,-CO-, or-N (RB1)-, R2 and R5, R3 and R6, R4 and R7, R5 and R8, R7 and R10, and / or R9 and R10 may be bonded to each other to form a ring, each of RB1 independently represents a hydrogen atom or an optionally substituted hydrocarbon group having 1-20 carbon atoms, and R6 represents a hydrogen atom or an optionally substituted hydrocarbon group having 1-20 carbon atoms. RA1 and RA2, RA3 and RA4, and RA5 and RA6 each independently represent a hydrogen atom, a-C (= O)-ORB3 group, a group represented by formula (i) or a group represented by formula (ii), RB3 each independently represents a hydrogen atom or an optionally substituted hydrocarbon group having 1-20 carbon atoms, provided that at least one of RA1 to RA6 represents a-C (= O)-ORB3 group. ] # imgabs0 #

Description

Technical Field

[0001] The present invention relates to a compound, a resin composition, a cured product of the resin composition, a color filter, a display device, a solid-state imaging element, and a method for producing the compound. Background Art

[0002] Color filter substrates, used in display devices such as liquid crystal displays, electroluminescent displays, and plasma displays, as well as solid-state imaging devices such as CCDs and CMOS sensors, have a structure in which a black base layer and color filters (e.g., red (R), green (G), and blue (B)) for forming each pixel are formed on a transparent substrate, and a protective film is optionally laminated on top. Furthermore, a patterned transparent pixel electrode is formed on top of the base layer.

[0003] As a colorant contained in a curable resin composition for forming such a color filter, for example, a terylene-based compound is known (Patent Documents 1 and 2).

[0004] Prior art literature

[0005] Patent Literature

[0006] Patent Document 1: Japanese Patent Application Laid-Open No. 2022-126586

[0007] Patent Document 2: International Publication No. 2009 / 027952 Summary of the Invention

[0008] Color filters are manufactured, for example, by dissolving the coloring compounds disclosed in Patent Documents 1 and 2 together with other components such as a curable resin in a solvent to prepare a curable resin composition, applying the curable resin composition to a substrate, developing it into a desired pattern, and then crosslinking the curable resin by post-baking at high temperature. From the perspective of obtaining uniform, high color filter performance, it is believed that when manufacturing the curable resin composition, each component needs to be fully dissolved in an organic solvent such as cyclohexanone. However, depending on the coloring compound, the solubility in the organic solvent is sometimes insufficient. In addition, due to insufficient heat resistance of the coloring compound, it is sometimes unable to withstand the high temperature heating in the post-baking process when manufacturing the color filter.

[0009] Therefore, an object of the present invention is to provide a compound having optical properties suitable for color filters and the like, and having high solubility in organic solvents and high heat resistance.

[0010] The present inventors have discovered that the above-mentioned object can be achieved by the compound of the present invention described below. That is, the present invention includes the following aspects.

[0011] [1] A compound represented by formula (I).

[0012]

[0013] [In formula (I),

[0014] R 1 ~R 10 Each independently represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, a halogen atom, a hydroxyl group, or a carboxyl group, wherein the methylene group contained in the hydrocarbon group may be substituted with -O-, -CO-, or -N(R B1 )-,R 2 and R 5 、R 3 and R 6 、R 4 and R 7 、R 5 and R 8 、R 7 and R 10 , and / or R 9 and R 10 can bond to each other to form a ring,

[0015] R B1 each independently represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent,

[0016] R A1 and R A2 、R A3 and R A4 , and R A5 and R A6 Each independently represents a hydrogen atom, -C(=O)-OR B3 a group represented by formula (i), or a group represented by formula (ii),

[0017]

[0018] [In formula (i), * represents A1 and R A2 、R A3 and R A4 , or R A5 and R A6 bonding sites of

[0019]

[0020] [In formula (ii),

[0021] R B2 represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent,

[0022] * indicates the same as R A1 and R A2 、R A3 and R A4 , or R A5 and R A6 bonding sites of

[0023] R B3 each independently represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent,

[0024] Among them, R A1 ~R A6 At least one of them represents -C(=O)-OR B3 base.]

[0025] [2] The compound according to [1], wherein R in formula (I) A1 and R A2 、R A3 and R A4 , and R A5 and R A6 Each independently represents -C(=O)-OR B3 or a group represented by formula (ii),

[0026] Among them, R A1 and R A2 、R A3 and R A4 , and R A5 and R A6 At least one of them represents -C(=O)-OR B3 base.

[0027] [3] The compound according to [1] or [2], wherein R in formula (I) 1 ~R 10 represents a hydrogen atom, R B2 Each independently represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.

[0028] [4] A colorant comprising the compound represented by formula (I) according to any one of [1] to [3].

[0029] [5] The colorant according to [4], comprising 90% by mass or more of the compound represented by formula (I) based on the total amount of the colorant.

[0030] [6] A resin composition comprising the compound represented by formula (I) according to any one of [1] to [3] and an alkali-soluble resin.

[0031] [7] A resin composition comprising the colorant described in [4] or [5] and an alkali-soluble resin.

[0032] [8] The resin composition according to [6] or [7], further comprising a polymerizable compound and a polymerization initiator.

[0033] [9] A cured product of the resin composition described in [8].

[0034]

[10] A color filter comprising the cured product described in [9].

[0035]

[11] A display device comprising the color filter described in

[10] .

[0036]

[12] A solid-state imaging element comprising the color filter described in

[10] .

[0037]

[13] A method for producing a compound represented by formula (VI), comprising reacting a compound represented by formula (IV) with a compound represented by formula (Vi) or a compound represented by formula (V-ii) in the presence of a catalyst.

[0038]

[0039] [In formula (IV),

[0040] R 1’ 、R 4’ 、R 7’ 、R 8’ 、R 9’ and R 10’ Each independently represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, a halogen atom, a hydroxyl group, or a carboxyl group, wherein the methylene group contained in the hydrocarbon group may be substituted with -O-, -CO-, or -N(R E1 )-,R 4’ and R 7’ and / or R 7’ and R 10’ can bond to each other to form a ring,

[0041] R E1 each independently represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent,

[0042] Z 1 and Z 2 each independently represents a bromine atom or an iodine atom,

[0043] R D1 and R D2 , and R D5 and R D6Each independently represents a hydrogen atom, -C(=O)-OR B3 a group represented by formula (i), or a group represented by formula (iii),

[0044]

[0045] [In formula (i), * represents D1 and R D2 , or R D5 and R D6 bonding sites of

[0046]

[0047] [In formula (iii),

[0048] R E2 represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent,

[0049] * indicates the same as R D1 and R D2 , or R D5 and R D6 The bonding site of ].

[0050]

[0051] [In formulas (Vi) and (V-ii),

[0052] R 2’ 、R 3’ 、R 5’ and R 6’ Each independently represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, a halogen atom, a hydroxyl group, or a carboxyl group, wherein the methylene group contained in the hydrocarbon group may be substituted with -O-, -CO-, or -N(R E1 )-,R 2’ and R 5’ and / or R 3’ and R 6’ can bond to each other to form a ring,

[0053] R E1 each independently represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent,

[0054] R D3 and R D4 Each independently represents a hydrogen atom, -C(=O)-OR B3 a group represented by formula (i), or a group represented by formula (iii),

[0055] A 1 ~A4 Each independently represents a hydroxyl group, a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, or -OR E3 base,

[0056] R E3 each independently represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent,

[0057] A 1 and A 2 and / or A 3 and A 4 Indicates -OR E3 Base time, 2-OR E3 The groups can bond to each other to form -OR E4 -represented by a divalent group, R E4 It is a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.]

[0058]

[0059] [In formula (VI),

[0060] R 1’ ~R 10’ and R D1 ~R D6 and R in formula (IV), formula (Vi) and (V-ii) 1’ ~R 10’ and R D1 ~R D6 has the same meaning.]

[0061] According to the present invention, a compound having optical properties suitable for a color filter and having high solubility in an organic solvent and high heat resistance can be provided. DETAILED DESCRIPTION

[0062] The following describes embodiments of the present invention in detail. It should be noted that the scope of the present invention is not limited to the embodiments described herein, and various modifications can be made without departing from the gist of the present invention. In addition, when multiple upper and lower limits are described for a specific parameter, any of these upper and lower limits can be combined to form a preferred numerical range.

[0063] [Compound represented by formula (I)]

[0064] The present invention provides a compound represented by formula (I).

[0065]

[0066] [In formula (I),

[0067] R1 ~R 10 Each independently represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, a halogen atom, a hydroxyl group, or a carboxyl group, wherein the methylene group contained in the hydrocarbon group may be substituted with -O-, -CO-, or -N(R B1 )-,R 2 and R 5 、R 3 and R 6 、R 4 and R 7 、R 5 and R 8 、R 7 and R 10 , and / or R 9 and R 10 can bond to each other to form a ring,

[0068] R B1 each independently represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent,

[0069] R A1 and R A2 、R A3 and R A4 , and R A5 and R A6 Each independently represents a hydrogen atom, -C(=O)-OR B3 a group represented by formula (i), or a group represented by formula (ii),

[0070]

[0071] [In formula (i), * represents A1 and R A2 、R A3 and R A4 , or R A5 and R A6 bonding sites of

[0072]

[0073] [In formula (ii),

[0074] R B2 represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent,

[0075] * indicates the same as R A1 and R A2 、R A3 and R A4 , or R A5 and R A6 bonding sites of

[0076] R B3 each independently represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent,

[0077] Among them, R A1 ~R A6 At least one of them represents -C(=O)-OR B3 base.]

[0078] In this specification, the compound represented by formula (I) is also referred to as compound (I). The same applies to other formulae. The symbols in formula (I) are explained below.

[0079] R in formula (I) 1 ~R 10 Each independently represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, a halogen atom, a hydroxyl group, or a carboxyl group, wherein the methylene group contained in the hydrocarbon group may be substituted with -O-, -CO-, or -N(R B1 )-,R 2 and R 5 、R 3 and R 6 、R 4 and R 7 、R 5 and R 8 、R 7 and R 10 , and / or R 9 and R 10 They may be bonded to each other to form a ring. B1 Each independently represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.

[0080] Examples of the hydrocarbon group having 1 to 20 carbon atoms include aliphatic hydrocarbon groups, aromatic hydrocarbon groups, and combinations thereof having 1 to 20 carbon atoms. The aliphatic hydrocarbon group may be saturated or unsaturated, and may be chain or alicyclic.

[0081] Examples of the saturated or unsaturated chain hydrocarbon group include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, a dodecyl group, a tridecyl group, a tetradecyl group, a pentadecyl group, a hexadecyl group, a heptadecyl group, an octadecyl group, a nonadecyl group, and an eicosyl group; an isopropyl group, a (1-ethyl)propyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a (1-ethyl)butyl group, a (2-ethyl)butyl group, a (1-propyl)butyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, a (2-methyl)pentyl group, a (1-ethyl)pentyl group, a (3-ethyl)pentyl group, a (1-propyl)pentyl group, a (1-butyl)pentyl group, an isohexyl group, a (2- Branched chain alkyl groups such as (1-methyl)hexyl, (5-methyl)hexyl, (2-ethyl)hexyl, (1-butyl)hexyl, (1-pentyl)hexyl, (2-methyl)heptyl, (2-ethyl)heptyl, (3-ethyl)heptyl, (1-hexyl)heptyl, (2-methyl)octyl, (2-ethyl)octyl, (1-heptyl)octyl, (2-ethyl)nonyl, and (1-octyl)nonyl; and alkenyl groups such as vinyl, 1-propenyl, 2-propenyl (allyl), (1-methyl)vinyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, (1-(2-propenyl))vinyl, (1,2-dimethyl)propenyl, and 2-pentenyl. The number of carbon atoms in the saturated chain hydrocarbon group is preferably 1 to 18, more preferably 2 to 15, and even more preferably 3 to 12. The unsaturated chain hydrocarbon group preferably has 2 to 18 carbon atoms, more preferably 2 to 15 carbon atoms, and even more preferably 3 to 12 carbon atoms.

[0082] Examples of the saturated or unsaturated alicyclic hydrocarbon group include cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl; cycloalkenyl groups such as cyclohexenyl (e.g., cyclohex-2-ene and cyclohex-3-ene), cycloheptenyl, and cyclooctenyl; and norbornyl, adamantyl, and bicyclo[2.2.2]octyl. The saturated or unsaturated alicyclic hydrocarbon group preferably has 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms.

[0083] Examples of the aromatic hydrocarbon group include phenyl, 1-naphthyl, 2-naphthyl, phenanthrenyl, anthracenyl, and pyrenyl. The aromatic hydrocarbon group preferably has 6 to 15 carbon atoms, more preferably 6 to 12 carbon atoms.

[0084] The hydrocarbon group having 1 to 20 carbon atoms may be a group formed by combining two or more of the chain hydrocarbon groups, alicyclic hydrocarbon groups, and / or aromatic hydrocarbon groups listed above, as long as the upper limit of the number of carbon atoms is 20 or less. Such a group may be, for example, a group formed by combining an aromatic hydrocarbon group with at least one group selected from chain hydrocarbon groups, alicyclic hydrocarbon groups, and aromatic hydrocarbon groups. In the hydrocarbon group obtained by the combination, the chain hydrocarbon group may be combined to form a divalent group (for example, an alkanediyl group). Examples of hydrocarbon groups obtained by the combination include aralkyl groups such as benzyl, phenethyl, and 1-methyl-1-phenylethyl; aralkyl groups such as phenylvinyl (phenylvinyl); arylalkynyl groups such as phenylethynyl; 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 Phenyl, 3,5-dimethylphenyl, 4-vinylphenyl, o-isopropylphenyl, m-isopropylphenyl, p-isopropylphenyl, 2,3-diisopropylphenyl, 2,4-diisopropylphenyl, 2,5-diisopropylphenyl, 2,6-diisopropylphenyl, 2,4,6-triisopropylphenyl, 4-butylphenyl, o-tert-butylphenyl, m-tert-butylphenyl, p-tert-butylphenyl, 2,6-di(tert-butyl)phenyl, 3,5-di(tert-butyl)phenyl, 3,6-di(tert-butyl)phenyl, 4-tert-butyl-2,6-dimethylphenyl, 4-pentylphenyl, 4-octylphenyl, 4-(2,4,4-trimethyl-2-pentyl)phenyl, 2-dodecylphenyl, 3-dodecylphenyl, 4-dodecylphenyl and other alkylaryl groups; 2,3-dihydro-4-indenyl, 1,2,3,5,6,7-hexahydro-4-s-indacenyl, 8-methyl-1,2,3,5,6,7-hexahydro- Aryl groups to which an alkanediyl group is bonded, such as 4-s-indacenyl, 5,6,7,8-tetrahydro-1-naphthyl, 5,6,7,8-tetrahydro-2-naphthyl, 3-methyl-5,6,7,8-tetrahydro-2-naphthyl, and 3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl; aryl groups to which one or more aryl groups are bonded, such as biphenyl and terphenyl; cyclohexylmethylphenyl, benzylphenyl, (dimethyl(phenyl)methyl)phenyl, and the like.The hydrocarbon group may be, for example, a hydrocarbon group obtained by combining a chain hydrocarbon group and an alicyclic hydrocarbon group. Examples thereof include 1-methylcyclopropyl, 1-methylcyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 1,2-dimethylcyclohexyl, 1,3-dimethylcyclohexyl, 1,4-dimethylcyclohexyl, 2,3-dimethylcyclohexyl, 2,4-dimethylcyclohexyl, 2,5-dimethylcyclohexyl, 2,6-dimethylcyclohexyl, 3,4-dimethylcyclohexyl, 3,5-dimethylcyclohexyl, 2,2-dimethylcyclohexyl. Alicyclic hydrocarbon groups to which one or more alkyl groups are bonded, such as 3,3-dimethylcyclohexyl, 4,4-dimethylcyclohexyl, 2,4,6-trimethylcyclohexyl, 2,2,6,6-tetramethylcyclohexyl, 3,3,5,5-tetramethylcyclohexyl, 4-pentylcyclohexyl, 4-octylcyclohexyl, and 4-cyclohexylcyclohexyl; and alkyl groups to which one or more alicyclic hydrocarbon groups are bonded, such as cyclopropylmethyl, cyclopropylethyl, cyclobutylmethyl, cyclobutylethyl, cyclopentylmethyl, cyclopentylethyl, cyclohexylmethyl, 2-methylcyclohexylmethyl, cyclohexylethyl, and adamantylmethyl. The number of carbon atoms in a group formed by combining two or more of a chain hydrocarbon group, alicyclic hydrocarbon group, and aromatic hydrocarbon group is preferably 6 to 18, and more preferably 6 to 15.

[0085] Examples of the substituents that the hydrocarbon group having 1 to 20 carbon atoms may have include a halogen atom; a nitrile group; a nitro group; an amino group; a hydroxyl group; an alkoxy group having 1 to 20 carbon atoms, such as a methoxy group and an ethoxy group; an aryloxy group having 6 to 20 carbon atoms, such as a phenoxy group, a 1-naphthyloxy group and a 2-naphthyloxy group; a thiol group; an alkylthio group having 1 to 20 carbon atoms, such as a methylthio group and an ethylthio group; an allylthio group; an arylthio group having 6 to 20 carbon atoms, such as a phenylthio group and a 1-naphthylthio group and a 2-naphthylthio group; a thioxy group; an alkylthiooxy group having 1 to 20 carbon atoms, such as a methylthiooxy group and an ethylthiooxy group; an arylthiooxy group having 6 to 20 carbon atoms, such as a phenylthiooxy group, a 1-naphthylthio group and a 2-naphthylthio group; a silyl group; a methylboryl group; Alkyl groups; alkylamino groups having 1 to 20 carbon atoms, such as monomethylamino, dimethylamino, trimethylamino, monoethylamino, diethylamino, and triethylamino; arylamino groups having 6 to 20 carbon atoms, such as monophenylamino, diphenylamino, and triphenylamino; aralkylamino groups having 7 to 20 carbon atoms, such as benzylamino; carboxyl groups; carbamoyl groups; alkylcarbonyl groups having 2 to 20 carbon atoms, such as acetyl and propionyl; arylcarbonyl groups having 7 to 20 carbon atoms, such as benzoyl, 1-naphthylcarbonyl, and 2-naphthylcarbonyl; alkoxycarbonyl groups having 2 to 20 carbon atoms, such as methoxycarbonyl and ethoxycarbonyl; aryloxycarbonyl groups having 7 to 20 carbon atoms, such as phenoxycarbonyl, 1-naphthyloxycarbonyl, and 2-naphthyloxycarbonyl. When a hydrocarbon group having 1 to 20 carbon atoms has a substituent as described above, the number of carbon atoms of the hydrocarbon group shall be the number of carbon atoms of the group after the substitution.

[0086] The methylene group (-CH2-) contained in the hydrocarbon group having 1 to 20 carbon atoms may be substituted with -O-, -CO- or -N(R B1 )-. It should be noted that at least one methylene group is substituted with -O-, -CO- or -N(R B1 )-before the carbon number of the hydrocarbon group. B1 Each independently represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent. Examples of the hydrocarbon group having 1 to 20 carbon atoms which may have a substituent include those mentioned above for R in formula (I). 1 ~R 10 The groups described, R 1 ~R 10 The same description of the preferred hydrocarbon groups having 1 to 20 carbon atoms applies to R B1 The methylene group contained in the hydrocarbon group having 1 to 20 carbon atoms may be substituted with -O-, -CO- or -N(R B1 )-, two or more methylene groups may be independently substituted with -O-, -CO- or -N(R B1 )-. In addition, by substituting two or more methylene groups with -N(R B1 )-and there are multiple R B1 When each R B1 They can be the same as each other or different.

[0087] When at least one methylene group contained in a hydrocarbon group having 1 to 20 carbon atoms is substituted with -O- or -CO-, the number of such groups may be one or two or more. Specific examples of groups in which at least one methylene group (-CH2-) contained in such a hydrocarbon group is substituted with -O- or -CO- include groups represented by the following formulae (Y-1) to (Y-60). * indicates a bonding site.

[0088]

[0089]

[0090]

[0091] The methylene group contained in the hydrocarbon group having 1 to 20 carbon atoms is substituted with -N(R B1 )-, the number thereof may be 1 or 2 or more. The methylene group (-CH2-) contained in the hydrocarbon group is substituted with -N(R B1 )-, specifically, groups represented by the following formulae (Z-1) to (Z-48) are mentioned. * represents a bonding site.

[0092]

[0093]

[0094] The above R 1 ~R 10 In, R 2 and R 5 、R 3 and R 6 、R 4 and R 7 、R 5 and R 8 、R 7 and R 10 , and / or R 9 and R 10 They may bond to each other to form a ring. 2 and R 5 When the same compounds are bonded to form a ring, 2 and R 5 The group to which the bond is bonded includes a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent (the methylene group contained in the hydrocarbon group may be substituted with -O-, -CO- or -N(R B1 )-) is a divalent group formed by removing one hydrogen atom. For example, as R 2 and R 5 、R 3 and R 6 、R 4 and R 7 、R 5 and R 8 、R 7 and R 10 , and / or R 9 and R 10 The bonded groups include *-CO-O-CO-* or *-CO-N(R B1 )-CO-*, *-CO-O-CO-* or *-CO-N(R B1 )-CO-* is a divalent group. In addition, * represents a bonding site.

[0095] As R 2 and R 5 、R 3 and R 6 、R 4 and R 7 、R 5 and R 8 、R 7 and R 10 , and / or R 9 and R 10Examples of the groups to be bonded include divalent groups represented by the following formulae (H-1) to (H-16). 2 and R 5 In the case of the bonded group, it means 2 and R 5 Each has a bonding site of the skeleton represented by formula (I). 3 and R 6 、R 4 and R 7 、R 5 and R 8 、R 7 and R 10 , and / or R 9 and R 10 The bonding groups also represent bonding sites to the skeleton represented by the formula (I) possessed by each of them.

[0096]

[0097] R in formula (I) A1 and R A2 、R A3 and R A4 , and R A5 and R A6 Each independently represents a hydrogen atom, -C(=O)-OR B3 a group represented by formula (i), or a group represented by formula (ii),

[0098]

[0099] [In formula (i), * represents A1 and R A2 、R A3 and R A4 , or R A5 and R A6 bonding sites of

[0100]

[0101] [In formula (ii),

[0102] R B2 represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent,

[0103] * indicates the same as R A1 and R A2 、R A3 and R A4 , or R A5 and R A6bonding sites of

[0104] R B3 each independently represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent,

[0105] Among them, R A1 ~R A6 At least one of them represents -C(=O)-OR B3 Base. R A1 and R A2 、R A3 and R A4 , and / or R A5 and R A6 Each independently represents a hydrogen atom, -C(=O)-OR B3 The group represented by formula (i) or the group represented by formula (ii) is R A1 and R A2 Combination of R A3 and R A4 Combination of, and / or R A5 and R A The combination of each independently represents a combination of a hydrogen atom and a hydrogen atom, or a hydrogen atom and -C(=O)-OR B3 A combination of groups, or -C(=O)-OR B3 -C(=O)-OR B3 A combination of groups, or two groups constitute a group represented by formula (i), and / or two groups constitute a group represented by formula (ii). A1 and R A2 、R A3 and R A4 , and R A5 and R A6 Such description also means the above-mentioned combination in other descriptions in this specification.

[0106] R B2 and R B3 Each independently represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent. Examples of the hydrocarbon group having 1 to 20 carbon atoms and the substituent that the hydrocarbon group may have include the following: 1 etc. and R B1 The described hydrocarbon groups and substituents.

[0107] The above-mentioned R B1 、R B2 and R B3In the case of a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, examples thereof include groups represented by the following formulae (D-1) to (D-47) and (G-1) to (G-24), and these groups substituted with the substituents described above. * indicates a bonding site.

[0108]

[0109]

[0110] Examples of the hydrocarbon group having 1 to 20 carbon atoms which may have a substituent in formula (ii) include the groups represented by the above-mentioned formulas (G-1) to (G-24), the groups represented by the above-mentioned formulas (D-1) to (D-47), and these groups substituted with the above-mentioned substituents. From the viewpoint of the optical properties, solubility in organic solvents, and heat resistance of the compound represented by formula (I), R B2 A group containing an aromatic group having 6 to 20 carbon atoms is preferred.

[0111] Examples of groups containing aromatic groups include aromatic groups such as phenyl, 1-naphthyl, 2-naphthyl, phenanthrenyl, anthracenyl, and pyrenyl; groups formed by combining the above aromatic groups with at least one group selected from chain hydrocarbon groups, alicyclic hydrocarbon groups, and aromatic groups (e.g., benzyl, phenethyl, etc.); and these groups substituted with the substituents described above. In the groups obtained by the above combinations, the chain hydrocarbon groups may be combined to form a divalent group (e.g., an alkanediyl or alkenyl group). The number of carbon atoms in the aromatic group is preferably 6 to 15, more preferably 6 to 12. Specifically, the groups containing aromatic groups are preferably (G-5) to (G-24), (D-4) to (D-14) and (D-36) to (D-47), more preferably (G-8) to (G-18) and (D-4) to (D-14), and even more preferably (G-8), (G-10), (G-13) and (D-12) to (D-14).

[0112] R B2 When it represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, examples of the hydrocarbon group having 1 to 20 carbon atoms which may have a substituent include the above-mentioned R in formula (I): 1 ~R 10 The groups described, R 1 ~R 10 The same description of the preferred hydrocarbon groups having 1 to 20 carbon atoms applies to R B2 A hydrocarbon group having 1 to 20 carbon atoms.

[0113] In a preferred embodiment of the present invention, R B2It is preferably a group containing an aromatic group having 6 to 20 carbon atoms which may have a substituent, and more preferably an aromatic group having 6 to 20 carbon atoms which may have a substituent. Examples of the group containing an aromatic group having 6 to 20 carbon atoms include groups containing aromatic rings such as phenyl, 1-naphthyl, 2-naphthyl, phenanthrenyl, anthracenyl, pyrenyl, benzyl, and phenethyl. The group containing an aromatic group is not particularly limited as long as it is a group containing an aromatic group. It may be an aromatic group or a group composed of the aromatic group and other groups. For example, in addition to the aromatic groups mentioned above, it may be a group in which a linear or branched hydrocarbon group having 1 to 6 carbon atoms (preferably an alkylene group having 1 to 6 carbon atoms) is bonded to the aromatic group (for example, a benzyl group). The number of carbon atoms in the aromatic group is preferably 6 to 15, and more preferably 6 to 12. Examples of substituents that the group containing an aromatic group having 6 to 20 carbon atoms may have include a halogen atom; a nitrile group; a nitro group; an amino group; a hydroxyl group; an alkoxy group having 1 to 14 carbon atoms, such as a methoxy group and an ethoxy group; an aryloxy group having 6 to 14 carbon atoms, such as a phenoxy group, a 1-naphthyloxy group and a 2-naphthyloxy group; a thiol group; an alkylthio group having 1 to 14 carbon atoms, such as a methylthio group and an ethylthio group; an allylthio group; an arylthio group having 6 to 14 carbon atoms, such as a phenylthio group, a 1-naphthylthio group and a 2-naphthylthio group; a thioxy group; an alkylthiooxy group having 1 to 14 carbon atoms, such as a methylthiooxy group and an ethylthiooxy group; and an arylthiooxy group having 6 to 14 carbon atoms, such as a phenylthiooxy group, a 1-naphthylthiooxy group and a 2-naphthylthio group. Silyl; boryl; alkylamino groups having 1 to 14 carbon atoms, such as monomethylamino, dimethylamino, trimethylamino, monoethylamino, diethylamino, and triethylamino; arylamino groups having 6 to 14 carbon atoms, such as monophenylamino and diphenylamino; arylalkylamino groups having 7 to 14 carbon atoms, such as benzylamino; carboxyl; carbamoyl; alkylcarbonyl groups having 2 to 14 carbon atoms, such as acetyl and propionyl; arylcarbonyl groups having 7 to 14 carbon atoms, such as benzoyl, 1-naphthylcarbonyl, and 2-naphthylcarbonyl; alkoxycarbonyl groups having 2 to 14 carbon atoms, such as methoxycarbonyl and ethoxycarbonyl; aryloxycarbonyl groups having 7 to 14 carbon atoms, such as phenoxycarbonyl, 1-naphthyloxycarbonyl, and 2-naphthyloxycarbonyl. When an aromatic group having 6 to 20 carbon atoms has a substituent as described above, the number of carbon atoms of the aromatic group shall be the number of carbon atoms of the group after the substitution.

[0114] R in formula (I) A1 ~R A6 At least one of them represents -C(=O)-OR B3 Base. R A1 ~R A6 At least one of them represents -C(=O)-OR B3When a group is present, the optical properties, solubility in organic solvents, and heat resistance of the compound represented by formula (I) can be improved.

[0115] As R B3 , the above-mentioned R in formula (I) can be cited. 1 The groups described in the above examples, R 1 Wait ~ R 10 The same description of the preferred hydrocarbon groups having 1 to 20 carbon atoms applies to R B3 A hydrocarbon group having 1 to 20 carbon atoms.

[0116] In a preferred embodiment of the present invention, R B3 It may be a linear or branched aliphatic hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and more preferably a linear aliphatic hydrocarbon group having 1 to 20 carbon atoms which may have a substituent. B3 The number of carbon atoms in the moiety is preferably 2-18, more preferably 3-16, and even more preferably 4-15.

[0117] Specific examples of the compound represented by formula (I) include the following.

[0118] (1)R A1 and R A2 、R A3 and R A4 , or R A5 and R A6 One of them represents a hydrogen atom and -C(=O)-OR B3 or both represent -C(=O)-OR B3 The remaining two compounds are groups of formula (i).

[0119] (2)R A1 and R A2 、R A3 and R A4 , or R A5 and R A6 One of them represents a hydrogen atom and -C(=O)-OR B3 or both represent -C(=O)-OR B3 , another 1 represents a group of formula (i), and the remaining 1 represents a group of formula (ii),

[0120] (3)R A1 and R A2 、R A3 and R A4 , or R A5 and R A6 One of them represents a hydrogen atom and -C(=O)-OR B3or both represent -C(=O)-OR B3 , and the other one represents a hydrogen atom, represents a hydrogen atom and -C(=O)-OR B3 or both represent -C(=O)-OR B3 , the remaining 1 represents a group of formula (i),

[0121] (4)R A1 and R A2 、R A3 and R A4 , or R A5 and R A6 One of them represents a hydrogen atom and -C(=O)-OR B3 or both represent -C(=O)-OR B3 The remaining two groups represent the compound of formula (ii)

[0122] (5)R A1 and R A2 、R A3 and R A4 , or R A5 and R A6 One of them represents a hydrogen atom and -C(=O)-OR B3 or both represent -C(=O)-OR B3 , and the other one represents a hydrogen atom, represents a hydrogen atom and -C(=O)-OR B3 or both represent -C(=O)-OR B3 , and the remaining 1 represents a group of formula (ii),

[0123] (6)R A1 and R A2 、R A3 and R A4 , or R A5 and R A6 One of them represents a hydrogen atom and -C(=O)-OR B3 or both represent -C(=O)-OR B3 The remaining two are hydrogen atoms, hydrogen atoms and -C(=O)-OR B3 or both represent -C(=O)-OR B3 Based compounds.

[0124] Specific examples of (4) to (6) in the above-mentioned (1) to (6) include the following compounds.

[0125] Formula I <![CDATA[R A1 and R A2 ]]> <![CDATA[R A3 and R A4 ]]> <![CDATA[R A5 and R A6 ]]> (4a) (a) Formula (ii) Formula (ii) (4b) Formula (ii) (a) Formula (ii) (4c) Formula (ii) Formula (ii) (a) (5a) (a) (a) or (b) Formula (ii) (5b) (a) Formula (ii) (a) or (b) (5c) Formula (ii) (a) (a) or (b) (5d) (a) or (b) (a) Formula (ii) (5e) Formula (ii) (a) or (b) (a) (5f) (a) or (b) Formula (ii) (a) (6a) (a) (a) or (b) (a) or (b) (6b) (a) or (b) (a) (a) or (b) (6c) (a) or (b) (a) or (b) (a)

[0126] In the above table, (a) refers to RA1 and R A2 Combination of R A3 and R A4 A combination of, or R A5 and R A6 The two groups in the combination represent a hydrogen atom and -C(=O)-OR B3 or both represent -C(=O)-OR B3 (b) means that both of the two groups represent hydrogen atoms, represent hydrogen atoms and -C(=O)-OR B3 or both represent -C(=O)-OR B3 In addition, the above (a) or (b) is preferably (a), and more preferably both are -C(=O)-OR B3 Furthermore, the above (a) are preferably -C(=O)-OR B3 base.

[0127] In a preferred embodiment of the present invention, from the viewpoint of optical properties, solubility in organic solvents, and heat resistance of the compound represented by formula (I), the compound represented by formula (I) is preferably A1 and R A2 、R A3 and R A4 , and R A5 and R A6 Each independently represents -C(=O)-OR B3 or a group represented by the above formula (ii), wherein R A1 and R A2 、R A3 and R A4 , or R A5 and R A6 At least one of them represents -C(=O)-OR B3 Based compounds.

[0128] In a more preferred embodiment of the present invention, from the viewpoint of the optical properties, solubility in organic solvents, and heat resistance of the compound represented by formula (I), the compound represented by formula (I) is preferably:

[0129] R in formula (I) A1 and R A2 、R A3 and R A4 , or R A5 and R A6 2 of them represent the group represented by the above formula (ii), and R in formula (ii) B2represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent (preferably a group containing an aromatic group having 6 to 20 carbon atoms which may have a substituent, more preferably an aromatic group having 6 to 20 carbon atoms which may have a substituent), and the remaining one represents -C(=O)-OR B3 Ji, R B3 A compound representing a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent (preferably an aliphatic hydrocarbon group having 1 to 20 carbon atoms which may have a substituent), or

[0130] R in formula (I) A1 and R A2 、R A3 and R A4 , or R A5 and R A6 One of them represents a group represented by the above formula (ii), and R in formula (ii) B2 represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent (preferably a group containing an aromatic group having 6 to 20 carbon atoms which may have a substituent, more preferably an aromatic group having 6 to 20 carbon atoms which may have a substituent), and the remaining two represent -C(=O)-OR B3 Ji, R B3 A compound representing a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent (preferably an aliphatic hydrocarbon group having 1 to 20 carbon atoms which may have a substituent), or

[0131] R in formula (I) A1 and R A2 、R A3 and R A4 , or R A5 and R A6 Represents -C(=O)-OR B3 Ji, R B3 A compound representing a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent (preferably an aliphatic hydrocarbon group having 1 to 20 carbon atoms which may have a substituent).

[0132] In a preferred embodiment of the present invention, the compound represented by formula (I) is 1 ~R 10 Represents a hydrogen atom, R B2 and R B3 Each independently represents a compound of a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.

[0133] In a preferred embodiment of the present invention, when the solubility of the compound represented by formula (I) in cyclohexanone is measured, it preferably exhibits a solubility of 0.5% or more, more preferably 0.8% or more, even more preferably 1.0% or more, and even more preferably 1.2% or more. The solubility can be measured by the method described in the Examples.

[0134] In a preferred embodiment of the present invention, the thermal decomposition temperature of the compound represented by formula (I) measured using TG-DTA is preferably 300°C or higher, more preferably 305°C or higher, and even more preferably 308°C or higher. The thermal decomposition temperature can be measured, for example, by the method described in the Examples. In another preferred embodiment of the present invention, the thermal decomposition temperature is preferably 320°C or higher, more preferably 330°C or higher.

[0135] In a preferred embodiment of the present invention, the compound represented by formula (I) has a maximum absorption wavelength λ of preferably 520 to 600 nm, more preferably 530 to 595 nm, and even more preferably 540 to 590 nm when an N,N-dimethylformamide solution of the compound (e.g., a concentration of 0.01 g / L) is used as a measurement sample and an absorption spectrum is measured using an ultraviolet-visible spectrophotometer within a wavelength range of 800 to 300 nm. max [nm]. Here, the λ max When compound (I) contains other compounds as impurities, the λ max The value may be different from the λ of the compound (I) with high purity. max In the present invention, in the colorant containing the compound represented by formula (I) described later, it is also preferred to satisfy the above-mentioned λ max .

[0136] In a preferred embodiment of the present invention, the maximum absorption wavelength λ of the absorption spectrum of the compound represented by formula (I) measured in the same manner as above is max When the absorption spectrum obtained by adjusting the absorbance value at [nm] to 2 is converted into a transmission spectrum, the average transmittance [%] in the wavelength range of 500 to 600 nm in the converted transmission spectrum is preferably 35% or less, more preferably 30% or less, and even more preferably 20% or less. Furthermore, in the converted transmission spectrum obtained in the same manner as above, the average transmittance [%] in the wavelength range of 630 nm and above is preferably 91% or more, more preferably 93% or more, and even more preferably 94% or more. The lower the average transmittance in the wavelength range of 500 to 600 nm and the greater the minimum transmittance above 630 nm, the more suitable it is for a red filter.

[0137] Furthermore, in the above-mentioned transmission spectrum, the average transmittance [%] in the wavelength range of 430-530 nm is preferably 35% or less, more preferably 30% or less, and even more preferably 20% or less. The average transmittance [%] in the wavelength range of 600 nm or more is preferably 91% or more, more preferably 93% or more, and even more preferably 95% or more. The lower the average transmittance in the wavelength range of 430-530 nm and the greater the minimum transmittance above 600 nm, the more suitable the filter is for use as a red color filter.

[0138] Here, the average transmittance [%] also applies. When compound (I) contains other compounds as impurities, the average transmittance of the mixture containing the impurities may differ from the average transmittance of the highly pure compound (I). In the present invention, the colorant containing the compound represented by formula (I) described later also preferably satisfies the above-mentioned average transmittance [%] in the wavelength range of 430 to 530 nm.

[0139] [Method for producing the compound represented by formula (I) or formula (IV)]

[0140] The method for producing compound (I) is not particularly limited. In a preferred embodiment of the present invention, compound (I) is preferably produced by the production method of the present invention described below.

[0141] The present invention also provides a method for producing the compound represented by formula (IV).

[0142]

[0143] [In formula (VI),

[0144] R 1’ ~R 10’ and R D1 ~R D6 and R in the formula (IV), formula (Vi) and (V-ii) described later 1’ ~R 10’ and R D1 ~R D6 has the same meaning.]

[0145] It should be noted that R in formula (VI) 1’ ~R 10’ R in formula (I) can be 1 ~R 10 , R in formula (VI) D1 ~R D6 R in formula (I) can be A1 ~R A6 In this case, the compound represented by formula (VI) corresponds to the compound represented by formula (I).

[0146] A method for producing a compound represented by formula (VI), comprising reacting a compound represented by formula (IV) with a compound represented by formula (Vi) or a compound represented by formula (V-ii) in the presence of a catalyst.

[0147]

[0148] [In formula (IV),

[0149] R 1’ 、R 4’ 、R 7’ 、R 8’ 、R 9’ and R 10’ Each independently represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, a halogen atom, a hydroxyl group, or a carboxyl group, wherein the methylene group contained in the hydrocarbon group may be substituted with -O-, -CO-, or -N(R E1 )-,R 4’ and R 7’ and / or R 7’ and R 10’ can bond to each other to form a ring,

[0150] R E1 each independently represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent,

[0151] Z 1 and Z 2 each independently represents a bromine atom or an iodine atom,

[0152] R D1 and R D2 , and R D5 and R D6 Each independently represents a hydrogen atom, -C(=O)-OR B3 a group represented by formula (i), or a group represented by formula (iii),

[0153]

[0154] [In formula (i), * represents D1 and R D2 , or R D5 and R D6 bonding sites of

[0155]

[0156] [In formula (iii),

[0157] R E2 represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent,

[0158] * indicates the same as R D1 and R D2 , or R D5 and R D6 The bonding site of ].

[0159]

[0160] [In formulas (Vi) and (V-ii),

[0161] R 2’ 、R 3’ 、R 5’ and R 6’ Each independently represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, a halogen atom, a hydroxyl group, or a carboxyl group, wherein the methylene group contained in the hydrocarbon group may be substituted with -O-, -CO-, or -N(R E1 )-,R 2’ and R 5’ and / or R 3’ and R 6’ can bond to each other to form a ring,

[0162] R E1 each independently represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent,

[0163] R D3 and R D4 Each independently represents a hydrogen atom, -C(=O)-OR B3 a group represented by formula (i), or a group represented by formula (iii),

[0164] A 1 ~A 4 Each independently represents a hydroxyl group, a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, or -OR E3 base,

[0165] R E3 each independently represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent,

[0166] A 1 and A 2 and / or A 3 and A 4 Indicates -OR E3 Base time, 2-OR E3 The groups can bond to each other to form -OR E4 -represented by a divalent group, R E4 It is a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.]

[0167] As R in formula (IV) 1’ 、R 4’ 、R 7’ 、R 8’ 、R 9’ and R 10’ , and R in formula (Vi) and (V-ii) 2’ 、R 3’ 、R 5’ and R 6’ Examples of R in formula (I) can also be cited. 1 ~R 10 The groups described as R E1’ Examples of R in formula (I) can also be cited. B1 The groups described.

[0168] Z 1 and Z 2 Each independently represents a bromine atom or an iodine atom, preferably a bromine atom.

[0169] As R in formula (iii) E2 Examples of R in formula (I) can also be cited. B2 Examples recorded.

[0170] In formula (Vi) and (V-ii), A 1 ~A 4 Each independently represents a hydroxyl group, a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, or -OR E3 Ji, R E3 Each independently represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent. Examples of the hydrocarbon group having 1 to 20 carbon atoms which may have a substituent include those mentioned above for R in formula (I). 1 The groups exemplified by the above. 1 and A 2 and / or A 3 and A 4 Indicates -OR E3 Base time, 2-OR E3 The groups can bond to each other to form -OR E4 -represented by a divalent group, R E4 is a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent. E4 The hydrocarbon group having 1 to 20 carbon atoms which may have a substituent may include the above-mentioned R in formula (I). 1 A divalent group in which one hydrogen atom is substituted as a bonding site in the groups exemplified by , etc.

[0171] In a preferred embodiment of the present invention, R in formula (IV) D1and R D2 、R D5 and R D6 , and R in formula (Vi) or (V-ii) D3 and R D4 Among these three combinations, at least one combination represents a hydrogen atom and -C(=O)-OR B3 or both represent -C(=O)-OR B3 When the groups are present, it is preferred that at least one combination represents -C(=O)-OR B3 In this case, the compound (I) can be produced with a high selectivity and the contamination of by-products can be suppressed, which is preferable.

[0172] In addition, it is known that when compound (VI) is designed such that R in formula (IV) D1 and R D2 、R D5 and R D6 , and R in formula (Vi) or (V-ii) D3 and R D4 When the structures have different groups in the above-mentioned compound (I), the production method of the present invention can produce the compound (I) having the desired structure at high purity as designed without performing complicated purification operations.

[0173] It should be noted that, for example, by referring to the method described in Japanese Patent Application Laid-Open No. 2022-126586, after preparing a compound having a polyester skeleton, reacting a maleic anhydride compound, and further reacting an amine compound, the compound represented by formula (I) can also be produced. However, it is known that when producing the compound represented by formula (I) by such a reaction, it is particularly difficult to convert R in formula (IV) into D1 and R D2 、R D5 and R D6 , and R in formula (Vi) or (V-ii) D3 and R D4 It is very difficult to separate and purify the compounds having different substituents by using a column or the like. A1 ~R A6 At least one of them represents -C(=O)-OR B3 Base, and then, in R A1 and R A2 、R A3 and R A4 , or R A5 and R A6 At least one of the B2In the case of a group represented by formula (ii) containing an optionally substituted aromatic group having 6 to 20 carbon atoms, the presence of the aromatic group having 6 to 20 carbon atoms makes it very difficult to separate and purify compound (I) from other by-products using a column or the like.

[0174] The method for producing the compound represented by the above formula (VI) comprises the step of reacting the compound (IV) with the compound (Vi) or the compound (V-ii) in the presence of a catalyst, a phosphine ligand, and a base.

[0175] The catalyst is not particularly limited as long as it can promote the reaction between compound (IV) and compound (Vi) or compound (V-ii). Examples thereof include tris(dibenzylideneacetone)dipalladium(0), bis(dibenzylideneacetone)palladium(0), palladium(II) acetate, palladium(II) chloride, sodium tetrachloropalladate(II), palladium(II) chloride (π-cinnamyl) (dimer), allylpalladium(II) chloride dimer, bis(benzonitrile)dichloropalladium(II), and bis(acetonitrile)dichloropalladium(II). From the viewpoint of suppressing by-products, bis(dibenzylideneacetone)palladium(0) is more preferred. From the viewpoint of high reactivity and suppression of impurities, the amount of the catalyst used is preferably 0.1 to 30 mol%, more preferably 0.5 to 20 mol%, and even more preferably 1 to 10 mol% relative to compound (IV).

[0176] Examples of the phosphine ligand include tributylphosphine, tri-tert-butylphosphine, tricyclohexylphosphine, triphenylphosphine, tri(o-tolyl)phosphine, tri(m-tolyl)phosphine, tri(p-tolyl)phosphine, tri(3-methoxyphenyl)phosphine, tri[3,5-bis(trifluoromethyl)phenyl]phosphine, ethyldiphenylphosphine, tri(2,6-dimethoxyphenyl)phosphine, tri(4-fluorophenyl), diphenylpropylphosphine, di-tert-butylphenylphosphine, tri(2-furyl)phosphine, tri(2-thiophene)phosphine, and the like. 1-[2-(di-tert-butylphosphino)phenyl]-3,5-diphenyl-1H-pyrazole, (4-dimethylaminophenyl)di-tert-butylphosphine, 2-(di-tert-butylphosphino)biphenyl, di-tert-butyl(1,1-diphenyl-1-propen-2-yl)phosphine, isopropyldiphenylphosphine, 2-(dicyclohexylphosphino)-2'-(dimethylamino)biphenyl, 2-(Dicyclohexylphosphino)biphenyl, 2-(Diphenylphosphino)biphenyl, 2-dicyclohexylphosphino-2'-methylbiphenyl, 2-dicyclohexylphosphino-2',6'-diisopropoxybiphenyl, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, dicyclohexyl(1-methyl-2,2-diphenylcyclopropyl)phosphine, di-tert-butyl(2',4',6'-triisopropyl-3,6-dimethoxy-[1,1'-biphenyl]-2-yl) Monodentate phosphine ligands such as phosphine, 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl, 2-diphenylphosphino-2'-(N,N-dimethylamino)biphenyl, 2-di-tert-butylphosphino-2',4',6'-triisopropylbiphenyl, dicyclohexyl(2',4',6'-triisopropyl-3,6-dimethoxy-[1,1'-biphenyl]-2-yl)phosphine, and dicyclohexyl(1,1-diphenyl-1-propen-2-yl)phosphine,

[0177] Bis(diphenylphosphino)methane, 1,2-bis(diphenylphosphino)ethane, 1,3-bis(diphenylphosphino)propane, 1,4-bis(diphenylphosphino)butane, 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl, 4,5-bis(dicyclohexylphosphino)-9,9-dimethylxanthene, 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene, 1',2'-bis[bis(3,5-dimethylphenyl)phosphino]-1, The bidentate phosphine ligands such as 1'-biphenyl, 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene, 1,3-bis(diphenylphosphino)propane, 1,1'-bis(di-tert-butylphosphino)ferrocene, bis[2-(diphenylphosphino)phenyl]ether, 1,1'-bis(diisopropylphosphino)ferrocene, and 1,1'-bis(diphenylphosphino)ferrocene are preferably monodentate phosphine ligands, more preferably tributylphosphine, tri-tert-butylphosphine, and tricyclohexylphosphine, and most preferably tricyclohexylphosphine are preferred.

[0178] From the viewpoint of high reactivity and suppression of impurities, the amount of the phosphine ligand used is preferably 0.2 to 60 mol %, more preferably 1 to 40 mol %, and even more preferably 2 to 20 mol % relative to compound (IV).

[0179] As the above-mentioned base, hydroxides, carbonates, bicarbonates, phosphates, carboxylates, alkoxides, etc. of alkali metals or alkaline earth metals as inorganic bases can be mentioned. Here, the form of the base that can be used can be anhydride form or hydrate form. Preferably, hydroxides, carbonates, bicarbonates, phosphates, and carboxylates of alkali metals or alkaline earth metals are mentioned, and carbonates and phosphates of alkali metals or alkaline earth metals are more preferred. As the alkali metal or alkaline earth metal salt, lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate, calcium carbonate, barium carbonate, lithium phosphate, sodium phosphate, potassium phosphate are preferred, and sodium carbonate, potassium carbonate, and potassium phosphate are more preferred.

[0180] From the viewpoint of high reactivity and suppression of impurities, the amount of the base used is preferably 100 to 5000 mol %, more preferably 200 to 3000 mol %, and even more preferably 500 to 2000 mol % relative to compound (IV).

[0181] When compound (IV) and compound (Vi) or compound (V-ii) are reacted in the presence of a catalyst, these compounds can generally be dissolved in a solvent and mixed, and then heated at a reaction temperature of, for example, 40 to 250° C., preferably 100 to 200° C., and more preferably 150 to 200° C., to thereby react these compounds to produce the compound of formula (VI). The reaction time can be appropriately determined depending on the reaction temperature, but is preferably 1 to 100 hours, more preferably 5 to 80 hours, and even more preferably 10 to 50 hours.

[0182] Colorant

[0183] The present invention also provides a colorant comprising a compound represented by formula (I). The colorant is also referred to as colorant (I), and colorant (I) at least comprises a compound represented by formula (I) of the present invention. Colorant (I) is a reagent that can be used as a raw material when manufacturing, for example, a color filter forming composition. When the amount of by-products during the manufacture of compound (I) contained in the colorant is large, the optical properties of compound (I) are sometimes impaired, and it is difficult to obtain the effect when the colorant is used in a color filter, etc. However, when compound (I) is manufactured, in the colorant comprising the compound (I), the amount of by-products having a structure similar to compound (I) is very small. The colorant is a red colorant. It should be noted that when colorant (I) is used in a resin composition, colorant (I) can be used in combination with other colorants, specifically, a yellow colorant and an orange colorant can be used in combination.

[0184] Examples of by-products having a structure similar to that of compound (I) include compounds represented by formula (X).

[0185]

[0186] [In formula (X),

[0187] R X1 and R X2 For example, for R in formula (I) A1 ~R A6 As defined,

[0188] R 1 ~R 10 and R A1 ~R A6 As for R in formula (I) 1 ~R 10 and R A1 ~R A6 as defined].

[0189] The compound represented by formula (X) is a compound not included in the compound represented by formula (I). In a preferred embodiment of the colorant containing compound (I), from the viewpoint of the optical properties of the colorant, the amount of the compound represented by formula (X) in the colorant is preferably 0 to 10% by mass, more preferably 0 to 5% by mass, further preferably 0 to 3% by mass, and even more preferably 0 to 2% by mass. In particular, R A1 and R A2 、R A3 and R A4 , or R A5 and R A6 At least one of the B2 In the case of a group represented by formula (ii) containing an aromatic group having 6 to 20 carbon atoms which may have a substituent, it is extremely difficult to purify compound (I) from a mixture containing compound (I) and compound (X).

[0190] From the viewpoint of the optical properties of the colorant, the colorant (I) containing the compound represented by formula (I) preferably contains 90% by mass or more, more preferably 93% by mass or more, further preferably 95% by mass or more, still further preferably 98% by mass or more, and particularly preferably 99% by mass or more of the compound represented by formula (I), based on the total amount of the colorant.

[0191] [Composition containing a compound represented by formula (I)]

[0192] The present invention also provides a resin composition comprising the compound represented by formula (I) and an alkali-soluble resin. Furthermore, the present invention also provides a resin composition comprising the colorant of the present invention and an alkali-soluble resin. This resin composition is a colored resin composition.

[0193] (Alkali-soluble resin)

[0194] The resin composition of the present invention preferably contains an alkali-soluble resin. The alkali-soluble resin is not particularly limited as long as it is different from a thermoplastic resin and can be used in the formation of a photoresist, but an alkali-soluble resin having a carboxylic acid is preferred. Alkalized positive resins are also referred to as resins (B). Examples of resins (B) include the following resins [K1] to [K6].

[0195] Resin [K1]: A copolymer comprising structural units derived from at least one type (a) selected from unsaturated carboxylic acids and unsaturated carboxylic anhydrides (hereinafter sometimes referred to as "(a)"), and structural units derived from a monomer (b) having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b)");

[0196] Resin [K2]: a copolymer having a structural unit derived from (a), a structural unit derived from (b), and a structural unit derived from a monomer (c) copolymerizable with (a) (which is different from (a) and (b)) (hereinafter sometimes referred to as "(c)");

[0197] Resin [K3]: a copolymer having a structural unit derived from (a) and a structural unit derived from (c);

[0198] Resin [K4]: a copolymer having a structural unit obtained by adding (b) to a structural unit derived from (a) and a structural unit derived from (c);

[0199] Resin [K5]: a copolymer having a structural unit obtained by adding (a) to a structural unit derived from (b) and a structural unit derived from (c);

[0200] Resin [K6]: A copolymer having a structural unit obtained by adding (a) to a structural unit derived from (b) and further adding a carboxylic acid anhydride, and a structural unit derived from (c).

[0201] Examples of the monomer (a) include acrylic acid, methacrylic acid, crotonic acid, and unsaturated monocarboxylic acids such as o-, m-, and p-vinylbenzoic acid;

[0202] 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;

[0203] Bicyclic unsaturated compounds containing a carboxyl group, such as methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo[2.2.1]hept-2-ene, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene, 5-carboxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-carboxy-6-methylbicyclo[2.2.1]hept-2-ene, and 5-carboxy-6-ethylbicyclo[2.2.1]hept-2-ene;

[0204] Carboxylic acid anhydrides such as anhydrides of the above-mentioned unsaturated dicarboxylic acids excluding fumaric acid and mesaconic acid;

[0205] Unsaturated mono-(meth)acryloyloxyalkyl) esters of di- or higher-valent polycarboxylic acids such as mono-(2-(meth)acryloyloxyethyl) succinate and mono-(2-(meth)acryloyloxyethyl phthalate;

[0206] Unsaturated acrylic acid esters containing a hydroxyl group and a carboxyl group in the same molecule, such as α-(hydroxymethyl)acrylate, etc.

[0207] Among these, acrylic acid, methacrylic acid, maleic anhydride, and the like are preferred from the viewpoint of copolymerization reactivity and solubility of the resulting resin in an aqueous alkali solution.

[0208] In this specification, "(meth)acrylic acid" refers to at least one selected from acrylic acid and methacrylic acid. The expressions "(meth)acryloyl" and "(meth)acrylate" also have the same meaning.

[0209] Monomer (b) is a polymerizable compound having a cyclic ether structure having 2 to 4 carbon atoms (e.g., at least one selected from an oxirane ring, an oxetane ring, and a tetrahydrofuran ring (oxolane ring)) and an ethylenically unsaturated bond. Monomer (b) is preferably a monomer having a cyclic ether structure having 2 to 4 carbon atoms and a (meth)acryloyloxy group.

[0210] Examples of monomer (b) include monomers having an oxirane group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "monomer (b1)"), monomers having an oxetane group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "monomer (b2)"), and monomers having a tetrahydrofuran group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "monomer (b3)").

[0211] Examples of the monomer (b1) include monomers having a structure obtained by epoxidizing an unsaturated aliphatic hydrocarbon (hereinafter sometimes referred to as "monomer (b1-1)") and monomers having a structure obtained by epoxidizing an unsaturated alicyclic hydrocarbon (hereinafter sometimes referred to as "monomer (b1-2)").

[0212] As monomer (b1-1), a monomer having a glycidyl group and an ethylenically unsaturated bond is preferred. As monomer (b1-1), specifically, glycidyl (meth)acrylate, β-methyl glycidyl (meth)acrylate, β-ethyl glycidyl (meth)acrylate, glycidyl vinyl ether, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether, α-methyl-o-vinylbenzyl glycidyl ether, α-methyl-m-vinylbenzyl glycidyl ether, α-methyl-p-vinylbenzyl glycidyl ether, 2,3-bis( styrene, 2,4-bis(glycidyloxymethyl)styrene, 2,5-bis(glycidyloxymethyl)styrene, 2,6-bis(glycidyloxymethyl)styrene, 2,3,4-tris(glycidyloxymethyl)styrene, 2,3,5-tris(glycidyloxymethyl)styrene, 2,3,6-tris(glycidyloxymethyl)styrene, 3,4,5-tris(glycidyloxymethyl)styrene, 2,4,6-tris(glycidyloxymethyl)styrene, and the like.

[0213] Examples of monomers (b1-2) include vinylcyclohexene monoxide, 1,2-epoxy-4-vinylcyclohexane (e.g., Celloxide (registered trademark) 2000; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., CYCLOMER (registered trademark) A400; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., CYCLOMER (registered trademark) M100; manufactured by Daicel Corporation), compounds represented by formula (BI) and compounds represented by formula (BII).

[0214]

[0215] In formula (BI) and formula (BII), R a and R b Each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, wherein the hydrogen atom contained in the alkyl group may be substituted by a hydroxyl group.

[0216] X a and X b Independently represent single bonds, *-R c -,*-R c-O-, *-R c -S- or *-R c -NH-.

[0217] R c It represents an alkanediyl group having 1 to 6 carbon atoms.

[0218] * indicates the bonding site with O.

[0219] Examples of the alkyl group having 1 to 4 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, and a tert-butyl group.

[0220] Examples of the alkyl group in which a hydrogen atom is substituted by a hydroxy group include a hydroxymethyl group, a 1-hydroxyethyl group, a 2-hydroxyethyl group, a 1-hydroxypropyl group, a 2-hydroxypropyl group, a 3-hydroxypropyl group, a 1-hydroxy-1-methylethyl group, a 2-hydroxy-1-methylethyl group, a 1-hydroxybutyl group, a 2-hydroxybutyl group, a 3-hydroxybutyl group, and a 4-hydroxybutyl group.

[0221] As R a and R b , preferably, 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.

[0222] Examples of the alkanediyl group include a methylene group, an ethylene group, a propane-1,2-diyl group, a propane-1,3-diyl group, a butane-1,4-diyl group, a pentane-1,5-diyl group, and a hexane-1,6-diyl group.

[0223] As X a and X b , preferably include a single bond, methylene, ethylene, *-CH2-O- group (* indicates a bonding site with O), *-CH2CH2-O- group, more preferably include a single bond, *-CH2CH2-O- group (* indicates a bonding site with O.).

[0224] The compound represented by formula (BI) and the compound represented by formula (BII) may be used alone or in combination. When used in combination, the molar ratio of the compound represented by formula (BI) to the compound represented by formula (BII) is preferably 5:95 to 95:5, more preferably 10:90 to 90:10, and even more preferably 20:80 to 80:20.

[0225] As the monomer (b2) having an oxetane group and an ethylenically unsaturated bond, a monomer having an oxetane group and a (meth)acryloyloxy group is more preferred. Examples of the monomer (b2) include 3-methyl-3-(meth)acryloyloxymethyloxetane, 3-ethyl-3-(meth)acryloyloxymethyloxetane, 3-methyl-3-(meth)acryloyloxyethyloxetane, and 3-ethyl-3-(meth)acryloyloxyethyloxetane.

[0226] As the monomer (b3) having a tetrahydrofuranyl group and an ethylenically unsaturated bond, a monomer having a tetrahydrofuranyl group and a (meth)acryloyloxy group is more preferred. Examples of the monomer (b3) include tetrahydrofurfuryl acrylate (e.g., Viscoat V#150, manufactured by Osaka Organic Chemical Industry Co., Ltd.) and tetrahydrofurfuryl methacrylate.

[0227] Examples of the monomer (c) include methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, sec-butyl (meth)acrylate, tert-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, dodecyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, cyclopentyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, tricyclo[5.2.1.0](meth)acrylate, 2,6 ] decane-8-yl ester (in this technical field, it is commonly known as "dicyclopentanyl (meth)acrylate". In addition, it is sometimes called "tricyclodecyl (meth)acrylate"), tricyclo[5.2.1.0 2,6 ] decane-9-yl ester, (meth) acrylic acid tricyclo[5.2.1.0 2,6 ] decen-8-yl ester (in this technical field, it is commonly known as "dicyclopentenyl (meth)acrylate"), tricyclo (meth)acrylate [5.2.1.0 2,6 (Meth)acrylates such as decen-9-yl (meth)acrylate, dicyclopentyloxyethyl (meth)acrylate, isobornyl (meth)acrylate, adamantyl (meth)acrylate, allyl (meth)acrylate, propargyl (meth)acrylate, phenyl (meth)acrylate, naphthyl (meth)acrylate, and benzyl (meth)acrylate;

[0228] (Meth)acrylates containing a hydroxyl group, such as 2-hydroxyethyl (meth)acrylate and 2-hydroxypropyl (meth)acrylate;

[0229] dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate, and diethyl itaconate;

[0230] Bicyclo[2.2.1]hept-2-ene, 5-methylbicyclo[2.2.1]hept-2-ene, 5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxybicyclo[2.2.1]hept-2-ene, 5-hydroxymethylbicyclo[2.2.1]hept-2-ene, 5-(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5-methoxybicyclo[2.2.1]hept-2-ene, 5-ethoxybicyclo[2.2.1]hept-2-ene, 5,6-dihydroxybicyclo[2.2.1]hept-2-ene, 5,6-bis(hydroxymethyl)bicyclo[2.2.1]hept-2-ene, 5,6-bis(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5,6-dimethoxybicyclo[2.2.1]hept-2-ene Bicyclic unsaturated compounds such as cyclo[2.2.1]hept-2-ene, 5,6-diethoxybicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxymethyl-5-methylbicyclo[2.2.1]hept-2-ene, 5-tert-butoxycarbonylbicyclo[2.2.1]hept-2-ene, 5-cyclohexyloxycarbonylbicyclo[2.2.1]hept-2-ene, 5-phenoxycarbonylbicyclo[2.2.1]hept-2-ene, 5,6-bis(tert-butoxycarbonyl)bicyclo[2.2.1]hept-2-ene, and 5,6-bis(cyclohexyloxycarbonyl)bicyclo[2.2.1]hept-2-ene;

[0231] dicarbonyl imide derivatives such as N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimidobenzoate, N-succinimidyl-4-maleimidobutyrate, N-succinimidyl-6-maleimidohexanoate, N-succinimidyl-3-maleimidopropionate and N-(9-acridinyl)maleimide;

[0232] Aromatic compounds containing vinyl groups such as styrene, o-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene and p-methoxystyrene; nitriles containing vinyl groups such as (meth)acrylonitrile; halogenated hydrocarbons such as vinyl chloride and vinylidene chloride; amides containing vinyl groups such as (meth)acrylamide; esters such as vinyl acetate; dienes such as 1,3-butadiene, isoprene and 2,3-dimethyl-1,3-butadiene, etc.

[0233] Among these, styrene, vinyltoluene, tricyclo[5.2.1.0 2,6 ] decane-8-yl ester, (meth) acrylic acid tricyclo[5.2.1.0 2,6 ] decane-9-yl ester, (meth) acrylic acid tricyclo[5.2.1.0 2,6]Decen-8-yl ester, (meth) acrylic acid tricyclo[5.2.1.0 2,6 ]decen-9-yl ester, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo[2.2.1]hept-2-ene and benzyl (meth)acrylate, etc.

[0234] In the resin [K1], the ratio of the structural units derived from each monomer in all the structural units constituting the resin [K1] is preferably:

[0235] Structural units derived from (a): 2 to 60 mol%

[0236] Structural units derived from (b): 40 to 98 mol%

[0237] More preferably:

[0238] Structural units derived from (a): 10 to 50 mol%

[0239] Structural units derived from (b): 50 to 90 mol%.

[0240] When the ratio of the structural unit of the resin [K1] is within the above range, the storage stability of the resin composition, the developability when forming a colored pattern, and the solvent resistance of the obtained optical filter tend to be excellent.

[0241] Resin [K1] can be produced, for example, by referring to the method described in the document "Experimental Methods for Polymer Synthesis" (written by Takayuki Otsu and published by Kagaku Doujin Co., Ltd., 1st edition, 1st printing, published on March 1, 1972) and the cited documents described in the document.

[0242] Specifically, the following method can be used: a predetermined amount of (a) and (b), a polymerization initiator, and a solvent are placed in a reaction vessel, and a deoxygenated atmosphere is formed, for example, by replacing oxygen with nitrogen. The mixture is then heated and kept warm while stirring. It should be noted that the polymerization initiator and solvent used herein are not particularly limited, and those commonly used in this field can be used. For example, polymerization initiators include azo compounds (2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), etc.) and organic peroxides (benzoyl peroxide, etc.). As a solvent, any solvent that dissolves the monomers can be used, and examples thereof include the solvents described below as solvents for the resin composition of the present invention.

[0243] It should be noted that the copolymer obtained may be used directly as the solution after the reaction, or as a concentrated or diluted solution, or as a solid (powder) obtained by reprecipitation or the like. In particular, by using the solvent contained in the resin composition of the present invention as the solvent during the polymerization, the solution after the reaction can be used directly to prepare the resin composition of the present invention, thereby simplifying the production process of the resin composition of the present invention.

[0244] In the resin [K2], the ratio of the structural units derived from each monomer in all the structural units constituting the resin [K2] is preferably:

[0245] Structural units derived from (a): 2 to 45 mol%

[0246] Structural units derived from (b): 2 to 95 mol%

[0247] Structural units derived from (c): 1 to 65 mol%

[0248] More preferably:

[0249] Structural units derived from (a): 5 to 40 mol%

[0250] Structural units derived from (b): 5 to 80 mol%

[0251] Structural units derived from (c): 5 to 60 mol%.

[0252] When the ratio of the structural units of the resin [K2] is within the above range, the storage stability of the resin composition, the developability when forming a colored pattern, and the obtained solvent resistance, heat resistance, and mechanical strength tend to be excellent.

[0253] The resin [K2] can be produced, for example, in the same manner as described as the method for producing the resin [K1].

[0254] In the resin [K3], the ratio of the structural units derived from each monomer in all the structural units constituting the resin [K3] is preferably:

[0255] Structural units derived from (a): 2 to 60 mol%

[0256] Structural units derived from (c): 40 to 98 mol%

[0257] More preferably:

[0258] Structural units derived from (a): 10 to 50 mol%

[0259] Structural units derived from (c): 50 to 90 mol%.

[0260] The resin [K3] can be produced, for example, in the same manner as described as the method for producing the resin [K1].

[0261] Resin [K4] can be produced by obtaining a copolymer of (a) and (c), and adding a cyclic ether having 2 to 4 carbon atoms contained in (b) to the carboxylic acid and / or carboxylic anhydride contained in (a).

[0262] First, a copolymer of (a) and (c) is produced in the same manner as described for the production of resin [K1]. In this case, the ratio of the structural units derived from each monomer is preferably the same as that exemplified for resin [K3].

[0263] Next, the cyclic ether having 2 to 4 carbon atoms contained in (b) is reacted with a portion of the carboxylic acid and / or carboxylic anhydride derived from (a) in the above copolymer.

[0264] After producing the copolymer of (a) and (c), the atmosphere in the flask is replaced from nitrogen to air, and (b), a reaction catalyst for carboxylic acid or carboxylic anhydride and cyclic ether (e.g., tris(dimethylaminomethyl)phenol, etc.), and a polymerization inhibitor (e.g., hydroquinone, etc.) are placed in the flask and reacted at, for example, 60 to 130° C. for 1 to 10 hours to produce resin [K4].

[0265] The amount of (b) used is preferably 5 to 80 mol, more preferably 10 to 75 mol, relative to 100 mol of (a). Within this range, the storage stability of the colored resin composition, the developability during pattern formation, and the balance between the solvent resistance, heat resistance, mechanical strength, and sensitivity of the resulting pattern tend to be improved. Because cyclic ethers have high reactivity and are less likely to leave unreacted (b), (b1) is preferred as (b) used in resin [K4], and (b1-1) is more preferred.

[0266] The amount of the reaction catalyst used is preferably 0.001 to 5 parts by mass relative to 100 parts by mass of the total amount of (a), (b) and (c). The amount of the polymerization inhibitor used is preferably 0.001 to 5 parts by mass relative to 100 parts by mass of the total amount of (a), (b) and (c).

[0267] The reaction conditions such as the feeding method, reaction temperature and time can be appropriately adjusted in consideration of the production equipment, the calorific value based on the polymerization, etc. In addition, the feeding method and reaction temperature can be appropriately adjusted in consideration of the production equipment, the calorific value based on the polymerization, etc., similarly to the polymerization conditions.

[0268] As a first step, a copolymer of (b) and (c) is obtained for resin [K5] in the same manner as for the production of resin [K1]. As described above, the obtained copolymer may be used as is, after the reaction, as a concentrated or diluted solution, or as a solid (powder) obtained by reprecipitation or the like.

[0269] The ratios of the structural units derived from (b) and (c) relative to the total number of moles of all structural units constituting the above-mentioned copolymer are preferably:

[0270] Structural units derived from (b): 5 to 95 mol%,

[0271] Structural units derived from (c): 5 to 95 mol%

[0272] More preferably:

[0273] Structural units derived from (b): 10 to 90 mol%

[0274] Structural units derived from (c): 10 to 90 mol%.

[0275] Furthermore, resin [K5] can be obtained by reacting the carboxylic acid or carboxylic anhydride contained in (a) with the cyclic ether derived from (b) contained in the copolymer of (b) and (c) under the same conditions as those in the method for producing resin [K4].

[0276] The amount of (a) reacted with the copolymer is preferably 5 to 80 mol per 100 mol of (b). (b) is preferably (b1), and more preferably (b1-1), as the (b) used in the resin [K5], because the cyclic ether has high reactivity and is less likely to leave unreacted (b).

[0277] Resin [K6] is obtained by further reacting resin [K5] with carboxylic acid anhydride. Carboxylic acid anhydride is reacted with hydroxyl groups generated by the reaction of cyclic ether with carboxylic acid or carboxylic acid anhydride.

[0278] Examples of the carboxylic anhydride include maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, and 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride. The amount of the carboxylic anhydride used is preferably 0.5 to 1 mol per 1 mol of (a).

[0279] Specific examples of the alkali-soluble resin include 3,4-epoxycyclohexylmethyl (meth)acrylate / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2.6] decyl ester / (meth) acrylic acid copolymer resins [K1]; (meth) acrylate glycidyl ester / (meth) acrylate benzyl ester / (meth) acrylic acid copolymer, (meth) acrylate glycidyl ester / styrene / (meth) acrylic acid copolymer, acrylic acid 3,4-epoxy tricyclic [5.2.1.0 2,6 ] decyl ester / (meth) acrylic acid / N-cyclohexylmaleimide copolymer, acrylic acid 3,4-epoxytricyclo[5.2.1.0 2,6 ] decyl ester / (meth)acrylic acid / N-cyclohexylmaleimide / 2-hydroxyethyl (meth)acrylate copolymer, 3-methyl-3-(meth)acryloyloxymethyloxetane / (meth)acrylic acid / styrene copolymer and other resins [K2]; benzyl (meth)acrylate / (meth)acrylic acid copolymer, styrene / (meth)acrylic acid copolymer and other resins [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, resins obtained by adding glycidyl (meth)acrylate to tricyclodecyl (meth)acrylate / styrene / (meth)acrylic acid copolymer, Resins such as a resin obtained by adding glycidyl (meth)acrylate to a copolymer of tricyclodecyl (meth)acrylate / benzyl (meth)acrylate / (meth)acrylic acid [K4]; a resin obtained by reacting (meth)acrylic acid with a copolymer of tricyclodecyl (meth)acrylate / glycidyl (meth)acrylate, a resin obtained by reacting (meth)acrylic acid with a copolymer of tricyclodecyl (meth)acrylate / styrene / glycidyl (meth)acrylate, etc. [K5]; a resin obtained by reacting (meth)acrylic acid with a copolymer of tricyclodecyl (meth)acrylate / glycidyl (meth)acrylate, and further reacting the resin with tetrahydrophthalic anhydride [K6], etc.

[0280] From the viewpoint of heat resistance, the alkali-soluble resin is more preferably the resin [K1] or the resin [K2], and particularly preferably the resin [K1].

[0281] The polystyrene-equivalent weight average molecular weight (Mw) of the alkali-soluble resin 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 this range, the solubility of the unexposed portion in the developer is high, and the residual film rate and hardness of the resulting pattern tend to be high.

[0282] The dispersion degree [weight average molecular weight (Mw) / number average molecular weight (Mn)] of the alkali-soluble resin is preferably 1 to 6, more preferably 1.001 to 4, and even more preferably 1.01 to 4.

[0283] The acid value (solids content conversion) of the alkali-soluble resin is preferably 10 mg-KOH / g to 300 mg-KOH / g, more preferably 20 mg-KOH / g to 250 mg-KOH / g, even more preferably 25 mg-KOH / g to 200 mg-KOH / g, even more preferably 30 mg-KOH / g to 150 mg-KOH / g, and particularly preferably 60 mg-KOH / g to 135 mg-KOH / g. The acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of the resin and can be determined, for example, by titration using an aqueous potassium hydroxide solution.

[0284] The content of the alkali-soluble resin in 100% by mass of the solid content of the resin composition is preferably 5 to 50% by mass, more preferably 10 to 40% by mass, and even more preferably 15 to 30% by mass. If the content of the alkali-soluble resin is within this range, the solubility of the unexposed portion in the developer tends to be high.

[0285] The resin composition of the present invention preferably further contains a polymerizable compound and a polymerization initiator in addition to the compound represented by formula (I) or a colorant containing the compound represented by formula (I) and an alkali-soluble resin.

[0286] (Polymerizable compound)

[0287] The polymerizable compound is a compound that can be polymerized by active radicals and / or acids generated by a polymerization initiator. Examples thereof include compounds having a polymerizable ethylenically unsaturated bond, and a (meth)acrylate compound is preferred.

[0288] Examples of the polymerizable compound having one ethylenically unsaturated bond include nonylphenyl carbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexyl carbitol acrylate, 2-hydroxyethyl acrylate, N-vinyl pyrrolidone, and the above-mentioned monomers (a), (b), and (c).

[0289] Examples of the polymerizable compound having two ethylenically unsaturated bonds include 1,6-hexanediol di(meth)acrylate, ethylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, bis(acryloyloxyethyl) ether of bisphenol A, and 3-methylpentanediol di(meth)acrylate.

[0290] Among them, the polymerizable compound 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, tri(2-(meth)acryloyloxy)acrylate, and tetrapentaerythritol octa(meth)acrylate. Examples of the present invention include ethylene glycol-modified pentaerythritol tetra(meth)acrylate, ethylene glycol-modified dipentaerythritol hexa(meth)acrylate, propylene glycol-modified pentaerythritol tetra(meth)acrylate, propylene glycol-modified dipentaerythritol hexa(meth)acrylate, caprolactone-modified pentaerythritol tetra(meth)acrylate, and caprolactone-modified dipentaerythritol hexa(meth)acrylate, and preferably dipentaerythritol penta(meth)acrylate and dipentaerythritol hexa(meth)acrylate.

[0291] The weight average molecular weight of the polymerizable compound is preferably 50 to 4,000, more preferably 70 to 3,500, further preferably 100 to 3,000, further preferably 150 to 2,900, and particularly preferably 250 to 1,500.

[0292] The content of the polymerizable compound is, for example, 1 to 99 mass %, preferably 5 to 90 mass %, more preferably 10 to 80 mass %, and further preferably 20 to 70 mass % relative to the total solid content of the resin composition.

[0293] (Polymerization initiator)

[0294] The polymerization initiator is not particularly limited as long as it is a compound that can generate active radicals, acids, etc. by the action of light or heat to initiate polymerization, and a known polymerization initiator can be used.

[0295] Examples of the polymerization initiator include O-acyl oxime compounds, alkylphenone compounds, biimidazole compounds, triazine compounds, and acylphosphine oxide compounds. Examples of these polymerization initiators include compounds described in JP-A-2022-126586.

[0296] The polymerization initiator is preferably a polymerization initiator containing at least one selected from an alkylphenone compound, a triazine compound, an acylphosphine oxide compound, an O-acyloxime compound, and a biimidazole compound, and more preferably a polymerization initiator containing an O-acyloxime compound.

[0297] The content of the polymerization initiator is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, relative to 100 parts by mass of the total amount of the alkali-soluble resin and the polymerizable compound contained in the resin composition. When the content of the polymerization initiator is within this range, there is a tendency for increased sensitivity and shortened exposure time, thereby improving the productivity of the color filter.

[0298] The resin composition of the present invention may contain other components in addition to the alkali-soluble resin, the polymerizable compound, and the polymerization initiator. Examples of such other components include colorants other than the compound represented by formula (I) or the colorant containing the compound represented by formula (I), polymerization initiation aids, solvents, leveling agents, and other components.

[0299] (Other colorants)

[0300] The resin composition of the present invention may contain, in addition to the compound represented by formula (I) or a colorant containing the compound represented by formula (I), a dye other than the compound represented by formula (I) (hereinafter sometimes referred to as dye (A1-1)) and / or a pigment (hereinafter sometimes referred to as pigment (A1-2)) (hereinafter, dye (A1-1) and pigment (A1-2) may be collectively referred to as colorant (A1)). These may be used alone or in combination of two or more.

[0301] Dye (A1-1) is not particularly limited as long as it is not a compound represented by formula (I), and known dyes can be used, for example, solvent dyes, acid dyes, direct dyes, mordant dyes, etc. can be enumerated. As dyes, for example, compounds classified as dyes in the Color Index (published by The Society of Dyers and Colourists) and known dyes described in the Dyeing Guide (Color Dyeing Company) can be enumerated. In addition, according to the chemical structure, azo dyes, cyanine dyes, triphenylmethane dyes, xanthene dyes, anthraquinone dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, azomethine dyes, square acid dyes can be enumerated. Dyes, acridine dyes, styryl dyes, coumarin dyes, quinoline dyes, nitro dyes, and phthalocyanine dyes, etc. Among these, organic solvent-soluble dyes are preferred.

[0302] The pigment (A1-2) is not particularly limited as long as it is not a compound represented by formula (I), and known pigments can be used. For example, pigments classified as pigments in the Color Index (published by The Society of Dyers and Colourists) can be mentioned.

[0303] 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;

[0304] CI Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73 and other orange pigments;

[0305] 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, 272, 273, 291 and other red pigments;

[0306] CI Pigment Blue 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 60 and other blue pigments;

[0307] CI Pigment Violet 1, 19, 23, 32, 36, 38 and other purple pigments;

[0308] CI Pigment Green 7, 36, 58, 59, 62, 63 and other green pigments;

[0309] Brown pigments such as CI Pigment Brown 23 and 25;

[0310] Black pigments such as CI Pigment Black 1 and 7.

[0311] As the colorant (A1), yellow, red or green dyes and pigments are preferred.

[0312] The colorant (A1) may be subjected to rosin treatment, surface treatment using a derivative having an acidic or basic group introduced therein, grafting treatment onto the surface of the colorant (A1) using a polymer compound, etc., micronization treatment using a sulfuric acid micronization method, etc., washing treatment using an organic solvent or water, etc. to remove impurities, and removal of ionic impurities using an ion exchange method, etc. The particle size of the colorant (A1) is preferably substantially uniform.

[0313] In the resin composition, in addition to the compound represented by formula (I) or the colorant (I) of the present invention comprising the compound represented by formula (I), a colorant (A1) may be further included as a colorant. In this case, the ratio of the colorant (I) (compound (I) or the colorant comprising compound (I)) relative to the total amount of the colorant as a whole contained in the resin composition is, for example, 1% by mass or more, preferably 2% by mass or more, more preferably 10% by mass or more, further preferably 25% by mass or more, and particularly preferably 50% by mass or more. In addition, when the colorant (A1) is further included, the ratio of the colorant (I) relative to the total amount of the colorant as a whole contained in the resin composition is, for example, less than 100% by mass. The colorant as a whole contained in the resin composition is also referred to as colorant (A) in this specification. From the viewpoint of optical properties, the amount of the compound represented by the above-mentioned formula (X) relative to the total amount of the colorant (A) is preferably 0-10% by mass, more preferably 0-5% by mass, further preferably 0-3% by mass, and even more preferably 0-2% by mass.

[0314] When the resin composition contains a solvent, a colorant-containing solution (sometimes referred to as a colored composition) containing a colorant (A) and a solvent can be prepared in advance, and the resin composition can be prepared using this colorant-containing solution. When the colorant (A) is insoluble in the solvent, for example, when the colorant (A) contains the pigment (A1-2), the colorant-containing solution can be prepared by dispersing the colorant (A) in the solvent and mixing. The colorant-containing solution may contain a portion or all of the solvent contained in the resin composition.

[0315] The solid content in the colorant-containing solution is preferably 0.01% by mass to 99.99% by mass, more preferably 0.1% by mass to 99.9% by mass, further preferably 0.1% by mass to 99% by mass, further preferably 0.5% by mass to 90% by mass, and particularly preferably 1% by mass to 50% by mass, relative to the total amount of the colorant-containing solution.

[0316] The colorant (A) can be dispersed uniformly in the solution by adding a dispersant to the colorant (A). When two or more colorants (A) are used in combination, each can be dispersed individually or as a mixture.

[0317] As dispersant, for example, surfactant etc. can be enumerated, and can be any surfactant in cationic, anionic, nonionic and amphoteric. Specifically, surfactant etc. of polyester, polyamine and acrylic acid can be enumerated. These dispersants can be used alone or in combination of two or more. As dispersant, when expressed by trade name, KP (Shin-Etsu Chemical Co., Ltd. system), FLOWLEN (Kyoeisha Chemical Co., Ltd. system), Solsperse (registered trademark) (Zeneca Co., Ltd. system), EFKA (registered trademark) (BASF company system), AJISPER (registered trademark) (Ajinomoto Fine Chemical Co., Ltd. system) and Disperbyk (registered trademark) (BYK-Chemie Co., Ltd. system), BYK (registered trademark) (BYK-Chemie Co., Ltd. system) etc. can be enumerated. As dispersant, resin (B) described later can be used.

[0318] When a dispersant is used, the amount of the dispersant (solid content) used is generally 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 the colorant (A). When the amount of the dispersant used is within the above range, a more uniformly dispersed colorant-containing solution tends to be obtained.

[0319] The content of the colorant (A) relative to the total solid content of the resin composition 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. When the content of the colorant (A) is within the above range, the color density of the resulting color filter is sufficient, and the composition can contain the desired amount of resin (B), thereby enabling the formation of a pattern with sufficient mechanical strength.

[0320] As used herein, the term "total solid content" refers to the amount obtained by subtracting the solvent from the total amount of the resin composition. The total solid content and the content of each component relative to the total solid content can be measured, for example, by known analytical methods such as liquid chromatography or gas chromatography.

[0321] (Polymerization initiator aid)

[0322] The polymerization initiation aid is a compound or sensitizer for accelerating the polymerization of a polymerizable compound initiated by a polymerization initiator. When the polymerization initiation aid is included, it is usually used in combination with a polymerization initiator.

[0323] Examples of the polymerization initiation aid include amine compounds, alkoxyanthracene compounds, thioxanthone compounds, and carboxylic acid compounds. Examples of these polymerization initiation aids include compounds described in JP-A-2022-126586.

[0324] When these polymerization initiation aids are used, the content thereof is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, based on 100 parts by mass of the total amount of the alkali-soluble resin and the polymerizable compound contained in the resin composition.

[0325] (Solvent)

[0326] The solvent is not particularly limited, and any solvent commonly used in this field can be used.

[0327] As solvent, for example, ester solvent (intramolecule including-COO- and not containing-O- solvent), ether solvent (intramolecule including-O- and not containing-COO- solvent), ether ester solvent (intramolecule including-COO- and-O- solvent), ketone solvent (intramolecule including-CO- and not containing-COO- solvent), alcohol solvent (intramolecule including OH and not containing-O-,-CO- and-COO- solvent), aromatic hydrocarbon solvent, amide solvent, dimethyl sulfoxide etc. can be enumerated.These solvents can be used alone or with more than two kinds.As these solvents, for example, the solvent described in record in Japanese Patent Laid-Open No. 2022-126586 gazette can be enumerated.

[0328] As the solvent, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate and cyclohexanone are preferred.

[0329] When a solvent is included, the content of the solvent is usually 99.99% by mass or less, preferably 40 to 99% by mass, more preferably 50 to 95% by mass, further preferably 70 to 95% by mass, and further preferably 75 to 90% by mass, relative to the total amount of the resin composition. In other words, the total amount of the solid content of the resin composition is usually 0.01% by mass or more, preferably 1 to 60% by mass, more preferably 5 to 50% by mass, further preferably 5 to 30% by mass, and further preferably 10 to 25% by mass or less. If the content of the solvent is within the above range, the flatness during coating is good, and the color concentration is not insufficient when forming a color filter, and therefore there is a trend of good display characteristics.

[0330] (Leveling agent)

[0331] As leveling agents, silicone surfactants, fluorine-based surfactants, and silicone surfactants having fluorine atoms can be mentioned. These can have polymerizable groups in the side chains. As these leveling agents, for example, the leveling agents described in Japanese Patent Application Laid-Open No. 2022-126586 can be mentioned.

[0332] When a leveling agent is included, the content of the leveling agent is preferably 0.0005 to 1% by mass, more preferably 0.001 to 0.5% by mass, and even more preferably 0.005 to 0.1% by mass relative to the total amount of the resin composition. When the content of the leveling agent is within the above range, the flatness of the optical filter can be improved.

[0333] (Other ingredients)

[0334] The resin composition may contain fillers, other polymer compounds, adhesion promoters, quenchers, antioxidants, light stabilizers, chain transfer agents, and other additives known in the art as needed. The content of other components is not particularly limited as long as it does not adversely affect the performance of the resin composition and the color filter obtained therefrom, but is generally about 0.0001 to 10% by mass, or about 0.0005 to 8% by mass, relative to the mass of the resin composition.

[0335] <Method for producing resin composition>

[0336] The resin composition can be prepared by mixing the compound of the present invention, an alkali-soluble resin, other colorants as needed, polymerizable compounds, polymerization initiators, solvents, leveling agents, and other components. Mixing can be performed using known or customary equipment and conditions.

[0337] The compound of formula (I), the colorant containing the compound of formula (I), and any other colorant used can be used in a state of being mixed with a part or all of the solvent in advance and dispersed using a bead mill or the like until the average particle size becomes about 0.2 μm or less, preferably in a dispersed state. In this case, part or all of the above-mentioned dispersant and alkali-soluble resin can be added as needed. In addition, the compound of formula (I), the colorant containing the compound of formula (I), and any other colorant used can be used in a state of being dissolved in a part or all of the solvent in advance. The target resin composition can be prepared by mixing the remaining components in a predetermined concentration in the colorant-containing solution obtained in this manner.

[0338] The resin composition is preferably filtered through a filter having a pore size of about 0.01 to 10 μm after mixing the components.

[0339] <Cured product of resin composition and method for producing color filter>

[0340] The resin composition of the present invention can be formed into a color filter that can be a color conversion layer. The color filter can be manufactured by a method including the step of curing the resin composition of the present invention, and comprises a cured product of the resin composition of the present invention. The present invention also provides a cured product of the resin composition of the present invention, and a color filter comprising the cured product. As a method for forming a colored pattern in a color filter, photolithography, inkjet method, printing method, etc. can be cited. Among them, photolithography is preferred. Photolithography is a method in which the above-mentioned resin composition is applied to a substrate and dried to form a resin composition layer, and the resin composition layer is exposed and developed across a photomask. In the photolithography, by not using a photomask and / or not developing during exposure, a colored coating film as a cured product of the above-mentioned resin composition layer can be formed. The colored pattern, colored coating film, etc. formed in this way are the color filter of the present invention, comprising a cured product of the resin composition of the present invention.

[0341] The film thickness of the produced color filter is not particularly limited and can be appropriately adjusted depending on the purpose and application. It is, for example, 0.1 to 30 μm, preferably 0.1 to 20 μm, and more preferably 0.5 to 6 μm.

[0342] As the substrate, glass plates such as quartz glass, borosilicate glass, aluminosilicate glass, and soda-lime glass coated with silica can be used; resin plates such as polycarbonate, polymethyl methacrylate, and polyethylene terephthalate; organic silicone; and substrates obtained by forming thin films of aluminum, silver, or silver / copper / palladium alloys on the above substrates. Other color filter layers, resin layers, transistors, and circuits can be formed on these substrates.

[0343] The formation of pixels of each color by photolithography can be performed using known or customary equipment and conditions. For example, the formation can be performed as follows.

[0344] First, a resin composition is applied on a substrate, and then dried by heating (prebaking) and / or drying under reduced pressure to remove volatile components such as a solvent, followed by drying to obtain a smooth colored resin composition layer.

[0345] Examples of the coating method include spin coating, slit coating, and slit and spin coating.

[0346] The temperature for heat drying is preferably 30 to 120°C, more preferably 50 to 110°C. The heating time is preferably 10 seconds to 60 minutes, more preferably 30 seconds to 30 minutes. When drying under reduced pressure, it is preferably performed at a pressure of 50 to 150 Pa and a temperature range of 20 to 25°C. The thickness of the resin composition layer is not particularly limited and can be appropriately selected depending on the thickness of the target color filter.

[0347] Next, the resin composition layer can be exposed via a photomask for forming a target coloring pattern. The pattern on the photomask is not particularly limited, and a pattern corresponding to the target application can be used. In addition, in order to be able to uniformly irradiate the entire exposure surface with parallel light and accurately align the photomask with the substrate formed with the resin composition layer, it is preferred to use an exposure device such as a mask aligner and a stepper.

[0348] The light source used for exposure is preferably one that generates light with a wavelength of 250 nm to 450 nm. For example, a filter that cuts off this wavelength range can be used to block light shorter than 350 nm, or a bandpass filter that selectively extracts light near 436 nm, 408 nm, and 365 nm can be used to filter out these wavelengths. Specific examples include mercury lamps, light-emitting diodes, metal halide lamps, and halogen lamps.

[0349] The exposed resin composition layer is brought into contact with a developer for development, thereby forming a colored pattern on the substrate. By development, the unexposed portion of the colored resin composition layer is dissolved in the developer and removed. As a developer, for example, aqueous solutions of alkaline compounds such as potassium hydroxide, sodium bicarbonate, sodium carbonate, and tetramethylammonium hydroxide are preferred. The concentration in the aqueous solution of these alkaline compounds is preferably 0.01 to 10% by mass, more preferably 0.03 to 5% by mass. In addition, the developer may contain a surfactant. The development method may be any one of a paddle method, an immersion method, and a spray method. And the substrate may be tilted at any angle during development. The developed substrate is preferably washed with water.

[0350] In addition, it is preferred that the obtained colored pattern be post-baked. The post-baking temperature is preferably 150 to 250° C., more preferably 160 to 240° C. The post-baking time is preferably 1 minute to 120 minutes, more preferably 10 minutes to 60 minutes. The compound (I) of the present invention is a compound having a very high thermal decomposition starting temperature and has very high heat resistance. Therefore, for example, it will not decompose at all in the post-baking for a certain period of time at a high temperature as described above. As a result, no decomposition products are contained in the obtained color filter. When a colorant with low heat resistance is used, a part of the colorant is sometimes decomposed and contains decomposition products in the post-baking process as described above. The inclusion of such decomposition products sometimes damages the optical properties of the color filter, but when using the compound (I) of the present invention or the colorant of the present invention containing the compound (I), such decomposition can be suppressed, and the optical properties can be further improved. For example, it is believed that a sharp absorption peak can be obtained, and the deviation of the optical properties in the color filter can be suppressed, thereby further improving the optical properties.

[0351] <Display Devices and Solid-State Imaging Devices>

[0352] The color filter is useful as a color filter used in display devices (eg, liquid crystal display devices, organic EL devices, electronic paper, etc.) and solid-state imaging devices, and is particularly useful as a color filter used in organic EL devices.

[0353] Example

[0354] The present invention will be described in more detail below with reference to the following examples. However, the present invention is not limited to the following examples and can be implemented with modifications as appropriate within the scope of the present invention. Such modifications are within the technical scope of the present invention. It should be noted that, unless otherwise specified, "parts" represent "parts by mass" and "%" represents "mass %."

[0355] In the following examples, the structures of the compounds were confirmed by mass spectrometry (MALDI-TOF MS; JMS-S3000 manufactured by JEOL Ltd.) and NMR (400-MR manufactured by Varian).

[0356] The polystyrene-equivalent weight average molecular weight (Mw) and number average molecular weight (Mn) of the resin were measured by GPC under the following conditions.

[0357] Device: HLC-8120GPC (manufactured by TOSOH Co., Ltd.)

[0358] Column: TSK-GELG2000HXL

[0359] Column temperature: 40°C

[0360] Solvent: tetrahydrofuran

[0361] Flow rate: 1.0 mL / min

[0362] Solid content concentration of analysis sample: 0.001 to 0.01 mass%

[0363] Injection volume: 50 μL

[0364] Detector: RI

[0365] Calibration standard substances: TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by TOSOH Corporation)

[0366] The ratio of the polystyrene-equivalent weight average molecular weight to the number average molecular weight (Mw / Mn) obtained above was defined as the degree of dispersion.

[0367] <Synthesis example 1>

[0368] Synthesis of compound (IV-b)

[0369] 13.6 parts of compound (IV-a) obtained in the example described in Chemical Communication 2019, 55, 14182-14185, 20.4 parts of bromine (manufactured by FUJIFILM Wako Chemicals Co., Ltd.) and 1508 parts of chlorobenzene (manufactured by Tokyo Chemical Industry Co., Ltd.) were mixed and stirred at 50°C for 4.5 hours. After the reaction was completed, it was cooled to 23°C, 40 parts of sodium sulfite (manufactured by Kanto Chemical Co., Ltd.) and 1000 parts of water were added, and a liquid separation operation was performed. The obtained organic phase was dehydrated with anhydrous sodium sulfate (manufactured by Kanto Chemical Co., Ltd.), and after filtering the sodium sulfate, the solvent was distilled off to obtain 15.5 parts (yield 98%) of the compound represented by formula (IV-b) as a yellow solid.

[0370]

[0371] Identification of compound (IV-b)

[0372] (Mass Spectrometry) Ionization Mode = MALDI-TOF + :m / z=560

[0373] Exact mass: 559

[0374] <Synthesis example 2>

[0375] Synthesis of compound (IV-c)

[0376] 10.0 parts of compound (IV-b) obtained in Synthesis Example 1, 403 parts of maleic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) and 8.77 parts of chloranil (manufactured by Tokyo Chemical Industry Co., Ltd.) were mixed and stirred at 125°C for 24 hours. After cooling to 80°C, the mixture was added dropwise to a mixed solution of 596 parts of concentrated hydrochloric acid, 7200 parts of water and 800 parts of acetone, resulting in a yellow precipitate. The mixture containing the yellow precipitate was filtered, and the filtered residue was washed with 100 parts of water and 20.0 parts of acetone in that order. The obtained residue was dried under reduced pressure at 60°C to obtain 11.7 parts of the compound represented by formula (IV-c) (yield 100%).

[0377]

[0378] Identification of compound (IV-c)

[0379] (Mass Spectrometry) Ionization Mode = MALDI-TOF - :m / z=652

[0380] Exact mass: 653

[0381] <Synthesis Example 3>

[0382] Synthesis of compound (IV-d)

[0383] 20.0 parts of compound (IV-c) obtained in Synthesis Example 2, 29.9 parts of 1-bromobutane (manufactured by Tokyo Chemical Industry Co., Ltd.), 19.4 parts of 1-butanol (manufactured by Tokyo Chemical Industry Co., Ltd.), 22.7 parts of 1,8-diazabicyclo[5.4.0]-7-undecene (manufactured by Tokyo Chemical Industry Co., Ltd.), and 280 parts of dehydrated N,N-dimethylformamide (manufactured by Tokyo Chemical Industry Co., Ltd.) were mixed and stirred at 60°C for 3 hours. After cooling to 23°C, the solvent was distilled off. The resulting yellow residue was purified on a silica gel column (solvent: chloroform) to obtain 19.4 parts of the compound represented by formula (IV-d) (yield 81%).

[0384]

[0385] Identification of compound (IV-d)

[0386] (Mass Spectrometry) Ionization Mode = MALDI-TOF + :m / z=784

[0387] Exact mass: 783

[0388] <Synthesis example 4>

[0389] Synthesis of compound (IV-e)

[0390] 18.0 parts of the compound represented by formula (IV-d) obtained in Synthesis Example 3, 6.40 parts of bis(pinacolato)diboron (manufactured by Tokyo Chemical Industry Co., Ltd.), 6.53 parts of potassium acetate (manufactured by Kanto Chemical Co., Ltd.), 0.839 parts of 1,1-bis(diphenylphosphino)ferrocenedichloropalladium(II) (manufactured by Fujifilm Wako Chemicals Co., Ltd.), and 540 parts of dehydrated N,N-dimethylformamide (manufactured by Kanto Chemical Co., Ltd.) were mixed and stirred at 70°C for 16 hours. The resulting mixture was filtered through celite, and the filtrate was concentrated, resulting in the precipitation of a solid substance of the compound represented by formula (IV-e). The precipitated solid substance was collected by filtration, washed with 18 parts of methanol, and dried under reduced pressure at 60°C to obtain 16.8 parts of the compound represented by formula (IV-e) (yield 88%).

[0391]

[0392] Identification of compound (IV-e)

[0393] (Mass Spectrometry) Ionization Mode = MALDI-TOF + :m / z=832

[0394] Exact mass: 831

[0395] <Synthesis Example 5>

[0396] Synthesis of compound (Va)

[0397] According to the synthesis described in Chemical Science 2022, Vol. 13, pp. 10119-10128, a compound represented by formula (Va) was obtained.

[0398]

[0399] Identification of compound (Va)

[0400] (Mass Spectrometry) Ionization Mode = MALDI-TOF + :m / z=514

[0401] Exact mass: 513

[0402] <Production Example 1 (Example 1)>

[0403] 20.0 parts of the compound (IV-e) obtained in Synthesis Example 4, 13.6 parts of the compound (Va) obtained in Synthesis Example 5, 2.20 parts of tris(dibenzylideneacetone)dipalladium(0) (manufactured by Tokyo Chemical Industry Co., Ltd.), 2.69 parts of tricyclohexylphosphine (manufactured by Fujifilm Wako Chemicals Co., Ltd.), 41.2 parts of potassium carbonate (manufactured by Kanto Chemical Co., Ltd.), and 1440 parts of dehydrated xylene (manufactured by Kanto Chemical Co., Ltd.) were mixed and stirred at 145°C for 18 hours. After cooling to 23°C, the mixture was filtered through celite and the filtrate was concentrated, resulting in precipitation of a solid substance of the compound represented by formula (I-1). The precipitated solid substance was collected by filtration, purified by silica gel column chromatography (solvent: chloroform), and dried under reduced pressure at 60°C to obtain 25.5 parts of the compound represented by formula (I-1) (compound (I-1)) (yield 81%). This manufacturing method is also an embodiment of the manufacturing method of the present invention.

[0404]

[0405] Identification of compound (I-1)

[0406] (Mass Spectrometry) Ionization Mode = MALDI-TOF + :m / z=1059

[0407] Exact mass: 1058

[0408] <Production Example 2 (Comparative Production Example 1)>

[0409] (a) Synthesis of Compound (III-1)

[0410] According to the description of Synthesis Example 9 in JP-A-2022-126586, a compound represented by formula (III-1) was obtained.

[0411]

[0412] Identification of compound (III-1)

[0413] (Mass Spectrometry) Ionization Mode = MALDI-TOF + :m / z=835

[0414] Exact mass: 834

[0415] (b) Synthesis of Compound (I-r1)

[0416] 35.0 parts of the compound represented by the following formula (III-r) were replaced with 27.9 parts of the compound represented by the formula (III-1). In addition, according to the description of Example 1 of WO2009 / 027952, a mixture consisting of a compound represented by the formula (I-r1), a compound represented by the formula (II-r1), and a compound represented by the formula (III-1) was obtained. From the point of view that the compound represented by the formula (I-r1) is a compound contained in the formula (I), the compound is a compound of the embodiment. However, the compound represented by the formula (I-r1) could not be separated from the obtained mixture by silica gel column chromatography. In addition, this production method is a comparative example of the production method of the present invention.

[0417]

[0418] (c) Synthesis of a mixture containing compound (I-1)

[0419] A mixture of 13.5 parts of compounds represented by Formula (I-1), Formula (II-1), and Formula (III-1) was obtained in the same manner as in Synthesis Example 3, except that 20.0 parts of the compound represented by Formula (IV-c) was replaced with 15.9 parts of the mixture of compounds represented by Formula (I-r1), Formula (II-r1), and Formula (III-1) obtained in Preparation Example 2 (Comparative Preparation Example 1) (b). A mixture of compounds represented by Formula (I-2), Formula (II-1), and Formula (III-1) was difficult to separate using silica gel column chromatography. The production ratio of each compound can be calculated from the absorbance ratio of each compound in the visible absorption spectrum (V-570): Compound (I-1): (II-1): (III-1) = 7:91:2 (absorbance (wavelength 586 nm): absorbance (wavelength 514 nm): absorbance (wavelength 654 nm)). The yield of Compound (I-1) was 5%. It should be noted that the compound represented by formula (I-1) is a compound included in formula (I), and is therefore a compound of the Examples. However, the compound represented by formula (I-1) cannot be separated from the resulting mixture. In addition, the manufacture method is a comparative example of the manufacture method of the present invention, and the manufacture method of manufacture example 2 is also referred to as comparative manufacture example 1.

[0420]

[0421] <Synthesis Example 6>

[0422] Synthesis of compound (Vb)

[0423] According to the synthesis described in Angewandte Chemie, International Edition 2023, 62, e202214997, the compound represented by formula (Vb) was obtained.

[0424]

[0425] Identification of compound (Vb)

[0426] (Mass Spectrometry) Ionization Mode = MALDI-TOF + :m / z=485

[0427] Exact mass: 484

[0428] <Synthesis Example 7>

[0429] Synthesis of compound (IV-f)

[0430] 30.0 parts of compound (IV-c) obtained in Synthesis Example 2, 12.2 parts of 2,6-diisopropylaniline (manufactured by Tokyo Chemical Industry Co., Ltd.), and 900 parts of propionic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) were mixed and stirred at 130°C for 6 hours. After cooling to 23°C, the solvent was distilled off. The resulting yellow residue was purified by silica gel column chromatography (solvent: chloroform) to obtain 31.3 parts of the compound represented by formula (IV-f) (yield 84%).

[0431]

[0432] Identification of compound (IV-f)

[0433] (Mass Spectrometry) Ionization Mode = MALDI-TOF + :m / z=813

[0434] Exact mass: 812

[0435] <Synthesis example 8>

[0436] Synthesis of compound (IV-g)

[0437] 16.9 parts of the compound represented by formula (IV-g) were obtained in the same manner as in Synthesis Example 4 except that 18.0 parts of the compound represented by formula (IV-d) was replaced with 18.7 parts of the compound represented by formula (IV-f) (yield 86%).

[0438]

[0439] Identification of compound (IV-g)

[0440] (Mass Spectrometry) Ionization Mode = MALDI-TOF + :m / z=865

[0441] Exact mass: 864

[0442] <Production Example 3 (Example 2)>

[0443] 20.0 parts of the compound represented by formula (IV-e) were replaced by 20.7 parts of the compound represented by formula (IV-g) obtained in Synthesis Example 8, and 13.6 parts of the compound represented by formula (Va) were replaced by 26.7 parts of the compound represented by formula (Vb) obtained in Synthesis Example 6. In addition, 21.1 parts of the compound represented by formula (I-2) were obtained in the same manner as in Example 1 (yield 83%).

[0444]

[0445] Identification of compound (IV-e)

[0446] (Mass Spectrometry) Ionization Mode = MALDI-TOF + :m / z=1059

[0447] Exact mass: 1058

[0448] <Production Example 4 (Comparative Production Example 2)>

[0449] (a) Synthesis of Compound (IV-r1)

[0450] Except that 18.0 parts of the compound represented by formula (IV-d) was replaced by 12.9 parts of the compound represented by formula (IV-b) obtained in Synthesis Example 1, 12.1 parts of the compound represented by formula (IV-r1) were obtained in the same manner as in Synthesis Example 4 (yield 87%).

[0451]

[0452] Identification of compound (IV-r1)

[0453] (Mass Spectrometry) Ionization Mode = MALDI-TOF + :m / z=608

[0454] Exact mass: 607

[0455] (b) Synthesis of Compound (III-2)

[0456] 20.0 parts of the compound represented by formula (IV-e) were replaced by 14.6 parts of the compound represented by formula (IV-r1) obtained in Preparation Example 4 (Comparative Preparation Example 2), and 13.6 parts of the compound represented by formula (Va) were replaced by 12.8 parts of the compound represented by formula (Vb) obtained in Synthesis Example 6. In addition, 15.9 parts of the compound represented by formula (III-2) were obtained in the same manner as in Example 1 (yield 82%).

[0457]

[0458] Identification of compound (III-2)

[0459] (Mass Spectrometry) Ionization Mode = MALDI-TOF + :m / z=806

[0460] Exact mass: 805

[0461] (c) Synthesis of Compound (I-r2)

[0462] Except that 35 parts of the compound represented by formula (III-r) was changed to 32 parts of the compound represented by formula (III-1), a mixture consisting of formula (I-r2), formula (II-r2) and formula (III-r2) was obtained according to the description of Example 1 of WO2009 / 027952.

[0463]

[0464] (d) Synthesis of a mixture containing compound (I-2)

[0465] A mixture of 22.0 parts of the compound represented by Formula (I-2), the compound represented by Formula (II-2), and the compound represented by Formula (III-2) was obtained in the same manner as in Synthesis Example 7, except that 30.0 parts of the compound represented by Formula (IV-c) was replaced with 22.8 parts of the mixture of the compounds represented by Formula (I-r2), Formula (II-r2), and Formula (III-2) obtained in Preparation Example 4 (Comparative Preparation Example 2) (c). A mixture of the compounds represented by Formula (I-2), Formula (II-2), and Formula (III-2) was difficult to separate using silica gel column chromatography. The production ratio of each compound can be calculated from the absorbance ratio of each compound in the visible absorption spectrum (V-570): Compound (I-2): (II-2): (III-2) = 11:84:5 (absorbance (wavelength 567 nm): absorbance (wavelength 487 nm): absorbance (wavelength 630 nm)). The compound represented by formula (I-2) is a compound of the Example in that it is a compound included in formula (I). In addition, this production method is a comparative example of the production method of the present invention.

[0466]

[0467] <Synthesis Example 9>

[0468] Synthesis of compound (IV-h)

[0469] 49.2 parts of compound (Vb) obtained in Synthesis Example 6, 23.0 parts of 4,4,5,5-tetramethyl-2-(1-naphthyl)-1,3,2-dioxaborolane naphthyl-1-boronic acid pinacol, 8.46 parts of tris(dibenzylideneacetone)dipalladium(0) (manufactured by Tokyo Chemical Industry Co., Ltd.), 10.3 parts of tricyclohexylphosphine (manufactured by Fujifilm Wako Chemicals Co., Ltd.), 158 parts of potassium carbonate (manufactured by Kanto Chemical Co., Ltd.), and 1656 parts of dehydrated xylene (manufactured by Kanto Chemical Co., Ltd.) were mixed and stirred at 145°C for 24 hours. After cooling to 23°C, the mixture was filtered through celite and the filtrate was concentrated. The resulting residue was purified on a silica gel column (solvent: chloroform) and dried under reduced pressure at 60°C to obtain 35.2 parts of the compound represented by formula (IV-h) (yield 79%).

[0470]

[0471] Identification of compound (IV-h)

[0472] (Mass Spectrometry) Ionization Mode = MALDI-TOF + :m / z=453

[0473] Exact mass: 452

[0474] <Synthesis Example 10>

[0475] Synthesis of compound (IV-i)

[0476] Except that 13.6 parts of the compound represented by formula (IV-a) was replaced by 12.8 parts of the compound represented by formula (IV-h) obtained in Synthesis Example 9, 12.5 parts of the compound represented by formula (IV-i) were obtained in the same manner as in Synthesis Example 1 (yield 83%).

[0477]

[0478] Identification of compound (IV-i)

[0479] (Mass Spectrometry) Ionization Mode = MALDI-TOF + :m / z=531

[0480] Exact mass: 530

[0481] <Synthesis Example 11>

[0482] Synthesis of compound (IV-j)

[0483] 11.2 parts of the compound represented by formula (IV-j) were obtained in the same manner as in Synthesis Example 2 except that 9.48 parts of the compound represented by formula (IV-i) obtained in Synthesis Example 10 were used in place of 10.0 parts of the compound represented by formula (IV-b) (yield 100%).

[0484]

[0485] Identification of compound (IV-j)

[0486] (Mass Spectrometry) Ionization Mode = MALDI-TOF + :m / z=625

[0487] Exact mass: 624

[0488] <Synthesis Example 12>

[0489] Synthesis of compound (IV-k)

[0490] 31.7 parts of the compound represented by formula (IV-k) were obtained in the same manner as in Synthesis Example 7 except that 30.0 parts of the compound represented by formula (IV-c) was replaced by 28.7 parts of the compound represented by formula (IV-j) obtained in Synthesis Example 11 (yield 88%).

[0491]

[0492] Identification of compound (IV-k)

[0493] (Mass Spectrometry) Ionization Mode = MALDI-TOF + :m / z=784

[0494] Exact mass: 783

[0495] <Synthesis Example 13>

[0496] Synthesis of compound (IV-m)

[0497] 16.7 parts of the compound represented by formula (IV-m) were obtained in the same manner as in Synthesis Example 4 except that the compound represented by formula (IV-d) was replaced by the compound represented by formula (IV-k) obtained in Synthesis Example 12 (yield 85%).

[0498]

[0499] Identification of compound (IV-m)

[0500] (Mass Spectrometry) Ionization Mode = MALDI-TOF + :m / z=832

[0501] Exact mass: 831

[0502] <Production Example 5 (Example 3)>

[0503] Synthesis of compound (I-3)

[0504] 20.0 parts of the compound represented by formula (IV-e) were replaced by 20.0 parts of the compound represented by formula (IV-m) obtained in Synthesis Example 13, and 13.6 parts of the compound represented by formula (Va) were replaced by 12.8 parts of the compound represented by formula (Vb) obtained in Synthesis Example 6. In addition, 18.3 parts of the compound represented by formula (I-3) were obtained in the same manner as in Example 1 (yield 74%).

[0505]

[0506] Identification of compound (I-3)

[0507] (Mass Spectrometry) Ionization Mode = MALDI-TOF + :m / z=1030

[0508] Exact mass: 1029

[0509] <Production Example 6 (Comparative Production Example 3)>

[0510] (a) Synthesis of Compound (III-3)

[0511] According to the description of Synthesis Example 10 in JP-A-2022-126586, a compound represented by formula (III-3) was obtained.

[0512]

[0513] Identification of compound (III-3)

[0514] (Mass Spectrometry) Ionization Mode = MALDI-TOF + :m / z=777

[0515] Exact mass: 776

[0516] (b) Synthesis of Compound (I-r3)

[0517] 35.0 parts of the compound represented by formula (III-r) are changed to 26.0 parts of the formula (III-3) obtained in Production Example 6 (Comparative Production Example 3) (a). In addition, according to the description of Example 1 of WO2009 / 027952, a mixture of compounds represented by formula (I-r3), formula (II-r3) and formula (III-3) is obtained.

[0518]

[0519] (d) Synthesis of a mixture containing compound (I-3)

[0520] A mixture of 21.8 parts of compounds represented by Formula (I-3), Formula (II-3), and Formula (III-3) was obtained in the same manner as in Synthesis Example 7, except that 30.0 parts of the compound represented by Formula (IV-c) was replaced with 22.1 parts of the mixture of compounds represented by Formula (I-r3), Formula (II-r3), and Formula (III-3) obtained in Preparation Example 6 (Comparative Preparation Example 3) (b). The mixture of compounds represented by Formula (I-3), Formula (II-3), and Formula (III-3) was difficult to separate using silica gel column chromatography. The production ratio of each compound can be calculated from the absorbance ratio of each compound in the visible absorption spectrum (V-570): Compound (I-3): (II-3): (III-3) = 11:84:5 (absorbance (wavelength 586 nm): absorbance (wavelength 514 nm): absorbance (wavelength 654 nm)). The yield of Compound (I-3) was 8%.

[0521]

[0522] <Synthesis Example 14>

[0523] Synthesis of compound (IV-n)

[0524] 20.0 parts of the compound represented by formula (IV-n) were obtained in the same manner as in Synthesis Example 3 except that 19.1 parts of the compound represented by formula (IV-j) obtained in Synthesis Example 10 was used in place of 20.0 parts of the compound represented by formula (IV-c) (yield 87%).

[0525]

[0526] Identification of compound (IV-n)

[0527] (Mass Spectrometry) Ionization Mode = MALDI-TOF + :m / z=755

[0528] Exact mass: 754

[0529] <Synthesis Example 15>

[0530] Synthesis of compound (IV-o)

[0531] 14.7 parts of the compound represented by formula (IV-o) were obtained in the same manner as in Synthesis Example 4 except that 18.0 parts of the compound represented by formula (IV-d) was replaced with 17.3 parts of the compound represented by formula (IV-n) obtained in Synthesis Example 14 (yield 80%).

[0532]

[0533] Identification of compound (IV-o)

[0534] (Mass Spectrometry) Ionization Mode = MALDI-TOF + :m / z=803

[0535] Exact mass: 802

[0536] <Production Example 7 (Example 4)>

[0537] Synthesis of compound (I-4)

[0538] 20.0 parts of the compound represented by formula (IV-e) were replaced by 19.3 parts of the compound represented by formula (IV-o) obtained in Synthesis Example 15, and 13.6 parts of the compound represented by formula (Va) were replaced by 12.8 parts of the compound represented by formula (Vb) obtained in Synthesis Example 6. In addition, 19.7 parts of the compound represented by formula (I-4) were obtained in the same manner as in Example 1 (yield 82%).

[0539]

[0540] Identification of compound (I-4)

[0541] (Mass Spectrometry) Ionization Mode = MALDI-TOF + :m / z=1001

[0542] Exact mass: 1000

[0543] <Production Example 8 (Comparative Production Example 4)>

[0544] (a) Synthesis of Compound (I-4)

[0545] 20.0 parts of the compound represented by formula (IV-c) was substituted for Preparation Example 6 (Comparative Preparation Example 3)

[0546] In addition to 14.7 parts of a mixture consisting of compounds represented by formula (I-r3), formula (II-r3) and formula (III-3) obtained in (b), 12.0 parts of a mixture consisting of compounds represented by formula (I-4), formula (II-4) and formula (III-4) were obtained in the same manner as in Synthesis Example 3. The compounds in this mixture are difficult to separate using silica gel column chromatography. The production ratio of each compound can be calculated from the absorbance ratio of the visible absorption spectrum (V-570) of each compound, compound (I-4): (II-4): (III-4) = 18:72:10 (absorbance (wavelength 535 nm): absorbance (wavelength 455 nm): absorbance (wavelength 593 nm)). The yield of compound (I-4) was 11%.

[0547]

[0548] [Table 1]

[0549] In the cases of Production Examples 1, 3, 5, and 7, which are embodiments of the production method of the present invention, the compound of formula (I) as the target compound was produced with high selectivity. In contrast, in the cases of Production Examples 2, 4, 6, and 8, which are comparative examples of the production method of the present invention, a mixture of compounds of formulae (I), (II), and (III) was obtained, but the compound of formula (I) as the target compound could not be isolated from the mixture. In addition, the selectivity for the compound of formula (I) was also low.

[0550] <Solubility in cyclohexanone>

[0551] The solubility of the compounds shown in Table 2 in a solvent (cyclohexanone) was measured. The results are shown in Table 2.

[0552] (Solubility determination method)

[0553] The solubility was determined as follows: about 50 mg of the compound (solute) obtained in the examples and comparative examples was weighed into a screw bottle, about 450 mg of cyclohexanone (solvent) was added thereto, the total amount of the solute and the solvent was weighed, and the mixture was stirred for 30 minutes using a stirring rotor. Thereafter, when dissolution was confirmed by visual observation, the solubility was determined according to the following formula (h) from the mass of the solute relative to the total mass of the solute and the solvent. When no dissolution was confirmed by visual observation, the solvent was continuously added at a rate of 100 to 500 mg each time until it dissolved, and the mixture was stirred for 30 minutes using a stirring rotor depending on the degree of addition. When dissolution was confirmed by visual observation, the solubility was determined according to the following formula (h) from the mass of the solute relative to the total mass of the solute and the solvent. The results are shown in Table 2.

[0554] Solubility (%) = (mass of solute) / (total mass of solute and cyclohexanone) × 100 (h)

[0555] [Table 2]

[0556] Compound Solubility [%] Example 1 (I-1) 1.2 Example 2 (I-2) 1.8 Example 3 (I-3) 2.2 Example 4 (I-4) 2.0 Comparative Example 5 (III-1) 0.05 Comparative Example 6 (III-2) 0.2 Comparative Example 7 (III-3) 0.1

[0557] Compounds (I-1) to (I-4) have high solubility in cyclohexanone and good solubility. Due to the high solubility of the compounds of the present invention in cyclohexanone, a uniform resin composition can be produced when manufacturing a color filter. As a result, it is believed that the uniformity of the optical properties of the resulting color filter can also be improved. In contrast, the compounds shown in Comparative Examples 5 to 7 were found to have low solubility in cyclohexanone.

[0558] <Absorption and Transmission Spectra of Compound (I) and Compound (III)>

[0559] In a volumetric flask, the compounds shown in Tables 3 and 4 were dissolved in N,N-dimethylformamide to prepare a solution with a concentration of 0.01 g / L. Using a UV-visible spectrophotometer (V-650DS; manufactured by JASCO Corporation) (quartz cuvette, optical path: 1 cm), the absorption spectrum was measured within the wavelength range of 800 to 300 nm, and the maximum absorption wavelength λ within this wavelength range was determined. max [nm]. Further max The absorbance at φ was normalized to 2 and converted into a transmittance spectrum.

[0560] The average transmittance in the wavelength range of 500 to 600 nm and the minimum transmittance at 630 nm or longer, or the average transmittance in the wavelength range of 430 to 530 nm and the minimum transmittance at 600 nm or longer are calculated.

[0561] The lower the average transmittance in the wavelength range of 500-600nm and the higher the minimum transmittance above 630nm, the more suitable it is for red color filters. Conversely, the lower the average transmittance in the wavelength range of 430-530nm and the higher the minimum transmittance above 600nm, the more suitable it is for orange colorants used in red color filters.

[0562] [Table 3]

[0563]

[0564] [Table 4]

[0565]

[0566] <Thermal Decomposition Starting Temperature of Compound (I)>

[0567] The compounds shown in Table 5 were measured for their thermal decomposition onset temperatures at 5% weight loss using TG-DTA (TG-DTA8122 manufactured by Rigaku Corporation) under a nitrogen atmosphere. All showed a temperature of 300°C or higher, indicating high heat resistance and usefulness as color filters.

[0568] [Table 5]

[0569] Colorant compounds Thermal decomposition starting temperature [℃] Example 1 (I-1) 352 Example 2 (I-2) 331 Example 3 (I-3) 331 Example 4 (I-4) 308

[0570] <Synthesis Example 16: Production of Alkali-Soluble Resin B1>

[0571] A suitable amount of nitrogen was introduced into a flask equipped with a reflux cooler, a dropping funnel, and a stirrer to replace the atmosphere with nitrogen. 280 parts of propylene glycol monomethyl ether acetate was added and heated to 80°C while stirring. Subsequently, 38 parts of acrylic acid and 3,4-epoxytricyclo[5.2.1.02，6 ]Decan-8-yl ester and 3,4-epoxytricyclo[5.2.1.0 2,6 ] A mixed solution of 289 parts of a mixture of 9-decane esters (containing a ratio of 1:1 by molar ratio) and 125 parts of propylene glycol monomethyl ether acetate. On the other hand, a solution prepared by dissolving 33 parts of 2,2-azobis(2,4-dimethylvaleronitrile) in 235 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After the addition was completed, the mixture was kept at 80°C for 4 hours and then cooled to room temperature to obtain a copolymer (resin B1) solution having a solid content of 35.1% and a viscosity of 125 mPa·s measured with a B-type viscometer (23°C). The weight average molecular weight Mw of the resulting copolymer was 9.2×10 3 The dispersion degree was 2.08, and the acid value based on solid content was 77 mg-KOH / g. Resin B1 had the following structural units.

[0572]

[0573] <Example 5>

[0574] (1) Preparation of Colored Resin Composition 1

[0575] The respective components were mixed at the following ratios to obtain a colored resin composition 1.

[0576]

[0577] (2) Preparation of Colored Resin Composition 1'

[0578] Next, each component was mixed at the following ratio to obtain a colored resin composition 1'.

[0579]

[0580] <Examples 6 to 8>

[0581] Instead of the compound represented by formula (I-1) in Example 1, the following compound was used:

[0582] Compound represented by formula (I-2) (Example 6)

[0583] Compound represented by formula (I-3) (Example 7)

[0584] Compound represented by formula (I-4) (Example 8)

[0585] Otherwise, colored resin compositions 2 to 4 were prepared in the same manner as in Example 5, and the same operation as in Example 16 was performed to obtain colored resin compositions 2' to 4'.

[0586] <Production of Colored Coating Films (Color Filters)>

[0587] The colored resin compositions 1' to 4' obtained in Examples 5 to 8 were applied onto a 5 cm square glass substrate (EAGLE XG; manufactured by CORNING) by spin coating so that the film thickness after post-baking was 2 μm. The resulting layer was pre-baked at 100°C for 3 minutes to form a colored composition layer. After cooling, the colored resin composition was exposed to light at 80 mJ / cm2 in an air atmosphere using an exposure machine (TME-150RSK; manufactured by TOPCON Co., Ltd.). 2 The colored composition layer formed on the substrate was irradiated with light at an exposure dose of 100 nm (based on 365 nm). After the light irradiation, the layer was post-baked in an oven at 230° C. for 30 minutes to obtain a colored coating film.

Claims

1. A compound represented by formula (I): In formula (I), R 1 ~R 10 Each independently represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, a halogen atom, a hydroxyl group, or a carboxyl group, wherein the methylene group contained in the hydrocarbon group may be substituted with -O-, -CO-, or -N(R B1 )-,R 2 and R 5 、R 3 and R 6 、R 4 and R 7 、R 5 and R 8 、R 7 and R 10 , and / or R 9 and R 10 can bond to each other to form a ring, R B1 each independently represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, R A1 and R A2 、R A3 and R A4 , and R A5 and R A6 Each independently represents a hydrogen atom, -C(=O)-OR B3 a group represented by formula (i), or a group represented by formula (ii), In formula (i), * represents A1 and R A2 、R A3 and R A4 , or R A5 and R A6 The bonding site of In formula (ii), R B2 represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, * indicates the same as R A1 and R A2 、R A3 and R A4 , or R A5 and R A6 The bonding site of R B3 each independently represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, in, R A1 ~R A6 At least one of them represents -C(=O)-OR B3 base.

2. The compound according to claim 1, wherein R in formula (I) A1 and R A2 、R A3 and R A4 , and R A5 and R A6 Each independently represents -C(=O)-OR B3 or a group represented by formula (ii), Among them, R A1 and R A2 、R A3 and R A4 , and R A5 and R A6 At least one of them represents -C(=O)-OR B3 base.

3. The compound according to claim 1, wherein R in formula (I) 1 ~R 10 represents a hydrogen atom, R B2 Each independently represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent. 4 . A colorant comprising the compound represented by formula (I) according to claim 1 .

5. The colorant according to claim 4, wherein The compound represented by formula (I) is contained in an amount of 90% by mass or more based on the total amount of the colorant. 6 . A resin composition comprising the compound represented by the formula (I) according to claim 1 and an alkali-soluble resin.

7. A resin composition comprising the colorant according to claim 4 or 5 and an alkali-soluble resin.

8. The resin composition according to claim 6, wherein It further contains a polymerizable compound and a polymerization initiator. 9 . A cured product, which is a cured product of the resin composition according to claim 8 . 10 . A color filter comprising the cured product according to claim 9 . A display device comprising the color filter according to claim 10 . 12 . A solid-state imaging element comprising the color filter according to claim 10 .

13. A method for producing a compound represented by formula (VI), comprising reacting a compound represented by formula (IV) with a compound represented by formula (Vi) or a compound represented by formula (V-ii) in the presence of a catalyst. In formula (IV), R 1’ 、R 4’ 、R 7’ 、R 8’ 、R 9’ and R 10’ Each independently represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, a halogen atom, a hydroxyl group, or a carboxyl group, wherein the methylene group contained in the hydrocarbon group may be substituted with -O-, -CO-, or -N(R E1 )-,R 4’ and R 7’ and / or R 7’ and R 10’ can bond to each other to form a ring, R E1 each independently represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, Z 1 and Z 2 each independently represents a bromine atom or an iodine atom, R D1 and R D2 , and R D5 and R D6 Each independently represents a hydrogen atom, -C(=O)-OR B3 a group represented by formula (i), or a group represented by formula (iii), In formula (i), * represents D1 and R D2 , or R D5 and R D6 The bonding site of In formula (iii), R E2 represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, * indicates the same as R D1 and R D2 , or R D5 and R D6 The bonding site of In formulas (Vi) and (V-ii), R 2’ 、R 3’ 、R 5’ and R 6’ Each independently represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, a halogen atom, a hydroxyl group, or a carboxyl group, wherein the methylene group contained in the hydrocarbon group may be substituted with -O-, -CO-, or -N(R E1 )-,R 2’ and R 5’ and / or R 3’ and R 6’ can bond to each other to form a ring, R E1 each independently represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, R D3 and R D4 Each independently represents a hydrogen atom, -C(=O)-OR B3 a group represented by formula (i), or a group represented by formula (iii), A 1 ~A 4 Each independently represents a hydroxyl group, a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, or -OR E3 base, R E3 each independently represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, A 1 and A 2 and / or A 3 and A 4 Indicates -OR E3 Base time, 2-OR E3 The groups can bond to each other to form -OR E4 -represented by a divalent group, R E4 is a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, In formula (VI), R 1’ ~R 10’ and R D1 ~R D6 and R in formula (IV), formula (Vi) and (V-ii) 1’ ~R 10’ and R D1 ~R D6 The meaning is the same.

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