Compound, resin composition, cured product of the resin composition, color filter, display device, and solid-state imaging element

Abstract

To provide a compound having optical properties suitable for use in color filters, exhibiting high solubility in organic solvents, and having excellent heat resistance.SOLUTION: For example, the invention provides a compound having a terrylene skeleton represented by Formula (I-1).SELECTED DRAWING: None

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, and a solid-state imaging device. [Background technology]

[0002] A color filter substrate, a component used in display devices such as liquid crystal display devices, electroluminescent display devices, and plasma displays, as well as solid-state imaging devices such as CCD and CMOS sensors, has a structure in which a black matrix layer and color filters, such as red (R), green (G), and blue (B), for forming pixels, are formed on a transparent substrate, and optionally a protective film is laminated on top of them, with patterned transparent pixel electrodes formed on top of that.

[0003] Known colorants contained in curable resin compositions for forming such color filters include, for example, terylene compounds (Patent Documents 1 and 2). [Prior art documents] [Patent documents]

[0004] [Patent Document 1] Japanese Patent Publication No. 2022-126586 [Patent Document 2] International Publication No. 2009 / 027952 Summary of the Invention [Problem to be solved by the invention]

[0005] Color filters are manufactured by dissolving a coloring compound, such as those disclosed in Patent Documents 1 and 2, in a solvent together with other components such as a curable resin to prepare a curable resin composition, applying the curable resin composition to a substrate, developing the composition into a desired pattern, and then post-baking the composition at a high temperature to crosslink the curable resin. To achieve uniform and high color filter performance, it is considered necessary to thoroughly dissolve each component in an organic solvent, such as cyclohexanone, when manufacturing the curable resin composition. However, some coloring compounds have insufficient solubility in organic solvents. Furthermore, coloring compounds may not be able to withstand high temperatures during post-baking processes, etc., during color filter manufacturing due to their insufficient heat resistance.

[0006] Therefore, an object of the present invention is to provide a compound that has optical properties suitable for color filters and the like, as well as high solubility in organic solvents and high heat resistance. [Means for solving the problem]

[0007] The present inventors have found that the above object can be achieved by the compounds of the present invention described below. That is, the present invention includes the following aspects. [1] A compound represented by formula (I): [ka] [In formula (I), R 1 ~R 5 , R 7 , R 8 , 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 hydroxy group, or a carboxy group, and a methylene group contained in the hydrocarbon group is -O-, -CO-, or -N(R B1 )- may be replaced by R 2 and R 5 , R 4 and R 7 , R 5 and R 8 , and / or R7 and R 10 may be bonded 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 , R A5 and R A6 , and R A7 and R A8 are each independently a hydrogen atom, -C(=O)-OR B3 Group, formula (i): [ka] [In formula (i), * represents R A1 and R A2 , R A3 and R A4 , R A5 and R A6 , or R A7 and R A8 represents a bond with or a group represented by formula (ii): [ka] [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 R A1 and R A2 , R A3 and R A4 , R A5 and R A6 , or R A7 and R A8 represents a bond with represents a group represented by R B3 each independently represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, However, R A1 ~R A8 At least one of the following is -C(=O)-OR B3represents a group.] [2] R in formula (I) A1 and R A2 , R A3 and R A4 , R A5 and R A6 , and R A7 and R A8 are each independently -C(=O)-OR B3 group or a group represented by formula (ii), However, R A1 and R A2 , R A3 and R A4 , R A5 and R A6 , and R A7 and R A8 At least one of the following is -C(=O)-OR B3 The compound according to [1], wherein the compound represents a group. [3] R in formula (I) 1 ~R 5 , R 7 , R 8 , and R 10 represents a hydrogen atom, and R B2 each independently represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent. [4] A resin composition containing a compound represented by formula (I) according to any one of [1] to [3] and an alkali-soluble resin. [5] The resin composition according to [4], further comprising a polymerizable compound and a polymerization initiator. [6] A cured product of the resin composition described in [5]. [7] A color filter comprising the cured product according to [6]. [8] A display device comprising the color filter according to [7]. [9] A solid-state imaging device comprising the color filter according to [7]. [Effects of the Invention]

[0008] According to the present invention, it is possible to provide a compound that has optical properties suitable for a color filter, is highly soluble in organic solvents, and has high heat resistance. DETAILED DESCRIPTION OF THE INVENTION

[0009] Hereinafter, embodiments of the present invention will be described in detail. Note 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 spirit of the present invention. Furthermore, when multiple upper and lower limit values ​​are specified for a specific parameter, any of these upper and lower limit values ​​can be combined to form a suitable numerical range.

[0010] [Compound represented by formula (I)] The present invention relates to a compound of formula (I): [ka] [In formula (I), R 1 ~R 5 , R 7 , R 8 , 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 hydroxy group, or a carboxy group, and a methylene group contained in the hydrocarbon group is -O-, -CO-, or -N(R B1 )- may be replaced by R 2 and R 5 , R 4 and R 7 , R 5 and R 8 , and / or R 7 and R 10 may be bonded 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 , R A5 and R A6 , and R A7 and R A8 are each independently a hydrogen atom, -C(=O)-OR B3 Group, formula (i): [ka] [In formula (i), * represents R A1 and R A2 , R A3 and R A4 , R A5 and R A6 , or R A7 and R A8 represents a bond with or a group represented by formula (ii): [ka] [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 R A1 and R A2 , R A3 and R A4 , R A5 and R A6 , or R A7 and R A8 represents a bond with represents a group represented by R B3 each independently represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, However, R A1 ~R A8 At least one of the following is -C(=O)-OR B3 represents a group.] The present invention provides a compound represented by the following formula: In this specification, the compound represented by formula (I) is also referred to as compound (I). The same applies to other formulas. The symbols in formula (I) will be explained below.

[0011] R in formula (I) 1 ~R 5 , R 7 , R 8 , and R 10each independently represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, a halogen atom, a hydroxy group, or a carboxy group, and a methylene group contained in the hydrocarbon group is -O-, -CO-, or -N(R B1 )- may be replaced by R 2 and R 5 , R 4 and R 7 , R 5 and R 8 , and / or R 7 and R 10 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.

[0012] Examples of the hydrocarbon group having 1 to 20 carbon atoms include aliphatic hydrocarbon groups, aromatic hydrocarbon groups, and combinations thereof, each having 1 to 20 carbon atoms. The aliphatic hydrocarbon group may be saturated or unsaturated, and may be linear or alicyclic.

[0013] Examples of saturated or unsaturated chain hydrocarbon groups include linear alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, and icosyl groups; isopropyl, (1-ethyl)propyl, isobutyl, sec-butyl, tert-butyl, (1-ethyl)butyl, (2-ethyl)butyl, (1-propyl)butyl, isopentyl, neopentyl, tert-pentyl, (2-methyl)pentyl, (1-ethyl)pentyl, (3-ethyl)pentyl, (1-propyl)pentyl, and (1-butyl)pentyl groups; isohexyl group, (2-methyl)hexyl group, (5-methyl)hexyl group, (2-ethyl)hexyl group, (1-butyl)hexyl group, (1-pentyl)hexyl group, (2-methyl)heptyl group, (2-ethyl)heptyl group, (3-ethyl)heptyl group, (1-hexyl)heptyl group, (2-methyl)octyl group, (2-ethyl)octyl group, (1-heptyl)octyl group, Examples include branched alkyl groups such as a (2-ethyl)nonyl group and a (1-octyl)nonyl group; and alkenyl groups such as a vinyl group, a 1-propenyl group, a 2-propenyl group (allyl group), a (1-methyl)ethenyl group, a 2-butenyl group, a 3-butenyl group, a 1,3-butadienyl group, a (1-(2-propenyl))ethenyl group, a (1,2-dimethyl)propenyl group, and a 2-pentenyl group. 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 number of carbon atoms in the unsaturated chain hydrocarbon group is preferably 2 to 18, more preferably 2 to 15, and even more preferably 3 to 12.

[0014] 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; norbornyl, adamantyl, and bicyclo[2.2.2]octyl. The saturated or unsaturated alicyclic hydrocarbon group preferably has 3 to 15 carbon atoms, and more preferably 3 to 12 carbon atoms.

[0015] Examples of the aromatic hydrocarbon group include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a phenanthryl group, an anthryl group, a pyrenyl group, etc. The aromatic hydrocarbon group preferably has 6 to 15 carbon atoms, and more preferably 6 to 12 carbon atoms.

[0016] The hydrocarbon group having 1 to 20 carbon atoms may be a group combining two or more of the above-mentioned chain hydrocarbon groups, alicyclic hydrocarbon groups, and / or aromatic hydrocarbon groups, as long as the upper limit of the carbon number is not more than 20. Such a group may be, for example, a group combining an aromatic hydrocarbon group with at least one group selected from a chain hydrocarbon group, an alicyclic hydrocarbon group, and an aromatic hydrocarbon group, and in such a hydrocarbon group combination, the chain hydrocarbon group may be combined as a divalent group (for example, an alkanediyl group).Examples of combined hydrocarbon groups include aralkyl groups such as benzyl, phenethyl, and 1-methyl-1-phenylethyl; arylalkenyl groups such as phenylethenyl (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, and 3,5-dimethylphenyl. ,5-dimethylphenyl group, 4-vinylphenyl group, o-isopropylphenyl group, m-isopropylphenyl group, p-isopropylphenyl group, 2,3-diisopropylphenyl group, 2,4-diisopropylphenyl group, 2,5-diisopropylphenyl group, 2,6-diisopropylphenyl group, 2,4,6-triisopropylphenyl group, 4-butylphenyl group, o-tert-butylphenyl group, m-tert-butylphenyl group, p-tert-butylphenyl group, 2,6-di(tert-butyl)phenyl group, 3,5- Alkylaryl groups such as 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, and 4-dodecylphenyl; 2,3-dihydro-4-indenyl, 1,2,3,5,6,7-hexahydro-4-s-indacenyl, and 8-methyl-1,2,3,5,6,7-hexahydro-4- Examples of such aryl groups include aryl groups having an alkanediyl group bonded thereto, such as an s-indacenyl group, a 5,6,7,8-tetrahydro-1-naphthyl group, a 5,6,7,8-tetrahydro-2-naphthyl group, a 3-methyl-5,6,7,8-tetrahydro-2-naphthyl group, and a 3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl group; aryl groups having one or more aryl groups bonded thereto, such as a biphenylyl group and a terphenylyl group; a cyclohexylmethylphenyl group, a benzylphenyl group, and a (dimethyl(phenyl)methyl)phenyl group.The hydrocarbon group may be, for example, a hydrocarbon group formed by combining a chain hydrocarbon group and an alicyclic hydrocarbon group, and examples thereof include a 1-methylcyclopropyl group, a 1-methylcyclohexyl group, a 2-methylcyclohexyl group, a 3-methylcyclohexyl group, a 4-methylcyclohexyl group, a 1,2-dimethylcyclohexyl group, a 1,3-dimethylcyclohexyl group, a 1,4-dimethylcyclohexyl group, a 2,3-dimethylcyclohexyl group, a 2,4-dimethylcyclohexyl group, a 2,5-dimethylcyclohexyl group, a 2,6-dimethylcyclohexyl group, a 3,4-dimethylcyclohexyl group, a 3,5-dimethylcyclohexyl group, a 2,2-dimethylcyclohexyl group, and a 3,3-dimethylcyclohexyl group. Examples of the alkyl groups include alicyclic hydrocarbon groups having one or more alkyl groups bonded thereto, such as an alkyl group, a 4,4-dimethylcyclohexyl group, a 2,4,6-trimethylcyclohexyl group, a 2,2,6,6-tetramethylcyclohexyl group, a 3,3,5,5-tetramethylcyclohexyl group, a 4-pentylcyclohexyl group, a 4-octylcyclohexyl group, and a 4-cyclohexylcyclohexyl group; and alkyl groups having one or more alicyclic hydrocarbon groups bonded thereto, such as a cyclopropylmethyl group, a cyclopropylethyl group, a cyclobutylmethyl group, a cyclobutylethyl group, a cyclopentylmethyl group, a cyclopentylethyl group, a cyclohexylmethyl group, a 2-methylcyclohexylmethyl group, a cyclohexylethyl group, and an adamantylmethyl group. The number of carbon atoms in the group formed by combining two or more of the chain hydrocarbon group, the alicyclic hydrocarbon group, and the aromatic hydrocarbon group is preferably 6 to 18, and more preferably 6 to 15.

[0017] Examples of the substituent 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 hydroxy group; an alkoxy group having 1 to 20 carbon atoms, such as a methoxy group or an ethoxy group; an aryloxy group having 6 to 20 carbon atoms, such as a phenyloxy group, a 1-naphthyloxy group or a 2-naphthyloxy group; a thiol group; an alkylthio group having 1 to 20 carbon atoms, such as a methylthio group or an ethylthio group; an allylthio group; an arylthio group having 6 to 20 carbon atoms, such as a phenylthio group, a 1-naphthylthio group or a 2-naphthylthio group; a sulfoxy group; an alkylsulfoxy group having 1 to 20 carbon atoms, such as a methylsulfoxy group or an ethylsulfoxy group; an arylsulfoxy group having 6 to 20 carbon atoms, such as a phenylsulfoxy group, a 1-naphthylsulfoxy group or a 2-naphthylsulfoxy group; a silyl group; a boryl group; a monomethylamino group, a dimethyl ... alkylamino groups having 1 to 20 carbon atoms such as a monophenylamino group, a trimethylamino group, a monoethylamino group, a diethylamino group, or a triethylamino group; arylamino groups having 6 to 20 carbon atoms such as a monophenylamino group, a diphenylamino group, or a triphenylamino group; aralkylamino groups having 7 to 20 carbon atoms such as a benzylamino group; carboxy groups; carbamoyl groups; alkylcarbonyl groups having 2 to 20 carbon atoms such as an acetyl group or a propionyl group; arylcarbonyl groups having 7 to 20 carbon atoms such as a benzoyl group, a 1-naphthylcarbonyl group, or a 2-naphthylcarbonyl group; alkoxycarbonyl groups having 2 to 20 carbon atoms such as a methoxycarbonyl group or an ethoxycarbonyl group; and aryloxycarbonyl groups having 7 to 20 carbon atoms such as a phenyloxycarbonyl group, a 1-naphthyloxycarbonyl group, or a 2-naphthyloxycarbonyl group. When a hydrocarbon group having 1 to 20 carbon atoms has a substituent as described above, the number of carbon atoms in the group after substitution is regarded as the number of carbon atoms in the hydrocarbon group.

[0018] The methylene group (-CH2-) contained in the hydrocarbon group having 1 to 20 carbon atoms is replaced by -O-, -CO- or -N(R B1 )-. In addition, at least one methylene group may be replaced by -O-, -CO- or -N(R B1 The number of carbon atoms before being replaced with - is the number of carbon atoms of the hydrocarbon group. B1each 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 R 1 A preferred description of the hydrocarbon group having 1 to 20 carbon atoms is R B1 The same applies to the hydrocarbon group having 1 to 20 carbon atoms in the above. The methylene group contained in the hydrocarbon group having 1 to 20 carbon atoms is such that one methylene group is -O-, -CO- or -N(R B1 )-, or two or more methylene groups may be each independently replaced by -O-, -CO-, or -N(R B1 )-. Also, two or more methylene groups may be replaced by -N(R B1 )-, which results in R B1 If there are multiple R B1 may be the same or different from each other.

[0019] When at least one methylene group contained in a hydrocarbon group having 1 to 20 carbon atoms is replaced with -O- or -CO-, the number may be 1 or 2 or more. Specific examples of the group in which at least one methylene group (-CH2-) contained in the hydrocarbon group is replaced with -O- or -CO- include groups represented by the following formulae (Y-1) to (Y-60). * represents a bond.

[0020] [ka]

[0021] [ka]

[0022] [ka]

[0023] The methylene group contained in the hydrocarbon group having 1 to 20 carbon atoms is -N(R B1When a methylene group (-CH2-) contained in the hydrocarbon group is replaced by -N(R)-, the number of the methylene group (-CH2-) may be one or more. B1 Specific examples of the group substituted with )- include groups represented by the following formulae (Z-1) to (Z-48), in which * represents a bond.

[0024] [ka]

[0025] [ka]

[0026] The above R 1 ~R 5 , R 7 , R 8 , and R 10 Among them, R 2 and R 5 , R 4 and R 7 , R 5 and R 8 , and / or R 7 and R 10 may be bonded to each other to form a ring. 2 and R 5 etc. are bonded to each other to form a ring, R 2 and R 5 Examples of the group to which the above-mentioned groups are bonded include hydrocarbon groups having 1 to 20 carbon atoms which may have a substituent (the methylene group contained in the hydrocarbon group may be -O-, -CO-, or -N(R B1 )-) ... 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 10The groups to which each is bonded are independently *-CO-O-CO-* or *-CO-N(R B1 )-CO-*, *-CO-O-CO-* or *-CO-N(R B1 )-CO-*, where * represents a bond.

[0027] R 2 and R 5 , R 4 and R 7 , R 5 and R 8 , and / or R 7 and R 10 Examples of the group to which R is bonded include divalent groups represented by the following formulae (H-1) to (H-16). In addition, * in formulae (H-1) to (H-16) indicates that R 2 and R 5 In the case of a group to which R is bonded, 2 and R 5 represents the bond to the skeleton represented by formula (I). 4 and R 7 , R 5 and R 8 , and / or R 7 and R 10 Similarly, in the case of a group to which these are bonded, each of these represents a bond to the skeleton represented by formula (I).

[0028] [ka]

[0029] [ka]

[0030] R in formula (I) A1 and R A2 , R A3 and R A4 , R A5 and R A6 , and R A7 and R A8 are each independently a hydrogen atom, -C(=O)-ORB3 Group, formula (i): [ka] [In formula (i), * represents R A1 and R A2 , R A3 and R A4 , R A5 and R A6 , or R A7 and R A8 represents a bond with or a group represented by formula (ii): [ka] [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 R A1 and R A2 , R A3 and R A4 , R A5 and R A6 , or R A7 and R A8 represents a bond with represents a group represented by R B3 each independently represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, However, R A1 ~R A6 At least one of the following is -C(=O)-OR B3 R represents a group. A1 and R A2 , R A3 and R A4 , R A5 and R A6 , and / or R A7 and R A8 are each independently a hydrogen atom, -C(=O)-OR B3 The group represented by formula (i) or the group represented by formula (ii) means R A1 and R A2 In combination with R A3 and R A4 In combination with RA5 and R A and / or R A7 and R A8 and each combination is independently a combination of a hydrogen atom and a hydrogen atom, or a combination of a hydrogen atom and -C(=O)-OR B3 or in combination with the group -C(=O)-OR B3 Group and -C(=O)-OR B3 It means that the two groups form a group represented by formula (i) and / or the two groups form a group represented by formula (ii). A1 and R A2 , R A3 and R A4 , R A5 and R A6 , and R A7 and R A8 The above description also applies to other descriptions in this specification, and represents the above combination in the same manner.

[0031] 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 which the hydrocarbon group may have include R 1 etc. and R B1 Examples of the hydrocarbon groups and substituents include those described above for .

[0032] The above mentioned R B1 , R B2 and R B3 When is a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, examples of the group include groups represented by the following formulae (D-1) to (D-47) and (G-1) to (G-24), as well as these groups substituted with the substituents described above. * represents a bond.

[0033] [ka]

[0034] [ka]

[0035] Examples of the hydrocarbon group having 1 to 20 carbon atoms in formula (ii) that may have a substituent include the groups represented by the above formulae (G-1) to (G-24), the groups represented by the above formulae (D-1) to (D-47), and these groups substituted with the substituents described above. B2 is preferably a group containing an aromatic group having 6 to 20 carbon atoms, from the viewpoints of the optical properties, solubility in organic solvents, and heat resistance of the compound represented by formula (I).

[0036] Examples of groups containing an aromatic group include aromatic groups such as phenyl, 1-naphthyl, 2-naphthyl, phenanthryl, anthryl, and pyrenyl; groups combining the above aromatic groups with at least one group selected from chain hydrocarbon groups, alicyclic hydrocarbon groups, and aromatic groups (e.g., benzyl and phenethyl); and these groups substituted with the above-described substituents. In the above-described combined groups, the chain hydrocarbon group may be combined as a divalent group (e.g., an alkanediyl or alkenyl group). The aromatic group preferably has 6 to 15 carbon atoms, more preferably 6 to 12 carbon atoms. Specifically, the groups containing an aromatic group 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).

[0037] R in formula (I) A1 ~R A8 At least one of the following is -C(=O)-OR B3 R represents a group. A1 ~R A8 At least one of the following is -C(=O)-OR B3 When the group is present, the optical properties, solubility in organic solvents, and heat resistance of the compound represented by formula (I) can be improved.

[0038] R B2 represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, the hydrocarbon group having 1 to 20 carbon atoms which may have a substituent is, for example, R 1 and the like, and R 1 A preferred description of the hydrocarbon group having 1 to 20 carbon atoms is R B2 The same applies to hydrocarbon groups having 1 to 20 carbon atoms in the above formula.

[0039] In one preferred embodiment of the present invention, R B2is 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. Examples of the group containing an aromatic group having 6 to 20 carbon atoms include hydrocarbon groups containing an aromatic ring such as a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a phenanthryl group, an anthryl group, a pyrenyl group, a benzyl group, and a phenethyl group. The number of carbon atoms in the aromatic hydrocarbon group is preferably 6 to 15, more preferably 6 to 12. Examples of the substituent that the aromatic group having 6 to 20 carbon atoms may have include a halogen atom; a nitrile group; a nitro group; an amino group; a hydroxy group; an alkoxy group having 1 to 14 carbon atoms, such as a methoxy group or an ethoxy group; an aryloxy group having 6 to 14 carbon atoms, such as a phenyloxy group, a 1-naphthyloxy group, or a 2-naphthyloxy group; a thiol group; an alkylthio group having 1 to 20 carbon atoms, such as a methylthio group or an ethylthio group; an allylthio group; an arylthio group having 6 to 20 carbon atoms, such as a phenylthio group, a 1-naphthylthio group, or a 2-naphthylthio group; a sulfoxy group; an alkylsulfoxy group having 1 to 20 carbon atoms, such as a methylsulfoxy group or an ethylsulfoxy group; an arylsulfoxy group having 6 to 20 carbon atoms, such as a phenylsulfoxy group, a 1-naphthylsulfoxy group, or a 2-naphthylsulfoxy group; a silyl group; a boryl group; a monomethylamino group, a dimethyl ... alkylamino groups having 1 to 20 carbon atoms such as a monophenylamino group, a trimethylamino group, a monoethylamino group, a diethylamino group, or a triethylamino group; arylamino groups having 6 to 20 carbon atoms such as a monophenylamino group, a diphenylamino group, or a triphenylamino group; aralkylamino groups having 7 to 20 carbon atoms such as a benzylamino group; carboxy groups; carbamoyl groups; alkylcarbonyl groups having 2 to 20 carbon atoms such as an acetyl group or a propionyl group; arylcarbonyl groups having 7 to 14 carbon atoms such as a benzoyl group, a 1-naphthylcarbonyl group, or a 2-naphthylcarbonyl group; alkoxycarbonyl groups having 2 to 14 carbon atoms such as a methoxycarbonyl group or an ethoxycarbonyl group; and aryloxycarbonyl groups having 7 to 14 carbon atoms such as a phenyloxycarbonyl group, a 1-naphthyloxycarbonyl group, or a 2-naphthyloxycarbonyl group. When an aromatic group having 6 to 20 carbon atoms has a substituent as described above, the number of carbon atoms in the group after substitution is regarded as the number of carbon atoms in the aromatic group.

[0040] R in formula (I) A1 ~R A8 At least one of the following is -C(=O)-OR B3 R represents a group. A1 ~R A8 At least one of the following is -C(=O)-OR B3 When the group is present, the optical properties, solubility in organic solvents, and heat resistance of the compound represented by formula (I) can be improved. R B3 As the group, R in formula (I) 1 and the like, and R 1 etc~R 10 A preferred description of the hydrocarbon group having 1 to 20 carbon atoms is R B3 The same applies to hydrocarbon groups having 1 to 20 carbon atoms in the above formula.

[0041] In one preferred embodiment of the present invention, R B3 R 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 is preferably 2 to 18, more preferably 3 to 16, and even more preferably 4 to 15.

[0042] Specific examples of the compound represented by formula (I) include the following. (1)R A1 and R A2 , R A3 and R A4 , R A5 and R A6 , or R A7 and R A8 One of them is -C(=O)-OR B3 a compound in which the remaining three represent a group of formula (i), (2)R A1 and R A2 , R A3 and R A4 , R A5 and R A6 , or R A7 and RA8 One of them is -C(=O)-OR B3 a compound in which two of the groups represent a group of formula (i) and one of the groups represents a group of formula (ii), (3)R A1 and R A2 , R A3 and R A4 , R A5 and R A6 , or R A7 and R A8 One of them is -C(=O)-OR B3 a compound in which two of the groups represent a group of formula (ii) and one of the groups represents a group of formula (i), (4)R A1 and R A2 , R A3 and R A4 , R A5 and R A6 , or R A7 and R A8 The two are -C(=O)-OR B3 a compound in which two of the groups represent a group of formula (i), (5)R A1 and R A2 , R A3 and R A4 , R A5 and R A6 , or R A7 and R A8 The three are -C(=O)-OR B3 a compound in which one of the groups represents a group of formula (i), (6)R A1 and R A2 , R A3 and R A4 , R A5 and R A6 , or R A7 and R A8 One of them is -C(=O)-OR B3 a compound in which the remaining three represent a group of formula (ii), (7)R A1 and R A2 , R A3 and R A4 , R A5 and R A6 , or R A7 and R A8One of the groups is a hydrogen atom and -C(=O)-OR B3 group, or both -C(=O)-OR B3 and the other represents a hydrogen atom, a hydrogen atom and a -C(=O)-OR group. B3 group, or both -C(=O)-OR B3 a compound in which two of the groups represent a group of formula (ii), (8)R A1 and R A2 , R A3 and R A4 , R A5 and R A6 , or R A7 and R A8 One of the groups is a hydrogen atom and -C(=O)-OR B3 group, or both -C(=O)-OR B3 and the other two are both hydrogen atoms, hydrogen atoms and -C(=O)-OR B3 group, or both -C(=O)-OR B3 a compound in which one of the groups represents a group of formula (ii) (9)R A1 and R A2 , R A3 and R A4 , R A5 and R A6 , and R A7 and R A8 One of the groups is a hydrogen atom and -C(=O)-OR B3 group, or both -C(=O)-OR B3 The other three represent a hydrogen atom, a hydrogen atom and a -C(=O)-OR group. B3 group, or both -C(=O)-OR B3 Compounds representing groups

[0043] Among the above (1) to (9), specific examples of (6) to (9) include the following compounds.

[0044] TIFF2025140650000018.tif160160

[0045] In the above table, (a) is R A1 and RA2 Combination of R A3 and R A4 Combination of R A5 and R A6 combination of or R A7 and R A8 The two groups in one of the combinations are a hydrogen atom and a -C(=O)-OR B3 group, or both -C(=O)-OR B3 (b) means that the two groups are both hydrogen atoms, or a hydrogen atom and a —C(═O)—OR B3 group, or both -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) is preferably a —C(═O)—OR group. B3 It is the base.

[0046] In a preferred embodiment of the present invention, the compound represented by formula (I) is preferably a compound represented by formula (I) in which R A1 and R A2 , R A3 and R A4 , R A5 and R A6 and R A7 and R A8 are each independently -C(=O)-OR B3 group, or a group represented by the formula (ii), provided that R A1 and R A2 , R A3 and R A4 , R A5 and R A6 and R A7 and R A8 At least one of the following is -C(=O)-OR B3 It is a compound representing the group.

[0047] In a more preferred embodiment of the present invention, the compound represented by formula (I) is preferably R in formula (I) A1 and R A2 , R A3 and R A4 , R A5 and R A6 , or R A7 and R A8 three of the groups represented by the formula (ii) are R 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 one is -C(=O)-OR B3 represents a group, and R B3 represents 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 R in formula (I) A1 and R A2 , R A3 and R A4 Or R A5 and R A6 two of the groups represented by the formula (ii) are R 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 are -C(=O)-OR B3 represents a group, and R B3 represents 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 R in formula (I) A1 and R A2 , R A3 and R A4 , R A5 and R A6 , or R A7 and R A8represents a group represented by the formula (ii), and R 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 three are -C(=O)-OR B3 represents a group, and R B3 represents 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 R in formula (I) A1 and R A2 , R A3 and R A4 , R A5 and R A6 , and R A7 and R A8 -C(=O)-OR B3 represents a group, and R B3 is 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).

[0048] In a preferred embodiment of the present invention, the compound represented by formula (I) is preferably a compound represented by formula (I) in which R A1 and R A2 , R A3 and R A4 , R A5 and R A6 , and R A7 and R A8 each independently represents a group of the formula -C(=O)-OR B3 group, or a group represented by the formula (ii), provided that R A1 and R A2 , R A3 and R A4 , R A5 and R A6 , or R A7 and R A8 At least one of the following is -C(=O)-OR B3 It is the base.

[0049] In one preferred embodiment, R A1 and R A2 , R A3 and R A4 , R A5 and R A6 , and R A7 and R A8 are each independently -C(=O)-OR B3 group or the group represented by formula (ii), R B2 and R B3 may be the same or different, but from the viewpoint of the optical properties, solubility in organic solvents, and heat resistance of the compound represented by formula (I), R B3 and R B2 Preferably, at least two of them are different from each other.

[0050] In a preferred embodiment of the present invention, the compound of formula (I) is 1 ~R 5 , R 7 , R 8 , and R 10 represents a hydrogen atom, and R B2 and R B3 are compounds each independently representing a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.

[0051] In a preferred embodiment of the present invention, the compound of formula (I) is 1 ~R 5 , R 7 , R 8 , and R 10 represents a hydrogen atom, and R B2 and R B3 are compounds each independently representing a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.

[0052] In a preferred embodiment of the present invention, the compound represented by formula (I) exhibits a solubility in cyclohexanone of preferably 0.5% or more, more preferably 0.8% or more, even more preferably 1.0% or more, even more preferably 1.5% or more, and particularly preferably 2.0% or more, when measured. The solubility can be measured by the method described in the Examples.

[0053] In a preferred embodiment of the present invention, the compound represented by formula (I) has a thermal decomposition temperature measured using TG-DTA of preferably 300° C. or higher, more preferably 305° C. or higher, and even more preferably 310° C. or higher. The thermal decomposition temperature can be measured, for example, by the method described in the Examples.

[0054] In a preferred embodiment of the present invention, the compound represented by formula (I) has a maximum absorption wavelength λ of preferably 440 to 550 nm, more preferably 445 to 540 nm, and even more preferably 450 to 530 nm, when the absorption spectrum is measured in a wavelength range of 800 to 300 nm using an ultraviolet-visible spectrophotometer with an N,N-dimethylformamide solution of the compound (for example, a concentration of 0.01 g / L) as a measurement sample. max [nm], where λ max When compound (I) contains other compounds as impurities, the λ max The value of λ max In the present invention, the above λ max It is preferable that the following is satisfied.

[0055] In a preferred embodiment of the present invention, the maximum absorption wavelength λ of the absorption spectrum measured in the same manner as above for the compound represented by formula (I) maxWhen the absorption spectrum obtained by adjusting the absorbance at wavelengths [nm] to 2 is converted into a transmission spectrum, the average transmittance [%] in the wavelength range of 400 to 490 nm in the converted transmission spectrum is preferably 35% or less, more preferably 30% or less, and even more preferably 20% or less. Furthermore, the average transmittance [%] in the wavelength range of 600 nm or more in the converted transmission spectrum obtained in the same manner as above is preferably 91% or more, more preferably 93% or more, and even more preferably 95% or more. The smaller the average transmittance in the wavelength range of 400 to 490 nm and the larger the minimum transmittance at wavelengths 600 nm or more, the more optimal the red color filter.

[0056] When compound (I) contains other compounds as impurities, the average transmittance [%] of the mixture containing the impurities may differ from the average transmittance of highly pure compound (I). In the present invention, it is preferable that the colorant containing the compound represented by formula (I) described below also satisfies the above-mentioned average transmittance [%] in the wavelength range of 400 to 490 nm.

[0057] [Method for producing the compound represented by formula (I)] The method for producing compound (I) is not particularly limited, and compound (I) can be produced by various production methods. Specifically, for example, referring to the method described in JP-A-2022-126586, compound (III) having a terylene skeleton is prepared, and then a maleic anhydride compound is reacted to obtain compound (Ir), which is then further reacted with an amine compound to produce a compound represented by formula (I). [ka]

[0058] Alternatively, compound (I) can be produced by obtaining compound (Ir) in the same manner as above and then reacting it with compound (IV-B). [ka]

[0059] In the above formula, R 1 ~R 5 , R 7 , R 8 , 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 hydroxy group, or a carboxy group, and a methylene group contained in the hydrocarbon group is -O-, -CO-, or -N(R B1 )- may be replaced by R 2 and R 5 , R 4 and R 7 , R 5 and R 8 , and / or R 7 and R 10 may be bonded 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 , R A5 and R A6 , and R A7 and R A8 are each independently a hydrogen atom, -C(=O)-OR B3 Group, or formula (ii): [ka] [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 R A1 and R A2 , R A3 and R A4 , R A5 and R A6 , or R A7 and R A8 represents a bond with represents a group represented by RB3 each independently represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, X B represents a halogen atom, and the same applies to the following formulae (III), (IV) and (V).

[0060] Compound (Ir) can be produced by reacting compound (III) with maleic anhydride in the presence of a dehydrogenating agent.

[0061] The amount of maleic anhydride used is usually 2 to 1,000 moles, preferably 2 to 800 moles, more preferably 2 to 600 moles, per mole of compound (III).

[0062] The dehydrogenating agent eliminates hydrogen from a six-membered ring compound to aromatize it. Preferred dehydrogenating agents include chloranil, p-benzoquinone, 2,5-dichloro-p-quinone, 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, tetramethyl-p-quinone, 2,5-diphenyl-p-quinone, and bromanil, and more preferred are chloranil and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone.

[0063] The reaction temperature is usually 20°C or higher and 300°C or lower.

[0064] Compound (I) can be produced by reacting compound (Ir) with compound (IV-A).

[0065] The amount of compound (IV-A) used is usually 2 to 20 moles, preferably 2 to 16 moles, and more preferably 2 to 10 moles, per mole of compound (Ir).

[0066] The reaction may be carried out in a solvent, such as water, nitrile solvents such as acetonitrile, alcohol solvents such as methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1-octanol, and phenol, ether solvents such as diethyl ether and tetrahydrofuran, ketone solvents such as acetone and methyl isobutyl ketone, ester solvents such as ethyl acetate, aliphatic hydrocarbon solvents such as hexane, aromatic hydrocarbon solvents such as toluene, halogenated hydrocarbon solvents such as methylene chloride, chloroform, and 1,2-dichlorobenzene, amide solvents such as N,N-dimethylformamide and N-methylpyrrolidone, sulfoxide solvents such as dimethyl sulfoxide, carboxylic acid solvents such as acetic acid, propionic acid, and butyric acid, and imidazole.

[0067] The amount of the solvent used is usually 1 to 1000 parts by mass per part by mass of compound (Ir).

[0068] The reaction temperature is usually from -100°C to 300°C.

[0069] Compound (I) can be produced by reacting compound (Ir) with compound (IV-B) and compound (IV-C) in the presence of a base.

[0070] X B Examples of the halogen atom represented by the formula (I) include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and a bromine atom or an iodine atom is preferred.

[0071] Examples of the compound represented by formula (IV-B) include 1-propanol, 1-butanol, 1-pentanol, 1-hexanol, 2-ethylhexanol, 1-heptanol, 1-octanol, 1-hexanol, benzyl alcohol, and cyclohexanemethanol.

[0072] The amount of compound (IV-B) used is usually 4 to 80 moles, preferably 4 to 32 moles, and more preferably 4 to 20 moles, per mole of compound (Ir).

[0073] Examples of the compound represented by formula (IV-C) include 1-bromopropane, 1-bromobutane, 1-bromopentane, 1-iodopentane, 1-bromohexane, 1-iodohexane, 1-bromo-2-ethylhexane, 1-iodo-2-ethylhexane, 1-bromoheptane, 1-iodoheptane, 1-bromooctane, 1-iodooctane, 1-bromohexane, 1-iodohexane, benzyl bromide, benzyl iodide, cyclohexylmethyl bromide, and cyclohexylmethyl iodide.

[0074] The amount of the compound represented by formula (IV-C) used is usually 2 to 40 moles, preferably 2 to 120 moles, per mole of the compound represented by formula (Ir).

[0075] Examples of the base to be used in the reaction of the compound represented by Formula (Ir) with the compounds represented by Formula (IV-B) and Formula (IV-C) include organic bases such as triethylamine, 4-(N,N-dimethylamino)pyridine, pyridine, piperidine, 1,8-diazabicyclo[5.4.0]undecene, and 1,5-diazabicyclo[4.3.0]nonene; metal alkoxides such as sodium methoxide, sodium ethoxide, sodium tert-butoxide, and potassium tert-butoxide; organometallic compounds such as methyllithium, butyllithium, tert-butyllithium, and phenyllithium; and inorganic bases such as sodium bicarbonate, potassium bicarbonate, sodium carbonate, potassium carbonate, lithium hydroxide, sodium hydroxide, and potassium hydroxide, with organic bases being preferred.

[0076] The amount of the base used is usually 0.2 to 200 moles, preferably 2 to 80 moles, per mole of the compound represented by formula (Ir).

[0077] The reaction of the compound represented by Formula (Ir) with the compounds represented by Formula (IV-B) and Formula (IV-C) may be carried out in a solvent. Examples of such a solvent include water; nitrile solvents such as acetonitrile; alcohol solvents such as methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1-octanol, and phenol; ether solvents such as diethyl ether and tetrahydrofuran; ketone solvents such as acetone and methyl isobutyl ketone; ester solvents such as ethyl acetate; aliphatic hydrocarbon solvents such as hexane; aromatic hydrocarbon solvents such as toluene; halogenated hydrocarbon solvents such as methylene chloride, chloroform, and 1,2-dichlorobenzene; amide solvents such as N,N-dimethylformamide and N-methylpyrrolidone; sulfoxide solvents such as dimethyl sulfoxide; carboxylic acid solvents such as acetic acid, propionic acid, and butyric acid; and imidazole. Among these, amide solvents are preferred, and N,N-dimethylformamide is more preferred.

[0078] The amount of the solvent used is usually 0.1 to 1000 parts by mass per part by mass of the compound represented by formula (Ir).

[0079] In addition to the above, the compound represented by formula (I) can also be produced by reacting compound (III) with compound (IV-D) or compound (IV-E) in the presence of a dehydrogenating agent. The wavy line in compound (IV-E) represents a bond that may be either cis or trans. [ka]

[0080] The compound of formula (I) may be a compound of formula (IV): [ka] and a compound represented by formula (Vi) or a compound represented by formula (V-ii): [ka] Alternatively, a compound represented by formula (IV'-i) or a compound represented by formula (IV'-ii): [ka] and a compound represented by formula (V'): [ka] and in the presence of a catalyst, a phosphine ligand, and a base. The compound obtained by the reaction can be used as the compound (III) to obtain the compound represented by the formula R A1 and R A2 and R A3 and R A4 It is possible to prepare compounds of formula (I) having different substituents in Z in formula (IV) and formula (V'). 1 and Z 2 each independently represents a bromine atom or an iodine atom, and is preferably a bromine atom. 1 ~A 4 are each independently a hydroxy group, a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, or -OR E3 represents a group, and 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 R 1 Examples of the groups exemplified above with respect to A etc. 1 and A 2 , and / or A 3 and A 4 -OR E3 When representing a group, two -OR E3 The groups are bonded to each other to form -OR E4 -, and R E4 R 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, is R 1In the groups exemplified above with respect to the above, examples include divalent groups in which one hydrogen atom is replaced by a bond.

[0081] The catalyst is not particularly limited as long as it promotes the reaction of the above compounds. Examples include tris(dibenzylideneacetone)dipalladium(0), bis(dibenzylideneacetone)palladium(0), palladium(II) acetate, palladium(II) chloride, sodium tetrachloropalladate(II), palladium(II)(π-cinnamyl)chloride (dimer), allylpalladium(II) chloride dimer, bis(benzonitrile)palladium(II) dichloride, and bis(acetonitrile)palladium(II) dichloride. From the viewpoint of suppressing by-products, bis(dibenzylideneacetone)palladium(0) is more preferred. The amount of 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), Compound (IV'-i), or Compound (IV'-ii) from the viewpoints of high reactivity and suppressing impurities.

[0082] Examples of the phosphine ligand include tributylphosphine, tri-tert-butylphosphine, tricyclohexylphosphine, triphenylphosphine, tri(o-tolyl)phosphine, tri(m-tolyl)phosphine, tri(p-tolyl)phosphine, tris(3-methoxyphenyl)phosphine, tris[3,5-bis(trifluoromethyl)phenyl]phosphine, ethyldiphenylphosphine, tris(2,6-dimethoxyphenyl)phosphine, tris(4-fluorophenyl), diphenylpropylphosphine, di-tert-butylphenylphosphine, tri(2-furyl)phosphine, tri(2-thienyl)phosphine, tris(4-methoxyphenyl)phosphine, tris(2-methoxyphenyl)phosphine, methyldiphenylphosphine, 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)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, dicyclohexyl(1,Monodentate phosphine ligands such as 1-diphenyl-1-propen-2-yl)phosphine, 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]-1,1'-biphenyl, 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene Examples of the phosphine ligand include bidentate phosphine ligands such as 9-dimethylxane, 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. Preferably, the phosphine ligand is a monodentate phosphine ligand. More preferably, tributylphosphine, tri-tert-butylphosphine, or tricyclohexylphosphine is used. Most preferably, the phosphine ligand is tricyclohexylphosphine.

[0083] 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), compound (IV'-i), or compound (IV'-ii).

[0084] Examples of the base include inorganic bases such as hydroxides, carbonates, bicarbonates, phosphates, carboxylates, and alkoxides of alkali metals or alkaline earth metals. The base used here may be in the form of an anhydrous or hydrated substance. Preferred examples include hydroxides, carbonates, bicarbonates, phosphates, and carboxylates of alkali metals or alkaline earth metals, with carbonates and phosphates of alkali metals or alkaline earth metals being more preferred. Preferred alkali metal or alkaline earth metal salts include lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate, calcium carbonate, barium carbonate, lithium phosphate, sodium phosphate, and potassium phosphate, with sodium carbonate, potassium carbonate, and potassium phosphate being more preferred.

[0085] From the viewpoint of high reactivity and suppression of impurities, the amount of 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), compound (IV'-i), or compound (IV'-ii).

[0086] When the above compounds are reacted in the presence of a catalyst, the compounds are usually dissolved in a solvent, mixed, and 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 react these compounds to produce a compound of formula (III). The reaction time may be determined appropriately 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. The compound of formula (III) thus produced can be further subjected to the above reaction to produce a compound represented by formula (I).

[0087] [Coloring Agent] A colorant containing a compound represented by formula (I) is also provided. This colorant is also referred to as colorant (I), and colorant (I) contains at least the compound represented by formula (I) of the present invention. Colorant (I) can be used, for example, as a raw material when producing a composition for forming a color filter. If the colorant contains a large amount of by-products produced during the production of compound (I), the optical properties of compound (I) may be impaired, making it difficult to achieve the desired effect when using the colorant in a color filter, etc. However, particularly when compound (I) is produced by the production method of the present invention, the amount of by-products having a structure similar to compound (I) in a colorant containing compound (I) is significantly reduced. This colorant is a red colorant. When colorant (I) is used in a resin composition, colorant (I) may be used in combination with another colorant, specifically a yellow colorant or an orange colorant.

[0088] From the viewpoint of the optical properties of the colorant, the colorant (I) containing the compound represented by formula (I) preferably contains 90 mass % or more, more preferably 93 mass % or more, even more preferably 95 mass % or more, still more preferably 98 mass % or more, and particularly preferably 99 mass % or more of the compound represented by formula (I) based on the total amount of the colorant.

[0089] [Composition containing a compound represented by formula (I)] The present invention also provides a resin composition containing the compound represented by formula (I) and an alkali-soluble resin. The present invention also provides a resin composition containing the colorant of the present invention and an alkali-soluble resin. The resin composition is a colored resin composition.

[0090] (alkali-soluble resin) 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 to form a photoresist, but an alkali-soluble resin having a carboxylic acid is preferred. The alkali-soluble resin is also referred to as resin (B). Examples of resin (B) include the following resins [K1] to [K6]. Resin [K1]: a copolymer having structural units derived from at least one member (a) (hereinafter sometimes referred to as "(a)") selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic acid anhydrides, and structural units derived from a monomer (b) (hereinafter sometimes referred to as "(b)") having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond; Resin [K2]: a copolymer having structural units derived from (a), structural units derived from (b), and structural units derived from a monomer (c) copolymerizable with (a) (however, different from (a) and (b)) (hereinafter, sometimes referred to as "(c)"); Resin [K3]: a copolymer having structural units derived from (a) and structural units derived from (c); Resin [K4]: a copolymer having a structural unit derived from (a) to which (b) has been added, and a structural unit derived from (c); Resin [K5]: a copolymer having a structural unit derived from (b) to which (a) has been added, and a structural unit derived from (c); Resin [K6]: A copolymer having a structural unit derived from (c) and a structural unit obtained by adding (a) to a structural unit derived from (b) and further adding a carboxylic acid anhydride.

[0091] Examples of the monomer (a) include unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, and o-, m-, and p-vinylbenzoic acid; Unsaturated dicarboxylic acids such as maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyltetrahydrophthalic acid, and 1,4-cyclohexenedicarboxylic acid; Bicyclounsaturated compounds containing a carboxy group, such as methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo[2.2.1]hept-2-ene, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene, 5-carboxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-carboxy-6-methylbicyclo[2.2.1]hept-2-ene, and 5-carboxy-6-ethylbicyclo[2.2.1]hept-2-ene; carboxylic acid anhydrides such as the anhydrides of the above unsaturated dicarboxylic acids except fumaric acid and mesaconic acid; Unsaturated mono[(meth)acryloyloxyalkyl] esters of divalent or higher polyvalent carboxylic acids, such as mono[2-(meth)acryloyloxyethyl] succinate and mono[2-(meth)acryloyloxyethyl] phthalate; Unsaturated acrylates containing a hydroxy group and a carboxy group in the same molecule, such as α-(hydroxymethyl)acrylic acid; and the like. Among these, acrylic acid, methacrylic acid, maleic anhydride, etc. are preferred from the viewpoint of copolymerization reactivity and solubility of the resulting resin in an alkaline aqueous solution. In this specification, "(meth)acrylic acid" refers to at least one selected from the group consisting of acrylic acid and methacrylic acid. The terms "(meth)acryloyl" and "(meth)acrylate" also have the same meaning.

[0092] Monomer (b) refers to a polymerizable compound having a cyclic ether structure having 2 to 4 carbon atoms (for example, at least one selected from the group consisting of an oxirane ring, an oxetane ring, and a tetrahydrofuran ring (oxolane ring)) and an ethylenically unsaturated bond. Monomer (b) is preferably a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth)acryloyloxy group.

[0093] Examples of the monomer (b) include a monomer having an oxiranyl group and an ethylenically unsaturated bond (hereinafter, sometimes referred to as "monomer (b1)"), a monomer having an oxetanyl group and an ethylenically unsaturated bond (hereinafter, sometimes referred to as "monomer (b2)"), and a monomer having a tetrahydrofuryl group and an ethylenically unsaturated bond (hereinafter, sometimes referred to as "monomer (b3)").

[0094] Examples of the monomer (b1) include a monomer having a structure in which an unsaturated aliphatic hydrocarbon is epoxidized (hereinafter, may be referred to as "monomer (b1-1)") and a monomer having a structure in which an unsaturated alicyclic hydrocarbon is epoxidized (hereinafter, may be referred to as "monomer (b1-2)").

[0095] As the monomer (b1-1), a monomer having a glycidyl group and an ethylenically unsaturated bond is preferred. Specific examples of the monomer (b1-1) include glycidyl (meth)acrylate, β-methylglycidyl (meth)acrylate, β-ethylglycidyl (meth)acrylate, glycidyl vinyl ether, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether, α-methyl-o-vinylbenzyl glycidyl ether, α-methyl-m-vinylbenzyl glycidyl ether, α-methyl-p-vinylbenzyl glycidyl ether, 2,3-bis( glycidyloxymethyl)styrene, 2,4-bis(glycidyloxymethyl)styrene, 2,5-bis(glycidyloxymethyl)styrene, 2,6-bis(glycidyloxymethyl)styrene, 2,3,4-tris(glycidyloxymethyl)styrene, 2,3,5-tris(glycidyloxymethyl)styrene, 2,3,6-tris(glycidyloxymethyl)styrene, 3,4,5-tris(glycidyloxymethyl)styrene, 2,4,6-tris(glycidyloxymethyl)styrene, and the like.

[0096] Examples of the monomer (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).

[0097] [ka]

[0098] In formula (BI) and formula (BII), R a and R b are each independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the hydrogen atom contained in the alkyl group may be substituted with a hydroxy group. X a and X b are, independently of each other, a single bond, *-R c -, *-R c -O-, *-R c -S- or *-R c represents -NH-. R c represents an alkanediyl group having 1 to 6 carbon atoms. * represents a bond to O.

[0099] 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.

[0100] Examples of alkyl groups in which a hydrogen atom is substituted with a hydroxy group include a hydroxymethyl group, a 1-hydroxyethyl group, a 2-hydroxyethyl group, a 1-hydroxypropyl group, a 2-hydroxypropyl group, a 3-hydroxypropyl group, a 1-hydroxy-1-methylethyl group, a 2-hydroxy-1-methylethyl group, a 1-hydroxybutyl group, a 2-hydroxybutyl group, a 3-hydroxybutyl group, and a 4-hydroxybutyl group.

[0101] R a and R b Preferred examples of the alkyl group include a hydrogen atom, a methyl group, a hydroxymethyl group, a 1-hydroxyethyl group, and a 2-hydroxyethyl group, and more preferred examples include a hydrogen atom and a methyl group.

[0102] 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.

[0103] X a and X b Preferred examples of the alkyl group include a single bond, a methylene group, an ethylene group, a *-CH2-O- (* represents a bond to O) group, and a *-CH2CH2-O- group, and more preferred examples include a single bond and a *-CH2CH2-O- group (* represents a bond to O).

[0104] The compound represented by formula (BI) and the compound represented by formula (BII) may be used alone, or the compound represented by formula (BI) and the compound represented by formula (BII) may be used in combination. When these are used in combination, the content ratio of the compound represented by formula (BI) and the compound represented by formula (BII) is preferably 5:95 to 95:5, more preferably 10:90 to 90:10, and even more preferably 20:80 to 80:20, on a molar basis.

[0105] The monomer (b2) having an oxetanyl group and an ethylenically unsaturated bond is preferably a monomer having an oxetanyl group and a (meth)acryloyloxy group. 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.

[0106] The monomer (b3) having a tetrahydrofuryl group and an ethylenically unsaturated bond is preferably a monomer having a tetrahydrofuryl group and a (meth)acryloyloxy group. Examples of the monomer (b3) include tetrahydrofurfuryl acrylate (e.g., Viscoat V#150, manufactured by Osaka Organic Chemical Industry Co., Ltd.) and tetrahydrofurfuryl methacrylate.

[0107] Examples of the monomer (c) include methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, sec-butyl (meth)acrylate, tert-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, dodecyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, cyclopentyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, tricyclo[5.2.1.0] 2,6 ]decan-8-yl(meth)acrylate (commonly known in the art as "dicyclopentanyl(meth)acrylate" and sometimes called "tricyclodecyl(meth)acrylate"), tricyclo[5.2.1.0 2,6 ] decan-9-yl (meth)acrylate, tricyclo[5.2.1.0 2,6 ]decen-8-yl(meth)acrylate (commonly known in the art as "dicyclopentenyl(meth)acrylate"), tricyclo[5.2.1.0 2,6](meth)acrylic acid esters such as decene-9-yl (meth)acrylate, dicyclopentanyloxyethyl (meth)acrylate, isobornyl (meth)acrylate, adamantyl (meth)acrylate, allyl (meth)acrylate, propargyl (meth)acrylate, phenyl (meth)acrylate, naphthyl (meth)acrylate, and benzyl (meth)acrylate; hydroxy group-containing (meth)acrylic acid esters such as 2-hydroxyethyl (meth)acrylate and 2-hydroxypropyl (meth)acrylate; dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate, and diethyl itaconate; Bicyclo[2.2.1]hept-2-ene, 5-methylbicyclo[2.2.1]hept-2-ene, 5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxybicyclo[2.2.1]hept-2-ene, 5-hydroxymethylbicyclo[2.2.1]hept-2-ene, 5-(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5-methoxybicyclo[2.2.1]hept-2-ene Bicyclo[2.2.1]hept-2-ene, 5-ethoxybicyclo[2.2.1]hept-2-ene, 5,6-dihydroxybicyclo[2.2.1]hept-2-ene, 5,6-di(hydroxymethyl)bicyclo[2.2.1]hept-2-ene, 5,6-di(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5,6-dimethoxybicyclo[2.2.1]hept bicyclounsaturated compounds such as 5-hydroxy-5-methylbicyclo[2.2.1]hept-2-ene, 5,6-diethoxybicyclo[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; dicarbonyl imide derivatives such as N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimidobenzoate, N-succinimidyl-4-maleimidobutyrate, N-succinimidyl-6-maleimidocaproate, N-succinimidyl-3-maleimidopropionate, and N-(9-acridinyl)maleimide; Examples include vinyl group-containing aromatic compounds such as styrene, o-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, and p-methoxystyrene; vinyl group-containing nitriles such as (meth)acrylonitrile; halogenated hydrocarbons such as vinyl chloride and vinylidene chloride; vinyl group-containing amides such as (meth)acrylamide; esters such as vinyl acetate; and dienes such as 1,3-butadiene, isoprene, and 2,3-dimethyl-1,3-butadiene. Among these, styrene, vinyltoluene, tricyclo[5.2.1.0] and cyclopentyl methyl ether are preferred from the viewpoint of copolymerization reactivity and heat resistance. 2,6 ]Decan-8-yl (meth)acrylate, tricyclo[5.2.1.0 2,6 ] decan-9-yl (meth)acrylate, tricyclo[5.2.1.0 2,6 ]decene-8-yl (meth)acrylate, tricyclo[5.2.1.0 2,6 ]decen-9-yl(meth)acrylate, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo[2.2.1]hept-2-ene, and benzyl(meth)acrylate are preferred.

[0108] In the resin [K1], the ratio of the structural units derived from each of these is as follows: Structural units derived from (a): 2 to 60 mol% Structural units derived from (b): 40 to 98 mol% It is preferred that Structural units derived from (a): 10 to 50 mol% Structural units derived from (b): 50 to 90 mol% It is more preferable that: When the ratio of the structural units 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.

[0109] Resin [K1] can be produced, for example, by the method described in the literature "Experimental Methods of Polymer Synthesis" (written by Takayuki Otsu, published by Kagaku Dojin Co., Ltd., 1st edition, 1st printing, published March 1, 1972) and by reference to the references described in said literature.

[0110] Specifically, a method can be exemplified in which predetermined amounts of (a) and (b), a polymerization initiator, a solvent, and the like are placed in a reaction vessel, and the atmosphere is deoxygenated, for example by replacing oxygen with nitrogen, followed by heating and keeping the temperature while stirring. The polymerization initiator, solvent, and the like used here are not particularly limited, and those commonly used in the relevant 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.). Solvents that dissolve the respective monomers can be used, and examples of the solvents for the resin composition of the present invention include the solvents described below.

[0111] The resulting copolymer may be used as a solution after the reaction as is, or may be a concentrated or diluted solution, or may be extracted as a solid (powder) by a method such as reprecipitation. In particular, by using a solvent contained in the resin composition of the present invention as a solvent during the polymerization, the solution after the reaction can be used as is for preparing the resin composition of the present invention, thereby simplifying the production process of the resin composition of the present invention.

[0112] In the resin [K2], the ratio of the structural units derived from each of these is as follows: Structural units derived from (a): 2 to 45 mol% Structural units derived from (b): 2 to 95 mol% Structural units derived from (c): 1 to 65 mol% It is preferred that Structural units derived from (a): 5 to 40 mol% Structural units derived from (b): 5 to 80 mol% Structural units derived from (c): 5 to 60 mol% It is more preferable that: 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 solvent resistance, heat resistance, and mechanical strength of the resulting optical filter tend to be excellent.

[0113] Resin [K2] can be produced, for example, in the same manner as described above for producing resin [K1].

[0114] In the resin [K3], the ratio of the structural units derived from each of these is as follows: Structural units derived from (a): 2 to 60 mol% Structural units derived from (c): 40 to 98 mol% It is preferred that Structural units derived from (a): 10 to 50 mol% Structural units derived from (c): 50 to 90 mol% It is more preferable that: Resin [K3] can be produced, for example, in the same manner as described above for producing resin [K1].

[0115] Resin [K4] can be produced by obtaining a copolymer of (a) and (c), and then adding the cyclic ether having 2 to 4 carbon atoms contained in (b) to the carboxylic acid and / or carboxylic acid anhydride contained in (a). First, a copolymer of (a) and (c) is produced in the same manner as described for the production of resin [K1]. In this case, the ratio of the structural units derived from each is preferably the same as that described for resin [K3].

[0116] Next, a part of the carboxylic acid and / or carboxylic acid anhydride derived from (a) in the copolymer is reacted with a cyclic ether having 2 to 4 carbon atoms contained in (b). Following the production of the copolymer of (a) and (c), the atmosphere in the flask is replaced with air from nitrogen, and (b), a reaction catalyst for the reaction of a carboxylic acid or a carboxylic acid anhydride with a cyclic ether (e.g., tris(dimethylaminomethyl)phenol, etc.), a polymerization inhibitor (e.g., hydroquinone, etc.), etc. are placed in the flask, and the mixture is reacted, for example, at 60 to 130°C for 1 to 10 hours to produce the resin [K4]. The amount of (b) used is preferably 5 to 80 mol, more preferably 10 to 75 mol, per 100 mol of (a). By using this range, the storage stability of the colored resin composition, the developability when forming a pattern, and the balance of the solvent resistance, heat resistance, mechanical strength, and sensitivity of the resulting pattern tend to be good. Because the reactivity of cyclic ethers is high and unreacted (b) is unlikely to remain, (b1) is preferred as (b) used in resin [K4], and (b1-1) is more preferred. The amount of the reaction catalyst used is preferably 0.001 to 5 parts by mass per 100 parts by mass of the total of (a), (b), and (c).The amount of the polymerization inhibitor used is preferably 0.001 to 5 parts by mass per 100 parts by mass of the total of (a), (b), and (c). The reaction conditions such as the charging method, reaction temperature and time can be appropriately adjusted in consideration of the production equipment, the amount of heat generated by the polymerization, etc. As with the polymerization conditions, the charging method and reaction temperature can be appropriately adjusted in consideration of the production equipment, the amount of heat generated by the polymerization, etc.

[0117] Resin [K5] is obtained in the first step by the same method as in the production of resin [K1] described above, to obtain a copolymer of (b) and (c). As in the above, the obtained copolymer may be used as a solution after the reaction as is, a concentrated or diluted solution, or a solid (powder) obtained by a method such as reprecipitation. The ratios of the structural units derived from (b) and (c) to the total number of moles of all structural units constituting the copolymer are as follows: Structural units derived from (b): 5 to 95 mol% Structural units derived from (c): 5 to 95 mol% It is preferred that Structural units derived from (b): 10 to 90 mol% Structural units derived from (c): 10 to 90 mol% It is more preferable that:

[0118] Furthermore, under the same conditions as in the production method of resin [K4], resin [K5] can be obtained by reacting the cyclic ether derived from (b) contained in the copolymer of (b) and (c) with the carboxylic acid or carboxylic anhydride contained in (a). The amount of (a) used to react with the copolymer is preferably 5 to 80 moles per 100 moles of (b). Because the reactivity of cyclic ethers is high and unreacted (b) is unlikely to remain, (b1) is preferred as (b) used in resin [K5], and (b1-1) is more preferred.

[0119] Resin [K6] is a resin obtained by further reacting resin [K5] with a carboxylic acid anhydride. The hydroxyl group generated by the reaction of a cyclic ether with a carboxylic acid or a carboxylic acid anhydride is reacted with the carboxylic acid anhydride. Examples of the carboxylic acid anhydride include maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride, etc. The amount of the carboxylic acid anhydride used is preferably 0.5 to 1 mole per mole of the amount of (a) used.

[0120] Specific examples of alkali-soluble resins include 3,4-epoxycyclohexylmethyl (meth)acrylate / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6] Decyl acrylate / (meth)acrylic acid copolymer and other resins [K1]; glycidyl (meth)acrylate / benzyl (meth)acrylate / (meth)acrylic acid copolymer, glycidyl (meth)acrylate / styrene / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] Decyl acrylate / (meth)acrylic acid / N-cyclohexylmaleimide copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl acrylate / (meth)acrylic acid / N-cyclohexylmaleimide / 2-hydroxyethyl (meth)acrylate copolymer, 3-methyl-3-(meth)acryloyloxymethyloxetane / (meth)acrylic acid / styrene copolymer, etc. [K2]; benzyl (meth)acrylate / (meth)acrylic acid copolymer, styrene / (meth)acrylic acid copolymer, etc. [K3]; resins obtained by adding glycidyl (meth)acrylate to benzyl (meth)acrylate / (meth)acrylic acid copolymer, resins obtained by adding glycidyl (meth)acrylate to tricyclodecyl (meth)acrylate / styrene / (meth)acrylic acid copolymer, tricyclodecyl Resins such as resins obtained by adding glycidyl (meth)acrylate to a (meth)acrylate / benzyl (meth)acrylate / (meth)acrylic acid copolymer [K4]; resins obtained by reacting a tricyclodecyl (meth)acrylate / glycidyl (meth)acrylate copolymer with (meth)acrylic acid, resins such as resins obtained by reacting a tricyclodecyl (meth)acrylate / styrene / glycidyl (meth)acrylate copolymer with (meth)acrylic acid [K5]; and resins such as resins obtained by reacting a tricyclodecyl (meth)acrylate / glycidyl (meth)acrylate copolymer with (meth)acrylic acid and further reacting tetrahydrophthalic anhydride with the resin [K6].

[0121] From the viewpoint of heat resistance, the alkali-soluble resin is more preferably resin [K1] or resin [K2], and particularly preferably resin [K1].

[0122] The weight-average molecular weight (Mw) of the alkali-soluble resin in terms of polystyrene is preferably 1,000 to 100,000, more preferably 2,000 to 50,000, and even more preferably 3,000 to 30,000. When the weight-average molecular weight is within this range, the solubility of the unexposed areas in a developer tends to be high, and the resulting pattern tends to have high film retention and hardness. The dispersity of the alkali-soluble resin [weight average molecular weight (Mw) / number average molecular weight (Mn)] is preferably 1-6, more preferably 1.001-4, and even more preferably 1.01-4.

[0123] The acid value (solid content equivalent) 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, still 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 measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of resin, and can be determined, for example, by titration with an aqueous potassium hydroxide solution.

[0124] The content of the alkali-soluble resin is preferably 5 to 50 mass %, more preferably 10 to 40 mass %, and even more preferably 15 to 30 mass %, based on 100 mass % of the solid content of the resin composition. When the content of the alkali-soluble resin is within the above range, the solubility of the unexposed area in a developer tends to be high.

[0125] 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 the colorant containing the compound represented by formula (I) and the alkali-soluble resin.

[0126] (polymerizable compound) The polymerizable compound is a compound that can be polymerized by active radicals and / or acids generated from a polymerization initiator, and examples thereof include compounds having a polymerizable ethylenically unsaturated bond, and are preferably (meth)acrylic acid ester compounds.

[0127] Examples of polymerizable compounds having one ethylenically unsaturated bond include nonylphenyl carbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexyl carbitol acrylate, 2-hydroxyethyl acrylate, N-vinylpyrrolidone, and the above-mentioned monomers (a), (b), and (c).

[0128] Examples of polymerizable compounds having two ethylenically unsaturated bonds include 1,6-hexanediol di(meth)acrylate, ethylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, bis(acryloyloxyethyl) ether of bisphenol A, and 3-methylpentanediol di(meth)acrylate.

[0129] 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, tris(2-(meth)acryloyloxyethyl)isocyanurate, ethylenediaminetetraacetic acid ester ... Examples of the dipentaerythritol tetra(meth)acrylate 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.

[0130] The weight average molecular weight of the polymerizable compound is preferably 50 to 4,000, more preferably 70 to 3,500, even more preferably 100 to 3,000, still more preferably 150 to 2,900, and particularly preferably 250 to 1,500.

[0131] 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 even more preferably 20 to 70 mass %, relative to the total amount of solids in the resin composition.

[0132] (Polymerization initiator) The polymerization initiator is not particularly limited as long as it is a compound that generates active radicals, acids, etc. by the action of light or heat and can initiate polymerization, and known polymerization initiators can be used.

[0133] Examples of the polymerization initiator include O-acyloxime compounds, alkylphenone compounds, biimidazole compounds, triazine compounds, and acylphosphine oxide compounds. Examples of these polymerization initiators include compounds described in JP-A-2022-126586.

[0134] The polymerization initiator is preferably a polymerization initiator containing at least one selected from the group consisting of an alkylphenone compound, a triazine compound, an acylphosphine oxide compound, an O-acyloxime compound, and a biimidazole compound, and more preferably a polymerization initiator containing an O-acyloxime compound.

[0135] 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 polymerizable compound contained in the resin composition. When the content of the polymerization initiator is within this range, sensitivity tends to be increased and exposure time tends to be shortened, thereby improving productivity of the color filter.

[0136] The resin composition of the present invention may contain components other than the alkali-soluble resin, the polymerizable compound, and the polymerization initiator. Examples of the other components include other colorants different from the compound represented by formula (I) or the colorant containing the compound represented by formula (I), polymerization initiator aids, solvents, leveling agents, and other components.

[0137] (Other colorants) The resin composition of the present invention may contain, as a colorant, 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.

[0138] The 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, such as solvent dyes, acid dyes, direct dyes, and mordant dyes. Examples of dyes include compounds classified as dyes in the Color Index (published by The Society of Dyers and Colourists) and known dyes listed in Dyeing Notes (Shikisensha). In addition, examples of dyes that can be used based on their chemical structure include azo dyes, cyanine dyes, triphenylmethane dyes, xanthene dyes, anthraquinone dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, azomethine dyes, squarylium dyes, acridine dyes, styryl dyes, coumarin dyes, quinoline dyes, nitro dyes, and phthalocyanine dyes. Among these, organic solvent-soluble dyes are preferred.

[0139] The pigment (A1-2) is not particularly limited, and any known pigment can be used as long as it is not a compound represented by formula (I), and examples thereof include pigments classified as pigments in the Color Index (published by The Society of Dyers and Colourists). Examples of pigments classified as pigments include yellow pigments such as CI Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 129, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 185, 194, 214, and 231; Orange pigments such as CI Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73; Red pigments such as 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; Blue pigments such as CI Pigment Blue 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 60; Violet pigments such as CI Pigment Violet 1, 19, 23, 32, 36, 38; Green pigments such as CI Pigment Green 7, 36, 58, 59, 62, 63; Brown pigments such as CI Pigment Brown 23 and 25; Black pigments such as CI Pigment Black 1 and 7;

[0140] As the colorant (A1), yellow, red or green dyes and pigments are preferred.

[0141] If necessary, the colorant (A1) may be subjected to a rosin treatment, a surface treatment using a derivative having an acidic or basic group introduced therein, a graft treatment onto the surface of the colorant (A1) using a polymer compound, etc., a particle size reduction treatment using a sulfuric acid atomization method, etc., a washing treatment using an organic solvent or water to remove impurities, a treatment to remove ionic impurities using an ion exchange method, etc. It is preferable that the particle size of the colorant (A1) is approximately uniform.

[0142] The resin composition may contain, as a colorant, a compound represented by formula (I) or a colorant (I) of the present invention containing a compound represented by formula (I), as well as an additional colorant (A1). In this case, the proportion of the colorant (I) (compound (I) or a colorant containing compound (I)) relative to the total amount of all colorants 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, even more preferably 25% by mass or more, and particularly preferably 50% by mass or more. Furthermore, when an additional colorant (A1) is contained, the proportion of the colorant (I) relative to the total amount of all colorants contained in the resin composition is, for example, less than 100% by mass. In this specification, all colorants contained in the resin composition are also referred to as colorant (A). From the viewpoint of optical properties, the amount of the compound represented by formula (X) relative to the total amount of colorant (A) is preferably 0 to 10% by mass, more preferably 0 to 5% by mass, even more preferably 0 to 3% by mass, and even more preferably 0 to 2% by mass.

[0143] When the resin composition contains a solvent, a colorant-containing liquid (sometimes referred to as a coloring composition) containing the colorant (A) and the solvent may be prepared in advance, and the resin composition may then be prepared using the colorant-containing liquid. When the colorant (A) is not soluble in the solvent, for example, when the colorant (A) contains a pigment (A1-2), the colorant-containing liquid can be prepared by dispersing the colorant (A) in a solvent and mixing it. The colorant-containing liquid may contain some or all of the solvent contained in the resin composition.

[0144] The solid content in the colorant-containing liquid is preferably 0.01% by mass or more and 99.99% by mass or less, more preferably 0.1% by mass or more and 99.9% by mass or less, even more preferably 0.1% by mass or more and 99% by mass or less, still more preferably 0.5% by mass or more and 90% by mass or less, and particularly preferably 1% by mass or more and 50% by mass or less, relative to the total amount of the colorant-containing liquid.

[0145] The colorant (A) can be made uniformly dispersed in the solution by adding a dispersant and carrying out a dispersion treatment. When two or more types of colorant (A) are used in combination, each may be dispersed individually, or multiple types may be mixed and dispersed.

[0146] Examples of dispersants include surfactants, which may be cationic, anionic, nonionic, or amphoteric. Specific examples include polyester, polyamine, and acrylic surfactants. These dispersants may be used alone or in combination of two or more. Examples of dispersants by trade name include KP (manufactured by Shin-Etsu Chemical Co., Ltd.), FLORENE (manufactured by Kyoeisha Chemical Co., Ltd.), Solsperse (registered trademark) (manufactured by Zeneca Corporation), EFKA (registered trademark) (manufactured by BASF), AJISPER (registered trademark) (manufactured by Ajinomoto Fine-Techno Co., Ltd.), Disperbyk (registered trademark) (manufactured by BYK), and BYK (registered trademark) (manufactured by BYK). Resin (B), which will be described later, may also be used as the dispersant.

[0147] When a dispersant is used, the amount of the dispersant (solid content) used is usually 1 part by mass to 10,000 parts by mass, preferably 5 parts by mass to 5,000 parts by mass, more preferably 10 parts by mass to 1,000 parts by mass, and even more preferably 15 parts by mass to 800 parts by mass, relative to 100 parts by mass of the colorant (A). When the amount of the dispersant used is within the above range, a colorant-containing liquid in a more uniformly dispersed state tends to be obtained.

[0148] The content of colorant (A) is preferably 0.1% by mass or more and 50% by mass or less, more preferably 0.5% by mass or more and 40% by mass or less, and even more preferably 1% by mass or more and 30% by mass or less, based on the total amount of solids in the resin composition. When the content of colorant (A) is within the above range, the color density when made into a color filter is sufficient, and since the necessary amount of resin (B) can be contained in the composition, a pattern with sufficient mechanical strength can be formed, which is preferable. Here, the "total amount of solids" in this specification refers to the amount obtained by subtracting the content of the solvent from the total amount of the resin composition. The total amount of solids and the content of each component relative to the total amount of solids can be measured by known analytical means such as liquid chromatography or gas chromatography.

[0149] (Polymerization initiator aid) The polymerization initiation aid is a compound or sensitizer used to promote the polymerization of a polymerizable compound whose polymerization has been initiated by a polymerization initiator. When a polymerization initiation aid is contained, it is usually used in combination with a polymerization initiator.

[0150] 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.

[0151] 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, per 100 parts by mass of the total amount of the alkali-soluble resin and polymerizable compound contained in the resin composition.

[0152] (solvent) The solvent is not particularly limited, and any solvent commonly used in the relevant field can be used. Examples of the solvent include ester solvents (solvents containing -COO- in the molecule but not containing -O-), ether solvents (solvents containing -O- in the molecule but not containing -COO-), ether ester solvents (solvents containing -COO- and -O- in the molecule), ketone solvents (solvents containing -CO- in the molecule but not containing -COO-), alcohol solvents (solvents containing OH in the molecule but not containing -O-, -CO-, and -COO-), aromatic hydrocarbon solvents, amide solvents, dimethyl sulfoxide, etc. These solvents may be used alone or in combination of two or more. Examples of these solvents include the solvents described in JP 2022-126586 A.

[0153] As the solvent, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate and cyclohexanone are preferred.

[0154] When a solvent is contained, the content of the solvent is typically 99.99% by mass or less, preferably 40 to 99% by mass, more preferably 50 to 95% by mass, even more preferably 70 to 95% by mass, and even more preferably 75 to 90% by mass, based on the total amount of the resin composition. In other words, the total amount of solids in the resin composition is typically 0.01% by mass or more, preferably 1 to 60% by mass, more preferably 5 to 50% by mass, even more preferably 5 to 30% by mass, and even more preferably 10 to 25% by mass or less. When the solvent content is within the above range, the flatness during application is good, and when a color filter is formed, the color density is not insufficient, which tends to improve the display characteristics.

[0155] (Leveling agent) Examples of leveling agents include silicone surfactants, fluorine surfactants, and silicone surfactants having fluorine atoms. These may have a polymerizable group in the side chain. Examples of these leveling agents include the leveling agents described in JP-A-2022-126586.

[0156] When a leveling agent is contained, the content of the leveling agent is preferably 0.0005 to 1 mass %, more preferably 0.001 to 0.5 mass %, and even more preferably 0.005 to 0.1 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.

[0157] (Other ingredients) The resin composition may contain additives known in the technical field, such as fillers, other polymer compounds, adhesion promoters, quenchers, antioxidants, light stabilizers, chain transfer agents, etc. The content of other components is not particularly limited as long as they do not adversely affect the performance of the resin composition and the color filter obtained from the resin composition, but is usually about 0.0001 to 10% by mass, or 0.0005 to 8% by mass, based on the mass of the resin composition.

[0158] <Method of manufacturing resin composition> The resin composition can be prepared by mixing the compound of the present invention, an alkali-soluble resin, other colorants (if necessary), a polymerizable compound, a polymerization initiator, a solvent, a leveling agent, and other components. Mixing can be carried out using known or conventional equipment and conditions.

[0159] The compound of formula (I), the colorant containing the compound of formula (I), and any other colorants that are optionally used may be mixed with part or all of the solvent in advance and dispersed using a bead mill or the like until the average particle size is approximately 0.2 μm or less. Preferably, these are used in this dispersed state. In this case, if necessary, some or all of the dispersant and alkali-soluble resin may be added. The compound of formula (I), the colorant containing the compound of formula (I), and any other colorants that are optionally used may be dissolved in part or all of the solvent in advance. The desired resin composition can be prepared by mixing the remaining components with the colorant-containing liquid obtained in this manner to a predetermined concentration.

[0160] After mixing the components, the resin composition is preferably filtered through a filter with a pore size of about 0.01 to 10 μm.

[0161] <Method for producing cured resin composition and color filter> A color filter, which may be a color conversion layer, can be formed from the resin composition of the present invention. The color filter can be produced by a method including curing the resin composition of the present invention, and includes 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 including the cured product. Methods for forming a colored pattern in a color filter include photolithography, inkjet printing, and printing. Among these, photolithography is preferred. The photolithography method involves applying the resin composition to a substrate and drying it to form a resin composition layer, exposing the resin composition layer through a photomask, and developing it. In the photolithography method, a colored coating film, which is a cured product of the resin composition layer, can be formed by not using a photomask during exposure and / or not developing. The colored pattern or colored coating film thus formed is the color filter of the present invention, and includes a cured product of the resin composition of the present invention.

[0162] The thickness of the color filter to be produced is not particularly limited and can be adjusted appropriately depending on the purpose and application, and is, for example, 0.1 to 30 μm, preferably 0.1 to 20 μm, and more preferably 0.5 to 6 μm.

[0163] The substrate may be a glass plate such as quartz glass, borosilicate glass, alumina silicate glass, or silica-coated soda lime glass, a resin plate such as polycarbonate, polymethyl methacrylate, or polyethylene terephthalate, silicon, or a substrate having a thin film of aluminum, silver, or a silver / copper / palladium alloy formed thereon. A separate color filter layer, a resin layer, a transistor, a circuit, or the like may be formed on these substrates.

[0164] The formation of each color pixel by photolithography can be carried out using known or conventional equipment and conditions. For example, it can be produced as follows. First, the resin composition is applied onto a substrate, and then dried by heating (pre-baking) and / or drying under reduced pressure to remove volatile components such as solvents, thereby obtaining a smooth colored resin composition layer. Examples of the coating method include spin coating, slit coating, and slit and spin coating. When drying by heating, the temperature 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 is performed, drying is preferably carried out under a pressure of 50 to 150 Pa at a temperature in the range of 20 to 25°C. The film thickness of the resin composition layer is not particularly limited and may be selected appropriately depending on the film thickness of the desired color filter.

[0165] Next, the resin composition layer is exposed through a photomask to form a desired color pattern. The pattern on the photomask is not particularly limited, and a pattern appropriate for the intended application is used. In addition, it is preferable to use an exposure device such as a mask aligner or a stepper, because this allows uniform irradiation of the entire exposure surface with parallel light and allows accurate alignment of the photomask with the substrate on which the resin composition layer is formed.

[0166] The light source used for exposure is preferably a light source that emits light with a wavelength of 250 nm or more and 450 nm or less. For example, light less than 350 nm may be cut using a filter that cuts this wavelength range, or light around 436 nm, 408 nm, and 365 nm may be selectively extracted using a bandpass filter that extracts these wavelength ranges. Specific examples include mercury lamps, light-emitting diodes, metal halide lamps, and halogen lamps.

[0167] A colored pattern is formed on the substrate by bringing the exposed resin composition layer into contact with a developer and developing it. The unexposed portions of the colored resin composition layer are dissolved in the developer and removed by development. The developer is preferably an aqueous solution of an alkaline compound such as potassium hydroxide, sodium bicarbonate, sodium carbonate, or tetramethylammonium hydroxide. The concentration of these alkaline compounds in the aqueous solution is preferably 0.01 to 10% by mass, more preferably 0.03 to 5% by mass. The developer may further contain a surfactant. The development method may be any of a puddle method, a dipping method, a spray method, or the like. Furthermore, the substrate may be tilted at any angle during development. The substrate after development is preferably washed with water.

[0168] Furthermore, it is preferable to post-bake the obtained colored pattern. The post-bake temperature is preferably 150 to 250°C, more preferably 160 to 240°C. The post-bake time is preferably 1 minute to 120 minutes, more preferably 10 minutes to 60 minutes. Compound (I) of the present invention has a very high thermal decomposition onset temperature and is highly heat-resistant. Therefore, even when post-baking is performed at a high temperature for a certain period of time, as described above, no decomposition occurs, and as a result, no decomposition products are present in the resulting color filter. When a colorant with low heat resistance is used, the colorant may partially decompose during the post-baking process, resulting in the inclusion of decomposition products. The inclusion of such decomposition products may impair the optical properties of the color filter. However, when compound (I) of the present invention or a colorant of the present invention containing compound (I) is used, such decomposition can be suppressed, thereby further improving the optical properties. For example, it is believed that the optical properties can be further improved by obtaining a sharp absorption peak and suppressing variations in optical properties within the color filter.

[0169] <Display device and solid-state image sensor> The color filter is useful as a color filter for use in display devices (for example, liquid crystal display devices, organic EL devices, electronic paper, etc.) and solid-state imaging devices, and particularly useful as a color filter for use in organic EL devices. [Example]

[0170] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to the following examples, and it is of course possible to carry out the invention by making appropriate modifications within the scope of the spirit of the invention, and all such modifications are included in the technical scope of the present invention. In the following, unless otherwise specified, "parts" means "parts by mass" and "%" means "% by mass".

[0171] 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 Ltd.).

[0172] 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. Apparatus: HLC-8120GPC (Tosoh Corporation) Column: TSK-GELG2000HXL Column temperature: 40℃ Solvent: tetrahydrofuran Flow rate: 1.0mL / min Solid concentration of the analytical sample: 0.001 to 0.01% by mass Injection volume: 50μL Detector: RI Calibration standard materials: TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Corporation) The ratio of the weight average molecular weight and the number average molecular weight (Mw / Mn) calculated in terms of polystyrene obtained above was taken as the dispersity.

[0173] <Synthesis Example 1> Synthesis of compound (III-1) Compound (III-1) represented by formula (III-1) was obtained according to the description of Synthesis Example 9 of JP 2022-126586 A.

[0174] [ka]

[0175] Identification of Compound (III-1) (Mass spectrometry) Ionization mode = MALDI-TOF + : m / z= 835 Exact Mass: 834

[0176] <Synthesis Example 2> Synthesis of compound (I-r1) 35.0 parts of the compound (III-1) obtained in Synthesis Example 1, 948 parts of maleic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), and 41.2 parts of chloranil (manufactured by Tokyo Chemical Industry Co., Ltd.) were mixed and stirred at 200°C for 24 hours. After cooling to 80°C, the mixture was added dropwise to a solution of 2083 parts of concentrated hydrochloric acid, 23,000 parts of water, and 3,000 parts of acetone, resulting in the formation of a yellow precipitate. The mixture containing this orange precipitate was filtered, and the residue after filtration was washed with 200 parts of water and 100 parts of acetone. The resulting residue was dried under reduced pressure at 60°C to obtain 42.9 parts of a compound represented by formula (I-r1) (yield 100%).

[0177] [ka]

[0178] Identification of compound (I-r1) (Mass spectrometry) Ionization mode = MALDI-TOF - : m / z= 1021 Exact Mass: 1022

[0179] Example 1 Synthesis of Compound (I-1) 22.0 parts of the compound (I-r1) obtained in Synthesis Example 2, 41.4 parts of 1-bromobutane (manufactured by Tokyo Chemical Industry Co., Ltd.), 26.9 parts of 1-butanol (manufactured by Tokyo Chemical Industry Co., Ltd.), 31.5 parts of 1,8-diazabicyclo[5.4.0]-7-undecene (manufactured by Tokyo Chemical Industry Co., Ltd.), and 308 parts of dehydrated N,N-dimethylformamide (manufactured by Tokyo Chemical Industry Co., Ltd.) were mixed and stirred at 60°C for 9 hours. After cooling to 23°C, the solvent was distilled off. The resulting orange residue was purified by silica gel column chromatography (solvent: chloroform) to obtain 20.4 parts of the compound represented by formula (I-1) (yield 75%).

[0180] [ka]

[0181] Identification of Compound (I-1) (Mass spectrometry) Ionization mode = MALDI-TOF + : m / z= 1234 Exact Mass: 1283

[0182] <Synthesis Example 3> Synthesis of compound (Vb) The compound represented by formula (Vb) was obtained according to the synthesis described in Angewandte Chemie, International Edition 2023, 62, e202214997.

[0183] [ka]

[0184] Identification of compound (Vb) (Mass spectrometry) Ionization mode = MALDI-TOF + : m / z= 485 Exact Mass: 484

[0185] <Synthesis Example 4> Synthesis of compound (IV-b) 13.6 parts of compound (IV-a) obtained in the example described in Chemical Communication 2019, 55, 14182-14185, 20.4 parts of bromine (Fujifilm Wako Pure Chemical Industries, Ltd.), and 1508 parts of chlorobenzene (Tokyo Chemical Industry Co., Ltd.) were mixed and stirred at 50 ° C for 4.5 hours. After the reaction was completed, the mixture was cooled to 23 ° C, and 40 parts of sodium sulfite (Kanto Chemical Co., Ltd.) and 1000 parts of water were added, followed by a separation operation. The resulting organic phase was dehydrated with anhydrous sodium sulfate (Kanto Chemical Co., Ltd.). After filtering the sodium sulfate, the solvent was distilled off, and 15.5 parts of the compound represented by formula (IV-b) were obtained as a yellow solid (yield 98%).

[0186] [ka]

[0187] Identification of compound (IV-b) (Mass spectrometry) Ionization mode = MALDI-TOF + : m / z= 560 Exact Mass: 559

[0188] <Synthesis Example 5> Synthesis of compound (IV-c) 12.9 parts of the compound represented by formula (IV-b) obtained in Synthesis Example 4, 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 Pure Chemical Industries, 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 compound represented by formula (IV-c). The precipitated solid was filtered, washed with 18 parts of methanol, and dried under reduced pressure at 60°C, yielding 12.1 parts of the compound represented by formula (IV-c) (yield 87%).

[0189] [ka]

[0190] Identification of compound (IV-c) (Mass spectrometry) Ionization mode = MALDI-TOF + : m / z= 608 Exact Mass: 607

[0191] <Synthesis Example 6> Synthesis of compound (III-2) 14.6 parts of the compound represented by formula (IV-c) obtained in Synthesis Example 5, 12.8 parts of compound (Vb) obtained in Synthesis Example 3, 2.20 parts of tris(dibenzylideneacetone)dipalladium(0) (Tokyo Chemical Industry Co., Ltd.), 2.69 parts of tricyclohexylphosphine (Fujifilm Wako Pure Chemical Industries, Ltd.), 41.2 parts of potassium carbonate (Kanto Chemical Co., Ltd.), and 1,440 parts of dehydrated xylene (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 the precipitation of a solid compound represented by formula (III-2). The precipitated solid was filtered, purified by silica gel column chromatography (solvent: chloroform), and dried under reduced pressure at 60°C, yielding 15.9 parts of the compound represented by formula (III-2) (yield 82%).

[0192] [ka]

[0193] Identification of compound (III-2) (Mass spectrometry) Ionization mode = MALDI-TOF + : m / z= 806 Exact Mass: 805

[0194] <Synthesis Example 7> Synthesis of compound (I-r2) In accordance with the procedure of Synthesis Example 2, except for replacing 35.0 parts of the compound represented by formula (III-1) with 33.8 parts of the compound represented by formula (III-2) obtained in Synthesis Example 6, 41.7 parts of the compound represented by formula (I-r2) were obtained (yield 100%).

[0195] [ka]

[0196] Identification of compound (I-r2) (Mass spectrometry) Ionization mode = MALDI-TOF - : m / z= 992 Exact Mass: 993

[0197] <Example 2> Synthesis of compound (I-2) 22.0 parts of the compound (I-r2) obtained in Synthesis Example 7, 16.1 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 18 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 26.1 parts of the compound represented by formula (I-2) (yield 66%).

[0198] [ka]

[0199] Identification of compound (I-2) (Mass spectrometry) Ionization mode = MALDI-TOF + : m / z= 1313 Exact Mass: 1312

[0200] Example 3 Synthesis of compound (I-3) In accordance with the procedure described in Example 1, except for replacing 22.0 parts of the compound represented by formula (I-r1) with 21.0 parts of the compound represented by formula (I-r2) obtained in Synthesis Example 7, 19.1 parts of the compound represented by formula (I-3) were obtained (yield 72%).

[0201] [ka]

[0202] Identification of compound (I-3) (Mass spectrometry) Ionization mode = MALDI-TOF + : m / z= 1255 Exact Mass: 1254

[0203] <Synthesis Example 8> Synthesis of compound (III-3) According to the description of Synthesis Example 10 of JP 2022-126586, a compound represented by formula (III-3) was obtained.

[0204] [ka]

[0205] Identification of compound (III-3) (Mass spectrometry) Ionization mode = MALDI-TOF + : m / z= 777 Exact Mass: 776

[0206] <Synthesis Example 9> Synthesis of compound (I-r3) In accordance with the procedure of Synthesis Example 2, except for replacing 35.0 parts of the compound represented by formula (III-1) with 32.6 parts of the compound represented by formula (III-3) obtained in Synthesis Example 6, 40.5 parts of the compound represented by formula (I-r3) were obtained (yield 100%).

[0207] [ka]

[0208] Identification of compound (I-r3) (Mass spectrometry) Ionization mode = MALDI-TOF - : m / z= 963 Exact Mass: 964

[0209] Example 4 Synthesis of compound (I-4) The same procedure as in Example 1 was repeated, except that 22.0 parts of the compound represented by formula (I-r1) was replaced with 20.4 parts of the compound represented by formula (I-r3) obtained in Synthesis Example 9, to obtain 19.5 parts of the compound represented by formula (I-4) (yield 75%).

[0210] [ka]

[0211] Identification of compound (I-4) (Mass spectrometry) Ionization mode = MALDI-TOF + : m / z= 1226 Exact Mass: 1225

[0212] <Solubility in cyclohexanone> The solubility of the compounds shown in Table 1 in a solvent (cyclohexanone) was measured. The results are shown in Table 1. (Method for measuring solubility) The solubility was measured by weighing approximately 50 mg of the compound (solute) obtained in each of the Examples and Comparative Examples into a screw tube, adding approximately 450 mg of cyclohexanone (solvent), and then weighing the total amount of solute and solvent. The mixture was then stirred for 30 minutes using a mixing rotor. If dissolution was confirmed visually, the solubility was calculated using the following formula (h) based on the ratio of the solute mass to the total mass of solute and solvent. If dissolution was not confirmed visually, 100 to 500 mg of solvent was added in increments until dissolution occurred, stirring was continued for 30 minutes using a mixing rotor after each addition. When dissolution was confirmed visually, the solubility was calculated using the ratio of the solute mass to the total mass of solute and solvent based on the following formula (h). The results are shown in Table 1. Solubility (%) = (mass of solute) / (total mass of solute and solvent) × 100 (h)

[0213] [Table 1]

[0214] Compounds (I-1) to (I-4) had high solubility in cyclohexanone and good solubility. Because the compounds of the present invention have high solubility in cyclohexanone, it is possible to produce a uniform resin composition when producing a color filter, and as a result, it is thought that the uniformity of the optical properties of the resulting color filter can also be improved. In contrast, it was confirmed that the compounds shown as Comparative Examples 5 to 7 had low solubility in cyclohexanone.

[0215] <Absorption and transmission spectra> In a measuring flask, 0.10 g of each compound shown in Table 2 was dissolved in N,N-dimethylformamide to a volume of 0.02 L, and 0.002 L of this solution was diluted with chloroform to a volume of 0.2 L (concentration: 0.01 g / L). The absorption spectrum was measured in the wavelength range of 800 to 300 nm using a UV-visible spectrophotometer (V-650DS; manufactured by JASCO Corporation) (quartz cell, optical path length: 1 cm). The wavelength at which the absorbance in this absorption spectrum was greatest was defined as the maximum absorption wavelength λ. max [nm] was calculated. max The absorbance at wavelength 400 to 490 nm was set to 2, and the absorbance was normalized and converted into a transmission spectrum. The average transmittance at wavelengths of 400 to 490 nm and the minimum transmittance at 630 nm or more were calculated. The smaller the average transmittance at wavelengths of 400 to 490 nm and the larger the minimum transmittance at 600 nm or more, the more optimal the red color filter.

[0216] [Table 2]

[0217] <Thermal decomposition start temperature> The compounds shown in Table 3 were used as measurement samples and heated under a nitrogen atmosphere using a TG-DTA (TG-DTA8122 manufactured by Rigaku Corporation). The temperature at which a 5% weight loss of the sample was observed was measured as the thermal decomposition onset temperature. All of the compounds of formulas (I-1) to (I-4) showed a thermal decomposition onset temperature of 300°C or higher, demonstrating their high heat resistance and their usefulness as color filters.

[0218] [Table 3]

[0219] Synthesis Example 10: Preparation of alkali-soluble resin B1 A flask equipped with a reflux condenser, a dropping funnel, and a stirrer was filled with nitrogen to replace the atmosphere, and 280 parts of propylene glycol monomethyl ether acetate was added, followed by heating to 80°C with stirring. Next, 38 parts of acrylic acid, 3,4-epoxytricyclo[5.2.1.0] 2,6 ]decan-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 2,6 A mixed solution of 289 parts of a mixture of decan-9-yl acrylate (content ratio 1:1 by molar ratio) and 125 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. Meanwhile, a solution of 33 parts of 2,2-azobis(2,4-dimethylvaleronitrile) dissolved in 235 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After the dropwise 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 with a solids content of 35.1% and a viscosity of 125 mPa·s measured with a Brookfield viscometer (23°C). The weight-average molecular weight Mw of the resulting copolymer was 9.2×10 3 The resin B1 had a polydispersity of 2.08 and an acid value calculated as solid content of 77 mg-KOH / g.

[0220] [ka]

[0221] <Example 5> (1) Preparation of Colored Resin Composition 1 The components were mixed in the following proportions to obtain a colored resin composition 1. (A) Colorant: 2.6 parts of a compound represented by formula (I-1) (B) Resin: 54 parts of resin B1 solution (E) Solvent: 420 parts of propylene glycol monomethyl ether acetate 200 parts cyclohexanone

[0222] (2) Preparation of Colored Resin Composition 1' Next, the components were mixed in the following proportions to obtain a colored resin composition 1'. Colored resin composition 1 478 parts (C) Polymerizable compound: dipentaerythritol hexaacrylate (Kayarad (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 40 parts (D) Polymerization initiator: N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine (Irgacure (registered trademark) OXE 01; manufactured by BASF) 2 parts (F) Leveling agent: Polyether-modified silicone oil (Toray Silicone SH8400: manufactured by Toray Dow Corning Co., Ltd.) 0.15 parts

[0223] <Examples 6 to 8> Instead of the compound represented by formula (I-1) in Example 1, Compound represented by formula (I-2) (Example 6) Compound represented by formula (I-3) (Example 7) Compound represented by formula (I-4) (Example 8) Colored resin compositions 2 to 4 were prepared in the same manner as in Example 5 except that the above was used, and then the same operation as in Example 13 was carried out to obtain colored resin compositions 2' to 4'.

[0224] <Production of colored coating film (color filter)> Each of the colored resin compositions 1' to 4' obtained in Examples 5 to 8 above was applied by spin coating onto a 5 cm square glass substrate (Eagle XG; manufactured by Corning Incorporated) so that the film thickness after post-baking would be 2 μm, and then pre-baked at 100 ° C. for 3 minutes to form a colored composition layer. After cooling, the colored composition layer formed on the substrate was exposed to 80 mJ / cm 2 in an air atmosphere using an exposure machine (TME-150RSK; manufactured by Topcon Corporation). 2 After the light irradiation, the film 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): 【Chemical 1】 [In formula (I), R １ ~R ５ , R ７ , R ８ , 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 hydroxy group, or a carboxy group, and a methylene group contained in the hydrocarbon group is -O-, -CO-, or -N(R Ｂ１ ) - may be replaced by R ２ and R ５ , R ４ and R ７ , R ５ and R ８ , and / or R ７ and R １０ may be bonded 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 , R Ａ５ and R Ａ６ , and R Ａ７ and R Ａ８ are each independently a hydrogen atom, —C(═O)—OR Ｂ３ Group, formula (i): 【Chemistry 2】 [In formula (i), * represents R Ａ１ and R Ａ２ , R Ａ３ and R Ａ４ , R Ａ５ and R Ａ６ , or R Ａ７ and R Ａ８ represents a bond with or a group represented by formula (ii): 【Chemistry 3】 [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 R Ａ１ and R Ａ２ , R Ａ３ and R Ａ４ , R Ａ５ and R Ａ６ , or R Ａ７ and R Ａ８ represents a bond with represents a group represented by R Ｂ３ each independently represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, However, R Ａ１ ~R Ａ８ At least one of the groups is —C(═O)—OR Ｂ３ represents a group.]

2. R in formula (I) Ａ１ and R Ａ２ , R Ａ３ and R Ａ４ , R Ａ５ and R Ａ６ , and R Ａ７ and R Ａ８ are each independently —C(═O)—OR Ｂ３ group or a group represented by formula (ii), However, R Ａ１ and R Ａ２ , R Ａ３ and R Ａ４ , R Ａ５ and R Ａ６ , and R Ａ７ and R Ａ８ At least one of the groups is —C(═O)—OR Ｂ３ 2. The compound of claim 1, wherein the compound represents a group.

3. R in formula (I) １ ~R ５ , R ７ , R ８ , and R １０ represents a hydrogen atom, R Ｂ２ and each independently represent a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.

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

5. The resin composition according to claim 4, further comprising a polymerizable compound and a polymerization initiator.

6. A cured product of the resin composition according to claim 5.

7. A color filter comprising the cured product according to claim 6.

8. A display device comprising the color filter according to claim 7.

9. A solid-state imaging device comprising the color filter according to claim 7.

Images