Method for producing compound and colored resin composition containing the compound

Abstract

To provide a production method that enables stable synthesis of a specified phthalocyanine compound with a predetermined or higher yield, and a colored resin composition that enables formation of a color filter with suppressed brightness irregularities even after long-term usage.SOLUTION: A method for producing compound (I) comprises reacting a specific phthalonitrile compound in the presence of a base and a specific aluminum compound. A colored resin composition comprises a colorant containing the compound (I) and an alkali-soluble resin. [In the formula, at least one of R1 to R16 is a specific aryloxy group].SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a method for producing a compound, and to a colored resin composition, a color filter, a display device, and a solid-state imaging device each containing the compound. [Background technology]

[0002] Phthalocyanine compounds are known as colorants such as dyes and pigments, and for example, a phthalocyanine compound represented by the following formula (I-e16) is disclosed in Non-Patent Document 1. Non-Patent Document 1 describes that the phthalocyanine compound represented by the following formula (II-16) was reacted in the presence of 1,8-diazabicyclo[5.4.0]-7-undecene (DBU) to synthesize the phthalocyanine compound represented by the formula (I-e16) in a yield of 52%.

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

[0004] [Patent Document 1] JP 2009-192661 A [Non-patent literature]

[0005] [Non-Patent Document 1] Dyes and Pigments 88 (2011) 187-194 Summary of the Invention [Problem to be solved by the invention]

[0006] However, the method described in Non-Patent Document 1 has low reproducibility, and the present inventors have been unable to substantially obtain the target compound by the method, and have been unable to reproduce the yield described in Non-Patent Document 1. Therefore, an object of the present invention is to provide a new production method that can stably synthesize a specific phthalocyanine compound in a predetermined yield or higher.

[0007] In addition, color filters used in display devices such as liquid crystal display devices, electroluminescent display devices, and plasma displays, and solid-state imaging devices such as CCD and CMOS sensors are manufactured from colored resin compositions. In particular, it is known that CI Pigment Green 58 is used as a colorant in colored resin compositions for producing green colored filters (green filters) in color filters (Patent Document 1). However, when a color filter formed from a colored resin composition containing CI Pigment Green 58 is applied to a display device, for example, when used for a long time, unevenness may occur due to a difference in brightness between the periphery and center of the colored filter. Therefore, the object of the present invention is to provide a colored resin composition capable of forming a color filter that can suppress uneven brightness even after long-term use. [Means for solving the problem]

[0008] The gist of the present invention is as follows. [1] A colored resin composition comprising a colorant and an alkali-soluble resin, the colorant comprising a compound represented by formula (I): [ka] [In formula (I), R 1 ~R 16 each independently represents a hydrogen atom, a bromine atom, an iodine atom, a hydrocarbon group having 1 to 6 carbon atoms which may have a substituent, a group represented by formula (ia), a group represented by formula (ib), or a group represented by formula (ic), in which -CH2- contained in the hydrocarbon group may be replaced by -O- or -CO-.1 ~R 16 at least one of them represents a group represented by formula (ia), a group represented by formula (ib), or a group represented by formula (ic); when there are a plurality of groups represented by formula (ia), they may be the same or different; when there are a plurality of groups represented by formula (ib), they may be the same or different; when there are a plurality of groups represented by formula (ic), they may be the same or different. [ka] [In formula (ia), R a1 ~R a5 each independently represents a hydrogen atom, a bromine atom, an iodine atom, a carboxy group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced by -O- or -CO-. a1 ~R a5 At least one of represents a bromine atom, an iodine atom, a carboxy group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent. * represents a bond.] [ka] [In formula (ib), R b1 ~R b7 each independently represents a hydrogen atom, a bromine atom, an iodine atom, a carboxy group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced by -O- or -CO-. b1 ~R b7 At least one of represents a bromine atom, an iodine atom, a carboxy group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent. * represents a bond.] [ka] [In formula (ic), R c1 ~Rc7 each independently represents a hydrogen atom, a bromine atom, an iodine atom, a carboxy group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced by -O- or -CO-. c1 ~R c7 At least one of represents a bromine atom, an iodine atom, a carboxy group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent. * represents a bond.] [2] R 1 ~R 4 At least one of the formulas (ia), (ib), or (ic) is a group represented by R 5 ~R 8 At least one of the formulas (ia), (ib), or (ic) is a group represented by R 9 ~R 12 At least one of the formulas (ia), (ib), or (ic) is a group represented by R 13 ~R 16 At least one of the above is a group represented by formula (ia), formula (ib), or formula (ic). [3] R 2 and R 3 At least one of the formulas (ia), (ib), or (ic) is a group represented by R 6 and R 7 At least one of the formulas (ia), (ib), or (ic) is a group represented by R 10 and R 11 At least one of the formulas (ia), (ib), or (ic) is a group represented by R 14 and R 15 At least one of the formulas (ia), (ib), or (ic) is a group represented by R 1 , R 4 , R 5 , R 8 , R 9 , R 12 , R 13 , and R 16 The colored resin composition according to [2], wherein [4] R 2 and R 3 is a group represented by formula (ia), formula (ib), or formula (ic), and R 6 and R 7 is a group represented by formula (ia), formula (ib), or formula (ic), and R 10 and R 11 is a group represented by formula (ia), formula (ib), or formula (ic), and R 14 and R 15 is a group represented by formula (ia), formula (ib), or formula (ic), and R 1 , R 4 , R 5 , R 8 , R 9 , R 12 , R 13 , and R 16 is a hydrogen atom, The colored resin composition according to [3], wherein the four groups represented by the formula (ia), the formula (ib), or the formula (ic) in the formula (I) are the same groups. [5] R 1 , R 5 , R 9 , and R 13 are each independently a group represented by formula (ia), formula (ib), or formula (ic), and R 2 ~R 4 , R 6 ~R 8 , R 10 ~R 12 , and R 14 ~R 16 The colored resin composition according to [2], wherein [6] The colored resin composition according to any one of [1] to [5], further comprising a polymerizable compound and a polymerization initiator. [7] A color filter formed from the colored resin composition according to any one of [1] 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].

[10] A method for producing a compound represented by formula (I) by reacting a compound represented by formulas (II-1) to (II-4) in the presence of a base and a compound represented by formula (III). [ka] [In formula (I), R 1 ~R 16 each independently represents a hydrogen atom, a bromine atom, an iodine atom, a hydrocarbon group having 1 to 6 carbon atoms which may have a substituent, a group represented by formula (ia), a group represented by formula (ib), or a group represented by formula (ic), in which -CH2- contained in the hydrocarbon group may be replaced by -O- or -CO-. 1 ~R 16 at least one of them represents a group represented by formula (ia), a group represented by formula (ib), or a group represented by formula (ic); when there are a plurality of groups represented by formula (ia), they may be the same or different; when there are a plurality of groups represented by formula (ib), they may be the same or different; when there are a plurality of groups represented by formula (ic), they may be the same or different. [ka] [In formula (ia), R a1 ~R a5 each independently represents a hydrogen atom, a bromine atom, an iodine atom, a carboxy group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced by -O- or -CO-. a1 ~R a5 At least one of represents a bromine atom, an iodine atom, a carboxy group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent. * represents a bond.] [ka] [In formula (ib), Rb1 ~R b7 each independently represents a hydrogen atom, a bromine atom, an iodine atom, a carboxy group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced by -O- or -CO-. b1 ~R b7 At least one of represents a bromine atom, an iodine atom, a carboxy group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent. * represents a bond.] [ka] [In formula (ic), R c1 ~R c7 each independently represents a hydrogen atom, a bromine atom, an iodine atom, a carboxy group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced by -O- or -CO-. c1 ~R c7 At least one of represents a bromine atom, an iodine atom, a carboxy group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent. * represents a bond.] [ka] [In formula (III), X M is a halogen atom, a hydroxyl group, or OR M R M represents a hydrocarbon group having 1 to 6 carbon atoms.] [ka] [In formulas (II-1) to (II-4), R 1 ~R 16 has the same meaning as above.]

[11] The method according to

[10] , wherein the amount of the compound represented by formula (III) used is 0.25 mol or more and 0.40 mol or less per 1 mol of the total amount of the compounds represented by formulae (II-1) to (II-4). Effect of the Invention

[0009] According to the production method of the present invention, a specific phthalocyanine compound can be stably synthesized in a predetermined yield or higher. In addition, the production method of the present invention is also preferable in that the specific phthalocyanine compound can be synthesized in a short reaction time. Moreover, according to the colored resin composition of the present invention containing a specific phthalocyanine compound as a colorant, it is possible to form a color filter capable of suppressing uneven brightness even after long-term use. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0010] [Colored resin composition] The present invention encompasses a colored resin composition comprising a colorant (hereinafter, sometimes referred to as colorant (A)) and an alkali-soluble resin (hereinafter, sometimes referred to as resin (B)), wherein the colorant (A) comprises a compound represented by formula (I) described below. It is preferable that the colored resin composition of the present invention further contains at least one (preferably both) of a polymerizable compound (hereinafter, sometimes referred to as a polymerizable compound (C)) and a polymerization initiator (hereinafter, sometimes referred to as a polymerization initiator (D)). It is preferable that the colored resin composition of the present invention further contains a solvent (hereinafter, may be referred to as solvent (E)). The colored resin composition of the present invention may contain a leveling agent (hereinafter, may be referred to as leveling agent (F)). In this specification, the compounds exemplified as each component may be used alone or in combination of two or more kinds, unless otherwise specified.

[0011] <Colorant (A)> The colored resin composition of the present invention contains a compound represented by formula (I) (hereinafter, sometimes referred to as compound (I)) as a colorant. A colored filter formed from a colored resin composition containing compound (I) as a colorant can reduce the brightness difference between the peripheral part and the center part even after long-term use, that is, a color filter with suppressed brightness unevenness can be formed. Hereinafter, the present invention will be described in more detail by listing the partial structures of compound (I).

[0012] [ka] [In formula (I), R 1 ~R 16 each independently represents a hydrogen atom, a bromine atom, an iodine atom, a hydrocarbon group having 1 to 6 carbon atoms which may have a substituent, a group represented by formula (ia), a group represented by formula (ib), or a group represented by formula (ic), in which -CH2- contained in the hydrocarbon group may be replaced by -O- or -CO-. 1 ~R 16 at least one of them represents a group represented by formula (ia), a group represented by formula (ib), or a group represented by formula (ic); when there are a plurality of groups represented by formula (ia), they may be the same or different; when there are a plurality of groups represented by formula (ib), they may be the same or different; when there are a plurality of groups represented by formula (ic), they may be the same or different. [ka] [In formula (ia), R a1 ~R a5 each independently represents a hydrogen atom, a bromine atom, an iodine atom, a carboxy group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced by -O- or -CO-. a1 ~R a5At least one of represents a bromine atom, an iodine atom, a carboxy group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent. * represents a bond.] [ka] [In formula (ib), R b1 ~R b7 each independently represents a hydrogen atom, a bromine atom, an iodine atom, a carboxy group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced by -O- or -CO-. b1 ~R b7 At least one of represents a bromine atom, an iodine atom, a carboxy group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent. * represents a bond.] [ka] [In formula (ic), R c1 ~R c7 each independently represents a hydrogen atom, a bromine atom, an iodine atom, a carboxy group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced by -O- or -CO-. c1 ~R c7 At least one of represents a bromine atom, an iodine atom, a carboxy group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent. * represents a bond.]

[0013] R 1 ~R 16 The hydrocarbon group having 1 to 6 carbon atoms represented by the formula (I) may be either an aliphatic hydrocarbon group or a phenyl group, and the aliphatic hydrocarbon group may be saturated or unsaturated, and may be linear or cyclic (alicyclic hydrocarbon group).

[0014] Examples of saturated chain hydrocarbon groups (hereinafter sometimes referred to as alkyl groups) include linear alkyl groups such as a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, and an n-hexyl group; and branched alkyl groups such as an isopropyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a 1,3-dimethylbutyl group, a 2-methyl-2-pentyl group, and a 2-ethylbutyl group. The alkyl group preferably has 1 to 4 carbon atoms, and more preferably has 1 to 3 carbon atoms.

[0015] Examples of the unsaturated chain hydrocarbon group include alkenyl groups such as ethenyl, propenyl (e.g., 1-propenyl, 2-propenyl), and butenyl (e.g., 1-butenyl, 3-butenyl) groups; and alkynyl groups such as ethynyl, propynyl (e.g., 1-propynyl, 2-propynyl), and butynyl (e.g., 1-butynyl, 3-butynyl) groups. The unsaturated chain hydrocarbon group preferably has 2 to 6 carbon atoms, and more preferably 2 to 4 carbon atoms.

[0016] Examples of the saturated alicyclic hydrocarbon group include cycloalkyl groups such as a cyclopropyl group, a 1-methylcyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group.

[0017] Examples of the unsaturated alicyclic hydrocarbon group include cycloalkenyl groups such as cyclohexenyl groups (for example, cyclohex-1-en-1-yl, cyclohex-2-en-1-yl, and cyclohex-3-en-1-yl).

[0018] The alicyclic hydrocarbon group preferably has 3 to 6 carbon atoms.

[0019] R 1 ~R 16The hydrocarbon group having 1 to 6 carbon atoms represented by the formula (I) may have a substituent. Examples of the substituent include halogen atoms such as fluorine atom, chlorine atom, bromine atom, and iodine atom; hydroxyl group; carboxyl group; unsubstituted amino group; substituted amino groups such as N-methylamino group, N,N-dimethylamino group, N-ethylamino group, N,N-diethylamino group, N-propylamino group, N,N-dipropylamino group, N-isopropylamino group, N,N-diisopropylamino group, N-phenylamino group, N,N-diphenylamino group, and N,N-ethylmethylamino group; cyano group; and the like. Among them, halogen atom is preferable, and chlorine atom is more preferable.

[0020] R 1 ~R 16 has 2 to 6 carbon atoms and has -CH2-, the -CH2- may be replaced with -O- or -CO-, provided that adjacent -CH2- are not simultaneously replaced with -O- in the hydrocarbon group having 1 to 6 carbon atoms, and the terminal -CH2- is not replaced with -O- or -CO-.

[0021] In this specification, when -CH2- in a hydrocarbon group is replaced by -O- or -CO-, the number of carbon atoms in the group replaced by -O- or -CO- means the number of carbon atoms in the hydrocarbon group before being replaced by -O- or -CO-. For example, a *-O-CH2-CH2-CH3 group is a hydrocarbon group having 4 carbon atoms (*-CH2-CH2-CH2-CH3) in which -CH2- is replaced by -O-. In addition, if there are multiple -CH2- that can be replaced in the hydrocarbon group, the number of replacements is not necessarily limited to one. For example, two -CH2- in a hydrocarbon group having 4 carbon atoms (*-CH2-CH2-CH2-CH3) can be replaced with -O- to become *-O-CH2-O-CH3, and one -CH2- can be replaced with -O- and one -CH2- can be replaced with -CO- to become *-O-CO-CH2-CH3 or *-CO-O-CH2-CH3. That is, groups in which two or more -CH2- are replaced with -O- or -CO-, such as *-O-CH2-O-CH3, *-O-CO-CH2-CH3, and *-CO-O-CH2-CH3, are also included in "groups in which -CH2- in a hydrocarbon group having 1 to 6 carbon atoms, which may have a substituent, is replaced with -O- or -CO-".

[0022] R 1 ~R 16 As the hydrocarbon group having 1 to 6 carbon atoms which may have a substituent, represented by the following formula, an alkyl group is preferable.

[0023] R a1 ~R a5 , R b1 ~R b7 and R c1 ~R c7 The hydrocarbon group having 1 to 20 carbon atoms represented by the formula (I) may be any of an aliphatic hydrocarbon group, an aromatic hydrocarbon group, and a combination thereof, and the aliphatic hydrocarbon group may be saturated or unsaturated, and may be linear or cyclic (alicyclic hydrocarbon group).

[0024] Examples of saturated chain hydrocarbon groups (alkyl groups) include linear alkyl groups such as methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, and n-decyl groups; and branched alkyl groups such as isopropyl, isobutyl, sec-butyl, tert-butyl, 1,3-dimethylbutyl, 2-ethylbutyl, 2-methyl-2-pentyl, and 2-ethylhexyl groups. The alkyl group preferably has 1 to 12 carbon atoms, more preferably 1 to 8 carbon atoms, further preferably 1 to 4 carbon atoms, and particularly preferably 1 to 3 carbon atoms.

[0025] Examples of the unsaturated chain hydrocarbon group include alkenyl groups such as ethenyl, propenyl (e.g., 1-propenyl, 2-propenyl), and butenyl (e.g., 1-butenyl, 3-butenyl) groups; and alkynyl groups such as ethynyl, propynyl (e.g., 1-propynyl, 2-propynyl), and butynyl (e.g., 1-butynyl, 3-butynyl) groups. The unsaturated chain hydrocarbon group preferably has 2 to 10 carbon atoms, more preferably 2 to 8 carbon atoms, and further preferably 2 to 4 carbon atoms.

[0026] Examples of the saturated alicyclic hydrocarbon group include cycloalkyl groups such as a cyclopropyl group, a 1-methylcyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a 2-methylcyclohexyl group.

[0027] Examples of the unsaturated alicyclic hydrocarbon group include cycloalkenyl groups such as a cyclohexenyl group (for example, a cyclohex-1-en-1-yl group, a cyclohex-2-en-1-yl group, a cyclohex-3-en-1-yl group), a cycloheptenyl group, and a cyclooctenyl group.

[0028] Examples of the alicyclic hydrocarbon group include polycyclic saturated alicyclic hydrocarbon groups such as a norbornyl group, an adamantyl group, and a bicyclo[2.2.2]octyl group; and polycyclic unsaturated alicyclic hydrocarbon groups such as a norbornenyl group.

[0029] The alicyclic hydrocarbon group preferably has 3-10 carbon atoms, and more preferably 4-8 carbon atoms.

[0030] Examples of the aromatic hydrocarbon group include a phenyl group, an o-tolyl group, an m-tolyl group, a p-tolyl group, a 2,4-dimethylphenyl group, a 2,6-dimethylphenyl group, a 2,4,6-trimethylphenyl group, a 2,4-diisopropylphenyl group, a 2,6-diisopropylphenyl group, a 4-vinylphenyl group, an o-tert-butylphenyl group, an m-tert-butylphenyl group, a p-tert-butylphenyl group, a 2,6-di(tert-butyl)phenyl group, a 3,5-di(tert-butyl)phenyl group, a 1-naphthyl group, a 2-naphthyl group, and a group in which one hydrogen atom has been removed from tetralin.

[0031] The aromatic hydrocarbon group preferably has 6 to 18 carbon atoms, more preferably 6 to 12 carbon atoms, and further preferably 6 to 10 carbon atoms.

[0032] R a1 ~R a5 , R b1 ~R b7 and R c1 ~R c7 The hydrocarbon group represented by the formula (I) may be a group formed by combining the above-listed hydrocarbon groups, so long as the total number of carbon atoms is 20 or less. Examples of the group formed by combining hydrocarbon groups include an aralkyl group and an alkyl group bonded to an alicyclic hydrocarbon group.

[0033] Examples of the aralkyl group include benzyl, (2-methylphenyl)methyl, (3-methylphenyl)methyl, (4-methylphenyl)methyl, (2-ethylphenyl)methyl, (3-ethylphenyl)methyl, (4-ethylphenyl)methyl, (2-(tert-butyl)phenyl)methyl, (3-(tert-butyl)phenyl)methyl, (4-(tert-butyl)phenyl)methyl, (3,5-dimethylphenyl)methyl, 1-phenylethyl, 1-methyl-1-phenylethyl, 1,1-diphenylethyl, (1-naphthyl)methyl, (2-naphthyl)methyl, and 9-fluorenylmethyl. The number of carbon atoms in the aralkyl group is preferably 7 to 18, and more preferably 7 to 12.

[0034] Examples of the alkyl group having an alicyclic hydrocarbon group bonded thereto include a cyclopropylmethyl group, a cyclopropylethyl group, a cyclobutylmethyl group, a cyclohexylmethyl group, a cyclohexylethyl group, an adamantylmethyl group, etc. The number of carbon atoms in the alkyl group having an alicyclic hydrocarbon group bonded thereto is preferably 4 to 20, more preferably 4 to 15, and further preferably 4 to 10.

[0035] R a1 ~R a5 , R b1 ~R b7 and R c1 ~R c7 Examples of the substituent that may be possessed by the hydrocarbon group having 1 to 20 carbon atoms represented by the formula: 1 ~R 16 These are the same as the examples of the substituent that may be possessed by the hydrocarbon group having 1 to 6 carbon atoms, represented by the following formula: Among these, a halogen atom is preferred, and a chlorine atom is more preferred.

[0036] R a1 ~R a5 , R b1 ~R b7 and R c1 ~R c7 When the hydrocarbon group represented by the formula (I) has 2 to 20 carbon atoms and has -CH2-, the -CH2- may be replaced with -O- or -CO-. However, in the hydrocarbon group having 1 to 20 carbon atoms, adjacent -CH2- are not simultaneously replaced with -O-, and the terminal -CH2- is not replaced with -O- or -CO-. In particular, the group in which -CH2- is replaced with -O- or -CO- is preferably an alkoxy group such as a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, or a tert-butoxy group, more preferably an alkoxy group having 1 to 10 carbon atoms, and even more preferably an alkoxy group having 1 to 4 carbon atoms.

[0037] R a1 ~R a5 , R b1 ~R b7 and R c1 ~R c7The hydrocarbon group having 1 to 20 carbon atoms, which may have a substituent represented by the formula (I), is preferably an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, or an aralkyl group having 7 to 20 carbon atoms, more preferably an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms, and even more preferably an alkyl group having 1 to 8 carbon atoms (particularly 1 to 4), a cycloalkyl group having 4 to 8 carbon atoms, an aromatic hydrocarbon group having 6 to 10 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms.

[0038] R a1 ~R a5 , R b1 ~R b7 and R c1 ~R c7 are each independently preferably a hydrogen atom, a bromine atom, an alkoxy group having 1 to 10 carbon atoms, or a hydrocarbon group having 1 to 20 carbon atoms, more preferably a hydrogen atom, a bromine atom, an alkoxy group having 1 to 10 carbon atoms, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, or an aralkyl group having 7 to 20 carbon atoms, and even more preferably a hydrogen atom, a bromine atom, an alkyl group having 1 to 8 (particularly 1 to 4) carbon atoms, a cycloalkyl group having 4 to 8 carbon atoms, an aromatic hydrocarbon group having 6 to 10 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms.

[0039] In the group represented by formula (ia), R a1 ~R a5 Among these, the total number of bromine atoms and iodine atoms is preferably 0 to 3, more preferably 0 to 2, and even more preferably 0 or 1. In the group represented by formula (ib), R b1 ~R b7 Among these, the total number of bromine atoms and iodine atoms is preferably 0 to 3, more preferably 0 to 2, and even more preferably 0 or 1. In the group represented by formula (ic), R c1 ~R c7Among these, the total number of bromine atoms and iodine atoms is preferably 0 to 3, more preferably 0 to 2, and even more preferably 0 or 1.

[0040] In the group represented by formula (ia), R a1 ~R a5 At least one of R is preferably a bromine atom, an iodine atom, a carboxy group, a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, or an alkoxy group having 1 to 10 carbon atoms; a1 ~R a5 More preferably, at least one of R is a bromine atom, a hydrocarbon group having 1 to 20 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms. a1 ~R a5 It is more preferable that at least one of them is a bromine atom, an alkyl group having 1 to 8 carbon atoms (particularly, 1 to 4 carbon atoms), a cycloalkyl group having 4 to 8 carbon atoms, an aromatic hydrocarbon group having 6 to 10 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms. In particular, R a1 ~R a5 Among these, it is preferred that 1 to 3 of them are each independently a bromine atom, an iodine atom, a carboxy group, a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, or an alkoxy group having 1 to 10 carbon atoms, and the remainder are a hydrogen atom; a1 ~R a5 Among R, it is more preferable that 1 to 3 of them are each independently a bromine atom, a hydrocarbon group having 1 to 20 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and the remainder are hydrogen atoms; a1 ~R a5 It is more preferable that 1 to 3 of these are each independently a bromine atom, an alkyl group having 1 to 8 carbon atoms (particularly, 1 to 4), a cycloalkyl group having 4 to 8 carbon atoms, an aromatic hydrocarbon group having 6 to 10 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and the remainder are a hydrogen atom.

[0041] In the group represented by formula (ib), R b1 ~R b7at least one of R is a bromine atom, an iodine atom, a carboxy group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent; b1 ~R b7 At least one of R is preferably a bromine atom or a hydrocarbon group having 1 to 20 carbon atoms. b1 ~R b7 It is more preferable that at least one of them is a bromine atom, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 4 to 8 carbon atoms, an aromatic hydrocarbon group having 6 to 10 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms. In particular, R b1 ~R b7 Among these, it is preferred that 1 to 3 of them are independently a bromine atom, an iodine atom, a carboxy group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and the remainder are hydrogen atoms; b1 ~R b7 It is more preferable that 1 to 3 of R are independently a bromine atom or a hydrocarbon group having 1 to 20 carbon atoms, and the remainder are hydrogen atoms. b1 ~R b7 It is more preferable that 1 to 3 of these are each independently a bromine atom, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 4 to 8 carbon atoms, an aromatic hydrocarbon group having 6 to 10 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms, and the remainder are a hydrogen atom.

[0042] In the group represented by formula (ic), R c1 ~R c7 at least one of R is a bromine atom, an iodine atom, a carboxy group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent; c1 ~R c7 At least one of R is preferably a bromine atom or a hydrocarbon group having 1 to 20 carbon atoms. c1 ~R c7 It is more preferable that at least one of them is a bromine atom, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 4 to 8 carbon atoms, an aromatic hydrocarbon group having 6 to 10 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms. In particular, R c1 ~R c7Among these, it is preferred that 1 to 3 of them are independently a bromine atom, an iodine atom, a carboxy group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and the remainder are hydrogen atoms; c1 ~R c7 It is more preferable that 1 to 3 of R are independently a bromine atom or a hydrocarbon group having 1 to 20 carbon atoms, and the remainder are hydrogen atoms. c1 ~R c7 It is more preferable that 1 to 3 of these are each independently a bromine atom, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 4 to 8 carbon atoms, an aromatic hydrocarbon group having 6 to 10 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms, and the remainder are a hydrogen atom.

[0043] Specific examples of the group represented by formula (ia) include groups represented by the following formulae (i-a1) to (i-a17).

[0044] [ka]

[0045] Specific examples of the group represented by formula (ib) include groups represented by the following formulae (i-b1) to (i-b4).

[0046] [ka]

[0047] Specific examples of the group represented by formula (ic) include groups represented by the following formulae (i-c1) to (i-c5).

[0048] [ka]

[0049] R 1 ~R 16are each independently preferably a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a group represented by formula (ia), more preferably a hydrogen atom or a group represented by formula (ia).

[0050] In compound (I), R 1 ~R 16 At least one of the formula (ia), formula (ib) or a group represented by formula (ic) (hereinafter, collectively referred to as "aryloxy group (i)"). 1 ~R 16 In the formula (I), the total number of aryloxy groups (i) is, for example, 2 to 16, preferably 4 to 16, more preferably 4 to 8, and even more preferably 4. When compound (I) has a plurality of groups represented by formula (ia), the groups represented by the plurality of formulas (ia) may be the same or different, but are preferably the same, when compound (I) has a plurality of groups represented by formula (ib), the groups represented by the plurality of formulas (ib) may be the same or different, but are preferably the same, and when compound (I) has a plurality of groups represented by formula (ic), the groups represented by the plurality of formulas (ic) may be the same or different, but are preferably the same.

[0051] Furthermore, when compound (I) has a plurality of aryloxy groups (i), they are more preferably the same.

[0052] The aryloxy group (i) is preferably a group represented by formula (ia) or formula (ib), more preferably a group represented by formula (ia).

[0053] R 1 ~R 16 In the above, the position of the aryloxy group (i) is not particularly limited, but Aspect (1): R 1 ~R 4 At least one of R is an aryloxy group (i); 5 ~R 8 At least one of R is an aryloxy group (i); 9~R 12 At least one of R is an aryloxy group (i), and R 13 ~R 16 At least one of the groups is preferably an aryloxy group (i), Aspect (2): R 2 and R 3 At least one of R is an aryloxy group (i); 6 and R 7 At least one of R is an aryloxy group (i); 10 and R 11 At least one of R is an aryloxy group (i), and R 14 and R 15 At least one of R is an aryloxy group (i); 1 , R 4 , R 5 , R 8 , R 9 , R 12 , R 13 , and R 16 is a hydrogen atom, or aspect (3): R 1 and R 4 At least one of R is an aryloxy group (i); 5 and R 8 At least one of R is an aryloxy group (i); 9 and R 12 At least one of R is an aryloxy group (i), and R 13 and R 16 At least one of R is an aryloxy group (i); 2 , R 3 , R 6 , R 7 , R 10 , R 11 , R 14 , and R 15 is more preferably a hydrogen atom, Aspect (4): R 2 and R 3 one of the groups is an aryloxy group (i), and R 6 and R 7 one of the groups is an aryloxy group (i), and R 10 and R11 one of the groups (i) is an aryloxy group, and R 14 and R 15 one of the groups is an aryloxy group (i), and R 1 , R 4 , R 5 , R 8 , R 9 , R 12 , R 13 , and R 16 is a hydrogen atom, or embodiment (5): R 1 and R 4 one of the groups is an aryloxy group (i), and R 5 and R 8 one of the groups is an aryloxy group (i), and R 9 and R 12 one of the groups (i) is an aryloxy group, and R 13 and R 16 one of the groups is an aryloxy group (i), and R 2 , R 3 , R 6 , R 7 , R 10 , R 11 , R 14 , and R 15 is more preferably a hydrogen atom, Aspect (6): R 2 and R 3 one of R is an aryloxy group (i) and the other is a hydrogen atom; 6 and R 7 one of R is an aryloxy group (i) and the other is a hydrogen atom; 10 and R 11 one of R is an aryloxy group (i) and the other is a hydrogen atom, and R 14 and R 15 one of R is an aryloxy group (i) and the other is a hydrogen atom; 1 , R 4 , R 5 , R 8 , R 9 , R 12 , R 13 , and R 16is a hydrogen atom, or embodiment (7): R 1 , R 5 , R 9 , and R 13 is an aryloxy group (i), and R 2 ~R 4 , R 6 ~R 8 , R 10 ~R 12 , and R 14 ~R 16 It is particularly preferable that is a hydrogen atom. In each of the above embodiments (1) to (7), the multiple aryloxy groups (i) in compound (I) may be the same or different, but are preferably the same.

[0054] From the viewpoint of further reducing unevenness in brightness of the resulting color filter after long-term use, embodiment (2) is preferred, embodiment (4) is more preferred, and embodiment (6) is even more preferred.

[0055] As compound (I), a compound represented by formula (IA) (hereinafter, compound (IA)) and / or a compound represented by formula (IB) (hereinafter, compound (IB)) are preferred, and from the viewpoint of further suppressing uneven brightness of the resulting color filter after long-term use, compound (IA) is preferred.

[0056] [ka] [In formula (IA), R 2A and R 3A one of the formulas is a group represented by formula (iA-a), (iA-b), or (iA-c), and the other is a hydrogen atom; R 6A and R 7A one of the formulas is a group represented by formula (iA-a), (iA-b), or (iA-c), and the other is a hydrogen atom; R 10A and R 11Aone of the formulas is a group represented by formula (iA-a), (iA-b), or (iA-c), and the other is a hydrogen atom; R 14A and R 15A one of the formulas is a group represented by formula (iA-a), (iA-b), or (iA-c), and the other is a hydrogen atom; R 1A , R 4A , R 5A , R 8A , R 9A , R 12A , R 13A , and R 16A is a hydrogen atom. In formula (IB), R 1B , R 5B , R 9B , and R 13B Each independently represents a formula (iA-a) or a formula (iA-b) or a group represented by formula (iA-c), and R 2B ~R 4B , R 6B ~R 8B , R 10B ~R 12B , and R 14B ~R 16B is a hydrogen atom.] [ka] [In formula (iA-a), R a1A ~R a5A each independently represents a hydrogen atom, a bromine atom, an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 12 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms. a1A ~R a5A At least one of represents a bromine atom, an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 12 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms. * represents a bond. In formula (iA-b), R b1A~R b7A each independently represents a hydrogen atom, a bromine atom, an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 12 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms. b1A ~R b7A At least one of represents a bromine atom, an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 12 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms. * represents a bond. In formula (iA-c), R c1A ~R c7A each independently represents a hydrogen atom, a bromine atom, an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 12 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms. c1A ~R c7A At least one of represents a bromine atom, an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 12 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms. * represents a bond.]

[0057] The four groups represented by formula (iA-a), formula (iA-b), or formula (iA-c) in compound (IA) may be the same or different, but are preferably the same. The four groups represented by formula (iA-a), formula (iA-b), or formula (iA-c) in compound (IB) may be the same or different, but are preferably the same.

[0058] In compound (IA), R 2A and R 3A , R 6A and R 7A , R 10A and R 11A , and R 14A and R 15Aare each independently preferably one of them is a group represented by formula (iA-a) and the other is a hydrogen atom, or one of them is a group represented by formula (iA-b) and the other is a hydrogen atom, and more preferably one of them is a group represented by formula (iA-a) and the other is a hydrogen atom. In compound (IB), R 1B , R 5B , R 9B , and R 13B are each independently preferably a group represented by formula (iA-a) or formula (iA-b), and more preferably a group represented by formula (iA-a).

[0059] R a1A ~R a5A , R b1A ~R b7A , and R c1A ~R c7A As the alkyl group having 1 to 8 carbon atoms represented by the formula: a1 ~R a5 , R b1 ~R b7 , and R c1 ~R c7 Among the groups explained as the alkyl group represented by the following formula, groups having 1 to 8 carbon atoms can be mentioned. R a1A ~R a5A , R b1A ~R b7A , and R c1A ~R c7A Examples of the cycloalkyl group having 3 to 10 carbon atoms represented by the formula: a1 ~R a5 , R b1 ~R b7 , and R c1 ~R c7 Among the groups explained as the cycloalkyl group represented by the following formula, groups having 3 to 10 carbon atoms can be mentioned. R a1A ~R a5A , R b1A ~R b7A , and R c1A ~R c7A As the aromatic hydrocarbon group having 6 to 12 carbon atoms represented by the formula: a1 ~R a5 , Rb1 ~R b7 , and R c1 ~R c7 Among the groups explained as the aromatic hydrocarbon group represented by the following formula, groups having 6 to 12 carbon atoms are exemplified. R a1A ~R a5A , R b1A ~R b7A , and R c1A ~R c7A As the aralkyl group having 7 to 12 carbon atoms represented by the formula: a1 ~R a5 , R b1 ~R b7 , and R c1 ~R c7 Among the groups explained as the aralkyl group represented by the following formula, groups having 7 to 12 carbon atoms can be mentioned. R a1A ~R a5A , R b1A ~R b7A , and R c1A ~R c7A Examples of the alkoxy group having 1 to 4 carbon atoms represented by the formula (I) include a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, and a tert-butoxy group.

[0060] R a1A ~R a5A , R b1A ~R b7A , and R c1A ~R c7A are preferably each independently a hydrogen atom, a bromine atom, an alkyl group having 1 to 8 carbon atoms (particularly, 1 to 4), a cycloalkyl group having 4 to 8 carbon atoms, an aromatic hydrocarbon group having 6 to 10 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms.

[0061] In the group represented by formula (iA-a), R a1A ~R a5A Among these, the number of bromine atoms is preferably 0 to 3, more preferably 0 to 2, and further preferably 0 or 1. In the group represented by formula (iA-b), R b1A ~R b7AAmong these, the number of bromine atoms is preferably 0 to 3, more preferably 0 to 2, and further preferably 0 or 1. In the group represented by formula (iA-c), R c1A ~R c7A Among these, the number of bromine atoms is preferably 0 to 3, more preferably 0 to 2, and further preferably 0 or 1.

[0062] In the group represented by formula (iA-a), R a1A ~R a5A At least one of these is preferably a bromine atom, an alkyl group having 1 to 8 carbon atoms (particularly, 1 to 4 carbon atoms), a cycloalkyl group having 4 to 8 carbon atoms, an aromatic hydrocarbon group having 6 to 10 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms. In particular, R a1A ~R a5A Among these, it is preferred that 1 to 3 of them are each independently a bromine atom, an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 12 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and the remainder are a hydrogen atom; a1A ~R a5A Among these, it is more preferable that 1 to 3 are each independently a bromine atom, an alkyl group having 1 to 8 carbon atoms (particularly, 1 to 4), a cycloalkyl group having 4 to 8 carbon atoms, an aromatic hydrocarbon group having 6 to 10 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and the remainder are a hydrogen atom.

[0063] In the group represented by formula (iA-b), R b1A ~R b7A At least one of them is preferably a bromine atom, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 4 to 8 carbon atoms, an aromatic hydrocarbon group having 6 to 10 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms. In particular, R b1A ~R b7AAmong these, it is preferred that 1 to 3 of them are each independently a bromine atom, an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms, and the remainder are a hydrogen atom; b1A ~R b7A Among these, it is more preferable that 1 to 3 are each independently a bromine atom, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 4 to 8 carbon atoms, an aromatic hydrocarbon group having 6 to 10 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms, and the remainder are a hydrogen atom.

[0064] In the group represented by formula (iA-c), R c1A ~R c7A at least one of R is preferably a bromine atom, an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms; c1A ~R c7A It is more preferable that at least one of them is a bromine atom, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 4 to 8 carbon atoms, an aromatic hydrocarbon group having 6 to 10 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms. In particular, R c1A ~R c7A Among these, it is preferred that 1 to 3 of them are each independently a bromine atom, an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms, and the remainder are a hydrogen atom; c1A ~R c7A Among these, it is more preferable that 1 to 3 are each independently a bromine atom, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 4 to 8 carbon atoms, an aromatic hydrocarbon group having 6 to 10 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms, and the remainder are a hydrogen atom.

[0065] Specific examples of the group represented by formula (iA-a) include the groups represented by the above formulas (i-a1) to (i-a17), etc.; specific examples of the group represented by formula (iA-b) include the groups represented by the above formulas (i-b1) to (i-b4), etc.; and specific examples of the group represented by formula (iA-c) include the groups represented by the above formulas (i-c1) to (i-c5), etc.

[0066] Specific examples of compound (I) include compounds (Ia-1) to (Ia-136) and compounds (Ib-1) to (Ib-17) shown in Tables 1 to 5.

[0067] [Table 1]

[0068] [Table 2]

[0069] [Table 3]

[0070] [Table 4]

[0071] [Table 5]

[0072] In Tables 1 to 5, i-a1 to i-a17 represent groups represented by the above formulas (i-a1) to (i-a17), and H represents a hydrogen atom.

[0073] [Method for producing compound (I)] The method for producing compound (I) is preferably to react compounds represented by formulas (II-1) to (II-4) in the presence of a base and a compound represented by formula (III). Hereinafter, such a method may be referred to as the method of the present invention. [ka] [In formula (III), X M is a halogen atom, a hydroxyl group, or OR M R M represents a hydrocarbon group having 1 to 6 carbon atoms.] [ka] [In formulas (II-1) to (II-4), R 1 ~R 16 has the same meaning as above.]

[0074] The present inventors have investigated the reaction of compounds represented by formulae (II-1) to (II-4) (hereinafter, collectively referred to as phthalonitrile compound (II)) in the presence of a base as in the above-mentioned Non-Patent Document 1 in producing compound (I), but have found that the method is poor in reproducibility and the yield of the target compound (I) is low. In particular, when the above-mentioned aryloxy group (i) is present, the yield tends to decrease. The present inventors have found that, by reacting phthalonitrile compound (II) in the presence of a base and a compound represented by formula (III) (hereinafter, sometimes referred to as aluminum compound (III)), the target compound (I) can be stably obtained in a predetermined yield or higher, even when the compound has an aryloxy group (i).

[0075] In addition, normally, when a phthalonitrile compound is reacted in the presence of an aluminum compound (III), an aluminum phthalocyanine having an aluminum atom as a central metal is preferentially obtained. However, when a phthalonitrile compound (II) having the above-mentioned aryloxy group (i) is reacted, unexpectedly, a metal-free phthalocyanine compound (I) is preferentially produced rather than an aluminum phthalocyanine represented by the following formula (IV) (hereinafter, sometimes referred to as aluminum phthalocyanine (IV) or compound (IV)), that is, the selectivity of the target compound (I) was good. Therefore, by adopting the production method of the present invention, the yield of the target compound (I) can be increased. In addition, by adopting the production method of the present invention, it is also preferable that the compound (I) can be produced in a short time.

[0076] [ka] [In formula (IV), R 1 ~R 16 and X M has the same meaning as above.]

[0077] The production method of the present invention will be described in detail below.

[0078] In formula (III), X M Examples of the halogen atom represented by the formula (I) include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc., and among these, a chlorine atom is preferred.

[0079] R M As the hydrocarbon group having 1 to 6 carbon atoms represented by the formula: 1 ~R 16 The examples of the hydrocarbon group having 1 to 6 carbon atoms and represented by the following formula are the same as those described above, and the preferred embodiments are also the same. OR MSpecific examples of the group include alkoxy groups having 1 to 6 carbon atoms, such as a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, and a tert-butoxy group, and a phenoxy group. Among these, an alkoxy group having 1 to 6 carbon atoms is preferred, and an alkoxy group having 1 to 4 carbon atoms is more preferred.

[0080] In formula (III), X M is preferably a halogen atom, a hydroxy group, or an alkoxy group having 1 to 4 carbon atoms, more preferably a chlorine atom or a hydroxy group, and particularly preferably a chlorine atom.

[0081] In the phthalonitrile compound (II), R 1 ~R 16 is R in compound (I). 1 ~R 16 The four compounds represented by formulae (II-1) to (II-4) may be the same or different, but are preferably the same compound.

[0082] The amount of the aluminum compound (III) used is preferably 0.25 to 0.40 moles, more preferably 0.27 to 0.34 moles, per mole of the total amount of the phthalonitrile compound (II). By adjusting the amount of the aluminum compound (III) relative to the phthalonitrile compound (II) to a predetermined value or more, the yield of the compound (I) can be increased and the reaction time can be shortened. In addition, by adjusting the amount of the aluminum compound (III) relative to the phthalonitrile compound (II) to a predetermined value or less, the compound (I) is more likely to be preferentially produced than the aluminum phthalocyanine (IV), that is, the selectivity of the compound (I) is more improved.

[0083] As the base, an inorganic base and / or an organic base can be used. Examples of inorganic bases include alkali metal carbonates such as sodium carbonate and potassium carbonate; alkali metal phosphates such as trisodium phosphate and tripotassium phosphate; alkali metal hydroxides such as sodium hydroxide, potassium hydroxide, and lithium hydroxide; and the like. Examples of the organic base include trialkylamines such as triethylamine and N,N-diisopropylethylamine; nitrogen-containing heterocyclic compounds such as pyridine, picoline, 1,8-diazabicyclo[5.4.0]-7-undecene (DBU), and 1,5-diazabicyclo[4.3.0]non-5-ene (DBN); and the like. Among these, organic bases are preferred, nitrogen-containing heterocyclic compounds are more preferred, and 1,8-diazabicyclo[5.4.0]-7-undecene is even more preferred.

[0084] The amount of the base used is preferably 1.0 to 5.0 mol, more preferably 1.3 to 2.0 mol, per mol of the total amount of the phthalonitrile compound (II).

[0085] The reaction of the phthalonitrile compound (II) may be carried out in the presence of a solvent or in the absence of a solvent, but is preferably carried out in the presence of a solvent from the viewpoint of improving the reaction efficiency.

[0086] The solvent is preferably an organic solvent, for example: Ester solvents such as methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutanoate, ethyl acetate, n-butyl acetate, isobutyl acetate, pentyl formate, isopentyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexanol acetate, and gamma-butyrolactone; Ether solvents such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenetole and methylanisole; Alcohol solvents such as methanol, ethanol, propanol, butanol, heptanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, diethylene glycol, triethylene glycol, and glycerin;

[0087] Among these, from the viewpoint of further improving the reaction efficiency, the solvent is preferably an alcohol solvent, more preferably a polyhydric alcohol solvent such as ethylene glycol, propylene glycol, diethylene glycol, triethylene glycol, or glycerin, and particularly preferably a polyhydric alcohol solvent having a boiling point of 160° C. or higher (preferably 200° C. or higher).

[0088] The amount of the solvent used is not particularly limited, but is, for example, 1 to 500 parts by mass, preferably 3 to 100 parts by mass, and more preferably 5 to 50 parts by mass, per part by mass of the total amount of the phthalonitrile compound (II).

[0089] The reaction temperature is, for example, 50°C to 200°C, preferably 90°C to 180°C, and more preferably 120°C to 160°C.

[0090] In the production method of the present invention, since the reaction is carried out in the presence of the aluminum compound (III), the yield of the compound (I) can be increased even if the reaction time is short. From the viewpoint of productivity, the reaction time is preferably 30 minutes to 50 hours, more preferably 1 to 40 hours, and further preferably 3 to 35 hours, and can also be 20 hours or less, or 15 hours or less.

[0091] The reaction mixture obtained by the above reaction contains the target compound (I). In the production method of the present invention, in which the reaction is carried out in the presence of the aluminum compound (III), the above aluminum phthalocyanine (IV) may be generated as a by-product, but since the synthesis uses the phthalonitrile compound (II) having at least one aryloxy group (i), the compound (I) is synthesized preferentially over the aluminum phthalocyanine (IV). Therefore, in the production method of the present invention, the amount of compound (I) obtained is preferably 1.5 mol or more, more preferably 2.0 mol or more, and can also be 3.0 mol or more, or 4.0 mol or more, per mol of aluminum phthalocyanine (IV). The amount of compound (I) relative to aluminum phthalocyanine (IV) can be calculated by isolating compound (I) and aluminum phthalocyanine (IV) from the reaction mixture and measuring the yield.

[0092] The method for isolating compound (I) and aluminum phthalocyanine (IV) from the reaction mixture is not particularly limited, and various known methods can be used. For example, compound (I) can be precipitated by cooling the reaction mixture to room temperature (e.g., 18 to 24°C) and adding water or ethyl acetate as necessary. At this time, if aluminum phthalocyanine (IV) is contained in the reaction mixture, aluminum phthalocyanine (IV) also precipitates together with compound (I). Thereafter, the precipitate is washed with water, acetone, methanol, etc. as necessary, and then purified by, for example, column chromatography, etc., to isolate compound (I) and aluminum phthalocyanine (IV).

[0093] The column chromatography is preferably a silica gel column chromatography. The mobile phase (developing solvent) used in the column chromatography is not particularly limited and may be appropriately selected depending on the compound to be isolated, but it is preferable to use an aromatic hydrocarbon solvent and an ether solvent, and it is more preferable to use a gradient method in which extraction is performed while changing the aromatic hydrocarbon solvent:ether solvent (mass ratio) from 100:0 to 0:100.

[0094] Examples of the aromatic hydrocarbon solvent include benzene, toluene, xylene, and mesitylene, and among these, toluene is preferred. The ether solvent may be any of those described above as the ether solvent used in the reaction of the phthalonitrile compound (II), and among these, tetrahydrofuran is preferred.

[0095] By employing the production method of the present invention, the yield of compound (I) from phthalonitrile compound (II) can be increased. The yield of compound (I) in the reaction for synthesizing compound (I) from phthalonitrile compound (II) is preferably 5% or more, more preferably 15% or more, further preferably 20% or more, and can be 30% or more or 40% or more.

[0096] The content of compound (I) in the total amount of colorant (A) is, for example, 20 to 100 mass%, preferably 30 to 100 mass%, more preferably 40 to 90 mass%, and further preferably 50 to 80 mass%. When the content of compound (I) in colorant (A) is within the above range, it becomes easier to obtain the desired spectrum, and also easier to suppress unevenness in brightness after long-term use.

[0097] The colorant (A) may further contain a colorant (hereinafter, may be referred to as colorant (A1)) different from the compound (I). The colorant (A1) may be either a dye or a pigment, but is preferably a pigment from the viewpoint of further suppressing unevenness in brightness after long-term use.

[0098] Examples of dyes include compounds classified as having a hue other than pigments in the Color Index (published by The Society of Dyers and Colourists) and known dyes described in Dyeing Notes (Shikisensha).

[0099] Examples of dyes include azo dyes, cyanine dyes, triphenylmethane dyes, xanthene dyes, thiazole dyes, oxazine dyes, quinophthalone 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.

[0100] Specific examples of dyes include CI Solvent Yellow 4 (hereinafter, the description of CI Solvent Yellow will be omitted and only the numbers will be described. The same applies to the others), 14, 15, 23, 24, 25, 38, 62, 63, 68, 79, 81, 82, 83, 89, 94, 98, 99, 117, 162, 163, 167, and 189; CI Solvent Red 24, 45, 49, 90, 91, 111, 118, 119, 122, 124, 125, 127, 130, 132, 143, 145, 146, 150, 151, 155, 160, 168, 169, 172, 175, 181, 207, 218, 222, 227, 230, 245, 247; CI Solvent Orange 2, 7, 11, 15, 26, 41, 54, 56, 77, 86, 99; CI Solvent Violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60; CI Solvent Blue 4, 5, 14, 18, 35, 36, 37, 38, 44, 45, 58, 59, 59:1, 63, 67, 68, 69, 70, 78, 79, 83, 90, 94, 97, 98, 100, 101, 102, 104, 105, 111, 112, 122, 128, 132, 136, 139; CI Solvent dyes such as CI Solvent Green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35; CI Acid Yellow 1, 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112, 113, 114, 116, 119, 123, 128, 134, 135, 138, 139, 140, 144, 150, 155, 157, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251; CI Acid Red 1, 4, 8, 14, 17, 18, 26, 27, 29, 31, 33, 34, 35, 37, 40, 42, 44, 50, 51, 52, 57, 66, 73, 76, 80, 87, 88, 91, 92, 94, 95, 97, 98, 103, 106, 111, 114, 129, 133, 134, 138, 143, 145, 150, 151, 155, 158, 160, 172, 176, 1 82, 183, 195, 198, 206, 211, 215, 216, 217, 227, 228, 249, 252, 257, 258, 260, 261, 266, 268, 270, 274, 277, 280, 281, 289, 308, 312, 315, 316, 339, 341, 345, 346, 349, 382, ​​383, 388, 394, 401, 412, 417, 418, 422, 426; CI Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 149, 162, 169, 173; CI Acid Violet 6B, 7, 9, 15, 16, 17, 19, 21, 23, 24, 25, 30, 34, 38, 49, 72, 102; CI Acid Blue 1, 3, 5, 7, 9, 11, 13, 15, 17, 18, 22, 23, 24, 25, 26, 27, 29, 34, 38, 40, 41, 42, 43, 45, 48, 51, 54, 59, 60, 62, 70, 72, 74, 75, 78, 80, 82, 83, 86, 87, 88, 90, 90:1, 91, 92, 93, 93:1, 96, 99, 100, 102, 103, 104, 108, 109, 110, 112, 113, 117, 119, 120, 123 , 126, 127, 129, 130, 131, 138, 140, 142, 143, 147, 150, 151, 154, 158, 161, 166, 167, 168, 170, 171, 175, 182, 183, 184, 187, 192, 199, 203, 204, 205, 210, 213, 229, 234, 236, 242, 243, 249, 256, 259, 267, 269, 278, 280, 285, 290, 296, 315, 324:1, 335, 340; CI Acid dyes such as CI Acid Green 1, 3, 5, 6, 7, 8, 9, 11, 13, 14, 15, 16, 22, 25, 27, 28, 41, 50, 50:1, 58, 63, 65, 80, 104, 105, 106, 109; CI Direct Yellow 2, 4, 28, 33, 34, 35, 38, 39, 43, 44, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129, 132, 136, 138, 141; CI Direct Red 79, 82, 83, 84, 91, 92, 96, 97, 98, 99, 105, 106, 107, 172, 173, 176, 177, 179, 181, 182, 184, 204, 207, 211, 213, 218, 220, 221, 222, 232, 233, 234, 241, 243, 246, 250; CI Direct Orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107; CI Direct Violet 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104; CI Direct Blue 1, 2, 3, 6, 8, 15, 22, 25, 28, 29, 40, 41, 42, 47, 52, 55, 57, 71, 76, 77, 78, 80, 81, 84, 85, 86, 87, 90, 93, 94, 95, 97, 98, 99, 100, 101, 106, 107, 108, 109, 113, 114, 115, 117, 119, 120, 137, 149, 150, 153, 155, 156, 158, 159, 160, 161, 162, 163, 164, 165, 16 6, 167, 168, 170, 171, 172, 173, 188, 189, 190, 192, 193, 194, 195, 196, 198, 199, 200, 201, 202, 203, 207, 209, 210, 212, 213, 214, 222, 225, 226, 228, 229, 236, 237, 238, 242, 243, 244, 245, 246, 247, 248, 249, 250, 251, 252, 256, 257, 259, 260, 268, 274, 275, 293; CI Direct Dyes, such as CI Direct Green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 79, 82; CI Disperse Yellow 51, 54, 76; CI Disperse Violet 26, 27; CI Disperse dyes such as CI Disperse Blue 1, 14, 56, 60; CI Basic Red 1, 9, 10; CI Basic Blue 1, 3, 5, 7, 9, 19, 21, 22, 24, 25, 26, 28, 29, 40, 41, 45, 47, 54, 58, 59, 60, 64, 65, 66, 67, 68, 81, 83, 88, 89; CI Basic Violet 2; CI Basic dyes, such as CI Basic Green 1; CI Reactive Yellow 2, 76, 116; CI Reactive Orange 16; CI Reactive dyes such as CI Reactive Red 36; CI Mordant Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65; CI Mordant Red 1, 2, 3, 4, 9, 11, 12, 14, 17, 18, 19, 22, 23, 24, 25, 26, 27, 29, 30, 32, 33, 36, 37, 38, 39, 41, 42, 43, 45, 46, 48, 52, 53, 56, 62, 63, 71, 74, 76, 78, 85, 86, 88, 90, 94, 95; CI Mordant Orange 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47, 48; CI Mordant Violet 1, 1:1, 2, 3, 4, 5, 6, 7, 8, 10, 11, 14, 15, 16, 17, 18, 19, 21, 22, 23, 24, 27, 28, 30, 31, 32, 33, 36, 37, 39, 40, 41, 44, 45, 47, 48, 49, 53, 58; CI Mordant Blue 1, 2, 3, 7, 8, 9, 12, 13, 15, 16, 19, 20, 21, 22, 23, 24, 26, 30, 31, 32, 39, 40, 41, 43, 44, 48, 49, 53, 61, 74, 77, 83, 84; CI Mordant dyes, such as CI Mordant Green 1, 3, 4, 5, 10, 13, 15, 19, 21, 23, 26, 29, 31, 33, 34, 35, 41, 43, 53; CI Vat Green 1; and other CI Vat dyes. These dyes may be one type of dye or a plurality of dyes for each color, or dyes of each color may be combined.

[0101] Examples of pigments include those classified as pigments in the Colour 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, 246, 254, 255, 264, 265, 266, 268, 269, 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, 25; Black pigments such as CI Pigment Black 1 and 7; With regard to these pigments, one kind of pigment or a plurality of pigments may be used for each color, and pigments of each color may be combined.

[0102] If necessary, the pigment may be subjected to a rosin treatment, a surface treatment using a pigment derivative having an acidic or basic group introduced therein, a graft treatment onto the pigment surface using a polymer compound or the like, a particle size reduction treatment using a sulfuric acid atomization method or the like, a washing treatment using an organic solvent or water to remove impurities, a removal treatment of ionic impurities using an ion exchange method or the like, etc. The particle size of the pigment is preferably approximately uniform.

[0103] The colorant (A1) may be appropriately selected depending on the desired spectrum. For example, when forming a green filter in a color filter, the colorant (A1) is preferably a yellow pigment, more preferably at least one selected from CI Pigment Yellow 138, 150, and 185, and even more preferably CI Pigment Yellow 138 and / or 185.

[0104] When a yellow pigment is used as the colorant (A1), the content of the yellow pigment relative to 100 parts by mass of the compound (I) is, for example, 1 to 200 parts by mass, preferably 5 to 150 parts by mass, more preferably 10 to 100 parts by mass, and further preferably 15 to 80 parts by mass. When the content of the yellow pigment is within the above range, the desired dispersion can be more easily obtained.

[0105] The content of the colorant (A) in the colored resin composition is, for example, 0.5 to 80 mass%, preferably 2 to 70 mass%, more preferably 8 to 55 mass%, and further preferably 25 to 50 mass%, based on the total amount of solids. When the content of the colorant (A) is within the above range, it becomes easier to obtain the desired spectrum and color density. In this specification, the term "total amount of solids" refers to the total amount of components excluding the solvent from the colored resin composition of the present invention. The total amount of solids and the content of each component relative thereto can be measured by known analytical means such as liquid chromatography and gas chromatography.

[0106] <Resin (B)> Resin (B) is an alkali-soluble resin. The resin (B) may be the following resin [K1]: ~[K6] etc. Resin [K1]: a copolymer of at least one monomer (a) (hereinafter sometimes referred to as "(a)") selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic anhydrides, and 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 of (a), (b), and a monomer (c) copolymerizable with (a) (however, different from (a) and (b)) (hereinafter sometimes referred to as "(c)"); Resin [K3]; copolymer of (a) and (c); Resin [K4]: A resin obtained by reacting a copolymer of (a) and (c) with (b); Resin [K5]: a resin obtained by reacting a copolymer of (b) and (c) with (a); Resin [K6]: A resin obtained by reacting a copolymer of (b) and (c) with (a) and further reacting it with a polyvalent carboxylic acid and / or a carboxylic anhydride.

[0107] Specific examples of (a) include unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, 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-5-ethylbicyclo[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; Unsaturated dicarboxylic acid anhydrides such as maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, and 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride; 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; Examples include unsaturated acrylates that contain a hydroxy group and a carboxy group in the same molecule, such as α-(hydroxymethyl)acrylic acid. Among these, acrylic acid, methacrylic acid, maleic anhydride, etc. are preferred from the standpoint of copolymerization reactivity and solubility of the resulting resin in an aqueous alkaline solution.

[0108] (b) is, for example, 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) and an ethylenically unsaturated bond. (b) is preferably a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth)acryloyloxy group. In this specification, the term "(meth)acrylic acid" refers to at least one selected from the group consisting of acrylic acid and methacrylic acid. The terms "(meth)acryloyl" and "(meth)acrylate" have the same meaning.

[0109] Examples of (b) include a monomer (b1) having an oxiranyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b1)"), a monomer (b2) having an oxetanyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b2)"), and a monomer (b3) having a tetrahydrofuryl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b3)").

[0110] Examples of (b1) include a monomer (b1-1) (hereinafter sometimes referred to as "(b1-1)") having a structure in which a linear or branched unsaturated aliphatic hydrocarbon has been epoxidized, and a monomer (b1-2) (hereinafter sometimes referred to as "(b1-2)") having a structure in which an alicyclic unsaturated hydrocarbon has been epoxidized.

[0111] Examples of (b1-1) include glycidyl (meth)acrylate, β-methyl glycidyl (meth)acrylate, β-ethyl glycidyl (meth)acrylate, glycidyl vinyl ether, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether, α-methyl-o-vinylbenzyl glycidyl ether, α-methyl-m-vinylbenzyl glycidyl ether, α-methyl-p-vinylbenzyl glycidyl ether, 2,3-bis(glycidyl Examples of such styrene include 2,4-bis(glycidyloxymethyl)styrene, 2,5-bis(glycidyloxymethyl)styrene, 2,6-bis(glycidyloxymethyl)styrene, 2,3,4-tris(glycidyloxymethyl)styrene, 2,3,5-tris(glycidyloxymethyl)styrene, 2,3,6-tris(glycidyloxymethyl)styrene, 3,4,5-tris(glycidyloxymethyl)styrene, and 2,4,6-tris(glycidyloxymethyl)styrene.

[0112] Examples of (b1-2) include vinylcyclohexene monoxide, 1,2-epoxy-4-vinylcyclohexane (e.g., Celloxide 2000; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., Cyclomer A400; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., Cyclomer M100; manufactured by Daicel Corporation), 3,4-epoxytricyclo[5.2.1.0]phenylene ether, and the like. 2,6 ]decyl (meth)acrylate, a compound represented by formula (R1) and a compound represented by formula (R2) are included.

[0113] [ka]

[0114] [In formula (R1) and formula (R2), R ra and R rb represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the hydrogen atom contained in the alkyl group may be substituted with a hydroxy group. X ra and X rb is a single bond, *-R rc -, *-R rc -O-, *-R rc -S- or *-R rc -NH-. R rc represents an alkanediyl group having 1 to 6 carbon atoms. * represents a bond to O.]

[0115] 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. Examples of the alkyl group 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. R ra and R rb 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.

[0116] 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. X ra and X rb Preferred examples of the group include a single bond, a methylene group, an ethylene group, *-CH2-O-, and *-CH2CH2-O-, and more preferred examples include a single bond and *-CH2CH2-O- (* represents a bond to O).

[0117] Examples of the compound represented by formula (R1) include compounds represented by any of formulas (R1-1) to (R1-15). Among them, compounds represented by formulas (R1-1), (R1-3), (R1-5), (R1-7), (R1-9) or (R1-11) to (R1-15) are preferred, and compounds represented by formulas (R1-1), (R1-7), (R1-9) or (R1-15) are more preferred.

[0118] [ka]

[0119] [ka]

[0120] Examples of the compound represented by formula (R2) include compounds represented by any of formulas (R2-1) to (R2-15). Among them, compounds represented by formulas (R2-1), (R2-3), (R2-5), (R2-7), (R2-9) or (R2-11) to (R2-15) are preferred, and compounds represented by formulas (R2-1), (R2-7), (R2-9) or (R2-15) are more preferred.

[0121] [ka]

[0122] [ka]

[0123] As (b2), a monomer having an oxetanyl group and a (meth)acryloyloxy group is more preferable. As (b2), 3-methyl-3-methacryloyloxymethyloxetane, 3-methyl-3-acryloyloxymethyloxetane, 3-ethyl-3-methacryloyloxymethyloxetane, 3-ethyl-3-acryloyloxymethyloxetane, 3-methyl-3-methacryloyloxyethyloxetane, 3-methyl-3-acryloyloxyethyloxetane, 3-ethyl-3-methacryloyloxyethyloxetane, 3-ethyl-3-acryloyloxyethyloxetane, and the like can be mentioned.

[0124] As (b3), a monomer having a tetrahydrofuryl group and a (meth)acryloyloxy group is more preferable. Specific examples of (b3) include tetrahydrofurfuryl acrylate (e.g., Viscoat V#150, manufactured by Osaka Organic Chemical Industry Co., Ltd.), tetrahydrofurfuryl methacrylate, etc.

[0125] As (b), (b1) is preferable in that the reliability of the heat resistance, chemical resistance, etc. of the obtained color filter can be improved. Furthermore, (b1-2) is more preferable in that the storage stability of the colored resin composition is excellent.

[0126] Examples of (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[5.2.1.02,6 ](meth)acrylic acid esters such as decene-8-yl (meth)acrylate (commonly known in the art as "dicyclopentenyl (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 chloro[2.2.1]hept-2-ene, 5-ethoxybicyclo[2.2.1]hept-2-ene, 5,6-dihydroxybicyclo[2.2.1]hept-2-ene, 5,6-di(hydroxymethyl)bicyclo[2.2.1]hept-2-ene, 5,6-di(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5,6-dimethoxybicyclo[2.2.1]hept -2-ene, 5,6-diethoxybicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxymethyl-5-methylbicyclo[2.2.1]hept-2-ene, 5-tert-butoxycarbonylbicyclo[2.2.1]hept-2-ene, bicyclounsaturated compounds such as 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 of the copolymer include styrene, α-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, p-methoxystyrene, acrylonitrile, methacrylonitrile, vinyl chloride, vinylidene chloride, acrylamide, methacrylamide, vinyl acetate, 1,3-butadiene, isoprene, and 2,3-dimethyl-1,3-butadiene. As (c), 2-ethylhexyl (meth)acrylate, dicyclopentanyl (meth)acrylate, benzyl (meth)acrylate, styrene, vinyltoluene, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo[2.2.1]hept-2-ene, etc. are preferred, and from the viewpoints of copolymerization reactivity and heat resistance, styrene, vinyltoluene, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo[2.2.1]hept-2-ene, etc. are more preferred.

[0127] In the resin [K1], the ratio of structural units derived from each of them is as follows among all structural units constituting the resin [K1]: 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 colored resin composition, the developability when forming a colored pattern, and the solvent resistance of the obtained color filter tend to be superior.

[0128] Resin [K1] can be produced, for example, by referring to 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 on March 1, 1972) and the cited references described in said literature.

[0129] Specifically, a method is exemplified in which predetermined amounts of (a) and (b), a polymerization initiator, a solvent, etc. are placed in a reaction vessel, and the atmosphere is deoxygenated by, for example, replacing oxygen with nitrogen, and the mixture is heated and kept warm while stirring. The polymerization initiator and solvent used here are not particularly limited, and those commonly used in the relevant field can be used. For example, examples of the polymerization initiator include azo compounds (2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), etc.) and organic peroxides (benzoyl peroxide, etc.), and examples of the solvent include those that dissolve each monomer, such as the solvent (E) described below.

[0130] The obtained copolymer may be used as it is after the reaction, or may be used after concentration or dilution, or may be used after extraction as a solid (powder) by a method such as reprecipitation. In particular, by using the solvent contained in the colored resin composition as the solvent during this polymerization, the solution after the reaction can be used as it is for the preparation of the colored resin composition, and therefore the manufacturing process of the colored resin composition can be simplified.

[0131] In the resin [K2], the ratio of structural units derived from each of them is as follows among all structural units constituting the resin [K2]: 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 colored resin composition, the developability when forming a colored pattern, and the solvent resistance, heat resistance, and mechanical strength of the resulting color filter tend to be superior.

[0132] Resin [K2] can be produced, for example, in the same manner as described above as the method for producing resin [K1].

[0133] In the resin [K3], the ratio of structural units derived from each of them is as follows among all structural units constituting the resin [K3]: 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 as the method for producing resin [K1].

[0134] 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 method 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].

[0135] 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 moles, more preferably 10 to 75 moles, relative to 100 moles of (a). By adjusting the amount within this range, the storage stability of the colored resin composition, the developability when forming a pattern, and the balance of the solvent resistance, heat resistance, mechanical strength, and sensitivity of the resulting pattern tend to be good. Since the reactivity of the cyclic ether is high and unreacted (b) is unlikely to remain, (b1) is preferable as (b) used in the resin [K4], and (b1-1) is more preferable. The amount of the reaction catalyst used is preferably 0.001 to 5 parts by mass per 100 parts by mass of the total amount of (a), (b) and (c).The amount of the polymerization inhibitor used is preferably 0.001 to 5 parts by mass per 100 parts by mass of the total amount of (a), (b) and (c). The reaction conditions such as the 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.

[0136] Resin [K5] is produced in the first step by the same method as the above-mentioned resin [K1] to obtain a copolymer of (b) and (c). As in the above, the obtained copolymer may be used as it is in the form of a solution after the reaction, or may be a concentrated or diluted solution, or may be extracted as a solid (powder) 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, respectively, 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:

[0137] Furthermore, under the same conditions as in the manufacturing 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) reacted with the copolymer is preferably 5 to 100 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.

[0138] 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 succinic anhydride, 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 0.1 to 1 mole per mole of the amount of (a) used.

[0139] Specific examples of the resin (B) 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 resin [K1]; 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl acrylate / benzyl (meth)acrylate / (meth)acrylic acid copolymer, 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 / vinyl toluene 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]; benzyl (meth)acrylate / (meth)acrylic acid copolymer to which glycidyl (meth)acrylate has been added, tricyclodecyl (meth)acrylate / styrene / (meth)acrylic acid copolymer to which glycidyl (meth)acrylate has been added, tricyclodecyl (meth)acrylate / benzyl (meth)acrylate / (meth)acrylic acid copolymer to which glycidyl (meth)acrylate has been added, tricyclodecyl (meth)acrylate / benzyl (meth)acrylate / (meth)acrylic acid copolymer to which glycidyl (meth)acrylate has been added, Resins such as resins to which acrylate has been added [K4]; resins obtained by reacting a copolymer of tricyclodecyl (meth)acrylate / glycidyl (meth)acrylate with (meth)acrylic acid, resins obtained by reacting a copolymer of tricyclodecyl (meth)acrylate / styrene / glycidyl (meth)acrylate with (meth)acrylic acid [K5]; resins obtained by reacting a copolymer of tricyclodecyl (meth)acrylate / glycidyl (meth)acrylate with (meth)acrylic acid and then reacting it with tetrahydrophthalic anhydride, resins obtained by reacting a copolymer of 2-ethylhexyl (meth)acrylate / glycidyl (meth)acrylate / dicyclopentanyl (meth)acrylate with (meth)acrylic acid and then reacting it with succinic anhydride [K6], and the like can be mentioned. Among these, as the resin (B), at least one selected from the group consisting of copolymers (resin [K1], resin [K2]) containing a structural unit derived from at least one selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic anhydrides, and a structural unit having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond, and resin [K6], is preferred, and resin [K1] and / or resin [K2] are more preferred.

[0140] The polystyrene-equivalent weight average molecular weight of resin (B) is preferably 500 to 100,000, more preferably 1,000 to 50,000, and even more preferably 3,000 to 30,000. When the molecular weight is within the above range, the hardness of the color filter is improved, the residual film rate is high, the solubility of the unexposed portion in the developer is good, and the resolution of the colored pattern tends to be improved.

[0141] The dispersity of the resin (B) [weight average molecular weight (Mw) / number average molecular weight (Mn)] is preferably 1.1-6, and more preferably 1.2-4.

[0142] The acid value of the resin (B) is preferably 10 to 170 mg-KOH / g, more preferably 30 to 155 mg-KOH / g, and further preferably 50 to 140 mg-KOH / g, calculated as solid content. The acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of the resin (B), and can be determined, for example, by titration with an aqueous potassium hydroxide solution.

[0143] The content of resin (B) is preferably 7 to 80 mass%, more preferably 13 to 70 mass%, further preferably 17 to 60 mass%, and even more preferably 20 to 50 mass%, based on the total amount of solids in the colored resin composition. When the content of resin (B) is within the above range, a colored pattern can be formed, and the resolution and residual film rate of the colored pattern tend to be improved. The content of the resin (B) is, for example, 30 to 200 parts by mass, preferably 50 to 180 parts by mass, and more preferably 80 to 150 parts by mass, relative to 100 parts by mass of the compound (I). By adjusting the content of the resin (B) within the above range, the above-mentioned effect of suppressing uneven brightness tends to be enhanced.

[0144] <Polymerizable compound (C)> The polymerizable compound (C) is a compound that can be polymerized by active radicals and / or acids generated from the polymerization initiator (D), and examples thereof include compounds having a polymerizable ethylenically unsaturated bond, and are preferably (meth)acrylic acid ester compounds.

[0145] Among them, the polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds. Examples of such polymerizable compounds include trimethylolpropane tri(meth)acrylate, pentaerythritol poly(meth)acrylate (e.g., pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate), dipentaerythritol poly(meth)acrylate (e.g., dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate), tripentaerythritol poly(meth)acrylate (e.g., tri(meth)acrylate ... pentaerythritol octa(meth)acrylate, tripentaerythritol hepta(meth)acrylate), tetrapentaerythritol poly(meth)acrylate (e.g., tetrapentaerythritol deca(meth)acrylate, tetrapentaerythritol nona(meth)acrylate), tris(2-(meth)acryloyloxyethyl)isocyanurate, alkoxylated pentaerythritol poly(meth)acrylate (e.g., ethoxylated pentaerythritol tri(meth)acrylate, ethoxylated alkoxylated pentaerythritol tetra(meth)acrylate, propoxylated pentaerythritol tri(meth)acrylate, propoxylated pentaerythritol tetra(meth)acrylate), alkoxylated dipentaerythritol poly(meth)acrylates (e.g., ethoxylated dipentaerythritol penta(meth)acrylate, ethoxylated dipentaerythritol hexa(meth)acrylate, propoxylated dipentaerythritol penta(meth)acrylate, propoxylated dipentaerythritol caprolactone-modified pentaerythritol poly(meth)acrylate (e.g., caprolactone-modified pentaerythritol tri(meth)acrylate, caprolactone-modified pentaerythritol tetra(meth)acrylate), caprolactone-modified dipentaerythritol poly(meth)acrylate (e.g., caprolactone-modified dipentaerythritol penta(meth)acrylate, caprolactone-modified dipentaerythritol hexa(meth)acrylate). Among them, at least one selected from the group consisting of trimethylolpropane tri(meth)acrylate and dipentaerythritol poly(meth)acrylate is preferable.

[0146] The weight average molecular weight of the polymerizable compound (C) is preferably 150 or more and 2,900 or less, and more preferably 250 or more and 1,500 or less.

[0147] The content of the polymerizable compound (C) is, for example, 5 to 65 mass%, preferably 6 to 50 mass%, more preferably 8 to 30 mass%, based on the total amount of solids in the colored resin composition. When the content of the polymerizable compound (C) is within the above range, the residual film rate during colored pattern formation and the chemical resistance of the color filter tend to be further improved.

[0148] <Polymerization initiator (D)> The polymerization initiator (D) is not particularly limited as long as it is a compound that can generate active radicals, acids, etc. by the action of light or heat and initiate polymerization, and any known polymerization initiator can be used.

[0149] Examples of polymerization initiators that generate active radicals include alkylphenone compounds, triazine compounds, acylphosphine oxide compounds, O-acyloxime compounds, and biimidazole compounds.

[0150] The O-acyloxime compound is a compound having a partial structure represented by formula (d1): In the following, * represents a bond.

[0151] [ka]

[0152] Examples of the O-acyloxime compound include N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethan-1-imine, N-acetoxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethyl-2,4-dioxacyclopentanylmethyloxy)benzoyl}-9H-carbazol-3-yl]ethan-1-imine, N- acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropan-1-imine, N-benzoyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropan-1-one-2-imine, N-acetyloxy-1-[4-(2-hydroxyethyloxy)phenylsulfanylphenyl]propan-1-one-2-imine, N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine, 2-[(acetyloxy)imino]-3-cyclohexyl-1-[4-(phenylsulfanyl)phenyl]propan-1-one, and the like. Commercially available products such as Irgacure OXE01, OXE02, and OXE03 (all manufactured by BASF), N-1919 (manufactured by ADEKA), PBG-314, PBG-317, PBG-326, PBG-327, and PBG-329 (all manufactured by Changzhou Strong Electronic New Materials Co., Ltd.) may also be used.Among them, the O-acyloxime compounds are N-acetyloxy-1-[4-(2-hydroxyethyloxy)phenylsulfanylphenyl]propan-1-one-2-imine, N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine, 2-[(acetyloxy)imino]-3-cyclohexyl-1-[4-(phenylsulfanyl)phenyl]propan-1-one, N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine, N-acetyl ... At least one selected from the group consisting of 2-[(acetyloxy)imino]-3-cyclohexyl-1-[4-(phenylsulfanyl)phenyl]propan-1-one, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine, and N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine is preferred, and at least one selected from the group consisting of 2-[(acetyloxy)imino]-3-cyclohexyl-1-[4-(phenylsulfanyl)phenyl]propan-1-one, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine, and N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine is more preferred. With these O-acyloxime compounds, a color filter with high brightness tends to be obtained.

[0153] The alkylphenone compound is a compound having a partial structure represented by formula (d2) or a partial structure represented by formula (d3). In these partial structures, the benzene ring may have a substituent.

[0154] [ka]

[0155] Examples of the compound having a partial structure represented by formula (d2) include 2-methyl-2-morpholino-1-(4-methylsulfanylphenyl)propan-1-one, 2-dimethylamino-1-(4-morpholinophenyl)-2-benzylbutan-1-one, 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]butan-1-one, etc. Commercially available products such as Irgacure 369, 907, and 379 (all manufactured by BASF) may also be used.

[0156] Examples of compounds having a partial structure represented by formula (d3) include 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy)phenyl]propan-1-one, 1-hydroxycyclohexyl phenyl ketone, oligomers of 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propan-1-one, α,α-diethoxyacetophenone, and benzyl dimethyl ketal. In terms of sensitivity, the alkylphenone compound is preferably a compound having a partial structure represented by formula (d2).

[0157] Examples of the triazine compound include 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxynaphthyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxystyryl)-1,3,5-triazine, and 2,4-bis(trichloromethyl)-6-[ 2-(5-methylfuran-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)ethenyl]-1,3,5-triazine, and the like.

[0158] The acylphosphine oxide compound may be 2,4,6-trimethylbenzoyldiphenylphosphine oxide, etc. Commercially available products such as Irgacure (registered trademark) 819 (manufactured by BASF) may also be used.

[0159] Examples of the biimidazole compound include 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3-dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole (see, for example, JP-A-6-75372 and JP-A-6-75373), 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(alkoxyphenyl) 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(dialkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(trialkoxyphenyl)biimidazole (see, for example, JP-B-48-38403 and JP-A-62-174204), and biimidazole compounds in which the phenyl groups at the 4,4',5,5'-positions are substituted with carboalkoxy groups (see, for example, JP-A-7-10913).

[0160] Further, examples of the polymerization initiator (D) include benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether; benzophenone compounds such as benzophenone, o-benzoyl methyl benzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, 3,3',4,4'-tetra(tert-butylperoxycarbonyl)benzophenone, and 2,4,6-trimethylbenzophenone; quinone compounds such as 9,10-phenanthrenequinone, 2-ethylanthraquinone, and camphorquinone; 10-butyl-2-chloroacridone, benzyl, methyl phenylglyoxylate, and titanocene compounds. These are preferably used in combination with the polymerization initiator aid (D1) described below (especially amine compounds).

[0161] Examples of the polymerization initiator that generates an acid include onium salts such as 4-hydroxyphenyl dimethylsulfonium p-toluenesulfonate, 4-hydroxyphenyl dimethylsulfonium hexafluoroantimonate, 4-acetoxyphenyl dimethylsulfonium p-toluenesulfonate, 4-acetoxyphenyl methylbenzylsulfonium hexafluoroantimonate, triphenylsulfonium p-toluenesulfonate, triphenylsulfonium hexafluoroantimonate, diphenyliodonium p-toluenesulfonate, and diphenyliodonium hexafluoroantimonate; nitrobenzyl tosylates; and benzoin tosylates.

[0162] The polymerization initiator (D) is preferably a polymerization initiator containing at least one selected from the group consisting of an alkylphenone compound, a triazine compound, an acylphosphine oxide compound, an O-acyloxime compound, and a biimidazole compound, and more preferably a polymerization initiator containing an O-acyloxime compound.

[0163] The content of the polymerization initiator (D) is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, and further preferably 2 to 10 parts by mass, based on 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). When the content of the polymerization initiator (D) is within the above range, the sensitivity is increased and the exposure time tends to be shortened, thereby improving the productivity of the color filter.

[0164] <Polymerization initiator aid (D1)> The polymerization initiation aid (D1) is a compound used to promote the polymerization of a polymerizable compound whose polymerization has been initiated by a polymerization initiator, or a sensitizer. When the polymerization initiation aid (D1) is contained, it is usually used in combination with the polymerization initiator (D). Examples of the polymerization initiator aid (D1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds, and carboxylic acid compounds.

[0165] Examples of the amine compound include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 2-ethylhexyl 4-dimethylaminobenzoate, N,N-dimethyl-p-toluidine, 4,4'-bis(dimethylamino)benzophenone (commonly known as Michler's ketone), 4,4'-bis(diethylamino)benzophenone, 4,4'-bis(ethylmethylamino)benzophenone, etc., and among these, 4,4'-bis(diethylamino)benzophenone is preferred. Commercially available products such as EAB-F (manufactured by Hodogaya Chemical Co., Ltd.) may also be used.

[0166] Examples of the alkoxyanthracene compound include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene, 9,10-dibutoxyanthracene, and 2-ethyl-9,10-dibutoxyanthracene.

[0167] Examples of the thioxanthone compound include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, and 1-chloro-4-propoxythioxanthone.

[0168] Examples of the carboxylic acid compound include phenylsulfanylacetic acid, methylphenylsulfanylacetic acid, ethylphenylsulfanylacetic acid, methylethylphenylsulfanylacetic acid, dimethylphenylsulfanylacetic acid, methoxyphenylsulfanylacetic acid, dimethoxyphenylsulfanylacetic acid, chlorophenylsulfanylacetic acid, dichlorophenylsulfanylacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, and naphthoxyacetic acid.

[0169] When these polymerization initiation aids (D1) are used, the content thereof is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, based on 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). When the amount of the polymerization initiation aid (D1) is within this range, a colored pattern can be formed with higher sensitivity, and the productivity of the color filter tends to improve.

[0170] <Solvent (E)> The solvent (E) is not particularly limited, and a solvent commonly used in the field can be used. For example, ester solvent (solvent containing -COO- in the molecule and not containing -O-), ether solvent (solvent containing -O- in the molecule and not containing -COO-), ether ester solvent (solvent containing -COO- and -O- in the molecule), ketone solvent (solvent containing -CO- in the molecule and not containing -COO-), alcohol solvent (solvent containing OH in the molecule and not containing -O-, -CO- and -COO-), aromatic hydrocarbon solvent, amide solvent, dimethyl sulfoxide, etc. can be mentioned.

[0171] Examples of ester solvents include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutanoate, ethyl acetate, n-butyl acetate, isobutyl acetate, pentyl formate, isopentyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexanol acetate, and γ-butyrolactone.

[0172] Examples of the ether solvent include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenetole, and methylanisole.

[0173] The ether ester solvents include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methyl ... Examples of the alkyl ether acetates include ethyl methoxy-2-methylpropionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, and diethylene glycol monobutyl ether acetate.

[0174] Ketone solvents include 4-hydroxy-4-methyl-2-pentanone (diacetone alcohol), acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone, and isophorone.

[0175] Examples of the alcohol solvent include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerin.

[0176] Aromatic hydrocarbon solvents include benzene, toluene, xylene, and mesitylene.

[0177] Amide solvents include N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.

[0178] Among the above-mentioned solvents, from the viewpoint of coatability and drying property, an organic solvent having a boiling point at 1 atm of 120° C. or more and 180° C. or less is preferred. As the solvent, at least one selected from the group consisting of propylene glycol monomethyl ether acetate, ethyl lactate, propylene glycol monomethyl ether, ethyl 3-ethoxypropionate, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, 4-hydroxy-4-methyl-2-pentanone and N,N-dimethylformamide is preferred, and at least one selected from the group consisting of propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, 4-hydroxy-4-methyl-2-pentanone, ethyl lactate and ethyl 3-ethoxypropionate is more preferred.

[0179] It is also preferable to use an ether ester solvent and a ketone solvent in combination as the solvent (E). In this case, the ether ester solvent is preferably C 2-3 Alkylene glycol mono C 1-4 Alkyl ether acetate is preferred, propylene glycol mono C 1-4 More preferred are alkyl ether acetates. A preferred ketone solvent is 4-hydroxy-4-methyl-2-pentanone. When an ether ester solvent and a ketone solvent are used in combination, the content of the ketone solvent is preferably 1 to 100 parts by mass, more preferably 3 to 50 parts by mass, and further preferably 5 to 20 parts by mass, per 100 parts by mass of the total of the ether ester solvent and the ketone solvent.

[0180] The content of the solvent (E) is preferably 70 to 95% by mass, more preferably 75 to 92% by mass, based on the total amount of the colored resin composition. In other words, the solid content of the colored resin composition is preferably 5 to 30% by mass, more preferably 8 to 25% by mass. When the content of the solvent (E) is within the above range, the flatness during coating is good, and the color density is not insufficient when a color filter is formed, so that the display characteristics and sensitivity tend to be good.

[0181] <Leveling agent (F)> Examples of the leveling agent (F) include silicone surfactants, fluorine surfactants, and silicone surfactants having fluorine atoms, which may have a polymerizable group in the side chain.

[0182] Examples of silicone surfactants include surfactants having a siloxane bond in the molecule.Specific examples include Toray Silicone DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, SH29PA, SH30PA, and SH8400 (trade name: manufactured by Toray Dow Corning Co., Ltd.), KP321, KP322, KP323, KP324, KP326, KP340, and KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452, and TSF4460 (manufactured by Momentive Performance Materials Japan LLC).

[0183] The fluorine-based surfactant may include surfactants having a fluorocarbon chain in the molecule.Specific examples include Fluorad (registered trademark) FC430, FC431 (manufactured by Sumitomo 3M Limited), Megafac (registered trademark) F142D, F171, F172, F173, F177, F183, F554, R30, RS-718-K (manufactured by DIC Corporation), F-top (registered trademark) EF301, EF303, EF351, EF352 (manufactured by Mitsubishi Materials Electronic Chemicals Co., Ltd.), Surflon (registered trademark) S381, S382, SC101, SC105 (manufactured by AGC Corporation (formerly Asahi Glass Co., Ltd.)) and E5844 (manufactured by Daikin Fine Chemical Research Institute Co., Ltd.).

[0184] Examples of the silicone surfactant having a fluorine atom include surfactants having a siloxane bond and a fluorocarbon chain in the molecule, such as Megafac (registered trademark) R08, BL20, F475, F477, and F443 (manufactured by DIC Corporation).

[0185] The content of the leveling agent (F) is preferably 0.001 to 0.2 mass%, more preferably 0.002 to 0.1 mass%, and even more preferably 0.005 to 0.05 mass%, based on the total amount of the colored resin composition. This content does not include the content of the pigment dispersant described below. When the content of the leveling agent (F) is within the above range, the flatness of the color filter can be improved.

[0186] <Other ingredients> The colored resin composition may contain additives known in the art, such as fillers, other polymer compounds, adhesion promoters, antioxidants, light stabilizers, and chain transfer agents, as necessary.

[0187] <Method of producing colored resin composition> The colored resin composition can be prepared, for example, by mixing the colorant (A) and the resin (B), as well as the polymerizable compound (C), polymerization initiator (D), solvent (E), leveling agent (F), polymerization initiator aid (D1) and other components that are used as necessary. The colored resin composition after mixing may be filtered through a filter having a pore size of about 0.01 to 10 μm.

[0188] The compound (I) as the colorant (A) and the pigment as the colorant (A1) used as required may be used as a dispersion liquid in a state of being uniformly dispersed in a solution by adding a pigment dispersant and carrying out a dispersion treatment. The remaining components are mixed with such a dispersion liquid to a predetermined concentration to prepare a desired colored resin composition. The compound (I) and the pigment may be dispersed alone or in a mixture of multiple types.

[0189] Examples of pigment 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 Co., Ltd.), EFKA (registered trademark) (manufactured by BASF), AJISPER (registered trademark) (manufactured by Ajinomoto Fine-Techno Co., Ltd.), Disperbyk (registered trademark), and BYK (registered trademark) (manufactured by BYK-Chemie Co., Ltd.).

[0190] When a pigment dispersant is used, the amount thereof is preferably 5 parts by mass or more and 200 parts by mass or less, more preferably 10 parts by mass or more and 150 parts by mass or less, and even more preferably 20 parts by mass or more and 130 parts by mass or less, relative to 100 parts by mass of the colorant (A) (specifically, the compound (I) and the pigment) in the dispersion. When the amount of the pigment dispersant used is within the above range, a dispersion in a more uniformly dispersed state tends to be obtained.

[0191] When the colorant (A) contains a dye, the dye may be dissolved in advance in a part or whole of the solvent (E) to prepare a solution. The solution is preferably filtered through a filter having a pore size of about 0.01 to 1 μm.

[0192] [Color Filter] Examples of the method for producing a colored pattern of a color filter from the colored resin composition of the present invention include a photolithography method, an inkjet method, and a printing method. Among them, the photolithography method is preferable. The photolithography method is a method in which the colored resin composition is applied to a substrate, dried to form a composition layer, and the composition layer is exposed through a photomask and developed. In the photolithography method, a colored coating film, which is a cured product of the composition layer, can be formed by not using a photomask during exposure and / or not developing.

[0193] The film thickness of the color filter (colored coating film or colored pattern) is, for example, 30 μm or less, preferably 20 μm or less, more preferably 6 μm or less, even more preferably 3 μm or less, even more preferably 1.5 μm or less, particularly preferably 0.5 μm or less, and is preferably 0.1 μm or more, more preferably 0.2 μm or more, and even more preferably 0.3 μm or more.

[0194] The substrate may be a glass plate such as quartz glass, borosilicate glass, alumina silicate glass, or soda lime glass with a silica-coated surface, a resin plate such as polycarbonate, polymethylmethacrylate, or polyethylene terephthalate, silicon, or a substrate having a thin film of aluminum, silver, or a silver / copper / palladium alloy formed thereon. On these substrates, another color filter layer, a resin layer, a transistor, a circuit, or the like may be formed. A silicon substrate having an HMDS treatment may also be used.

[0195] Formation of each color pixel (each color color filter) by photolithography can be performed with known or conventional equipment and conditions. For example, it can be produced as follows. First, a colored resin composition is applied onto a substrate, and volatile components such as a solvent are removed by heating and drying (pre-baking) and / or drying under reduced pressure to obtain a smooth composition layer. Examples of the application method include spin coating, slit coating, and slit and spin coating. The temperature when drying by heating is preferably 30 to 120°C, more preferably 50 to 110°C. The heating time is preferably 10 seconds to 60 minutes, more preferably 30 seconds to 30 minutes. When drying under reduced pressure, it is preferably performed under a pressure of 50 to 150 Pa at a temperature range of 20 to 25°C. The film thickness of the composition layer is not particularly limited and may be appropriately selected according to the film thickness of the desired color filter.

[0196] Next, the composition layer is exposed through a photomask for forming a desired colored pattern. The pattern on the photomask is not particularly limited, and a pattern according to the intended use is used. As the light source used for exposure, a light source that generates light with a wavelength of 250 to 450 nm is preferable. For example, light less than 250 nm may be cut using a filter that cuts this wavelength range, or light near 436 nm, near 408 nm, and near 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. It is preferable to use a reduced projection exposure device or a proximity exposure device such as a mask aligner and a stepper, since it is possible to uniformly irradiate the entire exposure surface with parallel light rays and to accurately align the photomask and the substrate.

[0197] The composition layer after exposure is brought into contact with a developer for development, thereby forming a colored pattern on the substrate. The unexposed portion of the composition layer is dissolved in the developer and removed by development. The developer is preferably an aqueous solution of an alkaline compound such as potassium hydroxide, sodium hydrogen carbonate, 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. Furthermore, the developer may contain a surfactant. The development method may be any of a paddle method, a dipping method, and a spray method. Furthermore, the substrate may be tilted at any angle during development. After development, it is preferable to wash with water.

[0198] Furthermore, it is preferable to perform post-baking on the obtained colored pattern. The post-baking temperature is preferably 80 to 250° C., more preferably 100 to 245° C. The post-baking time is preferably 1 to 120 minutes, more preferably 2 to 30 minutes.

[0199] The colored pattern and colored coating film thus obtained are useful as color filters, and the color filters are useful as color filters for use in display devices (e.g., liquid crystal display devices, organic EL devices, etc.), electronic paper, solid-state imaging devices, etc.

[0200] In particular, the colored pattern and colored coating film are useful as a green filter in a color filter. When the colored pattern or colored coating film has a film thickness of 2.0 μm, it is preferable that the colored pattern or colored coating film satisfies the following (i) and (ii). A colored resin composition capable of forming a colored pattern or colored coating film that satisfies the following (i) and (ii) can form a green filter with excellent spectral characteristics. In particular, from the viewpoint of being able to exhibit good spectral characteristics even after long-term use, it is preferable that the colored pattern and colored coating film satisfy the following (i) and (ii) even after the light irradiation test described in the Examples section below. (i) Transmittance at 550 nm is 35% or more and 99% or less (ii) Transmittance at 620 nm is 0.1% or more and 30% or less (preferably 0.1 to 20%) EXAMPLES

[0201] 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 can be modified as long as it satisfies 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".

[0202] In the following examples, the structures of the compounds were confirmed by mass spectrometry (MALDI-TOF MS; JMS-S3000 manufactured by JEOL Ltd.) or mass spectrometry (LC-MS (LC; 1200 model manufactured by Agilent; MS; LC / MSD model manufactured by Agilent)).

[0203] In the following examples, the maximum absorption wavelength was confirmed by ultraviolet, visible and near infrared absorption spectroscopy (JASCO: V-770).

[0204] (Synthesis Example 1) <Preparation of Compound (II-1)> Under a nitrogen atmosphere, 23 parts of 4-nitrophthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.), 20 parts of 2-(sec-butyl)phenol (manufactured by Tokyo Chemical Industry Co., Ltd.), 20 parts of potassium carbonate (manufactured by Kanto Chemical Co., Ltd.), and 160 parts of dehydrated acetonitrile (manufactured by Kanto Chemical Co., Ltd.) were mixed and heated to 80°C, and then stirred at the same temperature for 10 hours. The reaction liquid was cooled to room temperature (18 to 24°C) and filtered to obtain filtrate A and residue A. Residue A was washed with 160 parts of acetonitrile, and the obtained acetonitrile solution and filtrate A were combined, and the solvent in the solution was distilled off. The obtained residue was washed with 80 parts of ion-exchanged water and dried, and 35 parts of a compound represented by formula (II-1) (hereinafter, compound (II-1)) were obtained as a colorless solid (yield 96%).

[0205] [ka]

[0206] <Identification of Compound (II-1)> (Mass spectrometry) Ionization mode = MALDI-TOF - : m / z= 276 Exact Mass: 276

[0207] Example 1 <Preparation of compound (I-e1)> Under a nitrogen atmosphere, 10.0 parts of the compound (II-1) produced in Synthesis Example 1, 1.3 parts of anhydrous aluminum chloride (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.), 83.0 parts of triethylene glycol (manufactured by Tokyo Chemical Industry Co., Ltd.), and 8.3 parts of 1,8-diazabicyclo[5,4,0]-7-undecene (manufactured by Tokyo Chemical Industry Co., Ltd.) were mixed and heated at 140 ° C. for 10 hours. After the reaction was completed, the reaction solution was cooled to room temperature (18 to 24 ° C.) and poured into 100 parts of ion-exchanged water. The precipitated solid was separated by decantation in the order of 50 parts of ion-exchanged water twice and 50 parts of acetone once. The obtained crude product was purified by silica gel column chromatography (developing solvent: gradient from toluene to tetrahydrofuran) to obtain 2.41 parts (yield 24%) of a compound represented by formula (I-e1) (hereinafter, compound (I-e1)). However, the compound represented by formula (IV-e1) (hereinafter, compound (IV-e1)) was not obtained.

[0208] [ka]

[0209] <Identification of compound (I-e1)> (Mass spectrometry) Ionization mode = MALDI-TOF - : m / z= 1107 Exact Mass: 1107

[0210] (Synthesis Example 2) <Preparation of Compound (II-2)> Except for using 29 parts of 4-bromo-2,6-di(tert-butyl)phenol (Tokyo Chemical Industry Co., Ltd.) instead of 20 parts of 2-(sec-butyl)phenol, the same procedure as in Synthesis Example 1 was followed to obtain 35 parts (yield 76%) of a colorless solid compound represented by formula (II-2) (hereinafter, compound (II-2)).

[0211] [ka]

[0212] <Identification of compound (II-2)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 411 Exact Mass: 410

[0213] Example 2 <Preparation of compound (I-e2)> Except for using 14.9 parts of compound (II-2) obtained in Synthesis Example 2 instead of 10.0 parts of compound (II-1), the same procedure as in Example 1 was repeated to obtain 5.83 parts (yield 39%) of a compound represented by formula (I-e2) (hereinafter, compound (I-e2)) and 1.09 parts (yield 7%) of a compound represented by formula (IV-e2) (hereinafter, compound (IV-e2)).

[0214] [ka]

[0215] <Identification of compound (I-e2)> (Mass spectrometry) Ionization mode = MALDI-TOF - : m / z= 1642 Exact Mass: 1642 <Identification of compound (IV-e2)> It was confirmed by silica gel thin layer chromatography (TLC) that only two types of colored components were obtained in the reaction of Example 2. One type was confirmed to be compound (I-e2) by MALDI-TOF MS as described above. The remaining type was confirmed to be a metal body because it showed a unique spectral shape of a metal body in measurement (hereinafter referred to as UV-vis measurement) using an ultraviolet-visible near-infrared absorption spectrometer (JASCO: V-770). In view of the reaction substrate, it is clear that the metal body is an aluminum body. Furthermore, the Rf value (developing solvent toluene) in silica gel thin layer chromatography (TLC) was 0.30 for a compound represented by the following formula (IV-e16), which is a similar compound, and 0.28 for the above aluminum body, so that the aluminum body was identified to be compound (IV-e2).

[0216] [ka]

[0217] (Synthesis Example 3) <Preparation of Compound (II-3)> Except for using 18 parts of 2-isopropylphenol (Tokyo Chemical Industry Co., Ltd.) instead of 20 parts of 2-(sec-butyl)phenol, the same procedure as in Synthesis Example 1 was repeated to obtain 34 parts (yield 97%) of a colorless solid compound represented by formula (II-3) (hereinafter, compound (II-3)).

[0218] [ka]

[0219] <Identification of compound (II-3)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 263 Exact Mass: 262

[0220] Example 3 <Preparation of compound (I-e3)> Except for using 9.5 parts of compound (II-3) obtained in Synthesis Example 3 instead of 10.0 parts of compound (II-1), the same procedure as in Example 1 was repeated to obtain 4.1 parts (43% yield) of a compound represented by formula (I-e3) (hereinafter, compound (I-e3)) and 0.81 parts (8% yield) of a compound represented by formula (IV-e3) (hereinafter, compound (IV-e3)).

[0221] [ka]

[0222] <Identification of compound (I-e3)> (Mass spectrometry) Ionization mode = MALDI-TOF - : m / z= 1050 Exact Mass: 1050 <Identification of compound (IV-e3)> Silica gel thin layer chromatography (TLC) confirmed that only two types of colored components were obtained in the reaction of Example 3. One type was confirmed to be compound (I-e3) by MALDI-TOF MS as described above. The remaining type was confirmed to be a metal body because it showed a unique spectral shape of a metal body in UV-vis measurement. In view of the reaction substrate, it is clear that the metal body is an aluminum body. Furthermore, the Rf value (developing solvent toluene) in silica gel thin layer chromatography (TLC) was 0.30 for the compound represented by formula (IV-e16), which is a similar compound, and 0.33 for the above aluminum body, so that the aluminum body was identified as compound (IV-e3).

[0223] (Synthesis Example 4) <Preparation of Compound (II-4)> Except for using 25 parts of 2-cyclohexyl-5-methylphenol (Tokyo Chemical Industry Co., Ltd.) instead of 20 parts of 2-(sec-butyl)phenol, the same procedure as in Synthesis Example 1 was repeated to obtain 38 parts (yield 91%) of a compound represented by formula (II-4) (hereinafter, compound (II-4)) as a colorless solid.

[0224] [ka]

[0225] <Identification of Compound (II-4)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 317 Exact Mass: 316

[0226] Example 4 <Preparation of compound (I-e4)> Except for using 11.5 parts of compound (II-4) obtained in Synthesis Example 4 instead of 10.0 parts of compound (II-1), the same procedure as in Example 1 was repeated to obtain 3.80 parts (yield 33%) of a compound represented by formula (I-e4) (hereinafter, compound (I-e4)) and 0.60 parts (yield 5%) of a compound represented by formula (IV-e4) (hereinafter, compound (IV-e4)).

[0227] [ka]

[0228] <Identification of compound (I-e4)> (Mass spectrometry) Ionization mode = MALDI-TOF - : m / z= 1267 Exact Mass: 1267 <Identification of compound (IV-e4)> Silica gel thin layer chromatography (TLC) confirmed that only two types of colored components were obtained in the reaction of Example 4. One type was confirmed to be compound (I-e4) by MALDI-TOF MS as described above. The remaining type was confirmed to be a metal body because it showed a unique spectral shape of a metal body in UV-vis measurement. In view of the reaction substrate, it is clear that the metal body is an aluminum body. Furthermore, the Rf value (developing solvent toluene) in silica gel thin layer chromatography (TLC) was 0.30 for the compound represented by formula (IV-e16), which is a similar compound, and 0.35 for the above aluminum body, so the aluminum body was identified as compound (IV-e4).

[0229] (Synthesis Example 5) <Preparation of Compound (II-5)> Compound (II-5) was quantitatively obtained as a colorless liquid in the same manner as in Synthesis Example 1, except that 25 parts of 2-tert-butylphenol (manufactured by Tokyo Chemical Industry Co., Ltd.) was used instead of 20 parts of 2-(sec-butyl)phenol.

[0230] [ka]

[0231] <Identification of Compound (II-5)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 277 Exact Mass: 276

[0232] Example 5 <Preparation of compound (I-e5)> Except for using 10.0 parts of compound (II-5) obtained in Synthesis Example 5 instead of 10.0 parts of compound (II-1), the same procedure as in Example 1 was repeated to obtain 3.01 parts (yield 30%) of a compound represented by formula (I-e5) (hereinafter, compound (I-e5)) and 0.95 parts (yield 9%) of a compound represented by formula (IV-e5) (hereinafter, compound (IV-e5)).

[0233] [ka]

[0234] <Identification of compound (I-e5)> (Mass spectrometry) Ionization mode = MALDI-TOF - : m / z= 1107 Exact Mass: 1107 <Identification of compound (IV-e5)> Silica gel thin layer chromatography (TLC) confirmed that only two types of colored components were obtained in the reaction of Example 5. One type was confirmed to be compound (I-e5) by MALDI-TOF MS as described above. The remaining type was confirmed to be a metal body because it showed a unique spectral shape of a metal body in UV-vis measurement. In view of the reaction substrate, it is clear that the metal body is an aluminum body. Furthermore, the Rf value (developing solvent toluene) in silica gel thin layer chromatography (TLC) was 0.30 for the compound represented by formula (IV-e16), which is a similar compound, and 0.33 for the above aluminum body, so that the aluminum body was identified as compound (IV-e5).

[0235] (Synthesis Example 6) <Preparation of Compound (II-6)> Except for using 25 parts of 2-isopropyl-5-methylphenol (Tokyo Chemical Industry Co., Ltd.) instead of 20 parts of 2-(sec-butyl)phenol, the same procedure as in Synthesis Example 1 was repeated to obtain 39 parts (yield 93%) of a colorless solid compound represented by formula (II-6) (hereinafter, compound (II-6)).

[0236] [ka]

[0237] <Identification of compound (II-6)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 277 Exact Mass: 276

[0238] Example 6 <Preparation of compound (I-e6)> Except for using 10.0 parts of compound (II-6) obtained in Synthesis Example 6 instead of 10.0 parts of compound (II-1), the same procedure as in Example 1 was repeated to obtain 2.31 parts (yield 23%) of a compound represented by formula (I-e6) (hereinafter, compound (I-e6)) and 1.12 parts (yield 11%) of a compound represented by formula (IV-e6) (hereinafter, compound (IV-e6)).

[0239] [ka]

[0240] <Identification of compound (I-e6)> (Mass spectrometry) Ionization mode = MALDI-TOF - : m / z= 1107 Exact Mass: 1107 <Identification of compound (IV-e6)> Silica gel thin layer chromatography (TLC) confirmed that only two types of colored components were obtained in the reaction of Example 6. One type was confirmed to be compound (I-e6) by MALDI-TOF MS as described above. The remaining type was confirmed to be a metal body because it showed a unique spectral shape of a metal body in UV-vis measurement. In view of the reaction substrate, it is clear that the metal body is an aluminum body. Furthermore, the Rf value (developing solvent toluene) in silica gel thin layer chromatography (TLC) was 0.30 for the compound represented by formula (IV-e16), which is a similar compound, and 0.29 for the above aluminum body, so that the aluminum body was identified as compound (IV-e6).

[0241] (Synthesis Example 7) <Preparation of Compound (II-7)> Except for using 25 parts of 4-tert-butylphenol (Tokyo Chemical Industry Co., Ltd.) instead of 20 parts of 2-(sec-butyl)phenol, the same procedure as in Synthesis Example 1 was repeated to obtain 40 parts (yield 95%) of a colorless solid compound represented by formula (II-7) (hereinafter, compound (II-7)).

[0242] [ka]

[0243] <Identification of compound (II-7)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 277 Exact Mass: 276

[0244] Example 7 <Preparation of compound (I-e7)> Except for using 10.0 parts of compound (II-7) obtained in Synthesis Example 7 instead of 10.0 parts of compound (II-1), the same procedure as in Example 1 was repeated to obtain 3.10 parts (yield 31%) of a compound represented by formula (I-e7) (hereinafter, compound (I-e7)) and 1.07 parts (yield 10%) of a compound represented by formula (IV-e7) (hereinafter, compound (IV-e7)).

[0245] [ka]

[0246] <Identification of compound (I-e7)> (Mass spectrometry) Ionization mode = MALDI-TOF - : m / z= 1107 Exact Mass: 1107 <Identification of compound (IV-e7)> Silica gel thin layer chromatography (TLC) confirmed that only two types of colored components were obtained in the reaction of Example 7. One type was confirmed to be compound (I-e7) by MALDI-TOF MS as described above. The remaining type was confirmed to be a metal body because it showed a unique spectral shape of a metal body in UV-vis measurement. In view of the reaction substrate, it is clear that the metal body is an aluminum body. Furthermore, the Rf value (developing solvent toluene) in silica gel thin layer chromatography (TLC) was 0.30 for the compound represented by formula (IV-e16), which is a similar compound, and 0.27 for the above aluminum body, so that the aluminum body was identified as compound (IV-e7).

[0247] (Synthesis Example 8) <Preparation of Compound (II-8)> Except for using 18 parts of 2,3,6-trimethylphenol (Tokyo Chemical Industry Co., Ltd.) instead of 20 parts of 2-(sec-butyl)phenol, the same procedure as in Synthesis Example 1 was repeated to obtain 34 parts (yield 96%) of a colorless solid compound represented by formula (II-8) (hereinafter, compound (II-8)).

[0248] [ka]

[0249] <Identification of compound (II-8)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] +263 Exact Mass: 262

[0250] Example 8 <Preparation of compound (I-e8)> Except for using 9.50 parts of the compound (II-8) obtained in Synthesis Example 8 instead of 10.0 parts of the compound (II-1), the same procedure as in Example 1 was repeated to obtain 2.67 parts (yield 28%) of the compound represented by formula (I-e8) (hereinafter, compound (I-e8)). However, the compound represented by formula (IV-e8) (hereinafter, compound (IV-e8)) was not obtained.

[0251] [ka]

[0252] <Identification of compound (I-e8)> (Mass spectrometry) Ionization mode = MALDI-TOF - : m / z= 1050 Exact Mass: 1050

[0253] (Synthesis Example 9) <Preparation of Compound (II-9)> Except for using 24 parts of 2,6-diisopropylphenol (Tokyo Chemical Industry Co., Ltd.) instead of 20 parts of 2-(sec-butyl)phenol, the same procedure as in Synthesis Example 1 was repeated to obtain 36 parts (yield 90%) of a colorless solid compound represented by formula (II-9) (hereinafter, compound (II-9)).

[0254] [ka]

[0255] <Identification of Compound (II-9)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 305 Exact Mass: 304

[0256] Example 9 <Preparation of compound (I-e9)> Except for using 11.0 parts of compound (II-9) obtained in Synthesis Example 9 instead of 10.0 parts of compound (II-1), the same procedure as in Example 1 was repeated to obtain 5.65 parts (yield 51%) of a compound represented by formula (I-e9) (hereinafter, compound (I-e9)). However, a compound represented by formula (IV-e9) (hereinafter, compound (IV-e9)) was not obtained.

[0257] [ka]

[0258] <Identification of compound (I-e9)> (Mass spectrometry) Ionization mode = MALDI-TOF - : m / z= 1219 Exact Mass: 1219

[0259] (Synthesis Example 10) <Preparation of Compound (II-10)> Except for using 18 parts of 2-ethyl-6-methylphenol (Tokyo Chemical Industry Co., Ltd.) instead of 20 parts of 2-(sec-butyl)phenol, the same procedure as in Synthesis Example 1 was repeated to obtain 34 parts (yield 98%) of a colorless solid compound represented by formula (II-10) (hereinafter, compound (II-10)).

[0260] [ka]

[0261] <Identification of compound (II-10)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 263 Exact Mass: 262

[0262] Example 10 <Preparation of compound (I-e10)> Except for using 9.5 parts of the compound (II-10) obtained in Synthesis Example 10 instead of 10.0 parts of the compound (II-1), the same procedure as in Example 1 was repeated to obtain 1.81 parts (yield 19%) of the compound represented by formula (I-e10) (hereinafter, compound (I-e10)). However, the compound represented by formula (IV-e10) (hereinafter, compound (IV-e10)) was not obtained.

[0263] [ka]

[0264] <Identification of compound (I-10)> (Mass spectrometry) Ionization mode = MALDI-TOF - : m / z= 1050 Exact Mass: 1050

[0265] (Synthesis Example 11) <Preparation of Compound (II-11)> Except for using 33 parts of 2,6-diphenylphenol (Tokyo Chemical Industry Co., Ltd.) instead of 20 parts of 2-(sec-butyl)phenol, the same procedure as in Synthesis Example 1 was repeated to obtain 44 parts (yield 89%) of a colorless solid compound represented by formula (II-11) (hereinafter, compound (II-11)).

[0266] [ka]

[0267] <Identification of compound (II-11)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 373 Exact Mass: 372

[0268] Example 11 <Preparation of compound (I-e11)> Except for using 13.5 parts of the compound (II-11) obtained in Synthesis Example 11 instead of 10.0 parts of the compound (II-1), the same procedure as in Example 1 was repeated to obtain 2.44 parts (yield 18%) of the compound represented by formula (I-e11) (hereinafter, compound (I-e11)). However, the compound represented by formula (IV-e11) (hereinafter, compound (IV-e11)) was not obtained.

[0269] [ka]

[0270] <Identification of compound (I-e11)> (Mass spectrometry) Ionization mode = MALDI-TOF - : m / z= 1491 Exact Mass: 1491

[0271] (Synthesis Example 12) <Preparation of Compound (II-12)> Except for using 18 parts of 2,4,6-trimethylphenol (Tokyo Chemical Industry Co., Ltd.) instead of 20 parts of 2-(sec-butyl)phenol, the same procedure as in Synthesis Example 1 was repeated to obtain 34 parts (yield 97%) of a compound represented by formula (II-12) (hereinafter, compound (II-12)) as a colorless solid.

[0272] [ka]

[0273] <Identification of compound (II-12)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 263 Exact Mass: 262

[0274] Example 12 <Preparation of compound (I-e12)> Except for using 9.50 parts of compound (II-12) obtained in Synthesis Example 12 instead of 10.0 parts of compound (II-1), the same procedure as in Example 1 was repeated to obtain 4.87 parts (yield 51%) of a compound represented by formula (I-e12) (hereinafter, compound (I-e12)) and 1.20 parts (yield 12%) of a compound represented by formula (IV-e12) (hereinafter, compound (IV-e12)).

[0275] [ka]

[0276] <Identification of compound (I-e12)> (Mass spectrometry) Ionization mode = MALDI-TOF - : m / z= 1050 Exact Mass: 1050 <Identification of compound (IV-e12)> It was confirmed by silica gel thin layer chromatography (TLC) that only two types of colored components were obtained in the reaction of Example 12. One type was confirmed to be compound (I-e12) by MALDI-TOF MS as described above. The remaining type was confirmed to be a metal body because it showed a unique spectral shape of a metal body in UV-vis measurement. In view of the reaction substrate, it is clear that the metal body is an aluminum body. Furthermore, the Rf value (developing solvent toluene) in silica gel thin layer chromatography (TLC) was 0.30 for the compound represented by formula (IV-e16), which is a similar compound, and 0.32 for the above aluminum body, so that the aluminum body was identified as compound (IV-e12).

[0277] (Synthesis Example 13) <Preparation of Compound (II-13)> Except for using 22 parts of 2-tert-butyl-6-methylphenol (Tokyo Chemical Industry Co., Ltd.) instead of 20 parts of 2-(sec-butyl)phenol, the same procedure as in Synthesis Example 1 was repeated to obtain 38 parts (yield 97%) of a compound represented by formula (II-13) (hereinafter, compound (II-13)) as a colorless solid.

[0278] [ka]

[0279] <Identification of compound (II-13)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 291 Exact Mass: 290

[0280] Example 13 <Preparation of compound (I-e13)> Except for using 10.5 parts of compound (II-13) obtained in Synthesis Example 13 instead of 10.0 parts of compound (II-1), the same procedure as in Example 1 was followed to obtain 4.23 parts (40% yield) of a compound represented by formula (I-e13) (hereinafter, compound (I-e13)) and 1.22 parts (11% yield) of a compound represented by formula (IV-e13) (hereinafter, compound (IV-e13)).

[0281] [ka]

[0282] <Identification of compound (I-e13)> (Mass spectrometry) Ionization mode = MALDI-TOF - : m / z= 1163 Exact Mass: 1163 <Identification of compound (IV-e13)> Silica gel thin layer chromatography (TLC) confirmed that only two types of colored components were obtained in the reaction of Example 13. One type was confirmed to be compound (I-e13) by MALDI-TOF MS as described above. The remaining type was confirmed to be a metal body because it showed a unique spectral shape of a metal body in UV-vis measurement. In view of the reaction substrate, it is clear that the metal body is an aluminum body. Furthermore, the Rf value (developing solvent toluene) in silica gel thin layer chromatography (TLC) was 0.30 for the compound represented by formula (IV-e16), which is a similar compound, and 0.28 for the above aluminum body, so that the aluminum body was identified as compound (IV-e13).

[0283] (Synthesis Example 14) <Preparation of Compound (II-14)> Except for using 28 parts of 4-α-cumylphenol (Tokyo Chemical Industry Co., Ltd.) instead of 20 parts of 2-(sec-butyl)phenol, the same procedure as in Synthesis Example 1 was repeated to obtain 41 parts (yield 92%) of a compound represented by formula (II-14) (hereinafter, compound (II-14)) as a colorless solid.

[0284] [ka]

[0285] <Identification of compound (II-14)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 339 Exact Mass: 338

[0286] Example 14 <Preparation of compound (I-e14)> Except for using 12.3 parts of compound (II-14) obtained in Synthesis Example 14 instead of 10.0 parts of compound (II-1), the same procedure as in Example 1 was repeated to obtain 2.95 parts (yield 24%) of a compound represented by formula (I-e14) (hereinafter, compound (I-e14)) and 0.64 parts (yield 5%) of a compound represented by formula (IV-e14) (hereinafter, compound (IV-e14)).

[0287] [ka]

[0288] <Identification of compound (I-e14)> (Mass spectrometry) Ionization mode = MALDI-TOF - : m / z= 1355 Exact Mass: 1355 <Identification of compound (IV-e14)> (Mass spectrometry) Ionization mode = MALDI-TOF - : m / z= 1416 Exact Mass: 1415

[0289] (Synthesis Example 15) <Preparation of Compound (II-15)> Except for using 25 parts of 3-bromo-4-methylphenol (Tokyo Chemical Industry Co., Ltd.) instead of 20 parts of 2-(sec-butyl)phenol, the same procedure as in Synthesis Example 1 was repeated to obtain 40 parts (yield 95%) of a colorless solid compound represented by formula (II-15) (hereinafter, compound (II-15)).

[0290] [ka]

[0291] Example 15 <Preparation of compound (I-e15)> Except for using 11.4 parts of the compound (II-15) obtained in Synthesis Example 15 instead of 10.0 parts of the compound (II-1), the same procedure as in Example 1 was repeated to obtain 4.33 parts (yield 38%) of the compound represented by formula (I-e15) (hereinafter, compound (I-e15)). However, the compound represented by formula (IV-e15) (hereinafter, compound (IV-e15)) was not obtained.

[0292] [ka]

[0293] <Identification of compound (I-e15)> (Mass spectrometry) Ionization mode = MALDI-TOF - : m / z= 1251 Exact Mass: 1250 <Identification of compound (IV-e15)> (Mass spectrometry) Ionization mode = MALDI-TOF - : m / z= 1310 Exact Mass: 1310

[0294] (Synthesis Example 16) <Preparation of compound (II-16)> Except for using 25 parts of 2,6-dimethylphenol (Tokyo Chemical Industry Co., Ltd.) instead of 20 parts of 2-(sec-butyl)phenol, the same procedure as in Synthesis Example 1 was repeated to obtain 38 parts (yield 92%) of a colorless solid compound represented by formula (II-16) (hereinafter, compound (II-16)).

[0295] [ka]

[0296] Example 16 <Preparation of compound (I-e16)> Except for using 9.0 parts of compound (II-16) obtained in Synthesis Example 16 instead of 10.0 parts of compound (II-1), the same procedure as in Example 1 was followed to obtain 4.43 parts (yield 49%) of a compound represented by formula (I-e16) (hereinafter, compound (I-e16)) and 1.05 parts (yield 11%) of a compound represented by formula (IV-e16) (hereinafter, compound (IV-e16)).

[0297] [ka]

[0298] <Identification of compound (I-e16)> (Mass spectrometry) Ionization mode = MALDI-TOF - : m / z= 994 Exact Mass: 994 <Identification of compound (IV-e16)> (Mass spectrometry) Ionization mode = MALDI-TOF - : m / z= 1054 Exact Mass: 1054

[0299] (Synthesis Example 17) <Preparation of compound (II-17)> Except for using 39 parts of 4-methoxy-2,5-di(2-methylpentan-2-yl)phenol (Tokyo Chemical Industry Co., Ltd.) instead of 20 parts of 2-(sec-butyl)phenol, the same procedure as in Synthesis Example 1 was repeated to obtain 50 parts (yield 90%) of a colorless solid compound represented by formula (II-17) (hereinafter, compound (II-17)).

[0300] [ka]

[0301] (Example 17) <Preparation of compound (I-e17)> Except for using 15.1 parts of compound (II-17) obtained in Synthesis Example 17 instead of 10.0 parts of compound (II-1), the same procedure as in Example 1 was repeated to obtain 3.50 parts (yield 23%) of a compound represented by formula (I-e17) (hereinafter, compound (I-e17)) and 0.946 parts (yield 6%) of a compound represented by formula (IV-e17) (hereinafter, compound (IV-e17)).

[0302] [ka]

[0303] <Identification of compound (I-e17)> (Mass spectrometry) Ionization mode = MALDI-TOF - : m / z= 1675 Exact Mass: 1675 <Identification of compound (IV-e17)> (Mass spectrometry) Ionization mode = MALDI-TOF - : m / z= 1735 Exact Mass: 1735

[0304] (Synthesis Example 18) <Preparation of compound (II-18)> Except for using 16 parts of 2,6-dimethylphenol (manufactured by Tokyo Chemical Industry Co., Ltd.) instead of 20 parts of 2-(sec-butyl)phenol, and using 18.5 parts of 3-nitrophthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) instead of 23 parts of 4-nitrophthalonitrile, the same procedure as in Synthesis Example 1 was repeated to obtain 34 parts (yield 93%) of a colorless solid compound represented by formula (II-18) (hereinafter, compound (II-18)).

[0305] [ka]

[0306] <Identification of compound (II-18)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 249 Exact Mass: 248 (Example 18) <Preparation of compound (I-e18)> Except for using 9.0 parts of compound (II-18) obtained in Synthesis Example 18 instead of 10.0 parts of compound (II-1), the same procedure as in Example 1 was repeated to obtain 2.17 parts (yield 24%) of a compound represented by formula (I-e18) (hereinafter, compound (I-e18)) and 0.28 parts (yield 3%) of a compound represented by formula (IV-e18) (hereinafter, compound (IV-e18)).

[0307] [ka]

[0308] <Identification of compound (I-e18)> (Mass spectrometry) Ionization mode = MALDI-TOF - : m / z= 994 Exact Mass: 994 <Identification of compound (IV-e18)> (Mass spectrometry) Ionization mode = MALDI-TOF - : m / z= 1054 Exact Mass: 1054

[0309] Comparative Example 1 <Preparation of compound (I-e16)> A reaction was carried out in the same manner as in Example 16 except that anhydrous aluminum chloride was not used, but compound (I-e16) was not obtained.

[0310] [ka]

[0311] Comparative Example 2 <Preparation of compound (I-c1)> Under a nitrogen atmosphere, 43 parts of phthalonitrile, 15 parts of anhydrous aluminum chloride (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.), 105 parts of n-pentanol (manufactured by Tokyo Chemical Industry Co., Ltd.), and 51 parts of 1,8-diazabicyclo[5,4,0]-7-undecene (manufactured by Tokyo Chemical Industry Co., Ltd.) were mixed and heated at 136 ° C for 5 hours. After the reaction was completed, the reaction liquid was cooled to room temperature (18 to 24 ° C), and 630 parts of ethyl acetate were poured in. The precipitated solid was filtered, and the crude product was separated by decantation twice with 460 parts of ethyl acetate. The crude product was purified by repulping and washing with 630 parts of ion-exchanged water, and 32 parts (yield 65%) of the compound represented by formula (IV-c1) were obtained as a solid, but the compound represented by formula (I-c1) was not obtained.

[0312] [ka]

[0313] [Table 6]

[0314] In Table 6, the molar ratio (compound (I) / compound (IV)) indicates the amount of compound (I) per mole of compound (IV) isolated in each Example and Comparative Example.

[0315] As is clear from a comparison between Example 16 and Comparative Example 1, when the method of the present invention was employed, compound (I) could be synthesized in a short time and in a high yield. In addition, in the other Examples 1 to 15 and 17 to 18, compound (I) was preferentially produced over compound (IV), and compound (I) was obtained in a short time. Furthermore, since only aluminum phthalocyanine represented by formula (IV-c1) was obtained in Comparative Example 2, it is clear that the effect of adopting the production method of the present invention is specifically obtained in an embodiment having a specific aryloxy group (i).

[0316] (Resin synthesis example 1) <Preparation of Resin B-1> A suitable amount of nitrogen was flowed into a flask equipped with a reflux condenser, a dropping funnel and a stirrer to replace the atmosphere with nitrogen, 280 parts of propylene glycol monomethyl ether acetate was added, and the mixture was heated 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 completion of the dropwise addition, the mixture was kept at 80°C for 4 hours and then cooled to room temperature to obtain a copolymer (resin B-1) solution with a solid 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 B-1 had a polydispersity of 2.08 and an acid value calculated as solid content of 77 mg-KOH / g.

[0317] [ka]

[0318] (Resin synthesis example 2) <Synthesis of Resin B-2> A suitable amount of nitrogen was flowed into a flask equipped with a reflux condenser, a dropping funnel and a stirrer to replace the atmosphere with nitrogen, 350 parts of propylene glycol monomethyl ether acetate was added, and the mixture was heated to 85°C with stirring. Next, 70 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 2,6A mixture of 202 parts of a mixture of decan-9-yl acrylate (content ratio 1:1 by molar ratio), 78 parts of vinyl toluene (mixture of isomers), and 100 parts of propylene glycol monomethyl ether acetate was added dropwise over 4 hours. Meanwhile, a solution of 33 parts of the polymerization initiator 2,2-azobis(2,4-dimethylvaleronitrile) dissolved in 167 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. After the dropwise addition of the initiator solution was completed, the mixture was kept at 85°C for 4 hours and then cooled to room temperature to obtain a copolymer (resin B-2) solution with a viscosity of 431 mPa·s measured with a Brookfield viscometer (23°C) and a solid content of 38.1%. The weight average molecular weight Mw of the resulting copolymer was 1.04×10 4 The polydispersity was 2.03, and the acid value calculated as solid content was 139 mg-KOH / g. Resin B-2 has the following structural units.

[0319] [ka]

[0320] 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. Equipment: 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.

[0321] <Dispersion liquid preparation example 1> 5.0 parts of the compound (I-e17) obtained in Example 17, 3.5 parts of a dispersant (BYKLPN-6919 manufactured by BYK) (solid content equivalent), 3.5 parts of resin B-2 (solid content equivalent), 78 parts of propylene glycol monomethyl ether acetate, and 10 parts of diacetone alcohol were mixed, and 300 parts of 0.2 mm zirconia beads were added and shaken, and the zirconia beads were removed by filtration to obtain a dispersion (P-1).

[0322] <Dispersion Liquid Preparation Examples 2 to 4> Dispersions (P-2) to (P-4) were obtained in the same manner as in Dispersion Preparation Example 1, except that the compound (I-e17) in Dispersion Preparation Example 1 was changed to the compound below. Dispersion (P-2): Compound (I-e16) obtained in Example 16 Dispersion (P-3): Compound (I-e18) obtained in Example 17 Dispersion (P-4): Compound (I-e4) obtained in Example 18

[0323] <Dispersion Liquid Preparation Example 6> CI Pigment Green 58 14 parts Acrylic pigment dispersant (solid content equivalent) 1.9 parts Resin (B-2) (solid content equivalent) 6.5 parts Propylene glycol monomethyl ether acetate 78 parts The above ingredients were mixed and the pigment was dispersed using a bead mill to obtain a dispersion liquid (P-c1).

[0324] <Dispersion Liquid Preparation Example 7> CI Pigment Yellow 138 15 parts Acrylic pigment dispersant (solid content equivalent) 4.5 parts Resin (B-1) (solid content equivalent) 4.5 parts Propylene glycol monomethyl ether acetate 76 parts The above ingredients were mixed and the pigment was dispersed using a bead mill to obtain a dispersion liquid (A-1).

[0325] <Dispersion Liquid Preparation Example 8> CI Pigment Yellow 185 10 parts Acrylic pigment dispersant 4.0 parts Resin (B-2) (solid content equivalent) 3.6 parts Propylene glycol monomethyl ether acetate 82 parts The above ingredients were mixed and the pigment was dispersed using a bead mill to obtain a dispersion (A-2).

[0326] <Examples A1 to A5 and Comparative Examples A1 to A2> (Preparation of Colored Resin Composition) Colored resin compositions E1 to E5 and C1 to C2 were obtained by mixing the components shown in Table 7. In preparing the colored resin compositions, the ratio of the colorant in the solid content of the colored resin composition was 40 mass% in Examples A1 to A2 and Comparative Example A1, 35 mass% in Example A3 and Comparative Example A2, 36 mass% in Example A4, and 32 mass% in Example A5.

[0327] [Table 7]

[0328] In Table 7, each component represents the following compound. Resin (B-1): Resin B-1 (solid content equivalent) Polymerizable compound (C-1): Dipentaerythritol polyacrylate: Trade name A-9550: manufactured by Shin-Nakamura Chemical Co., Ltd. Polymerization initiator (D-1): N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine: Trade name PBG-327: O-acyloxime compound: Manufactured by Changzhou Strong Electronic New Materials Co., Ltd. Leveling agent (F-1): Polyether modified silicone oil: Product name: Toray Silicone SH8400: Manufactured by Toray Dow Corning Co., Ltd. Solvent (E-1): Propylene glycol monomethyl ether acetate In addition, the amount shown in the column for solvent (E-1) in Table 7 indicates the total amount including the amount of propylene glycol monomethyl ether acetate contained in resin (B-1).

[0329] <Examples B1 to B9 and Comparative Examples B1 to B4> (Preparation of colored patterns) Each of the colored resin compositions E1 to E5 and C1 to C2 was applied by spin coating onto a 5 cm square glass substrate (Eagle 2000; Corning Incorporated), and then prebaked at 100°C for 3 minutes to form a colored composition layer. After cooling, the substrate was exposed to light at 100 mJ / cm2 in the air without using a photomask using an exposure machine (TME-150RSK; Topcon Corporation). 2 The colored composition layer after the light irradiation was post-baked in an oven at 230° C. for 20 minutes to obtain a colored coating film. After cooling, the thickness of the obtained colored coating film was measured using a thickness measuring device (DEKTAK3; manufactured by Nippon Shinku Gijutsu Co., Ltd.), and the thickness of the obtained colored coating film was the same 2.0 μm in all Examples and Comparative Examples.

[0330] <Evaluation> (1) Measurement of initial brightness The resulting colored coating film was measured for spectroscopy using a colorimeter (OSP-SP-200; manufactured by Olympus Corporation), and the xy chromaticity coordinates (x, y) and stimulus value Y in the CIE XYZ color system were measured using the characteristic function of Illuminant C. A larger Y value indicates a higher lightness.

[0331] (2) Evaluation of brightness unevenness suppression An ultraviolet cut filter (COLORED OPTICAL GLASS L38; manufactured by HOYA Corporation; cuts light of 380 nm or less) was placed on the obtained colored coating film, and a light irradiation test was performed by irradiating the xenon lamp light for 48 or 120 hours (irradiation time is shown in Table 8) using a light resistance tester (Suntest CPS+: manufactured by Toyo Seiki Seisakusho Co., Ltd.). The relative value (%) of the irritation value Y after the light irradiation test, when the irritation value Y (initial luminosity obtained in (1) above) before the light irradiation test was taken as 100%, was calculated as the "luminosity change rate" and evaluated according to the following evaluation criteria. The results are shown in Table 8. When the luminosity change rate is 98.0% or more under these measurement conditions, the luminosity difference between the periphery and the center of the colored filter after long-term use becomes difficult for the human eye to distinguish, and it can be said that the color filter has sufficient performance. Brightness unevenness suppression ◎: Brightness change rate is 99.0% or more Suppression of uneven brightness: Brightness change rate is 98.0% or more and less than 99.0% Suppression of uneven brightness: Brightness change rate is less than 98.0%

[0332] [Table 8]

[0333] (3) Green spectral characteristics evaluation The colored coating film after the light irradiation test in "(2) Evaluation of brightness unevenness suppression" was subjected to spectrum measurement using an ultraviolet, visible, near infrared absorption spectrometer (JASCO: V-770) to evaluate the transmittance in the green region when the colored coating film had a thickness of 2.0 μm. The results are shown in Table 9. If the transmittance at 550 nm is 35% or more and 99% or less, and the transmittance at 620 nm is 0.1% or more and 30% or less, it can be said that the green filter in a color filter can exhibit better spectral characteristics even after long-term use.

[0334] [Table 9]

Claims

1. A colored resin composition comprising a colorant and an alkali-soluble resin, the colorant comprising a compound represented by formula (I): 【Chemistry 1】 [In formula (I), R 1 ~R 16 each independently represents a hydrogen atom, a bromine atom, an iodine atom, a hydrocarbon group having 1 to 6 carbon atoms which may have a substituent, a group represented by formula (ia), a group represented by formula (ib), or a group represented by formula (ic), and —CH 2 - may be replaced by -O- or -CO-. 1 ~R 16 Among these, at least one represents a group represented by formula (ia), a group represented by formula (ib) or a group represented by formula (ic), and when there are a plurality of groups represented by formula (ia), they may be the same or different, when there are a plurality of groups represented by formula (ib), they may be the same or different, and when there are a plurality of groups represented by formula (ic), they may be the same or different.] 【Chemistry 2】 [In formula (ia), R a1 ~R a5 each independently represents a hydrogen atom, a bromine atom, an iodine atom, a carboxy group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and -CH 2 - may be replaced by -O- or -CO-. a1 ~R a5 At least one of represents a bromine atom, an iodine atom, a carboxy group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent. * represents a bond.] 【Chemistry 3】 [In formula (ib), R b1 ~R b7 each independently represents a hydrogen atom, a bromine atom, an iodine atom, a carboxy group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and -CH 2 - may be replaced by -O- or -CO-. b1 ~R b7 At least one of represents a bromine atom, an iodine atom, a carboxy group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent. * represents a bond.] 【Chemistry 4】 [In formula (ic), R c1 ~R c7 each independently represents a hydrogen atom, a bromine atom, an iodine atom, a carboxy group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and -CH 2 - may be replaced by -O- or -CO-. c1 ~R c7 At least one of represents a bromine atom, an iodine atom, a carboxy group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent. * represents a bond.]

2. R 1 ~R 4 At least one of R is a group represented by formula (ia), formula (ib), or formula (ic), 5 ~R 8 At least one of R is a group represented by formula (ia), formula (ib), or formula (ic), 9 ~R 12 At least one of R is a group represented by formula (ia), formula (ib), or formula (ic), 13 ~R 16 The colored resin composition according to claim 1, wherein at least one of the formulas (ia), (ib), or (ic) is a group represented by the formula (ia), the formula (ib), or the formula (ic).

3. R 2 and R 3 At least one of R is a group represented by formula (ia), formula (ib), or formula (ic), 6 and R 7 At least one of R is a group represented by formula (ia), formula (ib), or formula (ic), 10 and R 11 At least one of R is a group represented by formula (ia), formula (ib), or formula (ic), 14 and R 15 At least one of R is a group represented by formula (ia), formula (ib), or formula (ic), 1 , R 4 , R 5 , R 8 , R 9 , R 12 , R 13 , and R 16 3. The colored resin composition according to claim 2, wherein: is a hydrogen atom.

4. R 2 and R 3 is a group represented by formula (ia), formula (ib), or formula (ic), and R 6 and R 7 is a group represented by formula (ia), formula (ib), or formula (ic), and R 10 and R 11 is a group represented by formula (ia), formula (ib), or formula (ic), and R 14 and R 15 is a group represented by formula (ia), formula (ib), or formula (ic), and R 1 , R 4 , R 5 , R 8 , R 9 , R 12 , R 13 , and R 16 is a hydrogen atom, The colored resin composition according to claim 3, wherein the four groups represented by formula (ia), formula (ib), or formula (ic) in formula (I) are the same group.

5. R 1 , R 5 , R 9 , and R 13 are each independently a group represented by formula (ia), formula (ib), or formula (ic), and R 2 ~R 4 , R 6 ~R 8 , R 10 ~R 12 , and R 14 ~R 16 The colored resin composition according to claim 2 , wherein is a hydrogen atom.

6. The colored resin composition according to claim 1 or 2, further comprising a polymerizable compound and a polymerization initiator.

7. A color filter formed from the colored resin composition 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.

10. A method for producing a compound represented by formula (I) by reacting a compound represented by formulas (II-1) to (II-4) in the presence of a base and a compound represented by formula (III). 【Chemistry 5】 [In formula (I), R 1 ~R 16 each independently represents a hydrogen atom, a bromine atom, an iodine atom, a hydrocarbon group having 1 to 6 carbon atoms which may have a substituent, a group represented by formula (ia), a group represented by formula (ib), or a group represented by formula (ic), and —CH 2 - may be replaced by -O- or -CO-. 1 ~R 16 Among these, at least one represents a group represented by formula (ia), a group represented by formula (ib), or a group represented by formula (ic), and when there are a plurality of groups represented by formula (ia), they may be the same or different, when there are a plurality of groups represented by formula (ib), they may be the same or different, and when there are a plurality of groups represented by formula (ic), they may be the same or different.] 【Chemistry 6】 [In formula (ia), R a1 ~R a5 each independently represents a hydrogen atom, a bromine atom, an iodine atom, a carboxy group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and -CH 2 - may be replaced by -O- or -CO-. a1 ~R a5 At least one of represents a bromine atom, an iodine atom, a carboxy group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent. * represents a bond.] 【Chemistry 7】 [In formula (ib), R b1 ~R b7 each independently represents a hydrogen atom, a bromine atom, an iodine atom, a carboxy group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and -CH 2 - may be replaced by -O- or -CO-. b1 ~R b7 At least one of represents a bromine atom, an iodine atom, a carboxy group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent. * represents a bond.] 【Chemistry 8】 [In formula (ic), R c1 ~R c7 each independently represents a hydrogen atom, a bromine atom, an iodine atom, a carboxy group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and -CH 2 - may be replaced by -O- or -CO-. c1 ~R c7 At least one of represents a bromine atom, an iodine atom, a carboxy group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent. * represents a bond.] 【Chemistry 9】 [In formula (III), X M is a halogen atom, a hydroxyl group, or OR M R represents a group. M represents a hydrocarbon group having 1 to 6 carbon atoms. 【Chemistry 10】 [In formulas (II-1) to (II-4), R 1 ~R 16 has the same meaning as above.]

11. The method according to claim 10, wherein the amount of the compound represented by formula (III) used is 0.25 mol or more and 0.40 mol or less per 1 mol of the total amount of the compounds represented by formulas (II-1) to (II-4).

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