Compounds and coloring compositions

Abstract

To reduce the viscosity of a coloring composition containing a pigment.SOLUTION: The coloring composition contains a compound represented by formula (I), and a pigment. [In formula (I), L1 represents a group represented by formula (ph1); R1 to R4 each independently represent a hydrogen atom, a hydrocarbon group that may have substituents, a heterocyclic group, -SO3 N(R5)4, a cyano group, or a halogen atom, provided that at least one of R1 to R4 is -SO3 N(R5)4, or a hydrocarbon group having one or more -SO3 N(R5)4 groups as substituents; and R5 represents a hydrogen atom or a hydrocarbon group, where multiple occurrences of R5 may be identical or different.]SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a compound, a colored composition containing the compound, a color filter formed from the colored composition, and a display device containing the color filter. [Background technology]

[0002] Color filters used in display devices such as liquid crystal displays, electroluminescent displays, and plasma displays, as well as solid-state image sensors such as CCDs and CMOS sensors, are manufactured from colored compositions. Various pigments, such as CI Pigment Orange 13 and CI Pigment Red 269, are known as colorants used in such colored compositions (Non-Patent Literature 1). [Prior art documents] [Non-patent literature]

[0003] [Non-Patent Document 1] Colour Index International (British Dye and Color Society, American Textile Chemical Technology and Dyeing Technology Association) [Overview of the project] [Problems that the invention aims to solve]

[0004] However, colored compositions containing the above-mentioned pigments sometimes had high viscosity. Therefore, the present invention aims to provide a compound that can reduce the viscosity of pigment-containing compositions. [Means for solving the problem]

[0005] The gist of this invention is as follows: [1] A colored composition comprising a compound represented by formula (I) and a pigment. [ka] [In formula (I), L 1represents a group represented by formula (ph1), R 1 ~R 4 each independently represents a hydrogen atom, a hydrocarbon group which may have a substituent, a heterocyclic group, -SO3N(R 5 ),4, a cyano group, or a halogen atom. However, at least one of R 1 ~R 4 is a hydrocarbon group having one or more -SO3N(R 5 )4 as a substituent or -SO3N(R 5 )4. R 5 represents a hydrogen atom or a hydrocarbon group, and a plurality of R 5 may be the same or different.]

Chemical formula

Chemical formula

[10] L 1 The compound described in [9] is a group represented by formula (ph2). [ka] [In formula (ph2), X 2 ~X 5 Each of these independently represents a hydrogen atom, a C1-C4 alkyl group, a substituted or unsubstituted amino group, an N-acylamino group, a carboxyl group, a C1-C4 alkoxy group, a C1-C4 alkylsulfanyl group, a cyano group, or a halogen atom. 2 and X 3 , X 4 and X 5 These elements may join together to form a ring. * represents a joining hand. [Effects of the Invention]

[0006] The compound of the present invention makes it possible to reduce the viscosity of compositions containing pigments. [Modes for carrying out the invention]

[0007] <Compound (I)> The compound according to the present invention is a compound represented by formula (I) (hereinafter sometimes referred to as compound (I)). By using compound (I), it is possible to reduce the viscosity of compositions containing pigments.

[0008] [ka] [In formula (I), L 1 This represents the group represented by formula (ph1), R 1 ~R 4 Each of these independently comprises a hydrogen atom, a hydrocarbon group which may have substituents, a heterocyclic group, and -SO3N(R 5 )4. Represents a cyano group or a halogen atom. However, R 1 ~R 4 At least one of them is -SO3N(R) 5 )4 hydrocarbon group or -SO3N(R 5 )4. R 5 R represents a hydrogen atom or hydrocarbon group, and there are multiple R 5 They may be the same or different. [ka] [In formula (ph1), X 1 x represents a substituent or optionally substituent hydrocarbon group, where -CH2- in the hydrocarbon group may be replaced by -O-, -CO-, or -NH-, and -CH= in the hydrocarbon group may be replaced by -N=. n represents an integer from 0 to 4. If n is an integer of 2 or more, there are multiple X 1 They may be the same or different. n represents an integer greater than or equal to 2, and there are multiple X 1 However, in formula (ph1), if the carbon atoms constituting the phenylene group are bonded to adjacent carbon atoms, then X is bonded to the adjacent carbon atoms. 1 These elements may join together to form a ring. * represents a joining hand.

[0009] Compound (I) will be described in detail below, but compound (I) will also include the resonance structures of formula (I), tautomers of formula (I), and compounds obtained by rotating each group in formula (I) around the bond axis of a single bond. Examples of tautomers of formula (I) include the compound represented by the following formula (I').

[0010] [ka] [In formula (I'), L 1 and R 1 ~R 4 This is the same as above.

[0011] X in equation (ph1) 1 Examples of substituents represented by (hereinafter sometimes referred to as substituent A) include substituted or unsubstituted amino groups, N-acylamino groups, carboxyl groups, alkoxy groups having 1 to 4 carbon atoms, alkylsulfanyl groups having 1 to 4 carbon atoms, cyano groups, halogen atoms, and the like.

[0012] X 1 The hydrocarbon group represented may be an aliphatic hydrocarbon group or an aromatic hydrocarbon group, and the aliphatic hydrocarbon group may be saturated or unsaturated, and may be linear or cyclic (alicyclic hydrocarbon group). The alicyclic hydrocarbon group may be monocyclic or polycyclic.

[0013] Examples of saturated chain hydrocarbon groups (hereinafter sometimes referred to as alkyl groups) include linear alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, and decyl groups; and branched alkyl groups such as isopropyl, isobutyl, sec-butyl, tert-butyl, 1,3-dimethylbutyl, 2-ethylbutyl, and 2-ethylhexyl groups.

[0014] Examples of unsaturated chain hydrocarbon groups include alkenyl groups such as ethenyl groups, propenyl groups (e.g., 1-propenyl groups, 2-propenyl groups), and butenyl groups (e.g., 1-butenyl groups, 3-butenyl groups); and alkynyl groups such as ethynyl groups, propynyl groups (e.g., 1-propynyl groups, 2-propynyl groups), and butynyl groups (e.g., 1-butynyl groups, 3-butynyl groups).

[0015] The number of carbon atoms in the saturated or unsaturated chain hydrocarbon group is preferably 1 to 15, more preferably 1 to 10, even more preferably 1 to 6, and particularly preferably 1 to 4.

[0016] Examples of saturated alicyclic hydrocarbon groups include cycloalkyl groups such as cyclopropyl, 1-methylcyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and 2-methylcyclohexyl.

[0017] Examples of unsaturated alicyclic hydrocarbon groups include cyclohexenyl groups (e.g., cyclohexa-1-en-1-yl, cyclohexa-2-en-1-yl, cyclohexa-3-en-1-yl), cycloheptenyl groups, and cyclooctenyl groups, as well as other cycloalkenyl groups.

[0018] Examples of alicyclic hydrocarbon groups include polycyclic saturated alicyclic hydrocarbon groups such as norbornyl, adamantyl, and bicyclo[2.2.2]octyl; and polycyclic unsaturated alicyclic hydrocarbon groups such as norbornenyl.

[0019] The number of carbon atoms in the alicyclic hydrocarbon group is preferably 3 to 12, more preferably 3 to 10, and even more preferably 3 to 8.

[0020] Aromatic hydrocarbon groups include phenyl group, o-tolyl group, m-tolyl group, p-tolyl group, 2,4-dimethylphenyl group, 2,6-dimethylphenyl group, 2,4,6-trimethylphenyl group, 2,4-diisopropylphenyl group, 2,6-diisopropylphenyl group, 4-vinylphenyl group, o-tert-butylphenyl group, m-tert-butylphenyl group, p-tert-butylphenyl group, 3,5-di(tert-butyl)phenyl group, 1-naphthyl group, 2-naphthyl group, and a group obtained by removing one hydrogen atom from tetralin.

[0021] The number of carbon atoms in the aromatic hydrocarbon group is preferably 6 to 18, more preferably 6 to 12, and even more preferably 6 to 10.

[0022] X 1 The hydrocarbon group represented by may be a combination of the hydrocarbon groups listed above, for example, an aralkyl group, an alkyl group to which an alicyclic hydrocarbon group is attached; an aromatic hydrocarbon group to which a cycloalkyl group is condensed; an alkyl group to which an aromatic hydrocarbon group to which a cycloalkyl group is condensed is attached; and so on.

[0023] Examples of aralkyl groups include benzyl groups, (4-methylphenyl)methyl groups, and phenethyl groups. The number of carbon atoms in the aralkyl group is preferably 7 to 18, more preferably 7 to 12, and even more preferably 7 to 10.

[0024] Examples of alkyl groups to which alicyclic hydrocarbon groups are bonded include cyclopropylmethyl group, cyclopropylethyl group, cyclobutylmethyl group, cyclohexylmethyl group, cyclohexylethyl group, and adamantylmethyl group. The number of carbon atoms in the alkyl group to which the alicyclic hydrocarbon group is bonded is preferably 4 to 20, more preferably 4 to 15, and even more preferably 4 to 10.

[0025] Examples of aromatic hydrocarbon groups formed by the condensation of cycloalkyl groups include the group obtained by removing one hydrogen atom from the benzene ring in indan, the group obtained by removing one hydrogen atom from the benzene ring in 1-methyl-indan, and the group obtained by removing one hydrogen atom from the benzene ring in 2-methyl-indan.

[0026] Examples of alkyl groups to which aromatic hydrocarbon groups formed by condensation of cycloalkyl groups are bonded include groups in indanes in which an alkyl group having 1 to 4 carbon atoms is bonded to the benzene ring, groups in 1-methyl-indanes in which an alkyl group having 1 to 4 carbon atoms is bonded to the benzene ring, and groups in 2-methyl-indanes in which an alkyl group having 1 to 4 carbon atoms is bonded to the benzene ring.

[0027] X 1 Examples of substituents that the hydrocarbon group represented by (hereinafter sometimes referred to as substituent B) may have include substituted or unsubstituted amino groups, N-acylamino groups, carboxyl groups, alkoxy groups having 1 to 4 carbon atoms, alkylsulfanyl groups having 1 to 4 carbon atoms, cyano groups, halogen atoms, hydroxyl groups, and the like.

[0028] The amino groups as substituents A and B may be unsubstituted amino groups or substituted amino groups. The substituted amino group is preferably an amino group having one or two hydrocarbon groups. The hydrocarbon group is the X mentioned above. 1 Examples of substituted amino groups include groups similar to the hydrocarbon group represented by , and are preferably alkyl groups. The number of carbon atoms in the hydrocarbon group is preferably 1 to 10, more preferably 1 to 4. Examples of substituted amino groups include N-methylamino group, N,N-dimethylamino group, N-ethylamino group, N,N-diethylamino group, N-propylamino group, N,N-dipropylamino group, N-isopropylamino group, N,N-diisopropylamino group, N-phenylamino group, N,N-diphenylamino group, and N,N-ethylmethylamino group.

[0029] The N-acylamino groups as substituents A and B are -NHCOR 7 It means a group represented by R7 R represents a hydrogen atom or a hydrocarbon group. 7 The hydrocarbon group represented by the above X 1 Examples of groups similar to the hydrocarbon group represented by R include R 7 The number of carbon atoms in the hydrocarbon group represented is preferably 2 to 20, more preferably 2 to 10, and even more preferably 2 to 6. Examples of N-acylamino groups include N-formylamino group, N-acetylamino group, N-propanoylamino group, N-butanoylamino group, and N-benzoylamino group.

[0030] Examples of alkoxy groups as substituents A and B include methoxy, ethoxy, propoxy, n-butoxy, and tert-butoxy groups. The alkoxy group preferably has 1 to 4 carbon atoms, and more preferably 1 or 2.

[0031] Examples of alkylsulfanyl groups as substituents A and B include methylsulfanyl group, ethylsulfanyl group, propylsulfanyl group, and n-butylsulfanyl group. The alkylsulfanyl group preferably has 1 to 4 carbon atoms, and more preferably 1 or 2 carbon atoms.

[0032] Examples of halogen atoms as substituents A and B include fluorine, chlorine, bromine, and iodine atoms, with fluorine, chlorine, or bromine atoms being preferred, and chlorine atoms being more preferred.

[0033] X 1 Preferably, the C1-C15 alkyl group, C1-C4 alkoxy group, cyano group, or halogen atom is preferred, and more preferably, the C1-C4 alkyl group, C1-C4 alkoxy group, cyano group, or halogen atom is preferred.

[0034] n is preferably an integer between 0 and 2.

[0035] In equation (ph1), if n is an integer greater than or equal to 2, then multiple X 1 They may be the same or different.

[0036] n is an integer greater than or equal to 2, and there are multiple X 1 However, in formula (ph1), if the carbon atoms constituting the phenylene group are bonded to adjacent carbon atoms, then X is bonded to the adjacent carbon atoms. 1 They may bond to each other to form a ring. X bonded to an adjacent carbon atom 1 Examples of rings formed by the bonding of these elements include the following: In the formula, * indicates a bond with an adjacent carbon atom on the phenylene group in formula (ph1).

[0037] [ka]

[0038] The positions of the two bonds in formula (ph1) are not particularly limited, but from the viewpoint of ease of obtaining raw materials, it is preferable that they be in a para position.

[0039] L in equation (I) 1 It is preferable that the group is represented by formula (ph2).

[0040] [ka] [In formula (ph2), X 2 ~X 5 Each of these independently represents a hydrogen atom, a C1-C4 alkyl group, a substituted or unsubstituted amino group, an N-acylamino group, a carboxyl group, a C1-C4 alkoxy group, a C1-C4 alkylsulfanyl group, a cyano group, or a halogen atom. 2 and X 3 , X 4 and X 5 These elements may join together to form a ring. * represents a joining hand.

[0041] X 2~X 5 As the alkyl group having 1 to 4 carbon atoms represented by 5 , a methyl group or an ethyl group is preferable.

[0042] X 2 ~X 5 As the substituted or unsubstituted amino group represented by 5 , the groups described as the substituted or unsubstituted amino group in substituent A and substituent B are exemplified, and the preferable range is also the same.

[0043] X 2 ~X 5 As the N-acylamino group represented by 5 , the groups described as the N-acylamino group in substituent A and substituent B are exemplified, and the preferable range is also the same.

[0044] X 2 ~X 5 As the alkoxy group represented by 5 , the groups described as the alkoxy group in substituent A and substituent B are exemplified, and the preferable range is also the same.

[0045] X 2 ~X 5 As the alkylsulfanyl group represented by 5 , the groups described as the alkylsulfanyl group in substituent A and substituent B are exemplified, and the preferable range is also the same.

[0046] X 2 ~X 5 As the halogen atom represented by 5 , those described as the halogen atom in substituent A and substituent B are exemplified, and the preferable range is also the same.

[0047] X 2 and X 3 、X 4 and X 5 The rings formed by X 1 binding to each other include those described as the rings formed by X

[0048] Among the groups represented by formula (ph2), it is preferable that the group is one of those represented by formulas (ph2-1) to (ph2-8), and more preferably one of those represented by formulas (ph2-1) to (ph2-7). In the formula, * represents a bond.

[0049] [ka]

[0050] R in equation (I) 1 ~R 4 The hydrocarbon group represented by the above X 1 The hydrocarbon groups described above are examples of hydrocarbon groups represented by the formula. Among these, alkyl groups having 1 to 10 carbon atoms, cycloalkyl groups having 3 to 10 carbon atoms, and aromatic hydrocarbon groups having 6 to 12 carbon atoms are preferred, and alkyl groups having 1 to 6 carbon atoms, cycloalkyl groups having 3 to 8 carbon atoms, and aromatic hydrocarbon groups having 6 to 10 carbon atoms are more preferred.

[0051] R 1 ~R 4 The substituents that the hydrocarbon group represented by (hereinafter sometimes referred to as substituent C) may have include a hydroxyl group, a carbon-1 to carbon-4 alkoxy group, a carbon-1 to carbon-4 alkylsulfanyl group, a carboxyl group, a substituted or unsubstituted amino group, an N-acylamino group, a cyano group, a halogen atom, -SO3H, -SO3N(R 5 )4, -SO3M, -SO3T 0.5 , -SO2N(R 6 )2nd class is an example. M represents alkali metal atoms, T represents alkaline earth metal atoms, and R 5 and R 6 Each of these independently represents a hydrogen atom or a hydrocarbon group. Substituents C include a hydroxyl group, an alkoxy group having 1 to 4 carbon atoms, a halogen atom, or -SO3N(R 5 )4 is preferred, and a halogen atom or -SO3N(R 5 )4 is more preferable.

[0052] Examples of alkoxy groups as substituent C include those described as alkoxy groups in substituents A and B, and the preferred range is the same.

[0053] Examples of alkylsulfanil groups as substituent C include those described as alkylsulfanil groups in substituents A and B, and the preferred range is the same.

[0054] Examples of substituted or unsubstituted amino groups as substituent C include those described as substituted or unsubstituted amino groups in substituents A and B, and the preferred range is the same.

[0055] Examples of N-acylamino groups as substituent C include those described as N-acylamino groups in substituents A and B, and the preferred range is the same.

[0056] Examples of halogen atoms as substituent C include those described as halogen atoms in substituents A and B, with chlorine, bromine, or fluorine atoms being preferred.

[0057] Examples of alkali metal atoms represented by M include sodium and potassium.

[0058] Examples of alkaline earth metal atoms represented by T include magnesium, calcium, and barium. 1 ~R 4 Either of the following is -SO3T 0.5 If the hydrocarbon group has one such group, compound (I) has the following structure.

[0059] [ka]

[0060] [In the formula, L 1 , R 1 ~R 4 , and T have the same meaning as above. -SO3 -R 1 ~R 4 In the table It is substituting one of the hydrogen atoms in the hydrocarbon group being modified.

[0061] R 5 R represents a hydrogen atom or hydrocarbon group. 5 They may be the same or different. 5 The hydrocarbon group represented by the above X 1 Examples of hydrocarbon groups represented by the above include the groups described above, and are preferably alkyl groups having 1 to 15 carbon atoms, cycloalkyl groups having 3 to 8 carbon atoms, and aromatic hydrocarbon groups having 6 to 10 carbon atoms. 5 These are preferably, independently, a hydrogen atom, an alkyl group having 1 to 15 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, or an aromatic hydrocarbon group having 6 to 10 carbon atoms, and more preferably a hydrogen atom or an alkyl group having 1 to 12 carbon atoms.

[0062] R 6 represents a hydrogen atom or a hydrocarbon group. Two R's 6 They may be the same or different, and it is preferable that one is a hydrogen atom and the other is a hydrocarbon group. 6 The hydrocarbon group represented by the above X 1 Examples of hydrocarbon groups represented by the formula include the groups described above, and are preferably C1-C10 alkyl groups, C3-C10 cycloalkyl groups, C3-C12 polycyclic saturated alicyclic hydrocarbon groups, and C6-C18 aromatic hydrocarbon groups.

[0063] R 1 ~R 4Examples of heterocyclic groups represented by include thienyl group, benzo[b]thienyl group, thianthrenyl group, furyl group, pyranyl group, isobenzofuranyl group, clomenyl group, xanthenyl group, pyrrolyl group, imidazolyl group, pyrazolyl group, pyridyl group, pyrazinyl group, pyrimidinyl group, pyridadinyl group, indolidine group, indolyl group, 1H-indazolyl group, isoquinolyl group, quinolyl group, phthalazinyl group, carbazolyl group, acridinyl group, clomanyl group, pyrrolidinyl group, piperidyl group, piperazinyl group, indolinyl group, isoindolinyl group, and benzimidazolonyl group. Among these, heterocyclic groups having a benzene ring, such as benzo[b]thienyl group, thianthrenyl group, isobenzofuranyl group, clomenyl group, xanthenyl group, indolyl group, 1H-indazolyl group, isoquinolyl group, quinolyl group, phthalazinyl group, carbazolyl group, acridinyl group, chromanyl group, indolinyl group, isoindolinyl group, and benzimidazolonyl group, are preferred.

[0064] R 1 ~R 4 Examples of halogen atoms represented by include those described as halogen atoms in substituents A and B, with chlorine atoms and fluorine atoms being preferred.

[0065] R 1 ~R 4 At least one of them is -SO3N(R) 5 )4 hydrocarbon group or -SO3N(R 5 )4. R 1 ~R 4 Of these, one to three are -SO3N(R) 5 It is preferable that the hydrocarbon group has 4, R 1 ~R 4 Of these, one or two are substituents -SO3N(R 5 It is more preferable that the hydrocarbon group has 4, R 1 and / or R 3 However, one or more substituents are -SO3N(R 5It is particularly preferable that the hydrocarbon group has -SO3N(R)4. 5 The number of )4 is preferably 1 to 3, and more preferably 1. -SO3N(R 5 The hydrocarbon group to which )4 is bonded is preferably an alkyl group or an aromatic hydrocarbon group, and more preferably an aromatic hydrocarbon group having 6 to 10 carbon atoms.

[0066] R 1 It has one or more substituents -SO3N(R 5 It is preferably a hydrocarbon group having 4, and more preferably one or more substituents -SO3N(R 5 Aromatic hydrocarbon group having )4, more preferably with substituent -SO3N(R 5 It is an aromatic hydrocarbon group having 6 to 10 carbon atoms and containing 4.

[0067] R 2 It is preferably an alkyl group which may have substituents, more preferably an alkyl group which may have a halogen atom, and even more preferably an alkyl group having 1 to 4 carbon atoms which may have a halogen atom.

[0068] R 3 Preferably, the substituent is an optionally substituted hydrocarbon group, more preferably an optionally substituted aromatic hydrocarbon group, and even more preferably -SO3N(R 5 )4 is an aromatic hydrocarbon group having 6 to 10 carbon atoms.

[0069] R 4 It is preferably an alkyl group which may have substituents, more preferably an alkyl group which may have a halogen atom, and even more preferably an alkyl group having 1 to 4 carbon atoms which may have a halogen atom.

[0070] Examples of compound (I) include compounds (I-1) to (I-98) shown in Tables 1-2. Compounds (I-1) to (I-84) are preferred as compound (I), and compounds (I-1) to (I-14) are more preferred.

[0071] [Table 1]

[0072] [Table 2]

[0073] In Tables 1 and 2, ph1-1 to ph1-7 represent groups represented by the following formulas (ph1-1) to (ph1-7), r1 to r3 represent groups represented by the following formulas (r1) to (r3), Me represents a methyl group, and CF3 represents a trifluoromethyl group.

[0074] [ka]

[0075] [ka]

[0076] Compound (I) can be, for example, R by the method described below. 1p ~R 4p After producing compound (II) in which at least one of the hydrocarbon groups has -SO3H as a substituent or -SO3H, the obtained compound (II) and N(R 5 It can be produced by reacting it with an ammonium salt represented as 4Z (where Z represents a halogen atom, a carboxyl group, or a hydroxyl group).

[0077] Specifically, first, the amine represented by formula (pt1) is diazotized to produce the diazonium salt represented by formula (q1). The obtained diazonium salt represented by formula (q1) is reacted with the compound represented by formula (pt2) to produce the compound represented by formula (q2). Next, the compound represented by formula (q2) is reduced to produce the amine represented by formula (q3). Furthermore, the obtained amine is diazotized to produce the diazonium salt represented by formula (q4), and then reacted with the compound represented by formula (pt3) to produce the compound represented by formula (II) (compound (II)).

[0078] [ka] [In equations (pt1) to (pt3), equations (q1) to (q4), and equation (II), X 1 And n has the same meaning as above. R 1p ~R 4p Each of these independently represents a hydrogen atom, an optionally substituted hydrocarbon group, a heterocyclic group, -SO3H, a cyano group, or a halogen atom. However, R 1p ~R 4p At least one of them is a hydrocarbon group or -SO3H having one or more -SO3H substituents. Q 1 and Q 2 Each of these independently represents either an inorganic anion or an organic anion.

[0079] The diazonium salt represented by formula (q1) can be obtained, for example, by diazotizing the amine represented by formula (pt1) with nitrite, nitrite salt, or nitrite ester. Such diazotization can be carried out by any known method.

[0080] Examples of the inorganic anions include fluoride ions, chloride ions, bromide ions, iodide ions, perchlorate ions, and hypochlorite ions. Examples of the organic anions include CH3COO - , C6H5COO- Examples include: Q 1 and Q 2 Preferably, chloride ions, bromide ions, CH3COO - That is the case.

[0081] When carrying out the diazotization reaction described above, an acidic catalyst may be used to ensure the reaction proceeds smoothly. Examples of acidic catalysts include sulfuric acid, mineral acids such as hydrochloric acid, and others.

[0082] The compound represented by formula (q2) can be produced by diazo coupling a diazonium salt represented by formula (q1) with the compound represented by formula (pt2). Such diazo coupling can be carried out by any known method, but the reaction temperature is preferably -5°C to 60°C, and more preferably 0°C to 30°C. The reaction time is preferably 30 minutes to 12 hours, and more preferably 1 hour to 4 hours. This reaction is preferably carried out in the presence of an aqueous solvent, and water is preferred as the aqueous solvent.

[0083] The compound represented by formula (q3) can be produced by reducing the compound represented by formula (q2). The reduction method is not particularly limited and can be carried out by any known method, but for example, reduction with a reducing agent such as a sulfide can be used. The sulfide is not particularly limited and examples include hydrosulfides such as sodium hydrosulfide, potassium hydrosulfide, and ammonium hydrosulfide, and sulfides such as sodium sulfide, potassium sulfide, and ammonium sulfide. These may be anhydrous or contain water of crystallization. The reduction reaction is preferably carried out in the presence of an aqueous solvent, and water is preferred as the aqueous solvent.

[0084] The diazonium salt represented by formula (q4) can be obtained by diazotizing the amine represented by formula (q3). The diazotization method can be the same as the diazotization method for the compound represented by formula (pt1) described above.

[0085] Compound (II) can be produced by diazo coupling a diazonium salt represented by formula (q4) with a compound represented by formula (pt3). The diazo coupling method can be the same as the diazo coupling method described above for the diazonium salt represented by formula (q1) and the compound represented by formula (pt2).

[0086] The obtained compound (II) and N(R 5 By reacting the ammonium salt represented by 4Z (where Z represents a halogen atom, carboxyl group, or hydroxyl group), the -SO3H in compound (II) is converted to -SO3N(R 5 ) is converted to 4, and compound (I) can be produced. In this reaction, the reaction temperature is preferably -5°C to 60°C, and more preferably 0°C to 30°C. The reaction time is preferably 30 minutes to 12 hours, and more preferably 1 hour to 4 hours. This reaction is preferably carried out in the presence of water or a hydrophilic organic solvent, and the hydrophilic organic solvents are preferably N,N-dimethylformamide, N,N-dimethyl sulfoxide, N-methyl-2-pyrrolidone, methanol, ethanol, propanol, isopropanol, etc.

[0087] Z is preferably a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a carboxyl group, or a hydroxyl group, and more preferably a chlorine atom, a carboxyl group, or a hydroxyl group. In particular, the above reaction is preferably carried out by reacting compound (II) with aqueous ammonia, in which case the -SO3H in compound (II) is converted to -SO3NH4.

[0088] The above reaction may be carried out simultaneously with the diazo coupling reaction between the diazonium salt represented by formula (q4) and the compound represented by formula (pt3). In this case, the diazonium salt represented by formula (q4) and N(R) are added to the solution containing the compound represented by formula (pt3). 5 By adding a solution containing the ammonium salt represented by 4Z dropwise and allowing it to react, a diazo coupling reaction and -SO3N(R) 5The conversion to )4 can be carried out simultaneously. In this case, the reaction temperature is preferably -5°C to 60°C, and more preferably 0°C to 30°C. The reaction time is preferably 30 minutes to 12 hours, and more preferably 1 hour to 4 hours.

[0089] The method for obtaining the target compound (I) from the reaction mixture is not particularly limited, and various known methods can be employed. Furthermore, if necessary, further purification may be performed by known methods such as recrystallization.

[0090] <Coloring composition> The colored composition of the present invention comprises compound (I) and a pigment (hereinafter sometimes referred to as pigment (A1)). Compound (I) and pigment (A1) can be used as a coloring agent (hereinafter sometimes referred to as coloring agent (A)). The colored composition of the present invention may contain at least one selected from a resin (hereinafter sometimes referred to as resin (B)), a polymerizable compound (hereinafter sometimes referred to as polymerizable compound (C)), a polymerization initiator (hereinafter sometimes referred to as polymerization initiator (D)), a solvent (hereinafter sometimes referred to as solvent (E)), and a leveling agent (hereinafter sometimes referred to as leveling agent (F)). It is preferable to contain at least one selected from resin (B), polymerizable compound (C), polymerization initiator (D), and solvent (E), and more preferable to contain at least one selected from resin (B) and solvent (E). Furthermore, if polymerizable compound (C) is included, it is preferable to also include polymerization initiator (D). In this specification, the compounds exemplified as components may be used individually or in combination, unless otherwise specified.

[0091] 1. Coloring agent (A) The coloring agent (A) comprises compound (I) and pigment (A1). The inclusion of compound (I) together with the pigment in the coloring agent (A) reduces the viscosity of the colored composition. This improves workability during mixing and application, and allows for the easy formation of color filters with superior properties using this colored composition. Furthermore, the inclusion of compound (I) together with the pigment in the coloring agent (A) preferably lowers the viscosity of the colored composition, improving its long-term storage stability.

[0092] 1-1. Compound (I) Compound (I) is the compound represented by the above formula (I), and its preferred embodiment is the same.

[0093] The content of compound (I) is preferably 0.08% by mass or more, more preferably 0.8% by mass or more, even more preferably 2.4% by mass or more, and preferably 50% by mass or less, more preferably 40% by mass or less, even more preferably 35% by mass or less, even more preferably 25% by mass or less, and particularly preferably 20% by mass or less, based on the total amount of coloring agent (A).

[0094] The content of compound (I) is preferably 0.001 parts by mass or more, more preferably 0.01 parts by mass or more, even more preferably 0.03 parts by mass or more, and also preferably 1 part by mass or less, more preferably 0.8 parts by mass or less, even more preferably 0.5 parts by mass or less, even more preferably 0.3 parts by mass or less, and particularly preferably 0.2 parts by mass or less, per 1 part by mass of pigment (A1). Furthermore, the content of compound (I) may be 0.2 parts by mass or more, or 0.3 parts by mass or more, per 1 part by mass of pigment (A1).

[0095] 1-2. Pigment (A1) As for pigment (A1), there are no particular limitations, and any known pigment can be used as long as it does not contain compound (I). Examples include pigments classified as pigments in the Color Index (published by The Society of Dyers and Colourists). Examples of pigments include yellow pigments such as CI Pigment Yellow 1, 3, 10, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 74, 81, 83, 86, 93, 94, 109, 110, 117, 125, 128, 129, 137, 138, 139, 147, 148, 150, 153, 154, 165, 166, 173, 185, 194, 214, 231, and 233; Orange pigments such as CI Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 62, 64, 65, 71, 72, 73; Red pigments such as CI Pigment Red 3, 9, 97, 105, 122, 123, 144, 149, 166, 168, 170, 176, 177, 179, 180, 190, 192, 202, 209, 215, 216, 224, 242, 244, 254, 255, 264, 265, 266, 268, 269, 273, 291, 295, 296; Blue pigments such as CI Pigment Blue 15, 15:3, 15:4, 15:6, 60; Violet pigments such as CI Pigment Violet 1, 19, 23, 29, 32, 36, 38; Green pigments such as CI Pigment Green 7, 36, 58, 59, 62, and 63; CI Pigment Brown 23, 25, and other brown pigments; Examples include black pigments such as CI Pigment Black 1 and 7.

[0096] Furthermore, according to the chemical structure, the pigment (A1) preferably includes azo pigments other than compound (I), quinophthalone pigments, diketopyrrolopyrrole pigments, phthalocyanine pigments, squarylium pigments, perylene pigments, xanthene pigments, isoindoline pigments, and quinacridone pigments, with azo pigments or diketopyrrolopyrrole pigments being more preferable.

[0097] The azo pigment is a pigment other than compound (I) that has an azo group in its molecule. Note that "pigments having an azo group in their molecule" also include pigments that have an azo group due to tautomerism. The azo pigment is preferably a monoazo compound having one azo group per molecule, or a disazo compound having two azo groups per molecule, and more preferably a disazo compound. The fact that pigment (A1) is a disazo compound provides a superior low-viscosity effect on the colored composition due to compound (I), and preferably results in better storage stability of the colored composition.

[0098] Examples of monoazo compounds include yellow pigments such as CI Pigment Yellow 3, 74, and 165; red pigments such as CI Pigment Red 3, 170, and 269; and among these, CI Pigment Red 269 is preferred.

[0099] As the disazo compound, the compound represented by formula (A1-1) is preferred.

[0100] [ka] [In formula (A1-1), L 2 is a phenylene group or biphenylene group which may have substituents, A and B are each independently one of the bases represented by equations (t1) to (t5). [ka] [In formulas (t1) to (t5), R 11 ~R 26 Each of these independently represents a hydrogen atom, an optionally substituted hydrocarbon group, a heterocyclic group, a cyano group, or a halogen atom. * represents L 2 This represents a combination of [two characters].

[0101] In formula (A1-1), L 2This is a phenylene group or biphenylene group which may have a substituent, and is preferably a phenylene group which may have a substituent.

[0102] L 2 Examples of substituents that the phenylene group and biphenylene group may have (hereinafter sometimes referred to as substituent D) include C1-C4 alkyl groups, substituted or unsubstituted amino groups, N-acylamino groups, carboxyl groups, C1-C4 alkoxy groups, C1-C4 alkylsulfanyl groups, cyano groups, halogen atoms, and the like.

[0103] The alkyl group having 1 to 4 carbon atoms in substituent D is preferably a methyl group or an ethyl group, and more preferably a methyl group.

[0104] Examples of substituent D include substituted or unsubstituted amino groups, N-acylamino groups, C1-C4 alkoxy groups, C1-C4 alkylsulfanyl groups, and halogen atoms as described for substituent A, and their preferred ranges are also as described.

[0105] The substituent D is preferably an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a cyano group, or a halogen atom, and more preferably a methyl group, an ethyl group, a methoxy group, an ethoxy group, a cyano group, a chlorine atom, or a fluorine atom.

[0106] The number of substituents D is preferably 1 to 4, and more preferably 1 or 2. If there are multiple substituents D, the substituents D may be the same or different, but it is preferable that they be the same.

[0107] The positions of the two bonds in the phenylene group and the biphenylene group are not particularly limited, but from the viewpoint of ease of obtaining raw materials, it is preferable that the bonds be at the 1,4 position in the case of the phenylene group and at the 4,4' position in the case of the biphenylene group.

[0108] L 2 Preferably, the group is one of the groups represented by formulas (ph3-1) to (ph3-12), and more preferably, one of the groups represented by formulas (ph3-1) to (ph3-7). In the formulas, * represents a bond.

[0109] [ka]

[0110] In formula (A1-1), A and B are each independently one of the groups represented by formulas (t1) to (t5), more preferably one of the groups represented by formulas (t1) to (t4), even more preferably one of the groups represented by formulas (t1) to (t3), and particularly preferably one of the groups represented by formula (t1). A and B may be the same or different, but it is preferable that they be the same.

[0111] R 11 ~R 26 The hydrocarbon group represented by the above X 1 The hydrocarbon groups described above are examples of hydrocarbon groups represented by the formula. Among these, alkyl groups having 1 to 10 carbon atoms, cycloalkyl groups having 3 to 10 carbon atoms, and aromatic hydrocarbon groups having 6 to 12 carbon atoms are preferred, and alkyl groups having 1 to 6 carbon atoms, cycloalkyl groups having 3 to 8 carbon atoms, and aromatic hydrocarbon groups having 6 to 10 carbon atoms are more preferred.

[0112] R 11 ~R 26 The substituents that the hydrocarbon group represented by (hereinafter sometimes referred to as substituent E) may have include a hydroxyl group, a carbon-1 to carbon-4 alkoxy group, a carbon-1 to carbon-4 alkylsulfanyl group, a carboxyl group, a substituted or unsubstituted amino group, an N-acylamino group, a cyano group, a halogen atom, -SO3H, -SO3M, and -SO3T. 0.5 , -SO2N(R 6Examples include 2. A substituent E may be a C1-C4 alkoxy group, a C1-C4 alkylsulfanyl group, a substituted or unsubstituted amino group, an N-acylamino group, a halogen atom, -SO3M, or -SO3T. 0.5 , and -SO2N(R 6 )2 includes alkoxy groups with 1 to 4 carbon atoms in substituent C, alkylsulfanyl groups with 1 to 4 carbon atoms, substituted or unsubstituted amino groups, N-acylamino groups, halogen atoms, -SO3M, -SO3T 0.5 , and -SO2N(R 6 The items described in 2 are examples, and their preferred ranges are similar.

[0113] R 11 ~R 26 The heterocyclic group represented by the above R is 1 ~R 4 The groups described as heterocyclic groups represented by are examples, and their preferred range is similar.

[0114] R 11 ~R 26 Examples of halogen atoms represented by include those described as halogen atoms in substituents A and B, with chlorine atoms and fluorine atoms being preferred.

[0115] R 11 It is preferably an aromatic hydrocarbon group which may have substituents, more preferably an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have substituents, and even more preferably an aromatic hydrocarbon group which may have substituents.

[0116] R 12 It is preferably an alkyl group which may have substituents, more preferably an alkyl group which may have a halogen atom, and even more preferably an alkyl group having 1 to 4 carbon atoms which may have a halogen atom.

[0117] R 13 and R 14Each of these is preferably independently a hydrogen atom, an alkyl group, a cycloalkyl group, or an aromatic hydrocarbon group, more preferably a hydrogen atom, a C1-C4 alkyl group, a C3-C8 cycloalkyl group, or a phenyl group. 13 and R 14 It is preferable that they be the same.

[0118] R 15 It is preferably an alkyl group or hydrogen atom which may have substituents, more preferably an alkyl group, and even more preferably an alkyl group having 1 to 4 carbon atoms.

[0119] R 16 It is preferably an alkyl group or cyano group which may have substituents, more preferably an alkyl group or cyano group which may have a halogen atom, and even more preferably an alkyl group or cyano group having 1 to 4 carbon atoms which may have a halogen atom.

[0120] R 17 It is preferably an alkyl group which may have substituents, more preferably an alkyl group which may have a halogen atom, and even more preferably an alkyl group having 1 to 4 carbon atoms which may have a halogen atom.

[0121] R 18 It is preferably an alkyl group which may have substituents, and more preferably an alkyl group having 1 to 4 carbon atoms.

[0122] R 19 It is preferably an alkyl group or hydrogen atom which may have substituents, and more preferably an alkyl group or hydrogen atom having 1 to 4 carbon atoms.

[0123] R 20 It is preferably an aromatic hydrocarbon group or heterocyclic group which may have substituents, more preferably a heterocyclic group having a phenyl group or benzene ring which may have substituents, and even more preferably a phenyl group or benzimidazolonyl group which may have a halogen atom.

[0124] R 21 ~R 26 Each of these is preferably an alkyl group or hydrogen atom which may have substituents, more preferably an alkyl group or hydrogen atom which may have a halogen atom, and even more preferably an alkyl group or hydrogen atom having 1 to 4 carbon atoms which may have a halogen atom.

[0125] The aforementioned quinophthalone pigments are pigments having a quinophthalone structure within their molecules, and specific examples include CI Pigment Yellow 138, 231, and 233.

[0126] The diketopyrrolopyrrole pigment is a pigment having a diketopyrrolopyrrole structure within its molecule, and compounds represented by formula (A1-3) are preferred.

[0127] [ka] [In formula (A1-3), X 31 and X 32 Each of these independently represents a hydrocarbon group, halogen atom, or cyano group, which may have substituents. n31 and n32 each independently represent integers from 0 to 5, and if n31 represents an integer of 2 or greater, then multiple X 31 They may be the same or different, and if n32 represents an integer of 2 or greater, multiple X 32 They may be the same or different.

[0128] X 31 and X 32 A hydrocarbon group which may have substituents represented by X 1 Examples of hydrocarbon groups that may have substituents represented by X include groups similar to those described above. 31 and X 32Preferably, each of these groups is independently a C1-C10 alkyl group which may have substituents, or a C6-C10 aromatic hydrocarbon group which may have substituents; more preferably a C1-C4 alkyl group which may have substituents, or a phenyl group which may have substituents; even more preferably a C1-C4 alkyl group which may have a halogen atom, or a phenyl group which may have a halogen atom; and particularly preferably a trifluoromethyl group or a phenyl group.

[0129] X 31 and X 32 Examples of halogen atoms represented by this formula include fluorine, chlorine, bromine, and iodine atoms.

[0130] X 31 and X 32 It is preferable that these are the same group.

[0131] n31 and n32 are preferably independent integers between 1 and 3, and more preferably 1. In particular, when n31 and n32 are 1, X 31 and X 32 The substitution position of X is preferably the para or meta position. 31 and X 32 If it is a hydrocarbon group or halogen atom which may have substituents, then at the para position, X 31 and X 32 If the group is a cyano group, it is more preferable that it is bonded at the meta position.

[0132] Examples of diketopyrrolopyrrole pigments include CI Pigment Red 254, 255, 264, 272, and CI Pigment Orange 71, 73.

[0133] The phthalocyanine pigments mentioned above are pigments having a phthalocyanine structure within the molecule, and specifically include CI Pigment Green 7, 36, 58, 59, CI Pigment Blue 15, 15:3, 15:4, 15:6, and the like.

[0134] As the squarylium pigment, it is a pigment having a squarylium structure in the molecule, and a compound represented by the formula (A1-5) is preferable.

[0135] [Chemical formula] [In the formula (A1-5), R 51 ~R 54 each independently represents a hydrogen atom or a hydroxy group, R 55 ~R 58 each independently represents a hydrocarbon group which may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced by -O-, -CO- or -NH-.]

[0136] R 51 ~R 54 It is preferable that all are hydroxy groups, or R 51 and R 54 are hydroxy groups, and R 52 and R 53 are hydrogen atoms.

[0137] R 55 ~R 58 Examples of the hydrocarbon group which may have a substituent represented by are the same as the groups described as the hydrocarbon group which may have a substituent represented by X 1 . R 55 ~R 58 are each independently preferably an alkyl group having 1 to 10 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a substituent, more preferably an alkyl group having 1 to 4 carbon atoms, or an aromatic hydrocarbon group having 6 to 10 carbon atoms, and even more preferably a methyl group, an ethyl group, an o-tolyl group, a m-tolyl group, or a p-tolyl group. In particular, R 55 ~R 58 is an alkyl group having 1 to 4 carbon atoms, or R 55and R 58 is an aromatic hydrocarbon group having 6 to 10 carbon atoms, and R 56 and R 57 It is preferable that the alkyl group has 1 to 4 carbon atoms.

[0138] The perylene pigments mentioned above are pigments having a perylene structure within the molecule, and specific examples include CI Pigment Red 179, 190, and 224.

[0139] The xanthene pigment is a pigment having a xanthene structure in its molecule, and compounds represented by formula (A1-7) are preferred.

[0140] [ka] [In formula (A1-7), R 71 ~R 74 Each of these independently represents a hydrocarbon group which may have a hydrogen atom or substituents, and the -CH2- contained in the hydrocarbon group may be replaced by -O-, -CO-, or -NH-.

[0141] R 71 ~R 74 A hydrocarbon group which may have substituents represented by X 1 Examples of hydrocarbon groups that may have substituents represented by R include groups similar to those described above. 71 ~R 74 Preferably, each of these is independently a hydrogen atom, a C1-C10 alkyl group which may have substituents, or a C6-C12 aromatic hydrocarbon group which may have substituents; more preferably a hydrogen atom, a C1-C4 alkyl group, or a C6-C10 aromatic hydrocarbon group; and even more preferably a hydrogen atom, a methyl group, an ethyl group, an o-tolyl group, a 2,4-dimethylphenyl group, a 2,6-dimethylphenyl group, or a 2,4,6-trimethylphenyl group. In particular, R 71 and R 74 is an aromatic hydrocarbon group having 6 to 10 carbon atoms, and R 72 and R73 Preferably, it is a hydrogen atom.

[0142] The isoindoline pigments mentioned above are pigments that have an isoindoline skeleton in their molecules, and specific examples include CI Pigment Yellow 110, 139, 185, etc.

[0143] The quinacridone pigment is a pigment having a quinacridone structure within its molecule, and compounds represented by formula (A1-8) are preferred.

[0144] [ka] [In formula (A1-8), R 81 and R 82 Each of these independently represents a hydrocarbon group which may have a hydrogen atom or a substituent, and the -CH2- contained in the hydrocarbon group may be replaced by -O-, -CO-, or -NH-. X 81 ~X 88 Each of these independently represents a hydrogen atom, a halogen atom, or a hydrocarbon group which may have substituents, and the -CH2- contained in the hydrocarbon group may be replaced with -O-, -CO-, or -NH-.

[0145] R 81 ~R 82 and X 81 ~X 88 A hydrocarbon group which may have substituents represented by X 1 Examples of hydrocarbon groups that may have substituents represented by the same formula as described above include groups similar to those described above. X 81 ~X 88 Examples of halogen atoms represented by include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms, with chlorine atoms being preferred among them.

[0146] R 81 and R 82Preferably, each of these is independently a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, which may have substituents, and more preferably an alkyl group having 1 to 4 carbon atoms, which may have hydrogen atoms or substituents.

[0147] X 81 ~X 88 Preferably, each of them is independently a hydrogen atom, a halogen atom, or an alkyl group having 1 to 10 carbon atoms which may have substituents, and more preferably a hydrogen atom, a halogen atom, or an alkyl group having 1 to 4 carbon atoms which may have substituents. In particular, X 81 ~X 88 The state in which all of them are hydrogen atoms; X 82 and X 86 X is a C1-C4 alkyl group which may have a halogen atom or substituents, 81 , X 83 ~X 85 , X 87 ~X 88 The aspect in which it is a hydrogen atom; X 83 and X 87 X is a C1-C4 alkyl group which may have a halogen atom or substituents, 81 , X 82 , X 84 ~X 86 , X 88 A mode in which X is a hydrogen atom; or, X 81 , X 83 , X 85 , X 87 X is a C1-C4 alkyl group which may have a halogen atom or substituents, 82 , X 84 , X 86 , X 88 A configuration in which is a hydrogen atom is preferred.

[0148] The total amount of compound (I) and pigment (A1) is preferably 80% by mass or more, more preferably 90% by mass or more, even more preferably 95% by mass or more, particularly preferably 98% by mass or more, and may also be 100% by mass, based on the total amount of colorant (A).

[0149] Compound (I) and pigment (A1) may, if necessary, be subjected to rosin treatment, surface treatment using pigment derivatives into which acidic or basic groups have been introduced, grafting treatment of the pigment surface with polymer compounds, atomization treatment by sulfuric acid atomization method, washing treatment with organic solvents or water to remove impurities, removal treatment of ionic impurities by ion exchange method, etc. It is preferable that compound (I) and pigment (A1) have uniform particle sizes. By dispersing them with a pigment dispersant, a colored composition can be obtained in which compound (I) and pigment (A1) are uniformly dispersed in the solution.

[0150] Examples of the aforementioned pigment dispersants include surfactants such as cationic, anionic, nonionic, amphoteric, polyester, polyamine, and acrylic types. These pigment dispersants may be used individually or in combination of two or more types. Examples of pigment dispersants by trade name include KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Floren (manufactured by Kyoeisha Chemical Co., Ltd.), Solspers (manufactured by Zeneca Corporation), EFKA (manufactured by CIBA), Azisper (manufactured by Ajinomoto Fine Techno Co., Ltd.), and Disperbyk (manufactured by Bic Chemie). When a pigment dispersant is used, the amount used is preferably 1% by mass or more and 100% by mass or less, and more preferably 5% by mass or more and 70% by mass or less, relative to the total amount of compound (I) and pigment (A1). When the amount of pigment dispersant used is within the above range, a colored composition with a uniform dispersion state tends to be obtained.

[0151] 1-3.Dye (A2) The colorant (A) may contain, in addition to the compound (I) and the pigment (A1), a dye (hereinafter sometimes referred to as dye (A2)). The dye (A2) is not particularly limited, and known dyes can be used. Examples include solvent dyes, acid dyes, direct dyes, mordant dyes, etc. Dyes include, for example, 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 the Dyeing Notes (Color Dyeing Co., Ltd.). Also, according to the chemical structure, azo dyes other than the compound (I), cyanine dyes, triphenylmethane dyes, xanthene dyes, phthalocyanine dyes, anthraquinone dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, azomethine dyes, squarylium dyes, acridine dyes, styryl dyes, coumarin dyes, quinoline dyes, and nitro dyes, etc. can be mentioned. Among these, organic solvent-soluble dyes are preferred.

[0152] Specifically, C.I. Solvent Yellow 4 (hereinafter, the description of C.I. Solvent Yellow will be omitted and only the number will be described), 14, 15, 23, 24, 38, 62, 63, 68, 82, 94, 98, 99, 117, 162, 163, 167, 189; C.I. Solvent Red 45, 49, 111, 125, 130, 143, 145, 146, 150, 151, 155, 168, 169, 172, 175, 181, 207, 218, 222, 227, 230, 245, 247; C.I. Solvent Orange 2, 7, 11, 15, 26, 56, 77, 86; C.I. Solvent Violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60; C.I. Solvent Blue 4, 5, 14, 18, 35, 36, 37, 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, etc. 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, 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, 1 23, 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, 256, 259, 267, 269, 278, 280, 285, 290, 296, 315, 324:1, 335, 340; CI Acid Green dyes such as 1, 3, 5, 6, 7, 8, 9, 11, 13, 14, 15, 16, 22, 25, 27, 28, 41, 50, 50:1, 58, 63, 65, 80, 104, 105, 106, 109, etc. CI Direct Yellow 2, 33, 34, 35, 38, 39, 43, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129, 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, 90, 93, 94, 95, 97, 98, 99, 100, 101, 106, 107, 108, 109, 113, 114, 115, 117, 119, 120, 137, 149, 150, 153, 155, 156, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 168, 170, 171, 172, 173, 188, 189, 190, 192, 193, 194, 195, 196, 198, 199, 200, 201, 202, 203, 207, 209, 210, 212, 213, 214, 222, 225, 226, 228, 229, 236, 237, 238, 242, 243, 244, 245, 246, 247, 248, 249, 250, 251, 252, 256, 257, 259, 260, 268, 274, 275, 293; CI Direct Green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 77, 79, 82 and other CI Direct dyes, CI Disperse Yellow 51, 54, 76; CI Disperse Violet 26, 27; CI Disperse Blue 1, 14, 56, 60 and other CI disperse dyes, CI Basic Red 1, 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 Red 9; CI Basic Green 1; and other CI Basic dyes, CI Reactive Yellow 2,76,116; CI Reactive Orange 16; CI Reactive Red 36; and other CI reactive dyes CI Mordant Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65; CI Modant Red 1, 2, 3, 4, 9, 11, 12, 14, 17, 18, 19, 22, 23, 24, 25, 26, 27, 29, 30, 32, 33, 36, 37, 38, 39, 41, 42, 43, 45, 46, 48, 52, 53, 56, 62, 63, 71, 74, 76, 78, 85, 86, 88, 90, 94, 95; CI Modern Orange 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47, 48; CI Mordant Violet 1, 1:1, 2, 3, 4, 5, 6, 7, 8, 10, 11, 14, 15, 16, 17, 18, 19, 21, 22, 23, 24, 27, 28, 30, 31, 32, 33, 36, 37, 39, 40, 41, 44, 45, 47, 48, 49, 53, 58; CI Modern Blue 1, 2, 3, 7, 8, 9, 12, 13, 15, 16, 19, 20, 21, 22, 23, 24, 26, 30, 31, 32, 39, 40, 41, 43, 44, 48, 49, 53, 61, 74, 77, 83, 84; CI Modant Green 1, 3, 4, 5, 10, 13, 15, 19, 21, 23, 26, 29, 31, 33, 34, 35, 41, 43, 53, etc. CI Modant dyes Examples include CI bat dyes such as CI bat green 1.

[0153] The content of dye (A2) is preferably 10% by mass or less, more preferably 5% by mass or less, even more preferably 2% by mass or less, particularly preferably 1% by mass or less, and may even be 0% by mass, based on the total amount of colorant (A).

[0154] The content of the coloring agent (A) is preferably 0.1% to 70% by mass, more preferably 5% to 60% by mass, and even more preferably 10% to 50% by mass, based on the total amount of solids. When the content of the coloring agent (A) is within the above range, the color density when used as a color filter is sufficient, and the composition can contain the required amount of resin (B) and polymerizable compound (C), so that a pattern with sufficient mechanical strength can be formed.

[0155] Herein, "total amount of solids" as used herein refers to the amount obtained by subtracting the solvent content from the total amount of the coloring composition. The total amount of solids and the content of each component therein can be measured by known analytical means such as liquid chromatography or gas chromatography.

[0156] 2.Resin (B) Resin (B) is preferably an alkali-soluble resin. Examples of resin (B) include the following resins [K1] to [K6]. Resin [K1]; a copolymer having structural units derived from at least one monomer (a) (hereinafter sometimes referred to as "(a)") selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic acid anhydrides, and structural units derived from monomer (b) (hereinafter sometimes referred to as "(b)") having a cyclic ether structure with 2 to 4 carbon atoms and an ethylenically unsaturated bond; Resin [K2]; a copolymer having structural units derived from (a) and structural units derived from (b) and a monomer (c) copolymerizable with (a) (however different from (a) and (b)) (hereinafter sometimes referred to as "(c)"); Resin [K3]; a copolymer having structural units derived from (a) and structural units derived from (c); Resin [K4]; a copolymer having structural units derived from (a) to which (b) is added and structural units derived from (c); Resin [K5]; a copolymer having structural units derived from (b) to which (a) is added and structural units derived from (c); A copolymer having a structural unit obtained by adding (a) to a resin [K6] and further adding a carboxylic acid anhydride, and a structural unit obtained by adding (c).

[0157] (a) specifically includes, for example, unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, and o-, m-, p-vinylbenzoic acid; Unsaturated dicarboxylic acids such as maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyltetrahydrophthalic acid, and 1,4-cyclohexenedicarboxylic acid; Bicyclounsaturated compounds containing carboxyl groups, such as methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo[2.2.1]hept-2-ene, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene, 5-carboxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-carboxy-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]hepto-2-ene anhydride; Unsaturated mono(meth)acryloyloxyalkyl) esters of divalent or higher polycarboxylic acids such as mono(2-(meth)acryloyloxyethyl) succinate and mono(2-(meth)acryloyloxyethyl) phthalate; Examples include unsaturated acrylates containing both a hydroxyl group and a carboxyl group in the same molecule, such as α-(hydroxymethyl)acrylic acid. Of these, acrylic acid, methacrylic acid, maleic anhydride, and the like are preferred in terms of copolymerization reactivity and the solubility of the resulting resin in alkaline aqueous solutions.

[0158] In this specification, "(meth)acrylic acid" refers to at least one selected from the group consisting of acrylic acid and methacrylic acid. The terms "(meth)acryloyl" and "(meth)acrylate" have the same meaning.

[0159] (b) refers to a polymerizable compound having, for example, a cyclic ether structure with 2 to 4 carbon atoms (for example, at least one selected from the group consisting of an oxirane ring, an oxetane ring, and a tetrahydrofuran ring) and an ethylenically unsaturated bond. (b) is preferably a monomer having a cyclic ether with 2 to 4 carbon atoms and a (meth)acryloyloxy group.

[0160] Examples of (b) include monomers having an oxyranyl group and an ethylenically unsaturated bond (b1) (hereinafter sometimes referred to as "(b1)"), monomers having an oxetanyl group and an ethylenically unsaturated bond (b2) (hereinafter sometimes referred to as "(b2)"), and monomers having a tetrahydrofuryl group and an ethylenically unsaturated bond (b3) (hereinafter sometimes referred to as "(b3)").

[0161] Examples of (b1) include monomers having a linear or branched aliphatic unsaturated hydrocarbon structure that has been epoxidized (b1-1) (hereinafter sometimes referred to as "(b1-1)") and monomers having a cyclic unsaturated hydrocarbon structure that has been epoxidized (b1-2) (hereinafter sometimes referred to as "(b1-2)").

[0162] (b1-1) includes glycidyl (meth)acrylate, β-methylglycidyl (meth)acrylate, β-ethylglycidyl (meth)acrylate, glycidyl vinyl ether, o-vinylbenzylglycidyl ether, m-vinylbenzylglycidyl ether, p-vinylbenzylglycidyl ether, α-methyl-o-vinylbenzylglycidyl ether, α-methyl-m-vinylbenzylglycidyl ether, α-methyl-p-vinylbenzylglycidyl ether, 2,3-bis(glycidyl Examples include oxymethylstyrene, 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.

[0163] Examples of (b1-2) include vinylcyclohexene monooxide, 1,2-epoxy-4-vinylcyclohexane (e.g., Celoxide 2000; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., Cyclomer A400; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., Cyclomer M100; manufactured by Daicel Corporation), compounds represented by formula (R1), and compounds represented by formula (R2).

[0164] [ka]

[0165] [In equations (R1) and (R2), R ra and R rb This represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the hydrogen atom contained in the alkyl group may be substituted with a hydroxyl group. X ra and X rb This is a single bond, *-Rrc -, *-R rc -O-, *-R rc -S- or *-R rc Represents -NH- R rc This represents an alkanediyl group with 1 to 6 carbon atoms. * represents a bond with O.

[0166] Examples of alkyl groups having 1 to 4 carbon atoms include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, and tert-butyl group. Examples of alkyl groups in which a hydrogen atom is substituted with hydroxyl include hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 1-hydroxypropyl group, 2-hydroxypropyl group, 3-hydroxypropyl group, 1-hydroxy-1-methylethyl group, 2-hydroxy-1-methylethyl group, 1-hydroxybutyl group, 2-hydroxybutyl group, 3-hydroxybutyl group, and 4-hydroxybutyl group. R ra and R rb Preferably, the group can be a hydrogen atom, a methyl group, a hydroxymethyl group, a 1-hydroxyethyl group, or a 2-hydroxyethyl group, and more preferably a hydrogen atom or a methyl group.

[0167] Examples of alkanediyl groups include methylene, ethylene, propane-1,2-diyl, propane-1,3-diyl, butane-1,4-diyl, pentane-1,5-diyl, and hexane-1,6-diyl. X ra and X rb Preferably, the bonds include single bonds, methylene groups, ethylene groups, *-CH2-O- and *-CH2CH2-O-, and more preferably, single bonds and *-CH2CH2-O- (* represents a bond with O).

[0168] Compounds represented by formula (R1) include those represented by any of the formulas (R1-1) to (R1-15). Among these, 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.

[0169] [ka]

[0170] [ka]

[0171] Compounds represented by formula (R2) include those represented by any of the formulas (R2-1) to (R2-15). Among these, 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.

[0172] [ka]

[0173] [ka]

[0174] The compound represented by formula (R1) and the compound represented by formula (R2) may be used individually or in combination of two or more. When the compound represented by formula (R1) and the compound represented by formula (R2) are used in combination, their content ratio [compound represented by formula (R1):compound represented by formula (R2)] is preferably 5:95 to 95:5, more preferably 20:80 to 80:20, on a molar basis.

[0175] For (b2), monomers having an oxetanyl group and a (meth)acryloyloxy group are more preferred. Examples of (b2) include 3-methyl-3-methacryloyloxymethyl oxetane, 3-methyl-3-acryloyloxymethyl oxetane, 3-ethyl-3-methacryloyloxymethyl oxetane, 3-methyl-3-methacryloyloxyethyl oxetane, 3-methyl-3-acryloyloxyethyl oxetane, 3-ethyl-3-methacryloyloxyethyl oxetane, and 3-ethyl-3-acryloyloxyethyl oxetane.

[0176] For (b3), monomers having a tetrahydrofurfuryl group and a (meth)acryloyloxy group are more preferred. Specifically for (b3), examples include tetrahydrofurfuryl acrylate (e.g., Viscoat V#150, manufactured by Osaka Organic Chemical Industry Co., Ltd.) and tetrahydrofurfuryl methacrylate.

[0177] (b) is preferable because it allows for greater reliability of the resulting color filter in terms of heat resistance, chemical resistance, etc., as is (b1). Furthermore, (b1-2) is more preferable because it provides excellent storage stability for the colored composition.

[0178] (c) For example, methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, sec-butyl (meth)acrylate, tert-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, dodecyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, cyclopentyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, tricyclo[5.2.1.0 2,6] Decane-8-yl(meth)acrylate (in the relevant technical field, it is commonly called "dicyclopentanyl(meth)acrylate". It is also sometimes called "tricyclodecyl(meth)acrylate"), tricyclo[5.2.1.0 2,6 Decen-8-yl (meth)acrylate (commonly known as "dicyclopentenyl (meth)acrylate" in the relevant art), dicyclopentanyloxyethyl (meth)acrylate, isobornyl (meth)acrylate, adamantyl (meth)acrylate, allyl (meth)acrylate, propargyl (meth)acrylate, phenyl (meth)acrylate, naphthyl (meth)acrylate, benzyl (meth)acrylate, and other (meth)acrylic acid esters; Hydroxyl group-containing (meth)acrylic acid esters such as 2-hydroxyethyl (meth)acrylate and 2-hydroxypropyl (meth)acrylate; Diethyl maleate, diethyl fumarate, diethyl itaconate, and other dicarboxylic acid diesters; Bicyclo[2.2.1]hept-2-ene, 5-methylbicyclo[2.2.1]hept-2-ene, 5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxybicyclo[2.2.1]hept-2-ene, 5-hydroxymethylbicyclo[2.2.1]hept-2-ene, 5-(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5-methoxybic Chlo[2.2.1]hept-2-ene, 5-ethoxybicyclo[2.2.1]hept-2-ene, 5,6-dihydroxybicyclo[2.2.1]hept-2-ene, 5,6-di(hydroxymethyl)bicyclo[2.2.1]hept-2-ene, 5,6-di(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5,6-dimethoxybicyclo[2.2.1]hept -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- 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; Dicarbonylimide derivatives such as N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimide benzoate, N-succinimidyl-4-maleimide butyrate, N-succinimidyl-6-maleimide caproate, N-succinimidyl-3-maleimide propionate, and N-(9-acridinyl)maleimide; Examples include styrene, α-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, p-methoxystyrene, acrylonitrile, methacrylonitrile, vinyl chloride, vinylidene chloride, acrylamide, methacrylamide, vinyl acetate, 1,3-butadiene, isoprene, 2,3-dimethyl-1,3-butadiene, and the like. Of these, styrene, vinyltoluene, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo[2.2.1]hept-2-ene, and 2-hydroxyethyl (meth)acrylate are preferred in terms of copolymerization reactivity and heat resistance.

[0179] In resin [K1], the ratio of structural units derived from each is, among all structural units constituting resin [K1], (a) Structural units derived from (a); 2-60 mol% (b) Structural units derived from (b); 40-98 mol% It is preferable that this be the case. (a) Structural units derived from (a); 10-50 mol% (b) Structural units derived from (b); 50-90 mol% It is preferable that it be so. When the ratio of structural units of resin [K1] falls within the above range, the storage stability of the colored composition, the developability when forming a colored pattern, and the solvent resistance of the resulting color filter tend to be excellent.

[0180] The resin [K1] can be manufactured, for example, by referring to the method described in the literature "Experimental Methods for Polymer Synthesis" (by Takayuki Otsu, published by Kagaku Dojin Co., Ltd., 1st edition, 1st printing, March 1, 1972) and the cited literature.

[0181] Specifically, a method involves placing predetermined amounts of (a) and (b), a polymerization initiator, and a solvent into a reaction vessel, creating a deoxygenated atmosphere by, for example, replacing oxygen with nitrogen, and heating and maintaining the temperature while stirring. The polymerization initiator and solvent used here are not particularly limited and can be those commonly used in the field. For example, examples of polymerization initiators include azo compounds (2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), etc.) and organic peroxides (benzoyl peroxide, etc.), and the solvent can be any solvent that dissolves each monomer. Examples of solvents include those described later as solvent (E) of the colored composition of the present invention.

[0182] The resulting copolymer may be used as is after the reaction, or after being concentrated or diluted, or after being extracted as a solid (powder) by methods such as reprecipitation. In particular, by using the solvent contained in the colored composition of the present invention as the solvent during polymerization, the solution after the reaction can be used directly in the preparation of the colored composition of the present invention, thereby simplifying the manufacturing process of the colored composition of the present invention.

[0183] In resin [K2], the ratio of structural units derived from each is, among all structural units constituting resin [K2], (a) Structural units derived from (a); 2-45 mol% (b) Structural units derived from (b); 2-95 mol% (c) Structural units derived from (c); 1-75 mol% It is preferable that this be the case. (a) Structural units derived from (a); 5-40 mol% (b) Structural units derived from (b); 5-80 mol% (c) Structural units derived from this structure; 5-70 mol% It is preferable that it be so. When the ratio of structural units of resin [K2] falls within the above range, the colored composition tends to exhibit excellent storage stability, developability when forming colored patterns, and solvent resistance, heat resistance, and mechanical strength of the resulting color filter.

[0184] Resin [K2] can be manufactured, for example, in the same manner as described as the method for manufacturing resin [K1].

[0185] In resin [K3], the ratio of structural units derived from each is, out of the total structural units constituting resin [K3], (a) Structural units derived from (a); 2-60 mol% (c) Structural units derived from (c); 40-98 mol% It is preferable that this be the case. (a) Structural units derived from (a); 10-50 mol% (c) Structural units derived from (c); 50-90 mol% It is preferable that it be so. Resin [K3] can be manufactured, for example, in the same manner as described as the method for manufacturing resin [K1].

[0186] The resin [K4] can be produced by obtaining a copolymer of (a) and (c), and adding the cyclic ether having 2 to 4 carbon atoms of (b) to the carboxylic acid and / or carboxylic acid anhydride of (a). First, a copolymer of (a) and (c) is produced in the same manner as described for the production of resin [K1]. In this case, it is preferable that the ratio of structural units derived from each is the same as that given for resin [K3].

[0187] Next, a portion of the carboxylic acid and / or carboxylic acid anhydride derived from (a) in the copolymer is reacted with a cyclic ether having 2 to 4 carbon atoms that (b) possesses. Following the production of the copolymer of (a) and (c), the atmosphere inside the flask is replaced from nitrogen to air, and (b), a reaction catalyst for the reaction between a carboxylic acid or carboxylic acid anhydride and a cyclic ether (e.g., tris(dimethylaminomethyl)phenol) and a polymerization inhibitor (e.g., hydroquinone) are added to the flask and the mixture is reacted at, for example, 60 to 130°C for 1 to 10 hours to produce resin [K4]. The amount of (b) used is preferably 5 to 80 moles, more preferably 10 to 75 moles, per 100 moles of (a). This range tends to result in a good balance of storage stability of the colored composition, developability when forming patterns, and solvent resistance, heat resistance, mechanical strength, and sensitivity of the resulting patterns. Since the cyclic ether is highly reactive and unreacted (b) is less likely to remain, (b1) is preferred as the (b) used in the resin [K4], and (b1-1) is even more preferred. The amount of the reaction catalyst used is preferably 0.001 to 5 parts by mass per 100 parts by mass of the total amount of (a), (b), and (c). The amount of the polymerization inhibitor used is preferably 0.001 to 5 parts by mass per 100 parts by mass of the total amount of (a), (b), and (c). The reaction conditions, such as the preparation method, reaction temperature, and time, can be adjusted as appropriate, taking into account the manufacturing equipment and the amount of heat generated by polymerization. Similarly, the preparation method and reaction temperature can be adjusted as appropriate, taking into account the manufacturing equipment and the amount of heat generated by polymerization.

[0188] As a first step, resin [K5] is produced in the same manner as the production method for resin [K1] described above to obtain a copolymer of (b) and (c). As described above, the obtained copolymer may be used as is after the reaction, or a concentrated or diluted solution may be used, or it may be used after being extracted as a solid (powder) by methods such as reprecipitation. The ratios of structural units derived from (b) and (c) are, in relation to the total number of moles of all structural units constituting the copolymer, respectively: (b) Structural units derived from (b); 5-95 mol% (c) Structural units derived from (c); 5-95 mol% It is preferable that this be the case. (b) Structural units derived from (b); 10-90 mol% (c) Structural units derived from (c); 10-90 mol% It is preferable that it be so.

[0189] Furthermore, resin [K5] can be obtained by reacting the cyclic ether derived from (b) in the copolymer of (b) and (c) with the carboxylic acid or carboxylic acid anhydride of (a) under the same conditions as for the production of resin [K4]. The amount of (a) used to react with the copolymer is preferably 5 to 80 moles per 100 moles of (b). Since the cyclic ether is highly reactive and unreacted (b) is less likely to remain, (b1) is preferred as the (b) used in the resin [K5], and (b1-1) is even more preferred.

[0190] Resin [K6] is a resin obtained by further reacting resin [K5] with a carboxylic acid anhydride. The hydroxyl group generated by the reaction of a cyclic ether with a carboxylic acid or carboxylic acid anhydride is reacted with the carboxylic acid anhydride. Examples of carboxylic acid anhydrides include maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, and 5,6-dicarboxybicyclo[2.2.1]hepto-2-ene anhydride. The amount of carboxylic acid anhydride used is preferably 0.5 to 1 mole per mole of (a).

[0191] Specifically, resin (B) is 3,4-epoxycyclohexylmethyl(meth)acrylate / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] Resins such as decyl acrylate / (meth)acrylic acid copolymer [K1]; glycidyl (meth)acrylate / benzyl (meth)acrylate / (meth)acrylic acid copolymer, glycidyl (meth)acrylate / styrene / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 Decyl acrylate / (meth)acrylic acid / N-cyclohexyl maleimide copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6Resins such as decyl acrylate / (meth)acrylic acid / N-cyclohexyl maleimide / 2-hydroxyethyl (meth)acrylate copolymer, 3-methyl-3-(meth)acryloyloxymethyl oxetane / (meth)acrylic acid / styrene copolymer [K2]; resins such as benzyl (meth)acrylate / (meth)acrylic acid copolymer, styrene / (meth)acrylic acid copolymer [K3]; resins obtained by adding glycidyl (meth)acrylate to benzyl (meth)acrylate / (meth)acrylic acid copolymer, resins obtained by adding glycidyl (meth)acrylate to tricyclodecyl (meth)acrylate / styrene / (meth)acrylic acid copolymer, tricyclodecyl Examples of resins include those obtained by adding glycidyl(meth)acrylate to a (meth)acrylate / benzyl(meth)acrylate / (meth)acrylic acid copolymer [K4]; resins obtained by reacting (meth)acrylic acid with a copolymer of tricyclodecyl(meth)acrylate / glycidyl(meth)acrylate, resins obtained by reacting (meth)acrylic acid with a copolymer of tricyclodecyl(meth)acrylate / styrene / glycidyl(meth)acrylate [K5]; and resins obtained by reacting tetrahydrophthalic anhydride with a resin obtained by reacting (meth)acrylic acid with a copolymer of tricyclodecyl(meth)acrylate / glycidyl(meth)acrylate [K6]. Among these, resins [K1] and [K2] are preferred as resin (B), with resin [K1] being particularly preferred.

[0192] The weight-average molecular weight of resin (B) in terms of polystyrene is preferably 3,000 to 100,000, more preferably 5,000 to 50,000, and even more preferably 5,000 to 30,000. When the molecular weight is within the above range, the hardness of the color filter improves, the residual film rate increases, the solubility of the unexposed areas in the developer solution improves, and the resolution of the color pattern tends to improve.

[0193] The degree of dispersion of resin (B) [weight-average molecular weight (Mw) / number-average molecular weight (Mn)] is preferably 1.1 or more and 6 or less, and more preferably 1.2 or more and 4 or less.

[0194] The acid value of resin (B), on a solid content basis, is preferably 50 mg-KOH / g to 170 mg-KOH / g, more preferably 60 mg-KOH / g to 150 mg-KOH / g, and even more preferably 70 mg-KOH / g to 135 mg-KOH / g. Here, the acid value is measured as the amount of potassium hydroxide (mg) required to neutralize 1 g of resin (B), and can be determined, for example, by titration using an aqueous potassium hydroxide solution.

[0195] The content of resin (B) is preferably 7% to 85% by mass, more preferably 13% to 80% by mass, and even more preferably 15% to 70% by mass, relative to the total amount of solids. 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 improve.

[0196] 3. 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). Examples include compounds having polymerizable ethylenically unsaturated bonds, and preferably (meth)acrylic acid ester compounds.

[0197] In particular, polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds. Examples of such polymerizable compounds include trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, tripentaerythritol octa(meth)acrylate, tripentaerythritol hepta(meth)acrylate, tetrapentaerythritol deca(meth)acrylate, tetrapentaerythritol nona(meth)acrylate, and tri Examples include (2-(meth)acryloyloxyethyl) isocyanurate, ethylene glycol-modified pentaerythritol tetra(meth)acrylate, ethylene glycol-modified dipentaerythritol hexa(meth)acrylate, propylene glycol-modified pentaerythritol tetra(meth)acrylate, propylene glycol-modified dipentaerythritol hexa(meth)acrylate, caprolactone-modified pentaerythritol tetra(meth)acrylate, and caprolactone-modified dipentaerythritol hexa(meth)acrylate. In particular, at least one selected from the group consisting of dipentaerythritol penta(meth)acrylate and dipentaerythritol hexa(meth)acrylate is preferred.

[0198] The weight-average molecular weight of the polymerizable compound (C) is preferably 150 to 2,900, more preferably 250 to 1,500.

[0199] The content of polymerizable compound (C) is preferably 5% to 75% by mass, more preferably 7% to 70% by mass, and even more preferably 15% to 70% by mass, based on the total amount of solids. When the content of polymerizable compound (C) is within the above range, the residual film rate when forming a colored pattern and the chemical resistance of the color filter tend to improve.

[0200] 4. 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., upon the action of light or heat and initiate polymerization; any known polymerization initiator can be used. Examples of polymerization initiators that generate active radicals include alkylphenone compounds, triazine compounds, acylphosphine oxide compounds, O-acyloxime compounds, and biimidazole compounds.

[0201] The O-acyloxime compound is a compound having a substructure represented by formula (d1). Hereinafter, * represents a bond.

[0202] [ka]

[0203] Examples of the O-acyloxime compounds include N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropane-1-one-2-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]ethane-1-imine, and N-acetoxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethyl Examples include {-2,4-dioxacyclopentanylmethyloxy)benzoyl}-9H-carbazole-3-yl]ethane-1-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]-3-cyclopentylpropane-1-imine, N-benzoyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]-3-cyclopentylpropane-1-one-2-imine, and N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropane-1-one-2-imine. Commercially available products such as Irgacure OXE01, OXE02 (both manufactured by BASF), N-1919 (manufactured by ADEKA), and PBG-327 (manufactured by Changzhou Strong Electronics New Materials Co., Ltd.) may also be used. In particular, the O-acyloxime compound is preferably at least one selected from the group consisting of N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine, N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropane-1-one-2-imine, and N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropane-1-one-2-imine, with N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine and N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropane-1-one-2-imine being more preferred.These O-acyloxime compounds tend to produce high-brightness color filters.

[0204] The alkylphenone compound is a compound having a substructure represented by formula (d2) or formula (d3). In these substructures, the benzene ring may have substituents.

[0205] [ka]

[0206] Examples of compounds having the substructure represented by formula (d2) include 2-methyl-2-morpholino-1-(4-methylsulfanylphenyl)propan-1-one, 2-dimethylamino-1-(4-morpholinophenyl)-2-benzylbutan-1-one, and 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]butan-1-one. Commercially available products such as Irgacure 369, 907, and 379 (all manufactured by BASF) may also be used. Examples of compounds having the substructure 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-hydroxycyclohexylphenyl ketone, oligomer of 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propan-1-one, α,α-diethoxyacetophenone, and benzyldimethyl ketal. In terms of sensitivity, alkylphenone compounds having the substructure represented by formula (d2) are preferred.

[0207] Examples of the aforementioned triazine compounds include 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxynaphthyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxystyryl)-1,3,5-triazine, and 2,4-bis(trichloromethyl)-6-[ Examples include 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, and 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)ethenyl]-1,3,5-triazine.

[0208] Examples of the aforementioned acylphosphine oxide compound include 2,4,6-trimethylbenzoyldiphenylphosphine oxide. Commercially available products such as Irgacure® 819 (manufactured by BASF) may also be used.

[0209] Examples of the biimidazole compounds include 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3-dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole (see, for example, Japanese Patent Publication No. 6-75372, Japanese Patent Publication No. 6-75373, etc.), 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, and 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(alkoxyph Examples include phenyl)biimidazole, 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, Japanese Patent Publication No. 48-38403, Japanese Patent Application Publication No. 62-174204, etc.), and imidazole compounds in which the phenyl group at the 4,4',5,5'-position is substituted with a carboalkoxy group (see, for example, Japanese Patent Application Publication No. 7-10913, etc.).

[0210] Furthermore, examples of polymerization initiators (D) include benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether; benzophenone compounds such as benzophenone, o-benzoyl methyl benzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, 3,3',4,4'-tetra(tert-butylperoxycarbonyl)benzophenone, and 2,4,6-trimethylbenzophenone; quinone compounds such as 9,10-phenanthrenequinone, 2-ethylanthraquinone, and camphorquinone; and 10-butyl-2-chloroacridone, benzyl, methyl phenylglyoxylate, and titanocene compounds. These are preferably used in combination with polymerization initiators (D1) (especially amines) described later.

[0211] Examples of acid generators include onium salts such as 4-hydroxyphenyldimethylsulfonium p-toluenesulfonate, 4-hydroxyphenyldimethylsulfonium hexafluoroantimonate, 4-acetoxyphenyldimethylsulfonium p-toluenesulfonate, 4-acetoxyphenyl methyl benzylsulfonium hexafluoroantimonate, triphenylsulfonium p-toluenesulfonate, triphenylsulfonium hexafluoroantimonate, diphenyliodonium p-toluenesulfonate, and diphenyliodonium hexafluoroantimonate, as well as nitrobenzyl tosylates and benzoin tosylates.

[0212] The polymerization initiator (D) is preferably one comprising at least one selected from the group consisting of alkylphenone compounds, triazine compounds, acylphosphine oxide compounds, O-acyloxime compounds, and biimidazole compounds, and more preferably a polymerization initiator comprising an O-acyloxime compound.

[0213] The content of the polymerization initiator (D) is preferably 0.1 parts by mass to 30 parts by mass, and more preferably 1 part by mass to 20 parts by mass, based on 100 parts by mass of the total amount of resin (B) and polymerizable compound (C). When the content of the polymerization initiator (D) is within the above range, sensitivity tends to increase and exposure time shortens, thus improving the productivity of color filters.

[0214] 5. Polymerization initiator (D1) Polymerization initiator (D1) is a compound or sensitizer used to accelerate the polymerization of a polymerizable compound whose polymerization has been initiated by a polymerization initiator. When polymerization initiator (D1) is included, it is usually used in combination with the polymerization initiator (D). Examples of polymerization initiators (D1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds, and carboxylic acid compounds.

[0215] Examples of the amine compounds include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 2-ethylhexyl 4-dimethylaminobenzoate, N,N-dimethylparatoluidine, 4,4'-bis(dimethylamino)benzophenone (commonly known as Michla's ketone), 4,4'-bis(diethylamino)benzophenone, and 4,4'-bis(ethylmethylamino)benzophenone, with 4,4'-bis(diethylamino)benzophenone being preferred. Commercial products such as EAB-F (manufactured by Hodogaya Chemical Co., Ltd.) may also be used.

[0216] Examples of the alkoxyanthracene compounds include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene, 9,10-dibutoxyanthracene, and 2-ethyl-9,10-dibutoxyanthracene.

[0217] Examples of the thioxanthone compounds include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, and 1-chloro-4-propoxythioxanthone.

[0218] Examples of the carboxylic acid compounds include phenylsulfanylacetic acid, methylphenylsulfanylacetic acid, ethylphenylsulfanylacetic acid, methylethylphenylsulfanylacetic acid, dimethylphenylsulfanylacetic acid, methoxyphenylsulfanylacetic acid, dimethoxyphenylsulfanylacetic acid, chlorophenylsulfanylacetic acid, dichlorophenylsulfanylacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, naphthoxyacetic acid, and the like.

[0219] When these polymerization initiators (D1) are used, their content is preferably 0.1 parts by mass to 30 parts by mass, and more preferably 1 part by mass to 20 parts by mass, based on 100 parts by mass of the total amount of resin (B) and polymerizable compound (C). When the amount of polymerization initiator (D1) is within this range, it is possible to form a colored pattern with even higher sensitivity, and the productivity of color filters tends to improve.

[0220] 6. Solvent (E) The solvent (E) is not particularly limited, and any solvent commonly used in the art may be used. Examples include ester solvents (solvents containing -COO- but not -O-), ether solvents (solvents containing -O- but not -COO-), ether ester solvents (solvents containing both -COO- and -O-), ketone solvents (solvents containing both -CO- and -COO-), alcohol solvents (solvents containing OH but not -O-, -CO-, and -COO-), aromatic hydrocarbon solvents, amide solvents, dimethyl sulfoxides, and the like.

[0221] 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, with ethyl lactate being preferred.

[0222] Examples of ether solvents include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenethole, and methylanisole, with propylene glycol monomethyl ether, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, and diethylene glycol monoethyl ether being preferred.

[0223] Examples of ether ester solvents include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, ethyl 2-ethoxy-2-methylpropionate, ethyl 3-methoxybutyl acetate, methyl- Examples include 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. Propylene glycol monomethyl ether acetate and ethyl 3-ethoxypropionate are preferred, and propylene glycol monomethyl ether acetate is particularly preferred.

[0224] Examples of ketone solvents include 4-hydroxy-4-methyl-2-pentanone (diacetone alcohol), acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone, and isophorone, with 4-hydroxy-4-methyl-2-pentanone being preferred.

[0225] Examples of alcoholic solvents include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerin.

[0226] Examples of aromatic hydrocarbon solvents include benzene, toluene, xylene, and mesitylene.

[0227] Examples of amide solvents include N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone, with N,N-dimethylformamide being preferred.

[0228] As the solvent (E), ester solvents, ether solvents, ether ester solvents, ketone solvents, and amide solvents are more preferred, ether ester solvents and ketone solvents are even more preferred, and ether ester solvents, or a combination of ether ester solvents and ketone solvents, are particularly preferred. When ether ester solvents and ketone solvents are combined, their volume ratio (ether ester solvent / ketone solvent) is, for example, 50 / 50 to 99 / 1, preferably 60 / 40 to 98 / 2, and more preferably 70 / 30 to 97 / 3.

[0229] Furthermore, from the viewpoint of applicability and drying properties, the above solvent is preferably selected from those with a boiling point of 120°C or higher and 180°C or lower at 1 atm. Examples of solvents that satisfy this boiling point condition are, for example, 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, and examples include propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate, ethyl 3-ethoxypropionate, and 4-hydroxy-4-methyl-2-pentanone.

[0230] The solvent (E) content is preferably 55% to 95% by mass, and more preferably 60% to 92% by mass, relative to the total amount of the colored composition of the present invention. In other words, the total solid content of the colored composition is preferably 5% to 45% by mass, and more preferably 8% to 40% by mass. When the solvent (E) content is within the above range, the flatness during application is good, and the display characteristics tend to be good because there is no shortage of color density when a color filter is formed.

[0231] 7. Leveling agent (F) Examples of leveling agents (F) include silicone-based surfactants, fluorine-based surfactants, and silicone-based surfactants containing fluorine atoms. These may have polymerizable groups in their side chains.

[0232] Examples of silicone-based surfactants include surfactants that have siloxane bonds in their molecules. Specifically, examples include Toray Silicone DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, SH29PA, SH30PA, SH8400 (product name: manufactured by Toray Dow Corning Co., Ltd.), KP321, KP322, KP323, KP324, KP326, KP340, KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452, and TSF4460 (manufactured by Momentive Performance Materials Japan LLC).

[0233] Examples of the aforementioned fluorine-based surfactants include surfactants having fluorocarbon chains in their molecules. Specifically, these include Florard® FC430, FC431 (manufactured by Sumitomo 3M Co., Ltd.), Megafac® F142D, F171, F172, F173, F177, F183, F554, R30, RS-718-K (manufactured by DIC Corporation), F-Top® EF301, EF303, EF351, EF352 (manufactured by Mitsubishi Materials Electronic Chemicals Co., Ltd.), Surflon® S381, S382, SC101, SC105 (manufactured by AGC Inc.), and E5844 (manufactured by Daikin Fine Chemical Laboratories, Inc.).

[0234] Examples of silicone-based surfactants containing fluorine atoms include surfactants having siloxane bonds and fluorocarbon chains in their molecules. Specifically, examples include Megafac® R08, BL20, F475, F477, and F443 (manufactured by DIC Corporation).

[0235] The content of the leveling agent (F) is preferably 0.001% by mass or more and 0.2% by mass or less, more preferably 0.002% by mass or more and 0.1% by mass or less, and even more preferably 0.01% by mass or more and 0.05% by mass or less, relative to the total amount of the colored composition. Note that this content does not include the content of the pigment dispersant. When the content of the leveling agent (F) is within the above range, the flatness of the color filter can be improved.

[0236] 8. Other ingredients The colored composition of the present invention may optionally contain additives known in the art, such as fillers, other polymer compounds, adhesion promoters, antioxidants, light stabilizers, and chain transfer agents.

[0237] <Method for producing colored composition> The colored compositions of the present invention can be prepared, for example, by mixing a compound (I) and a pigment (A1), and optionally a dye (A2), a resin (B), a polymerizable compound (C), a polymerization initiator (D), a solvent (E), a leveling agent (F), and other components. Mixing can be carried out using known or conventional apparatus and conditions.

[0238] In particular, when the coloring composition of the present invention is a coloring composition containing components other than compound (I) and pigment (A1), it is preferable to pre-mix compound (I) and pigment (A1) in the preparation of the coloring composition. Hereinafter, such a pre-prepared product will be referred to as coloring composition (2) (however, it does not contain polymerizable compound (C) and polymerization initiator (D)).

[0239] The colored composition (2) is preferably dispersed using a bead mill, solvent (E), etc. The diameter of the beads is preferably 0.05 mm or more and 0.5 mm or less, and the material of the beads can be glass, ceramic, metal, etc. The colored composition (2) may optionally contain part or all of at least one selected from the group consisting of the dispersant, resin (B), and solvent (E). The solid content of the colored composition (2) is preferably 5% by mass or more and 45% by mass or less, more preferably 9% by mass or more and 30% by mass or less, and particularly preferably 10% by mass or more and 25% by mass or less. Furthermore, the total content of compound (I) and pigment (A1) is preferably 3% by mass or more and 25% by mass or less based on the total amount of the colored composition (2). In addition, the total content of the dispersant and resin (B) is preferably 0% by mass or more and 25% by mass or less based on the total amount of the colored composition (2). The desired colored composition can be prepared by mixing the remaining components to the colored composition (2) obtained in this way to a predetermined concentration, as needed. As is evident from the fact that coloring composition (2) contains compound (I) and pigment (A1), coloring composition (2) is also included in the coloring compositions of the present invention.

[0240] The colored composition of the present invention preferably has a viscosity (initial viscosity) of 17 mPa·s or less, more preferably 15 mPa·s or less, and more preferably 2 mPa·s or more, and more preferably 3 mPa·s or more, as measured by an E-type viscometer at a temperature of 23°C and a rotation speed of 100 rpm. In particular, it is preferable that the viscosity of colored composition (2) is within the above range.

[0241] The colored compositions of the present invention preferably have excellent storage stability. In at least one of the colored compositions stored at 5°C for 7 days and the colored compositions stored at 23°C for 7 days, the viscosity measured with an E-type viscometer at a temperature of 23°C and a rotation speed of 100 rpm is preferably 20 mPa·s or less, more preferably 15 mPa·s or less, and preferably 2 mPa·s or more, and more preferably 3 mPa·s or more. In particular, it is preferable that the viscosity of colored composition (2) is within the above range.

[0242] <How to manufacture color filters> Methods for producing a colored pattern for a color filter from the colored composition of the present invention include photolithography, inkjet printing, and other printing methods. Among these, photolithography is preferred. Photolithography is a method in which the colored composition is applied to a substrate, dried to form a composition layer, exposed to light through a photomask, and developed to form a colored pattern. In photolithography, by not using a photomask during exposure and / or by not developing, a colored coating film, which is a cured product of the composition layer, can be formed. The colored pattern or colored coating film formed in this way is the color filter of the present invention.

[0243] The film thickness of the color filter is not particularly limited and can be adjusted as appropriate depending on the purpose and application. For example, it is 0.1 μm or more and 30 μm or less, preferably 0.1 μm or more and 20 μm or less, and more preferably 0.5 μm or more and 6 μm or less.

[0244] As substrates, glass plates such as quartz glass, borosilicate glass, aluminasilate glass, and soda-lime glass with a silica coating on the surface are used; resin plates such as polycarbonate, polymethyl methacrylate, and polyethylene terephthalate are used; silicon is used; and aluminum, silver, and silver / copper / palladium alloy thin films are formed on the substrate. Other color filter layers, resin layers, transistors, circuits, etc. may be formed on these substrates. Alternatively, a substrate treated with HMDS on a silicon substrate may be used.

[0245] The formation of each color pixel by photolithography can be carried out using known or conventional equipment and conditions. For example, it can be manufactured as follows: First, a colored composition is applied to a substrate, and volatile components such as solvents are removed by heat drying (pre-baking) and / or vacuum drying to obtain a smooth composition layer. Examples of application methods include spin coating, slit coating, and slit and spin coating. When performing heat drying, the temperature is preferably 30°C to 120°C, and more preferably 50°C to 110°C. The heating time is preferably 10 seconds to 60 minutes, and more preferably 30 seconds to 30 minutes. When performing vacuum drying, it is preferable to do so under a pressure of 50 to 150 Pa and at a temperature range of 20 to 25°C. The film thickness of the composition layer is not particularly limited and can be appropriately selected according to the film thickness of the desired color filter.

[0246] Next, the composition layer is exposed via a photomask to form the desired colored pattern. The pattern on the photomask is not particularly limited, and a pattern appropriate to the intended application is used. A light source that generates light with a wavelength of 250 to 450 nm is preferred for exposure. For example, light below 350 nm may be cut using a filter that cuts this wavelength range, or light around 436 nm, 408 nm, and 365 nm may be selectively extracted using a bandpass filter that extracts these wavelength ranges. Specifically, examples include mercury lamps, light-emitting diodes, metal halide lamps, halogen lamps, etc. It is preferable to use a reduction projection exposure apparatus or proximity exposure apparatus such as a mask aligner and stepper, as this allows for uniform irradiation of the entire exposure surface with parallel light rays and precise alignment of the photomask and the substrate.

[0247] A colored pattern is formed on the substrate by developing the exposed composition layer in contact with a developer. During development, the unexposed parts of the composition layer are dissolved and removed by the developer. As the developer, aqueous solutions of alkaline compounds such as potassium hydroxide, sodium bicarbonate, sodium carbonate, and tetramethylammonium hydroxide are preferred. The concentration of these alkaline compounds in the aqueous solution is preferably 0.01% by mass or more and 10% by mass or less, and more preferably 0.03% by mass or more and 5% by mass or less. Furthermore, the developer may also contain a surfactant. The development method may be any of the following: the paddle method, the dipping method, and the spray method. Furthermore, the substrate may be tilted at any angle during development. After developing, it is preferable to wash the film with water.

[0248] Furthermore, it is preferable to perform post-baking on the obtained coloring pattern. The post-baking temperature is preferably 80°C to 250°C, and more preferably 100°C to 245°C. The post-baking time is preferably 1 minute to 120 minutes, and more preferably 2 minutes to 30 minutes.

[0249] The colored patterns and colored coatings obtained in this manner are useful as color filters, and these color filters are useful as color filters used in display devices (e.g., liquid crystal display devices, organic EL devices, etc.), electronic paper, solid-state image sensors, etc. [Examples]

[0250] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples. In the examples and comparative examples, percentages and parts representing content or usage are by mass unless otherwise specified. In the following examples, the structure of the compounds was confirmed using a 400 MHz superconducting Fourier transform nuclear magnetic resonance spectrometer (Varian 400-MR; manufactured by Agilent).

[0251] [Compound synthesis example] <Synthesis of compound (I-1)>

[0252] 22 parts of 2,5-dichloro-4-nitroaniline were mixed with 56 parts of water, 22 parts of acetic acid, 45 parts of methanol, and 78 parts of 98% sulfuric acid, and the mixture was stirred. Under ice cooling, an aqueous solution of 15 parts of sodium nitrite dissolved in 22 parts of water was added to the reaction solution and the mixture was stirred for 2 hours to obtain a suspension containing the diazonium salt. Meanwhile, 17 parts of 3-methyl-1-phenyl-5-pyrazolone were mixed with 67 parts of methanol, and then 234 parts of a 25% sodium hydroxide aqueous solution were added under ice cooling and the mixture was stirred. The suspension containing the diazonium salt was then added dropwise. After the dropwise addition was complete, the mixture was stirred for another 1 hour at room temperature to obtain an orange suspension. The orange solid obtained by filtration was dried under reduced pressure at 60°C to obtain the compound represented by formula (1).

[0253] [ka]

[0254] Next, 38 parts of the compound represented by formula (1) were mixed with 129 parts of water, 16 parts of sodium bicarbonate, and 47 parts of sodium sulfide notahydrate, and the mixture was stirred at 85°C for 2 hours. After the reaction mixture was cooled to room temperature, it was neutralized to pH 6 with 35% hydrochloric acid, and the precipitated solid was filtered off. The obtained solid was washed with water, filtered, and the resulting red solid was dried under reduced pressure at 60°C to obtain the compound represented by formula (2).

[0255] [ka]

[0256] Next, 1.0 part of the compound represented by formula (2) was mixed with 4.1 parts of N-methyl-2-pyrrolidone, 1.5 parts of acetic acid, and 20 parts of 80% sulfuric acid, and the mixture was stirred. Under ice cooling, an aqueous solution of 0.2 parts of sodium nitrite dissolved in 0.4 parts of water was added to the reaction solution and stirred for 2 hours. Then, an aqueous solution of 0.1 parts of sulfamic acid dissolved in 0.5 parts of water and 5.1 parts of acetic acid was added to the reaction solution and stirred to obtain a suspension containing the diazonium salt. Meanwhile, 0.7 parts of 3-methyl-1-(4-sulfophenyl)-2-pyrazolin-5-one were mixed with 15 parts of N-methyl-2-pyrrolidone and 41 parts of water, and the mixture was stirred for 30 minutes. Under ice cooling, the suspension containing the diazonium salt and 23 parts of 25% aqueous ammonia were added dropwise, and the mixture was stirred at room temperature for 1 hour to obtain a red suspension. The red solid obtained by filtration was dispersed and washed with water and methanol for 30 minutes each, then filtered and dried under reduced pressure at 60°C to obtain 0.5 parts (yield 27%) of the azo compound represented by formula (I-1) (hereinafter referred to as compound (I-1)). 1 H-NMR (DMSO-d6): δ2.34(s,3H), δ2.35(s,3H), δ6.94-7.32(br,4H), δ7.23(t,1H), δ7.46(t, 2H),δ7.69(d,2H),δ7.86(d,2H),δ7.88(m,2H),δ7.99(s,1H),δ8.00(s,1H),δ13.50(br,2H)

[0257] [ka]

[0258] [Pigment synthesis example 1] Following the instructions in Dyes and Pigments 80 (2009) 245-253, the compound represented by formula (a-1) (hereinafter referred to as compound (a-1)) was synthesized.

[0259] [ka]

[0260] [Example of resin synthesis 1] A suitable amount of nitrogen was flowed into a flask equipped with a reflux condenser, dropping funnel, and stirrer to replace the atmosphere with nitrogen. 280 parts of propylene glycol monomethyl ether acetate were added, and the mixture was heated to 80°C while stirring. Then, 38 parts of acrylic acid and 3,4-epoxytricyclo[5.2.1.0 2,6 ] Decane-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 2,6 A mixture of 289 parts of decane-9-yl acrylate (with a molar ratio of 1:1) and 125 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. Meanwhile, a solution of 33 parts of 2,2-azobis(2,4-dimethylvaleronitrile) dissolved in 235 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After the addition was complete, the mixture was held at 80°C for 4 hours, then cooled to room temperature to obtain a copolymer (resin B-2) solution with a solid content of 35.1% and a viscosity of 125 mPas measured with a B-type viscometer (23°C). The weight-average molecular weight Mw of the resulting copolymer was 9.2 × 10⁻⁶. 3 The dispersion was 2.08, and the acid value on a solid content basis was 77 mg-KOH / g. Resin B-2 has the following structural units.

[0261] [ka]

[0262] The weight-average molecular weight (Mw) and number-average molecular weight (Mn) of the resin, calculated on a polystyrene basis, were measured using the GPC method under the following conditions. Equipment: HLC-8120GPC (manufactured by Tosoh Corporation) Column; TSK-GELG2000HXL Column temperature: 40°C Solvent; THF Flow rate: 1.0mL / min Test liquid solid content concentration: 0.001~0.01% by mass Injection volume: 50μL Detector; RI Calibration standard material ;TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (Manufactured by Tosoh Corporation) The ratio of the weight-average molecular weight to the number-average molecular weight (Mw / Mn) obtained above in polystyrene terms was defined as the degree of dispersion.

[0263] Example 1 4.5 parts of compound (a-1), 0.5 parts of compound (I-1), 3.5 parts of dispersant (BYKLPN-6919, manufactured by BYK) (based on solid content), 3.5 parts of resin (B-2) (based on solid content), 83 parts of propylene glycol monomethyl ether acetate (hereinafter sometimes referred to as PGMEA), and 5.0 parts of diacetone alcohol (hereinafter sometimes referred to as DAA) were mixed, 300 parts of 0.2 mm zirconia beads were added and shaken, and the zirconia beads were removed by filtration to obtain colored composition 1.

[0264] Examples 2-4 Colored compositions 2 to 4 were obtained in the same manner as in Example 1, except that compound (a-1) in Example 1 was replaced with the following compound. Example 2: Coloring composition 2: CI Pigment Orange 13 (hereinafter sometimes referred to as PO13). Example 3: Coloring composition 3: CI Pigment Red 269 (hereinafter sometimes referred to as PR269). Example 4: Coloring composition 4: CI Pigment Orange 71 (hereinafter sometimes referred to as PO71).

[0265] Example 5 3.8 parts of compound (a-1), 1.3 parts of compound (I-1), 3.5 parts of dispersant (BYKLPN-6919, manufactured by BYK) (based on solid content), 3.5 parts of resin (B-2) (based on solid content), 83 parts of PGMEA, and 5.0 parts of DAA were mixed, 300 parts of 0.2 mm zirconia beads were added and shaken, and the zirconia beads were removed by filtration to obtain colored composition 5.

[0266] Example 6 3.0 parts of compound (a-1), 2.0 parts of compound (I-1), 3.5 parts of dispersant (BYKLPN-6919, manufactured by BYK) (based on solid content), 3.5 parts of resin (B-2) (based on solid content), 83 parts of PGMEA, and 5.0 parts of DAA were mixed, 300 parts of 0.2 mm zirconia beads were added and shaken, and the zirconia beads were removed by filtration to obtain colored composition 6.

[0267] Comparative Example 1 5.0 parts of compound (a-1), 3.5 parts of dispersant (BYKLPN-6919, manufactured by BYK) (based on solid content), 3.5 parts of resin (B-2) (based on solid content), 83 parts of propylene glycol monomethyl ether acetate, and 5.0 parts of diacetone alcohol were mixed, 300 parts of 0.2 mm zirconia beads were added and shaken, and the zirconia beads were removed by filtration to obtain colored composition 7.

[0268] Comparative Examples 2-4 Colored compositions 8 to 10 were obtained in the same manner as in Comparative Example 1, except that compound (a-1) in Comparative Example 1 was replaced with the compound described below. Comparative Example 2: Coloring Composition 8: CI Pigment Orange 13 Comparative Example 3: Coloring Composition 9: CI Pigment Red 269 Comparative Example 4: Coloring Composition 10: CI Pigment Orange 71

[0269] [Table 3]

[0270] <Viscosity Evaluation> The viscosity of the colored composition immediately after manufacturing (=initial viscosity) was measured using a cone-plate type (E-type) viscometer (Viscometer TV-25, manufactured by Toki Sangyo Co., Ltd.) under conditions of a rotation speed of 100 rpm and a measurement temperature of 23°C. The results are shown in Table 4. In Table 4, × indicates that the viscosity was too high to measure. From the results below, it can be seen that compound (I) contributes to the reduction of viscosity of the pigment-containing composition.

[0271] [Table 4]

[0272] <Evaluation of viscosity stability over time> The viscosity of the colored compositions after storage at 5°C for 7 days and after storage at 23°C for 7 days was measured according to the method described above. The colored compositions of Examples 1-2 and 4-6 had low viscosity even after 7 days of storage, indicating good storage stability.

[0273] [Table 5] [Industrial applicability]

[0274] According to the compound of the present invention, the viscosity of the colored composition can be reduced, resulting in improved workability during mixing and application. By using this colored composition, a color filter with excellent properties can be easily formed.

Claims

1. A colored composition comprising a compound represented by formula (I) and a pigment. 【Chemistry 1】 [In formula (I), L 1 This represents the group represented by formula (ph1), R 1 ~R 4 each independently represents a hydrogen atom, a hydrocarbon group which may have a substituent, a heterocyclic group, -SO 3 N(R 5 ) 4 , a cyano group, or a halogen atom. However, at least one of R 1 ~R 4 is a hydrocarbon group having one or more -SO 3 N(R 5 ) 4 as a substituent or -SO 3 N(R 5 ) 4 . R 5 represents a hydrogen atom or a hydrocarbon group, and a plurality of R 5 may be the same or different.] 【Chemistry 2】 [In formula (ph1), X 1 -CH represents a hydrocarbon group which may have substituents, a substituted or unsubstituted amino group, an N-acylamino group, a carboxyl group, a C1-C4 alkoxy group, a C1-C4 alkylsulfanyl group, a cyano group, or a halogen atom, and the hydrocarbon group contains -CH 2 The - may be replaced by -O-, -CO-, or -NH-, and the -CH= contained in the hydrocarbon group may be replaced by -N=. n represents an integer from 0 to 4. If n represents an integer of 2 or more, multiple X 1 They may be the same or different. n represents an integer of 2 or more, and there are multiple X 1 However, in formula (ph1), when the carbon atoms constituting the phenylene group are bonded to adjacent carbon atoms, X is bonded to the adjacent carbon atoms. 1 These elements may join together to form a ring. * represents a joining hand.

2. L 1 The coloring composition according to claim 1, wherein is a group represented by formula (ph2). 【Transformation 3】 [In formula (ph2), X 2 ~X 5 Each of these independently represents a hydrogen atom, a C1-C4 alkyl group, a substituted or unsubstituted amino group, an N-acylamino group, a carboxyl group, a C1-C4 alkoxy group, a C1-C4 alkylsulfanyl group, a cyano group, or a halogen atom. 2 and X 3 , X 4 and X 5 These elements may join together to form a ring. * represents a joining hand.

3. The coloring composition according to claim 1 or 2, further comprising a solvent.

4. The colored composition according to any one of claims 1 to 3, further comprising a resin.

5. The coloring composition according to any one of claims 1 to 4, further comprising a polymerizable compound and a polymerization initiator.

6. The colored composition according to any one of claims 1 to 5, wherein the pigment is an azo pigment.

7. A color filter formed from a colored composition according to any one of claims 1 to 6.

8. A display device including the color filter described in claim 7.

9. A compound represented by formula (I). 【Chemistry 4】 [In formula (I), L 1 This represents the group represented by formula (ph1), R 1 ~R 4 Each of these independently comprises a hydrogen atom, a hydrocarbon group which may have substituents, a heterocyclic group, and -SO 3 N(R) 5 ) 4 , represents a cyano group or a halogen atom. However, R 1 ~R 4 At least one of them has one or more -SO as substituents. 3 N(R) 5 ) 4 A hydrocarbon group having -SO 3 N(R) 5 ) 4 That is. R 5 R represents a hydrogen atom or hydrocarbon group, and there are multiple R 5 They may be the same or different. 【Transformation 5】 [In formula (ph1), X 1 -CH represents a hydrocarbon group which may have substituents, a substituted or unsubstituted amino group, an N-acylamino group, a carboxyl group, a C1-C4 alkoxy group, a C1-C4 alkylsulfanyl group, a cyano group, or a halogen atom, and the hydrocarbon group contains -CH 2 The - may be replaced by -O-, -CO-, or -NH-, and the -CH= contained in the hydrocarbon group may be replaced by -N=. n represents an integer from 0 to 4. If n represents an integer of 2 or more, multiple X 1 They may be the same or different. n represents an integer of 2 or more, and there are multiple X 1 However, in formula (ph1), when the carbon atoms constituting the phenylene group are bonded to adjacent carbon atoms, X is bonded to the adjacent carbon atoms. 1 These elements may join together to form a ring. * represents a joining hand.

10. L 1 The compound according to claim 9, wherein is a group represented by formula (ph2). 【Transformation 6】 [In formula (ph2), X 2 ~X 5 Each of these independently represents a hydrogen atom, a C1-C4 alkyl group, a substituted or unsubstituted amino group, an N-acylamino group, a carboxyl group, a C1-C4 alkoxy group, a C1-C4 alkylsulfanyl group, a cyano group, or a halogen atom. 2 and X 3 , X 4 and X 5 These elements may join together to form a ring. * represents a joining hand.

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