Compound and method for producing said compound

Abstract

The present invention addresses the problem of providing a novel phthalocyanine compound capable of forming a color filter in which luminance unevenness can be suppressed even after long-term use. The above-mentioned problem can be solved by a compound represented by formula (I). [In formula (I), each of R1-R16 independently represents a hydrogen atom, a chlorine atom, an optionally substituted hydrocarbon group having 1-6 carbon atoms, or a specific aryloxy group containing a chlorine atom, and-CH2-contained in the hydrocarbon group may be substituted with-O-or-CO-. In this connection, at least one of R1-R16 represents a specific aryloxy group containing a chlorine atom. ] # imgabs0 #

Description

Technical Field

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

[0002] Color filters used in display devices such as liquid crystal display devices, electroluminescent display devices, and plasma displays, and solid-state imaging devices such as CCD or CMOS sensors are manufactured from colored resin compositions. As colorants used in such colored resin compositions, phthalocyanine compounds are known, and in particular, CI Pigment Green 58 (Patent Document 1) has been widely used as a colorant for making a green colored filter (green filter) in a color filter.

[0003] Prior art literature

[0004] Patent Literature

[0005] Patent Document 1: Japanese Patent Application Publication No. 2009-192661 Summary of the invention

[0006] However, when a color filter formed of a colored resin composition containing CI Pigment Green 58 is used in a display device, for example, unevenness may occur due to a difference in brightness between the peripheral portion and the central portion of the colored filter if used for a long time. Therefore, an object of the present invention is to provide a novel phthalocyanine compound that can form a color filter capable of suppressing uneven brightness even after long-term use.

[0007] In addition, the present inventors studied the reaction of the corresponding phthalonitrile compound in the presence of a base when producing the above-mentioned novel phthalocyanine compound, but found that the yield of the target compound was reduced in this method. Therefore, another object of the present invention is to provide a novel production method capable of increasing the yield of a specific phthalocyanine compound.

[0008] The gist of the present invention is as follows.

[0009] [1] A compound represented by formula (I).

[0010]

[0011] [In formula (I),

[0012] R 1 ~R 16 Each independently represents a hydrogen atom, a chlorine atom, a hydrocarbon group having 1 to 6 carbon atoms which may have a substituent, a group represented by formula (i-a), a group represented by formula (i-b), or a group represented by formula (i-c), wherein -CH2- contained in the hydrocarbon group may be substituted by -O- or -CO-.1 ~R 16 At least one of them represents a group represented by formula (i-a), a group represented by formula (i-b) or a group represented by formula (i-c); when there are multiple groups represented by formula (i-a), they may be the same or different; when there are multiple groups represented by formula (i-b), they may be the same or different; when there are multiple groups represented by formula (i-c), they may be the same or different.]

[0013]

[0014] [In formula (i-a),

[0015] R a1 ~R a5 Each independently represents a hydrogen atom, a chlorine atom, a bromine atom, a carboxyl group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, wherein -CH2- contained in the hydrocarbon group may be substituted by -O- or -CO-. a1 ~R a5 1 to 3 of them are chlorine atoms. * indicates the bonding site. ]

[0016]

[0017] [In formula (i-b),

[0018] R b1 ~R b7 Each independently represents a hydrogen atom, a chlorine atom, a bromine atom, a carboxyl group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, wherein -CH2- contained in the hydrocarbon group may be substituted by -O- or -CO-. b1 ~R b7 1 to 3 of them are chlorine atoms. * indicates the bonding site. ]

[0019]

[0020] [In formula (i-c),

[0021] R c1 ~R c7 Each independently represents a hydrogen atom, a chlorine atom, a bromine atom, a carboxyl group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, wherein -CH2- contained in the hydrocarbon group may be substituted by -O- or -CO-. c1 ~R c7 1 to 3 of them are chlorine atoms. * indicates the bonding site. ]

[0022] [2] The compound according to [1], wherein R 1 ~R 4At least one of them is a group represented by formula (i-a), formula (i-b) or formula (i-c), R 5 ~R 8 At least one of them is a group represented by formula (i-a), formula (i-b) or formula (i-c), R 9 ~R 12 At least one of them is a group represented by formula (i-a), formula (i-b) or formula (i-c), and R 13 ~R 16 At least one of them is a group represented by formula (i-a), formula (i-b) or formula (i-c).

[0023] [3] The compound according to [1] or [2], wherein R 2 and R 3 At least one of them is a group represented by formula (i-a), formula (i-b) or formula (i-c), R 6 and R 7 At least one of them is a group represented by formula (i-a), formula (i-b) or formula (i-c), R 10 and R 11 At least one of them is a group represented by formula (i-a), formula (i-b) or formula (i-c), and R 14 and R 15 At least one of them is a group represented by formula (i-a), formula (i-b) or formula (i-c), R 1 , R 4 , R 5 , R 8 , R 9 , R 12 , R 13 and R 16 A hydrogen atom.

[0024] [4] The compound according to any one of [1] to [3], wherein R 2 and R 3 Any one of them is a group represented by formula (i-a), formula (i-b) or formula (i-c), R 6 and R 7 Any one of them is a group represented by formula (i-a), formula (i-b) or formula (i-c), R 10 and R 11 Any one of them is a group represented by formula (i-a), formula (i-b) or formula (i-c), and R 14 and R 15 Any one of them is a group represented by formula (i-a), formula (i-b) or formula (i-c), R 1 , R 4 , R 5 , R 8, R 9 , R 12 , R 13 and R 16 is a hydrogen atom,

[0025] The four groups represented by the formula (i-a), the formula (i-b) or the formula (i-c) in the formula (I) are the same groups.

[0026] [5] The compound according to [2], wherein R 1 , R 5 , R 9 and R 13 are each independently a group represented by formula (i-a), formula (i-b) or formula (i-c), R 2 ~R 4 , R 6 ~R 8 , R 10 ~R 12 and R 14 ~R 16 A hydrogen atom.

[0027] [6] A colored resin composition comprising a colorant and a resin, wherein the colorant comprises the compound according to any one of [1] to [5].

[0028] [7] The colored resin composition according to [6], further comprising a polymerizable compound and a polymerization initiator.

[0029] [8] A color filter formed from the colored resin composition according to [7].

[0030] [9] A display device comprising the color filter described in [8].

[0031]

[10] A solid-state imaging element comprising the color filter described in [8].

[0032]

[11] A method for producing a compound represented by formula (I), comprising reacting compounds represented by formulae (II-1) to (II-4) in the presence of a base and a compound represented by formula (III).

[0033]

[0034] [In formula (I),

[0035] R 1 ~R 16Each independently represents a hydrogen atom, a chlorine atom, a hydrocarbon group having 1 to 6 carbon atoms which may have a substituent, a group represented by formula (i-a), a group represented by formula (i-b), or a group represented by formula (i-c), wherein -CH2- contained in the hydrocarbon group may be substituted by -O- or -CO-. 1 ~R 16 At least one of them represents a group represented by formula (i-a), a group represented by formula (i-b), or a group represented by formula (i-c); when there are multiple groups represented by formula (i-a), they may be the same or different; when there are multiple groups represented by formula (i-b), they may be the same or different; when there are multiple groups represented by formula (i-c), they may be the same or different.]

[0036]

[0037] [In formula (i-a),

[0038] R a1 ~R a5 Each independently represents a hydrogen atom, a chlorine atom, a bromine atom, a carboxyl group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, wherein -CH2- contained in the hydrocarbon group may be substituted by -O- or -CO-. a1 ~R a5 1 to 3 of them are chlorine atoms. * indicates the bonding site. ]

[0039]

[0040] [In formula (i-b),

[0041] R b1 ~R b7 Each independently represents a hydrogen atom, a chlorine atom, a bromine atom, a carboxyl group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, wherein -CH2- contained in the hydrocarbon group may be substituted by -O- or -CO-. b1 ~R b7 1 to 3 of them are chlorine atoms.]

[0042]

[0043] [In formula (i-c),

[0044] R c1 ~R c7 Each independently represents a hydrogen atom, a chlorine atom, a bromine atom, a carboxyl group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, wherein -CH2- contained in the hydrocarbon group may be substituted by -O- or -CO-. c1 ~R c71 to 3 of them are chlorine atoms. * indicates the bonding site. ]

[0045] AIX M 3 (III)

[0046] [In formula (III),

[0047] X M Represents a halogen atom, a hydroxyl group, or OR M Base. R M It represents a hydrocarbon group having 1 to 6 carbon atoms.]

[0048]

[0049] [In formulas (II-1) to (II-4),

[0050] R 1 ~R 16 Means the same as above.]

[0051]

[12] The production method according to

[11] , wherein the amount of the compound represented by formula (III) used is 0.25 mol to 0.40 mol relative to 1 mol of the total amount of the compounds represented by formulae (II-1) to (II-4).

[0052] According to the production method of the present invention, the yield of the specific phthalocyanine compound can be improved.

[0053] Furthermore, according to the phthalocyanine compound of the present invention, a color filter can be formed in which uneven brightness is suppressed even after long-term use. DETAILED DESCRIPTION

[0054] [Compound]

[0055] Hereinafter, the present invention will be described in more detail with reference to the partial structure of the compound represented by formula (I) (hereinafter, sometimes referred to as compound (I)).

[0056]

[0057] [In formula (I),

[0058] R 1 ~R 16 Each independently represents a hydrogen atom, a chlorine atom, a hydrocarbon group having 1 to 6 carbon atoms which may have a substituent, a group represented by formula (i-a), a group represented by formula (i-b), or a group represented by formula (i-c), wherein -CH2- contained in the hydrocarbon group may be substituted by -O- or -CO-. 1 ~R 16At least one of them represents a group represented by formula (i-a), a group represented by formula (i-b), or a group represented by formula (i-c); when there are multiple groups represented by formula (i-a), they may be the same or different; when there are multiple groups represented by formula (i-b), they may be the same or different; when there are multiple groups represented by formula (i-c), they may be the same or different.]

[0059]

[0060] [In formula (i-a),

[0061] R a1 ~R a5 Each independently represents a hydrogen atom, a chlorine atom, a bromine atom, a carboxyl group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, wherein -CH2- contained in the hydrocarbon group may be substituted by -O- or -CO-. a1 ~R a5 1 to 3 of them are chlorine atoms. * indicates the bonding site. ]

[0062]

[0063] [In formula (i-b),

[0064] R b1 ~R b7 Each independently represents a hydrogen atom, a chlorine atom, a bromine atom, a carboxyl group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, wherein -CH2- contained in the hydrocarbon group may be substituted by -O- or -CO-. b1 ~R b7 1 to 3 of them are chlorine atoms. * indicates the bonding site. ]

[0065]

[0066] [In formula (i-c),

[0067] R c1 ~R c7 Each independently represents a hydrogen atom, a chlorine atom, a bromine atom, a carboxyl group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, wherein -CH2- contained in the hydrocarbon group may be substituted by -O- or -CO-. c1 ~R c7 1 to 3 of them are chlorine atoms. * indicates the bonding site. ]

[0068] R 1 ~R 16 The hydrocarbon group having 1 to 6 carbon atoms represented by may be any of an aliphatic hydrocarbon group and a phenyl group. The aliphatic hydrocarbon group may be saturated or unsaturated, and may be chain-like or cyclic (alicyclic hydrocarbon group).

[0069] Examples of the saturated chain hydrocarbon group (hereinafter sometimes referred to as an alkyl group) include straight-chain alkyl groups such as methyl, ethyl, n-propyl, n-butyl, n-pentyl, and n-hexyl; and branched-chain alkyl groups such as isopropyl, isobutyl, sec-butyl, tert-butyl, 1,3-dimethylbutyl, and 2-ethylbutyl.

[0070] The alkyl group preferably has 1 to 4 carbon atoms, more preferably 1 to 3 carbon atoms.

[0071] Examples of the unsaturated chain hydrocarbon group include alkenyl groups such as ethenyl, propenyl (e.g., 1-propenyl, 2-propenyl), and butenyl (e.g., 1-butenyl, 3-butenyl); and alkynyl groups such as ethynyl, propynyl (e.g., 1-propynyl, 2-propynyl), and butynyl (e.g., 1-butynyl, 3-butynyl); and the like.

[0072] The unsaturated chain hydrocarbon group preferably has 2 to 6 carbon atoms, more preferably 2 to 4 carbon atoms.

[0073] Examples of the saturated alicyclic hydrocarbon group include cycloalkyl groups such as cyclopropyl, 1-methylcyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.

[0074] Examples of the unsaturated alicyclic hydrocarbon group include cycloalkenyl groups such as cyclohexenyl (for example, cyclohex-1-en-1-yl, cyclohex-2-en-1-yl, and cyclohex-3-en-1-yl).

[0075] The alicyclic hydrocarbon group preferably has 3 to 6 carbon atoms.

[0076] R 1 ~R 16 The hydrocarbon group having 1 to 6 carbon atoms represented by may have a substituent. Examples of the substituent include halogen atoms such as fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms; hydroxyl groups; carboxyl groups; unsubstituted amino groups; substituted amino groups such as N-methylamino, N,N-dimethylamino, N-ethylamino, N,N-diethylamino, N-propylamino, N,N-dipropylamino, N-isopropylamino, N,N-diisopropylamino, N-phenylamino, N,N-diphenylamino, and N,N-ethylmethylamino; and cyano groups. Among these, halogen atoms are preferred, and chlorine atoms are more preferred.

[0077] R 1 ~R 16 When the hydrocarbon group represented has 2 to 6 carbon atoms and the hydrocarbon group has -CH2-, the -CH2- may be substituted with -O- or -CO-. However, in the hydrocarbon group having 1 to 6 carbon atoms, adjacent -CH2- are not substituted with -O- at the same time, and the terminal -CH2- is not substituted with -O- or -CO-.

[0078] In the present specification, when -CH2- in a hydrocarbon group is substituted with -O- or -CO-, the number of carbon atoms in the group obtained by substitution with -O- or -CO- refers to the number of carbon atoms in the hydrocarbon group before substitution with -O- or -CO-. For example, *-O-CH2-CH2-CH3 group is a group obtained by substitution of -CH2- with -O- in a hydrocarbon group having 4 carbon atoms (*-CH2-CH2-CH2-CH3).

[0079] In addition, if there are multiple substitutable -CH2- groups in a hydrocarbon group, the number of substitutions is not necessarily limited to 1. For example, in a hydrocarbon group having 4 carbon atoms (*-CH2-CH2-CH2-CH3), two -CH2- groups may be substituted with -O- to form *-O-CH2-O-CH3, or one -CH2- group may be substituted with -O- and the other -CH2- group may be substituted with -CO- to form *-O-CO-CH2-CH3 or *-CO-O-CH2-CH3. That is, groups in which two or more -CH2- groups are substituted with -O- or -CO-, such as *-O-CH2-O-CH3, *-O-CO-CH2-CH3, and *-CO-O-CH2-CH3, are also included in the "group in which -CH2- groups in a hydrocarbon group having 1 to 6 carbon atoms which may have a substituent are substituted with -O- or -CO-".

[0080] As R 1 ~R 16 The hydrocarbon group having 1 to 6 carbon atoms which may have a substituent is preferably an alkyl group.

[0081] R a1 ~R a5 , R b1 ~R b7 and R c1 ~R c7 The hydrocarbon group having 1 to 20 carbon atoms represented by may be any of an aliphatic hydrocarbon group, an aromatic hydrocarbon group, and a combination thereof. The aliphatic hydrocarbon group may be saturated or unsaturated, and may be chain-like or cyclic (alicyclic hydrocarbon group).

[0082] Examples of the saturated chain hydrocarbon group (alkyl group) include straight-chain alkyl groups such as methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl and n-decyl; and branched-chain alkyl groups such as isopropyl, isobutyl, sec-butyl, tert-butyl, 1,3-dimethylbutyl, 2-ethylbutyl and 2-ethylhexyl.

[0083] The number of carbon atoms in the alkyl group is preferably 1 to 12, more preferably 1 to 8, further preferably 1 to 4, particularly preferably 1 to 3.

[0084] Examples of the unsaturated chain hydrocarbon group include alkenyl groups such as ethenyl, propenyl (e.g., 1-propenyl, 2-propenyl), and butenyl (e.g., 1-butenyl, 3-butenyl); and alkynyl groups such as ethynyl, propynyl (e.g., 1-propynyl, 2-propynyl), and butynyl (e.g., 1-butynyl, 3-butynyl); and the like.

[0085] The unsaturated chain hydrocarbon group has preferably 2 to 10 carbon atoms, more preferably 2 to 8 carbon atoms, and further preferably 2 to 4 carbon atoms.

[0086] Examples of the saturated alicyclic hydrocarbon group include cycloalkyl groups such as cyclopropyl, 1-methylcyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and 2-methylcyclohexyl.

[0087] Examples of the unsaturated alicyclic hydrocarbon group include cyclohexenyl groups (e.g., cyclohex-1-en-1-yl, cyclohex-2-en-1-yl, cyclohex-3-en-1-yl), cycloheptenyl groups, and cyclooctenyl groups.

[0088] Examples of the alicyclic hydrocarbon group 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.

[0089] The alicyclic hydrocarbon group has preferably 3 to 10 carbon atoms, more preferably 4 to 8 carbon atoms.

[0090] Examples of the aromatic hydrocarbon group include phenyl, o-tolyl, m-tolyl, p-tolyl, 2,4-dimethylphenyl, 2,6-dimethylphenyl, 2,4,6-trimethylphenyl, 2,4-diisopropylphenyl, 2,6-diisopropylphenyl, 4-vinylphenyl, o-tert-butylphenyl, m-tert-butylphenyl, p-tert-butylphenyl, 3,5-di(tert-butyl)phenyl, 1-naphthyl, 2-naphthyl, and a group obtained by removing one hydrogen atom from tetralin.

[0091] The number of carbon atoms in the aromatic hydrocarbon group is preferably 6-18, more preferably 6-12, and even more preferably 6-10.

[0092] R a1 ~R a5 , R b1 ~R b7 and R c1 ~R c7 The hydrocarbon group represented may be a group formed by combining the above-mentioned hydrocarbon groups as long as the total number of carbon atoms is 20 or less. Examples of the group formed by combining hydrocarbon groups include aralkyl groups and alkyl groups bonded to alicyclic hydrocarbon groups.

[0093] Examples of the aralkyl group include benzyl, (2-methylphenyl)methyl, (3-methylphenyl)methyl, (4-methylphenyl)methyl, (2-ethylphenyl)methyl, (3-ethylphenyl)methyl, (4-ethylphenyl)methyl, (2-(tert-butyl)phenyl)methyl, (3-(tert-butyl)phenyl)methyl, (4-(tert-butyl)phenyl)methyl, (3,5-dimethylphenyl)methyl, 1-phenylethyl, 1-methyl-1-phenylethyl, 1,1-diphenylethyl, (1-naphthyl)methyl, (2-naphthyl)methyl, and 9-fluorenylmethyl. The aralkyl group preferably has 7 to 18 carbon atoms, more preferably 7 to 12, and even more preferably 7 to 10 carbon atoms.

[0094] Examples of the alkyl group bonded with an alicyclic hydrocarbon group include cyclopropylmethyl, cyclopropylethyl, cyclobutylmethyl, cyclohexylmethyl, cyclohexylethyl, and adamantylmethyl. The alkyl group bonded with an alicyclic hydrocarbon group preferably has 4 to 20 carbon atoms, more preferably 4 to 15, and even more preferably 4 to 10 carbon atoms.

[0095] As R a1 ~R a5 , R b1 ~R b7 and R c1 ~R c7 The substituents that the hydrocarbon group having 1 to 20 carbon atoms represented by 1 ~R 16 The substituents which the hydrocarbon group having 1 to 6 carbon atoms represented may have are the same as those exemplified above.

[0096] R a1 ~R a5 , R b1 ~R b7 and R c1 ~R c7 When the hydrocarbon group represented has 2 to 20 carbon atoms and the hydrocarbon group has -CH2-, the -CH2- may be substituted with -O- or -CO-. However, in the hydrocarbon group having 1 to 20 carbon atoms, adjacent -CH2- are not substituted with -O- at the same time, and the terminal -CH2- is not substituted with -O- or -CO-.

[0097] As R a1 ~R a5 , R b1 ~R b7 and R c1 ~R c7The hydrocarbon group having 1 to 20 carbon atoms which may have a substituent is preferably an alkyl group, an aromatic hydrocarbon group, or an aralkyl group, more preferably an alkyl group having 1 to 8 carbon atoms, an aromatic hydrocarbon group having 6 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms, and further preferably an alkyl group having 1 to 4 carbon atoms.

[0098] R a1 ~R a5 , R b1 ~R b7 and R c1 ~R c7 Each independently preferably is a hydrogen atom, a chlorine atom, a bromine atom, a carboxyl group, an alkyl group having 1 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, or an aralkyl group having 7 to 20 carbon atoms, more preferably a hydrogen atom, a chlorine atom, a bromine atom, a carboxyl group, or an alkyl group having 1 to 8 carbon atoms, further preferably a hydrogen atom, a chlorine atom, a bromine atom, a carboxyl group, or an alkyl group having 1 to 4 carbon atoms.

[0099] In the group represented by formula (i-a), R a1 ~R a5 1 to 3 of them are chlorine atoms, preferably R a1 ~R a5 1 to 2 of them are chlorine atoms.

[0100] R is particularly preferred a1 ~R a5 1 to 3 of them are chlorine atoms, 0 to 1 is a bromine atom, 0 to 1 is a carboxyl group, 0 to 3 are hydrocarbon groups having 1 to 20 carbon atoms (preferably alkyl groups having 1 to 4 carbon atoms), and the rest are hydrogen atoms, and R is more preferably a1 ~R a5 1 to 2 of them are chlorine atoms, 0 to 1 are bromine atoms, 0 to 1 are carboxyl groups, 0 to 2 are hydrocarbon groups having 1 to 20 carbon atoms (preferably alkyl groups having 1 to 4 carbon atoms), and the remainder are hydrogen atoms.

[0101] In the group represented by formula (i-b), R b1 ~R b7 1 to 3 of them are chlorine atoms, preferably R b1 ~R b7 1 to 2 of them are chlorine atoms.

[0102] R is particularly preferred b1 ~R b7 1 to 3 of them are chlorine atoms, 0 to 1 is a carboxyl group, 0 to 3 are hydrocarbon groups having 1 to 20 carbon atoms (preferably alkyl groups having 1 to 4 carbon atoms), and the rest are hydrogen atoms, and R is more preferably b1 ~R b71 to 2 of them are chlorine atoms, 0 to 1 is a carboxyl group, 0 to 2 are hydrocarbon groups having 1 to 20 carbon atoms (preferably alkyl groups having 1 to 4 carbon atoms), and the remainder are hydrogen atoms.

[0103] In the group represented by formula (i-c), R c1 ~R c7 1 to 3 of them are chlorine atoms, preferably R c1 ~R c7 1 to 2 of them are chlorine atoms.

[0104] R is particularly preferred c1 ~R c7 1 to 3 of them are chlorine atoms, 0 to 1 is a carboxyl group, 0 to 3 are hydrocarbon groups having 1 to 20 carbon atoms (preferably alkyl groups having 1 to 4 carbon atoms), and the rest are hydrogen atoms, and more preferably R c1 ~R c7 1 to 2 of them are chlorine atoms, 0 to 1 is a carboxyl group, 0 to 2 are hydrocarbon groups having 1 to 20 carbon atoms (preferably alkyl groups having 1 to 4 carbon atoms), and the remainder are hydrogen atoms.

[0105] Specific examples of the group represented by formula (i-a) include groups represented by the following formulae (i-a1) to (i-a18).

[0106]

[0107] Specific examples of the group represented by formula (i-b) include groups represented by the following formulae (i-b1) to (i-b4), and among them, the group represented by formula (i-b1) is preferred.

[0108]

[0109] Specific examples of the group represented by formula (i-c) include groups represented by the following formulae (i-c1) to (i-c5), and among these, the group represented by formula (i-c1) is preferred.

[0110]

[0111] R 1 ~R 16 Each is independently preferably a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a group represented by formula (i-a), a group represented by formula (i-b), or a group represented by formula (i-c), and more preferably a hydrogen atom, a group represented by formula (i-a), a group represented by formula (i-b), or a group represented by formula (i-c).

[0112] In compound (I), R 1 ~R 16At least one of them represents a group represented by formula (i-a), formula (i-b), or formula (i-c) (hereinafter, sometimes collectively referred to as "aryloxy group (i)"). 1 ~R 16 In the formula (i), the total number of aryloxy groups (i) is, for example, 2 to 16, preferably 4 to 16, more preferably 4 to 8, and even more preferably 4. When compound (I) has a plurality of groups represented by formula (i-a), the plurality of groups represented by formula (i-a) may be the same or different, and are preferably the same; when compound (I) has a plurality of groups represented by formula (i-b), the plurality of groups represented by formula (i-b) may be the same or different, and are preferably the same; when compound (I) has a plurality of groups represented by formula (i-c), the plurality of groups represented by formula (i-c) may be the same or different, and are preferably the same.

[0113] When compound (I) has a plurality of aryloxy groups (i), they are more preferably the same.

[0114] As the aryloxy group (i), a group represented by the formula (i-a) or the formula (i-b) is preferred.

[0115] In R 1 ~R 16 In the formula (a), the position of the aryloxy group (i) is not particularly limited.

[0116] However, the preferred method (1): R 1 ~R 4 At least one of them is an aryloxy group (i), R 5 ~R 8 At least one of them is an aryloxy group (i), R 9 ~R 12 At least one of them is an aryloxy group (i), and R 13 ~R 16 At least one of them is an aryloxy group (i),

[0117] More preferred embodiment (2): R 2 and R 3 At least one of them is an aryloxy group (i), R 6 and R 7 At least one of them is an aryloxy group (i), R 10 and R 11 At least one of them is an aryloxy group (i), and R 14 and R 15 At least one of them is an aryloxy group (i), R 1 , R 4 , R 5 , R 8 , R 9 , R 12 , R 13 and R16 is a hydrogen atom, or (3): R 1 and R 4 At least one of them is an aryloxy group (i), R 5 and R 8 At least one of them is an aryloxy group (i), R 9 and R 12 At least one of them is an aryloxy group (i), and R 13 and R 16 At least one of them is an aryloxy group (i), R 2 , R 3 , R 6 , R 7 , R 10 , R 11 , R 14 and R 15 is a hydrogen atom,

[0118] Further preferred embodiment (4): R 2 and R 3 Any one of which is an aryloxy group (i), R 6 and R 7 Any one of which is an aryloxy group (i), R 10 and R 11 Any one of is an aryloxy group (i), and R 14 and R 15 Any one of which is an aryloxy group (i), R 1 , R 4 , R 5 , R 8 , R 9 , R 12 , R 13 and R 16 is a hydrogen atom, or (5): R 1 and R 4 Any one of which is an aryloxy group (i), R 5 and R 8 Any one of which is an aryloxy group (i), R 9 and R 12 Any one of is an aryloxy group (i), and R 13 and R 16 Any one of which is an aryloxy group (i), R 2 , R 3 , R 6 , R 7 , R 10 , R 11 , R 14 and R 15 is a hydrogen atom,

[0119] Particularly preferred embodiment (6): R2 and R 3 One of them is an aryloxy group (i) and the other is a hydrogen atom, R 6 and R 7 One of them is an aryloxy group (i) and the other is a hydrogen atom, R 10 and R 11 Any one of them is an aryloxy group (i) and the other is a hydrogen atom, and R 14 and R 15 One of them is an aryloxy group (i) and the other is a hydrogen atom, R 1 , R 4 , R 5 , R 8 , R 9 , R 12 , R 13 and R 16 is a hydrogen atom, or (7): R 1 , R 5 , R 9 and R 13 is an aryloxy group (i), and R 2 ~R 4 , R 6 ~R 8 , R 10 ~R 12 and R 14 ~R 16 A hydrogen atom.

[0120] In each of the above embodiments (1) to (7), the plurality of aryloxy groups (i) contained in the compound (I) may be the same or different, but are preferably the same.

[0121] From the viewpoint of further reducing uneven brightness of the obtained color filter after long-term use, the embodiment (2) is preferred, the embodiment (4) is more preferred, and the embodiment (6) is still more preferred.

[0122] As compound (I), a compound represented by formula (IA) (hereinafter referred to as compound (IA)) and / or a compound represented by formula (IB) (hereinafter referred to as compound (IB)) is preferred. From the viewpoint of further suppressing uneven brightness of the obtained color filter after long-term use, compound (IA) is preferred.

[0123]

[0124] [In formula (IA),

[0125] R 2A and R 3A Any one of them is a group represented by formula (iA-a), formula (iA-b) or formula (iA-c) and the other is a hydrogen atom,

[0126] R 6A and R 7A Any one of them is a group represented by formula (iA-a), formula (iA-b) or formula (iA-c) and the other is a hydrogen atom,

[0127] R 10A and R 11A Any one of them is a group represented by formula (iA-a), formula (iA-b) or formula (iA-c) and the other is a hydrogen atom,

[0128] R 14A and R 15A Any one of them is a group represented by formula (iA-a), formula (iA-b) or formula (iA-c) and the other is a hydrogen atom,

[0129] R 1A , R 4A , R 5A , R 8A , R 9A , R 12A , R 13A and R 16A A hydrogen atom.

[0130] In formula (IB),

[0131] R 1B , R 5B , R 9B and R 13B are each independently a group represented by formula (iA-a), formula (iA-b), or formula (iA-c), and R 2B ~R 4B , R 6B ~R 8B , R 10B ~R 12B and R 14B ~R 16B is a hydrogen atom.]

[0132]

[0133] [In formula (iA-a),

[0134] R a1A ~R a5A Each independently represents a hydrogen atom, a chlorine atom, a bromine atom, a carboxyl group, an alkyl group having 1 to 8 carbon atoms, an aromatic hydrocarbon group having 6 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms. a1A ~R a5A 1 to 3 of them are chlorine atoms. * indicates a bonding site.

[0135] In formula (iA-b),

[0136] R b1A ~R b7A Each independently represents a hydrogen atom, a chlorine atom, a bromine atom, a carboxyl group, an alkyl group having 1 to 8 carbon atoms, an aromatic hydrocarbon group having 6 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms. b1A ~R b7A 1 to 3 of them are chlorine atoms. * indicates a bonding site.

[0137] In formula (iA-c),

[0138] R c1A ~R c7A Each independently represents a hydrogen atom, a chlorine atom, a bromine atom, a carboxyl group, an alkyl group having 1 to 8 carbon atoms, an aromatic hydrocarbon group having 6 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms. c1A ~R c7A 1 to 3 of them are chlorine atoms. * indicates the bonding site. ]

[0139] The four groups represented by the formula (iA-a), formula (iA-b) or formula (iA-c) possessed by compound (IA) may be the same or different, but are preferably the same.

[0140] The four groups represented by the formula (iA-a), formula (iA-b) or formula (iA-c) possessed by the compound (IB) may be the same or different, but are preferably the same.

[0141] In compound (IA), R 2A and R 3A , R 6A and R 7A , R 10A and R 11A , and R 14A and R 15A It is preferred that either one of them is a group represented by formula (iA-a) and the other one is a hydrogen atom, or that either one of them is a group represented by formula (iA-b) and the other one is a hydrogen atom, respectively, independently of the other.

[0142] In compound (IB), R 1B , R 5B , R 9B and R 13B Each independently is preferably a group represented by formula (iA-a) or formula (iA-b).

[0143] As R a1A ~R a5A , R b1A ~R b7A and R c1A ~R c7AThe alkyl group having 1 to 8 carbon atoms represented by R a1 ~R a5 , R b1 ~R b7 and R c1 ~R c7 The groups described by representing an alkyl group are groups having 1 to 8 carbon atoms.

[0144] As R a1A ~R a5A , R b1A ~R b7A and R c1A ~R c7A The aromatic hydrocarbon group having 6 to 12 carbon atoms represented by R is exemplified by a1 ~R a5 , R b1 ~R b7 and R c1 ~R c7 Among the groups explained by representing an aromatic hydrocarbon group, the group has 6 to 12 carbon atoms.

[0145] As R a1A ~R a5A , R b1A ~R b7A and R c1A ~R c7A The aralkyl group having 7 to 12 carbon atoms represented by R is exemplified by a1 ~R a5 , R b1 ~R b7 and R c1 ~R c7 The groups described by referring to the aralkyl group are groups having 7 to 12 carbon atoms.

[0146] R a1A ~R a5A , R b1A ~R b7A and R c1A ~R c7A Each independently is preferably a hydrogen atom, a chlorine atom, a bromine atom, a carboxyl group or an alkyl group having 1 to 8 carbon atoms, and more preferably a hydrogen atom, a chlorine atom, a bromine atom, a carboxyl group or an alkyl group having 1 to 4 carbon atoms.

[0147] In the group represented by formula (iA-a), R a1A ~R a5A 1 to 3 of them are chlorine atoms, preferably R a1A ~R a5A 1 to 2 of them are chlorine atoms.

[0148] In particular, R a1A ~Ra5A 1 to 3 of them are chlorine atoms, 0 to 1 is a bromine atom, 0 to 1 is a carboxyl group, 0 to 3 are alkyl groups having 1 to 8 (preferably 1 to 4) carbon atoms, and the rest are hydrogen atoms, and R is more preferably a1A ~R a5A 1 to 2 of them are chlorine atoms, 0 to 1 are bromine atoms, 0 to 1 are carboxyl groups, 0 to 2 are alkyl groups having 1 to 8 (preferably 1 to 4) carbon atoms, and the remainder are hydrogen atoms.

[0149] In the group represented by formula (iA-b), R b1A ~R b7A 1 to 3 of them are chlorine atoms, preferably R b1A ~R b7A 1 to 2 of them are chlorine atoms.

[0150] In particular, R b1A ~R b7A 1 to 3 of them are chlorine atoms, 0 to 1 is a carboxyl group, 0 to 3 are alkyl groups having 1 to 8 (preferably 1 to 4) carbon atoms, and the remainder are hydrogen atoms, and R is more preferably b1A ~R b7A 1 to 2 of them are chlorine atoms, 0 to 1 are carboxyl groups, 0 to 2 are alkyl groups having 1 to 8 (preferably 1 to 4) carbon atoms, and the remainder are hydrogen atoms.

[0151] In the group represented by formula (iA-c), R c1A ~R c7A 1 to 3 of them are chlorine atoms, preferably R c1A ~R c7A 1 to 2 of them are chlorine atoms.

[0152] In particular, R c1A ~R c7A 1 to 3 of them are chlorine atoms, 0 to 1 is a carboxyl group, 0 to 3 are alkyl groups having 1 to 8 (preferably 1 to 4) carbon atoms, and the rest are hydrogen atoms, and R is more preferably c1A ~R c7A 1 to 2 of them are chlorine atoms, 0 to 1 are carboxyl groups, 0 to 2 are alkyl groups having 1 to 8 (preferably 1 to 4) carbon atoms, and the remainder are hydrogen atoms.

[0153] As the group represented by formula (iA-a), specifically, there are groups represented by the above-mentioned formulas (i-a1) to (i-a18), as the group represented by formula (iA-b), specifically, there are groups represented by the above-mentioned formulas (i-b1) to (i-b4), and as the group represented by formula (iA-c), specifically, there are groups represented by the above-mentioned formulas (i-c1) to (i-c5).

[0154] Specific examples of compound (I) include compounds (Ia-1) to (Ia-136) and compounds (Ib-1) to (Ib-17) shown in Tables 1 to 5.

[0155] [Table 1]

[0156] <![CDATA[R 1 ]]> <![CDATA[R 2 ]]> <![CDATA[R 3 ]]> <![CDATA[R 4 ]]> <![CDATA[R 5 ]]> <![CDATA[R 6 ]]> <![CDATA[R 7 ]]> <![CDATA[R 8 ]]> <![CDATA[R 9 ]]> <![CDATA[R 10 ]]> <![CDATA[R 11 ]]> <![CDATA[R 12 ]]> <![CDATA[R 13 ]]> <![CDATA[R 14 ]]> <![CDATA[R 15 ]]> <![CDATA[R 16 ]]> Ia-1 H i-a1 H H H i-a1 H H H i-a1 H H H H i-a1 H Ia-2 H i-a1 H H H i-a1 H H H H i-a1 H H H i-a1 H Ia-3 H i-a1 H H H H i-a1 H H i-a1 H H H H i-a1 H Ia-4 H i-a1 H H H H i-a1 H H H i-a1 H H H i-a1 H Ia-5 H H i-a1 H H i-a1 H H H i-a1 H H H H i-a1 H Ia-6 H H i-a1 H H i-a1 H H H H i-a1 H H H i-a1 H Ia-7 H H i-a1 H H H i-a1 H H i-a1 H H H H i-a1 H Ia-8 H H i-a1 H H H i-a1 H H H i-a1 H H H i-a1 H Ia-9 H i-a2 H H H i-a2 H H H i-a2 H H H H i-a2 H Ia-10 H i-a2 H H H i-a2 H H H H i-a2 H H H i-a2 H Ia-11 H i-a2 H H H H i-a2 H H i-a2 H H H H i-a2 H Ia-12 H i-a2 H H H H i-a2 H H H i-a2 H H H i-a2 H Ia-13 H H i-a2 H H i-a2 H H H i-a2 H H H H i-a2 H Ia-14 H H i-a2 H H i-a2 H H H H i-a2 H H H i-a2 H Ia-15 H H i-a2 H H H i-a2 H H i-a2 H H H H i-a2 H Ia-16 H H i-a2 H H H i-a2 H H H i-a2 H H H i-a2 H Ia-17 H i-a3 H H H i-a3 H H H i-a3 H H H H i-a3 H Ia-18 H i-a3 H H H i-a3 H H H H i-a3 H H H i-a3 H Ia-19 H i-a3 H H H H i-a3 H H i-a3 H H H H i-a3 H Ia-20 H i-a3 H H H H i-a3 H H H i-a3 H H H i-a3 H Ia-21 H H i-a3 H H i-a3 H H H i-a3 H H H H i-a3 H Ia-22 H H i-a3 H H i-a3 H H H H i-a3 H H H i-a3 H Ia-23 H H i-a3 H H H i-a3 H H i-a3 H H H H i-a3 H Ia-24 H H i-a3 H H H i-a3 H H H i-a3 H H H i-a3 H Ia-25 H i-a4 H H H i-a4 H H H i-a4 H H H H i-a4 H Ia-26 H i-a4 H H H i-a4 H H H H i-a4 H H H i-a4 H Ia-27 H i-a4 H H H H i-a4 H H i-a4 H H H H i-a4 H Ia-28 H i-a4 H H H H i-a4 H H H i-a4 H H H i-a4 H Ia-29 H H i-a4 H H i-a4 H H H i-a4 H H H H i-a4 H Ia-30 H H i-a4 H H i-a4 H H H H i-a4 H H H i-a4 H Ia-31 H H i-a4 H H H i-a4 H H i-a4 H H H H i-a4 H Ia-32 H H i-a4 H H H i-a4 H H H i-a4 H H H i-a4 H Ia-33 H i-a5 H H H i-a5 H H H i-a5 H H H H i-a5 H Ia-34 H i-a5 H H H i-a5 H H H H i-a5 H H H i-a5 H Ia-35 H i-a5 H H H H i-a5 H H i-a5 H H H H i-a5 H Ia-36 H i-a5 H H H H i-a5 H H H i-a5 H H H i-a5 H Ia-37 H H i-a5 H H i-a5 H H H i-a5 H H H H i-a5 H Ia-38 H H i-a5 H H i-a5 H H H H i-a5 H H H i-a5 H Ia-39 H H i-a5 H H H i-a5 H H i-a5 H H H H i-a5 H Ia-40 H H i-a5 H H H i-a5 H H H i-a5 H H H i-a5 H

[0157] [Table 2]

[0158] <![CDATA[R 1 ]]> <![CDATA[R 2 ]]> <![CDATA[R 3 ]]> <![CDATA[R 4 ]]> <![CDATA[R 5 ]]> <![CDATA[R 6 ]]> <![CDATA[R 7 ]]> <![CDATA[R 8 ]]> <![CDATA[R 9 ]]> <![CDATA[R 10 ]]> <![CDATA[R 11 ]]> <![CDATA[R 12 ]]> <![CDATA[R 13 ]]> <![CDATA[R 14 ]]> <![CDATA[R 15 ]]> <![CDATA[R 16 ]]> Ia-41 H i-a6 H H H i-a6 H H H i-a6 H H H H i-a6 H Ia-42 H i-a6 H H H i-a6 H H H H i-a6 H H H i-a6 H Ia-43 H i-a6 H H H H i-a6 H H i-a6 H H H H i-a6 H Ia-44 H i-a6 H H H H i-a6 H H H i-a6 H H H i-a6 H Ia-45 H H i-a6 H H i-a6 H H H i-a6 H H H H i-a6 H Ia-46 H H i-a6 H H i-a6 H H H H i-a6 H H H i-a6 H Ia-47 H H i-a6 H H H i-a6 H H i-a6 H H H H i-a6 H Ia-48 H H i-a6 H H H i-a6 H H H i-a6 H H H i-a6 H <h2 style=";text-align:left;direction:ltr">Ia-49 H <h2 style=";text-align:left;direction:ltr"> i-a7 H H H <h2 style=";text-align:left;direction:ltr"> i-a7 H H H <h2 style=";text-align:left;direction:ltr"> i-a7 H H H H <h2 style=";text-align:left;direction:ltr"> i-a7 H <h2 style=";text-align:left;direction:ltr"> Ia-50 H <h2 style=";text-align:left;direction:ltr"> i-a7 H H H <h2 style=";text-align:left;direction:ltr"> i-a7 H H H H <h2 style=";text-align:left;direction:ltr"> i-a7 H H H <h2 style=";text-align:left;direction:ltr"> i-a7 H <h2 style=";text-align:left;direction:ltr"> Ia-51 H <h2 style=";text-align:left;direction:ltr"> i-a7 H H H H <h2 style=";text-align:left;direction:ltr"> i-a7 H H <h2 style=";text-align:left;direction:ltr"> i-a7 H H H H <h2 style=";text-align:left;direction:ltr"> i-a7 H <h2 style=";text-align:left;direction:ltr"> Ia-52 H <h2 style=";text-align:left;direction:ltr"> i-a7 H H H H <h2 style=";text-align:left;direction:ltr"> i-a7 H H H <h2 style=";text-align:left;direction:ltr"> i-a7 H H H <h2 style=";text-align:left;direction:ltr"> i-a7 H <h2 style=";text-align:left;direction:ltr"> Ia-53 H H <h2 style=";text-align:left;direction:ltr"> i-a7 H H <h2 style=";text-align:left;direction:ltr"> i-a7 H H H <h2 style=";text-align:left;direction:ltr"> i-a7 H H H H <h2 style=";text-align:left;direction:ltr"> i-a7 H <h2 style=";text-align:left;direction:ltr"> Ia-54 H H <h2 style=";text-align:left;direction:ltr"> i-a7 H H <h2 style=";text-align:left;direction:ltr"> i-a7 H H H H <h2 style=";text-align:left;direction:ltr"> i-a7 H H H <h2 style=";text-align:left;direction:ltr"> i-a7 H <h2 style=";text-align:left;direction:ltr"> Ia-55 H H <h2 style=";text-align:left;direction:ltr"> i-a7 H H H <h2 style=";text-align:left;direction:ltr"> i-a7 H H <h2 style=";text-align:left;direction:ltr"> i-a7 H H H H <h2 style=";text-align:left;direction:ltr"> i-a7 H <h2 style=";text-align:left;direction:ltr"> Ia-56 H H <h2 style=";text-align:left;direction:ltr"> i-a7 H H H <h2 style=";text-align:left;direction:ltr"> i-a7 H H H <h2 style=";text-align:left;direction:ltr"> i-a7 H H H <h2 style=";text-align:left;direction:ltr"> i-a7 H <h2 style=";text-align:left;direction:ltr"> Ia-57 H <h2 style=";text-align:left;direction:ltr"> i-a8 H H H <h2 style=";text-align:left;direction:ltr"> i-a8 H H H <h2 style=";text-align:left;direction:ltr"> i-a8 H H H H <h2 style=";text-align:left;direction:ltr"> i-a8 H <h2 style=";text-align:left;direction:ltr"> Ia-58 H <h2 style=";text-align:left;direction:ltr"> i-a8 H H H <h2 style=";text-align:left;direction:ltr"> i-a8 H H H H <h2 style=";text-align:left;direction:ltr"> i-a8 H H H <h2 style=";text-align:left;direction:ltr"> i-a8 H 1a-59 H <h2 style=";text-align:left;direction:ltr"> i-a8 H H H H <h2 style=";text-align:left;direction:ltr"> i-a8 H H <h2 style=";text-align:left;direction:ltr"> i-a8 H H H H <h2 style=";text-align:left;direction:ltr"> i-a8 H <h2 style=";text-align:left;direction:ltr"> Ia-60 H <h2 style=";text-align:left;direction:ltr"> i-a8 H H H H <h2 style=";text-align:left;direction:ltr"> i-a8 H H H <h2 style=";text-align:left;direction:ltr"> i-a8 H H H <h2 style=";text-align:left;direction:ltr"> i-a8 H <h2 style=";text-align:left;direction:ltr"> Ia-61 H H <h2 style=";text-align:left;direction:ltr"> i-a8 H H <h2 style=";text-align:left;direction:ltr"> i-a8 H H H <h2 style=";text-align:left;direction:ltr"> i-a8 H H H H <h2 style=";text-align:left;direction:ltr"> i-a8 H <h2 style=";text-align:left;direction:ltr"> Ia-62 H H <h2 style=";text-align:left;direction:ltr"> i-a8 H H <h2 style=";text-align:left;direction:ltr"> i-a8 H H H H <h2 style=";text-align:left;direction:ltr"> i-a8 H H H <h2 style=";text-align:left;direction:ltr"> i-a8 H <h2 style=";text-align:left;direction:ltr"> Ia-63 H H <h2 style=";text-align:left;direction:ltr"> i-a8 H H H <h2 style=";text-align:left;direction:ltr"> i-a8 H H <h2 style=";text-align:left;direction:ltr"> i-a8 H H H H <h2 style=";text-align:left;direction:ltr"> i-a8 H <h2 style=";text-align:left;direction:ltr"> Ia-64 H H <h2 style=";text-align:left;direction:ltr"> i-a8 H H H <h2 style=";text-align:left;direction:ltr"> i-a8 H H H <h2 style=";text-align:left;direction:ltr"> i-a8 H H H <h2 style=";text-align:left;direction:ltr"> i-a8 H <h2 style=";text-align:left;direction:ltr"> Ia-65 H <h2 style=";text-align:left;direction:ltr"> i-a9 H H H <h2 style=";text-align:left;direction:ltr"> i-a9 H H H <h2 style=";text-align:left;direction:ltr"> i-a9 H H H H <h2 style=";text-align:left;direction:ltr"> i-a9 H <h2 style=";text-align:left;direction:ltr"> Ia-66 H <h2 style=";text-align:left;direction:ltr"> i-a9 H H H <h2 style=";text-align:left;direction:ltr"> i-a9 H H H H <h2 style=";text-align:left;direction:ltr"> i-a9 H H H <h2 style=";text-align:left;direction:ltr"> i-a9 H <h2 style=";text-align:left;direction:ltr"> Ia-67 H <h2 style=";text-align:left;direction:ltr"> i-a9 H H H H <h2 style=";text-align:left;direction:ltr"> i-a9 H H <h2 style=";text-align:left;direction:ltr"> i-a9 H H H H <h2 style=";text-align:left;direction:ltr"> i-a9 H <h2 style=";text-align:left;direction:ltr"> Ia-68 H <h2 style=";text-align:left;direction:ltr"> i-a9 H H H H <h2 style=";text-align:left;direction:ltr"> i-a9 H H H <h2 style=";text-align:left;direction:ltr"> i-a9 H H H <h2 style=";text-align:left;direction:ltr"> i-a9 H <h2 style=";text-align:left;direction:ltr"> Ia-69 H H <h2 style=";text-align:left;direction:ltr"> i-a9 H H <h2 style=";text-align:left;direction:ltr"> i-a9 H H H <h2 style=";text-align:left;direction:ltr"> i-a9 H H H H <h2 style=";text-align:left;direction:ltr"> i-a9 H <h2 style=";text-align:left;direction:ltr"> Ia-70 H H <h2 style=";text-align:left;direction:ltr"> i-a9 H H <h2 style=";text-align:left;direction:ltr"> i-a9 H H H H <h2 style=";text-align:left;direction:ltr"> i-a9 H H H <h2 style=";text-align:left;direction:ltr"> i-a9 H <h2 style=";text-align:left;direction:ltr"> Ia-71 H H <h2 style=";text-align:left;direction:ltr"> i-a9 H H H <h2 style=";text-align:left;direction:ltr"> i-a9 H H <h2 style=";text-align:left;direction:ltr"> i-a9 H H H H <h2 style=";text-align:left;direction:ltr"> i-a9 H <h2 style=";text-align:left;direction:ltr"> Ia-72 H H <h2 style=";text-align:left;direction:ltr"> i-a9 H H H <h2 style=";text-align:left;direction:ltr"> i-a9 H H H <h2 style=";text-align:left;direction:ltr"> i-a9 H H H <h2 style=";text-align:left;direction:ltr"> i-a9 H <h2 style=";text-align:left;direction:ltr"> Ia-73 H <h2 style=";text-align:left;direction:ltr"> i-a10 H H H <h2 style=";text-align:left;direction:ltr"> i-a10 H H H <h2 style=";text-align:left;direction:ltr"> i-a10 H H H H <h2 style=";text-align:left;direction:ltr"> i-a10 H <h2 style=";text-align:left;direction:ltr"> Ia-74 H <h2 style=";text-align:left;direction:ltr"> i-a10 H H H <h2 style=";text-align:left;direction:ltr"> i-a10 H H H H <h2 style=";text-align:left;direction:ltr"> i-a10 H H H <h2 style=";text-align:left;direction:ltr"> i-a10 H <h2 style=";text-align:left;direction:ltr"> Ia-75 H <h2 style=";text-align:left;direction:ltr"> i-a10 H H H H <h2 style=";text-align:left;direction:ltr"> i-a10 H H <h2 style=";text-align:left;direction:ltr"> i-a10 H H H H <h2 style=";text-align:left;direction:ltr"> i-a10 H <h2 style=";text-align:left;direction:ltr"> Ia-76 H <h2 style=";text-align:left;direction:ltr"> i-a10 H H H H <h2 style=";text-align:left;direction:ltr"> i-a10 H H H <h2 style=";text-align:left;direction:ltr"> i-a10 H H H <h2 style=";text-align:left;direction:ltr"> i-a10 H <h2 style=";text-align:left;direction:ltr"> Ia-77 H H <h2 style=";text-align:left;direction:ltr"> i-a10 H H <h2 style=";text-align:left;direction:ltr"> i-a10 H H H <h2 style=";text-align:left;direction:ltr"> i-a10 H H H H <h2 style=";text-align:left;direction:ltr"> i-a10 H <h2 style=";text-align:left;direction:ltr"> Ia-78 H H <h2 style=";text-align:left;direction:ltr"> i-a10 H H <h2 style=";text-align:left;direction:ltr"> i-a10 H H H H <h2 style=";text-align:left;direction:ltr"> i-a10 H H H <h2 style=";text-align:left;direction:ltr"> i-a10 H <h2 style=";text-align:left;direction:ltr"> Ia-79 H H <h2 style=";text-align:left;direction:ltr"> i-a10 H H H <h2 style=";text-align:left;direction:ltr"> i-a10 H H <h2 style=";text-align:left;direction:ltr"> i-a10 H H H H <h2 style=";text-align:left;direction:ltr"> i-a10 H <h2 style=";text-align:left;direction:ltr"> Ia-80 H H <h2 style=";text-align:left;direction:ltr"> i-a10 H H H <h2 style=";text-align:left;direction:ltr"> i-a10 H H H <h2 style=";text-align:left;direction:ltr"> i-a10 H H H <h2 style=";text-align:left;direction:ltr"> i-a10 H

[0159] [Table 3]

[0160] <![CDATA[R 1 ]]> <![CDATA[R 2 ]]> <![CDATA[R 3 ]]> <![CDATA[R 4 ]]> <![CDATA[R 5 ]]> <![CDATA[R 6 ]]> <![CDATA[R 7 ]]> <![CDATA[R 8 ]]> <![CDATA[R 9 ]]> <![CDATA[R 10 ]]> <![CDATA[R 11 ]]> <![CDATA[R 12 ]]> <![CDATA[R 13 ]]> <![CDATA[R 14 ]]> <![CDATA[R 15 ]]> <![CDATA[R 16 ]]> <h2 style=";text-align:left;direction:ltr"> Ia-81 H <h2 style=";text-align:left;direction:ltr"> i-a11 H H H <h2 style=";text-align:left;direction:ltr"> i-a11 H H H <h2 style=";text-align:left;direction:ltr"> i-a11 H H H H <h2 style=";text-align:left;direction:ltr"> i-a11 H <h2 style=";text-align:left;direction:ltr"> Ia-82 H <h2 style=";text-align:left;direction:ltr"> i-a11 H H H <h2 style=";text-align:left;direction:ltr"> i-a11 H H H H <h2 style=";text-align:left;direction:ltr"> i-a11 H H H <h2 style=";text-align:left;direction:ltr"> i-a11 H <h2 style=";text-align:left;direction:ltr"> Ia-83 H <h2 style=";text-align:left;direction:ltr"> i-a11 H H H H <h2 style=";text-align:left;direction:ltr"> i-a11 H H <h2 style=";text-align:left;direction:ltr"> i-a11 H H H H <h2 style=";text-align:left;direction:ltr"> i-a11 H <h2 style=";text-align:left;direction:ltr"> Ia-84 H <h2 style=";text-align:left;direction:ltr"> i-a11 H H H H <h2 style=";text-align:left;direction:ltr"> i-a11 H H H <h2 style=";text-align:left;direction:ltr"> i-a11 H H H <h2 style=";text-align:left;direction:ltr"> i-a11 H <h2 style=";text-align:left;direction:ltr"> Ia-85 H H <h2 style=";text-align:left;direction:ltr"> i-a11 H H <h2 style=";text-align:left;direction:ltr"> i-a11 H H H <h2 style=";text-align:left;direction:ltr"> i-a11 H H H H <h2 style=";text-align:left;direction:ltr"> i-a11 H <h2 style=";text-align:left;direction:ltr"> Ia-86 H H <h2 style=";text-align:left;direction:ltr"> i-a11 H H <h2 style=";text-align:left;direction:ltr"> i-a11 H H H H <h2 style=";text-align:left;direction:ltr"> i-a11 H H H <h2 style=";text-align:left;direction:ltr"> i-a11 H <h2 style=";text-align:left;direction:ltr"> Ia-87 H H <h2 style=";text-align:left;direction:ltr"> i-a11 H H H <h2 style=";text-align:left;direction:ltr"> i-a11 H H <h2 style=";text-align:left;direction:ltr"> i-a11 H H H H <h2 style=";text-align:left;direction:ltr"> i-a11 H <h2 style=";text-align:left;direction:ltr"> Ia-88 H H <h2 style=";text-align:left;direction:ltr"> i-a11 H H H <h2 style=";text-align:left;direction:ltr"> i-a11 H H H <h2 style=";text-align:left;direction:ltr"> i-a11 H H H <h2 style=";text-align:left;direction:ltr"> i-a11 H <h2 style=";text-align:left;direction:ltr"> Ia-89 H <h2 style=";text-align:left;direction:ltr"> i-a12 H H H <h2 style=";text-align:left;direction:ltr"> i-a12 H H H <h2 style=";text-align:left;direction:ltr"> i-a12 H H H H <h2 style=";text-align:left;direction:ltr"> i-a12 H <h2 style=";text-align:left;direction:ltr"> Ia-90 H <h2 style=";text-align:left;direction:ltr"> i-a12 H H H <h2 style=";text-align:left;direction:ltr"> i-a12 H H H H <h2 style=";text-align:left;direction:ltr"> i-a12 H H H <h2 style=";text-align:left;direction:ltr"> i-a12 H <h2 style=";text-align:left;direction:ltr"> Ia-91 H <h2 style=";text-align:left;direction:ltr"> i-a12 H H H H <h2 style=";text-align:left;direction:ltr"> i-a12 H H <h2 style=";text-align:left;direction:ltr"> i-a12 H H H H <h2 style=";text-align:left;direction:ltr"> i-a12 H <h2 style=";text-align:left;direction:ltr"> Ia-92 H <h2 style=";text-align:left;direction:ltr"> i-a12 H H H H <h2 style=";text-align:left;direction:ltr"> u-a12 H H H <h2 style=";text-align:left;direction:ltr"> i-a12 H H H <h2 style=";text-align:left;direction:ltr"> i-a12 H I-93 H H i-a12 H H i-a12 H H H i-a12 H H H H i-a12 H I-94 H H i-a12 H H i-a12 H H H H i-a12 H H H i-a12 H I-95 H H i-a12 H H H i-a12 H H i-a12 H H H H i-a12 H I-96 H H i-a12 H H H u-a12 H H H i-a12 H H H i-a12 H I-97 H i-b1 H H H i-b1 H H H i-b1 H H H H i-b1 H I-98 H i-b1 H H H i-b1 H H H H i-b1 H H H i-b1 H I-99 H i-b1 H H H H i-b1 H H i-b1 H H H H i-b1 H It's 100 H i-b1 H H H H i-b1 H H H i-b1 H H H i-b1 H It-101 H H i-b1 H H i-b1 H H H i-b1 H H H H i-b1 H I-102 H H i-b1 H H 1-b1 H H H H i-b1 H H H i-b1 H I-103 H H i-b1 H H H i-b1 H H i-b1 H H H H i-b1 H I-104 H H i-b1 H H H i-b1 H H H i-b1 H H H i-b1 H I-105 H i-c1 H H H i-c1 H H H i-c1 H H H H i-c1 H I-106 H i-c1 H H H i-c1 H H H H i-c1 H H H i-c1 H I-107 H i-c1 H H H H i-c1 H H i-c1 H H H H i-c1 H I-108 H i-c1 H H H H i-c1 H H H i-c1 H H H i-c1 H I-109 H H i-c1 H H u-c1 H H H i-c1 H H H H l-c1 H I-110 H H i-c1 H H i-c1 H H H H i-c1 H H H i-c1 H I-111 H H i-c1 H H H i-c1 H H i-c1 H H H H i-c1 H I-112 H H i-c1 H H H i-c1 H H H i-c1 H H H i-c1 H

[0161] [Table 4]

[0162] <![CDATA[R 1 ]]> <![CDATA[R 2 ]]> <![CDATA[R 3 ]]> <![CDATA[R 4 ]]> <![CDATA[R 5 ]]> <![CDATA[R 6 ]]> <![CDATA[R 7 ]]> <![CDATA[R 8 ]]> <![CDATA[R 9 ]]> <![CDATA[R 10 ]]> <![CDATA[R 11 ]]> <![CDATA[R 12 ]]> <![CDATA[R 13 ]]> <![CDATA[R 14 ]]> <![CDATA[R 15 ]]> <![CDATA[R 16 ]]> I-113 H i-a16 H H H i-a16 H H H i-a16 H H H H i-a16 H I-114 H i-a16 H H H i-a16 H H H H i-a16 H H H i-a16 H I-115 H i-a16 H H H H i-a16 H H i-a16 H H H H i-a16 H I-116 H i-a16 H H H H i-a16 H H H i-a16 H H H i-a16 H I-117 H H i-a16 H H i-a16 H H H i-a16 H H H H i-a16 H I-118 H H i-a16 H H i-a16 H H H H i-a16 H H H i-a16 H I-119 H H i-a16 H H H i-a16 H H i-a16 H H H H i-a16 H I-120 H H i-a16 H H H i-a16 H H H i-a16 H H H i-a16 H I-121 H i-a17 H H H i-a17 H H H i-a17 H H H H i-a17 H I-122 H i-a17 H H H i-a17 H H H H i-a17 H H H i-a17 H I-123 H i-a17 H H H H i-a17 H H i-a17 H H H H i-a17 H I-124 H i-a17 H H H H i-a17 H H H i-a17 H H H i-a17 H I-125 H H i-a17 H H i-a17 H H H i-a17 H H H H i-a17 H I-126 H H i-a17 H H i-a17 H H H H i-a17 H H H i-a17 H I-127 H H i-a17 H H H i-a17 H H i-a17 H H H H i-a17 H I-128 H H i-a17 H H H i-a17 H H H i-a17 H H H i-a17 H I-129 H i-a18 H H H i-a18 H H H i-a18 H H H H i-a18 H I-130 H i-a18 H H H i-a18 H H H H i-a18 H H H i-a18 H Ia-131 H i-a18 H H H H i-a18 H H i-a18 H H H H i-a18 H Ia-132 H i-a18 H H H H i-a18 H H H i-a18 H H H i-a18 H I-133 H H i-a18 H H i-a18 H H H i-a18 H H H H i-a18 H I-134 H H i-a18 H H i-a18 H H H H i-a18 H H H i-a18 H Ia-135 H H i-a18 H H H i-a18 H H i-a18 H H H H i-a18 H Ia-136 H H i-a18 H H H i-a18 H H H i-a18 H H H i-a18 H

[0163] [Table 5]

[0164] <![CDATA[R 1 ]]> <![CDATA[R 2 ]]> <![CDATA[R 3 ]]> <![CDATA[R 4 ]]> <![CDATA[R 5 ]]> <![CDATA[R 6 ]]> <![CDATA[R 7 ]]> <![CDATA[R 8 ]]> <![CDATA[R 9 ]]> <![CDATA[R 10 ]]> <![CDATA[R 11 ]]> <![CDATA[R 12 ]]> <![CDATA[R 13 ]]> <![CDATA[R 14 ]]> <![CDATA[R 15 ]]> <![CDATA[R 16 ]]> Ib-1 i-a1 H H H i-a1 H H H i-a1 H H H i-a1 H H H Ib-2 i-a2 H H H i-a2 H H H i-a2 H H H i-a2 H H H Ib-3 i-a3 H H H i-a3 H H H i-a3 H H H i-a3 H H H Ib-4 i-a4 H H H i-a4 H H H i-a4 H H H i-a4 H H H Ib-5 i-a5 H H H i-a5 H H H i-a5 H H H i-a5 H H H Ib-6 i-a6 H H H i-a6 H H H i-a6 H H H i-a6 H H H Ib-7 i-a7 H H H i-a7 H H H i-a7 H H H i-a7 H H H Ib-8 i-a8 H H H i-a8 H H H i-a8 H H H i-a8 H H H Ib-9 i-a9 H H H i-a9 H H H i-a9 H H H i-a9 H H H Ib-10 i-a10 H H H i-a10 H H H i-a10 H H H i-a10 H H H Ib-11 i-a11 H H H i-a11 H H H i-a11 H H H i-a11 H H H Ib-12 i-a12 H H H i-a12 H H H i-a12 H H H i-a12 H H H Ib-13 i-b1 H H H i-b1 H H H i-b1 H H H i-b1 H H H Ib-14 i-c1 H H H i-c1 H H H i-c1 H H H i-c1 H H H Ib-15 i-a16 H H H i-a16 H H H i-a16 H H H i-a16 H H H Ib-16 i-a17 H H H i-a17 H H H i-a17 H H H i-a17 H H H Ib-17 i-a18 H H H i-a18 H H H i-a18 H H H i-a18 H H H

[0165] In Tables 1 to 5, i-a1 to i-a12, i-a16 to i-a18, i-b1 and i-c1 represent the groups represented by the above-mentioned formulas (i-a1) to (i-a12), the groups represented by formulas (i-a16) to (i-a18), the groups represented by formula (i-b1) and the groups represented by formula (i-c1), and H represents a hydrogen atom.

[0166] [Method for producing compound (I)]

[0167] As a method for producing compound (I), it is preferred to react compounds represented by formulae (II-1) to (II-4) in the presence of a base and a compound represented by formula (III). Hereinafter, such a production method may be referred to as the production method of the present invention.

[0168] AIX M 3 (III)

[0169] [In formula (III),

[0170] X M Represents a halogen atom, a hydroxyl group, or OR M Base. R M It represents a hydrocarbon group having 1 to 6 carbon atoms.]

[0171]

[0172] [In formulas (II-1) to (II-4),

[0173] R 1~R 16 Means the same as above.]

[0174] The present inventors studied the method of reacting compounds represented by formula (II-1) to (II-4) (hereinafter sometimes collectively referred to as phthalonitrile compound (II)) in the presence of a base when producing compound (I), but found that the yield of compound (I) decreased in this method. In particular, when the above-mentioned aryloxy group (i) is present, there is a tendency for the yield to decrease. Next, the present inventors found that by reacting phthalonitrile compound (II) in the presence of a base and a compound represented by formula (III) (hereinafter sometimes referred to as an aluminum compound (III)), the yield of compound (I) as the target compound can be increased even when the compound has an aryloxy group (i).

[0175] It should be noted that, generally, when a phthalonitrile compound is reacted in the presence of an aluminum compound (III), aluminum phthalocyanine whose central metal is an aluminum atom is preferentially obtained. However, when a phthalonitrile compound (II) having the above-mentioned aryloxy group (i) is reacted, it is unexpectedly found that a compound (I) which is a phthalocyanine without a metal body is preferentially generated compared to an aluminum phthalocyanine represented by the following formula (IV) (hereinafter, sometimes referred to as aluminum phthalocyanine (IV)), that is, the selectivity of the compound (I) as the target compound is good. Therefore, by adopting the production method of the present invention, the yield of the compound (I) as the target compound can be increased. In addition, by adopting the production method of the present invention, the compound (I) can be produced in a short time and with good reproducibility, which is also preferred in this respect.

[0176]

[0177] [In formula (IV),

[0178] R 1 ~R 16 and X M Means the same as above.]

[0179] Hereinafter, the production method of the present invention will be described in detail.

[0180] In formula (III), as X M Examples of the halogen atom represented by include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom and the like, and among them, a chlorine atom is preferred.

[0181] As R M The hydrocarbon group having 1 to 6 carbon atoms represented by R includes 1 ~R 16 The same groups as those explained above with reference to the hydrocarbon group having 1 to 6 carbon atoms are also preferred.

[0182] As ORM The group specifically includes alkoxy groups having 1 to 6 carbon atoms such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, tert-butoxy, and phenoxy groups. Among them, alkoxy groups having 1 to 6 carbon atoms are preferred, and alkoxy groups having 1 to 4 carbon atoms are more preferred.

[0183] In formula (III), X M , preferably a halogen atom, a hydroxyl group, or an alkoxy group having 1 to 4 carbon atoms, more preferably a chlorine atom or a hydroxyl group, and particularly preferably a chlorine atom.

[0184] In the phthalonitrile compound (II), R 1 ~R 16 represents the same as R in compound (I) 1 ~R 16 The same meanings apply to the preferred embodiments thereof. The four compounds represented by formulae (II-1) to (II-4) may be the same or different, but are preferably the same compounds.

[0185] The amount of the aluminum compound (III) used is preferably 0.25 to 0.40 moles, more preferably 0.25 to 0.34 moles, relative to 1 mole of the total amount of the phthalonitrile compound (II). By adjusting the amount of the aluminum compound (III) relative to the phthalonitrile compound (II) to a predetermined value or more, the yield of the compound (I) can be further increased, and the reaction time can be further shortened. In addition, by adjusting the amount of the aluminum compound (III) relative to the phthalonitrile compound (II) to a predetermined value or less, it is easy to preferentially generate the compound (I) relative to the aluminum phthalocyanine (IV), that is, the selectivity of the compound (I) is further improved.

[0186] As the base, an inorganic base and / or an organic base can be used.

[0187] Examples of the inorganic base include alkali metal carbonates such as sodium carbonate and potassium carbonate; alkali metal phosphates such as trisodium phosphate and tripotassium phosphate; and alkali metal hydroxides such as sodium hydroxide, potassium hydroxide and lithium hydroxide.

[0188] Examples of the organic base include trialkylamines such as triethylamine and N,N-diisopropylethylamine; and nitrogen-containing heterocyclic compounds such as pyridine, picoline, 1,8-diazabicyclo[5.4.0]-7-undecene (DBU) and 1,5-diazabicyclo[4.3.0]non-5-ene (DBN).

[0189] Among them, an organic base is preferred, a nitrogen-containing heterocyclic compound is more preferred, and 1,8-diazabicyclo[5.4.0]-7-undecene is further preferred.

[0190] The amount of the base used is preferably 0.8 to 5.0 mol, more preferably 0.9 to 2.0 mol, and even more preferably 1.0 to 1.5 mol, based on 1 mol of the total amount of the phthalonitrile compounds (II).

[0191] The reaction of the phthalonitrile compound (II) may be carried out in the presence of a solvent or in the absence of a solvent. However, it is preferably carried out in the presence of a solvent from the viewpoint of improving the reaction efficiency.

[0192] As the above-mentioned solvent, an organic solvent is preferred, and examples thereof include:

[0193] Ester solvents such as methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutyrate, ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, isoamyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexanol acetate and γ-butyrolactone;

[0194] 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-dimethoxybutanol Ether solvents such as alkane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenethyl ether and methyl anisole;

[0195] Alcohol solvents such as methanol, ethanol, propanol, butanol, heptanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, diethylene glycol, triethylene glycol and glycerol, etc.

[0196] Among them, from the viewpoint of further improving the reaction efficiency, the above-mentioned solvent is preferably an alcohol solvent, more preferably a polyol solvent such as ethylene glycol, propylene glycol, diethylene glycol, triethylene glycol, glycerol, etc., and particularly preferably a polyol solvent having a boiling point of 160°C or above (preferably 200°C or above).

[0197] The amount of the solvent used is not particularly limited, and is, for example, 1 to 100 parts by mass, or preferably 3 to 50 parts by mass, relative to 1 part by mass of the total amount of the phthalonitrile compound (II).

[0198] The reaction temperature is, for example, 50 to 200°C, preferably 90 to 160°C or 120 to 160°C.

[0199] In the production method of the present invention, since the reaction is carried out in the presence of an aluminum compound (III), the yield of compound (I) can be increased even if the reaction time is short. From the viewpoint of productivity, the reaction time is preferably 30 minutes to 50 hours, more preferably 1 to 40 hours, further preferably 3 to 35 hours, and may be 20 hours or less or 15 hours or less.

[0200] The reaction mixture obtained by the above reaction contains the target compound (I). It should be noted that in the production method of the present invention in which the reaction is carried out in the presence of an aluminum compound (III), the above-mentioned aluminum phthalocyanine (IV) is sometimes generated as a by-product, but since the synthesis is performed using a phthalonitrile compound (II) having at least one aryloxy group (i), the compound (I) is preferentially synthesized over the aluminum phthalocyanine (IV).

[0201] Therefore, in the production method of the present invention, the amount of compound (I) obtained is preferably 2.5 mol or more, more preferably 3.5 mol or more, further preferably 4.5 mol or more, and further preferably 5.0 mol or more, based on 1 mol of aluminum phthalocyanine (IV).

[0202] The amount of compound (I) relative to aluminum phthalocyanine (IV) can be calculated by isolating compound (I) and aluminum phthalocyanine (IV) from the reaction mixture and measuring the yields.

[0203] The method for separating compound (I) and aluminum phthalocyanine (IV) from the reaction mixture is not particularly limited, and various known methods can be used. For example, the reaction mixture can be cooled to room temperature (e.g., 18 to 24° C.), and water and ethyl acetate can be added as needed to precipitate compound (I). At this time, when aluminum phthalocyanine (IV) is contained in the reaction mixture, aluminum phthalocyanine (IV) is also precipitated together with compound (I). Then, the precipitate is washed with water, acetone, methanol, etc. as needed, and purified, for example, by column chromatography, thereby separating compound (I) and aluminum phthalocyanine (IV).

[0204] In the above-mentioned column chromatography, silica gel column chromatography is preferably used. As the mobile phase (developing solvent) used in the column chromatography, there is no particular limitation, as long as it is appropriately selected according to the compound to be separated, preferably aromatic hydrocarbon solvents and ether solvents are used, and more preferably a gradient method in which aromatic hydrocarbon solvents: ether solvents (mass ratio) are varied from 100:0 to 0:100 for extraction.

[0205] Examples of the aromatic hydrocarbon solvent include benzene, toluene, xylene, and mesitylene. Among them, toluene is preferred.

[0206] Examples of the ether solvent include those described above as the solvent used in the reaction of the phthalonitrile compound (II), and among them, tetrahydrofuran is preferred.

[0207] By adopting the production method of the present invention, the yield of compound (I) obtained from phthalonitrile compound (II) can be increased. The yield of compound (I) in the reaction of synthesizing compound (I) from phthalonitrile compound (II) is preferably 5% or more, more preferably 15% or more, further preferably 20% or more, and may also be 35% or more or 40% or more.

[0208] [Colored resin composition]

[0209] The present invention includes a colored resin composition containing the above-mentioned compound (I) and a resin (hereinafter, sometimes referred to as resin (B)).

[0210] The colored resin composition of the present invention preferably contains the above-mentioned compound (I) as a colorant (hereinafter, sometimes referred to as a colorant (A)).

[0211] The colored resin composition of the present invention preferably further contains at least one (preferably both) of a polymerizable compound (hereinafter, sometimes referred to as a polymerizable compound (C)) and a polymerization initiator (hereinafter, sometimes referred to as a polymerization initiator (D)).

[0212] It is preferred that the colored resin composition of the present invention further contains a solvent (hereinafter, sometimes referred to as a solvent (E)).

[0213] The colored resin composition of the present invention may contain a leveling agent (hereinafter, sometimes referred to as a leveling agent (F)).

[0214] In the present specification, the compounds exemplified as the components may be used alone or in combination of two or more unless otherwise specified.

[0215] <Colorant (A)>

[0216] The colorant (A) contains the compound (I). The color filter formed from the colored resin composition containing the compound (I) as a colorant can reduce the brightness difference between the peripheral portion and the central portion even after long-term use, that is, can form a color filter with suppressed brightness unevenness.

[0217] The content of the compound (I) is, for example, 20 to 100% by mass, preferably 30 to 100% by mass, more preferably 40 to 90% by mass, and still more preferably 50 to 80% by mass in the total amount of the colorant (A). When the content of the compound (I) in the colorant (A) is within the above range, it is easier to obtain a desired spectrum and it is easier to suppress uneven brightness after long-term use.

[0218] The colorant (A) may further contain a colorant different from the compound (I) (hereinafter sometimes referred to as a colorant (A1)). The colorant (A1) may be any of a dye and a pigment, but is preferably a pigment from the viewpoint of further suppressing uneven brightness after long-term use.

[0219] Examples of the dye include compounds classified as substances 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 Guide (published by the Color Dyeing Co., Ltd.).

[0220] Examples of the dye include azo dyes, cyanine dyes, triphenylmethane dyes, xanthene dyes, thiazole dyes, Azomethine dyes, quinophthalone dyes, anthraquinone dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, azomethine dyes, square acid Dyes, acridine dyes, styryl dyes, coumarin dyes, quinoline dyes, nitro dyes and phthalocyanine dyes, etc. Among them, organic solvent-soluble dyes are preferred.

[0221] Specific examples of the dye include CI Solvent Yellow 4 (hereinafter, CI Solvent Yellow is omitted and only the number is described. The same applies to others), 14, 15, 23, 24, 25, 38, 62, 63, 68, 79, 81, 82, 83, 89, 94, 98, 99, 117, 162, 163, 167, and 189;

[0222] CI Solvent Red 24, 45, 49, 90, 91, 111, 118, 119, 122, 124, 125, 127, 130, 132, 143, 145, 146, 150, 151, 155, 160, 168, 169, 172, 175, 181, 207, 218, 222, 227, 230, 245, 247;

[0223] CI Solvent Orange 2, 7, 11, 15, 26, 41, 54, 56, 77, 86, 99;

[0224] CI Solvent Violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60;

[0225] CI Solvent Blue 4, 5, 14, 18, 35, 36, 37, 38, 44, 45, 58, 59, 59: 1, 63, 67, 68, 69, 70, 78, 79, 83, 90, 94, 97, 98, 100, 101, 102, 104, 105, 111, 112, 122, 128, 132, 136, 139;

[0226] CI solvent green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35; etc. CI solvent dyes,

[0227] 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, 156 7, 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;

[0228] 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, 182 , 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;

[0229] CI Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 149, 162, 169, 173;

[0230] CI Acid Violet 6B, 7, 9, 15, 16, 17, 19, 21, 23, 24, 25, 30, 34, 38, 49, 72, 102;

[0231] CI Acid Blue 1, 3, 5, 7, 9, 11, 13, 15, 17, 18, 22, 23, 24, 25, 26, 27, 29, 34, 38, 40, 41, 42, 43, 45, 48, 51, 54, 59, 60, 62, 70, 72, 74, 75, 78, 80, 82, 83, 86, 87, 88, 90, 90:1, 91, 92, 93, 93:1, 96, 99, 100, 102, 103, 104, 108, 109, 110, 112, 113, 117, 119, 120, 123, 1 26, 127, 129, 130, 131, 138, 140, 142, 143, 147, 150, 151, 154, 158, 161, 166, 167, 168, 170, 171, 175, 182, 183, 184, 187, 192, 199, 203, 204, 205, 210, 213, 229, 234, 236, 242, 243, 249, 256, 259, 267, 269, 278, 280, 285, 290, 296, 315, 324:1, 335, 340;

[0232] CI acid green 1, 3, 5, 6, 7, 8, 9, 11, 13, 14, 15, 16, 22, 25, 27, 28, 41, 50, 50:1, 58, 63, 65, 80, 104, 105, 106, 109; etc. CI acid dyes,

[0233] CI Direct Yellow 2, 4, 28, 33, 34, 35, 38, 39, 43, 44, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129, 132, 136, 138, 141;

[0234] 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;

[0235] CI Direct Orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107;

[0236] CI Direct Violet 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104;

[0237] CI Direct Blue 1, 2, 3, 6, 8, 15, 22, 25, 28, 29, 40, 41, 42, 47, 52, 55, 57, 71, 76, 77, 78, 80, 81, 84, 85, 86, 87, 90, 93, 94, 95, 97, 98, 99, 100, 101, 106, 107, 108, 109, 113, 114, 115, 117, 119, 120, 137, 149, 150, 153, 155, 156, 158, 159, 160, 161, 162, 163, 164, 165, 166, 1 67, 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;

[0238] CI direct green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 79, 82; etc. CI direct dyes,

[0239] CI Disperse Yellow 51, 54, 76;

[0240] CI Disperse Violet 26, 27;

[0241] CI disperse blue 1, 14, 56, 60; etc. CI disperse dyes,

[0242] CI Basic Red 1, 9, 10;

[0243] 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;

[0244] CI Basic Violet 2;

[0245] CI basic green 1; etc. CI basic dyes,

[0246] CI Reactive Yellow 2, 76, 116;

[0247] CI Reactive Orange 16;

[0248] CI Reactive Red 36; etc. CI Reactive Dyes,

[0249] CI Medium Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65;

[0250] CI Medium 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;

[0251] CI Medium Orange 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47, 48;

[0252] CI medium 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;

[0253] CI Medium 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;

[0254] CI mordant green 1, 3, 4, 5, 10, 13, 15, 19, 21, 23, 26, 29, 31, 33, 34, 35, 41, 43, 53; etc. CI mordant dyes,

[0255] CI vat green 1; etc. CI vat dyes, etc.

[0256] These dyes may be used alone or in combination of two or more dyes for each color.

[0257] Examples of the pigment include pigments classified as pigments in the Color Index (published by The Society of Dyers and Colourists).

[0258] Examples of pigments classified as pigments include yellow pigments such as CI Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 129, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 185, 194, 214, and 231;

[0259] CI Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73 and other orange pigments;

[0260] CI Pigment Red 9, 97, 105, 122, 144, 166, 168, 176, 177, 180, 190, 192, 209, 215, 216, 224, 242, 246, 254, 255, 264, 265, 266, 268, 269, 273, 291 and other red pigments;

[0261] CI Pigment Blue 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 60 and other blue pigments;

[0262] CI Pigment Violet 1, 19, 23, 32, 36, 38 and other purple pigments;

[0263] CI Pigment Green 7, 36, 58, 59, 62, 63 and other green pigments;

[0264] CI Pigment Brown 23, 25 and other brown pigments;

[0265] Black pigments such as CI Pigment Black 1, 7, etc.

[0266] These pigments may be used alone or in combination for each color.

[0267] The pigment may be subjected to rosin treatment, surface treatment using a pigment derivative into which an acidic group or a basic group is introduced, grafting treatment on the pigment surface using a polymer compound, micronization treatment using a sulfuric acid micronization method, or washing treatment using an organic solvent, water, or the like for removing impurities, or removal treatment of ionic impurities using an ion exchange method, etc. The particle size of the pigment is preferably substantially uniform.

[0268] The colorant (A1) may be appropriately selected and used according to the desired spectrum. For example, in the case of a green filter in a color filter, the colorant (A1) is preferably a yellow pigment, more preferably at least one selected from CI Pigment Yellow 138, 150 and 185, and further preferably CI Pigment Yellow 138 and / or 185. From the viewpoint of obtaining a green filter that easily exhibits good spectral characteristics even after long-term use, the yellow pigment is preferably CI Pigment Yellow 138.

[0269] When a yellow pigment is used as the colorant (A1), the content of the yellow pigment relative to 100 parts by mass of the compound (I) is, for example, 1 to 200 parts by mass, preferably 5 to 150 parts by mass, more preferably 10 to 100 parts by mass, and further preferably 20 to 80 parts by mass. If the content of the yellow pigment is within the above range, it is easier to obtain the desired spectrum.

[0270] The content of the colorant (A) in the colored resin composition is, for example, 0.5 to 80% by mass, preferably 2 to 70% by mass, more preferably 8 to 55% by mass, and further preferably 25 to 50% by mass relative to the total amount of the solid content. When the content of the colorant (A) is within the above range, it is easier to obtain a desired spectrum and color density.

[0271] It should be noted that the "total amount of solid content" in this specification refers to the total amount of components obtained by removing the solvent from the colored resin composition of the present invention. The total amount of solid content and the content of each component relative to the total amount can be measured by a known analytical method such as liquid chromatography or gas chromatography.

[0272] <Resin (B)>

[0273] The resin (B) is not particularly limited, but is preferably an alkali-soluble resin. Examples of the resin (B) include the following resins [K1] to [K6].

[0274] Resin [K1]: a copolymer of at least one monomer (a) selected from unsaturated carboxylic acids and unsaturated carboxylic anhydrides (hereinafter sometimes referred to as "(a)") and a monomer (b) having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b)");

[0275] Resin [K2]: a copolymer of (a) and (b) and a monomer (c) copolymerizable with (a) (but different from (a) and (b)) (hereinafter sometimes referred to as "(c)");

[0276] Resin [K3]: a copolymer of (a) and (c);

[0277] Resin [K4]: a resin obtained by reacting (b) with a copolymer of (a) and (c);

[0278] Resin [K5]: a resin obtained by reacting (a) with a copolymer of (b) and (c);

[0279] Resin [K6]: A resin obtained by reacting (a) with a copolymer of (b) and (c), and further reacting with a polyvalent carboxylic acid and / or a carboxylic anhydride.

[0280] Specific examples of (a) include unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, and o-, m-, and p-vinylbenzoic acid;

[0281] 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, 1,4-cyclohexenedicarboxylic acid, etc.;

[0282] Bicyclic unsaturated compounds containing a carboxyl group, such as methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo[2.2.1]hept-2-ene, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene, 5-carboxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-carboxy-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;

[0283] Unsaturated dicarboxylic 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, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride;

[0284] Unsaturated mono(meth)acryloyloxyalkyl) esters of polycarboxylic acids having a valence of 2 or more, such as mono(2-(meth)acryloyloxyethyl)succinate and mono(2-(meth)acryloyloxyethyl)phthalate;

[0285] Unsaturated acrylic acid esters containing a hydroxyl group and a carboxyl group in the same molecule, such as α-(hydroxymethyl)acrylic acid, etc.

[0286] Among them, acrylic acid, methacrylic acid, maleic anhydride and the like are preferred from the viewpoint of copolymerization reactivity and solubility of the obtained resin in an aqueous alkali solution.

[0287] (b) refers to a polymerizable compound having, for example, a cyclic ether structure having 2 to 4 carbon atoms (e.g., at least one selected from an oxirane ring, an oxetane ring, and a tetrahydrofuran ring) and an ethylenically unsaturated bond. (b) Preferably, the monomer has a cyclic ether having 2 to 4 carbon atoms and a (meth)acryloyloxy group.

[0288] In addition, in this specification, "(meth)acrylic acid" means at least one selected from acrylic acid and methacrylic acid. Expressions such as "(meth)acryloyl" and "(meth)acrylate" have the same meaning.

[0289] As (b), for example, there can be mentioned a monomer (b1) having an oxetane group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b1)"), a monomer (b2) having an oxetane group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b2)"), and a monomer (b3) having a tetrahydrofuran group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b3)").

[0290] Examples of (b1) include a monomer (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized (hereinafter sometimes referred to as "(b1-1)") and a monomer (b1-2) having a structure in which an alicyclic unsaturated hydrocarbon is epoxidized (hereinafter sometimes referred to as "(b1-2)").

[0291] Examples of (b1-1) include glycidyl (meth)acrylate, β-methyl glycidyl (meth)acrylate, β-ethyl glycidyl (meth)acrylate, glycidyl vinyl ether, o-vinyl benzyl glycidyl ether, m-vinyl benzyl glycidyl ether, p-vinyl benzyl glycidyl ether, α-methyl-o-vinyl benzyl glycidyl ether, α-methyl-m-vinyl benzyl glycidyl ether, α-methyl-p-vinyl benzyl glycidyl ether, 2,3-bis(glycidyl)acrylate, 2,4-bis(glycidyloxymethyl)styrene, 2,5-bis(glycidyloxymethyl)styrene, 2,6-bis(glycidyloxymethyl)styrene, 2,3,4-tris(glycidyloxymethyl)styrene, 2,3,5-tris(glycidyloxymethyl)styrene, 2,3,6-tris(glycidyloxymethyl)styrene, 3,4,5-tris(glycidyloxymethyl)styrene, 2,4,6-tris(glycidyloxymethyl)styrene, etc.

[0292] Examples of (b1-2) include vinylcyclohexene monoxide, 1,2-epoxy-4-vinylcyclohexane (e.g., Celloxide 2000; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., Cyclomer A400; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., Cyclomer M100; manufactured by Daicel Corporation), 3,4-epoxytricyclo[5.2.1.0](meth)acrylate, and 3,4-epoxytricyclo[5.2.1.0](meth)acrylate. 2,6 ]decyl ester, a compound represented by formula (R1) and a compound represented by formula (R2), etc.

[0293]

[0294] [In formula (R1) and formula (R2), R ra and R rb It 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 by a hydroxyl group.

[0295] X ra and X rb Indicates a single bond, *-R rc -, * - R rc -O-, *-R rc -S- or *-R rc -NH-.

[0296] R rc It represents an alkanediyl group having 1 to 6 carbon atoms.

[0297] * indicates the bonding site with O. ]

[0298] Examples of the alkyl group 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.

[0299] Examples of the alkyl group in which a hydrogen atom is substituted with a hydroxy group include hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 1-hydroxypropyl, 2-hydroxypropyl, 3-hydroxypropyl, 1-hydroxy-1-methylethyl, 2-hydroxy-1-methylethyl, 1-hydroxybutyl, 2-hydroxybutyl, 3-hydroxybutyl and 4-hydroxybutyl.

[0300] As R ra and R rb , preferably, a hydrogen atom, a methyl group, a hydroxymethyl group, a 1-hydroxyethyl group, and a 2-hydroxyethyl group are mentioned, and more preferably, a hydrogen atom and a methyl group are mentioned.

[0301] Examples of the alkanediyl group include a methylene group, an ethylene group, a propane-1,2-diyl group, a propane-1,3-diyl group, a butane-1,4-diyl group, a pentane-1,5-diyl group, and a hexane-1,6-diyl group.

[0302] As X ra and X rb , preferably, a single bond, a methylene group, an ethylene group, *-CH2-O- and *-CH2CH2-O- are mentioned, and more preferably, a single bond and *-CH2CH2-O- (* represents a bonding site with O) are mentioned.

[0303] Examples of the compound represented by formula (R1) include compounds represented by any one of formula (R1-1) to formula (R1-15). Among them, compounds represented by formula (R1-1), formula (R1-3), formula (R1-5), formula (R1-7), formula (R1-9) or formula (R1-11) to formula (R1-15) are preferred, and compounds represented by formula (R1-1), formula (R1-7), formula (R1-9) or formula (R1-15) are more preferred.

[0304]

[0305]

[0306] Examples of the compound represented by formula (R2) include compounds represented by any one of formula (R2-1) to formula (R2-15). Among them, compounds represented by formula (R2-1), formula (R2-3), formula (R2-5), formula (R2-7), formula (R2-9) or formula (R2-11) to formula (R2-15) are preferred, and compounds represented by formula (R2-1), formula (R2-7), formula (R2-9) or formula (R2-15) are more preferred.

[0307]

[0308]

[0309] As (b2), a monomer having an oxetane group and a (meth)acryloyloxy group is more preferred. Examples of (b2) include 3-methyl-3-methacryloyloxymethyloxetane, 3-methyl-3-acryloyloxymethyloxetane, 3-ethyl-3-methacryloyloxymethyloxetane, 3-ethyl-3-acryloyloxymethyloxetane, 3-methyl-3-methacryloyloxyethyloxetane, 3-methyl-3-acryloyloxyethyloxetane, 3-ethyl-3-methacryloyloxyethyloxetane, and 3-ethyl-3-acryloyloxyethyloxetane.

[0310] As (b3), a monomer having a tetrahydrofuranyl group and a (meth)acryloyloxy group is more preferred. Specific examples of (b3) include tetrahydrofurfuryl acrylate (for example, Viscoat V#150, manufactured by Osaka Organic Chemical Industry Co., Ltd.) and tetrahydrofurfuryl methacrylate.

[0311] As (b), (b1) is preferred because the reliability of the obtained color filter, such as heat resistance and chemical resistance, can be further improved. Furthermore, (b1-2) is more preferred because the storage stability of the colored resin composition is excellent.

[0312] Examples of (c) include methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, sec-butyl (meth)acrylate, tert-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, dodecyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, cyclopentyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, tricyclo[5.2.1.0](meth)acrylate, 2,6 ] decane-8-yl ester (in the technical field, it is commonly known as "dicyclopentanyl (meth)acrylate". It is also sometimes referred to as "tricyclodecyl (meth)acrylate"), tricyclo[5.2.1.0 2,6 (Meth)acrylates such as decen-8-yl ester (in the technical field, it is commonly referred to as "dicyclopentenyl (meth)acrylate"), dicyclopentyloxyethyl (meth)acrylate, isobornyl (meth)acrylate, adamantyl (meth)acrylate, allyl (meth)acrylate, propargyl (meth)acrylate, phenyl (meth)acrylate, naphthyl (meth)acrylate, and benzyl (meth)acrylate;

[0313] (Meth)acrylates containing a hydroxyl group, such as 2-hydroxyethyl (meth)acrylate and 2-hydroxypropyl (meth)acrylate;

[0314] Diethyl maleate, diethyl fumarate, diethyl itaconate and other dicarboxylic acid diesters;

[0315] Bicyclo[2.2.1]hept-2-ene, 5-methylbicyclo[2.2.1]hept-2-ene, 5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxybicyclo[2.2.1]hept-2-ene, 5-hydroxymethylbicyclo[2.2.1]hept-2-ene, 5-(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5-methoxybicyclo[2.2.1]hept-2-ene, 5-ethoxybicyclo[2.2.1]hept-2-ene, 5,6-dihydroxybicyclo[2.2.1]hept-2-ene, 5,6-bis(hydroxymethyl)bicyclo[2.2.1]hept-2-ene, 5,6-bis(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5,6-dimethoxybicyclo[2.2.1]hept-2-ene Bicyclic unsaturated compounds such as cyclo[2.2.1]hept-2-ene, 5,6-diethoxybicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxymethyl-5-methylbicyclo[2.2.1]hept-2-ene, 5-tert-butoxycarbonylbicyclo[2.2.1]hept-2-ene, 5-cyclohexyloxycarbonylbicyclo[2.2.1]hept-2-ene, 5-phenoxycarbonylbicyclo[2.2.1]hept-2-ene, 5,6-bis(tert-butoxycarbonyl)bicyclo[2.2.1]hept-2-ene, and 5,6-bis(cyclohexyloxycarbonyl)bicyclo[2.2.1]hept-2-ene;

[0316] Dicarbonyl imide derivatives such as N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimidobenzoate, N-succinimidyl-4-maleimidobutyrate, N-succinimidyl-6-maleimidohexanoate, N-succinimidyl-3-maleimidopropionate, and N-(9-acridinyl)maleimide;

[0317] 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, etc.

[0318] As (c), 2-ethylhexyl (meth)acrylate, dicyclopentyl (meth)acrylate, benzyl (meth)acrylate, styrene, vinyltoluene, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo[2.2.1]hept-2-ene and the like are preferred, and styrene, vinyltoluene, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo[2.2.1]hept-2-ene and the like are more preferred from the viewpoint of copolymerization reactivity and heat resistance.

[0319] In resin [K1], the ratio of the structural units derived from each unit is preferably 2 to 60 mol% of the structural units derived from (a) and 40 to 98 mol% of the structural units derived from (b), and more preferably 10 to 50 mol% of the structural units derived from (a) and 50 to 90 mol% of the structural units derived from (b), among all the structural units constituting resin [K1].

[0320] When the ratio of the structural unit of the resin [K1] is within the above range, the storage stability of the colored resin composition, the developability when forming a colored pattern, and the solvent resistance of the obtained color filter tend to be more excellent.

[0321] The resin [K1] can be produced, for example, by the method described in the document "Experimental Methods for Polymer Synthesis" (Otsu Takayuki Publishing Co., Ltd., Chemical Dojin, 1st edition, 1st printing, published on March 1, 1972) and the references described in the document.

[0322] Specifically, the following method can be cited: a predetermined amount of (a) and (b), a polymerization initiator, a solvent, etc. are added to a reaction container, and a deoxygenated atmosphere is formed by replacing oxygen with nitrogen, for example, and heating and heat preservation are performed while stirring. It should be noted that the polymerization initiator and solvent used here are not particularly limited, and polymerization initiators and solvents commonly used in this field can be used. For example, as a polymerization initiator, an azo compound (2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile)), an organic peroxide (benzoyl peroxide, etc.) can be cited, and as a solvent, as long as it is a solvent that dissolves each monomer, the solvent described later as solvent (E) can be cited.

[0323] In addition, the obtained copolymer may be used as a solution after the reaction, or may be used as a concentrated or diluted solution, or may be taken out as a solid (powder) by a method such as reprecipitation. In particular, by using the solvent contained in the colored resin composition as a solvent during the polymerization, the solution after the reaction can be used directly for preparing the colored resin composition, so that the production process of the colored resin composition of the present invention can be simplified.

[0324] In resin [K2], the ratio of the structural unit derived from each unit is preferably 2 to 45 mol% of the structural unit derived from (a), 2 to 95 mol% of the structural unit derived from (b), and 1 to 65 mol% of the structural unit derived from (c), among all the structural units constituting resin [K2]. It is more preferred that the structural unit derived from (a) is 5 to 40 mol%, the structural unit derived from (b) is 5 to 80 mol%, and the structural unit derived from (c) is 5 to 60 mol%.

[0325] When the ratio of the structural unit of the resin [K2] is within the above range, the storage stability of the colored resin composition, the developability when forming a colored pattern, and the solvent resistance, heat resistance, and mechanical strength of the obtained color filter tend to be more excellent.

[0326] The resin [K2] can be produced, for example, in the same manner as described as the method for producing the resin [K1].

[0327] In resin [K3], the ratio of the structural units derived from each unit is preferably 2 to 60 mol% of the structural units derived from (a) and 40 to 98 mol% of the structural units derived from (c), and more preferably 10 to 50 mol% of the structural units derived from (a) and 50 to 90 mol% of the structural units derived from (c), among all the structural units constituting resin [K3].

[0328] The resin [K3] can be produced, for example, in the same manner as described as the method for producing the resin [K1].

[0329] The resin [K4] can be produced by obtaining a copolymer of (a) and (c), and adding a cyclic ether having 2 to 4 carbon atoms contained in (b) to the carboxylic acid and / or carboxylic anhydride contained in (a).

[0330] First, a copolymer of (a) and (c) is produced in the same manner as described as the method for producing resin [K1]. In this case, the ratio of the structural units derived from each unit is preferably the same ratio as that exemplified in resin [K3].

[0331] Next, the cyclic ether having 2 to 4 carbon atoms contained in (b) is reacted with a part of the carboxylic acid and / or carboxylic anhydride derived from (a) in the above copolymer.

[0332] After the copolymer of (a) and (c) is produced, the atmosphere in the flask is replaced from nitrogen to air, (b), a reaction catalyst for carboxylic acid or carboxylic anhydride and cyclic ether (e.g., tris(dimethylaminomethyl)phenol, etc.), and a polymerization inhibitor (e.g., hydroquinone, etc.) are placed in the flask, and the reaction is carried out at, for example, 60 to 130° C. for 1 to 10 hours, thereby producing resin [K4].

[0333] The amount of (b) used is preferably 5 to 80 mol, more preferably 10 to 75 mol, relative to 100 mol of (a). By using the amount within this range, there is a tendency for the storage stability of the colored resin composition, the developability when forming a pattern, and the balance of the solvent resistance, heat resistance, mechanical strength and sensitivity of the obtained pattern to become good. Cyclic ethers have high reactivity and are less likely to leave unreacted (b). As the (b) used in the resin [K4], (b1) is preferred, and (b1-1) is further preferred.

[0334] The amount of the reaction catalyst used is preferably 0.001 to 5 parts by mass relative to 100 parts by mass of the total amount of (a), (b) and (c). The amount of the polymerization inhibitor used is preferably 0.001 to 5 parts by mass relative to 100 parts by mass of the total amount of (a), (b) and (c).

[0335] The reaction conditions such as the charging method, reaction temperature and time can be appropriately adjusted in consideration of the production equipment, the calorific value based on the polymerization, etc. It should be noted that the charging method and reaction temperature can be appropriately adjusted in consideration of the production equipment, the calorific value based on the polymerization, etc., similarly to the polymerization conditions.

[0336] As a first step, the resin [K5] is subjected to the same method as the above-mentioned method for producing the resin [K1] to obtain a copolymer of (b) and (c). As described above, the obtained copolymer may be used directly as a solution after the reaction, or may be used after a concentration or dilution, or may be used after being taken out in a solid (powder) form by a method such as reprecipitation.

[0337] The ratio of the structural units derived from (b) and (c) is preferably 5 to 95 mol% for the structural units derived from (b) and 5 to 95 mol% for the structural units derived from (c), respectively, relative to the total molar number of all the structural units constituting the above-mentioned copolymer, and more preferably 10 to 90 mol% for the structural units derived from (b) and 10 to 90 mol% for the structural units derived from (c).

[0338] Furthermore, resin [K5] can be obtained by reacting the carboxylic acid or carboxylic anhydride contained in (a) with the cyclic ether derived from (b) contained in the copolymer of (b) and (c) under the same conditions as in the method for producing resin [K4].

[0339] The amount of (a) to be reacted with the copolymer is preferably 5 to 100 mol per 100 mol of (b). Cyclic ethers have high reactivity and are less likely to leave unreacted (b). Therefore, (b1) is preferred as (b1-1) and more preferred as (b) to be used in the resin [K5].

[0340] The resin [K6] is obtained by further reacting the resin [K5] with a carboxylic acid anhydride. The carboxylic acid anhydride is reacted with the hydroxyl group generated by the reaction of the cyclic ether with the carboxylic acid or the carboxylic acid anhydride.

[0341] Examples of the carboxylic anhydride include succinic anhydride, maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride, etc. The amount of the carboxylic anhydride used is preferably 0.1 to 1 mol relative to 1 mol of the amount of (a) used.

[0342] Specific examples of the resin (B) include 3,4-epoxycyclohexylmethyl (meth)acrylate / (meth)acrylic acid copolymers, 3,4-epoxytricyclo[5.2.1.0 2,6 ] decyl ester / (meth) acrylic acid copolymer resin [K1]; acrylic acid 3,4-epoxy tricyclic [5.2.1.0 2,6 ]decyl ester / benzyl (meth)acrylate / (meth)acrylic acid copolymer, glycidyl (meth)acrylate / benzyl (meth)acrylate / (meth)acrylic acid copolymer, glycidyl (meth)acrylate / styrene / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl ester / (meth)acrylic acid / N-cyclohexylmaleimide copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl ester / (meth)acrylic acid / vinyl toluene copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6] decyl ester / (meth)acrylic acid / N-cyclohexylmaleimide / 2-hydroxyethyl (meth)acrylate copolymer, 3-methyl-3-(meth)acryloyloxymethyloxetane / (meth)acrylic acid / styrene copolymer and the like resins [K2]; benzyl (meth)acrylate / (meth)acrylic acid copolymer, styrene / (meth)acrylic acid copolymer and the like resins [K3]; resins obtained by adding glycidyl (meth)acrylate to benzyl (meth)acrylate / (meth)acrylic acid copolymer, resins obtained by adding glycidyl (meth)acrylate to tricyclodecyl (meth)acrylate / styrene / (meth)acrylic acid copolymer, resins obtained by adding glycidyl (meth)acrylate to tricyclodecyl (meth)acrylate / benzyl (meth)acrylate / (meth)acrylic acid copolymer, Resins such as resins obtained by addition of copolymers [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, etc. [K5]; resins obtained by reacting (meth)acrylic acid with a copolymer of tricyclodecyl (meth)acrylate / glycidyl (meth)acrylate and further reacting with tetrahydrophthalic anhydride, resins obtained by reacting (meth)acrylic acid with a copolymer of 2-ethylhexyl (meth)acrylate / glycidyl (meth)acrylate / dicyclopentanyl (meth)acrylate and further reacting with succinic anhydride, etc. [K6], etc.

[0343] Among them, as resin (B), at least one selected from copolymers containing structural units derived from at least one selected from unsaturated carboxylic acids and unsaturated carboxylic anhydrides and structural units having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond (resin [K1], resin [K2]), and resin [K6] is preferred, and resin [K1] and / or resin [K2] are more preferred.

[0344] The polystyrene-equivalent weight average molecular weight of the resin (B) is preferably 500 to 100000, more preferably 1000 to 50000, and further preferably 3000 to 30000. When the molecular weight is within the above range, the hardness of the color filter is improved, the residual film rate is high, the solubility of the unexposed portion in the developer is good, and the resolution of the colored pattern tends to be improved.

[0345] The dispersion degree [weight average molecular weight (Mw) / number average molecular weight (Mn)] of the resin (B) is preferably 1.1-6, more preferably 1.2-4.

[0346] The acid value of the resin (B) is preferably 10 to 170 mg-KOH / g, more preferably 30 to 155 mg-KOH / g, and further preferably 50 to 140 mg-KOH / g, based on solid content. Here, the acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of the resin (B), and can be determined, for example, by titration using a potassium hydroxide aqueous solution.

[0347] The content of the resin (B) is preferably 7 to 80% by mass, more preferably 13 to 70% by mass, further preferably 17 to 60% by mass, and further preferably 20 to 50% by mass relative to the total amount of the solid content of the colored resin composition. When the content of the resin (B) is within the above range, a colored pattern can be formed, and there is a tendency that the resolution and residual film rate of the colored pattern are improved.

[0348] The content of the resin (B) is, for example, 30 to 200 parts by mass, preferably 50 to 180 parts by mass, and more preferably 80 to 150 parts by mass, relative to 100 parts by mass of the compound (I). By adjusting the content of the resin (B) to be within the above range, there is a tendency to easily improve the above-mentioned brightness unevenness suppression effect.

[0349] <Polymerizable compound (C)>

[0350] The polymerizable compound (C) is a compound that can be polymerized by active radicals and / or acids generated from the polymerization initiator (D), and examples thereof include compounds having a polymerizable ethylenically unsaturated bond, and are preferably (meth)acrylate compounds.

[0351] Among them, the polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds. Examples of such polymerizable compounds include trimethylolpropane tri(meth)acrylate, pentaerythritol poly(meth)acrylate (e.g., pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate), dipentaerythritol poly(meth)acrylate (e.g., dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate), tripentaerythritol poly(meth)acrylate (e.g., tripentaerythritol octa(meth)acrylate, tripentaerythritol hepta(meth)acrylate), tetrapentaerythritol poly(meth)acrylate (e.g., tetrapentaerythritol deca(meth)acrylate, tetrapentaerythritol nona(meth)acrylate), tris(2-(meth)acryloyloxyethyl)isocyanurate, alkoxylated pentaerythritol poly(meth)acrylate (e.g., ethoxylated pentaerythritol tri(meth)acrylate, tetrapenta ... acrylate, ethoxylated pentaerythritol tetra(meth)acrylate, propoxylated pentaerythritol tri(meth)acrylate, propoxylated pentaerythritol tetra(meth)acrylate), alkoxylated dipentaerythritol poly(meth)acrylate (e.g., ethoxylated dipentaerythritol penta(meth)acrylate, ethoxylated dipentaerythritol hexa(meth)acrylate, propoxylated dipentaerythritol penta(meth)acrylate, propoxylated dipentaerythritol hexa(meth)acrylate), caprolactone-modified pentaerythritol poly(meth)acrylate (e.g., caprolactone-modified pentaerythritol tri(meth)acrylate, caprolactone-modified pentaerythritol tetra(meth)acrylate), caprolactone-modified dipentaerythritol poly(meth)acrylate (e.g., caprolactone-modified dipentaerythritol penta(meth)acrylate, caprolactone-modified dipentaerythritol hexa(meth)acrylate), and the like.

[0352] Among them, at least one selected from trimethylolpropane tri(meth)acrylate and dipentaerythritol poly(meth)acrylate is preferred.

[0353] The weight average molecular weight of the polymerizable compound (C) is preferably 150 to 2,900, more preferably 250 to 1,500.

[0354] The content of the polymerizable compound (C) is, for example, 5 to 65% by mass, preferably 6 to 50% by mass, and more preferably 8 to 30% by mass relative to the total amount of the solid content of the colored resin composition. When the content of the polymerizable compound (C) is within the above range, there is a tendency for the residual film rate during color pattern formation and the chemical resistance of the color filter to be further improved.

[0355] <Polymerization initiator (D)>

[0356] The polymerization initiator (D) is not particularly limited as long as it is a compound that can generate active radicals, acids, etc. under the action of light or heat to initiate polymerization, and a known polymerization initiator can be used.

[0357] Examples of the polymerization initiator that generates active radicals include alkylphenone compounds, triazine compounds, acylphosphine oxide compounds, O-acyloxime compounds, and biimidazole compounds.

[0358] The O-acyl oxime compound is a compound having a partial structure represented by formula (d1). Hereinafter, * represents a bonding site.

[0359]

[0360] Examples of the O-acyl oxime compound include N-benzoyloxy-1-(4-phenylthiophenyl)butane-1-one-2-imine, N-benzoyloxy-1-(4-phenylthiophenyl)octane-1-one-2-imine, N-benzoyloxy-1-(4-phenylthiophenyl)-3-cyclopentylpropane-1-one-2-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]ethane-1-imine, N-acetoxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethyl-2,4-dioxolanylmethyloxy)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, N-acetoxy-1-[4-(2-hydroxyethoxy)phenylthiophenyl]propane-1-one-2-imine, N-acetoxy-1-(4-phenylthiophenyl)-3-cyclohexylpropane-1-one-2-imine, 2-[(acetoxy)imino]-3-cyclohexyl-1-[4-(phenylthio)phenyl]propane-1-one and the like. Commercially available products such as Irgacure OXE01, OXE02, OXE03 (all manufactured by BASF), N-1919 (manufactured by ADEKA), PBG-314, PBG-317, PBG-326, PBG-327, and PBG-329 (all manufactured by Changzhou Qiangli Electronic New Materials Co., Ltd.) can be used. Among them, the O-acyl oxime compound is preferably selected from N-acetoxy-1-[4-(2-hydroxyethoxy)phenylthiophenyl]propane-1-one-2-imine, N-acetoxy-1-(4-phenylthiophenyl)-3-cyclohexylpropane-1-one-2-imine, 2-[(acetoxy)imino]-3-cyclohexyl-1-[4-(phenylthio)phenyl]propane-1-one, N-benzoyloxy-1-(4-phenylthiophenyl)butane-1-one-2-imine, N-benzoyloxy-1-(4-phenylthiophenyl)butane-1-one-2-imine, At least one selected from the group consisting of 2-[(acetyloxy)imino]-3-cyclohexyl-1-[4-(phenylthio)phenyl]propane-1-one, N-benzoyloxy-1-(4-phenylthiophenyl)octane-1-one-2-imine and N-acetoxy-1-(4-phenylthiophenyl)-3-cyclohexylpropane-1-one-2-imine is more preferred. In the case of these O-acyl oxime compounds, there is a tendency that a high brightness color filter can be obtained.

[0361] The alkylphenone compound is a compound having a partial structure represented by formula (d2) or a partial structure represented by formula (d3). In these partial structures, the benzene ring may have a substituent.

[0362]

[0363] Examples of the compound having a partial structure represented by formula (d2) include 2-methyl-2-morpholino-1-(4-methylthiophenyl)propane-1-one, 2-dimethylamino-1-(4-morpholinophenyl)-2-benzylbutane-1-one, and 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholino)phenyl]butane-1-one. Commercially available products such as Irgacure 369, 907, and 379 (all manufactured by BASF) can also be used.

[0364] Examples of the compound having a partial structure represented by formula (d3) include 2-hydroxy-2-methyl-1-phenylpropane-1-one, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy)phenyl]propane-1-one, 1-hydroxycyclohexyl phenyl ketone, oligomers of 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propane-1-one, α,α-diethoxyacetophenone, and benzil dimethyl ketal.

[0365] In terms of sensitivity, the alkylphenone compound is preferably a compound having a partial structure represented by formula (d2).

[0366] Examples of the triazine compound include 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxynaphthyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, and 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine. [2-(5-methylfuran-2-yl)vinyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)vinyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl)vinyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)vinyl]-1,3,5-triazine, and the like.

[0367] Examples of the acylphosphine oxide compound include 2,4,6-trimethylbenzoyldiphenylphosphine oxide, etc. Commercially available products such as Irgacure (registered trademark) 819 (manufactured by BASF Corporation) can be used.

[0368] Examples of the biimidazole compound include 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3-dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole (see, for example, Japanese Patent Application Laid-Open No. 6-75372 and Japanese Patent Application Laid-Open No. 6-75373), 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, and 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole. Biimidazole compounds in which the phenyl groups at the 4,4',5,5'-positions are substituted with carbonyl alkoxy groups (for example, see Japanese Patent Publication No. 7-10913, etc.).

[0369] In addition, examples of the polymerization initiator (D) include benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether; benzophenone compounds such as benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, 3,3',4,4'-tetra(tert-butylperoxycarbonyl)benzophenone, and 2,4,6-trimethylbenzophenone; quinone compounds such as 9,10-phenanthrenequinone, 2-ethylanthraquinone, and camphorquinone; 10-butyl-2-chloroacridone, benzil, methyl benzoylformate, and titanocene compounds, etc. These are preferably used in combination with the polymerization initiator aid (D1) (particularly amine compounds) described later.

[0370] Examples of the polymerization initiator that generates an acid include 4-hydroxyphenyldimethylsulfonium p-toluenesulfonate, 4-hydroxyphenyldimethylsulfonium hexafluoroantimonate, 4-acetoxyphenyldimethylsulfonium p-toluenesulfonate, 4-acetoxyphenylmethylbenzylsulfonium hexafluoroantimonate, triphenylsulfonium p-toluenesulfonate, triphenylsulfonium hexafluoroantimonate, and diphenyliodonium. p-Toluenesulfonate, diphenyl iodide Hexafluoroantimonate, etc. Salts, nitrobenzyl tosylate, benzoin tosylate, etc.

[0371] The polymerization initiator (D) preferably contains at least one selected from an alkylphenone compound, a triazine compound, an acylphosphine oxide compound, an O-acyloxime compound and a biimidazole compound, and more preferably contains an O-acyloxime compound.

[0372] The content of the polymerization initiator (D) is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, and further preferably 2 to 10 parts by mass relative to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). When the content of the polymerization initiator (D) is within the above range, there is a tendency to increase sensitivity and shorten exposure time, thereby improving the productivity of the color filter.

[0373] <Polymerization initiator aid (D1)>

[0374] The polymerization initiator aid (D1) is a compound or sensitizer for accelerating the polymerization of the polymerizable compound to be polymerized by the polymerization initiator. When the polymerization initiator aid (D1) is contained, it is usually used in combination with the polymerization initiator (D).

[0375] Examples of the polymerization initiation aid (D1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds, and carboxylic acid compounds.

[0376] Examples of the amine compound include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isopentyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 2-ethylhexyl 4-dimethylaminobenzoate, N,N-dimethyl-p-toluidine, 4,4'-bis(dimethylamino)benzophenone (commonly known as Michler's ketone), 4,4'-bis(diethylamino)benzophenone, and 4,4'-bis(ethylmethylamino)benzophenone. Among them, 4,4'-bis(diethylamino)benzophenone is preferred. Commercially available products such as EAB-F (manufactured by Hodogaya Chemical Industry Co., Ltd.) can be used.

[0377] Examples of the alkoxyanthracene compound include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene, 9,10-dibutoxyanthracene, and 2-ethyl-9,10-dibutoxyanthracene.

[0378] Examples of the thioxanthone compound include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, and 1-chloro-4-propoxythioxanthone.

[0379] Examples of the carboxylic acid compound include phenylthioacetic acid, methylphenylthioacetic acid, ethylphenylthioacetic acid, methylethylphenylthioacetic acid, dimethylphenylthioacetic acid, methoxyphenylthioacetic acid, dimethoxyphenylthioacetic acid, chlorophenylthioacetic acid, dichlorophenylthioacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, and naphthoxyacetic acid.

[0380] When these polymerization initiator aids (D1) are used, the content thereof is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, relative to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). When the amount of the polymerization initiator aid (D1) is within this range, a colored pattern can be formed with further high sensitivity, and there is a tendency that the productivity of the color filter is improved.

[0381] <Solvent (E)>

[0382] The solvent (E) is not particularly limited, and a solvent commonly used in this field can be used. For example, ester solvents (solvents containing -COO- and not containing -O- in the molecule), ether solvents (solvents containing -O- and not containing -COO- in the molecule), ether ester solvents (solvents containing -COO- and -O- in the molecule), ketone solvents (solvents containing -CO- and not containing -COO- in the molecule), alcohol solvents (solvents containing OH and not containing -O-, -CO- and -COO- in the molecule), aromatic hydrocarbon solvents, amide solvents, dimethyl sulfoxide, etc. can be mentioned.

[0383] Examples of the ester solvent include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutyrate, ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, isoamyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexanol acetate, and γ-butyrolactone.

[0384] Examples of the ether solvent include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dihydrofu ... Alkane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenethyl ether and methyl anisole, etc.

[0385] Examples of the ether ester solvent 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, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, and diethylene glycol monobutyl ether acetate.

[0386] Examples of the ketone solvent 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.

[0387] Examples of the alcohol solvent include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerin.

[0388] Examples of the aromatic hydrocarbon solvent include benzene, toluene, xylene, and mesitylene.

[0389] Examples of the amide solvent include N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.

[0390] Among the above solvents, an organic solvent having a boiling point of 120° C. to 180° C. at 1 atm is preferred from the viewpoint of coating properties and drying properties. As the solvent, at least one selected from propylene glycol monomethyl ether acetate, ethyl lactate, propylene glycol monomethyl ether, ethyl 3-ethoxypropionate, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, 4-hydroxy-4-methyl-2-pentanone and N,N-dimethylformamide is preferred, and at least one selected from propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, 4-hydroxy-4-methyl-2-pentanone, ethyl lactate and ethyl 3-ethoxypropionate is more preferred.

[0391] In addition, as the solvent (E), it is also preferable to use an ether ester solvent and a ketone solvent in combination. In this case, as the ether ester solvent, C 2-3 Alkylene glycol mono C 1-4 Alkyl ether acetate, more preferably propylene glycol mono-C 1-4 Alkyl ether acetate. As the ketone solvent, 4-hydroxy-4-methyl-2-pentanone is preferred.

[0392] When the ether ester solvent and the ketone solvent are used in combination, the content of the ketone solvent is preferably 1 to 100 parts by mass, more preferably 3 to 50 parts by mass, and even more preferably 5 to 20 parts by mass based on 100 parts by mass of the total of the ether ester solvent and the ketone solvent.

[0393] The content of the solvent (E) is preferably 70 to 95% by mass, more preferably 75 to 92% by mass, relative to the total amount of the colored resin composition. In other words, the solid content of the colored resin composition is preferably 5 to 30% by mass, more preferably 8 to 25% by mass. When the content of the solvent (E) is within the above range, the flatness during coating becomes good, and the color density is not insufficient when forming a color filter, so there is a tendency that the display characteristics and sensitivity become good.

[0394] <Leveling agent (F)>

[0395] Examples of the leveling agent (F) include silicone-based surfactants, fluorine-based surfactants, and silicone-based surfactants having fluorine atoms, etc. These may have a polymerizable group in a side chain.

[0396] Examples of the silicone surfactant include surfactants having a siloxane bond in the molecule, and more specifically, Toray Silicone DC3PA, Toray Silicone SH7PA, Toray Silicone DC11PA, Toray Silicone SH21PA, Toray Silicone SH28PA, Toray Silicone SH29PA, Toray Silicone SH30PA, Toray Silicone SH8400 (trade name: manufactured by Dow Corning Toray 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 Co., Ltd.).

[0397] Examples of the fluorine-based surfactant include surfactants having a fluorine carbon chain in the molecule. Specifically, examples include FLUORAD (registered trademark) FC430, FLUORAD FC431 (manufactured by Sumitomo 3M Co., Ltd.), MEGAFAC (registered trademark) F142D, MEGAFAC F171, MEGAFAC F172, MEGAFAC F173, MEGAFAC F177, MEGAFAC F183, MEGAFAC F554, MEGAFAC R30, MEGAFAC RS-718-K (manufactured by DIC Corporation), F-top (registered trademark) EF301, F-top EF303, F-top EF351, F-top EF352 (manufactured by Mitsubishi Materials Electronic Chemicals Co., Ltd.), Surflon (registered trademark) S381, Surflon S382, Surflon SC101, Surflon SC105 (manufactured by AGC Corporation (former Asahi Glass Corporation)) and E5844 (manufactured by Daikin Fine Chemicals Laboratories, Ltd.), etc.

[0398] Examples of the above-mentioned organosilicon-based surfactants having fluorine atoms include surfactants having a siloxane bond and a fluorocarbon chain in the molecule, and more specifically, MEGAFAC (registered trademark) R08, MEGAFAC BL20, MEGAFAC F475, MEGAFAC F477, and MEGAFAC F443 (manufactured by DIC Corporation).

[0399] The content of the leveling agent (F) is preferably 0.001 to 0.2 mass %, more preferably 0.002 to 0.1 mass %, and further preferably 0.005 to 0.05 mass % relative to the total amount of the colored resin composition. It should be noted that the content does not include the content of the pigment dispersant described later. When the content of the leveling agent (F) is within the above range, the flatness of the color filter can be improved.

[0400] <Other ingredients>

[0401] The colored resin composition may contain additives known in the technical field such as a filler, other polymer compounds, an adhesion promoter, an antioxidant, a light stabilizer, and a chain transfer agent, as required.

[0402] <Method for producing colored resin composition>

[0403] The colored resin composition can be prepared by mixing, for example, a colorant (A) and a resin (B), and, if necessary, a polymerizable compound (C), a polymerization initiator (D), a solvent (E), a leveling agent (F), a polymerization initiation aid (D1), and other components. The mixed colored resin composition can be filtered with a filter having a pore size of about 0.01 to 10 μm.

[0404] The compound (I) as the colorant (A) and the pigment as the colorant (A1) used as needed can be dispersed by containing a pigment dispersant and used as a dispersion in a state uniformly dispersed in a solution. By mixing the remaining components in such a dispersion to achieve a predetermined concentration, the target colored resin composition can be prepared. The compound (I) and the pigment can be dispersed alone or in a mixture of multiple types.

[0405] As the pigment dispersant, surfactants etc. can be mentioned, which can be any surfactant of cationic, anionic, nonionic and amphoteric. Specifically, surfactants such as polyester, polyamine and acrylic acid can be mentioned. These dispersants can be used alone or in combination of two or more. As dispersants, represented by trade names, KP (Shin-Etsu Chemical Industry (Strain) system), FLOWLEN (Kyoeisha Chemical (Strain) system), Solsperse (ZENECA company system), EFKA (CIBA company system), AJISPER (Ajinomoto Fine Chemicals (Strain) system), Disperbyk (registered trademark), BYK (registered trademark) (BYK-Chemie company system) etc. can be mentioned.

[0406] When a pigment dispersant is used, its usage amount is preferably 5 to 200 parts by mass, more preferably 10 to 150 parts by mass, and further preferably 20 to 130 parts by mass, relative to 100 parts by mass of the colorant (A) (specifically, compound (I) and pigment) in the dispersion. When the usage amount of the pigment dispersant is within the above range, there is a tendency to obtain a dispersion in a more uniform dispersed state.

[0407] When the colorant (A) contains a dye, the dye may be dissolved in part or all of the solvent (E) to prepare a solution, and the solution is preferably filtered through a filter having a pore size of about 0.01 to 1 μm.

[0408] [Color Filter]

[0409] As a method for manufacturing a coloring pattern of a color filter by the colored resin composition of the present invention, photolithography, inkjet method, printing method, etc. can be cited. Among them, photolithography is preferred. Photolithography is a method in which the above-mentioned colored resin composition is applied to a substrate and dried to form a composition layer, and the composition layer is exposed through a photomask and developed. In the photolithography, a colored coating film as a cured product of the above-mentioned composition layer can be formed by not using a photomask and / or not developing during exposure.

[0410] The film thickness of the color filter (colored coating or colored pattern) is, for example, 30 μm or less, preferably 20 μm or less, more preferably 6 μm or less, further preferably 3 μm or less, further preferably 1.5 μm or less, particularly preferably 0.5 μm or less, preferably 0.1 μm or more, more preferably 0.2 μm or more, further preferably 0.3 μm or more.

[0411] As the substrate, a glass plate such as quartz glass, borosilicate glass, aluminosilicate glass, soda-lime glass with silicon dioxide coated on the surface, a resin plate such as polycarbonate, polymethyl methacrylate, polyethylene terephthalate, silicon, or a substrate having aluminum, silver, or a silver / copper / palladium alloy thin film formed thereon can be used. Other color filter layers, resin layers, transistors, circuits, etc. can be formed on these substrates. In addition, a substrate obtained by subjecting a silicon substrate to HMDS treatment can also be used.

[0412] The formation of pixels of various colors (color filters of various colors) based on photolithography can be carried out using known or customary devices and conditions. For example, it can be produced as described below. First, the colored resin composition is applied to the substrate, and heat-dried (pre-baked) and / or dried under reduced pressure, thereby removing volatile components such as solvents and drying them to obtain a smooth composition layer. As coating methods, spin coating, slit coating, slit and spin coating, etc. can be cited. The temperature during heating and drying is preferably 30 to 120°C, more preferably 50 to 110°C. In addition, as a heating time, it is preferably 10 seconds to 60 minutes, more preferably 30 seconds to 30 minutes. When drying under reduced pressure, it is preferably carried out at a temperature range of 20 to 25°C under a pressure of 50 to 150Pa. The film thickness of the composition layer is not particularly limited, as long as it is appropriately selected according to the film thickness of the target color filter.

[0413] Next, the composition layer is exposed through a photomask for forming a target coloring pattern. The pattern on the photomask is not particularly limited, and a pattern corresponding to the target application is used. As the light source used for exposure, a light source that generates light with a wavelength of 250 to 450 nm is preferably used. For example, light less than 250 nm can be cut off using a filter that cuts off the wavelength region, or light near 436 nm, near 408 nm, and near 365 nm can be selectively extracted using a bandpass filter that extracts these wavelength regions. Specifically, mercury lamps, light emitting diodes, metal halide lamps, halogen lamps, etc. can be cited. In order to be able to evenly irradiate parallel light to the entire exposure surface and accurately align the photomask with the substrate, it is preferred to use a reduced projection exposure device or a close-type exposure device such as a mask aligner and a stepper.

[0414] The exposed composition layer is brought into contact with a developer for development, thereby forming a colored pattern on the substrate. The unexposed portion of the composition layer is dissolved in the developer by development and removed. As the developer, for example, aqueous solutions of alkaline compounds such as potassium hydroxide, sodium bicarbonate, sodium carbonate and tetramethylammonium hydroxide are preferred. The concentration in the aqueous solution of these alkaline compounds is preferably 0.01% to 10% by mass, more preferably 0.03% to 5% by mass. In addition, the developer may contain a surfactant. The development method may be any one of a paddle method, an immersion method and a spray method. Furthermore, the substrate is tilted at any angle during development.

[0415] The substrate after development is preferably washed with water.

[0416] The obtained colored pattern is preferably post-baked. The post-baking temperature is preferably 80 to 250° C., more preferably 100 to 245° C. The post-baking time is preferably 1 to 120 minutes, more preferably 2 to 30 minutes.

[0417] The colored pattern and colored coating film thus obtained are useful as a color filter, and the color filter is useful as a color filter used in a display device (for example, a liquid crystal display device, an organic EL device, etc.), electronic paper, a solid-state imaging element, and the like.

[0418] In particular, the above-mentioned colored pattern and colored coating are useful as green filters in color filters. When the above-mentioned colored pattern or colored coating has a film thickness of 2.0 μm, it is preferred to satisfy the following (i) and (ii). The colored resin composition that can form a colored pattern or colored coating that satisfies the following (i) and (ii) can form a green filter with excellent spectral characteristics. In particular, from the viewpoint of being able to show good spectral characteristics even after long-term use, the above-mentioned colored pattern and colored coating preferably also satisfy the following (i) and (ii) after the light irradiation test described in the embodiment column described later.

[0419] (i) Transmittance at 550nm is 35% to 99%

[0420] (ii) Transmittance at 620 nm is 0.1% to 20%

[0421] Example

[0422] Hereinafter, the present invention will be described in more detail by giving examples, but the present invention is not limited by the following examples, and can certainly be implemented by adding appropriate changes in the scope that can be suitable for the aforementioned and later-described purports, which are all included in the technical scope of the present invention. It should be noted that, below, "part" means "part by mass", and "%" means "% by mass", unless otherwise specified.

[0423] In the following examples, the structures of the compounds were confirmed by mass spectrometry (MALDI-TOF MS; JMS-S3000 manufactured by JEOL Ltd.).

[0424] (Synthesis example 1)

[0425] <Synthesis of Compound (II-1)>

[0426] Under a nitrogen atmosphere, 43 parts of 4-nitrophthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.), 40 parts of 2,6-dichlorophenol (manufactured by Tokyo Chemical Industry Co., Ltd.), 37 parts of potassium carbonate (manufactured by Kanto Chemical Co., Ltd.), and 211 parts of dehydrated acetonitrile (manufactured by Kanto Chemical Co., Ltd.) were mixed, heated to 80°C, and stirred at the same temperature for 10 hours. The reaction solution was cooled to room temperature (18 to 24°C) and filtered to obtain filtrate A and residue A. Residue A was washed with 300 parts of acetonitrile, and the obtained acetonitrile solution and filtrate A were combined, and the solvent in the solution was distilled off. The obtained residue was washed with 300 parts of ion-exchanged water and dried to obtain 60 parts of a compound represented by formula (II-1) (hereinafter referred to as compound (II-1)) as a colorless solid (yield 85%).

[0427]

[0428] <Identification of Compound (II-1)>

[0429] (Mass Spectrometry) Ionization Mode = MALDI-TOF-: m / z = 288

[0430] Exact molecular weight: 288

[0431] (Example 1)

[0432] <Synthesis of Compound (I-e1)>

[0433] Under nitrogen atmosphere, 60 parts of compound (II-1) prepared in Synthesis Example 1, 8.7 parts of anhydrous aluminum chloride (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.), 480 parts of triethylene glycol (manufactured by Tokyo Chemical Industry Co., Ltd.) and 55 parts of 1,8-diazabicyclo[5,4,0]-7-undecene (manufactured by Tokyo Chemical Industry Co., Ltd.) were mixed and heated at 140°C for 10 hours. After the reaction was completed, the reaction solution was cooled to room temperature (18 to 24°C) and poured into 600 parts of ion exchange water. The precipitated solid was separated by decantation in the order of 300 parts of ion exchange water twice and 300 parts of acetone once. The crude product was purified by silica gel column chromatography (developing solvent: gradient from toluene to tetrahydrofuran) to obtain 23.5 parts (yield 39%) of the compound represented by formula (I-e1) (hereinafter referred to as compound (I-e1)) and 4.5 parts (yield 7%) of the compound represented by formula (IV-e1) (hereinafter referred to as compound (IV-e1)) in solid form.

[0434]

[0435] <Identification of Compound (I-e1)>

[0436] (Mass Spectrometry) Ionization Mode = MALDI-TOF-: m / z = 1154

[0437] Exact molecular weight: 1154

[0438] <Identification of Compound (IV-e1)>

[0439] Silica gel thin layer chromatography (TLC) confirmed that there were only two colored components obtained in the reaction of Example 1. One was confirmed as compound (I-e1) by MALDI-TOF MS as described above. The remaining one was confirmed to be a metal body because it showed a unique spectral shape of a metal body in the measurement using an ultraviolet-visible-near-infrared absorption spectrometer (JASCO: V-770) (hereinafter referred to as UV-vis measurement). Based on the reaction substrate, it was shown that the metal body was an aluminum body. Furthermore, the Rf value (developing solvent toluene) in silica gel thin layer chromatography (TLC) was 0.35 in the compound represented by the following formula (IV-e11) as a similar compound, and the above-mentioned aluminum body was 0.30, so the aluminum body was identified as compound (IV-e1).

[0440]

[0441] (Synthesis example 2)

[0442] <Synthesis of Compound (II-2)>

[0443] 62 parts of a compound represented by formula (II-2) (hereinafter referred to as compound (II-2)) were obtained as a colorless solid in the same manner as in Synthesis Example 1 except that 40 parts of 2,6-dichlorophenol was replaced with 40 parts of 3,4-dichlorophenol (manufactured by Tokyo Chemical Industry Co., Ltd.) (yield 87%).

[0444]

[0445] <Identification of Compound (II-2)>

[0446] (Mass Spectrometry) Ionization Mode = MALDI-TOF-: m / z = 289

[0447] Exact molecular weight: 288

[0448] (Example 2)

[0449] <Synthesis of Compound (I-e2)>

[0450] Except that 60 parts of compound (II-1) were replaced by 60 parts of compound (II-2) obtained in Synthesis Example 2, 32 parts of a compound represented by formula (I-e2) (hereinafter referred to as compound (I-e2)) (yield 53%) and 7 parts of a compound represented by formula (IV-e2) (hereinafter referred to as compound (IV-e2)) (yield 11%) were obtained in the same manner as in Example 1.

[0451]

[0452] <Identification of Compound (I-e2)>

[0453] (Mass Spectrometry) Ionization Mode = MALDI-TOF-: m / z = 1156

[0454] Exact molecular weight: 1154

[0455] <Identification of Compound (IV-e2)>

[0456] (Mass Spectrometry) Ionization Mode = MALDI-TOF-: m / z = 1218

[0457] Exact molecular weight: 1219

[0458] (Synthesis example 3)

[0459] <Synthesis of Compound (II-3)>

[0460] 54 parts of a compound represented by formula (II-3) (hereinafter referred to as compound (II-3)) were obtained as a colorless solid in the same manner as in Synthesis Example 1 except that 40 parts of 2,6-dichlorophenol was replaced with 32 parts of 2-chlorophenol (manufactured by Tokyo Chemical Industry Co., Ltd.) (yield 87%).

[0461]

[0462] (Example 3)

[0463] <Synthesis of Compound (I-e3)>

[0464] Except that 60 parts of compound (II-1) were replaced by 53 parts of compound (II-3) obtained in Synthesis Example 3, 14 parts of a compound represented by formula (I-e3) (hereinafter referred to as compound (I-e3)) (yield 27%) and 4 parts of a compound represented by formula (IV-e3) (hereinafter referred to as compound (IV-e3)) (yield 7%) were obtained in the same manner as in Example 1.

[0465]

[0466] <Identification of Compound (I-e3)>

[0467] (Mass Spectrometry) Ionization Mode = MALDI-TOF-: m / z = 1020

[0468] Exact molecular weight: 1018

[0469] <Identification of Compound (IV-e3)>

[0470] By silica gel thin layer chromatography (TLC), it was confirmed that there were only two colored components obtained in the reaction of Example 3. One was confirmed as compound (I-e3) by MALDI-TOF MS as described above. The remaining one was confirmed to be a metal body because it showed a unique spectral shape of a metal body in UV-vis measurement. Based on the reaction substrate, it was confirmed that the metal body was an aluminum body. Furthermore, the Rf value (developing solvent toluene) in silica gel thin layer chromatography (TLC) was 0.35 in the compound represented by formula (IV-e11) as a similar compound, and the above-mentioned aluminum body was 0.32, so the aluminum body was identified as compound (IV-e3).

[0471] (Synthesis Example 4)

[0472] <Synthesis of Compound (II-4)>

[0473] 52 parts of a compound represented by formula (II-4) (hereinafter referred to as compound (II-4)) were obtained as a colorless solid in the same manner as in Synthesis Example 1 except that 40 parts of 2,6-dichlorophenol was replaced with 32 parts of 4-chlorophenol (manufactured by Tokyo Chemical Industry Co., Ltd.) (yield 83%).

[0474]

[0475] (Example 4)

[0476] <Synthesis of Compound (I-e4)>

[0477] Except that 60 parts of compound (II-1) were replaced by 53 parts of compound (II-4) obtained in Synthesis Example 4, 19 parts of a compound represented by formula (I-e4) (hereinafter referred to as compound (I-e4)) (yield 35%) and 4.5 parts of a compound represented by formula (IV-e4) (hereinafter referred to as compound (IV-e4)) (yield 8%) were obtained in the same manner as in Example 1.

[0478]

[0479] <Identification of Compound (I-e4)>

[0480] (Mass Spectrometry) Ionization Mode = MALDI-TOF-: m / z = 1020

[0481] Exact molecular weight: 1018

[0482] <Identification of Compound (IV-e4)>

[0483] By silica gel thin layer chromatography (TLC), it was confirmed that there were only two colored components obtained in the reaction of Example 4. One was confirmed as compound (I-e4) by MALDI-TOF MS as described above. The remaining one was confirmed to be a metal body because it showed a unique spectral shape of a metal body in UV-vis measurement. Based on the reaction substrate, it was confirmed that the metal body was an aluminum body. Furthermore, the Rf value (developing solvent toluene) in silica gel thin layer chromatography (TLC) was 0.35 in the compound represented by formula (IV-e11) as a similar compound, and the above-mentioned aluminum body was 0.29, so the aluminum body was identified as compound (IV-e4).

[0484] (Synthesis Example 5)

[0485] <Synthesis of Compound (II-5)>

[0486] 69 parts of a compound represented by the formula (II-5) (hereinafter referred to as compound (II-5)) were obtained as a colorless solid in the same manner as in Synthesis Example 1 except that 45 parts of 2-isopropyl-4-chloro-5-methylphenol (manufactured by Tokyo Chemical Industry Co., Ltd.) was used instead of 40 parts of 2,6-dichlorophenol. (Yield: 90%)

[0487]

[0488] (Example 5)

[0489] <Synthesis of Compound (I-e5)>

[0490] Except that 60 parts of compound (II-1) were replaced by 65 parts of compound (II-5) obtained in Synthesis Example 5, 14 parts of a compound represented by formula (I-e5) (hereinafter referred to as compound (I-e5)) (yield 22%) and 3 parts of a compound represented by formula (IV-e5) (hereinafter referred to as compound (IV-e5)) (yield 4%) were obtained in the same manner as in Example 1.

[0491]

[0492] <Identification of Compound (I-e5)>

[0493] (Mass Spectrometry) Ionization Mode = MALDI-TOF-: m / z = 1244

[0494] Exact molecular weight: 1242

[0495] <Identification of Compound (IV-e5)>

[0496] By silica gel thin layer chromatography (TLC), it was confirmed that there were only two colored components obtained in the reaction of Example 5. One was confirmed as compound (I-e5) by MALDI-TOF MS as described above. The remaining one was confirmed to be a metal body because it showed a unique spectral shape of a metal body in UV-vis measurement. Based on the reaction substrate, it was confirmed that the metal body was an aluminum body. Furthermore, the Rf value (developing solvent toluene) in silica gel thin layer chromatography (TLC) was 0.35 for the compound represented by formula (IV-e11) as a similar compound, and 0.37 for the above-mentioned aluminum body, so the aluminum body was identified as compound (IV-e5).

[0497] (Synthesis Example 6)

[0498] <Synthesis of Compound (II-6)>

[0499] 68 parts of a compound represented by formula (II-6) (hereinafter referred to as compound (II-6)) were obtained as a colorless solid in the same manner as in Synthesis Example 1 except that 40 parts of 2,6-dichlorophenol was replaced with 44 parts of 2,4-dichloro-6-methylphenol (manufactured by Tokyo Chemical Industry Co., Ltd.) (yield 92%).

[0500]

[0501] (Example 6)

[0502] <Synthesis of Compound (I-e6)>

[0503] Except that 60 parts of compound (II-1) were replaced by 63 parts of compound (II-6) obtained in Synthesis Example 6, 18 parts of a compound represented by formula (I-e6) (hereinafter referred to as compound (I-e6)) (yield 29%) and 4 parts of a compound represented by formula (IV-e6) (hereinafter referred to as compound (IV-e6)) (yield 6%) were obtained in the same manner as in Example 1.

[0504]

[0505] <Identification of Compound (I-e6)>

[0506] (Mass Spectrometry) Ionization Mode = MALDI-TOF - :m / z=1214

[0507] Exact molecular weight: 1210

[0508] <Identification of Compound (IV-e6)>

[0509] By silica gel thin layer chromatography (TLC), it was confirmed that there were only two colored components obtained in the reaction of Example 6. One was confirmed as compound (I-e6) by MALDI-TOF MS as described above. The remaining one was confirmed to be a metal body because it showed a unique spectral shape of a metal body in UV-vis measurement. Based on the reaction substrate, the metal body was confirmed to be an aluminum body. Furthermore, the Rf value (developing solvent toluene) in silica gel thin layer chromatography (TLC) was 0.35 for the compound represented by formula (IV-e11) as a similar compound, and 0.33 for the above-mentioned aluminum body, so the aluminum body was identified as compound (IV-e6).

[0510] (Synthesis Example 7)

[0511] <Synthesis of Compound (II-7)>

[0512] 61 parts of a compound represented by formula (II-7) (hereinafter referred to as compound (II-7)) were obtained as a colorless solid in the same manner as in Synthesis Example 1 except that 35 parts of 2-chloro-6-methylphenol (manufactured by Tokyo Chemical Industry Co., Ltd.) was used instead of 40 parts of 2,6-dichlorophenol. (Yield: 92%).

[0513]

[0514] <Identification of Compound (II-7)>

[0515] (Mass Spectrometry) Ionization Mode = MALDI-TOF-: m / z = 268

[0516] Exact molecular weight: 268

[0517] (Example 7)

[0518] <Synthesis of Compound (I-e7)>

[0519] 27 parts of a compound represented by formula (I-e7) (hereinafter referred to as compound (I-e7)) were obtained in the same manner as in Example 1, except that 56 parts of compound (II-7) obtained in Synthesis Example 7 were used instead of 60 parts of compound (II-1). The compound represented by formula (IV-e7) was not detected.

[0520]

[0521] <Identification of Compound (I-e7)>

[0522] (Mass Spectrometry) Ionization Mode = MALDI-TOF-: m / z = 1076

[0523] Exact molecular weight: 1074

[0524] (Synthesis Example 8)

[0525] <Synthesis of Compound (II-8)>

[0526] 75 parts of a compound represented by formula (II-8) (hereinafter referred to as compound (II-8)) was obtained as a colorless solid in the same manner as in Synthesis Example 1 except that 40 parts of 2,6-dichlorophenol was replaced with 47 parts of 2,4-dichloro-3,5-dimethylphenol (manufactured by Tokyo Chemical Industry Co., Ltd.) (yield 96%).

[0527]

[0528] <Identification of Compound (II-8)>

[0529] (Mass Spectrometry) Ionization Mode = MALDI-TOF-: m / z = 316

[0530] Exact molecular weight: 316

[0531] (Example 8)

[0532] <Synthesis of Compound (I-e8)>

[0533] 30 parts of a compound represented by formula (I-e8) (hereinafter referred to as compound (I-e8)) were obtained in the same manner as in Example 1 except that 60 parts of compound (II-1) were replaced with 66 parts of compound (II-8) obtained in Synthesis Example 8 (yield 45%). It should be noted that although the compound represented by formula (IV-e8) (hereinafter referred to as compound (IV-e8)) was confirmed to be produced by thin layer chromatography (developing solvent: toluene, Rf value: 0.28), the amount produced was very small (yield less than 1%) and could not be isolated.

[0534]

[0535] <Identification of Compound (I-e8)>

[0536] (Mass Spectrometry) Ionization Mode = MALDI-TOF-: m / z = 1270

[0537] Exact molecular weight: 1266

[0538] (Synthesis Example 9)

[0539] <Synthesis of Compound (II-9)>

[0540] 70 parts of a compound represented by formula (II-9) (hereinafter referred to as compound (II-9)) was obtained as a colorless solid in the same manner as in Synthesis Example 1 except that 40 parts of 2,6-dichlorophenol was replaced with 44 parts of 1-chloro-2-naphthol (manufactured by Tokyo Chemical Industry Co., Ltd.) (yield 94%).

[0541]

[0542] <Identification of Compound (II-9)>

[0543] (Mass Spectrometry) Ionization Mode = MALDI-TOF-: m / z = 305

[0544] Exact molecular weight: 304

[0545] (Example 9)

[0546] <Synthesis of Compound (I-e9)>

[0547] 28 parts of a compound represented by formula (I-e9) (hereinafter referred to as compound (I-e9)) were obtained in the same manner as in Example 1, except that 60 parts of compound (II-1) were replaced with 63 parts of compound (II-9) obtained in Synthesis Example 9 (yield 44%). It should be noted that although the compound represented by formula (IV-e9) (hereinafter referred to as compound (IV-e9)) was confirmed to be produced by thin layer chromatography (developing solvent: toluene, Rf value: 0.33), the amount produced was very small (yield less than 1%) and could not be isolated.

[0548]

[0549] <Identification of Compound (I-e9)>

[0550] (Mass Spectrometry) Ionization Mode = MALDI-TOF-: m / z = 1221

[0551] Exact molecular weight: 1218

[0552] (Synthesis Example 10)

[0553] <Synthesis of Compound (II-10)>

[0554] 25 parts of a compound represented by formula (II-10) (hereinafter referred to as compound (II-10)) were obtained as a colorless solid in the same manner as in Synthesis Example 1 except that 42 parts of 5-chlorosalicylic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) was used instead of 40 parts of 2,6-dichlorophenol. (Yield: 34%).

[0555]

[0556] <Identification of Compound (II-10)>

[0557] (Mass Spectrometry) Ionization Mode = MALDI-TOF - :m / z=299

[0558] Exact molecular weight: 298

[0559] (Example 10)

[0560] <Synthesis of Compound (I-e10)>

[0561] 55 parts of a compound represented by formula (I-e10) (hereinafter referred to as compound (I-e10)) were obtained in the same manner as in Example 1, except that 60 parts of compound (II-1) were replaced with 62 parts of compound (II-10) obtained in Synthesis Example 10 (yield 88%). It should be noted that although the compound represented by formula (IV-e10) (hereinafter referred to as compound (IV-e10)) was confirmed to be produced by thin layer chromatography (developing solvent: toluene, Rf value: 0.31), the amount produced was very small (yield less than 1%) and could not be isolated.

[0562]

[0563] <Identification of Compound (I-e10)>

[0564] (Mass Spectrometry) Ionization Mode = MALDI-TOF - :m / z=1196

[0565] Exact molecular weight: 1194

[0566] (Synthesis Example 11)

[0567] <Synthesis of Compound (II-11)>

[0568] Under a nitrogen atmosphere, 171 parts of 3-nitrophthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.), 127 parts of 4-chlorophenol (manufactured by Tokyo Chemical Industry Co., Ltd.), 150 parts of potassium carbonate (manufactured by Kanto Chemical Co., Ltd.), and 1117 parts of dehydrated acetonitrile (manufactured by Kanto Chemical Co., Ltd.) were mixed, heated to 80°C, and stirred at the same temperature for 10 hours. The reaction solution was cooled to room temperature (18 to 24°C) and filtered to obtain filtrate A and residue A. Residue A was washed with 559 parts of acetonitrile, and the obtained acetonitrile solution and filtrate A were combined, and the solvent in the solution was distilled off. The obtained residue was washed with 570 parts of ion-exchanged water and dried to obtain 209 parts of a compound represented by formula (II-11) (hereinafter referred to as compound (II-11)) as a colorless solid (yield 83%).

[0569]

[0570] <Identification of Compound (II-11)>

[0571] (Mass Spectrometry) Ionization Mode = MALDI-TOF - :m / z=255

[0572] Exact molecular weight: 254

[0573] (Example 11)

[0574] <Synthesis of Compound (I-e11)>

[0575] Under nitrogen atmosphere, 53 parts of compound (II-11) prepared in Synthesis Example 11, 7.5 parts of anhydrous aluminum chloride (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.), 435 parts of triethylene glycol (manufactured by Tokyo Chemical Industry Co., Ltd.) and 47 parts of 1,8-diazabicyclo[5,4,0]-7-undecene (manufactured by Tokyo Chemical Industry Co., Ltd.) were mixed and heated at 100°C for 30 hours. After the reaction was completed, the reaction solution was cooled to room temperature (18 to 24°C) and poured into 600 parts of ion exchange water. The precipitated solid was separated by decantation in the order of 420 parts of methanol twice and 450 parts of acetone once. The crude product was purified by silica gel column chromatography (developing solvent: gradient from toluene to tetrahydrofuran) to obtain 26 parts (yield 49%) of the compound represented by formula (I-e11) (hereinafter referred to as compound (I-e11)) and 2.2 parts (yield 4%) of the compound represented by formula (IV-e11) (hereinafter referred to as compound (IV-e11)) as solids.

[0576]

[0577] <Identification of Compound (I-e11)>

[0578] (Mass Spectrometry) Ionization Mode = MALDI-TOF - :m / z=1021

[0579] Exact molecular weight: 1018

[0580] <Identification of Compound (IV-e11)>

[0581] (Mass Spectrometry) Ionization Mode = MALDI-TOF - :m / z=1081

[0582] Exact molecular weight: 1078

[0583] (Synthesis Example 12)

[0584] <Synthesis of Compound (II-12)>

[0585] 224 parts of a compound represented by formula (II-12) (hereinafter referred to as compound (II-12)) was obtained as a colorless solid in the same manner as in Synthesis Example 11 except that 127 parts of 4-chlorophenol was replaced with 127 parts of 2-chlorophenol (manufactured by Tokyo Chemical Industry Co., Ltd.) (yield 89%).

[0586]

[0587] (Example 12)

[0588] <Synthesis of Compound (I-e12)>

[0589] Except that 53 parts of compound (II-11) were replaced by 53 parts of compound (II-12) obtained in Synthesis Example 12, 22 parts of a compound represented by formula (I-e12) (hereinafter referred to as compound (I-e12)) (yield 42%) and 2.8 parts of a compound represented by formula (IV-e12) (hereinafter referred to as compound (IV-e12)) (yield 5%) were obtained in the same manner as in Example 11.

[0590]

[0591] <Identification of Compound (I-e12)>

[0592] (Mass Spectrometry) Ionization Mode = MALDI-TOF - :m / z=1021

[0593] Exact molecular weight: 1018

[0594] <Identification of Compound (IV-e12)>

[0595] (Mass Spectrometry) Ionization Mode = MALDI-TOF - :m / z=1081

[0596] Exact molecular weight: 1078

[0597] (Synthesis Example 13)

[0598] <Synthesis of Compound (II-13)>

[0599] 263 parts of a compound represented by the formula (II-13) (hereinafter referred to as compound (II-13)) was obtained as a colorless solid in the same manner as in Synthesis Example 11 except that 127 parts of 4-chlorophenol was replaced with 154 parts of 2,6-dimethyl-4-chlorophenol (manufactured by Tokyo Chemical Industry Co., Ltd.) (yield 94%).

[0600]

[0601] (Example 13)

[0602] <Synthesis of Compound (I-e13)>

[0603] 11 parts (yield 18%) of a compound represented by formula (I-e13) (hereinafter referred to as compound (I-e13)) were obtained in the same manner as in Example 11, except that 53 parts of compound (II-11) were replaced with 59 parts of compound (II-13) obtained in Synthesis Example 13. It should be noted that although the compound represented by formula (IV-e13) (hereinafter referred to as compound (IV-e13)) was confirmed to be produced by thin layer chromatography (developing solvent: toluene, Rf value: 0.35), the amount produced was very small (yield 1% or less) and could not be isolated.

[0604]

[0605] <Identification of Compound (I-e13)>

[0606] (Mass Spectrometry) Ionization Mode = MALDI-TOF - :m / z=1132

[0607] Exact molecular weight: 1130

[0608] (Synthesis Example 14)

[0609] <Synthesis of Compound (II-14)>

[0610] Except that 40 parts of 2,6-dichlorophenol was replaced with 35 parts of 4-chloro-2-methylphenol (manufactured by Tokyo Chemical Industry Co., Ltd.), 56 parts of a compound represented by formula (II-14) (hereinafter referred to as compound (II-14)) were obtained as a white solid in the same manner as in Synthesis Example 1 (yield 85%).

[0611]

[0612] <Identification of Compound (II-14)>

[0613] (Mass Spectrometry) Ionization Mode = MALDI-TOF - :m / z=268

[0614] Exact molecular weight: 268

[0615] (Example 14)

[0616] <Synthesis of Compound (I-e14)>

[0617] 21 parts of a compound represented by formula (I-e14) (hereinafter referred to as compound (I-e14)) were obtained in the same manner as in Example 1, except that 56 parts of compound (II-14) obtained in Synthesis Example 14 were used instead of 60 parts of compound (II-1). The compound represented by formula (IV-e14) was not detected.

[0618]

[0619] <Identification of Compound (I-e14)>

[0620] (Mass Spectrometry) Ionization Mode = MALDI-TOF - :m / z=1076

[0621] Exact molecular weight: 1074

[0622] (Synthesis Example 15)

[0623] <Synthesis of Compound (II-15)>

[0624] 75 parts of a compound represented by formula (II-15) (hereinafter referred to as compound (II-15)) was obtained as a white solid in the same manner as in Synthesis Example 1 except that 40 parts of 2,6-dichlorophenol was replaced with 51 parts of 2-bromo-4-chlorophenol (manufactured by Tokyo Chemical Industry Co., Ltd.) (yield 92%).

[0625]

[0626] <Identification of Compound (II-15)>

[0627] (Mass Spectrometry) Ionization Mode = MALDI-TOF-: m / z = 332

[0628] Exact molecular weight: 332

[0629] (Example 15)

[0630] <Synthesis of Compound (I-e15)>

[0631] Except that 53 parts of compound (II-11) were replaced by 69 parts of compound (II-15) obtained in Synthesis Example 15, 19 parts of the compound represented by formula (I-e15) (hereinafter referred to as compound (I-e15)) (yield 28%) and 2.1 parts of the compound represented by formula (IV-e15) (hereinafter referred to as compound (IV-e15)) (yield 3%) were obtained in the same manner as in Example 11.

[0632]

[0633] <Identification of Compound (I-e15)>

[0634] (Mass Spectrometry) Ionization Mode = MALDI-TOF - :m / z=1334

[0635] Exact molecular weight: 1330

[0636] <Identification of Compound (IV-e15)>

[0637] By silica gel thin layer chromatography (TLC), it was confirmed that there were only two kinds of colored components obtained in the reaction of Example 15. One kind was confirmed as compound (I-e15) by MALDI-TOF MS as described above. The remaining one was confirmed as a metal body because it showed a unique spectral shape of a metal body in UV-vis measurement. Based on the reaction substrate, it was confirmed that the metal body was an aluminum body. Furthermore, the Rf value (developing solvent toluene) in silica gel thin layer chromatography (TLC) was 0.35 for the compound represented by formula (IV-e11) as a similar compound, and 0.31 for the above-mentioned aluminum body, so the aluminum body was identified as compound (IV-e15).

[0638] (Reference Example 1)

[0639] <Synthesis of Compound (I-e6)>

[0640] 2.5 parts of compound (I-e6) were obtained in the same manner as in Example 6 except that 8.7 parts of anhydrous aluminum chloride was not used (yield 4%).

[0641]

[0642] [Table 6]

[0643]

[0644] In Table 6, the molar ratio (Compound (I) / Compound (IV)) represents the amount of Compound (I) isolated in each Example and Reference Example relative to 1 mol of Compound (IV) (i.e., aluminum phthalocyanine (IV)).

[0645] (Resin Synthesis Example 1)

[0646] <Synthesis of Resin B-1>

[0647] An appropriate amount of nitrogen was introduced into a flask equipped with a reflux condenser, a dropping funnel, and a stirrer to replace the atmosphere with nitrogen, and 280 parts of propylene glycol monomethyl ether acetate was 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 ester and 3,4-epoxytricyclic acrylate [5.2.1.0 2 ,6 ] A mixed solution of 289 parts of a mixture of decane-9-yl ester (containing a ratio of 1:1 in molar ratio) and 125 parts of propylene glycol monomethyl ether acetate. On the other hand, a solution obtained by dissolving 33 parts of 2,2-azobis(2,4-dimethylvaleronitrile) in 235 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After the addition was completed, the mixture was kept at 80°C for 4 hours and then cooled to room temperature to obtain a copolymer (resin B-1) solution having a solid content of 35.1% and a viscosity of 125 mPa·s measured by a B-type viscometer (23°C). The weight average molecular weight Mw of the resulting copolymer was 9.2×10 3 , the dispersion degree was 2.08, and the acid value converted to solid content was 77 mg-KOH / g. Resin B-1 has the following structural units.

[0648]

[0649] (Resin Synthesis Example 2)

[0650] <Synthesis of Resin B-2>

[0651] An appropriate amount of nitrogen was introduced into a flask equipped with a reflux condenser, a dropping funnel, and a stirrer to replace the atmosphere with nitrogen, and 350 parts of propylene glycol monomethyl ether acetate was added, and the mixture was heated to 85°C while stirring. Next, 70 parts of acrylic acid and 3,4-epoxytricyclo[5.2.1.0 2,6 ]decane-8-yl ester and 3,4-epoxytricyclic acrylate [5.2.1.0 2 ,6] A mixed solution of 202 parts of a mixture of a mixture of decane-9-yl ester (containing a ratio of 1:1 in terms of molar ratio), 78 parts of vinyltoluene (isomer mixture), and 100 parts of propylene glycol monomethyl ether acetate. On the other hand, a solution obtained by dissolving 33 parts of a polymerization initiator 2,2-azobis(2,4-dimethylvaleronitrile) in 167 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. After the addition of the initiator solution was completed, it was kept at 85°C for 4 hours and cooled to room temperature to obtain a copolymer (resin B-2) solution having a viscosity of 431 mPa·s and a solid content of 38.1% as measured by a B-type viscometer (23°C). The weight average molecular weight Mw of the resulting copolymer is 1.04×10 4 , the degree of dispersion was 2.03, and the acid value converted to solid content was 139 mg-KOH / g. Resin B-2 has the following structural units.

[0652]

[0653] In addition, the polystyrene-equivalent weight average molecular weight (Mw) and number average molecular weight (Mn) of the resin were measured by the GPC method under the following conditions.

[0654] Equipment: HLC-8120GPC (manufactured by Tosoh Corporation)

[0655] Column: TSK-GELG2000HXL

[0656] Column temperature: 40°C

[0657] Solvent: Tetrahydrofuran

[0658] Flow rate: 1.0mL / min

[0659] Solid content concentration of the analysis sample: 0.001 to 0.01 mass%

[0660] Injection volume: 50 μL

[0661] Detector: RI

[0662] Calibration standard substances: TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Corporation)

[0663] The ratio (Mw / Mn) of the polystyrene-equivalent weight average molecular weight and the number average molecular weight obtained above was defined as the degree of dispersion.

[0664] <Dispersion Preparation Example 1>

[0665] 5.0 parts of the compound (I-e3) obtained in Example 3, 3.5 parts of a dispersant (BYKLPN-6919 manufactured by BYK) (calculated as solid content), 3.5 parts of a resin B-2 (calculated as solid content), 78 parts of propylene glycol monomethyl ether acetate, and 10 parts of diacetone alcohol are mixed, 300 parts of 0.2 mm zirconium oxide beads are added and shaken, and the zirconium oxide beads are removed by filtration to obtain a dispersion (P-1).

[0666] <Dispersion Preparation Examples 2 to 7>

[0667] Dispersions (P-2) to (P-7) were obtained by the same method as in Dispersion Preparation Example 1 except that the compound (I-e3) in Dispersion Preparation Example 1 was changed to the following compound.

[0668] Dispersion liquid (P-2): Compound (I-e5) obtained in Example 5

[0669] Dispersion liquid (P-3): Compound (I-e11) obtained in Example 11

[0670] Dispersion liquid (P-4): Compound (I-e6) obtained in Example 6

[0671] Dispersion liquid (P-5): Compound (I-e12) obtained in Example 12

[0672] Dispersion liquid (P-6): Compound (I-e15) obtained in Example 15

[0673] Dispersion liquid (P-7): Compound (I-e14) obtained in Example 14

[0674] <Dispersion Preparation Example 8>

[0675] The following components were mixed, and the pigment was dispersed using a bead mill to obtain a dispersion (P-c1).

[0676]

[0677] <Dispersion Preparation Example 9>

[0678] The following components were mixed, and the pigment was dispersed using a bead mill to obtain a dispersion (A-1).

[0679]

[0680] <Dispersion Preparation Example 10>

[0681] The following components were mixed, and the pigment was dispersed using a bead mill to obtain a dispersion (A-2).

[0682]

[0683] <Examples A1 to A11 and Comparative Examples A1 to A2>

[0684] (Preparation of Colored Resin Composition)

[0685] The components described in Table 7 were mixed to obtain colored resin compositions E1 to E11 and C1 to C2, respectively. In the preparation of the colored resin composition, the ratio of the colorant in the solid content of the colored resin composition was 40% by mass in Examples A1 to A3, A5 to A8, and Comparative Example A1, and was 35% by mass in Examples A4, A9 to A11, and Comparative Example A2.

[0686] [Table 7]

[0687]

[0688] In Table 7, each component represents the following compound.

[0689] Resin (B-1): Resin B-1 (solid content conversion)

[0690] Polymerizable compound (C-1): dipentaerythritol polyacrylate; trade name A-9550; manufactured by Shin-Nakamura Chemical Industry Co., Ltd.

[0691] Polymerization initiator (D-1): N-acetoxy-1-(4-phenylthiophenyl)-3-cyclohexylpropane-1-one-2-imine; trade name PBG-327; O-acyl oxime compound; manufactured by Changzhou Qiangli Electronic New Materials Co., Ltd.

[0692] Leveling agent (F-1): polyether-modified silicone oil: trade name Toray Silicone SH8400; manufactured by Dow Corning Toray Co., Ltd.

[0693] Solvent (E-1): Propylene glycol monomethyl ether acetate

[0694] In addition, the amount described in the column of the solvent (E-1) in Table 7 represents the total amount including the amount of propylene glycol monomethyl ether acetate contained in the resin (B-1).

[0695] <Examples B1 to B20 and Comparative Examples B1 to B4>

[0696] (Production of color coating film)

[0697] The colored resin compositions E1 to E11 and C1 to C2 were applied onto a 5 cm square glass substrate (EAGLE 2000; manufactured by CORNING) by spin coating, and then pre-baked at 100°C for 3 minutes to form a colored composition layer. After cooling, an exposure machine (TME-150RSK; manufactured by TOPCON Corporation) was used without using a photomask in an air atmosphere at 100 mJ / cm 2 The coloring composition layer after light irradiation was post-baked in an oven at 230°C for 20 minutes to obtain a color coating film. After cooling, the film thickness of the obtained color coating film was measured using a film thickness measuring device (DEKTAK3; manufactured by Japan Vacuum Technology Co., Ltd.). The film thickness of the obtained color coating film was the same as 2.0 μm in all examples and comparative examples.

[0698] <Evaluation>

[0699] (1) Measurement of initial brightness

[0700] The spectrum of the obtained colored coating film was measured using a colorimeter (OSP-SP-200; manufactured by Olympus Corporation), and the xy chromaticity coordinates (x, y) and the stimulus value Y in the XYZ colorimetric system of CIE were measured using the characteristic function of the C light source. A larger value of Y means higher brightness.

[0701] (2) Evaluation of brightness unevenness suppression

[0702] An ultraviolet cut filter (COLORED OPTICAL GLASS L38; manufactured by HOYA Co., Ltd.; cuts off light below 380 nm) was placed on the obtained colored coating film, and a light irradiation test with a xenon lamp was carried out for 48 or 120 hours (irradiation time is shown in Table 8) using a light resistance tester (SUNTEST CPS+: manufactured by Toyo Seiki Seisaku-sho, Ltd.). The relative value (%) of the stimulation value Y after the light irradiation test when the stimulation value Y before the light irradiation test (the initial brightness obtained in (1) above) was set to 100% was calculated as the "brightness change rate", and the evaluation was performed according to the following evaluation criteria. The results are shown in Table 8. When the brightness change rate under the present measurement conditions is 98.0% or more, the brightness difference between the peripheral part and the central part of the colored filter after long-term use becomes difficult for the human eye to distinguish, and it can be said that the performance is sufficient as a color filter.

[0703] Brightness unevenness suppression ◎: Brightness change rate is 99.0% or more

[0704] Brightness unevenness suppression ○: Brightness change rate is 98.0% or more and less than 99.0%

[0705] Brightness unevenness suppression ×: Brightness change rate less than 98.0%

[0706] [Table 8]

[0707]

[0708] (3) Evaluation of green spectral characteristics

[0709] The color coating film after the light irradiation test in the above "(2) Evaluation of brightness unevenness suppression" was measured using an ultraviolet visible near infrared absorption spectrometer (Japan Spectroscopy: V-770) to evaluate the transmittance of the green region when the film thickness of the color coating film was 2.0 μm. The results are shown in Table 9. If the transmittance at 550 nm is 35% to 99% and the transmittance at 620 nm is 0.1% to 20%, it can be said that the green filter in the color filter shows good spectral characteristics even after long-term use.

[0710] [Table 9]

[0711]

Claims

1. A compound represented by formula (I), In formula (I), R 1 ~R 16 Each independently represents a hydrogen atom, a chlorine atom, a hydrocarbon group having 1 to 6 carbon atoms which may have a substituent, a group represented by formula (i-a), a group represented by formula (i-b), or a group represented by formula (i-c), wherein -CH2- contained in the hydrocarbon group may be substituted by -O- or -CO-, wherein, R 1 ~R 16 At least one of the groups represents a group represented by formula (i-a), a group represented by formula (i-b) or a group represented by formula (i-c); when there are multiple groups represented by formula (i-a), they may be the same or different; when there are multiple groups represented by formula (i-b), they may be the same or different; when there are multiple groups represented by formula (i-c), they may be the same or different; In formula (i-a), R a1 ~R a5 Each independently represents a hydrogen atom, a chlorine atom, a bromine atom, a carboxyl group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, wherein the -CH2- in the hydrocarbon group may be substituted by -O- or -CO-, wherein R a1 ~R a5 1 to 3 of them are chlorine atoms, * indicates the bonding site, In formula (i-b), R b1 ~R b7 Each independently represents a hydrogen atom, a chlorine atom, a bromine atom, a carboxyl group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, wherein the -CH2- in the hydrocarbon group may be substituted by -O- or -CO-, wherein R b1 ~R b7 1 to 3 of them are chlorine atoms, * indicates the bonding site, In formula (i-c), R c1 ~R c7 Each independently represents a hydrogen atom, a chlorine atom, a bromine atom, a carboxyl group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, wherein the -CH2- in the hydrocarbon group may be substituted by -O- or -CO-, wherein R c1 ~R c7 1 to 3 of them are chlorine atoms, and * indicates a bonding site.

2. The compound according to claim 1, wherein R 1 ~R 4 At least one of them is a group represented by formula (i-a), formula (i-b) or formula (i-c), R 5 ~R 8 At least one of them is a group represented by formula (i-a), formula (i-b) or formula (i-c), R 9 ~R 12 At least one of them is a group represented by formula (i-a), formula (i-b) or formula (i-c), and R 13 ~R 16 At least one of them is a group represented by formula (i-a), formula (i-b) or formula (i-c).

3. The compound according to claim 2, wherein R 2 and R 3 At least one of them is a group represented by formula (i-a), formula (i-b) or formula (i-c), R 6 and R 7 At least one of them is a group represented by formula (i-a), formula (i-b) or formula (i-c), R 10 and R 11 At least one of them is a group represented by formula (i-a), formula (i-b) or formula (i-c), and R 14 and R 15 At least one of them is a group represented by formula (i-a), formula (i-b) or formula (i-c), R 1 , R 4 , R 5 , R 8 , R 9 , R 12 , R 13 and R 16 A hydrogen atom.

4. The compound according to claim 3, wherein R 2 and R 3 Any one of them is a group represented by formula (i-a), formula (i-b) or formula (i-c), R 6 and R 7 Any one of them is a group represented by formula (i-a), formula (i-b) or formula (i-c), R 10 and R 11 Any one of them is a group represented by formula (i-a), formula (i-b) or formula (i-c), and R 14 and R 15 Any one of them is a group represented by formula (i-a), formula (i-b) or formula (i-c), R 1 , R 4 , R 5 , R 8 , R 9 , R 12 , R 13 and R 16 is a hydrogen atom, The four groups represented by the formula (i-a), the formula (i-b) or the formula (i-c) in the formula (I) are the same groups.

5. The compound according to claim 2, wherein R 1 , R 5 , R 9 and R 13 are each independently a group represented by formula (i-a), formula (i-b) or formula (i-c), R 2 ~R 4 , R 6 ~R 8 , R 10 ~R 12 and R 14 ~R 16 A hydrogen atom. 6 . A colored resin composition comprising a colorant and a resin, wherein the colorant comprises the compound according to claim 1 or 2.

7. The colored resin composition according to claim 6, wherein It further contains a polymerizable compound and a polymerization initiator. 8 . A color filter formed from the colored resin composition according to claim 7 .

9. A display device comprising the color filter according to claim 8. 10 . A solid-state imaging element comprising the color filter according to claim 8 .

11. A method for producing a compound represented by formula (I), comprising reacting compounds represented by formulas (II-1) to (II-4) in the presence of a base and a compound represented by formula (III). In formula (I), R 1 ~R 16 Each independently represents a hydrogen atom, a chlorine atom, a hydrocarbon group having 1 to 6 carbon atoms which may have a substituent, a group represented by formula (i-a), a group represented by formula (i-b), or a group represented by formula (i-c), wherein -CH2- contained in the hydrocarbon group may be substituted by -O- or -CO-, wherein, R 1 ~R 16 At least one of the groups represents a group represented by formula (i-a), a group represented by formula (i-b), or a group represented by formula (i-c); when there are multiple groups represented by formula (i-a), they may be the same or different; when there are multiple groups represented by formula (i-b), they may be the same or different; when there are multiple groups represented by formula (i-c), they may be the same or different; In formula (i-a), R a1 ~R a5 Each independently represents a hydrogen atom, a chlorine atom, a bromine atom, a carboxyl group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, wherein the -CH2- in the hydrocarbon group may be substituted by -O- or -CO-, wherein R a1 ~R a5 1 to 3 of them are chlorine atoms, * indicates the bonding site, In formula (i-b), R b1 ~R b7 Each independently represents a hydrogen atom, a chlorine atom, a bromine atom, a carboxyl group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, wherein the -CH2- in the hydrocarbon group may be substituted by -O- or -CO-, wherein R b1 ~R b7 1 to 3 of them are chlorine atoms, In formula (i-c), Rc 1 ~Rc 7 Each independently represents a hydrogen atom, a chlorine atom, a bromine atom, a carboxyl group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, wherein the -CH2- in the hydrocarbon group may be substituted by -O- or -CO-, wherein Rc 1 ~Rc 7 1 to 3 of them are chlorine atoms, and * indicates the bonding site; AIXM3(III) In formula (III), X M Represents a halogen atom, a hydroxyl group, or OR M Ji, R M represents a hydrocarbon group having 1 to 6 carbon atoms; In formulas (II-1) to (II-4), R 1 ~R 16 Same meaning as above.

12. The manufacturing method according to claim 11, wherein: The amount of the compound represented by formula (III) used is 0.25 mol to 0.40 mol per 1 mol of the total amount of the compounds represented by formulae (II-1) to (II-4).

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