Colored resin composition

Abstract

The present invention aims to provide a colored resin composition containing an aluminum phthalocyanine dye that can form a colored coating film without generating foreign matter (preferably a colored coating film without generating foreign matter and having good adhesion). The colored resin composition of the present invention contains a colorant, a compound represented by formula (DA), a resin, and a solvent, wherein the colorant contains an aluminum phthalocyanine dye. [In formula (DA), R d1 represents a hydrocarbon group having 1 to 12 carbon atoms which may have a substituent. When the hydrocarbon group has 2 to 12 carbon atoms and the hydrocarbon group has -CH2-, the -CH2- may be substituted with -O-, -S- or -CO-. d2 and R d3 each independently represents a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms which may have a substituent, or represents R d2 With R d3 Bonded with -CO-NR d1 -CO- together to form a ring. ]

Description

Technical Field

[0001] The present invention relates to a colored resin composition, a color filter, a display device, and a solid-state imaging element. 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 elements such as CCD or CMOS sensors are manufactured from colored resin compositions. As colorants for the colored resin compositions, aluminum phthalocyanine pigments are known. Patent Document 1 describes a color filter coloring composition containing an aluminum phthalocyanine pigment.

[0003] On the other hand, Patent Document 2 describes the following: In order to improve the flow characteristics of a coloring composition in which nanomaterials such as nano organic pigments and dyes are dispersed and to achieve a high-quality coloring composition with low viscosity, low thixotropy, and a dispersed state that is stable over time and has little influence or change on the resistance value, an additive having a specific structure represented by the general formula (1) is applied.

[0004] Prior art literature

[0005] Patent Literature

[0006] Patent Document 1: Japanese Patent Application Publication No. 2016-075837

[0007] Patent Document 2: Japanese Patent Application Publication No. 2018-150498 Summary of the invention

[0008] The present inventors have conducted research and found that foreign matter is likely to be generated when a colored coating film is formed from a colored resin composition containing an aluminum phthalocyanine dye. In addition, it is also found that the formed colored coating film is likely to peel off.

[0009] Therefore, an object of the present invention is to provide a colored resin composition containing an aluminum phthalocyanine dye that can form a colored coating film that does not generate foreign matter (preferably a colored coating film that does not generate foreign matter and has good adhesion).

[0010] The present invention includes the following inventions.

[0011] [1] A colored resin composition comprising a colorant, a compound represented by formula (DA), a resin and a solvent,

[0012] The colorant includes an aluminum phthalocyanine pigment.

[0013]

[0014] [In formula (DA),

[0015] R d1It represents a hydrocarbon group having 1 to 12 carbon atoms which may have a substituent. When the hydrocarbon group has 2 to 12 carbon atoms and has -CH2-, the -CH2- may be substituted with -O-, -S- or -CO-.

[0016] R d2 and R d3 each independently represents a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms which may have a substituent, or represents R d2 With R d3 Bonding and -CO-NR d1 -CO- together to form a ring.]

[0017] [2] The colored resin composition according to [1], wherein the aluminum phthalocyanine dye is a compound represented by formula (Xa) or formula (Xb).

[0018]

[0019] [In formula (Xa),

[0020] Z represents a hydroxyl group, a chlorine atom, or -OP(=O)R a1 R a2 , or -O-SiR a3 R a4 R a5 .

[0021] R a1 ~R a5 Each independently represents a hydrogen atom, a hydroxyl group, or a hydrocarbon group having 1 to 21 carbon atoms which may have a substituent, and R a1 With R a2 or R a3 ~R a5 Any two of them may be bonded to each other to form a ring. When the hydrocarbon group has 2 to 21 carbon atoms and the hydrocarbon group has -CH2-, the -CH2- may be substituted with -O-, -S- or -CO-.

[0022] X x1 ~X x4 Each independently represents -R x4 、-OR x4 、-SR x4 , a halogen atom, a nitro group, or a sulfamoyl group which may have a substituent.

[0023] R x4 It represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and when the hydrocarbon group has 2 to 21 carbon atoms and the hydrocarbon group has -CH2-, the -CH2- may be substituted by -O-, -S- or -CO-.

[0024] nx1 to nx4 each independently represent an integer of 0 to 4.

[0025] In formula (Xb),

[0026] L stands for -O-SiR a6 R a7 -O-、-O-SiR a8 R a9 -O-SiR a10 R a11 -O-, or -OP(=O)R a12 -O-.

[0027] R a6 ~R a12 Each independently represents a hydrogen atom, a hydroxyl group, or a hydrocarbon group having 1 to 21 carbon atoms which may have a substituent, and R a6 With R a7 , R a8 With R a9 or R a10 With R a11 They may be bonded to each other to form a ring. When the hydrocarbon group has 2 to 21 carbon atoms and the hydrocarbon group has -CH2-, the -CH2- may be substituted with -O-, -S- or -CO-.

[0028] X x5 ~X x12 Each independently represents -R x5 、-OR x5 、-SR x5 , a halogen atom, a nitro group, or a sulfamoyl group which may have a substituent.

[0029] R x5 It represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.

[0030] nx5 to nx12 each independently represent an integer from 0 to 4.]

[0031] [3] The colored resin composition according to [2], wherein the compound represented by the formula (Xa) is a compound represented by the formula (XI), and the compound represented by the formula (Xb) is a compound represented by the formula (XII).

[0032]

[0033]

[0034] [In formula (XI),

[0035] R x1represents an unsaturated hydrocarbon group having 2 to 20 carbon atoms which may have a substituent or an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, R x2 represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, or a Z-linked x2 With R xI single key.

[0036] Z x1 and Z x2 Each independently represents a single bond or an oxygen atom.

[0037] X x1 ~X x4 , nx1~nx4 are the same as above.

[0038] In formula (XII),

[0039] R x3 It represents an unsaturated hydrocarbon group having 2 to 20 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent.

[0040] Z x3 represents a single bond or an oxygen atom.

[0041] X x5 ~X x12 , nx5~nx12 are the same as above. ]

[0042] [4] The colored resin composition according to [1], wherein the aluminum phthalocyanine dye is a compound represented by formula (YI) or formula (YII).

[0043]

[0044]

[0045] [In formula (YI),

[0046] R y1 It represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.

[0047] R y2 represents a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 20 carbon atoms, or a Z-linked y3 With R y1 single key.

[0048] Y 1 and Z y1 Each independently represents an oxygen atom or a sulfur atom.

[0049] Z y2 and Z y3 Each independently represents a single bond, an oxygen atom or a sulfur atom.

[0050] Among them, Y 1 , Z y1 , Z y2 and Z y3 At least one of them represents a sulfur atom.

[0051] X y1 ~X y4 Each independently represents -R y4 、-OR y4 、-SR y4 , a halogen atom, a nitro group or a sulfamoyl group which may have a substituent.

[0052] R y4 It represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.

[0053] ny1 to ny4 each independently represent an integer of 0 to 4.

[0054] In formula (YII),

[0055] R y3 It represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.

[0056] Y 2 and Z y4 Each independently represents an oxygen atom or a sulfur atom.

[0057] Z y5 represents a single bond, an oxygen atom, or a sulfur atom.

[0058] Among them, Y 2 , Z y4 and Z y5 At least one of them represents a sulfur atom.

[0059] X y5 ~X y12 Each independently represents -R y5 、-OR y5 、-SR y5 , a halogen atom, a nitro group or a sulfamoyl group which may have a substituent.

[0060] R y5 It represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.

[0061] ny5 to ny12 each independently represent an integer of 0 to 4.]

[0062] [5] The colored resin composition according to any one of [1] to [4], further comprising a polymerizable compound and a polymerization initiator.

[0063] [6] A color filter formed from the colored resin composition according to any one of [1] to [5].

[0064] [7] A display device comprising the color filter described in [6].

[0065] [8] A solid-state imaging element comprising the color filter described in [7].

[0066] According to the colored resin composition of the present invention, a colored coating film that does not generate foreign matter (preferably a colored coating film that does not generate foreign matter and has good adhesion) can be formed. DETAILED DESCRIPTION

[0067] 《Coloring resin composition》

[0068] The present invention includes a colored resin composition comprising a colorant (hereinafter, sometimes referred to as a colorant (A)), a compound represented by formula (DA), a resin (hereinafter, sometimes referred to as a resin (B)), and a solvent (hereinafter, sometimes referred to as a solvent (E)), wherein the colorant contains an aluminum phthalocyanine dye.

[0069] The present invention also preferably includes a colored resin composition containing 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)).

[0070] The colored resin composition of the present invention may contain a leveling agent (hereinafter, sometimes referred to as a leveling agent (F)).

[0071] In the present specification, the compounds exemplified as the components may be used alone or in combination of two or more, unless otherwise specified.

[0072] According to the colored resin composition of the present invention, a colored coating film without generating foreign matter can be formed. Moreover, the obtained colored coating film has good adhesion to the substrate. In addition, according to the colored resin composition of the present invention, it is also possible to expect improvements in exposure sensitivity, development speed, residue after development, residual film rate, and pattern shape.

[0073] <Colorant (A)>

[0074] The colored resin composition of the present invention contains an aluminum phthalocyanine dye as a colorant. Specifically, the aluminum phthalocyanine dye is a dye having a phthalocyanine skeleton and forming a complex with aluminum.

[0075] Specifically, the aluminum phthalocyanine dye is preferably a compound represented by formula (Xa) or formula (Xb). Below, the partial structure of the compound represented by formula (Xa) or formula (Xb) is given to explain the present invention in more detail. It should be noted that the definition common to formula (XI) or formula (XII) is described later.

[0076]

[0077] [In formula (Xa),

[0078] Z represents a hydroxyl group, a chlorine atom, or -OP(=O)R a1 R a2 , or -O-SiR a3 R a4 R a5 .

[0079] R a1 ~R a5 Each independently represents a hydrogen atom, a hydroxyl group, or a hydrocarbon group having 1 to 21 carbon atoms which may have a substituent, and R a1 With R a2 or R a3 ~R a5 Any two of them may be bonded to each other to form a ring. When the hydrocarbon group has 2 to 21 carbon atoms and the hydrocarbon group has -CH2-, the -CH2- may be substituted with -O-, -S- or -CO-.

[0080] X x1 ~X x4 Each independently represents -R x4 、-OR x4 、-SR x4 , a halogen atom, a nitro group, or a sulfamoyl group which may have a substituent.

[0081] R x4 It represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and when the hydrocarbon group has 2 to 21 carbon atoms and the hydrocarbon group has -CH2-, the -CH2- may be substituted by -O-, -S- or -CO-.

[0082] nx1 to nx4 each independently represent an integer of 0 to 4.

[0083] In formula (Xb),

[0084] L stands for -O-SiR a6 R a7 -O-、-O-SiR a8 R a9 -O-SiR a10 R a11 -O-, or -OP(=O)R a12 -O-.

[0085] R a6 ~R a12 Each independently represents a hydrogen atom, a hydroxyl group, or a hydrocarbon group having 1 to 21 carbon atoms which may have a substituent, and R a6 With R a7, R a8 With R a9 or R a10 With R a11 They may be bonded to each other to form a ring. When the hydrocarbon group has 2 to 21 carbon atoms and the hydrocarbon group has -CH2-, the -CH2- may be substituted with -O-, -S- or -CO-.

[0086] X x5 ~X x12 Each independently represents -R x5 、-OR x5 、-SR x5 , a halogen atom, a nitro group, or a sulfamoyl group which may have a substituent.

[0087] R x5 It represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.

[0088] nx5 to nx12 each independently represent an integer from 0 to 4.]

[0089] R a1 ~R a12 It represents a hydrocarbon group having 1 to 21 carbon atoms which may have a substituent.

[0090] R a1 With R a2 , R a3 ~R a5 Any two of R a6 With R a7 , R a8 With R a9 , or R a10 With R a11 They may be bonded to each other to form a ring.

[0091] When the hydrocarbon group has 2 to 21 carbon atoms and the hydrocarbon group has -CH2-, the -CH2- may be substituted with -O-, -S- or -CO-. In the hydrocarbon group having 2 to 21 carbon atoms, adjacent -CH2- are not substituted with -O- and / or -S- at the same time, and the terminal -CH2- is not substituted with -O-, -S- or -CO-.

[0092] It should be noted that when -CH2- in a hydrocarbon group having 1 to 21 carbon atoms which may have a substituent is substituted with -O-, -S- or -CO-, the number of carbon atoms of the group substituted with -O-, -S- or -CO- refers to the number of carbon atoms in the hydrocarbon group before being substituted with -O-, -S- or -CO-. For example, the *-O-CH2-CH2-CH3 group is a group obtained by replacing -CH2- in a hydrocarbon group having 4 carbon atoms (*-CH2-CH2-CH2-CH3) with -O-.

[0093] In addition, if there are multiple substitutable -CH2- groups in a hydrocarbon group having 1 to 21 carbon atoms, the number of substitutions is not necessarily limited to 1. For example, two -CH2- groups in a hydrocarbon group having 4 carbon atoms (*-CH2-CH2-CH2-CH3) may be substituted with -O- to become *-O-CH2-O-CH3. That is, groups in which two or more -CH2- groups are substituted with -O-, -S- or -CO-, such as *-O-CH2-O-CH3, are also included in "groups in which -CH2- groups in a hydrocarbon group having 1 to 21 carbon atoms which may have a substituent are substituted with -O-, -S- or -CO-".

[0094] In formula (Xa),

[0095] Z is preferably -OP(=O)R a1 R a2 .

[0096] R a1 Preferably -R b1 、-OR b1 、-SR b1 or-CO-R b1 .

[0097] R a2 Preferably -R b2 、-OR b2 、-SR b2 or-CO-R b2 .

[0098] R b1 and R b2 represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, R b1 and R b2 They may be bonded to each other to form a ring.

[0099] In formula (Xb),

[0100] L is preferably -OP(=O)R a12 -O-.

[0101] R a12 Preferably -R b3 、-OR b3 、-SR b3 or-CO-R b3 .

[0102] R b3 It represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.

[0103] The compound represented by the above formula (Xa) is preferably a compound represented by the formula (XI). In addition, the compound represented by the above formula (Xb) is preferably a compound represented by the formula (XII). Below, the partial structure of the compound represented by the formula (XI) or the formula (XII) is given to explain the present invention in more detail.

[0104]

[0105] [In formula (XI),

[0106] R x1 represents an unsaturated hydrocarbon group having 2 to 20 carbon atoms which may have a substituent or an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, R x2 represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, or a Zx-linked 2 With R x1 single key.

[0107] Z x1 and Z x2 Each independently represents a single bond or an oxygen atom.

[0108] X x1 ~X x4 , nx1~nx4 are the same as above.

[0109] In formula (XII),

[0110] R x3 It represents an unsaturated hydrocarbon group having 2 to 20 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent.

[0111] Z x3 represents a single bond or an oxygen atom.

[0112] X x5 ~X x12 , nx5~nx12 are the same as above. ]

[0113] The aluminum phthalocyanine dye is also preferably a compound represented by formula (YI) or formula (YII). The present invention will be described in more detail below with reference to partial structures of the compounds represented by formula (YI) or formula (YII).

[0114]

[0115] [In formula (YI),

[0116] R y1 It represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.

[0117] R y2represents a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 20 carbon atoms, or a Z-linked y3 With R y1 single key.

[0118] Y 1 and Z y1 Each independently represents an oxygen atom or a sulfur atom.

[0119] Z y2 and Z y3 Each independently represents a single bond, an oxygen atom or a sulfur atom.

[0120] Among them, Y 1 , Z y1 , Z y2 and Z y3 At least one of them represents a sulfur atom.

[0121] X y1 ~X y4 Each independently represents -R y4 、-OR y4 、-SR y4 , a halogen atom, a nitro group or a sulfamoyl group which may have a substituent.

[0122] R y4 It represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.

[0123] ny1 to ny4 each independently represent an integer of 0 to 4.

[0124] In formula (YII),

[0125] R y3 It represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.

[0126] Y 2 and Z y4 Each independently represents an oxygen atom or a sulfur atom.

[0127] Z y5 represents a single bond, an oxygen atom, or a sulfur atom.

[0128] Among them, Y 2 , Z y4 and Z y5 At least one of them represents a sulfur atom.

[0129] X y5 ~X y12 Each independently represents -R y5 、-OR y5 、-SR y5 , a halogen atom, a nitro group or a sulfamoyl group which may have a substituent.

[0130] R y5 It represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.

[0131] ny5 to ny12 each independently represent an integer of 0 to 4.]

[0132] It should be noted that the compound represented by formula (YI) includes a compound having a resonance structure represented by formula (YIa) or a compound existing in an equilibrium relationship represented by formula (YIb), and the compound represented by formula (YII) includes a compound having a resonance structure represented by formula (YIIa) or a compound existing in an equilibrium relationship represented by formula (YIIb).

[0133]

[0134]

[0135] [In formula (YI), formula (YIa) and formula (YIb),

[0136] R y1 It represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.

[0137] R y2 represents a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 20 carbon atoms, or a Z-linked y3 With R y1 single key.

[0138] Y I and Z y1 Each independently represents an oxygen atom or a sulfur atom.

[0139] Z y2 and Z y3 Each independently represents a single bond, an oxygen atom or a sulfur atom.

[0140] Among them, Y 1 , Z y1 , Z y2 and Z y3 At least one of them represents a sulfur atom.

[0141] X y1 ~X y4 Each independently represents -R y4 、-OR y4 、-SR y4 , a halogen atom, a nitro group or a sulfamoyl group which may have a substituent.

[0142] R y4 It represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.

[0143] ny1 to ny4 each independently represent an integer of 0 to 4.

[0144] In formula (YII), formula (YIIa) and formula (YIIb),

[0145] R y3 It represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.

[0146] Y 2 and Z y4 Each independently represents an oxygen atom or a sulfur atom.

[0147] Z y5 represents a single bond, an oxygen atom, or a sulfur atom.

[0148] Among them, Y 2 , Z y4 and Z y5 At least one of them represents a sulfur atom.

[0149] X y5 ~X y12 Each independently represents -R y5 、-OR y5 、-SR y5 , a halogen atom, a nitro group or a sulfamoyl group which may have a substituent.

[0150] R y5 It represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.

[0151] ny5 to ny12 each independently represent an integer of 0 to 4.]

[0152] R x1 and R x3 The unsaturated hydrocarbon group represented by is preferably 2 to 20, more preferably 2 to 10, further preferably 2 to 7, particularly preferably 2 to 5.

[0153] R x1 and R x3 The unsaturated hydrocarbon group represented by may be chain-like or cyclic (alicyclic hydrocarbon group).

[0154] As R x1 and R x3The unsaturated chain hydrocarbon group represented by the present invention includes vinyl, propenyl (e.g., 1-propenyl, 2-propenyl (allyl)), 1-methylvinyl, butenyl (e.g., 1-butenyl, 2-butenyl, 3-butenyl), 3-methyl-1-butenyl, 1-methyl-1-butenyl, 3-methyl-2-butenyl, 1,3-butadienyl, 3-methyl-1,2-butadienyl, 1-(2-propenyl) 1-(1-methylvinyl)vinyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1-ethyl-2-propenyl, pentenyl (e.g., 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl), 1-(1,1-dimethylethyl)vinyl, 1,3-dimethyl-1-butenyl, hexenyl (e.g., 1-hexenyl, 5-hexenyl), heptenyl Alkenyl groups such as 1-heptenyl (e.g., 1-heptenyl, 6-heptenyl), octenyl (e.g., 1-octenyl, 7-octenyl), nonenyl (e.g., 1-nonenyl, 8-nonenyl), decenyl (e.g., 1-decenyl, 9-decenyl), undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl, octadecenyl, nonadecenyl, eicosenyl, etc.; ethynyl, propynyl Alkynyl groups such as 1-propynyl, 2-propynyl, butynyl (e.g., 1-butynyl, 2-butynyl, 3-butynyl), pentynyl, hexynyl, heptynyl, octynyl (e.g., 1-octynyl, 7-octynyl), nonynyl, decynyl, undecynyl, dodecynyl, tridecynyl, tetradecynyl, pentadecynyl, hexadecynyl, heptadecenyl, octadecynyl, nonadecenyl and eicosynyl are examples thereof.

[0155] As R x1 and R x3 Examples of the unsaturated alicyclic hydrocarbon group include cycloalkenyl groups such as cyclohexenyl (e.g., cyclohex-1-en-1-yl, cyclohex-2-en-1-yl, cyclohex-3-en-1-yl), cycloheptenyl and cyclooctenyl; and unsaturated polycyclic hydrocarbon groups such as norbornene.

[0156] R x1 and R x3 The unsaturated hydrocarbon group having 2 to 20 carbon atoms represented by may have a substituent.

[0157] As R x1 and R x3 The substituent of the unsaturated hydrocarbon group having 2 to 20 carbon atoms represented by , may be an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, a heterocyclic group which may have a substituent, a halogen atom, a nitro group, a cyano group, -OR xa1 、-CO2R xa1 、-SR xa1 、-SO2Rxa1 、-SO3R xa1 、-SO2NR xa1 R xa2 and-NR xa1 R xa2 wait.

[0158] Here, R xa1 and R xa2 Each independently represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms. xa1 and R xa2 The hydrocarbon group having 1 to 20 carbon atoms represented by b1 ~R b3 , R x2 , R x4 , R x5 and R y1 ~R y5 The hydrocarbon groups having 1 to 20 carbon atoms represented are the same.

[0159] As can be used as R x1 and R x3 The aromatic hydrocarbon group having 6 to 20 carbon atoms as the substituent of the unsaturated hydrocarbon group having 2 to 20 carbon atoms represented by phenyl, o-tolyl, m-tolyl, p-tolyl, 2-ethylphenyl, 3-ethylphenyl, 4-ethylphenyl, 2,3-dimethylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, 3,4-dimethylphenyl, 3,5-dimethylphenyl, 4-vinylphenyl, o-isopropylphenyl, m-isopropylphenyl, p-isopropylphenyl, o-tert-butylphenyl, m-tert-butylphenyl, p-tert-butylphenyl, 3,5-di(tert-butyl)phenyl, 3 ... , 5-di(tert-butyl)-4-methylphenyl, 4-butylphenyl, 4-pentylphenyl, 2,6-bis(1-methylethyl)phenyl, 2,4,6-tri(1-methylethyl)phenyl, 4-cyclohexylphenyl, 2,4,6-trimethylphenyl, 4-octylphenyl, 4-(1,1,3,3-tetramethylbutyl)phenyl, 1-naphthyl, 2-naphthyl, 6-methyl-2-naphthyl, 5,6,7,8-tetrahydro-1-naphthyl, 5,6,7,8-tetrahydro-2-naphthyl, fluorenyl, phenanthrenyl, anthracenyl, 2-dodecylphenyl, 3-dodecylphenyl, 4-dodecylphenyl, peryl, Aromatic hydrocarbon groups such as pyrenyl and pyrene.

[0160] The aromatic hydrocarbon group preferably has 6 to 10 carbon atoms, more preferably 6 to 8 carbon atoms.

[0161] The aromatic hydrocarbon group may have a substituent, and examples of the substituent include a halogen atom, a nitro group, a cyano group, -OR xa1 、-CO2R xa1 、-SR xa1、-SO2R xa1 、-SO3R xa1 、-SO2NR xa1 R xa2 and-NR xa1 R xa2 etc. (Among which, R xa1 and R xa2 Same as above).

[0162] As R x1 and R x3 The heterocyclic group used as a substituent of the unsaturated hydrocarbon group having 2 to 20 carbon atoms represented by may be a monocyclic or polycyclic group, and is preferably a heterocyclic ring containing a heteroatom as a ring constituent. Examples of the heteroatom include a nitrogen atom, an oxygen atom, and a sulfur atom.

[0163] Examples of the heterocycle containing only nitrogen atoms as heteroatoms include monocyclic saturated heterocycles such as aziridine, azetidine, pyrrolidine, piperidine and piperazine; five-membered unsaturated heterocycles such as pyrrole, pyrazole, imidazole, 1,2,3-triazole and 1,2,4-triazole; six-membered unsaturated heterocycles such as pyridine, pyridazine, pyrimidine, pyrazine and 1,3,5-triazine; condensed bicyclic heterocycles such as indazole, indoline, isoindoline, isoindoline-1,3-dione, indole, indolizine, benzimidazole, quinoline, isoquinoline, quinoxaline, quinazoline, cinnoline, phthalazine, naphthyridine, purine, pteridine, benzopyrazole and benzopiperidine; condensed tricyclic heterocycles such as carbazole, acridine and phenolazine, etc.

[0164] Examples of the heterocyclic ring containing only oxygen atoms as heteroatoms include oxirane, oxetane, tetrahydrofuran, tetrahydropyran, 1,3-dihydropyran, Alkane, 1,4-di 1,4-dioxaspiro[4.5]decane and 1,4-dioxaspiro[4.5]nonane; 1,4-dioxaspiro[4.5]nonane and other saturated bicyclic heterocyclic rings; α-acetone, β-propiolactone, γ-butyrolactone, δ-valerolactone and other lactone heterocyclic rings; 5-membered unsaturated heterocyclic rings such as furan; 6-membered unsaturated heterocyclic rings such as 2H-pyran and 4H-pyran; 1-benzofuran, benzopyran, benzodioxole, chroman, isochroman and other condensed bicyclic heterocyclic rings; 1,4-dioxaspiro[4.5]decane, 1,4-dioxaspiro[4.5]nonane and other saturated bicyclic heterocyclic rings; 1,4-dioxaspiro[4.5]nonane and other condensed tricyclic heterocyclic rings such as xanthene and dibenzofuran; etc.

[0165] Examples of the heterocycle containing only a sulfur atom as a heteroatom include a five-membered saturated heterocycle such as dithiolane; a six-membered saturated heterocycle such as cyclopentyl sulfide and 1,3-cyclopentyl disulfide; a five-membered unsaturated heterocycle such as thiophene, 4H-thiopyran, benzothiopyran and other benzothiopyrans; a condensed bicyclic heterocycle such as benzothiophene; and a condensed tricyclic heterocycle such as thianthrene and dibenzothiophene.

[0166] Examples of the heterocycle containing nitrogen and oxygen atoms as heteroatoms include monocyclic saturated heterocycles such as morpholine, 2-pyrrolidone, and 2-piperidone; Azoles, Isopropylamine Monocyclic unsaturated heterocyclic rings such as azoles; benzo azole, benzyl isocyanate Azoles, benzo Azine, benzodioxadiazine Alkane, benzimidazolinium and other fused bicyclic heterocyclic rings; phenanthracene Oxazine and other fused tricyclic heterocyclic rings, etc.

[0167] Examples of the heterocycle containing a nitrogen atom and a sulfur atom as heteroatoms include monocyclic heterocycles such as thiazole; condensed bicyclic heterocycles such as benzothiazole; and condensed tricyclic heterocycles such as phenothiazine.

[0168] The heterocyclic group has preferably 2 to 30 carbon atoms, more preferably 3 to 22 carbon atoms, and even more preferably 3 to 20 carbon atoms.

[0169] The heterocyclic group may have a substituent, and examples of the substituent include a halogen atom, a nitro group, a cyano group, -OR xa1 、-CO2R xa1 、-SR xa1 、-SO2R xa1 、-SO3R xa1 、-SO2NR xa1 R xa2 and-NR xa1 R xa2 etc. (Among which, R xa1 and R xa2 Same as above).

[0170] In addition, the bonding position of the heterocyclic ring is a portion after any hydrogen atom contained in each ring is removed.

[0171] As R x1 and R x3 Examples of the halogen atom used as a substituent for the unsaturated hydrocarbon group having 2 to 20 carbon atoms represented by include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

[0172] R x1 and R x3 The number of carbon atoms in the aromatic hydrocarbon group represented by is preferably 6 to 20, more preferably 6 to 10, further preferably 6 to 8, and particularly preferably 6.

[0173] As R x1 and R x3The aromatic hydrocarbon group represented by the present invention includes phenyl, o-tolyl, m-tolyl, p-tolyl, 2-ethylphenyl, 3-ethylphenyl, 4-ethylphenyl, 2,3-dimethylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, 3,4-dimethylphenyl, 3,5-dimethylphenyl, 4-vinylphenyl, o-isopropylphenyl, m-isopropylphenyl, p-isopropylphenyl, o-tert-butylphenyl, m-tert-butylphenyl, p-tert-butylphenyl, 3,5-di(tert-butyl)phenyl, 3,5-di(tert-butyl)-4-methylphenyl, phenyl, 4-butylphenyl, 4-pentylphenyl, 2,6-bis(1-methylethyl)phenyl, 2,4,6-tris(1-methylethyl)phenyl, 4-cyclohexylphenyl, 2,4,6-trimethylphenyl, 4-octylphenyl, 4-(1,1,3,3-tetramethylbutyl)phenyl, 1-naphthyl, 2-naphthyl, 6-methyl-2-naphthyl, 5,6,7,8-tetrahydro-1-naphthyl, 5,6,7,8-tetrahydro-2-naphthyl, fluorenyl, phenanthrenyl, anthracenyl, 2-dodecylphenyl, 3-dodecylphenyl, 4-dodecylphenyl, peryl, Aromatic hydrocarbon groups such as pyrenyl and pyrene.

[0174] R x1 and R x3 The aromatic hydrocarbon group having 6 to 20 carbon atoms represented by may have a substituent.

[0175] As R x1 and R x3 The substituents of the aromatic hydrocarbon group having 6 to 20 carbon atoms represented by hereinafter include halogen atoms such as fluorine, chlorine, bromine and iodine atoms, nitro, cyano, -OR xa1 、-CO2R xa1 、-SR xa1 、-SO2R xa1 、-SO3R xa1 、-SO2NR xa1 R xa2 and-NR xa1 R xa2 etc. (Among which, R xa1 and R xa2 Same as above).

[0176] R a1 ~R a12 The hydrocarbon group represented by is preferably 1-21, more preferably 1-15.

[0177] R b1 ~R b3 , R x2 , R x4 , R x5 and R y1 ~R y5The hydrocarbon group represented by is preferably 1-20, more preferably 1-15.

[0178] R a1 ~R a12 A hydrocarbon group having 1 to 21 carbon atoms represented by b1 ~R b3 , R x2 , R x4 , R x5 and R y1 ~R y5 The hydrocarbon group having 1 to 20 carbon atoms represented by may be an aliphatic hydrocarbon group or an aromatic hydrocarbon group. The aliphatic hydrocarbon group may be saturated or unsaturated, and may be chain-like or cyclic (alicyclic hydrocarbon group).

[0179] As R a1 ~R a12 , R b1 ~R b3 , R x2 , R x4 , R x5 and R y1 ~R y5The saturated or unsaturated chain hydrocarbon group represented by the present invention includes straight-chain alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl and eicosyl; isopropyl, isobutyl, sec-butyl, tert-butyl, 2-ethylbutyl, 3,3-dimethylbutyl, 1,1,3,3-tetramethylbutyl, 1-methylbutyl, 1-ethylpropyl, 3-methylbutyl, neopentyl, 1,1-dimethylpropyl, 2-methylpentyl, 3-ethylpentyl, 1,3-dimethylbutyl, 2-propylpentyl, 1-ethyl-1,2-dimethylpropyl, 1-methylpentyl, 4 branched-chain alkyl groups such as 1-methylpentyl, 4-methylhexyl, 5-methylhexyl, 2-ethylhexyl, 1-methylhexyl, 1-ethylpentyl, 1-propylbutyl, 3-ethylheptyl, 2,2-dimethylheptyl, 1-methylheptyl, 1-ethylhexyl, 1-propylpentyl, 1-methyloctyl, 1-ethylheptyl, 1-propylhexyl, 1-butylpentyl, 1-methylnonyl, 1-ethyloctyl, 1-propylheptyl and 1-butylhexyl; vinyl (vinyl), propenyl (e.g., 1-propenyl, 2-propenyl (allyl)), 1-methylvinyl, butenyl (e.g., 1-butenyl, 2-butenyl, 3-butenyl), 3-methyl-1-butenyl, 1-methyl-1-butenyl, 3-methyl-2-butenyl, 3-methyl-3-butenyl, 3-methyl-4-butenyl, 3-methyl-5-butenyl, 3-methyl-6-butenyl, 3-methyl-7-butenyl, 3-methyl-8-butenyl, 3-methyl-9-butenyl, 3-methyl-1-butenyl, 3-methyl-2-butenyl, 3-methyl-1-butenyl, 3-methyl-2-butenyl, 3-methyl-3 ... 1-(1-methylvinyl)vinyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1-ethyl-2-propenyl, pentenyl (e.g., 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl), 1-(1,1-dimethylethyl)vinyl, 1,3-dimethyl-1-butenyl, hexenyl (e.g., 1-hexenyl, 5-hexenyl), heptenyl (e.g., 1-heptenyl, 6-heptenyl), octenyl (e.g., 1-octenyl, 7-octenyl), nonenyl (e.g., 1-nonenyl, 8-nonenyl), Alkenyl groups include, for example, 1-decenyl, 9-decenyl, 1-undecenyl, 1-dodecenyl, 1-tridecenyl, 1-tetradecenyl, 1-pentadecenyl, 2-heptylenyl, 2-heptylenyl, 3-butynyl, 1-pentynyl, 2-heptylenyl, 3-butynyl, 2-heptylenyl, 4-heptylenyl, 5-heptylenyl, 6-heptylenyl, 7-heptylenyl, 8-heptylenyl, 9-heptylenyl, 1-decenyl, 2-decenyl, 3-decenyl, 4-decenyl, 1-undecenyl, 2-decenyl, 1-decenyl, 2-decenyl, 3-decenyl, 4-decenyl, 5 ...

[0180] R a1 ~Ra12 , R b1 ~R b3 , R x2 , R x4 , R x5 and R y1 ~R y5 The saturated chain hydrocarbon group represented by is preferably 1-10, more preferably 1-7, and even more preferably 1-5.

[0181] R a1 ~R a12 , R b1 ~R b3 , R x2 , R x4 , R x5 and R y1 ~R y5 The unsaturated chain hydrocarbon group represented by is preferably 2-10, more preferably 2-7, and even more preferably 2-5.

[0182] As R a1 ~R a12 , R b1 ~R b3 , R x2 , R x4 , R x5 and R y1 ~R y5 The saturated or unsaturated alicyclic hydrocarbon group represented by the present invention includes cyclopropyl, 1-methylcyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, 1-methylcyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 1,2-dimethylcyclohexyl, 1,3-dimethylcyclohexyl, 1,4-dimethylcyclohexyl, 2,3-dimethylcyclohexyl, 2,4-dimethylcyclohexyl, 2,5-dimethylcyclohexyl, 2,6-dimethylcyclohexyl, 3,4-dimethylcyclohexyl, 3,5-dimethylcyclohexyl, 2,2-dimethylcyclohexyl, 3,3 -cycloalkyl groups such as dimethylcyclohexyl, 4,4-dimethylcyclohexyl, cyclooctyl, 2,4,6-trimethylcyclohexyl, 2,2,6,6-tetramethylcyclohexyl, 3,3,5,5-tetramethylcyclohexyl, 4-pentylcyclohexyl, 4-octylcyclohexyl and 4-cyclohexylcyclohexyl; cycloalkenyl groups such as cyclohexenyl (for example, cyclohex-1-en-1-yl, cyclohex-2-en-1-yl, cyclohex-3-en-1-yl), cycloheptenyl and cyclooctenyl; saturated or unsaturated polycyclic hydrocarbon groups such as norbornyl, norbornenyl, adamantyl and bicyclo[2.2.2]octyl, etc.

[0183] R a1 ~R a12 , R b1 ~R b3 , R x2, R x4 , R x5 and R y1 ~R y5 The saturated or unsaturated alicyclic hydrocarbon group represented by is preferably 3 to 10 carbon atoms.

[0184] As R a1 ~R a12 , R b1 ~R b3 , R x2 , R x4 , R x5 and R y1 ~R y5 The aromatic hydrocarbon groups represented by the present invention include phenyl, o-tolyl, m-tolyl, p-tolyl, 2-ethylphenyl, 3-ethylphenyl, 4-ethylphenyl, 2,3-dimethylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, 3,4-dimethylphenyl, 3,5-dimethylphenyl, 4-vinylphenyl, o-isopropylphenyl, m-isopropylphenyl, p-isopropylphenyl, o-tert-butylphenyl, m-tert-butylphenyl, p-tert-butylphenyl, 3,5-di(tert-butyl)phenyl, 3,5-di(tert-butyl)-4-methylphenyl, phenyl, 4-butylphenyl, 4-pentylphenyl, 2,6-bis(1-methylethyl)phenyl, 2,4,6-tris(1-methylethyl)phenyl, 4-cyclohexylphenyl, 2,4,6-trimethylphenyl, 4-octylphenyl, 4-(1,1,3,3-tetramethylbutyl)phenyl, 1-naphthyl, 2-naphthyl, 6-methyl-2-naphthyl, 5,6,7,8-tetrahydro-1-naphthyl, 5,6,7,8-tetrahydro-2-naphthyl, fluorenyl, phenanthrenyl, anthracenyl, 2-dodecylphenyl, 3-dodecylphenyl, 4-dodecylphenyl, peryl, Aromatic hydrocarbon groups such as pyrenyl and pyrene.

[0185] R a1 ~R a12 , R b1 ~R b3 , R x2 , R x4 , R x5 and R y1 ~R y5 The number of carbon atoms in the aromatic hydrocarbon group represented by is preferably 6 to 20, more preferably 6 to 10, and even more preferably 6 to 8.

[0186] R a1 ~R a12 , R b1 ~R b3 , R x2 , R x4 , R x5 and R y1 ~Ry5 The hydrocarbon group represented by the formula (a) may be a group formed by combining the above-mentioned hydrocarbon groups (e.g., an aromatic hydrocarbon group and at least one of a chain hydrocarbon group and an alicyclic hydrocarbon group), and examples thereof 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, )methyl, 1-phenylethyl, 1-methyl-1-phenylethyl, 1,1-diphenylethyl, (1-naphthyl)methyl and (2-naphthyl)methyl; arylalkenyl such as 1-phenylethenyl, 2-phenylethenyl (phenylethenyl), 2,2-diphenylethenyl, 2-phenyl-2-(1-naphthyl)ethenyl; arylalkynyl such as phenylethynyl; phenyl formed by bonding more than one phenyl group such as biphenyl and terphenyl; cyclohexylmethylphenyl, benzylphenyl, (dimethyl(phenyl)methyl)phenyl, etc.

[0187] These preferably have 7-18 carbon atoms, and more preferably 7-15 carbon atoms.

[0188] R a1 ~R a12 , R b1 ~R b3 , R x2 , R x4 , R x5 and R y1 ~R y5 The group represented by the above-mentioned hydrocarbon groups (for example, chain hydrocarbon groups and alicyclic hydrocarbon groups) may be a group obtained by combining the above-mentioned hydrocarbon groups (for example, chain hydrocarbon groups and alicyclic hydrocarbon groups), for example, an alkyl group obtained by bonding one or more alicyclic hydrocarbon groups such as cyclopropylmethyl, cyclopropylethyl, cyclobutylmethyl, cyclobutylethyl, cyclopentylmethyl, cyclopentylethyl, cyclohexylmethyl, (2-methylcyclohexyl)methyl, cyclohexylethyl, and adamantylmethyl.

[0189] These preferably have 4 to 15 carbon atoms, and more preferably 4 to 10 carbon atoms.

[0190] R a1 ~R a12 A hydrocarbon group having 1 to 21 carbon atoms represented by b1 ~R b3 , R x2 , R x4 , R x5 and R y1 ~R y5 The hydrocarbon group having 1 to 20 carbon atoms represented by may have a substituent.

[0191] As R a1 ~Ra12 A hydrocarbon group having 1 to 21 carbon atoms represented by b1 ~R b3 , R x2 , R x4 , R x5 and R y1 ~R y5 The substituent of the hydrocarbon group having 1 to 20 carbon atoms represented by , may be a heterocyclic group which may have a substituent, a halogen atom, a nitro group, a cyano group, -OR xa1 、-CO2R xa1 、-SR xa1 、-SO2R xa1 、-SO3R xa1 、-SO2NR xa1 R xa2 and-NR xa1 R xa2 etc. (Among which, R xa1 and R xa2 Same as above).

[0192] As R a1 ~R a12 A hydrocarbon group having 1 to 21 carbon atoms represented by b1 ~R b3 , R x2 , R x4 , R x5 and R y1 ~R y5 The heterocyclic group used as a substituent of the hydrocarbon group having 1 to 20 carbon atoms represented by may be a monocyclic or polycyclic group, and is preferably a heterocyclic ring containing a heteroatom as a ring constituent. Examples of the heteroatom include a nitrogen atom, an oxygen atom, and a sulfur atom.

[0193] Examples of the heterocyclic ring include x1 and R x3 The heterocyclic group used as a substituent for the unsaturated hydrocarbon group having 2 to 20 carbon atoms represented by is the same heterocyclic group as that used for the substituent for the unsaturated hydrocarbon group having 2 to 20 carbon atoms represented by

[0194] The heterocyclic group has preferably 2 to 30 carbon atoms, more preferably 3 to 22 carbon atoms, and even more preferably 3 to 20 carbon atoms.

[0195] The heterocyclic group may have a substituent, and examples of the substituent include a halogen atom, a nitro group, a cyano group, -OR xa1 、-CO2R xa1 、-SR xa1 、-SO2R xa1 、-SO3R xa1 、-SO2NR xa1 R xa2 and-NR xa1 Rxa2 etc. (Among which, R xa1 and R xa2 Same as above).

[0196] In addition, the bonding position of the heterocyclic ring is a portion after any hydrogen atom contained in each ring is removed.

[0197] As R a1 ~R a12 A hydrocarbon group having 1 to 21 carbon atoms represented by b1 ~R b3 , R x2 , R x4 , R x5 and R y1 ~R y5 Examples of the halogen atom used as a substituent for the hydrocarbon group having 1 to 20 carbon atoms represented by include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

[0198] R x2 To connect Z x2 With R x1 When the single bond of x1 Part or all of *-Z x2 -P(=O)-Z x1 -* (* indicates the bonding site) together form a ring. That is, R x2 To connect Z x2 With R x1 When the single bond is x1 Any carbon atom in an unsaturated hydrocarbon group having 2 to 20 carbon atoms which may have a substituent or any carbon atom in an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent (preferably any carbon atom in an unsaturated hydrocarbon group having 2 to 20 carbon atoms which may have a substituent) represented by Z x2 The bond that can share a pair of electrons is equivalent to R x2 Represents a single bond.

[0199] R x1 Part or all of *-Z x2 -P(=O)-Z x1 -* (* represents a bonding site) together, an unsaturated bond may be formed between carbon atoms that are constituent members of the ring, an unsaturated bond may be formed between a carbon atom that is a constituent member of the ring and a carbon atom other than the constituent members of the ring, or an unsaturated bond may be formed between carbon atoms other than the constituent members of the ring.

[0200] In addition, R y2 To connect Z y3 With R y1 When the single bond of y1is a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, R y1 Part or all of *-Z y3 -P(=Z y1 )-Z y2 -* (* indicates the bonding site) together form a ring. That is, R y2 To connect Z y3 With R y1 When the single bond is y1 Any carbon atom in the optionally substituted hydrocarbon group having 1 to 20 carbon atoms represented by Z y3 The bond that can share a pair of electrons is equivalent to R y2 Represents a single bond.

[0201] As X x1 ~X x12 Examples of the halogen atom represented by include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, and a fluorine atom is preferred.

[0202] X x1 ~X x12 The sulfamoyl group represented by is represented by *-SO2-NH2 (* represents a bonding site).

[0203] X x1 ~X x12 The sulfamoyl group represented by X may have a substituent. x1 ~X x12 The substituent of the sulfamoyl group represented by R x1 and R x3 The substituents of the unsaturated hydrocarbon group having 2 to 20 carbon atoms represented by the above are the same, and specifically, there can be mentioned an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, a heterocyclic group which may have a substituent, a halogen atom, a nitro group, a cyano group, -OR xa1 、-CO2R xa1 、-SR xa1 、-SO2R xa1 、-SO3R xa1 、-SO2NR xa1 R xa2 and-NR xa1 R xa2 etc. (Among which, R xa1 and R xa2 Same as above).

[0204] X x1 ~X x4 -R x4 , X x5 ~X x12 -R x5 , X y1 ~X y4-R y4 or X y5 ~X y12 -R y5 An aliphatic hydrocarbon group having 1 to 20 carbon atoms is preferred, a saturated chain hydrocarbon group having 1 to 20 carbon atoms is more preferred, a saturated chain hydrocarbon group having 1 to 10 carbon atoms is further preferred, a branched alkyl group having 1 to 5 carbon atoms is further preferred, and a tert-butyl group is particularly preferred.

[0205] In formula (XI),

[0206] R x1 An unsaturated chain hydrocarbon group having 2 to 20 carbon atoms which may have a substituent or an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent is preferred, an unsaturated chain hydrocarbon group having 2 to 10 carbon atoms which may have a substituent or an aromatic hydrocarbon group having 6 to 8 carbon atoms which may have a substituent is more preferred, an unsaturated chain hydrocarbon group having 2 to 7 carbon atoms which may have a substituent or an aromatic hydrocarbon group having 6 to 7 carbon atoms which may have a substituent is further preferred, and a vinyl group which may have a substituent, a propenyl group which may have a substituent, a butenyl group which may have a substituent, a 3-methyl-2-butenyl group which may have a substituent, a 3-methyl-1,2-butadienyl group which may have a substituent, a heptenyl group which may have a substituent, an ethynyl group which may have a substituent, a propynyl group which may have a substituent, a butynyl group which may have a substituent, or a phenyl group which may have a substituent is particularly preferred.

[0207] R x1 When the unsaturated hydrocarbon group having 2 to 20 carbon atoms represented by has a substituent, the substituent is preferably a phenyl group.

[0208] R x2 An aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent or an unsaturated hydrocarbon group having 2 to 20 carbon atoms which may have a substituent is preferred, an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent or an unsaturated chain hydrocarbon group having 2 to 20 carbon atoms which may have a substituent is more preferred, an aromatic hydrocarbon group having 6 to 8 carbon atoms which may have a substituent or an unsaturated chain hydrocarbon group having 2 to 7 carbon atoms which may have a substituent is further preferred, and a phenyl group which may have a substituent, a vinyl group which may have a substituent, a propenyl group which may have a substituent, a butenyl group which may have a substituent, a 3-methyl-2-butenyl group which may have a substituent, a 3-methyl-1,2-butadienyl group which may have a substituent, a heptenyl group which may have a substituent, an ethynyl group which may have a substituent, a propynyl group which may have a substituent, or a butynyl group which may have a substituent is particularly preferred.

[0209] R x2 When the unsaturated hydrocarbon group having 2 to 20 carbon atoms represented by has a substituent, the substituent is preferably a phenyl group.

[0210] In formula (Xa) or formula (XI),

[0211] X x1 ~X x4 Each independently preferably -R x4 or halogen atoms.

[0212] Each of nx1 to nx4 is independently preferably 0-2, more preferably 0-1.

[0213] In formula (XII),

[0214] R x3 An unsaturated chain hydrocarbon group having 2 to 20 carbon atoms which may have a substituent or an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent is preferred, an unsaturated chain hydrocarbon group having 2 to 10 carbon atoms which may have a substituent or an aromatic hydrocarbon group having 6 to 8 carbon atoms which may have a substituent is more preferred, an unsaturated chain hydrocarbon group having 2 to 5 carbon atoms which may have a substituent or an aromatic hydrocarbon group having 6 to 7 carbon atoms which may have a substituent is further preferred, and a vinyl group which may have a substituent, a propenyl group which may have a substituent, a butenyl group which may have a substituent, an ethynyl group which may have a substituent, a propynyl group which may have a substituent, a butynyl group which may have a substituent, or a phenyl group which may have a substituent is particularly preferred.

[0215] R x3 When the unsaturated hydrocarbon group having 2 to 20 carbon atoms represented by has a substituent, the substituent is preferably a phenyl group.

[0216] In formula (Xb) or formula (XII),

[0217] X x5 ~X x12 Each independently preferably -R x5 or halogen atoms.

[0218] Each of nx5 to nx12 is independently preferably 0-2, more preferably 0-1.

[0219] As the aluminum phthalocyanine dye (preferably a compound represented by the formula (XI)), compounds represented by the formula (XIA) to the formula (XIE) are preferred.

[0220]

[0221]

[0222] [In formula (XIA) to formula (XIE), R x1 , R x2 , Z x1 and Z x2 Same as above.]

[0223] Examples of the compound represented by formula (XIA) include compounds represented by formula (XIA-1) to formula (XIA-190) shown in Tables 1 to 4.

[0224] Examples of the compound represented by formula (XIB) include compounds represented by formula (XIB-1) to formula (XIB-190) shown in Tables 5 to 8.

[0225] Examples of the compound represented by formula (XIC) include compounds represented by formula (XIC-1) to formula (XIC-190) shown in Tables 9 to 12.

[0226] Examples of the compound represented by formula (XID) include compounds represented by formula (XID-1) to formula (XID-190) shown in Tables 13 to 16.

[0227] Examples of the compound represented by formula (XIE) include compounds represented by formula (XIE-1) to formula (XIE-190) shown in Tables 17 to 20.

[0228] It should be noted that the “R x1 ” column and “R x2 The symbols described in the "" column correspond to the groups represented by formula (xi-1) to formula (xi-12) and formula (xii-1), respectively.

[0229] In addition, the “R x1 With R x2 The symbols recorded in the "Groups Formed" column correspond to the groups represented by Formula (Xca-1) to Formula (Xca-2), Formula (Xcb-1), and Formula (Xcc-1). It should be noted that "R x1 With R x2 The group formed in R x2 To connect Z x2 With R x1 When the single bond is *-Z x2 -P(=O)-Z x1 -* (* represents a bonding site) is a group to which the bonding site * is bonded.

[0230] In formula (xca-1) to formula (xca-2), R x6 and R x7 Each independently represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent. Examples of the hydrocarbon group having 1 to 20 carbon atoms which may have a substituent include b1 ~Rb3 , R x2 , R x4 , R x5 and R y1 ~R y5 The groups represented by the above are the same as the hydrocarbon groups having 1 to 20 carbon atoms.

[0231] * indicates bonding site.

[0232] In formula (xcb-1), R x8 Corresponding to the group represented by formula (xcc-1), R x9 Corresponding to a hydrogen atom or a hydroxyl group.

[0233] * indicates bonding site.

[0234]

[0235] [Table 1]

[0236]

[0237] [Table 2]

[0238]

[0239] [Table 3]

[0240]

[0241] [Table 4]

[0242]

[0243] As the compound represented by formula (XIA), preferably, formula (XIA-1) to formula (XIA-12), formula (XIA-91) to formula (XIA-102), formula (XIA-103) to formula (XIA-108), formula (XIA-115) to formula (XIA-119), formula (XIA-126) to formula (XIA-129), formula (XIA-136) to formula (XIA-138), formula (XIA-140) to formula (XIA-141), formula (XIA-142) to formula (XIA-143), formula (XIA-144) to formula (XIA-145), formula (XIA-146) to formula (XIA-147), formula (XIA-148) to formula (XIA-149), formula (XIA-150) to formula (XIA-151) The compounds represented by formula (XIA-145) to formula (XIA-146), formula (XIA-153), formula (XIA-181) to formula (XIA-190), more preferably formula (XIA-1) to formula (XIA-12), formula (XIA-103) to formula (XIA-105), formula (XIA-115) to formula (XIA-116), formula (XIA-126), formula (XIA-136) to formula (XIA-137) 8), compounds represented by formula (XIA-145) to (XIA-146), (XIA-153), (XIA-181) to (XIA-182), (XIA-183) to (XIA-184), (XIA-187) to (XIA-188), further preferred are compounds represented by formula (XIA-1), (XIA-10), (XIA-11), (XIA-12), (XIA-115), (XIA-126), (XIA-145), (XIA-153), (XIA-181), (XIA-182), (XIA-183), (XIA-184), and (XIA-187), and further preferred are compounds represented by formula (XIA-115), (XIA-126), and (XIA-182).

[0244] [Table 5]

[0245]

[0246] [Table 6]

[0247]

[0248] [Table 7]

[0249]

[0250] [Table 8]

[0251]

[0252] As the compound represented by formula (XIB), preferred are compounds represented by formula (XIB-1) to formula (XIB-12), formula (XIB-91) to formula (XIB-102), formula (XIB-103) to formula (XIB-108), formula (XIB-115) to formula (XIB-119), formula (XIB-126) to formula (XIB-129), formula (XIB-136) to formula (XIB-138), formula (XIB-145) to formula (XIB-146), formula (XIB-153), and formula (XIB-181) to formula (XIB-190), more preferred are compounds represented by formula (XIB-1) to formula (XIB-12), and further preferred are compounds represented by formula (XIB-1).

[0253] [Table 9]

[0254]

[0255] [Table 10]

[0256]

[0257] [Table 11]

[0258]

[0259] [Table 12]

[0260]

[0261] As the compound represented by formula (XIC), preferably, formula (XIC-1) to formula (XIC-12), formula (XIC-91) to formula (XIC-102), formula (XIC-103) to formula (XIC-108), formula (XIC-115) to formula (XIC-119), formula (XIC-126) to formula (XIC-129), formula (XIC-136) to formula (XIC-138), formula (XIC-145) to formula (XIC-146) The compounds represented by formula (XIC-1) to (XIC-12), formula (XIC-103) to (XIC-105), formula (XIC-115) to (XIC-116), and formula (XIC-126) are more preferred, and the compounds represented by formula (XIC-1) and (XIC-115) are further preferred.

[0262] [Table 13]

[0263]

[0264] [Table 14]

[0265]

[0266] [Table 15]

[0267]

[0268] [Table 16]

[0269]

[0270] As the compound represented by formula (XID), preferred are compounds represented by formula (XID-1) to formula (XID-12), formula (XID-91) to formula (XID-102), formula (XID-103) to formula (XID-108), formula (XID-115) to formula (XID-119), formula (XID-126) to formula (XID-129), formula (XID-136) to formula (XID-138), formula (XID-145) to formula (XID-146), formula (XID-153), and formula (XID-181) to formula (XID-190), more preferred are compounds represented by formula (XID-1) to formula (XID-12), and further preferred are compounds represented by formula (XID-1).

[0271] [Table 17]

[0272]

[0273] [Table 18]

[0274]

[0275] [Table 19]

[0276]

[0277] [Table 20]

[0278]

[0279] As the compound represented by formula (XIE), preferably, formula (XIE-1) to formula (XIE-12), formula (XIE-91) to formula (XIE-102), formula (XIE-103) to formula (XIE-108), formula (XIE-115) to formula (XIE-119), formula (XIE-126) to formula (XIE-129), formula (XIE-136) to formula (XIE-138), formula (XIE-145) to formula (XIE-146) The compounds represented by formula (XIE-1) to (XIE-12), formula (XIE-103) to (XIE-105), formula (XIE-115) to (XIE-116), and formula (XIE-126) are more preferred, and the compounds represented by formula (XIE-1) and (XIE-115) are further preferred.

[0280] As the aluminum phthalocyanine dye (preferably a compound represented by the formula (XII)), compounds represented by the formula (XIIA) to the formula (XIIE) are preferred.

[0281]

[0282]

[0283] [In Formula (XIIA) to Formula (XIIE), R x3 and Z x3 Same as above.]

[0284] Examples of the compound represented by formula (XIIA) include compounds represented by formula (XIIA-1) to formula (XIIA-18) shown in Table 21.

[0285] Examples of the compound represented by formula (XIIB) include compounds represented by formula (XIIB-1) to formula (XIIB-18) shown in Table 22.

[0286] Examples of the compound represented by formula (XIIC) include compounds represented by formula (XIIC-1) to formula (XIIC-18) shown in Table 23.

[0287] Examples of the compound represented by formula (XIID) include compounds represented by formula (XIID-1) to formula (XIID-18) shown in Table 24.

[0288] Examples of the compound represented by formula (XIIE) include compounds represented by formula (XIIE-1) to formula (XIIE-18) shown in Table 25.

[0289] It should be noted that the “Rx3 The symbols described in the "" column correspond to the groups represented by formula (xiii-1) to formula (xiii-9).

[0290] * indicates bonding site.

[0291]

[0292] [Table 21]

[0293]

[0294] As the compound represented by formula (XIIA), compounds represented by formula (XIIA-1) to formula (XIIA-6) and formula (XIIA-10) to formula (XIIA-15) are preferred.

[0295] [Table 22]

[0296]

[0297] As the compound represented by formula (XIIB), compounds represented by formula (XIIB-1) to formula (XIIB-6) and formula (XIIB-10) to formula (XIIB-15) are preferred.

[0298] [Table 23]

[0299]

[0300] As the compound represented by formula (XIIC), compounds represented by formula (XIIC-1) to formula (XIIC-6) and formula (XIIC-10) to formula (XIIC-15) are preferred.

[0301] [Table 24]

[0302]

[0303] As the compound represented by formula (XIID), compounds represented by formula (XIID-1) to formula (XIID-6) and formula (XIID-10) to formula (XIID-15) are preferred.

[0304] [Table 25]

[0305]

[0306] As the compound represented by formula (XIIE), compounds represented by formula (XIIE-1) to formula (XIIE-6) and formula (XIIE-10) to formula (XIIE-15) are preferred.

[0307] It should be noted that the compound represented by formula (XI) and the compound represented by formula (XII) include novel compounds.

[0308] The compound represented by the formula (XI) can be produced, for example, by appropriately reacting a compound represented by the formula (XIII) with a compound represented by the formula (XIV).

[0309] The compound represented by formula (XII) can be produced, for example, by appropriately reacting the compound represented by formula (XIII) with the compound represented by formula (XV).

[0310]

[0311] [In formula (XI), formula (XIII) and formula (XIV), R x1 , Rx 2 , Z x1 , Z x2 , X x1 ~X x4 and nx1 to nx4 are the same as above.]

[0312]

[0313] [In formula (XII), formula (XIII) and formula (XV), R x3 、Zx 3 , X x1 ~X x12 and nx1 to nx12 are the same as above.]

[0314] In formula (YI),

[0315] R y1 An aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent is preferred, an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent is more preferred, an aromatic hydrocarbon group having 6 to 8 carbon atoms which may have a substituent is further preferred, and a phenyl group which may have a substituent is particularly preferred.

[0316] R y2 An unsaturated hydrocarbon group having 2 to 20 carbon atoms which may have a substituent or an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent is preferred, an unsaturated chain hydrocarbon group having 2 to 10 carbon atoms which may have a substituent or an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent is more preferred, an unsaturated chain hydrocarbon group having 2 to 7 carbon atoms which may have a substituent or an aromatic hydrocarbon group having 6 to 8 carbon atoms which may have a substituent is further preferred, an alkenyl group having 2 to 7 carbon atoms which may have a substituent or an aromatic hydrocarbon group having 6 to 8 carbon atoms which may have a substituent is further preferred, and a vinyl group which may have a substituent or a phenyl group which may have a substituent is particularly preferred.

[0317] Each of ny1 to ny4 is independently preferably 0 to 2, more preferably 0 to 1, and further preferably 0.

[0318] X y1 ~X y4 Each independently preferably -R y4 or halogen atoms.

[0319] Y 1 , Z y1 , Z y2 and Z y3 At least one of them represents a sulfur atom, and preferably satisfies at least one of the following aspects, that is, Y 1 is a sulfur atom and Z y1 In the form of oxygen atoms, Y 1 is an oxygen atom and Z y1 The sulfur atom and Z y2 and Z y3 The sulfur atom is represented by y2 When Z is an unsaturated hydrocarbon group, it is preferred that y2 and Z y3 For a single key.

[0320] In formula (YII),

[0321] R y3 An unsaturated hydrocarbon group having 2 to 20 carbon atoms which may have a substituent or an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent is preferred, an unsaturated chain hydrocarbon group having 2 to 10 carbon atoms which may have a substituent or an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent is more preferred, an unsaturated chain hydrocarbon group having 2 to 7 carbon atoms which may have a substituent or an aromatic hydrocarbon group having 6 to 8 carbon atoms which may have a substituent is further preferred, an alkenyl group having 2 to 7 carbon atoms which may have a substituent or an aromatic hydrocarbon group having 6 to 8 carbon atoms which may have a substituent is further preferred, and a vinyl group which may have a substituent or a phenyl group which may have a substituent is particularly preferred.

[0322] Each of ny5 to ny12 is independently preferably 0 to 2, more preferably 0 to 1, and further preferably 0.

[0323] X y5 ~X y12 Each independently preferably -R y5 or halogen atoms.

[0324] Y 2 , Z y4 and Z y5 At least one of them represents a sulfur atom. y3 When Z is an unsaturated hydrocarbon group, it is preferred that y5 For a single key.

[0325] Examples of the compound represented by formula (YI) include compounds represented by formula (YIA) to formula (YIE).

[0326]

[0327]

[0328] [In formula (YIA) to formula (YIE), R y1 , R y2 , Y 1 , Z y1 , Z y2 and Z y3 Same as above.]

[0329] Examples of the compound represented by formula (YIA) include compounds represented by formula (YIA-1) to formula (YIA-24) shown in Table 26.

[0330] Examples of the compound represented by formula (YIB) include compounds represented by formula (YIB-1) to formula (YIB-24) shown in Table 27.

[0331] Examples of the compound represented by formula (YIC) include compounds represented by formula (YIC-1) to formula (YIC-24) shown in Table 28.

[0332] Examples of the compound represented by formula (YID) include compounds represented by formula (YID-1) to formula (YID-24) shown in Table 29.

[0333] Examples of the compound represented by formula (YIE) include compounds represented by formula (YIE-1) to formula (YIE-24) shown in Table 30.

[0334] In addition, "yi-1" in Tables 26 to 30 represents a phenyl group, and "yi-2" represents a vinyl group.

[0335] [Table 26]

[0336] <![CDATA[Y 1 ]]> <![CDATA[Z y1 ]]> <![CDATA[Z y2 ]]> <![CDATA[Z y3 ]]> <![CDATA[R y1 ]]> <![CDATA[R y2 ]]> (YIA-1) Sulfur Atom Oxygen Atom single bond single bond yi-1 yi-1 (YIA-2) Sulfur Atom Oxygen Atom single bond Oxygen Atom yi-1 yi-1 (YIA-3) Sulfur Atom Oxygen Atom single bond Sulfur Atom yi-1 yi-1 (YIA-4) Sulfur Atom Oxygen Atom Oxygen Atom Oxygen Atom yi-1 yi-1 (YIA-5) Sulfur Atom Oxygen Atom Oxygen Atom Sulfur Atom yi-1 yi-1 (YIA-6) Sulfur Atom Oxygen Atom Sulfur Atom Sulfur Atom yi-1 yi-1 (YIA-7) Sulfur Atom Sulfur Atom single bond single bond yi-1 yi-1 (YIA-8) Sulfur Atom Sulfur Atom single bond Oxygen Atom yi-1 yi-1 (YIA-9) Sulfur Atom Sulfur Atom single bond Sulfur Atom yi-1 yi-1 (YIA-10) Sulfur Atom Sulfur Atom Oxygen Atom Oxygen Atom yi-1 yi-1 (YIA-11) Sulfur Atom Sulfur Atom Oxygen Atom Sulfur Atom yi-1 yi-1 (YIA-12) Sulfur Atom Sulfur Atom Sulfur Atom Sulfur Atom yi-1 yi-1 (YIA-13) Oxygen Atom Sulfur Atom single bond single bond yi-1 yi-1 (YIA-14) Oxygen Atom Sulfur Atom single bond Oxygen Atom yi-1 yi-1 (YIA-15) Oxygen Atom Sulfur Atom single bond Sulfur Atom yi-1 yi-1 (YIA-16) Oxygen Atom Sulfur Atom Oxygen Atom Oxygen Atom yi-1 yi-1 (YIA-17) Oxygen Atom Sulfur Atom Oxygen Atom Sulfur Atom yi-1 yi-1 (YIA-18) Oxygen Atom Sulfur Atom Sulfur Atom Sulfur Atom yi-1 yi-1 (YIA-19) Oxygen Atom Oxygen Atom single bond Sulfur Atom yi-1 yi-1 (YIA-20) Oxygen Atom Oxygen Atom Oxygen Atom Sulfur Atom yi-1 yi-1 (YIA-21) Oxygen Atom Oxygen Atom Sulfur Atom Sulfur Atom yi-1 yi-1 (YIA-22) Sulfur Atom Oxygen Atom single bond single bond yi-1 yi-2 (YIA-23) Sulfur Atom Sulfur Atom single bond single bond yi-1 yi-2 (YIA-24) Oxygen Atom Sulfur Atom single bond single bond yi-1 yi-2

[0337] As the compound represented by formula (YIA), preferred are compounds represented by formula (YIA-1) to formula (YIA-6), formula (YIA-13) to formula (YIA-18), formula (YIA-21), formula (YIA-22) to formula (YIA-24), and more preferred are compounds represented by formula (YIA-1), formula (YIA-13), formula (YIA-21), formula (YIA-23), and formula (YIA-24).

[0338] [Table 27]

[0339] <![CDATA[Y 1 ]]> <![CDATA[Z y1 ]]> <![CDATA[Z y2 ]]> <![CDATA[Z y3 ]]> <![CDATA[R y1 ]]> <![CDATA[R y2 ]]> (YIB-1) Sulfur Atom Oxygen Atom single bond single bond yi-1 yi-1 (YIB-2) Sulfur Atom Oxygen Atom single bond Oxygen Atom yi-1 yi-1 (YIB-3) Sulfur Atom Oxygen Atom single bond Sulfur Atom yi-1 yi-1 (YIB-4) Sulfur Atom Oxygen Atom Oxygen Atom Oxygen Atom yi-1 yi-1 (YIB-5) Sulfur Atom Oxygen Atom Oxygen Atom Sulfur Atom yi-1 yi-1 (YIB-6) Sulfur Atom Oxygen Atom Sulfur Atom Sulfur Atom yi-1 yi-1 (YIB-7) Sulfur Atom Sulfur Atom single bond single bond yi-1 yi-1 (YIB-8) Sulfur Atom Sulfur Atom single bond Oxygen Atom yi-1 yi-1 (YIB-9) Sulfur Atom Sulfur Atom single bond Sulfur Atom yi-1 yi-1 (YIB-10) Sulfur Atom Sulfur Atom Oxygen Atom Oxygen Atom yi-1 yi-1 (YIB-11) Sulfur Atom Sulfur Atom Oxygen Atom Sulfur Atom yi-1 yi-1 (YIB-12) Sulfur Atom Sulfur Atom Sulfur Atom Sulfur Atom yi-1 yi-1 (YIB-13) Oxygen Atom Sulfur Atom single bond single bond yi-1 yi-1 (YIB-14) Oxygen Atom Sulfur Atom single bond Oxygen Atom yi-1 yi-1 (YIB-15) Oxygen Atom Sulfur Atom single bond Sulfur Atom yi-1 yi-1 (YIB-16) Oxygen Atom Sulfur Atom Oxygen Atom Oxygen Atom yi-1 yi-1 (YIB-17) Oxygen Atom Sulfur Atom Oxygen Atom Sulfur Atom yi-1 yi-1 (YIB-18) Oxygen Atom Sulfur Atom Sulfur Atom Sulfur Atom yi-1 yi-1 (YIB-19) Oxygen Atom Oxygen Atom single bond Sulfur Atom yi-1 yi-1 (YIB-20) Oxygen Atom Oxygen Atom Oxygen Atom Sulfur Atom yi-1 yi-1 (YIB-21) Oxygen Atom Oxygen Atom Sulfur Atom Sulfur Atom yi-1 yi-1 (YIB-22) Sulfur Atom Oxygen Atom single bond single bond yi-1 yi-2 (YIB-23) Sulfur Atom Sulfur Atom single bond single bond yi-1 yi-2 (YIB-24) Oxygen Atom Sulfur Atom single bond single bond yi-1 yi-2

[0340] As the compound represented by formula (YIB), preferred are compounds represented by formula (YIB-1) to formula (YIB-6), formula (YIB-13) to formula (YIB-18), formula (YIB-21), formula (YIB-22) to formula (YIB-24), and more preferred are compounds represented by formula (YIB-1), formula (YIB-13), formula (YIB-21), formula (YIB-23) and formula (YIB-24).

[0341] [Table 28]

[0342] <![CDATA[Y 1 ]]> <![CDATA[Z y1 ]]> <![CDATA[Z y2 ]]> <![CDATA[Z y3 ]]> <![CDATA[R y1 ]]> <![CDATA[R y2 ]]> (YIC-1) Sulfur Atom Oxygen Atom single bond single bond yi-1 yi-1 (YIC-2) Sulfur Atom Oxygen Atom single bond Oxygen Atom yi-1 yi-1 (YIC-3) Sulfur Atom Oxygen Atom single bond Sulfur Atom yi-1 yi-1 (YIC-4) Sulfur Atom Oxygen Atom Oxygen Atom Oxygen Atom yi-1 yi-1 (YIC-5) Sulfur Atom Oxygen Atom Oxygen Atom Sulfur Atom yi-1 yi-1 (YIC-6) Sulfur Atom Oxygen Atom Sulfur Atom Sulfur Atom yi-1 yi-1 (YIC-7) Sulfur Atom Sulfur Atom single bond single bond yi-1 yi-1 (YIC-8) Sulfur Atom Sulfur Atom single bond Oxygen Atom yi-1 yi-1 (YIC-9) Sulfur Atom Sulfur Atom single bond Sulfur Atom yi-1 yi-1 (YIC-10) Sulfur Atom Sulfur Atom Oxygen Atom Oxygen Atom yi-1 yi-1 (YIC-11) Sulfur Atom Sulfur Atom Oxygen Atom Sulfur Atom yi-1 yi-1 (YIC-12) Sulfur Atom Sulfur Atom Sulfur Atom Sulfur Atom yi-1 yi-1 (YIC-13) Oxygen Atom Sulfur Atom single bond single bond yi-1 yi-1 (YIC-14) Oxygen Atom Sulfur Atom single bond Oxygen Atom yi-1 yi-1 (YIC-15) Oxygen Atom Sulfur Atom single bond Sulfur Atom yi-1 yi-1 (YIC-16) Oxygen Atom Sulfur Atom Oxygen Atom Oxygen Atom yi-1 yi-1 (YIC-17) Oxygen Atom Sulfur Atom Oxygen Atom Sulfur Atom yi-1 yi-1 (YIC-18) Oxygen Atom Sulfur Atom Sulfur Atom Sulfur Atom yi-1 yi-1 (YIC-19) Oxygen Atom Oxygen Atom single bond Sulfur Atom yi-1 yi-1 (YIC-20) Oxygen Atom Oxygen Atom Oxygen Atom Sulfur Atom yi-1 yi-1 (YIC-21) Oxygen Atom Oxygen Atom Sulfur Atom Sulfur Atom yi-1 yi-1 (YIC-22) Sulfur Atom Oxygen Atom single bond single bond yi-1 yi-2 (YIC-23) Sulfur Atom Sulfur Atom single bond single bond yi-1 yi-2 (YIC-24) Oxygen Atom Sulfur Atom single bond single bond yi-1 yi-2

[0343] As the compound represented by formula (YIC), preferred are compounds represented by formula (YIC-1) to formula (YIC-6), formula (YIC-13) to formula (YIC-18), formula (YIC-21), formula (YIC-22) to formula (YIC-24), and more preferred are compounds represented by formula (YIC-1), formula (YIC-13), formula (YIC-21), formula (YIC-23), and formula (YIC-24).

[0344] [Table 29]

[0345] <![CDATA[Y 1 ]]> <![CDATA[Z y1 ]]> <![CDATA[Z y2 ]]> <![CDATA[Z y3 ]]> <![CDATA[R y1 ]]> <![CDATA[R y2 ]]> (YID-1) Sulfur Atom Oxygen Atom single bond single bond yi-1 yi-1 (YID-2) Sulfur Atom Oxygen Atom single bond Oxygen Atom yi-1 yi-1 (YID-3) Sulfur Atom Oxygen Atom single bond Sulfur Atom yi-1 yi-1 (YID-4) Sulfur Atom Oxygen Atom Oxygen Atom Oxygen Atom yi-1 yi-1 (YID-5) Sulfur Atom Oxygen Atom Oxygen Atom Sulfur Atom yi-1 yi-1 (YID-6) Sulfur Atom Oxygen Atom Sulfur Atom Sulfur Atom yi-1 yi-1 (YID-7) Sulfur Atom Sulfur Atom single bond single bond yi-1 yi-1 (YID-8) Sulfur Atom Sulfur Atom single bond Oxygen Atom yi-1 yi-1 (YID-9) Sulfur Atom Sulfur Atom single bond Sulfur Atom yi-1 yi-1 (YID-10) Sulfur Atom Sulfur Atom Oxygen Atom Oxygen Atom yi-1 yi-1 (YID-11) Sulfur Atom Sulfur Atom Oxygen Atom Sulfur Atom yi-1 yi-1 (YID-12) Sulfur Atom Sulfur Atom Sulfur Atom Sulfur Atom yi-1 yi-1 (YID-13) Oxygen Atom Sulfur Atom single bond single bond yi-1 yi-1 (YID-14) Oxygen Atom Sulfur Atom single bond Oxygen Atom yi-1 yi-1 (YID-15) Oxygen Atom Sulfur Atom single bond Sulfur Atom yi-1 yi-1 (YID-16) Oxygen Atom Sulfur Atom Oxygen Atom Oxygen Atom yi-1 yi-1 (YID-17) Oxygen Atom Sulfur Atom Oxygen Atom Sulfur Atom yi-1 yi-1 (YID-18) Oxygen Atom Sulfur Atom Sulfur Atom Sulfur Atom yl-1 yi-1 (YID-19) Oxygen Atom Oxygen Atom single bond Sulfur Atom yi-1 yi-1 (YID-20) Oxygen Atom Oxygen Atom Oxygen Atom Sulfur Atom yi-1 yi-1 (YID-21) Oxygen Atom Oxygen Atom Sulfur Atom Sulfur Atom yi-1 yi-1 (YID-22) Sulfur Atom Oxygen Atom single bond single bond yi-1 yi-2 (YID-23) Sulfur Atom Sulfur Atom single bond single bond yi-1 yi-2 (YID-24) Oxygen Atom Sulfur Atom single bond single bond yi-1 yi-2

[0346] As the compound represented by formula (YID), preferred are compounds represented by formula (YID-1) to formula (YID-6), formula (YID-13) to formula (YID-18), formula (YID-21), formula (YID-22) to formula (YID-24), and more preferred are compounds represented by formula (YID-1), formula (YID-13), formula (YID-21), formula (YID-23), and formula (YID-24).

[0347] [Table 30]

[0348] <![CDATA[Y 1 ]]> <![CDATA[Z y1 ]]> <![CDATA[Z y2 ]]> <![CDATA[Z y3 ]]> <![CDATA[R y1 ]]> <![CDATA[R y2 ]]> (YIE-1) Sulfur Atom Oxygen Atom single bond single bond yi-1 yi-1 (YIE-2) Sulfur Atom Oxygen Atom single bond Oxygen Atom yi-1 yi-1 (YIE-3) Sulfur Atom Oxygen Atom single bond Sulfur Atom yi-1 yi-1 (YIE-4) Sulfur Atom Oxygen Atom Oxygen Atom Oxygen Atom yi-1 yi-1 (YIE-5) Sulfur Atom Oxygen Atom Oxygen Atom Sulfur Atom yi-1 yi-1 (YIE-6) Sulfur Atom Oxygen Atom Sulfur Atom Sulfur Atom yi-1 yi-1 (YIE-7) Sulfur Atom Sulfur Atom single bond single bond yi-1 yi-1 (YIE-8) Sulfur Atom Sulfur Atom single bond Oxygen Atom yi-1 yi-1 (YIE-9) Sulfur Atom Sulfur Atom single bond Sulfur Atom yi-1 yi-1 (YIE-10) Sulfur Atom Sulfur Atom Oxygen Atom Oxygen Atom yi-1 yi-1 (YIE-11) Sulfur Atom Sulfur Atom Oxygen Atom Sulfur Atom yi-1 yi-1 (YIE-12) Sulfur Atom Sulfur Atom Sulfur Atom Sulfur Atom yi-1 yi-1 (YIE-13) Oxygen Atom Sulfur Atom single bond single bond yi-1 yi-1 (YIE-14) Oxygen Atom Sulfur Atom single bond Oxygen Atom yi-1 yi-1 (YIE-15) Oxygen Atom Sulfur Atom single bond Sulfur Atom yi-1 yi-1 (YIE-16) Oxygen Atom Sulfur Atom Oxygen Atom Oxygen Atom yi-1 yi-1 (YIE-17) Oxygen Atom Sulfur Atom Oxygen Atom Sulfur Atom yi-1 yi-1 (YIE-18) Oxygen Atom Sulfur Atom Sulfur Atom Sulfur Atom yi-1 yi-1 (YIE-19) Oxygen Atom Oxygen Atom single bond Sulfur Atom yi-1 yi-1 (YIE-20) Oxygen Atom Oxygen Atom Oxygen Atom Sulfur Atom yi-1 yi-1 (YIE-21) Oxygen Atom Oxygen Atom Sulfur Atom Sulfur Atom yi-1 yi-1 (YIE-22) Sulfur Atom Oxygen Atom single bond single bond yi-1 yi-2 (YIE-23) Sulfur Atom Sulfur Atom single bond single bond yi-1 yi-2 (YIE-24) Oxygen Atom Sulfur Atom single bond single bond yi-1 yi-2

[0349] As the compound represented by formula (YIE), preferred are compounds represented by formula (YIE-1) to formula (YIE-6), formula (YIE-13) to formula (YIE-18), formula (YIE-21), formula (YIE-22) to formula (YIE-24), and more preferred are compounds represented by formula (YIE-1), formula (YIE-13), formula (YIE-21), formula (YIE-23), and formula (YIE-24).

[0350] Examples of the compound represented by formula (YII) include compounds represented by formula (YIIA) to formula (YIIE).

[0351]

[0352] [In formula (YIIA) ~ formula (YIIE), R y3 , Y 2 , Z y4 and Z y5 Same as above.]

[0353] Examples of the compound represented by formula (YIIA) include compounds represented by formula (YIIA-1) to formula (YIIA-13) shown in Table 31.

[0354] Examples of the compound represented by formula (YIIB) include compounds represented by formula (YIIB-1) to formula (YIIB-13) shown in Table 32.

[0355] Examples of the compound represented by formula (YIIC) include compounds represented by formula (YIIC-1) to formula (YIIC-13) shown in Table 33.

[0356] Examples of the compound represented by formula (YIID) include compounds represented by formula (YIID-1) to formula (YIID-13) shown in Table 34.

[0357] Examples of the compound represented by formula (YIIE) include compounds represented by formula (YIIE-1) to formula (YIIE-13) shown in Table 35.

[0358] In addition, "yi-1" in Tables 31 to 35 represents a phenyl group, and "yi-2" represents a vinyl group.

[0359] [Table 31]

[0360] <![CDATA[Y 2 ]]> <![CDATA[Z y4 ]]> <![CDATA[Z y5 ]]> <![CDATA[R y3 ]]> (YIIA-1) Sulfur Atom Oxygen Atom single bond yi-1 (YIIA-2) Sulfur Atom Oxygen Atom Oxygen Atom yi-1 (YIIA-3) Sulfur Atom Oxygen Atom Sulfur Atom yi-1 (YI IA-4) Sulfur Atom Sulfur Atom single bond yi-1 (YIIA-5) Sulfur Atom Sulfur Atom Oxygen Atom yi-1 (YIIA-6) Sulfur Atom Sulfur Atom Sulfur Atom yi-1 (YIIA-7) Oxygen Atom Oxygen Atom Sulfur Atom yi-1 (YIIA-8) Oxygen Atom Sulfur Atom single bond yi-1 (YIIA-9) Oxygen Atom Sulfur Atom Oxygen Atom yi-1 (YIIA-10) Oxygen Atom Sulfur Atom Sulfur Atom yi-1 (YIIA-11) Sulfur Atom Oxygen Atom single bond yi-2 (YIIA-12) Sulfur Atom Sulfur Atom single bond yi-2 (YIIA-13) Oxygen Atom Sulfur Atom single bond yi-2

[0361] As the compound represented by formula (YIIA), preferred are compounds represented by formula (YIIA-1), formula (YIIA-2), formula (YIIA-8), formula (YIIA-9), formula (YIIA-12), and formula (YIIA-13), and more preferred are compounds represented by formula (YIIA-1), formula (YIIA-8), formula (YIIA-12), and formula (YIIA-13).

[0362] [Table 32]

[0363] <![CDATA[Y 2 ]]> <![CDATA[Z y4 ]]> <![CDATA[Z y5 ]]> <![CDATA[R y3 ]]> (YIIB-1) Sulfur Atom Oxygen Atom single bond yi-1 (YIIB-2) Sulfur Atom Oxygen Atom Oxygen Atom yi-1 (YIIB-3) Sulfur Atom Oxygen Atom Sulfur Atom yi-1 (YIIB-4) Sulfur Atom Sulfur Atom single bond yi-1 (YIIB-5) Sulfur Atom Sulfur Atom Oxygen Atom yi-1 (YIIB-6) Sulfur Atom Sulfur Atom Sulfur Atom yi-1 (YIIB-7) Oxygen Atom Oxygen Atom Sulfur Atom yi-1 (YIIB-8) Oxygen Atom Sulfur Atom single bond yi-1 (YIIB-9) Oxygen Atom Sulfur Atom Oxygen Atom yi-1 (YIIB-10) Oxygen Atom Sulfur Atom Sulfur Atom yi-1 (YIIB-11) Sulfur Atom Oxygen Atom single bond yi-2 (YIIB-12) Sulfur Atom Sulfur Atom single bond yi-2 (YIlB-13) Oxygen Atom Sulfur Atom single bond yi-2

[0364] As the compound represented by formula (YIIB), preferred are compounds represented by formula (YIIB-1), formula (YIIB-2), formula (YIIB-8), formula (YIIB-9), formula (YIIB-12), and formula (YIIB-13), and more preferred are compounds represented by formula (YIIB-1), formula (YIIB-8), formula (YIIB-12), and formula (YIIB-13).

[0365] [Table 33]

[0366] <![CDATA[Y 2 ]]> <![CDATA[Z y4 ]]> <![CDATA[Z y5 ]]> <![CDATA[R y3 ]]> (YIIC-1) Sulfur Atom Oxygen Atom single bond yi-1 (YIIC-2) Sulfur Atom Oxygen Atom Oxygen Atom yi-1 (YIIC-3) Sulfur Atom Oxygen Atom Sulfur Atom yi-1 (YIIC-4) Sulfur Atom Sulfur Atom single bond yi-1 (YIIC-5) Sulfur Atom Sulfur Atom Oxygen Atom yi-1 (YIIC-6) Sulfur Atom Sulfur Atom Sulfur Atom yi-1 (YIIC-7) Oxygen Atom Oxygen Atom Sulfur Atom yi-1 (YIIC-8) Oxygen Atom Sulfur Atom single bond yi-1 (YIIC-9) Oxygen Atom Sulfur Atom Oxygen Atom yi-1 (YIIC-10) Oxygen Atom Sulfur Atom Sulfur Atom yi-1 (YIIC-11) Sulfur Atom Oxygen Atom single bond yi-2 (YIIC-12) Sulfur Atom Sulfur Atom single bond yi-2 (YIIC-13) Oxygen Atom Sulfur Atom single bond yi-2

[0367] As the compound represented by formula (YIIC), preferred are compounds represented by formula (YIIC-1), formula (YIIC-2), formula (YIIC-8), formula (YIIC-9), formula (YIIC-12), and formula (YIIC-13), and more preferred are compounds represented by formula (YIIC-1), formula (YIIC-8), formula (YIIC-12), and formula (YIIC-13).

[0368] [Table 34]

[0369] <![CDATA[Y 2 ]]> <![CDATA[Z y4 ]]> <![CDATA[Z y5 ]]> <![CDATA[R y3 ]]> (YIID-1) Sulfur Atom Oxygen Atom single bond yi-1 (YIID-2) Sulfur Atom Oxygen Atom Oxygen Atom yi-1 (YIID-3) Sulfur Atom Oxygen Atom Sulfur Atom yi-1 (YIID-4) Sulfur Atom Sulfur Atom single bond yi-1 (YIID-5) Sulfur Atom Sulfur Atom Oxygen Atom yi-1 (YIID-6) Sulfur Atom Sulfur Atom Sulfur Atom yi-1 (YIID-7) Oxygen Atom Oxygen Atom Sulfur Atom yi-1 (YIID-8) Oxygen Atom Sulfur Atom single bond yi-1 (YIID-9) Oxygen Atom Sulfur Atom Oxygen Atom yi-1 (YIID-10) Oxygen Atom Sulfur Atom Sulfur Atom yi-1 (YIID-11) Sulfur Atom Oxygen Atom single bond yi-2 (YIID-12) Sulfur Atom Sulfur Atom single bond yi-2 (YIID-13) Oxygen Atom Sulfur Atom single bond yi-2

[0370] As the compound represented by formula (YIID), preferred are compounds represented by formula (YIID-1), formula (YIID-2), formula (YIID-8), formula (YIID-9), formula (YIID-12), and formula (YIID-13), and more preferred are compounds represented by formula (YIID-1), formula (YIID-8), formula (YIID-12), and formula (YIID-13).

[0371] [Table 35]

[0372] <![CDATA[Y 2 ]]> <![CDATA[Z y4 ]]> <![CDATA[Z y5 ]]> <![CDATA[R y3 ]]> (YIIE-1) Sulfur Atom Oxygen Atom single bond yi-1 (YIIE-2) Sulfur Atom Oxygen Atom Oxygen Atom yi-1 (YIIE-3) Sulfur Atom Oxygen Atom Sulfur Atom yi-1 (YIIE-4) Sulfur Atom Sulfur Atom single bond yi-1 (YIIE-5) Sulfur Atom Sulfur Atom Oxygen Atom yi-1 (YIIE-6) Sulfur Atom Sulfur Atom Sulfur Atom yi-1 (YIIE-7) Oxygen Atom Oxygen Atom Sulfur Atom yi-1 (YIIE-8) Oxygen Atom Sulfur Atom single bond yi-1 (YIIE-9) Oxygen Atom Sulfur Atom Oxygen Atom yi-1 (YIIE-10) Oxygen Atom Sulfur Atom Sulfur Atom yi-1 (YIIE-11) Sulfur Atom Oxygen Atom single bond yi-2 (YIIE-12) Sulfur Atom Sulfur Atom single bond yi-2 (YIIE-13) Oxygen Atom Sulfur Atom single bond yi-2

[0373] As the compound represented by formula (YIIE), preferred are compounds represented by formula (YIIE-1), formula (YIIE-2), formula (YIIE-8), formula (YIIE-9), formula (YIIE-12), and formula (YIIE-13), and more preferred are compounds represented by formula (YIIE-1), formula (YIIE-8), formula (YIIE-12), and formula (YIIE-13).

[0374] The compound represented by formula (YI) can be produced, for example, by appropriately reacting a compound represented by formula (YIII) with a compound represented by formula (YIV).

[0375] The compound represented by formula (YII) can be produced, for example, by appropriately reacting the compounds represented by formula (YIIIa) and formula (YIIIb) with the compound represented by formula (YV).

[0376]

[0377] [In formula (YI), formula (YIII) and formula (YIV), R y1 , R y2 , Y 1 , Z y1 , Z y2 , Z y3 , X y1 ~X y4 and ny1 to ny4 are the same as above.]

[0378]

[0379] [In formula (YII), formula (YIIIa), formula (YIIIb) and formula (YV), R y3 , Y 2 , Z y4 , Z y5 , X y5 ~X y12 Same as above for ny5 to ny12.]

[0380] The content of the aluminum phthalocyanine dye is preferably 0.5 to 70% by mass, more preferably 1 to 55% by mass, and even more preferably 2 to 50% by mass in the total amount of the solid content of the colored resin composition.

[0381] In this specification, the "total amount of solid content" 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.

[0382] The content of the aluminum phthalocyanine dye is preferably 20 to 100% by mass, more preferably 30 to 100% by mass, further preferably 40 to 100% by mass, and further preferably 60 to 100% by mass in the total amount of the colorant (A).

[0383] The colorant (A) may further contain a colorant different from the aluminum phthalocyanine dye (hereinafter, sometimes referred to as a colorant (A2)).

[0384] The colorant (A2) may be either a dye or a pigment.

[0385] 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 Seishin Co., Ltd.).

[0386] As the dye, for example, an azo dye, a cyanine dye, a triphenylmethane dye, a thiazole dye, As the oxazine dye, quinophthalone dye, anthraquinone dye, naphthoquinone dye, quinoneimine dye, methine dye, azomethine dye, squarylium dye, acridine dye, styryl dye, coumarin dye, quinoline dye, nitro dye and the like, known dyes are used.

[0387] Specific examples of the dye include CI Solvent Yellow 4 (hereinafter, CI Solvent Yellow is omitted and only the number is described), 14, 15, 23, 24, 38, 62, 63, 68, 82, 94, 99, 117, 162, 163, 167, and 189;

[0388] CI Solvent Red 111, 125, 130, 143, 145, 146, 150, 151, 155, 168, 169, 172, 175, 181, 207, 222, 227, 230, 245, 247;

[0389] CI Solvent Orange 2, 7, 11, 15, 26, 56, 77, 86;

[0390] CI Solvent Violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60;

[0391] CI Solvent Blue 4, 5, 14, 18, 35, 36, 37, 45, 58, 59, 59: 1, 63, 68, 69, 78, 79, 83, 90, 94, 97, 98, 100, 101, 102, 104, 1 05, 111, 112, 122, 128, 132, 136, 139;

[0392] CI solvent dyes such as CI solvent green 1, 3, 5, 7, 28, 29, 32, 33, 34, 35, CI acid yellow 1, 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112, 113, 114, 116, 119, 123, 128, 134, 135, 138, 139 , 140, 144, 150, 155, 157, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251;

[0393] CI Acid Red 1, 4, 8, 14, 17, 18, 26, 27, 29, 31, 33, 34, 35, 37, 40, 42, 44, 57, 66, 73, 76, 80, 88, 97, 103, 106, 111, 114, 129, 133, 134, 138, 143, 145, 150, 151, 155, 158, 160, 172, 176, 182, 183, 195, 1 98, 206, 211, 215, 216, 217, 227, 228, 249, 252, 257, 258, 260, 261, 266, 268, 270, 274, 277, 280, 281, 308, 312, 315, 316, 339, 341, 345, 346, 349, 382, ​​383, 394, 401, 412, 417, 418, 422, 426;

[0394] CI Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 169, 173;

[0395] CI Acid Violet 6B, 7, 15, 16, 17, 19, 21, 23, 24, 25, 34, 38, 49, 72;

[0396] CI Acid Blue 1, 3, 5, 7, 9, 11, 13, 15, 17, 18, 22, 23, 24, 25, 26, 27, 29, 34, 38, 40, 41, 42, 43, 45, 48, 51, 54, 59, 60, 62, 70, 72, 74, 75, 78, 80, 82, 83, 86, 87, 88, 90, 90:1, 91, 92, 93, 93:1, 96, 99, 100, 102, 103, 104, 108, 109, 110, 112, 113, 117, 119, 120 , 123, 126, 127, 129, 130, 131, 138, 140, 142, 143, 147, 150, 151, 154, 158, 161, 166, 167, 168, 170, 171, 175, 182, 183, 184, 187, 192, 199, 203, 204, 205, 210, 213, 229, 234, 236, 256, 259, 267, 269, 278, 280, 285, 290, 296, 315, 324: 1, 335, 340;

[0397] 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 and other CI acid dyes,

[0398] CI Direct Yellow 2, 33, 34, 35, 38, 39, 43, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129, 136, 138, 141;

[0399] 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;

[0400] CI Direct Orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107;

[0401] CI Direct Violet 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104;

[0402] 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, 90, 93, 94, 95, 97, 98, 99, 100, 101, 106, 107, 108, 109, 113, 114, 115, 117, 119, 120, 137, 149, 150, 153, 155, 156, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 168, 170, 171, 172, 173, 188, 190, 192, 193, 194, 195, 196, 198, 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;

[0403] CI direct green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 77, 79, 82 and other CI direct dyes,

[0404] CI Disperse Yellow 51, 54, 76;

[0405] CI Disperse Violet 26, 27;

[0406] CI disperse blue 1, 14, 56, 60 and other CI disperse dyes,

[0407] 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;

[0408] CI Basic Violet 2;

[0409] CI Basic Red 9;

[0410] CI basic dyes such as CI basic green 1,

[0411] CI Reactive Yellow 2, 76, 116;

[0412] CI Reactive Orange 16;

[0413] CI reactive dyes such as CI Reactive Red 36,

[0414] CI Medium Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65;

[0415] CI Medium Red 1, 2, 3, 4, 9, 11, 12, 14, 17, 18, 19, 22, 23, 24, 25, 26, 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;

[0416] 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;

[0417] 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;

[0418] 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, 83, 84;

[0419] CI mordant dyes such as CI mordant green 1, 3, 4, 5, 10, 13, 15, 19, 21, 23, 26, 29, 31, 33, 34, 35, 41, 43, 53;

[0420] CI vat dyes such as CI vat green 1, etc.

[0421] These dyes may be used alone or in combination of two or more dyes for each color.

[0422] Examples of the pigment include pigments classified as pigments in the Color Index (published by The Society of Dyers and Colourists), and the following pigments can be exemplified.

[0423] Green pigment: CI Pigment Green 7, 36, 58, etc.

[0424] Yellow pigment: 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, etc.

[0425] Orange pigment: CI Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73, etc.

[0426] Red pigment: CI Pigment Red 9, 97, 105, 122, 144, 149, 166, 168, 176, 177, 180, 192, 209, 215, 216, 242, 254, 255, 264, 265, etc.

[0427] Blue pigment: CI pigment blue 16, 60, etc.

[0428] Purple pigment: CI pigment violet 19, 23, 29, 32, 36, 38, etc.

[0429] These pigments may be used alone or in combination for each color.

[0430] The pigment may be subjected to rosin treatment, surface treatment using pigment derivatives into which acidic or basic groups are introduced, grafting treatment on the pigment surface based on polymer compounds, micronization treatment based on sulfuric acid micronization method, cleaning treatment based on organic solvents, water, etc. for removing impurities, removal treatment of ionic impurities based on ion exchange method, etc. as needed. The particle size of the pigment is preferably roughly uniform. The pigment may be a pigment dispersion in a state of being uniformly dispersed in a pigment dispersant solution by dispersing treatment containing a pigment dispersant. The pigments may be dispersed individually or a plurality of them may be mixed and dispersed.

[0431] Examples of the pigment dispersant include the same pigment dispersants as those which may be contained in the coloring resin composition described later.

[0432] When a pigment dispersant is used, its usage amount is preferably 10 to 200 parts by mass, more preferably 15 to 180 parts by mass, and further preferably 20 to 160 parts by mass, relative to 100 parts by mass of the pigment. When the usage amount of the pigment dispersant is within the above range, there is a tendency to obtain a pigment dispersion liquid in a more uniform dispersed state when two or more pigments are used.

[0433] When the colorant (A) contains the colorant (A2), the content of the colorant (A2) is preferably 1 to 80% by mass, more preferably 1 to 70% by mass, and even more preferably 1 to 60% by mass in the total amount of the colorant (A).

[0434] The content of the colorant (A) in the colored resin composition is preferably 0.5 to 80% by mass, more preferably 1 to 70% by mass, and even more preferably 2 to 55% 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 the desired spectrum and color density.

[0435] <Compound represented by formula (DA)>

[0436] The colored resin composition of the present invention contains a compound represented by formula (DA). Although the compound represented by formula (DA) may reduce the adhesion effect when combined with a copper phthalocyanine dye among phthalocyanines, it significantly improves the adhesion effect when combined with an aluminum phthalocyanine dye.

[0437]

[0438] [In formula (DA),

[0439] R d1 It represents a hydrocarbon group having 1 to 12 carbon atoms which may have a substituent. When the hydrocarbon group has 2 to 12 carbon atoms and has -CH2-, the -CH2- may be substituted with -O-, -S- or -CO-.

[0440] R d2 and R d3 each independently represents a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms which may have a substituent, or represents R d2 With R d3 Bonding and -CO-NR d1 -CO- together to form a ring.]

[0441] R d1 ~R d3 The number of carbon atoms of the hydrocarbon group represented is 1 to 12, more preferably 1 to 10, further preferably 1 to 6, and further preferably 1 to 3.

[0442] R d1 The number of carbon atoms of the hydrocarbon group represented by R d2 or R d3 The number of carbon atoms of the hydrocarbon group represented by R d2 With R d3 Bonding and -CO-NR d1 -CO- forms a ring with the number of carbon atoms.

[0443] R d1~R d3 The hydrocarbon group having 1 to 12 carbon atoms represented by may be an aliphatic hydrocarbon group or an aromatic hydrocarbon group. The aliphatic hydrocarbon group may be saturated or unsaturated, and may be chain-like or cyclic (alicyclic hydrocarbon group).

[0444] As R d1 ~R d3 The saturated or unsaturated chain hydrocarbon group represented by R x2 The saturated or unsaturated chain hydrocarbon group having 1 to 12 carbon atoms represented by is the same group.

[0445] R d1 ~R d3 The saturated chain hydrocarbon group represented by is preferably 1 to 10, more preferably 1 to 6, and even more preferably 1 to 3.

[0446] R d1 ~R d3 The unsaturated chain hydrocarbon group represented by is preferably 2 to 10 carbon atoms, more preferably 2 to 6 carbon atoms, and further preferably 2 to 3 carbon atoms.

[0447] As R d1 ~R d3 The saturated or unsaturated alicyclic hydrocarbon group represented by R x2 The saturated or unsaturated alicyclic hydrocarbon group having 3 to 12 carbon atoms in the saturated or unsaturated alicyclic hydrocarbon group represented by is the same group.

[0448] R d1 ~R d3 The saturated or unsaturated alicyclic hydrocarbon group represented by is preferably 3 to 10 carbon atoms.

[0449] As R d1 ~R d3 The aromatic hydrocarbon group represented by R x2 The aromatic hydrocarbon groups having 6 to 12 carbon atoms among the aromatic hydrocarbon groups represented by are the same groups.

[0450] R d1 ~R d3 The aromatic hydrocarbon group represented by is preferably 6 to 10, more preferably 6 to 8.

[0451] R d1 ~R d3 The hydrocarbon group represented by may be a group formed by combining the above-mentioned hydrocarbon groups (e.g., an aromatic hydrocarbon group and at least one of a chain hydrocarbon group and an alicyclic hydrocarbon group). x2 The groups having 7 to 12 carbon atoms among the exemplified groups are the same groups.

[0452] They preferably have 7 to 10 carbon atoms.

[0453] R d1 ~R d3 The group represented may be an alkyl group in which one or more alicyclic hydrocarbon groups are bonded, such as a group in which the above-mentioned hydrocarbon groups (for example, a chain hydrocarbon group and an alicyclic hydrocarbon group) are combined (for example, cyclopropylmethyl group, etc.).

[0454] They preferably have 4 to 10 carbon atoms.

[0455] As R d1 The hydrocarbon group having 1 to 12 carbon atoms represented by (wherein -CH2- in the hydrocarbon group may be substituted by -O-, -S- or -CO-) includes, for example, the following groups.

[0456]

[0457] R d1 In the hydrocarbon group having 1 to 12 carbon atoms represented by , when the hydrocarbon group has 2 to 12 carbon atoms and the hydrocarbon group has -CH2-, the -CH2- may be substituted with -O-, -S- or -CO-. In the hydrocarbon group having 2 to 12 carbon atoms, adjacent -CH2- are not substituted with -O- and / or -S- at the same time, and the terminal -CH2- is not substituted with -O-, -S- or -CO-.

[0458] As R d1 Examples of the group in which -CH2- of the hydrocarbon group having 1 to 12 carbon atoms represented by is substituted with -O-, -S- or -CO- include the following groups.

[0459]

[0460]

[0461]

[0462] R d1 ~R d3 The hydrocarbon group having 1 to 12 carbon atoms represented by may have a substituent.

[0463] As R d1 ~R d3 The substituent of the hydrocarbon group having 1 to 12 carbon atoms represented by , may be a heterocyclic group which may have a substituent, a halogen atom, a nitro group, a cyano group, -OR xa1 、-CO2R xa1 、-SR xa1 、-SO2R xa1 、-SO3R xa1 、-SO2NR xa1 R xa2and-NR xa1 R xa2 etc. (Among which, R xa1 and R xa2 Same as above).

[0464] As R d1 ~R d3 The heterocyclic group used as a substituent of the hydrocarbon group having 1 to 12 carbon atoms represented by may be a monocyclic or polycyclic group, and is preferably a heterocyclic ring containing a heteroatom as a ring constituent. Examples of the heteroatom include a nitrogen atom, an oxygen atom, and a sulfur atom.

[0465] Examples of the heterocyclic ring include x1 and R x3 The heterocyclic group used as a substituent for the unsaturated hydrocarbon group having 2 to 20 carbon atoms represented by is the same heterocyclic group as that used for the substituent for the unsaturated hydrocarbon group having 2 to 20 carbon atoms.

[0466] The heterocyclic group has preferably 2 to 30 carbon atoms, more preferably 3 to 22 carbon atoms, and even more preferably 3 to 20 carbon atoms.

[0467] The heterocyclic group may have a substituent, and examples of the substituent include a halogen atom, a nitro group, a cyano group, -OR xa1 、-CO2R xa1 、-SR xa1 、-SO2R xa1 、-SO3R xa1 、-SO2NR xa1 R xa2 and-NR xa1 R xa2 etc. (Among which, R xa1 and R xa2 Same as above).

[0468] In addition, the bonding position of the heterocyclic ring is a portion after any hydrogen atom contained in each ring is removed.

[0469] As R d1 ~R d3 Examples of the halogen atom used as a substituent for the hydrocarbon group having 1 to 12 carbon atoms represented by include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

[0470] As R d1 ~R d3 The substituent of the hydrocarbon group having 1 to 12 carbon atoms represented by is preferably -OR xa1 (R xa1 It is preferably a hydrogen atom or a saturated chain hydrocarbon group having 1 to 15 carbon atoms, more preferably a hydrogen atom or a straight-chain alkyl group or a branched-chain alkyl group having 1 to 10 carbon atoms, further preferably a hydrogen atom or a methyl group, ethyl group, propyl group, isopropyl group or tert-butyl group, and further preferably a hydrogen atom), -CO2Rxa1 (R xa1 It is preferably a hydrogen atom or a saturated chain hydrocarbon group having 1 to 15 carbon atoms, more preferably a hydrogen atom or a straight-chain alkyl group or a branched-chain alkyl group having 1 to 10 carbon atoms, further preferably a hydrogen atom or a methyl group, ethyl group, propyl group, isopropyl group or tert-butyl group, and further preferably a hydrogen atom).

[0471] R d2 With R d3 Bonding and -CO-NR d1 When -CO- forms a ring together, the following rings can be exemplified as the ring formed. In formula (r-1) to formula (r-7), * represents a d1 bonding site.

[0472]

[0473] In formula (DA),

[0474] R d1 Preferably with -CO2R xa1 (R xa1 Preferably, it is a hydrogen atom or a saturated chain hydrocarbon group having 1 to 15 carbon atoms, more preferably a hydrogen atom or a straight-chain alkyl group or a branched alkyl group having 1 to 10 carbon atoms, further preferably a hydrogen atom or a methyl group, an ethyl group, a propyl group, an isopropyl group, or a tert-butyl group, and further preferably a hydrogen atom) as a substituent having 1 to 12 carbon atoms, more preferably a saturated aliphatic hydrocarbon group having -CO2R xa1 (R xa1 Preferably, it is a hydrogen atom or a saturated chain hydrocarbon group having 1 to 15 carbon atoms, more preferably a hydrogen atom or a straight-chain alkyl group or a branched-chain alkyl group having 1 to 10 carbon atoms, further preferably a hydrogen atom or a methyl group, an ethyl group, a propyl group, an isopropyl group, or a tert-butyl group, and further preferably a hydrogen atom) as a substituent having a saturated chain hydrocarbon group having 1 to 12 carbon atoms, further preferably a -CO2R xa1 (R xa1 Preferably, it is a hydrogen atom or a saturated chain hydrocarbon group having 1 to 10 carbon atoms, more preferably a hydrogen atom or a straight-chain alkyl group or a branched-chain alkyl group having 1 to 8 carbon atoms, further preferably a hydrogen atom or a methyl group, an ethyl group, a propyl group, an isopropyl group, or a tert-butyl group, and further preferably a hydrogen atom) as a substituent having a saturated chain hydrocarbon group having 1 to 5 carbon atoms, and further preferably a -CO2R xa1 (R xa1 Preferably, it is a hydrogen atom or a saturated chain hydrocarbon group having 1 to 5 carbon atoms, more preferably a hydrogen atom or a straight-chain alkyl group or a branched alkyl group having 1 to 4 carbon atoms, further preferably a hydrogen atom or a methyl group, ethyl group, propyl group, isopropyl group or tert-butyl group, and further preferably a hydrogen atom) as a substituent having a straight-chain alkyl group having 1 to 5 carbon atoms, and particularly preferably a -CO2Rxa1 (R xa1 Preferably, it is a hydrogen atom or a methyl group, an ethyl group, a propyl group, an isopropyl group or a tert-butyl group, and more preferably a methyl group, an ethyl group, a propyl group, a butyl group or a pentyl group having a hydrogen atom as a substituent.

[0475] R d2 and R d3 Preferred R d2 With R d3 Bonding and -CO-NR d1 -CO- together to form a ring, preferably R d2 With R d3 Bonding and -CO-NR d1 -CO- together form a ring represented by formula (r-1) or formula (r-2).

[0476] Specific examples of the compound represented by formula (DA) include compounds represented by formula (da-1) to formula (da-10).

[0477]

[0478] As the compound represented by formula (DA), preferred are compounds represented by formula (da-1), formula (da-2), formula (da-4), formula (da-5), formula (da-6), formula (da-9), and formula (da-10), and more preferred are compounds represented by formula (da-1) and formula (da-2).

[0479] The colored resin composition of the present invention contains one or more compounds represented by formula (DA). That is, the compound represented by formula (DA) may be used alone or in combination of a plurality of compounds having different structures.

[0480] When the colored resin composition contains two or more compounds represented by the formula (DA), the compound represented by the formula (DA) preferably contains R d2 With R d3 Bonding and -CO-NR d1 -CO- together with the compound represented by formula (DA) to form a ring represented by formula (r-1) or formula (r-2), more preferably comprises at least two or more compounds selected from the compounds represented by formulas (da-1) to (da-10), further preferably comprises at least two or more compounds selected from the compounds represented by formulas (da-1), (da-2), (da-4), (da-5), (da-6), (da-9) and (da-10), and particularly preferably comprises compounds represented by formulas (da-1) and (da-2).

[0481] When the colored resin composition contains two or more compounds represented by the formula (DA), the two or more compounds represented by the formula (DA) may be contained in equal amounts or in different amounts. When the two or more compounds represented by the formula (DA) are contained in different amounts, the content ratio of the smallest compound represented by the formula (DA) to the largest compound represented by the formula (DA) in the colored resin composition is preferably 1:1.1 to 1:10, more preferably 1:1.5 to 1:8, and even more preferably 1:2 to 1:8 in terms of molar ratio.

[0482] The content of the compound represented by formula (DA) (the total content of two or more compounds represented by formula (DA)) is preferably 1 to 180 parts by mass, more preferably 5 to 170 parts by mass, further preferably 10 to 160 parts by mass, further preferably 15 to 160 parts by mass, further preferably 25 to 150 parts by mass, and particularly preferably 45 to 140 parts by mass relative to 100 parts by mass of the aluminum phthalocyanine dye. When the amount of the compound represented by formula (DA) is within this range, a colored coating film is formed that suppresses the generation of foreign matter and has good adhesion to the substrate.

[0483] The content of the compound represented by formula (DA) in the colored resin composition (the total content of the compounds represented by two or more formulas (DA)) is preferably 0.1 to 30% by mass, more preferably 2.0 to 25% by mass, further preferably 3.5 to 20% by mass, and further preferably 6.0 to 20% by mass relative to the total amount of the solid content. When the content of the compound represented by formula (DA) is within the above range, a colored coating film is formed in which the generation of foreign matter is suppressed and the adhesion to the substrate is good.

[0484] <Dispersant>

[0485] The colored resin composition of the present invention may contain a dispersant. As a dispersant, a surfactant may be mentioned, which may be any of a cationic, anionic, nonionic and amphoteric surfactant. Specifically, surfactants such as polyester, polyamine and acrylic acid may be mentioned. These dispersants may be used alone or in combination of two or more. As a dispersant, when expressed by a trade name, KP (Shin-Etsu Chemical Co., Ltd.), FLOWLEN (Kyoeisha Chemical Co., Ltd.), Solsperse (registered trademark) (Zeneca Co., Ltd.), EFKA (registered trademark) (BASF Co., Ltd.), AJISPER (registered trademark) (Ajinomoto Fine Chemical Co., Ltd.), Disperbyk (registered trademark), BYK (registered trademark) (BYK-Chemie Co., Ltd.), etc. may be mentioned.

[0486] The amount of the dispersant used is preferably 1 to 150 parts by mass, more preferably 10 to 130 parts by mass, further preferably 20 to 120 parts by mass, and further preferably 30 to 110 parts by mass, based on 100 parts by mass of the aluminum phthalocyanine dye.

[0487] The amount of the dispersant used is preferably 1 to 300 parts by mass, more preferably 10 to 150 parts by mass, further preferably 15 to 85 parts by mass, and further preferably 20 to 75 parts by mass, relative to 100 parts by mass of the compound represented by formula (DA). When the amount of the dispersant is within this range, a colored coating film is formed that suppresses the generation of foreign matter and has good adhesion to the substrate.

[0488] <Resin (B)>

[0489] 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].

[0490] Resin [K1]: a copolymer of at least one (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)");

[0491] Resin [K2]: a copolymer of (a) and (b), and a monomer (c) copolymerizable with (a) (which is different from (a) and (b)) (hereinafter sometimes referred to as "(c)");

[0492] Resin [K3]: a copolymer of (a) and (c);

[0493] Resin [K4]: a resin obtained by reacting (b) with a copolymer of (a) and (c);

[0494] Resin [K5]: a resin obtained by reacting (a) with a copolymer of (b) and (c);

[0495] Resin [K6]: A resin obtained by reacting a copolymer of (a), (b) and (c), and further reacting the copolymer with a polycarboxylic acid and / or a carboxylic anhydride.

[0496] Specific examples of (a) include unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, and o-, m-, and p-vinylbenzoic acid;

[0497] 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.;

[0498] 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;

[0499] Unsaturated dicarboxylic acid anhydrides such as maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride;

[0500] Unsaturated mono-(meth)acryloyloxyalkyl) esters of divalent or higher polycarboxylic acids such as mono-(2-(meth)acryloyloxyethyl) succinate and mono-(2-(meth)acryloyloxyethyl) phthalate;

[0501] Unsaturated acrylic acid esters containing a hydroxyl group and a carboxyl group in the same molecule, such as α-(hydroxymethyl) acrylate.

[0502] 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.

[0503] (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.

[0504] 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.

[0505] 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)"), a monomer (b3) having a tetrahydrofuran group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b3)"), and the like.

[0506] As (b1), for example, there can be mentioned a monomer (b1-1) having a structure in which a straight-chain or branched aliphatic unsaturated hydrocarbon is epoxidized (hereinafter sometimes referred to as "(b1-1)") and a monomer (b1-2) having a structure in which alicyclic unsaturated hydrocarbon is epoxidized (hereinafter sometimes referred to as "(b1-2)").

[0507] 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, and the like.

[0508] Examples of (b1-2) include vinylcyclohexene monoxide, 1,2-epoxy-4-vinylcyclohexane (e.g., Celloxide 2000; manufactured by Daicel Co., Ltd.), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., CYCLOMERA 400; manufactured by Daicel Co., Ltd.), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., CYCLOMER M100; manufactured by Daicel Co., Ltd.), 3,4-epoxytricyclo[5.2.1.0; manufactured by Daicel Co., Ltd.), 2，6 ]decyl ester, a compound represented by formula (R1) and a compound represented by formula (R2), etc.

[0509]

[0510] [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.

[0511] X ra and X rb Indicates a single bond, *-R rc -,*-R rc -O-, *-R rc -S- or *-Rrc -NH-.

[0512] R rc It represents an alkanediyl group having 1 to 6 carbon atoms.

[0513] * indicates the bonding site with O. ]

[0514] 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.

[0515] 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.

[0516] 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.

[0517] 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.

[0518] As X ra and X rb , preferably include a single bond, methylene, ethylene, *-CH2-O- and *-CH2CH2-O-, and more preferably include a single bond and *-CH2CH2-O- (* represents a bonding site with O).

[0519] As the compound represented by formula (R1), there can be mentioned compounds represented by any one of formula (R1-1) to formula (R1-15). Among them, preferred are 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), and more preferred are compounds represented by formula (R1-1), formula (R1-7), formula (R1-9) or formula (R1-15).

[0520]

[0521] Examples of the compound represented by formula (R2) include compounds represented by any one of formula (R2-1) to formula (R2-15). Among them, preferred are 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), and more preferred are compounds represented by formula (R2-1), formula (R2-7), formula (R2-9) or formula (R2-15).

[0522]

[0523] As (b2), a monomer having an oxetane group and a (meth)acryloyloxy group is more preferred. As (b2), 3-methyl-3-methacryloyloxymethyloxetane, 3-methyl-3-acryloyloxymethyloxetane, 3-ethyl-3-methacryloyloxymethyloxetane, 3-ethyl-3-acryloyloxymethyloxetane, 3-methyl-3-methacryloyloxyethyloxetane, 3-methyl-3-acryloyloxyethyloxetane, 3-ethyl-3-methacryloyloxyethyloxetane, 3-ethyl-3-methacryloyloxyethyloxetane, 3-ethyl-3-acryloyloxyethyloxetane, etc. can be mentioned.

[0524] 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.

[0525] As (b), (b1) is preferred because the reliability of the obtained color filter, such as heat resistance and chemical resistance, can be further improved. Moreover, (b1-2) is more preferred because the storage stability of the colored resin composition is excellent.

[0526] 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 "dicyclopentyl (meth)acrylate". In addition, it is sometimes called "tricyclodecyl (meth)acrylate"), tricyclo[5.2.1.0 2，6(Meth)acrylates such as decen-8-yl ester (also known as "dicyclopentenyl (meth)acrylate" as a common name in the art), 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;

[0527] (Meth)acrylates containing a hydroxyl group, such as 2-hydroxyethyl (meth)acrylate and 2-hydroxypropyl (meth)acrylate;

[0528] Diethyl maleate, diethyl fumarate, diethyl itaconate and other dicarboxylic acid diesters;

[0529] 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 5-(tert-butoxycarbonyl)bicyclo[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;

[0530] 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;

[0531] 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.

[0532] Among them, styrene, vinyltoluene, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo[2.2.1]hept-2-ene and the like are preferred from the viewpoint of copolymerization reactivity and heat resistance.

[0533] In resin [K1], the ratio of the structural units derived from each monomer 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) in all the structural units constituting resin [K1]. It is more preferred that the structural units derived from (a) are 10 to 50 mol% and the structural units derived from (b) are 50 to 90 mol%.

[0534] 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 excellent.

[0535] 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.

[0536] Specifically, the following method can be cited: a predetermined amount of (a) and (b), a polymerization initiator and a solvent are loaded into a reaction vessel, for example, a deoxygenated atmosphere is formed by replacing oxygen with nitrogen, 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) etc.) and 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.

[0537] It should be noted that 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 the production process of the colored resin composition can be simplified.

[0538] In resin [K2], the ratio of the structural units derived from each monomer in all the structural units constituting resin [K2] is preferably 2 to 45 mol% for the structural units derived from (a), 2 to 95 mol% for the structural units derived from (b), and 1 to 65 mol% for the structural units derived from (c). It is more preferred that the structural units derived from (a) are 5 to 40 mol%, the structural units derived from (b) are 5 to 80 mol%, and the structural units derived from (c) are 5 to 60 mol%.

[0539] 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 excellent.

[0540] The resin [K2] can be produced, for example, in the same manner as described as the method for producing the resin [K1].

[0541] In resin [K3], the ratio of the structural units derived from each monomer in all the structural units constituting resin [K3] is preferably 2 to 60 mol% for the structural units derived from (a) and 40 to 98 mol% for the structural units derived from (c), and more preferably 10 to 50 mol% for the structural units derived from (a) and 50 to 90 mol% for the structural units derived from (c).

[0542] The resin [K3] can be produced, for example, in the same manner as described as the method for producing the resin [K1].

[0543] 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).

[0544] 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 monomer is preferably the same ratio as that exemplified in resin [K3].

[0545] 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.

[0546] After the production of the copolymer of (a) and (c), 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].

[0547] The amount of (b) used is preferably 5 to 80 mol, more preferably 10 to 75 mol, relative to 100 mol of (a). By being 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. From the perspective that the cyclic ether has high reactivity and is less likely to leave unreacted (b), (b1) is preferred as the (b) used in the resin [K4], and (b1-1) is more preferred.

[0548] 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).

[0549] 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.

[0550] As for resin [K5], as the first stage, a copolymer of (b) and (c) is obtained in the same manner as in the production method of resin [K1]. As in the above, the obtained copolymer may be used directly as a solution after the reaction, or may be used as a concentrated or diluted solution, or may be used as a solid (powder) obtained by a method such as reprecipitation.

[0551] The ratio of the structural units derived from (b) and (c) to the total molar number of all structural units constituting the above-mentioned copolymer 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), 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).

[0552] Furthermore, resin [K5] can be obtained by reacting the carboxylic acid or carboxylic anhydride contained in (a) with the cyclic ether derived from (b) contained in the copolymer of (b) and (c) under the same conditions as those in the method for producing resin [K4].

[0553] The amount of (a) to be reacted with the copolymer is preferably 5 to 80 mol relative to 100 mol of (b). Since the cyclic ether has high reactivity and unreacted (b) is less likely to remain, (b1) is preferred as (b) used in the resin [K5], and (b1-1) is more preferred.

[0554] The resin [K6] is a resin obtained by further reacting the resin [K5] with a carboxylic acid anhydride. The hydroxyl group generated by the reaction of the cyclic ether with the carboxylic acid or the carboxylic acid anhydride is reacted with the carboxylic acid anhydride.

[0555] Examples of the carboxylic anhydride include maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride, etc. The amount of the carboxylic anhydride used is preferably 0.5 to 1 mol relative to 1 mol of the amount of (a) used.

[0556] 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-cyclohexyl maleimide copolymer, acrylic acid 3,4-epoxy tricyclo[5.2.1.0 2，6] decyl ester / (meth)acrylic acid / N-cyclohexylmaleimide / 2-hydroxyethyl (meth)acrylate copolymer, 3-methyl-3-(meth)acryloyloxymethyloxetane / (meth)acrylic acid / styrene copolymer and other resins [K2]; benzyl (meth)acrylate / (meth)acrylic acid copolymer, styrene / (meth)acrylic acid copolymer and other resins [K3]; resins obtained by adding benzyl (meth)acrylate / (meth)acrylic acid copolymer to glycidyl (meth)acrylate, resins obtained by adding tricyclodecyl (meth)acrylate / styrene / (meth)acrylic acid copolymer to glycidyl (meth)acrylate, resins obtained by adding (meth)acrylate / tricyclodecyl (meth)acrylate / styrene / (meth)acrylic acid copolymer to glycidyl (meth)acrylate, Resins such as a resin obtained by adding glycidyl (meth)acrylate to a copolymer of tricyclodecyl ester / benzyl (meth)acrylate / (meth)acrylate [K4]; a resin obtained by reacting a copolymer of tricyclodecyl (meth)acrylate / glycidyl (meth)acrylate with (meth)acrylic acid, a resin obtained by reacting a copolymer of tricyclodecyl (meth)acrylate / styrene / glycidyl (meth)acrylate with (meth)acrylic acid, and the like [K5]; a resin obtained by reacting a copolymer of tricyclodecyl (meth)acrylate / glycidyl (meth)acrylate with (meth)acrylic acid, and further reacting the resin with tetrahydrophthalic anhydride [K6], and the like.

[0557] Among them, the resin (B) is preferably the resin [K1] and the resin [K2].

[0558] The resin (B) is preferably a copolymer comprising a structural unit derived from at least one selected from an unsaturated carboxylic acid and an unsaturated carboxylic anhydride, and a structural unit having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond (resin [K1] or resin [K2]), and more preferably resin [K2].

[0559] The polystyrene-equivalent weight average molecular weight of the resin (B) is preferably 500 to 100000, more preferably 600 to 50000, and still more preferably 700 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.

[0560] 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.

[0561] The acid value of the resin (B) is preferably 50 to 170 mg-KOH / g, more preferably 60 to 150 mg-KOH / g, and further preferably 70 to 135 mg-KOH / g, based on solid content. Here, the acid value refers to 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 an aqueous potassium hydroxide solution.

[0562] The content of the resin (B) is preferably 7 to 80% by mass, more preferably 13 to 75% by mass, and further preferably 17 to 70% by mass relative to the total amount of the solid component. When the content of the resin (B) is within the above range, a colored pattern can be formed, and the resolution and residual film rate of the colored pattern tend to be improved.

[0563] <Polymerizable Compound (C)>

[0564] 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.

[0565] 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 tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, tripentaerythritol octa(meth)acrylate, tripentaerythritol hepta(meth)acrylate, tetrapentaerythritol deca(meth)acrylate, tetrapentaerythritol nona(meth)acrylate, tris(2-(meth)acryloyloxyethyl)isocyanurate, ethylene glycol-modified pentaerythritol tetra(meth)acrylate, ethylene glycol-modified dipentaerythritol hexa(meth)acrylate, propylene glycol-modified pentaerythritol tetra(meth)acrylate, propylene glycol-modified dipentaerythritol hexa(meth)acrylate, caprolactone-modified pentaerythritol tetra(meth)acrylate, and caprolactone-modified dipentaerythritol hexa(meth)acrylate.

[0566] Among them, trimethylolpropane tri(meth)acrylate, dipentaerythritol penta(meth)acrylate, and dipentaerythritol hexa(meth)acrylate are preferred.

[0567] The weight average molecular weight of the polymerizable compound (C) is preferably 150 to 2,900, more preferably 250 to 1,500.

[0568] The content of the polymerizable compound (C) is preferably 7 to 65% by mass, more preferably 13 to 60% by mass, and further preferably 17 to 55% by mass relative to the total amount of the solid component. 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 improved.

[0569] <Polymerization Initiator (D)>

[0570] The polymerization initiator (D) is not particularly limited as long as it is a compound that can generate active free radicals, acids, etc. and initiate polymerization by the action of light or heat, and a known polymerization initiator can be used. Examples of polymerization initiators that generate active free radicals include alkylphenone compounds, triazine compounds, acylphosphine oxide compounds, O-acyloxime compounds, and biimidazole compounds.

[0571] The O-acyl oxime compound is a compound having a partial structure represented by formula (d1).

[0572]

[0573] 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-carbazol-3-yl]ethane-1-imine, N-acetoxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethyl-2,4-dioxolanylmethyloxy)benzoyl}-9H-carbazol-3-yl]ethane-1-imine, -1-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropane-1-imine, N-benzoyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropane-1-one-2-imine, N-acetoxy-1-[4-(2-hydroxyethyloxy)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, etc. Irgacure OXE01 can also be used. ·, OXE02, OXE03 (all manufactured by BASF), N-1919 (manufactured by ADEKA), PBG-314, PBG-317, PBG-326, PBG-327, PBG-329 (all manufactured by Changzhou Qiangli Electronic New Materials Co., Ltd.) and other commercial products. Among them, the O-acyl oxime compound is preferably selected from N-acetoxy-1-[4-(2-hydroxyethyloxy)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 At least one of 2-[(acetyloxy)imino]-3-cyclohexyl-1-[4-(phenylthio)phenyl]propane-1-one and N-benzoyloxy-1-(4-phenylthiophenyl)octane-1-one-2-imine. In the case of these O-acyl oxime compounds, there is a tendency to obtain a color filter with high brightness.

[0574] 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.

[0575]

[0576] Examples of compounds 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, 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholino)phenyl]butane-1-one, etc. Commercially available products such as Irgacure 369, 907, and 379 (all manufactured by BASF) can be used.

[0577] As the compound having a partial structure represented by formula (d3), for example, there can be mentioned 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, benzil dimethyl ketal, etc.

[0578] In terms of sensitivity, the alkylphenone compound is preferably a compound having a partial structure represented by formula (d2).

[0579] 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, 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.

[0580] 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) may also be used.

[0581] 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, 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.).

[0582] 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 amines) described later.

[0583] Examples of the polymerization initiator that generates an acid include onium salts such as 4-hydroxyphenyldimethylsulfonium p-toluenesulfonate, 4-hydroxyphenyldimethylsulfonium hexafluoroantimonate, 4-acetoxyphenyldimethylsulfonium p-toluenesulfonate, 4-acetoxyphenylmethylbenzylsulfonium hexafluoroantimonate, triphenylsulfonium p-toluenesulfonate, triphenylsulfonium hexafluoroantimonate, diphenyliodonium p-toluenesulfonate, and diphenyliodonium hexafluoroantimonate, nitrobenzyl p-toluenesulfonate, and benzoin p-toluenesulfonate.

[0584] The polymerization initiator (D) is preferably a polymerization initiator containing at least one selected from an alkylphenone compound, a triazine compound, an acylphosphine oxide compound, an O-acyl oxime compound and a biimidazole compound, and more preferably a polymerization initiator containing an O-acyl oxime compound.

[0585] The content of the polymerization initiator (D) 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 content of the polymerization initiator (D) is within the above range, there is a tendency for high sensitivity and shortened exposure time, thereby improving the productivity of the color filter.

[0586] <Polymerization initiator aid (D1)>

[0587] 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).

[0588] Examples of the polymerization initiation aid (D1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds, and carboxylic acid compounds.

[0589] 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.

[0590] 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.

[0591] Examples of the thioxanthone compound include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, and 1-chloro-4-propoxythioxanthone.

[0592] 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.

[0593] 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.

[0594] <Solvent (E)>

[0595] The solvent (E) is not particularly limited, and a solvent commonly used in this field can be used. For example, an ester solvent (a solvent containing -COO- and not containing -O- in the molecule), an ether solvent (a solvent containing -O- and not containing -COO- in the molecule), an ether ester solvent (a solvent containing -COO- and -O- in the molecule), a ketone solvent (a solvent containing -CO- and not containing -COO- in the molecule), an alcohol solvent (a solvent containing OH and not containing -O-, -CO- and -COO- in the molecule), an aromatic hydrocarbon solvent, an amide solvent, dimethyl sulfoxide, etc. can be mentioned.

[0596] 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.

[0597] 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.

[0598] 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.

[0599] Examples of the ketone solvent include 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone and isophorone.

[0600] Examples of the alcohol solvent include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerin.

[0601] Examples of the aromatic hydrocarbon solvent include benzene, toluene, xylene, and mesitylene.

[0602] Examples of the amide solvent include N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.

[0603] The solvent is preferably at least one selected from ether solvents, ether ester solvents and amide solvents, more preferably contains ether solvents, ether ester solvents and amide solvents, and further preferably contains diethylene glycol methyl ethyl ether, propylene glycol monomethyl ether acetate and N-methylpyrrolidone.

[0604] Among the above solvents, organic solvents having a boiling point of 120° C. to 180° C. at 1 atm are preferred from the viewpoint of coating properties and drying properties. As the solvent, 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 are preferred, and propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate and ethyl 3-ethoxypropionate are more preferred.

[0605] 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 become good.

[0606] <Leveling agent (F)>

[0607] 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.

[0608] Examples of the silicone-based surfactant include surfactants having a siloxane bond in the molecule. Specific examples include 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 (Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452, and TSF4460 (manufactured by Momentive Performance Materials Japan Co., Ltd.).

[0609] 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 Co., Ltd.), 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 (formerly manufactured by Asahi Glass Co., Ltd.) and E5844 (manufactured by Daikin Fine Chemicals Laboratories, Ltd.), etc.

[0610] Examples of the above-mentioned silicone-based surfactant having a fluorine atom 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).

[0611] 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 this content does not include the content of the above-mentioned pigment dispersant. When the content of the leveling agent (F) is within the above range, the flatness of the color filter can be improved.

[0612] <Other ingredients>

[0613] 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.

[0614] <Method for producing colored resin composition>

[0615] The colored resin composition can be prepared by mixing, for example, a colorant (A) containing an aluminum phthalocyanine dye, a compound represented by formula (DA), a resin (B), a solvent (E), and, if necessary, a polymerizable compound (C), a polymerization initiator (D), a leveling agent (F), a polymerization initiator aid (D1), and other components.

[0616] The aluminum phthalocyanine dye may be contained in the pigment dispersion in advance. The target colored resin composition can be prepared by mixing the remaining components into the pigment dispersion so as to have a predetermined concentration.

[0617] When a dye is included, the dye may be dissolved in part or all of the solvent (E) to prepare a solution. The solution is preferably filtered through a filter having a pore size of about 0.01 to 1 μm.

[0618] The mixed colored resin composition is preferably filtered through a filter having a pore size of about 0.01 to 10 μm.

[0619] [Color Filter]

[0620] As a method for manufacturing a coloring pattern of a color filter from 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 and developed through a photomask. 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. The colored pattern and colored coating film formed in this way are the color filter of the present invention.

[0621] The film thickness of the color filter (color coating film) 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.

[0622] 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, and circuits can be formed on these substrates. In addition, a substrate obtained by subjecting a silicon substrate to HMDS treatment can also be used.

[0623] The formation of each color pixel by photolithography can be performed using a known or customary device and conditions. For example, the formation can be performed as follows.

[0624] First, a colored resin composition is applied onto a substrate, and volatile components such as a solvent are removed by heating and drying (pre-baking) and / or drying under reduced pressure, thereby obtaining a smooth composition layer.

[0625] Examples of the coating method include spin coating, slit coating, and slit-spin coating.

[0626] The temperature during heat drying is preferably 30 to 120° C., more preferably 50 to 110° C. The heating time is preferably 10 seconds to 60 minutes, more preferably 30 seconds to 30 minutes.

[0627] When drying under reduced pressure is performed, it is preferably performed at a pressure of 50 to 150 Pa and a temperature range of 20 to 25° C. The film thickness of the composition layer is not particularly limited and may be appropriately selected depending on the film thickness of the target color filter.

[0628] 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 can be used.

[0629] As the light source used for exposure, a light source generating light with a wavelength of 250 to 450 nm is preferred. For example, light less than 350 nm may be cut off using a filter that cuts off this wavelength region, or light near 436 nm, 408 nm, and 365 nm may be selectively extracted using a bandpass filter that extracts these wavelength regions. Specifically, mercury lamps, light emitting diodes, metal halide lamps, halogen lamps, etc. may be cited.

[0630] In order to uniformly irradiate parallel light onto the entire exposure surface and precisely align the photomask and the substrate, it is preferable to use a reduction projection exposure apparatus such as a mask aligner and a stepper, or a contact exposure apparatus.

[0631] 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 and removed by development. As the developer, for example, an aqueous solution of an alkaline compound such as potassium hydroxide, sodium bicarbonate, sodium carbonate, and tetramethylammonium hydroxide is preferable. 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, a spray method, etc. Further, the substrate can be tilted at an arbitrary angle during development.

[0632] It is preferable to perform water washing after development.

[0633] It is further preferable to perform post-baking on the obtained colored pattern. The post-baking temperature is preferably 80 to 250°C, more preferably 100 to 245°C. The post-baking time is preferably 1 to 120 minutes, more preferably 2 to 30 minutes.

[0634] The obtained colored pattern and colored coating film are useful as a color filter, and this 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.), an electronic paper, a solid-state imaging element, etc.

[0635] This application claims the benefit of priority based on Japanese Patent Application No. 2020-150532 filed on September 8, 2020. The entire contents of the specification of Japanese Patent Application No. 2020-150532 filed on September 8, 2020 are incorporated herein by reference.

[0636] Examples

[0637] Hereinafter, the present invention will be described more specifically with reference to examples. However, the present invention is not originally limited by the following examples, and of course, appropriate modifications can be made within the scope suitable for the above and the following gists and implemented, and these are all included in the technical scope of the present invention. In the examples, % and parts indicating content or usage amount are on a mass basis unless otherwise specified.

[0638] The structure of the compound was confirmed by mass spectrometry (MALDI-TOF MS; JMS-S3000 manufactured by JEOL Ltd.).

[0639] <Conditions for MALDI>

[0640] Matrix: DCTB (trans-2-[3-(4-tert-butylphenyl)-2-methyl-2-propenylidene]malononitrile)

[0641] Solvent: THF (with stabilizer)

[0642] Ionizing agent: None

[0643] <Synthesis of Coloring Agent>

[0644] [Colorant Synthesis Example 1]

[0645] The compound represented by formula (1) was obtained according to the synthesis method described in JP-A-2016-75837.

[0646]

[0647] [Colorant Synthesis Example 2]

[0648] The compound represented by formula (2) was obtained according to the synthesis method described in the Supporting Information of Ryan B. Snitynsky et al. "Synthesis of Nitrogen-Containing Furanose Sugar Nucleotides for Use as Enzymatic Probes" (Org. Lett. 2014, 16, 1, 212-215).

[0649]

[0650] 1.0 part of the compound represented by formula (3) (manufactured by Tokyo Chemical Industry Co., Ltd.), 0.34 part of the compound represented by formula (2), and 5.0 parts of N-methylpyrrolidone (NMP) (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) were mixed at room temperature, heated to 120°C and stirred for 6 hours. After the reaction solution was cooled to room temperature, 50 parts of ion exchange water was added. The obtained precipitate was obtained as a suction filtration residue, washed with 50 parts of ion exchange water, and dried under reduced pressure at 60°C to obtain 1.18 parts of the compound represented by formula (4).

[0651]

[0652] Identification of the compound represented by formula (4)

[0653] (Mass analysis) Ionization mode = MALDI-TOF-:

[0654] m / z=716.3

[0655] Exact molecular weight: 716.2

[0656] [Colorant Synthesis Example 3]

[0657] In the method for synthesizing the compound represented by formula (2) in Colorant Synthesis Example 2, the alcohol used was changed to 3-butene-1-ol to obtain a compound represented by formula (5).

[0658]

[0659] 1.0 part of the compound represented by formula (3) (manufactured by Tokyo Chemical Industry Co., Ltd.), 0.39 part of the compound represented by formula (5), and 5.0 parts of NMP were mixed at room temperature, heated to 120°C and stirred for 6 hours. After the reaction solution was cooled to room temperature, 50 parts of ion exchange water was added. The obtained precipitate was obtained as a suction filtration residue, washed with 50 parts of ion exchange water, and dried under reduced pressure at 60°C to obtain 1.24 parts of the compound represented by formula (6).

[0660]

[0661] Identification of the compound represented by formula (6)

[0662] (Mass analysis) Ionization mode = MALDI-TOF - :

[0663] m / z=744.4

[0664] Exact molecular weight: 744.2

[0665] [Colorant Synthesis Example 4]

[0666] 1.5 parts of aluminum chloride (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.), 6.2 parts of 4-tert-butylphthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.), 5.1 parts of 1,8-diazabicyclo[5.4.0]-7-undecene (manufactured by Tokyo Chemical Industry Co., Ltd.), and 11 parts of 1-pentanol (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) were mixed at room temperature, heated to 160°C, and stirred for 13 hours. After the reaction solution was cooled to room temperature, 63 parts of ethyl acetate was added. The obtained precipitate was obtained as a suction filtration residue, washed with 89 parts of ion exchange water, and then dried under reduced pressure at 60°C to obtain 3.4 parts of the compound represented by formula (7).

[0667]

[0668] Identification of the compound represented by formula (7)

[0669] (Mass analysis) Ionization mode = MALDI-TOF - :m / z=798.5

[0670] Exact molecular weight: 798.4

[0671] 1.1 parts of the compound represented by formula (7), 0.25 parts of the compound represented by formula (8) ("API-9" manufactured by Katayama Chemical Industry Co., Ltd.), and 5.5 parts of NMP were mixed at room temperature, heated to 120°C, and stirred for 7 hours. After the reaction solution was cooled to room temperature, 28 parts of ion exchange water was added. The obtained precipitate was obtained as a suction filtration residue, washed with 11 parts of methanol, and dried under reduced pressure at 60°C to obtain 1.2 parts of the compound represented by formula (9).

[0672]

[0673] Identification of the compound represented by formula (9)

[0674] (Mass analysis) Ionization mode = MALDI-TOF - :m / z=930.6

[0675] Exact molecular weight: 930.4

[0676] <Synthesis of Resin>

[0677] [Resin Synthesis Example 1]

[0678] An appropriate amount of nitrogen was introduced into a flask equipped with a reflux cooler, a dropping funnel and a stirrer to replace the atmosphere with nitrogen, and 340 parts of propylene glycol monomethyl ether acetate was added and heated to 80°C while stirring. Then, 57 parts of acrylic acid, 3,4-epoxytricyclo[5.2.1.0 2，6 ]decane-8-yl ester and 3,4-epoxytricyclo[5.2.1.0 2，6 ] A mixed solution of 54 parts of a mixture of 9-decane decyl ester (containing a molar ratio of 1:1), 239 parts of benzyl methacrylate, and 73 parts of propylene glycol monomethyl ether acetate. On the other hand, a solution of 40 parts of a polymerization initiator 2,2-azobis(2,4-dimethylvaleronitrile) dissolved in 197 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After the addition of the solution containing the polymerization initiator was completed, it was kept at 80°C for 3 hours and then cooled to room temperature to obtain a copolymer (resin (B-1)) solution having a viscosity of 137 mPa·s and a solid content of 36.8% by weight as measured by a B-type viscometer (23°C). The weight average molecular weight of the resulting copolymer in terms of polystyrene was 1.0×10 3 , a dispersion degree of 1.97, and an acid value of 111 mg-KOH / g in terms of solid content. Resin (B-1) has the following structural units.

[0679]

[0680] <Preparation of Dispersion Liquid>

[0681] [Dispersion Preparation Example 1]

[0682] 5 parts of the compound represented by formula (1), 2 parts of a dispersant (BYK LPN-6919 manufactured by BYK) (in terms of solid content), 2 parts of a resin (B-1) (in terms of solid content), 1 part of a mixture of a compound represented by formula (da-1) and a compound represented by formula (da-2) (containing ratio in terms of molar ratio of 5:1), and 90 parts of propylene glycol monomethyl ether acetate were mixed, 300 parts of 0.2 μm zirconium oxide beads were added, and the mixture was shaken for 30 minutes using a paint conditioner (manufactured by LAU). The zirconium oxide beads were then removed by filtration to obtain a dispersion (A-1).

[0683]

[0684] [Dispersion Preparation Example 2 to Dispersion Preparation Example 9]

[0685] Except having changed each component as shown in Table 36, the same method as Dispersion Preparation Example 1 was carried out to obtain dispersions (A-2) to (A-9).

[0686] [Table 36]

[0687]

[0688] *1 Solid content conversion

[0689] [Dispersion Preparation Example 10 to Dispersion Preparation Example 15]

[0690] Except having changed each component as shown in Table 37, the same method as Dispersion Preparation Example 1 was carried out to obtain dispersions (A-10) to (A-15).

[0691] [Table 37]

[0692]

[0693] *1 Solid content conversion

[0694] <Preparation of Colored Resin Composition>

[0695] [Coloring resin composition 1]

[0696] The colored resin composition 1 was obtained by mixing the following components.

[0697]

[0698] [Colored resin composition 2 to colored resin composition 8, comparative colored resin composition 1]

[0699] Except having changed each component as shown in Table 38, by the same method as the colored resin composition 1, the colored resin composition 2 - the colored resin composition 8 and the comparative colored resin composition 1 were obtained.

[0700] [Table 38]

[0701]

[0702] * 1Solid composition calculation

[0703] [Colored resin composition 9 to colored resin composition 13, comparative colored resin composition 2]

[0704] Except having changed each component as shown in Table 39, by the method similar to the colored resin composition 1, the colored resin composition 9 - the colored resin composition 13 and the comparative colored resin composition 2 were obtained.

[0705] [Table 39]

[0706]

[0707] *1 Solid content conversion

[0708] <Evaluation of foreign matter in coating film>

[0709] [Formation of Colored Coating Film]

[0710] The colored resin compositions prepared in the colored resin compositions 1 to 8, 9 to 13 and the comparative colored resin compositions 1 and 2 were applied onto a 5 cm square glass substrate (EAGLE 2000; manufactured by CORNING) by spin coating, and then pre-baked at 90° C. for 2 minutes to form a colored composition layer. After cooling, an exposure machine (TME-150RSK; manufactured by TOPCON Corporation) was used to expose the colored resin compositions at 60 mJ / cm in an air atmosphere. 2 The colored composition layer was irradiated with light at an exposure amount of 100 nm (based on 365 nm). Then, post-baking was performed at 230° C. for 5 minutes to obtain a colored coating film.

[0711] [Observation of coating properties]

[0712] The colored coating film on the obtained glass substrate was checked for the presence or absence of foreign matter (coarse particles) in the colored coating film using a laser microscope (LEXT OLS4100; manufactured by Olympus Corporation).

[0713] ○: No foreign matter was observed

[0714] ×: Foreign matter was observed

[0715] According to Tables 38 and 39, no foreign matter was observed in the colored coating films of Colored Resin Compositions 1 to 8 and 9 to 13. On the other hand, many foreign matter was observed in Comparative Colored Resin Compositions 1 and 2.

[0716] <Adhesion Evaluation>

[0717] [Formation of dot pattern]

[0718] The colored resin compositions prepared in the colored resin compositions 9 to 13 and the comparative colored resin composition 2 were applied onto a 4-inch silicon wafer (manufactured by Rokko Electronics Co., Ltd.) by spin coating, and then pre-baked at 90° C. for 2 minutes to form a colored composition layer. After cooling, an exposure machine (NSR-2205i11D; manufactured by Nikon Corporation, NA=0.63, σ=0.60) was used in an air atmosphere at 400 mJ / cm 2 The colored composition layer was irradiated with light at an exposure amount (365 nm reference). During the light irradiation, an exposure mask was arranged between the irradiation light source and the substrate, and the colored composition layer was irradiated with light in a manner of forming a 0.9 μm dot pattern (pitch of 1.8 μm). Then, after the colored composition layer was developed, it was post-baked at 230° C. for 5 minutes to obtain a colored coating film.

[0719] [Confirmation of Adhesion]

[0720] The dot pattern of the colored coating film on the obtained substrate was observed using a laser microscope (LEXT OLS4100; manufactured by Olympus Corporation). The higher the adhesion between the substrate and the colored coating film, the more likely the dot pattern will remain on the substrate, and the lower the adhesion, the more likely the dot pattern will peel off from the substrate.

[0721] ○: 0.9 μm dot pattern was formed, no peeling

[0722] △: Although a 0.9 μm dot pattern was formed, some peeling was observed

[0723] ×: 0.9 μm dot pattern is completely peeled off from the substrate

[0724] In the comparative colored resin composition 2, the 0.9 μm dot pattern was completely peeled off from the substrate (evaluation: ×). On the other hand, in the colored resin compositions 9 to 13, a 0.9 μm dot pattern was formed and no peeling occurred (evaluation: ○). From the comparison between the comparative colored resin composition 2 and the colored resin compositions 9 to 13, it can be seen that when the content of the compound represented by the formula (DA) is preferably 1 part by mass or more (more preferably 10 parts by mass or more, and further preferably 15 parts by mass or more) relative to 100 parts by mass of the aluminum phthalocyanine dye, a colored coating film having higher adhesion to the substrate is formed.

Claims

1. A colored resin composition comprising a colorant, a compound represented by formula (DA), a resin and a solvent, The colorant comprises aluminum phthalocyanine pigment, The aluminum phthalocyanine pigment is a compound represented by formula (Xa), and the resin is an alkali-soluble resin. In formula (DA), R d1 Indicates that it has -CO2R xa1 or -SO3R xa1 A saturated aliphatic hydrocarbon group having 1 to 12 carbon atoms as a substituent, R xa1 is a hydrogen atom, R d2 and R d3 Represents R d2 With R d3 Bonded with -CO-NR d1 -CO- together form any one of the rings represented by formula (r-1) to formula (r-7), * indicates the same as R d1 The bonding site of In formula (Xa), Z represents a hydroxyl group, a chlorine atom, or -OP(=O)R a1 R a2 , R a1 ~R a2 Each independently represents a hydrogen atom, a hydroxyl group, or a hydrocarbon group having 1 to 21 carbon atoms, and R a1 With R a2 They are not bonded to each other to form a ring or are bonded to each other to form a ring, and when the number of carbon atoms of the hydrocarbon group is 2 to 21 and the hydrocarbon group has -CH2-, the -CH2- is not substituted or is substituted with -O-, -S- or -CO-, X x1 ~X x4 Each independently represents -R x4 ,-OR x4 , or a halogen atom, R x4 represents a hydrocarbon group having 1 to 20 carbon atoms, and when the hydrocarbon group has 1 to 20 carbon atoms and the hydrocarbon group has -CH2-, the -CH2- is unsubstituted or substituted with -O-, -S- or -CO-, nx1 to nx4 each independently represent an integer of 0 to 4.

2. The colored resin composition according to claim 1, wherein The compound represented by the formula (Xa) is a compound represented by the formula (XI), In formula (XI), R x1 represents an unsaturated hydrocarbon group having 2 to 20 carbon atoms or an aromatic hydrocarbon group having 6 to 20 carbon atoms, R x2 represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, or a Z-linked x2 With R x1 A single key, Z x1 and Z x2 each independently represents a single bond or an oxygen atom, X x1 ~X x4 Each independently represents -R x4 ,-OR x4 , or a halogen atom, R x4 represents a hydrocarbon group having 1 to 20 carbon atoms, and when the hydrocarbon group has 1 to 20 carbon atoms and the hydrocarbon group has -CH2-, the -CH2- is unsubstituted or substituted with -O-, -S- or -CO-, nx1 to nx4 each independently represent an integer of 0 to 4.

3. The colored resin composition according to claim 1, wherein The aluminum phthalocyanine pigment is a compound represented by formula (YI), In formula (YI), R y1 represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms, R y2 represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, or a Z-linked y3 With R y1 A single key, Y 1 and Z y1 each independently represents an oxygen atom or a sulfur atom, Z y2 and Z y3 each independently represents a single bond, an oxygen atom or a sulfur atom, Among them, Y 1 , Z y1 , Z y2 and Z y3 At least one of represents a sulfur atom, X y1 ~X y4 Each independently represents -R y4 ,-OR y4 , or a halogen atom, R y4 represents a hydrocarbon group having 1 to 20 carbon atoms, ny1 to ny4 each independently represent an integer of 0 to 4.

4. The colored resin composition according to any one of claims 1 to 3, wherein It further includes a polymerizable compound and a polymerization initiator. 5 . A color filter formed from the colored resin composition according to claim 1 . A display device comprising the color filter according to claim 5 . 7 . A solid-state imaging element comprising the color filter according to claim 5 .

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