Colored resin composition, color filter, display device, and solid-state image sensor

Abstract

The present invention addresses the problem of providing a colored resin composition containing an aluminum phthalocyanine pigment, the composition being capable of forming colored coating films free from the formation of inclusions (preferably ones free from the formation of inclusions and having satisfactory adhesiveness). This colored resin composition comprises a colorant, a compound represented by formula (DA), a resin, and a solvent, wherein the colorant includes an aluminum phthalocyanine pigment. [In formula (DA), Rd1 represents an optionally substituted hydrocarbon group having 1-12 carbon atoms, and when the hydrocarbon group has 2-12 carbon atoms and includes -CH2-, then the -CH2- may have been replaced by -O-, -S-, or -CO-; and Rd2 and Rd3 each independently represent a hydrogen atom or an optionally substituted hydrocarbon group having 1-12 carbon atoms, or Rd2 and Rd3 are bonded to each other to form a ring in cooperation with the -CO-NRd1-CO-.]

Description

[Technical Field]

[0001] The present invention relates to a colored resin composition, a color filter, a display device, and a solid-state image sensor. [Background technology]

[0002] Color filters used in display devices such as liquid crystal displays, electroluminescent displays, and plasma displays, as well as solid-state image sensors such as CCDs and CMOS sensors, are manufactured from colored resin compositions. Aluminum phthalocyanine dyes are known as colorants for such colored resin compositions. Patent Document 1 describes a colored composition for color filters containing an aluminum phthalocyanine pigment.

[0003] On the other hand, Patent Document 2 describes that in order to improve the flow characteristics of a colored composition in which nanomaterials such as nanoorganic pigments and dyes are dispersed, and to achieve a dispersion state with low viscosity, low thixotropy, and stability over time, and to obtain a high-quality colored composition that has little effect or change on the electrical resistance value, an additive having a specific structure represented by general formula (1) is applied. [Prior art documents] [Patent Documents]

[0004] [Patent Document 1] Japanese Patent Publication No. 2016-075837 [Patent Document 2] Japanese Patent Publication No. 2018-150498 [Overview of the Initiative] [Problems that the invention aims to solve]

[0005] The inventors' investigations revealed that colored resin compositions containing aluminum phthalocyanine dyes tend to produce foreign matter when a colored coating film is formed. Furthermore, the formed colored coating film is also prone to peeling.

[0006] Accordingly, an object of the present invention is to provide a colored resin composition containing an aluminum phthalocyanine dye capable of forming a colored coating film free from foreign matter generation (preferably a colored coating film free from foreign matter generation and having good adhesion). [Means for Solving the Problem]

[0007] The present invention includes the following inventions. [1] A colored resin composition comprising a colorant, a compound represented by formula (DA), a resin and a solvent, wherein the colorant comprises an aluminum phthalocyanine dye. [Chemical Formula] [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 replaced with -O-, -S- or -CO-. R d2 and R d3 each independently represent a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms which may have a substituent, or R d2 and R d3 are bonded to each other to form a ring together with -CO-NR d1 -CO-.] [2] The colored resin composition according to [1], wherein the aluminum phthalocyanine dye is a compound represented by formula (Xa) or formula (Xb). [Chemical Formula] [Chemical Formula] [In formula (Xa), Z is a hydroxy group, a chlorine atom, -OP(=O)R a1 R a2 , or -O-SiR a3 R a4 Ra5 It represents. R a1 ~R a5 Each of these independently represents a hydrogen atom, a hydroxyl group, or a hydrocarbon group having 1 to 21 carbon atoms that may have substituents, and R a1 and R a2 , or R a3 ~R a5 Any two of these may be bonded together to form a ring. If the hydrocarbon group has 2 to 21 carbon atoms and contains -CH2-, the -CH2- may be replaced by -O-, -S-, or -CO-. X x1 ~X x4 These are, independently, -R x4 , -OR x4 , -SR x4 This represents a halogen atom, a nitro group, or a sulfamoyl group which may have a substituent. R x4 represents a hydrocarbon group having 1 to 20 carbon atoms, which may have substituents. If the hydrocarbon group has 2 to 21 carbon atoms and contains -CH2-, then -CH2- may be replaced by -O-, -S-, or -CO-. nx1 to nx4 each independently represent an integer from 0 to 4. In formula (Xb), L is -O-SiR a6 R a7 -O-, -O-SiR a8 R a9 -O-SiR a10 R a11 -O-, or -OP(=O)R a12 Represents -O- R a6 ~R a12 Each of these independently represents a hydrogen atom, a hydroxyl group, or a hydrocarbon group having 1 to 21 carbon atoms that may have substituents, and R a6 and R a7 , R a8 and R a9 , or R a10 and R a11These may bond to each other to form a ring. If the hydrocarbon group has 2 to 21 carbon atoms and contains -CH2-, the -CH2- may be replaced by -O-, -S-, or -CO-. X x5 ~X x12 These are, independently, -R x5 , -OR x5 , -SR x5 This represents a halogen atom, a nitro group, or a sulfamoyl group which may have a substituent. R x5 This represents a hydrocarbon group having 1 to 20 carbon atoms, which may have substituents. nx5 to nx12 each independently represent integers from 0 to 4. [3] The colored resin composition according to [2], wherein the compound represented by formula (Xa) is the compound represented by formula (XI), and the compound represented by formula (Xb) is the compound represented by formula (XII). [ka] [ka] [In formula (XI), R x1 R represents an unsaturated hydrocarbon group having 2 to 20 carbon atoms that may have substituents, or an aromatic hydrocarbon group having 6 to 20 carbon atoms that may have substituents. x2 is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms which may have substituents, or Z x2 and R x1 This represents a single bond connecting two things. Z x1 and Z x2 Each of these independently represents either a single bond or an oxygen atom. X x1 ~X x4 nx1 to nx4 are the same as described above. In formula (XII), R x3 This represents an unsaturated hydrocarbon group having 2 to 20 carbon atoms that may have substituents, or an aromatic hydrocarbon group having 6 to 20 carbon atoms that may have substituents. Z x3 This represents a single bond or an oxygen atom. X x5 ~X x12 nx5~nx12 are the same as above. [4] The colored resin composition according to [1], wherein the aluminum phthalocyanine dye is a compound represented by formula (YI) or formula (YII). [ka] [ka] [In formula (YI), R y1 This represents a hydrocarbon group having 1 to 20 carbon atoms, which may have a hydrogen atom or substituents. R y2 This is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms which may have substituents, or Z y3 and R y1 This represents a single bond connecting two things. Y 1 and Z y1 Each of these independently represents either an oxygen atom or a sulfur atom. Z y2 and Z y3 Each of these independently represents a single bond, an oxygen atom, or a sulfur atom. However, Y 1 , Z y1 , Z y2 and Z y3 At least one of them represents a sulfur atom. X y1 ~X y4 These are, independently, -R y4 , -OR y4 , -SR y4 This represents a halogen atom, a nitro group, or a sulfamoyl group which may have a substituent. R y4 This represents a hydrocarbon group having 1 to 20 carbon atoms, which may have substituents. ny1 to ny4 each independently represent an integer from 0 to 4. In formula (YII), Ry3 represents a hydrogen atom or an optionally substituted hydrocarbon group having 1 to 20 carbon atoms. Y 2 and Z y4 each independently represent an oxygen atom or a sulfur atom. Z y5 represents a single bond, an oxygen atom or a sulfur atom. provided that at least one of Y 2 , Z y4 and Z y5 is a sulfur atom. X y5 to X y12 each independently represent -R y5 , -OR y5 , -SR y5 , a halogen atom, a nitro group, or an optionally substituted sulfamoyl group. R y5 represents an optionally substituted hydrocarbon group having 1 to 20 carbon atoms. ny5 to ny12 each independently represent an integer of 0 to 4.] [5] The colored resin composition according to any one of [1] to [4], further comprising a polymerizable compound and a polymerization initiator. [6] A color filter formed from the colored resin composition according to any one of [1] to [5]. [7] A display device comprising the color filter according to [6]. [8] A solid-state image sensor comprising the color filter according to [7]. [Effects of the Invention]

[0008] According to the colored resin composition of the present invention, a colored coating film free of foreign matter (preferably a colored coating film free of foreign matter and having good adhesion) can be formed. [Mode for Carrying Out the Invention]

[0009] <<Colored Resin Composition>> The present invention includes a colored resin composition containing a colorant (hereinafter sometimes referred to as colorant (A)), a compound represented by formula (DA), a resin (hereinafter sometimes referred to as resin (B)) and a solvent (hereinafter sometimes referred to as solvent (E)), wherein the colorant contains an aluminum phthalocyanine dye. Furthermore, the present invention preferably includes a colored resin composition containing a polymerizable compound (hereinafter sometimes referred to as polymerizable compound (C)) and a polymerization initiator (hereinafter sometimes referred to as polymerization initiator (D)). The colored resin composition of the present invention may optionally contain a leveling agent (hereinafter sometimes referred to as leveling agent (F)). In the present specification, unless otherwise specified, the compounds exemplified as each component may be used alone or in combination of two or more thereof.

[0010] According to the colored resin composition of the present invention, a colored coating film free from generation of foreign matters can be formed. Furthermore, the obtained colored coating film has good adhesion to a substrate. In addition, according to the colored resin composition of the present invention, improvements in exposure sensitivity, development speed, residue after development, residual film ratio, and pattern shape can also be expected.

[0011] <Colorant (A)> The colored resin composition according to the present invention contains an aluminum phthalocyanine dye as a colorant. Specifically, the aluminum phthalocyanine dye refers to a dye having a phthalocyanine skeleton, in which the phthalocyanine skeleton and aluminum form a complex.

[0012] Specifically, the aluminum phthalocyanine dye is preferably a compound represented by formula (Xa) or formula (Xb). Hereinafter, the present invention will be described more specifically with reference to partial structures of the compounds represented by formula (Xa) or formula (Xb). Definitions common to formula (XI) and formula (XII) will be described later.

[0013]

Chemical Formula

[0014] [Chem.]]

[0015] In formula (Xa), Z represents a hydroxy group, a chlorine atom, -OP(=O)R a1 R a2 , or -O-SiR a3 R a4 R a5 . R a1 to R a5 each independently represent a hydrogen atom, a hydroxy group, or a hydrocarbon group having 1 to 21 carbon atoms which may have a substituent, and R a1 and R a2 , or any two of R a3 to R a5 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-. X x1 to X x4 each independently represent -R x4 , -OR x4 , -SR x4 , a halogen atom, a nitro group, or a sulfamoyl group which may have a substituent. R x4 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 with -O-, -S- or -CO-. nx1 to nx4 each independently represent an integer of 0 to 4. In formula (Xb), L represents -O-SiR a6 R a7 -O-, -O-SiR a8 R a9 -O-SiR a10 R a11 -O-, or -O-P(=O)R a12 -O-. R a6 to R a12Each of these independently represents a hydrogen atom, a hydroxyl group, or a hydrocarbon group having 1 to 21 carbon atoms that may have substituents, and R a6 and R a7 , R a8 and R a9 , or R a10 and R a11 These may bond to each other to form a ring. If the hydrocarbon group has 2 to 21 carbon atoms and contains -CH2-, the -CH2- may be replaced by -O-, -S-, or -CO-. X x5 ~X x12 These are, independently, -R x5 , -OR x5 , -SR x5 This represents a halogen atom, a nitro group, or a sulfamoyl group which may have a substituent. R x5 This represents a hydrocarbon group having 1 to 20 carbon atoms, which may have substituents. nx5 to nx12 each independently represent integers from 0 to 4.

[0016] R a1 ~R a12 This represents a hydrocarbon group having 1 to 21 carbon atoms, which may have substituents. R a1 and R a2 , R a3 ~R a5 Any two of R a6 and R a7 , R a8 and R a9 , or R a10 and R a11 These elements may be joined together to form a ring.

[0017] If the hydrocarbon group has 2 to 21 carbon atoms and contains -CH2-, then the -CH2- may be replaced by -O-, -S-, or -CO-. However, in the hydrocarbon group having 2 to 21 carbon atoms, adjacent -CH2- may not be simultaneously replaced by -O- and / or -S-, and terminal -CH2- may not be replaced by -O-, -S-, or -CO-.

[0018] Furthermore, when a -CH2- in a hydrocarbon group having 1 to 21 carbon atoms, which may have substituents, is replaced with -O-, -S-, or -CO-, the number of carbon atoms in the group replaced with -O-, -S-, or -CO- represents the number of carbon atoms in the hydrocarbon group before the replacement with -O-, -S-, or -CO-. For example, the *-O-CH2-CH2-CH3 group is a hydrocarbon group having 4 carbon atoms (*-CH2-CH2-CH2-CH3) in which the -CH2- is replaced with -O-. Furthermore, if there are multiple replaceable -CH2- groups in a hydrocarbon group having 1 to 21 carbon atoms, the number of replacements is not necessarily limited to one. For example, in a hydrocarbon group having 4 carbon atoms (*-CH2-CH2-CH2-CH3), two -CH2- groups can be replaced with -O- groups to become *-O-CH2-O-CH3. In other words, groups in which two or more -CH2- groups are replaced with -O-, -S-, or -CO- groups, such as *-O-CH2-O-CH3, are also included in "groups in which -CH2- groups in hydrocarbon groups having 1 to 21 carbon atoms that may have substituents are replaced with -O-, -S-, or -CO- groups."

[0019] In equation (Xa), Z is preferably -OP(=O)R a1 R a2 That is the case. R a1 Preferably -R b1 , -OR b1 , -SR b1 , or -CO-R b1 That is the case. R a2 Preferably -R b2 , -OR b2 , -SR b2 , or -CO-R b2 That is the case. R b1 and R b2 R represents a hydrocarbon group having 1 to 20 carbon atoms, which may have substituents. b1 and R b2 These elements may be joined together to form a ring.

[0020] In equation (Xb), L is preferably -O-P(=O)R a12 -O-. R a12 is preferably -R b3 , -O-R b3 , -S-R b3 , or -CO-R b3 . R b3 represents a C1-C20 hydrocarbon group which may have a substituent.

[0021] The compound represented by said formula (Xa) is preferably a compound represented by formula (XI). Further, the compound represented by said formula (Xb) is preferably a compound represented by formula (XII). Hereinafter, the present invention will be described more specifically with reference to the partial structures of the compounds represented by formula (XI) or formula (XII).

[0022]

Chemical Formula

[0023]

Chemical Formula

[0024] [In formula (XI), R x1 represents a C2-C20 unsaturated hydrocarbon group which may have a substituent or a C6-C20 aromatic hydrocarbon group which may have a substituent, R x2 represents a hydrogen atom, a C1-C20 hydrocarbon group which may have a substituent, or a single bond connecting Z x2 and R x1 . Z x1 and Z x2 each independently represent a single bond or an oxygen atom. X x1 to X x4 and nx1 to nx4 are as defined above. In formula (XII), R x3This represents an unsaturated hydrocarbon group having 2 to 20 carbon atoms that may have substituents, or an aromatic hydrocarbon group having 6 to 20 carbon atoms that may have substituents. Z x3 This represents a single bond or an oxygen atom. X x5 ~X x12 nx5~nx12 are the same as above.

[0025] Furthermore, the aluminum phthalocyanine dye is preferably a compound represented by formula (YI) or formula (YII). The present invention will be described more specifically below with reference to the partial structures of the compounds represented by formula (YI) or formula (YII).

[0026] [ka]

[0027] [ka]

[0028] [In formula (YI), R y1 This represents a hydrocarbon group having 1 to 20 carbon atoms, which may have a hydrogen atom or substituents. R y2 This is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms which may have substituents, or Z y3 and R y1 This represents a single bond connecting two things. Y 1 and Z y1 Each of these independently represents either an oxygen atom or a sulfur atom. Z y2 and Z y3 Each of these independently represents a single bond, an oxygen atom, or a sulfur atom. However, Y 1 , Z y1 , Z y2 and Z y3 At least one of them represents a sulfur atom. X y1 ~X y4 These are, independently, -R y4, -OR y4 , -SR y4 This represents a halogen atom, a nitro group, or a sulfamoyl group which may have a substituent. R y4 This represents a hydrocarbon group having 1 to 20 carbon atoms, which may have substituents. ny1 to ny4 each independently represent an integer from 0 to 4. In formula (YII), R y3 This represents a hydrocarbon group having 1 to 20 carbon atoms, which may have a hydrogen atom or substituents. Y 2 and Z y4 Each of these independently represents either an oxygen atom or a sulfur atom. Z y5 represents a single bond, an oxygen atom, or a sulfur atom. However, Y 2 , Z y4 and Z y5 At least one of them represents a sulfur atom. X y5 ~X y12 These are, independently, -R y5 , -OR y5 , -SR y5 This represents a halogen atom, a nitro group, or a sulfamoyl group which may have a substituent. R y5 This represents a hydrocarbon group having 1 to 20 carbon atoms, which may have substituents. ny5 to ny12 each independently represent an integer between 0 and 4.

[0029] Furthermore, compounds represented by formula (YI) include compounds having a resonance structure represented by formula (YIa) or compounds in equilibrium relationship represented by formula (YIb), and compounds represented by formula (YII) include compounds having a resonance structure represented by formula (YIIa) or compounds in equilibrium relationship represented by formula (YIIb).

[0030] [ka]

[0031] [ka]

[0032] [In equations (YI), (YIa), and (YIb), R y1 This represents a hydrocarbon group having 1 to 20 carbon atoms, which may have a hydrogen atom or substituents. R y2 This is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms which may have substituents, or Z y3 and R y1 This represents a single bond connecting two things. Y 1 and Z y1 Each of these independently represents either an oxygen atom or a sulfur atom. Z y2 and Z y3 Each of these independently represents a single bond, an oxygen atom, or a sulfur atom. However, Y 1 , Z y1 , Z y2 and Z y3 At least one of them represents a sulfur atom. X y1 ~X y4 These are, independently, -R y4 , -OR y4 , -SR y4 This represents a halogen atom, a nitro group, or a sulfamoyl group which may have a substituent. R y4 This represents a hydrocarbon group having 1 to 20 carbon atoms, which may have substituents. ny1 to ny4 each independently represent an integer from 0 to 4. In equations (YII), (YIIa), and (YIIb), R y3 This represents a hydrocarbon group having 1 to 20 carbon atoms, which may have a hydrogen atom or substituents. Y 2 and Z y4 Each of these independently represents either an oxygen atom or a sulfur atom. Z y5 represents a single bond, an oxygen atom, or a sulfur atom. However, Y 2 , Zy4 and Z y5 At least one of them represents a sulfur atom. X y5 ~X y12 These are, independently, -R y5 , -OR y5 , -SR y5 This represents a halogen atom, a nitro group, or a sulfamoyl group which may have a substituent. R y5 This represents a hydrocarbon group having 1 to 20 carbon atoms, which may have substituents. ny5 to ny12 each independently represent an integer between 0 and 4.

[0033] R x1 and R x3 The number of carbon atoms in the unsaturated hydrocarbon group represented is preferably 2 to 20, more preferably 2 to 10, even more preferably 2 to 7, and particularly preferably 2 to 5.

[0034] R x1 and R x3 The unsaturated hydrocarbon group represented by may be in the form of a chain or a cyclic (alicyclic hydrocarbon group).

[0035] R x1 and R x3 As an unsaturated chain hydrocarbon group represented by, Ethenyl group (vinyl group), propenyl group (e.g., 1-propenyl group, 2-propenyl group (allyl group)), 1-methylethenyl group, butenyl group (e.g., 1-butenyl group, 2-butenyl group, 3-butenyl group), 3-methyl-1-butenyl group, 1-methyl-1-butenyl group, 3-methyl-2-butenyl group, 1,3-butadienyl group, 3-methyl-1,2-butadienyl group, 1-(2-propenyl)ethenyl group, 1-(1-methylethenyl)ethenyl group, 1,1-dimethyl-2-propenyl group, 1,2-dimethyl-1-propenyl group, 1-ethyl-2-propenyl group, pentenyl group (e.g., 1-pentenyl group, 2-pentenyl group, 3-pentenyl group) Alkenyl groups such as nyl group, 4-pentenyl group, 1-(1,1-dimethylethyl)ethenyl group, 1,3-dimethyl-1-butenyl group, hexenyl group (e.g., 1-hexenyl group, 5-hexenyl group), heptenyl group (e.g., 1-heptenyl group, 6-heptenyl group), octenyl group (e.g., 1-octenyl group, 7-octenyl group), nonenyl group (e.g., 1-nonenyl group, 8-nonenyl group), decenyl group (e.g., 1-decenyl group, 9-decenyl group), undecenyl group, dodecenyl group, tridecenyl group, tetradecenyl group, pentadecenyl group, hexadecenyl group, heptadecenyl group, octadecenyl group, nonadecenyl group, icocenyl group, etc. Alkynyl groups such as ethynyl group, propynyl group (e.g., 1-propynyl group, 2-propynyl group), butynyl group (e.g., 1-butynyl group, 2-butynyl group, 3-butynyl group), pentynyl group, hexynyl group, heptynyl group, octinyl group (e.g., 1-octinyl group, 7-octinyl group), noninyl group, desinyl group, undecynyl group, dodecynyl group, tridecynyl group, tetradecynyl group, pentadecynyl group, hexadecinyl group, heptadecinyl group, octadecynyl group, nonadecinyl group, and icosinyl group; These are some examples.

[0036] R x1 and R x3 As an example of an unsaturated alicyclic hydrocarbon group, Cyclohexenyl groups such as cyclohexa-1-en-1-yl, cyclohexa-2-en-1-yl, cyclohexa-3-en-1-yl, cycloheptenyl, and cyclooctenyl; Unsaturated polycyclic hydrocarbon groups such as norborneyl groups; These are some examples.

[0037] R x1 and R x3 The unsaturated hydrocarbon group with 2 to 20 carbon atoms represented by may have substituents. R x1 and R x3 The substituents for the carbon 2-20 unsaturated hydrocarbon group represented by include optionally substituted carbon 6-20 aromatic hydrocarbon groups, optionally substituted heterocyclic groups, halogen atoms, nitro groups, cyano groups, and -OR xa1 , -CO2R xa1 , -SR xa1 , -SO2R xa1 , -SO3R xa1 -SO2NR xa1 R xa2 and -NR xa1 R xa2 These are some examples. Here, R xa1 and R xa2 Each of these independently represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms. xa1 and R xa2 The hydrocarbon group with 1 to 20 carbon atoms represented is R, which will be discussed later. b1 ~R b3 , R x2 , R x4 , R x5 and R y1 ~R y5 This is equivalent to a hydrocarbon group with 1 to 20 carbon atoms represented by .

[0038] R x1 and R x3 As for aromatic hydrocarbon groups with 6 to 20 carbon atoms that can be used as substituents on unsaturated hydrocarbon groups with 2 to 20 carbon atoms represented by , Phenyl group, o-tolyl group, m-tolyl group, p-tolyl group, 2-ethylphenyl group, 3-ethylphenyl group, 4-ethylphenyl group, 2,3-dimethylphenyl group, 2,4-dimethylphenyl group, 2,5-dimethylphenyl group, 2,6-dimethylphenyl group, 3,4-dimethylphenyl group, 3,5-dimethylphenyl group, 4-vinylphenyl group, o-isopropylphenyl group, m-isopropylphenyl group, p-isopropylphenyl group, o-tert-butylphenyl group, m-tert-butylphenyl group, p-tert-butylphenyl group, 3,5-di(tert-butyl)phenyl group, 3,5-di(tert-butyl)-4-methylphenyl group, 4-butylphenyl group, Aromatic hydrocarbon groups such as 4-pentylphenyl group, 2,6-bis(1-methylethyl)phenyl group, 2,4,6-tris(1-methylethyl)phenyl group, 4-cyclohexylphenyl group, 2,4,6-trimethylphenyl group, 4-octylphenyl group, 4-(1,1,3,3-tetramethylbutyl)phenyl group, 1-naphthyl group, 2-naphthyl group, 6-methyl-2-naphthyl group, 5,6,7,8-tetrahydro-1-naphthyl group, 5,6,7,8-tetrahydro-2-naphthyl group, fluorenyl group, phenanthryl group, anthryl group, 2-dodecylphenyl group, 3-dodecylphenyl group, 4-dodecylphenyl group, perilenyl group, crisenyl group, and pyrenyl group; and so on. The number of carbon atoms in the aromatic hydrocarbon group is preferably 6 to 10, and more preferably 6 to 8. The aromatic hydrocarbon group may have substituents, such as halogen atoms, nitro groups, cyano groups, and -OR groups. xa1 , -CO2R xa1 , -SR xa1 , -SO2R xa1 , -SO3R xa1 -SO2NR xa1 R xa2 and -NR xa1 R xa2 Examples include (however, R xa1 and R xa2 (The same applies as above.)

[0039] R x1 and R x3The heterocyclic group used as a substituent for the carbon-2 to carbon-20 unsaturated hydrocarbon group represented by may be monocyclic or polycyclic, and is preferably a heterocyclic ring containing a heteroatom as a ring component. Examples of heteroatoms include nitrogen, oxygen, and sulfur atoms. Examples of heterocycles containing only a nitrogen atom as a heteroatom 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, indidine, benzimidazole, quinoline, isoquinoline, quinoxaline, quinazoline, cinnoline, phthalazine, naphthyridine, purine, pteridine, benzopyrazole, and benzopiperidine; and condensed tricyclic heterocycles such as carbazole, acridine, and phenazine. Examples of heterocycles containing only an oxygen atom as a heteroatom include monocyclic saturated heterocycles such as oxiran, oxetane, tetrahydrofuran, tetrahydropyran, 1,3-dioxane, and 1,4-dioxane; bicyclic saturated heterocycles such as 1,4-dioxaspiro[4.5]decane and 1,4-dioxaspiro[4.5]nonane; lactone heterocycles such as α-acetolactone, β-propiolactone, γ-butyrolactone, and δ-valerolactone; five-membered unsaturated heterocycles such as furan; six-membered unsaturated heterocycles such as 2H-pyran and 4H-pyran; condensed bicyclic heterocycles such as 1-benzofuran, benzopyran, benzodioxol, chroman, and isochroman; and condensed tricyclic heterocycles such as xanthene and dibenzofuran. Examples of heterocycles containing only a sulfur atom as a heteroatom include five-membered saturated heterocycles such as dithiolane; six-membered saturated heterocycles such as thiane and 1,3-dithiane; five-membered unsaturated heterocycles such as thiophene, 4H-thiopyran, and benzothiopyran; fused bicyclic heterocycles such as benzothiophene; and fused tricyclic heterocycles such as thiantrene and dibenzothiophene. Examples of heterocycles containing nitrogen and oxygen atoms as heteroatoms include monocyclic saturated heterocycles such as morpholine, 2-pyrrolidone, and 2-piperidone; monocyclic unsaturated heterocycles such as oxazole and isoxazole; condensed bicyclic heterocycles such as benzoxazole, benzoisoxazole, benzoxazine, benzodioxane, and benzimidazoline; and condensed tricyclic heterocycles such as phenoxazine. Examples of heterocycles containing nitrogen and sulfur atoms as heteroatoms include monocyclic heterocycles such as thiazoles; fused bicyclic heterocycles such as benzothiazoles; and fused tricyclic heterocycles such as phenothiazines. The number of carbon atoms in the heterocyclic group is preferably 2 to 30, more preferably 3 to 22, and even more preferably 3 to 20. The heterocyclic group may have substituents, such as halogen atoms, nitro groups, cyano groups, and -OR groups. xa1 , -CO2R xa1 , -SR xa1 , -SO2R xa1 , -SO3R xa1 -SO2NR xa1 R xa2 and -NR xa1 R xa2 Examples include (however, R xa1 and R xa2 (The same applies as above.) The bonding positions of the heterocycle are the regions where any hydrogen atom contained in each ring has been removed.

[0040] R x1 and R x3 Examples of halogen atoms used as substituents on unsaturated hydrocarbon groups having 2 to 20 carbon atoms, as represented by , include fluorine, chlorine, bromine, and iodine atoms.

[0041] R x1 and R x3 The number of carbon atoms in the aromatic hydrocarbon group represented is preferably 6 to 20, more preferably 6 to 10, even more preferably 6 to 8, and particularly preferably 6.

[0042] R x1 and Rx3 Aromatic hydrocarbon groups represented by include phenyl group, o-tolyl group, m-tolyl group, p-tolyl group, 2-ethylphenyl group, 3-ethylphenyl group, 4-ethylphenyl group, 2,3-dimethylphenyl group, 2,4-dimethylphenyl group, 2,5-dimethylphenyl group, 2,6-dimethylphenyl group, 3,4-dimethylphenyl group, 3,5-dimethylphenyl group, 4-vinylphenyl group, o-isopropylphenyl group, m-isopropylphenyl group, p-isopropylphenyl group, o-tert-butylphenyl group, m-tert-butylphenyl group, p-tert-butylphenyl group, 3,5-di(tert-butyl)phenyl group, 3,5-di(tert-butyl)-4-methylphenyl group, 4- Aromatic hydrocarbon groups such as butylphenyl group, 4-pentylphenyl group, 2,6-bis(1-methylethyl)phenyl group, 2,4,6-tris(1-methylethyl)phenyl group, 4-cyclohexylphenyl group, 2,4,6-trimethylphenyl group, 4-octylphenyl group, 4-(1,1,3,3-tetramethylbutyl)phenyl group, 1-naphthyl group, 2-naphthyl group, 6-methyl-2-naphthyl group, 5,6,7,8-tetrahydro-1-naphthyl group, 5,6,7,8-tetrahydro-2-naphthyl group, fluorenyl group, phenanthryl group, anthryl group, 2-dodecylphenyl group, 3-dodecylphenyl group, 4-dodecylphenyl group, perilenyl group, chrysenyl group, and pyrenyl group; and the like.

[0043] R x1 and R x3 The aromatic hydrocarbon group having 6 to 20 carbon atoms represented by may have substituents. R x1 and R x3 Substituents for the C6-C20 aromatic hydrocarbon group represented by include halogen atoms such as fluorine, chlorine, bromine, and iodine, nitro groups, cyano groups, and -OR groups. xa1 , -CO2R xa1 , -SR xa1 , -SO2R xa1 , -SO3R xa1 -SO2NR xa1 R xa2 and -NR xa1 Rxa2 Examples include (however, R xa1 and R xa2 (The same applies as above.)

[0044] R a1 ~R a12 The number of carbon atoms in the hydrocarbon group represented is preferably 1 to 21, and more preferably 1 to 15. R b1 ~R b3 , R x2 , R x4 , R x5 and R y1 ~R y5 The number of carbon atoms in the hydrocarbon group represented is preferably 1 to 20, and more preferably 1 to 15.

[0045] R a1 ~R a12 A hydrocarbon group having 1 to 21 carbon atoms, represented by R 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, and the aliphatic hydrocarbon group may be saturated or unsaturated, and may be linear or cyclic (alicyclic hydrocarbon group).

[0046] R a1 ~R a12 , R b1 ~R b3 , R x2 , R x4 , R x5 and R y1 ~R y5 The saturated or unsaturated linear hydrocarbon groups represented by include linear alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, and eicosyl; Isopropyl group, isobutyl group, sec-butyl group, tert-butyl group, 2-ethylbutyl group, 3,3-dimethylbutyl group, 1,1,3,3-tetramethylbutyl group, 1-methylbutyl group, 1-ethylpropyl group, 3-methylbutyl group, neopentyl group, 1,1-dimethylpropyl group, 2-methylpentyl group, 3-ethylpentyl group, 1,3-dimethylbutyl group, 2-propylpentyl group, 1-ethyl-1,2-dimethylpropyl group, 1-methylpentyl group, 4-methylpentyl group, 4-methylpentyl group Branched alkyl groups such as hexyl group, 5-methylhexyl group, 2-ethylhexyl group, 1-methylhexyl group, 1-ethylpentyl group, 1-propylbutyl group, 3-ethylheptyl group, 2,2-dimethylheptyl group, 1-methylheptyl group, 1-ethylhexyl group, 1-propylpentyl group, 1-methyloctyl group, 1-ethylheptyl group, 1-propylhexyl group, 1-butylpentyl group, 1-methylnonyl group, 1-ethyloctyl group, 1-propylheptyl group, and 1-butylhexyl group; Ethenyl group (vinyl group), propenyl group (e.g., 1-propenyl group, 2-propenyl group (allyl group)), 1-methylethenyl group, butenyl group (e.g., 1-butenyl group, 2-butenyl group, 3-butenyl group), 3-methyl-1-butenyl group, 1-methyl-1-butenyl group, 3-methyl-2-butenyl group, 1,3-butadienyl group, 3-methyl-1,2-butadienyl group, 1-(2-propenyl)ethenyl group, 1-(1-methylethenyl)ethenyl group, 1,1-dimethyl-2-propenyl group, 1,2-dimethyl-1-propenyl group, 1-ethyl-2-propenyl group, pentenyl group (e.g., 1-pentenyl group, 2-pentenyl group, 3-pentenyl group) Alkenyl groups such as nyl group, 4-pentenyl group, 1-(1,1-dimethylethyl)ethenyl group, 1,3-dimethyl-1-butenyl group, hexenyl group (e.g., 1-hexenyl group, 5-hexenyl group), heptenyl group (e.g., 1-heptenyl group, 6-heptenyl group), octenyl group (e.g., 1-octenyl group, 7-octenyl group), nonenyl group (e.g., 1-nonenyl group, 8-nonenyl group), decenyl group (e.g., 1-decenyl group, 9-decenyl group), undecenyl group, dodecenyl group, tridecenyl group, tetradecenyl group, pentadecenyl group, hexadecenyl group, heptadecenyl group, octadecenyl group, nonadecenyl group, icocenyl group, etc. Alkynyl groups such as ethynyl group, propynyl group (e.g., 1-propynyl group, 2-propynyl group), butynyl group (e.g., 1-butynyl group, 2-butynyl group, 3-butynyl group), pentynyl group, hexynyl group, heptynyl group, octinyl group (e.g., 1-octinyl group, 7-octinyl group), noninyl group, desinyl group, undecynyl group, dodecynyl group, tridecynyl group, tetradecynyl group, pentadecynyl group, hexadecinyl group, heptadecinyl group, octadecynyl group, nonadecinyl group, and icosinyl group; These are some examples. R a1 ~R a12 , R b1 ~R b3 , R x2 , R x4 , R x5 and R y1 ~R y5The number of carbon atoms in the saturated chain hydrocarbon group represented is preferably 1 to 10, more preferably 1 to 7, and even more preferably 1 to 5. 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 unsaturated chain hydrocarbon group represented by is preferably 2 to 10, more preferably 2 to 7, and even more preferably 2 to 5.

[0047] R a1 ~R a12 , R b1 ~R b3 , R x2 , R x4 , R x5 and R y1 ~R y5 Examples of saturated or unsaturated alicyclic hydrocarbon groups represented by include cyclopropyl group, 1-methylcyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, 1-methylcyclohexyl group, 2-methylcyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 1,2-dimethylcyclohexyl group, 1,3-dimethylcyclohexyl group, 1,4-dimethylcyclohexyl group, 2,3-dimethylcyclohexyl group, 2,4-dimethylcyclohexyl group, and 2,5-dimethylcyclohexyl group. Cycloalkyl groups such as 2,6-dimethylcyclohexyl group, 3,4-dimethylcyclohexyl group, 3,5-dimethylcyclohexyl group, 2,2-dimethylcyclohexyl group, 3,3-dimethylcyclohexyl group, 4,4-dimethylcyclohexyl group, cyclooctyl group, 2,4,6-trimethylcyclohexyl group, 2,2,6,6-tetramethylcyclohexyl group, 3,3,5,5-tetramethylcyclohexyl group, 4-pentylcyclohexyl group, 4-octylcyclohexyl group, and 4-cyclohexylcyclohexyl group; Cyclohexenyl groups such as cyclohexa-1-en-1-yl, cyclohexa-2-en-1-yl, cyclohexa-3-en-1-yl, cycloheptenyl, and cyclooctenyl; Saturated or unsaturated polycyclic hydrocarbon groups such as norbornyl, norbornenyl, adamantyl, and bicyclo[2.2.2]octyl; These are some examples. 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 saturated or unsaturated alicyclic hydrocarbon group represented by is preferably 3 to 10.

[0048] R a1 ~R a12 , R b1 ~R b3 , R x2 , R x4 , R x5 and R y1 ~R y5Aromatic hydrocarbon groups represented by include phenyl group, o-tolyl group, m-tolyl group, p-tolyl group, 2-ethylphenyl group, 3-ethylphenyl group, 4-ethylphenyl group, 2,3-dimethylphenyl group, 2,4-dimethylphenyl group, 2,5-dimethylphenyl group, 2,6-dimethylphenyl group, 3,4-dimethylphenyl group, 3,5-dimethylphenyl group, 4-vinylphenyl group, o-isopropylphenyl group, m-isopropylphenyl group, p-isopropylphenyl group, o-tert-butylphenyl group, m-tert-butylphenyl group, p-tert-butylphenyl group, 3,5-di(tert-butyl)phenyl group, 3,5-di(tert-butyl)-4-methylphenyl group, 4- Aromatic hydrocarbon groups such as butylphenyl group, 4-pentylphenyl group, 2,6-bis(1-methylethyl)phenyl group, 2,4,6-tris(1-methylethyl)phenyl group, 4-cyclohexylphenyl group, 2,4,6-trimethylphenyl group, 4-octylphenyl group, 4-(1,1,3,3-tetramethylbutyl)phenyl group, 1-naphthyl group, 2-naphthyl group, 6-methyl-2-naphthyl group, 5,6,7,8-tetrahydro-1-naphthyl group, 5,6,7,8-tetrahydro-2-naphthyl group, fluorenyl group, phenanthryl group, anthryl group, 2-dodecylphenyl group, 3-dodecylphenyl group, 4-dodecylphenyl group, perilenyl group, chrysenyl group, and pyrenyl group; and the like. 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 is preferably 6 to 20, more preferably 6 to 10, and even more preferably 6 to 8.

[0049] R a1 ~R a12 , R b1 ~R b3 , R x2 , R x4 , R x5 and R y1 ~Ry5 The hydrocarbon group represented by may be a group formed by combining the hydrocarbon groups listed above (for example, an aromatic hydrocarbon group and at least one of a chain hydrocarbon group and an alicyclic hydrocarbon group), Aralkyl groups such as benzyl group, (2-methylphenyl)methyl group, (3-methylphenyl)methyl group, (4-methylphenyl)methyl group, (2-ethylphenyl)methyl group, (3-ethylphenyl)methyl group, (4-ethylphenyl)methyl group, (2-(tert-butyl)phenyl)methyl group, (3-(tert-butyl)phenyl)methyl group, (4-(tert-butyl)phenyl)methyl group, (3,5-dimethylphenyl)methyl group, 1-phenylethyl group, 1-methyl-1-phenylethyl group, 1,1-diphenylethyl group, (1-naphthyl)methyl group and (2-naphthyl)methyl group; Aryl alkenyl groups such as 1-phenylethenyl group, 2-phenylethenyl group (phenylvinyl group), 2,2-diphenylethenyl group, and 2-phenyl-2-(1-naphthyl)ethenyl group; Arylalkynyl groups such as phenylethynyl groups; A phenyl group to which one or more phenyl groups, such as a biphenylyl group or a terphenylyl group, are bonded; Cyclohexylmethylphenyl group, benzylphenyl group, (dimethyl(phenyl)methyl)phenyl group; These are some examples. These carbon numbers are preferably 7 to 18, and more preferably 7 to 15.

[0050] R a1 ~R a12 , R b1 ~R b3 , R x2 , R x4 , R x5 and R y1 ~R y5The group represented by may be an alkyl group to which one or more alicyclic hydrocarbon groups are bonded, such as a group formed by combining the hydrocarbon groups listed above (for example, a chain hydrocarbon group and an alicyclic hydrocarbon group), including cyclopropylmethyl group, cyclopropylethyl group, cyclobutylmethyl group, cyclobutylethyl group, cyclopentylmethyl group, cyclopentylethyl group, cyclohexylmethyl group, (2-methylcyclohexyl)methyl group, cyclohexylethyl group, and adamantylmethyl group. These carbon numbers are preferably 4 to 15, and more preferably 4 to 10.

[0051] R a1 ~R a12 A hydrocarbon group having 1 to 21 carbon atoms, represented by R 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 substituents. R a1 ~R a12 A hydrocarbon group having 1 to 21 carbon atoms, represented by R b1 ~R b3 , R x2 , R x4 , R x5 and R y1 ~R y5 The substituents of the hydrocarbon group having 1 to 20 carbon atoms represented by include heterocyclic groups which may have substituents, halogen atoms, nitro groups, cyano groups, and -OR xa1 , -CO2R xa1 , -SR xa1 , -SO2R xa1 , -SO3R xa1 -SO2NR xa1 R xa2 and -NR xa1 R xa2 Examples include (however, R xa1 and R xa2 (The same applies as above.)

[0052] R a1 ~R a12A hydrocarbon group having 1 to 21 carbon atoms, represented by R b1 ~R b3 , R x2 , R x4 , R x5 and R y1 ~R y5 The heterocyclic group used as a substituent for a hydrocarbon group having 1 to 20 carbon atoms, represented by , may be monocyclic or polycyclic, and is preferably a heterocyclic ring containing a heteroatom as a ring component. Examples of heteroatoms include nitrogen, oxygen, and sulfur atoms. The complex ring is R x1 and R x3 Examples include heterocyclic groups used as substituents on unsaturated hydrocarbon groups with 2 to 20 carbon atoms, as represented by [the formula shown]. The number of carbon atoms in the heterocyclic group is preferably 2 to 30, more preferably 3 to 22, and even more preferably 3 to 20. The heterocyclic group may have substituents, such as halogen atoms, nitro groups, cyano groups, and -OR groups. xa1 , -CO2R xa1 , -SR xa1 , -SO2R xa1 , -SO3R xa1 -SO2NR xa1 R xa2 and -NR xa1 R xa2 Examples include (however, R xa1 and R xa2 (The same applies as above.) The bonding positions of the heterocycle are the regions where any hydrogen atom contained in each ring has been removed.

[0053] R a1 ~R a12 A hydrocarbon group having 1 to 21 carbon atoms, represented by R b1 ~R b3 , R x2 , R x4 , R x5 and R y1 ~R y5 Examples of halogen atoms used as substituents on hydrocarbon groups having 1 to 20 carbon atoms, as represented by , include fluorine, chlorine, bromine, and iodine atoms.

[0054] R x2 is Z x2 and R x1 When it is a single bond connecting R, x1 Part or all of *-Z x2 -P(=O)-Z x1 -*(* represents a bond) forms a ring together. That is, R x2 is Z x2 and R x1 When it is a single bond connecting R, x1 Any carbon atom in an unsaturated hydrocarbon group having 2 to 20 carbon atoms that may have substituents, or any carbon atom in an aromatic hydrocarbon group having 6 to 20 carbon atoms that may have substituents (preferably any carbon atom in an unsaturated hydrocarbon group having 2 to 20 carbon atoms that may have substituents) and Z x2 A bond is formed between them by the sharing of a pair of electrons. x2 This corresponds to a single bond represented by .

[0055] R x1 Part or all of *-Z x2 -P(=O)-Z x1 -In a ring formed together with *(* represents a bond), unsaturated bonds may be formed between carbon atoms that are members of the ring, unsaturated bonds may be formed between carbon atoms that are members of the ring and carbon atoms that are not members of the ring, and unsaturated bonds may be formed between carbon atoms that are not members of the ring.

[0056] Also R y2 is Z y3 and R y1 When it is a single bond connecting R, y1 R is a hydrocarbon group having 1 to 20 carbon atoms, which may have substituents. y1 Part or all of *-Z y3 -P(=Z y1 )-Z y2 -*(* represents a bond) forms a ring together. That is, R y2 is Z y3 and R y1 When it is a single bond connecting R, y1Any carbon atom in a C1-C20 hydrocarbon group which may have substituents represented by Z y3 A bond is formed between them by the sharing of a pair of electrons. y2 This corresponds to a single bond represented by .

[0057] X x1 ~X x12 Examples of halogen atoms represented by include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms, with fluorine atoms being preferred.

[0058] X x1 ~X x12 The sulfamoyl group represented by is represented as *-SO2-NH2 (where * represents a bond). X x1 ~X x12 The sulfamoyl group represented by may have substituents. x1 ~X x12 The substituents of the sulfamoyl group represented by R x1 and R x3 These are the same substituents as the unsaturated hydrocarbon groups having 2 to 20 carbon atoms represented by , specifically, aromatic hydrocarbon groups having 6 to 20 carbon atoms which may have substituents, heterocyclic groups which may have substituents, halogen atoms, nitro groups, cyano groups, -OR xa1 , -CO2R xa1 , -SR xa1 , -SO2R xa1 , -SO3R xa1 -SO2NR xa1 R xa2 and -NR xa1 R xa2 Examples include (however, R xa1 and R xa2 (The same applies as above.)

[0059] X x1 ~X x4 -R, represented by x4 , X x5 ~X x12 -R, represented by x5 , X y1 ~X y4 -R, represented by y4 or X y5 ~Xy12 -R, represented by y5 The group is preferably an aliphatic hydrocarbon group having 1 to 20 carbon atoms, more preferably a saturated chain hydrocarbon group having 1 to 20 carbon atoms, even more preferably a saturated chain hydrocarbon group having 1 to 10 carbon atoms, even more preferably a branched chain alkyl group having 1 to 5 carbon atoms, and particularly preferably a tert-butyl group.

[0060] In equation (XI), R x1 teeth, A C2-C20 unsaturated chain hydrocarbon group which may have substituents, or a C6-C10 aromatic hydrocarbon group which may have substituents, is preferred. More preferably, an unsaturated chain hydrocarbon group having 2 to 10 carbon atoms, which may have substituents, or an aromatic hydrocarbon group having 6 to 8 carbon atoms, which may have substituents, More preferably, an unsaturated chain hydrocarbon group having 2 to 7 carbon atoms that may have substituents, or an aromatic hydrocarbon group having 6 to 7 carbon atoms that may have substituents, Particularly preferred are optionally substituted ethenyl groups, optionally substituted propenyl groups, optionally substituted butenyl groups, optionally substituted 3-methyl-2-butenyl groups, optionally substituted 3-methyl-1,2-butadienyl groups, optionally substituted heptenyl groups, optionally substituted ethynyl groups, optionally substituted propynyl groups, optionally substituted butynyl groups, or optionally substituted phenyl groups. R x1 When the unsaturated hydrocarbon group having 2 to 20 carbon atoms represented by has substituents, a phenyl group is preferred as the substituent. R x2 teeth, A C6-C20 aromatic hydrocarbon group which may have substituents or a C2-C20 unsaturated hydrocarbon group which may have substituents is preferred. A more preferable option is an aromatic hydrocarbon group having 6 to 10 carbon atoms that may have substituents, or an unsaturated chain hydrocarbon group having 2 to 20 carbon atoms that may have substituents. A more preferable option is an aromatic hydrocarbon group having 6 to 8 carbon atoms, which may have substituents, or an unsaturated chain hydrocarbon group having 2 to 7 carbon atoms, which may have substituents. Particularly preferred are optionally substituted phenyl groups, optionally substituted ethenyl groups, optionally substituted propenyl groups, optionally substituted butenyl groups, optionally substituted 3-methyl-2-butenyl groups, optionally substituted 3-methyl-1,2-butadienyl groups, optionally substituted heptenyl groups, optionally substituted ethynyl groups, optionally substituted propynyl groups, or optionally substituted butynyl groups. R x2 When the unsaturated hydrocarbon group having 2 to 20 carbon atoms represented by has substituents, a phenyl group is preferred as the substituent.

[0061] In equation (Xa) or equation (XI), X x1 ~X x4 These are, independently, -R x4 Alternatively, halogen atoms are preferred. nx1 to nx4 are each independently preferably 0 to 2, and more preferably 0 to 1.

[0062] In equation (XII), R x3 teeth, A C2-C20 unsaturated chain hydrocarbon group which may have substituents, or a C6-C10 aromatic hydrocarbon group which may have substituents, is preferred. More preferably, an unsaturated chain hydrocarbon group having 2 to 10 carbon atoms, which may have substituents, or an aromatic hydrocarbon group having 6 to 8 carbon atoms, which may have substituents, More preferably, an unsaturated chain hydrocarbon group having 2 to 5 carbon atoms, which may have substituents, or an aromatic hydrocarbon group having 6 to 7 carbon atoms, which may have substituents, Particularly preferred are optionally substituted ethenyl groups, optionally substituted propenyl groups, optionally substituted butenyl groups, optionally substituted ethynyl groups, optionally substituted propynyl groups, optionally substituted butynyl groups, or optionally substituted phenyl groups. R x3 When the unsaturated hydrocarbon group having 2 to 20 carbon atoms represented by has substituents, a phenyl group is preferred as the substituent.

[0063] In equation (Xb) or equation (XII), X x5 ~X x12 These are, independently, -R x5 Alternatively, halogen atoms are preferred. nx5 to nx12 are each independently preferably 0 to 2, more preferably 0 to 1.

[0064] As for aluminum phthalocyanine dyes (preferably compounds represented by formula (XI)), compounds represented by formulas (XIA) to (XIE) are preferred.

[0065] [ka]

[0066] [ka]

[0067] [ka]

[0068] [ka]

[0069] [ka]

[0070] [In formula (XIA) ~ formula (XIE), R x1 , R x2 , Z x1 and Z x2 The same applies as above.

[0071] Examples of compounds represented by formula (XIA) include those represented by formulas (XIA-1) to (XIA-190) shown in Tables 1 to 4. Examples of compounds represented by formula (XIB) include those represented by formulas (XIB-1) to (XIB-190) shown in Tables 5 to 8. Examples of compounds represented by formula (XIC) include the compounds represented by formulas (XIC-1) to (XIC-190) shown in Tables 9 to 12. Examples of compounds represented by formula (XID) include the compounds represented by formulas (XID-1) to (XID-190) shown in Tables 13 to 16. Examples of compounds represented by formula (XIE) include those represented by formulas (XIE-1) to (XIE-190) shown in Tables 17 to 20. Note that in Tables 1-3, 5-7, 9-11, 13-15, and 17-19, "R x1 " column and "R x2 The symbols listed in the column correspond to the bases represented by equations (xi-1) to (xi-12) and (xii-1), respectively. Also, in Tables 4, 8, 12, 16, and 20, "R x1 and R x2 The symbols listed in the "Groups formed by" column correspond to the groups represented by formulas (xca-1) to (xca-2), (xcb-1), and (xcc-1), respectively. x1 and R x2 The group formed by R x2 is Z x2 and R x1 When it is a single bond connecting and , *-Z x2 -P(=O)-Z x1 -* (where * represents a bond) represents the group that joins to the bond *. In formula (xca-1) ~ formula (xca-2), R x6 and R x7 Each of these independently represents a hydrogen atom or a C1-C20 hydrocarbon group which may have substituents, and the C1-C20 hydrocarbon group which may have substituents is R b1 ~R b3 , R x2 , R x4 , R x5 and R y1 ~R y5 Examples include hydrocarbon groups with 1 to 20 carbon atoms represented by . * represents a bond. In formula (xcb-1), R x8 This corresponds to the group represented by formula (xcc-1), and R x9 This corresponds to a hydrogen atom or a hydroxyl group. * represents a bond.

[0072] [ka]

[0073] [ka]

[0074] [ka]

[0075] [ka]

[0076] [Table 1]

[0077] [Table 2]

[0078] [Table 3]

[0079] [Table 4]

[0080] Compounds represented by formula (XIA) include: Compounds represented by formulas (XIA-1) to (XIA-12), (XIA-91) to (XIA-102), (XIA-103) to (XIA-108), (XIA-115) to (XIA-119), (XIA-126) to (XIA-129), (XIA-136) to (XIA-138), (XIA-145) to (XIA-146), (XIA-153), and (XIA-181) to (XIA-190) are preferred. Compounds represented by formulas (XIA-1) to (XIA-12), (XIA-103) to (XIA-105), (XIA-115) to (XIA-116), (XIA-126), (XIA-136) to (XIA-138), (XIA-145) to (XIA-146), (XIA-153), (XIA-181) to (XIA-182), (XIA-183) to (XIA-184), and (XIA-187) to (XIA-188) are more preferred. Compounds represented by formulas (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) are more preferably: Compounds represented by formulas (XIA-115), (XIA-126), and (XIA-182) are even more preferred.

[0081] [Table 5]

[0082] [Table 6]

[0083] [Table 7]

[0084] [Table 8]

[0085] Compounds represented by formula (XIB) include: Compounds represented by formulas (XIB-1) to (XIB-12), (XIB-91) to (XIB-102), (XIB-103) to (XIB-108), (XIB-115) to (XIB-119), (XIB-126) to (XIB-129), (XIB-136) to (XIB-138), (XIB-145) to (XIB-146), (XIB-153), and (XIB-181) to (XIB-190) are preferred. Compounds represented by formulas (XIB-1) to (XIB-12) are more preferred. Compounds represented by formula (XIB-1) are even more preferred.

[0086] [Table 9]

[0087] [Table 10]

[0088] [Table 11]

[0089] [Table 12]

[0090] Compounds represented by formula (XIC) include: Compounds represented by formulas (XIC-1) to (XIC-12), (XIC-91) to (XIC-102), (XIC-103) to (XIC-108), (XIC-115) to (XIC-119), (XIC-126) to (XIC-129), (XIC-136) to (XIC-138), (XIC-145) to (XIC-146), (XIC-153), and (XIC-181) to (XIC-190) are preferred. Compounds represented by formulas (XIC-1) to (XIC-12), (XIC-103) to (XIC-105), (XIC-115) to (XIC-116), and (XIC-126) are more preferred. Compounds represented by formulas (XIC-1) and (XIC-115) are even more preferred.

[0091] [Table 13]

[0092] [Table 14]

[0093] [Table 15]

[0094] [Table 16]

[0095] Compounds represented by formula (XID) include: Compounds represented by formulas (XID-1) to (XID-12), (XID-91) to (XID-102), (XID-103) to (XID-108), (XID-115) to (XID-119), (XID-126) to (XID-129), (XID-136) to (XID-138), (XID-145) to (XID-146), (XID-153), and (XID-181) to (XID-190) are preferred. Compounds represented by formulas (XID-1) to (XID-12) are more preferred. A compound represented by formula (XID-1) is even more preferred.

[0096] [Table 17]

[0097] [Table 18]

[0098] [Table 19]

[0099] [Table 20]

[0100] Compounds represented by formula (XIE) include: Compounds represented by formulas (XIE-1) to (XIE-12), (XIE-91) to (XIE-102), (XIE-103) to (XIE-108), (XIE-115) to (XIE-119), (XIE-126) to (XIE-129), (XIE-136) to (XIE-138), (XIE-145) to (XIE-146), (XIE-153), and (XIE-181) to (XIE-190) are preferred. Compounds represented by formulas (XIE-1) to (XIE-12), (XIE-103) to (XIE-105), (XIE-115) to (XIE-116), and (XIE-126) are more preferred. Compounds represented by formulas (XIE-1) and (XIE-115) are even more preferred.

[0101] As the aluminum phthalocyanine dye (preferably the compound represented by formula (XII)), compounds represented by formulas (XIIA) to (XIIE) are preferred.

[0102] [ka]

[0103] [ka]

[0104] [ka]

[0105] [ka]

[0106] [ka]

[0107] [In formula (XIIA) ~ formula (XIIE), R x3 and Z x3 The same applies as above.

[0108] Examples of compounds represented by formula (XIIA) include those represented by formulas (XIIA-1) to (XIIA-18) shown in Table 21. Examples of compounds represented by formula (XIIB) include those represented by formulas (XIIB-1) to (XIIB-18) shown in Table 22. Examples of compounds represented by formula (XIIC) include those represented by formulas (XIIC-1) to (XIIC-18) shown in Table 23. Examples of compounds represented by formula (XIID) include the compounds represented by formulas (XIID-1) to (XIID-18) shown in Table 24. Examples of compounds represented by formula (XIIE) include those represented by formulas (XIIE-1) to (XIIE-18) shown in Table 25. Note that in Tables 21 to 25, "R x3 The symbols listed in the column correspond to the bases represented by equations (xiii-1) to (xiii-9). * represents a bond.

[0109] [ka]

[0110] [Table 21]

[0111] Compounds represented by formula (XIIA) include: Compounds represented by formulas (XIIA-1) to (XIIA-6) and (XIIA-10) to (XIIA-15) are preferred.

[0112] [Table 22]

[0113] Compounds represented by formula (XIIB) include: Compounds represented by formulas (XIIB-1) to (XIIB-6) and (XIIB-10) to (XIIB-15) are preferred.

[0114] [Table 23]

[0115] Compounds represented by formula (XIIC) include: Compounds represented by formulas (XIIC-1) to (XIIC-6) and (XIIC-10) to (XIIC-15) are preferred.

[0116] [Table 24]

[0117] Compounds represented by formula (XIID) include: Compounds represented by formulas (XIID-1) to (XIID-6) and (XIID-10) to (XIID-15) are preferred.

[0118] [Table 25]

[0119] Compounds represented by formula (XIIE) include: Compounds represented by formulas (XIIE-1) to (XIIE-6) and (XIIE-10) to (XIIE-15) are preferred.

[0120] Note that the compounds represented by formula (XI) and formula (XII) include novel compounds. The compound represented by formula (XI) can be produced, for example, by appropriately reacting the compound represented by formula (XIII) with the compound represented by formula (XIV). Furthermore, 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).

[0121] [ka]

[0122] [In equations (XI), (XIII), and (XIV), R x1 , R x2 , Zx1 , Z x2 , X x1 ~X x4 , and nx1~nx4 are the same as above.

[0123] [ka]

[0124] [In equations (XII), (XIII), and (XV), R x3 , Z x3 , X x1 ~X x12 , and nx1~nx12 are the same as above.

[0125] In equation (YI), R y1 teeth, A C6 to C20 aromatic hydrocarbon group, which may have substituents, is preferred. A more preferable option is an aromatic hydrocarbon group having 6 to 10 carbon atoms, which may have substituents. A more preferred option is an aromatic hydrocarbon group having 6 to 8 carbon atoms, which may have substituents. Phenyl groups that may have substituents are particularly preferred. R y2 teeth, Preferably, an unsaturated hydrocarbon group having 2 to 20 carbon atoms, which may have substituents, or an aromatic hydrocarbon group having 6 to 20 carbon atoms, which may have substituents. More preferably, an unsaturated chain hydrocarbon group having 2 to 10 carbon atoms, which may have substituents, or an aromatic hydrocarbon group having 6 to 10 carbon atoms, which may have substituents. More preferably, an unsaturated chain hydrocarbon group having 2 to 7 carbon atoms, which may have substituents, or an aromatic hydrocarbon group having 6 to 8 carbon atoms, which may have substituents, More preferably, an alkenyl group having 2 to 7 carbon atoms that may have substituents, or an aromatic hydrocarbon group having 6 to 8 carbon atoms that may have substituents, A substituted ethenyl group or a substituted phenyl group is particularly preferred. Each of ny1 to ny4 is independently preferably 0 to 2, more preferably 0 to 1, and even more preferably 0. X y1 ~X y4 These are, independently, -R y4 Alternatively, halogen atoms are preferred. Y 1 , Z y1 , Z y2 and Z y3 At least one of them represents a sulfur atom, Y 1 The sulfur atom is Z y1 The mode in which is an oxygen atom, Y 1 is an oxygen atom and Z y1 The embodiment in which is a sulfur atom and Z y2 and Z y3 It is preferable that at least one of the embodiments in which is a sulfur atom is satisfied. However, R y2 If it is an unsaturated hydrocarbon group, then Z y2 and Z y3 It is preferable that the bond is a single bond.

[0126] In equation (YII), R y3 teeth, Preferably, an unsaturated hydrocarbon group having 2 to 20 carbon atoms, which may have substituents, or an aromatic hydrocarbon group having 6 to 20 carbon atoms, which may have substituents. More preferably, an unsaturated chain hydrocarbon group having 2 to 10 carbon atoms, which may have substituents, or an aromatic hydrocarbon group having 6 to 10 carbon atoms, which may have substituents. More preferably, an unsaturated chain hydrocarbon group having 2 to 7 carbon atoms, which may have substituents, or an aromatic hydrocarbon group having 6 to 8 carbon atoms, which may have substituents, More preferably, an alkenyl group having 2 to 7 carbon atoms that may have substituents, or an aromatic hydrocarbon group having 6 to 8 carbon atoms that may have substituents, A substituted ethenyl group or a substituted phenyl group is particularly preferred. Each of ny5 to ny12 is independently preferably 0 to 2, more preferably 0 to 1, and even more preferably 0. Xy5 ~X y12 These are, independently, -R y5 Alternatively, halogen atoms are preferred. Y 2 , Z y4 and Z y5 At least one of them represents a sulfur atom. However, R y3 If it is an unsaturated hydrocarbon group, then Z y5 It is preferable that the bond is a single bond.

[0127] Compounds represented by formula (YI) include those represented by formulas (YIA) to (YIE).

[0128] [ka]

[0129] [ka]

[0130] [ka]

[0131] [ka]

[0132] [ka]

[0133] [Formula (YIA) ~ Formula (YIE), R y1 , R y2 , Y 1 , Z y1 , Z y2 and Z y3 The same applies as above.

[0134] Examples of compounds represented by formula (YIA) include those represented by formulas (YIA-1) to (YIA-24) shown in Table 26. Examples of compounds represented by formula (YIB) include those represented by formulas (YIB-1) to (YIB-24) shown in Table 27. Examples of compounds represented by formula (YIC) include those represented by formulas (YIC-1) to (YIC-24) shown in Table 28. Examples of compounds represented by formula (YID) include the compounds represented by formulas (YID-1) to (YID-24) shown in Table 29. Examples of compounds represented by formula (YIE) include those represented by formulas (YIE-1) to (YIE-24) shown in Table 30. In Tables 26 to 30, "yi-1" represents a phenyl group, and "yi-2" represents an ethenyl group.

[0135] [Table 26]

[0136] Compounds represented by formula (YIA) include: Compounds represented by formulas (YIA-1) to (YIA-6), (YIA-13) to (YIA-18), (YIA-21), and (YIA-22) to (YIA-24) are preferred. Compounds represented by formulas (YIA-1), (YIA-13), (YIA-21), (YIA-23), and (YIA-24) are more preferred.

[0137] [Table 27]

[0138] Compounds represented by formula (YIB) include: Compounds represented by formulas (YIB-1) to (YIB-6), (YIB-13) to (YIB-18), (YIB-21), and (YIB-22) to (YIB-24) are preferred. Compounds represented by formulas (YIB-1), (YIB-13), (YIB-21), (YIB-23), and (YIB-24) are more preferred.

[0139] [Table 28]

[0140] Compounds represented by formula (YIC) include: Compounds represented by formulas (YIC-1) to (YIC-6), (YIC-13) to (YIC-18), (YIC-21), and (YIC-22) to (YIC-24) are preferred. Compounds represented by formulas (YIC-1), (YIC-13), (YIC-21), (YIC-23), and (YIC-24) are more preferred.

[0141] [Table 29]

[0142] Compounds represented by formula (YID) include: Compounds represented by formulas (YID-1) to (YID-6), (YID-13) to (YID-18), (YID-21), and (YID-22) to (YID-24) are preferred. Compounds represented by formulas (YID-1), (YID-13), (YID-21), (YID-23), and (YID-24) are more preferred.

[0143] [Table 30]

[0144] Compounds represented by formula (YIE) include: Compounds represented by formulas (YIE-1) to (YIE-6), (YIE-13) to (YIE-18), (YIE-21), and (YIE-22) to (YIE-24) are preferred. Compounds represented by formulas (YIE-1), (YIE-13), (YIE-21), (YIE-23), and (YIE-24) are more preferred.

[0145] Compounds represented by formula (YII) include those represented by formulas (YIIA) to (YIIE).

[0146] [ka]

[0147] [ka]

[0148] [ka]

[0149] [ka]

[0150] [ka]

[0151] [In equations (YIIA) to (YIIE), R y3 , Y 2 , Z y4 and Z y5 The same applies as above.

[0152] Examples of compounds represented by formula (YIIA) include the compounds represented by formulas (YIIA-1) to (YIIA-13) shown in Table 31. Examples of compounds represented by formula (YIIB) include those represented by formulas (YIIB-1) to (YIIB-13) shown in Table 32. Examples of compounds represented by formula (YIIC) include the compounds represented by formulas (YIIC-1) to (YIIC-13) shown in Table 33. Examples of compounds represented by formula (YIID) include the compounds represented by formulas (YIID-1) to (YIID-13) shown in Table 34. Examples of compounds represented by formula (YIIE) include the compounds represented by formulas (YIIE-1) to (YIIE-13) shown in Table 35. In Tables 31 to 35, "yi-1" represents a phenyl group, and "yi-2" represents an ethenyl group.

[0153] [Table 31]

[0154] Compounds represented by formula (YIIA) include: Compounds represented by formulas (YIIA-1), (YIIA-2), (YIIA-8), (YIIA-9), (YIIA-12), and (YIIA-13) are preferred. Compounds represented by formulas (YIIA-1), (YIIA-8), (YIIA-12), and (YIIA-13) are more preferred.

[0155] [Table 32]

[0156] Compounds represented by formula (YIIB) include: Compounds represented by formulas (YIIB-1), (YIIB-2), (YIIB-8), (YIIB-9), (YIIB-12), and (YIIB-13) are preferred. Compounds represented by formulas (YIIB-1), (YIIB-8), (YIIB-12), and (YIIB-13) are more preferred.

[0157] [Table 33]

[0158] Compounds represented by formula (YIIC) include: Compounds represented by formulas (YIIC-1), (YIIC-2), (YIIC-8), (YIIC-9), (YIIC-12), and (YIIC-13) are preferred. Compounds represented by formulas (YIIC-1), (YIIC-8), (YIIC-12), and (YIIC-13) are more preferred.

[0159] [Table 34]

[0160] Compounds represented by formula (YIID) include: Compounds represented by formulas (YIID-1), (YIID-2), (YIID-8), (YIID-9), (YIID-12), and (YIID-13) are preferred. Compounds represented by formulas (YIID-1), (YIID-8), (YIID-12), and (YIID-13) are more preferred.

[0161] [Table 35]

[0162] Compounds represented by formula (YIIE) include: Compounds represented by formulas (YIIE-1), (YIIE-2), (YIIE-8), (YIIE-9), (YIIE-12), and (YIIE-13) are preferred. Compounds represented by formulas (YIIE-1), (YIIE-8), (YIIE-12), and (YIIE-13) are more preferred.

[0163] The compound represented by formula (YI) can be produced, for example, by appropriately reacting the compound represented by formula (YIII) with the compound represented by formula (YIV). Furthermore, the compound represented by formula (YII) can be produced, for example, by appropriately reacting the compounds represented by formulas (YIIIa) and (YIIIb) with the compound represented by formula (YV).

[0164] [ka]

[0165] [In equations (YI), (YIII), and (YIV), R y1 , R y2 , Y 1 , Z y1 , Z y2 , Z y3 , X y1 ~X y4 And ny1~ny4 are the same as above.

[0166] [ka]

[0167] [In equations (YII), (YIIIa), (YIIIb), and (YV), R y3 , Y 2 , Z y4 , Z y5 , X y5 ~X y12 , and ny5~ny12 are the same as above.

[0168] The content of 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, of the total amount of solids in the colored resin composition. In this specification, "total amount of solids" refers to the total amount of components from the colored resin composition of the present invention, excluding the solvent. The total amount of solids and the content of each component therein can be measured by known analytical means such as liquid chromatography or gas chromatography.

[0169] Furthermore, the content of aluminum phthalocyanine dye is preferably 20 to 100% by mass, more preferably 30 to 100% by mass, even more preferably 40 to 100% by mass, and even more preferably 60 to 100% by mass, based on the total amount of coloring agent (A).

[0170] The coloring agent (A) may further contain a coloring agent different from aluminum phthalocyanine dye (hereinafter sometimes referred to as coloring agent (A2)).

[0171] The coloring agent (A2) may be either a dye or a pigment.

[0172] Examples of dyes include compounds classified as having hue other than pigments in the Color Index (published by The Society of Dyers and Colourists), and known dyes listed in the Dyeing Notes (Irozome-sha).

[0173] As dyes, for example, azo dyes, cyanine dyes, triphenylmethane dyes, thiazole dyes, oxazine dyes, quinophthalone dyes, anthraquinone dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, azomethine dyes, squarylium dyes, acridine dyes, styryl dyes, coumarin dyes, quinoline dyes, and nitro dyes may be used, and known dyes are used for each of these.

[0174] Specifically, the dyes used are CI Solvent Yellow 4 (hereinafter, the designation "CI Solvent Yellow" will be omitted, and only the numbers will be listed), 14, 15, 23, 24, 38, 62, 63, 68, 82, 94, 99, 117, 162, 163, 167, and 189; CI Solvent Red 111, 125, 130, 143, 145, 146, 150, 151, 155, 168, 169, 172, 175, 181, 207, 222, 227, 230, 245, 247; CI Solvent Orange 2, 7, 11, 15, 26, 56, 77, 86; CI Solvent Violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60; CI Solvent Blue 4, 5, 14, 18, 35, 36, 37, 45, 58, 59, 59:1, 63, 68, 69, 78, 79, 83, 90, 94, 97, 98, 100, 101, 102, 104, 105, 111, 112, 122, 128, 132, 136, 139; CI solvent dyes such as CI Solvent Green 1, 3, 5, 7, 28, 29, 32, 33, 34, 35, etc. CI Acid Yellow 1, 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112, 113, 114, 116, 119, 123, 128, 134, 135, 138, 139, 140, 144, 150, 155, 157, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251; CI Acid Red 1, 4, 8, 14, 17, 18, 26, 27, 29, 31, 33, 34, 35, 37, 40, 42, 44, 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 ,198,206,211,215,216,217,227,228,249,252,257,258,260,261,266,268,270,274,277,280,281,308,312,315,316,339,341,345,346,349,382,383,394,401,412,417,418,422,426; CI Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 169, 173; CI Acid Violet 6B, 7, 15, 16, 17, 19, 21, 23, 24, 25, 34, 38, 49, 72; 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, 1 20, 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; CI Acid Green dyes such as 1, 3, 5, 6, 7, 8, 9, 11, 13, 14, 15, 16, 22, 25, 27, 28, 41, 50, 50:1, 58, 63, 65, 80, 104, 105, 106, 109, etc. CI Direct Yellow 2, 33, 34, 35, 38, 39, 43, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129, 136, 138, 141; CI Direct Red 79, 82, 83, 84, 91, 92, 96, 97, 98, 99, 105, 106, 107, 172, 173, 176, 177, 179, 181, 182, 184, 204, 207, 211, 213, 218, 220, 221, 222, 232, 233, 234, 241, 243, 246, 250; CI Direct Orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107; CI Direct Violet 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104; CI Direct Blue 1, 2, 3, 6, 8, 15, 22, 25, 28, 29, 40, 41, 42, 47, 52, 55, 57, 71, 76, 77, 78, 80, 81, 84, 85, 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, 1 66, 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; CI Direct Green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 77, 79, 82 and other CI Direct dyes, CI Disperse Yellow 51, 54, 76; CI Disperse Violet 26, 27; CI Disperse Blue 1, 14, 56, 60 and other CI disperse dyes, CI Basic Blue 1, 3, 5, 7, 9, 19, 21, 22, 24, 25, 26, 28, 29, 40, 41, 45, 47, 54, 58, 59, 60, 64, 65, 66, 67, 68, 81, 83, 88, 89; CI Basic Violet 2; CI Basic Red 9; CI Basic Green 1; and other CI Basic dyes, CI Reactive Yellow 2,76,116; CI Reactive Orange 16; CI Reactive Red 36; and other CI reactive dyes, CI Mordant Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65; CI Modant Red 1, 2, 3, 4, 9, 11, 12, 14, 17, 18, 19, 22, 23, 24, 25, 26, 29, 30, 32, 33, 36, 37, 38, 39, 41, 42, 43, 45, 46, 48, 52, 53, 56, 62, 63, 71, 74, 76, 78, 85, 86, 88, 90, 94, 95; CI Modern Orange 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47, 48; CI Mordant Violet 1, 1:1, 2, 3, 4, 5, 6, 7, 8, 10, 11, 14, 15, 16, 17, 18, 19, 21, 22, 23, 24, 27, 28, 30, 31, 32, 33, 36, 37, 39, 40, 41, 44, 45, 47, 48, 49, 53, 58; CI Modern Blue 1, 2, 3, 7, 8, 9, 12, 13, 15, 16, 19, 20, 21, 22, 23, 24, 26, 30, 31, 32, 39, 40, 41, 43, 44, 48, 49, 53, 61, 74, 83, 84; CI Modant Green dyes such as 1, 3, 4, 5, 10, 13, 15, 19, 21, 23, 26, 29, 31, 33, 34, 35, 41, 43, 53, etc. Examples include CI bat dyes such as CI bat green 1. These dyes may use one or more dyes for each color, or a combination of dyes for each color.

[0175] Examples of pigments include those classified as pigments in the Color Index (published by The Society of Dyers and Colourists), and the following pigments can be given as examples.

[0176] Green pigments: CI Pigment Green 7, 36, 58, etc. Yellow pigments: 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. Orange pigments: CI Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73, etc. Red pigments: CI Pigment Red 9, 97, 105, 122, 144, 149, 166, 168, 176, 177, 180, 192, 209, 215, 216, 242, 254, 255, 264, 265, etc. Blue pigment: CI Pigment Blue 16, 60, etc. Purple pigments: CI Pigment Violet 19, 23, 29, 32, 36, 38, etc. These pigments may use one or more pigments for each color, or a combination of pigments for each color.

[0177] The pigment may be subjected to rosin treatment, surface treatment using pigment derivatives into which acidic or basic groups have been introduced, grafting treatment of the pigment surface with polymer compounds, atomization treatment by sulfuric acid atomization method, washing treatment with organic solvents or water to remove impurities, removal treatment of ionic impurities by ion exchange method, etc. The particle size of the pigment is preferably substantially uniform. The pigment can be dispersed by dispersing it with a pigment dispersant to obtain a pigment dispersion in which it is uniformly dispersed in a pigment dispersant solution. The pigments may be dispersed individually or mixed together.

[0178] Examples of pigment dispersants include the same dispersants that may be included in the colored resin composition described later.

[0179] When a pigment dispersant is used, the amount used is preferably 10 to 200 parts by mass, more preferably 15 to 180 parts by mass, and even more preferably 20 to 160 parts by mass, per 100 parts by mass of pigment. When the amount of pigment dispersant used is within the above range, a pigment dispersion with a more uniform dispersion state tends to be obtained when two or more types of pigments are used.

[0180] When colorant (A) contains colorant (A2), the content of 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, of the total amount of colorant (A).

[0181] The content of 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 solids. When the content of colorant (A) is within the above range, it becomes easier to obtain the desired spectral characteristics and color density.

[0182] <Compounds represented by formula (DA)> The colored resin composition according to the present invention contains a compound represented by formula (DA). Among phthalocyanines, the compound represented by formula (DA) may have a reduced adhesion effect when combined with copper phthalocyanine dye, but when combined with aluminum phthalocyanine dye, the adhesion improvement effect is significantly enhanced.

[0183] [ka]

[0184] [In formula (DA), R d1 represents a hydrocarbon group having 1 to 12 carbon atoms, which may have substituents. If the hydrocarbon group has 2 to 12 carbon atoms and contains -CH2-, the -CH2- may be replaced by -O-, -S-, or -CO-. R d2 and R d3Each independently represents a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms which may have substituents, or R d2 and R d3 These are combined, -CO-NR d1 This indicates the formation of a ring with -CO-.

[0185] R d1 ~R d3 The number of carbon atoms in the hydrocarbon group represented is 1 to 12, more preferably 1 to 10, even more preferably 1 to 6, and even more preferably 1 to 3. R d1 The number of carbon atoms in the hydrocarbon group represented by R is d2 or R d3 The number of carbon atoms in the hydrocarbon group represented by R, d2 and R d3 These are combined, -CO-NR d1 The number of carbon atoms in the ring formed with -CO- may be smaller than the number of carbon atoms in the ring.

[0186] 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, and the aliphatic hydrocarbon group may be saturated or unsaturated, and may be linear or cyclic (alicyclic hydrocarbon group).

[0187] R d1 ~R d3 As a saturated or unsaturated chain hydrocarbon group represented by R, x2 Examples include saturated or unsaturated chain hydrocarbon groups with 1 to 12 carbon atoms represented by . R d1 ~R d3 The number of carbon atoms in the saturated chain hydrocarbon group represented is preferably 1 to 10, more preferably 1 to 6, and even more preferably 1 to 3. R d1 ~R d3 The number of carbon atoms in the unsaturated chain hydrocarbon group represented is preferably 2 to 10, more preferably 2 to 6, and even more preferably 2 to 3.

[0188] Rd1 ~R d3 As a saturated or unsaturated alicyclic hydrocarbon group represented by R, x2 Examples include saturated or unsaturated alicyclic hydrocarbon groups with 3 to 12 carbon atoms represented by . R d1 ~R d3 The number of carbon atoms in the saturated or unsaturated alicyclic hydrocarbon group represented by is preferably 3 to 10.

[0189] R d1 ~R d3 As an aromatic hydrocarbon group represented by R x2 Examples of aromatic hydrocarbon groups represented by include those with 6 to 12 carbon atoms. R d1 ~R d3 The number of carbon atoms in the aromatic hydrocarbon group represented is preferably 6 to 10, and more preferably 6 to 8.

[0190] R d1 ~R d3 The hydrocarbon group represented by may be a group formed by combining the hydrocarbon groups listed above (for example, an aromatic hydrocarbon group and at least one of a chain hydrocarbon group and an alicyclic hydrocarbon group). A specific example of such a group is R x2 The same groups with 7 to 12 carbon atoms as those exemplified are shown. These carbon numbers are preferably 7 to 10.

[0191] R d1 ~R d3 The group represented by may be an alkyl group to which one or more alicyclic hydrocarbon groups are bonded, such as a group formed by combining the hydrocarbon groups listed above (for example, a chain hydrocarbon group and an alicyclic hydrocarbon group) (for example, a cyclopropylmethyl group). These carbon numbers are preferably 4 to 10.

[0192] R d1 Examples of hydrocarbon groups with 1 to 12 carbon atoms represented by (where the -CH2- in the hydrocarbon group is not replaced by -O-, -S-, or -CO-) include the following groups:

[0193] [ka]

[0194] R d1 In a hydrocarbon group having 1 to 12 carbon atoms represented by , if the hydrocarbon group has 2 to 12 carbon atoms and has -CH2-, the -CH2- may be replaced by -O-, -S-, or -CO-. However, in the hydrocarbon group having 2 to 12 carbon atoms, adjacent -CH2- may not be simultaneously replaced by -O- and / or -S-, and terminal -CH2- may not be replaced by -O-, -S-, or -CO-. R d1 Examples of groups in which the -CH2- of a hydrocarbon group having 1 to 12 carbon atoms, represented by , is replaced by -O-, -S-, or -CO- include the following groups.

[0195] [ka]

[0196] [ka]

[0197] [ka]

[0198] [ka]

[0199] [ka]

[0200] [ka]

[0201] R d1 ~R d3 The hydrocarbon group having 1 to 12 carbon atoms represented by may have substituents. R d1 ~R d3 The substituents of the hydrocarbon group having 1 to 12 carbon atoms represented by include heterocyclic groups which may have substituents, halogen atoms, nitro groups, cyano groups, and -OR groups. xa1 , -CO2R xa1 , -SR xa1 , -SO2R xa1 , -SO3R xa1 -SO2NR xa1 R xa2 and -NR xa1 R xa2 Examples include (however, R xa1 and R xa2 (The same applies as above.)

[0202] R d1 ~R d3 The heterocyclic group used as a substituent for a hydrocarbon group having 1 to 12 carbon atoms, represented by , may be monocyclic or polycyclic, and is preferably a heterocyclic ring containing a heteroatom as a component of the ring. Examples of heteroatoms include nitrogen, oxygen, and sulfur atoms. The complex ring is R x1 and R x3 Examples include heterocyclic groups used as substituents on unsaturated hydrocarbon groups with 2 to 20 carbon atoms, as represented by [the formula shown]. The number of carbon atoms in the heterocyclic group is preferably 2 to 30, more preferably 3 to 22, and even more preferably 3 to 20. The heterocyclic group may have substituents, such as halogen atoms, nitro groups, cyano groups, and -OR groups. xa1 , -CO2R xa1 , -SR xa1 , -SO2R xa1 , -SO3R xa1 -SO2NR xa1 R xa2 and -NR xa1 R xa2 Examples include (however, R xa1 and R xa2 (The same applies as above.) The bonding positions of the heterocycle are the regions where any hydrogen atom contained in each ring has been removed.

[0203] R d1 ~R d3 Examples of halogen atoms used as substituents on hydrocarbon groups having 1 to 12 carbon atoms, as represented by , include fluorine, chlorine, bromine, and iodine atoms.

[0204] R d1 ~R d3 Examples of substituents for the hydrocarbon group having 1 to 12 carbon atoms represented by include -OR xa1 (R xa1 Preferably a hydrogen atom or a saturated hydrocarbon group having 1 to 15 carbon atoms, more preferably a hydrogen atom or a linear alkyl group having 1 to 10 carbon atoms, a branched alkyl group, even more preferably a hydrogen atom or a methyl group, ethyl group, propyl group, isopropyl group, t-butyl group, even more preferably a hydrogen atom), -CO2R xa1 (R xa1 Preferably, the group consists of a hydrogen atom or a saturated hydrocarbon group having 1 to 15 carbon atoms, more preferably a hydrogen atom or a linear alkyl group having 1 to 10 carbon atoms, a branched alkyl group, even more preferably a hydrogen atom or a methyl group, ethyl group, propyl group, isopropyl group, t-butyl group, and even more preferably a hydrogen atom.

[0205] R d2 and R d3 These are combined, -CO-NR d1 When forming a ring with -CO-, the following are examples of the rings that can be formed. Note that in equations (r-1) to (r-7), * represents R d1 This represents a combination of two things.

[0206] [ka]

[0207] In equation (DA), R d1 teeth, Preferably -CO2R xa1(R xa1 The substituent is preferably a hydrogen atom or a saturated chain hydrocarbon group having 1 to 15 carbon atoms, more preferably a hydrogen atom or a linear alkyl group having 1 to 10 carbon atoms, a branched alkyl group having 1 to 10 carbon atoms, even more preferably a hydrogen atom or a methyl group, ethyl group, propyl group, isopropyl group, t-butyl group, and even more preferably a hydrogen atom) as a substituent, and is a saturated aliphatic hydrocarbon group having 1 to 12 carbon atoms. comfortable-CO2R xa1 (R xa1 The substituent is preferably a hydrogen atom or a saturated chain hydrocarbon group having 1 to 15 carbon atoms, more preferably a hydrogen atom or a linear alkyl group having 1 to 10 carbon atoms, a branched alkyl group having 1 to 10 carbon atoms, even more preferably a hydrogen atom or a methyl group, ethyl group, propyl group, isopropyl group, t-butyl group, and even more preferably a hydrogen atom) and having 1 to 12 carbon atoms as substituents. More preferably -CO2R xa1 (R xa1 The substituent is preferably a hydrogen atom or a saturated chain hydrocarbon group having 1 to 10 carbon atoms, more preferably a hydrogen atom or a linear alkyl group having 1 to 8 carbon atoms, a branched alkyl group having 1 to 8 carbon atoms, even more preferably a hydrogen atom or a methyl group, ethyl group, propyl group, isopropyl group, t-butyl group, and even more preferably a hydrogen atom) as a substituent, and is a saturated chain hydrocarbon group having 1 to 5 carbon atoms. Even more even -CO2R xa1 (R xa1 Preferably, it is a linear alkyl group having 1 to 5 carbon atoms as a substituent, more preferably a hydrogen atom or a saturated hydrocarbon group having 1 to 5 carbon atoms, more preferably a linear alkyl group having 1 to 4 carbon atoms, a branched alkyl group, even more preferably a hydrogen atom or a methyl group, ethyl group, propyl group, isopropyl group, t-butyl group, and even more preferably a hydrogen atom) (linear alkyl group having 1 to 5 carbon atoms). Especially preferred -CO2R xa1 (R xa1 The substituent is preferably a hydrogen atom or a methyl group, ethyl group, propyl group, propyl group, isopropyl group, t-butyl group, more preferably a hydrogen atom), and is a methyl group, ethyl group, propyl group, butyl group, or pentyl group. R d2 and Rd3 teeth, R d2 and R d3 These are combined, -CO-NR d1 It is preferable to form a ring with -CO-. R d2 and R d3 These are combined, -CO-NR d1 It is more preferable to form a ring represented by formula (r-1) or formula (r-2) together with -CO-.

[0208] Examples of compounds represented by formula (DA) include those represented by formulas (da-1) to (da-10).

[0209] [ka]

[0210] The compounds represented by formula (DA) are preferably those represented by formula (da-1), formula (da-2), formula (da-4), formula (da-5), formula (da-6), formula (da-9), and formula (da-10). Compounds represented by formulas (da-1) and (da-2) are more preferred.

[0211] The colored resin composition of the present invention contains one or more compounds represented by formula (DA). That is, the compounds represented by formula (DA) may be used individually or in combination of multiple compounds with different structures.

[0212] If the colored resin composition contains two or more compounds represented by formula (DA), then the compounds represented by formula (DA) are: R d2 and R d3 These are combined, -CO-NR d1 It is preferable that the compound represented by formula (DA) contains a ring represented by formula (r-1) or formula (r-2) together with -CO-, It is more preferable that the compound contains at least two compounds selected from the group consisting of compounds represented by formulas (da-1) to (da-10), It is even more preferable that the compound contains at least two selected from the group consisting of compounds represented by formulas (da-1), (da-2), (da-4), (da-5), (da-6), (da-9), and (da-10). It is particularly preferable that the compound is represented by formulas (da-1) and (da-2).

[0213] When a colored resin composition contains two or more compounds represented by formula (DA), the two or more compounds represented by formula (DA) may be present in equal amounts or in different amounts. When two or more compounds represented by formula (DA) are present in different amounts, the molar ratio of the compound represented by formula (DA) that is least abundant to the compound represented by 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.

[0214] The content of the compound represented by formula (DA) (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, even more preferably 10 to 160 parts by mass, even more preferably 15 to 160 parts by mass, even more preferably 25 to 150 parts by mass, and particularly preferably 45 to 140 parts by mass, per 100 parts by mass of aluminum phthalocyanine dye. When the amount of the compound represented by formula (DA) is within this range, the generation of foreign matter is suppressed and a colored coating film with good adhesion to the substrate is formed.

[0215] The content of the compound represented by formula (DA) in the colored resin composition (the total content of two or more compounds represented by formula (DA)) is preferably 0.1 to 30% by mass, more preferably 2.0 to 25% by mass, even more preferably 3.5 to 20% by mass, and even more preferably 6.0 to 20% by mass, relative to the total amount of solids. When the content of the compound represented by formula (DA) is within the above range, the generation of foreign matter is suppressed, and a colored coating film with good adhesion to the substrate is formed.

[0216] <Dispersant> The colored resin composition according to the present invention may contain a dispersant. Examples of dispersants include surfactants, which may be cationic, anionic, nonionic, or amphoteric. Specifically, examples include polyester-based, polyamine-based, and acrylic-based surfactants. These dispersants may be used alone or in combination of two or more. Examples of dispersants, as trade names, include KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Floren (manufactured by Kyoeisha Chemical Co., Ltd.), Solspers® (registered trademark) (manufactured by Zeneca Co., Ltd.), EFKA® (registered trademark) (manufactured by BASF Ltd.), Adisper® (registered trademark) (manufactured by Ajinomoto Fine Techno Co., Ltd.), Disperbyk® (registered trademark), BYK® (registered trademark) (manufactured by Bic Chemie Inc.).

[0217] The amount of dispersant used is preferably 1 to 150 parts by mass, more preferably 10 to 130 parts by mass, even more preferably 20 to 120 parts by mass, and even more preferably 30 to 110 parts by mass, per 100 parts by mass of aluminum phthalocyanine dye.

[0218] The amount of dispersant used is preferably 1 to 300 parts by mass, more preferably 10 to 150 parts by mass, even more preferably 15 to 85 parts by mass, and even more preferably 20 to 75 parts by mass, per 100 parts by mass of the compound represented by formula (DA). When the amount of dispersant is within this range, the generation of foreign matter is suppressed, and a colored coating film with good adhesion to the substrate is formed.

[0219] <Resin (B)> The resin (B) is not particularly limited, but is preferably an alkali-soluble resin. Examples of resin (B) include the following resins [K1] to [K6]. Resin [K1]; a copolymer of at least one (a) selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic acid anhydrides (hereinafter sometimes referred to as "(a)") and a monomer (b) having a cyclic ether structure with 2 to 4 carbon atoms and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b)"); Resin [K2]; a copolymer of (a) and (b) and a monomer (c) copolymerizable with (a) (however different from (a) and (b)) (hereinafter sometimes referred to as "(c)"); Resin [K3]; copolymer of (a) and (c); Resin [K4]; a resin obtained by reacting (b) with a copolymer of (a) and (c); Resin [K5]; a resin obtained by reacting (a) with a copolymer of (b) and (c); Resin [K6]; A resin obtained by reacting (a) with a copolymer of (b) and (c), and further reacting it with a polycarboxylic acid and / or carboxylic acid anhydride.

[0220] (a) specifically includes, for example, unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, and o-, m-, p-vinylbenzoic acid; Unsaturated dicarboxylic acids such as maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyltetrahydrophthalic acid, and 1,4-cyclohexenedicarboxylic acid; Bicyclounsaturated compounds containing carboxyl groups, such as methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo[2.2.1]hept-2-ene, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene, 5-carboxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-carboxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-carboxy-6-methylbicyclo[2.2.1]hept-2-ene, and 5-carboxy-6-ethylbicyclo[2.2.1]hept-2-ene; Unsaturated dicarboxylic acid anhydrides such as maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, and 5,6-dicarboxybicyclo[2.2.1]hepto-2-ene anhydride; Unsaturated mono(meth)acryloyloxyalkyl) esters of divalent or higher polycarboxylic acids such as mono(2-(meth)acryloyloxyethyl) succinate and mono(2-(meth)acryloyloxyethyl) phthalate; Examples include unsaturated acrylates containing both a hydroxyl group and a carboxyl group in the same molecule, such as α-(hydroxymethyl)acrylic acid. Of these, acrylic acid, methacrylic acid, maleic anhydride, and the like are preferred in terms of copolymerization reactivity and the solubility of the resulting resin in alkaline aqueous solutions.

[0221] (b) refers to a polymerizable compound having, for example, a cyclic ether structure with 2 to 4 carbon atoms (for example, at least one selected from the group consisting of an oxirane ring, an oxetane ring, and a tetrahydrofuran ring) and an ethylenically unsaturated bond. (b) is preferably a monomer having a cyclic ether with 2 to 4 carbon atoms and a (meth)acryloyloxy group. In this specification, "(meth)acrylic acid" refers to at least one selected from the group consisting of acrylic acid and methacrylic acid. The terms "(meth)acryloyl" and "(meth)acrylate" have the same meaning.

[0222] Examples of (b) include monomers having an oxyranyl group and an ethylenically unsaturated bond (b1) (hereinafter sometimes referred to as "(b1)"), monomers having an oxetanyl group and an ethylenically unsaturated bond (b2) (hereinafter sometimes referred to as "(b2)"), and monomers having a tetrahydrofuryl group and an ethylenically unsaturated bond (b3) (hereinafter sometimes referred to as "(b3)").

[0223] Examples of (b1) include monomers having a linear or branched aliphatic unsaturated hydrocarbon structure that has been epoxidized (b1-1) (hereinafter sometimes referred to as "(b1-1)") and monomers having a cyclic unsaturated hydrocarbon structure that has been epoxidized (b1-2) (hereinafter sometimes referred to as "(b1-2)").

[0224] (b1-1) includes glycidyl (meth)acrylate, β-methylglycidyl (meth)acrylate, β-ethylglycidyl (meth)acrylate, glycidyl vinyl ether, o-vinylbenzylglycidyl ether, m-vinylbenzylglycidyl ether, p-vinylbenzylglycidyl ether, α-methyl-o-vinylbenzylglycidyl ether, α-methyl-m-vinylbenzylglycidyl ether, α-methyl-p-vinylbenzylglycidyl ether, 2,3-bis(glycidyl Examples include oxymethylstyrene, 2,4-bis(glycidyloxymethyl)styrene, 2,5-bis(glycidyloxymethyl)styrene, 2,6-bis(glycidyloxymethyl)styrene, 2,3,4-tris(glycidyloxymethyl)styrene, 2,3,5-tris(glycidyloxymethyl)styrene, 2,3,6-tris(glycidyloxymethyl)styrene, 3,4,5-tris(glycidyloxymethyl)styrene, and 2,4,6-tris(glycidyloxymethyl)styrene.

[0225] (b1-2) includes vinylcyclohexene monooxide, 1,2-epoxy-4-vinylcyclohexane (e.g., Celoxide 2000; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., Cyclomer A400; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., Cyclomer M100; manufactured by Daicel Corporation), and 3,4-epoxytricyclo[5.2.1.0 2,6 Examples include decyl (meth)acrylate, compounds represented by formula (R1), and compounds represented by formula (R2).

[0226] [ka]

[0227] [In equations (R1) and (R2), R ra and R rb This represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the hydrogen atom contained in the alkyl group may be substituted with a hydroxyl group. X ra and X rb This is a single bond, *-R rc -, *-R rc -O-, *-R rc -S- or *-R rc Represents -NH- R rc This represents an alkanediyl group with 1 to 6 carbon atoms. * represents a bond with O.

[0228] Examples of alkyl groups having 1 to 4 carbon atoms include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, and tert-butyl group. Examples of alkyl groups in which a hydrogen atom is substituted with hydroxyl include hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 1-hydroxypropyl group, 2-hydroxypropyl group, 3-hydroxypropyl group, 1-hydroxy-1-methylethyl group, 2-hydroxy-1-methylethyl group, 1-hydroxybutyl group, 2-hydroxybutyl group, 3-hydroxybutyl group, and 4-hydroxybutyl group. R ra and R rb Preferably, the group can be a hydrogen atom, a methyl group, a hydroxymethyl group, a 1-hydroxyethyl group, or a 2-hydroxyethyl group, and more preferably a hydrogen atom or a methyl group.

[0229] Examples of alkanediyl groups include methylene, ethylene, propane-1,2-diyl, propane-1,3-diyl, butane-1,4-diyl, pentane-1,5-diyl, and hexane-1,6-diyl. X ra and X rb Preferably, the bonds include single bonds, methylene groups, ethylene groups, *-CH2-O- and *-CH2CH2-O-, and more preferably, single bonds and *-CH2CH2-O- (* represents a bond with O).

[0230] Compounds represented by formula (R1) include those represented by any of the formulas (R1-1) to (R1-15). Among these, compounds represented by formulas (R1-1), (R1-3), (R1-5), (R1-7), (R1-9), or (R1-11) to (R1-15) are preferred, and compounds represented by formulas (R1-1), (R1-7), (R1-9), or (R1-15) are more preferred.

[0231] [ka]

[0232] [ka]

[0233] Compounds represented by formula (R2) include those represented by any of the formulas (R2-1) to (R2-15). Among these, compounds represented by formulas (R2-1), (R2-3), (R2-5), (R2-7), (R2-9), or (R2-11) to (R2-15) are preferred, and compounds represented by formulas (R2-1), (R2-7), (R2-9), or (R2-15) are more preferred.

[0234] [ka]

[0235] [ka]

[0236] For (b2), monomers having an oxetanyl group and a (meth)acryloyloxy group are more preferred. Examples of (b2) include 3-methyl-3-methacryloyloxymethyl oxetane, 3-methyl-3-acryloyloxymethyl oxetane, 3-ethyl-3-methacryloyloxymethyl oxetane, 3-methyl-3-methacryloyloxyethyl oxetane, 3-methyl-3-acryloyloxyethyl oxetane, 3-ethyl-3-methacryloyloxyethyl oxetane, and 3-ethyl-3-acryloyloxyethyl oxetane.

[0237] For (b3), monomers having a tetrahydrofurfuryl group and a (meth)acryloyloxy group are more preferred. Specifically for (b3), examples include tetrahydrofurfuryl acrylate (e.g., Viscoat V#150, manufactured by Osaka Organic Chemical Industry Co., Ltd.) and tetrahydrofurfuryl methacrylate.

[0238] (b) is preferable because it allows for greater reliability of the heat resistance, chemical resistance, etc., of the resulting color filter. Furthermore, (b1-2) is more preferable because it provides excellent storage stability for the colored resin composition.

[0239] (c) For example, methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, sec-butyl (meth)acrylate, tert-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, dodecyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, cyclopentyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, tricyclo[5.2.1.0 2,6 ] Decane-8-yl(meth)acrylate (in the relevant technical field, it is commonly called "dicyclopentanyl(meth)acrylate". It is also sometimes called "tricyclodecyl(meth)acrylate"), tricyclo[5.2.1.02,6 Decen-8-yl (meth)acrylate (commonly known as "dicyclopentenyl (meth)acrylate" in the relevant art), dicyclopentanyloxyethyl (meth)acrylate, isobornyl (meth)acrylate, adamantyl (meth)acrylate, allyl (meth)acrylate, propargyl (meth)acrylate, phenyl (meth)acrylate, naphthyl (meth)acrylate, benzyl (meth)acrylate, and other (meth)acrylic acid esters; Hydroxyl group-containing (meth)acrylic acid esters such as 2-hydroxyethyl (meth)acrylate and 2-hydroxypropyl (meth)acrylate; Diethyl maleate, diethyl fumarate, diethyl itaconate, and other dicarboxylic acid diesters; Bicyclo[2.2.1]hept-2-ene, 5-methylbicyclo[2.2.1]hept-2-ene, 5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxybicyclo[2.2.1]hept-2-ene, 5-hydroxymethylbicyclo[2.2.1]hept-2-ene, 5-(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5-methoxybic Chlo[2.2.1]hept-2-ene, 5-ethoxybicyclo[2.2.1]hept-2-ene, 5,6-dihydroxybicyclo[2.2.1]hept-2-ene, 5,6-di(hydroxymethyl)bicyclo[2.2.1]hept-2-ene, 5,6-di(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5,6-dimethoxybicyclo[2.2.1]hept -2-ene, 5,6-diethoxybicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxymethyl-5-methylbicyclo[2.2.1]hept-2-ene, 5-tert-butoxycarbonylbicyclo[2.2.1]hept-2- Bicyclounsaturated compounds such as ene, 5-cyclohexyloxycarbonylbicyclo[2.2.1]hept-2-ene, 5-phenoxycarbonylbicyclo[2.2.1]hept-2-ene, 5,6-bis(tert-butoxycarbonyl)bicyclo[2.2.1]hept-2-ene, and 5,6-bis(cyclohexyloxycarbonyl)bicyclo[2.2.1]hept-2-ene; Dicarbonylimide derivatives such as N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimide benzoate, N-succinimidyl-4-maleimide butyrate, N-succinimidyl-6-maleimide caproate, N-succinimidyl-3-maleimide propionate, and N-(9-acridinyl)maleimide; Examples include styrene, α-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, p-methoxystyrene, acrylonitrile, methacrylonitrile, vinyl chloride, vinylidene chloride, acrylamide, methacrylamide, vinyl acetate, 1,3-butadiene, isoprene, 2,3-dimethyl-1,3-butadiene; and others. Of these, styrene, vinyltoluene, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, and bicyclo[2.2.1]hept-2-ene are preferred in terms of copolymerization reactivity and heat resistance.

[0240] In resin [K1], the ratio of structural units derived from each is, among all structural units constituting resin [K1], (a) Structural units derived from (a); 2-60 mol% (b) Structural units derived from (b); 40-98 mol% It is preferable that this be the case. (a) Structural units derived from (a); 10-50 mol% (b) Structural units derived from (b); 50-90 mol% It is preferable that it be so. When the ratio of structural units of resin [K1] falls within the above range, the storage stability of the colored resin composition, the developability when forming a colored pattern, and the solvent resistance of the resulting color filter tend to be excellent.

[0241] The resin [K1] can be manufactured, for example, by referring to the method described in the literature "Experimental Methods for Polymer Synthesis" (by Takayuki Otsu, published by Kagaku Dojin Co., Ltd., 1st edition, 1st printing, March 1, 1972) and the cited literature.

[0242] Specifically, a method involves placing predetermined amounts of (a) and (b), a polymerization initiator, and a solvent into a reaction vessel, creating a deoxygenated atmosphere by, for example, replacing oxygen with nitrogen, and heating and maintaining the temperature while stirring. The polymerization initiator and solvent used here are not particularly limited and can be those commonly used in the field. For example, examples of polymerization initiators include azo compounds (2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), etc.) and organic peroxides (benzoyl peroxide, etc.), and the solvent can be any solvent that dissolves each monomer, with solvent (E) being an example of a solvent described later.

[0243] The resulting copolymer may be used as is after the reaction, or after being concentrated or diluted, or after being extracted as a solid (powder) by methods such as reprecipitation. In particular, by using the solvent contained in the colored resin composition as the solvent during this polymerization, the solution after the reaction can be used directly in the preparation of the colored resin composition, thereby simplifying the manufacturing process of the colored resin composition.

[0244] In resin [K2], the ratio of structural units derived from each is, among all structural units constituting resin [K2], (a) Structural units derived from (a); 2-45 mol% (b) Structural units derived from (b); 2-95 mol% (c) Structural units derived from (c); 1-65 mol% It is preferable that this be the case. (a) Structural units derived from (a); 5-40 mol% (b) Structural units derived from (b); 5-80 mol% (c) Structural units derived from (c); 5-60 mol% It is preferable that it be so. When the ratio of structural units of resin [K2] is within the above range, the colored resin composition tends to have excellent storage stability, developability when forming colored patterns, and solvent resistance, heat resistance, and mechanical strength of the resulting color filter.

[0245] Resin [K2] can be manufactured, for example, in the same manner as described as the method for manufacturing resin [K1].

[0246] In resin [K3], the ratio of structural units derived from each is, out of the total structural units constituting resin [K3], (a) Structural units derived from (a); 2-60 mol% (c) Structural units derived from (c); 40-98 mol% It is preferable that this be the case. (a) Structural units derived from (a); 10-50 mol% (c) Structural units derived from (c); 50-90 mol% It is preferable that it be so. Resin [K3] can be manufactured, for example, in the same manner as described as the method for manufacturing resin [K1].

[0247] The resin [K4] can be produced by obtaining a copolymer of (a) and (c), and adding the cyclic ether having 2 to 4 carbon atoms of (b) to the carboxylic acid and / or carboxylic acid anhydride of (a). First, a copolymer of (a) and (c) is produced in the same manner as described for the production of resin [K1]. In this case, it is preferable that the ratio of structural units derived from each is the same as that given for resin [K3].

[0248] Next, a portion of the carboxylic acid and / or carboxylic acid anhydride derived from (a) in the copolymer is reacted with a cyclic ether having 2 to 4 carbon atoms that (b) possesses. Following the production of the copolymer of (a) and (c), the atmosphere inside the flask is replaced from nitrogen to air, and (b), a reaction catalyst for the reaction between a carboxylic acid or carboxylic acid anhydride and a cyclic ether (e.g., tris(dimethylaminomethyl)phenol) and a polymerization inhibitor (e.g., hydroquinone) are added to the flask and the mixture is reacted at, for example, 60 to 130°C for 1 to 10 hours to produce resin [K4]. The amount of (b) used is preferably 5 to 80 moles, more preferably 10 to 75 moles, per 100 moles of (a). This range tends to result in a good balance of storage stability of the colored resin composition, developability when forming patterns, and solvent resistance, heat resistance, mechanical strength, and sensitivity of the resulting patterns. Since the cyclic ether is highly reactive and unreacted (b) is less likely to remain, (b1) is preferred as the (b) used in the resin [K4], and (b1-1) is more preferred. The amount of the reaction catalyst used is preferably 0.001 to 5 parts by mass per 100 parts by mass of the total amount of (a), (b), and (c). The amount of the polymerization inhibitor used is preferably 0.001 to 5 parts by mass per 100 parts by mass of the total amount of (a), (b), and (c). The reaction conditions, such as the preparation method, reaction temperature, and time, can be adjusted as appropriate, taking into account the manufacturing equipment and the amount of heat generated by polymerization. Similarly, the preparation method and reaction temperature can be adjusted as appropriate, taking into account the manufacturing equipment and the amount of heat generated by polymerization.

[0249] As a first step, resin [K5] is produced in the same manner as the production method for resin [K1] described above to obtain a copolymer of (b) and (c). As described above, the obtained copolymer may be used as is after the reaction, or a concentrated or diluted solution may be used, or it may be used after being extracted as a solid (powder) by methods such as reprecipitation. The ratios of structural units derived from (b) and (c) are, in relation to the total number of moles of all structural units constituting the copolymer, respectively: (b) Structural units derived from (b); 5-95 mol% (c) Structural units derived from (c); 5-95 mol% It is preferable that this be the case. (b) Structural units derived from (b); 10-90 mol% (c) Structural units derived from (c); 10-90 mol% It is preferable that it be so.

[0250] Furthermore, resin [K5] can be obtained by reacting the cyclic ether derived from (b) in the copolymer of (b) and (c) with the carboxylic acid or carboxylic acid anhydride of (a) under the same conditions as for the production of resin [K4]. The amount of (a) used to react with the copolymer is preferably 5 to 80 moles per 100 moles of (b). Since the cyclic ether is highly reactive and unreacted (b) is less likely to remain, (b1) is preferred as the (b) used in the resin [K5], and (b1-1) is more preferred.

[0251] Resin [K6] is a resin obtained by further reacting resin [K5] with a carboxylic acid anhydride. The hydroxyl group generated by the reaction of a cyclic ether with a carboxylic acid or carboxylic acid anhydride is reacted with the carboxylic acid anhydride. Examples of carboxylic acid anhydrides include maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, and 5,6-dicarboxybicyclo[2.2.1]hepto-2-ene anhydride. The amount of carboxylic acid anhydride used is preferably 0.5 to 1 mole per mole of (a).

[0252] Specific resins (B) include 3,4-epoxycyclohexylmethyl(meth)acrylate / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2.6 ] Resins such as decyl acrylate / (meth)acrylic acid copolymer [K1]; 3,4-epoxy tricyclo[5.2.1.0 2,6 Decyl acrylate / benzyl (meth)acrylate / (meth)acrylic acid copolymer, glycidyl (meth)acrylate / benzyl (meth)acrylate / (meth)acrylic acid copolymer, glycidyl (meth)acrylate / styrene / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6Decyl acrylate / (meth)acrylic acid / N-cyclohexyl maleimide copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 Resins such as decyl acrylate / (meth)acrylic acid / N-cyclohexyl maleimide / 2-hydroxyethyl (meth)acrylate copolymer, 3-methyl-3-(meth)acryloyloxymethyl oxetane / (meth)acrylic acid / styrene copolymer [K2]; resins such as benzyl (meth)acrylate / (meth)acrylic acid copolymer, styrene / (meth)acrylic acid copolymer [K3]; resins obtained by adding glycidyl (meth)acrylate to benzyl (meth)acrylate / (meth)acrylic acid copolymer, resins obtained by adding glycidyl (meth)acrylate to tricyclodecyl (meth)acrylate / styrene / (meth)acrylic acid copolymer, tricyclodecyl Examples of resins include those obtained by adding glycidyl(meth)acrylate to a (meth)acrylate / benzyl(meth)acrylate / (meth)acrylic acid copolymer [K4]; resins obtained by reacting (meth)acrylic acid with a copolymer of tricyclodecyl(meth)acrylate / glycidyl(meth)acrylate, resins obtained by reacting (meth)acrylic acid with a copolymer of tricyclodecyl(meth)acrylate / styrene / glycidyl(meth)acrylate [K5]; and resins obtained by reacting tetrahydrophthalic anhydride with a resin obtained by reacting (meth)acrylic acid with a copolymer of tricyclodecyl(meth)acrylate / glycidyl(meth)acrylate [K6]. Among these, resins [K1] and [K2] are preferred as resin (B).

[0253] Resin (B) is preferably a copolymer (resin [K1] or resin [K2]) comprising structural units derived from at least one selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic acid anhydrides, and structural units having a cyclic ether structure with 2 to 4 carbon atoms and an ethylenically unsaturated bond, and more preferably resin [K2].

[0254] The weight-average molecular weight of resin (B) in terms of polystyrene is preferably 500 to 100,000, more preferably 600 to 50,000, and even more preferably 700 to 30,000. When the molecular weight is within the above range, the hardness of the color filter is improved, the residual film rate is high, the solubility of the unexposed areas in the developer is good, and the resolution of the color pattern tends to improve.

[0255] The degree of dispersion of resin (B) [weight-average molecular weight (Mw) / number-average molecular weight (Mn)] is preferably 1.1 to 6, and more preferably 1.2 to 4.

[0256] The acid value of resin (B) is preferably 50 to 170 mg-KOH / g, more preferably 60 to 150 mg-KOH / g, and even more preferably 70 to 135 mg-KOH / g, based on solid content. Here, the acid value is measured as the amount of potassium hydroxide (mg) required to neutralize 1 g of resin (B), and can be determined, for example, by titration using an aqueous potassium hydroxide solution.

[0257] The content of resin (B) is preferably 7 to 80% by mass, more preferably 13 to 75% by mass, even more preferably 17 to 70% by mass, and even more preferably 17 to 55% by mass, relative to the total amount of solids. When the content of resin (B) is within the above range, a colored pattern can be formed, and the resolution and residual film rate of the colored pattern tend to improve.

[0258] <Polymerizable compound (C)> The polymerizable compound (C) is a compound that can be polymerized by active radicals and / or acids generated from the polymerization initiator (D), and examples include compounds having polymerizable ethylenically unsaturated bonds, and is preferably a (meth)acrylic acid ester compound.

[0259] In particular, polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds. Examples of such polymerizable compounds include trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, tripentaerythritol octa(meth)acrylate, tripentaerythritol hepta(meth)acrylate, tetrapentaerythritol deca(meth)acrylate, tetrapentaerythritol nona(meth)acrylate, and tri Examples include (2-(meth)acryloyloxyethyl) isocyanurate, ethylene glycol-modified pentaerythritol tetra(meth)acrylate, ethylene glycol-modified dipentaerythritol hexa(meth)acrylate, propylene glycol-modified pentaerythritol tetra(meth)acrylate, propylene glycol-modified dipentaerythritol hexa(meth)acrylate, caprolactone-modified pentaerythritol tetra(meth)acrylate, and caprolactone-modified dipentaerythritol hexa(meth)acrylate. Among these, trimethylolpropane tri(meth)acrylate, dipentaerythritol penta(meth)acrylate, and dipentaerythritol hexa(meth)acrylate are preferred.

[0260] The weight-average molecular weight of the polymerizable compound (C) is preferably 150 to 2,900, more preferably 250 to 1,500.

[0261] The content of polymerizable compound (C) is preferably 7 to 65% by mass, more preferably 13 to 60% by mass, and even more preferably 17 to 55% by mass, based on the total amount of solids. When the content of polymerizable compound (C) is within the above range, the residual film rate when forming a colored pattern and the chemical resistance of the color filter tend to improve.

[0262] <Polymerization initiator (D)> The polymerization initiator (D) is not particularly limited as long as it is a compound that can generate active radicals, acids, etc., upon the action of light or heat and initiate polymerization; any known polymerization initiator can be used. Examples of polymerization initiators that generate active radicals include alkylphenone compounds, triazine compounds, acylphosphine oxide compounds, O-acyloxime compounds, and biimidazole compounds.

[0263] The O-acyloxime compound is a compound having a substructure represented by formula (d1). Hereinafter, * represents a bond.

[0264] [ka]

[0265] Examples of the O-acyloxime compounds include N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropane-1-one-2-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]ethane-1-imine, N-acetoxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethyl-2,4-dioxacyclopentanylmethyloxy)benzoyl}-9H-carbazole-3-yl]ethane-1-imine, N- Examples include acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]-3-cyclopentylpropan-1-imine, N-benzoyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]-3-cyclopentylpropan-1-one-2-imine, N-acetyloxy-1-[4-(2-hydroxyethyloxy)phenylsulfanylphenyl]propan-1-one-2-imine, N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine, and 2-[(acetyloxy)imino]-3-cyclohexyl-1-[4-(phenylsulfanyl)phenyl]propan-1-one. Commercially available products such as Irgacure OXE01, OXE02, OXE03 (all manufactured by BASF), N-1919 (manufactured by ADEKA), PBG-314, PBG-317, PBG-326, PBG-327, PBG-329 (all manufactured by Changzhou Strong Electronic New Materials Co., Ltd.) may also be used.Among them, O-acyloxime compounds include N-acetyloxy-1-[4-(2-hydroxyethyloxy)phenylsulfanylphenyl]propan-1-one-2-imine, N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine, 2-[(acetyloxy)imino]-3-cyclohexyl-1-[4-(phenylsulfanyl)phenyl]propan-1-one, N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, At least one compound selected from the group consisting of N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine and N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropane-1-one-2-imine is preferred, with 2-[(acetyloxy)imino]-3-cyclohexyl-1-[4-(phenylsulfanyl)phenyl]propane-1-one and N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine being more preferred. These O-acyloxime compounds tend to yield high-brightness color filters.

[0266] The alkylphenone compound is a compound having a substructure represented by formula (d2) or formula (d3). In these substructures, the benzene ring may have substituents.

[0267] [ka]

[0268] Examples of compounds having the substructure represented by formula (d2) include 2-methyl-2-morpholino-1-(4-methylsulfanylphenyl)propan-1-one, 2-dimethylamino-1-(4-morpholinophenyl)-2-benzylbutan-1-one, and 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]butan-1-one. Commercially available products such as Irgacure 369, 907, and 379 (all manufactured by BASF) may also be used.

[0269] Examples of compounds having the substructure represented by formula (d3) include 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy)phenyl]propan-1-one, 1-hydroxycyclohexylphenyl ketone, oligomer of 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propan-1-one, α,α-diethoxyacetophenone, and benzyldimethyl ketal. In terms of sensitivity, alkylphenone compounds having the substructure represented by formula (d2) are preferred.

[0270] Examples of the aforementioned triazine compounds include 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxynaphthyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxystyryl)-1,3,5-triazine, and 2,4-bis(trichloromethyl)-6-[ Examples include 2-(5-methylfuran-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl)ethenyl]-1,3,5-triazine, and 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)ethenyl]-1,3,5-triazine.

[0271] Examples of the aforementioned acylphosphine oxide compound include 2,4,6-trimethylbenzoyldiphenylphosphine oxide. Commercially available products such as Irgacure® 819 (manufactured by BASF) may also be used.

[0272] Examples of the biimidazole compounds include 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3-dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole (see, for example, Japanese Patent Publication No. 6-75372, Japanese Patent Publication No. 6-75373, etc.), 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, and 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(alkoxyphen Examples include (nyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(dialkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(trialkoxyphenyl)biimidazole (see, for example, Japanese Patent Publication No. 48-38403, Japanese Patent Application Publication No. 62-174204, etc.), and biimidazole compounds in which the phenyl group at the 4,4',5,5'-position is substituted with a carboalkoxy group (see, for example, Japanese Patent Application Publication No. 7-10913, etc.).

[0273] Furthermore, examples of polymerization initiators (D) include benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether; benzophenone compounds such as benzophenone, o-benzoyl methyl benzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, 3,3',4,4'-tetra(tert-butylperoxycarbonyl)benzophenone, and 2,4,6-trimethylbenzophenone; quinone compounds such as 9,10-phenanthrenequinone, 2-ethylanthraquinone, and camphorquinone; and 10-butyl-2-chloroacridone, benzyl, methyl phenylglyoxylate, and titanocene compounds. These are preferably used in combination with polymerization initiators (D1) (especially amines) described later.

[0274] Examples of polymerization initiators that generate acids 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, as well as nitrobenzyl tosylates and benzoin tosylates.

[0275] The polymerization initiator (D) is preferably one comprising at least one selected from the group consisting of alkylphenone compounds, triazine compounds, acylphosphine oxide compounds, O-acyloxime compounds, and biimidazole compounds, and more preferably a polymerization initiator comprising an O-acyloxime compound.

[0276] The content of the polymerization initiator (D) is preferably 0.1 to 30 parts by mass, and more preferably 1 to 20 parts by mass, based on 100 parts by mass of the total amount of resin (B) and polymerizable compound (C). When the content of the polymerization initiator (D) is within the above range, sensitivity tends to increase and exposure time is shortened, thus improving the productivity of color filters.

[0277] <Polymerization initiator (D1)> Polymerization initiator (D1) is a compound or sensitizer used to accelerate the polymerization of a polymerizable compound whose polymerization has been initiated by a polymerization initiator. When polymerization initiator (D1) is included, it is usually used in combination with the polymerization initiator (D). Examples of polymerization initiators (D1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds, and carboxylic acid compounds.

[0278] Examples of the amine compounds include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 2-ethylhexyl 4-dimethylaminobenzoate, N,N-dimethylparatoluidine, 4,4'-bis(dimethylamino)benzophenone (commonly known as Michla's ketone), 4,4'-bis(diethylamino)benzophenone, and 4,4'-bis(ethylmethylamino)benzophenone, with 4,4'-bis(diethylamino)benzophenone being preferred. Commercial products such as EAB-F (manufactured by Hodogaya Chemical Co., Ltd.) may also be used.

[0279] Examples of the alkoxyanthracene compounds include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene, 9,10-dibutoxyanthracene, and 2-ethyl-9,10-dibutoxyanthracene.

[0280] Examples of the thioxanthone compounds include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, and 1-chloro-4-propoxythioxanthone.

[0281] Examples of the carboxylic acid compounds include phenylsulfanylacetic acid, methylphenylsulfanylacetic acid, ethylphenylsulfanylacetic acid, methylethylphenylsulfanylacetic acid, dimethylphenylsulfanylacetic acid, methoxyphenylsulfanylacetic acid, dimethoxyphenylsulfanylacetic acid, chlorophenylsulfanylacetic acid, dichlorophenylsulfanylacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, naphthoxyacetic acid, and the like.

[0282] When these polymerization initiators (D1) are used, their content is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, based on 100 parts by mass of the total amount of resin (B) and polymerizable compound (C). When the amount of polymerization initiator (D1) is within this range, it is possible to form a colored pattern with even higher sensitivity, and the productivity of color filters tends to improve.

[0283] <Solvent (E)> The solvent (E) is not particularly limited, and any solvent commonly used in the art may be used. Examples include ester solvents (solvents containing -COO- but not -O-), ether solvents (solvents containing -O- but not -COO-), ether ester solvents (solvents containing both -COO- and -O-), ketone solvents (solvents containing both -CO- and -COO-), alcohol solvents (solvents containing OH but not -O-, -CO-, and -COO-), aromatic hydrocarbon solvents, amide solvents, dimethyl sulfoxides, and the like.

[0284] Examples of ester solvents include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutanoate, ethyl acetate, n-butyl acetate, isobutyl acetate, pentyl formate, isopentyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexanol acetate, and γ-butyrolactone.

[0285] Examples of ether solvents include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenethole, and methylanisole.

[0286] Examples of ether ester solvents include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, 2-ethoxypropionate Examples include ethyl xy-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.

[0287] Examples of ketone solvents include 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone, and isophorone.

[0288] Examples of alcoholic solvents include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerin.

[0289] Examples of aromatic hydrocarbon solvents include benzene, toluene, xylene, and mesitylene.

[0290] Examples of amide solvents include N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.

[0291] The solvent is preferably one or more selected from the group consisting of ether solvents, ether ester solvents, and amide solvents, more preferably containing ether solvents, ether ester solvents, and amide solvents, and even more preferably containing diethylene glycol methyl ethyl ether, propylene glycol monomethyl ether acetate, and N-methylpyrrolidone.

[0292] Of the above solvents, organic solvents having a boiling point of 120°C or higher and 180°C or lower at 1 atm are preferred from the viewpoint of applicability and drying properties. Preferred solvents include 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, with propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate, and ethyl 3-ethoxypropionate being more preferred.

[0293] The solvent (E) content is preferably 70 to 95% by mass, and 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, and more preferably 8 to 25% by mass. When the solvent (E) content is within the above range, the flatness during coating is good, and the display characteristics tend to be good because there is no shortage of color density when a color filter is formed.

[0294] <Leveling agent (F)> Examples of leveling agents (F) include silicone-based surfactants, fluorine-based surfactants, and silicone-based surfactants containing fluorine atoms. These may have polymerizable groups in their side chains. Examples of silicone-based surfactants include surfactants that have siloxane bonds in their molecules. Specifically, examples include Toray Silicone DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, SH29PA, SH30PA, SH8400 (product name: manufactured by Toray Dow Corning Co., Ltd.), KP321, KP322, KP323, KP324, KP326, KP340, KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452, and TSF4460 (manufactured by Momentive Performance Materials Japan LLC).

[0295] Examples of the aforementioned fluorine-based surfactants include surfactants having fluorocarbon chains in their molecules. Specifically, these include Florard® FC430, FC431 (manufactured by Sumitomo 3M Co., Ltd.), Megafac® F142D, F171, F172, F173, F177, F183, F554, R30, RS-718-K (manufactured by DIC Corporation), F-Top® EF301, EF303, EF351, EF352 (manufactured by Mitsubishi Materials Electronic Chemicals Co., Ltd.), Surflon® S381, S382, SC101, SC105 (manufactured by AGC Inc. (formerly Asahi Glass Co., Ltd.)), and E5844 (manufactured by Daikin Fine Chemical Laboratories, Inc.).

[0296] Examples of silicone-based surfactants containing fluorine atoms include surfactants having siloxane bonds and fluorocarbon chains in their molecules. Specifically, examples include Megafac® R08, BL20, F475, F477, and F443 (manufactured by DIC Corporation).

[0297] The content of the leveling agent (F) is preferably 0.001 to 0.2% by mass, more preferably 0.002 to 0.1% by mass, and even more preferably 0.005 to 0.05% by mass, relative to the total amount of the colored resin composition. Note that this content does not include the content of the pigment dispersant. When the content of the leveling agent (F) is within the above range, the flatness of the color filter can be improved.

[0298] <Other ingredients> The colored resin composition may optionally contain additives known in the art, such as fillers, other polymer compounds, adhesion promoters, antioxidants, light stabilizers, and chain transfer agents.

[0299] <Method for producing colored resin composition> A colored resin composition can be prepared, for example, by mixing a colorant (A) containing an aluminum phthalocyanine dye, a compound represented by formula (DA), a resin (B), and a solvent (E), as well as a polymerizable compound (C), a polymerization initiator (D), a leveling agent (F), a polymerization initiator aid (D1), and other components as needed. The aluminum phthalocyanine dye may be included in the pigment dispersion beforehand. The desired colored resin composition can be prepared by mixing the remaining components into the pigment dispersion to a predetermined concentration. If the solution contains a dye, the dye may be dissolved in part or all of the solvent (E) beforehand to prepare the solution. It is preferable to filter the solution through a filter with a pore size of about 0.01 to 1 μm. It is preferable to filter the mixed colored resin composition through a filter with a pore size of approximately 0.01 to 10 μm.

[0300] [Color Filter] Methods for producing a colored pattern for a color filter from the colored resin composition of the present invention include photolithography, inkjet printing, and other printing methods. Among these, photolithography is preferred. Photolithography is a method in which the colored resin composition is applied to a substrate, dried to form a composition layer, and then exposed to light through a photomask for development. In photolithography, by not using a photomask during exposure and / or by not developing, a colored coating film, which is a cured product of the composition layer, can be formed. The colored pattern or colored coating film formed in this way is the color filter of the present invention.

[0301] The film thickness of the color filter (colored coating) is, for example, 30 μm or less, preferably 20 μm or less, more preferably 6 μm or less, even more preferably 3 μm or less, even more preferably 1.5 μm or less, particularly preferably 0.5 μm or less, preferably 0.1 μm or more, more preferably 0.2 μm or more, and even more preferably 0.3 μm or more.

[0302] As substrates, glass plates such as quartz glass, borosilicate glass, aluminasilate glass, and soda-lime glass with a silica coating on the surface are used; resin plates such as polycarbonate, polymethyl methacrylate, and polyethylene terephthalate are used; silicon is used; and aluminum, silver, and silver / copper / palladium alloy thin films are formed on the substrate. Other color filter layers, resin layers, transistors, circuits, etc. may be formed on these substrates. Alternatively, a substrate treated with HMDS on a silicon substrate may be used.

[0303] The formation of each color pixel by photolithography can be carried out using known or conventional equipment and conditions. For example, it can be manufactured as follows. First, a colored resin composition is applied to a substrate, and volatile components such as solvents are removed by heat drying (pre-baking) and / or vacuum drying, and then dried to obtain a smooth composition layer. Coating methods include spin coating, slit coating, and slit and spin coating. The temperature for heat drying is preferably 30 to 120°C, and more preferably 50 to 110°C. The heating time is preferably 10 seconds to 60 minutes, and more preferably 30 seconds to 30 minutes. When performing vacuum drying, it is preferable to do so under a pressure of 50 to 150 Pa and at a temperature range of 20 to 25°C. The thickness of the composition layer is not particularly limited and can be appropriately selected according to the desired thickness of the color filter.

[0304] Next, the composition layer is exposed through a photomask to form the desired colored pattern. The pattern on the photomask is not particularly limited, and a pattern appropriate to the intended application is used. For exposure, a light source that generates light with a wavelength of 250 to 450 nm is preferred. For example, light below 350 nm can be filtered out using a filter that cuts out this wavelength range, or light around 436 nm, 408 nm, and 365 nm can be selectively extracted using a bandpass filter that extracts these wavelength ranges. Specific examples include mercury lamps, light-emitting diodes, metal halide lamps, and halogen lamps. It is preferable to use a reduction projection exposure apparatus or proximity exposure apparatus such as a mask aligner and stepper, as this allows for uniform irradiation of the entire exposure surface with parallel light rays and precise alignment of the photomask and the substrate.

[0305] A colored pattern is formed on the substrate by developing the exposed composition layer in contact with a developer. During development, the unexposed parts of the composition layer are dissolved and removed by the developer. As the developer, aqueous solutions of alkaline compounds such as potassium hydroxide, sodium bicarbonate, sodium carbonate, and tetramethylammonium hydroxide are preferred. The concentration of these alkaline compounds in the aqueous solution is preferably 0.01 to 10% by mass, and more preferably 0.03 to 5% by mass. Furthermore, the developer may also contain a surfactant. The development method may be any of the following: the paddle method, the dipping method, and the spray method. Furthermore, the substrate may be tilted at any angle during development. After development, washing with water is preferred.

[0306] Further, it is preferable to perform post-baking on the obtained colored pattern. The post-baking temperature is preferably 80 to 250°C, more preferably 100 to 245°C. The post-baking time is preferably 1 to 120 minutes, more preferably 2 to 30 minutes.

[0307] The colored pattern and colored coating film obtained in this manner are useful as a color filter, and the color filter is useful as a color filter used in display devices (e.g., liquid crystal display devices, organic EL devices, etc.), electronic paper, solid-state image sensors, and the like.

[0308] The present application claims the benefit of priority based on Japanese Patent Application No. 2020-150532 filed on September 8, 2020. The entire content of the specification of Japanese Patent Application No. 2020-150532 filed on September 8, 2020 is incorporated herein by reference.

Examples

[0309] Hereinafter, the present invention will be described more specifically with reference to examples. However, the present invention is not limited by the following examples. It is of course possible to appropriately modify the implementation within a range that conforms to the gist of the preceding and following description, and all such modifications are included in the technical scope of the present invention. In the examples, % and parts representing content or usage are based on mass unless otherwise specified.

[0310] The structure of the compound was confirmed by mass spectrometry (MALDI-TOF MS; JMS-S3000 manufactured by JEOL Ltd.). <MALDI Conditions> Matrix: DCTB (trans-2-[3-(4-tert-butylphenyl)-2-methyl-2-propenylidene]malononitrile) Solvent: THF (containing stabilizer) Ionization aid: None

[0311] <Synthesis of Colorant> [Example of colorant synthesis 1] The compound represented by formula (1) was obtained by the synthesis method described in Japanese Patent Publication No. 2016-75837.

[0312] [ka]

[0313] [Example of colorant synthesis 2] The compound represented by formula (2) was obtained using 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).

[0314] [ka]

[0315] 1.0 part of the compound represented by formula (3) (manufactured by Tokyo Chemical Industry Co., Ltd.), 0.34 parts 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 and the mixture was heated to 120°C and stirred for 6 hours. After the reaction mixture was cooled to room temperature, 50 parts of deionized water were added. The resulting precipitate was obtained as residue after suction filtration, washed with 50 parts of deionized water, and then dried under reduced pressure at 60°C to obtain 1.18 parts of the compound represented by formula (4).

[0316] [ka]

[0317] [ka]

[0318] Identification of the compound represented by formula (4) (Mass Spectrometry) Ionization Mode = MALDI-TOF - : m / z = 716.3 Exact Mass: 716.2

[0319] [Example of colorant synthesis 3] In the synthesis method of the compound represented by formula (2) in Colorant Synthesis Example 2, the alcohol used was changed to 3-buten-1-ol to obtain the compound represented by formula (5).

[0320] [ka]

[0321] 1.0 part of the compound represented by formula (3) (manufactured by Tokyo Chemical Industry Co., Ltd.), 0.39 parts of the compound represented by formula (5), and 5.0 parts of NMP were mixed at room temperature and the mixture was heated to 120°C and stirred for 6 hours. After the reaction mixture was cooled to room temperature, 50 parts of deionized water were added. The resulting precipitate was obtained as residue after suction filtration, washed with 50 parts of deionized water, and then dried under reduced pressure at 60°C to obtain 1.24 parts of the compound represented by formula (6).

[0322] [ka]

[0323] Identification of the compound represented by formula (6) (Mass Spectrometry) Ionization Mode = MALDI-TOF - : m / z = 744.4 Exact Mass: 744.2

[0324] [Example of colorant synthesis 4] 1.5 parts aluminum chloride (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.), 6.2 parts 4-tert-butylphthalonitrile (manufactured by Tokyo Chemical Industries, Ltd.), 5.1 parts 1,8-diazabicyclo[5.4.0]-7-undecene (manufactured by Tokyo Chemical Industries, Ltd.), and 11 parts 1-pentanol (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) were mixed at room temperature and the mixture was heated to 160°C and stirred for 13 hours. After the reaction mixture was cooled to room temperature, 63 parts ethyl acetate was added. The resulting precipitate was obtained as residue after suction filtration, washed with 89 parts ion-exchanged water, and dried under reduced pressure at 60°C to obtain 3.4 parts of the compound represented by formula (7).

[0325] [ka]

[0326] Identification of the compound represented by formula (7) (Mass Spectrometry) Ionization Mode = MALDI-TOF - :m / z = 798.5 Exact Mass: 798.4

[0327] 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 Industries Co., Ltd.), and 5.5 parts of NMP were mixed at room temperature and the mixture was heated to 120°C and stirred for 7 hours. After the reaction mixture was cooled to room temperature, 28 parts of deionized water were added. The resulting precipitate was obtained as residue after suction filtration, 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).

[0328] [ka]

[0329] [ka]

[0330] Identification of the compound represented by formula (9) (Mass Spectrometry) Ionization Mode = MALDI-TOF -:m / z = 930.6 Exact Mass: 930.4

[0331] <Synthesis of resins> [Example of resin synthesis 1] A suitable amount of nitrogen was flowed into a flask equipped with a reflux condenser, dropping funnel, and stirrer to replace the atmosphere with nitrogen. 340 parts of propylene glycol monomethyl ether acetate were added and heated to 80°C while stirring. Then, 57 parts of acrylic acid and 3,4-epoxytricyclo[5.2.1.0 2,6 ] Decane-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 2,6 A mixed solution of 54 parts of decane-9-yl acrylate (with a molar ratio of 1:1), 239 parts of benzyl methacrylate, and 73 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. Meanwhile, a solution of 40 parts of the 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 polymerization initiator solution was complete, the mixture was held at 80°C for 3 hours, then cooled to room temperature to obtain a copolymer (resin (B-1)) solution with 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 × 10⁻⁶. 3 The dispersion was 1.97, and the acid value on a solid content basis was 111 mg-KOH / g. Resin (B-1) has the following structural units.

[0332] [ka]

[0333] <Preparation of dispersion> [Example of dispersion preparation 1] Five parts of the compound represented by formula (1), two parts of a dispersant (BYKLPN-6919, manufactured by BYK) (on a solids basis), two parts of resin (B-1) (on a solids basis), one part of a mixture of the compound represented by formula (da-1) and the compound represented by formula (da-2) (with a molar ratio of 5:1), and 90 parts of propylene glycol monomethyl ether acetate were mixed. 300 parts of 0.2 μm zirconia beads were added, and the mixture was shaken for 30 minutes using paint conditioner (manufactured by LAU). The zirconia beads were then removed by filtration to obtain dispersion (A-1).

[0334] [ka]

[0335] [Dispersion preparation examples 2 to 9] Dispersions (A-2) to (A-9) were obtained using the same method as in Dispersion Preparation Example 1, except that each component was changed as shown in Table 36.

[0336] [Table 36]

[0337] [Dispersion preparation examples 10-15] Dispersions (A-10) to (A-15) were obtained using the same method as in Dispersion Preparation Example 1, except that the components were changed as shown in Table 37.

[0338] [Table 37]

[0339] <Preparation of colored resin composition> [Colored resin composition 1] A colored resin composition 1 was obtained by mixing the following components. Dispersion liquid (A-1) 360 parts Resin (B-1) (solid content equivalent) 44.9 parts Polymerizable compound (C-1): Dipentaerythritol polyacrylate: Product Name A-9550: Manufactured by Shin-Nakamura Chemical Industry Co., Ltd. 17.4 parts Polymerizable compound (C-2): Trimethylolpropane triacrylate: Product Name A-TMPT: Manufactured by Shin-Nakamura Chemical Industry Co., Ltd. 17.4 parts Polymerization initiator (D): 2-[(acetyloxy)imino]-3-cyclohex Lu-1-[4-(phenylsulfanyl)phenyl]propan-1-one: Product name PBG-327: O-acyl oxime compound; Changzhou Strong Electronic New Materials ( Manufactured by (Co., Ltd.) 4.34 units Solvent (E): Propylene glycol monomethyl ether acetate 556 copies Leveling agent (F): Polyether-modified silicone oil: Product name: Toreshi Ricohne SH8400: Manufactured by Toray Dow Corning Co., Ltd. 0.1 part

[0340] [Colored resin composition 2 to colored resin composition 8, comparative colored resin composition 1] Colored resin compositions 2 to 8 and comparative colored resin composition 1 were obtained in the same manner as colored resin composition 1, except that each component was changed as shown in Table 38.

[0341] [Table 38]

[0342] [Colored resin composition 9 to colored resin composition 13, comparative colored resin composition 2] Colored resin compositions 9 to 13 and comparative colored resin composition 2 were obtained in the same manner as colored resin composition 1, except that each component was changed as shown in Table 39.

[0343] [Table 39]

[0344] <Evaluation of foreign matter in coatings> [Formation of colored coating] A colored resin composition prepared with colored resin compositions 1-8, 9-13, and comparative colored resin compositions 1 and 2 was applied to a 5cm square glass substrate (Eagle 2000; Corning Corporation) by spin coating, and then pre-baked at 90°C for 2 minutes to form a colored composition layer. After cooling, the substrate was exposed to air at 60 mJ / cm² using an exposure machine (TME-150RSK; Topcon Corporation) in an atmospheric environment. 2 The colored composition layer was irradiated with light at the specified exposure level (based on 365 nm). Subsequently, post-baking was performed at 230°C for 5 minutes to obtain a colored coating film. [Observation of coating film properties] The colored coating film obtained on the glass substrate was examined using a laser microscope (LEXT OLS4100; manufactured by Olympus Corporation) to confirm the presence or absence of foreign matter (coarse particles) in the colored coating film. ○: No foreign objects were observed. ×: A foreign object was observed.

[0345] As shown in Tables 38 and 39, no foreign matter was found in the colored coating of colored resin compositions 1-8 and 9-13. On the other hand, numerous foreign matter was found in comparative colored resin compositions 1 and 2.

[0346] <Adhesion Evaluation> [Formation of dot patterns] A 4-inch silicon wafer (manufactured by Rokko Electronics Co., Ltd.) was coated with colored resin compositions 9-13 and comparative colored resin composition 2 using a spin-coating method. The wafer was then pre-baked at 90°C for 2 minutes to form a colored composition layer. After cooling, the wafer was exposed to 400 mJ / cm² under an atmospheric atmosphere using an exposure machine (NSR-2205i11D; manufactured by Nikon Corporation, NA=0.63, σ=0.60). 2 The colored composition layer was irradiated with light at an exposure level of 365 nm. During irradiation, an exposure mask was placed between the light source and the substrate, and the colored composition layer was irradiated to form a 0.9 μm dot pattern (with a pitch of 1.8 μm). After developing the colored composition layer, post-bake was performed at 230°C for 5 minutes to obtain a colored coating.

[0347] [Confirmation of adhesion] The dot patterns of the colored coatings obtained on the substrates were observed using a laser microscope (LEXT OLS4100; manufactured by Olympus Corporation). Note that the higher the adhesion between the substrate and the colored coating, the more likely the dot patterns are to remain on the substrate; conversely, the lower the adhesion, the more likely the dot patterns are to peel off the substrate. ○: A 0.9μm dot pattern was formed, and there was no peeling. △: Although a 0.9μm dot pattern was formed, some peeling was observed. ×: The entire 0.9μm dot pattern has peeled off the substrate.

[0348] In comparative colored resin composition 2, all 0.9 μm dot patterns peeled off the substrate (evaluation: ×). On the other hand, in colored resin compositions 9 to 13, 0.9 μm dot patterns were formed and there was no peeling (evaluation: ○). From the comparison between comparative colored resin composition 2 and colored resin compositions 9 to 13, it can be seen that when the content of the compound represented by formula (DA) is preferably 1 part by mass or more (more preferably 10 parts by mass or more, and even more preferably 15 parts by mass or more) per 100 parts by mass of aluminum phthalocyanine dye, a colored coating film with higher adhesion to the substrate is formed.

Claims

1. It contains a coloring agent, a compound represented by formula (DA), a resin, and a solvent. The aforementioned coloring agent contains aluminum phthalocyanine dye, A colored resin composition in which the compound represented by the formula (DA) is contained in an amount of 15 parts by mass or more and 180 parts by mass or less per 100 parts by mass of aluminum phthalocyanine dye. 【Chemistry 1】 [In formula (DA), R d1 is, -CO 2 R xa1 R represents a hydrocarbon group having 1 to 6 carbon atoms. xa1 This represents a hydrogen atom. R d2 and R d3 are R d2 and R d3 are bonded, and -CO-NR d1 together with -CO- form a ring represented by any one of formulas (r-1) to (r-7).] 【Chemistry 2】

2. The colored resin composition according to claim 1, wherein the aluminum phthalocyanine dye is a compound represented by formula (Xa) or formula (Xb). 【Transformation 3】 【Chemistry 4】 [In equation (Xa), Z is a hydroxyl group, a chlorine atom, and -OP(=O)R a1 R a2 , or -O-SiR a3 R a4 R a5 It represents. R a1 ~R a5 Each of these independently represents a hydrogen atom, a hydroxyl group, or a hydrocarbon group having 1 to 21 carbon atoms which may have substituents, and R a1 and R a2 , or R a3 ~R a5 Any two of these may bond to each other to form a ring. The hydrocarbon group has 2 to 21 carbon atoms and the hydrocarbon group is -CH 2 If it has -, the -CH 2 The dash may be replaced by -O-, -S-, or -CO-. X x1 ~X x4 Each of these is independently of -R x4 , -OR x4 ,-SR x4 This represents a halogen atom, a nitro group, or a sulfamoyl group which may have a substituent. R x4 This represents a hydrocarbon group having 1 to 20 carbon atoms, which may have substituents, wherein the hydrocarbon group has 2 to 21 carbon atoms and the hydrocarbon group is -CH 2 If it has -, the -CH 2 The dash may be replaced by -O-, -S-, or -CO-. nx1 to nx4 each independently represent an integer from 0 to 4. In formula (Xb), L is -O-SiR a6 R a7 -O-, -O-SiR a8 R a9 -O-SiR a10 R a11 -O-, or -O-P (=O)R a12 It represents -O-. R a6 ~R a12 Each of these independently represents a hydrogen atom, a hydroxyl group, or a hydrocarbon group having 1 to 21 carbon atoms which may have substituents, and R a6 and R a7 , R a8 and R a9 , or R a10 and R a11 These may bond to each other to form a ring. The hydrocarbon group has 2 to 21 carbon atoms and the hydrocarbon group is -CH 2 If it has -, the -CH 2 The dash may be replaced by -O-, -S-, or -CO-. X x5 ~X x12 Each of these is independently of -R x5 , -OR x5 ,-SR x5 This represents a halogen atom, a nitro group, or a sulfamoyl group which may have a substituent. R x5 This represents a hydrocarbon group having 1 to 20 carbon atoms, which may have substituents. nx5 to nx12 each independently represent an integer from 0 to 4.

3. The colored resin composition according to claim 2, wherein the compound represented by formula (Xa) is the compound represented by formula (XI), and the compound represented by formula (Xb) is the compound represented by formula (XII). 【Transformation 5】 【Transformation 6】 [In formula (XI), R x1 R represents an unsaturated hydrocarbon group having 2 to 20 carbon atoms which may have substituents, or an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have substituents. x2 is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms which may have substituents, or Z x2 and R x1 This represents a single bond connecting two things. Z x1 and Z x2 Each of these independently represents either a single bond or an oxygen atom. X x1 ~X x4 nx1 to nx4 are the same as described above. In formula (XII), R x3 This represents an unsaturated hydrocarbon group having 2 to 20 carbon atoms that may have substituents, or an aromatic hydrocarbon group having 6 to 20 carbon atoms that may have substituents. Z x3 This represents a single bond or an oxygen atom. X x5 ~X x12 nx5 to nx12 are the same as described above.

4. The colored resin composition according to claim 1, wherein the aluminum phthalocyanine dye is a compound represented by formula (YI) or formula (YII). 【Transformation 7】 【Transformation 8】 [In formula (YI), R y1 This represents a hydrocarbon group having 1 to 20 carbon atoms, which may have a hydrogen atom or substituents. R y2 This includes a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms which may have substituents, or Z y3 and R y1 This represents a single bond connecting two things. Y 1 and Z y1 Each of these independently represents either an oxygen atom or a sulfur atom. Z y2 and Z y3 Each of these independently represents a single bond, an oxygen atom, or a sulfur atom. However, Y 1 Z y1 Z y2 and Z y3 At least one of them represents a sulfur atom. X y1 ~X y4 Each of these is independently of -R y4 , -OR y4 ,-SR y4 This represents a halogen atom, a nitro group, or a sulfamoyl group which may have a substituent. R y4 This represents a hydrocarbon group having 1 to 20 carbon atoms, which may have substituents. ny1 to ny4 each independently represent an integer from 0 to 4. In formula (YII), R y3 This represents a hydrocarbon group having 1 to 20 carbon atoms, which may have a hydrogen atom or substituents. Y 2 and Z y4 Each of these independently represents either an oxygen atom or a sulfur atom. Z y5 represents a single bond, an oxygen atom, or a sulfur atom. Provided that Y 2 , Z y4 and Z y5 at least one of which represents a sulfur atom. X y5 ~X y12 Each of these is independently of -R y5 , -OR y5 ,-SR y5 This represents a halogen atom, a nitro group, or a sulfamoyl group which may have a substituent. R y5 This represents a hydrocarbon group having 1 to 20 carbon atoms, which may have substituents. ny5 to ny12 each independently represent an integer from 0 to 4.

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

6. A color filter formed from a colored resin composition according to any one of claims 1 to 5.

7. A display device including the color filter described in claim 6.

8. A solid-state image sensor including the color filter described in claim 6.

Images