Phthalocyanine compound, resin composition, optical filter, and solid-state imaging element

Abstract

To provide a phthalocyanine compound having a maximum absorption wavelength in an NIR region with a sufficiently wide half-value width.SOLUTION: A phthalocyanine compound is represented by formula (I). In the formula (I), M1 represents a metal atom. n represents 1 to 3. RA1 and RA2 represent a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, or an ORA51 group. RA51 represents a hydrocarbon group having 1 to 20 carbon atoms. A1 and A2 represent an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms. RB1 and RB2 represent a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, or an ORB51 group. RB51 represents a hydrocarbon group having 1 to 20 carbon atoms. B1 and B2 represent an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a phthalocyanine compound, a resin composition, an optical filter, and a solid-state imaging device. [Background technology]

[0002] Compounds that absorb light in the near-infrared region (NIR region) are expected to be applied to various optical fields such as optical filters, security marking, lithography, optical recording media, etc. Known compounds that absorb light in the NIR region include compounds represented by the following formula (I-1) or (II-1) (see, for example, Patent Document 1):

[0003] [ka]

[0004] [ka] [Prior art documents] [Patent documents]

[0005] [Patent Document 1] Japanese Patent Application Publication No. 2023-184451 Summary of the Invention [Problem to be solved by the invention]

[0006] A main object of the present invention is to provide a phthalocyanine compound having a maximum absorption wavelength with a sufficiently wide half-value width. [Means for solving the problem]

[0007] The present invention provides the phthalocyanine compound according to [1] and [2], the resin composition according to [3] and [4], the optical filter according to [5], and the solid-state imaging device according to [6].

[0008] [1] A phthalocyanine compound represented by formula (I). [ka] [In formula (I), M 1 represents a metal atom. n represents an integer of 1 to 3. R A1 and R A2 are each independently a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, or OR A51 represents a group, and two or more R A1 and R A2 When present, they may be the same or different from one another. R A51 represents a hydrocarbon group having 1 to 20 carbon atoms, and two or more R A51 When present, they may be the same or different from one another. A 1 and A 2 each independently represents an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 3 to 20 carbon atoms, and two or more A 1 and A 2 When present, they may be the same or different from one another. R B1 and R B2 are each independently a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, or OR B51 represents a group, and two or more R B1 and R B2 When present, they may be the same or different from one another. R B51 represents a hydrocarbon group having 1 to 20 carbon atoms, and two or more R B51 When present, they may be the same or different from one another. B 1 and B 2 each independently represents an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 3 to 20 carbon atoms, and two or more B 1 and B 2When present, they may be the same or different from one another. * represents a bond. A double line consisting of a solid line and a dashed line represents a single bond or a double bond.] [2] A phthalocyanine compound represented by formula (I-1), formula (I-2), formula (I-3), or formula (I-4). [ka] [In formula (I-1), M 1 represents a metal atom. R A1 and R A2 are each independently a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, or OR A51 represents a group, and two or more R A1 and R A2 When present, they may be the same or different from one another. R A51 represents a hydrocarbon group having 1 to 20 carbon atoms, and two or more R A51 When present, they may be the same or different from one another. A 1 and A 2 each independently represents an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 3 to 20 carbon atoms, and two or more A 1 and A 2 When present, they may be the same or different from one another. R B1 and R B2 are each independently a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, or OR B51 represents a group, and two or more R B1 and R B2 When present, they may be the same or different from one another. R B51 represents a hydrocarbon group having 1 to 20 carbon atoms, and two or more R B51 When present, they may be the same or different from one another. B 1 and B 2each independently represents an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 3 to 20 carbon atoms, and two or more B 1 and B 2 When present, they may be the same or different from each other.] [ka] [In formula (I-2), M 1 , R A1 , R A2 , A 1 , A 2 , R B1 , R B2 , B 1 , and B 2 has the same meaning as above.] [ka] [In formula (I-3), M 1 , R A1 , R A2 , A 1 , A 2 , R B1 , R B2 , B 1 , and B 2 has the same meaning as above.] [ka] [In formula (I-4), M 1 , R A1 , R A2 , A 1 , A 2 , R B1 , R B2 , B 1 , and B 2 has the same meaning as above.] [3] Contains a colorant, a resin, and a solvent; A resin composition, wherein the colorant contains the phthalocyanine compound according to [1] or [2]. [4] The resin composition according to [3], further comprising a polymerizable compound and a polymerization initiator. [5] An optical filter formed from the resin composition according to [3] or [4]. [6] A solid-state imaging device comprising the optical filter according to [5]. [Effects of the Invention]

[0009] According to the present invention, there is provided a phthalocyanine compound having a maximum absorption wavelength in the NIR region with a sufficiently wide half-width. Furthermore, according to the present invention, there is provided a resin composition containing such a phthalocyanine compound. The resin composition of the present invention can form a cured coating film (e.g., an optical filter) that has a sufficiently high average transmittance in the range of 940 to 1200 nm and generates sufficiently little foreign matter. Furthermore, according to the present invention, there are provided an optical filter formed from such a resin composition and a solid-state imaging device including the optical filter. DETAILED DESCRIPTION OF THE INVENTION

[0010] Hereinafter, embodiments of the present invention will be described in detail, but the present invention is not limited to the following embodiments.

[0011] In this specification, a numerical range indicated using "to" indicates a range that includes the numerical values ​​before and after "to" as the minimum and maximum values, respectively. In numerical ranges described in stages in this specification, the upper or lower limit value described in one numerical range may be replaced with the upper or lower limit value of another numerical range described in stages. Furthermore, in numerical ranges described in this specification, the upper or lower limit value of that numerical range may be replaced with a value shown in an example.

[0012] In this specification, (meth)acrylate means an acrylate or the corresponding methacrylate. The same applies to other similar expressions such as a (meth)acryloyl group and a (meth)acrylic acid ester.

[0013] In this specification, unless otherwise specified, the materials exemplified below may be used alone or in combination of two or more within the range that meets the conditions. When multiple substances corresponding to each component are present, the content of each component means the total amount of the multiple substances unless otherwise specified.

[0014] In this specification, the near-infrared region (NIR region) refers to a region with wavelengths of 700 to 2500 nm.

[0015] [Phthalocyanine compounds] The phthalocyanine compound of this embodiment is a phthalocyanine compound represented by formula (I) or a phthalocyanine compound represented by formula (I-1), (I-2), (I-3), or (I-4). Such a phthalocyanine compound has a maximum absorption wavelength with a sufficiently wide half-value width in the NIR region.

[0016] [ka]

[0017] The phthalocyanine compound represented by formula (I) means a phthalocyanine compound composed of a structural unit represented by formula (A) and a structural unit represented by formula (B). The phthalocyanine compound represented by formula (I) has at least one structural unit represented by formula (A) and at least one structural unit represented by formula (B). The total number of structural units represented by formula (A) and structural units represented by formula (B) is four.

[0018] [ka]

[0019] [ka]

[0020] M 1 represents a metal atom. 1is preferably a divalent metal atom. Examples of divalent metal atoms include atoms of copper, zinc, iron, cobalt, nickel, ruthenium, lead, rhodium, palladium, platinum, manganese, and tin. Among these, the divalent metal atom is preferably an iron atom, nickel atom, palladium atom, platinum atom, copper atom, or zinc atom, more preferably a nickel atom, palladium atom, or copper atom, even more preferably a nickel atom or palladium atom, and particularly preferably a nickel atom.

[0021] n represents an integer of 1 to 3.

[0022] R A1 and R A2 are each independently a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, or OR A51 represents a group, and two or more R A1 and R A2 When R is present, they may be the same or different from each other. A1 and R A2 In one embodiment, may be a hydrogen atom.

[0023] R A1 and R A2 Examples of the hydrocarbon group having 1 to 20 carbon atoms in the formula (I) include alkyl groups such as methyl, ethyl, propyl, butyl, hexyl, octyl, and dodecyl; aryl groups such as phenyl, o-tolyl, m-tolyl, p-tolyl, 2,4,6-trimethylphenyl, and naphthyl; and aralkyl groups such as benzyl and phenethyl. Some of the hydrogen atoms in these alkyl, aryl, and aralkyl groups may be substituted with halogen atoms (such as fluorine, chlorine, bromine, and iodine atoms).

[0024] R A51 represents a hydrocarbon group having 1 to 20 carbon atoms, and two or more R A51 When R is present, they may be the same or different from each other. A51 As the hydrocarbon group having 1 to 20 carbon atoms in A1 and R A2Examples of the hydrocarbon groups include those having 1 to 20 carbon atoms.

[0025] A 1 and A 2 each independently represents an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 3 to 20 carbon atoms, and two or more A 1 and A 2 When present, they may be the same or different. Some of the hydrogen atoms of the aryl group and heteroaryl group may be substituted with halogen atoms (fluorine atom, chlorine atom, bromine atom, iodine atom, etc.) or alkoxy groups having 1 to 20 carbon atoms. A 1 and A 2 In one embodiment, may be a phenyl group optionally substituted with an alkoxy group having 1 to 20 carbon atoms.

[0026] A 1 and A 2The aryl group having 6 to 20 carbon atoms in the formula (I) may be, for example, a monocyclic or polycyclic (for example, bicyclic or tricyclic) aryl group. Specific examples of the aryl group include a phenyl group, an o-tolyl group, an m-tolyl group, a p-tolyl group, a 2-ethylphenyl group, a 3-ethylphenyl group, a 4-ethylphenyl group, a 2,3-dimethylphenyl group, a 2,4-dimethylphenyl group, a 2,5-dimethylphenyl group, a 2,6-dimethylphenyl group, a 3,4-dimethylphenyl group, a 3,5-dimethylphenyl group, a 4-vinylphenyl group, an o-isopropylphenyl group, an m-isopropylphenyl group, a p-isopropylphenyl group, an o-tert-butylphenyl group, an m-tert-butylphenyl group, a p-tert-butylphenyl group, a 3,5-di(tert-butyl)phenyl group, a 3,5-di(tert-butyl)-4-methylphenyl group, Examples of the aryl group include a 4-butylphenyl group, a 4-pentylphenyl group, a 2,6-bis(1-methylethyl)phenyl group, a 2,4,6-tris(1-methylethyl)phenyl group, a 4-cyclohexylphenyl group, a 2,4,6-trimethylphenyl group, a 4-octylphenyl group, a 4-(1,1,3,3-tetramethylbutyl)phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 6-methyl-2-naphthyl group, a 5,6,7,8-tetrahydro-1-naphthyl group, a 5,6,7,8-tetrahydro-2-naphthyl group, a fluorenyl group, a phenanthryl group, an anthryl group, a 2-dodecylphenyl group, a 3-dodecylphenyl group, a 4-dodecylphenyl group, a phenanthryl group, a fluorenyl group, and a biphenyl group. The number of carbon atoms in the aryl group is preferably 6 to 18, more preferably 6 to 15, and even more preferably 6 to 12.

[0027] A 1 and A 2The heteroaryl group having 3 to 20 carbon atoms in the formula (I) may be, for example, a monocyclic or polycyclic (e.g., bicyclic or tricyclic) heteroaryl group. Specific examples of the heteroaryl group include a furanyl group, a benzofuranyl group, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a thienyl group, a benzothienyl group, an oxazolyl group, a benzoxazolyl group, a thiazolyl group, a benzothiazolyl group, an indolyl group, a carbazolyl group, an acridinyl group, an imidazolyl group, a benzimidazolyl group, a quinolyl group, and an isoquinolyl group. The number of carbon atoms in the heteroaryl group is preferably 3 to 18, more preferably 3 to 12, and even more preferably 3 to 9. The number of atoms constituting the ring of the heteroaryl group is preferably 5 to 10.

[0028] A 1 and A 2 Examples of the alkoxy group which may substitute some of the hydrogen atoms of the aryl group and heteroaryl group in the formula (I) include a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, an isobutoxy group, an s-butoxy group, a t-butoxy group, an n-pentyloxy group, an isopentyloxy group, a neopentyloxy group, an n-hexyloxy group, a cyclohexyloxy group, an n-heptyloxy group, an n-octyloxy group, a 2-ethylhexyloxy group, a t-octyloxy group, a decyloxy group, an undecyloxy group, a dodecyloxy group, a tridecyloxy group, a tetradecyloxy group, a pentadecyloxy group, a hexadecyloxy group, a heptadecyloxy group, an octadecyloxy group, a nonadecyloxy group, etc. The number of carbon atoms in the alkoxy group is preferably 1 to 18, more preferably 1 to 15, even more preferably 1 to 10, and particularly preferably 1 to 8.

[0029] R B1 and R B2 are each independently a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, or OR B51 represents a group, and two or more R B1 and R B2 When R is present, they may be the same or different from each other. B1 and R B2In one embodiment, OR B51 It may be a group.

[0030] R B1 and R B2 As the hydrocarbon group having 1 to 20 carbon atoms in A1 and R A2 Examples of the hydrocarbon groups include those having 1 to 20 carbon atoms.

[0031] R B51 represents a hydrocarbon group having 1 to 20 carbon atoms, and two or more R B51 When present, they may be the same or different from one another.

[0032] R B51 As the hydrocarbon group having 1 to 20 carbon atoms in A1 and R A2 Examples of the hydrocarbon groups include those having 1 to 20 carbon atoms.

[0033] B 1 and B 2 each independently represents an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 3 to 20 carbon atoms, and two or more B 1 and B 2 When B is present, they may be the same or different. Some of the hydrogen atoms of the aryl group and heteroaryl group may be substituted with halogen atoms (fluorine atom, chlorine atom, bromine atom, iodine atom, etc.) or alkoxy groups having 1 to 20 carbon atoms. 1 and B 2 In one embodiment, may be a phenyl group optionally substituted with an alkoxy group having 1 to 20 carbon atoms.

[0034] B 1 and B 2 As the aryl group having 6 to 20 carbon atoms, A 1 and A 2 Examples of the aryl group include the aryl groups having 6 to 20 carbon atoms in the above formula.

[0035] B 1 and B2 As the heteroaryl group having 3 to 20 carbon atoms in A, 1 and A 2 Examples of the heteroaryl group include those having 3 to 20 carbon atoms.

[0036] B 1 and B 2 Examples of the alkoxy group which may replace some of the hydrogen atoms of the aryl group and heteroaryl group in A 1 and A 2 Examples of the alkoxy groups which may be substituted with some of the hydrogen atoms of the aryl and heteroaryl groups in the above formula (1) include the alkoxy groups substituted with some of the hydrogen atoms of the aryl and heteroaryl groups in the above formula (1).

[0037] * represents a bond, and a double line consisting of a solid line and a dashed line represents a single bond or a double bond. However, the structure formed by the bond represented by these double lines does not have adjacent (contiguous) double bonds.

[0038] Specific examples of the phthalocyanine compound represented by formula (I) include phthalocyanine compounds represented by formula (I-1), formula (I-2), formula (I-3), and formula (I-4).

[0039] [ka]

[0040] In formula (I-1), M 1 , R A1 , R A2 , A 1 , A 2 , R B1 , R B2 , B 1 , and B 2 has the same meaning as above.

[0041] [ka]

[0042] In formula (I-2), M 1 , RA1 , R A2 , A 1 , A 2 , R B1 , R B2 , B 1 , and B 2 has the same meaning as above.

[0043] [ka]

[0044] In formula (I-3), M 1 , R A1 , R A2 , A 1 , A 2 , R B1 , R B2 , B 1 , and B 2 has the same meaning as above.

[0045] [ka]

[0046] In formula (I-4), M 1 , R A1 , R A2 , A 1 , A 2 , R B1 , R B2 , B 1 , and B 2 has the same meaning as above.

[0047] The phthalocyanine compound of the present embodiment may be, for example, a phthalodinitrile compound represented by the following formula (A1), a phthalodinitrile compound represented by the following formula (B1), and M 1 The compound can be obtained by reacting the compound with a salt containing the compound represented by the formula (I) in an alcoholic solvent in the presence of a base.

[0048] [ka]

[0049] [ka]

[0050] M 1 Examples of anions constituting salts containing the above include inorganic anions and organic anions. Examples of anions include hydroxide ions, halide ions such as chloride ions, bromide ions, and iodide ions, carbonate ions, nitrate ions, sulfate ions, and organic carboxylate ions such as formate ions, acetate ions, and propionate ions.

[0051] Examples of the base include DBU (1,8-diazabicyclo[5,4,0]-7-undecene); DBN (1,5-diazabicyclo[4.3.0]-5-nonene); and metal alkoxides such as sodium methoxide, potassium methoxide, lithium methoxide, sodium ethoxide, potassium ethoxide, sodium isopropoxide, and potassium isopropoxide.

[0052] Examples of alcohol solvents include 1-pentanol, 1-hexanol, 1-methoxyethanol, and 1-ethoxyethanol.

[0053] The phthalocyanine compound represented by formula (I-1) tends to be easily obtained as a main product by, for example, reacting a phthalodinitrile compound represented by formula (A1) with a phthalodinitrile compound represented by formula (B1) in a molar ratio of approximately 3:1.

[0054] The phthalocyanine compound represented by formula (I-2) and the phthalocyanine compound represented by formula (I-3) tend to be easily obtained as the main product by, for example, reacting a phthalodinitrile compound represented by formula (A1) with a phthalodinitrile compound represented by formula (B1) in a molar ratio of approximately 1:1.

[0055] The phthalocyanine compound represented by formula (I-4) tends to be easily obtained as a main product by, for example, reacting a phthalodinitrile compound represented by formula (A1) with a phthalodinitrile compound represented by formula (B1) in a molar ratio of approximately 1:3.

[0056] In the above method, a mixture of two or more phthalocyanine compounds selected from the group consisting of phthalocyanine compounds represented by formula (I-1), phthalocyanine compounds represented by formula (I-2), phthalocyanine compounds represented by formula (I-3), and phthalocyanine compounds represented by formula (I-4) may be obtained. When such a mixture is used as colorant (A1) described later, the compounds may be isolated before use, or the mixture may be used as is without isolation.

[0057] [Resin composition and method for producing the same] The resin composition of this embodiment contains a colorant (hereinafter sometimes referred to as "colorant (A)"), a resin (hereinafter sometimes referred to as "resin (B)"), and a solvent (hereinafter sometimes referred to as "solvent (E)"). The resin composition of this embodiment may further contain a polymerizable compound (hereinafter sometimes referred to as "polymerizable compound (C)") and a polymerization initiator (hereinafter sometimes referred to as "polymerization initiator (D)"). The resin composition of this embodiment may contain a leveling agent (hereinafter sometimes referred to as "leveling agent (F)").

[0058] <Colorant (A)> The colorant (A) contains the above-mentioned phthalocyanine compound (hereinafter, may be referred to as "colorant (A1)"). When the colorant (A) contains the colorant (A1), an optical filter having near-infrared transmittance can be obtained.

[0059] The content of the colorant (A1) is preferably 10 to 100 mass%, more preferably 20 to 100 mass%, and even more preferably 30 to 100 mass%, based on the total amount of the colorant (A). In one embodiment, the content of the colorant (A1) may be 100 mass%, based on the total amount of the colorant (A).

[0060] The colorant (A) may further contain a colorant (hereinafter, sometimes referred to as "colorant (A2)") that is different from the colorant (A1).

[0061] Examples of the colorant (A2) include dyes and pigments.

[0062] Examples of dyes include compounds classified as compounds having a hue other than pigments in the Color Index (published by The Society of Dyers and Colourists), and known dyes described in Dyeing Notes (Shikisensha Co., Ltd.).

[0063] Xanthene dyes are dyes containing compounds with a xanthene skeleton in the molecule. Examples of xanthene dyes include CI Acid Red 51 (hereinafter, the term "CI Acid Red" will be omitted and only the number will be used. Similarly, other similar expressions may also be used only with the number), 52, 87, 92, 94, 289, and 388; CI Acid Violet 9, 30, and 102; CI Basic Red 1 (Rhodamine 6G), 2, 3, 4, 8, 10, and 11; CI Basic Violet 10 (Rhodamine B), 11; CI Solvent Red 218; CI Mordant Red 27; CI Reactive Red 36 (Rose Bengal B); sulforhodamine G; xanthene dyes described in JP 2010-32999 A; and xanthene dyes described in Japanese Patent No. 4492760 A. Preferably, the xanthene dye is soluble in an organic solvent.

[0064] As the xanthene dye, commercially available xanthene dyes (for example, "Chugai Aminol Fast Pink RH / C" manufactured by Chugai Chemical Industry Co., Ltd. and "Rhodamin 6G" manufactured by Taoka Chemical Co., Ltd.) can also be used. In addition, the xanthene dye can also be synthesized using a commercially available xanthene dye as a starting material with reference to JP-A-2010-32999.

[0065] As dyes other than xanthene dyes, azo dyes, cyanine dyes, triphenylmethane dyes, thiazole dyes, oxazine dyes, phthalocyanine dyes, quinophthalone dyes, anthraquinone dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, azomethine dyes, squarylium dyes, acridine dyes, styryl dyes, coumarin dyes, quinoline dyes, nitro dyes, etc. As the dyes other than xanthene dyes, known dyes can be used.

[0066] Specific examples of dyes other than xanthene dyes include CI Solvent Yellow 4 (hereinafter, the term CI Solvent Yellow will be omitted and only the number will be used. Other similar expressions may also be referred to by only the number.), 14, 15, 23, 24, 38, 62, 63, 68, 82, 94, 98, 99, 117, 162, 163, 167, and 189; CI Solvent Red 45, 49, 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, 67, 68, 69, 70, 78, 79, 83, 90, 94, 97, 98, 100, 101, 102, 104, 105, 111, 112, 122, 128, 132, 136, 139; CI solvent dyes such as CI Solvent Green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, and 35; CI Acid Yellow 1, 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112, 113, 114, 116, 119, 123, 128, 134, 135, 138, 139, 140, 144, 150, 155, 157, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251; CI Acid Red 1, 4, 8, 14, 17, 18, 26, 27, 29, 31, 33, 34, 35, 37, 40, 42, 44, 50, 57, 66, 73, 76, 80, 88, 91, 95, 97, 98, 103, 106, 111, 114, 129, 133, 134, 138, 143, 145, 150, 151, 155, 158, 160, 172, 176, 182, 183, 184, 185, 186, 187, 188, 189, 190, 191, 192, 193, 194, 195, 196, 197, 198, 199, 200, 201, 202, 203, 204, 205, 206, 207, 208, 209, 210, 211, 212, 213, 214, 215, 216, 217, 218, 219, 220, 221, 222, 223, 224, 225, 226, 227, 228, 229, 230, 231, 232, 233, 234, 235, 236, 237, 238, 240, 241, 242, 243, 245, 24 83, 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, 120, 121, 122, 123, 124, 125, 126, 127, 128, 129, 130, 131, 132, 133, 134, 135, 136, 137, 138, 139, 140, 141, 142, 143, 144, 145, 146, 147, 148, 149, 150, 151, 152, 153, 154, 155, 156, 157, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 168, 169, 170, 1 23, 126, 127, 129, 130, 131, 138, 140, 142, 143, 147, 150, 151, 154, 158, 161, 166, 167, 168, 170, 171, 175, 182, 183, 184, 187, 192, 199, 203, 204, 205, 210, 213, 229, 234, 236, 242, 243, 256, 259, 267, 269, 278, 280, 285, 290, 296, 315, 324, 335, 340; CI Acid Dyes such as CI Acid Green 1, 3, 5, 6, 7, 8, 9, 11, 13, 14, 15, 16, 22, 25, 27, 28, 41, 50, 50:1, 58, 63, 65, 80, 104, 105, 106, 109, CI Direct Yellow 2, 33, 34, 35, 38, 39, 43, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129, 136, 138, 141; CI Direct Red 79, 82, 83, 84, 91, 92, 96, 97, 98, 99, 105, 106, 107, 172, 173, 176, 177, 179, 181, 182, 184, 204, 207, 211, 213, 218, 220, 221, 222, 232, 233, 234, 241, 243, 246, 250; CI Direct Orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107; CI Direct Violet 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104; CI Direct Blue 1, 2, 3, 6, 8, 15, 22, 25, 28, 29, 40, 41, 42, 47, 52, 55, 57, 71, 76, 77, 78, 80, 81, 84, 85, 86, 90, 93, 94, 95, 97, 98, 99, 100, 101, 106, 107, 108, 109, 113, 114, 115, 117, 119, 120, 137, 149, 150, 153, 155, 156, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 168, 170, 171, 172, 173, 188, 189, 190, 192, 193, 194, 195, 196, 198, 199, 200, 201, 202, 203, 207, 209, 210, 212, 213, 214, 222, 225, 226, 228, 229, 236, 237, 238, 242, 243, 244, 245, 246, 247, 248, 249, 250, 251, 252, 256, 257, 259, 260, 268, 274, 275, 293; CI Direct dyes such as CI Direct Green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 77, 79, and 82; CI Disperse Yellow 51, 54, 76; CI Disperse Violet 26, 27; CI Disperse dyes such as CI Disperse Blue 1, 14, 56, and 60, 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 dyes such as CI Basic Green 1, CI Reactive Yellow 2, 76, 116; CI Reactive Orange 16; CI reactive dyes such as CI Reactive Red 36, CI Mordant Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65; CI Mordant Red 1, 2, 3, 4, 9, 11, 12, 14, 17, 18, 19, 22, 23, 24, 25, 26, 29, 30, 32, 33, 36, 37, 38, 39, 41, 42, 43, 45, 46, 48, 52, 53, 56, 62, 63, 71, 74, 76, 78, 85, 86, 88, 90, 94, 95; CI Mordant Orange 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47, 48; CI Mordant Violet 1, 1:1, 2, 3, 4, 5, 6, 7, 8, 10, 11, 14, 15, 16, 17, 18, 19, 21, 22, 23, 24, 27, 28, 30, 31, 32, 33, 36, 37, 39, 40, 41, 44, 45, 47, 48, 49, 53, 58; CI Mordant Blue 1, 2, 3, 7, 8, 9, 12, 13, 15, 16, 19, 20, 21, 22, 23, 24, 26, 30, 31, 32, 39, 40, 41, 43, 44, 48, 49, 53, 61, 74, 77, 83, 84; CI Mordant dyes such as CI Mordant Green 1, 3, 4, 5, 10, 13, 15, 19, 21, 23, 26, 29, 31, 33, 34, 35, 41, 43, and 53; Examples include CI Vat dyes such as CI Vat Green 1.

[0067] Examples of pigments include those classified as pigments in the Color Index (published by The Society of Dyers and Colourists). Examples of such pigments include the following pigments:

[0068] Green pigments: CI Pigment Green 7, 36, 58, 59, 62, 63, 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, 123, 144, 149, 166, 168, 176, 177, 180, 192, 209, 215, 216, 224, 242, 254, 255, 264, 265, 272, 291, etc. Blue pigments: CI Pigment Blue 15, 15:3, 15:4, 15:6, 60, etc. Purple pigments: CI Pigment Violet 1, 19, 23, 29, 32, 36, 38, etc. Black pigment: CI Pigment Black 1, 7, 31, 32, etc.

[0069] One or more of these pigments may be used for each color, or pigments of each color may be combined.

[0070] The colorant (A2) is preferably one or more pigments, more preferably two or more pigments, even more preferably two or more pigments selected from the group consisting of orange pigments, purple pigments, blue pigments, and black pigments, and particularly preferably a combination of an orange pigment, a purple pigment, and a blue pigment, or a combination of a blue pigment and a black pigment.

[0071] The pigment may be subjected to, as necessary, rosin treatment; surface treatment using a pigment derivative or the like into which an acidic or basic group has been introduced; grafting treatment onto the pigment surface with a polymer compound or the like; atomization treatment using a sulfuric acid atomization method or the like; washing treatment with an organic solvent, water, or the like to remove impurities; or treatment to remove ionic impurities using an ion exchange method or the like. The pigment particle size is preferably approximately uniform. By adding a pigment dispersant and performing a dispersion treatment, the pigment can be made into a pigment dispersion in which the pigment is uniformly dispersed in the pigment dispersant solution. The pigments may be dispersed individually or in a mixture of multiple types.

[0072] Examples of pigment dispersants include silicone-based, fluorine-based, ester-based, cationic, anionic, nonionic, amphoteric, polyester-based, polyamine-based, and acrylic surfactants. Examples of surfactants include polyoxyethylene alkyl ethers, polyoxyethylene alkylphenyl ethers, polyethylene glycol diesters, sorbitan fatty acid esters, fatty acid-modified polyesters, tertiary amine-modified polyurethanes, and polyethyleneimines. Examples of commercially available surfactants include KP (manufactured by Shin-Etsu Chemical Co., Ltd.), FLOWRENE (manufactured by Kyoeisha Chemical Co., Ltd.), Solsperse (manufactured by Zeneca Corporation), EFKA (manufactured by BASF Japan Ltd.), AJISPER (registered trademark) (manufactured by Ajinomoto Fine-Techno Co., Ltd.), and Disperbyk (manufactured by BYK-Chemie).

[0073] 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, relative to 100 parts by mass of the pigment. When the amount of the pigment dispersant used is within the above range, a pigment dispersion in a more uniformly dispersed state tends to be obtained when two or more pigments are used.

[0074] The content of the colorant (A2) is preferably 0 to 90 mass %, more preferably 0 to 80 mass %, and even more preferably 0 to 70 mass %, based on the total amount of the colorant (A).

[0075] The content of colorant (A) is preferably 1 to 60 mass%, more preferably 3 to 50 mass%, and even more preferably 5 to 40 mass%, based on the total amount of solids in the resin composition. When the content of colorant (A) is within the above range, it tends to be easier to obtain the desired spectral response and color density. In this specification, the "total amount of solids in the resin composition" refers to the total amount of components in the resin composition excluding the solvent. The total amount of solids in the resin composition and the content of each component relative to the total amount can be measured by known analytical means, such as liquid chromatography or gas chromatography.

[0076] <Resin (B)> Resin (B) is preferably an alkali-soluble resin, such as the following resins [K1] to [K6]. Resin [K1]: A copolymer having structural units derived from at least one member (a) (hereinafter sometimes referred to as "(a)") selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic acid anhydrides, and structural units derived from a monomer (b) (hereinafter sometimes referred to as "(b)") having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond. Resin [K2]: A copolymer having structural units derived from (a), structural units derived from (b), and structural units derived from a monomer (c) copolymerizable with (a) (however, different from (a) and (b)) (hereinafter, sometimes referred to as "(c)"). Resin [K3]: A copolymer having structural units derived from (a) and structural units derived from (c) Resin [K4]: A copolymer having a structural unit derived from (a) plus (b) and a structural unit derived from (c). Resin [K5]: A copolymer having a structural unit in which (a) is added to a structural unit derived from (b) and a structural unit derived from (c). Resin [K6]: A copolymer having a structural unit obtained by adding (a) to a structural unit derived from (b) and further adding a carboxylic acid anhydride, and a structural unit derived from (c).

[0077] Specific examples of (a) include unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, o-, m-, and p-vinylbenzoic acid; Unsaturated dicarboxylic acids such as maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyltetrahydrophthalic acid, and 1,4-cyclohexenedicarboxylic acid; bicyclounsaturated compounds containing a carboxy group, such as methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo[2.2.1]hept-2-ene, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene, 5-carboxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-carboxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-carboxy-6-methylbicyclo[2.2.1]hept-2-ene, and 5-carboxy-6-ethylbicyclo[2.2.1]hept-2-ene; unsaturated dicarboxylic acid anhydrides such as maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, and 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride; Unsaturated mono[(meth)acryloyloxyalkyl] esters of divalent or higher polyvalent carboxylic acids, such as mono[2-(meth)acryloyloxyethyl] succinate and mono[2-(meth)acryloyloxyethyl] phthalate; Examples include unsaturated acrylates containing a hydroxy group and a carboxy group in the same molecule, such as α-(hydroxymethyl)acrylic acid.

[0078] Of these, (a) is preferably acrylic acid, methacrylic acid or maleic anhydride from the viewpoint of copolymerization reactivity and solubility of the resulting resin in an alkaline aqueous solution.

[0079] (b) may be, for example, a polymerizable compound having a cyclic ether structure having 2 to 4 carbon atoms (for example, at least one selected from the group consisting of an oxirane ring, an oxetane ring, and a tetrahydrofuran ring) and an ethylenically unsaturated bond. (b) is preferably a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth)acryloyloxy group.

[0080] Examples of (b) include a monomer (b1) having an oxiranyl group and an ethylenically unsaturated bond (hereinafter, sometimes referred to as "(b1)"), a monomer (b2) having an oxetanyl group and an ethylenically unsaturated bond (hereinafter, sometimes referred to as "(b2)"), and a monomer (b3) having a tetrahydrofuryl group and an ethylenically unsaturated bond (hereinafter, sometimes referred to as "(b3)").

[0081] Examples of (b1) include a monomer (b1-1) (hereinafter, sometimes referred to as "(b1-1)") having a structure in which a linear or branched aliphatic unsaturated hydrocarbon has been epoxidized, and a monomer (b1-2) (hereinafter, sometimes referred to as "(b1-2)") having a structure in which an alicyclic unsaturated hydrocarbon has been epoxidized.

[0082] Examples of (b1-1) include glycidyl (meth)acrylate, β-methylglycidyl (meth)acrylate, β-ethylglycidyl (meth)acrylate, glycidyl vinyl ether, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether, α-methyl-o-vinylbenzyl glycidyl ether, α-methyl-m-vinylbenzyl glycidyl ether, α-methyl-p-vinylbenzyl glycidyl ether, 2,3-bis(glycidyl Examples of such styrene include 2,4-bis(glycidyloxymethyl)styrene, 2,5-bis(glycidyloxymethyl)styrene, 2,6-bis(glycidyloxymethyl)styrene, 2,3,4-tris(glycidyloxymethyl)styrene, 2,3,5-tris(glycidyloxymethyl)styrene, 2,3,6-tris(glycidyloxymethyl)styrene, 3,4,5-tris(glycidyloxymethyl)styrene, and 2,4,6-tris(glycidyloxymethyl)styrene.

[0083] Examples of (b1-2) include vinylcyclohexene monoxide, 1,2-epoxy-4-vinylcyclohexane (e.g., Celloxide 2000 (manufactured by Daicel Corporation)), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., Cyclomer A400 (manufactured by Daicel Corporation)), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., Cyclomer M100 (manufactured by Daicel Corporation)), 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl (meth)acrylate (3,4-epoxytricyclo[5.2.1.0 2,6 ] decan-8-yl (meth)acrylate, 3,4-epoxytricyclo[5.2.1.0 2,6 ]decan-9-yl(meth)acrylate, etc.), 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyloxyethyl (meth)acrylate, and the like.

[0084] (b2) is more preferably a monomer having an oxetanyl group and a (meth)acryloyloxy group. Examples of (b2) include 3-methyl-3-methacryloyloxymethyloxetane, 3-methyl-3-acryloyloxymethyloxetane, 3-ethyl-3-methacryloyloxymethyloxetane, 3-ethyl-3-acryloyloxymethyloxetane, 3-methyl-3-methacryloyloxyethyloxetane, 3-methyl-3-acryloyloxyethyloxetane, 3-ethyl-3-methacryloyloxyethyloxetane, and 3-ethyl-3-acryloyloxyethyloxetane.

[0085] (b3) is more preferably a monomer having a tetrahydrofuryl group and a (meth)acryloyloxy group. Examples of (b3) include tetrahydrofurfuryl acrylate (for example, Viscoat V#150 (manufactured by Osaka Organic Chemical Industry Ltd.)), tetrahydrofurfuryl methacrylate, etc.

[0086] (b) is preferably (b1) in that it can further increase the reliability of the obtained optical filter in terms of heat resistance, chemical resistance, etc. Furthermore, (b) is more preferably (b1-2) in that the storage stability of the resin composition is excellent.

[0087] Examples of (c) include methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, sec-butyl (meth)acrylate, tert-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, dodecyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, cyclopentyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, tricyclo[5.2.1.0] 2,6 ]decan-8-yl(meth)acrylate (commonly known in the art as "dicyclopentanyl(meth)acrylate" and sometimes as "tricyclodecyl(meth)acrylate"), tricyclo[5.2.1.02,6 (meth)acrylic acid esters such as ]decen-8-yl (meth)acrylate (commonly known as "dicyclopentenyl (meth)acrylate" in the technical field), dicyclopentanyloxyethyl (meth)acrylate, isobornyl (meth)acrylate, adamantyl (meth)acrylate, allyl (meth)acrylate, propargyl (meth)acrylate, phenyl (meth)acrylate, naphthyl (meth)acrylate, and benzyl (meth)acrylate; hydroxy group-containing (meth)acrylic acid esters such as 2-hydroxyethyl (meth)acrylate and 2-hydroxypropyl (meth)acrylate; dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate, and diethyl itaconate; Bicyclo[2.2.1]hept-2-ene, 5-methylbicyclo[2.2.1]hept-2-ene, 5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxybicyclo[2.2.1]hept-2-ene, 5-hydroxymethylbicyclo[2.2.1]hept-2-ene, 5-(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5-methoxybicyclo[2.2.1]hept-2-ene Bicyclo[2.2.1]hept-2-ene, 5-ethoxybicyclo[2.2.1]hept-2-ene, 5,6-dihydroxybicyclo[2.2.1]hept-2-ene, 5,6-di(hydroxymethyl)bicyclo[2.2.1]hept-2-ene, 5,6-di(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5,6-dimethoxybicyclo[2.2.1]hept -2-ene, 5,6-diethoxybicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxymethyl-5-methylbicyclo[2.2.1]hept-2-ene, 5-tert-butoxycarbonylbicyclo[2.2.1]hept-2-ene bicyclounsaturated compounds such as ene, 5-cyclohexyloxycarbonylbicyclo[2.2.1]hept-2-ene, 5-phenoxycarbonylbicyclo[2.2.1]hept-2-ene, 5,6-bis(tert-butoxycarbonyl)bicyclo[2.2.1]hept-2-ene, and 5,6-bis(cyclohexyloxycarbonyl)bicyclo[2.2.1]hept-2-ene; dicarbonyl imide derivatives such as N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimidobenzoate, N-succinimidyl-4-maleimidobutyrate, N-succinimidyl-6-maleimidocaproate, N-succinimidyl-3-maleimidopropionate, and N-(9-acridinyl)maleimide; Examples include styrene, α-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, p-methoxystyrene, acrylonitrile, methacrylonitrile, vinyl chloride, vinylidene chloride, acrylamide, methacrylamide, vinyl acetate, 1,3-butadiene, isoprene, and 2,3-dimethyl-1,3-butadiene.

[0088] Among these, in terms of copolymerization reactivity and heat resistance, (c) is preferably styrene, vinyltoluene, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, or bicyclo[2.2.1]hept-2-ene.

[0089] In the resin [K1], the ratio of the structural units derived from each of these is as follows: Structural units derived from (a): 2 to 60 mol% Structural units derived from (b): 40 to 98 mol% It is preferred that Structural units derived from (a): 10 to 50 mol% Structural units derived from (b): 50 to 90 mol% It is more preferable that:

[0090] When the ratio of the structural units in the resin [K1] is within the above range, the storage stability of the resin composition, the developability when forming a pattern, and the solvent resistance of the resulting optical filter tend to be excellent.

[0091] Resin [K1] can be produced, for example, by referring to the method described in the document "Experimental Methods for Polymer Synthesis" (written by Takayuki Otsu, published by Kagaku Dojin Co., Ltd., 1st edition, 1st printing, published March 1, 1972) and the references cited therein.

[0092] Specifically, a method can be exemplified in which predetermined amounts of (a) and (b), a polymerization initiator, a solvent, and the like are placed in a reaction vessel, and a deoxygenated atmosphere is created, for example, by replacing oxygen with nitrogen, followed by heating and keeping the temperature while stirring. The polymerization initiator, solvent, and the like used here are not particularly limited, and those commonly used in the relevant field can be used. Examples of polymerization initiators include azo compounds (2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), etc.) and organic peroxides (benzoyl peroxide, etc.). Any solvent capable of dissolving each monomer can be used, and examples thereof include those exemplified as solvent (E) described below.

[0093] The resulting copolymer may be used as a solution after the reaction as is, or may be used as a concentrated or diluted solution. The resulting copolymer may also be used after being extracted as a solid (powder) by a method such as reprecipitation. In particular, by using a solvent (E) described below as a solvent during the polymerization, the solution after the reaction can be used to prepare a resin composition, thereby simplifying the manufacturing process of the resin composition of this embodiment.

[0094] In the resin [K2], the ratio of the structural units derived from each of these is as follows: Structural units derived from (a): 2 to 45 mol% Structural units derived from (b): 2 to 95 mol% Structural units derived from (c): 1 to 65 mol% It is preferred that Structural units derived from (a): 5 to 40 mol% Structural units derived from (b): 5 to 80 mol% Structural units derived from (c): 5 to 60 mol% It is more preferable that:

[0095] When the ratio of the structural units of the resin [K2] is within the above range, the storage stability of the resin composition, the developability when forming a pattern, and the solvent resistance, heat resistance, and mechanical strength of the resulting optical filter tend to be excellent.

[0096] Resin [K2] can be produced, for example, in the same manner as described above for producing resin [K1].

[0097] In the resin [K3], the ratio of the structural units derived from each of these is as follows: Structural units derived from (a): 2 to 60 mol% Structural units derived from (c): 40 to 98 mol% It is preferred that Structural units derived from (a): 10 to 50 mol% Structural units derived from (c): 50 to 90 mol% It is more preferable that:

[0098] Resin [K3] can be produced, for example, in the same manner as described above for producing resin [K1].

[0099] Resin [K4] can be produced by obtaining a copolymer of (a) and (c), and then adding the cyclic ether having 2 to 4 carbon atoms contained in (b) to the carboxylic acid and / or carboxylic acid anhydride contained in (a).

[0100] First, a copolymer of (a) and (c) is produced in the same manner as described for the production of resin [K1]. In this case, the ratio of the structural units derived from each is preferably the same as that exemplified for resin [K3].

[0101] 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 contained in (b). Following the production of the copolymer of (a) and (c), the nitrogen atmosphere in the flask is replaced with air, and (b), a reaction catalyst for the carboxylic acid or carboxylic acid anhydride with the cyclic ether (e.g., tris(dimethylaminomethyl)phenol), a polymerization inhibitor (e.g., hydroquinone), etc. are placed in the flask, and the reaction is carried out, for example, at 60 to 130°C for 1 to 10 hours to produce resin [K4].

[0102] The amount of (b) used is preferably 5 to 80 mol, more preferably 10 to 75 mol, per 100 mol of (a). This range tends to improve the storage stability of the resin composition, the developability during pattern formation, and the balance of the solvent resistance, heat resistance, mechanical strength, and sensitivity of the resulting pattern. Because the reactivity of cyclic ethers is high and unreacted (b) is unlikely to remain, (b) used in resin [K4] is preferably (b1), and more preferably (b1-1).

[0103] The amount of the reaction catalyst used is preferably 0.001 to 5 parts by mass per 100 parts by mass of the total 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 of (a), (b), and (c).

[0104] The reaction conditions such as the charging method, reaction temperature and time can be appropriately adjusted taking into consideration the production equipment, the amount of heat generated by polymerization, and the like.

[0105] Resin [K5] is prepared in the first step by obtaining a copolymer of (b) and (c) in the same manner as in the production method for resin [K1] described above. As described above, the resulting copolymer may be used as a solution after the reaction, or a concentrated or diluted solution. Alternatively, the resulting copolymer may be extracted as a solid (powder) by a method such as reprecipitation.

[0106] The ratios of the structural units derived from (b) and (c) to the total number of moles of all structural units constituting the copolymer are as follows: Structural units derived from (b): 5 to 95 mol% Structural units derived from (c): 5 to 95 mol% It is preferred that Structural units derived from (b): 10 to 90 mol% Structural units derived from (c): 10 to 90 mol% It is more preferable that:

[0107] Furthermore, under the same conditions as in the production method of resin [K4], resin [K5] can be obtained by reacting the cyclic ether derived from (b) contained in the copolymer of (b) and (c) with the carboxylic acid or carboxylic anhydride contained in (a).

[0108] The amount of (a) used to react with the above copolymer is preferably 5 to 80 moles per 100 moles of (b). Because the reactivity of cyclic ethers is high and unreacted (b) is unlikely to remain, (b) used in resin [K5] is preferably (b1), and more preferably (b1-1).

[0109] Resin [K6] is a resin obtained by further reacting resin [K5] with a carboxylic acid anhydride. The hydroxyl group generated by the reaction of a cyclic ether with a carboxylic acid or a carboxylic acid anhydride is reacted with the carboxylic acid anhydride.

[0110] Examples of the carboxylic acid anhydride include maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride, etc. The amount of the carboxylic acid anhydride used is preferably 0.5 to 1 mole per mole of the amount of (a) used.

[0111] Specific examples of the resin (B) include 3,4-epoxycyclohexylmethyl (meth)acrylate / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] Decyl acrylate / (meth)acrylic acid copolymer and other resins [K1]; glycidyl (meth)acrylate / benzyl (meth)acrylate / (meth)acrylic acid copolymer, glycidyl (meth)acrylate / styrene / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6] Decyl acrylate / (meth)acrylic acid / benzyl (meth)acrylate, 3,4-epoxytricyclo[5.2.1.0 2,6 ] Decyl acrylate / (meth)acrylic acid / N-cyclohexylmaleimide copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl acrylate / (meth)acrylic acid / N-cyclohexylmaleimide / 2-hydroxyethyl (meth)acrylate copolymer, 3-methyl-3-(meth)acryloyloxymethyloxetane / (meth)acrylic acid / styrene copolymer, etc. [K2]; benzyl (meth)acrylate / (meth)acrylic acid copolymer, styrene / (meth)acrylic acid copolymer, etc. [K3]; resin obtained by adding glycidyl (meth)acrylate to benzyl (meth)acrylate / (meth)acrylic acid copolymer, resin obtained by adding glycidyl (meth)acrylate to tricyclodecyl (meth)acrylate / styrene / (meth)acrylic acid copolymer, tricyclodecyl ( Resins such as [K4] in which glycidyl (meth)acrylate is added to a (meth)acrylate copolymer; resins such as [K5] in which a tricyclodecyl (meth)acrylate / glycidyl (meth)acrylate copolymer is reacted with (meth)acrylic acid, and resins such as [K6] in which a tricyclodecyl (meth)acrylate / glycidyl (meth)acrylate copolymer is reacted with (meth)acrylic acid and then further reacted with tetrahydrophthalic anhydride;

[0112] Resin (B) is preferably a copolymer containing at least a structural unit derived from at least one selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic acid anhydrides, and a structural unit having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond, more preferably resin [K1] or resin [K2], and even more preferably resin [K2].

[0113] The polystyrene-equivalent weight-average molecular weight of resin (B) is preferably 3,000 to 100,000, more preferably 5,000 to 50,000, and even more preferably 5,000 to 30,000. When the weight-average molecular weight is within the above range, the hardness of the optical filter is improved, the residual film rate is high, the solubility of the unexposed areas in the developer is good, and the pattern resolution tends to be improved.

[0114] The polydispersity of the resin (B) [weight average molecular weight (Mw) / number average molecular weight (Mn)] is preferably 1.1-6, more preferably 1.2-4.

[0115] The acid value of the 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, calculated as solid content. Here, the acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of the resin (B), and can be determined, for example, by titration with an aqueous potassium hydroxide solution.

[0116] The content of resin (B) is preferably 5 to 60 mass %, more preferably 10 to 55 mass %, and even more preferably 20 to 50 mass %, based on the total amount of solids in the resin composition. When the content of resin (B) is within the above range, a pattern can be formed, and the resolution and residual film rate of the pattern tend to be improved.

[0117] <Polymerizable compound (C)> The polymerizable compound (C) is a compound that can be polymerized by active radicals and / or acids generated from the polymerization initiator (D). Examples of the polymerizable compound (C) include compounds having a polymerizable ethylenically unsaturated bond. The polymerizable compound (C) is preferably a (meth)acrylic acid ester compound.

[0118] The polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds. Examples of such polymerizable compounds include trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, tripentaerythritol octa(meth)acrylate, tripentaerythritol hepta(meth)acrylate, tetrapentaerythritol deca(meth)acrylate, tetrapentaerythritol nona(meth)acrylate, tri(meth)acrylate, tetra ... Examples of the polymerizable compound (C) include trimethylolpropane triacrylate, dipentaerythritol penta(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, the polymerizable compound (C) is preferably trimethylolpropane triacrylate, dipentaerythritol penta(meth)acrylate, or dipentaerythritol hexa(meth)acrylate.

[0119] The molecular weight or weight average molecular weight of the polymerizable compound (C) is preferably 150 to 2,900, more preferably 250 to 1,500.

[0120] The content of the polymerizable compound (C) is preferably 5 to 60 mass %, more preferably 10 to 50 mass %, and even more preferably 20 to 40 mass %, based on the total amount of solids in the resin composition. When the content of the polymerizable compound (C) is within the above range, the residual film rate during pattern formation and the chemical resistance of the optical filter tend to be improved.

[0121] <Polymerization initiator (D)> The polymerization initiator (D) is not particularly limited as long as it is a compound that can generate active radicals, acids, etc. by the action of light or heat and initiate polymerization, and known polymerization initiators can be used. Examples of polymerization initiators that generate active radicals include O-acyloxime compounds, alkylphenone compounds, triazine compounds, acylphosphine oxide compounds, and biimidazole compounds.

[0122] An O-acyloxime compound is a compound having a partial structure represented by formula (d1). Hereinafter, * represents a bond.

[0123] [ka]

[0124] Examples of the O-acyloxime compound include N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethan-1-imine, N-acetoxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethyl N-acetyl-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethan-1-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropan-1-imine, N-benzoyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropan-1-one-2-imine, N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine, and the like. As the O-acyloxime compound, commercially available products such as Irgacure (registered trademark, hereinafter the same) OXE01 (N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine), Irgacure OXE02 (N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethan-1-imine) (both manufactured by BASF), and N-1919 (manufactured by ADEKA Corporation) may be used.

[0125] Among these, O-acyloxime compounds include N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethan-1-imine, and N-benzoyloxy-1-( Preferably, the O-acyl oxime compound is at least one selected from the group consisting of N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine, or N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethan-1-imine. The use of such O-acyl oxime compounds tends to result in optical filters with high brightness.

[0126] The alkylphenone compound is a compound having a partial structure represented by formula (d2) or (d3). In these partial structures, the benzene ring may have a substituent.

[0127] [ka]

[0128] Examples of compounds having a partial structure represented by formula (d2) include 2-methyl-2-morpholino-1-(4-methylsulfanylphenyl)propan-1-one, 2-dimethylamino-1-(4-morpholinophenyl)-2-benzylbutan-1-one, 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]butan-1-one, etc. As compounds having a partial structure represented by formula (d2), commercially available products such as Irgacure 369, 907, and 379 (all manufactured by BASF) may also be used.

[0129] Examples of compounds having a partial structure represented by formula (d3) include 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy)phenyl]propan-1-one, 1-hydroxycyclohexyl phenyl ketone, oligomers of 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propan-1-one, α,α-diethoxyacetophenone, and benzyl dimethyl ketal.

[0130] In terms of sensitivity, the alkylphenone compound is preferably a compound having a partial structure represented by formula (d2).

[0131] Examples of the triazine compound include 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxynaphthyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxystyryl)-1,3,5-triazine, and 2,4-bis(trichloromethyl)-6-[2 -(5-methylfuran-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)ethenyl]-1,3,5-triazine, and the like.

[0132] Examples of the acylphosphine oxide compound include 2,4,6-trimethylbenzoyldiphenylphosphine oxide, etc. Commercially available acylphosphine oxide compounds such as Irgacure 819 (manufactured by BASF) may also be used.

[0133] Examples of the biimidazole compound include 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3-dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole (see, for example, JP-A-6-75372 and JP-A-6-75373), 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(alkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(alkoxyphenyl)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, JP-B No. 48-38403 and JP-A No. 62-174204), and biimidazole compounds in which the phenyl groups at the 4,4',5,5'-positions are substituted with carboalkoxy groups (see, for example, JP-A No. 7-10913).

[0134] Further examples of the polymerization initiator (D) include benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether; benzophenone compounds such as benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, 3,3',4,4'-tetra(tert-butylperoxycarbonyl)benzophenone, and 2,4,6-trimethylbenzophenone; quinone compounds such as 9,10-phenanthrenequinone, 2-ethylanthraquinone, and camphorquinone; 10-butyl-2-chloroacridone, benzyl, methyl phenylglyoxylate, and titanocene compounds. These are preferably used in combination with the polymerization initiator aid (D1) (especially amines) described below.

[0135] Examples of the polymerization initiator that generates an acid include onium salts such as 4-hydroxyphenyldimethylsulfonium p-toluenesulfonate, 4-hydroxyphenyldimethylsulfonium hexafluoroantimonate, 4-acetoxyphenyldimethylsulfonium p-toluenesulfonate, 4-acetoxyphenylmethylbenzylsulfonium hexafluoroantimonate, triphenylsulfonium p-toluenesulfonate, triphenylsulfonium hexafluoroantimonate, diphenyliodonium p-toluenesulfonate, and diphenyliodonium hexafluoroantimonate; nitrobenzyl tosylates; and benzoin tosylates.

[0136] The polymerization initiator (D) is preferably a polymerization initiator containing at least one selected from the group consisting of O-acyloxime compounds, alkylphenone compounds, triazine compounds, acylphosphine oxide compounds, and biimidazole compounds, and more preferably a polymerization initiator containing an O-acyloxime compound.

[0137] The content of the polymerization initiator (D) is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, relative to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). When the content of the polymerization initiator (D) is within the above range, sensitivity tends to be increased and exposure time tends to be shortened, so that improvement in productivity of the optical filter can be expected.

[0138] <Polymerization initiator aid (D1)> The polymerization initiation aid (D1) is a compound or sensitizer used to promote the polymerization of a polymerizable compound. When the resin composition contains the polymerization initiation aid (D1), it is usually used in combination with the polymerization initiator (D).

[0139] Examples of the polymerization initiation aid (D1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds, and carboxylic acid compounds.

[0140] Examples of the amine compound include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 2-ethylhexyl 4-dimethylaminobenzoate, N,N-dimethyl-p-toluidine, 4,4'-bis(dimethylamino)benzophenone (commonly known as Michler's ketone), 4,4'-bis(diethylamino)benzophenone, and 4,4'-bis(ethylmethylamino)benzophenone. Commercially available amine compounds, such as EAB-F (manufactured by Hodogaya Chemical Co., Ltd.), may also be used. Among these, the amine compound is preferably 4,4'-bis(diethylamino)benzophenone.

[0141] Examples of the alkoxyanthracene compound include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene, 9,10-dibutoxyanthracene, and 2-ethyl-9,10-dibutoxyanthracene.

[0142] Examples of thioxanthone compounds include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, and 1-chloro-4-propoxythioxanthone.

[0143] Examples of the carboxylic acid compound include phenylsulfanylacetic acid, methylphenylsulfanylacetic acid, ethylphenylsulfanylacetic acid, methylethylphenylsulfanylacetic acid, dimethylphenylsulfanylacetic acid, methoxyphenylsulfanylacetic acid, dimethoxyphenylsulfanylacetic acid, chlorophenylsulfanylacetic acid, dichlorophenylsulfanylacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, and naphthoxyacetic acid.

[0144] When these polymerization initiation aids (D1) are used, the content thereof is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, relative to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). When the amount of the polymerization initiation aid (D1) is within this range, patterns can be formed with even higher sensitivity, and the productivity of optical filters tends to improve.

[0145] <Solvent (E)> The solvent (E) is not particularly limited, and a solvent commonly used in the art can be used. Examples thereof include ester solvents (solvents containing -COO- but not -O- in the molecule), ether solvents (solvents containing -O- but not -COO- in the molecule), ether ester solvents (solvents containing -COO- and -O- in the molecule), ketone solvents (solvents containing -CO- but not -COO- in the molecule), alcohol solvents (solvents containing OH in the molecule but not -O-, -CO-, or -COO-), aromatic hydrocarbon solvents, amide solvents, dimethyl sulfoxide, etc.

[0146] 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.

[0147] Examples of the ether solvent include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenetole, and methylanisole.

[0148] Ether ester solvents include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methyl ...propionate, methyl 2-ethoxypropionate, methyl 2-ethoxypropionate, methyl 2-ethoxypropionate, methyl 2-ethoxypropionate, methyl 2-ethoxypropionate, methyl 2-ethoxypropionate, methyl Examples of the alkyl ether acetate include ethyl 2-methoxypropionate, 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.

[0149] 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.

[0150] Examples of alcohol solvents include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerin.

[0151] Examples of aromatic hydrocarbon solvents include benzene, toluene, xylene, and mesitylene.

[0152] Examples of the amide solvent include N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.

[0153] Among these, the solvent (E) is preferably at least one selected from the group consisting of ether ester solvents and ether solvents, and more preferably propylene glycol monomethyl ether acetate or diethylene glycol ethyl methyl ether.

[0154] The content of the solvent (E) is preferably 70 to 95% by mass, more preferably 75 to 92% by mass, based on the total amount of the resin composition. In other words, the content of the solid content of the resin composition is preferably 5 to 30% by mass, more preferably 8 to 25% by mass, based on the total amount of the resin composition. When the content of the solvent (E) is within the above range, the flatness during application is good, and when an optical filter is formed, the color density is less likely to be insufficient, which tends to result in good display characteristics.

[0155] When an ether ester solvent is used, the content of the ether ester solvent is preferably 10 to 100 mass %, more preferably 15 to 90 mass %, and even more preferably 17 to 80 mass %, based on the total amount of solvents.

[0156] When an ether solvent is used, the content of the ether solvent is preferably 20 to 90 mass %, more preferably 30 to 85 mass %, and even more preferably 40 to 80 mass %, based on the total amount of the solvent.

[0157] <Leveling Agent (F)> Examples of the leveling agent (F) include silicone surfactants, fluorine surfactants, silicone surfactants containing fluorine atoms, etc. These may have a polymerizable group in the side chain.

[0158] Examples of silicone surfactants include surfactants having a siloxane bond in the molecule, such as Toray Silicone DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, SH29PA, SH30PA, and SH8400 (trade names, manufactured by Dow Corning Toray Co., Ltd.), KP321, KP322, KP323, KP324, KP326, KP340, and KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), and TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452, and TSF4460 (manufactured by Momentive Performance Materials Japan, LLC).

[0159] Examples of fluorine-based surfactants include surfactants having a fluorocarbon chain in the molecule, such as Fluorad (registered trademark) FC430 and FC431 (manufactured by Sumitomo 3M Limited), Megafac (registered trademark) F142D, F171, F172, F173, F177, F183, F554, R30, and RS-718-K (manufactured by DIC Corporation), Ftop (registered trademark) EF301, EF303, EF351, and EF352 (manufactured by Mitsubishi Materials Electronic Chemicals Co., Ltd.), Surflon (registered trademark) S381, S382, SC101, and SC105 (manufactured by AGC Corporation (formerly Asahi Glass Co., Ltd.)), and E5844 (manufactured by Daikin Fine Chemicals Research Institute, Ltd.).

[0160] Examples of silicone surfactants having fluorine atoms include surfactants having a siloxane bond and a fluorocarbon chain in the molecule, such as Megafac (registered trademark) R08, BL20, F475, F477, and F443 (manufactured by DIC Corporation).

[0161] The content of the leveling agent (F) is preferably 0.001 to 0.2 mass%, more preferably 0.002 to 0.1 mass%, and even more preferably 0.01 to 0.05 mass%, based on the total amount of the resin composition. 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 optical filter can be improved.

[0162] <Other ingredients> The resin composition of the present embodiment may contain additives known in the technical field, such as dispersants, fillers, other polymer compounds, adhesion promoters, antioxidants, light stabilizers, and chain transfer agents, as necessary.

[0163] The resin composition of the present embodiment can be prepared, for example, by mixing the colorant (A), the resin (B), and the solvent (E), as well as the polymerizable compound (C), the polymerization initiator (D), the leveling agent (F), the polymerization initiation aid (D1), and other components that are used as needed.

[0164] The colorant (A) may be prepared as a dispersion or pigment dispersion containing the colorant (A1). For example, the desired resin composition can be prepared by mixing the remaining components into the dispersion or pigment dispersion to a predetermined concentration.

[0165] When the resin composition contains a dye as the colorant (A2), the dye may be dissolved in advance in part or all of the solvent (E) to prepare a solution. The solution is preferably filtered through a filter with a pore size of about 0.01 to 1 μm.

[0166] After mixing the components of the resin composition, it is preferable to filter the mixture through a filter with a pore size of about 0.01 to 10 μm.

[0167] [Optical filter and its manufacturing method] Methods for producing a pattern from the resin composition of this embodiment include photolithography, inkjet printing, and printing. Among these, the method for producing a pattern is preferably photolithography. The photolithography method is a method in which a resin composition is applied to a substrate, dried to form a coating film, and then exposed and developed through a photomask. In the photolithography method, a cured coating film, which is a cured product of the coating film, can be formed by not using a photomask during exposure and / or not developing. Note that the cured coating film can also be formed by heating the coating film without applying photolithography or the like. The pattern or cured coating film thus formed is the optical filter of this embodiment.

[0168] The film thickness of the optical filter to be produced is not particularly limited and can be adjusted appropriately depending on the purpose, use, etc. The film thickness of the optical filter may be, for example, 0.1 to 30 μm, preferably 0.1 to 20 μm, and more preferably 0.5 to 6 μm.

[0169] Examples of the substrate include glass plates such as quartz glass, borosilicate glass, alumina silicate glass, and silica-coated soda lime glass; resin plates such as polycarbonate, polymethyl methacrylate, and polyethylene terephthalate; silicon substrates; and substrates having a thin film of aluminum, silver, silver / copper / palladium alloy, etc. formed on the substrate. These substrates may have other optical filters (patterns or cured coatings), resin films, transistors, circuits, etc. formed on them.

[0170] The formation of each color pixel by photolithography can be carried out using known or conventional equipment, conditions, etc. The formation of each color pixel by photolithography can be carried out, for example, as follows.

[0171] First, the resin composition is applied onto a substrate, and then dried by heating (pre-baking) and / or drying under reduced pressure to remove volatile components such as solvents, thereby obtaining a smooth coating film.

[0172] Examples of coating methods include spin coating, slit coating, and slit and spin coating. When drying by heating, the temperature 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 drying under reduced pressure, it is preferably performed under a pressure of 50 to 150 Pa at a temperature of 20 to 25°C.

[0173] The thickness of the coating film is not particularly limited and can be appropriately selected depending on the thickness of the desired optical filter.

[0174] The coating film is then exposed to light through a photomask to form a desired pattern. The pattern on the photomask is not particularly limited, and a pattern appropriate for the intended use is used.

[0175] The light source used for exposure is preferably a light source that generates light with a wavelength of 250 to 450 nm. The light source used for exposure may be, for example, one that cuts out light of less than 350 nm using a filter that cuts out this wavelength range, or one that selectively extracts light of around 436 nm, around 408 nm, and around 365 nm using a bandpass filter that extracts these wavelength ranges. Specific examples of light sources used for exposure include mercury lamps, light-emitting diodes, metal halide lamps, and halogen lamps.

[0176] For exposure, it is preferable to use an exposure device such as a mask aligner or stepper, since this allows for uniform irradiation of the entire exposure surface with parallel light and allows for accurate alignment of the photomask with the substrate on which the coating film is formed.

[0177] A pattern is formed on the substrate by bringing the exposed coating film (i.e., the cured coating film) into contact with a developer and developing it. The unexposed areas of the coating film are dissolved in the developer and removed by development. Examples of the developer include aqueous solutions of alkaline compounds such as potassium hydroxide, sodium bicarbonate, sodium carbonate, and tetramethylammonium hydroxide. The concentration of these alkaline compounds in the aqueous solution is preferably 0.01 to 10% by mass, more preferably 0.03 to 5% by mass. The developer may further contain a surfactant.

[0178] Examples of the developing method include a puddle method, a dipping method, a spray method, etc. During development, the substrate may be tilted at any angle. After development, it is preferable to wash the resulting pattern with water.

[0179] The pattern thus obtained is preferably post-baked at a temperature of preferably 150 to 250° C., more preferably 160 to 235° C. The post-baking time is preferably 1 to 120 minutes, more preferably 10 to 60 minutes.

[0180] When no pattern is to be produced, a cured coating film, which is a cured product of the coating film, can also be formed, for example, by forming a coating film from a resin composition and then heating the coating film without exposing it to light. The heating conditions may be, for example, the same conditions as those for post-baking.

[0181] [Solid-state imaging device] The solid-state imaging device of this embodiment includes an optical filter that is a pattern, a cured coating film, or the like.

[0182] The resin composition of the present embodiment can be used to produce, for example, a near-infrared transmission filter, which is useful as a film for use in display devices (e.g., liquid crystal display devices, organic EL devices, electronic paper, etc.) and solid-state imaging devices. [Example]

[0183] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to the following examples, and it is of course possible to carry out the present invention with appropriate modifications within the scope of the above and below spirit, all of which are included within the technical scope of the present invention. In the following, unless otherwise specified, "parts" means "parts by mass" and "%" means "% by mass."

[0184] In the following examples, the structures of the compounds were confirmed by mass spectrometry (LC: Agilent 1200 model, MASS: Agilent LC / MSD6130 model, or MALDI-TOF MS: JEOL JMS-S3000).

[0185] In the following examples, the maximum absorption wavelength was confirmed by ultraviolet-visible-near infrared absorption spectroscopy (V-770 manufactured by JASCO Corporation).

[0186] The polystyrene-equivalent weight average molecular weight (Mw) and number average molecular weight (Mn) of the resin were measured by GPC under the following conditions. Apparatus: HLC-8120GPC (Tosoh Corporation) Column: TSK-GELG2000HXL Column temperature: 40℃ Solvent: tetrahydrofuran Flow rate: 1.0mL / min Solid concentration of the analytical sample: 0.001 to 0.01% by mass Injection volume: 50μL Detector: RI Calibration standard materials: TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Corporation)

[0187] The ratio of the weight average molecular weight and the number average molecular weight (Mw / Mn) calculated in terms of polystyrene obtained above was taken as the dispersity.

[0188] (Synthesis Example 1) <Synthesis of Compound (Ia)> Under a nitrogen atmosphere, 48 parts of 3,6-dihydroxyphthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.), 96 parts of dehydrated pyridine (manufactured by Kanto Chemical Co., Ltd.), and 1,296 parts of methylene chloride (dehydrated product, manufactured by Kanto Chemical Co., Ltd.) were mixed and cooled to −78°C in a dry ice-acetone bath. 211 parts of trifluoromethanesulfonic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) were added dropwise over 30 minutes, ensuring that the temperature in the system did not rise above −50°C. After the addition was completed, the dry ice-acetone bath was removed, and the mixture was allowed to return to room temperature (18–24°C) and stirred at that temperature for 22 hours. The reaction solution was poured into 600 parts of pure water, and liquid-liquid extraction was performed. The separated organic layer was washed successively with 1,000 parts of 1 M hydrochloric acid (manufactured by Kanto Chemical Co., Ltd.), 1,000 parts of ion-exchanged water, and 1,000 parts of saturated saline, and then dehydrated with anhydrous sodium sulfate (manufactured by Kanto Chemical Co., Ltd.). After filtering off the sodium sulfate, the solvent was distilled off, and the crude product was recrystallized from methylene chloride to obtain 53 parts of a colorless crystalline compound represented by formula (Ia) (compound (Ia)) (yield: 42%).

[0189] [ka]

[0190] <Identification of Compound (Ia)> (Mass spectrometry) Ionization mode = ESI + : m / z=[M+H] + 425 Exact Mass: 424

[0191] (Synthesis Example 2) <Synthesis of compound (Ib)> Under a nitrogen atmosphere, 42 parts of compound (Ia) obtained in Synthesis Example 1, 57 parts of potassium carbonate (Kanto Chemical Co., Inc.), and 819 parts of dimethyl sulfoxide (Kanto Chemical Co., Inc., dehydrated product) were mixed and stirred at 23°C for 18 hours. While maintaining the resulting mixture at 40°C or below, 22 parts of thiophenol (Tokyo Chemical Industry Co., Ltd.) were added dropwise over 30 minutes. After the addition was completed, the mixture was stirred at room temperature (18-24°C) for 19 hours. After the reaction was completed, the reaction solution was poured into 15,000 parts of purified water, and liquid-liquid extraction was performed three times using 5,000 parts of methylene chloride. The separated organic layer was dehydrated with anhydrous sodium sulfate (Kanto Chemical Co., Inc.), and the sodium sulfate was filtered off, followed by distillation to remove the solvent. The crude product was purified by silica gel column chromatography (solvent: chloroform) to obtain 17 parts of a compound represented by formula (Ib) (compound (Ib)) as pale yellow crystals (yield: 51%).

[0192] [ka]

[0193] <Identification of compound (Ib)> (Mass spectrometry) Ionization mode = ESI + : m / z=[M+H] + 345 Exact Mass: 344

[0194] (Synthesis Example 3) <Synthesis of Compound (II-a)> Under a nitrogen atmosphere, 10 parts of 2,3-dichloro-5,6-dicyano-p-benzoquinone (Tokyo Chemical Industry Co., Ltd.), 13 parts of sodium hydrosulfite (Fujifilm Wako Pure Chemical Industries, Ltd.), 170 parts of ion-exchanged water, and 170 parts of toluene (Kanto Chemical Co., Ltd.) were mixed and stirred at room temperature (18-24°C) for 1 hour. After the reaction was completed, the precipitated solid was filtered and washed with 30 parts of ice-cooled ion-exchanged water and 30 parts of n-hexane. The crude product was recrystallized from acetone / water to obtain 7.0 parts of a colorless crystalline compound represented by formula (II-a) (compound (II-a)) (yield: 70%).

[0195] [ka]

[0196] <Identification of Compound (II-a)> (Mass spectrometry) Ionization mode = ESI + : m / z=[M+H] + 229 Exact Mass: 228

[0197] (Synthesis Example 4) <Synthesis of Compound (II-b)> Under a nitrogen atmosphere, 30 parts of compound (II-a) obtained in Synthesis Example 3, 54 parts of 1-bromobutane (manufactured by Tokyo Chemical Industry Co., Ltd.), 109 parts of potassium carbonate (manufactured by Kanto Chemical Industry Co., Ltd.), 43 parts of potassium iodide (manufactured by Kanto Chemical Industry Co., Ltd.), and 669 parts of N,N-dimethylformamide (dehydrated product, manufactured by Kanto Chemical Industry Co., Ltd.) were mixed and stirred at 80°C for 3 hours. After completion of the reaction, the mixture was cooled to room temperature (18 to 24°C) and filtered through Celite. After washing with 3,000 parts of ethyl acetate, 1,300 parts of ion-exchanged water was added to the obtained filtrate, and liquid-liquid extraction was performed. The separated organic layer was dehydrated with anhydrous sodium sulfate (manufactured by Kanto Chemical Industry Co., Ltd.), the sodium sulfate was filtered, and the solvent was distilled off. The crude product was purified by silica gel column chromatography (solvent: hexane / chloroform = 1 / 1 (volume / volume)), yielding 33 parts of a colorless crystalline compound represented by formula (II-b) (compound (II-b)) (yield 75%).

[0198] [ka]

[0199] <Identification of Compound (II-b)> (Mass spectrometry) Ionization mode = ESI + : m / z=[M+H] + 348 Exact Mass: 347

[0200] (Synthesis Example 5) <Synthesis of compound (II-c)> Under a nitrogen atmosphere, 18 parts of potassium hydroxide (Kanto Chemical Co., Ltd.), 36 parts of thiophenol (Tokyo Chemical Industry Co., Ltd.), and 78 parts of ion-exchanged water were mixed. A solution consisting of 50 parts of compound (II-b) obtained in Synthesis Example 4 and 588 parts of acetone (dehydrated product, Kanto Chemical Co., Ltd.) was added at 40°C over 30 minutes, and the mixture was stirred at 60°C for 2 hours. 2,000 parts of ethyl acetate and 1,000 parts of ion-exchanged water were added, and liquid-liquid extraction was performed. The separated organic layer was dehydrated with anhydrous sodium sulfate (Kanto Chemical Co., Ltd.), and the sodium sulfate was filtered, and the solvent was distilled off. The crude product was purified by silica gel column chromatography (solvent: chloroform) to obtain 59 parts of a compound represented by formula (II-c) (compound (II-c)) as pale yellow crystals (yield: 83%).

[0201] [ka]

[0202] <Identification of Compound (II-c)> (Mass spectrometry) Ionization mode = ESI + : m / z=[M+H] + 489 Exact Mass: 488

[0203] [Synthesis and Evaluation of Phthalocyanine Compounds] (Example 1-1) <Synthesis of Compound (III-1), Compound (III-2), Compound (III-4), and Mixture A of Compound (III-4)> Under a nitrogen atmosphere, 13 parts of compound (Ib) obtained in Synthesis Example 2, 19 parts of compound (II-c) obtained in Synthesis Example 5, 5 parts of nickel(II) chloride (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.), 25 parts of 1-pentanol (manufactured by Tokyo Chemical Industry Co., Ltd.), and 12 parts of 1,8-diazabicyclo[5,4,0]-7-undecene (manufactured by Tokyo Chemical Industry Co., Ltd.) were mixed and refluxed at 160°C for 7 hours. After completion of the reaction, the reaction solution was cooled to room temperature and poured into 1,000 parts of methanol. The precipitated solid was filtered and washed by decantation twice with 200 parts of ion-exchanged water and twice with 200 parts of methanol, in that order. The crude product was purified by silica gel column chromatography to obtain 20 parts (60% yield) of a mixture A of a compound represented by formula (III-1) (compound (III-1)), a compound represented by formula (III-2) (compound (III-2)), a compound represented by formula (III-3) (compound (III-3)), and a compound represented by formula (III-4) (compound (III-4)) as a gray solid.

[0204] [ka]

[0205] <Identification of Compound (III-1)> (Mass spectrometry) Ionization mode = MALDI-TOF + : m / z=1578 Exact Mass: 1578 <Identification of Compound (III-2) and Compound (III-3)> (Mass spectrometry) Ionization mode = MALDI-TOF + : m / z=1722 Exact Mass: 1722 <Identification of Compound (III-4)> (Mass spectrometry) Ionization mode = MALDI-TOF + : m / z=1866 Exact Mass: 1866

[0206] <Calculation of half-width of maximum absorption wavelength by ultraviolet-visible-near-infrared absorption spectroscopy> A 28 mg / L chloroform solution of mixture A was prepared, and the absorption spectrum was measured to calculate the half-width of the maximum absorption wavelength. The results are shown in Table 1.

[0207] (Example 1-2) <Synthesis of Compound (III-1), Compound (III-2), Compound (III-4), and Mixture B of Compound (III-4)> Compound (III-1), compound (III-2), compound (III-4), and 20 parts of a mixture B of compound (III-4) were obtained as a gray solid (yield 62%) in the same manner as in Example 1-1, except that the amount of compound (Ib) obtained in Synthesis Example 2 was changed from 13 parts to 16 parts, and that the amount of compound (II-c) obtained in Synthesis Example 5 was changed from 19 parts to 15 parts.

[0208] <Identification of Compound (III-1)> (Mass spectrometry) Ionization mode = MALDI-TOF + : m / z=1578 Exact Mass: 1578 <Identification of Compound (III-2) and Compound (III-3)> (Mass spectrometry) Ionization mode = MALDI-TOF + : m / z=1722 Exact Mass: 1722 <Identification of Compound (III-4)> (Mass spectrometry) Ionization mode = MALDI-TOF + : m / z=1866 Exact Mass: 1866

[0209] <Calculation of half-width of maximum absorption wavelength by ultraviolet-visible-near-infrared absorption spectroscopy> A 28 mg / L chloroform solution of mixture B was prepared, and the absorption spectrum was measured to calculate the half-width of the maximum absorption wavelength. The results are shown in Table 1.

[0210] (Comparative Example 1-1) <Synthesis of Compound (IV)> Under a nitrogen atmosphere, 8.6 parts of compound (Ib) obtained in Synthesis Example 2, 0.81 parts of nickel(II) chloride (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.), 808 parts of 1-pentanol (manufactured by Tokyo Chemical Industry Co., Ltd.), and 20 parts of 1,8-diazabicyclo[5,4,0]-7-undecene (manufactured by Tokyo Chemical Industry Co., Ltd.) were mixed and refluxed at 160°C for 7 hours. After completion of the reaction, the reaction solution was cooled to room temperature and poured into 8,000 parts of methanol. The precipitated solid was filtered and washed by decantation twice with 200 parts of ion-exchanged water and twice with 200 parts of methanol. The crude product was purified by silica gel column chromatography to obtain 4.9 parts (yield 55%) of a compound represented by formula (IV) (compound (IV)) as a dark green solid.

[0211] [ka]

[0212] <Identification of Compound (IV)> (Mass spectrometry) Ionization mode = ESI + : m / z=[M+H] + 1435 Exact Mass: 1434

[0213] <Calculation of half-width of maximum absorption wavelength by ultraviolet-visible-near-infrared absorption spectroscopy> A 28 mg / L chloroform solution of compound (IV) was prepared, and the absorption spectrum was measured. However, the shape of the spectrum was distorted for compound (IV), and the half-width of the maximum absorption wavelength could not be calculated.

[0214] (Comparative Example 1-2) <Synthesis of Compound (V)> Under a nitrogen atmosphere, 8.6 parts of compound (II-c) obtained in Synthesis Example 5, 0.57 parts of nickel(II) chloride (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.), 808 parts of 1-pentanol (manufactured by Tokyo Chemical Industry Co., Ltd.), and 141 parts of 1,8-diazabicyclo[5,4,0]-7-undecene (manufactured by Tokyo Chemical Industry Co., Ltd.) were mixed and refluxed at 160°C for 15 hours. After completion of the reaction, the reaction solution was cooled to room temperature and poured into 8,000 parts of methanol. The precipitated solid was filtered and washed by decantation twice with 200 parts of ion-exchanged water and twice with 200 parts of methanol. The crude product was purified by silica gel column chromatography to obtain 5.3 parts (yield 59%) of a compound represented by formula (V) (compound (V)) as a dark green solid.

[0215] [ka]

[0216] <Identification of Compound (V)> (Mass spectrometry) Ionization mode = ESI + : m / z=[M+H] + 2011 Exact Mass: 2011

[0217] <Calculation of half-width of maximum absorption wavelength by ultraviolet-visible-near-infrared absorption spectroscopy> A 28 mg / L chloroform solution of compound (V) was prepared, and the absorption spectrum was measured to calculate the half-width of the maximum absorption wavelength. The results are shown in Table 1.

[0218] [Table 1]

[0219] As shown in Table 1, it was confirmed that the phthalocyanine compound of the present invention has a maximum absorption wavelength with a sufficiently wide half-value width in the NIR region.

[0220] (Synthesis Example 6) <Synthesis of Resin B-1> A suitable amount of nitrogen was passed into a flask equipped with a reflux condenser, a dropping funnel, and a stirrer to replace the atmosphere with nitrogen, and 340 parts of propylene glycol monomethyl ether acetate was added and heated to 80°C with stirring. Next, 57 parts of acrylic acid, 3,4-epoxytricyclo[5.2.1.0] 2,6 ]decan-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 2,6 A mixed solution containing 54 parts of a mixture of decan-9-yl acrylate (content ratio 1:1 by molar ratio), 239 parts of benzyl methacrylate, and 73 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. Meanwhile, an initiator solution prepared by dissolving 40 parts of the polymerization initiator 2,2-azobis(2,4-dimethylvaleronitrile) in 197 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. The mixture was then maintained at 80°C for 3 hours and cooled to room temperature to obtain a copolymer (Resin B-1) solution with a solids content of 37.0% and a viscosity of 127 mPas measured with a Brookfield viscometer (23°C). The weight-average molecular weight Mw of the resulting copolymer was 9.4 x 10 3 The resin B-1 had a polydispersity of 1.89 and an acid value of 114 mg-KOH / g in terms of solid content.

[0221] [ka]

[0222] Example 2-1 <Preparation of Dispersion 1A> 25.0 parts of Mixture A, 25.0 parts of Dispersant (BYK BYKLPN-6919) (solids content equivalent), 40.5 parts of Resin B-1 (solids content equivalent), 409 parts of propylene glycol monomethyl ether acetate, and 1500 parts of 0.2 mm zirconia beads were mixed, and the resulting mixture was shaken for 1 hour using a Paint Conditioner (LAU). The zirconia beads were then removed by filtration to obtain Dispersion 1A.

[0223] <Preparation of Resin Composition 1A> Resin composition 1A was obtained by mixing the following components. Colorant (A): Dispersion 1A 415 parts Resin (B): 84.3 parts (solid equivalent) of Resin B-1 obtained in Synthesis Example 6 Polymerizable compound (C): 64.5 parts of dipentaerythritol polyacrylate (trade name A-9550, manufactured by Shin-Nakamura Chemical Co., Ltd.) Polymerization initiator (D): 12.9 parts N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine (trade name TR-PBG327, manufactured by Changzhou Strong Electronic New Materials Co., Ltd.) Solvent (E): 1500 parts propylene glycol monomethyl ether acetate Leveling agent (F): 0.1 part polyether-modified silicone oil (Toray Silicone SH8400, manufactured by Toray Dow Corning Co., Ltd.)

[0224] <Preparation of cured coating film> The obtained resin composition 1A was applied by spin coating onto a 5 cm square glass substrate (Eagle 2000, manufactured by Corning Incorporated) and then pre-baked at 100°C for 3 minutes to obtain a coating film, which was then post-baked in an oven at 230°C for 5 minutes to obtain a cured coating film.

[0225] <Evaluation of foreign matter in cured coatings> The resulting cured coating film was subjected to spectral analysis using a colorimeter (OSP-SP-200 manufactured by Olympus Corporation). The magnitude of the average transmittance from 940 to 1200 nm was calculated to evaluate the presence of foreign matter. Mixture A has no absorption in the 940 to 1200 nm range. Therefore, if no foreign matter is present in the cured coating film, the average transmittance will be close to 100%. On the other hand, if foreign matter is present, the foreign matter will scatter light, causing a decrease in the average transmittance. Therefore, the higher the average transmittance from 940 to 1200 nm, the more likely it is that a cured coating film with sufficiently little foreign matter has been produced. The results are shown in Table 2.

[0226] (Example 2-2) <Preparation and evaluation of cured coating film> Dispersion 2A and resin composition 2A were obtained in the same manner as in Example 2-1, except that 25.0 parts of mixture A obtained in Example 1-1 was replaced with 25.0 parts of mixture B obtained in Example 1-2. Then, a cured coating film was produced using resin composition 2A. The cured coating film was evaluated for foreign matter in the same manner as in Example 2-1. The results are shown in Table 2.

[0227] (Comparative Example 2-1) <Preparation and evaluation of cured coating film> Dispersion 1a and resin composition 1a were obtained in the same manner as in Example 2-1, except that 25.0 parts of the mixture A obtained in Example 1-1 was replaced with 25.0 parts of the compound (V) obtained in Comparative Example 1-2. Then, a cured coating film was produced using resin composition 1a. The cured coating film was evaluated for foreign matter in the same manner as in Example 2-1. The results are shown in Table 2.

[0228] [Table 2]

[0229] As shown in Table 2, the cured coating films formed from the resin compositions of Examples 2-1 and 2-2 had higher average transmittance in the range of 940 to 1200 nm than the cured coating film formed from the resin composition of Comparative Example 2-1. These results demonstrate that the resin composition of the present invention can be used to form a cured coating film (e.g., an optical filter) with sufficiently low generation of foreign matter.

Claims

1. A phthalocyanine compound represented by formula (I): 【Chemical 1】 [In formula (I), M １ represents a metal atom. n represents an integer of 1 to 3. R Ａ１ and R Ａ２ are each independently a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, or OR Ａ５１ represents a group, and two or more R Ａ１ and R Ａ２ When present, they may be the same or different from one another. R Ａ５１ represents a hydrocarbon group having 1 to 20 carbon atoms, and two or more R Ａ５１ When present, they may be the same or different from one another. A １ and A ２ each independently represents an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 3 to 20 carbon atoms, and two or more A １ and A ２ When present, they may be the same or different from one another. R Ｂ１ and R Ｂ２ are each independently a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, or OR Ｂ５１ represents a group, and two or more R Ｂ１ and R Ｂ２ When present, they may be the same or different from one another. R Ｂ５１ represents a hydrocarbon group having 1 to 20 carbon atoms, and two or more R Ｂ５１ When present, they may be the same or different from one another. B １ and B ２ each independently represents an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 3 to 20 carbon atoms, and two or more B １ and B ２ When present, they may be the same or different from one another. * represents a bond. A double line consisting of a solid line and a dashed line represents a single bond or a double bond.]

2. A phthalocyanine compound represented by formula (I-1), formula (I-2), formula (I-3), or formula (I-4). 【Chemistry 2】 [In formula (I-1), M １ represents a metal atom. R Ａ１ and R Ａ２ are each independently a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, or OR Ａ５１ represents a group, and two or more R Ａ１ and R Ａ２ When present, they may be the same or different from one another. R Ａ５１ represents a hydrocarbon group having 1 to 20 carbon atoms, and two or more R Ａ５１ When present, they may be the same or different from one another. A １ and A ２ each independently represents an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 3 to 20 carbon atoms, and two or more A １ and A ２ When present, they may be the same or different from one another. R Ｂ１ and R Ｂ２ are each independently a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, or OR Ｂ５１ represents a group, and two or more R Ｂ１ and R Ｂ２ When present, they may be the same or different from one another. R Ｂ５１ represents a hydrocarbon group having 1 to 20 carbon atoms, and two or more R Ｂ５１ When present, they may be the same or different from one another. B １ and B ２ each independently represents an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 3 to 20 carbon atoms, and two or more B １ and B ２ When present, they may be the same or different from each other. 【Chemistry 3】 [In formula (I-2), M １ , R Ａ１ , R Ａ２ , A １ , A ２ , R Ｂ１ , R Ｂ２ , B １ , and B ２ has the same meaning as above.] 【Chemistry 4】 [In formula (I-3), M １ , R Ａ１ , R Ａ２ , A １ , A ２ , R Ｂ１ , R Ｂ２ , B １ , and B ２ has the same meaning as above.] 【Chemistry 5】 [In formula (I-4), M １ , R Ａ１ , R Ａ２ , A １ , A ２ , R Ｂ１ , R Ｂ２ , B １ , and B ２ has the same meaning as above.]

3. Contains a colorant, a resin, and a solvent, A resin composition, wherein the colorant comprises the phthalocyanine compound according to claim 1 or 2.

4. The resin composition according to claim 3 , further comprising a polymerizable compound and a polymerization initiator.

5. An optical filter formed from the resin composition according to claim 3.

6. A solid-state imaging device comprising the optical filter according to claim 5 .

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