Coloring Curing Resin Composition

Abstract

The objective of this invention is to provide a coloring-curing resin composition capable of preventing fading of the cured product (capable of reducing ΔE*ab). This invention relates to a coloring-curing resin composition comprising a colorant, a dispersant, a resin, a polymerizable compound, a polymerization initiator, and a solvent, wherein the colorant contains a squaric acid dye having maximum absorption in the visible light region, and the dispersant has an amine value exceeding 0 mg KOH / g and below 30 mg KOH / g.

Description

Technical Field

[0001] This invention relates to a color-curing resin composition, a color filter, a liquid crystal display device, and a method for manufacturing the color-curing resin composition. Background Technology

[0002] Color filters used in display devices such as liquid crystal displays, electroluminescent displays, and plasma displays, as well as solid-state imaging elements such as CCDs and CMOS sensors, are manufactured from color-curing resin compositions. Squaric acid is known as a colorant used in such color-curing resin compositions. Dyes (Patent Document 1, etc.).

[0003] Existing technical documents

[0004] Patent documents

[0005] Patent Document 1: Japanese Patent Application Publication No. 2019-163233 Summary of the Invention

[0006] However, for those containing squaric acid The aforementioned coloring and curing resin compositions for dyes require post-baking in the film-forming process to prevent fading (reducing ΔE*ab). Therefore, the objective of this invention is to provide a coloring and curing resin composition capable of preventing fading of the cured product (capable of reducing ΔE*ab). Furthermore, in a preferred embodiment of the invention, the objective is also to provide a coloring and curing resin composition that, in addition to preventing fading, improves one or both of the absorbance retention rate and contrast of the cured product.

[0007] That is, the essence of the present invention is as follows.

[0008] [1] A coloring and curing resin composition comprising a colorant, a dispersant, a resin, a polymerizable compound, a polymerization initiator, and a solvent.

[0009] The aforementioned colorant contains squaric acid, which has maximum absorption in the visible light region. dye,

[0010] The amine value of the above dispersants exceeds 0 mg KOH / g and is below 30 mg KOH / g.

[0011] [2] According to the coloring and curing resin composition of [1], wherein the above-mentioned squaric acid The dye is a compound represented by formula (AI).

[0012]

[0013] In formula (AI),

[0014] R 1 ~R4 Each of these groups independently represents a hydrogen atom, a halogen atom, a hydroxyl group, or a monovalent saturated hydrocarbon group with 1 to 20 carbon atoms that may have substituents. The methylene group constituting this monovalent saturated hydrocarbon group may be substituted with -O- or -S-.

[0015] R 5 ~R 8 Each can be used independently to represent a hydrogen atom or a hydroxyl group.

[0016] Ar 1 and Ar 2 Each group is represented independently by formula (i).

[0017]

[0018] In formula (i),

[0019] R 12 This indicates a monovalent saturated hydrocarbon group or hydroxyl or carboxyl group with 1 to 20 carbon atoms, where m represents an integer from 0 to 5. The methylene group constituting this monovalent saturated hydrocarbon group can be substituted with -O- or -S-. When m is 2 or more, multiple R... 12 They can be the same or different. * indicates the bonding site with the nitrogen atom.

[0020] R 9 and R 10 Each of these groups independently represents a monovalent saturated hydrocarbon group with 1 to 20 carbon atoms that may have substituents, or a group represented by formula (i). The methylene group constituting this monovalent saturated hydrocarbon group may be substituted with -O- or -S-.

[0021] [3] The coloring and curing resin composition according to [1] or [2], wherein the above-mentioned squaric acid The dye is a compound represented by formula (AII).

[0022]

[0023] In formula (AII),

[0024] R 1 ~R 4 Each of these groups independently represents a hydrogen atom, a halogen atom, a hydroxyl group, or a monovalent saturated hydrocarbon group with 1 to 20 carbon atoms that may have substituents. The methylene group constituting this monovalent saturated hydrocarbon group may be substituted with -O- or -S-.

[0025] R 5 ~R 8 Each can be used independently to represent a hydrogen atom or a hydroxyl group.

[0026] Ar 1 and Ar 2Each group is represented independently by formula (i).

[0027]

[0028] In formula (i),

[0029] R 12 This indicates a monovalent saturated hydrocarbon group or hydroxyl or carboxyl group with 1 to 20 carbon atoms, where m represents an integer from 0 to 5. The methylene group constituting this monovalent saturated hydrocarbon group can be substituted with -O- or -S-. When m is 2 or more, multiple R... 12 They can be the same or different. * indicates the bonding site with the nitrogen atom.

[0030] R 13 and R 14 Each of these groups independently represents a monovalent saturated hydrocarbon group with 1 to 20 carbon atoms, having either a hydroxyl or a carboxyl group. The methylene group constituting this monovalent saturated hydrocarbon group can be substituted with -O- or -S-.

[0031] [4] The coloring curable resin composition according to any one of [1] to [3], wherein the dispersant has a basic functional group of tertiary amino or nitrogen-containing heterocyclic ring.

[0032] [5] The coloring curable resin composition according to any one of [1] to [4], wherein the content of the dispersant is 0.1 to 50 parts by weight relative to 100 parts by weight of the colorant.

[0033] [6] The coloring curable resin composition according to any one of [1] to [5], wherein the coloring agent is dispersed in a solvent by the dispersant to form a dispersion.

[0034] [7] A color filter formed from any one of the color-curing resin compositions described in [1] to [6].

[0035] [8] A liquid crystal display device comprising the color filter described in [7].

[0036] [9] A method for manufacturing a coloring and curing resin composition, comprising the following steps:

[0037] The process of obtaining a dispersion of a colorant dispersed in a solvent by means of a dispersant, and

[0038] The step of adding resin, polymerizable compound and polymerization initiator to the above dispersion;

[0039] The aforementioned colorant contains squaric acid, which has maximum absorption in the visible light region. dye,

[0040] The amine value of the above dispersants exceeds 0 mg KOH / g and is below 30 mg KOH / g.

[0041] According to the present invention, a color-curing resin composition that prevents the cured product from fading can be provided. Furthermore, according to a preferred embodiment of the present invention, a color-curing resin composition that, in addition to preventing fading, also improves one or both of the absorbance retention rate and contrast of the cured product can be provided. Detailed Implementation

[0042] <Coloring and Curing Resin Composition>

[0043] The coloring and curing resin composition of the present invention contains a colorant (hereinafter, sometimes referred to as colorant (A)), a dispersant (hereinafter, sometimes referred to as dispersant (P)), a resin (hereinafter, sometimes referred to as resin (B)), a polymerizable compound (hereinafter, sometimes referred to as polymerizable compound (C)), a polymerization initiator (hereinafter, sometimes referred to as polymerization initiator (D)) and a solvent (hereinafter, sometimes referred to as solvent (E)), wherein the colorant (A) contains squaric acid, which has maximum absorption in the visible light region. The dye has an amine value exceeding 0 mg KOH / g and below 30 mg KOH / g.

[0044] It should be noted that the compounds exemplified as ingredients in this specification may be used alone or in combination unless otherwise specified.

[0045] <Coloring Agent (A)>

[0046] Colorant (A) contains squaric acid, which has maximum absorption in the visible light region. Dyes. The above-mentioned squaric acid The dye is preferably a compound that has maximum absorption at 380 nm or higher (preferably 400 nm or higher) and less than 700 nm (preferably 650 nm or lower).

[0047] As the above-mentioned squaric acid Dyes, as long as they are compounds with maximum absorption in the visible light region, are not particularly limited and can use well-known squaric acid. The dye is preferably a compound represented by formula (AI).

[0048]

[0049] In formula (AI),

[0050] R 1 ~R 4Each of these groups independently represents a hydrogen atom, a halogen atom, a hydroxyl group, or a monovalent saturated hydrocarbon group with 1 to 20 carbon atoms that may have substituents. The methylene group constituting this monovalent saturated hydrocarbon group may be substituted with -O- or -S-.

[0051] R 5 ~R 8 Each can be used independently to represent a hydrogen atom or a hydroxyl group.

[0052] Ar 1 and Ar 2 Each group is represented independently by formula (i).

[0053]

[0054] In formula (i),

[0055] R 12 This indicates a monovalent saturated hydrocarbon group or hydroxyl or carboxyl group with 1 to 20 carbon atoms, where m represents an integer from 0 to 5. The methylene group constituting this monovalent saturated hydrocarbon group can be substituted with -O- or -S-. When m is 2 or more, multiple R... 12 They can be the same or different. * indicates the bonding site with the nitrogen atom.

[0056] R 9 and R 10 Each of these groups independently represents a monovalent saturated hydrocarbon group with 1 to 20 carbon atoms that may have substituents, or a group represented by formula (i). The methylene group constituting this monovalent saturated hydrocarbon group may be substituted with -O- or -S-.

[0057] As R 1 ~R 4 The halogen atom represented can be fluorine, chlorine, bromine, or iodine.

[0058] As R 1 ~R 4 R 9 R 10 and R 12 The term refers to monovalent saturated hydrocarbon groups with 1 to 20 carbon atoms. Examples of such groups include straight-chain alkyl groups with 1 to 20 carbon atoms, such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, hexadecyl, and eicosyl; branched alkyl groups with 3 to 20 carbon atoms, such as isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, neopentyl, and 2-ethylhexyl; and alicyclic saturated hydrocarbon groups with 3 to 20 carbon atoms, such as cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, tricyclodecyl, and adamantyl.

[0059] Examples of substituents for these saturated hydrocarbon groups include halogen atoms such as fluorine, chlorine, and iodine; hydroxyl groups; carboxyl groups; and -NR groups.a R b (R a and R b Each group can be a hydrogen atom or an alkyl group having 1 to 20 carbon atoms; a nitro group; an alkoxycarbonyl group having 1 to 10 carbon atoms, such as a methoxycarbonyl or ethoxycarbonyl group; etc., as a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, for example, groups represented by the following formulas. In the following formulas, * indicates a bonding site.

[0060] *-CF3 *-CH2CF3

[0061] *-CH2CF2CF3

[0062] *-CH2CF2CF2CF3

[0063] As a group in which the methylene group constituting these saturated hydrocarbon groups is replaced by -O- or -S-, examples can be given of groups represented by the following formulas. In the following formulas, * indicates a bonding site.

[0064]

[0065] R 12 The monovalent saturated hydrocarbon group representing 1 to 20 carbon atoms can be a monovalent unsaturated hydrocarbon group representing 2 to 20 carbon atoms, as R 12 The unsaturated hydrocarbon group with 2 to 20 carbon atoms in the group includes, for example, vinyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, and decenyl.

[0066] As R 1 ~R 4 Preferably, hydrogen atoms, hydroxyl groups, and alkyl groups having 1 to 4 carbon atoms are used; more preferably, hydrogen atoms, hydroxyl groups, and methyl groups are used; and even more preferably, hydrogen atoms are used.

[0067] As R 5 ~R 8 Preferably, at least one of them is a hydroxyl group, more preferably R 5 and R 6 At least one of them is hydroxyl and R 7 and R 8 At least one of them is a hydroxyl group, and R is further preferred. 5 and R 6 Either of them is a hydroxyl group and R 7 and R 8 Either of them is a hydroxyl group.

[0068] As R 9 and R 10Preferably, straight-chain alkyl groups with 1 to 20 carbon atoms that may have substituents and branched alkyl groups with 3 to 20 carbon atoms that may have substituents are preferred. More preferably, straight-chain alkyl groups with 1 to 10 carbon atoms that may have substituents and branched alkyl groups with 3 to 10 carbon atoms that may have substituents are preferred. Even more preferably, straight-chain alkyl groups with 1 to 5 carbon atoms that have a hydroxyl group at the end, straight-chain alkyl groups with 1 to 5 carbon atoms that have a carboxyl group at the end, and branched alkyl groups with 3 to 10 carbon atoms are preferred. Still more preferably, straight-chain alkyl groups with 1 to 5 carbon atoms that have a hydroxyl group at the end and straight-chain alkyl groups with 1 to 5 carbon atoms that have a carboxyl group at the end are preferred.

[0069] As R 12 Preferably, it is a monovalent saturated hydrocarbon group having 1 to 10 carbon atoms and having hydroxyl or carboxyl groups; more preferably, it is a straight-chain alkyl group having 1 to 5 carbon atoms and having hydroxyl or carboxyl groups; even more preferably, it is a straight-chain alkyl group having 1 to 5 carbon atoms or a straight-chain alkyl group having 1 to 5 carbon atoms and having hydroxyl or carboxyl groups.

[0070] m is preferably 1 to 5, more preferably 1 to 3, and even more preferably 2 or 3.

[0071] As Ar 1 and Ar 2 Preferably, it is a group represented by formula (ii).

[0072]

[0073] In formula (ii),

[0074] R 15 This indicates a monovalent saturated hydrocarbon group or hydroxyl or carboxyl group with 1 to 20 carbon atoms, where p represents an integer from 0 to 5. The methylene group constituting this monovalent saturated hydrocarbon group can be replaced by -O- or -S-. When p is 2 or higher, multiple R... 15 They can be the same or different.

[0075] R 16 This indicates a monovalent saturated hydrocarbon group with 1 to 20 carbon atoms that may have substituents, or a monovalent unsaturated hydrocarbon group with 2 to 20 carbon atoms that may have substituents, where q represents an integer from 0 to 5. Here, p+q represents an integer from 0 to 5. The methylene group constituting this monovalent saturated hydrocarbon group can be substituted with -O- or -S-. When q is 2 or more, multiple R... 16 They can be the same or different.

[0076] * Indicates the bonding site with a nitrogen atom.

[0077] As R 15The monovalent saturated hydrocarbon group having 1 to 20 carbon atoms can be exemplified by the groups described above that have 1 to 20 monovalent saturated hydrocarbon groups having 1 to 20 carbon atoms. Among these, straight-chain alkyl groups having 1 to 20 carbon atoms are preferred, straight-chain alkyl groups having 1 to 10 carbon atoms are more preferred, and straight-chain alkyl groups having 1 to 5 carbon atoms are even more preferred.

[0078] The hydroxyl or carboxyl groups of a monovalent saturated hydrocarbon group with 1 to 20 carbon atoms are preferably bonded to the end of the molecular chain of the saturated hydrocarbon group.

[0079] Examples of monovalent saturated hydrocarbon groups having 1 to 20 carbon atoms and containing a hydroxyl or carboxyl group include groups represented by the following formulas. In the following formulas, * indicates a bonding site.

[0080]

[0081] As R 15 Preferably, it is a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms and a hydroxyl group. Furthermore, it is preferred to have R... 15 At least one of the methylene groups in a monovalent saturated hydrocarbon group representing 1 to 20 carbon atoms is replaced by -O-. As a constituent of R 15 The methylene group of a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms has at least one group substituted with -O-, for example, the group represented by the following formula. In the following formula, * represents a bonding site.

[0082]

[0083] As R 16 The groups represented as monovalent saturated hydrocarbon groups having 1 to 20 carbon atoms that may have substituents and monovalent unsaturated hydrocarbon groups having 2 to 20 carbon atoms that may have substituents are the groups exemplified above as monovalent saturated hydrocarbon groups having 1 to 20 carbon atoms that may have substituents and monovalent unsaturated hydrocarbon groups having 2 to 20 carbon atoms that may have substituents.

[0084] Examples of substituents for this unsaturated hydrocarbon group include halogen atoms such as fluorine, chlorine, and iodine; hydroxyl groups; carboxyl groups; and -NR groups. c R d (R c and R d Each of these groups is independently composed of hydrogen atoms or alkyl groups with 1 to 20 carbon atoms; nitro group; alkoxy group with 1 to 10 carbon atoms, such as methoxy and ethoxy; alkoxycarbonyl group with 1 to 10 carbon atoms, such as methoxycarbonyl and ethoxycarbonyl; etc.

[0085] Preferably, the substituent is a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms; more preferably, it is a straight-chain alkyl group having 1 to 5 carbon atoms; even more preferably, it is a straight-chain alkyl group having 1 to 3 carbon atoms; and particularly preferably, it is methyl.

[0086] p is preferably an integer from 0 to 3, more preferably an integer from 0 to 1, and even more preferably 1.

[0087] q is preferably an integer from 1 to 3, more preferably an integer from 1 to 2, and even more preferably 2.

[0088] p is 0 or 1, and q is particularly preferably 2.

[0089] Ar 1 and Ar 2 They can be the same or different, but the same is preferred.

[0090] Among the compounds represented by formula (AI), compounds represented by formula (AII) are more preferred. By making the above-mentioned squaric acid... The dye is a compound represented by formula (AII), which can further suppress the decrease in maximum absorption after post-baking, and can also further suppress fading changes before and after post-baking.

[0091]

[0092] In formula (AII),

[0093] R 1 ~R 8 Ar 1 and Ar 2 Same as above.

[0094] R 13 and R 14 Each of these groups independently represents a monovalent saturated hydrocarbon group with 1 to 20 carbon atoms, having either a hydroxyl or a carboxyl group. The methylene group constituting this monovalent saturated hydrocarbon group can be substituted with -O- or -S-.

[0095] As R 13 and R 14 The monovalent saturated hydrocarbon group having 1 to 20 carbon atoms can be exemplified by the groups described above that have 1 to 20 monovalent saturated hydrocarbon groups having 1 to 20 carbon atoms. Among these, straight-chain alkyl groups having 1 to 20 carbon atoms are preferred, straight-chain alkyl groups having 1 to 10 carbon atoms are more preferred, and straight-chain alkyl groups having 1 to 5 carbon atoms are even more preferred.

[0096] The hydroxyl or carboxyl groups of a monovalent saturated hydrocarbon group with 1 to 20 carbon atoms are preferably bonded to the end of the molecular chain of the saturated hydrocarbon group.

[0097] Examples of monovalent saturated hydrocarbon groups having 1 to 20 carbon atoms and containing a hydroxyl or carboxyl group include groups represented by the following formulas. In the following formulas, * indicates a bonding site.

[0098]

[0099] R in equation (AII) 1 ~R 8 Ar 1 and Ar 2 The preferred method is the same as described above.

[0100] Squamous acid The dye (preferably a compound represented by formula (AI), more preferably a compound represented by formula (AII)) preferably has one or more hydroxyl groups, more preferably has two or more hydroxyl groups, even more preferably has two or more hydroxyl groups and two or more carboxyl groups, and even more preferably has three or more hydroxyl groups.

[0101] As for compounds represented by formula (AI), for example, compounds represented by formulas (AI-1) to (AI-60) shown in Tables 1 to 2 can be cited. Among them, from the viewpoint of the availability of raw materials, compounds represented by formulas (AI-1) to (AI-20) are preferred.

[0102] The compounds represented by formula (AI) are more preferably compounds represented by formulas (AI-1) to (AI-5) and (AI-11) to (AI-20).

[0103] Further preferred are compounds represented by formulas (AI-11) to (AI-20).

[0104] More preferably, compounds represented by formula (AI-15) or formula (AI-16) are preferred.

[0105] [Table 1]

[0106] <![CDATA[R 1 ~R 4 ]]> <![CDATA[R 5 ]]> <![CDATA[R 6 ]]> <![CDATA[R 7 ]]> <![CDATA[R 8 ]]> <![CDATA[R 9 ]]> <![CDATA[R 10 ]]> <![CDATA[Ar 1 ]]> <![CDATA[Ar 2 ]]> (AI-1) H H OH OH H x-1 x-1 y-1 y-1 (AI-2) H H OH OH H x-1 x-1 y-2 y-2 (AI-3) H H OH OH H x-1 x-1 y-3 y-3 (AI-4) H H OH OH H x-1 x-1 y-4 y-4 (AI-5) H H OH OH H x-1 x-1 y-5 y-5 (AI-6) H H OH OH H x-2 x-2 y-1 y-1 (AI-7) H H OH OH H x-2 x-2 y-2 y-2 (AI-8) H H OH OH H x-2 x-2 y-3 y-3 (AI-9) H H OH OH H x-2 x-2 y-4 y-4 (AI-10) H H OH OH H x-2 x-2 y-5 y-5 (AI-11) H H OH OH H x-3 x-3 y-1 y-1 (AI-12) H H OH OH H x-3 x-3 y-2 y-2 (AI-13) H H OH OH H x-3 x-3 y-3 y-3 (AI-14) H H OH OH H x-3 x-3 y-4 y-4 (AI-15) H H OH OH H x-3 x-3 y-5 y-5 (AI-16) H H OH OH H x-4 x-4 y-1 y-1 (AI-17) H H OH OH H x-4 x-4 y-2 y-2 (AI-18) H H OH OH H x-4 x-4 y-3 y-3 (AI-19) H H OH OH H x-4 x-4 y-4 y-4 (AI-20) H H OH OH H x-4 x-4 y-5 y-5 (AI-21) H H H H H x-1 x-1 y-1 y-1 (AI-22) H H H H H x-1 x-1 y-2 y-2 (AI-23) H H H H H x-1 x-1 y-3 y-3 (AI-24) H H H H H x-1 x-1 y-4 y-4 (AI-25) H H H H H x-1 x-1 y-5 y-5 (AI-26) H H H H H x-2 x-2 y-1 y-1 (AI-27) H H H H H x-2 x-2 y-2 y-2 (AI-28) H H H H H x-2 x-2 y-3 y-3 (AI-29) H H H H H x-2 x-2 y-4 y-4 (AI-30) H H H H H x-2 x-2 y-5 y-5

[0107] [Table 2]

[0108] <![CDATA[R 1 ~R 4 ]]> <![CDATA[R 5 ]]> <![CDATA[R 6 ]]> <![CDATA[R 7 ]]> <![CDATA[R 8 ]]> <![CDATA[R 9 ]]> <![CDATA[R 10 ]]> <![CDATA[Ar 1 ]]> <![CDATA[Ar 2 ]]> (AI-31) H H H H H x-3 x-3 y-1 y-1 (AI-32) H H H H H x-3 x-3 y-2 y-2 (AI-33) H H H H H x-3 x-3 y-3 y-3 (AI-34) H H H H H x-3 x-3 y-4 y-4 (AI-35) H H H H H x-3 x-3 y-5 y-5 (AI-36) H H H H H x-4 x-4 y-1 y-1 (AI-37) H H H H H x-4 x-4 y-2 y-2 (AI-38) H H H H H x-4 x-4 y-3 y-3 (AI-39) H H H H H x-4 x-4 y-4 y-4 (AI-40) H H H H H x-4 x-4 y-5 y-5 (AI-41) H OH OH OH OH x-1 x-1 y-1 y-1 (AI-42) H OH OH OH OH x-1 x-1 y-2 y-2 (AI-43) H OH OH OH OH x-1 x-1 y-3 y-3 (AI-44) H OH OH OH OH x-1 x-1 y-4 y-4 (AI-45) H OH OH OH OH x-1 x-1 y-5 y-5 (AI-46) H OH OH OH OH x-2 x-2 y-1 y-1 (AI-47) H OH OH OH OH x-2 x-2 y-2 y-2 (AI-48) H OH OH OH OH x-2 x-2 y-3 y-3 (AI-49) H OH OH OH OH x-2 x-2 y-4 y-4 (AI-50) H OH OH OH OH x-2 x-2 y-5 y-5 (AI-51) H OH OH OH OH x-3 x-3 y-1 y-1 (AI-52) H OH OH OH OH x-3 x-3 y-2 y-2 (AI-53) H OH OH OH OH x-3 x-3 y-3 y-3 (AI-54) H OH OH OH OH x-3 x-3 y-4 y-4 (AI-55) H OH OH OH OH x-3 x-3 y-5 y-5 (AI-56) H OH OH OH OH x-4 x-4 y-1 y-1 (AI-57) H OH OH OH OH x-4 x-4 y-2 y-2 (AI-58) H OH OH OH OH x-4 x-4 y-3 y-3 (AI-59) H OH OH OH OH x-4 x-4 y-4 y-4 (AI-60) H OH OH OH OH x-4 x-4 y-5 y-5

[0109] In Tables 1 and 2, x-1 to x-4 represent the groups shown in the following formulas (* indicates the bonding site).

[0110]

[0111] In Tables 1 and 2, y-1 to y-5 represent the groups shown in the following formulas (* indicates the bonding site).

[0112]

[0113] The compound represented by formula (AI) can be produced, for example, by reacting the compound represented by formula (pt1), the compound represented by formula (pt2), and the compound represented by formula (pt3). In this reaction, the total amount of the compound represented by formula (pt1) and the compound represented by formula (pt2) used is preferably 1.5 to 2.5 mol relative to 1 mol of the compound represented by formula (pt3).

[0114]

[0115] In the formula, R 1 ~R 10 Ar 1 and Ar 2 They represent the same meanings as described above.

[0116] The reaction temperature is preferably 30℃~180℃, more preferably 80℃~140℃. The reaction time is preferably 1 hour~12 hours, more preferably 3 hours~8 hours.

[0117] From a yield perspective, the reaction is preferably carried out in an organic solvent. Examples of organic solvents include hydrocarbon solvents such as toluene and xylene; halogenated hydrocarbon solvents such as chlorobenzene, dichlorobenzene, and chloroform; alcohol solvents such as methanol, ethanol, isopropanol, and butanol; nitro hydrocarbon solvents such as nitrobenzene; ketone solvents such as methyl isobutyl ketone; and amide solvents such as 1-methyl-2-pyrrolidone; etc., and they can be used in combination. A mixture of butanol and toluene is preferred. The amount of organic solvent used is preferably 10 to 200 parts by mass, more preferably 30 to 150 parts by mass, relative to the total mass of the compounds represented by formula (pt1) and (pt2).

[0118] There are no particular limitations on the method for obtaining the target compound represented by formula (AI) from the reaction mixture, and various known methods can be used. For example, methods such as distilling off the solvent from the reaction solution to obtain the target compound, or cooling and filtering the precipitated crystals after the reaction is complete, can be cited. The filtered crystals are preferably washed with water or the like and then dried. In addition, further purification can be performed as needed using known methods such as column chromatography or recrystallization.

[0119] The above-mentioned squaric acid in colorant (A) The dye content is preferably 50% by mass or more, more preferably 70% by mass or more, even more preferably 80% by mass or more, particularly preferably 90% by mass or more, and can be 95% by mass or more, or 100% by mass.

[0120] Colorant (A) in addition to the above-mentioned squaric acid In addition to dyes, it may also contain substances similar to the aforementioned squaric acid. Different colorants in dyes, and the above-mentioned squaric acid Different colorants for dyes can be either dyes (hereinafter, sometimes referred to as dyes (A1)) or pigments (hereinafter, sometimes referred to as pigments (A2)). (The text abruptly ends here, seemingly mid-sentence.) Different colorants for dyes may contain one or both of these dyes (A1) and pigments (A2).

[0121] Dye (A1) as long as it does not contain the aforementioned squaric acid There are no particular limitations on the dyes used; well-known dyes can be used, such as solvent dyes, acid dyes, direct dyes, and mordant dyes. Examples of dyes include compounds classified as hues other than pigments in color indexes (published by The Society of Dyers and Colourists) and well-known dyes listed in dyeing guides (for dyeing companies). Furthermore, based on their chemical structure, examples include azo dyes, cyanide dyes, triphenylmethane dyes, xanthocyanin dyes, phthalocyanine dyes, anthraquinone dyes, naphthoquinone dyes, quinone imine dyes, methylene dyes, azomethyl base dyes, acridine dyes, styryl dyes, coumarin dyes, quinoline dyes, and nitro dyes. Among these, organic solvent-soluble dyes are preferred.

[0122] Specifically, examples include CI Solvent Yellow 4 (hereinafter, CI Solvent Yellow is omitted and only numbered), 14, 15, 23, 24, 38, 62, 63, 68, 82, 94, 98, 99, 117, 162, 163, 167, and 189.

[0123] CI Solvent Red 45, 49, 111, 125, 130, 143, 145, 146, 150, 151, 155, 168, 169, 172, 175, 181, 207, 218, 222, 227, 230, 245, 247;

[0124] CI Solvent Orange 2, 7, 11, 15, 26, 56, 77, 86;

[0125] CI Solvent Violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60;

[0126] 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;

[0127] CI solvent green dyes 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35, etc.

[0128] 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, 15 7, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251;

[0129] CI Acid Red 1, 4, 8, 14, 17, 18, 26, 27, 29, 31, 33, 34, 35, 37, 40, 42, 44, 50, 51, 52, 57, 66, 73, 76, 80, 87, 88, 91, 92, 94, 95, 97, 98, 103, 106, 111, 114, 129, 133, 134, 138, 143, 145, 150, 151, 155, 158, 160, 172, 176, 182 183, 195, 198, 206, 211, 215, 216, 217, 227, 228, 249, 252, 257, 258, 260, 261, 266, 268, 270, 274, 277, 280, 281, 289, 308, 312, 315, 316, 339, 341, 345, 346, 349, 382, ​​383, 388, 394, 401, 412, 417, 418, 422, 426;

[0130] CI Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 169, 173;

[0131] CI Acid Violet 6B, 7, 9, 15, 16, 17, 19, 21, 23, 24, 25, 30, 34, 38, 49, 72, 102;

[0132] Acid Blue (CI) 1, 3, 5, 7, 9, 11, 13, 15, 17, 18, 22, 23, 24, 25, 26, 27, 29, 34, 38, 40, 41, 42, 43, 45, 48, 51, 54, 59, 60, 62, 70, 72, 74, 75, 78, 80, 82, 83, 86, 87, 88, 90, 90:1, 91, 92, 93, 93:1, 96, 99, 100, 102, 103, 104, 108, 109, 110, 112, 113, 117, 119, 120, 123 126, 127, 129, 130, 131, 138, 140, 142, 143, 147, 150, 151, 154, 158, 161, 166, 167, 168, 170, 171, 175, 182, 183, 184, 187, 192, 199, 203, 204, 205, 210, 213, 229, 234, 236, 242, 243, 256, 259, 267, 269, 278, 280, 285, 290, 296, 315, 324: 1, 335, 340;

[0133] CI Acid Green 1, 3, 5, 6, 7, 8, 9, 11, 13, 14, 15, 16, 22, 25, 27, 28, 41, 50, 50: 1, 58, 63, 65, 80, 104, 105, 106, 109, etc. CI acid dyes

[0134] 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;

[0135] 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;

[0136] CI direct orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107;

[0137] CI Direct Violet 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104;

[0138] 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, 16 7, 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;

[0139] CI Direct Green includes CI direct dyes such as 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 77, 79, and 82.

[0140] CI Disperse Yellow 51, 54, 76;

[0141] CI Disperse Violet 26, 27;

[0142] CI disperse blue 1, 14, 56, 60 and other CI disperse dyes,

[0143] CI Basic Red 1, 10;

[0144] 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;

[0145] CI Basic Violet 2;

[0146] CI Basic Red 9;

[0147] CI Basic Green 1 and other CI basic dyes

[0148] CI Active Yellow 2, 76, 116;

[0149] CI Active Orange 16;

[0150] CI reactive dyes such as CI Reactive Red 36

[0151] CI Media Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65;

[0152] CI Media Red 1, 2, 3, 4, 9, 11, 12, 14, 17, 18, 19, 22, 23, 24, 25, 26, 27, 29, 30, 32, 33, 36, 37, 38, 39, 41, 42, 43, 45, 46, 48, 52, 53, 56, 62, 63, 71, 74, 76, 78, 85, 86, 88, 90, 94, 95;

[0153] CI Media Orange 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47, 48;

[0154] CI Media Purple 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;

[0155] CI Media 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;

[0156] CI mordant green dyes include 1, 3, 4, 5, 10, 13, 15, 19, 21, 23, 26, 29, 31, 33, 34, 35, 41, 43, and 53.

[0157] CI vat green 1 and other CI vat dyes, etc.

[0158] These dyes can be appropriately selected to match the spectroscopic spectrum of the desired color filter.

[0159] As for pigment (A2), there are no particular limitations, and well-known pigments can be used, for example, pigments classified as pigments in the Color Index (published by The Society of Dyers and Colourists).

[0160] As pigments, examples include CI pigments yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 194, 214, etc.

[0161] CI pigments include orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73, and other orange pigments;

[0162] CI pigments include red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 180, 192, 209, 215, 216, 224, 242, 254, 255, 264, 265, etc.

[0163] CI pigment blue 15:6, 60 and other blue pigments;

[0164] CI pigments include purple 1, 19, 23, 29, 32, 36, 38, and other purple pigments;

[0165] CI pigments include green 7, 36, and 58, among other green pigments.

[0166] CI pigments, such as brown 23 and 25;

[0167] CI pigments, black 1, 7, and other black pigments, etc.

[0168] Pigments can be subjected to various treatments as needed, such as rosin treatment, surface treatment using pigment derivatives with introduced acidic or basic groups, grafting treatment of the pigment surface using polymeric compounds, micronization treatment based on sulfuric acid micronization, cleaning treatment based on organic solvents or water to remove impurities, and removal treatment of ionic impurities based on ion exchange.

[0169] The pigment is preferably of uniform particle size. Furthermore, by dispersing the pigment with a pigment dispersant, a pigment dispersion in which the pigment is uniformly dispersed in the solution can be obtained.

[0170] Examples of pigment dispersants include cationic, anionic, nonionic, amphoteric, polyester, polyamine, and acrylic surfactants. These pigment dispersants can be used alone or in combination of two or more. Examples of pigment dispersants by trade name include KP (Shin-Etsu Chemical Co., Ltd.), FLOWLEN (Kyoeisha Chemical Co., Ltd.), Solsperse (Lubrizol Corporation), EFKA (CIBA Corporation), AJISPER (Ajinomoto Fine Chemicals Co., Ltd.), and Disperbyk (BYK-Chemie Corporation). The pigment dispersant may be included in the coloring and curing resin composition as the same component as the dispersant (P) described later, or as a different component from the dispersant (P) described later.

[0171] When using a pigment dispersant, its amount relative to the total amount of pigment (A2) is preferably 1% to 100% by mass, more preferably 5% to 50% by mass. When the amount of pigment dispersant used is within the above range, there is a tendency to obtain a pigment dispersion in a uniformly dispersed state.

[0172] The content of colorant (A) in the coloring curable resin composition is preferably 0.1% to 70% by mass relative to the total amount of solid components, more preferably 0.5% to 60% by mass, and even more preferably 1% to 50% by mass. When the content of colorant (A) is within the above range, the color concentration when the filter is made is sufficient, and the composition contains the required amount of resin (B) and polymeric compound (C), thus enabling the formation of patterns with sufficient mechanical strength.

[0173] Here, "total solids content" in this specification refers to the amount obtained by removing the solvent content from the total amount of the coloring and curing resin composition. The total solids content and the content of each component relative to that total solids content can be determined, for example, using known analytical methods such as liquid chromatography or gas chromatography.

[0174] <Dispersant (P)>

[0175] The dispersant (P) is not particularly limited as long as it is a dispersant used to disperse colorants, but it has an amine value exceeding 0 mg KOH / g and less than 30 mg KOH / g, preferably 0.5 mg KOH / g to 25 mg KOH / g, more preferably 1 mg KOH / g to 15 mg KOH / g, and even more preferably less than 10 mg KOH / g. In the present invention, when a color-curing resin composition is prepared by mixing or dispersing a dispersant with an amine value of 0, foreign matter may sometimes form in the coating film using the color-curing resin composition, making it impossible to produce a suitable coating film. In addition, in the present invention, when a color-curing resin composition is prepared by mixing or dispersing a dispersant with an amine value exceeding 30 mg KOH / g, the heat resistance of the coating film using the color-curing resin composition may sometimes be insufficient. Here, "color-curing resin composition prepared by mixing or dispersing a dispersant" refers to a color-curing resin composition obtained by pre-mixing and dispersing the dispersant in a colorant and solvent to form a dispersion and then mixing it with other components, or a color-curing resin composition obtained by directly mixing the dispersant with other components.

[0176] As a dispersant (P), for example, polymeric dispersants can be cited.

[0177] The dispersant (P) mentioned above is a different component from the resin (B) described later, and may also differ in amine value and / or acid value.

[0178] Examples of such polymeric dispersants include acrylic dispersants and polyurethane dispersants.

[0179] As an acrylic dispersant, examples include acrylic block copolymers. Among acrylic block copolymers, it is preferable to use colorant adsorption blocks that further contain acid groups as colorant adsorption groups on colorant adsorption blocks containing basic groups as colorant adsorption groups (also known as dye adsorption groups), and block copolymers that do not contain colorant adsorption groups.

[0180] As a colorant adsorption block that further contains an acid group on a colorant adsorption block containing a basic group as the above-mentioned colorant adsorption group, an example is a block formed by using a monomer with an acid group together with a monomer having a basic group.

[0181] The monomers with basic groups mentioned above are monomers having primary, secondary, tertiary, or quaternary ammonium groups.

[0182] Specifically, examples include N,N-dimethylaminoethyl (meth)acrylate, N,N-diethylaminoethyl (meth)acrylate, N,N-dimethylacrylamide, diethylacrylamide, dimethylaminopropylmethacrylamide, acryloylmorpholine, vinylimidazole, 2-vinylpyridine, monomers with amino and caprolactone skeletons, glycidyl acrylate and other monomers with glycidyl groups reacting with compounds having one secondary amino group, and (meth)acryloylalkyl isocyanate compounds reacting with 4-(2-aminomethyl)-pyridine, 4-(2-aminoethyl)-pyridine, 4-(2-hydroxyethyl)pyridine, 1-(2-aminoethyl)-piperazine, 2-amino-6-methoxybenzothiazole, 1-(2-hydroxyethylimidazole), N,N-diallyl melamine, and N,N-dimethyl-1,3-propanediamine, etc.

[0183] As monomers with acidic groups, they are monomers with carboxyl, sulfonic acid, or phosphoric acid groups. Specifically, examples of monomers with carboxyl groups include unsaturated monocarboxylic acid compounds such as acrylic acid, methacrylic acid, and crotonic acid, as well as unsaturated dicarboxylic acid compounds and their half-esters such as maleic acid, fumaric acid, and itaconic acid. Examples of monomers with sulfonic acid groups include 2-acrylamido-2-methyl-1-propanesulfonic acid, 2-methacrylamido-2-methyl-1-propanesulfonic acid, and styrene sulfonic acid. Examples of monomers with phosphoric acid groups include acid phosphono(meth)acrylate and acid (meth)acrylate phosphonoethyl ester.

[0184] Examples of components that are blocks without colorant adsorption groups include aromatic vinyl compounds such as styrene, α-methylstyrene, and vinyltoluene; unsaturated alkyl carboxylic acids such as methyl methacrylate, ethyl methacrylate, and butyl methacrylate; unsaturated aryl alkyl carboxylic acids such as benzyl methacrylate; monomers containing polycaprolactone; and polyalkylene glycol monoester monomers.

[0185] The aforementioned acrylic block copolymers can be obtained by living anionic polymerization or other methods, and conventionally known polymerization methods can be used.

[0186] The amine value of the above-mentioned acrylic block copolymer exceeds 0 mg KOH / g and is below 30 mg KOH / g, preferably 0.5 mg KOH / g to 15 mg KOH / g.

[0187] It should be noted that the amine value refers to the amine value per 1g of solid component of the acrylic block copolymer. It is determined by potentiometric titration using a 0.1mol / L hydrochloric acid aqueous solution (e.g., COMTITE (AUTO TITRATOR COM-900, BURET B-900, TITSTATIO NK-900), manufactured by Hiranuma Kogyo Co., Ltd.), and then converted to the equivalent of potassium hydroxide.

[0188] Commercially available examples of the aforementioned acrylic block copolymers include “Disperbyk-2000 (amine value 4 mg KOH / g)”, “Disperbyk-2001 (amine value 29 mg KOH / g)”, “Disperbyk-2009 (amine value 4 mg KOH / g)”, “Disperbyk-2050 (amine value 30 mg KOH / g)”, and “Disperbyk-2070 (amine value 20 mg KOH / g)” manufactured by BYK-Chemie Japan.

[0189] As the aforementioned polyurethane-based dispersant, substances obtained by reacting compounds with a number average molecular weight of 300 to 10,000 having one or more hydroxyl groups and compounds containing basic functional groups that can react with isocyanate groups with the isocyanate groups of polyisocyanate compounds can be utilized. As a method for obtaining such a polyurethane-based dispersant, the method described in Japanese Patent Application Publication No. 60-166318, etc., can be employed.

[0190] Examples of polyisocyanate compounds constituting the above-mentioned polyurethane dispersants include isocyanate compounds having two or more isocyanate groups, such as 2,4-toluene diisocyanate, dimers of 2,4-toluene diisocyanate, 2,6-toluene diisocyanate, p-xylene diisocyanate, m-xylene diisocyanate, 4,4'-diphenylmethane diisocyanate, 1,5-naphthalene diisocyanate, 3,3'-dimethylbiphenyl-4,4'-diisocyanate, and other aromatic diisocyanate compounds; hexamethylene diisocyanate, isophorone, etc. Diisocyanates, 4,4'-methylenebis(cyclohexyl isocyanate), methylcyclohexane-2,4 (or 2,6)-diisocyanate, 1,3-(isocyanate methylene)cyclohexane, and other aliphatic or alicyclic polyisocyanates; polyisocyanates based on the above diisocyanates having isocyanuric acid groups (such as polyisocyanates with isocyanuric acid groups formed by trimerization of the above diisocyanates), polyisocyanates obtained by reacting diisocyanates with polyols, and polyisocyanates obtained by reacting diisocyanate compounds with biuret. Among the above polyisocyanate compounds, for example, toluene diisocyanate, isophorone diisocyanate, and other diisocyanates based on diisocyanates having isocyanuric acid groups are preferred.

[0191] Compounds having one or more hydroxyl groups within their molecules that constitute the above-mentioned polyurethane dispersants include, for example, polyether compounds and polyester compounds.

[0192] Examples of the aforementioned polyether compounds include, for instance, polyalkylene glycols such as polyethylene glycol, polypropylene glycol, polybutane glycol, and polytetramethylene glycol; alkylene glycols such as ethylene glycol, propane glycol, propylene glycol, tetramethylene glycol, pentamethylene glycol, hexane glycol, neopentyl glycol, glycerol, trimethylolpropane, pentaerythritol, diglycerol, di(trimethylol)propane, and dipentaerythritol; and low-molecular-weight monohydric alcohols such as methanol and ethanol, including ethylene oxide modified compounds, propylene oxide modified compounds, butane oxide modified compounds, and tetrahydrofuran modified compounds.

[0193] Examples of the aforementioned polyester compounds include, for instance, ε-caprolactone modified compounds, γ-butyrolactone modified compounds, δ-valerate modified compounds, and methylvalerate modified compounds of alkylene glycols such as ethylene glycol, propanediol, propylene glycol, tetramethylene glycol, pentamethylene glycol, hexanediol, neopentyl glycol, glycerol, trimethylolpropane, pentaerythritol, diglycerol, di(trimethylol)propane, and dipentaerythritol, as well as low molecular weight monohydric alcohols such as methanol and ethanol; and esterifications of aliphatic dicarboxylic acids such as adipic acid and dimer acids with polyols such as neopentyl glycol and methylpentyl glycol. Polyester polyols; polyester polyols such as aromatic polyester polyols that are esterifications of aromatic dicarboxylic acids such as terephthalic acid and polyols such as neopentyl glycol; polycarbonate polyols, acrylic polyols, polytetramethylene hexaglycerol ether (a tetrahydrofuran-modified hexaglycerol) and esterifications of dicarboxylic acids such as fumaric acid, phthalic acid, isophthalic acid, itaconic acid, adipic acid, sebacic acid, and maleic acid; and compounds containing multiple hydroxyl groups, such as monoglycerides, obtained by transesterification of compounds containing multiple hydroxyl groups, such as glycerol, with fatty acid esters. Among the above compounds having one or more hydroxyl groups in the molecule, ε-caprolactone adducts of alcohols are preferred.

[0194] The number-average molecular weight of the compounds having one or more hydroxyl groups is, for example, 300 to 10,000, preferably 300 to 6,000. It should be noted that the number-average molecular weight can be determined by column chromatography.

[0195] The compounds constituting the aforementioned polyurethane-based dispersants, which contain basic groups and have functional groups capable of reacting with isocyanate groups, are not particularly limited, but are preferably selected from at least one compound among polyols, polythiols, and amines having N,N-disubstituted amino groups or heterocyclic nitrogen atoms. Compounds conventionally known in the art of dispersants can be used as these compounds. These compounds have a Zerewitinoff active hydrogen atom and at least one basic group containing a nitrogen atom. Examples of such compounds include N,N-dimethyl-1,3-propanediamine, N,N-diethyl-1,4-butanediamine, 2-dimethylaminoethanol, 1-(2-aminoethyl)-piperazine, 2-(1-pyrrolyl)-ethylamine, 4-amino-2-methoxypyrimidine, 4-(2-aminoethyl)-pyridine, 1-(2-hydroxyethyl)-piperazine, 4-(2-hydroxyethyl)-morpholine, 2-mercaptopyrimidine, 2-mercaptobenzimidazole, 2-amino-6-methoxybenzothiazole, N,N-diallyl-melamine, 3-amino-1,2,4-triazole, 1-(2-hydroxyethyl)-imidazole, and 3-mercapto-1,2,4-triazole. Among these, amines having a heterocyclic nitrogen atom are preferred.

[0196] The reaction in the synthesis of the above-mentioned polyurethane-based dispersant is not particularly limited and can be carried out using conventionally known methods. Furthermore, the amine value of the above-mentioned polyurethane-based dispersant is greater than 0 mg KOH / g and less than 30 mg KOH / g, preferably 0.5 mg KOH / g to 15 mg KOH / g.

[0197] In addition, commercially available products as the aforementioned polyurethane-based dispersants include Disperbyk-161 (amine value 11 mg KOH / g, manufactured by BYK-Chemie), Disperbyk-162 (amine value 13 mg KOH / g, manufactured by BYK-Chemie), Disperbyk-167 (amine value 13 mg KOH / g, manufactured by BYK-Chemie), Disperbyk-182 (amine value 13 mg KOH / g, manufactured by BYK-Chemie), Disperbyk-2163 (amine value 10 mg KOH / g, manufactured by BYK-Chemie), and Disperbyk-2164 (amine value 14 mg KOH / g, manufactured by BYK-Chemie).

[0198] The dispersant is preferably the above-mentioned acrylic dispersant, and the dispersant preferably has a basic functional group with a tertiary amino group or a nitrogen-containing heterocyclic group (e.g., pyridine, pyrimidine, pyrazine, isocyanate), and more preferably has a tertiary amino group.

[0199] The content of the dispersant relative to 100 parts by weight of the colorant is preferably 0.1 to 50 parts by weight, more preferably 1 to 45 parts by weight, further preferably 2 to 40 parts by weight, even more preferably 3 to 35 parts by weight, particularly preferably 4 to 30 parts by weight, and may also be less than 20 parts by weight or less than 10 parts by weight.

[0200] The content of the dispersant in 100% by mass of the solids component of the coloring and curing resin composition is preferably 0.001 to 5% by mass, more preferably 0.05 to 3% by mass, and even more preferably 0.10 to 1% by mass.

[0201] From the viewpoint of improving processability, it is preferable to mix the dispersant with the solvent (hereinafter also referred to as a solution containing the dispersant) before mixing with other components.

[0202] In a solution containing a dispersant, the content of the dispersant, expressed in terms of solids, is, for example, 10 to 60% by mass, preferably 20 to 50% by mass.

[0203] In this invention, the lower the amine value of the dispersant and the lower the content of the dispersant, the more effective the colorant dispersion treatment is, and the better it can prevent fading, improve absorbance retention and contrast.

[0204] The colorant may be contained in a dispersant or in a dispersion formed by dispersing a solution containing a dispersant in a solvent, and the dispersion may be used in a color-curing resin composition.

[0205] <Resin (B)>

[0206] The resin (B) is not particularly limited, but an alkali-soluble resin is preferred. Examples of resin (B) include resins [K1] to [K6].

[0207] Resin [K1]: A copolymer having structural units derived from at least one (a) selected from unsaturated carboxylic acids and unsaturated carboxylic anhydrides (hereinafter sometimes referred to as "(a)") and structural units derived from monomers (b) having a cyclic ether structure having 2 to 4 carbon atoms and an olefinic unsaturated bond (hereinafter sometimes referred to as "(b)");

[0208] Resin [K2]: A copolymer having structural units from (a), structural units from (b), and structural units from monomer (c) (which is different from (a) and (b)) (hereinafter sometimes referred to as "(c)");

[0209] Resin [K3]: A copolymer having structural units from (a) and structural units from (c);

[0210] Resin [K4]: A copolymer having a structural unit obtained by adding (b) with a structural unit from (a) and a structural unit from (c);

[0211] Resin [K5]: A copolymer having structural units obtained by adding structural units (a) to structural units from (b) and structural units from (c);

[0212] Resin [K6]: A copolymer having a structural unit obtained by adding (a) to a structural unit from (b), and further adding to a carboxylic anhydride, and a structural unit from (c).

[0213] As for (a), specifically, examples include unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, o-vinylbenzoic acid, m-vinylbenzoic acid, and p-vinylbenzoic acid;

[0214] Unsaturated dicarboxylic acids such as maleic acid, fumaric acid, citraconic acid, zeaxanthin, itaconic acid, 3-vinyl phthalic acid, 4-vinyl phthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyltetrahydrophthalic acid, and 1,4-cyclohexene dicarboxylic acid.

[0215] 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, 5-carboxy-6-ethylbicyclo[2.2.1]hept-2-ene, etc., are bicyclic unsaturated compounds containing carboxyl groups;

[0216] Maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinyl phthalic anhydride, 4-vinyl phthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, bicyclo[2.2.1]hept-2-ene-5,6-dicarboxylic anhydride and other unsaturated dicarboxylic anhydrides;

[0217] Unsaturated mono[(meth)acryloyloxyethyl] esters of polycarboxylic acids with two or more members, such as mono[2-(meth)acryloyloxyethyl] ester of succinate and mono[2-(meth)acryloyloxyethyl] ester of phthalate.

[0218] Unsaturated acrylates containing both hydroxyl and carboxyl groups in the same molecule, such as α-(hydroxymethyl)acrylic acid; etc.

[0219] Among these, considering the copolymerization reactivity and the solubility of the resulting resin in alkaline aqueous solution, acrylic acid, methacrylic acid, and maleic anhydride are preferred.

[0220] (b) For example, it refers to a polymeric compound having a cyclic ether structure having 2 to 4 carbon atoms (e.g., selected from at least one of oxecyclopropane ring, oxecyclobutane ring, and tetrahydrofuran ring) and an olefinic unsaturated bond. (b) Preferably, it is a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth)acryloyloxy group.

[0221] As (b), examples include monomers having oxetyl and olefinic unsaturated bonds (b1) (hereinafter sometimes referred to as "(b1)"), monomers having oxetyl and olefinic unsaturated bonds (b2) (hereinafter sometimes referred to as "(b2)"), and monomers having tetrahydrofuranyl and olefinic unsaturated bonds (b3) (hereinafter sometimes referred to as "(b3)").

[0222] As (b1), for example, examples include monomers (b1-1) (hereinafter sometimes referred to as "(b1-1)") having a structure in which aliphatic unsaturated hydrocarbons are epoxidized in a straight or branched manner, and monomers (b1-2) (hereinafter sometimes referred to as "(b1-2)") having a structure in which alicyclic unsaturated hydrocarbons are epoxidized.

[0223] Examples of (b1-1) include glycidyl (meth)acrylate, β-methyl glycidyl (meth)acrylate, β-ethyl glycidyl (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, and 2,3-bis(meth)acrylate. (Epoxypropoxymethyl)styrene, 2,4-bis(epoxypropoxymethyl)styrene, 2,5-bis(epoxypropoxymethyl)styrene, 2,6-bis(epoxypropoxymethyl)styrene, 2,3,4-tris(epoxypropoxymethyl)styrene, 2,3,5-tris(epoxypropoxymethyl)styrene, 2,3,6-tris(epoxypropoxymethyl)styrene, 3,4,5-tris(epoxypropoxymethyl)styrene, 2,4,6-tris(epoxypropoxymethyl)styrene, etc.

[0224] Examples of (b1-2) include vinylcyclohexene monooxide, 1,2-epoxy-4-vinylcyclohexane (e.g., Celloxide 2000; manufactured by Daicel Co., Ltd.), methyl 3,4-epoxycyclohexyl methacrylate (e.g., Cyclomer A400; manufactured by Daicel Co., Ltd.), methyl 3,4-epoxycyclohexyl methacrylate (e.g., Cyclomer M100; manufactured by Daicel Co., Ltd.), compounds represented by formula (I), and compounds represented by formula (II).

[0225]

[0226] In equations (I) and (II), R a and R b It refers to an alkyl group having 1 to 4 hydrogen atoms or carbon atoms, wherein the hydrogen atoms in the alkyl group can be replaced by hydroxyl groups.

[0227] X a and X b Indicates a single bond, *-R c -、*-R c -O-、*-R c -S- or *-R c -NH-.

[0228] R cIt represents alkyl diols with 1 to 6 carbon atoms.

[0229] * Indicates the binding site with O.

[0230] Examples of alkyl groups having 1 to 4 carbon atoms include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, and tert-butyl.

[0231] Examples of alkyl groups in which hydrogen atoms are replaced by hydroxyl groups include hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 1-hydroxypropyl, 2-hydroxypropyl, 3-hydroxypropyl, 1-hydroxy-1-methylethyl, 2-hydroxy-1-methylethyl, 1-hydroxybutyl, 2-hydroxybutyl, 3-hydroxybutyl, and 4-hydroxybutyl.

[0232] As R a and R b Examples of suitable materials include hydrogen atoms, methyl groups, hydroxymethyl groups, 1-hydroxyethyl groups, and 2-hydroxyethyl groups; examples of more suitable materials include hydrogen atoms and methyl groups.

[0233] Examples of alkyl dimethyl groups include methylene, ethylene, propane-1,2-dimethyl, propane-1,3-dimethyl, butane-1,4-dimethyl, pentane-1,5-dimethyl, and hexane-1,6-dimethyl.

[0234] As X a and X b Examples of preferred components include single bonds, methylene, ethylene, *-CH2-O- and *-CH2CH2-O-, and examples of more preferred components include single bonds and *-CH2CH2-O- (* indicates the bonding site with O).

[0235] Examples of compounds represented by formula (I) include compounds represented by any of formulas (I-1) to (I-15). Among these, compounds represented by formulas (I-1), (I-3), (I-5), (I-7), (I-9), or (I-11) to (I-15) are preferred, and compounds represented by formulas (I-1), (I-7), (I-9), or (I-15) are more preferred.

[0236]

[0237]

[0238] Examples of compounds represented by formula (II) include compounds represented by any of formulas (II-1) to (II-15). Among these, compounds represented by formulas (II-1), (II-3), (II-5), (II-7), (II-9), or (II-11) to (II-15) are preferred, and compounds represented by formulas (II-1), (II-7), (II-9), or (II-15) are more preferred.

[0239]

[0240] The compounds represented by formula (I) and formula (II) may be used individually or in combination of two or more. When the compounds represented by formula (I) and formula (II) are used together, their content ratio [compound represented by formula (I):compound represented by formula (II)] on a molar basis is preferably 5:95 to 95:5, more preferably 20:80 to 80:20.

[0241] As (b2), monomers having an oxetyl group and a (meth)acryloyloxy group are more preferred. Examples of (b2) include 3-methyl-3-methacryloyloxymethyloxetane, 3-methyl-3-acryloyloxymethyloxetane, 3-ethyl-3-methacryloyloxymethyloxetane, 3-ethyl-3-acryloyloxymethyloxetane, 3-methyl-3-methacryloyloxyethyloxetane, 3-methyl-3-acryloyloxyethyloxetane, 3-ethyl-3-methacryloyloxyethyloxetane, 3-ethyl-3-acryloyloxyethyloxetane, etc.

[0242] As (b3), monomers having tetrahydrofuranyl and (meth)acryloyloxy groups are more preferred. Specifically, examples of (b3) include tetrahydrofurfuryl acrylate (e.g., Viscoat V#150, manufactured by Osaka Organic Chemicals Co., Ltd.), tetrahydrofurfuryl methacrylate, etc.

[0243] As for (b), (b1) is preferred in terms of further improving the reliability of the obtained color filter, such as its heat resistance and chemical resistance. Furthermore, (b1-2) is more preferred in terms of excellent storage stability of the color-curing resin composition.

[0244] Examples of (c) include methyl methacrylate, ethyl methacrylate, n-butyl methacrylate, sec-butyl methacrylate, tert-butyl methacrylate, 2-ethylhexyl methacrylate, dodecyl methacrylate, lauryl methacrylate, stearyl methacrylate, cyclopentyl methacrylate, cyclohexyl methacrylate, 2-methylcyclohexyl methacrylate, and tricyclo[5.2.1.0] 2,6 ] Decane-8-yl ester (in this technical field, it is commonly referred to as "(meth)acrylate dicyclopentyl ester". Additionally, it is sometimes called "(meth)acrylate tricyclodecyl ester"), (meth)acrylate tricyclo[5.2.1.0] 2,6 Decen-8-yl ester (in this technical field, it is commonly referred to as "(meth)acrylate dicyclopentenyl ester"), (meth)acrylate dicyclopentoxyethyl ester, (meth)acrylate isobornyl ester, (meth)acrylate adamantane ester, (meth)acrylate allyl ester, (meth)acrylate propargyl ester, (meth)acrylate phenyl ester, (meth)acrylate naphthyl ester and (meth)acrylate benzyl ester, etc. (meth)acrylates;

[0245] 2-Hydroxyethyl methacrylate, 2-Hydroxypropyl methacrylate, and other methacrylates containing hydroxyl groups;

[0246] Dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate, and diethyl itaconic acid;

[0247] Bicyclo[2.2.1]hept-2-ene, 5-methylbicyclo[2.2.1]hept-2-ene, 5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxybicyclo[2.2.1]hept-2-ene, 5-hydroxymethylbicyclo[2.2.1]hept-2-ene, 5-(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5-methoxybicyclo[2.2.1]hept-2-ene, 5-ethoxybicyclo[2.2.1]hept-2-ene, 5,6-dihydroxybicyclo[2.2.1]hept-2-ene, 5,6-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 Bicyclic unsaturated compounds such as cyclo[2.2.1]hept-2-ene, 5,6-diethoxybicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxymethyl-5-methylbicyclo[2.2.1]hept-2-ene, 5-tert-butoxycarbonylbicyclo[2.2.1]hept-2-ene, 5-cyclohexyloxycarbonylbicyclo[2.2.1]hept-2-ene, 5-phenoxycarbonylbicyclo[2.2.1]hept-2-ene, 5,6-bis(tert-butoxycarbonyl)bicyclo[2.2.1]hept-2-ene, and 5,6-bis(cyclohexyloxycarbonyl)bicyclo[2.2.1]hept-2-ene;

[0248] Dicarbonyl imide derivatives such as N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimide-3-maleimide benzoate, N-succinimide-4-maleimide butyrate, N-succinimide-6-maleimide hexanoate, N-succinimide-3-maleimide propionate, and N-(9-acridyl)maleimide;

[0249] Styrene, α-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, p-methoxystyrene, acrylonitrile, methacrylonitrile, vinyl chloride, vinylidene chloride, acrylamide, methacrylamide, vinyl acetate, 1,3-butadiene, isoprene, 2,3-dimethyl-1,3-butadiene, etc.

[0250] Among them, considering copolymerization reactivity and heat resistance, preferred materials include 2-hydroxyethyl methacrylate, styrene, vinyltoluene, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo[2.2.1]hept-2-ene, and 2-ethylhexyl methacrylate.

[0251] In resin [K1], the ratio of structural units from each monomer is preferably 2 to 60 mol% from (a) and 40 to 98 mol% from (b) among all structural units constituting resin [K1], more preferably 10 to 50 mol% from (a) and 50 to 90 mol% from (b).

[0252] When the ratio of the structural units of resin [K1] is within the above range, there is a tendency for the color curable resin composition to have excellent storage stability, developability when forming a color pattern, and solvent resistance of the resulting color filter.

[0253] The resin [K1] can be manufactured, for example, by referring to the method described in the document "Experimental Method for Polymer Synthesis" (Otsu Takayuki Publishing Co., Ltd. Chemical Dojin 1st Edition 1st Printing, March 1, 1972) and the references described in that document.

[0254] Specifically, the following method can be used: A specified amount of (a) and (b), the polymerization initiator, and the solvent are loaded into a reaction vessel. For example, a deoxygenated atmosphere is created by replacing oxygen with nitrogen. The mixture is stirred while being heated and kept at a constant temperature. It should be noted that the polymerization initiator and solvent used herein are not particularly limited; commonly used polymerization initiators and solvents in this field can be used. For example, as polymerization initiators, examples include azo compounds (2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylpentanonitrile) etc.) and organic peroxides (benzoyl peroxide, etc.). As solvents, any solvent capable of dissolving the monomers is acceptable; examples include the solvents described later as solvent (E) for the coloring and curing resin composition of the present invention.

[0255] It should be noted that the obtained copolymer can be used directly from the reaction solution, or from a concentrated or diluted solution, or from a substance extracted in solid (powder) form by methods such as reprecipitation. In particular, by using the solvent contained in the coloring and curing resin composition of the present invention as a solvent during the polymerization, the reaction solution can be directly used to prepare the coloring and curing resin composition of the present invention, thus simplifying the manufacturing process of the coloring and curing resin composition of the present invention.

[0256] In resin [K2], the ratio of structural units from each monomer among all structural units constituting resin [K2] is preferably 2 to 45 mol% from (a), 2 to 95 mol% from (b), and 1 to 65 mol% from (c), more preferably 5 to 40 mol% from (a), 5 to 80 mol% from (b), and 5 to 60 mol% from (c).

[0257] When the ratio of the structural units of resin [K2] is within the above range, there is a tendency for the color curable resin composition to have excellent storage stability, developability when forming color patterns, and solvent resistance, heat resistance and mechanical strength of the resulting color filter.

[0258] Resin [K2] can be manufactured, for example, in the same manner as the method described in the manufacturing method of resin [K1].

[0259] In resin [K3], the ratio of structural units from each monomer is preferably 2 to 60 mol% from (a) and 40 to 98 mol% from (c) among all structural units constituting resin [K3], more preferably 10 to 50 mol% from (a) and 50 to 90 mol% from (c).

[0260] Resin [K3] can be manufactured, for example, in the same manner as the method described in the manufacturing method of resin [K1].

[0261] The resin [K4] can be manufactured by obtaining a copolymer of (a) and (c) and adding the cyclic ether having 2 to 4 carbon atoms in (b) to the carboxylic acid and / or carboxylic anhydride in (a).

[0262] First, the copolymer of (a) and (c) is manufactured in the same manner as described in the method for manufacturing resin [K1]. In this case, the ratio of structural units from each monomer is preferably the same as the ratio mentioned in resin [K3].

[0263] Next, the cyclic ether having 2 to 4 carbon atoms in (b) is reacted with a portion of the carboxylic acid and / or carboxylic anhydride from (a) in the copolymer described above.

[0264] After producing the copolymer of (a) and (c), the atmosphere inside the flask is replaced with air instead of nitrogen, and (b), a reaction catalyst (e.g., tris(dimethylaminomethyl)phenol) and a polymerization inhibitor (e.g., hydroquinone) are placed inside the flask. For example, the reaction is carried out at 60 to 130°C for 1 to 10 hours, thereby producing resin [K4].

[0265] The amount of (b) used relative to 100 moles of (a) is preferably 5 to 80 moles, more preferably 10 to 75 moles. Within this range, there is a tendency for a good balance to be achieved in terms of the storage stability of the coloring and curing resin composition, the developability when forming a pattern, and the solvent resistance, heat resistance, mechanical strength, and sensitivity of the resulting pattern. From the perspective of the high reactivity of cyclic ethers and the low likelihood of unreacted (b) residue, (b1) is preferred as (b) used in resin [K4], and more preferably (b1-1).

[0266] The amount of the above-mentioned reaction catalyst used is preferably 0.001 to 5 parts by mass relative to the total mass of (a), (b), and (c) 100 parts by mass. The amount of the above-mentioned polymerization inhibitor used is preferably 0.001 to 5 parts by mass relative to the total mass of (a), (b), and (c) 100 parts by mass.

[0267] The reaction conditions, such as the feeding method, reaction temperature, and time, can be appropriately adjusted taking into account the manufacturing equipment and the calorific value of polymerization. It should be noted that the feeding method and reaction temperature can be appropriately adjusted, similarly to the polymerization conditions, taking into account the manufacturing equipment and the calorific value of polymerization.

[0268] For resin [K5], as a first stage, copolymers (b) and (c) are obtained in the same manner as resin [K1] described above. Similarly, for the obtained copolymer, the solution after the reaction can be used directly, or a concentrated or diluted solution can be used, or a substance extracted in solid (powder) form using methods such as reprecipitation can be used.

[0269] The ratio of structural units from (b) and (c) relative to the total molar number of all structural units constituting the copolymer is preferably 5-95 mol% from (b) and 5-95 mol% from (c), more preferably 10-90 mol% from (b) and 10-90 mol% from (c).

[0270] Furthermore, under the same conditions as the manufacturing method of resin [K4], the carboxylic acid or carboxylic anhydride contained in (a) is reacted with the cyclic ether from (b) contained in the copolymer of (b) and (c), thereby obtaining resin [K5].

[0271] The amount of (a) reacting with the above copolymer is preferably 5 to 80 moles relative to 100 moles of (b). Given the high reactivity of cyclic ethers and the low likelihood of unreacted (b) residue, (b1) is preferred as (b1) for use in resin [K5], and more preferably (b1-1).

[0272] Resin [K6] is a resin obtained by further reacting carboxylic anhydride with resin [K5]. The carboxylic anhydride is reacted with a hydroxyl group generated from the reaction of a cyclic ether with a carboxylic acid or a carboxylic anhydride.

[0273] Examples of carboxylic anhydrides include maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, and bicyclo[2.2.1]hept-2-ene-5,6-dicarboxylic anhydride. The amount of carboxylic anhydride used is preferably 0.5 to 1 mole relative to the amount used in (a).

[0274] As resin (B), examples specifically include methyl 3,4-epoxycyclohexyl methacrylate / (meth)acrylate copolymer and 3,4-epoxytricyclic methacrylate [5.2.1.0]. 2,6 Resins such as decyl acrylate / (meth)acrylic acid copolymer [K1]; glycidyl acrylate / benzyl acrylate / (meth)acrylic acid copolymer, glycidyl acrylate / styrene / (meth)acrylic acid copolymer, 3,4-epoxy tricyclic acrylic acid [5.2.1.0] 2,6 ] Decyl acrylate / (meth)acrylic acid / N-cyclohexylmaleimide copolymer, 3,4-epoxy tricyclic acrylate [5.2.1.0] 2,6 Resins such as decyl acrylate / (meth)acrylic acid / N-cyclohexylmaleimide / (meth)acrylic acid 2-hydroxyethyl ester copolymer, 3-methyl-3-(meth)acryloyloxymethyloxetane / (meth)acrylic acid / styrene copolymer [K2]; resins such as benzyl acrylate / (meth)acrylic acid copolymer, styrene / (meth)acrylic acid copolymer [K3]; resins obtained by adding glycidyl methacrylate to benzyl acrylate / (meth)acrylic acid copolymer, resins obtained by adding glycidyl methacrylate to tricyclodecyl acrylate / styrene ... / (meth)acrylic acid copolymer, resins obtained by adding glycidyl methacrylate to tricyclodecyl acrylate / (meth)acrylic acid / (meth)acrylic acid copolymer, resins obtained by adding glycidyl methacrylate Resins such as those obtained by adding glycidyl methacrylate to a copolymer of tricyclodecyl methacrylate / benzyl methacrylate / methacrylic acid [K4]; resins obtained by reacting a copolymer of tricyclodecyl methacrylate / methacrylic acid and glycidyl methacrylate; resins obtained by reacting a copolymer of tricyclodecyl methacrylate / styrene / glycidyl methacrylate with a copolymer of tricyclodecyl methacrylate / styrene / glycidyl methacrylate [K5]; and resins obtained by further reacting a resin obtained by reacting a copolymer of tricyclodecyl methacrylate / methacrylic acid and glycidyl methacrylate with tetrahydrophthalic anhydride [K6].

[0275] Among them, resin [K1] and resin [K2] are preferred as resin (B), and resin [K1] is particularly preferred.

[0276] The weight-average molecular weight of the polystyrene-converted 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 molecular weight is within the above range, there is a trend of increased hardness of the color filter, high residual film rate, good solubility of the unexposed portion in the developer, and improved resolution of the colored pattern.

[0277] The dispersion of resin (B) [weight average molecular weight (Mw) / number average molecular weight (Mn)] is preferably 1.1 to 6, more preferably 1.2 to 4.

[0278] The acid value of resin (B), converted from solid content, is preferably 10 to 170 mg KOH / g, more preferably 20 to 150 mg KOH / g, and even more preferably 30 to 135 mg KOH / g. Here, the acid value is a value determined as the amount (mg) of potassium hydroxide required to neutralize 1 g of resin (B), and can be obtained, for example, by titration using an aqueous solution of potassium hydroxide.

[0279] The content of resin (B) relative to the total amount of solid components is preferably 7 to 65% by mass, more preferably 13 to 60% by mass, and even more preferably 17 to 55% by mass. When the content of resin (B) is within the above range, there is a tendency to form colored patterns, and the resolution and residual film rate of the colored patterns are improved.

[0280] <Polymerizing Compound (C)>

[0281] The polymerizable compound (C) is a compound capable of polymerization by active free radicals and / or acids generated by a polymerization initiator (D). Examples include compounds with polymerizable olefinic unsaturated bonds, preferably (meth)acrylate compounds.

[0282] The polymeric compound (C) is preferably a polymeric compound having three or more olefinic unsaturated bonds. Examples of such polymeric compounds include, for instance, trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, tripentaerythritol octa(meth)acrylate, tripentaerythritol hepta(meth)acrylate, tetrapentaerythritol deca(meth)acrylate, tetrapentaerythritol nona(meth)acrylate, tris(2-(meth)acryloyloxyethyl)isocyanurate, ethylene glycol-modified pentaerythritol tetra(meth)acrylate, ethylene glycol-modified dipentaerythritol hexa(meth)acrylate, propylene glycol-modified pentaerythritol tetra(meth)acrylate, propylene glycol-modified dipentaerythritol hexa(meth)acrylate, caprolactone-modified pentaerythritol tetra(meth)acrylate, and caprolactone-modified dipentaerythritol hexa(meth)acrylate.

[0283] Among them, dipentaerythritol penta(meth)acrylate and dipentaerythritol hexa(meth)acrylate are preferred.

[0284] The content of the polymeric compound (C) relative to the total amount of solid components is preferably 1 to 65% by mass, more preferably 5 to 60% by mass, and even more preferably 10 to 55% by mass. When the content of the polymeric compound (C) is within the above range, there is a tendency for the residual film rate during the formation of the colored pattern and the chemical resistance of the color filter to increase.

[0285] <Polymerization Initiator (D)>

[0286] The polymerization initiator (D) is not particularly limited as long as it is a compound that can generate active free radicals, acids, etc., under the action of light and heat and initiate polymerization; known polymerization initiators can be used. Examples of polymerization initiators that generate active free radicals include O-acyl oxime compounds, alkyl phenyl ketone compounds, triazine compounds, acylphosphine oxide compounds, and biimidazole compounds.

[0287] Examples of the aforementioned O-acyl oxime compounds include, for instance, N-benzoyloxy-1-(4-phenylthiophenyl)butane-1-one-2-imine, N-benzoyloxy-1-(4-phenylthiophenyl)octane-1-one-2-imine, N-benzoyloxy-1-(4-phenylthiophenyl)-3-cyclopentylpropane-1-one-2-imine, and N-acetoxy-1-(4-phenylthiophenyl)-3-cyclohexylpropane-1-one-2-imine, which are O-acyl oxime compounds with a diphenyl sulfide skeleton; N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]ethane-1-imine, and N-acetoxy-1-[9-ethyl-6-{2-yl]ethane-1-imine, etc. O-acyl oxime compounds with a carbazole skeleton, such as methyl-4-(3,3-dimethyl-2,4-dioxane-pentylmethoxy)benzoyl}-9H-carbazole-3-yl]ethane-1-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]-3-cyclopentylpropane-1-imine, N-benzoyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]-3-cyclopentylpropane-1-one-2-imine; and O-acyl oxime compounds with a fluorene skeleton, such as 1-[7-(2-methylbenzoyl)-9,9-dipropyl-9H-fluorene-2-yl]acetone-O-acetyl oxime; etc. You can also use commercially available products such as Irgacure (registered trademark) OXE01, OXE02 (all of which are manufactured by BASF), N-1919 (manufactured by ADEKA), and DFI-091 (manufactured by Daito Chemix Co., Ltd.). The O-acyl oxime compound is preferably selected from at least one of N-benzoyloxy-1-(4-phenylthiophenyl)octane-1-one-2-imine, N-acetoxy-1-(4-phenylthiophenyl)-3-cyclohexylpropane-1-one-2-imine, N-acetoxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethyl-2,4-dioxacyclopentylmethoxy)benzoyl}-9H-carbazole-3-yl]ethane-1-imine, and 1-[7-(2-methylbenzoyl)-9,9-dipropyl-9H-fluoren-2-yl]acetophenone-O-acetyl oxime. When using these O-acyl oxime compounds, there is a tendency to obtain color filters with high brightness.

[0288] Examples of the aforementioned alkyl phenyl ketone compounds include, for example, 2-methyl-2-morpholino-1-(4-methylthiophenyl)propane-1-one, 2-dimethylamino-1-(4-morpholinophenyl)-2-benzylbutane-1-one, 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholino)phenyl]butane-1-one, 2-hydroxy-2-methyl-1-phenylpropane-1-one, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy)phenyl]propane-1-one, 1-hydroxycyclohexylphenyl ketone, oligomers of 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propane-1-one, α,α-diethoxyacetophenone, and benzoyladimethyl ketal. You can also use commercially available products such as Irgacure (registered trademark) 369, 907, and 379 (all of which are manufactured by BASF).

[0289] Examples of the aforementioned triazine compounds include, for instance, 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-piperyl-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)vinyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)vinyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl)vinyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)vinyl]-1,3,5-triazine, etc.

[0290] Examples of the aforementioned acylphosphine oxide compounds include 2,4,6-trimethylbenzoyl diphenylphosphine oxide. Commercially available products such as Irgacure 819 (manufactured by BASF) can be used.

[0291] Examples of the aforementioned biimidazole compounds include, for example, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3-dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole (e.g., see Japanese Patent Application Publication Nos. 6-75372 and 6-75373), 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, and 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 (e.g., see Japanese Patent Publication No. 48-38403, Japanese Patent Application Publication No. 62-174204, etc.), and biimidazole compounds in which the phenyl group at the 4,4',5,5'-position is substituted with a carbonyl alkoxy group (e.g., see Japanese Patent Application Publication No. 7-10913, etc.).

[0292] Examples of polymerization initiators that generate acids include, for example, 4-hydroxyphenyl dimethyl sulfonium p-toluenesulfonate, 4-hydroxyphenyl dimethyl sulfonium hexafluoroantimonate, 4-acetoxyphenyl dimethyl sulfonium p-toluenesulfonate, 4-acetoxyphenyl methyl benzyl sulfonium hexafluoroantimonate, triphenyl sulfonium p-toluenesulfonate, triphenyl sulfonium hexafluoroantimonate, and diphenyl iodide. p-Toluenesulfonate, diphenyliodine Hexafluoroantimonates, etc. Salts, nitrobenzyl toluenesulfonates, benzoin toluenesulfonates, etc.

[0293] In addition, examples of polymerization initiators (D) include benzoin compounds such as benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether; benzophenone compounds such as methyl benzoyl peroxybenzoate, 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-phenanthroquinone, 2-ethylanthraquinone, and camphorquinone; and 10-butyl-2-chloroacridone, benzoyl, methyl benzoylformate, and titanium dioxide compounds.

[0294] As a polymerization initiator (D), it is preferable to have a polymerization initiator containing at least one selected from O-acyl oxime compounds, alkyl phenyl ketone compounds, triazine compounds, acylphosphine oxide compounds and bimidazole compounds, and more preferably a polymerization initiator containing an O-acyl oxime compound.

[0295] The content of polymerization initiator (D) relative to the total mass of resin (B) and polymerizable compound (C) is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass. When the content of polymerization initiator (D) is within the above range, there is a tendency to increase sensitivity and shorten the exposure time, thereby improving the productivity of the color filter.

[0296] <Solvent (E)>

[0297] The coloring and curing resin composition of the present invention contains a solvent (E). The solvent (E) is not particularly limited, and solvents commonly used in the art can be used. Examples include ester solvents (solvents containing -COO- but not -O-), ether solvents (solvents containing -O- but not -COO-), ether ester solvents (solvents containing both -COO- and -O-), ketone solvents (solvents containing -CO- but not -COO-), alcohol solvents (solvents containing OH- but not -O-, -CO-, and -COO-), aromatic hydrocarbon solvents, amide solvents, and dimethyl sulfoxide.

[0298] Examples of ester solvents include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutyrate, ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, isoamyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexanol acetate, and γ-butyrolactone.

[0299] Examples of ether solvents include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenethyl ether, and methyl anisole.

[0300] Examples of ether ester solvents include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, ethyl 2-ethoxy-2-methylpropionate, ethyl 2-methoxy-2-methylpropionate, ethyl 3-methoxybutylacetate, 3-methyl-3-methoxybutylacetate, 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.

[0301] Examples of ketone solvents include 4-hydroxy-4-methyl-2-pentanone (hereinafter sometimes referred to as diacetone alcohol), acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone, and isophorone.

[0302] Examples of alcohol solvents include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerol.

[0303] Examples of aromatic hydrocarbon solvents include benzene, toluene, xylene, and mesitylene.

[0304] Examples of amide solvents include N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.

[0305] Of the solvents mentioned above, organic solvents with a boiling point of 120°C to 180°C at 1 atm are preferred, considering their coatability and drying properties. Preferably, propylene glycol monomethyl ether acetate, ethyl lactate, propylene glycol monomethyl ether, ethyl 3-ethoxypropionate, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diacetone alcohol, and N,N-dimethylformamide are preferred. More preferably, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, diacetone alcohol, ethyl lactate, and ethyl 3-ethoxypropionate are preferred. Even more preferably, propylene glycol monomethyl ether acetate or a combination of propylene glycol monomethyl ether acetate and diacetone alcohol are preferred.

[0306] When the solvent (E) contains propylene glycol monomethyl ether acetate, the content of propylene glycol monomethyl ether acetate in the total amount of solvent (E) is preferably 40-100% by mass, more preferably 50-90% by mass, and even more preferably 60-80% by mass. The content of a solvent different from propylene glycol monomethyl ether acetate (preferably diacetone alcohol) in the total amount of solvent (E) is preferably 0-60% by mass, more preferably 10-50% by mass, and even more preferably 20-40% by mass.

[0307] The solvent (E) content relative to the total amount of the color-curing resin composition of the present invention is preferably 70 to 95% by mass, more preferably 75 to 92% by mass. In other words, the total content of the solid components of the color-curing resin composition is preferably 5 to 30% by mass, more preferably 8 to 25% by mass. When the solvent (E) content is within the above range, the flatness during coating becomes good, and the color concentration is not insufficient when forming a color filter, thus tending to improve the display properties.

[0308] <Leveling Agent (F)>

[0309] The coloring and curing resin composition of the present invention may further contain a leveling agent (F). Examples of leveling agents (F) include silicone surfactants, fluorinated surfactants, and silicone surfactants having fluorine atoms. They may have polymerizable groups on their side chains.

[0310] As organosilicon surfactants, examples include surfactants with intramolecular siloxane bonds. Specifically, examples include Toray Silicone DC3PA, Toray Silicone SH7PA, Toray Silicone DC11PA, Toray Silicone SH21PA, Toray Silicone SH28PA, Toray Silicone SH29PA, Toray Silicone SH30PA, Toray Silicone SH8400 (trade name: Dow Corning Toray Co., Ltd.), KP321, KP322, KP323, KP324, KP326, KP340, KP341 (Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452, and TSF4460 (Momentive Performance Materials Japan Co., Ltd.).

[0311] Examples of fluorinated surfactants include those with intramolecular fluorocarbon chains. Specifically, examples include FLUORAD (registered trademark) FC430, FLUORAD FC431 (manufactured by Sumitomo 3M Co., Ltd.), MEGAFAC (registered trademark) F142D, MEGAFAC F171, MEGAFAC F172, MEGAFAC F173, MEGAFAC F177, MEGAFAC F183, MEGAFAC F554, MEGAFAC R30, MEGAFAC RS-718-K (manufactured by DIC Co., Ltd.), F-top (registered trademark) EF301, F-top EF303, F-top EF351, F-top EF352 (manufactured by Mitsubishi Materials Electronics Chemicals Co., Ltd.), Surflon (registered trademark) S381, Surflon S382, Surflon SC101, and Surflon... SC105 (manufactured by AGC Corporation) and E5844 (manufactured by Daikin Fine Chemicals Research Institute Co., Ltd.), etc.

[0312] As examples of organosilicon surfactants containing fluorine atoms, surfactants with intramolecular siloxane bonds and fluorocarbon chains can be cited. Specifically, examples include MEGAFAC (registered trademark) R08, MEGAFAC BL20, MEGAFACF475, MEGAFAC F477, and MEGAFAC F443 (manufactured by DIC Corporation).

[0313] The content of leveling agent (F) relative to the total amount of the color-curing resin composition is preferably 0.001% to 0.2% by mass, more preferably 0.002% to 0.2% by mass, and even more preferably 0.005% to 0.2% by mass. It should be noted that this content does not include the content of the dispersant described above. When the content of leveling agent (F) is within the above range, the flatness of the color filter can be improved.

[0314] <Other Ingredients>

[0315] The coloring and curing resin composition of the present invention may contain, as needed, polymerization initiators, fillers, other polymer compounds, adhesion promoters, light stabilizers, chain transfer agents, and other additives known in the art.

[0316] <Method for manufacturing coloring and curing resin compositions>

[0317] The method for manufacturing the coloring and curing resin composition of the present invention includes the following steps: obtaining a dispersion (also called a colorant dispersion) formed by dispersing a colorant (A) in a solvent (E) using a dispersant (P); and adding a resin (B), a polymerizable compound (C), a polymerization initiator (D), a leveling agent (F), and other components as needed to the dispersion; wherein the colorant contains squaric acid, which has maximum absorption in the visible light region. For dyes, the amine value of the above dispersant is greater than 0 mg KOH / g and less than 30 mg KOH / g.

[0318] The coloring and curing resin composition can be prepared by mixing all the components, preferably by pre-mixing or dispersing the colorant dispersion, and more preferably by including a step of obtaining a dispersion in which the colorant (A) is dispersed in a solvent (E) by a dispersant (P). When using the dispersion, compared with the case where no dispersion is used, it is possible to prevent fading, improve absorbance retention, and enhance contrast by at least one of these.

[0319] Method for manufacturing colorant dispersion

[0320] A colorant dispersion can be manufactured by dispersing the colorant (A) in a solvent (E) with a dispersant (P) and further dispersing the resin (B) in the solvent (E) as needed.

[0321] Dispersion treatment refers to mixing particles such as colorant (A) and resin (B) until they reach a dispersed state. This dispersion treatment pulverizes the particles into very small pieces. Furthermore, the dispersed state indicates the distribution of each particle within the other components; preferably, the particles are distributed approximately uniformly within the other components.

[0322] The colorant dispersion preferably contains a colorant (A), a dispersant (P), a resin (B), and a solvent (E).

[0323] The content of colorant (A) in the colorant dispersion of the present invention is preferably 2% by mass or more, more preferably 3% by mass or more, more preferably 30% by mass or less, and more preferably 20% by mass or less, relative to the total amount of the colorant dispersion.

[0324] In addition, the content of solvent (E) relative to the total amount of colorant dispersion is preferably 60% by mass or more, more preferably 75% by mass or more, preferably 95% by mass or less, more preferably 93% by mass or less, and most preferably 91% by mass or less.

[0325] When the colorant dispersion contains resin (B), the content of resin (B) relative to the total amount of the colorant dispersion is preferably 1% by mass or more, more preferably 2% by mass or more, more preferably 15% by mass or less, and more preferably 7% by mass or less. When the content of resin (B) is within the above range, there is a tendency for the dispersion state of the colorant to become more stable.

[0326] The content of dispersant (P) in the colorant dispersion relative to the total amount of the colorant dispersion is preferably 0.1% by mass or more, more preferably 0.3% by mass or more, preferably 20% by mass or less, more preferably 10% by mass or less, and even more preferably 7% by mass or less. When the content of dispersant (P) is within the above range, there is a tendency for the dispersion state of the colorant to become stable.

[0327] The temperature at which the colorant (A) is dispersed in the solvent (E) and at which the mixture is dispersed is preferably 120°C or lower, more preferably 70°C or lower. The lower limit of the dispersion temperature is not particularly limited, but is typically 20°C.

[0328] The dispersion time is preferably 0.5 hours or more, more preferably 2 hours or more, preferably 48 hours or less, and more preferably 20 hours or less.

[0329] Examples of devices used in dispersion include roller mills, high-speed mixing devices, bead mills, ball mills, sand mills, paint conditioners, ultrasonic dispersers, and high-pressure dispersers.

[0330] The obtained colorant dispersion is preferably filtered using a filter with a pore size of about 1.0 to 5.0 μm.

[0331] <Method for Manufacturing Color Filters>

[0332] Examples of methods for manufacturing colored patterns using the color-curing resin composition of the present invention include photolithography, inkjet printing, and printing. Photolithography is preferred. Photolithography involves coating the aforementioned color-curing resin composition onto a substrate, drying it to form a colored composition layer, exposing the colored composition layer through a photomask, and then developing it. In photolithography, a colored coating film, which is a cured film of the aforementioned colored composition layer, can be formed during exposure without using a photomask and / or without development. The resulting colored pattern and colored coating film constitute the color filter of the present invention.

[0333] The thickness of the filter film is not particularly limited and can be adjusted appropriately according to the purpose and application, for example, 0.1 to 30 μm, preferably 0.1 to 20 μm, and more preferably 0.5 to 6 μm.

[0334] As substrates, various glass plates can be used, including quartz glass, borosilicate glass, aluminosilicate glass, and soda-lime glass with a silica coating, as well as resin plates such as polycarbonate, polymethyl methacrylate, and polyethylene terephthalate, silicon substrates, and substrates on which aluminum, silver, or silver / copper / palladium alloy thin films are formed. Other color filter layers, resin layers, transistors, circuits, etc., can be formed on these substrates. Alternatively, substrates that have undergone HMDS treatment on silicon substrates can be used.

[0335] The formation of pixels of various colors based on photolithography can be carried out using known or conventional apparatus and conditions. For example, it can be fabricated as described below.

[0336] First, the coloring curable resin composition is coated onto a substrate and then dried by heating (pre-baking) and / or by vacuum drying to remove volatile components such as solvents, resulting in a smooth coloring composition layer.

[0337] Examples of coating methods include spin coating, slot coating, and slot spin coating.

[0338] The preferred temperature for heating and drying is 30–120°C, more preferably 50–110°C. The preferred heating time is 10 seconds to 60 minutes, more preferably 30 seconds to 30 minutes.

[0339] When performing vacuum drying, it is preferable to carry out the process at a pressure of 50–150 Pa and a temperature range of 20–25 °C.

[0340] There is no particular limitation on the film thickness of the coloring composition layer; it can be appropriately selected according to the film thickness of the target color filter.

[0341] Next, the coloring composition layer is exposed to form a color coating. Alternatively, when forming the color pattern, the coloring composition layer is exposed through a photomask. The pattern on the photomask is not particularly limited; a pattern appropriate for the intended use is used.

[0342] As the light source used for exposure, a light source that produces light with wavelengths of 250–450 nm is preferred. For example, light with wavelengths less than 350 nm can be cut off using a filter that cuts off that wavelength region, or light near 436 nm, 408 nm, and 365 nm can be selectively extracted using a bandpass filter that extracts these wavelength regions. Specifically, examples include mercury lamps, light-emitting diodes, metal halide lamps, and halogen lamps.

[0343] In order to uniformly illuminate the entire exposure surface with parallel light and to accurately align the photomask with the substrate on which the colored composition layer is formed, it is preferable to use a reduction projection exposure device or a proximity exposure device, such as a mask aligner and a stepper.

[0344] The exposed coloring composition layer is brought into contact with a developing solution for development, thereby forming a colored pattern on the substrate. The unexposed portions of the coloring composition layer are dissolved in the developing solution and removed during development. As the developing solution, an aqueous solution of an alkaline compound such as potassium hydroxide, sodium bicarbonate, sodium carbonate, and tetramethylammonium hydroxide is preferred. 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. Furthermore, the developing solution may contain a surfactant.

[0345] The development method can be any of the following: immersion, dipping, or spraying. Furthermore, the substrate can be tilted at any angle during development.

[0346] After development, it is preferable to wash with water.

[0347] Furthermore, it is preferable to perform a post-baking process on the obtained colored coating or colored pattern. The post-baking temperature is preferably 80–250°C, more preferably 100–235°C. The post-baking time is preferably 1–120 minutes, more preferably 2–30 minutes.

[0348] According to the present invention, a color-curing resin composition with high adaptability to film-forming processes can be provided. Color filters made from this color-curing resin composition are useful as color filters used in display devices (e.g., liquid crystal display devices, organic EL display devices, electronic paper, etc.) and solid-state imaging elements.

[0349] [Example]

[0350] The present invention will be described in more detail below with examples. However, the present invention is not limited to the examples described below. Appropriate modifications can be made to implement the invention within the scope suitable for the above and following spirit, and these modifications are all included within the technical scope of the present invention. In the examples, unless otherwise specified, % and parts representing content or usage amount refer to mass percentage and mass parts, respectively.

[0351] [Example 1 of colorant synthesis]

[0352] 50 parts of m-bromophenol (manufactured by Tokyo Chemical Industry Co., Ltd.) and 30 parts of imidazole (manufactured by Tokyo Chemical Industry Co., Ltd.) were dissolved in 500 parts of dichloromethane (manufactured by Kanto Chemical Co., Ltd.). After cooling to 0°C, 48 parts of tert-butyldimethylchlorosilane (manufactured by Tokyo Chemical Industry Co., Ltd.) were added dropwise. After the addition was complete, the temperature was raised to 23°C and stirred for 16 hours. After the reaction was complete, water was added, the organic layer was extracted, the solvent was concentrated, and the mixture was purified by silica gel column chromatography to obtain 74 parts of the compounds represented by formulas (1-7). The structures of the compounds were then confirmed by mass spectrometry (LC; Agilent 1200 type, MASS; Agilent LC / MSD type).

[0353] Identification: (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 287.0

[0354] Precise molecular weight: +286.0

[0355]

[0356] 15 parts of 2,4-dimethylaniline (manufactured by Tokyo Chemical Industry Co., Ltd.), 35 parts of the compound represented by formula (1-7), 14 parts of potassium hydroxide (manufactured by Wako Pure Chemical Industries Co., Ltd.), 2 parts of tetrabutylammonium bromide (manufactured by Tokyo Chemical Industry Co., Ltd.), and 0.6 parts of bis(tri-tert-butylphosphine)palladium(0) (manufactured by Aldrich Co., Ltd.) were dissolved in 250 parts of toluene (manufactured by Kanto Chemical Co., Ltd.) and 15 parts of water. The mixture was heated to 90°C and stirred for 30 minutes. After the reaction was completed, the organic layer was extracted and concentrated, and then purified by silica gel column chromatography to obtain 14 parts of the compound represented by formula (1-8).

[0357] Identification: (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 328.3

[0358] Precise molecular weight: +327.2

[0359]

[0360] 14 parts of the compound represented by formula (1-8) and 10 parts of methyl 4-chloro-4-oxobutyrate (manufactured by Tokyo Chemical Industry Co., Ltd.) were dissolved in 255 parts of toluene (manufactured by Kanto Chemical Co., Ltd.), and the mixture was heated to 90°C and stirred for 1 hour. After the reaction was completed, water was added to extract the organic layer, and the solvent was concentrated and purified by silica gel chromatography to obtain 15 parts of the compound represented by formula (1-9).

[0361] Identification: (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 442.3

[0362] Precise molecular weight: +441.2

[0363]

[0364] Dissolve 15 parts of the compound represented by formula (1-9) in 150 parts of tetrahydrofuran (manufactured by Kanto Chemical Co., Ltd.), cool to 0°C, and then add dropwise 15 parts of tetra-n-butylammonium fluoride 1M tetrahydrofuran solution (manufactured by Tokyo Chemical Industry Co., Ltd.). After the addition is complete, raise the temperature to 23°C and stir for 2 hours. After the reaction is complete, concentrate the solvent and separate and purify by silica gel column chromatography to obtain 12 parts of the compound represented by formula (1-10).

[0365] Identification: (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 328.2

[0366] Precise molecular weight: +327.2

[0367]

[0368] Twelve parts of the compound represented by formula (1-10) were dissolved in 240 parts of tetrahydrofuran (manufactured by Kanto Chemical Co., Ltd.). After cooling to 0°C, 180 parts of a 1M tetrahydrofuran solution (manufactured by Kanto Chemical Co., Ltd.) in borane were added dropwise. After the addition was complete, the mixture was stirred for 30 minutes, water was added, and the tetrahydrofuran was concentrated. The organic layer was extracted with ethyl acetate. After the solvent was concentrated, the mixture was separated and purified by silica gel column chromatography to obtain six parts of the compound represented by formula (1-11).

[0369] Identification: (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 314.2

[0370] Precise molecular weight: +313.2

[0371]

[0372] Six parts of the compound represented by formula (1-11) and 0.2 parts of lithium hydroxide monohydrate (manufactured by Wako Pure Chemical Industries, Ltd.) were dissolved in 20 parts of methanol (manufactured by Kanto Chemical Co., Ltd.), 20 parts of tetrahydrofuran (manufactured by Kanto Chemical Co., Ltd.), and 10 parts of water. The mixture was stirred at 23°C for 1 hour. After the reaction was completed, the organic solvent was concentrated, the organic layer was extracted with ethyl acetate, and the mixture was separated and purified by silica gel column chromatography to obtain four parts of the compound represented by formula (1-12).

[0373] Identification: (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 300.2

[0374] Precise molecular weight: +299.2

[0375]

[0376] Four parts of the compound represented by formula (1-12) and 0.8 parts of 3,4-dihydroxy-3-cyclobutene-1,2-dione (manufactured by Wako Pure Chemical Industries, Ltd.) were dissolved in 40 parts of toluene (manufactured by Kanto Chemical Co., Ltd.) and 10 parts of n-butanol (manufactured by Kanto Chemical Co., Ltd.). The mixture was heated to 140°C and stirred for 2 hours. After concentrating the solvent, the mixture was purified by silica gel column chromatography to obtain 1.6 parts of the compound represented by formula (AI-16).

[0377] Identification: (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] +677.3

[0378] Precise molecular weight: +676.3

[0379]

[0380] [Example 2 of colorant synthesis]

[0381] 50 parts of m-bromophenol (manufactured by Tokyo Chemical Industry Co., Ltd.) and 30 parts of imidazole (manufactured by Tokyo Chemical Industry Co., Ltd.) were dissolved in 500 parts of dichloromethane (manufactured by Kanto Chemical Co., Ltd.). After cooling to 0°C, 48 parts of tert-butyldimethylchlorosilane (manufactured by Tokyo Chemical Industry Co., Ltd.) were added dropwise. After the addition was complete, the temperature was raised to 23°C and stirred for 16 hours. After the reaction was complete, the organic layer was extracted with water, the solvent was concentrated, and the mixture was separated and purified by silica gel column chromatography to obtain 74 parts of the compound represented by formula (2-10). The structures of the compounds were confirmed by mass spectrometry (LC; Agilent 1200 type, MASS; Agilent LC / MSD type).

[0382] Identification: (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 287.0

[0383] Precise molecular weight: +286.0

[0384]

[0385] 45 parts of 4-amino-3,5-xylenol (manufactured by Tokyo Chemical Industry Co., Ltd.) were dissolved in 400 parts of tetrahydrofuran (manufactured by Kanto Chemical Co., Ltd.). 127 parts of di-tert-butyl dicarbonate (manufactured by Tokyo Chemical Industry Co., Ltd.) were added to this solution and dissolved. The mixture was stirred at 23°C for 16 hours to allow the reaction to proceed. After the reaction was complete, the solvent was distilled off to obtain 51 parts of crude product. The crude product was purified by stirring at 23°C for 2 hours in a mixed solvent of 90 parts of ethyl acetate (manufactured by Kanto Chemical Co., Ltd.) and 272 parts of n-hexane (manufactured by Kanto Chemical Co., Ltd.) to obtain 47 parts of the compound represented by formula (1-33).

[0386] Identification: (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 238.3

[0387] Precise molecular weight: +237.1

[0388]

[0389] 20 parts of 2-bromoethanol (manufactured by Tokyo Chemical Industry Co., Ltd.) were dissolved in 333 parts of dichloromethane (manufactured by Kanto Chemical Co., Ltd.). 32.4 parts of triethylamine (manufactured by Kanto Chemical Co., Ltd.) and 0.156 parts of 4-dimethylaminopyridine (manufactured by Kanto Chemical Co., Ltd.) were added to this solution, and 28.95 parts of tert-butyldimethylchlorosilane (manufactured by Tokyo Chemical Industry Co., Ltd.) were added while stirring until dissolved. The mixture was stirred at 23°C for 16 hours to allow the reaction to proceed. The solvent was distilled off to obtain 20 parts of crude product. The crude product was purified by column chromatography to obtain 20 parts of the compound represented by formula (1-34).

[0390] Identification: (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 239.1

[0391] Precise molecular weight: +238.0

[0392]

[0393] 47 parts of the compound represented by formula (1-33) were dissolved in 141.5 parts of the compound represented by formula (1-34) and 447 parts of dimethylformamide (manufactured by Kanto Chemical Co., Ltd.). 138.2 parts of potassium carbonate (manufactured by Kanto Chemical Co., Ltd.) were added to this solution, and the mixture was stirred at 70°C for 16 hours to allow the reaction to proceed. After the reaction was complete, the solvent was distilled off, and extraction was performed using an organic solvent to obtain 49 parts of crude product. The crude product was then purified by column chromatography to obtain 41 parts of the compound represented by formula (1-35).

[0394] Identification: (Mass spectrometry) Ionization mode = ESI+: m / z = [M+Ht-Bu] + ] + Precise molecular weight: +395.3 339.2

[0395]

[0396] Forty-one parts of the compound represented by formula (1-35) were dissolved in 424 parts of 1,4-dioxane (manufactured by Kanto Chemical Co., Ltd.), and 263 parts of hydrogen chloride (approximately 4 mol / L 1,4-dioxane solution) (manufactured by Tokyo Chemical Industry Co., Ltd.) were added. The mixture was stirred at 23°C for 1 hour to deprotect it. After the reaction was completed, the solvent was distilled off to obtain 36 parts of crude product. The crude product was purified by column chromatography to obtain 22 parts of the compound represented by formula (1-36).

[0397] Identification: (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 182.2

[0398] Precise molecular weight: +181.1

[0399]

[0400] 22 parts of the compound represented by formula (1-36) were dissolved in 293 parts of dichloromethane (manufactured by Kanto Chemical Co., Ltd.). 10.8 parts of imidazole (manufactured by Kanto Chemical Co., Ltd.) and 22 parts of tert-butyldimethylchlorosilane (manufactured by Tokyo Chemical Industry Co., Ltd.) were added to this solution and dissolved. The mixture was stirred at 23°C for 16 hours to allow the reaction to proceed. The solvent was distilled off to obtain 23 parts of crude product. The crude product was purified by column chromatography to obtain 20 parts of the compound represented by formula (1-37).

[0401] Identification: (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 296.3

[0402] Precise molecular weight: +295.2

[0403]

[0404] 15 parts of the compound represented by formula (2-10) were dissolved in 14.5 parts of the compound represented by formula (1-37) and 130 parts of toluene (manufactured by Kanto Chemical Co., Ltd.). In this solution, 5.7 parts of potassium hydroxide (manufactured by Kanto Chemical Co., Ltd.), 15 parts of water, 2 parts of tetrabutylammonium bromide (manufactured by Tokyo Chemical Industry Co., Ltd.), and 0.26 parts of bis(tri-tert-butylphosphine)palladium(0) (manufactured by Tokyo Chemical Industry Co., Ltd.) were mixed. After heating to 90°C and stirring for 20 minutes, an organic layer was obtained by extraction. The solvent was distilled off to obtain 15 parts of crude product. The crude product was purified by column chromatography to obtain 12 parts of the compound represented by formula (1-38).

[0405] Identification: (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 502.4

[0406] Precise molecular weight: +501.3

[0407]

[0408] 12 parts of the compound represented by formula (1-38), 11.9 parts of methyl 4-chloro-4-oxobutyrate (manufactured by Tokyo Chemical Industry Co., Ltd.), and 41.6 parts of toluene (manufactured by Kanto Chemical Co., Ltd.) were mixed and heated at 90°C with stirring for 1 hour. After the reaction was completed, the solvent was distilled off, and the crude product was separated and purified by column chromatography to obtain 5.9 parts of the compound represented by formula (1-39).

[0409] Identification: (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 616.3

[0410] Precise molecular weight: +615.3

[0411]

[0412] 5.9 parts of the compound represented by formula (1-39) were dissolved in 52.4 parts of tetrahydrofuran (manufactured by Kanto Chemical Co., Ltd.). After cooling to 0°C, 11 parts of a 1M tetrabutylammonium fluoride tetrahydrofuran solution (manufactured by Tokyo Chemical Industry Co., Ltd.) were added dropwise. After the addition was completed, the mixture was stirred at 23°C for 2 hours. After the reaction was completed, water was added, and the crude product obtained by distilling off the tetrahydrofuran solvent was subjected to an organic solvent-based extraction operation. After concentration, 4.3 parts of the compound represented by formula (1-40) were obtained.

[0413] Identification: (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 388.2

[0414] Precise molecular weight: +387.2

[0415]

[0416] 4.3 parts of the compound represented by formula (1-40), 56.4 parts of 1M borane tetrahydrofuran solution (manufactured by Kanto Chemical Co., Ltd.), and 38.2 parts of tetrahydrofuran (manufactured by Kanto Chemical Co., Ltd.) were mixed at 0°C, and the mixture was heated to 23°C and stirred for 16 hours. After the reaction was completed, water was added to quench the reaction, and the mixture was extracted with an organic solvent. The solvent was distilled off, and the crude product was purified by silica gel column chromatography to obtain 2.3 parts of the compound represented by formula (1-41).

[0417] Identification: (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 346.3

[0418] Precise molecular weight: +345.2

[0419]

[0420] 2.3 parts of the compound represented by formula (1-41) and 0.38 parts of 3,4-dihydroxy-3-cyclobutene-1,2-dione (manufactured by Fujifilm and Koko Pure Chemicals Co., Ltd.) were dissolved in 80 parts of toluene (manufactured by Kanto Chemical Co., Ltd.) and 19 parts of n-butanol (manufactured by Kanto Chemical Co., Ltd.), and the mixture was heated at 120°C with stirring for 4 hours. After the reaction was completed, the crude product obtained by distillation to remove the solvent was separated and purified by silica gel column chromatography to obtain 1.3 parts of the compound represented by formula (AI-15).

[0421] Identification: (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 769.8

[0422] Precise molecular weight: +768.4

[0423]

[0424] [Example of resin synthesis]

[0425] A suitable amount of nitrogen was poured into a flask equipped with a reflux condenser, a dropping funnel, and a stirrer to create a nitrogen atmosphere. 280 parts of propylene glycol monomethyl ether acetate were then added, and the mixture was heated to 80°C while stirring. Next, 38 parts of acrylic acid and 3,4-epoxytricyclic acrylic acid [5.2.1.0] were added dropwise over 5 hours. 2,6 ] Decane-8-yl ester and 3,4-epoxytricyclic acrylate [5.2.1.0] 2,6 A mixed solution of 289 parts of a mixture of decane-9-yl ester (mixed in a 1:1 ratio) and 125 parts of propylene glycol monomethyl ether acetate was prepared. On the other hand, a mixed solution was prepared by dropwise addition of 33 parts of 2,2-azobis(2,4-dimethylpentanones) to 235 parts of propylene glycol monomethyl ether acetate over 6 hours. After the addition was completed, the flask was kept at 80°C for 4 hours and then cooled to room temperature to obtain a copolymer (resin (B-1)) solution with a type B viscosity (23°C) of 125 mPa·s and a solid content of 35.1%. The resulting copolymer had a weight-average molecular weight (Mw) of 9200, a dispersion of 2.08, and an acid value of 77 mg-KOH / g. Resin (B-1) has the following structural units.

[0426]

[0427] [Preparation Example 1: Preparation of Dispersion 1]

[0428] 5.0 parts of the compound represented by formula (AI-16) (colorant (A-1)), 1.5 parts of dispersant (P-1) (solid component), 4.0 parts of resin (B-1) (solid component), and 89.5 parts of solvent (E-1) were weighed, and then 300 parts of 0.2 μm zirconia beads were added. The mixture was shaken for 1 hour using a Paint Conditioner (LAU manufactured), and the zirconia beads were removed by filtration to prepare dispersion 1.

[0429] [Preparation Example 2: Preparation of Dispersion 2]

[0430] Dispersion 2 was prepared in the same manner as in Preparation Example 1, except that the solid components of dispersant (P-1) were replaced with 0.5 parts and the solvent (E-1) was 90.5 parts.

[0431] [Preparation Example 3: Preparation of Dispersion 3]

[0432] Dispersion 3 was prepared in the same manner as in Preparation Example 1, except that 1.5 parts of the solid component of dispersant (P-1) was replaced with 1.5 parts of the solid component of dispersant (P-2).

[0433] [Preparation Example 4: Preparation of Dispersion 4]

[0434] Dispersion 4 was prepared in the same manner as in Preparation Example 1, except that 1.5 parts of the solid component of dispersant (P-1) was replaced with 0.5 parts of the solid component of dispersant (P-2), and 89.5 parts of solvent (E-1) were replaced with 90.5 parts of solvent (E-1).

[0435] [Preparation Example 5: Preparation of Dispersion 5]

[0436] Dispersion 5 was prepared in the same manner as in Preparation Example 1, except that 1.5 parts of the solid component of dispersant (P-1) was replaced with 1.5 parts of the solid component of dispersant (P-3).

[0437] [Preparation Example 6: Preparation of Dispersion 6]

[0438] Dispersion 6 was prepared in the same manner as in Preparation Example 1, except that 1.5 parts of the solid component of dispersant (P-1) was replaced with 0.5 parts of the solid component of dispersant (P-3), and 89.5 parts of solvent (E-1) were replaced with 90.5 parts of solvent (E-1).

[0439] [Preparation Example 7: Preparation of Dispersion 7]

[0440] The dispersion 7 was prepared in the same manner as in Preparation Example 1, except that 5.0 parts of colorant (A-1) were replaced with 5.0 parts of colorant (A-2), 1.5 parts of dispersant (P-1) were replaced with 5.0 parts of dispersant (P-1), 89.5 parts of solvent (E-1) were replaced with 76.0 parts of solvent (E-1) and 10 parts of solvent (E-2).

[0441] [Preparation Example 8: Preparation of Dispersion 8]

[0442] The dispersion 8 was prepared in the same manner as in Preparation Example 1, except that 5.0 parts of colorant (A-1) were replaced with 5.0 parts of colorant (A-2), 1.5 parts of dispersant (P-1) were replaced with 2.5 parts of dispersant (P-1), and 89.5 parts of solvent (E-1) were replaced with 78.5 parts of solvent (E-1) and 10 parts of solvent (E-2).

[0443] [Preparation Example 9: Preparation of Dispersion 9]

[0444] The dispersion 9 was prepared in the same manner as in Preparation Example 1, except that 5.0 parts of colorant (A-1) were replaced with 5.0 parts of colorant (A-2), 89.5 parts of solvent (E-1) were replaced with 79.5 parts of solvent (E-1) and 10 parts of solvent (E-2).

[0445] [Preparation Example 10: Preparation of Dispersion 10]

[0446] Dispersion 10 was prepared in the same manner as in Preparation Example 1, except that 5.0 parts of colorant (A-1) were replaced with 5.0 parts of colorant (A-2), 1.5 parts of dispersant (P-1) were replaced with 0.5 parts of dispersant (P-1), 89.5 parts of solvent (E-1) were replaced with 80.5 parts of solvent (E-1) and 10 parts of solvent (E-2).

[0447]

[0448] [Examples 1-14, Comparative Example 1]

[0449] [Preparation of Coloring and Curing Resin Compositions]

[0450] A coloring and curing resin composition was obtained by mixing each dispersion 1 to 10, resin (B), polymerizable compound (C), polymerization initiator (D), solvent (E), and leveling agent (F) in the manner shown in Table 4 (dispersion 1 was used in Example 1, and each dispersion 2 to 10 was used in Examples 2 to 10 respectively). It should be noted that the unit of content of each component in Table 4 is "parts".

[0451] It should be noted that in Examples 11-14 and Comparative Example 1, a colored curable resin composition was prepared by mixing a colorant (A), a resin (B), a polymerizable compound (C), a polymerization initiator (D), a solvent (E), a leveling agent (F), and a dispersant (P) as needed, without using a dispersion.

[0452]

[0453] In Table 4, each component represents the following compound (※ indicates the amount introduced from the dispersion).

[0454] Colorant (A): (A-1): Compound represented by formula (AI-16)

[0455] Colorant (A): (A-2): Compound represented by formula (AI-15)

[0456] Dispersant (P): Dispersant (P-1) is an acrylic dispersant (amine value 1 mg KOH / g, containing tertiary amines).

[0457] Dispersant (P): Dispersant (P-2) is an acrylic dispersant (amine value 14 mg KOH / g, containing tertiary amines).

[0458] Dispersant (P): Dispersant (P-3) is an acrylic dispersant (amine value 28 mg KOH / g, containing tertiary amines).

[0459] Resin (B): Resin (B-1) (Conversion of solid components)

[0460] Polymerizable compound (C): (C-1): Dipentaerythritol hexaacrylate (KAYARAD DPHA; manufactured by Nippon Kayaku Co., Ltd.)

[0461] Polymerization initiator (D): (D-1): N-acetoxy-1-(4-phenylthiophenyl)-3-cyclohexylpropane-1-one-2-imine (PBG-327; O-acyl oxime compound; manufactured by Changzhou Qiangli Electronic New Materials Co., Ltd.)

[0462] Solvent (E): (E-1): Propylene glycol monomethyl ether acetate

[0463] Solvent (E): (E-2): 4-Hydroxy-4-methyl-2-pentanone

[0464] Leveling agent (F): (F-1): Polyether modified silicone oil (Dow Corning Toray Co., Ltd. "Toray SiliconeSH8400")

[0465] [Preparation of a colored coating (color filter)]

[0466] The coloring and curing resin composition was spin-coated onto a 5cm square glass substrate (EAGLE 2000; CORNING) with a post-baking film thickness of 2.0μm. The substrate was then pre-baked at 100°C for 3 minutes to form the coloring composition layer. After cooling, an exposure machine (TME-150RSK; TOPCON Co., Ltd.) was used to expose the substrate at 100mJ / cm² under atmospheric conditions. 2 The coloring composition layer was irradiated with light at an exposure level (365 nm reference). Subsequently, it was baked in an oven at 230°C for 30 minutes to obtain the color filter.

[0467] [evaluate]

[0468] 1. Colorfastness (ΔE*ab)

[0469] Colorimetric measurements were performed before and after pre-baking using a colorimeter (OSP-SP-200; manufactured by Olympus Corporation). The spectrum was measured using a C-light source, and the xy chromaticity coordinates (x, y) and stimulus value Y in the CIE XYZ colorimetric system were determined using the characteristic function of the C light source. The color difference ΔE*ab was calculated from these measurements using the method described in JIS Z 8730:2009 (7. Calculation Method of Color Difference), and the results are shown in Table 4. A smaller ΔE*ab indicates less color change (higher heat resistance).

[0470] 2. Absorbance retention rate

[0471] The spectra were measured using a colorimeter (OSP-SP-200; manufactured by Olympus Corporation) after pre-baking and post-baking. The maximum absorbance in the visible light region was determined from the obtained spectra, and the retention rate of the maximum absorbance was calculated according to the following formula. The results are shown in Table 4.

[0472] Absorbance retention rate (ΔAbs.Max) = Maximum absorbance after post-baking / Maximum absorbance after pre-baking

[0473] A higher absorbance retention rate means higher suitability in the film-forming process.

[0474] 3. Contrast

[0475] For the post-baked color filters, the contrast was measured using a contrast meter (CT-1: manufactured by Tsubosaka Electric Co., Ltd., colorimeter BM-5A: manufactured by TOPCON, light source: F-10, polarizing film: manufactured by Tsubosaka Electric Co., Ltd.) with a blank value set to 30000. If the contrast in the colored coating is high, it can be said that the contrast in the colored pattern is also high. The results are shown in Table 4.

[0476] Compared with Comparative Example 1, Examples 1-14 showed lower ΔE*ab, indicating anti-fading properties.

[0477] On the other hand, when comparing Examples 2 and 11, Examples 3 and 12, Examples 4 and 13, and Examples 6 and 14 with and without the colorant dispersion, it can be seen that when the colorant dispersion is used, at least one of the following is further improved: anti-fading property, absorbance retention rate, and contrast.

[0478] Industrial availability

[0479] According to the present invention, a color-curing resin composition is provided that can form a color coating film that prevents fading (preferably with improved absorbance retention and contrast, or both), and is therefore useful as a color-curing resin composition for use in color filters of display devices and solid-state imaging elements.

Claims

1. A coloring and curing resin composition comprising a colorant, a dispersant, a resin, a polymerizable compound, a polymerization initiator, and a solvent. The colorant contains squaric acid, which has maximum absorption in the visible light region. dye, The amine value of the dispersant is greater than 0 mg KOH / g and less than 30 mg KOH / g; The square acid Dyes are compounds represented by the formula (AI). In formula (AI), R 1 ~R 4 Each of these groups independently represents a hydrogen atom, a halogen atom, a hydroxyl group, or a monovalent saturated hydrocarbon group with 1 to 20 carbon atoms that may have substituents. The methylene group constituting this monovalent saturated hydrocarbon group can be replaced by -O- or -S-. R 5 ~R 8 Each can independently represent a hydrogen atom or a hydroxyl group. Ar 1 and Ar 2 Each group represented by formula (i) is independently represented. In equation (i), R 12 This indicates a monovalent saturated hydrocarbon group or hydroxyl or carboxyl group with 1 to 20 carbon atoms, where m represents an integer from 0 to 5. The methylene group constituting this monovalent saturated hydrocarbon group can be replaced by -O- or -S-. When m is 2 or more, multiple R groups are represented. 12 They can be the same or different; * indicates the bonding site with the nitrogen atom. R 9 and R 10 Each of the above independently represents a monovalent saturated hydrocarbon group with 1 to 20 carbon atoms that may have substituents, or a group represented by formula (i), wherein the methylene group constituting the monovalent saturated hydrocarbon group may be replaced by -O- or -S-.

2. The coloring and curing resin composition according to claim 1, wherein, The square acid The dye is a compound represented by formula (AII). In formula (AII), R 1 ~R 4 Each of these groups independently represents a hydrogen atom, a halogen atom, a hydroxyl group, or a monovalent saturated hydrocarbon group with 1 to 20 carbon atoms that may have substituents. The methylene group constituting this monovalent saturated hydrocarbon group can be replaced by -O- or -S-. R 5 ~R 8 Each can independently represent a hydrogen atom or a hydroxyl group. Ar 1 and Ar 2 Each group represented by formula (i) is independently represented. In equation (i), R 12 This indicates a monovalent saturated hydrocarbon group or hydroxyl or carboxyl group with 1 to 20 carbon atoms, where m represents an integer from 0 to 5. The methylene group constituting this monovalent saturated hydrocarbon group can be replaced by -O- or -S-. When m is 2 or more, multiple R groups are represented. 12 They can be the same or different; * indicates the bonding site with the nitrogen atom. R 13 and R 14 Each of these groups independently represents a monovalent saturated hydrocarbon group with 1 to 20 carbon atoms having a hydroxyl or carboxyl group, wherein the methylene group constituting the monovalent saturated hydrocarbon group can be replaced by -O- or -S-.

3. The coloring and curing resin composition according to claim 1 or 2, wherein, The dispersant has a basic functional group consisting of a tertiary amino group or a nitrogen-containing heterocyclic group.

4. The coloring and curing resin composition according to claim 1 or 2, wherein, The content of the dispersant is 0.1 to 50 parts by mass relative to 100 parts by mass of the colorant.

5. The coloring and curing resin composition according to claim 1 or 2, wherein, A dispersion containing the colorant dispersed in a solvent by the dispersant.

6. A color filter formed from the color-curing resin composition of claim 1 or 2.

7. A liquid crystal display device comprising the color filter as described in claim 6.

8. A method for manufacturing a coloring and curing resin composition, comprising the following steps: The process of obtaining a dispersion of a colorant dispersed in a solvent by means of a dispersant, and The step of adding resin, polymerizable compound and polymerization initiator to the dispersion; The colorant contains squaric acid, which has maximum absorption in the visible light region. dye, The amine value of the dispersant is greater than 0 mg KOH / g and less than 30 mg KOH / g; The square acid Dyes are compounds represented by the formula (AI). In formula (AI), R 1 ~R 4 Each of these groups independently represents a hydrogen atom, a halogen atom, a hydroxyl group, or a monovalent saturated hydrocarbon group with 1 to 20 carbon atoms that may have substituents. The methylene group constituting this monovalent saturated hydrocarbon group can be replaced by -O- or -S-. R 5 ~R 8 Each can independently represent a hydrogen atom or a hydroxyl group. Ar 1 and Ar 2 Each group represented by formula (i) is independently represented. In equation (i), R 12 This indicates a monovalent saturated hydrocarbon group or hydroxyl or carboxyl group with 1 to 20 carbon atoms, where m represents an integer from 0 to 5. The methylene group constituting this monovalent saturated hydrocarbon group can be replaced by -O- or -S-. When m is 2 or more, multiple R groups are represented. 12 They can be the same or different; * indicates the bonding site with the nitrogen atom. R 9 and R 10 Each of the above independently represents a monovalent saturated hydrocarbon group with 1 to 20 carbon atoms that may have substituents, or a group represented by formula (i), wherein the methylene group constituting the monovalent saturated hydrocarbon group may be replaced by -O- or -S-.

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