Colored curable resin composition, color filter, display device, and solid-state imaging device

Abstract

The invention relates to a colored curable resin composition, a color filter, a display device and a solid-state imaging device. The purpose of the present invention is to provide a colored curable resin composition capable of producing a color filter having improved color separability from green light. [Solution] The colored curable resin composition according to the present invention is characterized by containing a colorant, a resin, a polymerizable compound, and a polymerization initiator, the colorant including xanthene pigment, purple pigment, and blue pigment, and the content of the xanthene pigment is 8-45 parts by mass per 100 parts by mass of the blue pigment.

Description

TECHNICAL FIELD

[0001] The present application relates to a colored curable resin composition, a color filter formed from the colored curable resin composition, a display device including the color filter, and a solid-state imaging device. BACKGROUND

[0002] A color filter used in a liquid crystal display device, an electroluminescent display device, a plasma display, and the like, a solid-state imaging device such as a CCD, and a CMOS sensor is generally composed of each color pixel (specifically, a red color filter, a green color filter, and a blue color filter), and each color filter is formed from a colored curable resin composition. For example, Patent Literature 1 describes that a colorant containing 60 to 85% by weight of a blue pigment (A-1), 5 to 20% by weight of a blue pigment (A-2) other than the aforementioned blue pigment (A-1), 5 to 20% by weight of a violet pigment (B), and 0.5 to 5% by weight of a violet dye (C) with respect to the total weight of the colorant is used in a composition for forming a blue color filter.

[0003] PRIOR ART DOCUMENTS

[0004] PATENT LITERATURE

[0005] Patent Literature 1: Japanese Patent Application Laid-Open No. 2023-124822 SUMMARY

[0006] PROBLEMS TO BE SOLVED BY THE INVENTION

[0007] However, for a color filter formed from the composition described in the aforementioned Patent Literature 1, further improvement in color separation is required, and for example, in a blue color filter, leakage of green light is required to be suppressed. Therefore, an object of the present application is to provide a colored curable resin composition capable of producing a color filter in which color separation with respect to green light is improved.

[0008] MEANS FOR SOLVING THE PROBLEMS

[0009] The gist of the present application is as described below.

[0010] [1] A colored curable resin composition containing a colorant, a resin, a polymerizable compound, and a polymerization initiator,

[0011] The aforementioned colorant contains a xanthene dye, a violet pigment, and a blue pigment,

[0012] The content of the aforementioned xanthene dye is 8 to 45 parts by mass with respect to 100 parts by mass of the aforementioned blue pigment.

[0013] [2] The coloring curable resin composition as described in [1], wherein the content of the aforementioned colorant is 35% by mass or more relative to the total amount of solid components in the coloring curable resin composition.

[0014] [3] The coloring curable resin composition as described in [1] or [2], wherein the content of the aforementioned purple pigment is 5 to 250 parts by weight relative to 100 parts by weight of the aforementioned pyrithione pigment.

[0015] [4] The coloring curable resin composition as described in any one of [1] to [3], wherein the content of the aforementioned zeolite pigment is 8 to 32 parts by weight relative to 100 parts by weight of the aforementioned blue pigment.

[0016] [5] The coloring curable resin composition as described in any one of [1] to [3], wherein the content of the aforementioned zeolite pigment is 35 to 45 parts by weight relative to 100 parts by weight of the aforementioned blue pigment.

[0017] [6] The coloring curable resin composition as described in any one of [1] to [5], wherein the content of the purple pigment is 5 to 100 parts by weight relative to 100 parts by weight of the aforementioned pyrrolizin pigment.

[0018] [7] The coloring curable resin composition as described in any one of [1] to [5], wherein the content of the purple pigment is greater than 100 parts by weight relative to 100 parts by weight of the aforementioned zeolite pigment.

[0019] [8] The coloring and curing resin composition as described in any one of [1] to [3], wherein the content of the aforementioned zeolite pigment is 8 to 20 parts by weight relative to 100 parts by weight of the aforementioned blue pigment, and

[0020] Compared to 100 parts by weight of the aforementioned zeolite pigment, the content of the aforementioned purple pigment is less than 90 parts by weight.

[0021] [9] A color filter, which is formed using any one of the color-curing resin compositions described in [1] to [8].

[0022]

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

[0023]

[11] A solid-state imaging device comprising the color filter described in [9].

[0024] Invention Effects

[0025] According to the color-curing resin composition of the present invention, it is possible to produce a color filter with improved color separation from green light. Detailed Implementation

[0026] [Colored curable resin composition]

[0027] The present application includes a colored curable resin composition containing a colorant (hereinafter, sometimes referred to as colorant (A)), a resin (hereinafter, sometimes referred to as resin (B)), a polymerizable compound (hereinafter, sometimes referred to as polymerizable compound (C)), and a polymerization initiator (hereinafter, sometimes referred to as polymerization initiator (D)), the aforementioned colorant (A) containing a xanthene pigment, a violet pigment, and a blue pigment, the content of the aforementioned xanthene pigment being 8 to 45 parts by mass with respect to 100 parts by mass of the aforementioned blue pigment. By using such a colored curable resin composition, it is possible to produce a color filter in which color separation from green light is improved, and preferably a color filter in which color separation from red light is also improved.

[0028] The colored curable resin composition of the present application preferably further contains a solvent (hereinafter, sometimes referred to as solvent (E)).

[0029] The colored curable resin composition of the present application can contain a leveling agent (hereinafter, sometimes referred to as leveling agent (F)).

[0030] In the present specification, unless otherwise specified, the compounds exemplified as each component can be used alone or in combination of a plurality of kinds.

[0031] <Colorant (A)>

[0032] The xanthene pigment (hereinafter, sometimes referred to as xanthene pigment (al)) contained in the aforementioned colorant (A) is a compound having a xanthene skeleton within the molecule. As the xanthene pigment (al), for example, C.I. Acid Red 51 (hereinafter, the description of C.I. Acid Red is omitted and only the number is described. The same applies to others.), 52, 87, 92, 94, 289, 388, C.I. Acid Violet 9, 30, 102, C.I. Basic Red 1 (Rhodamine 6G), 2, 3, 4, 8, 10, 11, C.I. Basic Violet 10 (Rhodamine B), 11, C.I. Solvent Red 218, C.I. Mordant Red 27, C.I. Reactive Red 36 (Rose Bengal B), sulforhodamine G, C.I. Pigment Red 81, 169, 173, C.I. Pigment Violet 1, 2, the xanthene pigments described in Japanese Patent Application Publication No. 2010-32999, the xanthene pigments described in Japanese Patent No. 4492760, and the like can be exemplified.

[0033] As the xanthene pigment (al), a compound represented by formula (1) is preferable. The compound represented by formula (1) can also be a tautomer thereof.

[0034]

[0035] [In formula (1),

[0036] R 1 ~R 4 each independently represents a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms which can have a substituent, an aromatic hydrocarbon group having 6 to 30 carbon atoms which can have a substituent, or a group represented by *-R 12 -Si(R 13 )3 (wherein * represents a bonding position to a nitrogen atom),

[0037] R 1 and R 2 may form a ring containing a nitrogen atom together. 3 and R 4 may form a ring containing a nitrogen atom together.

[0038] R 5 represents -OH, -SO3 - , -SO3H, -SO3 - Z + , -CO2H, -CO2 - Z + , -CO2R 8 , -SO3R 8 , or -SO2NR 9 R 10 .

[0039] R 6 ~R 7 each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.

[0040] R 8 represents a saturated hydrocarbon group having 1 to 20 carbon atoms which can be substituted with a halogen atom.

[0041] R 9 and R 10 each independently represents a hydrogen atom or a saturated hydrocarbon group having 1 to 20 carbon atoms which can have a substituent, and R 9 and R 10 may form a ring containing a nitrogen atom together.

[0042] R 12 represents an alkane diyl group having 1 to 10 carbon atoms, and -CH2- included in the aforementioned alkane diyl group can be replaced with -O-, -CO-, -NR 8 -, -OCO-, -COO-, -OCONH-, -CONH-, or -NHCO-.

[0043] R 13 represents a hydrogen atom, a hydroxyl group, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and a plurality of R 13 may be the same or different.

[0044] Z + It represents any cation.

[0045] X represents a halogen atom.

[0046] 'a' represents 0 or 1.

[0047] m represents an integer from 0 to 5. When m is greater than 2, multiple R... 5 They can be the same or different.

[0048] R 1 ~R 4 and R 8 ~R 10 The saturated hydrocarbon group representing 1 to 20 carbon atoms can be in any form, either chain-like or cyclic. Examples include straight-chain or branched alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, hexadecyl, eicosyl, isopropyl, isobutyl, tert-butyl, isopentyl, neopentyl, and 2-ethylhexyl; cycloalkyl groups such as cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and tricyclodecyl; and so on.

[0049] As R 1 ~R 4 The saturated hydrocarbon group represented by carbon atoms is preferably an alkyl group with carbon atoms of ...

[0050] As R 8 The saturated hydrocarbon group represented by the carbon group having 1 to 20 carbon atoms is preferably an alkyl group having 1 to 20 carbon atoms, more preferably an alkyl group having 1 to 10 carbon atoms, and even more preferably an alkyl group having 1 to 4 carbon atoms.

[0051] As R 9 ~R 10 The saturated hydrocarbon group represented by the carbon number 1 to 20 is preferably an alkyl group with a carbon number 1 to 20, more preferably an alkyl group with a carbon number 1 to 10, and even more preferably an alkyl group with a carbon number 4 to 10.

[0052] R 1 ~R 4The saturated hydrocarbon group with 1 to 20 carbon atoms may have substituents. Examples of such substituents include aryl groups such as phenyl, tolyl, xylyl, and mesitylelel; halogen atoms such as fluorine, chlorine, bromine, and iodine; hydroxyl groups; alkoxy groups such as methoxy, ethoxy, propoxy, and butoxy; carboxyl groups; alkoxycarbonyl groups such as methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, and butoxycarbonyl; amino groups; alkyl-substituted amino groups such as N-methylamino, N-ethylamino, and N,N-dimethylamino; and so on. Among these, halogen atoms, hydroxyl groups, and carboxyl groups are preferred, and carboxyl groups are more preferred.

[0053] R 8 The saturated hydrocarbon group with 1 to 20 carbon atoms can be replaced by a halogen atom. Examples of such halogen atoms include fluorine, chlorine, bromine, and iodine.

[0054] R 9 and R 10 The saturated hydrocarbon group representing 1 to 20 carbon atoms may have substituents. Examples of such substituents include those related to R. 1 ~R 4 The saturated hydrocarbon group representing 1 to 20 carbon atoms may have the same substituents. Among them, halogen atoms and hydroxyl groups are preferred.

[0055] As R 1 ~R 4 Aromatic hydrocarbon groups with 6 to 30 carbon atoms can be represented by phenyl; alkylphenyl groups such as tolyl, xylyl, mesitylelel, propylphenyl, and butylphenyl; arylphenyl groups such as biphenyl and diphenylphenyl; naphthyl; and so on.

[0056] As alkyl groups constituting alkylphenyl groups, examples include those that are R 1 ~R 4 The group described is an alkyl group among saturated hydrocarbon groups having 1 to 20 carbon atoms, preferably an alkyl group having 1 to 10 carbon atoms, more preferably an alkyl group having 1 to 4 carbon atoms, and even more preferably a methyl group. As an alkylphenyl group, it is preferably a group having an alkyl group at at least one of the two bonding positions adjacent to the N atom bonded to the phenyl group, more preferably a group having an alkyl group at two bonding positions adjacent to the N atom bonded to the phenyl group.

[0057] Examples of aryl groups constituting arylphenyl groups include phenyl, tolyl, xylyl, mesitylene, propylphenyl, butylphenyl, and other alkylphenyl groups; among which, aryl groups having 6 to 10 carbon atoms are preferred, and phenyl is more preferred. As an arylphenyl group, it is preferred to have an aryl group at at least one of the two bonding positions adjacent to the N bonded to the phenyl group, and more preferably, it is a group having an aryl group at two bonding positions adjacent to the N bonded to the phenyl group.

[0058] In particular, as R 1 ~R 4 represents an aromatic hydrocarbon group having 6 to 30 carbon atoms, and

[0059] Preferably, it is an aromatic hydrocarbon group having 6 to 20 carbon atoms, and

[0060] More preferably, it is a group having an alkyl group at at least one of the two bonding positions which are ortho with respect to the N bonded to the phenyl group, as an alkylphenyl group; or a group having an aryl group at at least one of the two bonding positions which are ortho with respect to the N bonded to the phenyl group, as an arylphenyl group,

[0061] Further preferably, it is a group having an alkyl group at both of the two bonding positions which are ortho with respect to the N bonded to the phenyl group, as an alkylphenyl group; or a group having an aryl group at both of the two bonding positions which are ortho with respect to the N bonded to the phenyl group, as an arylphenyl group.

[0062] R 1 ~R 4 The aromatic hydrocarbon group having 6 to 30 carbon atoms represented by R 8 , -SO3 - , -SO3H, -SO3 - Z + , -CO2H, -CO2R 8 , -SR 8 , -SO2R 8 , -SO3R 8 , -SO2NR 9 R 10 , etc. Among them, -SO3 - , -SO3H, -SO3 - Z + , -SO2NR 9 R 10 , -SO3 - Z + , -SO2NR 9 R 10 are preferable. As -SO3 - Z + in this case, -SO3 - N + (R 11 )4 is preferable. Note that in the case where the aromatic hydrocarbon group having 6 to 30 carbon atoms has a substituent, the substituent is preferably directly bonded to the aromatic hydrocarbon ring.

[0063] Z + is preferably an ammonium cation, Na +or K + , more preferably an ammonium cation. Note that in the present specification, the ammonium cation is not limited to NH4 + , and is defined to include the meanings of primary ammonium cation, secondary ammonium cation, tertiary ammonium cation, quaternary ammonium cation, and the like, among which a quaternary ammonium cation is preferable. As the aforementioned ammonium cation, for example, a polymer having -N + (R 11 )3 as a partial structure, N + (R 11 )4 can be given. The plurality of R 11 may be the same or different.

[0064] R 11 represents a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms.

[0065] As the saturated hydrocarbon group having 1 to 20 carbon atoms represented by R 11 , a saturated alkyl group having 1 to 20 carbon atoms is preferable, and a saturated alkyl group having 1 to 15 carbon atoms is more preferable.

[0066] As the aralkyl group having 7 to 10 carbon atoms represented by R 11 , a benzyl group, a phenylethyl group, a phenylpropyl group, a phenylbutyl group, a naphthylmethyl group, and the like can be given.

[0067] As the aforementioned N + (R 11 )4, it is preferable that at least two of the four R 11 be a saturated hydrocarbon group having 5 to 20 carbon atoms (particularly, an alkyl group having 5 to 20 carbon atoms) in the N + (R 11 )4. In addition, the total number of carbon atoms of the four R 11 is preferably 20 to 80, and more preferably 20 to 60.

[0068] As -OR 8 , a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, a hexyloxy group, a heptyloxy group, an octyloxy group, a 2-ethylhexyloxy group, a eicosyloxy group, and the like can be given.

[0069] As -CO2R 8 , a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, a butoxycarbonyl group, a hexyloxycarbonyl group, a eicosyloxycarbonyl group, and the like can be given.

[0070] As -SR 8 , a methylsulfanyl group, an ethylsulfanyl group, a butylsulfanyl group, a hexylsulfanyl group, a decylsulfanyl group, a eicosylsulfanyl group, and the like can be given.

[0071] As -SO2R 8Examples include methylsulfonyl, ethylsulfonyl, butylsulfonyl, hexylsulfonyl, decylsulfonyl, and eicosylsulfonyl.

[0072] As -SO3R 8 Examples include methoxysulfonyl, ethoxysulfonyl, propoxysulfonyl, butoxysulfonyl, hexyloxysulfonyl, and eicosyloxysulfonyl.

[0073] As -SO2NR 9 R 10 Examples include:

[0074] Aminosulfonyl;

[0075] N-Methylaminosulfonyl, N-ethylaminosulfonyl, N-propylaminosulfonyl, N-isopropylaminosulfonyl, N-butylaminosulfonyl, N-isobutylaminosulfonyl, N-sec-butylaminosulfonyl, N-tert-butylaminosulfonyl, N-pentylaminosulfonyl, N-(1-ethylpropyl)aminosulfonyl, N-(1,1-dimethylpropyl)aminosulfonyl, N-(1,2-dimethylpropyl)aminosulfonyl, N-(2,2-dimethylpropyl)aminosulfonyl, N-(1-methylbutyl)aminosulfonyl, N-(2-methylbutyl)aminosulfonyl, N -(3-methylbutyl)aminosulfonyl, N-cyclopentylaminosulfonyl, N-hexylaminosulfonyl, N-(1,3-dimethylbutyl)aminosulfonyl, N-(3,3-dimethylbutyl)aminosulfonyl, N-heptylaminosulfonyl, N-(1-methylhexyl)aminosulfonyl, N-(1,4-dimethylpentyl)aminosulfonyl, N-octylaminosulfonyl, N-(2-ethylhexyl)aminosulfonyl, N-(1,5-dimethyl)hexylaminosulfonyl, N-(1,1,2,2-tetramethylbutyl)aminosulfonyl and other N-1 substituted aminosulfonyl groups;

[0076] N,N-dimethylaminosulfonyl, N,N-ethylmethylaminosulfonyl, N,N-diethylaminosulfonyl, N,N-propylmethylaminosulfonyl, N,N-isopropylmethylaminosulfonyl, N,N-tert-butylmethylaminosulfonyl, N,N-butylethylaminosulfonyl, N,N-bis(1-methylpropyl)aminosulfonyl, N,N-heptylmethylaminosulfonyl and other N,N-2-substituted aminosulfonyl groups; etc.

[0077] As R 12 Examples of alkane dimethyl groups with 1 to 10 carbon atoms include methylene, ethylene, 1,3-propylene, 1,4-butylene, 1,5-pentylene, 1,6-hexylene, isopropylene, isobutylene, 2-methyl-1,3-propylene, isopentylene, isohexylene, isooctylene, and 2-ethylhexylene. Among these, alkane dimethyl groups with 1 to 6 carbon atoms are preferred, and alkane dimethyl groups with 1 to 4 carbon atoms are more preferred.

[0078] R 12 The -CH2- in the indicated alkane dimethyl group can be replaced with -O-, -CO-, or -NR. 8 -、-OCO-、-COO-、-OCONH-、-CONH- or -NHCO-.

[0079] As R 13 Alkyl groups having 1 to 4 carbon atoms are represented, for example, methyl, ethyl, propyl, and butyl.

[0080] As R 13 The alkoxy group represents alkoxy groups with 1 to 4 carbon atoms, for example, methoxy, ethoxy, propoxy, tert-butoxy, etc.

[0081] R 13 Preferably, it is methyl, ethyl, methoxy, or ethoxy, and more preferably methoxy or ethoxy.

[0082] As R 1 With R 2 R 3 With R 4 R 9 With R 10 The nitrogen-containing rings formed together can be exemplified by the following rings. In the following structures, * denotes a connecting bond.

[0083]

[0084] R 1 ~R 4 Preferably, each is an independent hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms that may have substituents, or an aromatic hydrocarbon group having 6 to 30 carbon atoms that may have substituents; more preferably, each is an independent hydrogen atom, an alkyl group having 1 to 10 carbon atoms that may have substituents, or an aromatic hydrocarbon group having 6 to 20 carbon atoms that may have substituents.

[0085] In particular, preferred R 1 and R 4 Each can independently represent an aromatic hydrocarbon group with 6 to 30 carbon atoms that may have substituents, R 2 and R 3 Each can independently represent a hydrogen atom or a saturated hydrocarbon group with 1 to 20 carbon atoms that may have substituents; more preferably, R 1 and R 4 Each can independently represent an aromatic hydrocarbon group with 6 to 20 carbon atoms that may have substituents, R 2 and R 3 Each of the following independently represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms that may have substituents; R is further preferred. 1 and R 4each independently represents an alkylphenyl group having 7 to 20 carbon atoms which can have a substituent, or an arylphenyl group having 12 to 20 carbon atoms which can have a substituent, R 2 and R 3 each independently represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms which can have a substituent.

[0086] R 9 and R 10 each independently is preferably a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, more preferably a hydrogen atom or a branched alkyl group having 3 to 10 carbon atoms, further preferably a hydrogen atom or a 2-ethylhexyl group. In particular, R 9 is a hydrogen atom, R 10 is an alkyl group having 1 to 10 carbon atoms, more preferably R 9 is a hydrogen atom, R 10 is a branched alkyl group having 3 to 10 carbon atoms, further preferably R 9 is a hydrogen atom, R 10 is a 2-ethylhexyl group.

[0087] As R 6 to R 7 represent an alkyl group having 1 to 6 carbon atoms, for example, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, and the like can be mentioned.

[0088] R 6 to R 7 each independently is preferably a hydrogen atom, a methyl group, or an ethyl group, more preferably a hydrogen atom.

[0089] R 5 is preferably -CO2H, -CO2 - Z + , -CO2R 8 , -SO3 - , -SO3 - Z + , -SO3H, -SO2NR 9 R 10 , more preferably -SO3 - , -SO3 - Z + , -SO3H, -SO2NR 9 R 10 , further preferably -SO3 - .

[0090] m is preferably 1 to 4, more preferably 1 or 2, further preferably 1.

[0091] R 5The bonding position is not particularly limited, but is preferably at least one of the two bonding positions that are ortho with respect to the xanthene skeleton, and more preferably one of the two bonding positions that are ortho with respect to the xanthene skeleton. In addition, in the case where m is 2 or more, it is preferable that at least one of the two bonding positions that are ortho with respect to the xanthene skeleton, and a bonding position that is para with respect to the xanthene skeleton be bonded, and more preferably one of the two bonding positions that are ortho with respect to the xanthene skeleton, and a bonding position that is para with respect to the xanthene skeleton be bonded.

[0092] As the halogen atom represented by X, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, and the like can be given.

[0093] In formula (1), the -SO3 - is preferably 0 or 1, and more preferably 1.

[0094] a represents 0 or 1, and is preferably 0.

[0095] The compound represented by formula (1) is preferably electrically neutral. That is, in the case where the compound represented by formula (1) has one -SO3 - in an ionic form, a is preferably 0, and in the case where the compound represented by formula (1) does not have -SO3 - in an ionic form, a is preferably 1.

[0096] The compound represented by formula (1) preferably has one or more groups selected from the group consisting of -SO3 - , -SO3H, -SO3 - Z + , and -SO2NR 9 R 10 consisting of 1 to 10 carbon atoms, which can have a substituent.

[0097] As the xanthene dye (al), a compound represented by formula (2) is more preferable. The compound represented by formula (2) can also be a tautomer thereof.

[0098]

[0099] [In formula (2),

[0100] R 21 and R 22 each independently represent a hydrogen atom, or an alkyl group having 1 to 10 carbon atoms, which can have a substituent.

[0101] R 23 and R 24 each independently represent an alkyl group having 1 to 4 carbon atoms, an aromatic hydrocarbon group having 6 to 10 carbon atoms, -SO3- -SO3H, -SO3 - Z + 、or -SO2NR 29 R 30 .

[0102] p and q each independently represent integers from 0 to 5. When p is greater than 2, multiple R... 23 They can be the same or different; when q is greater than 2, multiple Rs... 24 They can be the same or different.

[0103] R 25 Indicates -SO3 - -SO3H, -SO3 - Z + 、or -SO2NR 29 R 30 .

[0104] R 29 and R 30 Each can be independently represented by an alkyl group having 1 to 10 hydrogen or carbon atoms.

[0105] a, m, X, and Z + Same as above.

[0106] a, m, X, and Z + This also includes its preferred method in the mainland and a, m, X, and Z in equation (1). + same.

[0107] As R 21 ~R 22 and R 29 ~R 30 The alkyl group refers to alkyl groups with 1 to 10 carbon atoms. Specifically, examples include straight-chain or branched alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, isopropyl, isobutyl, tert-butyl, isopentyl, neopentyl, and 2-ethylhexyl.

[0108] R 21 and R 22 The alkyl group representing 1 to 10 carbon atoms may have substituents; examples of such substituents include those related to R. 1 ~R 4 The saturated hydrocarbon group representing 1 to 20 carbon atoms may have the same substituents. Among them, halogen atoms, hydroxyl groups, and carboxyl groups are preferred, and carboxyl groups are more preferred.

[0109] R 21 and R 22Each of R1and R2is independently preferably a hydrogen atom, or an alkyl group having a carbon number of 1 to 10 which can have a carboxyl group, more preferably a hydrogen atom, or an alkyl group having a carbon number of 1 to 5 which can have a carboxyl group, further preferably a hydrogen atom, or an alkyl group having a carbon number of 2 to 4 which can have a carboxyl group.

[0110] R 29 and R 30 Each of R1and R2is independently preferably a hydrogen atom, or an alkyl group having a carbon number of 1 to 10 which can have a carboxyl group, more preferably a hydrogen atom, or an alkyl group having a carbon number of 1 to 5 which can have a carboxyl group, further preferably a hydrogen atom, or an alkyl group having a carbon number of 2 to 4 which can have a carboxyl group. 29 is a hydrogen atom, R 30 is an alkyl group having a carbon number of 1 to 10, more preferably R 29 is a hydrogen atom, R 30 is an alkyl group having a carbon number of 3 to 10, further preferably R 29 is a hydrogen atom, R 30 is a 2-ethylhexyl group.

[0111] As the alkyl group having a carbon number of 1 to 4 represented by R 23 and R 24 , for example, a methyl group, an ethyl group, a propyl group, a butyl group, an isopropyl group, an isobutyl group, a sec-butyl group, a t-butyl group, or the like can be given, of which an alkyl group having a carbon number of 1 to 2 is preferred, and a methyl group is more preferred.

[0112] As the aromatic hydrocarbon group having a carbon number of 6 to 10 represented by R 23 and R 24 , for example, a phenyl group; an alkylphenyl group such as a tolyl group, a xylyl group, a mesityl group, a propylphenyl group, a butylphenyl group, or the like; and the like can be given, of which a phenyl group is preferred.

[0113] R 23 and R 24 Each of R1and R2is independently preferably an alkyl group having a carbon number of 1 to 4, or an aromatic hydrocarbon group having a carbon number of 6 to 10, more preferably a methyl group or a phenyl group.

[0114] As the bonding position of R 23 and R 24 , at least one of the 2 bonding positions which are ortho positions with respect to N is preferred, and the 2 bonding positions which are ortho positions with respect to N are more preferred.

[0115] Each of p and q is independently preferably an integer of 0 to 3, more preferably an integer of 1 to 3, further preferably an integer of 1 to 2, and particularly preferably 2.

[0116] R 25 is particularly preferably -SO3 - .

[0117] In formula (2), the number of -SO3 - is preferably 0 or 1, more preferably 1.

[0118] The compound represented by formula (2) is preferably electrically neutral. That is, in the case where the compound represented by formula (2) has one -SO3 - group in an ionic form, a is preferably 0, and in the case where the compound represented by formula (2) has no -SO3 - group in an ionic form, a is preferably 1.

[0119] The compound represented by formula (2) preferably has one or more groups selected from the group consisting of -SO3 - , -SO3H, -SO3 - Z + , and -SO2NR 9 R 10 , more preferably 1 to 4, and further preferably 1 to 2.

[0120] As the xanthene dye (a1), for example, a compound represented by formula (1-1) to formula (1-42) can be given. Note that, in the following formulae, Ra represents a 2-ethylhexyl group.

[0121]

[0122]

[0123]

[0124]

[0125] Further, as the xanthene dye (a1), a salt-forming compound formed from any one of the compounds represented by the following formulae (a) to (d) and a copolymer having a glass transition temperature of 30 to 60°C and an ammonium salt value of 30 to 40 mgKOH / g in terms of a solid content, the copolymer being a copolymer of a monomer group including methyl methacrylate, 2-ethylhexyl methacrylate, and dimethylaminoethyl methacrylate chloride salt, etc. can be specifically given. Note that the aforementioned glass transition temperature can be calculated from the Fox equation, and the aforementioned ammonium salt value can be calculated by titrating with a 0.1N silver nitrate aqueous solution after using a 5% potassium chromate aqueous solution as an indicator and converting into the equivalent of potassium hydroxide.

[0126]

[0127] The colored curable resin composition of the present application can include one or two or more xanthene dyes (a1).

[0128] As the violet pigment (hereinafter, sometimes referred to as violet pigment (a2)) contained in the aforementioned colorant (A), known violet pigments can be used, and, for example, pigments having a hue of violet among pigments classified as pigments in the Dye Index (published by The Society of Dyers and Colourists) can be mentioned (wherein xanthene pigments are excluded). The colored curable resin composition of the present application can contain one or two or more kinds of violet pigments.

[0129] As the violet pigment (a2), specifically, C.I. Pigment Violet 19, 23, 29, 32, 36, 38, and the like can be mentioned, and at least one selected from the group consisting of C.I. Pigment Violet 19, 23, 29 is preferred, and C.I. Pigment Violet 19 and / or 23 is more preferred.

[0130] As the blue pigment (hereinafter, sometimes referred to as blue pigment (a3)) contained in the aforementioned colorant (A), known blue pigments can be used, and, for example, pigments having a hue of blue among pigments classified as pigments in the Dye Index (published by The Society of Dyers and Colourists) can be mentioned. The colored curable resin composition of the present application can contain one or two or more kinds of blue pigments (a3).

[0131] As the blue pigment (a3), specifically, C.I. Pigment Blue 15, 15:3, 15:4, 15:6, 16, 60, 80, and the like can be mentioned, and phthalocyanine-based blue pigments such as C.I. Pigment Blue 15, 15:3, 15:4, 15:6, 16, and the like are preferred, and copper phthalocyanine-based blue pigments such as C.I. Pigment Blue 15, 15:3, 15:4, 15:6, and the like are more preferred, and C.I. Pigment Blue 15:4 and / or 15:6 is further preferred, and at least containing C.I. Pigment Blue 15:6 is particularly preferred.

[0132] The content ratio of C.I. Pigment Blue 15:6 in 100 mass% of the blue pigment (a3) is preferably 30 mass% or more, more preferably 50 mass% or more, further preferably 70 mass% or more, and particularly preferably 80 mass% or more, and can be 100 mass%.

[0133] The content of the xanthene pigment (a1) with respect to the total amount of the colorant (A) is preferably 1 to 60 mass%, more preferably 3 to 45 mass%, further preferably 6 to 35 mass%, and can be 10 to 30 mass%.

[0134] The content of the violet pigment (a2) with respect to the total amount of the colorant (A) is preferably 0.1 to 40 mass%, more preferably 0.5 to 30 mass%, and further preferably 0.8 to 20 mass%.

[0135] The content of the blue pigment (a3) is preferably 30 to 98 mass%, more preferably 50 to 94 mass%, and further preferably 60 to 90 mass%, relative to the total amount of the colorant (A).

[0136] The content of the xanthene dye (al) is 8 to 45 parts by mass, relative to 100 parts by mass of the blue pigment (a3). In the composition containing the xanthene dye (al), the violet pigment (a2), and the blue pigment (a3), by adjusting the content of the xanthene dye (al) to the above range, the leakage of green light in the obtained color filter can be suppressed. In addition, from the viewpoint of further suppressing the leakage of red light in the obtained color filter, the content of the xanthene dye (al) is preferably 8 to 40 parts by mass, more preferably 8 to 32 parts by mass, and can also be 8 to 20 parts by mass, relative to 100 parts by mass of the blue pigment (a3).

[0137] In addition, by adjusting the content of the xanthene dye (al) to 35 to 45 parts by mass, relative to 100 parts by mass of the blue pigment (a3), the effect of suppressing the leakage of green light in the obtained color filter can be significantly improved.

[0138] The content of the violet pigment (a2) is preferably 5 to 250 parts by mass, relative to 100 parts by mass of the xanthene dye (al). In particular, from the viewpoint of further suppressing the leakage of green light, the aforementioned content is more preferably 5 to 100 parts by mass, and can also be 5 to 85 parts by mass.

[0139] In addition, by adjusting the content of the violet pigment (a2) to more than 100 parts by mass, preferably 130 to 250 parts by mass, relative to 100 parts by mass of the xanthene dye (al), the leakage of red light can be suppressed and the amount of the colorant can be reduced, so that a blue color filter having more excellent reliability such as chemical resistance, heat resistance, and pattern formability can be formed, and from this point of view, it is preferable.

[0140] In addition, from the viewpoint of significantly improving the effect of suppressing the leakage of red light, it is preferable to adjust the content of the xanthene dye (al) to 8 to 20 parts by mass, relative to 100 parts by mass of the blue pigment (a3), and to adjust the content of the violet pigment (a2) to 90 parts by mass or less, in particular 5 to 85 parts by mass, relative to 100 parts by mass of the xanthene dye (al).

[0141] The total content of the xanthene dye (al), the violet pigment (a2), and the blue pigment (a3) is preferably 60 mass% or more, more preferably 80 mass% or more, further preferably 90 mass% or more, particularly preferably 95 mass% or more, and can also be 100 mass%, relative to the total amount of the colorant (A).

[0142] The colorant (A) can include one or two or more colorants other than the xanthene colorant (al), the violet colorant (a2), and the blue colorant (a3) (hereinafter, sometimes referred to as other colorants (a4)).

[0143] As the other colorant (a4), any colorant among dyes (hereinafter, sometimes referred to as dyes (a4-1)) and pigments (hereinafter, sometimes referred to as pigments (a4-2)) can be used.

[0144] The dye (a4-1) is not particularly limited, and known dyes can be used. For example, solvent dyes, acid dyes, direct dyes, mordant dyes, and the like can be given. As the dyes, for example, compounds classified as dyes in the Dye Index (published by The Society of Dyers and Colourists), known dyes described in the Dyeing Guide (Sanchin Co., Ltd.) can be given. In addition, depending on the chemical structure, azo dyes, cyanine dyes, triarylmethane dyes, thiazole dyes, oxazine dyes, anthraquinone dyes, naphthoquinone dyes, quinonimine dyes, methine dyes, methenimine dyes, squarylium dyes, acridine dyes, styryl dyes, coumarin dyes, quinoline dyes, nitro dyes, phthalocyanine dyes, perylene dyes, quinophthalone dyes, isoindoline dyes, and the like can be given.

[0145] As the dye (a4-1), specifically, the following can be given:

[0146] C.I. Solvent Yellow 4, 14, 15, 23, 24, 38, 62, 63, 68, 82, 94, 98, 99, 117, 162, 163, 167, 189;

[0147] C.I. Solvent Red 45, 49, 111, 125, 130, 143, 145, 146, 150, 151, 155, 168, 169, 172, 175, 181, 207, 222, 227, 230, 245, 247;

[0148] C.I. Solvent Orange 2, 7, 11, 15, 26, 56, 77, 86;

[0149] C.I. Solvent Violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60;

[0150] C.I. 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;

[0151] C.I. Solvent Green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35 and the like C.I. Solvent dyes,

[0152] C.I. Acid Yellow 1, 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112, 113, 114, 116, 119, 123, 128, 134, 135, 138, 139, 140, 144, 150, 155, 157, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251;

[0153] C.I. Acid Red 1, 4, 8, 14, 17, 18, 26, 27, 29, 31, 33, 34, 35, 37, 40, 42, 44, 50, 57, 66, 73, 76, 80, 88, 91, 95, 97, 98, 103, 106, 111, 114, 129, 133, 134, 138, 143, 145, 150, 151, 155, 158, 160, 172, 176, 182, 183, 195, 198, 206, 211, 215, 216, 217, 227, 228, 249, 252, 257, 258, 260, 261, 266, 268, 270, 274, 277, 280, 281, 308, 312, 315, 316, 339, 341, 345, 346, 349, 382, 383, 394, 401, 412, 417, 418, 422, 426;

[0154] C.I. Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 169, 173;

[0155] C.I. Acid Violet 6B, 7, 15, 16, 17, 19, 21, 23, 24, 25, 34, 38, 49, 72;

[0156] C.I. Acid Blue 1, 3, 5, 7, 9, 11, 13, 15, 17, 18, 22, 23, 24, 25, 26, 27, 29, 34, 38, 40, 41, 42, 43, 45, 48, 51, 54, 59, 60, 62, 70, 72, 74, 75, 78, 80, 82, 83, 86, 87, 88, 90, 90:1, 91, 92, 93, 93:1, 96, 99, 100, 102, 103, 104, 108, 109, 110, 112, 113, 117, 119, 120, 123, 126, 127, 129, 130, 131, 138, 140, 142, 143, 147, 150, 151, 154, 158, 161, 166, 167, 168, 170, 171, 175, 182, 183, 184, 187, 192, 199, 203, 204, 205, 210, 213, 229, 234, 236, 242, 243, 256, 259, 267, 269, 278, 280, 285, 290, 296, 315, 324:1, 335, 340;

[0157] C.I. Acid Green 1, 3, 5, 6, 7, 8, 9, 11, 13, 14, 15, 16, 22, 25, 27, 28, 41, 50, 50:1, 58, 63, 65, 80, 104, 105, 106, 109 and the like C.I. Acid dyes,

[0158] C.I. 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;

[0159] C.I. 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;

[0160] C.I. Direct Orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107;

[0161] C.I. Direct Violet 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104;

[0162] C.I. Direct Blue 1, 2, 3, 6, 8, 15, 22, 25, 28, 29, 40, 41, 42, 47, 52, 55, 57, 71, 76, 77, 78, 80, 81, 84, 85, 86, 90, 93, 94, 95, 97, 98, 99, 100, 101, 106, 107, 108, 109, 113, 114, 115, 117, 119, 120, 137, 149, 150, 153, 155, 156, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 168, 170, 171, 172, 173, 188, 189, 190, 192, 193, 194, 195, 196, 198, 199, 200, 201, 202, 203, 207, 209, 210, 212, 213, 214, 222, 225, 226, 228, 229, 236, 237, 238, 242, 243, 244, 245, 246, 247, 248, 249, 250, 251, 252, 256, 257, 259, 260, 268, 274, 275, 293;

[0163] C.I. Direct Green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 77, 79, 82 and the like C.I. Direct dyes,

[0164] C.I. Disperse Yellow 51, 54, 76;

[0165] C.I. Disperse Violet 26, 27;

[0166] C.I. Disperse Blue 1, 14, 56, 60 and the like C.I. Disperse dyes,

[0167] C.I. 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;

[0168] C.I. Basic Violet 2;

[0169] C.I. Basic Red 9;

[0170] C.I. Basic Green 1 ; and the like C.I. Basic dyes,

[0171] C.I. Reactive Yellow 2, 76, 116;

[0172] C.I. Reactive Orange 16;

[0173] C.I. Reactive Red 36; and the like C.I. Reactive Dyes,

[0174] C.I. Mordant Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65;

[0175] C.I. Mordant Red 1, 2, 3, 4, 9, 11, 12, 14, 17, 18, 19, 22, 23, 24, 25, 26, 29, 30, 32, 33, 36, 37, 38, 39, 41, 42, 43, 45, 46, 48, 52, 53, 56, 62, 63, 71, 74, 76, 78, 85, 86, 88, 90, 94, 95;

[0176] C.I. Mordant Orange 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47, 48;

[0177] C.I. Mordant Violet 1, 1:1, 2, 3, 4, 5, 6, 7, 8, 10, 11, 14, 15, 16, 17, 18, 19, 21, 22, 23, 24, 27, 28, 30, 31, 32, 33, 36, 37, 39, 40, 41, 44, 45, 47, 48, 49, 53, 58;

[0178] C.I. Mordant Blue 1, 2, 3, 7, 8, 9, 12, 13, 15, 16, 19, 20, 21, 22, 23, 24, 26, 30, 31, 32, 39, 40, 41, 43, 44, 48, 49, 53, 61, 74, 77, 83, 84;

[0179] C.I. Mordant Green 1, 3, 4, 5, 10, 13, 15, 19, 21, 23, 26, 29, 31, 33, 34, 35, 41, 43, 53 and the like C.I. Mordant Dyes,

[0180] C.I. Vat Green 1 and the like C.I. Vat Dyes and the like.

[0181] These dyes (a4-1) can use one dye or a plurality of dyes for each color, or can combine the dyes of each color.

[0182] As the pigments (a4-2), for example, pigments classified as pigments in the Dye Index (published by The Society of Dyers and Colourists) can be mentioned.

[0183] As the pigments classified as pigments, specifically, pigments classified as pigments in the Dye Index (published by The Society of Dyers and Colourists) can be mentioned.

[0184] C.I. Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 129, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 185, 194, 214, 231, 235, 236, and the like yellow pigments;

[0185] C.I. Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73, and the like orange pigments;

[0186] C.I. Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 178, 179, 180, 190, 192, 202, 209, 215, 216, 224, 242, 254, 255, 264, 265, 266, 268, 269, 272, 273, 291, 297, and the like red pigments;

[0187] C.I. Pigment Green 7, 36, 58, 59, 62, 63, 64, 65, 66, 67, and the like green pigments;

[0188] C.I. Pigment Brown 23, 25, and the like brown pigments;

[0189] C.I. Pigment Black 1, 7, 31, 32, and the like black pigments; and the like.

[0190] These pigments (a4-2) can use one pigment or a plurality of pigments for each color, and can combine pigments of each color.

[0191] The xanthene pigment (al), the violet pigment (a2), the blue pigment (a3), and the pigment (a4-2) can be subjected to rosin treatment, surface treatment using a pigment derivative into which an acidic group or a basic group is introduced, graft treatment onto the surface of the pigment using a high molecular compound or the like, microparticulation treatment using a sulfuric acid microparticulation method or the like, washing treatment for removing impurities using an organic solvent, water, or the like, removal treatment of ionic impurities using an ion exchange method or the like, as needed. The particle diameters of these colorants are preferably substantially uniform. In addition, by subjecting these colorants to dispersion treatment by containing a pigment dispersant, a colorant dispersion liquid in a state of being uniformly dispersed in a pigment dispersant solution can be produced. These colorants can each be individually subjected to dispersion treatment, or a plurality of kinds can be mixed and subjected to dispersion treatment.

[0192] As the pigment dispersant, a surfactant or the like can be used, and any of a cationic type, an anionic type, a nonionic type, and an amphoteric type can be used. Specifically, a polyester type, a polyamine type, an acrylic acid type, and the like can be used. These pigment dispersants can be used alone or in combination with two or more. As the pigment dispersant, if expressed by a trade name, KP (manufactured by Shin-Etsu Chemical Co., Ltd.), FLOREN (manufactured by Kyoeisha Chemical Co., Ltd.), Solsperse (registered trademark) (manufactured by Zeneca Co., Ltd.), EFA (registered trademark) (manufactured by BASF), AJISPER (registered trademark) (manufactured by Ajinomoto Fine Techno Co., Ltd.), Disperbyk (registered trademark), BYK (registered trademark) (manufactured by BYK-Chemie Co., Ltd.), and the like can be used.

[0193] In the case of using a pigment dispersant, the amount of use is preferably 5 to 200 parts by mass, more preferably 8 to 150 parts by mass, and further preferably 10 to 100 parts by mass, with respect to 100 parts by mass of the colorant. If the amount of use of the pigment dispersant is within the aforementioned range, in the case of producing a colorant dispersion liquid containing two or more kinds of colorants, there is a tendency that a more uniform dispersion state of the colorant dispersion liquid can be obtained.

[0194] The content ratio of the aforementioned colorant (A) is, for example, 10 to 75% by mass, preferably 20 to 60% by mass, more preferably 30 to 60% by mass, further preferably 35 to 55% by mass, and still further preferably 35 to 43% by mass, in the total amount of solid components. By adjusting the content ratio of the colorant (A) to be equal to or higher than the aforementioned lower limit value, it becomes easier to obtain a suitable spectral transmittance, color density as a color filter. In addition, by adjusting the content ratio of the colorant (A) to be equal to or lower than the aforementioned upper limit value, reliability, pattern formability can be improved, that is, it is preferable from the viewpoint that color separation, and reliability, pattern formability can be simultaneously achieved.

[0195] Note that, in the present specification, the total amount of solid components refers to the total amount of components after the solvent is removed from the colored curable resin composition of the present application. The total amount of solid components and the content of each component relative thereto can be determined by known analytical means such as liquid chromatography, gas chromatography, and the like.

[0196] <Resin (B)>

[0197] The resin (B) is not particularly limited, but is preferably an alkali-soluble resin. As the resin (B), the following resins [K1] to [K6] and the like can be given.

[0198] Resin [K1]: a copolymer having a structural unit from at least one monomer (a) selected from the group consisting of an unsaturated carboxylic acid and an unsaturated carboxylic anhydride (hereinafter sometimes referred to as "(a)") and a structural unit from a monomer (b) having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenic unsaturated bond (hereinafter sometimes referred to as "(b)");

[0199] Resin [K2]: a copolymer having a structural unit from the aforementioned (a), a structural unit from the aforementioned (b), and a structural unit from a monomer (c) capable of copolymerization with (a) (but different from (a) and (b)). (Hereinafter sometimes referred to as "(c)");

[0200] Resin [K3]: a copolymer having a structural unit from the aforementioned (a) and a structural unit from the aforementioned (c);

[0201] Resin [K4]: a copolymer having a structural unit in which the aforementioned (b) is added to a structural unit from the aforementioned (a), and a structural unit from the aforementioned (c), and is a copolymer containing a structural unit from (a) to which (b) is not added;

[0202] Resin [K4']: a copolymer having a structural unit in which the aforementioned (b) is added to a structural unit from the aforementioned (a), and a structural unit from the aforementioned (c), and is a copolymer not containing a structural unit from (a) to which (b) is not added;

[0203] Resin [K5]: a copolymer having a structural unit in which the aforementioned (a) is added to a structural unit from the aforementioned (b), and a structural unit from the aforementioned (c) (may contain a structural unit from (b) to which (a) is not added, but is preferably not contained);

[0204] Resin [K6]: a copolymer having a structural unit in which the aforementioned (a) is added to a structural unit from the aforementioned (b) and further a carboxylic anhydride is added, and a structural unit from the aforementioned (c).

[0205] As (a), specifically, for example, the following can be given:

[0206] Unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, o-, m-, p-vinylbenzoic acid, and the like;

[0207] Unsaturated dicarboxylic acids such as maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyltetrahydrophthalic acid, 1,4-cyclohexene dicarboxylic acid, and the like;

[0208] Carboxyl-containing bicyclic unsaturated compounds such as methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo[2.2.1]hept-2-ene, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene, 5-carboxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-carboxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-carboxy-6-methylbicyclo[2.2.1]hept-2-ene, 5-carboxy-6-ethylbicyclo[2.2.1]hept-2-ene, and the like;

[0209] Unsaturated dicarboxylic anhydrides such as maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride, and the like;

[0210] Unsaturated mono[(meth)acryloyloxyalkyl] esters of polycarboxylic acids having 2 or more valences such as succinic acid mono[2-(meth)acryloyloxyethyl] ester, phthalic acid mono[2-(meth)acryloyloxyethyl] ester, and the like;

[0211] Unsaturated acrylic esters having a hydroxyl group and a carboxyl group in the same molecule such as α-(hydroxymethyl)acrylic acid, and the like.

[0212] Among them, from the aspect of copolymerizability, the solubility of the obtained resin in an aqueous alkaline solution, acrylic acid, methacrylic acid, maleic anhydride, and the like are preferred.

[0213] (b) is, for example, a polymerizable compound having a cyclic ether structure having 2 to 4 carbon atoms (for example, at least one selected from the group consisting of an oxirane ring, an oxetane ring, and a tetrahydrofuran ring) and an ethylenic unsaturated bond. (b) is preferably a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth)acryloyloxy group.

[0214] Note that in the present specification, "(meth)acrylic acid" means at least one selected from the group consisting of acrylic acid and methacrylic acid. The expressions "(meth)acryl" and "(meth)acrylate" and the like also have the same meaning.

[0215] As (b), for example, monomer (b1) having an epoxyethyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b1)"), monomer (b2) having an oxetanyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b2)"), monomer (b3) having a tetrahydrofuryl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b3)") and the like can be given.

[0216] As (b1), for example, monomer (b1-1) having a structure in which a straight-chain or branched-chain aliphatic unsaturated hydrocarbon is epoxidized (hereinafter sometimes referred to as "(b1-1)"), monomer (b1-2) having a structure in which a alicyclic unsaturated hydrocarbon is epoxidized (hereinafter sometimes referred to as "(b1-2)") can be given.

[0217] As (b1-1), (meth)acrylic acid glycidyl ester, β-methyl (meth)acrylic acid glycidyl ester, β-ethyl (meth)acrylic acid glycidyl ester, glycidyl vinyl ether, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether, a-methyl-o-vinylbenzyl glycidyl ether, a-methyl-m-vinylbenzyl glycidyl ether, a-methyl-p-vinylbenzyl glycidyl ether, 2,3-bis(glycidyloxymethyl)styrene, 2,4-bis(glycidyloxymethyl)styrene, 2,5-bis(glycidyloxymethyl)styrene, 2,6-bis(glycidyloxymethyl)styrene, 2,3,4-tris(glycidyloxymethyl)styrene, 2,3,5-tris(glycidyloxymethyl)styrene, 2,3,6-tris(glycidyloxymethyl)styrene, 3,4,5-tris(glycidyloxymethyl)styrene, 2,4,6-tris(glycidyloxymethyl)styrene and the like can be given.

[0218] As (b1-2), vinylcyclohexene monoxide, 1,2-epoxy-4-vinylcyclohexane (for example, Celloxide 2000; manufactured by Daicel Corp.), (meth)acrylic acid 3,4-epoxycyclohexylmethyl ester (for example, Cyclomer A400; manufactured by Daicel Corp.), (meth)acrylic acid 3,4-epoxycyclohexylmethyl ester (for example, Cyclomer M100; manufactured by Daicel Corp.), a compound represented by formula (BI) and a compound represented by formula (BII) and the like can be given.

[0219]

[0220] In formulas (BI) and (BII), R e and R f It represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, wherein the hydrogen atom contained in the alkyl group may be replaced by a hydroxyl group.

[0221] X e and X f Indicates a single bond, *-R g -、*-R g -O-、*-R g -S- or *-R g -NH-.

[0222] R g It represents the dimethyl groups of alkanes with 1 to 6 carbon atoms.

[0223] * indicates a connection to 'O'.

[0224] Examples of alkyl groups having 1 to 4 carbon atoms include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, and tert-butyl.

[0225] 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.

[0226] As R e and R f Preferably, hydrogen atoms, methyl groups, hydroxymethyl groups, 1-hydroxyethyl groups, and 2-hydroxyethyl groups are included; more preferably, hydrogen atoms and methyl groups are included.

[0227] Examples of alkane 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.

[0228] As X e and X f Preferred examples include single bonds, methylene, ethylene, *-CH2-O- and *-CH2CH2-O-, and more preferably single bonds and *-CH2CH2-O- (* indicates a bond with O).

[0229] As the compound represented by formula (BI), mention can be made of a compound represented by any one of formulae (BI-1) to (BI-15), and the like. Among them, preferred are a compound represented by formula (BI-1), formula (BI-3), formula (BI-5), formula (BI-7), formula (BI-9), or formula (BI-11) to (BI-15), and more preferred are a compound represented by formula (BI-1), formula (BI-7), formula (BI-9), or formula (BI-15).

[0230]

[0231] As the compound represented by formula (BI), mention can be made of a compound represented by any one of formulae (BI-1) to (BI-15), and the like. Among them, preferred are a compound represented by formula (BI-1), formula (BI-3), formula (BI-5), formula (BI-7), formula (BI-9), or formula (BI-11) to (BI-15), and more preferred are a compound represented by formula (BI-1), formula (BI-7), formula (BI-9), or formula (BI-15).

[0232]

[0233] The compound represented by formula (BI) and the compound represented by formula (BII) can each be used alone, or two or more kinds thereof can be used in combination. In the case where the compound represented by formula (BI) and the compound represented by formula (BII) are used in combination, their contained ratio [compound represented by formula (BI) : compound represented by formula (BII)] is preferably 5 : 95 to 95 : 5, and more preferably 20 : 80 to 80 : 20, on a molar basis.

[0234] As (b2), more preferred is a monomer having an oxetanyl group and a (meth)acryloyloxy group. As (b2), mention can be made of 3-methyl-3-(meth)acryloyloxymethyl oxetane, 3-ethyl-3-(meth)acryloyloxymethyl oxetane, 3-methyl-3-(meth)acryloyloxyethyl oxetane, 3-ethyl-3-(meth)acryloyloxyethyl oxetane, and the like.

[0235] As (b3), more preferred is a monomer having a tetrahydrofurfuryl group and a (meth)acryloyloxy group. As (b3), specifically, mention can be made of tetrahydrofurfuryl acrylate (for example, Viscoat V#150, manufactured by Osaka Organic Chemical Industry Co., Ltd.), tetrahydrofurfuryl methacrylate, and the like.

[0236] As for (b), from the perspective of further improving the reliability of the obtained color filter, such as heat resistance and chemical resistance, (b1) is preferred. Furthermore, from the perspective of excellent storage stability of the color-curing resin composition, (b1-2) is more preferred.

[0237] Examples of (c) include (meth)acrylate monomers, unsaturated carboxylic acid esters such as unsaturated dicarboxylic acid esters; vinyl monomers such as vinyl monomers having unsaturated aliphatic hydrocarbon rings or aromatic rings; maleimides; and so on.

[0238] Examples of (meth)acrylate monomers include:

[0239] Methyl methacrylate, ethyl methacrylate, n-butyl methacrylate, sec-butyl methacrylate, tert-butyl methacrylate, 2-ethylhexyl methacrylate, dodecyl methacrylate, lauryl methacrylate, stearyl methacrylate, cyclopentyl methacrylate, and other (meth)acrylates with straight or branched aliphatic saturated hydrocarbon groups.

[0240] (Meth)acrylates such as allyl methacrylate and propargyl methacrylate are aliphatic unsaturated hydrocarbon groups with straight or branched chains.

[0241] Cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, tricyclohexyl (meth)acrylate [5.2.1.0] 2 ,6 Decane-8-yl ester (commonly referred to as "(meth)acrylate dicyclopentyl ester" in this technical field; sometimes also called "(meth)acrylate tricyclodecyl ester"), isobornyl ester of (meth)acrylate, adamantane ester of (meth)acrylate, and other (meth)acrylates having cyclic saturated hydrocarbon groups;

[0242] (Meth)acrylate tricyclic [5.2.1.0] 2,6 Decen-8-yl ester (commonly referred to as "(meth)acrylate dicyclopentenyl ester"), (meth)acrylate dicyclopentyloxyethyl ester, and other (meth)acrylates having cyclic unsaturated aliphatic hydrocarbon groups;

[0243] (Meth)acrylates such as phenyl methacrylate, naphthyl methacrylate, benzyl methacrylate, and phenoxybenzyl methacrylate contain aromatic rings.

[0244] (Meth)acrylates containing hydroxyl groups, such as 2-hydroxyethyl methacrylate and 2-hydroxypropyl methacrylate.

[0245] As the unsaturated dicarboxylic acid ester, there are mentioned diethyl maleate, diethyl fumarate, diethyl itaconate and the like.

[0246] Among these unsaturated carboxylic acid esters, there are preferably:

[0247] methyl methacrylate, 2-ethylhexyl acrylate and the like (meth)acrylic acid C 1-10 alkyl ester;

[0248] (meth)acrylic acid tricyclo[5.2.1.0 2,6 ]dec-8-yl ester and the like (meth)acrylic acid ester having a cyclic saturated hydrocarbon group;

[0249] (meth)acrylic acid tricyclo[5.2.1.0 2,6 ]decen-8-yl ester and the like (meth)acrylic acid ester having a cyclic unsaturated aliphatic hydrocarbon group;

[0250] (meth)acrylic acid benzyl ester, (meth)acrylic acid phenoxybenzyl ester and the like (meth)acrylic acid ester having an aromatic ring and the like.

[0251] As the vinyl monomer having an unsaturated aliphatic hydrocarbon ring, there are mentioned bicyclo[2.2.1]hept-2-ene (or also called 2-norbornene), 5-methylbicyclo[2.2.1]hept-2-ene, 5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxybicyclo[2.2.1]hept-2-ene, 5-hydroxymethylbicyclo[2.2.1]hept-2-ene, 5-(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5-methoxybicyclo[2.2.1]hept-2-ene, 5-ethoxybicyclo[2.2.1]hept-2-ene, 5,6-dihydroxybicyclo[2.2.1]hept-2-ene, 5,6-bis(hydroxymethyl)bicyclo[2.2.1]hept-2-ene, 5,6-bis(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5,6-dimethoxybicyclo[2.2.1]hept-2-ene, 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-t-butoxycarbonylbicyclo[2.2.1]hept-2-ene, 5-cyclohexyloxycarbonylbicyclo[2.2.1]hept-2-ene, 5-phenoxy-carbonylbicyclo[2.2.1]hept-2-ene, 5,6-bis(t-butoxycarbonyl)bicyclo[2.2.1]hept-2-ene, 5,6-bis(cyclohexyloxycarbonyl)bicyclo[2.2.1]hept-2-ene and the like bicyclic unsaturated compounds.

[0252] As the vinyl monomer having an aromatic ring, styrene, α-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, p-methoxystyrene, and the like styrene-based monomers can be given.

[0253] As other vinyl monomers, monomers containing a nitrile group such as acrylonitrile, methacrylonitrile, and the like can be given.

[0254] Monomers containing a halogen atom such as vinyl chloride, vinylidene chloride, and the like can be given.

[0255] Acrylamide, methacrylamide, vinyl acetate, 1,3-butadiene, isoprene, 2,3-dimethyl-1,3-butadiene, and the like can be given.

[0256] Among these vinyl monomers, from the aspects of copolymerizability and heat resistance, styrene, styrene-based monomers such as vinyltoluene, and bicyclo[2.2.1]hept-2-ene (or also called 2-norbornene), bicyclic unsaturated compounds, and the like are preferred.

[0257] As the maleimide, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimidobenzoate, N-succinimidyl-4-maleimidobutyrate, N-succinimidyl-6-maleimidohexanoate, N-succinimidyl-3-maleimidopropionate, N-(9-acridinyl)maleimide, and the like can be given.

[0258] Among these maleimides, from the aspects of copolymerizability and heat resistance, maleimides having an alicyclic hydrocarbon group or an aromatic hydrocarbon group such as N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, and the like are preferred.

[0259] The structural unit resulting from addition of (b) to the structural unit from (a) means a unit resulting from addition of (b) to the structural unit from (a) constituting the main chain of the copolymer, having a side chain unsaturated group from (b). In this structural unit, (a) can be any one of the aforementioned examples, and (b) can also be any one of the aforementioned examples. As (a), an unsaturated monocarboxylic acid such as (meth)acrylic acid is preferred. As (b), a monomer (b1) having an epoxyethyl group and an ethylenic unsaturated bond is preferred, and a monomer (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized is more preferred.

[0260] The structural unit in which (a) is added to the structural unit from (b) is a unit in which (a) is bonded to the structural unit from (b) constituting the main chain of the copolymer by addition, and has a side chain unsaturated group from (a). In this structural unit, (b) can be any one of the aforementioned examples, and (a) can also be any one of the aforementioned examples. As (b), a monomer (bl) having an epoxy ethyl group and an ethylenic unsaturated bond is preferable, and a monomer (bl-1) having a structure in which a straight-chain or branched-chain aliphatic unsaturated hydrocarbon is epoxidized is more preferable. As (a), an unsaturated monocarboxylic acid such as (meth)acrylic acid is preferable.

[0261] The structural unit in which (a) is added to the structural unit from (b) and further a carboxylic anhydride is added is a structural unit in which a carboxylic anhydride is bonded by half-esterification to a hydroxyl group generated in the structural unit from (b) to which (a) is bonded to constitute the main chain of the copolymer by addition, and has a side chain carboxyl group from the carboxylic anhydride and a side chain unsaturated group from (a). In this structural unit, (b) can be any one of the aforementioned examples, and (a) can also be any one of the aforementioned examples. As (b), a monomer (bl) having an epoxy ethyl group and an ethylenic unsaturated bond is preferable, and a monomer (bl-1) having a structure in which a straight-chain or branched-chain aliphatic unsaturated hydrocarbon is epoxidized is more preferable. As (a), an unsaturated monocarboxylic acid such as (meth)acrylic acid is preferable.

[0262] As the carboxylic anhydride, a saturated aliphatic polycarboxylic anhydride such as malonic anhydride, succinic anhydride, glutaric anhydride, adipic anhydride; an unsaturated aliphatic polycarboxylic anhydride such as maleic anhydride, citraconic anhydride, itaconic anhydride; an aromatic polycarboxylic anhydride such as 3-vinylphthalic anhydride, 4-vinylphthalic anhydride; an alicyclic polycarboxylic anhydride such as 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 the like can be exemplified.

[0263] In the resin [K1], the ratio of the structural unit from each of (a) and (b) in all the structural units constituting the resin [K1] is preferably:

[0264] Structural unit from (a): 2 to 60 mol%

[0265] Structural unit from (b): 40 to 98 mol%,

[0266] More preferably, the ratio of the structural unit from each of (a) and (b) in all the structural units constituting the resin [K1] is:

[0267] Structural unit from (a): 10 to 50 mol%

[0268] Structural unit from (b): 50 to 90 mol%.

[0269] Further, it is preferable that the coloring curable resin composition of the present application substantially not contain the structural unit from (c).

[0270] The total of the structural unit from (a) and the structural unit from (b) among all the structural units constituting the resin [Kl] is, for example, 90 mol% or more, preferably 95 mol% or more, more preferably 98 mol% or more, and particularly preferably 100 mol%.

[0271] If the ratio of the structural units of the resin [Kl] is within the above range, the tendency of the storage stability of the coloring curable resin composition, the developability at the time of forming a colored pattern, and the solvent resistance of the obtained color filter are excellent.

[0272] The resin [Kl] can be produced, for example, by the method described in the reference "Kakozai no Shikenho Jikkenho" (Kakozai no Shikenho Jikkenho) (Takahiro Otsu, issued by Kogyo Tsushinsha Co., Ltd., 1st edition, 1st printing, March 1, 1972) and the references described in the reference.

[0273] Specifically, the following method can be mentioned: a prescribed amount of (a) and (b), a polymerization initiator, and a solvent or the like are added to a reaction vessel, and, for example, oxygen is replaced with nitrogen to thereby create a deoxygenated atmosphere, and heating and incubation are performed while stirring. Note that the polymerization initiator and the solvent or the like used here are not particularly limited, and substances generally used in the field can be used. For example, as the polymerization initiator, azo compounds (2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), and the like), organic peroxides (benzoyl peroxide, tert-butyl peroxy-2-ethylhexanoate, and the like) can be mentioned, and as the solvent, solvents described later as the solvent (E) of the coloring curable resin composition of the present application and the like can be mentioned as long as the respective monomers are dissolved.

[0274] Note that, as the obtained copolymer, the solution after the reaction can be used as it is, a concentrated or diluted solution can be used, and a substance taken out in the form of a solid (powder) by reprecipitation or the like can be used. In particular, by using the solvent contained in the coloring curable resin composition of the present application as the solvent at the time of the polymerization, the solution after the reaction can be directly used for the production of the coloring curable resin composition of the present application, and thus the manufacturing process of the coloring curable resin composition of the present application can be simplified.

[0275] In the resin [K2], the ratio of the structural unit from each among all the structural units constituting the resin [K2] is preferably:

[0276] Structural unit from (a): 1 to 70 mol%

[0277] Structural unit from (b): 1 to 60 mol%

[0278] Structural unit from (c): 20 to 95 mol%,

[0279] More preferably:

[0280] Structural unit from (a): 3 to 50 mol%

[0281] Structural unit from (b): 3 to 40 mol%

[0282] Structural unit from (c): 30 to 90 mol%,

[0283] More preferably:

[0284] Structural unit from (a): 5 to 40 mol%

[0285] Structural unit from (b): 5 to 30 mol%

[0286] Structural unit from (c): 40 to 80 mol%.

[0287] The total of the structural unit from (a), the structural unit from (b), and the structural unit from (c) in all the structural units constituting the resin [K2] is, for example, 90 mol% or more, preferably 95 mol% or more, more preferably 98 mol% or more, and particularly preferably 100 mol%.

[0288] If the ratio of the structural units of the resin [K2] is within the above range, the storage stability of the colored curable resin composition, the developability at the time of forming a colored pattern, and the solvent resistance, heat resistance, and mechanical strength of the obtained color filter are excellent.

[0289] In the resin [K2], (a) is preferably an unsaturated monocarboxylic acid such as (methyl) acrylic acid. As (b), a monomer (bl) having an epoxy ethyl group and an ethylenic unsaturated bond is preferred, and a monomer (bl-2) having a structure in which an alicyclic unsaturated hydrocarbon is epoxidized is more preferred. As (c), a (methyl) acrylate having a cyclic unsaturated aliphatic hydrocarbon group, a (methyl) acrylate having an aromatic ring, and a dicarbonyl imide derivative are preferred.

[0290] The resin [K2] can be produced, for example, in the same manner as the method described as the production method of the resin [K1].

[0291] In the resin [K3], the ratio of the structural unit from each of (a), (b), and (c) in all the structural units constituting the resin [K3] is preferably:

[0292] Structural unit from (a): 2 to 60 mol%

[0293] structural units from (c): 40 to 98 mol%,

[0294] More preferably:

[0295] structural units from (a): 10 to 50 mol%

[0296] structural units from (c): 50 to 90 mol%,

[0297] More preferably:

[0298] structural units from (a): 35 to 45 mol%

[0299] structural units from (c): 55 to 65 mol%.

[0300] Further, it is preferable that substantially no structural units from (b) be contained.

[0301] In the entire structural units constituting the resin [K3], the total of the structural units from (a) and the structural units from (c) is, for example, 90 mol% or more, preferably 95 mol% or more, more preferably 98 mol% or more, and particularly preferably 100 mol%.

[0302] In the resin [K3], (a) is preferably an unsaturated monocarboxylic acid such as (meth)acrylic acid. (c) is preferably a (meth)acrylate having an aromatic ring.

[0303] The resin [K3] can be produced, for example, in the same manner as the method described as the production method of the resin [Kl].

[0304] In the resin [K4], in the entire structural units constituting the resin [K4], the ratio of the structural units from each of (a), (b), and (c) is preferably:

[0305] structural units from (a) (not added with (b)): 1 to 60 mol%

[0306] structural units resulting from addition of (b) to the structural units from (a): 1 to 50 mol%

[0307] structural units from (c): 30 to 90 mol%,

[0308] More preferably:

[0309] structural units from (a) (not added with (b)): 5 to 50 mol%

[0310] structural units resulting from addition of (b) to the structural units from (a): 5 to 40 mol%

[0311] structural units from (c): 35 to 80 mol%,

[0312] Still more preferably:

[0313] Structural unit from (a) (not added (b)): 10 to 40 mol%

[0314] Structural unit from (a) (not added (b)): 10 to 40 mol%

[0315] Structural unit from (c): 40 to 75 mol%.

[0316] In the entire structural units constituting the resin [K4], the total of the structural unit from (a) (not added (b)), the structural unit from (a) to which (b) is added, and the structural unit from (c) is, for example, 90 mol% or more, preferably 95 mol% or more, more preferably 98 mol% or more, and particularly preferably 100 mol%.

[0317] As the structural unit from (a) (not added (b)), a structural unit from an unsaturated monocarboxylic acid such as (meth)acrylic acid is preferred. As the structural unit from (a) to which (b) is added, a structural unit from a monomer (b1-1) having a structure in which an aliphatic unsaturated hydrocarbon having a linear or branched chain is epoxidized is added to a structural unit from an unsaturated monocarboxylic acid such as (meth)acrylic acid is preferred. As the structural unit from (c), one or more kinds, more preferably two or more kinds, selected from the group consisting of (meth)acrylate esters having an aliphatic saturated hydrocarbon group having a linear or branched chain, (meth)acrylate esters having a cyclic saturated hydrocarbon group, (meth)acrylate esters having an aromatic ring, a bicyclic unsaturated compound, and a styrene-based monomer are preferred. In the case where two structural units from (c) are present, two are selected from the group consisting of unsaturated carboxylic acid esters such as (meth)acrylate esters, (meth)acrylate esters having a cyclic saturated hydrocarbon group, (meth)acrylate esters having an aromatic ring, and the like, and preferably two or more kinds selected from the group consisting of a bicyclic unsaturated compound, a styrene-based monomer, and the like are selected.

[0318] The resin [K4] can be produced by obtaining a copolymer of (a) and (c), and adding a cyclic ether having 2 to 4 carbon atoms possessed by (b) to a carboxylic acid and / or a carboxylic anhydride possessed by (a).

[0319] First, a copolymer of (a) and (c) is produced in the same manner as the method described as the production method of the resin [K1]. In this case, the ratio of the structural units from each is preferably the same as that exemplified in the resin [K3].

[0320] Next, a cyclic ether having 2 to 4 carbon atoms possessed by (b) is reacted with a part of the carboxylic acid and / or the carboxylic anhydride from (a) in the aforementioned copolymer.

[0321] After the copolymer of (a) and (c) is produced, the atmosphere in the flask is replaced from nitrogen to air, a reaction catalyst (e.g., tris(dimethylaminomethyl)phenol, triphenylphosphine, etc.) of (b), a carboxylic acid or a carboxylic anhydride and a cyclic ether, and a polymerization inhibitor (e.g., hydroquinone, p-hydroxyanisole, etc.) or the like are added to the flask, and the reaction is carried out at 60 to 130°C for 1 to 10 hours, for example, whereby the resin [K4] can be produced.

[0322] The amount of use of (b) is preferably 5 to 80 moles, more preferably 10 to 75 moles, relative to 100 moles of (a). By setting within this range, there is a tendency that the balance of the storage stability of the colored curable resin composition, the developability at the time of pattern formation, and the solvent resistance, heat resistance, mechanical strength and sensitivity of the obtained pattern become good.

[0323] The amount of use of the aforementioned reaction catalyst is preferably 0.001 to 5 parts by mass, relative to 100 parts by mass of the total amount of (a), (b) and (c). The amount of use of the aforementioned polymerization inhibitor is preferably 0.001 to 5 parts by mass, relative to 100 parts by mass of the total amount of (a), (b) and (c).

[0324] The charging method, reaction temperature and time, and the like reaction conditions can be appropriately adjusted in consideration of the manufacturing equipment, the amount of heat generation by polymerization, and the like. Note that the charging method, reaction temperature can be appropriately adjusted in consideration of the manufacturing equipment, the amount of heat generation by polymerization, and the like as with the polymerization conditions.

[0325] In the resin [K4'], the ratio of the structural units from each of (a), (b) and (c) in all the structural units constituting the resin [K4'] is preferably:

[0326] Structural unit resulting from addition of (b) to the structural unit from (a): 5 to 95 mole%

[0327] Structural unit from (c): 5 to 95 mole%,

[0328] More preferably:

[0329] Structural unit resulting from addition of (b) to the structural unit from (a): 15 to 90 mole%

[0330] Structural unit from (c): 10 to 85 mole%,

[0331] Still more preferably:

[0332] Structural unit resulting from addition of (b) to the structural unit from (a): 20 to 80 mole%

[0333] Structural unit from (c): 20 to 80 mole%.

[0334] In addition, substantially no structural unit from (a) to which (b) is not added is contained.

[0335] In the entire structural units constituting the resin [K4'], the total of the structural unit to which (b) is added to the structural unit from (a) and the structural unit from (c) is, for example, 90 mol% or more, preferably 95 mol% or more, more preferably 98 mol% or more, and particularly preferably 100 mol%.

[0336] As the structural unit to which (b) is added to the structural unit from (a), a structural unit to which a monomer (b1-1) having a structure in which an aliphatic unsaturated hydrocarbon having a linear or branched chain is epoxidized is added to a structural unit from an unsaturated monocarboxylic acid such as a (meth)acrylic acid is preferable. As the structural unit from (c), one or more kinds selected from (meth)acrylate esters having an aliphatic saturated hydrocarbon group having a linear or branched chain, (meth)acrylate esters having a cyclic saturated hydrocarbon group are preferable, and two or more kinds are more preferable.

[0337] As for the resin [K4'], the production method of the resin [K4] described above can be referred to, and the use amount of (b) is preferably 100 mol or more, and more preferably 100 mol, with respect to 100 mol of (a).

[0338] In the resin [K5], in the entire structural units constituting the resin [K5], the ratio of the structural unit from each is preferably:

[0339] Structural unit from (b) (to which (a) is not added): 0 to 30 mol%

[0340] Structural unit to which (a) is added to the structural unit from (b): 5 to 95 mol%

[0341] Structural unit from (c): 5 to 95 mol%,

[0342] More preferably:

[0343] Structural unit from (b) (to which (a) is not added): 0 to 10 mol%

[0344] Structural unit to which (a) is added to the structural unit from (b): 15 to 90 mol%

[0345] Structural unit from (c): 10 to 85 mol%,

[0346] Further preferably:

[0347] Structural unit from (b) (to which (a) is not added): 0 to 5 mol%

[0348] the structural unit resulting from addition of (a) to the structural unit from (b): 20 to 80 mol%

[0349] the structural unit from (c): 20 to 80 mol%.

[0350] The total of the structural unit from (b) (not added with (a)), the structural unit resulting from addition of (a) to the structural unit from (b), and the structural unit from (c) is, for example, 90 mol% or more, preferably 95 mol% or more, more preferably 98 mol% or more, and particularly preferably 100 mol%, in the total structural units constituting the resin [K5].

[0351] As the structural unit from (b) (not added with (a)), the structural unit from the monomer (b1-1) having a structure in which a straight-chain or branched-chain aliphatic unsaturated hydrocarbon is epoxidized is preferred. As the structural unit resulting from addition of (a) to the structural unit from (b), the structural unit resulting from addition of an unsaturated monocarboxylic acid such as (meth)acrylic acid to the structural unit from the monomer (b1-1) having a structure in which a straight-chain or branched-chain aliphatic unsaturated hydrocarbon is epoxidized is preferred. As the structural unit from (c), one or more selected from the group consisting of (meth)acrylate esters having a straight-chain or branched-chain aliphatic saturated hydrocarbon group, (meth)acrylate esters having a cyclic saturated hydrocarbon group are preferred, and two or more are more preferred.

[0352] As to the resin [K5], as the first stage, a copolymer of (b) and (c) is obtained in the same manner as the production method of the resin [K1] described above. As to the obtained copolymer, the solution after the reaction can be used as it is, or a solution after concentration or dilution can be used, or a substance taken out in the form of a solid (powder) by a method such as reprecipitation can be used, in the same manner as described above.

[0353] The ratio of the structural unit from (b) and (c) is, with respect to the total number of moles of the total structural units constituting the copolymer described above, preferably each:

[0354] the structural unit from (b): 5 to 95 mol%

[0355] the structural unit from (c): 5 to 95 mol%,

[0356] More preferably, the ratio of the structural unit from (b) is:

[0357] the structural unit from (b): 10 to 90 mol%

[0358] the structural unit from (c): 10 to 90 mol%.

[0359] Further, the resin [K5] can be obtained by reacting the carboxylic acid or carboxylic anhydride possessed by (a) with the cyclic ether from (b) possessed by the copolymer of (b) and (c) under the same conditions as in the production method of the resin [K4] or the resin [K4'].

[0360] The use amount of (a) reacted with the aforementioned copolymer with respect to 100 moles of (b) is preferably 5 to 100 moles, more preferably 60 to 100 moles. As the (b) used in the resin [K5], (bl) is preferred, and (bl-1) is further preferred, in view of the high reactivity of the cyclic ether and the difficulty of leaving unreacted (b).

[0361] In the resin [K6], the ratio of the structural units from each of (a), (b) and (c) in the total structural units constituting the resin [K6] is preferably:

[0362] Structural unit from (b) (not added with (a)): 0 to 30 mol%

[0363] Structural unit from (a) added to the structural unit from (b): 5 to 70 mol%

[0364] Structural unit from (a) added to the structural unit from (b) and further added with carboxylic anhydride: 10 to 80 mol%

[0365] Structural unit from (c): 10 to 60 mol%,

[0366] More preferably:

[0367] Structural unit from (b) (not added with (a)): 0 to 10 mol%

[0368] Structural unit from (a) added to the structural unit from (b) (not added with carboxylic anhydride): 10 to 50 mol%

[0369] Structural unit from (a) added to the structural unit from (b) and further added with carboxylic anhydride: 25 to 60 mol%

[0370] Structural unit from (c): 15 to 50 mol%,

[0371] Further more preferably:

[0372] Structural unit from (b) (not added with (a)): 0 to 5 mol%

[0373] Structural unit from (a) added to the structural unit from (b) (not added with carboxylic anhydride): 15 to 35 mol%

[0374] a structure unit resulting from addition of (a) to a structure unit from (b) and further addition of a carboxylic anhydride: 35 to 55 mol%

[0375] a structure unit from (c): 20 to 40 mol%.

[0376] In the entire structure units constituting the resin [K6], the total of the structure unit from (b) (not added with (a)), the structure unit resulting from addition of (a) to a structure unit from (b) (not added with a carboxylic anhydride), the structure unit resulting from addition of (a) to a structure unit from (b) and further addition of a carboxylic anhydride, and the structure unit from (c) is, for example, 90 mol% or more, preferably 95 mol% or more, more preferably 98 mol% or more, and particularly preferably 100 mol%.

[0377] As the structure unit from (b) (not added with (a)), a structure unit from the monomer (bl-1) having a structure in which a straight-chain or branched-chain aliphatic unsaturated hydrocarbon is epoxidized is preferred. As the structure unit resulting from addition of (a) to a structure unit from (b) (not added with a carboxylic anhydride), a structure unit resulting from addition of an unsaturated monocarboxylic acid such as (meth)acrylic acid to a structure unit from the monomer (bl-1) having a structure in which a straight-chain or branched-chain aliphatic unsaturated hydrocarbon is epoxidized is preferred. As the structure unit resulting from addition of (a) to a structure unit from (b) and further addition of a carboxylic anhydride, a structure unit resulting from addition of an unsaturated monocarboxylic acid such as (meth)acrylic acid to a structure unit from the monomer (bl-1) having a structure in which a straight-chain or branched-chain aliphatic unsaturated hydrocarbon is epoxidized and further addition of a saturated aliphatic polycarboxylic anhydride such as succinic anhydride is preferred. As the structure unit from (c), one or more kinds, more preferably two or more kinds, selected from the group consisting of (meth)acrylates having a straight-chain or branched-chain aliphatic saturated hydrocarbon group and (meth)acrylates having a cyclic saturated hydrocarbon group are preferred.

[0378] As to the resin [K6], as the first stage, a copolymer of (b) and (c) is obtained in the same manner as in the production method of the resin [Kl] described above. As to the obtained copolymer, a solution after the reaction can be used as it is, or a solution after concentration or dilution can be used, or a substance taken out in the form of a solid (powder) by a method such as reprecipitation can be used.

[0379] The ratio of the structure unit from (b) and (c) is, with respect to the total number of moles of the entire structure units constituting the copolymer described above, preferably each:

[0380] a structure unit from (b): 5 to 95 mol%

[0381] a structure unit from (c): 5 to 95 mol%,

[0382] More preferably:

[0383] Structural units from (b): 10 to 90 mol%

[0384] Structural units from (c): 10 to 90 mol%.

[0385] Further, the carboxylic acid or carboxylic anhydride possessed by (a) is reacted with the cyclic ether possessed by the copolymer of (b) and (c) from (b) under the same conditions as in the production method of the resin [K4]. The use amount of (a) is preferably 80 to 100 mol with respect to 100 mol of (b).

[0386] The hydroxyl group produced by the reaction of the aforementioned cyclic ether with the carboxylic acid or carboxylic anhydride possessed by (a) is reacted with a carboxylic anhydride.

[0387] The use amount of the carboxylic anhydride is preferably 0.05 to 1 mol, more preferably 0.10 to 0.8 mol, and further more preferably 0.13 to 0.7 mol with respect to 1 mol of the use amount of (a) (in other words, 1 mol of the hydroxyl group produced by the use of (a)).

[0388] As the resin (B), specifically, there can be mentioned, for example:

[0389] a 3,4-epoxycyclohexylmethyl (meth)acrylate / (meth)acrylic acid copolymer, a 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl acrylate / (meth)acrylic acid copolymer, and the like resin [K1];

[0390] a glycidyl (meth)acrylate / benzyl (meth)acrylate / (meth)acrylic acid copolymer, a glycidyl (meth)acrylate / styrene / (meth)acrylic acid copolymer, a 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl acrylate / (meth)acrylic acid / N-cyclohexyl maleimide copolymer, a 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl acrylate / (meth)acrylic acid / N-cyclohexyl maleimide / (meth)acrylic acid tricyclo[5.2.1.0 2,6 ]decen-8-yl ester copolymer, a 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl acrylate / (meth)acrylic acid / benzyl (meth)acrylate copolymer, a 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl acrylate / (meth)acrylic acid / phenoxybenzyl (meth)acrylate copolymer, a 3-methyl-3-(meth)acryloyloxy-methyl oxetane / (meth)acrylic acid / styrene copolymer, and the like resin [K2];

[0391] Resins [K3] such as benzyl (meth)acrylate / (meth)acrylic acid copolymer, styrene / (meth)acrylic acid copolymer, and the like;

[0392] Resins [K4] such as a resin in which glycidyl (meth)acrylate is added to a part of carboxylic acid groups of benzyl (meth)acrylate / (meth)acrylic acid copolymer, a resin in which glycidyl (meth)acrylate is added to a part of carboxylic acid groups of tricyclodecane (meth)acrylate / styrene / (meth)acrylic acid copolymer, a resin in which glycidyl (meth)acrylate is added to a part of carboxylic acid groups of tricyclodecane (meth)acrylate / benzyl (meth)acrylate / (meth)acrylic acid copolymer, a resin in which glycidyl (meth)acrylate is added to a part of carboxylic acid groups of norbornene / ethyltoluene / (meth)acrylic acid copolymer, a resin in which glycidyl (meth)acrylate is added to a part of carboxylic acid groups of norbornene / styrene / (meth)acrylic acid copolymer, and the like;

[0393] Resins [K4'] such as a resin in which glycidyl (meth)acrylate is reacted with tricyclodecane (meth)acrylate / (meth)acrylic acid copolymer, a resin in which glycidyl (meth)acrylate is reacted with tricyclodecane (meth)acrylate / styrene / (meth)acrylic acid copolymer, and the like;

[0394] Resins [K5] such as a resin in which (meth)acrylic acid is reacted with tricyclodecane (meth)acrylate / glycidyl (meth)acrylate copolymer, a resin in which (meth)acrylic acid is reacted with tricyclodecane (meth)acrylate / glycidyl (meth)acrylate copolymer, and the like;

[0395] Resins [K6] and the like such as a resin in which (meth)acrylic acid is further reacted with a resin in which (meth)acrylic acid is reacted with tricyclodecane (meth)acrylate / glycidyl (meth)acrylate copolymer, a resin in which succinic anhydride is further reacted with a resin in which (meth)acrylic acid is reacted with 2-ethylhexyl (meth)acrylate / tricyclodecane (meth)acrylate / glycidyl (meth)acrylate copolymer, a resin in which succinic anhydride is further reacted with a resin in which (meth)acrylic acid is reacted with methyl (meth)acrylate / 2-ethylhexyl (meth)acrylate / tricyclodecane (meth)acrylate / glycidyl (meth)acrylate copolymer, and the like.

[0396] The resin (B) can be used singly or in combination of two or more. As the resin (B), at least one selected from the group consisting of resin [Kl], resin [K2], resin [K4], and resin [K6] is preferable, and resin [K2] and / or resin [K6] is more preferable.

[0397] In the case of using two or more in combination as the resin (B), a preferable combination includes, for example, a combination of resin [K2] and [K6]. By using resin [K2] and [K6] in combination, the balance between the pattern formability and the reliability becomes better. In the case of combining resin [K2] and [K6], the content of resin [K2] is, for example, 5 to 99.9 mass%, preferably 15 to 95.0 mass%, and more preferably 25 to 90.0 mass%, relative to 100 mass% of the total of resin [K2] and resin [K6].

[0398] The weight average molecular weight of the resin (B) in terms of polystyrene is preferably 3,000 to 100,000, more preferably 5,000 to 50,000, and further preferably 5,000 to 30,000. If the molecular weight is within the aforementioned range, there is a tendency that the hardness of the color filter is improved, the residual film rate is high, the solubility of the unexposed portion in the developing solution is good, and the resolution of the colored pattern is improved.

[0399] The dispersity [weight average molecular weight (Mw) / number average molecular weight (Mn)] of the resin (B) is preferably 1.1 to 6, and more preferably 1.2 to 4.

[0400] The acid value of the resin (B) is preferably 20 to 170 mg-KOH / g, more preferably 50 to 150 mg-KOH / g, and further preferably 80 to 135 mg-KOH / g, in terms of solid content. Here, the acid value is a value measured as the amount (mg) of potassium hydroxide required for neutralization of 1 g of the resin (B), and can be obtained, for example, by titration using an aqueous potassium hydroxide solution.

[0401] The content of the resin (B) is preferably 5 to 65 mass%, more preferably 12 to 55 mass%, and further preferably 20 to 50 mass%, relative to the total amount of the solid content of the colored curable resin composition. If the content of the resin (B) is within the aforementioned range, there is a tendency that a colored pattern can be formed, and the resolution and the residual film rate of the colored pattern are improved.

[0402]

[0403] The polymerizable compound (C) is a compound that can be polymerized by the active radicals and / or acid generated from the polymerization initiator (D), and examples thereof include a compound having a polymerizable ethylenic unsaturated bond, and the like, and a (meth)acrylate compound is preferable. ​

[0404] Among them, the polymerizable compound (C) is preferably a polymerizable compound having 3 or more ethylenic unsaturated bonds. As such a polymerizable compound, for example, trimethylolpropane tri(meth)acrylate, pentaerythritol poly(meth)acrylate (for example, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate), dipentaerythritol poly(meth)acrylate (for example, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate), tripentaerythritol poly(meth)acrylate (for example, tripentaerythritol octa(meth)acrylate, tripentaerythritol hepta(meth)acrylate), tetrapentaerythritol poly(meth)acrylate (for example, tetrapentaerythritol deca(meth)acrylate, tetrapentaerythritol nona(meth)acrylate), tris(2-(meth)acryloyloxyethyl)isocyanurate, alkoxylated pentaerythritol poly(meth)acrylate (for example, ethoxylated pentaerythritol tri(meth)acrylate, ethoxylated pentaerythritol tetra(meth)acrylate, propoxylated pentaerythritol tri(meth)acrylate, propoxylated pentaerythritol tetra(meth)acrylate), alkoxylated dipentaerythritol poly(meth)acrylate (for example, ethoxylated dipentaerythritol penta(meth)acrylate, ethoxylated dipentaerythritol hexa(meth)acrylate, propoxylated dipentaerythritol penta(meth)acrylate, propoxylated dipentaerythritol hexa(meth)acrylate), caprolactone-modified pentaerythritol poly(meth)acrylate (for example, caprolactone-modified pentaerythritol tri(meth)acrylate, caprolactone-modified pentaerythritol tetra(meth)acrylate), caprolactone-modified dipentaerythritol poly(meth)acrylate (for example, caprolactone-modified dipentaerythritol penta(meth)acrylate, caprolactone-modified dipentaerythritol hexa(meth)acrylate), and the like can be given.

[0405] Among them, at least 1 kind selected from the group consisting of trimethylolpropane tri(meth)acrylate, dipentaerythritol poly(meth)acrylate, alkoxylated dipentaerythritol poly(meth)acrylate is preferable. In particular, from the viewpoint of improving the developability when forming a colored pattern, alkoxylated dipentaerythritol poly(meth)acrylate is preferable, and ethoxylated dipentaerythritol poly(meth)acrylate such as ethoxylated dipentaerythritol penta(meth)acrylate, ethoxylated dipentaerythritol hexa(meth)acrylate, and the like is more preferable, and ethoxylated dipentaerythritol polyacrylate such as ethoxylated dipentaerythritol pentaacrylate, ethoxylated dipentaerythritol hexaacrylate is further preferable.

[0406] It is to be noted that the addition mole number of the alkoxyl group in the aforementioned alkoxylated dipentaerythritol poly(meth)acrylate is preferably 2 to 30, more preferably 5 to 20, and further preferably 8 to 15. Also, the addition mole number of the ethoxyl group in the ethoxylated dipentaerythritol poly(meth)acrylate, ethoxylated dipentaerythritol polyacrylate is preferably adjusted to the above range.

[0407] The content ratio of the polymerizable compound (C) is, for example, 5 to 65% by mass, preferably 6 to 50% by mass, and more preferably 8 to 30% by mass, relative to the total amount of the solid components of the colored curable resin composition. If the content ratio of the polymerizable compound (C) is within the aforementioned range, there is a tendency that the residual film rate at the time of forming a colored pattern and the chemical resistance of the color filter are further improved.

[0408] <Polymerization initiator (D)>

[0409] The polymerization initiator (D) is not particularly limited as long as it is a compound capable of initiating polymerization by generating an active radical, an acid, or the like under the action of light or heat, and a known polymerization initiator can be used.

[0410] As the polymerization initiator generating an active radical, for example, an alkyl phenone compound, a triazine compound, an acyl phosphine oxide compound, an O-acyl oxime compound, and a bisimidazole compound can be given.

[0411] The aforementioned O-acyl oxime compound is a compound having a partial structure represented by formula (d1).

[0412] Hereinafter, * represents a bond.

[0413]

[0414] As the aforementioned O-acyl oxime compound, for example, N-benzoyloxy-1- (4-phenylsulfanylphenyl) butane-1-one-2-imine, N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-one-2-imine, N-benzoyloxy-1- (4-phenylsulfanylphenyl)-3-cyclopentylpropane-1-one-2-imine, N-acetyloxy-1- [9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethane-1-imine, N-acetyloxy-1- [9-ethyl-6-{2-methyl-4-(3,3-dimethyl-2,4-dioxocyclopentylmethyloxy)benzoyl}- 9H-carbazol-3-yl]ethane-1-imine, N-acetyloxy-1- [9-ethyl-6-(2-methylbenzoyl)- 9H-carbazol-3-yl]-3-cyclopentylpropane-1-imine, N-benzoyloxy-1- [9-ethyl-6- (2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropane-1-one-2-imine, N-acetyloxy-1-[4-(2-hydroxyethyloxy)phenylsulfanylphenyl]propane-1-one-2- imine, N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropane-1-one-2- imine, 2-[(acetyloxy)imino]-3-cyclohexyl-1-[4-(phenylsulfanyl)phenyl]propane-1- one, and the like can be given. Commercially available products such as Irgacure (registered trademark) OXE01, OXE02, OXE03, OXE04, OXE05 (all of which are manufactured by BASF), ADEKA ARK LS (registered trademark) N-1919, NCI-730, NCI-831, NCI-930 (all of which are manufactured by ADEKA), PBG-314, PBG-317, PBG-326, PBG-327, PBG-329 (all of which are manufactured by Qiangli Electronics New Materials Co., Ltd.), and the like can be used. Among them, the O-acyl oxime compound is preferably selected from the group consisting of N-acetyloxy-1-[4-(2-hydroxyethyloxy)phenylsulfanylphenyl]propane-1- one-2-imine, N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropane-1-one- 2-imine, 2-[(acetyloxy)imino]-3-cyclohexyl-1-[4-(phenylsulfanyl)phenyl]propane-1- one, N-benzoyloxy-1-(4-phenylsulfanylphenyl)butane-1-one-2-imine, N- benzoyloxy-1-(4-phenylsulfanylphenyl)octane-1-one-2-imine, N-benzoyloxy-1- (4-phenylsulfanylphenyl)-3-cyclopentylpropane-1-one-2-imine, N-acetyloxy-1- [9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethane-1-imine, N-acetyloxy-1- [9-ethyl-6-{2-methyl-4-(3,3-dimethyl-2,4-dioxocyclopentylmethyloxy)benzoyl}- 9H-carbazol-3-yl]ethane-1-imine, and N-acetyloxy-1- [9-ethyl-6-(2-methylbenzoyl)- 9H-carbazol-3-yl]-3-cyclopentylpropane-1-imine.

[0415] at least one selected from the group consisting of 2-[(acetyloxy)imino]-3-cyclohexyl-1- [4-(phenylsulfanyl)phenyl]propan-1-one, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan- 1-one-2-imine, and N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2- imine. If these O-acyl oxime compounds, there is a tendency to obtain a filter with high brightness.

[0416] The aforementioned alkylphenone compound is preferably a compound having a partial structure represented by formula (d2) or a partial structure represented by formula (d3). In these partial structures, the benzene ring can have a substituent.

[0417]

[0418] As the compound having the partial structure represented by formula (d2), for example, 2-methyl-2-morpholino-1-(4-methylsulfanylphenyl)propan-1-one, 2-dimethylamino-1-(4- morpholinophenyl)-2-benzylbutan-1-one, 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1- [4-(4-morpholinyl)phenyl]butan-1-one, and the like can be given. Commercially available products such as Irgacure (registered trademark) 369, 907, 379 (all manufactured by BASF), and the like can be used.

[0419] As the compound having the partial structure represented by formula (d3), for example, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1-[4-(2- hydroxyethoxy)phenyl]propan-1-one, 1-hydroxycyclohexyl phenyl ketone, an oligomer of 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propan-1-one, α,α-diethoxyacetophenone, benzil dimethyl ketal, and the like can be given.

[0420] From the aspect of sensitivity, as the alkylphenone compound, a compound having a partial structure represented by formula (d2) is preferable.

[0421] As the aforementioned triazine compound, for example, 2,4-bis(trichloromethyl)-6-(4- methoxyphenyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxynaphthyl)-1,3,5- triazine, 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4- methoxystyryl)-1,3,5-triazine, 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, and the like can be mentioned.

[0422] As the aforementioned acylphosphine oxide compound, 2,4,6-trimethylbenzoyldiphenylphosphine oxide and the like can be mentioned. Commercially available products such as Irgacure (registered trademark) 819 (manufactured by BASF) and the like can be used.

[0423] As the aforementioned bisimidazole compound, for example, 2,2'-bis(2-chlorophenyl)- 4,4',5,5'-tetraphenylbisimidazole, 2,2'-bis(2,3-dichlorophenyl)-4,4',5,5'-tetraphenylbisimidazole (for example, see Japanese Patent Application Publication No. 6-75372, Japanese Patent Application Publication No. 6-75373, and the like), 2,2'-bis(2-chlorophenyl)-4,4',5,5'- tetra(alkoxylphenyl)bisimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(dialkoxyphenyl) bisimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(trialkoxyphenyl)bisimidazole (for example, see Japanese Patent Application Publication No. 48-38403, Japanese Patent Application Publication No. 62-174204, and the like), a bisimidazole compound in which the phenyl group at the 4,4',5,5'-positions is substituted with an alkoxycarbonyl group (for example, see Japanese Patent Application Publication No. 7-10913 and the like), and the like can be mentioned.

[0424] 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 peroxide, 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, benzoin, methyl phenylglyoxylate, and titanium dioxide compounds. These are preferably used in combination with polymerization initiators (D1) (especially amine compounds) described later.

[0425] Examples of polymerization initiators that generate acids include, for example, onion salts such as 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, diphenyliodonium p-toluenesulfonate, diphenyliodonium hexafluoroantimonate, nitrobenzyl toluenesulfonate, and benzoin toluenesulfonate.

[0426] As the polymerization initiator (D), it is preferably a polymerization initiator comprising at least one compound selected from the group consisting of alkyl phenyl ketone compounds, triazine compounds, acylphosphine oxide compounds, O-acyl oxime compounds, and biimidazole compounds, more preferably a polymerization initiator comprising an O-acyl oxime compound. In 100% by mass of the polymerization initiator (D), the content of the O-acyl oxime compound is, for example, 30 to 100% by mass, preferably 50% by mass or more, more preferably 80% by mass or more, and even more preferably 90% by mass or more.

[0427] The content of polymerization initiator (D) is preferably 0.1 to 30 parts by mass relative to 100 parts by mass of the total amount of resin (B) and polymerizable compound (C), more preferably 1 to 20 parts by mass, and even more preferably 2 to 10 parts by mass. If the content of polymerization initiator (D) is within the aforementioned range, there is a tendency to achieve higher sensitivity and shorter exposure time, thereby increasing the productivity of the color filter.

[0428] <Polymerization Initiator (D1)>

[0429] The coloring and curing resin composition of the present invention may further comprise a polymerization initiator (D1). The polymerization initiator (D1) is a compound or sensitizer used to promote the polymerization of a polymerizable compound that is initiated by a polymerization initiator.

[0430] Examples of polymerization initiators (D1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds, and carboxylic acid compounds.

[0431] As the aforementioned amine compound, mention can be made of triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 2-ethylhexyl 4-dimethylaminobenzoate, N,N-dimethyl-p-toluidine, 4,4'-bis(dimethylamino)benzophenone (commonly known as Michler's ketone), 4,4'-bis(diethylamino)benzophenone, 4,4'-bis(ethylmethylamino)benzophenone, and the like, of which 4,4'-bis(diethylamino)benzophenone is preferred. Commercially available products such as EAB-F (manufactured by Hokoku Corporation) can be used.

[0432] As the aforementioned alkoxyanthracene compound, mention can be made of 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene, 9,10-dibutoxyanthracene, 2-ethyl-9,10-dibutoxyanthracene, and the like.

[0433] As the aforementioned thioxanthone compound, mention can be made of 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, 1-chloro-4-propoxythioxanthone, and the like.

[0434] As the aforementioned carboxylic acid compound, mention can be made of phenylsulfanylacetic acid, methylphenylsulfanylacetic acid, ethylphenylsulfanylacetic acid, methylethylphenylsulfanylacetic acid, dimethylphenylsulfanylacetic acid, methoxyphenylsulfanylacetic acid, dimethoxyphenylsulfanylacetic acid, chlorophenylsulfanylacetic acid, dichlorophenylsulfanylacetic acid, N-phenylglycine, phenoxyacetic acid, naphthalene thioacetic acid, N-naphthylglycine, naphthaleneoxyacetic acid, and the like.

[0435] When these polymerization initiator aids (D1) are used, the content thereof is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, relative to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). If the amount of the polymerization initiator aid (D1) is within this range, there is a tendency for the colored pattern to be formed with higher sensitivity and for the productivity of the color filter to be improved.

[0436] <solvent (E)>

[0437] The solvent (E) is not particularly limited, and a solvent generally used in the field can be used. For example, ester solvents (solvents containing -COO- in the molecule and not containing -O-), ether solvents (solvents containing -O- in the molecule and not containing -COO-), ether ester solvents (solvents containing -COO- and -O- in the molecule), ketone solvents (solvents containing -CO- in the molecule and not containing -COO-), alcohol solvents (solvents containing OH in the molecule and not containing -O-, -CO-, and -COO-), aromatic hydrocarbon solvents, amide solvents, dimethyl sulfoxide, and the like can be mentioned.

[0438] As the ester solvent, 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, γ-butyrolactone, and the like can be mentioned.

[0439] As the ether solvent, 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-l-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, phenetol, and methyl anisole, and the like can be mentioned.

[0440] As the ether ester solvent, 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-methyl-2-methoxypropionate, ethyl 2-ethyl-2-methoxypropionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, and the like can be mentioned.

[0441] As the ketone solvent, 4-hydroxy-4-methyl-2-pentanone (dipropyl carbinol), acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone, isophorone, and the like can be mentioned.

[0442] As the alcohol solvent, methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerol can be given.

[0443] As the aromatic hydrocarbon solvent, benzene, toluene, xylene, and mesitylene can be given.

[0444] As the amide solvent, N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone can be given.

[0445] Among the above solvents, from the viewpoint of coatability and drying property, an organic solvent having a boiling point of 120°C or higher and 180°C or lower at 1 atm is preferred. As the solvent, at least one selected from the group consisting of propylene glycol monomethyl ether acetate, ethyl lactate, propylene glycol monomethyl ether, ethyl 3-ethoxypropionate, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, 4-hydroxy-4-methyl-2-pentanone, and N,N-dimethylformamide is preferred, and at least one selected from the group consisting of propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, 4-hydroxy-4-methyl-2-pentanone, ethyl lactate, and ethyl 3-ethoxypropionate is more preferred.

[0446] Further, as the solvent (E), it is also preferred to use an ether solvent and an ether ester solvent in combination. In this case, as the ether solvent, a C 2-3 alkylene glycol mono C 1-4 alkyl ether is more preferred. Further, as the ether ester solvent, a C 1-4 alkylene glycol mono C 2-3 alkyl ether is more preferred. Further, as the ether ester solvent, a C 1-4 alkylene glycol mono C 1-4 alkyl ether acetate is more preferred.

[0447] In the case where an ether solvent and an ether ester solvent are used in combination, the content of the ether solvent is preferably 0.1 to 30 parts by mass, and more preferably 1 to 10 parts by mass, relative to 100 parts by mass of the total of the ether solvent and the ether ester solvent. If the content of the ether solvent is within the above range, there is a tendency that the solubility and dispersibility of components other than the solvent included in the colored curable resin composition are improved, and the planarity at the time of coating becomes good.

[0448] The content ratio of the solvent (E) is preferably 70 to 95% by mass, and more preferably 75 to 92% by mass, relative to the total amount of the colored curable resin composition. In other words, the solid content of the colored curable resin composition is preferably 5 to 30% by mass, and more preferably 8 to 25% by mass. If the content ratio of the solvent (E) is within the above range, the planarity at the time of coating becomes good, and in addition, since the color density does not become insufficient at the time of forming a color filter, there is a tendency that the display characteristics and the sensitivity become good.

[0449] <Leveling agent (F)>

[0450] As the leveling agent (F), a silicone-based surfactant, a fluorine-based surfactant, and a silicone-based surfactant having a fluorine atom, and the like can be given. They can have a polymerizable group in a side chain.

[0451] As the silicone-based surfactant, a surfactant having a siloxane bond in a molecule, and the like can be given. Specifically, TORAY SILICONE DC3PA, TORAY SILICONE SH7PA, TORAY SILICONE DC11PA, TORAY SILICONE SH21PA, TORAY SILICONE SH28PA, TORAY SILICONE SH29PA, TORAY SILICONE SH30PA, TORAY SILICONE SH8400 (trade name: manufactured by Toray Dow Corning Silicone Co., Ltd.), KP321, KP322, KP323, KP324, KP326, KP340, KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452, and TSF4460 (manufactured by Momentive Performance Materials Japan Co., Ltd.), and the like can be given.

[0452] As the aforementioned fluorine-based surfactant, a surfactant having a fluorocarbon chain in a molecule, and the like can be given. Specifically, FLOURAD (registered trademark) FC430, FLOURAD FC431 (manufactured by Sumitomo 3M Co., Ltd.), MEGAFACE (registered trademark) F142D, MEGAFACE F171, MEGAFACE F172, MEGAFACE F173, MEGAFACE F177, MEGAFACE F183, MEGAFACE F554, MEGAFACE R30, MEGAFACE RS-718-K (manufactured by DIC Corp.), EFTOP (registered trademark) EF301, EFTOP EF303, EFTOP EF351, EFTOP EF352 (manufactured by Mitsubishi Rayon Co., Ltd.), SURFLON (registered trademark) S381, SURFLON S382, SURFLON SC101, SURFLON SC105 (manufactured by AGC Inc. (former Asahi Glass Co., Ltd.)), and E5844 (manufactured by Daikin Fine Chemicals Ltd.), and the like can be given.

[0453] As the aforementioned organosilicon-based surfactant having a fluorine atom, a surfactant having a siloxane bond and a fluorocarbon chain in the molecule, etc. can be given. Specifically, MEGAFACE (registered trademark) R08, MEGAFACE BL20, MEGAFACE F475, MEGAFACE F477, and MEGAFACE F443 (manufactured by DIC Corporation), etc. can be given.

[0454] The content ratio of the leveling agent (F) is preferably 0.001 to 0.2% by mass, more preferably 0.002 to 0.1% by mass, and further preferably 0.005 to 0.05% by mass, relative to the total amount of the colored curable resin composition. Note that the content ratio does not include the content ratio of the aforementioned pigment dispersant. If the content ratio of the leveling agent (F) is within the aforementioned range, the planarity of the color filter can be made good.

[0455] <Other components>

[0456] The colored curable resin composition can include, as necessary, a filler, another high molecular compound, an adhesion promoter, an antioxidant, a light stabilizer, a chain transfer agent, and the like, which are known in the technical field.

[0457] <Method for producing the colored curable resin composition>

[0458] The colored curable resin composition can be produced, for example, by mixing the colorant (A), the resin (B), the polymerizable compound (C), the polymerization initiator (D), and the solvent (E), the leveling agent (F), the polymerization initiation aid (D1), and other components, as necessary. The mixed colored curable resin composition can be filtered using a filter having a pore size of about 0.01 to 10 μm.

[0459] The colorant (A) can be dispersed by being mixed with a pigment dispersant as described above, and used as a colorant dispersion liquid in which the colorant is uniformly dispersed in a solution. The remaining components can be mixed with the colorant dispersion liquid to make the target colored curable resin composition.

[0460] In addition, in the case where the colorant (A) includes a dye, the dye can be dissolved in a part or all of the solvent (E) in advance to produce a solution. The solution can be filtered using a filter having a pore size of about 0.01 to 1 μm.

[0461] [Color filter]

[0462] As a method of producing a colored pattern of a color filter from the colored curable resin composition of the present application, photolithography, inkjet method, printing method, and the like can be given. Among them, photolithography is preferred. Photolithography is a method in which the aforementioned colored curable resin composition is applied to a substrate, dried to form a composition layer, the composition layer is exposed through a photomask, and developed. In photolithography, by not using a photomask at the time of exposure and / or not developing, a colored coating film which is a cured product of the aforementioned composition layer can be formed.

[0463] The film thickness of the color filter (colored coating film or colored pattern) is, for example, 30 μm or less, preferably 20 μm or less, more preferably 6 μm or less, further preferably 3 μm or less, further more preferably 1.5 μm or less, particularly preferably 1.0 μm or less, preferably 0.1 μm or more, more preferably 0.2 μm or more, further preferably 0.3 μm or more.

[0464] As the substrate, a glass plate such as quartz glass, borosilicate glass, aluminosilicate glass, soda-lime glass coated with silica on the surface, a resin plate such as polycarbonate, polymethyl methacrylate, polyethylene terephthalate, silicon, a substrate on which an aluminum, silver, silver / copper / palladium alloy thin film, or the like is formed on the aforementioned substrate can be used. Other color filter layers, resin layers, transistors, circuits, and the like can also be formed on these substrates. In addition, a substrate obtained by performing HMDS treatment on a silicon substrate can also be used.

[0465] The formation of each color pixel (color filter of each color) by photolithography can be performed by known or conventional means and conditions. For example, it can be produced in the following manner. First, the colored curable resin composition is applied to a substrate, and by performing heat drying (pre-baking) and / or reduced pressure drying, volatile components such as solvents are removed and dried to obtain a smooth composition layer. As the application method, spin coating method, slit coating method, slit and spin coating method, and the like can be given. In the case of heat drying, the temperature is preferably 30 to 120°C, more preferably 50 to 110°C. In addition, as the heating time, 10 seconds to 60 minutes is preferred, more preferably 30 seconds to 30 minutes. In the case of reduced pressure drying, it is preferably performed at a pressure of 50 to 150 Pa in a temperature range of 20 to 25°C. The film thickness of the composition layer is not particularly limited, and can be appropriately selected depending on the film thickness of the color filter targeted.

[0466] Next, the composition layer is exposed through a photomask for forming a target colored pattern. The pattern on the photomask is not particularly limited, and a pattern corresponding to the target use can be used. As a light source used for the exposure, a light source generating light having a wavelength of 250 to 450 nm is preferable. For example, a filter cutting off the wavelength region can be used to cut off light of less than 250 nm; or a band pass filter extracting the wavelength region can be used to selectively extract light around 436 nm, around 408 nm, or around 365 nm. Specifically, a mercury lamp, a light emitting diode, a metal halide lamp, a halogen lamp, or the like can be mentioned. In order to be able to uniformly irradiate parallel light to the entire exposure surface or to accurately align the photomask and the substrate, a reduction projection exposure device such as a mask aligner and a stepper, or a proximity exposure device is preferably used.

[0467] The colored pattern is formed on the substrate by developing the exposed composition layer by bringing it into contact with a developing solution. By the development, the unexposed part of the composition layer is dissolved in the developing solution and removed. As the developing solution, for example, an aqueous solution of an alkali compound such as potassium hydroxide, sodium bicarbonate, sodium carbonate, tetramethylammonium hydroxide, or the like is preferable. The concentration of the alkali compound in the aqueous solution is preferably 0.01 to 10% by mass, and more preferably 0.03 to 5% by mass. In addition, the developing solution can contain a surfactant. The developing method can be any of a spin-coating immersion method, an immersion method, a spray method, or the like. In addition, the substrate can be inclined at an arbitrary angle at the time of development.

[0468] After the development, water washing is preferably performed.

[0469] The obtained colored pattern is preferably further subjected to post-baking. The post-baking temperature is preferably 80 to 250°C, and more preferably 100 to 245°C. The post-baking time is preferably 1 to 120 minutes, and more preferably 2 to 30 minutes.

[0470] The colored pattern and the colored coating film thus obtained are useful as a color filter, and are useful as a color filter used in a display device (for example, a liquid crystal display device, an organic EL device, or the like), electronic paper, a solid-state imaging device, or the like.

[0471] In particular, the aforementioned colored pattern and colored coating film are useful as a blue pixel (blue color filter) in a color filter.

[0472] For the aforementioned colored pattern or colored coating film, in the case where the film thickness is adjusted so that the maximum transmittance at a wavelength of 400 to 500 nm becomes 83%, the transmittance at 530 nm is preferably 13.0% or less, more preferably 11.0% or less, further preferably 8.0% or less, and particularly preferably 5.0% or less or 3.0% or less. By reducing the transmittance at 530 nm, the leakage of green light can be suppressed, and the color separation as a blue color filter can be improved. Note that the lower limit of the aforementioned transmittance at 530 nm is not particularly limited, and can be, for example, 0.5% or more.

[0473] In addition, for the aforementioned colored pattern or colored coating film, in the case where the film thickness is adjusted so that the maximum transmittance at a wavelength of 400 to 500 nm becomes 83%, the transmittance at 640 nm is preferably 10.0% or less, more preferably 7.0% or less, further preferably 5.0% or less, and particularly preferably 3.0% or less. By reducing the transmittance at 640 nm, the leakage of red light can be suppressed, and the color separation as a blue color filter can be further improved. Note that the lower limit of the aforementioned transmittance at 640 nm is not particularly limited, and can be, for example, 0.5% or more.

[0474] Examples

[0475] Hereinafter, the present application will be described more specifically by citing examples, but the present application is not at all limited by the following examples, and of course, can be appropriately changed within a range that can be adapted to the gist described in the foregoing and the following, and they are included in the technical scope of the present application. Note that hereinafter, unless otherwise specified, "parts" means "mass parts", and "%" means "mass%".

[0476] In the following examples, the structure of the compound was confirmed by mass spectrometry (LC: Model 1200 manufactured by Agilent, MASS: LC / MSD6130 manufactured by Agilent).

[0477] The measurement of the weight average molecular weight (Mw) and the number average molecular weight (Mn) of the resin in terms of polystyrene was performed using a GPC method under the following conditions.

[0478] Apparatus: HLC-8120 GPC (manufactured by TOSOH Corporation)

[0479] Column: TSK-GEL G2000HXL

[0480] Column temperature: 40°C

[0481] Solvent: Tetrahydrofuran

[0482] Flow rate: 1.0 mL / minute

[0483] The concentration of the solid component of the sample was analyzed: 0.001 to 0.01%

[0484] Injection volume: 50 μL

[0485] Detector: RI

[0486] Calibration standard: TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (TOSOH Corporation)

[0487] The ratio of the weight average molecular weight to the number average molecular weight (Mw / Mn) obtained above in terms of polystyrene was used as the dispersity.

[0488] <Colorant Synthesis Example 1>

[0489] A compound represented by formula (II-X) 40.5 parts and 2,6- dimethylaniline (Tokyo Chemical Industry Co., Ltd.) 60.5 parts were mixed under light shielding conditions, and stirred in N-methylpyridone 200 parts at 150°C for 8 hours. After the resulting reaction solution was cooled to room temperature, it was added to a mixture of water 1200 parts and 35% hydrochloric acid 75 parts, and stirred at room temperature for 1 hour, as a result, crystals were precipitated. The precipitated crystals were obtained as a residue of suction filtration, and after washing with methanol 100 parts, they were dried under reduced pressure at 60°C for 12 hours, to obtain a compound represented by formula (II-1) 49 parts. The yield was 85%.

[0490]

[0491] Identification of the compound represented by formula (II-1)

[0492] (Mass spectrum) Ionization mode = ESI+: m / z = [M+H] + 575

[0493] Exact Mass: 574

[0494] <Colorant Synthesis Example 2>

[0495] The compound represented by formula (II-X) 4.0 parts, 2,6-diphenyl aniline 9.69 parts, zinc chloride (manufactured by FUJIFILM Wako Pure Chemical Corporation) 2.69 parts, sulfolane (manufactured by Tokyo Chemical Industry Co., Ltd.) 24 parts were mixed at room temperature, warmed to 250°C, and stirred for 4 hours. After the reaction solution was cooled to room temperature, 1N hydrochloric acid 48 parts was added, and the resulting precipitate was obtained as a residue of suction filtration, and further washed with toluene 24 parts, N,N-dimethylformamide 18 parts, N,N-dimethylformamide 20 parts in this order. The resulting residue was dried to obtain the compound represented by formula (II-2) 5.18 parts. The yield was 64%.

[0496]

[0497] Identification of the compound represented by formula (II-2)

[0498] (Mass spectrum) Ionization mode = ESI+: m / z = [M+H] + 823.3

[0499] Exact Mass: 823.3

[0500] <Resin Synthesis Example 1: Synthesis of Resin (B-1)>

[0501] A flask equipped with a reflux condenser, a dropping funnel, and a stirrer was replaced with a nitrogen atmosphere by flowing an appropriate amount of nitrogen, and propylene glycol monomethyl ether acetate 340 parts was charged. While stirring, it was heated to 80°C. Next, a mixture (containing 1:1 by mole ratio) of acrylic acid 3,4-epoxytricyclo[5.2.1.0 2,6 ]decane-8-yl ester and acrylic acid 3,4-epoxytricyclo[5.2.1.0 2,6 ]decane-9-yl ester 54 parts, benzyl methacrylate 239 parts, and a mixed solution of propylene glycol monomethyl ether acetate 73 parts was added dropwise over 5 hours. On the other hand, a solution in which a polymerization initiator 2,2-azobis(2,4-dimethylpentanenitrile) 40 parts was dissolved in propylene glycol monomethyl ether acetate 197 parts was added dropwise over 6 hours. After the completion of the addition of the initiator solution, it was maintained at 80°C for 3 hours, and then cooled to room temperature to obtain a copolymer (resin (B-1)) solution having a viscosity of 127 mPa-s and a solid content of 37.0% as measured by a B-type viscometer (23°C). The weight average molecular weight Mw of the generated copolymer was 9.4 x 10 3, the dispersity was 1.89, and the acid value, calculated as solid content, was 114 mg-KOH / g. The resin (B-1) had the following structural units.

[0502]

[0503] <Resin Synthesis Example 2: Synthesis of Resin (B-2)>

[0504] Into a flask equipped with a stirring device, a dropping funnel, a condenser, a thermometer, and a gas inlet tube, was added propylene glycol monomethyl ether acetate 241 parts, and while stirring, nitrogen was introduced and the temperature was raised to 130°C. Next, a substance obtained by adding 34 parts of t-butyl peroxy-2-ethylhexanoate to a monomer mixture of 2-ethylhexyl acrylate 73 parts, glycidyl methacrylate 145 parts, and dicyclopentyl methacrylate 10 parts was added dropwise from the dropping funnel into the flask over 2 hours. After the dropwise addition was completed, stirring was continued for 30 minutes, and a copolymerization reaction was carried out. Then, the inside of the flask was replaced with air, and acrylic acid 74 parts, triphenylphosphine 1 part, and p-hydroxyanisole 1 part were added, and the reaction was continued at 120°C for 10 hours. Next, succinic anhydride 65 parts was added to the reaction system, and the reaction was further continued for 1.5 hours, and a polymer was obtained. Finally, propylene glycol monomethyl ether 300 parts was added to the reaction solution, and propylene glycol monomethyl ether acetate was added, and a copolymer (resin (B-2)) solution having a viscosity of 26 mPa-s, measured by a B-type viscometer (23°C), and a solid content of 38.5% was obtained. The weight average molecular weight Mw of the copolymer thus obtained was 6600, and the acid value, calculated as solid content, was 92.5 mg-KOH / g.

[0505] <Dispersion Preparation Example 1: Preparation of Dispersion (A-1)>

[0506] The following ingredients were mixed to obtain dispersion (A-1):

[0507]

[0508] <Dispersion Preparation Example 2: Preparation of Dispersion (A-2)>

[0509] The following ingredients were mixed to obtain dispersion (A-2):

[0510]

[0511] <Dispersion Preparation Example 3: Preparation of Dispersion (A-3)>

[0512] The following ingredients were mixed to obtain dispersion (A-3):

[0513]

[0514]

[0515] <Preparation Example 4: Preparation of Dispersion (A-4)> The following ingredients were mixed to obtain a dispersion (A-4):

[0516] <Preparation Example 5: Preparation of Dispersion (A-5)> The following ingredients were mixed to obtain a dispersion (A-5):

[0517] <Preparation Example 6: Preparation of Dispersion (A-6)> The following ingredients were mixed to obtain a dispersion (A-6):

[0518] <Preparation Example 7: Preparation of Dispersion (A-7)> The following ingredients were mixed to obtain a dispersion (A-7):

[0519]

[0520]

[0521] Note that the compound represented by formula (II-3) is synthesized by the method described in Japanese Patent Application Publication No. 2017-226814.

[0522]

[0523] [Examples 1 to 12 and Comparative Examples]

[0524] <Preparation of Colored Curable Resin Composition>

[0525] Each ingredient was mixed at the compounding ratio (on a mass basis) described in Table 1 to obtain a colored curable resin composition.

[0526] [Table 1]

[0527]

[0528] Dispersion (A-1): Dispersion (A-1) obtained in Preparation Example 1 Dispersion (A-2): Dispersion (A-2) obtained in Preparation Example 2 Dispersion (A-3): Dispersion (A-3) obtained in Preparation Example 3 Dispersion (A-4): Dispersion (A-4) obtained in Preparation Example 4

[0529] Dispersion (A-5): Dispersion (A-5) obtained in Preparation Example 5

[0530] Dispersion (A-6): The dispersion (A-6) obtained in Dispersion Preparation Example 6

[0531] Dispersion (A-7): The dispersion (A-7) obtained in Dispersion Preparation Example 7

[0532] Resin solution (B-2): The resin (B-2) solution obtained in Resin Synthesis Example 2

[0533] Polymerizable compound (C-1): A compound represented by the following formula (NK ester A-DP H-12E: manufactured by Shin-Nakamura Chemical Co., Ltd.)

[0534]

[0535] Polymerization initiator (D-1): N-acetyloxy-l-(4-phenylsulfanylphenyl)-3- cyclohexylpropan-l-one-2-imine (trade name PBG-327: O-acyloxime compound: manufactured by Changzhou Qiangli Electronics New Material Co., Ltd.)

[0536] Solvent (E-1): Propylene glycol monomethyl ether acetate

[0537] Leveling agent (F-1): Polyether-modified silicone oil (trade name TORAY SILICONE SH8400: manufactured by Toray Dow Corning Silicone Co., Ltd.)

[0538] <Formation of colored pattern (color filter)>

[0539] On the surface of a 4-inch glass substrate, a colored curable resin composition was applied by a spin coating method, and pre-baking was performed at 100°C for 2 minutes to obtain a colored composition layer. After cooling, the substrate on which the colored composition layer was formed was subjected to light irradiation at an exposure amount of 1500 J / m2 (based on 365 nm) using an exposure machine (NSR-2205i11D; manufactured by Nikon Corporation). The colored composition layer after light irradiation was subjected to 30 seconds of immersion development in an aqueous developer containing 0.3% of tetramethylammonium hydroxide at 23°C, and after water washing, post-baking was performed using a hot plate at 220°C for 5 minutes to produce a colored pattern. Note that the film thickness of the colored pattern was adjusted so that the maximum transmittance at a wavelength of 400 to 500 nm became 83%. 2

[0540] <Measurement of film thickness>

[0541] The film thickness of the obtained colored pattern was measured using a film thickness measuring device (DEKTAK3; manufactured by Veeco Metrology Group). The film thickness of the colored pattern obtained in each of Examples 1 to 12 and Comparative Example was 0.6 μm.

[0542] <Transmittance evaluation>​

[0543] For the resulting colored patterns, the transmittance in the wavelength region of 380 nm to 780 nm was measured at intervals of 1 nm using a colorimeter (OSP-SP-200; manufactured by Olympus Corporation).

[0544] (1) Transmittance at 530 nm

[0545] Based on the above measurement results, the transmittance at 530 nm was confirmed for each colored pattern. The results are shown in Table 2. The lower the transmittance at 530 nm, the less the green light leaks out, and it can be said that the color separation performance as a color filter (particularly, a blue color filter) is more excellent.

[0546] [Table 2]

[0547]

[0548] (2) Transmittance at 640 nm

[0549] Based on the above measurement results, the transmittance at 640 nm was confirmed for each colored pattern. The results are shown in Table 3. The lower the transmittance at 640 nm, the less the red light leaks out, and it can be said that the color separation performance as a color filter (particularly, a blue color filter) is more excellent.

[0550] [Table 3]

[0551]

Claims

1. A colored curable resin composition comprising a colorant, a resin, a polymerizable compound, and a polymerization initiator, the colorant comprises a xanthene dye, a violet pigment, and a blue pigment, the content of the xanthene dye is 8 to 45 parts by mass relative to 100 parts by mass of the blue pigment.

2. The colored curable resin composition according to claim 1, wherein The content rate of the colorant is 35% by mass or more relative to the total amount of solid components of the colored curable resin composition.

3. The colored curable resin composition according to claim 1, wherein The content of the violet pigment is 5 to 250 parts by mass relative to 100 parts by mass of the xanthene dye.

4. A color filter formed using the colored curable resin composition according to any one of claims 1 to 3.

5. A display device comprising the color filter according to claim 4.

6. A solid-state imaging device comprising the color filter according to claim 4.

Images