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, and the colorant contains a xanthene pigment (a1) having a maximum absorption wavelength of 510 nm or more and 535 nm or less, a xanthene pigment (a2) having a maximum absorption wavelength of more than 535 nm and 570 nm or less, and a blue pigment (a3).

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 is used in a composition for forming a blue color filter, the colorant containing, relative to the total weight of the colorant, 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).

[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 (al) having a maximum absorption wavelength of 510 nm or more and 535 nm or less, a xanthene dye (a2) having a maximum absorption wavelength of more than 535 nm and 570 nm or less, and a blue pigment (a3).

[0012] [2] The colored curable resin composition according to [1], wherein the content ratio (al / a2) of the xanthene dye (al) to the xanthene dye (a2) is 0.1 to 15 on a mass basis.

[0013] [3] The colored curable resin composition according to [1] or [2], wherein the total content of the xanthene dye (al) and the xanthene dye (a2) is 8 mass parts or more relative to 100 mass parts of the blue pigment (a3).

[0014] [4] The colored curable resin composition according to any one of [1] to [3], wherein the content ratio of the colorant is 35 mass% or more relative to the total amount of solid components of the colored curable resin composition.

[0015] [5] The colored curable resin composition according to any one of [1] to [4], wherein the content ratio (al / a2) of the xanthene dye (al) to the xanthene dye (a2) is 10 or less on a mass basis.

[0016] [6] The colored curable resin composition according to any one of [1] to [5], wherein the content of the xanthene dye (al) is 7 to 15 mass% in 100 mass% of the colorant.

[0017] [7] The colored curable resin composition according to any one of [1] to [6], wherein the content ratio (al / a2) of the xanthene dye (al) to the xanthene dye (a2) is 1.0 to 10 on a mass basis.

[0018] [8] The colored curable resin composition according to any one of [1] to [7], wherein the xanthene dye (a2) comprises a compound represented by formula (1).

[0019]

[0020] [In formula (1),

[0021] 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),

[0022] R 1 and R 2 may form a ring containing a nitrogen atom together, R 3 and R 4may form a ring containing a nitrogen atom together with R 1 ~R 4 The total number of aromatic hydrocarbon rings possessed is 4 or more.

[0023] R 5 represents -OH, -SO3 - , -SO3H, -SO3 - Z + , -CO2H, -CO2 - Z + , -CO2R 8 , -SO3R 8 or -SO2NR 9 R 10 .

[0024] R 6 ~R 7 each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.

[0025] R 8 represents a saturated hydrocarbon group having 1 to 20 carbon atoms which can be substituted with a halogen atom.

[0026] 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, R 9 and R 10 may form a ring containing a nitrogen atom together.

[0027] 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-.

[0028] 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.

[0029] Z + represents an arbitrary cation.

[0030] X represents a halogen atom.

[0031] a represents 0 or 1.

[0032] m represents an integer of 0 to 5, and when m is 2 or more, a plurality of R 5 may be the same or different.

[0033] [9] A color filter formed using the colored curable resin composition described in any one of [1] to [8].

[0034]

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

[0035]

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

[0036] Effects of the Invention

[0037] The colored curable resin composition according to the present application enables production of a color filter in which color separation from green light is improved. DETAILED DESCRIPTION

[0038] [Colored Curable Resin Composition]

[0039] 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 dye (al) having a maximum absorption wavelength of 510 nm or more and 535 nm or less, a xanthene dye (a2) having a maximum absorption wavelength of more than 535 nm and 570 nm or less, and a blue pigment (a3). 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 both color separation from green light and color separation from red light are improved, or a color filter that enables production of a solid-state imaging device with high sensitivity.

[0040] The colored curable resin composition of the present application preferably further contains a solvent (hereinafter, sometimes referred to as solvent (E)).

[0041] The colored curable resin composition of the present application can contain a leveling agent (hereinafter, sometimes referred to as leveling agent (F)).

[0042] 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.

[0043] [Colorant (A)]

[0044] The xanthene dye (al) and the xanthene dye (a2) are dyes that are compounds containing a xanthene skeleton in the molecule, and are dyes each having a specific maximum absorption wavelength.

[0045] The xanthene dye (al) has a maximum absorption wavelength of 510 to 535 nm, and preferably 515 to 530 nm.

[0046] The xanthene dye (a2) has a maximum absorption wavelength of more than 535 nm and 570 nm or less, preferably 536 to 560 nm, more preferably 536 to 545 nm.

[0047] Note that the maximum absorption wavelength of the xanthene dye can be measured by the method described in the Examples below.

[0048] Preferably, one or both of the xanthene dye (al) and the xanthene dye (a2) is a compound represented by formula (1). Preferably, the xanthene dye (al) and the xanthene dye (a2) are combined by selecting from the compounds represented by formula (1) based on the maximum absorption wavelength. The compound represented by formula (1) can also be a tautomer thereof.

[0049]

[0050] [In formula (1),

[0051] 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),

[0052] R 1 and R 2 may form a ring containing a nitrogen atom together, R 3 and R 4 may form a ring containing a nitrogen atom together.

[0053] R 5 represents -OH, -SO3 - , -SO3H, -SO3 - Z + , -CO2H, -CO2 - Z + , -CO2R 8 , -SO3R 8 , or -SO2NR 9 R 10 .

[0054] R 6 ~R 7 each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.

[0055] R 8 represents a saturated hydrocarbon group having 1 to 20 carbon atoms which can be substituted with a halogen atom.

[0056] R9 and R 10 Each independently represents a hydrogen atom or a saturated hydrocarbon group with 1 to 20 carbon atoms that may have substituents, R 9 With R 10 They can form a ring containing nitrogen atoms together.

[0057] R 12 This refers to alkane diesters with 1 to 10 carbon atoms, where the -CH2- group can be replaced with -O-, -CO-, or -NR. 8 -、-OCO-、-COO-、-OCONH-、-CONH- or -NHCO-.

[0058] R 13 Represents hydrogen atoms, hydroxyl groups, alkyl groups with 1 to 4 carbon atoms, or alkoxy groups with 1 to 4 carbon atoms, and multiple R groups. 13 They can be the same or different.

[0059] Z + It represents any cation.

[0060] X represents a halogen atom.

[0061] 'a' represents 0 or 1.

[0062] m represents an integer from 0 to 5. When m is greater than 2, multiple R... 5 They can be the same or different.

[0063] 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.

[0064] As R 1 ~R 4 The saturated hydrocarbon group represented by carbon atoms is preferably an alkyl group with carbon atoms of ...

[0065] As R 8The 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.

[0066] 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.

[0067] R 1 ~R 4 The 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.

[0068] 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.

[0069] 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.

[0070] 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.

[0071] As alkyl groups constituting alkylphenyl groups, examples include those that are R 1 ~R 4an alkyl group having 1 to 20 carbon atoms, as described for the alkyl group in the alkyl group having 1 to 20 carbon atoms, wherein an alkyl group having 1 to 10 carbon atoms is preferred, an alkyl group having 1 to 4 carbon atoms is more preferred, and a methyl group is further preferred. As the alkylphenyl group, a group having an alkyl group at at least one of the two bonding positions that are ortho with respect to the N bonded to the phenyl group is preferred, and a group having an alkyl group at both of the two bonding positions that are ortho with respect to the N bonded to the phenyl group is more preferred. In particular, the xanthene dye (al) preferably contains a compound in which at least one of R 1 4 1 4 1 4

[0072] As the aryl group constituting the arylphenyl group, a phenyl group; an alkylphenyl group such as a tolyl group, a xylyl group, a mesityl group, a propylphenyl group, a butylphenyl group, and the like; and the like can be given, wherein an aryl group having 6 to 10 carbon atoms is preferred, and a phenyl group is more preferred. As the arylphenyl group, a group having an aryl group at at least one of the two bonding positions that are ortho with respect to the N bonded to the phenyl group is preferred, and a group having an aryl group at both of the two bonding positions that are ortho with respect to the N bonded to the phenyl group is more preferred. In particular, the xanthene dye (a2) preferably contains a compound in which at least one of R 1 4 1 4 1 4

[0073] In particular, the aromatic hydrocarbon group having 6 to 30 carbon atoms represented by R 1 4 is preferably an aromatic hydrocarbon group having 6 to 20 carbon atoms,

[0074]

[0075] more preferably: a group that is an alkylphenyl group and has an alkyl group at at least one of the two bonding positions that are ortho with respect to the N bonded to the phenyl group; or a group that is an arylphenyl group and has an aryl group at at least one of the two bonding positions that are ortho with respect to the N bonded to the phenyl group,

[0076] ​​​​​​​​​​​​​​Further preferred are: a group which is an alkylphenyl group having an alkyl group at two bonding positions which are ortho with respect to the N bonded to the phenyl group; or, a group which is an arylphenyl group having an aryl group at two bonding positions which are ortho with respect to the N bonded to the phenyl group.

[0077] R 1 ~R 4 The aromatic hydrocarbon group having 6 to 30 carbon atoms represented by the above formula can have a substituent, and as the substituent, a halogen atom, -OH, -OR 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 - , -SO3 - Z + , -SO2NR 9 R 10 , -SO3 - are more preferred. As -SO3 - Z + in this case, -SO3 - N + (R 11 )4 is preferred. 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.

[0078] Z + is preferably an ammonium cation, Na + , or K + , and more preferably an ammonium cation. Note that in this specification, the ammonium cation is not limited to NH4 + , but is defined to include primary ammonium cations, secondary ammonium cations, tertiary ammonium cations, quaternary ammonium cations, and the like, and among them, a quaternary ammonium cation is preferred. 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 R11 may be the same or different.

[0079] 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.

[0080] As the saturated hydrocarbon group having 1 to 20 carbon atoms represented by R 11 , an alkyl group having 1 to 20 carbon atoms is preferable, and an alkyl group having 1 to 15 carbon atoms is more preferable.

[0081] As the saturated hydrocarbon group having 1 to 20 carbon atoms represented by R 11 , an alkyl group having 1 to 20 carbon atoms is preferable, and an alkyl group having 1 to 15 carbon atoms is more preferable.

[0082] As the aforementioned N + (R 11 )4, four R 11 's are preferably N + (R 11 )4 in which at least two of the four R 11 's are a saturated hydrocarbon group having 5 to 20 carbon atoms (particularly, an alkyl group having 5 to 20 carbon atoms). In addition, the total number of carbon atoms of the four R 8 's is preferably 20 to 80, and more preferably 20 to 60.

[0083] As -OR 8 , methoxy group, ethoxy group, propoxy group, butoxy group, pentoxy group, hexyloxy group, heptyloxy group, octyloxy group, 2-ethylhexyloxy group, and icosyloxy group, and the like can be given.

[0084] As -CO2R 8 , methoxycarbonyl group, ethoxycarbonyl group, propoxycarbonyl group, butoxycarbonyl group, hexyloxycarbonyl group, and icosyloxycarbonyl group, and the like can be given.

[0085] As -SR 8 , methylsulfanyl group, ethylsulfanyl group, butylsulfanyl group, hexylsulfanyl group, decylsulfanyl group, and icosylsulfanyl group, and the like can be given.

[0086] As -SO2R 8 , methylsulfonyl group, ethylsulfonyl group, butylsulfonyl group, hexylsulfonyl group, decylsulfonyl group, and icosylsulfonyl group, and the like can be given.

[0087] As -SO3R 9 , methoxysulfonyl group, ethoxysulfonyl group, propoxysulfonyl group, butoxysulfonyl group, hexyloxysulfonyl group, and icosyloxysulfonyl group, and the like can be given.

[0088] As -SO2NR 10 , the following can be given:

[0089] Sulfamoyl group;

[0090] N-methylsulfamoyl group, N-ethylsulfamoyl group, N-propylsulfamoyl group, N-isopropylsulfamoyl group, N-butylsulfamoyl group, N-isobutylsulfamoyl group, N-sec-butylsulfamoyl group, N-tert-butylsulfamoyl group, N-pentylsulfamoyl group, N-(l-ethylpropyl)sulfamoyl group, N-(l,l-dimethylpropyl)sulfamoyl group, N-(l,2-dimethylpropyl)sulfamoyl group, N-(2,2-dimethylpropyl)sulfamoyl group, N-(l-methylbutyl)sulfamoyl group, N-(2-methylbutyl)sulfamoyl group, N-(3-methylbutyl)sulfamoyl group, N-cyclopentylsulfamoyl group, N-hexylsulfamoyl group, N-(l,3-dimethylbutyl)sulfamoyl group, N-(3,3-dimethylbutyl)sulfamoyl group, N-heptylsulfamoyl group, N-(l-methylhexyl)sulfamoyl group, N-(l,4-dimethylpentyl)sulfamoyl group, N-octylsulfamoyl group, N-(2-ethylhexyl)sulfamoyl group, N-(l,5-dimethylhexyl)sulfamoyl group, N-(l,l,2,2-tetramethylbutyl)sulfamoyl group, and the like.

[0091] N,N-dimethylsulfamoyl group, N,N-ethylmethylsulfamoyl group, N,N-diethylsulfamoyl group, N,N-propylmethylsulfamoyl group, N,N-isopropylmethylsulfamoyl group, N,N-tert-butylmethylsulfamoyl group, N,N-butylethylsulfamoyl group, N,N-bis(l-methylpropyl)sulfamoyl group, N,N-heptylmethylsulfamoyl group, and the like.

[0092] alkanediyl group having 1 to 10 carbon atoms represented by R 12 For example, methylene, ethylene, 1,3-propylene, 1,4-butylene, 1,5-pentylene, 1,6-hexylene, isopropylene, isobutylene, 2-methyl-l,3-propylene, isopentylene, isohexylene, isooctylene, 2-ethylhexylene, and the like can be given. Among them, alkanediyl group having 1 to 6 carbon atoms is preferred, and alkanediyl group having 1 to 4 carbon atoms is more preferred.

[0093] R 12 -CH2- included in the alkanediyl group represented by R 8 may be replaced with -O-, -CO-, -NR

[0094] alkyl group having 1 to 4 carbon atoms represented by R 13 For example, methyl, ethyl, propyl, butyl can be given.

[0095] as R 13 as R 13 is preferably a methyl group, an ethyl group, a methoxy group, an ethoxy group, more preferably a methoxy group or an ethoxy group.

[0096] R 13 is preferably a methyl group, an ethyl group, a methoxy group, an ethoxy group, more preferably a methoxy group or an ethoxy group.

[0097] as R 1 as R 2 , R 3 as R 4 , R 9 as R 10 forming a ring containing a nitrogen atom together with R

[0098]

[0099] R 1 ~ R 4 are each independently a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms which can have a substituent, or an aromatic hydrocarbon group having 6 to 30 carbon atoms which can have a substituent, more preferably are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms which can have a substituent, or an aromatic hydrocarbon group having 6 to 30 carbon atoms which can have a substituent, further preferably are each independently a hydrogen atom, an alkyl group having 1 to 10 carbon atoms which can have a substituent, or an aromatic hydrocarbon group having 6 to 20 carbon atoms which can have a substituent.

[0100] In particular, in xanthene dye (a1), R 1 and R 4 each independently represent an aromatic hydrocarbon group having 6 to 30 carbon atoms which can have a substituent, R 2 and R 3 each independently represent a hydrogen atom or a saturated hydrocarbon group having 1 to 20 carbon atoms which can have a substituent; more preferably R 1 and R 4 each independently represent an aromatic hydrocarbon group having 6 to 20 carbon atoms which can have a substituent, R 2 and R 3 each independently represent a hydrogen atom or an alkyl group having 1 to 10 carbon atoms which can have a substituent; further preferably R 1 and R 4 each independently represent an alkylphenyl group having 7 to 20 carbon atoms which can have a substituent, R 2 and R 3 each independently represent a hydrogen atom or an alkyl group having 1 to 10 carbon atoms which can have a substituent.

[0101] In addition, in xanthene dye (a2), R 1 and R4 each independently represents a saturated hydrocarbon group having 1 to 20 carbon atoms which can have a substituent or an aromatic hydrocarbon group having 6 to 30 carbon atoms which can have a substituent, R 2 and R 3 each independently represents a hydrogen atom or a saturated hydrocarbon group having 1 to 20 carbon atoms which can have a substituent; more preferably R 1 and R 4 each independently represents an alkyl group having 1 to 10 carbon atoms which can have a substituent or an aromatic hydrocarbon group having 6 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; further preferably R 1 and R 4 each independently represents an alkyl group having 1 to 10 carbon atoms which can have a substituent, 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.

[0102] 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.

[0103] 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.

[0104] R 6 to R 7 each independently is preferably a hydrogen atom, a methyl group, or an ethyl group, more preferably a hydrogen atom.

[0105] R 5 is preferably -CO2H, -CO2 - Z + , -CO2R 8 , -SO3 - , -SO3- Z + -SO3H, -SO2NR 9 R 10 -SO3 - -SO3 - Z + -SO3H, -SO2NR 9 R 10 -SO3 - -SO3 - Z + .

[0106] m is preferably 1 to 4, more preferably 1 or 2, and further preferably 1.

[0107] R 5 The bonding position of R is not particularly limited, but is preferably at least one of the two bonding positions ortho to the xanthene skeleton, and more preferably one of the two bonding positions ortho to the xanthene skeleton. In addition, in the case where m is 2 or more, it is preferable that R be bonded to at least one of the two bonding positions ortho to the xanthene skeleton and the bonding position para to the xanthene skeleton, and more preferably one of the two bonding positions ortho to the xanthene skeleton and the bonding position para to the xanthene skeleton.

[0108] 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.

[0109] In formula (1), the number of -SO3 - in ionic form is preferably 0 or 1, and more preferably 1.

[0110] a represents 0 or 1, and is preferably 0.

[0111] 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 ionic form, a is preferably 0, and in the case where the compound represented by formula (1) has no -SO3 - in ionic form, a is preferably 1.

[0112] 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 , more preferably 1 to 4, and further preferably 1 to 2.

[0113] The xanthene dye (al) and the xanthene dye (a2) are more preferably compounds having the above-mentioned specific maximum absorption wavelength among the compounds represented by formula (2) or formula (3). The compound represented by formula (2) can also be a tautomer thereof, and the compound represented by formula (3) can also be a tautomer thereof.

[0114]

[0115] [In formula (2),

[0116] 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.

[0117] 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 .

[0118] p and q each independently represent an integer of 0 to 5, and when p is 2 or more, the plurality of R 23 may be the same or different, and when q is 2 or more, the plurality of R 24 may be the same or different.

[0119] R 25 represents -SO3 - , -SO3H, -SO3 - Z + , or -SO2NR 29 R 30 .

[0120] R 29 and R 30 each independently represent a hydrogen atom or an alkyl group having 1 to 10 carbon atoms.

[0121] a, m, X, and Z + are the same as described above.

[0122]

[0123] [In formula (3),

[0124] R 31 and R 34 each independently represent an alkyl group having 1 to 10 carbon atoms which can have a substituent.

[0125] R32 and R 33 each independently represents a hydrogen atom, or an alkyl group having 1 to 10 carbon atoms which can have a substituent.

[0126] R 35 represents -SO3 - , -SO3H, -SO3 - Z + , or -SO2NR 29 R 30 .

[0127] R 29 and R 30 each independently represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms.

[0128] a, m, X, and Z + are the same as those in the foregoing.

[0129] In formula (2) and formula (3), a, m, X, and Z + are also the same as a, m, X, and Z + in formula (1).

[0130] As the alkyl group having 1 to 10 carbon atoms represented by R 21 to R 22 , R 29 to R 30 , and R 31 to R 34 , specifically, straight-chain or branched-chain alkyl groups such as a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an isopropyl group, an isobutyl group, a tert-butyl group, an isopentyl group, a neopentyl group, and a 2-ethylhexyl group can be mentioned.

[0131] R 21 to R 22 , and R 31 to R 34 The alkyl group having 1 to 10 carbon atoms represented by R 1 to R 4 may have a substituent, and as the substituent, the same groups as those which the saturated hydrocarbon group having 1 to 20 carbon atoms represented by R 1 to R 4 may have can be mentioned. Among them, a halogen atom, a hydroxyl group, a carboxyl group, and more preferably a carboxyl group are preferred.

[0132] R 21 and R 22 each independently are preferably a hydrogen atom, or an alkyl group having 1 to 10 carbon atoms which can have a carboxyl group, more preferably a hydrogen atom, or an alkyl group having 1 to 5 carbon atoms which can have a carboxyl group, and further preferably a hydrogen atom.

[0133] R 29 and R30 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 29 is a hydrogen atom, R 30 is an alkyl group having 1 to 10 carbon atoms, more preferably R 29 is a hydrogen atom, R 30 is a branched alkyl group having 3 to 10 carbon atoms, further preferably R 29 is a hydrogen atom, R 30 is a 2-ethylhexyl group.

[0134] R 31 and R 34 each independently is preferably an alkyl group having 1 to 8 carbon atoms which can have a substituent, more preferably an alkyl group having 1 to 5 carbon atoms which can have a substituent, further preferably an alkyl group having 2 to 4 carbon atoms which can have a substituent.

[0135] R 32 and R 33 each independently is preferably a hydrogen atom or an alkyl group having 1 to 8 carbon atoms which can have a substituent, more preferably a hydrogen atom or an alkyl group having 1 to 5 carbon atoms which can have a substituent, further preferably a hydrogen atom or an alkyl group having 2 to 4 carbon atoms which can have a substituent, particularly preferably an alkyl group having 2 to 4 carbon atoms which can have a substituent.

[0136] As the alkyl group having 1 to 4 carbon atoms represented by R 23 and R 24 , for example, straight-chain or branched-chain alkyl groups such as 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, and the like can be given, of which an alkyl group having 1 to 2 carbon atoms is preferred, and a methyl group is more preferred.

[0137] As the aromatic hydrocarbon group having 6 to 10 carbon atoms represented by R 23 and R 24 , a phenyl group; an alkylphenyl group such as a tolyl group, a xylyl group, a mesityl group, a propylphenyl group, a butylphenyl group, and the like; and the like can be given, of which a phenyl group is preferred.

[0138] R 23 and R 24 each independently is preferably an alkyl group having 1 to 4 carbon atoms, an aromatic hydrocarbon group having 6 to 10 carbon atoms, or a -SO3 - , more preferably an alkyl group having 1 to 4 carbon atoms or an aromatic hydrocarbon group having 6 to 10 carbon atoms, and more preferably a methyl group or a phenyl group.

[0139] In particular, in the xanthene dye (al), R 23 and R 24Each of R1to R4is independently preferably an alkyl group having 1 to 4 carbon atoms, more preferably a methyl group.

[0140] In addition, in the xanthene dye (a2), R 23 and R 24 Each of R1to R4is independently preferably an alkyl group having 1 to 4 carbon atoms, an aromatic hydrocarbon group having 6 to 10 carbon atoms, or -SO3 - , more preferably an alkyl group having 1 to 4 carbon atoms, or an aromatic hydrocarbon group having 6 to 10 carbon atoms, further preferably an aromatic hydrocarbon group having 6 to 10 carbon atoms, particularly preferably a phenyl group.

[0141] As for the bonding position of R 23 and R 24 , it is preferably at least one of the two bonding positions that are ortho with respect to N, more preferably both of the two bonding positions that are ortho with respect to N.

[0142] 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, particularly preferably 2.

[0143] R 25 is particularly preferably -SO3 - .

[0144] R 35 is preferably -SO3 - or -SO3 - Z + .

[0145] In formulae (2) and (3), the number of -SO3 - in ionic form is preferably 0 or 1, more preferably 1.

[0146] The compound represented by formulae (2) and (3) is preferably electrically neutral. That is, in the case where there is one -SO3 - in ionic form, a is preferably 0, and in the case where there is no -SO3 - in ionic form, a is preferably 1.

[0147] The compound represented by formulae (2) and (3) 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, further preferably one or two.

[0148] In particular, the thallium pigment (a1) is preferably a compound represented by formula (1), and more preferably a compound represented by formula (2). Furthermore, as a compound represented by formula (2), having one molecule selected from -SO3... - -SO3H, -SO3 - Z + and -SO2NR 9 R 10 The substituents in the group, and R 23 and R 24 Each is independently an alkyl group having 1 to 4 carbon atoms, or -SO3 - -SO3H, -SO3 - Z + or -SO2NR 29 R 30 Compounds of that type are also preferred.

[0149] The pyrithione pigment (a2) is preferably a compound represented by formula (1), and more preferably a compound represented by formula (2) or (3).

[0150] Xanthan pigment (a2) is also preferably a compound represented by formula (1) having two or more (especially two to four) selected from -SO3. - -SO3H, -SO3 - Z + and -SO2NR 9 R 10 The compounds comprising the group (hereinafter referred to as compound (i)) are more preferably compounds represented by formula (2) or (3) having two or more (especially two to four) groups selected from -SO3. - -SO3H, -SO3 - Z + and -SO2NR 9 R 10 Compounds consisting of groups in a group.

[0151] Xanthan pigment (a2) is also preferably R, which is a compound represented by formula (1). 1 ~R 4 Compounds having a total number of 4 or more aromatic hydrocarbon rings (preferably benzene rings) (hereinafter referred to as compound (ii)). In compound (ii), R 1 ~R 4 The total number of aromatic hydrocarbon rings is more preferably 4 to 6. The aforementioned compound (ii) is more preferably a compound having at least one (especially two) aromatic hydrocarbon groups having 6 to 10 carbon atoms, as represented by formula (2). 23and has at least one (especially two) R that is an aromatic hydrocarbon group having 6 to 10 carbon atoms 24 of the compound.

[0152] That is, the xanthene dye (a2) is also preferably the aforementioned compound (i) or the aforementioned compound (ii), and more preferably at least contains the compound (ii).

[0153] As the compound represented by the aforementioned formula (1), for example, there can be mentioned the compounds represented by formulae (1-1) to (1-56). Note that, in the following formulae, Ra represents 2-ethylhexyl.

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160] In addition, as the compound represented by the aforementioned formula (1), there can be mentioned, for example, 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 solid content, the copolymer being a copolymer of a monomer group containing methyl methacrylate, 2-ethylhexyl methacrylate, and dimethylaminoethyl methacrylate chloride salt. 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 using a 5% potassium chromate aqueous solution as an indicator and then converting to the equivalent of potassium hydroxide.

[0161]

[0162] Note that the colored curable resin composition of the present application can contain one or two or more kinds of the xanthene dye (a1), and can also contain one or two or more kinds of the xanthene dye (a2).

[0163] As the blue pigment (a3) included in the aforementioned colorant (A), known blue pigments can be used, and, for example, pigments having a blue hue 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 include one or two or more kinds of blue pigments (a3).

[0164] As the blue pigment (a3), specifically, C.I. Pigment Blue 15, 15:3, 15:4, 15:6, 16, 60, 80, or the like can be mentioned, of which, phthalocyanine-based blue pigments such as C.I. Pigment Blue 15, 15:3, 15:4, 15:6, 16, or the like are preferred, copper phthalocyanine-based blue pigments such as C.I. Pigment Blue 15, 15:3, 15:4, 15:6, or the like are more preferred, and C.I. Pigment Blue 15:4 and / or 15:6 is further preferred, and at least C.I. Pigment Blue 15:6 is particularly preferred.

[0165] The content of C.I. Pigment Blue 15:6 in 100% by mass of the blue pigment (a3) is preferably 30% by mass or more, more preferably 50% by mass or more, further preferably 70% by mass or more, and particularly preferably 80% by mass or more or 85% by mass or more, and can also be 100% by mass.

[0166] The content of the xanthene pigment (a1) with respect to the total amount of the colorant (A) is preferably 1 to 40% by mass, more preferably 5 to 20% by mass, and further preferably 7 to 15% by mass. By adjusting the content of the xanthene pigment (a1) to the above range, the leakage of red light in the obtained color filter can be further suppressed. In addition, it is also preferable that the xanthene pigment (a1) represented by formula (2) be 7% by mass or more from the viewpoint of further suppressing the leakage of red light in the obtained color filter.

[0167] The content of the xanthene pigment (a2) with respect to the total amount of the colorant (A) is preferably 0.1 to 40% by mass, more preferably 0.5 to 30% by mass, further preferably 0.8 to 25% by mass, and can also be 0.8 to 15% by mass.

[0168] The content ratio (a1 / a2) of the aforementioned xanthene pigment (a1) with respect to the aforementioned xanthene pigment (a2) is preferably 0.05 to 20 by mass ratio, more preferably 0.1 to 15 by mass ratio, further preferably 1.0 to 10 by mass ratio, and particularly preferably 1.0 to 7 by mass ratio. By adjusting the mass ratio (a1 / a2) to the above range, the leakage of green light in the obtained color filter can be further suppressed. In addition, by adjusting the mass ratio (a1 / a2) to 1.0 to 10 (preferably 1.0 to 7), a color filter that enables the production of a solid-state imaging device with higher sensitivity can be formed.

[0169] The content of the blue pigment (a3) is preferably 30 to 98% by mass, more preferably 50 to 94% by mass, and further preferably 60 to 90% by mass, relative to the total amount of the colorant (A).

[0170] The total content of the xanthene pigment (al) and the xanthene pigment (a2) is, for example, 3 to 60 parts by mass, preferably 8 to 50 parts by mass, more preferably 12 to 40 parts by mass, and further more preferably 20 to 40 parts by mass, relative to 100 parts by mass of the blue pigment (a3). By adjusting the total content to be equal to or higher than the lower limit value described above, it is easy to further suppress the leakage of green light of the obtained color filter. In addition, by adjusting the total content to be equal to or lower than the upper limit value described above, it is easy to further suppress the leakage of red light of the obtained color filter.

[0171] The total content of the xanthene pigment (al), the xanthene pigment (a2), and the blue pigment (a3) is preferably 60% by mass or more, more preferably 80% by mass or more, further preferably 90% by mass or more, and particularly preferably 95% by mass or more, and can be 98% by mass or more or 100% by mass, relative to the total amount of the colorant (A).

[0172] The colorant (A) can include one or two or more colorants other than the xanthene pigment (al), the xanthene pigment (a2), and the blue pigment (a3) (hereinafter sometimes referred to as other colorants (a4)).

[0173] 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.

[0174] The dye (a4-1) is not particularly limited, and a known dye can be used. For example, solvent dyes, acid dyes, direct dyes, mordant dyes, and the like can be given. As the dye, 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 (Saiden Co.), and the like can be given. In addition, depending on the chemical structure, xanthene dyes other than the xanthene pigment (al) and the xanthene pigment (a2), azo dyes, cyanine dyes, triarylmethane dyes, thiazole dyes, oxazine dyes, anthraquinone dyes, naphthoquinone dyes, quinone imine 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.

[0175] Specifically, as the dye (a4-1), for example, the following can be given:

[0176] C.I. Solvent Yellow 4, 14, 15, 23, 24, 38, 62, 63, 68, 82, 94, 98, 99, 117, 162, 163, 167, 189;

[0177] 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;

[0178] C.I. Solvent Orange 2, 7, 11, 15, 26, 56, 77, 86;

[0179] C.I. Solvent Violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60;

[0180] 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;

[0181] C.I. Solvent Green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35 and C.I. Solvent dyes,

[0182] 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;

[0183] 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;

[0184] 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;

[0185] C.I. Acid Violet 6B, 7, 15, 16, 17, 19, 21, 23, 24, 25, 34, 38, 49, 72;

[0186] 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;

[0187] 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,

[0188] 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 ;

[0189] 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;

[0190] C.I. Direct Orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107;

[0191] C.I. Direct Violet 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104;

[0192] 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;

[0193] 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,

[0194] C.I. Disperse Yellow 51, 54, 76;

[0195] C.I. Disperse Violet 26, 27;

[0196] C.I. Disperse Blue 1, 14, 56, 60 and the like C.I. Disperse dyes,

[0197] 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;

[0198] C.I. Basic Violet 2;

[0199] C.I. Basic Red 9;

[0200] C.I. Basic Green 1 ; and the like C.I. Basic dyes,

[0201] C.I. Reactive Yellow 2, 76, 116;

[0202] C.I. Reactive Orange 16;

[0203] C.I. Reactive Red 36; etc. C.I. Reactive dyes,

[0204] C.I. Med. Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65;

[0205] C.I. Med. 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;

[0206] C.I. Med. Orange 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47, 48;

[0207] C.I. Med. 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;

[0208] C.I. Med. 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;

[0209] C.I. Med. Green 1, 3, 4, 5, 10, 13, 15, 19, 21, 23, 26, 29, 31, 33, 34, 35, 41, 43, 53, etc. C.I. Med. dyes,

[0210] C.I. Vat Green 1, etc. C.I. Vat dyes, etc.

[0211] These dyes (a4-1) can use one dye or a plurality of dyes for each color, or can combine the dyes of each color.

[0212] 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 given.

[0213] As the pigments classified as pigments (a4-2), specifically, pigments classified as pigments in the Dye Index (published by The Society of Dyers and Colourists) can be given.

[0214] 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;

[0215] C.I. Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73, and the like orange pigments;

[0216] 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;

[0217] C.I. Pigment Green 7, 36, 58, 59, 62, 63, 64, 65, 66, 67, and the like green pigments;

[0218] C.I. Pigment Violet 1, 19, 23, 29, 32, 36, 38, and the like violet pigments;

[0219] C.I. Pigment Brown 23, 25, and the like brown pigments;

[0220] C.I. Pigment Black 1, 7, 31, 32, and the like black pigments; and the like.

[0221] These pigments (a4-2) can use one pigment or a plurality of pigments for each color, or can combine pigments of each color.

[0222] The xanthene pigment (al), the xanthene 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 to 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 be each individually subjected to dispersion treatment, or a plurality of them can be mixed and subjected to dispersion treatment.

[0223] As the pigment dispersant, a surfactant or the like can be mentioned, and any of cationic, anionic, nonionic, and amphoteric surfactants can be used. Specifically, surfactants such as polyester-based, polyamine-based, and acrylic-based surfactants, and the like can be mentioned. These pigment dispersants can be used alone or in combination of two or more. As the pigment dispersant, if expressed by trade names, 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 mentioned.

[0224] In the case of using the 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 preparing a colorant dispersion liquid containing two or more colorants, there is a tendency that a more uniform colorant dispersion liquid can be obtained.

[0225] The content ratio of the aforementioned colorant (A) is, for example, 10 to 75% by mass, preferably 20 to 65% by mass, more preferably 30 to 55% by mass, and further preferably 35 to 55% by mass, in the total amount of solid components. By adjusting the content ratio of the colorant (A) to be equal to or more than the aforementioned lower limit value, it becomes easier to obtain suitable spectral transmittance, color density as a color filter, and in addition, by adjusting the content ratio of the colorant (A) to be equal to or less than the aforementioned upper limit value, reliability, pattern formability can be improved. In particular, by using the colored curable resin composition of the present application, it is possible to manufacture a color filter having good color separation while suppressing the colorant concentration, and based on the point that color separation and reliability such as chemical resistance, heat resistance, and pattern formability can be simultaneously achieved, it can also be said to be preferable.

[0226] Note that, in the present specification, the "total amount of solid components" means the total amount of components after removing the solvent from the colored curable resin composition of the present application. The total amount of solid components and the content of each component with respect thereto can be measured by known analysis means such as liquid chromatography, gas chromatography, and the like.

[0227] <Resin (B)>

[0228] The resin (B) is not particularly limited, but an alkali-soluble resin is preferable. As the resin (B), the following resins [K1] to [K6], and the like can be mentioned.

[0229] Resin [K1]: a copolymer having a structural unit from at least one monomer (a) (hereinafter sometimes referred to as "(a)") selected from the group consisting of an unsaturated carboxylic acid and an unsaturated carboxylic anhydride, and a structural unit from a monomer (b) (hereinafter sometimes referred to as "(b)") having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenic unsaturated bond;

[0230] 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) (but different from (a) and (b)) capable of copolymerization with (a) (hereinafter sometimes referred to as "(c)");

[0231] Resin [K3]: a copolymer having a structural unit from the aforementioned (a) and a structural unit from the aforementioned (c);

[0232] 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;

[0233] 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;

[0234] 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 preferably does not contain);

[0235] 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).

[0236] As (a), specifically, for example, the following can be given:

[0237] Acrylic acid, methacrylic acid, crotonic acid, o-, m-, p-vinylbenzoic acid, and the like unsaturated monocarboxylic acids;

[0238] 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 unsaturated dicarboxylic acids;

[0239] Bicyclic unsaturated compounds containing a carboxyl group such as methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo[2.2.1]hept-2-ene, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene, 5-carboxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-carboxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-carboxy-6-methylbicyclo[2.2.1]hept-2-ene, 5-carboxy-6-ethylbicyclo[2.2.1]hept-2-ene, and the like;

[0240] 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;

[0241] Unsaturated mono-[(meth)acryloyloxyalkyl] esters of a polybasic carboxylic acid having 2 or more valences such as succinic acid mono[2-(meth)acryloyloxyethyl] ester, phthalic acid mono[2-(meth)acryloyloxyethyl] ester, and the like;

[0242] Unsaturated acrylate esters having a hydroxyl group and a carboxyl group in the same molecule such as α-(hydroxymethyl)acrylic acid; and the like.

[0243] Among them, from the viewpoint of copolymerizability, and the solubility of the obtained resin in an aqueous alkaline solution, acrylic acid, methacrylic acid, maleic anhydride, and the like are preferred.

[0244] (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.

[0245] 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 same applies to "(meth)acryloyl" and "(meth)acrylate".

[0246] As (b), for example, a monomer (b1) having an oxiranyl group and an ethylenic unsaturated bond (hereinafter sometimes referred to as "(b1)"), a monomer (b2) having an oxetanyl group and an ethylenic unsaturated bond (hereinafter sometimes referred to as "(b2)"), a monomer (b3) having a tetrahydrofuryl group and an ethylenic unsaturated bond (hereinafter sometimes referred to as "(b3)"), and the like can be given.

[0247] 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 an alicyclic unsaturated hydrocarbon is epoxidized (hereinafter sometimes referred to as "(b1-2)") can be given.

[0248] As (b1-1), glycidyl (meth)acrylate, β-methyl glycidyl (meth)acrylate, β-ethyl glycidyl (meth)acrylate, glycidyl vinyl ether, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether, α-methyl-o-vinylbenzyl glycidyl ether, α-methyl-m-vinylbenzyl glycidyl ether, α-methyl-p-vinylbenzyl glycidyl ether, 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.

[0249] As (b1-2), vinyl cyclohexene monoxide, 1,2-epoxy-4-vinylcyclohexane (for example, Celloxide 2000; manufactured by Daicel Corp.), 3,4-epoxycyclohexylmethyl (meth)acrylate (for example, Cyclomer A400; manufactured by Daicel Corp.), 3,4-epoxycyclohexylmethyl (meth)acrylate (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.

[0250]

[0251] [In formula (BI) and formula (BII), R e and R f represent a hydrogen atom, or an alkyl group having 1 to 4 carbon atoms, and the hydrogen atom included in the alkyl group can be substituted with a hydroxyl group.

[0252] X e and X f represent a single bond, a *-R g -, a *-R g -O-, a *-R g -S-, or a *-R g -NH-.

[0253] R g represents an alkane diyl group having 1 to 6 carbon atoms.

[0254] * represents a bond to O.

[0255] As the alkyl group having 1 to 4 carbon atoms, there are mentioned methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, t-butyl group, and the like.

[0256] As the alkyl group having 1 to 4 carbon atoms, there are mentioned methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, t-butyl group, and the like.

[0257] As R e and R f , there are mentioned hydrogen atom, methyl group, hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, more preferably hydrogen atom, methyl group.

[0258] As the alkane diyl group, there are mentioned methylene group, ethylene group, propane-1, 2-diyl group, propane-1, 3-diyl group, butane-1, 4-diyl group, pentane-1, 5-diyl group, hexane-1, 6-diyl group, and the like.

[0259] As X e and X f , there are mentioned single bond, methylene group, ethylene group, *-CH2-O-, and *-CH2CH2-O- (* represents a bond to O), more preferably single bond, *-CH2CH2-O- (* represents a bond to O).

[0260] As the compound represented by formula (BI), there are mentioned the compounds represented by any one of formula (BI-1) to formula (BI-15), and the like. Among them, there are mentioned the compounds represented by formula (BI-1), formula (BI-3), formula (BI-5), formula (BI-7), formula (BI-9), or formula (BI-11) to formula (BI-15), more preferably the compounds represented by formula (BI-1), formula (BI-7), formula (BI-9), or formula (BI-15).

[0261]

[0262] As the compound represented by formula (BII), mention can be made of a compound represented by any one of formulae (BII-1) to (BII-15), and the like. Among them, preferred are a compound represented by formula (BII-1), formula (BII-3), formula (BII-5), formula (BII-7), formula (BII-9), or formula (BII-11) to (BII-15), and more preferred are a compound represented by formula (BII-1), formula (BII-7), formula (BII-9), or formula (BII-15).

[0263]

[0264] 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, the ratio of the content thereof [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.

[0265] 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.

[0266] 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.

[0267] As (b), from the viewpoint of being able to further improve the reliability such as heat resistance and chemical resistance of the obtained color filter, (b1) is preferred. Further, from the viewpoint of the storage stability of the colored curable resin composition being excellent, (b1-2) is more preferred.

[0268] As (c), mention can be made of (meth)acrylate-based monomers, unsaturated carboxylic acid esters such as unsaturated dicarboxylic acid esters; vinyl monomers such as vinyl monomers having an unsaturated aliphatic hydrocarbon ring or an aromatic ring; maleimide-based monomers; and the like.

[0269] As the (meth)acrylate-based monomer, for example, mention can be made of:

[0270] (meth)acrylic acid methyl ester, (meth)acrylic acid ethyl ester, (meth)acrylic acid n-butyl ester, (meth)acrylic acid sec-butyl ester, (meth)acrylic acid tert-butyl ester, (meth)acrylic acid 2-ethylhexyl ester, (meth)acrylic acid dodecyl ester, (meth)acrylic acid lauryl ester, (meth)acrylic acid stearyl ester, (meth)acrylic acid cyclopentyl ester, and the like (meth)acrylic acid esters having a straight chain or branched chain aliphatic saturated hydrocarbon group;

[0271] (meth)acrylic acid allyl ester, (meth)acrylic acid propargyl ester, and the like (meth)acrylic acid esters having a straight chain or branched chain aliphatic unsaturated hydrocarbon group;

[0272] (meth)acrylic acid cyclohexyl ester, (meth)acrylic acid 2-methylcyclohexyl ester, (meth)acrylic acid tricyclo[5.2.1.0 2 ,6 ]decane-8-yl ester (which is called as "(meth)acrylic acid dicyclopentyl ester" as a conventional name in the technical field. In addition, sometimes called as "(meth)acrylic acid tricyclodecyl ester"), (meth)acrylic acid isobornyl ester, (meth)acrylic acid adamantyl ester, and the like (meth)acrylic acid esters having a cyclic saturated hydrocarbon group;

[0273] (meth)acrylic acid tricyclo[5.2.1.0 2,6 ]decene-8-yl ester (which is called as "(meth)acrylic acid dicyclopentenyl ester" as a conventional name in the technical field), (meth)acrylic acid dicyclopentyloxyethyl ester, and the like (meth)acrylic acid esters having a cyclic unsaturated aliphatic hydrocarbon group;

[0274] (meth)acrylic acid phenyl ester, (meth)acrylic acid naphthyl ester, (meth)acrylic acid benzyl ester, (meth)acrylic acid phenoxybenzyl ester, and the like (meth)acrylic acid esters having an aromatic ring;

[0275] (meth)acrylic acid 2-hydroxyethyl ester, (meth)acrylic acid 2-hydroxypropyl ester, and the like (meth)acrylic acid esters containing a hydroxyl group.

[0276] As the unsaturated dicarboxylic acid ester, dicarboxylic acid diesters such as maleic acid diethyl ester, fumaric acid diethyl ester, itaconic acid diethyl ester can be given.

[0277] Among these unsaturated carboxylic acid esters, the following are preferable:

[0278] (meth)acrylic acid C 1-10 alkyl ester;

[0279] (meth)acrylic acid tricyclo[5.2.1.0 2,6 ]decane-8-yl ester, and the like (meth)acrylic acid esters having a cyclic saturated hydrocarbon group;

[0280] tricyclo[5.2.1.0 2,6 ]decen-8-yl esters and the like (meth)acrylates having a cyclic unsaturated aliphatic hydrocarbon group;

[0281] benzyl (meth)acrylate, phenoxybenzyl (meth)acrylate and the like (meth)acrylates having an aromatic ring and the like.

[0282] As the vinyl monomer having an unsaturated aliphatic hydrocarbon ring, mention can be made of 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.

[0283] As the vinyl monomer having an aromatic ring, mention can be made of styrene, α-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, p-methoxystyrene and the like styrene-based monomers.

[0284] As other vinyl monomers, mention can be made of: acrylonitrile, methacrylonitrile and the like monomers containing a nitrile group;

[0285] chloroethylene, vinylidene chloride and the like monomers containing a halogen atom;

[0286] acrylamide, methacrylamide, vinyl acetate, 1,3-butadiene, isoprene, 2,3-dimethyl-1,3-butadiene and the like.

[0287] Among these vinyl monomers, from the aspects of copolymerizability and heat resistance, styrene, styrene-based monomers such as vinyltoluene, bicyclo[2.2.1]hept-2-ene (or also called 2-norbornene), and the like bicyclic unsaturated compounds are preferred.

[0288] As the maleimides, 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.

[0289] Among these maleimides, from the aspects of copolymerizability and heat resistance, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, and the like maleimides having an alicyclic hydrocarbon group or an aromatic hydrocarbon group are preferred.

[0290] The structural unit in which (b) is added to the structural unit from (a) means a unit constituted by adding (b) to the structural unit from (a) constituting the main chain of the copolymer, and 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 (bl) having an epoxyethyl group and an ethylenic unsaturated bond is preferred, and a monomer (bl-1) having a structure in which a straight-chain or branched-chain aliphatic unsaturated hydrocarbon is epoxidized is more preferred.

[0291] The structural unit in which (a) is added to the structural unit from (b) means a unit constituted by adding (a) to the structural unit from (b) constituting the main chain of the copolymer, and having 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 epoxyethyl group and an ethylenic unsaturated bond is preferred, and a monomer (bl-1) having a structure in which a straight-chain or branched-chain aliphatic unsaturated hydrocarbon is epoxidized is more preferred. As (a), an unsaturated monocarboxylic acid such as (meth)acrylic acid is preferred.

[0292] The structural unit resulting from the addition of (a) to the structural unit from (b) and further addition of carboxylic anhydride means a structural unit resulting from the half-esterification of carboxylic anhydride to the hydroxyl group produced by the addition of (a) to the structural unit from (b) constituting the main chain of the copolymer, 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 of the aforementioned examples, and (a) can also be any of the aforementioned examples. As (b), a monomer (b1) having an epoxyethyl group and an ethylenic unsaturated bond is preferable, and a monomer (b1-1) 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.

[0293] As the carboxylic anhydride, saturated aliphatic polybasic carboxylic anhydrides such as malonic anhydride, succinic anhydride, glutaric anhydride, and adipic anhydride; unsaturated aliphatic polybasic carboxylic anhydrides such as maleic anhydride, citraconic anhydride, and itaconic anhydride; aromatic polybasic carboxylic anhydrides such as 3-vinylphthalic anhydride and 4-vinylphthalic anhydride; alicyclic polybasic carboxylic anhydrides such as 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, and bicyclo[2.2.1]hept-2-ene-5,6-dicarboxylic anhydride; and other polybasic carboxylic anhydrides can be mentioned.

[0294] In the resin [K1], the ratio of the structural units from each of (a) and (b) in all the structural units constituting the resin [K1] is preferably:

[0295] Structural unit from (a): 2 to 60 mol%

[0296] Structural unit from (b): 40 to 98 mol%,

[0297] More preferably:

[0298] Structural unit from (a): 10 to 50 mol%

[0299] Structural unit from (b): 50 to 90 mol%.

[0300] Further, it is preferable that the structural unit from (c) be substantially excluded.

[0301] The total of the structural unit from (a) and the structural unit from (b) in all the structural units constituting the resin [K1] is, for example, 90 mol% or more, preferably 95 mol% or more, more preferably 98 mol% or more, and particularly preferably 100 mol%.

[0302] If the ratio of the structural units of the resin [Kl] 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 of the obtained color filter are excellent.

[0303] The resin [Kl] can be produced, for example, by the method described in the reference "Kakozai Gosei no Shikenho" (Kakozai Gosei no Shikenho) (Takeru Otsu, issued by Kogyo Gijutsu Center Co., Ltd., 1st edition, 1st printing, March 1, 1972) and the references cited in the reference.

[0304] 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 an oxygen-free atmosphere is created by, for example, replacing the oxygen with nitrogen, and heating and maintaining the temperature 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 recited later as the solvent (E) of the colored curable resin composition of the present application and the like can be mentioned as long as the respective monomers are dissolved.

[0305] 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 included in the colored 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 colored curable resin composition of the present application, and thus the manufacturing process of the colored curable resin composition of the present application can be simplified.

[0306] In the resin [K2], the ratio of the structural units from each of the following is preferably:

[0307] Structural unit from (a): 1 to 70 mol%

[0308] Structural unit from (b): 1 to 60 mol%

[0309] Structural unit from (c): 20 to 95 mol%,

[0310] More preferably:

[0311] Structural unit from (a): 3 to 50 mol%

[0312] Structural unit from (b): 3 to 40 mol%

[0313] Structural units from (c): 30–90 mol%.

[0314] A further preferred option is:

[0315] Structural units from (a): 5–40 mol%

[0316] Structural units from (b): 5–30 mol%

[0317] Structural units from (c): 40–80 mol%.

[0318] Of all the structural units constituting resin [K2], the total of the structural units from (a), (b), and (c) is, for example, 90 mol% or more, preferably 95 mol% or more, more preferably 98 mol% or more, and particularly preferably 100 mol%.

[0319] If the ratio of the structural units of resin [K2] is within the above range, the color-curing resin composition tends to have excellent storage stability, developability when forming color patterns, and solvent resistance, heat resistance and mechanical strength of the obtained color filter.

[0320] In resin [K2], (a) is preferably an unsaturated monocarboxylic acid such as (meth)acrylic acid. As (b), a monomer (b1) having an epoxy ethyl and olefinic unsaturated bond is preferred, and a monomer (b1-2) having a structure in which an alicyclic unsaturated hydrocarbon is epoxidized is more preferred. As (c), (meth)acrylates having cyclic unsaturated aliphatic hydrocarbon groups, (meth)acrylates having aromatic rings, and dicarbonylimide derivatives are preferred.

[0321] Resin [K2] can be manufactured, for example, in the same manner as the method described for manufacturing resin [K1].

[0322] In resin [K3], the preferred ratio of structural units from each of the constituent structural units is as follows:

[0323] Structural units from (a): 2–60 mol%

[0324] Structural units from (c): 40–98 mol%.

[0325] More preferably:

[0326] Structural units from (a): 10–50 mol%

[0327] Structural units from (c): 50–90 mol%.

[0328] A further preferred option is:

[0329] Structural unit from (a): 35 to 45 mol%

[0330] Structural unit from (c): 55 to 65 mol%.

[0331] Further, it is preferable that substantially no structural unit from (b) be contained.

[0332] In the entire structural units constituting the resin [K3], the total of 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%.

[0333] 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.

[0334] The resin [K3] can be produced, for example, in the same manner as the method described as the production method of the resin [Kl].

[0335] In the resin [K4], in the entire structural units constituting the resin [K4], the ratio of the structural unit from each of (a), (b), and (c) is preferably:

[0336] Structural unit from (a) (not added with (b)): 1 to 60 mol%

[0337] Structural unit resulting from addition of (b) to the structural unit from (a): 1 to 50 mol%

[0338] Structural unit from (c): 30 to 90 mol%,

[0339] More preferably:

[0340] Structural unit from (a) (not added with (b)): 5 to 50 mol%

[0341] Structural unit resulting from addition of (b) to the structural unit from (a): 5 to 40 mol%

[0342] Structural unit from (c): 35 to 80 mol%,

[0343] Further more preferably:

[0344] Structural unit from (a) (not added with (b)): 10 to 40 mol%

[0345] Structural unit resulting from addition of (b) to the structural unit from (a): 10 to 25 mol%

[0346] Structural unit from (c): 40 to 75 mol%.

[0347] In the entire structural units constituting the resin [K4], the total of the structural units from (a) (not added with (b)), the structural units in which (b) is added to 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%.

[0348] As the structural units from (a) (not added with (b)), the structural units from an unsaturated monocarboxylic acid such as (meth)acrylic acid are preferable. As the structural units in which (b) is added to the structural units from (a), the structural units in 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 the structural units from an unsaturated monocarboxylic acid such as (meth)acrylic acid are preferable. As the structural units from (c), one or more kinds, more preferably two or more kinds, selected from the group consisting of (meth)acrylates having an aliphatic saturated hydrocarbon group having a linear or branched chain, (meth)acrylates having a cyclic saturated hydrocarbon group, (meth)acrylates having an aromatic ring, a bicyclic unsaturated compound, and a styrene-based monomer are preferable. 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)acrylates, (meth)acrylates having a cyclic saturated hydrocarbon group, (meth)acrylates 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, which are vinyl monomers.

[0349] 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 carboxylic acid and / or carboxylic anhydride possessed by (a).

[0350] First, a copolymer of (a) and (c) is produced in the same manner as the method described as a 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].

[0351] Next, a cyclic ether having 2 to 4 carbon atoms possessed by (b) is reacted with a part of carboxylic acid and / or carboxylic anhydride from (a) in the aforementioned copolymer.

[0352] After the copolymer of (a) and (c) is produced, the atmosphere in the flask is replaced from nitrogen to air, and (b), a reaction catalyst of carboxylic acid or carboxylic anhydride and a cyclic ether (for example, tris(dimethylaminomethyl)phenol, triphenylphosphine, or the like), a polymerization inhibitor (for example, hydroquinone, p-hydroxyanisole, or the like), and the like are added to the flask, and, for example, reacted at 60 to 130°C for 1 to 10 hours, whereby the resin [K4] can be produced.

[0353] 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.

[0354] 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).

[0355] 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, and the like 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.

[0356] 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:

[0357] Structural unit resulting from addition of (b) to the structural unit from (a): 5 to 95 mol%

[0358] Structural unit from (c): 5 to 95 mol%,

[0359] More preferably:

[0360] Structural unit resulting from addition of (b) to the structural unit from (a): 15 to 90 mol%

[0361] Structural unit from (c): 10 to 85 mol%,

[0362] Still more preferably:

[0363] Structural unit resulting from addition of (b) to the structural unit from (a): 20 to 80 mol%

[0364] Structural unit from (c): 20 to 80 mol%.

[0365] In addition, the structural unit from (a) to which (b) is not added is substantially not contained.

[0366] In all the structural units constituting the resin [K4'], the total of the structural unit resulting from addition of (b) 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%.

[0367] As the structural unit resulting from addition of (b) to the structural unit from (a), a structural unit resulting from addition of a monomer (b1-1) having a structure in which an aliphatic unsaturated hydrocarbon having a linear or branched chain is epoxidized to the 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, 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 are preferable.

[0368] For the resin [K4'], the production method of the above-described resin [K4] can be referred to, and the use amount of (b) is preferably 100 moles or more, more preferably 100 moles, relative to 100 moles of (a).

[0369] In the resin [K5], the ratio of the structural unit from each of (a), (b) and (c) in all the structural units constituting the resin [K5] is preferably:

[0370] Structural unit from (b) (not added with (a)): 0 to 30 moles

[0371] Structural unit resulting from addition of (a) to the structural unit from (b): 5 to 95 moles

[0372] Structural unit from (c): 5 to 95 moles,

[0373] More preferably:

[0374] Structural unit from (b) (not added with (a)): 0 to 10 moles

[0375] Structural unit resulting from addition of (a) to the structural unit from (b): 15 to 90 moles

[0376] Structural unit from (c): 10 to 85 moles,

[0377] Further preferably:

[0378] Structural unit from (b) (not added with (a)): 0 to 5 moles

[0379] Structural unit resulting from addition of (a) to the structural unit from (b): 20 to 80 moles

[0380] Structural unit from (c): 20 to 80 moles.

[0381] In the entire structural units constituting the resin [K5], the total of the structural units from (b) (not added with (a)), the structural units resulting from addition of (a) to the structural units from (b), 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%.

[0382] As the structural units from (b) (not added with (a)), the structural units from the monomer (b1-1) having a structure in which a straight-chain or branched-chain aliphatic unsaturated hydrocarbon is epoxidized are preferred. As the structural units resulting from addition of (a) to the structural units from (b), the structural units resulting from addition of an unsaturated monocarboxylic acid such as (meth)acrylic acid to the structural units from the monomer (b1-1) having a structure in which a straight-chain or branched-chain aliphatic unsaturated hydrocarbon is epoxidized are preferred. As the structural units from (c), one or more kinds, more preferably two or more kinds, 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.

[0383] As to the resin [K5], as the first stage, a copolymer of (b) and (c) is obtained in the same manner as in 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.

[0384] The ratio of the structural units from (b) and (c) is, with respect to the total number of moles of the entire structural units constituting the aforementioned copolymer, preferably each:

[0385] Structural units from (b): 5 to 95 mol%

[0386] Structural units from (c): 5 to 95 mol%,

[0387] More preferably:

[0388] Structural units from (b): 10 to 90 mol%

[0389] Structural units from (c): 10 to 90 mol%.

[0390] Further, under the same conditions as in the production method of the resin [K4] or the resin [K4'], the carboxylic acid or carboxylic anhydride possessed by (a) is reacted with the cyclic ether from (b) possessed by the copolymer of (b) and (c), whereby the resin [K5] can be obtained.

[0391] The amount of (a) used in reaction with the aforementioned copolymer is preferably 5 to 100 moles relative to 100 moles of (b), more preferably 60 to 100 moles. Considering the high reactivity of cyclic ethers and the low likelihood of unreacted (b) residue, (b1) is preferred as (b) used in resin [K5], and even more preferably (b1-1).

[0392] In resin [K6], the preferred ratio of structural units from each of the various structural units constituting resin [K6] is:

[0393] Structural units from (b) (unadded to (a)): 0–30 mol%

[0394] Structural unit (unadditional carboxylic anhydride) formed by adding (a) to the structural unit from (b): 5–70 mol%

[0395] The structural unit formed by adding (a) to the structural unit from (b) and further adding carboxylic anhydride: 10–80 mol%

[0396] Structural units from (c): 10–60 mol%.

[0397] More preferably:

[0398] Structural units from (b) (unadded to (a)): 0–10 mol%

[0399] Structural unit (unadditional carboxylic anhydride) formed by adding (a) to the structural unit from (b): 10–50 mol%

[0400] The structural unit formed by adding (a) to the structural unit from (b) and further adding carboxylic anhydride: 25–60 mol%

[0401] Structural units from (c): 15–50 mol%.

[0402] A further preferred option is:

[0403] Structural units from (b) (unadded to (a)): 0–5 mol%

[0404] Structural unit (unadditional carboxylic anhydride) formed by adding (a) to the structural unit from (b): 15–35 mol%.

[0405] The structural unit formed by adding (a) to the structural unit from (b) and further adding carboxylic anhydride: 35–55 mol%.

[0406] Structural units from (c): 20–40 mol%.

[0407] The total of the structural units from (b) (not added with (a)), the structural units added with (a) to the structural units from (b) (not added with carboxylic anhydride), the structural units added with (a) to the structural units from (b) and further added with carboxylic anhydride, 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%.

[0408] As the structural units from (b) (not added with (a)), the structural units from the monomer (b1-1) having a structure in which a straight-chain or branched-chain aliphatic unsaturated hydrocarbon is epoxidized are preferred. As the structural units added with (a) to the structural units from (b) (not added with carboxylic anhydride), the structural units added with an unsaturated monocarboxylic acid such as (meth)acrylic acid to the structural units from the monomer (b1-1) having a structure in which a straight-chain or branched-chain aliphatic unsaturated hydrocarbon is epoxidized are preferred. As the structural units added with (a) to the structural units from (b) and further added with carboxylic anhydride, the structural units added with an unsaturated monocarboxylic acid such as (meth)acrylic acid to the structural units from the monomer (b1-1) having a structure in which a straight-chain or branched-chain aliphatic unsaturated hydrocarbon is epoxidized and further added with a saturated aliphatic polycarboxylic anhydride such as succinic anhydride are preferred. As the structural units from (c), one or more kinds selected from the group consisting of (meth)acrylates having a straight-chain or branched-chain aliphatic saturated hydrocarbon group, (meth)acrylates having a cyclic saturated hydrocarbon group are preferred, and two or more kinds are more preferred.

[0409] As to the resin [K6], 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.

[0410] The ratio of the structural units from (b) and (c) is, with respect to the total number of moles of the total of the structural units constituting the copolymer described above, preferably each:

[0411] The structural units from (b): 5 to 95 mol%

[0412] The structural units from (c): 5 to 95 mol%,

[0413] More preferably:

[0414] The structural units from (b): 10 to 90 mol%

[0415] The structural units from (c): 10 to 90 mol%.

[0416] Further, the carboxylic acid or carboxylic anhydride possessed by (a) is reacted with the cyclic ether derived from (b) possessed by the copolymer of (b) and (c) under the same conditions as those in the production method of the resin [K4]. The amount of (a) used is preferably 80 to 100 moles per 100 moles of (b).

[0417] 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.

[0418] The amount of the carboxylic anhydride used is preferably 0.05 to 1 mole, more preferably 0.10 to 0.8 moles, and further more preferably 0.13 to 0.7 moles, per 1 mole of the amount of (a) used (in other words, 1 mole of the hydroxyl group produced by the use of (a)).

[0419] As the resin (B), specifically, there can be mentioned, for example:

[0420] a (meth)acrylic acid 3,4-epoxycyclohexylmethyl ester / (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];

[0421] a (meth)acrylic acid glycidyl ester / (meth)acrylic acid benzyl ester / (meth)acrylic acid copolymer, a (meth)acrylic acid glycidyl ester / 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 / (meth)acrylic acid benzyl ester copolymer, a 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl acrylate / (meth)acrylic acid / (meth)acrylic acid phenoxybenzyl ester copolymer, a 3-methyl-3-(meth)acryloyloxy-methyl oxetane / (meth)acrylic acid / styrene copolymer, and the like resin [K2];

[0422] a (meth)acrylic acid benzyl ester / (meth)acrylic acid copolymer, a styrene / (meth)acrylic acid copolymer, and the like resin [K3];

[0423] a resin in which (meth) acrylic acid glycidyl ester is added to a part of carboxylic acid groups of a benzyl (meth) acrylate / (meth) acrylic acid copolymer, a resin in which (meth) acrylic acid glycidyl ester is added to a part of carboxylic acid groups of a tricyclodecane (meth) acrylate / styrene / (meth) acrylic acid copolymer, a resin in which (meth) acrylic acid glycidyl ester is added to a part of carboxylic acid groups of a tricyclodecane (meth) acrylate / benzyl (meth) acrylate / (meth) acrylic acid copolymer, a resin in which (meth) acrylic acid glycidyl ester is added to a part of carboxylic acid groups of a norbornene / ethylbenzene / (meth) acrylic acid copolymer, a resin in which (meth) acrylic acid glycidyl ester is added to a part of carboxylic acid groups of a norbornene / styrene / (meth) acrylic acid copolymer, and the like [K4];

[0424] a resin in which (meth) acrylic acid glycidyl ester is reacted with a tricyclodecane (meth) acrylate / (meth) acrylic acid copolymer, a resin in which (meth) acrylic acid glycidyl ester is reacted with a tricyclodecane (meth) acrylate / styrene / (meth) acrylic acid copolymer, and the like [K4'];

[0425] a resin in which (meth) acrylic acid is reacted with a tricyclodecane (meth) acrylate / (meth) acrylic acid glycidyl ester copolymer, a resin in which (meth) acrylic acid is reacted with a tricyclodecane (meth) acrylate / styrene / (meth) acrylic acid glycidyl ester copolymer, and the like [K5];

[0426] a resin in which (meth) acrylic acid is further reacted with tetrahydrophthalic anhydride, obtained by reacting a resin in which (meth) acrylic acid is reacted with a tricyclodecane (meth) acrylate / (meth) acrylic acid glycidyl ester copolymer, a resin in which (meth) acrylic acid is further reacted with succinic anhydride, obtained by reacting a resin in which (meth) acrylic acid is reacted with a 2-ethylhexyl (meth) acrylate / tricyclodecane (meth) acrylate / (meth) acrylic acid glycidyl ester copolymer, a resin in which (meth) acrylic acid is further reacted with succinic anhydride, obtained by reacting a resin in which (meth) acrylic acid is reacted with a methyl (meth) acrylate / 2-ethylhexyl (meth) acrylate / tricyclodecane (meth) acrylate / (meth) acrylic acid glycidyl ester copolymer, and the like [K6].

[0427] The resin (B) can be used alone or in combination of two or more. As the resin (B), at least one selected from the group consisting of the resin [K1], the resin [K2], the resin [K4], and the resin [K6] is preferable, and the resin [K2] and / or the resin [K6] is more preferable.

[0428] In the case where two or more kinds of resins (B) are used in combination, a preferred combination includes, for example, a combination of the resin [K2] and the resin [K6]. By using the resin [K2] and the resin [K6] in combination, the balance between the pattern formability and the reliability becomes more favorable. In the case where the resin [K2] and the resin [K6] are combined, the resin [K2] is, for example, 5 to 99.9% by mass, preferably 50 to 99.8% by mass, and more preferably 75 to 99.7% by mass, relative to 100% by mass of the total of the resin [K2] and the resin [K6].

[0429] 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 foregoing 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.

[0430] 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.

[0431] 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.

[0432] The content ratio of the resin (B) is preferably 5 to 65% by mass, more preferably 12 to 55% by mass, and further preferably 20 to 45% by mass, relative to the total amount of the solid content of the colored curable resin composition. If the content ratio of the resin (B) is within the foregoing 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.

[0433]

[0434] The polymerizable compound (C) is a compound that can be polymerized using active radicals and / or acids generated by the polymerization initiator (D), and examples include a compound having a polymerizable ethylenic unsaturated bond, and the like, and is preferably a (meth)acrylate compound.

[0435] ​The polymeric compound (C) is preferably a polymeric compound having 3 or more ethylenically unsaturated bonds. As such polymeric compounds, for example, trimethylolpropane tri(meth)acrylate, pentaerythritol poly(meth)acrylate (e.g., pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate), dipentaerythritol poly(meth)acrylate (e.g., dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate), tripentaerythritol poly(meth)acrylate (e.g., tripentaerythritol octa(meth)acrylate, tripentaerythritol hepta(meth)acrylate), tetrapentaerythritol poly(meth)acrylate (e.g., tetrapentaerythritol deca(meth)acrylate, tetrapentaerythritol nona(meth)acrylate), tris(2-(meth)acryloyloxyethyl)isocyanurate, alkoxylated pentaerythritol poly(meth)acrylate (e.g., 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 (e.g., 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 (e.g., caprolactone-modified pentaerythritol tri(meth)acrylate, caprolactone-modified pentaerythritol tetra(meth)acrylate), caprolactone-modified dipentaerythritol poly(meth)acrylate (e.g., caprolactone-modified dipentaerythritol penta(meth)acrylate, caprolactone-modified dipentaerythritol hexa(meth)acrylate), and the like can be given.

[0436] Preferably, at least one selected from the group consisting of trimethylolpropane tri(meth)acrylate, dipentaerythritol poly(meth)acrylate, and alkoxylated dipentaerythritol poly(meth)acrylate is used. From the viewpoint of improving 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 and ethoxylated dipentaerythritol hexa(meth)acrylate is more preferable, and ethoxylated dipentaerythritol polyacrylate such as ethoxylated dipentaerythritol pentaacrylate and ethoxylated dipentaerythritol hexaacrylate is further preferable.

[0437] 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.

[0438] 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.

[0439] <Polymerization initiator (D)>

[0440] 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.

[0441] 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.

[0442] The aforementioned O-acyl oxime compound is a compound having a partial structure represented by formula (d1).

[0443] Hereinafter, * represents a bond.

[0444]

[0445] As the aforementioned O-acyl oxime compound, for example, N-benzoyloxy-1- (4-phenylsulfanylphenyl) butane-1-ketone-2-imine, N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-ketone-2-imine, N-benzoyloxy-1- (4-phenylsulfanylphenyl)-3-cyclopentylpropane-1-ketone-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-ketone-2-imine, N- acetyloxy-1-[4-(2-hydroxyethyloxy)phenylsulfanylphenyl]propane-1-ketone-2- imine, N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropane-1-ketone-2- imine, 2-[(acetyloxy)imino]-3-cyclohexyl-1-[4-(phenylsulfanyl)phenyl]propane-1- ketone, and the like can be given. Commercially available products such as Irgacure OXE01, OXE02, OXE03 (manufactured by BASF), N-1919 (manufactured by ADEKA), PBG-314, PBG-317, PBG-326, PBG-327, PBG-329 (manufactured by Q-Force Electronics New Materials Co., Ltd.), and the like can be used. Among them, the O-acyl oxime compound is preferably at least one selected from the group consisting of N-acetyloxy-1-[4-(2-hydroxyethyloxy)phenylsulfanylphenyl]propane-1-ketone-2-imine, N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropane-1-ketone-2-imine, 2-[(acetyloxy)imino]-3-cyclohexyl-1-[4-(phenylsulfanyl)phenyl]propane-1-ketone, N-benzoyloxy-1-(4-phenylsulfanylphenyl)butane-1-ketone-2-imine, N-benzoyloxy-1- (4-phenylsulfanylphenyl)octane-1-ketone-2-imine, and N-benzoyloxy-1-(4- phenylsulfanylphenyl)-3-cyclopentylpropane-1-ketone-2-imine, more preferably at least one selected from the group consisting of 2-[(acetyloxy)imino]-3-cyclohexyl-1-[4- (phenylsulfanyl)phenyl]propane-1-ketone, N-benzoyloxy-1-(4-phenylsulfanylphenyl) octane-1-ketone-2-imine, and N-acetyloxy-1-(4-phenylsulfanylphenyl)-3- cyclohexylpropane-1-ketone-2-imine.If these are O-acyl oxime compounds, there is a tendency to obtain a filter with high brightness.

[0446] 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.

[0447]

[0448] As the compound having a partial structure represented by formula (d2), for example, 2-methyl-2-morpholino-l-(4-methylsulfanylphenyl)propan-l-one, 2-dimethylamino-l-(4-morpholinophenyl)-2-benzylbutan-l-one, 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-l-[4-(4-morpholinyl)phenyl]butan-l-one, and the like can be given. Commercially available products such as Irgacure 369, 907, 379 (all manufactured by BASF), and the like can be used.

[0449] As the compound having a partial structure represented by formula (d3), for example, 2-hydroxy-2-methyl-l-phenylpropan-l-one, 2-hydroxy-2-methyl-l-[4-(2-hydroxyethoxy)phenyl]propan-l-one, 1-hydroxycyclohexyl phenyl ketone, an oligomer of 2-hydroxy-2-methyl-l-(4-isopropenylphenyl)propan-l-one, α,α-diethoxyacetophenone, benzil dimethyl ketal, and the like can be given.

[0450] From the aspect of sensitivity, as the alkylphenone compound, a compound having a partial structure represented by formula (d2) is preferable.

[0451] As the aforementioned triazine compound, for example, 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-l,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxynaphthyl)-l,3,5-triazine, 2,4-bis(trichloromethyl)-6-piperonyl-l,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxystyryl)-l,3,5-triazine, 2,4-bis(trichloromethyl)-6-〔2-(5-methylfuran-2-yl)vinyl〕-l,3,5-triazine, 2,4-bis(trichloromethyl)-6-〔2-(furan-2-yl)vinyl〕-l,3,5-triazine, 2,4-bis(trichloromethyl)-6-〔2-(4-diethylamino-2-methylphenyl)vinyl〕-l,3,5-triazine, 2,4-bis(trichloromethyl)-6-〔2-(3,4-dimethoxyphenyl)vinyl〕-l,3,5-triazine, and the like can be given.

[0452] As the aforementioned acylphosphine oxide compound, 2,4,6-trimethylbenzoyl diphenylphosphine oxide and the like can be given. Commercially available products such as Irgacure (registered trademark) 819 (manufactured by BASF) and the like can be used.

[0453] As the aforementioned biimidazole compound, for example, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3-dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole (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)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(dialkoxylphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(trialkoxylphenyl)biimidazole (for example, see Japanese Patent Application Publication No. 48-38403, Japanese Patent Application Publication No. 62-174204, and the like), a biimidazole 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 given.

[0454] Further, as the polymerization initiator (D), benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether and the like benzoin compounds; benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyl diphenyl sulfide, 3,3',4,4'-tetra(t-butylperoxycarbonyl)benzophenone, 2,4,6-trimethylbenzophenone and the like benzophenone compounds; 9,10-phenanthrenequinone, 2-ethylanthraquinone, camphorquinone and the like quinone compounds; 10-butyl-2-chloroacridone, benzil, methyl phenylglyoxylate, a titanocene compound and the like can be given. They are preferably used in combination with the polymerization initiation aid (D1) (particularly an amine compound) described later.

[0455] As the acid-generating polymerization initiator, for example, 4-hydroxyphenyldimethylsulfonium p-toluenesulfonate, 4-hydroxyphenyldimethylsulfonium hexafluoroantimonate, 4-acetyloxyphenyldimethylsulfonium p-toluenesulfonate, 4-acetyloxyphenylmethylbenzylsulfonium hexafluoroantimonate, triphenylsulfonium p-toluenesulfonate, triphenylsulfonium hexafluoroantimonate, diphenyliodonium p-toluenesulfonate, diphenyliodonium hexafluoroantimonate and the like onium salts, nitrobenzyltoluenesulfonates, benzoin toluenesulfonates and the like can be given.

[0456] As the polymerization initiator (D), a polymerization initiator containing at least one selected from the group consisting of an alkyl phenone compound, a triazine compound, an acyl phosphine oxide compound, an O-acyl oxime compound, and a bisimidazole compound is preferred, and a polymerization initiator containing an O-acyl oxime compound is more preferred. The content of the O-acyl oxime compound in 100 mass% of the polymerization initiator (D) is, for example, 30 to 100 mass%, preferably 50 mass% or more, more preferably 80 mass% or more, and further preferably 90 mass% or more.

[0457] The content of the polymerization initiator (D) is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, and further preferably 2 to 10 parts by mass, relative to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). If the content of the polymerization initiator (D) is within the aforementioned range, there is a tendency that high sensitivity is achieved and the exposure time is shortened, and thus the productivity of the color filter is improved.

[0458] <Polymerization initiation aid (D1)>

[0459] The colored curable resin composition of the present application can further contain a polymerization initiation aid (D1). The polymerization initiation aid (D1) is a compound for promoting the polymerization of the polymerizable compound initiated by the polymerization initiator, or a sensitizer.

[0460] As the polymerization initiation aid (D1), an amine compound, an alkoxyanthracene compound, a thioxanthone compound, a carboxylic acid compound, and the like can be given.

[0461] As the aforementioned amine compound, triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-diethylaminoethyl 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 can be given, of which 4,4'-bis(diethylamino)benzophenone is preferred. Commercially available products such as EAB-F (manufactured by Showa Denko K.K.) can be used.

[0462] As the aforementioned alkoxyanthracene compound, 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 can be given.

[0463] As the aforementioned thioxanthone compounds, 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, 1-chloro-4-propoxythioxanthone, and the like can be given.

[0464] As the aforementioned carboxylic acid compounds, 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 can be given.

[0465] In the case where 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 that the colored pattern can be formed with higher sensitivity and the productivity of the color filter is improved.

[0466] <Solvent (E)>

[0467] 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- within the molecule and not containing -O-), ether solvents (solvents containing -O- within the molecule and not containing -COO-), ether ester solvents (solvents containing -COO- and -O- within the molecule), ketone solvents (solvents containing -CO- within the molecule and not containing -COO-), alcohol solvents (solvents containing OH within the molecule and not containing -O-, -CO-, and -COO-), aromatic hydrocarbon solvents, amide solvents, dimethyl sulfoxide, and the like can be given.

[0468] As the ester solvents, methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutyrate, ethyl acetate, n-butyl acetate, isobutyl acetate, pentyl formate, isoamyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexanol acetate, and γ-butyrolactone, and the like can be given.

[0469] 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 given.

[0470] 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, and diethylene glycol monobutyl ether acetate, and the like can be given.

[0471] As the ketone solvent, 4-hydroxy-4-methyl-2-pentanone (diacetone alcohol), acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone, isophorone, and the like can be given.

[0472] As the alcohol solvent, methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, glycerol, and the like can be given.

[0473] As the aromatic hydrocarbon solvent, benzene, toluene, xylene, and mesitylene, and the like can be given.

[0474] As the amide solvent, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, and the like can be given.

[0475] Among the above-mentioned solvents, from the viewpoints of coatability and dryability, 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.

[0476] 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.

[0477] 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-mentioned 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.

[0478] 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-mentioned 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.

[0479] <Leveling agent (F)>

[0480] As the leveling agent (F), organic silicon-based surfactants, fluorine-based surfactants, and organic silicon-based surfactants having a fluorine atom, and the like can be given. They can have a polymerizable group in a side chain.

[0481] As the organic silicone-based surfactant, a surfactant having a siloxane bond in the molecule, etc. 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 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.), etc. can be given.

[0482] As the aforementioned fluorine-based surfactant, a surfactant having a fluorocarbon chain in the molecule, etc. 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 Industries, Ltd.), etc. can be given.

[0483] As the aforementioned organic silicone-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 Corp.), etc. can be given.

[0484] The content of the leveling agent (F) is preferably 0.001 to 0.2% by mass, more preferably 0.002 to 0.1% by mass, and further preferably 0.005 to 0.05% by mass, relative to the total amount of the colored curable resin composition. Note that this content does not include the content of the aforementioned pigment dispersant. If the content of the leveling agent (F) is within the aforementioned range, the planarity of the color filter can be made good.

[0485] <Other components>

[0486] The colored curable resin composition can include, as needed, fillers, other high-molecular compounds, adhesion promoters, antioxidants, light stabilizers, chain transfer agents, and the like, which are known in the art.

[0487] <Method for producing colored curable resin composition>

[0488] 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, as needed, the solvent (E), the leveling agent (F), the polymerization initiator aid (D1), and other components. The mixed colored curable resin composition can be filtered using a filter having a pore size of about 0.01 to 10 μm.

[0489] 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 this colorant dispersion liquid to make the target colored curable resin composition.

[0490] In the case where the colorant (A) includes a dye, the dye can be dissolved in part or all of the solvent (E) in advance to produce a solution. This solution is preferably filtered using a filter having a pore size of about 0.01 to 1 μm.

[0491] [Color filter]

[0492] As a method for 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. Of these, 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, a colored coating film, which is a cured product of the aforementioned composition layer, can be formed by not using a photomask at the time of exposure and / or not developing.

[0493] 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.

[0494] 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. A color filter layer, a resin layer, a transistor, a circuit or 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.

[0495] 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, a colored curable resin composition is applied to a substrate, and by performing heat drying (pre-baking) and / or reduced pressure drying, the volatile components such as solvent are removed and dried, thereby obtaining a smooth composition layer. As the application method, spin coating, slit coating, slit and spin coating or the like can be mentioned. In the case of performing heat drying, the temperature is preferably 30 to 120°C, more preferably 50 to 110°C. In addition, as the heat time, it is preferably 10 seconds to 60 minutes, more preferably 30 seconds to 30 minutes. In the case of performing 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 it can be appropriately selected depending on the film thickness of the color filter targeted.

[0496] 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 the light source used for exposure, a light source generating light of a wavelength of 250 to 450 nm is preferable. For example, for light of less than 250 nm, a filter cutting off the wavelength region can be used to cut off; for light around 436 nm, around 408 nm, around 365 nm, a band pass filter extracting these wavelength regions can be used to selectively extract. 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 or a proximity exposure device using a mask aligner and a stepper or the like is preferably used.

[0497] The colored pattern is formed on the substrate by developing the composition layer after exposure by bringing it into contact with a developing solution. By 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 preferred. The concentration of these alkali compounds in the aqueous solution is preferably 0.01 to 10% by mass, 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, a dipping method, a spray method, or the like. In addition, the substrate can be inclined at an arbitrary angle at the time of development.

[0498] After development, water washing is preferably performed.

[0499] The obtained colored pattern is preferably further subjected to post-baking. The post-baking temperature is preferably 80 to 250°C, more preferably 100 to 245°C. The post-baking time is preferably 1 to 120 minutes, more preferably 2 to 30 minutes.

[0500] The colored pattern and the colored coating film thus obtained are useful as a color filter, which is 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.

[0501] In particular, the aforementioned colored pattern and colored coating film are useful as a blue pixel (blue color filter) in a color filter.

[0502] 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, particularly preferably 6.0% or less or 4.0% 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.

[0503] 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 5.0% or less, further preferably 3.5% or less, and can be set to 2.0% 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.

[0504] In addition, for the aforementioned colored pattern or colored coating film, in a case where the film thickness is adjusted so that the maximum transmittance at a wavelength of 400 to 500 nm is 83%, the absolute value of the slope of the transmittance spectrum obtained by the method described in the Examples below is preferably 0.013 or greater, more preferably 0.015 or greater, and further preferably 0.017 or greater. By increasing the absolute value of the slope, a color filter having a large amount of transmitted light can be produced, and thus the sensitivity of a solid-state imaging device including the color filter is increased. Note that the upper limit of the absolute value of the slope is not particularly limited, and can be, for example, 0.05 or less.

[0505] Examples

[0506] Hereinafter, the present application will be described more specifically by citing examples, but the present application is not limited at all by the following examples, and can of course be modified as appropriate within a range that can be adapted to the gist described in the foregoing and the following, and they are all included in the technical scope of the present application. Note that in the following, "parts" means "mass parts" and "%" means "mass %" unless otherwise specified.

[0507] In the following examples, the structure of the compound was confirmed by mass spectrometry (LC: Model 1200 by Agilent, MASS: LC / MSD 6130 by Agilent).

[0508] The weight average molecular weight (Mw) and the number average molecular weight (Mn) of the resin, which are converted to polystyrene, were measured by a GPC method under the following conditions.

[0509] Apparatus: HLC-8120 GPC (manufactured by TOSOH Corporation)

[0510] Column: TSK-GEL G2000HXL

[0511] Column temperature: 40°C

[0512] Solvent: Tetrahydrofuran

[0513] Flow rate: 1.0 mL / minute

[0514] Analytical sample: Solid content concentration: 0.001 to 0.01%

[0515] Injection amount: 50 μL

[0516] Detector: RI

[0517] Calibration standard substance: TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by TOSOH Corporation)

[0518] The ratio (Mw / Mn) of the weight average molecular weight to the number average molecular weight in terms of polystyrene obtained above was used as the dispersity.

[0519] <Colorant Synthesis Example 1>

[0520] A mixture of 40.5 parts of the compound represented by formula (II-X) and 60.5 parts of 2,6-dimethylaniline (manufactured by Tokyo Chemical Industry Co., Ltd.) was stirred at 150°C for 8 hours in 200 parts of N-methylpyrrolidone under light shielding conditions. After the resulting reaction solution was cooled to room temperature, it was added to a mixture of 1200 parts of water and 75 parts of 35% hydrochloric acid, 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, washed with 100 parts of methanol, and dried under reduced pressure at 60°C for 12 hours to obtain 49 parts of the compound represented by formula (II-1). The yield was 85%.

[0521]

[0522] Identification of the compound represented by formula (II-1)

[0523] (Mass spectrum) Ionization mode = ESI+: m / z = [M+H] + 575

[0524] Exact Mass: 574

[0525] <Colorant Synthesis Example 2>

[0526] 2,6-Diphenylaniline was synthesized with reference to the method described in ARKIVOC, 2012, 9, 62-75. A mixture of 4.0 parts of the compound represented by formula (II-X), 9.69 parts of 2,6-diphenylaniline, 2.69 parts of zinc chloride (manufactured by FUJIFILM Wako Pure Chemical Corporation), and 24 parts of sulfolane (manufactured by Tokyo Chemical Industry Co., Ltd.) was stirred at 250°C for 4 hours at room temperature. After the reaction solution was cooled to room temperature, 48 parts of IN hydrochloric acid 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, and N,N-dimethylformamide 20 parts in this order. The resulting residue was dried to obtain 5.18 parts of the compound represented by formula (II-2). The yield was 64%.

[0527]

[0528] Identification of the compound represented by formula (II-2)

[0529] (Mass spectrum) Ionization mode = ESI+: m / z = [M+H] +823.3

[0530] Exact Mass: 823.3

[0531] <Resin Synthesis Example 1: Synthesis of Resin (B-1)>

[0532] A flask equipped with a reflux condenser, a dropping funnel, and a stirrer was charged with propylene glycol monomethyl ether acetate 340 parts, and the inside was replaced with nitrogen atmosphere by flowing in nitrogen. The inside was heated to 80°C while stirring. Subsequently, a mixed solution of a mixture 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 (containing 1:1 by molar ratio) 54 parts, benzyl methacrylate 239 parts, and propylene glycol monomethyl ether acetate 73 parts was added dropwise over 5 hours. On the other hand, a solution of a polymerization initiator, 2,2-azobis(2,4-dimethylpentanenitrile) 40 parts, 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, the inside 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 as measured by a B-type viscometer (23°C) and a solid content of 37.0%. The weight average molecular weight Mw of the copolymer produced was 9.4 x 10 3 , the dispersity was 1.89, and the acid value converted to the solid content was 114 mg-KOH / g. The resin (B-1) had the following structural units.

[0533]

[0534] <Resin Synthesis Example 2: Synthesis of Resin (B-2)>

[0535] To a flask equipped with a stirring device, a dropping funnel, a condenser, a thermometer, and a gas introduction tube, was added propylene glycol monomethyl ether acetate 241 parts, and while stirring with nitrogen replacement, 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 to the flask over 2 hours. After the addition was completed, stirring was further continued for 30 minutes, and a copolymerization reaction was performed. Then, 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, to obtain a polymer. Finally, propylene glycol monomethyl ether 300 parts was added to the reaction solution, and propylene glycol monomethyl ether acetate was added, to obtain a copolymer (resin (B-2)) solution having a viscosity of 26 mPa-s and a solid content of 38.5% as measured by a B-type viscometer (23°C). The weight average molecular weight Mw of the copolymer thus obtained was 6600, and the acid value as converted to the solid content was 92.5 mg-KOH / g.

[0536] <Dispersion Preparation Examples 1 to 7>

[0537] The components were mixed in the blending ratios described in Table 1, and dispersed by a bead mill, to obtain colorant dispersions (A-1) to (A-7), respectively. Note that in Table 1, resin (B-1) indicates the resin (B-1) obtained in Resin Synthesis Example 1 (as converted to the solid content), PGME indicates propylene glycol monomethyl ether, and PGMEA indicates propylene glycol monomethyl ether acetate. In addition, C.I. Acid Red 289 is a mixture of a compound represented by formula (II-3) and a compound represented by formula (II-4), and C.I. Acid Red 52 is a compound represented by formula (II-5).

[0538]

[0539] [Table 1]

[0540] Preparation Example 1 Preparation Example 2 Preparation Example 3 Preparation Example 4 Preparation Example 5 Preparation Example 6 Preparation Example 7 Colorant dispersion liquid (A-1) (A-2) (A-3) (A-4) (A-5) (A-6) (A-7) C.I. Pigment Blue 15:6 12.0 8.4 C.I. Pigment Blue 15:4 12.0 C.I. Pigment Violet 23 3.6 Compound represented by formula (II-1) 8.0 Compound represented by formula (II-2) 8.0 C.I. Acid Red 289 8.0 C.I. Acid Red 52 8.0 Acrylic pigment dispersant 2.2 3.0 3.6 2.9 2.9 2.9 2.9 Resin (B-1) 5.6 4.2 4.8 2.9 2.9 2.9 2.9 PGME 0.3 5.0 0.5 5.1 4.4 4.4 4.4 PGMEA 80 76 80 81 82 82 82

[0541] Measurement of Maximum Absorption Wavelength of Xanthene Pigment

[0542] In a volumetric flask, 0.005 g of each of the compounds shown in Table 2 was dissolved in dimethylformamide and the volume was made 0.1 L, 0.01 L of which was diluted with chloroform to make the volume 0.25 L (concentration: 0.002 g / L), and the absorption spectrum was measured in the range of wavelengths from 800 to 300 nm using a UV-visible spectrophotometer (V-650DS; Japan Spectroscopic Co., Ltd.) (quartz cell, optical path length: 1 cm), and the maximum absorption wavelength was found. The maximum absorption wavelength of each compound is shown in Table 2.

[0543] [Table 2]

[0544]

[0545] [Examples 1 to 6 and Comparative Examples]

[0546] Preparation of colored curable resin composition

[0547] Each component was mixed at the compounding ratio (on a mass basis) described in Table 3 to obtain a colored curable resin composition.

[0548] [Table 3]

[0549]

[0550] Colorant dispersion liquid (A-1): colorant dispersion liquid (A-1) obtained in Dispersion liquid preparation example 1

[0551] Colorant dispersion liquid (A-2): colorant dispersion liquid (A-2) obtained in Dispersion liquid preparation example 2

[0552] Colorant dispersion liquid (A-3): colorant dispersion liquid (A-3) obtained in Dispersion liquid preparation example 3

[0553] Colorant dispersion liquid (A-4): colorant dispersion liquid (A-4) obtained in Dispersion liquid preparation example 4

[0554] Colorant dispersion liquid (A-5): colorant dispersion liquid (A-5) obtained in Dispersion liquid preparation example 5

[0555] Colorant dispersion liquid (A-6): colorant dispersion liquid (A-6) obtained in Dispersion liquid preparation example 6

[0556] Colorant dispersion liquid (A-7): colorant dispersion liquid (A-7) obtained in Dispersion liquid preparation example 7

[0557] Resin solution (B-2): resin (B-2) solution obtained in Resin synthesis example 2

[0558] Polymerizable compound (C-1): a compound represented by the following formula (NK ester A-DP H-12E: manufactured by Shin-Nakamura Chemical Co., Ltd.)

[0559]

[0560] 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.)

[0561] Solvent (E-1): propylene glycol monomethyl ether acetate

[0562] Leveling agent (F-1): polyether-modified silicone oil (trade name TORAY SILICONE SH8400: manufactured by Toray Dow Corning Silicone Co., Ltd.)

[0563] <Formation of colored pattern (color filter)>

[0564] On the surface of a 4-inch glass substrate, a colored curable resin composition was coated 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 immersion development in an aqueous developer containing 0.3% of tetramethylammonium hydroxide at 23°C for 30 seconds, 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

[0565] <Measurement of film thickness>

[0566] 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 6 and Comparative Example was 0.6 μm.

[0567] <Transmittance evaluation>

[0568] The transmittance in a wavelength region of 380 nm to 780 nm was measured at an interval of 1 nm using a colorimeter (OSP-SP-200; manufactured by Olympus Corporation) with respect to the obtained colored pattern.

[0569] (1) Transmittance at 530 nm

[0570] ​Based on the above measurement results, the transmittance at 530 nm for each colored pattern was confirmed. The results are shown in Table 4. 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.

[0571] [Table 4]

[0572]

[0573] (2) Transmittance at 640 nm

[0574] Based on the above measurement results, the transmittance at 640 nm for each colored pattern was confirmed. The results are shown in Table 5. 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.

[0575] [Table 5]

[0576]

[0577] (3) Slope of transmittance spectrum

[0578] Based on the above measurement results, the slope of the spectrum was calculated from the wavelength at which the transmittance became 70% and the wavelength at which the transmittance became 20% on the long wavelength side compared to the maximum transmittance. The results are shown in Table 6. The larger the absolute value of the slope of the spectrum, the more a color filter that transmits a large amount of light can be produced, and the sensitivity of a solid-state imaging device including the color filter can be improved.

[0579] [Table 6]

[0580]

Claims

1. A colored curable resin composition containing a colorant, a resin, a polymerizable compound, and a polymerization initiator, the colorant includes a xanthene dye (al) having a maximum absorption wavelength of 510 nm or more and 535 nm or less, a xanthene dye (a2) having a maximum absorption wavelength of more than 535 nm and 570 nm or less, and a blue pigment (a3).

2. The colored curable resin composition according to claim 1, wherein The content ratio (al / a2) of the xanthene dye (al) to the xanthene dye (a2) is 0.1 to 15 on a mass basis.

3. The colored curable resin composition according to claim 1, wherein The total content of the xanthene dye (al) and the xanthene dye (a2) is 8 mass parts or more relative to 100 mass parts of the blue pigment (a3).

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

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

6. A display device including the color filter according to claim 5.

7. A solid-state imaging device including the color filter according to claim 5.

Images