Coloring composition
A coloring composition with a specific colorant and alkali-soluble resin enhances UV ashing resistance in color filters, addressing the resistance issues of conventional filters.
Patent Information
- Application Number
- JP2022552027
- Authority / Receiving Office
- JP · JP
- Patent Type
- Patents
- Current Assignee / Owner
- Priority Date
- 2020-09-28
- Filing Date
- 2021-09-22
- Publication Date
- 2025-12-16
- Estimated Expiration
- 2041-09-22
AI Technical Summary
Conventional color filters formed from colored resin compositions using certain compounds lack sufficient UV ashing resistance.
A coloring composition comprising a colorant containing a compound represented by formula (I) and an alkali-soluble resin, which may include a polymerizable compound and a polymerization initiator, to enhance UV ashing resistance.
The composition provides a color filter with improved UV ashing resistance and optionally heat resistance.
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Abstract
Description
[Technical Field]
[0001] The present invention relates to a coloring composition, a color filter formed from the coloring composition, and a display device including the color filter. [Background technology]
[0002] Color filters used in displays such as liquid crystal displays, electroluminescent displays, and plasma displays, and solid-state imaging devices such as CCD and CMOS sensors, are produced from colored resin compositions. A compound represented by formula (x1) is known as a colorant used in such colored resin compositions (Patent Document 1).
[0003] [ka] [Prior art documents] [Patent documents]
[0004] [Patent Document 1] Japanese Patent Application Laid-Open No. 2015-61907 Summary of the Invention [Problem to be solved by the invention]
[0005] However, conventionally known color filters formed from colored resin compositions using the above-mentioned compounds have sometimes failed to fully satisfy UV ashing resistance. Therefore, an object of the present invention is to provide a colored composition capable of forming a color filter having excellent UV ashing resistance. [Means for solving the problem]
[0006] The gist of the present invention is as follows. [1] A coloring composition comprising a colorant containing a compound represented by formula (I) and an alkali-soluble resin. [ka] [In formula (I), L 1 represents a group represented by formula (ph1), A represents a group represented by formula (ia): B represents a group represented by formula (ib). [ka] [In formula (ph1), X 1 represents a hydrocarbon group which may have a substituent or which may have a substituent, -CH2- contained in the hydrocarbon group may be replaced by -O-, -CO- or -NH-, and -CH= contained in the hydrocarbon group may be replaced by -N=. n represents an integer of 0 to 4. When n represents an integer of 2 or more, multiple X 1 may be the same or different. n represents an integer of 2 or more, and X 1 is attached to adjacent carbon atoms, X is attached to adjacent carbon atoms 1 may be bonded to each other to form a ring. * represents a bond to A, and ** represents a bond to B.] [ka] [In formula (ia) and formula (ib), X 6 ~X 9 each independently represents a hydrocarbon group which may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced with -O-, -CO- or -NH-, -CH= contained in the hydrocarbon group may be replaced with -N=, and -C< contained in the hydrocarbon group may be replaced with -N<. X 6 and X 7 may be bonded to each other to form a ring, and X 8 and X 9 may be bonded to each other to form a ring. * is L 1 represents a bond with .] [2] L 1 The coloring composition according to [1], wherein [ka] [In formula (ph2), X 2 ~X 5 X each independently represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an amino group, an amido group, a carboxyl group, an alkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, a cyano group, or a halogen atom. 2 and X 3 , X 4 and X 5 may be bonded to each other to form a ring. * represents a bond to A, and ** represents a bond to B.] [3] The colored composition according to [1] or [2], wherein the group represented by formula (ia) and the group represented by formula (ib) are each independently any of the groups represented by formulas (t1) to (t5). [ka] [In formulas (t1) to (t5), R 1 ~R 16 each independently represents a hydrogen atom, a hydrocarbon group which may have a substituent, a heterocyclic group, a cyano group, or a halogen atom. 1 represents a bond with .] [4] The colored composition according to any one of [1] to [3], further comprising a polymerizable compound and a polymerization initiator. [5] A color filter formed from the colored composition according to any one of [1] to [4]. [6] A display device comprising the color filter according to [5]. [Effects of the Invention]
[0007] According to the colored composition of the present invention, a color filter having excellent UV ashing resistance can be provided. DETAILED DESCRIPTION OF THE INVENTION
[0008] The colored composition of the present invention contains a colorant containing a compound represented by formula (I) (hereinafter, may be referred to as colorant (A)) and an alkali-soluble resin (hereinafter, may be referred to as resin (B)). The colored composition of the present invention preferably further contains a polymerizable compound (hereinafter, may be referred to as a polymerizable compound (C)) and a polymerization initiator (hereinafter, may be referred to as a polymerization initiator (D)). The colored composition of the present invention preferably further contains a solvent (hereinafter, may be referred to as solvent (E)). The colored composition of the present invention may further contain a leveling agent (hereinafter, may be referred to as leveling agent (F)). In this specification, the compounds exemplified as each component can be used alone or in combination, unless otherwise specified.
[0009] <Colorant (A)> The colorant (A) contains a compound represented by formula (I) (hereinafter, may be referred to as compound (I)). When the colorant (A) contains compound (I), the UV ashing resistance of the obtained color filter is improved, and preferably the UV ashing resistance and heat resistance are improved.
[0010] [ka] [In formula (I), L 1 represents a group represented by formula (ph1), A represents a group represented by formula (ia): B represents a group represented by formula (ib). [ka] [In formula (ph1), X 1represents a hydrocarbon group which may have a substituent or which may have a substituent, -CH2- contained in the hydrocarbon group may be replaced by -O-, -CO- or -NH-, and -CH= contained in the hydrocarbon group may be replaced by -N=. n represents an integer of 0 to 4. When n represents an integer of 2 or more, multiple X 1 may be the same or different. n represents an integer of 2 or more, and X 1 is attached to adjacent carbon atoms, X is attached to adjacent carbon atoms 1 may be bonded to each other to form a ring. * represents a bond to A, and ** represents a bond to B.] [ka] [In formula (ia) and formula (ib), X 6 ~X 9 each independently represents a hydrocarbon group which may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced with -O-, -CO- or -NH-, -CH= contained in the hydrocarbon group may be replaced with -N=, and -C< contained in the hydrocarbon group may be replaced with -N<. X 6 and X 7 may be bonded to each other to form a ring, and X 8 and X 9 may be bonded to each other to form a ring. * is L 1 represents a bond with .]
[0011] Compound (I) will be described in detail below, but compound (I) also includes the resonance structure of formula (I), tautomers of formula (I), and compounds obtained by rotating each group in formula (I) around the bond axis of the single bond. Examples of tautomers of formula (I) include a compound in which A in formula (I) is a group represented by formula (iia); a compound in which B in formula (I) is a group represented by formula (iib); and a compound in which A in formula (I) is a group represented by formula (iia) and B in formula (I) is a group represented by formula (iib).
[0012] [ka] [In formula (iia) and formula (iib), X 6 ~X 9 and * are as above.]
[0013] X in formula (ph1) 1 Examples of the substituent represented by the formula (hereinafter sometimes referred to as substituent A) include an amino group, an amide group, a carboxyl group, an alkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, a cyano group, and a halogen atom.
[0014] X 1 The hydrocarbon group represented by the formula (I) may be an aliphatic hydrocarbon group or an aromatic hydrocarbon group, and the aliphatic hydrocarbon group may be saturated or unsaturated, and may be linear or cyclic (alicyclic hydrocarbon group). The alicyclic hydrocarbon group may be monocyclic or polycyclic.
[0015] Examples of saturated chain hydrocarbon groups (hereinafter sometimes referred to as alkyl groups) include linear alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, and decyl groups; and branched alkyl groups such as isopropyl, isobutyl, sec-butyl, tert-butyl, 1,3-dimethylbutyl, 2-ethylbutyl, and 2-ethylhexyl groups.
[0016] Examples of the unsaturated chain hydrocarbon group include alkenyl groups such as ethenyl, propenyl (e.g., 1-propenyl, 2-propenyl), and butenyl (e.g., 1-butenyl, 3-butenyl) groups; and alkynyl groups such as ethynyl, propynyl (e.g., 1-propynyl, 2-propynyl), and butynyl (e.g., 1-butynyl, 3-butynyl) groups.
[0017] The saturated or unsaturated chain hydrocarbon group preferably has 1 to 10 carbon atoms, more preferably 1 to 6 carbon atoms, and even more preferably 1 to 4 carbon atoms.
[0018] Examples of saturated alicyclic hydrocarbon groups include cycloalkyl groups such as cyclopropyl, 1-methylcyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and 2-methylcyclohexyl groups.
[0019] Examples of the unsaturated alicyclic hydrocarbon group include cycloalkenyl groups such as a cyclohexenyl group (for example, a cyclohex-1-en-1-yl group, a cyclohex-2-en-1-yl group, and a cyclohex-3-en-1-yl group), a cycloheptenyl group, and a cyclooctenyl group.
[0020] Examples of the alicyclic hydrocarbon group include polycyclic saturated alicyclic hydrocarbon groups such as norbornyl, adamantyl, and bicyclo[2.2.2]octyl; and polycyclic unsaturated alicyclic hydrocarbon groups such as norbornenyl.
[0021] The alicyclic hydrocarbon group preferably has 3 to 12 carbon atoms, more preferably 3 to 10 carbon atoms, and even more preferably 3 to 8 carbon atoms.
[0022] Examples of aromatic hydrocarbon groups include a phenyl group, an o-tolyl group, an m-tolyl group, a p-tolyl group, a 2,4-dimethylphenyl group, a 2,6-dimethylphenyl group, a 2,4,6-trimethylphenyl group, a 2,4-diisopropylphenyl group, a 2,6-diisopropylphenyl group, a 4-vinylphenyl group, an o-tert-butylphenyl group, an m-tert-butylphenyl group, a p-tert-butylphenyl group, a 3,5-di(tert-butyl)phenyl group, a 1-naphthyl group, a 2-naphthyl group, and a group in which one hydrogen atom has been removed from tetralin.
[0023] The aromatic hydrocarbon group preferably has 6 to 18 carbon atoms, more preferably 6 to 12 carbon atoms, and even more preferably 6 to 10 carbon atoms.
[0024] X 1The hydrocarbon group represented by the formula (I) may be a group obtained by combining the hydrocarbon groups listed above, and examples thereof include an aralkyl group, an alkyl group to which an alicyclic hydrocarbon group is bonded; an aromatic hydrocarbon group to which a cycloalkyl group is condensed; and an alkyl group to which an aromatic hydrocarbon group to which a cycloalkyl group is condensed is bonded.
[0025] Examples of the aralkyl group include a benzyl group, a (4-methylphenyl)methyl group, and a phenethyl group. The aralkyl group preferably has 7 to 18 carbon atoms, more preferably 7 to 12 carbon atoms, and even more preferably 7 to 10 carbon atoms.
[0026] Examples of the alkyl group having an alicyclic hydrocarbon group bonded thereto include a cyclopropylmethyl group, a cyclopropylethyl group, a cyclobutylmethyl group, a cyclohexylmethyl group, a cyclohexylethyl group, an adamantylmethyl group, etc. The number of carbon atoms in the alkyl group having an alicyclic hydrocarbon group bonded thereto is preferably 4 to 20, more preferably 4 to 15, and even more preferably 4 to 10.
[0027] Examples of aromatic hydrocarbon groups condensed with a cycloalkyl group include a group in which one hydrogen atom has been removed from the benzene ring of indane, a group in which one hydrogen atom has been removed from the benzene ring of 1-methyl-indane, and a group in which one hydrogen atom has been removed from 2-methyl-indane.
[0028] Examples of the alkyl group having an aromatic hydrocarbon group condensed with a cycloalkyl group bonded thereto include an indane group in which an alkyl group having 1 to 4 carbon atoms is bonded to the benzene ring, a 1-methyl-indane group in which an alkyl group having 1 to 4 carbon atoms is bonded to the benzene ring, and a 2-methyl-indane group in which an alkyl group having 1 to 4 carbon atoms is bonded to the benzene ring.
[0029] X 1Examples of the substituent that the hydrocarbon group represented by the formula (hereinafter, sometimes referred to as "substituent B") may have include an amino group, an amide group, a carboxyl group, an alkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, a cyano group, a halogen atom, and a hydroxy group.
[0030] The amino group as the substituent A and the substituent B may be an unsubstituted amino group or a substituted amino group. The substituted amino group is preferably an amino group having one or two hydrocarbon groups. The hydrocarbon group may be any of the above-mentioned X 1 Examples of the substituted amino group include the same groups as the hydrocarbon group represented by the following formula: and an alkyl group is preferred. The number of carbon atoms in the hydrocarbon group is preferably 1 to 10, more preferably 1 to 4. Examples of the substituted amino group include an N-methylamino group, an N,N-dimethylamino group, an N-ethylamino group, an N,N-diethylamino group, an N-propylamino group, an N,N-dipropylamino group, an N-isopropylamino group, an N,N-diisopropylamino group, an N-phenylamino group, an N,N-diphenylamino group, and an N,N-ethylmethylamino group.
[0031] The amide group as the substituent A and the substituent B means a group in which one hydrogen atom bonded to a nitrogen atom has been removed from an amide, and examples thereof include a formamide group, an acetamide group, a propylamide group, a butylamide group, a benzamide group, a trifluoroacetamide group, a pentafluorobenzamide group, etc. The number of carbon atoms in the amide group is preferably 2 to 20, more preferably 2 to 10, and even more preferably 2 to 6.
[0032] Examples of the alkoxy group as the substituent A and the substituent B include a methoxy group, an ethoxy group, a propoxy group, an n-butoxy group, a tert-butoxy group, etc. The alkoxy group preferably has 1 to 4 carbon atoms, and more preferably 1 or 2 carbon atoms.
[0033] Examples of the alkylthio group as the substituent A and the substituent B include a methylthio group, an ethylthio group, a propylthio group, and an n-butylthio group. The alkylthio group preferably has 1 to 4 carbon atoms, and more preferably 1 or 2 carbon atoms.
[0034] Examples of the halogen atom as the substituent A and the substituent B include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Among these, a fluorine atom, a chlorine atom, or a bromine atom is preferred, and a chlorine atom is more preferred.
[0035] X 1 is preferably an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a cyano group, or a halogen atom, and more preferably an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a cyano group, or a halogen atom.
[0036] n is preferably an integer of 0 to 2.
[0037] In formula (ph1), when n is an integer of 2 or more, a plurality of X 1 may be the same or different.
[0038] n is an integer of 2 or more, and a plurality of X 1 is bonded to adjacent carbon atoms of the phenylene group in formula (ph1), X bonded to the adjacent carbon atoms 1 may be bonded to each other to form a ring. X bonded to adjacent carbon atoms 1 Examples of the ring formed by bonding together include the following: In the formula, * indicates a bond to the adjacent carbon atom on the phenylene group in formula (ph1).
[0039] [ka]
[0040] The positions of the two bonds in formula (ph1) are not particularly limited, but from the viewpoint of easy availability of raw materials, it is preferable that the bonds are at the 1- and 4-positions.
[0041] L in compound (I) 1 is preferably a group represented by formula (ph2).
[0042] [ka] [In formula (ph2), X 2 ~X 5 X each independently represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an amino group, an amido group, a carboxyl group, an alkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, a cyano group, or a halogen atom. 2 and X 3 , X 4 and X 5 may be bonded to each other to form a ring. * represents a bond to A, and ** represents a bond to B.]
[0043] X 2 ~X 5 Examples of the alkyl group having 1 to 4 carbon atoms represented by the formula (I) include a methyl group, an ethyl group, a propyl group, an n-butyl group, an isobutyl group, a tert-butyl group, etc. Among these, a methyl group or an ethyl group is preferred.
[0044] X 2 ~X 5 Examples of the amino group represented by the formula (I) include the groups explained as the amino group in the substituents A and B, and the preferred ranges thereof are also the same.
[0045] X 2 ~X 5 Examples of the amide group represented by the formula (I) include the groups described as the amide group in the substituents A and B, and the preferred ranges thereof are also the same.
[0046] X 2 ~X 5Examples of the alkoxy group represented by the formula (I) include the groups explained as the alkoxy group in the substituent A and the substituent B, and the preferred ranges thereof are also the same.
[0047] X 2 ~X 5 Examples of the alkylthio group represented by the formula: include the groups described as the alkylthio group in the substituents A and B, and the preferred ranges thereof are also the same.
[0048] X 2 ~X 5 Examples of the halogen atom represented by the formula (I) include those described as the halogen atoms in the substituents A and B, and the preferred ranges thereof are also the same.
[0049] X 2 and X 3 , X 4 and X 5 The ring formed by bonding together includes the above-mentioned X 1 are bonded to each other to form a ring.
[0050] Among the groups represented by formula (ph2), any of the groups represented by formulas (ph2-1) to (ph2-12) is preferred, and any of the groups represented by formulas (ph2-1) to (ph2-11) is more preferred. In the formulas, * represents a bond to A, and ** represents a bond to B.
[0051] [ka]
[0052] X in formula (ia) and formula (ib) 6 ~X 9 The hydrocarbon group represented by the formula 1 Examples of the hydrocarbon group represented by X include the groups described above. 6 ~X 9 -CH2- contained in the hydrocarbon group represented by the formula (I) may be replaced by -O-, -CO- or -NH-, and X 6 ~X9 -CH= contained in the hydrocarbon group represented by the formula (I) may be replaced by -N=, and X 6 ~X 9 The -C< contained in the hydrocarbon group represented by the formula may be replaced with -N<.
[0053] Also, X 6 and X 7 may be bonded to each other to form a ring, and X 8 and X 9 may be bonded to each other to form a ring. 6 and X 7 and X 8 and X 9 a form in which -CH2- in the ring formed by bonding together is replaced with -O-, -CO- or -NH-; X 6 and X 7 and X 8 and X 9 a ring formed by bonding together, in which -CH= is replaced with -N=; X 6 and X 7 and X 8 and X 9 The present invention also includes an embodiment in which -C< in the ring formed by bonding together is replaced with -N<.
[0054] In formula (ia), X 6 and X 7 are bonded to each other to form a ring, and X 8 and X 9 Examples of groups in which L are bonded to each other to form a ring include the following: 1 At least one hydrogen atom of the group represented by the following formula may be replaced with a substituent C described below.
[0055] [ka]
[0056] [ka]
[0057] X 6 ~X 9 Examples of the substituent that the hydrocarbon group represented by the formula (hereinafter, sometimes referred to as "substituent C") may have include a hydroxy group, an alkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, a carboxyl group, an amino group, an amido group, a cyano group, a halogen atom, -SO3H, -SO3M, and -SO3T. 0.5 , -SO2N(R 17 M represents an alkali metal atom, T represents an alkaline earth metal atom, and R 17 represents a hydrogen atom or a hydrocarbon group.
[0058] Examples of the alkoxy group as the substituent C include those described as the alkoxy group in the substituents A and B, and the preferred ranges thereof are also the same.
[0059] Examples of the alkylthio group as the substituent C include those described as the alkylthio group in the substituents A and B, and the preferred ranges thereof are also the same.
[0060] Examples of the amino group as the substituent C include those described as the amino group in the substituents A and B, and the preferred ranges thereof are also the same.
[0061] Examples of the amide group as the substituent C include those described as the amide group in the substituents A and B, and the preferred ranges thereof are also the same.
[0062] Examples of the halogen atom as the substituent C include those described as the halogen atoms in the substituents A and B, and a chlorine atom, a bromine atom or a fluorine atom is preferred.
[0063] Examples of the alkali metal atom represented by M include sodium and potassium.
[0064] Examples of alkaline earth metal atoms represented by T include magnesium, calcium, and barium. 6 ~X 9 Either -SO3T 0.5 When the hydrocarbon group has one aryl group, compound (I) has the following structure:
[0065] [ka]
[0066] [In the formula, L 1 , A, B, and T have the same meanings as above. - is the X in A and B 6 ~X 9 In the formula (I), one of the hydrogen atoms of the hydrocarbon group represented by the formula (I) is substituted.
[0067] R 17 represents a hydrogen atom or a hydrocarbon group. 17 may be the same or different, and it is preferable that one is a hydrogen atom and the other is a hydrocarbon group. 17 The hydrocarbon group represented by the formula 1 and preferably an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a polycyclic saturated alicyclic hydrocarbon group having 3 to 12 carbon atoms, or an aromatic hydrocarbon group having 6 to 18 carbon atoms.
[0068] It is preferable that the group represented by formula (ia) and the group represented by formula (ib) are the same. 6 and X 8 represent the same group, and X 7 and X 9 It is preferable that the groups represented by formula (ia) and (ib) represent the same group. When the group represented by formula (ia) and the group represented by formula (ib) are the same, the color density when made into a color filter becomes better.
[0069] The group represented by formula (ia) and the group represented by formula (ib) are each independently more preferably any of the groups represented by formulas (t1) to (t5), further preferably any of the groups represented by formulas (t1) to (t4), and particularly preferably any of the groups represented by formulas (t1) to (t3). [ka] [In formulas (t1) to (t5), R 1 ~R 16 each independently represents a hydrogen atom, a hydrocarbon group which may have a substituent, a heterocyclic group, a cyano group, or a halogen atom. 1 represents a bond with .]
[0070] R 1 ~R 16 The hydrocarbon group represented by the formula 1 Among these, alkyl groups having 1 to 10 carbon atoms, cycloalkyl groups having 3 to 10 carbon atoms, and aromatic hydrocarbon groups having 6 to 12 carbon atoms are preferred, and alkyl groups having 1 to 6 carbon atoms, cycloalkyl groups having 3 to 8 carbon atoms, and phenyl groups are more preferred.
[0071] R 1 ~R 16 Examples of the substituent that the hydrocarbon group represented by the following formula may have include the groups explained above as the substituent C, and the preferred ranges thereof are also the same.
[0072] R 1 ~R 16Examples of the heterocyclic group represented by the formula (I) include a thienyl group, a benzo[b]thienyl group, a thianthrenyl group, a furyl group, a pyranyl group, an isobenzofuranyl group, a chromenyl group, a xanthenyl group, a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an indolizinyl group, an indolyl group, a 1H-indazolyl group, an isoquinolyl group, a quinolyl group, a phthalazinyl group, a carbazolyl group, an acridinyl group, a chromanyl group, a pyrrolidinyl group, a piperidyl group, a piperazinyl group, an indolinyl group, an isoindolinyl group, and a benzimidazolonyl group. Among these, heterocyclic groups having a benzene ring, such as a benzo[b]thienyl group, a thianthrenyl group, an isobenzofuranyl group, a chromenyl group, a xanthenyl group, an indolyl group, a 1H-indazolyl group, an isoquinolyl group, a quinolyl group, a phthalazinyl group, a carbazolyl group, an acridinyl group, a chromanyl group, an indolinyl group, an isoindolinyl group, or a benzimidazolonyl group, are preferred, and an indolyl group, a 1H-indazolyl group, an isoquinolyl group, a quinolyl group, a phthalazinyl group, a carbazolyl group, an acridinyl group, an indolinyl group, an isoindolinyl group, or a benzimidazolonyl group is more preferred.
[0073] R 1 ~R 16 Examples of the halogen atom represented by the formula (I) include those described as the halogen atoms in the substituents A and B, and among these, a chlorine atom and a fluorine atom are preferred.
[0074] R 1 is preferably an aromatic hydrocarbon group which may have a substituent, more preferably a phenyl group which may have a substituent, even more preferably a phenyl group which may have a substituent at the para position, and even more preferably a halogen atom, -SO3H, -SO3T 0.5 , -SO3M, or -SO2N(R 17 )2 at the para position, particularly preferably a halogen atom, —SO3H, or —SO2N(R 17 )2 is a phenyl group which may have at the para position.
[0075] R2 is preferably an alkyl group which may have a substituent, more preferably an alkyl group which may have a halogen atom, and even more preferably an alkyl group having 1 to 4 carbon atoms which may have a halogen atom.
[0076] R 3 and R 4 are each independently preferably a hydrogen atom, an alkyl group, a cycloalkyl group, or an aromatic hydrocarbon group, and more preferably a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, or a phenyl group. 3 and R 4 are preferably the same.
[0077] R 5 is preferably an alkyl group which may have a substituent or a hydrogen atom, more preferably an alkyl group, and even more preferably an alkyl group having 1 to 4 carbon atoms.
[0078] R 6 is preferably an alkyl group or a cyano group which may have a substituent, more preferably an alkyl group or a cyano group which may have a halogen atom, and even more preferably an alkyl group or a cyano group having 1 to 4 carbon atoms which may have a halogen atom.
[0079] R 7 is preferably an alkyl group which may have a substituent, more preferably an alkyl group which may have a halogen atom, and even more preferably an alkyl group having 1 to 4 carbon atoms which may have a halogen atom.
[0080] R 8 is preferably an alkyl group which may have a substituent, and more preferably an alkyl group having 1 to 4 carbon atoms.
[0081] R 9 is preferably an alkyl group which may have a substituent or a hydrogen atom, more preferably an alkyl group having 1 to 4 carbon atoms or a hydrogen atom.
[0082] R 10 is preferably an aromatic hydrocarbon group or a heterocyclic group which may have a substituent, more preferably a phenyl group or a heterocyclic group having a benzene ring which may have a substituent, and even more preferably a phenyl group or a benzimidazolonyl group which may have a halogen atom.
[0083] R 11 ~R 16 are each independently preferably an alkyl group which may have a substituent or a hydrogen atom, more preferably an alkyl group which may have a halogen atom or a hydrogen atom, and even more preferably an alkyl group having 1 to 4 carbon atoms which may have a halogen atom or a hydrogen atom.
[0084] Examples of compound (I) include compounds (AI-1) to (AI-748) shown in Tables 1 to 7.
[0085] [Table 1]
[0086] [Table 2]
[0087] [Table 3]
[0088] [Table 4]
[0089] [Table 5]
[0090] [Table 6]
[0091] [Table 7]
[0092] In Tables 1 to 7, ph3 to ph10 represent groups represented by formula (ph3) to formula (ph10), in which * represents a bond to A, and ** represents a bond to B.
[0093] [ka]
[0094] In Tables 1 to 7, t6 to t16 represent groups represented by formulas (t6) to (t16). 18 represents a 2-methylcyclohexyl group, a phenyl group, a 3,5-di-tert-butylphenyl group, an adamantyl group, or a 1,3-dimethylbutyl group, and * represents L 1 This shows the bond between .
[0095] [ka]
[0096] Further, examples of compound (I) include the following compounds (AI-749) to (AI-753).
[0097] [ka]
[0098] Compound (I) is preferably Compound (AI-1) to Compound (AI-682) and Compound (AI-749) to Compound (AI-753), More preferably, in the compounds (AI-1) to (AI-682), A and B are any of the groups represented by formula (t6) to formula (t15); More preferred are compounds (AI-1) to (AI-10), compounds (AI-67) to (AI-76), compounds (AI-188) to (AI-197), compounds (AI-309) to (AI-318), compounds (AI-430) to (AI-439), compounds (AI-551) to (AI-560), and compounds (AI-617) to (AI-626).
[0099] Compound (I) can be produced, for example, by the following method.
[0100] When compound (I) is a compound represented by formula (I') (hereinafter, sometimes referred to as compound (I')), first, an amine represented by formula (pt1) is diazotized to produce a diazonium salt represented by formula (q1). The resulting diazonium salt represented by formula (q1) is reacted with a compound represented by formula (pt2) to produce a compound represented by formula (q2). Subsequently, the compound represented by formula (q2) is reduced to produce an amine represented by formula (q3). Furthermore, the resulting amine is diazotized to produce a diazonium salt represented by formula (q4), and then the compound represented by formula (pt3) is reacted to produce a compound represented by formula (I').
[0101] [ka] [In formulas (pt1) to (pt3), formulas (q1) to (q4), and formula (I'), X 1 and n have the same meaning as above. X 6p ~X 9peach independently represents a hydrocarbon group which may have as a substituent a hydroxy group, an alkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, a carboxyl group, an amino group, an amido group, a cyano group, a halogen atom, or -SO3H, and -CH2- in the hydrocarbon group may be replaced with -O-, -CO-, or -NH-, -CH= in the hydrocarbon group may be replaced with -N=, and -C< in the hydrocarbon group may be replaced with -N<. X 6p and X 7p may be bonded to each other to form a ring, and X 8p and X 9p may be bonded to each other to form a ring. Q 1 and Q 2 each independently represents an inorganic anion or an organic anion.
[0102] The diazonium salt of formula (q1) can be obtained, for example, by diazotizing an amine of formula (pt1) with nitrous acid, a nitrite, or a nitrite ester. Such diazotization can be carried out by any known method.
[0103] Examples of the inorganic anion include a fluoride ion, a chloride ion, a bromide ion, an iodide ion, a perchlorate ion, and a hypochlorite ion. Examples of the organic anion include a CH3COO - , C6H5COO - Q 1 and Q 2 The cations are preferably chloride ions, bromide ions, CH3COO - is.
[0104] In carrying out the diazotization reaction, an acidic catalyst may be used to ensure smooth progress of the reaction. Examples of the acidic catalyst include mineral acids such as sulfuric acid and hydrochloric acid.
[0105] A compound represented by formula (q2) can be produced by diazo coupling a diazonium salt represented by formula (q1) with a compound represented by formula (pt2). Such diazo coupling can be carried out by any known method. This reaction is preferably carried out in the presence of an aqueous solvent. Examples of the aqueous solvent include water-soluble organic solvents such as methanol, ethanol, propanol, and 2-propanol, water, or a mixed solvent of water and the above-mentioned water-soluble organic solvents. A mixed solvent of water and a water-soluble organic solvent is preferred.
[0106] A compound represented by formula (q3) can be produced by reducing a compound represented by formula (q2). The reduction method is not particularly limited and can be carried out by any known method. For example, reduction using a reducing agent such as a sulfide can be used. The sulfide is not particularly limited and examples include hydrosulfides such as sodium hydrosulfide, potassium hydrosulfide, and ammonium hydrosulfide, as well as sulfides such as sodium sulfide, potassium sulfide, and ammonium sulfide. These may be anhydrous or contain water of crystallization. The reduction reaction is preferably carried out in the presence of an aqueous solvent. Examples of the aqueous solvent include the same solvents as those described above, with water being preferred.
[0107] The diazonium salt of formula (q4) can be obtained by diazotizing the amine of formula (q3). The diazotization method can be the same as that for the diazotization of the compound of formula (pt1) described above.
[0108] Compound (I') can be produced by diazo coupling a diazonium salt represented by formula (q4) with a compound represented by formula (pt3). As the diazo coupling method, the same method as the diazo coupling between the diazonium salt represented by formula (q1) and the compound represented by formula (pt2) described above can be used.
[0109] In addition, X in compound (I) 6 ~X 9At least one of -SO3M or -SO3T 0.5 In the case of producing a compound (hereinafter sometimes referred to as compound (I'')) in which X is a hydrocarbon group having X as a substituent, 6p ~X 9p After preparing compound (I'), at least one of which is a hydrocarbon group having a sulfonic acid group as a substituent, the resulting compound (I') having a sulfonic acid group as a substituent is reacted with an alkali metal salt or an alkaline earth metal salt. By this reaction, the sulfonic acid group in compound (I') is converted to -SO3M or -SO3T. 0.5 to produce compound (I″).
[0110] Examples of the alkali metal compound or alkaline earth metal compound include salts with chloride ions, salts with iodide ions, salts with bromide ions, salts with acetate ions, salts with formate ions, and salts with benzoate ions, with the salts with acetate ions being preferred.
[0111] This reaction is preferably carried out in the presence of a mixed solvent of an organic solvent and an aqueous solvent. Examples of the aqueous solvent include the same solvents as those mentioned above, with water being preferred. Examples of the organic solvent include ester solvents such as ethyl lactate, butyl lactate, n-butyl acetate, ethyl butyrate, and methyl acetoacetate; ether solvents such as ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, and propylene glycol monomethyl ether; ketone solvents such as diacetone alcohol; amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone; and halogenated solvents such as chloroform and methylene chloride, with amide solvents being preferred.
[0112] In addition, X in compound (I) 6 ~X 9 At least one of -SO2N(R 17 In order to produce a compound (hereinafter sometimes referred to as compound (I''')) in which X is a hydrocarbon group having X as a substituent, first, 6p ~X 9pAfter preparing a compound (I') in which at least one of the groups is a hydrocarbon group having a sulfonic acid group as a substituent, the compound (I') having a sulfonic acid group is reacted with a halogenating agent. A base and NH(R 17 )2 is added and reacted. By the above reaction, the sulfonic acid group of compound (I') is converted to -SO2N(R 17 )2 to produce compound (I''').
[0113] Examples of the halogenating agent include thionyl chloride, oxalyl chloride, phosphorus trichloride, and phosphorus pentachloride.
[0114] The reaction is preferably carried out in the presence of an organic solvent, such as the same organic solvents as those mentioned above, preferably amide solvents and halogenated solvents.
[0115] Examples of the base include organic bases such as triethylamine, 4-(N,N-dimethylamino)pyridine, pyridine, and piperidine, metal alkoxides such as sodium methoxide, sodium ethoxide, sodium tert-butoxide, and potassium tert-butoxide, organometallic compounds such as butyllithium, tert-butyllithium, and phenyllithium, and inorganic bases such as lithium hydroxide, sodium hydroxide, and potassium hydroxide. Of these, organic bases are preferred.
[0116] The method for obtaining the target compound, Compound (I) (e.g., Compounds (I') to (I''')), from the reaction mixture is not particularly limited, and various known methods can be used. For example, an acid (e.g., acetic acid, etc.) can be added to the reaction mixture as needed, and the precipitated crystals can be collected by filtration. Alternatively, after completion of the reaction, the solvent in the reaction mixture can be distilled off, a small amount of methanol can be added and stirred, and an acid (e.g., acetic acid, etc.) and water can be added to the resulting solution, and the precipitated crystals can be collected by filtration. The filtered crystals are preferably washed with water, methanol, or the like, and then dried. If necessary, they can be further purified by known methods such as recrystallization.
[0117] The content of compound (I) in the total amount of colorant (A) is preferably 5% by mass or more, more preferably 10% by mass or more, and even more preferably 20% by mass or more, and may be 100% by mass, 98% by mass or less, or 93% by mass or less.
[0118] In addition to the compound (I), the colorant (A) may contain a colorant different from the compound (I). The colorant different from the compound (I) may be either a dye (hereinafter sometimes referred to as a dye (A1)) or a pigment (hereinafter sometimes referred to as a pigment (A2)). The colorant different from the compound (I) may contain one or both of the dye (A1) and the pigment (A2).
[0119] The dye (A1) is not particularly limited as long as it does not contain compound (I), and known dyes can be used, such as solvent dyes, acid dyes, direct dyes, and mordant dyes. Examples of dyes include compounds classified as non-pigment dyes with hues in the Color Index (published by The Society of Dyers and Colourists) and known dyes listed in Dyeing Notes (Shikisensha). In terms of chemical structure, examples include azo dyes other than compound (I), cyanine dyes, triphenylmethane dyes, xanthene dyes, phthalocyanine dyes, anthraquinone dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, azomethine dyes, squarylium dyes, acridine dyes, styryl dyes, coumarin dyes, quinoline dyes, and nitro dyes. Among these, organic solvent-soluble dyes are preferred.
[0120] Specifically, CI Solvent Yellow 4 (hereinafter, the notation CI Solvent Yellow will be omitted and only the numbers will be listed), 14, 15, 23, 24, 38, 62, 63, 68, 82, 94, 98, 99, 117, 162, 163, 167, 189; CI Solvent Red 45, 49, 111, 125, 130, 143, 145, 146, 150, 151, 155, 168, 169, 172, 175, 181, 207, 218, 222, 227, 230, 245, 247; CI Solvent Orange 2, 7, 11, 15, 26, 56, 77, 86; CI Solvent Violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60; CI Solvent Blue 4, 5, 14, 18, 35, 36, 37, 45, 58, 59, 59:1, 63, 67, 68, 69, 70, 78, 79, 83, 90, 94, 97, 98, 100, 101, 102, 104, 105, 111, 112, 122, 128, 132, 136, 139; CI solvent dyes such as CI Solvent Green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, and 35; CI Acid Yellow 1, 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112, 113, 114, 116, 119, 123, 128, 134, 135, 138, 139, 140, 144, 150, 155, 157, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251; CI Acid Red 1, 4, 8, 14, 17, 18, 26, 27, 29, 31, 33, 34, 35, 37, 40, 42, 44, 50, 51, 52, 57, 66, 73, 76, 80, 87, 88, 91, 92, 94, 95, 97, 98, 103, 106, 111, 114, 129, 133, 134, 138, 143, 145, 150, 151, 155, 158, 160, 172, 176, 177, 178, 180, 181, 182, 183, 184, 185, 186, 187, 188, 189, 190, 191, 192, 193, 194, 195, 196, 197, 198, 199, 200, 201, 202, 203, 204, 205, 206, 207, 208, 209, 210, 211, 212, 213, 214, 215, 216, 217, 218, 219, 220, 221, 222, 223, 224, 225, 226, 227, 228, 229, 230, 231, 232, 233, 234, 235, 23 82, 183, 195, 198, 206, 211, 215, 216, 217, 227, 228, 249, 252, 257, 258, 260, 261, 266, 268, 270, 274, 277, 280, 281, 289, 308, 312, 315, 316, 339, 341, 345, 346, 349, 382, 383, 388, 394, 401, 412, 417, 418, 422, 426; CI Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 169, 173; CI Acid Violet 6B, 7, 9, 15, 16, 17, 19, 21, 23, 24, 25, 30, 34, 38, 49, 72, 102; CI Acid Blue 1, 3, 5, 7, 9, 11, 13, 15, 17, 18, 22, 23, 24, 25, 26, 27, 29, 34, 38, 40, 41, 42, 43, 45, 48, 51, 54, 59, 60, 62, 70, 72, 74, 75, 78, 80, 82, 83, 86, 87, 88, 90, 90:1, 91, 92, 93, 93:1, 96, 99, 100, 102, 103, 104, 108, 109, 110, 112, 113, 117, 119, 120, 121, 122, 123, 124, 125, 126, 127, 128, 129, 130, 131, 132, 133, 134, 135, 136, 137, 138, 139, 140, 141, 142, 143, 144, 145, 146, 147, 148, 149, 150, 151, 152, 153, 154, 155, 156, 157, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 168, 169, 170, 1 23, 126, 127, 129, 130, 131, 138, 140, 142, 143, 147, 150, 151, 154, 158, 161, 166, 167, 168, 170, 171, 175, 182, 183, 184, 187, 192, 199, 203, 204, 205, 210, 213, 229, 234, 236, 242, 243, 256, 259, 267, 269, 278, 280, 285, 290, 296, 315, 324, 335, 340; CI Acid Dyes such as CI Acid Green 1, 3, 5, 6, 7, 8, 9, 11, 13, 14, 15, 16, 22, 25, 27, 28, 41, 50, 50:1, 58, 63, 65, 80, 104, 105, 106, 109, CI Direct Yellow 2, 33, 34, 35, 38, 39, 43, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129, 136, 138, 141; CI Direct Red 79, 82, 83, 84, 91, 92, 96, 97, 98, 99, 105, 106, 107, 172, 173, 176, 177, 179, 181, 182, 184, 204, 207, 211, 213, 218, 220, 221, 222, 232, 233, 234, 241, 243, 246, 250; CI Direct Orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107; CI Direct Violet 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104; CI Direct Blue 1, 2, 3, 6, 8, 15, 22, 25, 28, 29, 40, 41, 42, 47, 52, 55, 57, 71, 76, 77, 78, 80, 81, 84, 85, 86, 90, 93, 94, 95, 97, 98, 99, 100, 101, 106, 107, 108, 109, 113, 114, 115, 117, 119, 120, 137, 149, 150, 153, 155, 156, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 168, 170, 171, 172, 173, 188, 189, 190, 192, 193, 194, 195, 196, 198, 199, 200, 201, 202, 203, 207, 209, 210, 212, 213, 214, 222, 225, 226, 228, 229, 236, 237, 238, 242, 243, 244, 245, 246, 247, 248, 249, 250, 251, 252, 256, 257, 259, 260, 268, 274, 275, 293; CI Direct dyes such as CI Direct Green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 77, 79, and 82; CI Disperse Yellow 51, 54, 76; CI Disperse Violet 26, 27; CI Disperse dyes such as CI Disperse Blue 1, 14, 56, and 60, CI Basic Red 1, 10; CI Basic Blue 1, 3, 5, 7, 9, 19, 21, 22, 24, 25, 26, 28, 29, 40, 41, 45, 47, 54, 58, 59, 60, 64, 65, 66, 67, 68, 81, 83, 88, 89; CI Basic Violet 2; CI Basic Red 9; CI Basic dyes, such as CI Basic Green 1; CI Reactive Yellow 2,76,116; CI Reactive Orange 16; CI Reactive dyes, such as CI Reactive Red 36; CI Mordant Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65; CI Mordant Red 1, 2, 3, 4, 9, 11, 12, 14, 17, 18, 19, 22, 23, 24, 25, 26, 27, 29, 30, 32, 33, 36, 37, 38, 39, 41, 42, 43, 45, 46, 48, 52, 53, 56, 62, 63, 71, 74, 76, 78, 85, 86, 88, 90, 94, 95; CI Mordant Orange 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47, 48; CI Mordant Violet 1, 1:1, 2, 3, 4, 5, 6, 7, 8, 10, 11, 14, 15, 16, 17, 18, 19, 21, 22, 23, 24, 27, 28, 30, 31, 32, 33, 36, 37, 39, 40, 41, 44, 45, 47, 48, 49, 53, 58; CI Mordant Blue 1, 2, 3, 7, 8, 9, 12, 13, 15, 16, 19, 20, 21, 22, 23, 24, 26, 30, 31, 32, 39, 40, 41, 43, 44, 48, 49, 53, 61, 74, 77, 83, 84; CI Mordant dyes such as CI Mordant Green 1, 3, 4, 5, 10, 13, 15, 19, 21, 23, 26, 29, 31, 33, 34, 35, 41, 43, and 53; Examples include CI Vat dyes such as CI Vat Green 1.
[0121] Further examples include a compound represented by formula (z) and a compound represented by formula (z1).
[0122] [ka]
[0123] [ka]
[0124] These dyes may be appropriately selected in accordance with the desired spectral spectrum of the color filter.
[0125] When the colorant (A) contains the dye (A1), the content thereof is preferably 1% by mass or more, more preferably 3% by mass or more, and even more preferably 5% by mass or more, of the total amount of the colorant (A), and is preferably 20% by mass or less, more preferably 15% by mass or less.
[0126] The pigment (A2) is not particularly limited and any known pigment can be used, and examples thereof include pigments classified as pigments in the Color Index (published by The Society of Dyers and Colourists). Examples of pigments include yellow pigments such as CI Pigment Yellow 1, 3, 10, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 81, 83, 86, 93, 94, 109, 110, 117, 125, 128, 129, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 185, 194, 214, and 231; Orange pigments such as CI Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 62, 64, 65, 71, 72, 73; Red pigments such as CI Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 179, 180, 190, 192, 202, 209, 215, 216, 224, 242, 254, 255, 264, 265, 266, 268, 269, 273, 291, 295, 296; Blue pigments such as CI Pigment Blue 15, 15:3, 15:4, 15:6, 60; Violet pigments such as CI Pigment Violet 1, 19, 23, 29, 32, 36, 38; Green pigments such as CI Pigment Green 7, 36, 58, 59, 62, 63; Brown pigments such as CI Pigment Brown 23 and 25; Examples include black pigments such as CI Pigment Black 1 and 7.
[0127] The pigment may be subjected, as necessary, to a rosin treatment, a surface treatment using a pigment derivative into which an acidic group or a basic group has been introduced, a graft treatment onto the pigment surface using a polymer compound or the like, a microparticle treatment using a sulfuric acid microparticle method or the like, a washing treatment using an organic solvent or water to remove impurities, a treatment to remove ionic impurities using an ion exchange method or the like, or the like. The pigment preferably has a uniform particle size. By adding a pigment dispersant and carrying out a dispersion treatment, it is possible to obtain a pigment dispersion liquid in which the pigment is uniformly dispersed in the solution.
[0128] Examples of the pigment dispersant include cationic, anionic, nonionic, amphoteric, polyester, polyamine, and acrylic surfactants. These pigment dispersants may be used alone or in combination of two or more. Examples of the pigment dispersant include trade names such as KP (manufactured by Shin-Etsu Chemical Co., Ltd.), FLOWRENE (manufactured by Kyoeisha Chemical Co., Ltd.), Solsperse (manufactured by Zeneca Corporation), EFKA (manufactured by CIBA), AJISPER (manufactured by Ajinomoto Fine-Techno Co., Ltd.), and Disperbyk (manufactured by BYK-Chemie). When a pigment dispersant is used, the amount thereof is preferably from 1 to 100% by mass, more preferably from 5 to 50% by mass, based on the total amount of the pigment (A2). When the amount of the pigment dispersant used is within the above range, a pigment dispersion in a uniformly dispersed state tends to be obtained.
[0129] The content of colorant (A) is preferably 0.1% by mass or more and 70% by mass or less, more preferably 0.5% by mass or more and 60% by mass or less, and even more preferably 1% by mass or more and 50% by mass or less, based on the total amount of solids. When the content of colorant (A) is within the above range, the color density when made into a color filter is sufficient, and since the necessary amounts of resin (B) and polymerizable compound (C) can be contained in the composition, a pattern with sufficient mechanical strength can be formed.
[0130] Here, the "total amount of solids" in this specification refers to the amount obtained by excluding the content of the solvent from the total amount of the colored composition. The total amount of solids and the content of each component relative to the total amount of solids can be measured by known analytical means such as liquid chromatography or gas chromatography.
[0131] <Resin (B)> Resin (B) is an alkali-soluble resin. Examples of resin (B) include the following resins [K1] to [K6]. Resin [K1]: a copolymer having structural units derived from at least one member (a) (hereinafter sometimes referred to as "(a)") selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic acid anhydrides, and structural units derived from a monomer (b) (hereinafter sometimes referred to as "(b)") having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond; Resin [K2]: a copolymer having structural units derived from (a), structural units derived from (b), and structural units derived from a monomer (c) copolymerizable with (a) (however, different from (a) and (b)) (hereinafter, sometimes referred to as "(c)"); Resin [K3]: a copolymer having structural units derived from (a) and structural units derived from (c); Resin [K4]: a copolymer having a structural unit derived from (a) to which (b) has been added, and a structural unit derived from (c); Resin [K5]: a copolymer having a structural unit derived from (b) to which (a) has been added and a structural unit derived from (c); Resin [K6]: A copolymer having a structural unit derived from (c) and a structural unit obtained by adding (a) to a structural unit derived from (b) and further adding a carboxylic acid anhydride.
[0132] Specific examples of (a) include unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, o-, m-, and p-vinylbenzoic acid; Unsaturated dicarboxylic acids such as maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyltetrahydrophthalic acid, and 1,4-cyclohexenedicarboxylic acid; bicyclounsaturated compounds containing a carboxy group, such as methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo[2.2.1]hept-2-ene, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene, 5-carboxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-carboxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-carboxy-6-methylbicyclo[2.2.1]hept-2-ene, and 5-carboxy-6-ethylbicyclo[2.2.1]hept-2-ene; Unsaturated dicarboxylic acid anhydrides such as maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, and 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride; Unsaturated mono[(meth)acryloyloxyalkyl] esters of divalent or higher polyvalent carboxylic acids, such as mono[2-(meth)acryloyloxyethyl] succinate and mono[2-(meth)acryloyloxyethyl] phthalate; Examples include unsaturated acrylates containing a hydroxy group and a carboxy group in the same molecule, such as α-(hydroxymethyl)acrylic acid. Among these, acrylic acid, methacrylic acid, maleic anhydride, etc. are preferred from the viewpoint of copolymerization reactivity and solubility of the resulting resin in an alkaline aqueous solution.
[0133] In this specification, "(meth)acrylic acid" refers to at least one selected from the group consisting of acrylic acid and methacrylic acid. The terms "(meth)acryloyl" and "(meth)acrylate" also have the same meaning.
[0134] (b) refers to, for example, a polymerizable compound having a cyclic ether structure having 2 to 4 carbon atoms (for example, at least one selected from the group consisting of an oxirane ring, an oxetane ring, and a tetrahydrofuran ring) and an ethylenically unsaturated bond. (b) is preferably a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth)acryloyloxy group.
[0135] Examples of (b) include a monomer (b1) having an oxiranyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b1)"), a monomer (b2) having an oxetanyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b2)"), and a monomer (b3) having a tetrahydrofuryl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b3)").
[0136] Examples of (b1) include a monomer (b1-1) (hereinafter sometimes referred to as "(b1-1)") having a structure in which a linear or branched aliphatic unsaturated hydrocarbon has been epoxidized, and a monomer (b1-2) (hereinafter sometimes referred to as "(b1-2)") having a structure in which an alicyclic unsaturated hydrocarbon has been epoxidized.
[0137] Examples of (b1-1) include glycidyl (meth)acrylate, β-methylglycidyl (meth)acrylate, β-ethylglycidyl (meth)acrylate, glycidyl vinyl ether, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether, α-methyl-o-vinylbenzyl glycidyl ether, α-methyl-m-vinylbenzyl glycidyl ether, α-methyl-p-vinylbenzyl glycidyl ether, 2,3-bis(glycidyl Examples of such styrene include 2,4-bis(glycidyloxymethyl)styrene, 2,5-bis(glycidyloxymethyl)styrene, 2,6-bis(glycidyloxymethyl)styrene, 2,3,4-tris(glycidyloxymethyl)styrene, 2,3,5-tris(glycidyloxymethyl)styrene, 2,3,6-tris(glycidyloxymethyl)styrene, 3,4,5-tris(glycidyloxymethyl)styrene, and 2,4,6-tris(glycidyloxymethyl)styrene.
[0138] Examples of (b1-2) include vinylcyclohexene monoxide, 1,2-epoxy-4-vinylcyclohexane (e.g., Celloxide 2000; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., Cyclomer A400; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., Cyclomer M100; manufactured by Daicel Corporation), compounds represented by formula (R1), and compounds represented by formula (R2).
[0139] [ka]
[0140] [In formula (R1) and formula (R2), R ra and R rb represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the hydrogen atom contained in the alkyl group may be substituted with a hydroxy group. X ra and X rb is a single bond, *-Rrc -, *-R rc -O-, *-R rc -S- or *-R rc represents -NH-. R rc represents an alkanediyl group having 1 to 6 carbon atoms. * represents a bond to O.]
[0141] Examples of the alkyl group having 1 to 4 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, and a tert-butyl group. Examples of alkyl groups in which a hydrogen atom is substituted with a hydroxy group include a hydroxymethyl group, a 1-hydroxyethyl group, a 2-hydroxyethyl group, a 1-hydroxypropyl group, a 2-hydroxypropyl group, a 3-hydroxypropyl group, a 1-hydroxy-1-methylethyl group, a 2-hydroxy-1-methylethyl group, a 1-hydroxybutyl group, a 2-hydroxybutyl group, a 3-hydroxybutyl group, and a 4-hydroxybutyl group. R ra and R rb Preferred examples of the alkyl group include a hydrogen atom, a methyl group, a hydroxymethyl group, a 1-hydroxyethyl group, and a 2-hydroxyethyl group, and more preferred examples include a hydrogen atom and a methyl group.
[0142] Examples of the alkanediyl group include a methylene group, an ethylene group, a propane-1,2-diyl group, a propane-1,3-diyl group, a butane-1,4-diyl group, a pentane-1,5-diyl group, and a hexane-1,6-diyl group. X ra and X rb Preferred examples of the group include a single bond, a methylene group, an ethylene group, *-CH2-O-, and *-CH2CH2-O-, and more preferred examples include a single bond and *-CH2CH2-O- (* represents a bond to O).
[0143] Examples of compounds represented by formula (R1) include compounds represented by any of formulas (R1-1) to (R1-15). Among these, compounds represented by formula (R1-1), (R1-3), (R1-5), (R1-7), (R1-9), or (R1-11) to (R1-15) are preferred, and compounds represented by formula (R1-1), (R1-7), (R1-9), or (R1-15) are more preferred.
[0144] [ka]
[0145] [ka]
[0146] Compounds represented by formula (R2) include compounds represented by any of formulas (R2-1) to (R2-15). Among these, compounds represented by formula (R2-1), (R2-3), (R2-5), (R2-7), (R2-9), or (R2-11) to (R2-15) are preferred, and compounds represented by formula (R2-1), (R2-7), (R2-9), or (R2-15) are more preferred.
[0147] [ka]
[0148] [ka]
[0149] The compound represented by formula (R1) and the compound represented by formula (R2) may be used alone or in combination of two or more. When the compound represented by formula (R1) and the compound represented by formula (R2) are used in combination, the content ratio thereof [compound represented by formula (R1) : compound represented by formula (R2)] is preferably 5:95 to 95:5, more preferably 20:80 to 80:20 on a molar basis.
[0150] As (b2), a monomer having an oxetanyl group and a (meth)acryloyloxy group is more preferred. Examples of (b2) include 3-methyl-3-methacryloyloxymethyloxetane, 3-methyl-3-acryloyloxymethyloxetane, 3-ethyl-3-methacryloyloxymethyloxetane, 3-ethyl-3-acryloyloxymethyloxetane, 3-methyl-3-methacryloyloxyethyloxetane, 3-methyl-3-acryloyloxyethyloxetane, 3-ethyl-3-methacryloyloxyethyloxetane, 3-ethyl-3-acryloyloxyethyloxetane, and the like.
[0151] As (b3), a monomer having a tetrahydrofuryl group and a (meth)acryloyloxy group is more preferred. Specific examples of (b3) include tetrahydrofurfuryl acrylate (for example, Viscoat V#150, manufactured by Osaka Organic Chemical Industry Co., Ltd.) and tetrahydrofurfuryl methacrylate.
[0152] As (b), (b1) is preferable in that it can further increase the reliability of the obtained color filter in terms of heat resistance, chemical resistance, etc. Furthermore, (b1-2) is more preferable in that it provides excellent storage stability of the colored composition.
[0153] Examples of (c) include methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, sec-butyl (meth)acrylate, tert-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, dodecyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, cyclopentyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, tricyclo[5.2.1.0] 2,6]decan-8-yl(meth)acrylate (commonly known in the art as "dicyclopentanyl(meth)acrylate" and sometimes called "tricyclodecyl(meth)acrylate"), tricyclo[5.2.1.0 2,6 (meth)acrylic acid esters such as ]decen-8-yl (meth)acrylate (commonly known as "dicyclopentenyl (meth)acrylate" in the technical field), dicyclopentanyloxyethyl (meth)acrylate, isobornyl (meth)acrylate, adamantyl (meth)acrylate, allyl (meth)acrylate, propargyl (meth)acrylate, phenyl (meth)acrylate, naphthyl (meth)acrylate, and benzyl (meth)acrylate; hydroxy group-containing (meth)acrylic acid esters such as 2-hydroxyethyl (meth)acrylate and 2-hydroxypropyl (meth)acrylate; dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate, and diethyl itaconate; Bicyclo[2.2.1]hept-2-ene, 5-methylbicyclo[2.2.1]hept-2-ene, 5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxybicyclo[2.2.1]hept-2-ene, 5-hydroxymethylbicyclo[2.2.1]hept-2-ene, 5-(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5-methoxybicyclo[2.2.1]hept-2-ene Bicyclo[2.2.1]hept-2-ene, 5-ethoxybicyclo[2.2.1]hept-2-ene, 5,6-dihydroxybicyclo[2.2.1]hept-2-ene, 5,6-di(hydroxymethyl)bicyclo[2.2.1]hept-2-ene, 5,6-di(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5,6-dimethoxybicyclo[2.2.1]hept -2-ene, 5,6-diethoxybicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxymethyl-5-methylbicyclo[2.2.1]hept-2-ene, 5-tert-butoxycarbonylbicyclo[2.2.1]hept-2-ene bicyclounsaturated compounds such as ene, 5-cyclohexyloxycarbonylbicyclo[2.2.1]hept-2-ene, 5-phenoxycarbonylbicyclo[2.2.1]hept-2-ene, 5,6-bis(tert-butoxycarbonyl)bicyclo[2.2.1]hept-2-ene, and 5,6-bis(cyclohexyloxycarbonyl)bicyclo[2.2.1]hept-2-ene; dicarbonyl imide derivatives such as N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimidobenzoate, N-succinimidyl-4-maleimidobutyrate, N-succinimidyl-6-maleimidocaproate, N-succinimidyl-3-maleimidopropionate, and N-(9-acridinyl)maleimide; Examples include styrene, α-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, p-methoxystyrene, acrylonitrile, methacrylonitrile, vinyl chloride, vinylidene chloride, acrylamide, methacrylamide, vinyl acetate, 1,3-butadiene, isoprene, and 2,3-dimethyl-1,3-butadiene. Among these, styrene, vinyltoluene, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo[2.2.1]hept-2-ene, 2-hydroxyethyl (meth)acrylate, and the like are preferred from the viewpoint of copolymerization reactivity and heat resistance.
[0154] In the resin [K1], the ratio of the structural units derived from each of these is as follows: Structural units derived from (a): 2 to 60 mol% Structural units derived from (b): 40 to 98 mol% Preferably, Structural units derived from (a): 10 to 50 mol% Structural units derived from (b): 50 to 90 mol% It is more preferable that: When the ratio of the structural units of the resin [K1] is within the above range, the colored composition tends to have excellent storage stability, developability when forming a colored pattern, and solvent resistance of the resulting color filter.
[0155] Resin [K1] can be produced, for example, by the method described in the literature "Experimental Methods of Polymer Synthesis" (written by Takayuki Otsu, published by Kagaku Dojin Co., Ltd., 1st edition, 1st printing, published March 1, 1972) and by reference to the references described in said literature.
[0156] Specifically, a method can be exemplified in which predetermined amounts of (a) and (b), a polymerization initiator, a solvent, etc. are placed in a reaction vessel, and the atmosphere is deoxygenated, for example by replacing oxygen with nitrogen, followed by heating and keeping the temperature while stirring. The polymerization initiator, solvent, etc. used here are not particularly limited, and those commonly used in the relevant field can be used. For example, polymerization initiators include azo compounds (2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), etc.) and organic peroxides (benzoyl peroxide, etc.). Solvents that dissolve each monomer can be used, and examples of the solvent (E) for the colored composition of the present invention include the solvents described below.
[0157] The obtained copolymer may be used as a solution after the reaction as it is, or may be used as a concentrated or diluted solution, or may be used as a solid (powder) extracted by a method such as reprecipitation. In particular, by using the solvent contained in the colored composition of the present invention as a solvent during this polymerization, the solution after the reaction can be used as it is for preparing the colored composition of the present invention, and therefore the production process of the colored composition of the present invention can be simplified.
[0158] In the resin [K2], the ratio of the structural units derived from each of these is as follows: Structural units derived from (a): 2 to 45 mol% Structural units derived from (b): 2 to 95 mol% Structural units derived from (c): 1 to 75 mol% Preferably, Structural units derived from (a): 5 to 40 mol% Structural units derived from (b): 5 to 80 mol% Structural units derived from (c): 5 to 70 mol% It is more preferable that: When the ratio of the structural units of the resin [K2] is within the above range, the colored composition tends to have excellent storage stability, the developability when forming a colored pattern, and the solvent resistance, heat resistance, and mechanical strength of the obtained color filter tend to be excellent.
[0159] Resin [K2] can be produced, for example, in the same manner as described above for producing resin [K1].
[0160] In the resin [K3], the ratio of the structural units derived from each of these is as follows: Structural units derived from (a): 2 to 60 mol% Structural units derived from (c): 40 to 98 mol% Preferably, Structural units derived from (a): 10 to 50 mol% Structural units derived from (c): 50 to 90 mol% It is more preferable that: Resin [K3] can be produced, for example, in the same manner as described above for producing resin [K1].
[0161] Resin [K4] can be produced by obtaining a copolymer of (a) and (c), and then adding the cyclic ether having 2 to 4 carbon atoms contained in (b) to the carboxylic acid and / or carboxylic acid anhydride contained in (a). First, a copolymer of (a) and (c) is produced in the same manner as described for the production of resin [K1]. In this case, the ratio of the structural units derived from each is preferably the same as that described for resin [K3].
[0162] Next, a part of the carboxylic acid and / or carboxylic acid anhydride derived from (a) in the copolymer is reacted with a cyclic ether having 2 to 4 carbon atoms contained in (b). Following the production of the copolymer of (a) and (c), the atmosphere in the flask is replaced with air from nitrogen, and (b), a reaction catalyst for the reaction of a carboxylic acid or a carboxylic acid anhydride with a cyclic ether (e.g., tris(dimethylaminomethyl)phenol, etc.), a polymerization inhibitor (e.g., hydroquinone, etc.), etc. are placed in the flask, and the mixture is reacted, for example, at 60 to 130°C for 1 to 10 hours to produce the resin [K4]. The amount of (b) used is preferably 5 to 80 mol, more preferably 10 to 75 mol, per 100 mol of (a). By using this range, the storage stability of the colored composition, the developability when forming a pattern, and the balance of the solvent resistance, heat resistance, mechanical strength, and sensitivity of the resulting pattern tend to be good. Because the reactivity of cyclic ethers is high and unreacted (b) is unlikely to remain, (b1) is preferred as (b) used in resin [K4], and (b1-1) is more preferred. The amount of the reaction catalyst used is preferably 0.001 to 5 parts by mass per 100 parts by mass of the total of (a), (b), and (c).The amount of the polymerization inhibitor used is preferably 0.001 to 5 parts by mass per 100 parts by mass of the total of (a), (b), and (c). The reaction conditions such as the charging method, reaction temperature and time can be appropriately adjusted in consideration of the production equipment, the amount of heat generated by the polymerization, etc. As with the polymerization conditions, the charging method and reaction temperature can be appropriately adjusted in consideration of the production equipment, the amount of heat generated by the polymerization, etc.
[0163] Resin [K5] is obtained in the first step by the same method as in the production of resin [K1] described above, to obtain a copolymer of (b) and (c). As in the above, the obtained copolymer may be used as a solution after the reaction as is, a concentrated or diluted solution, or a solid (powder) obtained by a method such as reprecipitation. The ratios of the structural units derived from (b) and (c) to the total number of moles of all structural units constituting the copolymer are as follows: Structural units derived from (b): 5 to 95 mol% Structural units derived from (c): 5 to 95 mol% Preferably, Structural units derived from (b): 10 to 90 mol% Structural units derived from (c): 10 to 90 mol% It is more preferable that:
[0164] Furthermore, under the same conditions as in the production method of resin [K4], resin [K5] can be obtained by reacting the cyclic ether derived from (b) contained in the copolymer of (b) and (c) with the carboxylic acid or carboxylic anhydride contained in (a). The amount of (a) used to react with the copolymer is preferably 5 to 80 moles per 100 moles of (b). Because the reactivity of cyclic ethers is high and unreacted (b) is unlikely to remain, (b1) is preferred as (b) used in resin [K5], and (b1-1) is more preferred.
[0165] Resin [K6] is a resin obtained by further reacting resin [K5] with a carboxylic acid anhydride. The hydroxyl group generated by the reaction of a cyclic ether with a carboxylic acid or a carboxylic acid anhydride is reacted with the carboxylic acid anhydride. Examples of the carboxylic acid anhydride include maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride, etc. The amount of the carboxylic acid anhydride used is preferably 0.5 to 1 mole per mole of the amount of (a) used.
[0166] Specific examples of the resin (B) include 3,4-epoxycyclohexylmethyl (meth)acrylate / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2.6 ] Decyl acrylate / (meth)acrylic acid copolymer and other resins [K1]; glycidyl (meth)acrylate / benzyl (meth)acrylate / (meth)acrylic acid copolymer, glycidyl (meth)acrylate / styrene / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] Decyl acrylate / (meth)acrylic acid / N-cyclohexylmaleimide copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6]decyl acrylate / (meth)acrylic acid / N-cyclohexylmaleimide / 2-hydroxyethyl (meth)acrylate copolymer, 3-methyl-3-(meth)acryloyloxymethyloxetane / (meth)acrylic acid / styrene copolymer, etc. [K2]; benzyl (meth)acrylate / (meth)acrylic acid copolymer, styrene / (meth)acrylic acid copolymer, etc. [K3]; resins obtained by adding glycidyl (meth)acrylate to benzyl (meth)acrylate / (meth)acrylic acid copolymer, resins obtained by adding glycidyl (meth)acrylate to tricyclodecyl (meth)acrylate / styrene / (meth)acrylic acid copolymer, tricyclodecyl Resins such as resins obtained by adding glycidyl (meth)acrylate to a (meth)acrylate / benzyl (meth)acrylate / (meth)acrylic acid copolymer [K4]; resins obtained by reacting a tricyclodecyl (meth)acrylate / glycidyl (meth)acrylate copolymer with (meth)acrylic acid, resins such as resins obtained by reacting a tricyclodecyl (meth)acrylate / styrene / glycidyl (meth)acrylate copolymer with (meth)acrylic acid [K5]; and resins such as resins obtained by reacting a tricyclodecyl (meth)acrylate / glycidyl (meth)acrylate copolymer with (meth)acrylic acid and further reacting tetrahydrophthalic anhydride with the resin [K6]. Among these, the resin (B) is preferably at least one selected from the group consisting of the resin [K1] and the resin [K2], and the resin [K2] is particularly preferred.
[0167] The polystyrene-equivalent weight average molecular weight of resin (B) is preferably from 3,000 to 100,000, more preferably from 5,000 to 50,000, and even more preferably from 5,000 to 30,000. When the molecular weight is within the above range, the hardness of the color filter is improved, the residual film rate is high, the solubility of the unexposed areas in the developer is good, and the resolution of the colored pattern tends to be improved.
[0168] The polydispersity of the resin (B) [weight average molecular weight (Mw) / number average molecular weight (Mn)] is preferably 1.1 or more and 6 or less, and more preferably 1.2 or more and 4 or less.
[0169] The acid value of resin (B) is preferably 50 mg-KOH / g or more and 170 mg-KOH / g or less, more preferably 60 mg-KOH / g or more and 150 mg-KOH / g or less, and even more preferably 70 mg-KOH / g or more and 135 mg-KOH / g or less, calculated on a solids basis. The acid value is measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of resin (B), and can be determined, for example, by titration with an aqueous potassium hydroxide solution.
[0170] The content of resin (B) is preferably 7% by mass or more and 85% by mass or less, more preferably 13% by mass or more and 80% by mass or less, and even more preferably 15% by mass or more and 70% by mass or less, based on the total amount of solids. When the content of resin (B) is within the above range, a colored pattern can be formed, and the resolution and residual film rate of the colored pattern tend to be improved.
[0171] <Polymerizable compound (C)> The polymerizable compound (C) is a compound that can be polymerized by active radicals and / or acids generated from the polymerization initiator (D), and examples thereof include compounds having a polymerizable ethylenically unsaturated bond, and are preferably (meth)acrylic acid ester compounds.
[0172] Among them, the polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds. Examples of such polymerizable compounds include trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, tripentaerythritol octa(meth)acrylate, tripentaerythritol hepta(meth)acrylate, tetrapentaerythritol deca(meth)acrylate, tetrapentaerythritol nona(meth)acrylate, tri(meth)acrylate, tetra ... Examples of the acrylate copolymer include 2-(2-(meth)acryloyloxyethyl)isocyanurate, ethylene glycol-modified pentaerythritol tetra(meth)acrylate, ethylene glycol-modified dipentaerythritol hexa(meth)acrylate, propylene glycol-modified pentaerythritol tetra(meth)acrylate, propylene glycol-modified dipentaerythritol hexa(meth)acrylate, caprolactone-modified pentaerythritol tetra(meth)acrylate, and caprolactone-modified dipentaerythritol hexa(meth)acrylate. Among these, at least one selected from the group consisting of dipentaerythritol penta(meth)acrylate and dipentaerythritol hexa(meth)acrylate is preferred.
[0173] The weight average molecular weight of the polymerizable compound (C) is preferably 150 or more and 2,900 or less, more preferably 250 or more and 1,500 or less.
[0174] The content of the polymerizable compound (C) is preferably 5% by mass or more and 75% by mass or less, more preferably 7% by mass or more and 70% by mass or less, and even more preferably 15% by mass or more and 70% by mass or less, based on the total amount of solids. When the content of the polymerizable compound (C) is within the above range, the residual film rate during color pattern formation and the chemical resistance of the color filter tend to be improved.
[0175] <Polymerization initiator (D)> The polymerization initiator (D) is not particularly limited as long as it is a compound that can generate active radicals, acids, etc. by the action of light or heat and initiate polymerization, and known polymerization initiators can be used. Examples of polymerization initiators that generate active radicals include alkylphenone compounds, triazine compounds, acylphosphine oxide compounds, O-acyloxime compounds, and biimidazole compounds.
[0176] The O-acyloxime compound is a compound having a partial structure represented by formula (d1): Hereinafter, * represents a bond.
[0177] [ka]
[0178] Examples of the O-acyloxime compound include N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethan-1-imine, N-acetoxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethylphenyl)-2-methylbenzoyl]ethan-1-imine, N-acetoxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethylphenyl) ... Examples of suitable hydroxybenzoates include N-acetyl-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethan-1-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropan-1-imine, N-benzoyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropan-1-one-2-imine, and N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine. Commercially available hydroxybenzoates include Irgacure OXE01 and OXE02 (manufactured by BASF), N-1919 (manufactured by ADEKA), and PBG-327 (manufactured by Changzhou New Power Electronic Materials Co., Ltd.). Among these, the O-acyloxime compound is preferably at least one selected from the group consisting of N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine, N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine, and N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine, and more preferably N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine and N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine.These O-acyloxime compounds tend to provide color filters with high brightness.
[0179] The alkylphenone compound is preferably a compound having a partial structure represented by formula (d2) or (d3), wherein the benzene ring in these partial structures may have a substituent.
[0180] [ka]
[0181] Examples of compounds having a partial structure represented by formula (d2) include 2-methyl-2-morpholino-1-(4-methylsulfanylphenyl)propan-1-one, 2-dimethylamino-1-(4-morpholinophenyl)-2-benzylbutan-1-one, 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]butan-1-one, etc. Commercially available products such as Irgacure 369, 907, and 379 (all manufactured by BASF) may also be used. Examples of compounds having a partial structure represented by formula (d3) include 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy)phenyl]propan-1-one, 1-hydroxycyclohexyl phenyl ketone, oligomers of 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propan-1-one, α,α-diethoxyacetophenone, and benzyl dimethyl ketal. In terms of sensitivity, the alkylphenone compound is preferably a compound having a partial structure represented by formula (d2).
[0182] Examples of the triazine compound include 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxynaphthyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxystyryl)-1,3,5-triazine, and 2,4-bis(trichloromethyl)-6-[ 2-(5-methylfuran-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)ethenyl]-1,3,5-triazine, and the like.
[0183] Examples of the acylphosphine oxide compound include 2,4,6-trimethylbenzoyldiphenylphosphine oxide, etc. Commercially available products such as Irgacure (registered trademark) 819 (manufactured by BASF) may also be used.
[0184] Examples of the biimidazole compound include 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3-dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole (see, for example, JP-A-6-75372 and JP-A-6-75373), 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(alkoxyphenyl)biimidazole, ... 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(dialkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(trialkoxyphenyl)biimidazole (see, for example, JP-B-48-38403 and JP-A-62-174204), and imidazole compounds in which the phenyl groups at the 4,4',5,5'-positions are substituted with carboalkoxy groups (see, for example, JP-A-7-10913).
[0185] Further examples of the polymerization initiator (D) include benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether; benzophenone compounds such as benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, 3,3',4,4'-tetra(tert-butylperoxycarbonyl)benzophenone, and 2,4,6-trimethylbenzophenone; quinone compounds such as 9,10-phenanthrenequinone, 2-ethylanthraquinone, and camphorquinone; 10-butyl-2-chloroacridone, benzyl, methyl phenylglyoxylate, and titanocene compounds. These are preferably used in combination with the polymerization initiator aid (D1) (especially amines) described below.
[0186] Examples of the acid generator include onium salts such as 4-hydroxyphenyldimethylsulfonium p-toluenesulfonate, 4-hydroxyphenyldimethylsulfonium hexafluoroantimonate, 4-acetoxyphenyldimethylsulfonium p-toluenesulfonate, 4-acetoxyphenylmethylbenzylsulfonium hexafluoroantimonate, triphenylsulfonium p-toluenesulfonate, triphenylsulfonium hexafluoroantimonate, diphenyliodonium p-toluenesulfonate, and diphenyliodonium hexafluoroantimonate; nitrobenzyl tosylates; and benzoin tosylates.
[0187] The polymerization initiator (D) is preferably a polymerization initiator containing at least one selected from the group consisting of an alkylphenone compound, a triazine compound, an acylphosphine oxide compound, an O-acyloxime compound, and a biimidazole compound, and more preferably a polymerization initiator containing an O-acyloxime compound.
[0188] The content of the polymerization initiator (D) is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, relative to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). When the content of the polymerization initiator (D) is within the above range, sensitivity tends to be increased and exposure time tends to be shortened, thereby improving productivity of the color filter.
[0189] <Polymerization initiator aid (D1)> The polymerization initiation aid (D1) is a compound or sensitizer used to promote the polymerization of a polymerizable compound whose polymerization has been initiated by a polymerization initiator. When the polymerization initiation aid (D1) is contained, it is usually used in combination with the polymerization initiator (D). Examples of the polymerization initiation aid (D1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds, and carboxylic acid compounds.
[0190] Examples of the amine compound include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 2-ethylhexyl 4-dimethylaminobenzoate, N,N-dimethyl-p-toluidine, 4,4'-bis(dimethylamino)benzophenone (commonly known as Michler's ketone), 4,4'-bis(diethylamino)benzophenone, and 4,4'-bis(ethylmethylamino)benzophenone, among which 4,4'-bis(diethylamino)benzophenone is preferred. Commercially available products such as EAB-F (manufactured by Hodogaya Chemical Co., Ltd.) may also be used.
[0191] Examples of the alkoxyanthracene compound include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene, 9,10-dibutoxyanthracene, and 2-ethyl-9,10-dibutoxyanthracene.
[0192] Examples of the thioxanthone compound include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, and 1-chloro-4-propoxythioxanthone.
[0193] Examples of the carboxylic acid compound include phenylsulfanylacetic acid, methylphenylsulfanylacetic acid, ethylphenylsulfanylacetic acid, methylethylphenylsulfanylacetic acid, dimethylphenylsulfanylacetic acid, methoxyphenylsulfanylacetic acid, dimethoxyphenylsulfanylacetic acid, chlorophenylsulfanylacetic acid, dichlorophenylsulfanylacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, and naphthoxyacetic acid.
[0194] When these polymerization initiation aids (D1) are used, the content thereof is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, relative to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). When the amount of the polymerization initiation aid (D1) is within this range, a colored pattern can be formed with even higher sensitivity, and the productivity of the color filter tends to improve.
[0195] <Solvent (E)> The solvent (E) is not particularly limited, and a solvent commonly used in the art can be used. Examples thereof include ester solvents (solvents containing -COO- but not -O- in the molecule), ether solvents (solvents containing -O- but not -COO- in the molecule), ether ester solvents (solvents containing -COO- and -O- in the molecule), ketone solvents (solvents containing -CO- but not -COO- in the molecule), alcohol solvents (solvents containing OH in the molecule but not -O-, -CO-, or -COO-), aromatic hydrocarbon solvents, amide solvents, and dimethyl sulfoxide.
[0196] Examples of the ester solvent include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutanoate, ethyl acetate, n-butyl acetate, isobutyl acetate, pentyl formate, isopentyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexanol acetate, and γ-butyrolactone.
[0197] Examples of the ether solvent include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenetole, and methylanisole.
[0198] Ether ester solvents include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, methyl 2-ethoxy ... Examples of the alkyl ether acetate include ethyl 2-methoxy-2-methylpropionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, and diethylene glycol monobutyl ether acetate.
[0199] Examples of ketone solvents include 4-hydroxy-4-methyl-2-pentanone (diacetone alcohol), acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone, and isophorone.
[0200] Examples of alcohol solvents include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerin.
[0201] Aromatic hydrocarbon solvents include benzene, toluene, xylene, and mesitylene.
[0202] Examples of the amide solvent include N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.
[0203] Among the above solvents, from the viewpoint of coatability and drying property, organic solvents having a boiling point at 1 atm of 120° C. or more and 180° C. or less are preferred. As the solvent, a solvent containing 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 a solvent containing at least one selected from the group consisting of propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate, ethyl 3-ethoxypropionate, and 4-hydroxy-4-methyl-2-pentanone is more preferred.
[0204] The content of the solvent (E) is preferably 55% by mass or more and 95% by mass or less, more preferably 60% by mass or more and 92% by mass or less, based on the total amount of the colored composition of the present invention. In other words, the total content of the solids in the colored composition is preferably 5% by mass or more and 45% by mass or less, more preferably 8% by mass or more and 40% by mass or less. When the content of the solvent (E) is within the above range, the flatness during coating is good, and when a color filter is formed, the color density is not insufficient, so the display characteristics tend to be good.
[0205] <Leveling Agent (F)> Examples of the leveling agent (F) include silicone surfactants, fluorine surfactants, and silicone surfactants containing fluorine atoms, which may have a polymerizable group in the side chain.
[0206] Examples of silicone surfactants include surfactants having a siloxane bond in the molecule, such as Toray Silicone DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, SH29PA, SH30PA, and SH8400 (trade names: manufactured by Dow Corning Toray Co., Ltd.), KP321, KP322, KP323, KP324, KP326, KP340, and KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), and TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452, and TSF4460 (manufactured by Momentive Performance Materials Japan, LLC).
[0207] Examples of the fluorine-based surfactant include surfactants having a fluorocarbon chain in the molecule, such as Fluorad (registered trademark) FC430 and FC431 (manufactured by Sumitomo 3M Limited), Megafac (registered trademark) F142D, F171, F172, F173, F177, F183, F554, R30, and RS-718-K (manufactured by DIC Corporation), Ftop (registered trademark) EF301, EF303, EF351, and EF352 (manufactured by Mitsubishi Materials Electronic Chemicals Co., Ltd.), Surflon (registered trademark) S381, S382, SC101, and SC105 (manufactured by Asahi Glass Co., Ltd.), and E5844 (manufactured by Daikin Fine Chemical Research Institute, Inc.).
[0208] Examples of the silicone surfactant having a fluorine atom include surfactants having a siloxane bond and a fluorocarbon chain in the molecule, such as Megafac (registered trademark) R08, BL20, F475, F477, and F443 (manufactured by DIC Corporation).
[0209] The content of the leveling agent (F) is preferably 0.00001% by mass or more and 0.2% by mass or less, more preferably 0.00002% by mass or more and 0.1% by mass or less, and even more preferably 0.0001% by mass or more and 0.05% by mass or less, relative to the total amount of the coloring composition. Note that this content does not include the content of the pigment dispersant. When the content of the leveling agent (F) is within the above range, the flatness of the color filter can be improved.
[0210] <Other ingredients> The colored composition of the present invention may contain additives known in the art, such as fillers, other polymer compounds, adhesion promoters, antioxidants, light stabilizers, and chain transfer agents, as needed.
[0211] <Method of producing colored composition> The colored composition of the present invention can be prepared, for example, by mixing the colorant (A) and resin (B), as well as the polymerizable compound (C), polymerization initiator (D), solvent (E), leveling agent (F), and other components that are used as needed. Mixing can be carried out using known or conventional equipment and conditions.
[0212] The colorant (A) may be mixed in advance with part or all of the solvent (E) and dispersed using a bead mill or the like until the average particle size becomes approximately 0.2 μm or less. At this time, the dispersant and part or all of the resin (B) may be added as needed. The remaining components are preferably mixed with the dispersion thus obtained to a predetermined concentration to prepare the desired colored composition. When using a bead mill, the diameter of the beads is preferably 0.05 mm or more and 0.5 mm or less, and the material of the beads may be glass, ceramic, metal, or the like.
[0213] <Color filter manufacturing method> Methods for producing a colored pattern of a color filter from the colored composition of the present invention include photolithography, inkjet printing, and printing. Among these, photolithography is preferred. The photolithography is a method in which the colored composition is applied to a substrate, dried to form a composition layer, and then exposed to light through a photomask and developed. In the photolithography, a colored coating film, which is a cured product of the composition layer, can be formed by not using a photomask during exposure and / or not developing.
[0214] The film thickness of the color filter (cured film) is not particularly limited and can be adjusted appropriately depending on the purpose, application, etc., and is, for example, 0.1 μm or more and 30 μm or less, preferably 0.1 μm or more and 20 μm or less, and more preferably 0.5 μm or more and 6 μm or less.
[0215] The substrate may be a glass plate such as quartz glass, borosilicate glass, alumina silicate glass, or silica-coated soda lime glass; a resin plate such as polycarbonate, polymethyl methacrylate, or polyethylene terephthalate; silicon; or a substrate having a thin film of aluminum, silver, or a silver / copper / palladium alloy formed thereon. A separate color filter layer, a resin layer, a transistor, a circuit, or the like may be formed on these substrates. Alternatively, a silicon substrate treated with HMDS may be used.
[0216] Formation of each color pixel by photolithography can be carried out using known or conventional equipment and conditions. For example, it can be produced as follows. First, a coloring composition is applied to a substrate, and volatile components such as solvents are removed by heat drying (pre-baking) and / or vacuum drying to obtain a smooth composition layer. Examples of application methods include spin coating, slit coating, and slit and spin coating. When heat drying is performed, the temperature is preferably 30°C to 120°C, more preferably 50°C to 110°C. The heating time is preferably 10 seconds to 60 minutes, more preferably 30 seconds to 30 minutes. When vacuum drying is performed, it is preferably performed under a pressure of 50 to 150 Pa at a temperature of 20 to 25°C. The film thickness of the composition layer is not particularly limited and may be appropriately selected depending on the film thickness of the desired color filter.
[0217] Next, the composition layer is exposed through a photomask to form a desired color pattern. The pattern on the photomask is not particularly limited, and a pattern appropriate for the intended application is used. The light source used for exposure is preferably a light source that emits light with a wavelength of 250 to 450 nm. For example, light less than 350 nm may be cut using a filter that cuts this wavelength range, or light around 436 nm, 408 nm, and 365 nm may be selectively extracted using a bandpass filter that extracts these wavelength ranges. Specific examples include mercury lamps, light-emitting diodes, metal halide lamps, and halogen lamps. It is preferable to use a reduction projection exposure device or proximity exposure device such as a mask aligner or stepper, as this allows for uniform irradiation of the entire exposure surface with parallel light and allows for accurate alignment of the photomask and substrate.
[0218] A colored pattern is formed on the substrate by contacting the exposed composition layer with a developer and developing it. The unexposed portions of the composition layer are dissolved and removed by development. The developer is preferably an aqueous solution of an alkaline compound such as potassium hydroxide, sodium bicarbonate, sodium carbonate, or tetramethylammonium hydroxide. The concentration of these alkaline compounds in the aqueous solution is preferably 0.01% by mass or more and 10% by mass or less, more preferably 0.03% by mass or more and 5% by mass or less. The developer may also contain a surfactant. The development method may be any of a puddle method, a dipping method, a spray method, or the like. Furthermore, the substrate may be tilted at any angle during development. After development, it is preferable to wash with water.
[0219] Furthermore, the obtained colored pattern is preferably post-baked. The post-baking temperature is preferably 80° C. or higher and 250° C. or lower, and more preferably 100° C. or higher and 245° C. or lower. The post-baking time is preferably 1 minute or higher and 120 minutes or lower, and more preferably 2 minutes or higher and 30 minutes or lower.
[0220] The colored patterns and colored coating films thus obtained are useful as color filters, and the color filters are useful as color filters used in display devices (e.g., liquid crystal display devices, organic EL devices, etc.), electronic paper, solid-state imaging devices, etc.
[0221] This application claims the benefit of priority to Japanese Patent Application No. 2020-162452, filed on September 28, 2020. The entire content of the specification of Japanese Patent Application No. 2020-162452, filed on September 28, 2020, is incorporated herein by reference. [Example]
[0222] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples. In the examples and comparative examples, % and parts representing the content or amount used are by mass unless otherwise specified. In the following examples, the structures of the compounds were confirmed by mass spectrometry (LC; Agilent 1200 model, MASS; Agilent LC / MSD6130 model).
[0223] [Colorant synthesis example] Synthesis Example 1 <Synthesis of Colorant (A-1)> 5.0 parts of 2,5-dichloro-4-nitroaniline were mixed with 4.0 parts of water, 10 parts of acetic acid, 10 parts of methanol, and 25 parts of 98% sulfuric acid and stirred. Under ice cooling, an aqueous solution of 2.0 parts of sodium nitrite dissolved in 3.0 parts of water was added to the reaction solution and stirred for 2 hours to obtain a suspension containing a diazonium salt. Meanwhile, 15 parts of methanol was added to 3.0 parts of barbituric acid (α), and then 100 parts of a 25% aqueous sodium hydroxide solution was added under ice cooling and stirred. The suspension containing the diazonium salt was added dropwise to the mixture. After the dropwise addition, the mixture was further stirred at room temperature for 1 hour to obtain an orange suspension. The orange solid obtained by filtration was dried under reduced pressure at 60°C to obtain a compound represented by formula (1).
[0224] [ka]
[0225] Next, 97 parts of water, 4.1 parts of sodium bicarbonate, and 3.8 parts of sodium sulfide nonahydrate were added to 8.4 parts of the compound represented by formula (1), and the mixture was stirred at 85°C for 2 hours. After cooling the reaction solution to room temperature, the reaction solution was neutralized to pH 6 with 35% hydrochloric acid, and the precipitated solid was collected by filtration. The resulting solid was washed with water, and the red solid obtained by filtration was dried at 60°C under reduced pressure to obtain 6.3 parts of the compound represented by formula (2).
[0226] [ka]
[0227] Next, 2.1 parts of the compound represented by formula (2) were added to 20 parts of water, 6.7 parts of acetic acid, and 3.3 parts of 98% sulfuric acid and stirred. Under ice cooling, an aqueous solution of 0.6 parts of sodium nitrite dissolved in 3.3 parts of water was added to the reaction solution and stirred for 2 hours to obtain a suspension containing a diazonium salt. Meanwhile, 0.8 parts of barbituric acid (β) were added to 0.8 parts of methanol, and then 15 parts of 25% aqueous sodium hydroxide solution was added under ice cooling and stirred. The suspension containing the diazonium salt was added dropwise to the mixture. After the dropwise addition was completed, the mixture was stirred at room temperature for an additional hour to obtain a red suspension. The red solid obtained by filtration was dispersed and washed with acetic acid for 30 minutes, then filtered and dried at 60°C under reduced pressure to obtain 1.7 parts of the compound represented by formula (A-1) (yield 57%). MS(ESI) m / z=453.0[MH] -
[0228] [ka]
[0229] Synthesis Example 2 <Synthesis of Colorant (A-2)> 0.4 parts (yield 15%) of the compound represented by formula (A-2) was obtained in the same manner as in Synthesis Example 1, except that 3.0 parts of barbituric acid (α) was replaced with 5.1 parts of 1,3-dicyclohexylbarbituric acid (α) and 0.8 parts of barbituric acid (β) was replaced with 0.7 parts of 1,3-dicyclohexylbarbituric acid (β). MS(ESI) m / z=783.4[M+H] +
[0230] [ka]
[0231] Synthesis Example 3 <Synthesis of Colorant (A-3)> 3.9 parts (yield 66%) of the compound represented by formula (A-3) were obtained in the same manner as in Synthesis Example 1, except that 3.0 parts of barbituric acid (α) were replaced with 1.8 parts of 3-cyano-1-butyl-6-hydroxy-4-methyl-2-pyridone (α) and 0.8 parts of barbituric acid (β) were replaced with 1.4 parts of 3-cyano-1-butyl-6-hydroxy-4-methyl-2-pyridone (β). MS(ESI) m / z=609.2[MH] -
[0232] [ka]
[0233] Synthesis Example 4 <Synthesis of Colorant (A-4)> 0.8 parts of the compound represented by formula (A-4) (yield 53%) was obtained in the same manner as in Synthesis Example 1, except that 3.0 parts of barbituric acid (α) was replaced with 4.2 parts of 3-methyl-1-phenyl-5-pyrazolone (α) and 0.8 parts of barbituric acid (β) was replaced with 0.5 parts of 3-methyl-1-phenyl-5-pyrazolone (β). MS(ESI) m / z=547.2[M+H] +
[0234] [ka]
[0235] Synthesis Example 5 <Synthesis of Colorant (A-5)> 1.2 parts (yield 58%) of the compound represented by formula (A-5) was obtained in the same manner as in Synthesis Example 1, except that 3.0 parts of barbituric acid (α) was replaced with 4.9 parts of 3-methyl-1-(4-sulfophenyl)-2-pyrazolin-5-one (α) and 0.8 parts of barbituric acid (β) was replaced with 0.7 parts of 3-methyl-1-(4-sulfophenyl)-2-pyrazolin-5-one (β). MS(ESI) m / z=705.0[MH] -
[0236] [ka]
[0237] Synthesis Example 6 <Synthesis of Colorant (A-6)> 1.9 parts (yield 56%) of the compound represented by formula (A-6) was obtained in the same manner as in Synthesis Example 1, except that 0.8 parts of barbituric acid (β) was changed to 1.2 parts of 3-cyano-1-butyl-6-hydroxy-4-methyl-2-pyridone. MS(ESI) m / z=533.0[M+H] +
[0238] [ka]
[0239] Synthesis Example 7 <Synthesis of Colorant (A-7)> 1.5 parts (yield 54%) of the compound represented by formula (A-7) were obtained in the same manner as in Synthesis Example 1, except that 0.8 parts of barbituric acid (β) was replaced with 1.0 part of 3-methyl-1-phenyl-5-pyrazolone. MS(ESI) m / z=499.1[MH] -
[0240] [ka]
[0241] Synthesis Example 8 <Synthesis of Colorant (A-8)> 1.2 parts (yield 37%) of the compound represented by formula (A-8) was obtained in the same manner as in Synthesis Example 1, except that 0.8 parts of barbituric acid (β) was replaced with 0.5 parts of 3-methyl-1-(4-sulfophenyl)-2-pyrazolin-5-one. MS(ESI) m / z=579.0[MH] -
[0242] [ka]
[0243] Synthesis Example 9 <Synthesis of Colorant (A-9)> 0.3 parts (yield 31%) of the compound represented by formula (A-9) was obtained in the same manner as in Synthesis Example 2, except that 0.7 parts of 1,3-dicyclohexylbarbituric acid (β) was replaced with 0.2 parts of 3-methyl-1-phenyl-5-pyrazolone. MS(ESI) m / z=664.0[M] -
[0244] [ka]
[0245] Synthesis Example 10 <Synthesis of Colorant (A-10)> 35 parts (yield 73%) of the compound represented by formula (A-10) was obtained in the same manner as in Synthesis Example 4, except that 4.2 parts of 3-methyl-1-phenyl-5-pyrazolone (α) was replaced with 18 parts of 3-methyl-1-(4-sulfophenyl)-2-pyrazolin-5-one. MS(ESI) m / z=625.1[MH] -
[0246] [ka]
[0247] Synthesis Example 11 <Synthesis of Colorant (A-11)> To 1.5 parts of the compound represented by formula (A-10), 15 parts of chloroform and 0.4 parts of N,N-dimethylformamide were added, and 0.6 parts of thionyl chloride was added dropwise while stirring and maintaining the temperature at 20°C or below. After the dropwise addition, the mixture was heated to 50°C and reacted at that temperature for 3 hours, then cooled to 20°C. To the cooled reaction solution, a mixture of 0.5 parts of 2-methylcyclohexylamine and 1.9 parts of triethylamine was added dropwise while stirring and maintaining the temperature at 20°C or below. The reaction was then continued for 5 hours at the same temperature. The resulting reaction mixture was then distilled off using a rotary evaporator, after which a small amount of methanol was added and the mixture was stirred vigorously. This mixture was added to 45 parts of a 20% aqueous sodium chloride solution with stirring to precipitate crystals. The precipitated crystals were filtered off, washed with water, and dried under reduced pressure at 60°C to obtain 1.2 parts of the compound represented by formula (A-11) (yield: 74%). MS(ESI) m / z=720.2[MH] -
[0248] [ka]
[0249] Synthesis Example 12 <Synthesis of Colorant (A-12)> 0.8 parts (yield 58%) of a compound represented by formula (A-12) was obtained in the same manner as in Synthesis Example 11, except that 0.5 parts of 2-methylcyclohexylamine was changed to 2.1 parts of 3,5-di-tert-butylaniline. MS(ESI) m / z=813.2[M] -
[0250] [ka]
[0251] Synthesis Example 13 <Synthesis of Colorant (A-13)> The same method as in Synthesis Example 11 was repeated, except that 0.5 parts of 2-methylcyclohexylamine was replaced with 1.3 parts of aniline, to obtain 1.2 parts (yield 74%) of a compound represented by formula (A-13). MS(ESI) m / z=701.1[M] -
[0252] [ka]
[0253] Synthesis Example 14 <Synthesis of Colorant (A-14)> 0.9 parts (yield 59%) of a compound represented by formula (A-14) was obtained in the same manner as in Synthesis Example 11, except that 0.5 parts of 2-methylcyclohexylamine was changed to 1.8 parts of 1-adamantanamine. MS(ESI) m / z=759.2[M] -
[0254] [ka]
[0255] Synthesis Example 15 <Synthesis of Colorant (A-15)> 0.9 parts (yield 62%) of a compound represented by formula (A-15) was obtained in the same manner as in Synthesis Example 11, except that 0.5 parts of 2-methylcyclohexylamine was changed to 1.2 parts of 1,3-dimethylbutylamine. MS(ESI) m / z=709.2[M] -
[0256] [ka]
[0257] Synthesis Example 16 <Synthesis of Colorant (A-16)> 60 parts of water and 60 parts of N,N-dimethylformamide were added to 0.5 parts of the compound represented by formula (A-10), and 1.2 parts of barium acetate was added under stirring. The mixture was heated to 60°C and reacted at the same temperature for 2 hours, and then cooled to 20°C. After cooling, the reaction solution was filtered, washed with methanol, and dried under reduced pressure at 60°C to obtain 0.4 parts of the compound represented by formula (A-16) (yield 76%).
[0258] [ka]
[0259] Synthesis Example 17 <Synthesis of Colorant (A-17)> 0.4 parts of a compound represented by formula (A-17) (yield 28%) was obtained in the same manner as in Synthesis Example 11, except that 1.5 parts of the compound represented by formula (A-10) was changed to 1.2 parts of the compound represented by formula (A-5), 0.4 parts of N,N-dimethylformamide was changed to 0.3 parts, 0.6 parts of thionyl chloride was changed to 9.4 parts, 0.5 parts of 2-methylcyclohexylamine was changed to 2.3 parts, and 1.9 parts of triethylamine was changed to 5.3 parts. MS(ESI) m / z=895.2[MH] -
[0260] [ka]
[0261] Synthesis Example 18 <Synthesis of Colorant (A-18)> 3.2 parts (yield 65%) of the compound represented by formula (A-18) were obtained in the same manner as in Synthesis Example 7, except that 5.0 parts of 2,5-dichloro-4-nitroaniline was replaced with 3.0 parts of 2-methyl-4-nitroaniline. MS(ESI) m / z=445.2[MH] -
[0262] [ka]
[0263] Synthesis Example 19 <Synthesis of Colorant (A-19)> The same method as in Synthesis Example 10 was repeated, except that 5.0 parts of 2,5-dichloro-4-nitroaniline was replaced with 6.0 parts of 2-methyl-4-nitroaniline, to obtain 4.0 parts (yield 90%) of the compound represented by formula (A-19). MS(ESI) m / z=571.2[MH] -
[0264] [ka]
[0265] Synthesis Example 20 <Synthesis of Colorant (A-20)> 0.3 parts (yield 20%) of a compound represented by formula (A-20) was obtained in the same manner as in Synthesis Example 11, except that 1.5 parts of a compound represented by formula (A-10) was replaced with 1.5 parts of a compound represented by formula (A-19). MS(ESI) m / z=666.3[MH] -
[0266] [ka]
[0267] Synthesis Example 21 <Synthesis of Colorant (A-21)> 1.3 parts (yield 40%) of the compound represented by formula (A-21) was obtained in the same manner as in Synthesis Example 4, except that 5.0 parts of 2,5-dichloro-4-nitroaniline was changed to 3.0 parts of 2-chloro-4-nitroaniline. MS(ESI) m / z=513.3[M+H] +
[0268] [ka]
[0269] Synthesis Example 22 <Synthesis of Colorant (A-22)> 0.3 parts of the compound represented by formula (A-22) (yield 21%) was obtained in the same manner as in Synthesis Example 4, except that 5.0 parts of 2,5-dichloro-4-nitroaniline was replaced with 3 parts of 2,6-dichloro-4-nitroaniline. MS(ESI) m / z=545.3[MH] -
[0270] [ka]
[0271] Synthesis Example 23 <Synthesis of Colorant (A-23)> 2.4 parts (yield 73%) of the compound represented by formula (A-23) was obtained in the same manner as in Synthesis Example 4, except that 5.0 parts of 2,5-dichloro-4-nitroaniline was changed to 2.0 parts of 4-nitroaniline. MS(ESI) m / z=479.5[M+H] +
[0272] [ka]
[0273] Synthesis Example 24 <Synthesis of Colorant (A-24)> 0.3 parts (yield 15%) of the compound represented by formula (A-24) was obtained in the same manner as in Synthesis Example 4, except that 5.0 parts of 2,5-dichloro-4-nitroaniline was replaced with 1.0 part of 2,5-dimethoxy-4-nitroaniline. MS(ESI) m / z=537.2[MH] -
[0274] [ka]
[0275] <Synthesis of Colorant (I-1)> A compound represented by formula (a) was synthesized according to the method described in JP-A-2002-179979.
[0276] [ka]
[0277] <Synthesis of colorant (x1)> A compound represented by formula (x1) was synthesized according to the method described in JP 2015-61907 A.
[0278] [ka]
[0279] [Resin synthesis example] <Resin synthesis example 1> A suitable amount of nitrogen was passed into a flask equipped with a reflux condenser, a dropping funnel, and a stirrer to replace the atmosphere with nitrogen, and 141 parts of ethyl lactate and 178 parts of propylene glycol monomethyl ether acetate were added and heated to 85°C with stirring. Next, 38 parts of acrylic acid and 3,4-epoxytricyclo[5.2.1.0] were added. 2,6 ]dec-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 2,6 A mixed solution of 25 parts of a mixture of dec-9-yl acrylate (1:1 content), 137 parts of cyclohexylmaleimide, 50 parts of 2-hydroxyethyl methacrylate, and 338 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. Meanwhile, a mixed solution of 5 parts of 2,2-azobisisobutyronitrile dissolved in 88 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After the addition was completed, the mixture was maintained at the same temperature for 4 hours and then cooled to room temperature to obtain a copolymer (Resin B-1) solution with a solids content of 25.6%. The resulting copolymer had a weight-average molecular weight (Mw) of 8000, a polydispersity of 2.1, and an acid value calculated as solids of 111 mg-KOH / g. Resin B-1 has the following structural units:
[0280] [ka]
[0281] <Resin synthesis example 2> A flask equipped with a reflux condenser, a dropping funnel, and a stirrer was filled with nitrogen to replace the atmosphere, and 280 parts of propylene glycol monomethyl ether acetate was added, followed by heating to 80°C with stirring. Next, 38 parts of acrylic acid, 3,4-epoxytricyclo[5.2.1.0] 2,6 ]decan-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 2,6 A mixed solution of 289 parts of a mixture of decan-9-yl acrylate (content ratio 1:1 by molar ratio) and 125 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. Meanwhile, a solution of 33 parts of 2,2-azobis(2,4-dimethylvaleronitrile) dissolved in 235 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After the dropwise addition was completed, the mixture was kept at 80°C for 4 hours and then cooled to room temperature to obtain a copolymer (Resin B-2) solution with a solids content of 35.1% and a viscosity of 125 mPas measured with a Brookfield viscometer (23°C). The weight-average molecular weight Mw of the resulting copolymer was 9.2 x 10 3 The resin B-2 had a polydispersity of 2.08 and an acid value of 77 mg-KOH / g in terms of solid content.
[0282] [ka]
[0283] The polystyrene-equivalent weight average molecular weight (Mw) and number average molecular weight (Mn) of the resin were measured by GPC under the following conditions. Apparatus: HLC-8120GPC (Tosoh Corporation) Column: TSK-GELG2000HXL Column temperature: 40°C Solvent: THF Flow rate: 1.0mL / min Test liquid solid content concentration: 0.001~0.01% by mass Injection volume: 50μL Detector: RI Calibration standard material ;TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (Manufactured by Tosoh Corporation) The ratio of the weight average molecular weight and the number average molecular weight (Mw / Mn) calculated in terms of polystyrene obtained above was taken as the dispersity.
[0284] <Dispersion liquid preparation example 1> 4.5 parts of the compound represented by formula (A-1) obtained in Synthesis Example 1, 0.5 parts of the compound represented by formula (a), 5.7 parts of a dispersant (BYKLPN-6919 manufactured by BYK) (solid content equivalent), 9.9 parts of resin B-2 (solid content equivalent), 74.3 parts of propylene glycol monomethyl ether acetate, and 5.0 parts of diacetone alcohol were mixed, and 300 parts of 0.2 mm zirconia beads were added, followed by shaking, and the zirconia beads were removed by filtration to obtain dispersion (P-1).
[0285] <Dispersion Preparation Examples 2 to 9> Dispersions (P-2) to (P-9) were obtained in the same manner as in Dispersion Preparation Example 1, except that the compound represented by formula (A-1) in Dispersion Preparation Example 1 was changed to the compound below. Dispersion (P-2): Compound represented by formula (A-3) obtained in Synthesis Example 3 Dispersion (P-3): Compound represented by formula (A-4) obtained in Synthesis Example 4 Dispersion (P-4): Compound represented by formula (A-6) obtained in Synthesis Example 6 Dispersion (P-5): Compound represented by formula (A-7) obtained in Synthesis Example 7 Dispersion (P-6): Compound represented by formula (A-11) obtained in Synthesis Example 11 Dispersion (P-7): Compound represented by formula (A-18) obtained in Synthesis Example 18 Dispersion (P-8): Compound represented by formula (A-21) obtained in Synthesis Example 21 Dispersion (P-9): Compound represented by formula (A-23) obtained in Synthesis Example 23
[0286] [Examples 1 to 9, Comparative Example 1] [Preparation of Coloring Composition] A colored composition was obtained by mixing the components of the dispersion liquid (P), colorant (x1), resin (B), polymerizable compound (C), polymerization initiator (D), solvent (E), and leveling agent (F) so as to obtain the composition shown in Table 8.
[0287] [Table 8]
[0288] In Table 8, each component represents the following compound. Resin (B-1): Resin B-1 (solid content equivalent) Polymerizable compound (C-1): Dipentaerythritol polyacrylate: Product name A-9550: manufactured by Shin-Nakamura Chemical Co., Ltd. Polymerization initiator (D-1): N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine (trade name: PBG-327; O-acyloxime compound; manufactured by Changzhou Powerful New Electronic Materials Co., Ltd.) Solvent (E-1): Propylene glycol monomethyl ether acetate Solvent (E-2): Ethyl lactate Leveling agent (F-1): Polyether-modified silicone oil: Toray Silicone SH8400 (manufactured by Toray Dow Corning Co., Ltd.)
[0289] [Formation of color filters (colored coatings)] The colored compositions obtained in Examples 1 to 9 and Comparative Example 1 were applied by spin coating onto a 2-inch square glass substrate (Eagle XG; manufactured by Corning Incorporated), and then prebaked at 100°C for 3 minutes to obtain a colored composition layer. After cooling, the colored compositions were exposed to 60 mJ / cm 2 in the air using an exposure machine (TME-150RSK; manufactured by Topcon Corporation) without using a photomask. 2 The colored composition layer after the light irradiation was post-baked in an oven at 230°C for 20 minutes to obtain a colored coating film. After cooling, the film thickness of the obtained colored coating film was measured using a film thickness measuring device (DEKTAK3; manufactured by Nippon Shinku Gijutsu Co., Ltd.).
[0290] [Chromaticity evaluation] The spectrum of the obtained colored coating film was measured using a colorimeter (OSP-SP-200; manufactured by Olympus Corporation), and the xy chromaticity coordinates (x, y) and tristimulus value Y in the CIE XYZ color system were measured using the characteristic function of the C illuminant.
[0291] [UV ashing resistance evaluation] The resulting colored coating was subjected to 2000mW / cm irradiation using an ultraviolet ozone cleaning device (UV-312 manufactured by technovision.inc.). 3 The xy chromaticity coordinates (x, y) and Y were measured before and after irradiation, and the color difference ΔEab was calculated from the measured values according to the method described in JIS Z 8730:2009 (7. Calculation method for color difference). * The results are shown in Table 9. * The smaller the value, the smaller the color change. * If the value is 5 or less, it can be said that the colored coating film presents no practical problems as a color filter. Furthermore, if the UV ashing resistance of a colored coating film is good, it can be said that a colored pattern produced from the same colored composition also has good UV ashing resistance.
[0292] [Table 9] [Industrial Applicability]
[0293] According to the colored composition of the present invention, a color filter having excellent UV ashing resistance can be formed.
Claims
1. A coloring composition comprising a colorant containing a compound represented by formula (I) and an alkali-soluble resin. 【Chemistry 1】 [In formula (I), L 1 represents a group represented by formula (ph1), A represents a group represented by formula (ia): B represents a group represented by formula (ib). 【Chemistry 2】 [In formula (ph1), X 1 represents a hydrocarbon group which may have a substituent or a substituent, and —CH 2 - may be replaced by -O-, -CO- or -NH-, and -CH= contained in the hydrocarbon group may be replaced by -N=. n represents an integer of 0 to 4. When n represents an integer of 2 or more, a plurality of X 1 may be the same or different. n represents an integer of 2 or more, and X 1 is bonded to an adjacent carbon atom, X is bonded to an adjacent carbon atom 1 may be bonded to each other to form a ring. * represents a bond to A, and ** represents a bond to B.] 【Transformation 3】 [In formula (ia) and formula (ib), X 6 ~X 9 each independently represents a hydrocarbon group which may have a substituent, and —CH 2 - may be replaced by -O-, -CO- or -NH-, -CH= contained in the hydrocarbon group may be replaced by -N=, and -C< contained in the hydrocarbon group may be replaced by -N<. X 6 and X 7 may be bonded to each other to form a ring, and X 8 and X 9 may be bonded to each other to form a ring. * is L 1 represents a bond with .]
2. L 1 The colored composition according to claim 1, wherein is a group represented by formula (ph2): 【Chemistry 4】 [In formula (ph2), X 2 ~X 5 each independently represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an amino group, an amide group, a carboxyl group, an alkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, a cyano group, or a halogen atom. 2 and X 3 , X 4 and X 5 may be bonded to each other to form a ring. * represents a bond to A, and ** represents a bond to B.]
3. The colored composition according to claim 1 or 2, wherein the group represented by formula (ia) and the group represented by formula (ib) are each independently any of groups represented by formulas (t1) to (t5). 【Transformation 5】 [In formulas (t1) to (t5), R 1 ~R 16 each independently represents a hydrogen atom, a hydrocarbon group which may have a substituent, a heterocyclic group, a cyano group, or a halogen atom. 1 represents a bond with .]
4. A coloring composition described in any one of claims 1 to 3, wherein the acid value of the alkali-soluble resin is 50 mg-KOH / g or more and 170 mg-KOH / g or less, calculated as solid content.
5. The colored composition according to any one of claims 1 to 4, further comprising a polymerizable compound and a polymerization initiator.
6. A color filter formed from the coloring composition according to any one of claims 1 to 5.
7. A display device comprising the color filter according to claim 6.
Citation Information
Patent Citations
P-phenylenediamine bisazo organic pigment and preparation method thereof
CN103087544A
Disazo compound, manufacture and use
JP1985228570A
Method for processing silver halide color photographic sensitive material
JP1988146041A
Benzofuran-2-ones as colorants for organic materials
JP2002539122A
Coloring curable composition
JP2015061907A