Benzoperylene compounds and colored curable resin compositions

Abstract

The present invention aims to provide a compound having high fluorescence intensity as a fluorescent dye, and a colored curable resin composition capable of forming a color filter having excellent fluorescence intensity. The present invention relates to a colored curable resin composition containing a colorant, a resin, a polymerizable compound, and a polymerization initiator, the colorant comprising a benzo perylene compound.

Description

Technical Field

[0001] This invention relates to colorants, particularly benzo[a]perylene compounds useful as dyes, and color-curing resin compositions containing benzo[a]perylene compounds. Background Technology

[0002] Color filters used in display devices such as liquid crystal displays, electroluminescent displays, and plasma displays, as well as solid-state imaging devices such as CCDs and CMOS sensors, are manufactured from color-curing resin compositions. Various colorants are used as the color-curing resin compositions used to form these color filters. Furthermore, perylene compounds are known as fluorescent dyes (Non-Patent Document 1), and examples of using perylene compounds in color conversion layers are also known (Patent Document 1).

[0003] Existing technical documents

[0004] Patent documents

[0005] Patent Document 1: Japanese Patent Application Publication No. 2018-124553

[0006] Non-patent literature

[0007] Non-Patent Document 1: BASF Technical Report (BASF Corporation Technical Report) (Lumogen (registered trademark) F), BASF Corporation, November 1997, 2-6 Summary of the Invention

[0008] The problem that the invention aims to solve

[0009] However, the aforementioned perylene compounds known in the past sometimes fail to adequately meet fluorescence intensity requirements. Therefore, the object of the present invention is to provide colorants, particularly compounds having higher fluorescence intensity as fluorescent dyes, and color-curable resin compositions comprising compounds (preferably dyes) capable of forming color filters with excellent fluorescence intensity.

[0010] Methods for solving problems

[0011] The gist of this invention is as follows.

[0012] [1] A coloring and curing resin composition comprising a colorant, a resin, a polymerizable compound, and a polymerization initiator.

[0013] The aforementioned colorants contain benzo[a]perylene compounds.

[0014] [2] The coloring curable resin composition as described in [1], wherein the benzo[1] perylene compound is a compound represented by formula (I).

[0015]

[0016] In formula (I),

[0017] R 1 and R 2 Each of these terms independently represents a hydrocarbon group having 1 to 30 carbon atoms that may have substituents, an aromatic heterocyclic group having 1 to 30 carbon atoms that may have substituents, or a group formed by bonding the aforementioned hydrocarbon group that may have substituents with the aforementioned aromatic heterocyclic group that may have substituents.

[0018] R 3 ~R 10 Each can be used to independently represent a hydrogen atom, *-R 11 、*-OR 11 、*-CO-OR 11 Halogen atom, hydroxyl group, carboxyl group or nitro group.

[0019] R 3 With R 4 R 4 With R 5 R 5 With R 6 R 7 With R 8 R 8 With R 9 and R 9 With R 10 They can independently form compounds containing *-CO-O-CO-* or *-CO-N(R) 11 )-CO-* ring.

[0020] R 11 This refers to a hydrocarbon group with 1 to 30 carbon atoms that can have substituents, and the presence of multiple R groups. 11 In certain circumstances, they can be different from each other.

[0021] * indicates a connection key.

[0022] [3] The coloring curable resin composition as described in [1] or [2], wherein the colorant further comprises a perylene compound.

[0023] [4] A color filter, which is formed from any one of the color-curing resin compositions described in [1] to [3].

[0024] [5] A display device comprising the color filter described in [4].

[0025] [6] Compound represented by formula (Ia).

[0026]

[0027] In formula (Ia),

[0028] R 1aand R 2a Each can be independently represented as an aryl group having 6 to 20 carbon atoms that may have substituents, or a heteroaryl group having 1 to 20 carbon atoms that may have substituents.

[0029] R 3a R 6a R 7a R 8a R 9a and R 10a Each can be used to independently represent a hydrogen atom, *-R 11a 、*-OR 11a 、*-CO-OR 11a Halogen atom, hydroxyl group, carboxyl group or nitro group.

[0030] R 11a This refers to a hydrocarbon group with 1 to 20 carbon atoms that can have substituents, and the presence of multiple R groups. 11a In certain circumstances, they can be different from each other.

[0031] R 4a and R 5a Each can be represented independently as *-CO-OR 11a , or R 4a and R 5a The groups represented by formula (a) or formula (b) are bonded together.

[0032]

[0033] In equations (a) and (b),

[0034] R b1 and R b2 Each can be independently represented as a hydrocarbon group with 1 to 20 carbon atoms that may have substituents.

[0035] R c1 This indicates an aryl group with 6 to 20 carbon atoms that can have substituents.

[0036] R 4a and R 5a In the case where R is the group represented by formula (b), 1a R 2a and R c1 These three cannot be the same group.

[0037] * indicates a connection key.

[0038] Invention Effects

[0039] According to the present invention, compounds capable of forming color filters with excellent fluorescence intensity and color curable resin compositions can be provided. Detailed Implementation

[0040] The coloring curable resin composition of the present invention comprises a colorant (hereinafter, sometimes referred to as colorant (A)), a resin (hereinafter, sometimes referred to as resin (B)), a polymerizable compound (hereinafter, sometimes referred to as polymerizable compound (C)) and a polymerization initiator (hereinafter, sometimes referred to as polymerization initiator (D)).

[0041] The coloring and curing resin composition of the present invention may further contain a solvent (hereinafter, sometimes referred to as solvent (E)).

[0042] The coloring and curing resin composition of the present invention may further contain a polymerization initiator (hereinafter, sometimes referred to as polymerization initiator (D1)).

[0043] The coloring and curing resin composition of the present invention may further contain a leveling agent (hereinafter, sometimes referred to as leveling agent (F)).

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

[0045] <Coloring Agent (A)>

[0046] Colorant (A) comprises a benzo[a]perylene compound. A benzo[a]perylene compound is a compound having any substituents bonded to 1,12-benzo[a]perylene, preferably a compound having carbonyl substituents bonded to the 3,4 and 9,10 positions. The carbonyl groups of the substituents at the 3 and 4 positions are preferably bonded via oxygen atoms to form a lactone ring, or via nitrogen atoms to form an imide ring. The carbonyl groups of the substituents at the 9 and 10 positions are also preferably bonded via oxygen atoms to form a lactone ring, or via nitrogen atoms to form an imide ring. The benzo[a]perylene compound described above is particularly preferred to be a compound represented by formula (I) (hereinafter, sometimes referred to as compound (I)).

[0047] <<Compound (I)>>

[0048]

[0049] In formula (I),

[0050] R 1 and R 2 Each of the above can be independently represented as a hydrocarbon group having 1 to 30 carbon atoms that may have a substituent (A1), an aromatic heterocyclic group having 1 to 30 carbon atoms that may have a substituent (A1), or a group formed by bonding the above-mentioned hydrocarbon group having a substituent (A1) with the above-mentioned aromatic heterocyclic group having a substituent (A1).

[0051] R 3 ~R 10 Each can be used to independently represent a hydrogen atom, *-R11 、*-OR 11 、*-CO-OR 11 Halogen atom, hydroxyl group, carboxyl group or nitro group.

[0052] R 3 With R 4 R 4 With R 5 R 5 With R 6 R 7 With R 8 R 8 With R 9 and R 9 With R 10 They can independently form compounds containing *-CO-O-CO-* or *-CO-N(R) 11 )-CO-* ring.

[0053] R 11 This indicates a hydrocarbon group with 1 to 30 carbon atoms that can have substituents (A1), and multiple R groups exist. 11 In certain circumstances, they can be different from each other.

[0054] * indicates a connection key.

[0055] As R 1 R 2 and R 11 The hydrocarbon groups represented have 1 to 30 carbon atoms, including aliphatic and aromatic hydrocarbon groups. Aliphatic hydrocarbon groups can be saturated or unsaturated, and can be chain-like or alicyclic.

[0056] As R 1 R 2 and R 11Examples of saturated or unsaturated chain hydrocarbon groups include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecanyl, octadecyl, nonadecanyl, eicosyl, and other straight-chain alkyl groups; isopropyl, (1-ethyl)propyl, isobutyl, sec-butyl, tert-butyl, (1-ethyl)butyl, (2-ethyl)butyl, (1-propyl)butyl, isopentyl, neopentyl, tert-pentyl, (2-methyl)pentyl, (1-ethyl)pentyl, (3-ethyl)pentyl, (1-propyl)pentyl, (1-butyl)pentyl, isohexyl, (2-methyl ...3-ethyl)pentyl, (1-propyl)pentyl, (1-butyl)pentyl, isohexyl, (3-ethyl)pentyl, (3-ethyl)pentyl, (1-propyl)pentyl, (1-butyl)pentyl Branched alkyl groups such as (5-methyl)hexyl, (2-ethyl)hexyl, (1-butyl)hexyl, (1-pentyl)hexyl, (2-methyl)heptyl, (2-ethyl)heptyl, (3-ethyl)heptyl, (1-hexyl)heptyl, (2-methyl)octyl, (2-ethyl)octyl, (1-heptyl)octyl, (2-ethyl)nonyl, (1-octyl)nonyl, etc.; vinyl, 1-propenyl, 2-propenyl(allyl), (1-methyl)vinyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, (1-(2-propenyl))vinyl, (1,2-dimethyl)propenyl, 2-pentenyl, etc.; etc. The number of carbon atoms in the saturated chain hydrocarbon group is preferably 1 to 25, more preferably 1 to 20, and even more preferably 1 to 18. In addition, the number of carbon atoms in the unsaturated chain hydrocarbon group is preferably 2 to 25, more preferably 2 to 20, and even more preferably 2 to 18.

[0057] As R 1 R 2 and R 11 Examples of saturated or unsaturated alicyclic hydrocarbon groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and other cycloalkyl groups; cyclohexenyl (e.g., cyclohex-2-ene, cyclohex-3-ene), cycloheptenyl, cyclooctenyl, and other cycloalkenyl groups; norbornyl, adamantyl, bicyclo[2.2.2]octyl, etc. The number of carbon atoms in the saturated or unsaturated alicyclic hydrocarbon group is preferably 3 to 25, more preferably 3 to 20, and even more preferably 3 to 15.

[0058] As R 1 R 2 and R 11 Examples of aromatic hydrocarbon groups include phenyl, 1-naphthyl, 2-naphthyl, phenanthryl, anthraceneyl, and pyrene. The number of carbon atoms in the aromatic hydrocarbon group is preferably 6 to 25, more preferably 6 to 20, and even more preferably 6 to 15.

[0059] For R 1 R 2 and R 11For the hydrocarbon group represented, as long as the upper limit for the number of carbon atoms is 30 or less, it can be a group composed of two or more chain hydrocarbon groups, alicyclic hydrocarbon groups, and aromatic hydrocarbon groups listed above. Such a group can be, for example, a group composed of an aromatic hydrocarbon group combined with at least one group selected from chain hydrocarbon groups, alicyclic hydrocarbon groups, and aromatic hydrocarbon groups, wherein the chain hydrocarbon group can be combined as a divalent group (e.g., alkanediyl). Examples of hydrocarbon groups based on combinations include aralkyl groups such as benzyl, phenethyl, and 1-methyl-1-phenylethyl; aryl alkenyl groups such as phenylvinyl (styryl); aryl alkynyl groups such as phenylethynyl; o-tolyl, m-tolyl, p-tolyl, 2-ethylphenyl, 3-ethylphenyl, 4-ethylphenyl, 2,3-dimethylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, and 3,4-dimethylphenyl. 3,5-Dimethylphenyl, 4-Vinylphenyl, o-Isopropylphenyl, m-Isopropylphenyl, p-Isopropylphenyl, 2,3-Diisopropylphenyl, 2,4-Diisopropylphenyl, 2,5-Diisopropylphenyl, 2,6-Diisopropylphenyl, 2,4,6-Triisopropylphenyl, 4-Butylphenyl, o-T-butylphenyl, m-T-butylphenyl, p-T-butylphenyl, 2,6-Di(T-butyl)phenyl, 3,5-Di(T-butyl)phenyl 3,6-Di(tert-butyl)phenyl, 4-tert-butyl-2,6-dimethylphenyl, 4-pentylphenyl, 4-octylphenyl, 4-(2,4,4-trimethyl-2-pentyl)phenyl, 2-dodecylphenyl, 3-dodecylphenyl, 4-dodecylphenyl and other alkylaryl groups; 2,3-dihydro-4-indenyl, 1,2,3,5,6,7-hexahydro-4-s-indaryl, 8-methyl-1,2,3,5,6,7-hexahydro- Aryl groups bonded with alkane dimethyl groups, such as 4-s-indane, 5,6,7,8-tetrahydro-1-naphthyl, 5,6,7,8-tetrahydro-2-naphthyl, 3-methyl-5,6,7,8-tetrahydro-2-naphthyl, and 3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl; aryl groups bonded with one or more aryl groups, such as biphenyl and terphenyl; cyclohexylmethylphenyl, benzylphenyl, and (dimethyl(phenyl)methyl)phenyl.Furthermore, the aforementioned hydrocarbon group can be, for example, a hydrocarbon group based on a combination of a chain hydrocarbon group and an alicyclic hydrocarbon group. Examples include 1-methylcyclopropyl, 1-methylcyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 1,2-dimethylcyclohexyl, 1,3-dimethylcyclohexyl, 1,4-dimethylcyclohexyl, 2,3-dimethylcyclohexyl, 2,4-dimethylcyclohexyl, 2,5-dimethylcyclohexyl, 2,6-dimethylcyclohexyl, 3,4-dimethylcyclohexyl, 3,5-dimethylcyclohexyl, and 2,2-dimethylcyclohexyl. The groups may include alicyclic hydrocarbon groups such as 3,3-dimethylcyclohexyl, 4,4-dimethylcyclohexyl, 2,4,6-trimethylcyclohexyl, 2,2,6,6-tetramethylcyclohexyl, 3,3,5,5-tetramethylcyclohexyl, 4-pentylcyclohexyl, 4-octylcyclohexyl, and 4-cyclohexylcyclohexyl; and alkyl groups such as cyclopropylmethyl, cyclopropylethyl, cyclobutylmethyl, cyclobutylethyl, cyclopentylmethyl, cyclopentylethyl, cyclohexylmethyl, 2-methylcyclohexylmethyl, cyclohexylethyl, and adamantylmethyl, which are bonded with one or more alicyclic hydrocarbon groups. The number of carbon atoms in groups formed by combining two or more chain hydrocarbon groups, alicyclic hydrocarbon groups, and aromatic hydrocarbon groups is preferably 4 to 28, more preferably 5 to 25, and even more preferably 6 to 20.

[0060] As R 1 and R 2 The aromatic heterocyclic group with 1 to 30 carbon atoms can be exemplified by aromatic heterocyclic groups containing at least one heteroatom such as a nitrogen atom, an oxygen atom, or a sulfur atom. Specifically, examples of aromatic heterocyclic groups include furanyl, pyrroleyl, thiopheneyl, oxazolyl, pyridyl, quinolinyl, thiazolyl, benzothiazolyl, and carbazoleyl, etc., and the number of carbon atoms is preferably 2 to 20, more preferably 3 to 15.

[0061] As R 1 and R 2 The group formed by bonding the aforementioned hydrocarbon group with the aforementioned aromatic heterocyclic group can be a group formed by bonding two or more hydrocarbon groups mentioned above with an aromatic heterocyclic group. For example, it can be a group formed by bonding at least one of a chain hydrocarbon group, an alicyclic hydrocarbon group, and an aromatic hydrocarbon group with an aromatic heterocyclic group. In this bonded group, the chain hydrocarbon group can be bonded as a divalent group (e.g., an alkane diene). Examples of groups formed by bonding the aforementioned hydrocarbon group with the aforementioned aromatic heterocyclic group include 2-methylpyridinyl, 4-ethyl-2-methylpyridinyl, indolyl, benzimidazolyl, benzofuranyl, benzothiopheneyl, etc. The number of carbon atoms in the group formed by bonding the aforementioned hydrocarbon group with the aforementioned aromatic heterocyclic group is preferably 7 to 30, more preferably 8 to 30, and even more preferably 10 to 30.

[0062] As R 1 R2 and R 11 The hydrocarbon group representing 1 to 30 carbon atoms, and R 1 and R 2 The aromatic heterocyclic groups with 1 to 30 carbon atoms may have substituents (A1), for example, halogen atoms; nitrile groups; nitro groups; amino groups; hydroxyl groups; alkoxy groups with 1 to 20 carbon atoms such as methoxy and ethoxy; aryloxy groups with 6 to 20 carbon atoms such as phenyloxy, 1-naphthyloxy, and 2-naphthyloxy; thiols; alkylthio groups with 1 to 20 carbon atoms such as methylthio and ethylthio; allylthio; arylthio groups with 6 to 20 carbon atoms such as phenylthio, 1-naphthylthio, and 2-naphthylthio; sulfoxy groups. (group); alkylsulfonoxy groups with 1 to 20 carbon atoms, such as methylsulfonoxy and ethylsulfonoxy; arylsulfonoxy groups with 6 to 20 carbon atoms, such as phenylsulfonoxy, 1-naphthylsulfonoxy, and 2-naphthylsulfonoxy; silyl groups; boronyl groups; alkylamino groups with 1 to 20 carbon atoms, such as monomethylamino, dimethylamino, trimethylamino, monoethylamino, diethylamino, and triethylamino; arylsulfonoxy groups with 6 to 20 carbon atoms, such as monophenylamino, diphenylamino, and triphenylamino. Arylamino groups with 7 to 20 carbon atoms, such as benzylamino; carboxyl; carbamoyl; alkyl carbonyl groups with 2 to 20 carbon atoms, such as acetyl and propionyl; aryl carbonyl groups with 7 to 20 carbon atoms, such as benzoyl, 1-naphthylcarbonyl, and 2-naphthylcarbonyl; alkoxy carbonyl groups with 2 to 20 carbon atoms, such as methoxycarbonyl and ethoxycarbonyl; aryloxy carbonyl groups with 7 to 20 carbon atoms, such as phenyloxycarbonyl, 1-naphthyloxycarbonyl, and 2-naphthyloxycarbonyl; and so on.

[0063] Examples of halogen atoms include fluorine, chlorine, bromine, and iodine. From a synthetic point of view, chlorine and bromine atoms are preferred, and bromine atoms are more preferred.

[0064] As R 1 R 2 and R 11 For example, the groups represented by formulas (D-1) to (D-47) and (G-1) to (G-22) can be cited below. * indicates a linking bond.

[0065]

[0066]

[0067] As R 1 and R 2The groups are preferably saturated chain hydrocarbon groups that may have substituents (A1), aromatic hydrocarbon groups that may have substituents (A1), or groups formed by combining aromatic hydrocarbon groups that may have substituents (A1) with chain hydrocarbon groups. From the viewpoint of improving the solubility of compound (I) in a solvent, the saturated chain hydrocarbon group is preferably a saturated branched hydrocarbon group. The number of carbon atoms in the saturated chain hydrocarbon group (preferably a saturated branched hydrocarbon group) can be 1 to 30, preferably 1 to 20, more preferably 3 to 15. The number of carbon atoms in the aromatic hydrocarbon group, or the group formed by combining aromatic hydrocarbon groups with chain hydrocarbon groups, is preferably 6 to 20, more preferably 6 to 15, and even more preferably 8 to 15. From the viewpoint of improving the fluorescence intensity of the obtained color filter, as R 1 and R 2 More preferably, it is a group represented by formulas (D-4) to (D-14) or formulas (G-5) to (G-22), and even more preferably, it is a group represented by any one of formulas (D-4) to (D-14), (G-5), (G-7), (G-8), (G-11) to (G-13), (G-15), (G-16), (G-19), (G-21), or (G-22), and particularly preferably, it is a group represented by any one of formulas (D-4) to (D-14), (G-7), (G-11), (G-13), (G-15), or (G-16).

[0068] Additionally, as R 1 and R 2 Preferably, they are the same group.

[0069] As R 11 Preferably, the group is a saturated chain hydrocarbon group that may have a substituent (A1), a saturated alicyclic hydrocarbon group that may have a substituent (A1), a group formed by combining alicyclic hydrocarbon groups that may have a substituent (A1) with a chain hydrocarbon group, an aromatic hydrocarbon group that may have a substituent (A1), or a group formed by combining aromatic hydrocarbon groups that may have a substituent (A1) with a chain hydrocarbon group. The number of carbon atoms in the aforementioned saturated chain hydrocarbon group can be 1 to 30, preferably 1 to 25, more preferably 1 to 20, further preferably 1 to 18, and even more preferably 3 to 15. The number of carbon atoms in the aforementioned saturated alicyclic hydrocarbon group, or the group formed by combining alicyclic hydrocarbon groups with a chain hydrocarbon group, is preferably 3 to 20, more preferably 6 to 20, and even more preferably 6 to 15. The number of carbon atoms in the aforementioned aromatic hydrocarbon group, or the group formed by combining an aromatic hydrocarbon group with a chain hydrocarbon group, is preferably 6 to 20, more preferably 7 to 20, even more preferably 8 to 20, and even more preferably 10 to 20. From the viewpoint of improving the solubility of compound (I) in a solvent, as R... 11Preferably, the group represented by formulas (D-4) to (D-31), (D-34) to (D-46), (G-1), or (G-5) to (G-22) is preferred, more preferably the group represented by formulas (D-4) to (D-14), or (G-5) to (G-22) is preferred, even more preferably the group represented by any one of formulas (D-4) to (D-14), (G-5), (G-7), (G-8), (G-11) to (G-13), (G-15), (G-16), (G-19), (G-21), or (G-22) is preferred, and particularly preferably the group represented by any one of formulas (D-4) to (D-14), (G-7), (G-11), (G-13), (G-15), or (G-16) is preferred.

[0070] Additionally, R 1 and R 2 In the case of the same group, R is preferred. 11 With R 1 and R 2 These are different groups.

[0071] As R 3 ~R 10 The *-OR symbol represents 11 Examples of R mentioned above can be cited. 11 Examples of oxygen groups include alkoxy groups with 1 to 30 carbon atoms and aryloxy groups with 1 to 30 carbon atoms. As *-OR 11 Specifically, examples include methoxy, ethoxy, propoxy, butoxy, pentoxy, phenoxy, naphthyloxy, etc.

[0072] As R 3 ~R 10 The *-CO-OR symbol 11 Examples of R mentioned above can be cited. 11 Examples of oxycarbonyl groups include alkoxycarbonyl groups with 1 to 30 carbon atoms and aryloxycarbonyl groups with 1 to 30 carbon atoms. As *-CO-OR 11 The R it possesses 11Preferably, it is a saturated chain hydrocarbon group, a saturated alicyclic hydrocarbon group, a group formed by combining an alicyclic hydrocarbon group and a chain hydrocarbon group, an aromatic hydrocarbon group, or a group formed by combining an aromatic hydrocarbon group and a chain hydrocarbon group. More preferably, it is a saturated chain hydrocarbon group with 1 to 20 carbon atoms, a saturated alicyclic hydrocarbon group with 3 to 15 carbon atoms, a group formed by combining an alicyclic hydrocarbon group with 4 to 15 carbon atoms and a chain hydrocarbon group, an aromatic hydrocarbon group with 6 to 20 carbon atoms, or a group formed by combining an aromatic hydrocarbon group with 7 to 20 carbon atoms and a chain hydrocarbon group. More preferably, it is a saturated chain hydrocarbon group with 3 to 18 carbon atoms, a group formed by combining an alicyclic hydrocarbon group with 4 to 10 carbon atoms and a chain hydrocarbon group, or a group formed by combining an aromatic hydrocarbon group with 7 to 15 carbon atoms and a chain hydrocarbon group. As *-CO-OR 11 Specifically, examples include methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, sec-butoxycarbonyl, tert-butoxycarbonyl, butoxycarbonyl, pentyloxycarbonyl, (1-ethyl)pentyloxycarbonyl, hexyloxycarbonyl, (2-ethyl)hexyloxycarbonyl, heptyloxycarbonyl, (1-butyl)heptyloxycarbonyl, octyloxycarbonyl, (1-heptyl)octyloxycarbonyl, nonyloxycarbonyl, decyloxycarbonyl, undecyloxycarbonyl, dodecyloxycarbonyl, tridecyloxycarbonyl, tetradecyloxycarbonyl, pentadecyloxycarbonyl, hexadecyloxycarbonyl, heptadecanyloxycarbonyl, octadecyloxycarbonyl, phenyloxycarbonyl, benzyloxycarbonyl, cyclohexyloxycarbonyl, cyclohexylmethoxycarbonyl, eicosyloxycarbonyl, etc.

[0073] As R 3 ~R 10 Examples of halogen atoms include fluorine, chlorine, bromine, and iodine.

[0074] As R 3 With R 4 R 4 With R 5 R 5 With R 6 R 7 With R 8 R 8 With R 9 and R 9 With R 10 Each forms a compound containing either *-CO-O-CO-* or *-CO-N(R) 11 A ring of )-CO-* (* indicates a connecting bond), for example, R 3 With R 4 R 4 With R 5 R 5 With R 6 R 7 With R 8R 8 With R 9 and R 9 With R 10 The cases where each group is a divalent group represented independently by the following formulas (H-1) to (H-16). In formulas (H-1) to (H-16), * denotes R. 3 With R 4 R 4 With R 5 R 5 With R 6 R 7 With R 8 R 8 With R 9 or R 9 With R 10 It possesses linkages with the benzo[a]perylene skeleton.

[0075]

[0076] It should be noted that, as mentioned above, *-CO-N(R) 11 The R-CO-* ring possesses 11 Preferably, the substituent is a saturated chain hydrocarbon group having a substituent (A1), an aromatic hydrocarbon group having a substituent (A1), or a group formed by combining an aromatic hydrocarbon group having a substituent (A1) with a chain hydrocarbon group. More preferably, the substituent is a saturated chain hydrocarbon group having 3 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 15 carbon atoms, or a group formed by combining an aromatic hydrocarbon group having 7 to 20 carbon atoms, and more preferably, a saturated chain hydrocarbon group having 6 to 18 carbon atoms, or a group formed by combining an aromatic hydrocarbon group having 7 to 18 carbon atoms, and a chain hydrocarbon group. From the viewpoint of improving the solubility of compound (I) in a solvent, the above-mentioned saturated chain hydrocarbon group is preferably a saturated branched chain hydrocarbon group. In addition, the substituent (A1) is preferably a halogen atom (especially a bromine atom).

[0077] Specifically, examples of groups represented by formula (H-9) include those represented by formulas (H-9-1) to (H-9-16). In formulas (H-9-1) to (H-9-16), * denotes R. 3 With R 4 R 4 With R 5 R 5 With R 6 R 7 With R 8 R 8 With R 9 or R 9 With R 10It possesses linkages with the benzo[a]perylene skeleton.

[0078]

[0079] As R 3 and R 6 ~R 10 Preferably, it contains hydrogen atoms. R 3 and R 6 ~R 10 By combining them appropriately, compounds with desired absorption and fluorescence wavelengths can be formed.

[0080] As R 4 and R 5 Preferred to be independent of each other as *-OR 11 or*-CO-OR 11 , or by R 4 and R 5 Forming a compound containing *-CO-O-CO-* or *-CO-N(R) 11 The ring of )-CO-*. From the viewpoint of improving the solubility of compound (I) in solvent and increasing the fluorescence intensity of the obtained filter, the above-mentioned *-OR 11 or*-CO-OR 11 More preferably, it is an alkoxy group with 1 to 20 carbon atoms, an alkoxycarbonyl group with 1 to 20 carbon atoms, or an aryloxycarbonyl group with 6 to 20 carbon atoms; even more preferably, it is an alkoxy group with 1 to 15 carbon atoms, an alkoxycarbonyl group with 1 to 15 carbon atoms, or an aryloxycarbonyl group with 7 to 15 carbon atoms; even more preferably, it is an alkoxy group with 1 to 10 carbon atoms or an alkoxycarbonyl group with 1 to 10 carbon atoms; particularly preferably, it is an alkoxycarbonyl group with 1 to 10 carbon atoms. From the above R... 4 and R 5 Forming a compound containing *-CO-O-CO-* or *-CO-N(R) 11 In the case of a )-CO-* ring, R is more preferred. 4 With R 5 The compound (I) may form a group represented by formulas (H-1) to (H-3) or (H-9) to (H-11), and more preferably, a group represented by formulas (H-1) to (H-3) or (H-9-1) to (H-9-16). From the viewpoint of improving the solubility of compound (I) in a solvent and improving the fluorescence intensity of the obtained filter, it is particularly preferred to form a group represented by any one of formulas (H-1), (H-9-5), (H-9-6), (H-9-9), (H-9-11), (H-9-12), and (H-9-14) to (H-9-16).

[0081] Specific examples of compound (I) include compounds (I-1) to (1-87) shown in Tables 1 to 3 below.

[0082] [Table 1]

[0083]

[0084] [Table 2]

[0085]

[0086] [Table 3]

[0087]

[0088] In Tables 1-3, H represents a hydrogen atom. D-6, D-13, G-7, H-1, H-9-6, H-9-9, H-9-11, H-9-12, H-9-14, H-9-15, and H-9-16 refer to the groups represented by the formulas (D-6), (D-13), (G-7), (H-1), (H-9-6), (H-9-9), (H-9-11), (H-9-12), (H-9-14), (H-9-15), and (H-9-16), respectively. F-1 to F-21 refer to the groups represented by the formulas (F-1) to (F-21), respectively. * indicates a connecting bond.

[0089]

[0090] From the viewpoint of improving the solubility of compound (I) in the solvent and improving the fluorescence intensity of the obtained filter, compounds (I-2), (I-3), (I-9), (I-10), (I-12), (I-13), (I-19) to (I-31), (I-34) to (I-50), (I-53) to (I-69), or (I-72) to (I-87) are preferred, compounds (I-3), (I-9), (I-12), (I-13), (I-21) to (I-30), (I-69), or (I-72) to (I-87) are more preferred, and compounds (I-3), (I-9), (I-12), (I-13), (I-21) to (I-30), (I-69), (I-72) to (I-83), (I-85), or (I-87) are even more preferred.

[0091] Compound (I) is preferably a compound represented by formula (Ia).

[0092] <<Compounds represented by formula (Ia)>>

[0093]

[0094] In formula (Ia),

[0095] R 1a and R 2a Each can be independently represented as an aryl group having 6 to 20 carbon atoms that may have a substituent (A2) or a heteroaryl group having 1 to 20 carbon atoms that may have a substituent (A2).

[0096] R 3a R 6a R 7a R 8a R 9a and R 10a Each can be used to independently represent a hydrogen atom, *-R 11a 、*-OR 11a 、*-CO-OR 11a Halogen atom, hydroxyl group, carboxyl group or nitro group.

[0097] R 11a This refers to a hydrocarbon group with 1 to 20 carbon atoms that can have substituents (A1), and the presence of multiple R groups. 11a In certain circumstances, they can be different from each other.

[0098] R 4a and R 5a Each can be represented independently as *-CO-OR 11a , or R 4a and R 5a The groups represented by formula (a) or formula (b) are bonded together.

[0099]

[0100] In equations (a) and (b),

[0101] R b1 and R b2 Each can be independently represented as a hydrocarbon group having 1 to 20 carbon atoms that may have a substituent (A1).

[0102] R c1 This indicates an aryl group with 6 to 20 carbon atoms and a substituent (A2).

[0103] R 4a and R 5a In the case where R is the group represented by formula (b), 1a R 2a and R c1 These three cannot be the same group.

[0104] * indicates a connection key.

[0105] As R 1a R 2aand R c1 Examples of aryl groups with 6 to 20 carbon atoms include phenyl, 1-naphthyl, 2-naphthyl, phenanthryl, anthraceneyl, and pyreneyl, with 6 to 18 carbon atoms being the most preferred, and 6 to 15 more preferred.

[0106] As R 1a and R 2a Examples of heteroaryl groups with 1 to 20 carbon atoms include furanyl, pyrroleyl, thiophenyl, oxazolyl, pyridyl, quinolinyl, thiazolyl, benzothiazolyl, and carbazoleyl. The number of carbon atoms is preferably 2 to 20, and more preferably 3 to 15.

[0107] As R 1a R 2a and R c1 The aryl group representing 6 to 20 carbon atoms and R 1a and R 2aThe heteroaryl groups represented by carbon atoms with 1 to 20 carbon atoms may have substituents (A2), for example, halogen atoms; nitrile groups; nitro groups; amino groups; hydroxyl groups; alkyl groups with 1 to 20 carbon atoms such as methyl, ethyl, isopropyl, and tert-butyl; cycloalkyl groups with 3 to 20 carbon atoms such as cyclopropyl and cyclobutyl; alkenyl groups with 2 to 20 carbon atoms such as vinyl and 1-propenyl; aryl groups with 6 to 20 carbon atoms such as phenyl and 1-naphthyl; aralkyl groups with 7 to 20 carbon atoms such as benzyl and phenethyl; phenyl vinyl (styryl), etc. Aryl alkenyl groups with 8 to 20 carbon atoms; alkoxy groups with 1 to 20 carbon atoms, such as methoxy and ethoxy; aryloxy groups with 6 to 20 carbon atoms, such as phenyloxy, 1-naphthyloxy, and 2-naphthyloxy; thiol groups; alkyl thio groups with 1 to 20 carbon atoms, such as methyl thio and ethyl thio; allyl thio; aryl thio groups with 6 to 20 carbon atoms, such as phenyl thio, 1-naphthyl thio, and 2-naphthyl thio; sulfonoxy groups; alkyl sulfonoxy groups with 1 to 20 carbon atoms, such as methyl sulfonoxy and ethyl sulfonoxy; phenyl sulfonoxy... Arylsulfonyl groups with 6 to 20 carbon atoms, such as 1-naphthylsulfonyl, 2-naphthylsulfonyl, etc.; silyl groups; boranyl groups; alkylamino groups with 1 to 20 carbon atoms, such as monomethylamino, dimethylamino, trimethylamino, monoethylamino, diethylamino, triethylamino, etc.; arylamino groups with 6 to 20 carbon atoms, such as monophenylamino, diphenylamino, triphenylamino, etc.; aralkylamino groups with 7 to 20 carbon atoms, such as benzylamino; carboxyl groups; carbamoyl groups; acetyl groups, propionyl groups, etc., with 2 to 20 carbon atoms. aryl carbonyl groups; aryl carbonyl groups with 7 to 20 carbon atoms, such as benzoyl, 1-naphthyl carbonyl, and 2-naphthyl carbonyl; alkoxy carbonyl groups with 2 to 20 carbon atoms, such as methoxy carbonyl and ethoxy carbonyl; aryloxy carbonyl groups with 7 to 20 carbon atoms, such as phenyloxy carbonyl, 1-naphthyloxy carbonyl, and 2-naphthyloxy carbonyl; heterocyclic groups with 1 to 20 carbon atoms, such as furanyl, pyrroleyl, and thiopheneyl; ethynyl; and alkane dimethyl groups with 1 to 20 carbon atoms that form a ring with at least two carbon atoms of the above-mentioned aryl groups; etc.

[0108] Examples of halogen atoms include fluorine, chlorine, bromine, and iodine. From a synthetic point of view, chlorine and bromine atoms are preferred, and bromine atoms are more preferred.

[0109] As R 1a and R 2a The aryl groups are preferably aryl groups that can have substituents (A2), and each group is independent of the others. The number of carbon atoms in the aryl group is preferably 6 to 15, more preferably 6 to 10, and phenyl is particularly preferred as the aryl group.

[0110] Additionally, as R 1a and R 2a Preferably, they are the same group.

[0111] As R 1aand R 2a The aryl group representing 6 to 20 carbon atoms and the heteroaryl group representing 1 to 20 carbon atoms preferably have a substituent (A2). The substituent (A2) is preferably an alkyl group or a halogen atom representing 1 to 20 carbon atoms, more preferably an alkyl group or a halogen atom representing 1 to 10 carbon atoms, even more preferably an alkyl group representing 1 to 6 carbon atoms, and even more preferably an alkyl group representing 1 to 4 carbon atoms.

[0112] R 1a and R 2a When the aryl group having 6 to 20 carbon atoms and the heteroaryl group having 1 to 20 carbon atoms have a substituent (A2), the number of substituents (A2) is not limited; it can be one or more, preferably two to four, and more preferably two from the viewpoint of improving the fluorescence intensity of the obtained filter. It should be noted that the substituent (A2) is preferably located in at least one ortho position, and more preferably in two ortho positions.

[0113] R 1a and R 2a When aryl groups with 6 to 20 carbon atoms and heteroaryl groups with 1 to 20 carbon atoms have multiple substituents (A2), they can be the same group or different groups.

[0114] As R c1 The number of carbon atoms of the aryl group that may have a substituent (A2) is preferably 6 to 15, more preferably 6 to 10, and phenyl is particularly preferred as the aryl group.

[0115] As R c1 The aryl group representing 6 to 20 carbon atoms preferably has a substituent (A2). The substituent (A2) is preferably an alkyl group, a halogen atom, or an alkane diene group with 1 to 20 carbon atoms that forms a ring with at least 2 carbon atoms of the aryl group. More preferably, it is an alkyl group, a halogen atom, or an alkane diene group with 1 to 10 carbon atoms that forms a ring with at least 2 carbon atoms of the aryl group.

[0116] Additionally, as R c1 The aryl group represented by the carbon number 6 to 20 is preferably a substituent (A2) consisting of an alkyl group having at least one carbon number 4 to 20, a halogen atom, or any group consisting of an alkane diene having at least one carbon number 1 to 20 that forms a ring with at least two carbon atoms of the aryl group.

[0117] R c1 When the aryl group representing 6 to 20 carbon atoms has a substituent (A2), the number of substituents (A2) is not limited, and can be 1 or more, preferably 1 to 3.

[0118] R c1 When an aryl group representing 6 to 20 carbon atoms has multiple substituents (A2), they can be the same group or different groups.

[0119] As R 11a R b1 and R b2 The hydrocarbon groups representing 1 to 20 carbon atoms, excluding examples with 21 or more carbon atoms, can be exemplified by R. 1 R 2 and R 11 Examples that represent the same hydrocarbon group.

[0120] As R 11a R b1 and R b2 The substituents (Al) that can be present in hydrocarbon groups with 1 to 20 carbon atoms can be exemplified by those related to R. 1 R 2 and R 11 Examples of hydrocarbon groups with 1 to 30 carbon atoms that may have the same substituent (A1).

[0121] As R 11a Preferably, it is a saturated aliphatic hydrocarbon group having 1 to 20 carbon atoms that may have a substituent (A1), an aromatic hydrocarbon group having 6 to 20 carbon atoms that may have a substituent (A1), or a group formed by combining an aromatic hydrocarbon group having 7 to 20 carbon atoms that may have a substituent (A1) with a chain hydrocarbon group. More preferably, it is a saturated chain hydrocarbon group having 1 to 20 carbon atoms that may have a substituent (A1), a group formed by combining a saturated alicyclic hydrocarbon group having 4 to 20 carbon atoms that may have a substituent (A1) with a chain hydrocarbon group, or a group formed by combining an aromatic hydrocarbon group having 7 to 20 carbon atoms that may have a substituent (A1) with a chain hydrocarbon group. More preferably, it is a group formed by combining a saturated alicyclic hydrocarbon group having 4 to 20 carbon atoms that may have a substituent (A1) with a chain hydrocarbon group. The group may be composed of 18 saturated chain hydrocarbon groups, a group formed by combining a saturated alicyclic hydrocarbon group with 4 to 15 carbon atoms that may have a substituent (A1) with a chain hydrocarbon group, or a group formed by combining an aromatic hydrocarbon group with 7 to 15 carbon atoms that may have a substituent (A1) with a chain hydrocarbon group. More preferably, it may be a branched alkyl group with 3 to 15 carbon atoms that may have a substituent (A1), a straight-chain alkyl group with 4 to 18 carbon atoms that may have a substituent (A1), a group formed by combining a saturated alicyclic hydrocarbon group with 6 to 15 carbon atoms that may have a substituent (A1) with a chain hydrocarbon group, or a group formed by combining an aromatic hydrocarbon group with 7 to 15 carbon atoms that may have a substituent (A1) with a chain hydrocarbon group. As R 11a Specifically, the preferred groups are those represented by the formulas (D-4) to (D-31) or (D-34) to (D-46) above.

[0122] As R b1 and R b2 The groups are preferably saturated chain hydrocarbon groups that may have substituents (A1), saturated alicyclic hydrocarbon groups that may have substituents (A1), or groups formed by combining chain hydrocarbon groups that may have substituents (A1) with alicyclic hydrocarbon groups, and more preferably saturated chain hydrocarbon groups that may have substituents (A1). The aforementioned saturated chain hydrocarbon groups are preferably saturated straight-chain hydrocarbon groups, and the number of carbon atoms in the aforementioned saturated chain hydrocarbon groups (preferably saturated straight-chain hydrocarbon groups) can be 1 to 20, preferably 3 to 20, more preferably 3 to 15, and even more preferably 3 to 10.

[0123] Additionally, as R b1 and R b2 Preferably, the total number of carbon atoms in the two groups is 6 or more.

[0124] As R b1 and R b2 Preferably, they are the same group.

[0125] As R 3a R 6a R 7a R 8a R 9a and R 10a The *-OR symbol represents 11a Examples of R can be cited. 3 ~R 10 The *-OR symbol represents 11 The same example.

[0126] As R 3a ~R 10a The *-CO-OR symbol 11a Examples of R can be cited. 3 ~R 10 The *-CO-OR symbol 11 The same example.

[0127] As R 3a R 6a R 7a R 8a R 9a and R 10a The halogen atom represented can be exemplified by R. 3 ~R 10 Examples that represent the same halogen atom.

[0128] As R 3a R 6a R 7a R 8a R 9a and R10a From a synthetic point of view, hydrogen atoms are preferred. 3a R 6a R 7a R 8a R 9a and R 10a By combining them appropriately, compounds with desired absorption and fluorescence wavelengths can be formed.

[0129] As R 4a and R 5a The groups represented by formula (a) formed by bonding can be specifically exemplified by the groups represented by formulas (H-9-5) and (H-9-6) above.

[0130] As R 4a and R 5a The groups represented by formula (b) formed by bonding can be specifically exemplified by the groups represented by formulas (H-9-10) to (H-9-16) above.

[0131] Among compounds (Ia), from the viewpoint of improving the fluorescence intensity of the obtained color filter and improving the solubility of compound (I) in the solvent, compounds represented by formulas (Ii) to (I-iii) are preferred.

[0132] <<<Compounds represented by formula (Ii)>>>

[0133]

[0134] In formula (Ii),

[0135] R 1i ~R 4i R 11i and R 12i Each can be independently represented as a hydrocarbon group having 1 to 20 carbon atoms that may have a substituent (A1).

[0136] R 5i ~R 10i R 3ai R 6ai R 7ai R 8ai R 9ai and R 10ai Independently representing hydrogen atoms, hydrocarbon groups with 1 to 20 carbon atoms that may have substituents (A1), halogen atoms, hydroxyl groups, alkoxy groups with 1 to 20 carbon atoms, aryloxy groups with 6 to 20 carbon atoms, carboxyl groups, alkoxycarbonyl groups with 2 to 20 carbon atoms, and nitro groups.

[0137] <<<Compounds represented by formula (I-ii)>>>

[0138]

[0139] In formula (I-ii),

[0140] R 1i ~R 4i R b1i and R b2i Each can be independently represented as a hydrocarbon group having 1 to 20 carbon atoms that may have a substituent (A1).

[0141] R 5i ~R 10i R 3ai R 6ai R 7ai R 8ai R 9ai and R 10ai Independently representing hydrogen atoms, hydrocarbon groups with 1 to 20 carbon atoms that may have substituents (A1), halogen atoms, hydroxyl groups, alkoxy groups with 1 to 20 carbon atoms, aryloxy groups with 6 to 20 carbon atoms, carboxyl groups, alkoxycarbonyl groups with 2 to 20 carbon atoms, and nitro groups.

[0142] <<<Compounds represented by formulas (I-iii)>>>

[0143]

[0144] In formula (I-iii),

[0145] Ar 7i ~Ar 9i Each can independently represent an aryl group with 6 to 20 carbon atoms that may have a substituent (A2). However, Ar 7 ~Ar 9 These three will not all be the same group.

[0146] R 3ai R 6ai R 7ai R 8ai R 9ai and R 10ai Independently representing hydrogen atoms, hydrocarbon groups with 1 to 20 carbon atoms that may have substituents (A1), halogen atoms, hydroxyl groups, alkoxy groups with 1 to 20 carbon atoms, aryloxy groups with 6 to 20 carbon atoms, carboxyl groups, alkoxycarbonyl groups with 2 to 20 carbon atoms, and nitro groups.

[0147] In equations (Ii) to (I-iii), R is used as 1i ~R 12i R 3ai R 6ai ~R 10ai R b1i and Rb2i The hydrocarbon groups representing 1 to 20 carbon atoms, excluding examples with 21 or more carbon atoms, can be exemplified by R. 1 R 2 and R 11 Examples that represent the same hydrocarbon group.

[0148] As R 1i ~R 12i R 3ai R 6ai ~R 10ai R b1i and R b2i The substituents (Al) that can be present in hydrocarbon groups with 1 to 20 carbon atoms can be exemplified by those related to R. 1 R 2 and R 11 Examples of hydrocarbon groups with 1 to 30 carbon atoms that may have the same substituent (A1).

[0149] As Ar 7i ~Ar 9i Aryl groups representing 6 to 20 carbon atoms can be exemplified by those related to R. 1a R 2a and R c1 Examples of aryl groups with the same number of carbon atoms, ranging from 6 to 20.

[0150] As Ar 7i ~Ar 9i The aryl group representing 6 to 20 carbon atoms can have substituents (A2), and examples of substituents related to R can be given. 1a R 2a and R c1 Examples of aryl groups with 6 to 20 carbon atoms that can have the same substituent (A2).

[0151] As R 5i ~R 10i R 3ai R 6ai R 7ai R 8ai R 9ai and R 10ai The halogen atom represented can be exemplified by R. 3 ~R 10 Examples where the halogen atoms are the same. From a synthetic point of view, chlorine or bromine atoms are preferred.

[0152] As R 5i ~R 10i R 3ai R 6ai R 7ai R 8ai R 9aiand R 10ai Alkoxy groups representing 1 to 20 carbon atoms include, for example, methoxy, ethoxy, propoxy, butoxy, pentoxy, etc.

[0153] As R 5i ~R 10i R 3ai R 6ai R 7ai R 8ai R 9ai and R 10ai Aryloxy groups representing 6 to 20 carbon atoms include phenoxy, 1-naphthyloxy, and 2-naphthyloxy.

[0154] As R 5i ~R 10i R 3ai R 6ai R 7ai R 8ai R 9ai and R 10ai Examples of alkoxycarbonyl groups with 2 to 20 carbon atoms include methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, sec-butoxycarbonyl, tert-butoxycarbonyl, butoxycarbonyl, pentyloxycarbonyl, (1-ethyl)pentyloxycarbonyl, hexyloxycarbonyl, and (2-ethyl)hexyloxycarbonyl.

[0155] As R 1i ~R 4i The alkyl groups are preferably alkyl groups having 1 to 20 carbon atoms, more preferably alkyl groups having 1 to 10 carbon atoms, even more preferably alkyl groups having 1 to 6 carbon atoms, and even more preferably alkyl groups having 1 to 4 carbon atoms.

[0156] As R 5i ~R 10i Each of these atoms is preferably a hydrogen atom or a halogen atom, and more preferably a hydrogen atom.

[0157] As R 3ai R 6ai ~R 10ai Preferably, it contains hydrogen atoms.

[0158] As R 11i and R 12iThe groups are preferably, independently, saturated aliphatic hydrocarbon groups with 1 to 20 carbon atoms, aromatic hydrocarbon groups with 6 to 20 carbon atoms, or groups composed of aromatic hydrocarbon groups with 7 to 20 carbon atoms and chain hydrocarbon groups. More preferably, they are saturated chain hydrocarbon groups with 1 to 20 carbon atoms, groups composed of saturated alicyclic hydrocarbon groups with 4 to 20 carbon atoms and chain hydrocarbon groups, or groups composed of aromatic hydrocarbon groups with 7 to 20 carbon atoms and chain hydrocarbon groups. Even more preferably, they are saturated chain hydrocarbon groups with 3 to 18 carbon atoms, groups composed of saturated alicyclic hydrocarbon groups with 4 to 15 carbon atoms and chain hydrocarbon groups. The group formed by combining aromatic hydrocarbon groups with 7 to 15 carbon atoms with chain hydrocarbon groups is more preferably a branched alkyl group with 3 to 15 carbon atoms, a straight-chain alkyl group with 4 to 18 carbon atoms, a group formed by combining saturated alicyclic hydrocarbon groups with 6 to 15 carbon atoms with chain hydrocarbon groups, or a group formed by combining aromatic hydrocarbon groups with 7 to 15 carbon atoms with chain hydrocarbon groups. Particularly preferred are branched alkyl groups with 3 to 12 carbon atoms, straight-chain alkyl groups with 5 to 18 carbon atoms, or a group formed by combining aromatic hydrocarbon groups with 7 to 12 carbon atoms with chain hydrocarbon groups. Additionally, as R... 11i and R 12i Preferably, they are the same group.

[0159] As R b1i and R b2i The preferred groups are, independently, saturated chain hydrocarbon groups with 1 to 20 carbon atoms that may have substituents (A1), saturated alicyclic hydrocarbon groups with 3 to 20 carbon atoms that may have substituents (A1), or groups formed by combining chain hydrocarbon groups with 4 to 20 carbon atoms that may have substituents (A1) with alicyclic hydrocarbon groups; more preferably, saturated chain hydrocarbon groups with 3 to 20 carbon atoms; even more preferably, saturated straight-chain hydrocarbon groups with 3 to 20 carbon atoms; even more preferably, saturated straight-chain hydrocarbon groups with 3 to 15 carbon atoms; and particularly preferably, saturated straight-chain hydrocarbon groups with 3 to 10 carbon atoms. Additionally, as R... b1i and R b2i Preferably, the total number of carbon atoms in the two groups is 6 or more. Furthermore, as R... b1i and R b2i Preferably, they are the same group.

[0160] As Ar 7i and Ar 8iThe aryl group (A2) is preferably an aryl group with 6 to 15 carbon atoms, more preferably an aryl group with 6 to 10 carbon atoms, and even more preferably a phenyl group with a substituent (A2). The substituent (A2) is preferably an alkyl group with 1 to 20 carbon atoms or a halogen atom, more preferably an alkyl group with 1 to 10 carbon atoms or a halogen atom, more preferably an alkyl group with 1 to 6 carbon atoms, and even more preferably an alkyl group with 1 to 4 carbon atoms. The number of substituents (A2) is not particularly limited, but is preferably 2 to 4, more preferably 2, and particularly preferably 2 substituents (A2) are located in the ortho position. Furthermore, as Ar... 7i and Ar 8i Preferably, they are the same group.

[0161] As Ar 9i Preferably, the substituent (A2) is an aryl group having 6 to 15 carbon atoms, more preferably an aryl group having 6 to 10 carbon atoms, even more preferably a phenyl group having a substituent (A2), and even more preferably a phenyl group having a substituent (A2). The substituent (A2) is preferably an alkyl group having 1 to 20 carbon atoms, a halogen atom, or an alkane diel group having 1 to 20 carbon atoms that forms a ring with at least two carbon atoms of the aryl group, more preferably an alkyl group having 1 to 10 carbon atoms, a halogen atom, or an alkane diel group having 1 to 10 carbon atoms that forms a ring with at least two carbon atoms of the aryl group. The number of the substituent (A2) is not particularly limited, but is preferably 1 to 3.

[0162] Compound (I) can be prepared, for example, by reacting a compound represented by the following formula (pt1) with maleic anhydride or maleic anhydride imide in the presence of a dehydrogenating agent. It should be noted that the compound (I) containing R... 4 and R 5 A compound that forms a ring containing *-CO-O-CO-* (* represents a linking bond) is called compound (I)'. The compound (I) contains R... 4 and R 5 Formation containing *-CO-N(R) 11 Compounds with a ring of )-CO-* (* indicates a connecting bond) are called compounds (I)”'.

[0163]

[0164] [In the formula, R] 1 ~R 3 and R 6 ~R 11 Same as the definition above.

[0165] As a compound represented by formula (pt1), for example, N 1 N 2 -Bis(2,6-diisopropylphenyl)perylene-3,4,9,10-tetracarboxylic acid diimide, N 1 N 2 -Bis(3-pentyl)perylene-3,4,9,10-tetracarboxylic acid diimide, N 1 N 2 -Bis(3-pentyl)perylene-3,4,9,10-tetracarboxylic acid diimide, etc.

[0166] The amount of maleic anhydride or maleic anhydride imide used is generally more than 1 mole and less than 1,000 moles relative to 1 mole of the compound represented by formula (pt1), preferably more than 1 mole and less than 800 moles, more preferably more than 1 mole and less than 600 moles, and even more preferably more than 1 mole and less than 400 moles.

[0167] The aforementioned dehydrogenating agent refers to a substance that removes hydrogen from a 6-membered ring compound, thereby aromaticating it. Preferably, tetrachlorobenzoquinone, p-benzoquinone, 2,5-dichloro-p-benzoquinone, 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, tetramethyl-p-benzoquinone, 2,5-diphenyl-p-benzoquinone, or tetrabromobenzoquinone are preferred, with tetrachlorobenzoquinone and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone being more preferred.

[0168] The reaction temperature is usually between -100℃ and 300℃.

[0169] Additionally, R in compound (I) 4 and R 5 Independent of each other as *-CO-OR 11a (* indicates a connecting bond) A compound (hereinafter, sometimes referred to as compound (I)”) can be produced, for example, by reacting compound (I)’ with compounds represented by formula (MA1-1) and (MA1-2) in a solvent.

[0170] In addition to the manufacturing methods described above, compound (I)' can also be manufactured, for example, by reacting a compound represented by formula (MA2) with compound (I)' in a solvent.

[0171] In the compound represented by formula (MA1-1), X represents a halogen atom, preferably a chlorine atom or a bromine atom. The compound represented by formula (MA1-1) can be used alone or in combination with two or more other compounds, and the compound represented by formula (MA1-2) can also be used alone or in combination with two or more other compounds.

[0172] The total amount of compounds represented by formulas (MA1-1) and (MA1-2) used relative to 1 mole of compound (I) is generally 1 mole or more and 20 moles or less, preferably 1 mole or more and 15 moles or less, and more preferably 1 mole or more and 10 moles or less.

[0173] The amount of compound represented by formula (MA2) used relative to 1 mole of compound (I) is generally 1 mole or more and 10 moles or less, preferably 1 mole or more and 8 moles or less, more preferably 1 mole or more and 6 moles or less, and even more preferably 1 mole or more and 4 moles or less.

[0174] Examples of solvents mentioned above include water; acetonitrile solvents such as acetonitrile; alcohol solvents such as methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1-octanol, and phenol; ether solvents such as diethyl ether and tetrahydrofuran; ketone solvents such as acetone and methyl isobutyl ketone; ester solvents such as ethyl acetate; aliphatic hydrocarbon solvents such as hexane; aromatic hydrocarbon solvents such as toluene; halogenated hydrocarbon solvents such as dichloromethane, chloroform, and 1,2-dichlorobenzene; amide solvents such as N,N-dimethylformamide and N-methylpyrrolidone; sulfoxide solvents such as dimethyl sulfoxide; carboxylic acid solvents such as acetic acid, propionic acid, and butyric acid; and imidazole.

[0175] The amount of solvent used, whether in the manufacture of compound (I)” or in the manufacture of compound (I)”', is generally 1 to 1000 parts by mass relative to 1 part by mass of compound (I)'.

[0176] The reaction temperature is typically between -100°C and 300°C, whether in the case of manufacturing compound (I)” or in the case of manufacturing compound (I)”'.

[0177] After the reaction is complete, there are no particular limitations on the method for removing compound (I)', compound (I)" or compound (I)"', and various known methods can be used. After removal, the residue can be purified by column chromatography or recrystallization. The chemical structure of the obtained compound can be determined using known analytical methods and conditions. There are no particular limitations on such analytical methods; examples include X-ray crystallography, mass spectrometry (LC), NMR analysis, and elemental analysis. X-ray crystallography can be performed, for example, according to Chemistry of Materials, 2012, Vol. 24, pp. 4647-4652.

[0178] Benzo[a]perylene compounds exhibit high and good solubility in solvents such as propylene glycol monomethyl ether acetate and cyclohexanone (especially propylene glycol monomethyl ether acetate). It should be noted that for solubility determination, approximately 50 mg of the compound whose solubility is to be measured (hereinafter, sometimes referred to as the solute) can be weighed into a 20 mL threaded tube, and approximately 500 mg of solvent can be added. The total mass of solute and solvent is weighed, and the mixture is stirred with a mix rotor for 30 minutes. If dissolution is visually confirmed, the mass of the solute relative to the total mass of the solute and solvent is calculated using the following formula (h). If dissolution is not visually confirmed, solvent can be continuously added in increments of 500 mg until dissolution occurs, stirring with a mix rotor for 30 minutes after each addition. The solubility is calculated using the following formula (h) based on the mass of the solute relative to the total mass of the solute and solvent at the point of visual confirmation of dissolution.

[0179] Solubility (%) = (mass of solute) / (total mass of solute and solvent) × 100 (h)

[0180] Regarding the solubility of benzo[a]perylene compounds, the solubility in propylene glycol monomethyl ether acetate at 20°C is preferably 0.5% by mass or more, more preferably 0.8% by mass or more, even more preferably 1.0% by mass or more, and can be 15% by mass or less.

[0181] From the viewpoint of improving the fluorescence intensity of the obtained color filter, the content of benzo[a]perylene compound in the total amount of colorant (A) can be 100% by mass, as a lower limit, for example, it can be 0.1% by mass or more, preferably 5% by mass or more, more preferably 10% by mass or more, further preferably 15% by mass or more, and even more preferably 20% by mass or more.

[0182] Compared to perylene compounds used in conventional color-curing resin compositions, benzo[a]perylene compounds exhibit superior fluorescence intensity and better retention of fluorescence intensity after heat resistance testing. Therefore, color filters formed from color-curing resin compositions containing benzo[a]perylene compounds tend to have high fluorescence intensity and excellent brightness. It should be noted that the retention rate of fluorescence intensity after heat resistance testing can be measured by subjecting the color filter formed from the color-curing resin composition to a heating test, and the result is expressed as the retention rate of fluorescence intensity before and after the test. For example, a method of maintaining the temperature at approximately 200–250°C for 2–6 hours can be used for measurement.

[0183] The colorant (A) may also contain a perylene compound. Preferably, the perylene compound is a compound having substituents having carbonyl groups bonded at positions 3, 4, and 9, 10. The carbonyl groups at positions 3 and 4 are preferably bonded via oxygen atoms to form a lactone ring, or via nitrogen atoms to form an imide ring. Similarly, the carbonyl groups at positions 9 and 10 are preferably bonded via oxygen atoms to form a lactone ring, or via nitrogen atoms to form an imide ring. Furthermore, the perylene compound is preferably a compound having substituents having oxygen groups bonded independently at positions 1, 6, 7, and 12. Additionally, the perylene compound is preferably a red fluorescent dye. From the viewpoint of improving solubility in solvents and increasing the fluorescence intensity of the obtained filter, the compound represented by formula (II) (hereinafter sometimes referred to as compound (II)) is particularly preferred.

[0184] <<Compound (II)>>

[0185]

[0186] In formula (II),

[0187] Ar 21 ~Ar 26 Each can be independently represented as an aryl group with 6 to 20 carbon atoms that may have a substituent (A3).

[0188] R 21 ~R 24 Each of these can independently represent a hydrogen atom, a hydrocarbon group (1-20 carbon atoms, which may have substituents (A4)), a halogen atom, or a nitro group.

[0189] As Ar 21 ~Ar 26 Examples of aryl groups include phenyl and naphthyl groups, with phenyl being the most preferred.

[0190] As Ar 21 ~Ar 26The aryl group represented may have substituents (A3), including halogen atoms; nitrile groups; nitro groups; amino groups; amide groups; sulfonamide groups; hydroxyl groups; alkyl groups with 1 to 10 carbon atoms such as methyl, ethyl, isopropyl, and tert-butyl; cycloalkyl groups with 1 to 20 carbon atoms such as cyclopropyl and cyclobutyl; alkenyl groups with 2 to 10 carbon atoms such as vinyl and 1-propenyl; aryl groups with 6 to 10 carbon atoms such as phenyl and 1-naphthyl; aralkyl groups with 7 to 10 carbon atoms such as benzyl and phenethyl; and aralkyl groups with 8 to 10 carbon atoms such as phenylvinyl (styryl). Alkenyl groups; alkoxy groups with 1 to 10 carbon atoms, such as methoxy and ethoxy; aryloxy groups with 6 to 10 carbon atoms, such as phenyloxy, 1-naphthyloxy, and 2-naphthyloxy; thiols; alkylthio groups with 1 to 10 carbon atoms, such as methylthio and ethylthio; allylthio; arylthio groups with 6 to 10 carbon atoms, such as phenylthio, 1-naphthylthio, and 2-naphthylthio; sulfonyl groups; alkylsulfonyl groups with 1 to 10 carbon atoms, such as methylsulfonyl and ethylsulfonyl; phenylsulfonyl, 1-naphthylsulfonyl, and 2-naphthylsulfonyl... Arylsulfonyl groups with 6 to 10 carbon atoms; silyl groups; boranyl groups; alkylamino groups with 1 to 10 carbon atoms, such as monomethylamino, dimethylamino, trimethylamino, monoethylamino, diethylamino, and triethylamino; arylamino groups with 6 to 10 carbon atoms, such as monophenylamino; aralkylamino groups with 7 to 10 carbon atoms, such as benzylamino; alkylaminosulfonyl groups, such as N-methylaminosulfonyl, N,N-dimethylaminosulfonyl, and N-ethylaminosulfonyl, and carboxyl groups; carbamoyl groups; acetyl groups. Alkyl carbonyl groups with 2 to 10 carbon atoms, such as alkyl or propionyl; aryl carbonyl groups with 7 to 10 carbon atoms, such as benzoyl; alkoxy carbonyl groups with 2 to 10 carbon atoms, such as methoxycarbonyl or ethoxycarbonyl; aryloxy carbonyl groups with 7 to 20 carbon atoms, such as phenyloxycarbonyl; heterocyclic groups with 1 to 20 carbon atoms, such as furanyl, pyrroleyl, or thiophene; alkyl groups with 1 to 10 carbon atoms, such as chloromethyl, dichloromethyl, fluoromethyl, trifluoromethyl, or pentafluoroethyl, where some or all of the hydrogen atoms are replaced by halogen atoms; pentafluorothioalkyl; ethynyl, etc. Preferably, the alkyl groups and halogen atoms have 1 to 10 carbon atoms.

[0191] Examples of halogen atoms include fluorine, chlorine, bromine, and iodine. From a synthetic point of view, fluorine and chlorine atoms are preferred.

[0192] The alkyl group having 1 to 10 carbon atoms is preferably an alkyl group having 1 to 6 carbon atoms, and more preferably an alkyl group having 1 to 4 carbon atoms.

[0193] Ar 21 ~Ar 26 The aryl group may or may not have one or more substituents (A3).

[0194] As Ar21 ~Ar 26 For example, the groups represented by the following formulas (E-1) to (E-27) can be cited. * indicates a linking bond.

[0195]

[0196] From the viewpoint of improving the solubility of compound (II) in the solvent and increasing the fluorescence intensity of the obtained filter, as Ar 21 and Ar 22 Preferably, any group represented by formulas (E-5), (E-7), (E-8), and (E-11) is preferred. From the viewpoint of improving the solubility of compound (II) in the solvent and increasing the fluorescence intensity of the obtained filter, as an Ar... 23 ~Ar 26 Preferably, any group represented by formulas (E-1), (E-4), (E-9), (E-10), (E-17), and (E-18) is preferred.

[0197] As Ar 21 ~Ar 26 It can consist entirely of the same functional groups or of different functional groups.

[0198] Ar 21 with Ar 22 Preferably, they are the same group.

[0199] As R 21 ~R 24 The hydrocarbon groups representing 1 to 20 carbon atoms, excluding examples with 21 or more carbon atoms, can be exemplified by the R groups mentioned above. 1 R 2 and R 11 Examples that represent the same hydrocarbon group.

[0200] As R 21 ~R 24 The substituents (A4) that can be present in hydrocarbon groups with 1 to 20 carbon atoms can be exemplified by those related to the R group mentioned above. 1 R 2 and R 11 Examples of hydrocarbon groups with 1 to 30 carbon atoms that may have the same substituent (A1).

[0201] As R 21 ~R 24 Examples of halogen atoms include fluorine, chlorine, bromine, and iodine.

[0202] As R 21 ~R 24 Preferably, it contains hydrogen atoms.

[0203] As specific examples of compound (II), the compounds shown in Table 4 below can be cited.

[0204] [Table 4]

[0205]

[0206] In Table 4, H represents a hydrogen atom, and E-1, E-6, E-7, E-10, E-17, E-18, and E-19 refer to the groups represented by the above formulas (E-1), (E-6), (E-7), (E-10), (E-17), (E-18), and (E-19), respectively.

[0207] As compound (II), it is preferably compound (II-1) to (II-6), (II-9), (II-10), (II-15), (II-16), (II-21), or (II-22), and more preferably compound (II-3), (II-4), (II-9), (II-10), (II-15), or (II-16).

[0208] Compound (II) can be produced, for example, by reacting the compound represented by formula (pt2), the compound represented by formula (AR1), and the compound represented by formula (AR2) in a solvent.

[0209]

[0210] [In the formula, R] 21 ~R 24 Same as the definition above.

[0211] Ar X -NH2(AR1)

[0212] Ar X -OH(AR2)

[0213] [In the formula, Ar] X Compared with the above Ar 21 ~Ar 26 The definitions are the same.

[0214] Examples of compounds represented by formula (pt2) include 1,6,7,12-tetrachloroperylenetetracarboxylic dianhydride.

[0215] Examples of compounds represented by formula (AR1) include 2,6-diisopropylaniline, aniline, 3,5-dimethylaniline, and 3,5-di-tert-butylaniline. Compounds represented by formula (AR1) can be used alone or in combination with two or more other compounds.

[0216] Examples of compounds represented by formula (AR2) include phenol, 4-fluorophenol, 4-chlorophenol, and 4-bromophenol. Compounds represented by formula (AR1) can be used alone or in combination with two or more other compounds.

[0217] The total amount of the compound represented by formula (AR1) and the compound represented by formula (AR2) used relative to 1 mole of the compound represented by formula (pt2) is generally 1 mole or more and 10 moles or less, preferably 1 mole or more and 8 moles or less, more preferably 1 mole or more and 6 moles or less, and even more preferably 1 mole or more and 4 moles or less.

[0218] Examples of solvents include water; nitrile solvents such as acetonitrile; alcohol solvents such as methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1-octanol, and phenol; ether solvents such as diethyl ether and tetrahydrofuran; ketone solvents such as acetone and methyl isobutyl ketone; ester solvents such as ethyl acetate; aliphatic hydrocarbon solvents such as hexane; aromatic hydrocarbon solvents such as toluene; halogenated hydrocarbon solvents such as dichloromethane, chloroform, and 1,2-dichlorobenzene; amide solvents such as N,N-dimethylformamide and N-methylpyrrolidone; sulfoxide solvents such as dimethyl sulfoxide; carboxylic acid solvents such as acetic acid, propionic acid, and butyric acid; and imidazole. N-methylpyrrolidone, imidazole, and propionic acid are preferred.

[0219] The amount of solvent used is typically 1 to 1000 parts by mass relative to 1 part by mass of the compound represented by formula (pt2).

[0220] The reaction temperature is typically between -100°C and 300°C, preferably between -90°C and 200°C, and more preferably between -10°C and 150°C.

[0221] After the reaction is complete, there is no particular limitation on the method for removing compound (II), and various known methods can be used. For example, compound (II) can be removed by distillation of the solvent. Furthermore, after distillation of the solvent, the residue obtained can be purified by column chromatography or recrystallization. Alternatively, after the reaction is complete, compound (II) can be removed by filtration. After filtration, the residue obtained can be purified by column chromatography or recrystallization. The chemical structure of the obtained compound (II) can be determined using known analytical methods and conditions. Such analytical methods are not particularly limited, and examples include X-ray crystallography, mass spectrometry (LC), NMR analysis, and elemental analysis. X-ray crystallography can be performed, for example, according to Chemistry of Materials, 2012, Vol. 24, pp. 4647-4652.

[0222] The above compound (II-3) can be prepared by reacting 1,6,7,12-tetrachloroperyltetracarboxylic dianhydride with 2,6-diisopropylaniline and phenol in a solvent.

[0223] Representative commercially available products of compound (II-3) include Lumogen (registered trademark) F RED305.

[0224] When the colorant (A) contains a perylene compound, the perylene compound content in the total amount of colorant (A) is, for example, 0.1% by mass or more, preferably 1% by mass or more, more preferably 3% by mass or more, further preferably 5% by mass or more, further more preferably 10% by mass or more, for example, 95% by mass or less, preferably 90% by mass or less, more preferably 85% by mass or less, further preferably 80% by mass or less, and further more preferably 75% by mass or less.

[0225] In addition, when the colorant (A) contains a perylene compound, the perylene compound content is, for example, 3% by mass or more, preferably 5% by mass or more, more preferably 10% by mass or more, for example 95% by mass or less, preferably 90% by mass or less, more preferably 85% by mass or less, relative to the total amount of benzo[a]perylene compound and perylene compound.

[0226] When benzo[a]perylene compound and perylene compound are included as coloring agents (A), the benzo[a]perylene compound may also be used as a sensitizer of the perylene compound.

[0227] <<Coloring Agent (A1)>>

[0228] The coloring and curing resin composition of the present invention may also contain dyes (hereinafter, sometimes referred to as dyes (A1-1)) and / or pigments (hereinafter, sometimes referred to as pigments (A1-2)) other than benzo[a]perylene compounds and perylene compounds as coloring agents (A) (hereinafter, dyes (A1-1) and pigments (A1-2) are sometimes referred to together as coloring agent (A1)). They can be used alone or in combination of two or more.

[0229] The dye (A1-1) need not contain benzo[a]perylene compounds or perylene compounds; known dyes can be used without particular limitation, such as solvent dyes, acid dyes, direct dyes, and mordant dyes. Examples of dyes include compounds classified as dyes in the Dye Index (published by The Society of Dyers and Colourists) and known dyes listed in dyeing guides (for dyeing companies). Furthermore, based on chemical structure, examples include azo dyes, cyanine dyes, triphenylmethane dyes, xanthones, anthraquinone dyes, naphthoquinone dyes, quinone imine dyes, methylbenzene dyes, methylimine dyes, squaric acid dyes, acridine dyes, styryl dyes, coumarin dyes, quinoline dyes, nitro dyes, and phthalocyanine dyes. Among these, organic solvent-soluble dyes are preferred.

[0230] As pigments (A1-2), as long as they do not contain benzo[a]perylene compounds and perylene compounds, known pigments can be used without particular limitation. For example, pigments classified as pigments in the Dye Index (published by The Society of Dyers and Colourists) can be cited.

[0231] Pigments, as classified as pigments, include, for example:

[0232] CI pigment yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 129, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 185, 194, 214, 231, etc.

[0233] CI pigments include orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73, and other orange pigments;

[0234] CI pigments include reds 9, 97, 105, 122, 144, 166, 168, 176, 177, 180, 190, 192, 209, 215, 216, 224, 242, 254, 255, 264, 265, 266, 268, 269, and 273.

[0235] CI pigment blue 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 60 and other blue pigments;

[0236] CI pigments include purple 1, 19, 23, 32, 36, 38, and other purple pigments;

[0237] CI pigments include green 7, 36, 58, 59, 62, and 63, among other green pigments.

[0238] CI pigments, such as brown 23 and 25;

[0239] CI Pigment Black 1, 7, and other black pigments.

[0240] As a coloring agent (A1), red or green dyes and pigments are preferred.

[0241] The colorant (A1) can be subjected to various treatments as needed, such as rosin treatment, surface treatment using derivatives with introduced acidic or basic groups, grafting treatment using polymeric compounds, micronization treatment using sulfuric acid micronization, cleaning treatment using organic solvents or water to remove impurities, and removal treatment using ion exchange. The particle size of the colorant (A1) is preferably approximately uniform.

[0242] When colorant (A) further comprises colorant (A1), the lower limit of the content of the total amount of benzo[a]perylene compound and perylene compound in colorant (A) relative to the total amount of colorant (A) is, for example, 1% by mass or more, preferably 2% by mass or more, more preferably 10% by mass or more, further preferably 25% by mass or more, and particularly preferably 50% by mass or more. On the other hand, when colorant (A) further comprises colorant (A1), the upper limit of the content of the total amount of benzo[a]perylene compound and perylene compound in colorant (A) relative to the total amount of colorant (A) is, for example, less than 100% by mass.

[0243] When a coloring-curing resin composition contains a solvent (E), a colorant-containing liquid (sometimes also called a coloring composition) containing a colorant (A) and a solvent (E) can be prepared in advance, and then the coloring-curing resin composition can be prepared using this colorant-containing liquid. In cases where the colorant (A) is insoluble in the solvent (E), such as when the colorant (A) contains pigments (A1-2), the colorant-containing liquid can be prepared by dispersing the colorant (A) in the solvent (E) and mixing them. The colorant-containing liquid may contain part or all of the solvent (E) contained in the coloring-curing resin composition.

[0244] The content of solid components in the liquid containing colorant is preferably 0.01% by mass or more and 99.99% by mass or less, more preferably 0.1% by mass or more and 99.9% by mass or less, even more preferably 0.1% by mass or more and 99% by mass or less, even more preferably 0.5% by mass or more and 90% by mass or less, and particularly preferably 1% by mass or more and 50% by mass or less, relative to the total amount of the liquid containing colorant.

[0245] The colorant (A) can be dispersed by including a dispersant, thereby achieving a uniform dispersion of the colorant (A) in the solution. When using two or more colorants (A) in combination, each can be dispersed individually or by mixing multiple types for dispersion.

[0246] As dispersants, examples include surfactants, which can be cationic, anionic, nonionic, or amphoteric surfactants. Specifically, examples include polyester-based, polyamine-based, and acrylic surfactants. These dispersants can be used alone or in combination of two or more. Examples of dispersants by trade name include KP (manufactured by Shin-Etsu Chemical Co., Ltd.), FLOREN (manufactured by Kyoeisha Chemical Co., Ltd.), Solsperse (registered trademark) (manufactured by Zeneca Co., Ltd.), EFKA (registered trademark) (manufactured by BASF Corporation), AJISPER (registered trademark) (manufactured by Ajinomoto Finetechno Co., Ltd.), Disperbyk (registered trademark) (manufactured by BYK-Chemie Co., Ltd.), and BYK (registered trademark) (manufactured by BYK-Chemie Co., Ltd.). Resin (B), described later, can also be used as a dispersant.

[0247] When using a dispersant, the amount of the dispersant (solid component) used is typically 1 part to 10,000 parts by mass relative to 100 parts by mass of the colorant (A), preferably 5 parts to 5,000 parts by mass, more preferably 10 parts to 1,000 parts by mass, and even more preferably 15 parts to 800 parts by mass. If the amount of the dispersant used is within the above range, there is a tendency to obtain a liquid containing the colorant with a more uniform dispersion.

[0248] The content of colorant (A) relative to the total amount of solid components in the color-curing resin composition is preferably 0.1% by mass or more and 50% by mass or less, more preferably 0.5% by mass or more and 40% by mass or less, and even more preferably 1% by mass or more and 30% by mass or less. If the content of colorant (A) is within the above range, the color concentration when the filter is made is sufficient, and the composition contains the required amount of resin (B). Therefore, it is possible to form a pattern with sufficient mechanical strength, which is preferred.

[0249] Here, "total amount of solid components" in this specification refers to the amount remaining after removing the solvent content from the total amount of the coloring and curing resin composition. The total amount of solid components and the content of each component therein can be determined, for example, using known analytical methods such as liquid chromatography or gas chromatography.

[0250] <Resin (B)>

[0251] As resin (B), there is no particular limitation, but it is preferably an alkali-soluble resin, and more preferably a polymer having structural units of at least one monomer (hereinafter sometimes referred to as "monomer (a)") selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic anhydrides.

[0252] Resin (B) is preferably a copolymer having structural units derived from monomers (hereinafter sometimes referred to as "monomer (b)") having a cyclic ether structure having 2 to 4 carbon atoms and an olefinic unsaturated bond, as well as other structural units.

[0253] Other structural units include structural units derived from monomers capable of copolymerizing with monomer (a) (however, different from monomer (a) and monomer (b). Hereinafter, they are sometimes referred to as "monomer (c)"), structural units having olefinic unsaturated bonds, etc.

[0254] As a monomer (a), for example, the following can be cited:

[0255] Acrylic acid, methacrylic acid, crotonic acid, and ortho-, meta-, and p-vinylbenzoic acid are unsaturated monocarboxylic acids.

[0256] Unsaturated dicarboxylic acids such as maleic acid, fumaric acid, citraconic acid, zeaxanthin, itaconic acid, 3-vinyl phthalic acid, 4-vinyl phthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyltetrahydrophthalic acid, and 1,4-cyclohexenedicarboxylic acid.

[0257] 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-6-methylbicyclo[2.2.1]hept-2-ene and 5-carboxy-6-ethylbicyclo[2.2.1]hept-2-ene, etc., are bicyclic unsaturated compounds containing carboxyl groups;

[0258] Anhydrides of the above-mentioned unsaturated dicarboxylic acids, excluding fumaric acid and medronic acid;

[0259] Unsaturated mono[(meth)acryloyloxyethyl] esters of polycarboxylic acids with two or more members, such as succinic acid mono[2-(meth)acryloyloxyethyl] ester and phthalic acid mono[2-(meth)acryloyloxyethyl] ester.

[0260] Unsaturated acrylates such as α-(hydroxymethyl)acrylic acid, which contain both hydroxyl and carboxyl groups in the same molecule; and so on.

[0261] Among these, acrylic acid, methacrylic acid, and maleic anhydride are preferred, considering both copolymerization reactivity and the solubility of the resulting resin in alkaline aqueous solutions.

[0262] It should be noted that in this specification, "(meth)acrylic acid" means at least one selected from the group consisting of acrylic acid and methacrylic acid. The terms "(meth)acryloyl" and "(meth)acrylate" have the same meaning.

[0263] Monomer (b) refers to a polymerizable compound having a cyclic ether structure with 2 to 4 carbon atoms (for example, selected from at least one group consisting of ethylene oxide ring, oxetane ring, and tetrahydrofuran ring (oxetane ring)) and an olefinic unsaturated bond. Monomer (b) is preferably a monomer having a cyclic ether with 2 to 4 carbon atoms and a (meth)acryloyloxy group.

[0264] Examples of monomers (b) include monomers having an oxetyl group and an olefinic unsaturated bond (hereinafter sometimes referred to as "monomer (b1)"), monomers having an oxetyl group and an olefinic unsaturated bond (hereinafter sometimes referred to as "monomer (b2)"), and monomers having a tetrahydrofuranyl group and an olefinic unsaturated bond (hereinafter sometimes referred to as "monomer (b3)").

[0265] As monomers (b1), examples include monomers having a structure in which unsaturated aliphatic hydrocarbons are epoxidized (hereinafter, sometimes referred to as "monomers (b1-1)") and monomers having a structure in which unsaturated alicyclic hydrocarbons are epoxidized (hereinafter, sometimes referred to as "monomers (b1-2)").

[0266] As monomer (b1-1), monomers having a glycidyl group and an olefinic unsaturated bond are preferred. Specifically, examples of monomer (b1-1) include glycidyl (meth)acrylate, β-methyl glycidyl (meth)acrylate, β-ethyl glycidyl (meth)acrylate, glycidyl vinyl ether, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether, α-methylo-vinylbenzyl glycidyl ether, α-methylm-vinylbenzyl glycidyl ether, α-methylp-vinylbenzyl glycidyl ether, and 2,3-bis(glycidyloxy) 2,4-Bis(glycidoxymethyl)styrene, 2,5-Bis(glycidoxymethyl)styrene, 2,6-Bis(glycidoxymethyl)styrene, 2,3,4-Tris(glycidoxymethyl)styrene, 2,3,5-Tris(glycidoxymethyl)styrene, 2,3,6-Tris(glycidoxymethyl)styrene, 3,4,5-Tris(glycidoxymethyl)styrene, 2,4,6-Tris(glycidoxymethyl)styrene, etc.

[0267] Examples of monomers (b1-2) include vinylcyclohexene monoxide, 1,2-epoxy-4-vinylcyclohexane (e.g., Celloxide 2000; manufactured by Daicel Co., Ltd.), 3,4-epoxycyclohexyl methyl methacrylate (e.g., Cyclomer A400; manufactured by Daicel Co., Ltd.), 3,4-epoxycyclohexyl methyl methacrylate (e.g., Cyclomer M100; manufactured by Daicel Co., Ltd.), compounds represented by formula (BI), and compounds represented by formula (BII).

[0268]

[0269] In formulas (BI) and (BII), R a and R b Each of the above can independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, wherein the hydrogen atom contained in the alkyl group may be replaced by a hydroxyl group.

[0270] X a and X b Each can be used independently to represent a single bond, *-R c -、*-R c -O-、*-R c -S- or *-R c -NH-.

[0271] R c It represents the dimethyl groups of alkanes with 1 to 6 carbon atoms.

[0272] * indicates a connection to O.

[0273] Examples of alkyl groups having 1 to 4 carbon atoms include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, and tert-butyl.

[0274] Examples of alkyl groups in which hydrogen atoms are replaced by hydroxyl groups include hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 1-hydroxypropyl, 2-hydroxypropyl, 3-hydroxypropyl, 1-hydroxy-1-methylethyl, 2-hydroxy-1-methylethyl, 1-hydroxybutyl, 2-hydroxybutyl, 3-hydroxybutyl, 4-hydroxybutyl, etc.

[0275] As R a and R b Preferably, hydrogen atoms, methyl groups, hydroxymethyl groups, 1-hydroxyethyl groups, and 2-hydroxyethyl groups are included; more preferably, hydrogen atoms and methyl groups are included.

[0276] Examples of alkane dimethyl groups include methylene, ethylene, propane-1,2-dimethyl, propane-1,3-dimethyl, butane-1,4-dimethyl, pentane-1,5-dimethyl, and hexane-1,6-dimethyl.

[0277] As X a and X b Preferred examples include single bonds, methylene, ethylene, *-CH2-O- (* indicates a bond with O) group, and *-CH2CH2-O- group; more preferred examples include single bonds and *-CH2CH2-O- group (* indicates a bond with O).

[0278] Examples of compounds represented by formula (BI) include compounds represented by any of formulas (BI-1) to (BI-15). Among these, compounds represented by formulas (BI-1), (BI-3), (BI-5), (BI-7), (BI-9), and (BI-11) to (BI-15) are preferred, and compounds represented by formulas (BI-1), (BI-7), (BI-9), and (BI-15) are more preferred.

[0279]

[0280] Examples of compounds represented by formula (BII) include compounds represented by any one of formulas (BII-1) to (BII-15), among which compounds represented by formulas (BII-1), (BII-3), (BII-5), (BII-7), (BII-9), and (BII-11) to (BII-15) are preferred, and compounds represented by formulas (BII-1), (BII-7), (BII-9), and (BII-15) are more preferred.

[0281]

[0282] The compounds represented by formula (BI) and formula (BII) can be used individually or in combination. When used in combination, the content ratio of the compounds represented by formula (BI) and (BII) is preferably 5:95 to 95:5, more preferably 10:90 to 90:10, and even more preferably 20:80 to 80:20.

[0283] The monomer (b2) having an oxetyl group and an olefinic unsaturated bond is more preferably a monomer having an oxetyl group and a (meth)acryloyloxy group. Examples of monomers (b2) include 3-methyl-3-(meth)acryloyloxymethyloxetane, 3-ethyl-3-(meth)acryloyloxymethyloxetane, 3-methyl-3-(meth)acryloyloxyethyloxetane, and 3-ethyl-3-(meth)acryloyloxyethyloxetane.

[0284] The monomer (b3) having a tetrahydrofuran group and an olefinic unsaturated bond is more preferably a monomer having a tetrahydrofuran group and a (meth)acryloyloxy group. Examples of monomers (b3) include, for example, tetrahydrofurfuryl acrylate (e.g., Viscoat V#150, manufactured by Osaka Organic Chemicals Co., Ltd.) and tetrahydrofurfuryl methacrylate.

[0285] As a monomer (c), for example, the following can be cited:

[0286] Methyl methacrylate, ethyl methacrylate, n-butyl methacrylate, sec-butyl methacrylate, tert-butyl methacrylate, 2-ethylhexyl methacrylate, dodecyl methacrylate, lauryl methacrylate, stearyl methacrylate, cyclopentyl methacrylate, cyclohexyl methacrylate, 2-methylcyclohexyl methacrylate, tricyclo[5.2.1.0] 2,6 ] Decane-8-yl ester (in this technical field, it is commonly referred to as "(meth)acrylate dicyclopentyl ester". Additionally, it is sometimes called "(meth)acrylate tricyclodecyl ester".), (meth)acrylate tricyclo[5.2.1.0] 2,6 ] Decane-9-yl ester, (meth)acrylate tricyclic [5.2.1.0] 2,6 ] Decen-8-yl ester (commonly referred to as "(meth)acrylate dicyclopentenyl ester" in this technical field), (meth)acrylate tricyclo[5.2.1.0] 2,6 Decen-9-yl ester, dicyclopentyloxyethyl ester (meth)acrylate, isobornyl ester (meth)acrylate, adamantane ester (meth)acrylate, allyl ester (meth)acrylate, propargyl ester (meth)acrylate, phenyl ester (meth)acrylate, naphthyl ester (meth)acrylate, and benzyl ester (meth)acrylate, etc. (meth)acrylates;

[0287] 2-Hydroxyethyl methacrylate and 2-Hydroxypropyl methacrylate are hydroxyl-containing methacrylates.

[0288] Dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate, and diethyl itaconic acid;

[0289] Bicyclo[2.2.1]hept-2-ene, 5-methylbicyclo[2.2.1]hept-2-ene, 5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxybicyclo[2.2.1]hept-2-ene, 5-hydroxymethylbicyclo[2.2.1]hept-2-ene, 5-(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5-methoxybicyclo[2.2.1]hept-2-ene, 5-ethoxybicyclo[2.2.1]hept-2-ene, 5,6-dihydroxybicyclo[2.2.1]hept-2-ene, 5,6-di(hydroxymethyl)bicyclo[2.2.1]hept-2-ene, 5,6-di(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5,6-dimethoxybicyclo[2.2.1]hept-2-ene Bicyclic unsaturated compounds such as cyclo[2.2.1]hept-2-ene, 5,6-diethoxybicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxymethyl-5-methylbicyclo[2.2.1]hept-2-ene, 5-tert-butoxycarbonylbicyclo[2.2.1]hept-2-ene, 5-cyclohexyloxycarbonylbicyclo[2.2.1]hept-2-ene, 5-phenoxycarbonylbicyclo[2.2.1]hept-2-ene, 5,6-bis(tert-butoxycarbonyl)bicyclo[2.2.1]hept-2-ene, and 5,6-bis(cyclohexyloxycarbonyl)bicyclo[2.2.1]hept-2-ene;

[0290] N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimide-3-maleimide benzoate, N-succinimide-4-maleimide butyrate, N-succinimide-6-maleimide hexanoate, N-succinimide-3-maleimide propionate and N-(9-acridyl)maleimide and other dicarbonylimide derivatives;

[0291] Aromatic compounds containing vinyl groups, such as styrene, o-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, and p-methoxystyrene; nitrile compounds containing vinyl groups, such as (meth)acrylonitrile; halogenated hydrocarbons such as vinyl chloride and vinylidene chloride; amides containing vinyl groups, such as (meth)acrylamide; esters such as vinyl acetate; dienes such as 1,3-butadiene, isoprene, and 2,3-dimethyl-1,3-butadiene; and so on.

[0292] Among these, considering copolymerization reactivity and heat resistance, styrene, vinyltoluene, and tricyclic (meth)acrylate [5.2.1.0] are preferred. 2,6 ] Decane-8-yl ester, (meth)acrylate tricyclic [5.2.1.0] 2,6 ] Decane-9-yl ester, (meth)acrylate tricyclic [5.2.1.0] 2,6] Decen-8-yl ester, (meth)acrylate tricyclic [5.2.1.0] 2,6 [Decene-9-yl ester, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo[2.2.1]hept-2-ene and (meth)acrylate benzyl ester, etc.]

[0293] The structural unit having an olefinic unsaturated bond is preferably a structural unit having a (meth)acryloyl group. A resin having such a structural unit can be obtained by adding a group having an olefinic unsaturated bond that can react with the groups of monomers (a) and (b) to a polymer having structural units from monomers (a) and (b).

[0294] Examples of such structural units include those obtained by adding glycidyl methacrylate to a (meth)acrylic acid unit, those obtained by adding 2-hydroxyethyl (meth)acrylic acid to a maleic anhydride unit, and those obtained by adding (meth)acrylic acid to a glycidyl methacrylate unit. Furthermore, when these structural units have a hydroxyl group, the structural units obtained by further adding a carboxylic anhydride to them can also be cited as structural units having an olefinic unsaturated bond.

[0295] Polymers having structural units derived from monomer (a) can be manufactured, for example, by polymerizing the monomers constituting the structural units of the polymer in a solvent in the presence of a polymerization initiator. The polymerization initiator and solvent are not particularly limited, and substances commonly used in this field can be used. Examples of polymerization initiators include azo compounds (2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylpentanonitrile) etc.) and organic peroxides (benzoyl peroxide, etc.). As for the solvent, any solvent that dissolves the monomers is acceptable; solvents such as those described later (E) can be used.

[0296] It should be noted that the resulting copolymer can be used directly from the reaction solution, or from a concentrated or diluted solution, or from a substance extracted in solid (powder) form through methods such as reprecipitation. In particular, by using the solvent (E) described later as a solvent during the polymerization, the reaction solution can be used directly, simplifying the manufacturing process.

[0297] Depending on the requirements, reaction catalysts (such as tris(dimethylaminomethyl)phenol) and polymerization inhibitors (such as hydroquinone) can be used to react carboxylic acids or carboxylic anhydrides with cyclic ethers.

[0298] Examples of carboxylic anhydrides include maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinyl phthalic anhydride, 4-vinyl phthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, and 5,6-dicarboxylic bicyclo[2.2.1]hept-2-ene anhydride.

[0299] As resin (B), specifically, examples include: methyl 3,4-epoxycyclohexyl methacrylate / (meth)acrylate copolymer, methyl 3,4-epoxytricyclo(meth)acrylate [5.2.1.0] 2,6 Decyl ester / (meth)acrylic acid copolymer, glycidyl methacrylate / benzyl methacrylate / (meth)acrylic acid copolymer, glycidyl methacrylate / styrene / (meth)acrylic acid copolymer, 3,4-epoxy tricyclic (meth)acrylic acid [5.2.1.0] 2,6 Decyl ester / (meth)acrylic acid / N-cyclohexylmaleimide copolymer, (meth)acrylic acid 3,4-epoxy tricyclic [5.2.1.0] 2,6 Decyl ester / (meth)acrylic acid / N-cyclohexylmaleimide / (meth)acrylic acid 2-hydroxyethyl ester copolymer, (meth)acrylic acid 3,4-epoxy tricyclic [5.2.1.0] 2,6 Decyl ester / (meth)acrylic acid / vinyl toluene copolymer, (meth)acrylic acid 3,4-epoxy tricyclic [5.2.1.0] 2,6 Decyl ester / (meth)acrylic acid / (meth)acrylic acid benzyl ester / (meth)acrylic acid copolymer, (meth)acrylic acid 3,4-epoxy tricyclic [5.2.1.0] 2,6 Decyl ester / (meth)acrylic acid / (meth)acrylic acid 2-ethylhexyl ester copolymer, (meth)acrylic acid 3,4-epoxy tricyclic [5.2.1.0] 2,6 Decyl ester / (meth)acrylate tricyclo[5.2.1.0] 2,6 [The following are examples of resins:] decenyl ester / (meth)acrylic acid / N-cyclohexylmaleimide copolymer, 3-methyl-3-(meth)acryloyloxymethyloxetane / (meth)acrylic acid / styrene copolymer, benzyl (meth)acrylic acid / (meth)acrylic acid copolymer, styrene / (meth)acrylic acid copolymer, and resins described in Japanese Patent Application Publication Nos. 9-106071, 2004-29518, and 2004-361455.

[0300] Among them, the resin (B) is preferably a copolymer containing structural units from monomer (a) and structural units from monomer (b).

[0301] Resin (B) can be composed of two or more types. In this case, for resin (B),

[0302] Preferably, it is a copolymer containing at least one type of structural unit comprising structural units from monomer (a) and structural units from monomer (b).

[0303] More preferably, it contains at least one copolymer comprising structural units from monomer (a) and structural units from monomer (b1).

[0304] Further preferred are copolymers containing at least one type of structural unit comprising structural units from monomer (a) and structural units from monomers (b1-2).

[0305] More preferably, it contains at least one component selected from (meth)acrylic acid 3,4-epoxytricyclo[5.2.1.0]. 2,6 Decyl ester / (meth)acrylic acid copolymer, (meth)acrylic acid 3,4-epoxy tricyclic [5.2.1.0] 2,6 Decyl ester / (meth)acrylic acid / N-cyclohexylmaleimide / (meth)acrylic acid 2-hydroxyethyl ester copolymer, (meth)acrylic acid 3,4-epoxy tricyclic [5.2.1.0] 2,6 Decyl ester / (meth)acrylic acid / vinyl toluene copolymer, (meth)acrylic acid 3,4-epoxy tricyclic [5.2.1.0] 2,6 One or more of the following: decyl ester / (meth)acrylic acid / (meth)acrylic acid 2-ethylhexyl ester copolymer.

[0306] The weight-average molecular weight (Mw) of resin (B) converted to polystyrene is preferably 1,000 to 100,000, more preferably 2,000 to 50,000, and even more preferably 3,000 to 30,000. If the weight-average molecular weight is within the above range, there is a tendency for the unexposed portion to have high solubility in the developer, resulting in a high residual film rate and high hardness of the obtained pattern.

[0307] The dispersion of resin (B) [weight average molecular weight (Mw) / number average molecular weight (Mn)] is preferably 1 to 6 and less, more preferably 1.001 to 4 and less, and even more preferably 1.01 to 4 and less.

[0308] The acid value (converted from solid component value) of resin (B) is preferably 10 mg-KOH / g or more and 300 mg-KOH / g or less, more preferably 20 mg-KOH / g or more and 250 mg-KOH / g or less, even more preferably 25 mg-KOH / g or more and 200 mg-KOH / g or less, even more preferably 30 mg-KOH / g or more and 150 mg-KOH / g or less, and particularly preferably 60 mg-KOH / g or more and 135 mg-KOH / g or less. Here, the acid value is a value determined as the amount (mg) of potassium hydroxide required to neutralize 1g of resin, and can be obtained, for example, by titration using an aqueous solution of potassium hydroxide.

[0309] In the solid component of the color-curing resin composition, the content of resin (B) is preferably 5 to 50% by mass, more preferably 10 to 40% by mass, and even more preferably 15 to 30% by mass. If the content of resin (B) is within the above range, there is a tendency for the unexposed portion to have high solubility in the developer.

[0310] <Polymerizing Compound (C)>

[0311] The polymerizable compound (C) is a compound that can be polymerized using active free radicals and / or acids generated by the polymerization initiator (D). Examples include compounds with polymerizable olefinic unsaturated bonds, and (meth)acrylate compounds are preferred.

[0312] Examples of polymeric compounds having one olefinic unsaturated bond include, for example, nonylphenyl carbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexyl carbitol acrylate, 2-hydroxyethyl acrylate, N-vinylpyrrolidone, and the monomers (a), (b), and (c) described above.

[0313] Examples of polymeric compounds having two olefinic unsaturated bonds include 1,6-hexanediol di(meth)acrylate, ethylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, bis(acryloyloxyethyl) ether of bisphenol A, and 3-methylpentyl glycol di(meth)acrylate.

[0314] The polymerizable compound (C) is preferably a polymerizable compound having three or more olefinic unsaturated bonds. Examples of such polymerizable compounds include, for instance, trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, tripentaerythritol octa(meth)acrylate, tripentaerythritol hepta(meth)acrylate, tetrapentaerythritol deca(meth)acrylate, tetrapentaerythritol nona(meth)acrylate, and tri(2-(meth)acryloyl) Oxyethyl 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, etc., preferably dipentaerythritol penta(meth)acrylate and dipentaerythritol hexa(meth)acrylate.

[0315] The weight-average molecular weight of the polymeric compound (C) is preferably 50 or more and 4,000 or less, more preferably 70 or more and 3,500 or less, even more preferably 100 or more and 3,000 or less, even more preferably 150 or more and 2,900 or less, and particularly preferably 250 or more and 1,500 or less.

[0316] The content of polymeric compound (C) relative to the total amount of solid components in the coloring and curing resin composition can be, for example, 1% by mass or more and 99% by mass or less, preferably 5% by mass or more and 90% by mass or less, more preferably 10% by mass or more and 80% by mass or less, and even more preferably 20% by mass or more and 70% by mass or less.

[0317] <Polymerization Initiator (D)>

[0318] The polymerization initiator (D) can be any compound that can generate active free radicals, acids, etc. under the action of light and heat and can initiate polymerization. There are no special restrictions, and known polymerization initiators can be used.

[0319] Examples of polymerization initiators (D) include O-acyl oxime compounds, alkyl phenyl ketone compounds, biimidazole compounds, triazine compounds, and acylphosphine oxide compounds.

[0320] Examples of O-acyl oxime compounds include, for example, N-benzoyloxy-1-(4-phenylthiophenyl)butane-1-one-2-imine, N-benzoyloxy-1-(4-phenylthiophenyl)octane-1-one-2-imine, N-benzoyloxy-1-(4-phenylthiophenyl)-3-cyclopentylpropane-1-one-2-imine, N-acetoxy-1-(4-phenylthiophenyl)-3-cyclopentylpropane-1-one-2-imine, N-acetoxy-1-(4-phenylthiophenyl)-3-cyclohexylpropane-1-one-2-imine, and N-acetoxy-1-[ 9-Ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]ethane-1-imine, N-acetoxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethyl-2,4-dioxolane ... In addition, commercially available products such as Irgacure (registered trademark) OXE01, OXE02 (both manufactured by BASF) and N-1919 (manufactured by ADEKA Co., Ltd.) can be used as O-acyl oxime compounds. Among them, the O-acyl oxime compound is preferably selected from at least one of the group consisting of N-benzoyloxy-1-(4-phenylthiophenyl)butane-1-one-2-imine, N-benzoyloxy-1-(4-phenylthiophenyl)octane-1-one-2-imine and N-benzoyloxy-1-(4-phenylthiophenyl)-3-cyclopentylpropane-1-one-2-imine, and more preferably N-benzoyloxy-1-(4-phenylthiophenyl)octane-1-one-2-imine.

[0321] Examples of alkyl phenyl ketone compounds include 2-methyl-2-morpholino-1-(4-methylthioalkylphenyl)propane-1-one, 2-dimethylamino-1-(4-morpholinophenyl)-2-benzylbutane-1-one, and 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholino)phenyl]butane-1-one. Commercially available alkyl phenyl ketone compounds include Irgacure (registered trademark) 369, 907, and 379 (manufactured by BASF).

[0322] Examples of alkyl phenyl ketone compounds include oligomers of 2-hydroxy-2-methyl-1-phenylpropane-1-one, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy)phenyl]propane-1-one, 1-hydroxycyclohexylphenyl ketone, 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propane-1-one, α,α-diethoxyacetophenone, and benzoyladimethyl ketal.

[0323] Examples of biimidazole compounds include, for example, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3-dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole (see, for example, Japanese Patent Application Publication Nos. 6-75372 and 6-75373, etc.), 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(alkoxyphenyl)biimidazole, and 2,2'-bis(2-chlorophenyl)biimidazole. -4,4',5,5'-tetra(dialkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(trialkoxyphenyl)biimidazole (e.g., see Japanese Patent Publication No. 48-38403, Japanese Patent Application Publication No. 62-174204, etc.) and biimidazole compounds in which the phenyl group at the 4,4',5,5'-position is replaced by a carboalkoxy group (e.g., see Japanese Patent Application Publication No. 7-10913, etc.).

[0324] Examples of triazine compounds 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-piperyl-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxystyryl)-1,3,5-triazine, and 2,4-bis(trichloromethyl)-6-[2- [5-Methylfuran-2-yl]vinyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)vinyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl)vinyl]-1,3,5-triazine, and 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)vinyl]-1,3,5-triazine, etc.

[0325] Examples of acylphosphine oxide compounds include 2,4,6-trimethylbenzoyl diphenylphosphine oxide. Commercially available products such as Irgacure (registered trademark) 819 (manufactured by BASF) can be used.

[0326] In addition, examples of polymerization initiators (D) include benzoin compounds such as benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether; benzophenone compounds such as methyl benzoyl peroxide, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, 3,3',4,4'-tetra(tert-butylperoxycarbonyl)benzophenone, and 2,4,6-trimethylbenzophenone; quinone compounds such as 9,10-phenanthroquinone, 2-ethylanthraquinone, and camphorquinone; and 10-butyl-2-chloroacridone, benzoin, methyl phenylglyoxylate, and titanium decene compounds.

[0327] They are preferably used in combination with polymerization initiators (D1) (especially amines) described later.

[0328] The polymerization initiator (D) is preferably a polymerization initiator comprising at least one selected from the group consisting of alkyl phenyl ketone compounds, triazine compounds, acylphosphine oxide compounds, O-acyl oxime compounds and bimidazole compounds, and more preferably a polymerization initiator comprising an O-acyl oxime compound.

[0329] Relative to 100 parts by mass of the total amount of resin (B) and polymeric compound (C) contained in the color-curing resin composition, the content of polymerization initiator (D) is preferably 0.1 parts by mass or more than 30 parts by mass, and more preferably 1 part by mass or more than 20 parts by mass. If the content of polymerization initiator (D) is within the above range, there is a tendency to achieve higher sensitivity and shorten the exposure time, thereby increasing the productivity of the color filter.

[0330] <Polymerization Initiator (D1)>

[0331] A polymerization initiator (D1) is a compound or sensitizer used to promote the polymerization of a polymerizable compound (C) that is initiated by a polymerization initiator (D). In cases where a polymerization initiator (D1) is included, it is typically used in combination with the polymerization initiator (D).

[0332] Examples of polymerization initiators (D1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds, and carboxylic acid compounds.

[0333] Examples of amine compounds 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 benzophenone), 4,4'-bis(diethylamino)benzophenone, and 4,4'-bis(ethylmethylamino)benzophenone, with 4,4'-bis(diethylamino)benzophenone being a preferred example. Additionally, commercially available products such as EAB-F (manufactured by Hodogaya Chemical Industry Co., Ltd.) can be used as amine compounds.

[0334] Examples of alkoxyanthracene compounds 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.

[0335] Examples of thioxanthone compounds include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, and 1-chloro-4-propoxythioxanthone.

[0336] Examples of carboxylic acid compounds include phenylthioacetic acid, methylphenylthioacetic acid, ethylphenylthioacetic acid, methylethylphenylthioacetic acid, dimethylphenylthioacetic acid, methoxyphenylthioacetic acid, dimethoxyphenylthioacetic acid, chlorophenylthioacetic acid, dichlorophenylthioacetic acid, N-phenylglycine, phenoxyacetic acid, naphthioacetic acid, N-naphthylglycine, and naphthoxyacetic acid.

[0337] When using these polymerization initiators (D1), the content is preferably 0.1 parts by mass or more and 30 parts by mass or less, more preferably 1 part by mass or more and 20 parts by mass or less, relative to 100 parts by mass of the total amount of resin (B) and polymeric compound (C) contained in the coloring and curing resin composition.

[0338] <Solvent (E)>

[0339] Solvent (E) is not particularly limited and solvents commonly used in this field can be used.

[0340] Solvents (E) include, for example, ester solvents (solvents containing -COO- but not -O-), ether solvents (solvents containing -O- but not -COO-), ether-ester solvents (solvents containing both -COO- and -O-), ketone solvents (solvents containing -CO- but not -COO-), alcohol solvents (solvents containing OH but not -O-, -CO-, and -COO-), aromatic hydrocarbon solvents, amide solvents, dimethyl sulfoxide, etc. Two or more of these solvents can be used in combination.

[0341] Examples of ester solvents include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutyrate, ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, isoamyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexanol acetate, and γ-butyrolactone.

[0342] Examples of ether solvents include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenethyl ether, and methyl anisole.

[0343] Examples of ether ester solvents include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, ethyl 2-ethoxy-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, diethylene glycol monobutyl ether acetate, and dipropylene glycol methyl ether acetate.

[0344] Examples of ketone solvents include 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone, and isophorone.

[0345] Examples of alcohol solvents include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerol.

[0346] Examples of aromatic hydrocarbon solvents include benzene, toluene, xylene, and mesitylene.

[0347] Examples of amide solvents include N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.

[0348] As solvent (E), propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate and cyclohexanone are preferred.

[0349] When solvent (E) is included, the content of solvent (E) relative to the total amount of the color-curing resin composition is generally 99.99% by mass or less, preferably 40% by mass or more and 99% by mass or less, more preferably 50% by mass or more and 95% by mass or less, further preferably 70% by mass or more and 95% by mass or less, and even more preferably 75% by mass or more and 90% by mass or less. In other words, the total amount of solid components in the color-curing resin composition is generally 0.01% by mass or more, preferably 1% by mass or more and 60% by mass or less, more preferably 5% by mass or more and 50% by mass or less, further preferably 5% by mass or more and 30% by mass or less, and even more preferably 10% by mass or more and 25% by mass or less. If the content of solvent (E) is within the above range, the flatness during coating becomes good, and since the color concentration is not insufficient when forming the color filter, there is a tendency for the display characteristics to become good.

[0350] <Leveling Agent (F)>

[0351] Examples of leveling agents (F) include silicone surfactants, fluorinated surfactants, and silicone surfactants containing fluorine atoms. They may have polymerizable groups on their side chains.

[0352] Examples of organosilicon surfactants include surfactants that have intramolecular siloxane bonds. Specifically, examples include TORAY SILICONE DC3PA, TORAY SILICONE SH7PA, TORAY SILICONE DC11PA, TORAY SILICONE SH21PA, TORAY SILICONE SH28PA, TORAY SILICONE SH29PA, TORAY SILICONE SH30PA, TORAY SILICONE SH8400 (trade name: Toray Corning Co., Ltd.), KP321, KP322, KP323, KP324, KP326, KP340, KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452, and TSF4460 (manufactured by Momentive Advanced Materials Japan Contract Co., Ltd.).

[0353] Fluorinated surfactants include those with intramolecular fluorocarbon chains. Specifically, examples include FLOURAD (registered trademark) FC430, FLOURAD FC431 (manufactured by Sumitomo 3M Co., Ltd.), MEGAFAC (registered trademark) F142D, MEGAFAC F171, MEGAFAC F172, MEGAFAC F173, MEGAFAC F177, MEGAFAC F183, MEGAFAC F554, MEGAFAC R30, MEGAFAC RS-718-K (manufactured by DIC Co., Ltd.), EFTOP (registered trademark) EF301, EFTOP EF303, EFTOP EF351, EFTOP EF352 (manufactured by Mitsubishi Materials Electronics & Chemicals Co., Ltd.), SURFLON (registered trademark) S381, SURFLON S382, SURFLON SC101, and SURFLON... SC105 (manufactured by Asahi Glass Co., Ltd.) and E5844 (manufactured by Daikin Fine Chemicals Research Institute Co., Ltd.), etc.

[0354] Organosilicon surfactants containing fluorine atoms include surfactants with siloxane bonds and fluorocarbon chains within the molecule. Specifically, examples include MEGAFAC (registered trademark) R08, MEGAFAC BL20, MEGAFAC F475, MEGAFAC F477, and MEGAFAC F443 (manufactured by DIC Corporation).

[0355] When a leveling agent (F) is included, the content of the leveling agent (F) relative to the total amount of the color-curing resin composition is preferably 0.0005% by mass or more and 1% by mass or less, more preferably 0.001% by mass or more and 0.5% by mass or less, and even more preferably 0.005% by mass or more and 0.1% by mass or less. It should be noted that this content does not include the content of the pigment dispersant. If the content of the leveling agent (F) is within the above-mentioned range, the flatness of the color filter can be well achieved.

[0356] <Other Ingredients>

[0357] Coloring and curing resin compositions may include, as needed, fillers, other polymeric compounds, adhesion promoters, quenchers, antioxidants, light stabilizers, chain transfer agents, and other additives known in the art.

[0358] <Method for manufacturing coloring and curing resin compositions>

[0359] Colored curable resin compositions can be prepared by mixing a colorant (A), a resin (B), a polymerizable compound (C), a polymerization initiator (D), and, as needed, a solvent (E), a leveling agent (F), and other components. Mixing can be carried out using known or conventional apparatus and conditions.

[0360] Regarding the colorant (A), it can be pre-mixed with part or all of the solvent (E) and dispersed using a bead mill or similar device until the average particle size is approximately 0.2 μm or less, preferably in a dispersed state. At this time, the aforementioned dispersant and part or all of the resin (B) can be added as needed. Alternatively, the colorant (A) can be used in a state where it is pre-dissolved in part or all of the solvent (E). By mixing the remaining components into the liquid containing the colorant obtained in this manner to a predetermined concentration, a target-colored curable resin composition can be prepared.

[0361] <Method for Manufacturing Color Filters>

[0362] A color filter (which can be a color conversion layer) can be formed from a color-curable resin composition. Methods for forming the color pattern include photolithography, inkjet printing, and printing. Photolithography is preferred. The photolithography method involves coating the aforementioned color-curable resin composition onto a substrate, drying it to form a color-curable resin composition layer, exposing the color-curable resin composition layer through a photomask, and then developing it. In the photolithography method, by not using a photomask during exposure and / or not developing, a colored coating film, which is a cured product of the aforementioned color-curable resin composition layer, can be formed. The color pattern and colored coating film thus formed constitute the color filter of the present invention.

[0363] The thickness of the filter film is not particularly limited and can be adjusted appropriately according to the purpose and application. For example, it can be 0.1μm to 30μm, preferably 0.1μm to 20μm, and more preferably 0.5μm to 6μm.

[0364] As substrates, the following can be used: glass plates such as quartz glass, borosilicate glass, aluminosilicate glass, and soda-lime glass with a silica coating; resin plates such as polycarbonate, polymethyl methacrylate, and polyethylene terephthalate; silicon; and substrates on which aluminum, silver, or silver / copper / palladium alloy thin films are formed. Other color filter layers, resin layers, transistors, circuits, etc., can also be formed on these substrates.

[0365] The formation of individual color pixels using photolithography can be carried out using known or conventional devices and conditions. For example, it can be fabricated in the following manner.

[0366] First, a coloring curable resin composition is coated onto a substrate, and volatile components such as solvents are removed by heating and drying (pre-baking) and / or vacuum drying, thereby obtaining a smooth coloring curable resin composition layer.

[0367] Examples of coating methods include spin coating, slot coating, and a combination of slot and spin coating.

[0368] The temperature for heating and drying is preferably 30°C to 120°C, more preferably 50°C to 110°C. Furthermore, the heating time is preferably 10 seconds to 60 minutes, more preferably 30 seconds to 30 minutes.

[0369] When performing vacuum drying, it is preferable to carry out the process under a pressure of 50 Pa to 150 Pa and a temperature range of 20°C to 25°C.

[0370] There is no particular limitation on the film thickness of the color-curing resin composition layer; it can be appropriately selected according to the film thickness of the target color filter.

[0371] Next, the color-curable resin composition layer is exposed through a photomask used to form the target color pattern. The pattern on the photomask is not particularly limited; a pattern appropriate to the intended use can be used. Furthermore, in order to uniformly illuminate the entire exposure surface with parallel light and to accurately align the photomask with the substrate on which the color-curable resin composition layer is formed, exposure equipment such as a mask aligner and a stepper is preferably used.

[0372] The light source used for exposure is preferably a light source that produces light with wavelengths between 250 nm and 450 nm. For example, a filter that cuts off the wavelength region can be used to cut off light with wavelengths less than 350 nm; or a bandpass filter that extracts the wavelength regions around 436 nm, 408 nm, and 365 nm can be used to selectively extract light. Specifically, examples include mercury lamps, light-emitting diodes, metal halide lamps, and halogen lamps.

[0373] A colored pattern is formed on a substrate by contacting the exposed color-curable resin composition layer with a developing solution. During development, the unexposed portions of the color-curable resin composition layer dissolve in the developing solution and are removed. As the developing solution, an aqueous solution of an alkaline compound such as potassium hydroxide, sodium bicarbonate, sodium carbonate, or tetramethylammonium hydroxide is preferred. 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. Furthermore, the developing solution may contain a surfactant.

[0374] The development method can be any of the following: spin-dip, immersion, or spray. Furthermore, the substrate can be tilted at any angle during development.

[0375] The substrate after development is preferably washed with water.

[0376] Preferably, the obtained colored pattern is further baked. The post-baking temperature is preferably 150°C to 250°C, more preferably 160°C to 240°C. The post-baking time is preferably 1 minute to 120 minutes, more preferably 10 minutes to 60 minutes.

[0377] <Display Device>

[0378] The aforementioned color filter is useful as a color filter used in display devices (e.g., liquid crystal display devices, organic EL devices, electronic paper, etc.) and solid-state imaging devices, especially as a color filter used in organic EL devices.

[0379] The benzo[a]perylene compound of the present invention and the color filter formed by the color curable resin composition have high fluorescence intensity, thus enabling the manufacture of a color filter with excellent brightness.

[0380] Fluorescence intensity can be measured, for example, using a fluorescence spectrophotometer (FluoroMAX-3; manufactured by Horiba Corporation).

[0381] Furthermore, the benzo[a]perylene compound of the present invention has high solubility in solvents (such as propylene glycol monomethyl ether acetate). In addition, the benzo[a]perylene compound of the present invention and the color filter formed from the color-curing resin composition not only exhibit high fluorescence intensity and excellent brightness, but also tend to have excellent heat resistance and lightfastness.

[0382] Example

[0383] The present invention will be described in more detail below with examples, but the present invention is not limited to the following examples at all. Of course, it can be implemented by appropriate modifications within the scope of the spirit described above and below, and all such modifications are included within the technical scope of the present invention. It should be noted that, unless otherwise specified, "parts" in the following text refers to "parts by mass" and "%" refers to "% by mass".

[0384] In the following examples, the structures of the compounds were confirmed using mass spectrometry (LC; Agilent 1200, MASS; Agilent LC / MSD6130).

[0385] The weight-average molecular weight (Mw) and number-average molecular weight (Mn) of the resin, converted to polystyrene, were determined using the GPC method under the following conditions.

[0386] Device: HLC-8120GPC (manufactured by Tosoh Corporation)

[0387] Column: TSK-GELG2000HXL

[0388] Column temperature: 40℃

[0389] y: Tetrahydrofuran

[0390] Flow rate: 1.0 mL / min

[0391] The concentration of solid components in the analytical sample was 0.001–0.01% by mass.

[0392] Injection volume: 50μL

[0393] Detector: RI

[0394] Calibration standard materials: TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Corporation)

[0395] The ratio of weight-average molecular weight to number-average molecular weight (Mw / Mn) obtained above for conversion to polystyrene is used as the dispersity.

[0396] (Synthesis example 1)

[0397] <Preparation of Compound (I-21)>

[0398] Add N 1 N 2 20 parts of bis(2,6-diisopropylphenyl)perylene-3,4,9,10-tetracarboxylic diimide (manufactured by Tokyo Chemical Industry Co., Ltd.), 788 parts of maleic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), and 12 parts of tetrachloro-p-benzoquinone (manufactured by Tokyo Chemical Industry Co., Ltd.) were stirred at 170°C for 25 hours. While keeping the resulting mixture below 70°C, 800 parts of pre-prepared 1 mol / L hydrochloric acid (manufactured by Kanto Chemical Co., Ltd.) and 300 parts of acetone (manufactured by Kanto Chemical Co., Ltd.) were added, resulting in a yellow precipitate. The mixture containing this yellow precipitate was filtered, and the residue was washed with 400 parts of water and 200 parts of methanol. The residue was dried under reduced pressure at 60°C to obtain 15 parts of N represented by formula (I-21). 1 N 2 - bis(2,6-diisopropylphenyl)benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid-2,3,8,9-bisimide-11,12-anhydride (hereinafter, sometimes referred to as compound (I-21)) (75% yield).

[0399]

[0400] <Identification of Compound (I-21)>

[0401] (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 805

[0402] Accurate quality: 804

[0403] (Synthesis example 2)

[0404] <Preparation of Compound (I-23)>

[0405] Add N obtained from Synthesis Example 1 1 N 2 2.0 parts of bis(2,6-diisopropylphenyl)benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid-2,3,8,9-diimide-11,12-anhydride, 0.88 parts of 2,6-diisopropylaniline (manufactured by Tokyo Chemical Industry Co., Ltd.), and 120 parts of propionic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) were stirred at 140°C for 6 hours. The resulting mixture was concentrated, and 5 parts of methanol were added, resulting in a yellow precipitate. The mixture containing the yellow precipitate was filtered, and the residue was washed with 2 parts of methanol. The residue was dried under reduced pressure at 60°C and purified by silica gel column chromatography (solvent: chloroform), resulting in 1.7 parts of N represented by formula (I-23).1 N 2 N 3 - Tris(2,6-diisopropylphenyl)benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acidtriimide (hereinafter, sometimes referred to as compound (I-23)) (yield 68%).

[0406]

[0407] <Identification of Compound (I-23)>

[0408] (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 965

[0409] Accurate quality: 964

[0410] (Synthesis example 3)

[0411] <Preparation of Compound (I-1)>

[0412] Add N 1 N 2 1.6 parts of bis(3-pentyl)perylene-3,4,9,10-tetracarboxylic diimide (Aldrich), 84 parts of maleic anhydride (Tokyo Chemical Industries, Ltd.), and 1.3 parts of tetrachloro-p-benzoquinone (Tokyo Chemical Industries, Ltd.) were stirred at 220°C for 30 hours. While maintaining the resulting mixture below 70°C, 256 parts of pre-prepared 1 mol / L hydrochloric acid (Kanto Chemical Co., Ltd.) and 96 parts of acetone (Kanto Chemical Co., Ltd.) were added, resulting in a yellow precipitate. The mixture containing this yellow precipitate was filtered, and the residue was washed with 400 parts of water and 200 parts of methanol. The residue was dried under reduced pressure at 60°C to obtain 1.4 parts of N represented by formula (I-1). 1 N 2 - bis(3-pentyl)benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid-2,3,8,9-bisimide-11,12-anhydride (hereinafter, sometimes referred to as compound (I-1)) (75% yield).

[0413]

[0414] <Identification of Compound (I-1)>

[0415] (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 625

[0416] Accurate quality: 624

[0417] <Preparation of Compound (I-3)>

[0418] Separately, N 1 N 2 2.0 parts of bis(2,6-diisopropylphenyl)benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid-2,3,8,9-bisimide-11,12-anhydride were replaced with 2.5 parts of the above-mentioned compound (I-1), and 0.88 parts of 2,6-diisopropylaniline were replaced with 1.4 parts. Otherwise, the procedure was the same as in Synthesis Example 2, yielding 1.8 parts of N represented by formula (I-3). 1 N 2 -bis(3-pentyl)-N 3 -(2,6-diisopropylphenyl)-benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid triimide (hereinafter, sometimes referred to as compound (I-3)) (yield 85%).

[0419]

[0420] <Identification of Compound (I-3)>

[0421] (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 784

[0422] Accurate quality: 783

[0423] (Synthesis Example 4)

[0424] <Preparation of Compound (I-22)>

[0425] 0.88 parts of 2,6-diisopropylaniline (manufactured by Tokyo Chemical Industry Co., Ltd.) were replaced with 1.0 part of 7-tridecylamine, and the procedure was otherwise performed in the same manner as in Synthesis Example 2 to obtain 1.4 parts of N represented by formula (I-22). 1 N 2 -bis(2,6-diisopropylphenyl)-N 3 -(7-tetrazyl)-benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid triimide (hereinafter, sometimes referred to as compound (I-22)) (yield 58%).

[0426]

[0427] <Identification of Compound (I-22)>

[0428] (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 987

[0429] Accurate quality: 986

[0430] (Synthesis Example 5)

[0431] <Preparation of Compound (I-24)>

[0432] 0.88 parts of 2,6-diisopropylaniline (manufactured by Tokyo Chemical Industry Co., Ltd.) were replaced with 1.0 part of 2,5-di-tert-butylaniline, and the procedure was otherwise performed in the same manner as in Synthesis Example 2 to obtain 2.0 parts of N represented by formula (I-24). 1 N 2 -bis(2,6-diisopropylphenyl)-N 3 -(2,5-di-tert-butylphenyl)-benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid triimide (hereinafter, sometimes referred to as compound (I-24)) (yield 81%).

[0433]

[0434] <Identification of Compound (I-24)>

[0435] (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 993

[0436] Accurate quality: 992

[0437] (Synthesis Example 6)

[0438] <Preparation of Compound (I-25)>

[0439] 0.88 parts of 2,6-diisopropylaniline (manufactured by Tokyo Chemical Industry Co., Ltd.) were replaced with 0.88 parts of 4-tert-butyl-2,6-dimethylaniline (manufactured by Aldrich), and the procedure was otherwise performed in the same manner as in Synthesis Example 2, yielding 2.4 parts of N represented by formula (I-25). 1 N 2 -bis(2,6-diisopropylphenyl)-N 3 -(4-tert-butyl-2,6-dimethylphenyl)-benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid triimide (hereinafter, sometimes referred to as compound (I-25)) (77% yield).

[0440]

[0441] <Identification of Compound (I-25)>

[0442] (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 964

[0443] Accurate quality: 963

[0444] (Synthesis Example 7)

[0445] <Preparation of Compound (I-26)>

[0446] 0.88 parts of 2,6-diisopropylaniline (manufactured by Tokyo Chemical Industry Co., Ltd.) were replaced with 1.1 parts of 4-bromo-2,6-diisopropylaniline (manufactured by Aldrich), and the procedure was otherwise performed in the same manner as in Synthesis Example 2, yielding 1.7 parts of N represented by formula (I-26). 1 N 2 -bis(2,6-diisopropylphenyl)-N 3 -(4-bromo-2,6-diisopropylphenyl)-benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid triimide (hereinafter, sometimes referred to as compound (I-26)) (70% yield).

[0447]

[0448] <Identification of Compound (I-26)>

[0449] (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 1043

[0450] Accurate quality: 1041

[0451] (Synthesis Example 8)

[0452] <Preparation of Compound (I-27)>

[0453] 0.88 parts of 2,6-diisopropylaniline (manufactured by Tokyo Chemical Industry Co., Ltd.) were replaced with 0.92 parts of 3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthyl-2-amine (manufactured by AmBeed), and the procedure was otherwise performed in the same manner as in Synthesis Example 2, to obtain 1.7 parts of N represented by formula (I-27). 1 N 2 -bis(2,6-diisopropylphenyl)-N 3 -(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphth-2-yl)-benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid triimide (hereinafter, sometimes referred to as compound (I-27)) (70% yield).

[0454]

[0455] <Identification of Compound (I-27)>

[0456] (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H]+ 1004

[0457] Accurate quality: 1003

[0458] (Synthesis Example 9)

[0459] <Preparation of Compound (I-28)>

[0460] 0.88 parts of 2,6-diisopropylaniline (manufactured by Tokyo Chemical Industry Co., Ltd.) were replaced with 0.74 parts of 1,2,3,5,6,7-hexahydro-s-indarsen-4-amine (manufactured by AChemBlock), and the procedure was otherwise performed in the same manner as in Synthesis Example 2, to obtain 1.6 parts of N represented by formula (I-28). 1 N 2 -bis(2,6-diisopropylphenyl)-N 3 -(1,2,3,5,6,7-hexahydro-s-indarsen-4-yl)-benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid triimide (hereinafter, sometimes referred to as compound (I-28)) (yield 66%).

[0461]

[0462] <Identification of Compound (I-28)>

[0463] (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 960

[0464] Accurate quality: 959

[0465] (Synthesis Example 10)

[0466] <Preparation of Compound (I-11)>

[0467] N 1 N 2 -Bis(3-pentyl)perylene-3,4,9,10-tetracarboxylic diimide is replaced with N 1 N 2 -bis(7-tetranyl)perylene-3,4,9,10-tetracarboxylic acid diimide, except that, the procedure was the same as in Synthetic Example 3, yielding 2.1 parts of N represented by formula (I-11). 1 N 2 - bis(7-tetrayl)benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid-2,3,8,9-bisimide-11,12-anhydride (hereinafter, sometimes referred to as compound (I-11)) (yield 74%).

[0468]

[0469] <Identification of Compound (I-11)>

[0470] (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 849

[0471] Accurate quality: 848

[0472] <Preparation of Compound (I-12)>

[0473] Separately, N 1 N 2 2.0 parts of bis(2,6-diisopropylphenyl)benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid-2,3,8,9-bisimide-11,12-anhydride were replaced with 3.0 parts of the above-mentioned compound (I-11), and 0.88 parts of 2,6-diisopropylaniline were replaced with 1.2 parts of 7-tridecylamine (manufactured by Tokyo Chemical Industry Co., Ltd.). Otherwise, the procedure was the same as in Synthesis Example 2, yielding 2.7 parts of N represented by formula (I-12). 1 N 2 N 3 -Tri(7-tetrayl)benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid triimide (hereinafter, sometimes referred to as compound (I-12)) (75% yield).

[0474]

[0475] <Identification of Compound (I-12)>

[0476] (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 1031

[0477] Accurate quality: 1030

[0478] (Synthesis Example 11)

[0479] <Preparation of Compound (I-13)>

[0480] N 1 N 2 2.0 parts of bis(2,6-diisopropylphenyl)benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid-2,3,8,9-bisimide-11,12-anhydride were replaced with 3.0 parts of the above-mentioned compound (I-11), and 0.88 parts of 2,6-diisopropylaniline were replaced with 1.1 parts. Otherwise, the procedure was the same as in Synthesis Example 2, yielding 2.9 parts of N represented by formula (I-13). 1 N 2 -bis(7-tridecyl)-N3 -(2,6-Diisopropylphenyl)-benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid triimide (hereinafter, sometimes referred to as compound (I-13)) (yield 80%).

[0481]

[0482] <Identification of Compound (I-13)>

[0483] (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 1009

[0484] Accurate quality: 1008

[0485] (Synthesis Example 12)

[0486] <Preparation of Compound (I-29)>

[0487] Add N obtained from Synthesis Example 1 1 N 2 5.0 parts of bis(2,6-diisopropylphenyl)benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid-2,3,8,9-bisimide-11,12-anhydride, 6.1 parts of 2-bromobutane (manufactured by Tokyo Chemical Industry Co., Ltd.), 4.0 parts of 2-butanol (manufactured by Tokyo Chemical Industry Co., Ltd.), and 70 parts of N,N-dimethylformamide (manufactured by Kanto Chemical Co., Ltd.) were added dropwise and stirred at 23°C for 1 hour. 4.6 parts of 1,8-diazabicyclo[5.4.0]-7-undecene (manufactured by Tokyo Chemical Industry Co., Ltd.) were further added dropwise, and the mixture was stirred at 60°C for 6 hours. The resulting mixture was concentrated by adding 30 parts of methanol, resulting in a yellow precipitate. The mixture containing this yellow precipitate was filtered, and the residue was washed with 5 parts of methanol. The residue was dried under reduced pressure at 60°C and purified by silica gel column chromatography (solvent: chloroform). The result was 5.0 parts of N represented by formula (I-29). 1 N 2 - bis(2,6-diisopropylphenyl)benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid-2,3,8,9-bisimide-11,12-bis(2-butyl ester) (hereinafter, sometimes referred to as compound (I-29)) (yield 86%).

[0488]

[0489] <Identification of Compound (I-29)>

[0490] (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 935

[0491] Accurate quality: 934

[0492] (Synthesis Example 13)

[0493] <Preparation of Compound (I-30)>

[0494] 6.1 parts of 2-bromobutane were replaced with 8.2 parts of 1-bromo-2-ethylhexane (manufactured by Tokyo Chemical Industry Co., Ltd.), and 4.0 parts of 2-butanol were replaced with 6.7 parts of 2-ethylhexanol (manufactured by Tokyo Chemical Industry Co., Ltd.). Otherwise, the procedure was the same as in Synthesis Example 12, yielding 4.9 parts of N represented by formula (I-30). 1 N 2 - bis(2,6-diisopropylphenyl)benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid-2,3,8,9-bisimide-11,12-bis(2-ethylhexyl ester) (hereinafter, sometimes referred to as compound (I-30)) (yield 75%).

[0495]

[0496] <Identification of Compound (I-30)>

[0497] (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 1048

[0498] Accurate quality: 1047

[0499] (Synthesis Example 14)

[0500] <Preparation of Compound (I-9)>

[0501] Add N obtained from synthesis example 3 1 N 2 4.0 parts of bis(3-pentyl)benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid-2,3,8,9-bisimide-11,12-anhydride, 6.3 parts of 2-bromobutane (manufactured by Tokyo Chemical Industry Co., Ltd.), 4.1 parts of 2-butanol (manufactured by Tokyo Chemical Industry Co., Ltd.), and 56 parts of N,N-dimethylformamide (manufactured by Kanto Chemical Co., Ltd.) were added dropwise and stirred at 23°C for 1 hour. 4.7 parts of 1,8-diazabicyclo[5.4.0]-7-undecene (manufactured by Tokyo Chemical Industry Co., Ltd.) were added dropwise and stirred at 60°C for 9 hours. The resulting mixture was concentrated by adding 31 parts of methanol, resulting in a yellow precipitate. The mixture containing this yellow precipitate was filtered, and the residue was washed with 4 parts of methanol. The residue was dried under reduced pressure at 60°C and purified by silica gel column chromatography (solvent: chloroform). The result was 4.1 parts of N represented by formula (I-9).1 N 2 - bis(3-pentyl)benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid-2,3,8,9-bisimide-11,12-bis(2-butyl ester) (hereinafter, sometimes referred to as compound (I-9)) (yield 84%).

[0502]

[0503] <Identification of Compound (I-9)>

[0504] (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 755

[0505] Accurate quality: 754

[0506] (Synthesis Example 15)

[0507] <Preparation of Compound (I-75)>

[0508] 6.1 parts of 2-bromobutane were replaced with 7.3 parts of 1-bromohexane (manufactured by Tokyo Chemical Industry Co., Ltd.), and 4.0 parts of 2-butanol were replaced with 5.4 parts of 1-hexanol (manufactured by Tokyo Chemical Industry Co., Ltd.). Otherwise, the procedure was the same as in Synthesis Example 12, yielding 4.3 parts of N represented by formula (I-75). 1 N 2 - bis(2,6-diisopropylphenyl)benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid-2,3,8,9-bisimide-11,12-bis(1-hexyl ester) (hereinafter, sometimes referred to as compound (I-75)) (70% yield).

[0509]

[0510] <Identification of Compound (I-75)>

[0511] (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 991

[0512] Accurate quality: 990

[0513] (Synthesis Example 16)

[0514] <Preparation of Compound (I-81)>

[0515] By replacing 6.1 parts of 2-bromobutane with 12 parts of 1-bromotetradecane (manufactured by Tokyo Chemical Industry Co., Ltd.), and replacing 4.0 parts of 2-butanol with 11 parts of 1-tetradecanol (manufactured by Tokyo Chemical Industry Co., Ltd.), the same procedure as in Synthesis Example 12 was performed to obtain 5.6 parts of N represented by formula (I-81).1 N 2 - bis(2,6-diisopropylphenyl)benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid-2,3,8,9-bisimide-11,12-bis(1-tetradecyl ester) (hereinafter, sometimes referred to as compound (I-81)) (75% yield).

[0516]

[0517] <Identification of Compound (I-81)>

[0518] (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 1215

[0519] Accurate quality: 1214

[0520] (Synthesis Example 17)

[0521] <Preparation of Compound (I-82)>

[0522] By replacing 6.1 parts of 2-bromobutane with 13 parts of 1-bromohexadecane (manufactured by Tokyo Chemical Industry Co., Ltd.), and replacing 4.0 parts of 2-butanol with 13 parts of 1-hexadecanol (manufactured by Tokyo Chemical Industry Co., Ltd.), the same procedure as in Synthesis Example 12 was performed to obtain 5.6 parts of N represented by formula (I-82). 1 N 2 - bis(2,6-diisopropylphenyl)benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid-2,3,8,9-bisimide-11,12-bis(1-hexadecyl ester) (hereinafter, sometimes referred to as compound (I-82)) (yield 71%).

[0523]

[0524] <Identification of Compound (I-82)>

[0525] (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 1271

[0526] Accurate quality: 1270

[0527] (Synthesis Example 18)

[0528] <Preparation of Compound (I-87)>

[0529] 6.1 parts of 2-bromobutane were replaced with 7.5 parts of benzyl bromide (manufactured by Tokyo Chemical Industry Co., Ltd.), and 4.0 parts of 2-butanol were replaced with 5.7 parts of benzyl alcohol (manufactured by Tokyo Chemical Industry Co., Ltd.). Otherwise, the procedure was the same as in Synthesis Example 12, yielding 5.0 parts of N represented by formula (I-87). 1 N 2 - bis(2,6-diisopropylphenyl)benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid-2,3,8,9-bisimide-11,12-bis(dibenzyl ester) (hereinafter, sometimes referred to as compound (I-87)) (yield 80%).

[0530]

[0531] <Identification of Compound (I-87)>

[0532] (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 1003

[0533] Accurate quality: 1002

[0534] (Synthesis Example 19)

[0535] <Preparation of Compound (I-85)>

[0536] 6.1 parts of 2-bromobutane were replaced with 7.8 parts of cyclohexylmethylbromide (manufactured by Tokyo Chemical Industry Co., Ltd.), and 4.0 parts of 2-butanol were replaced with 6.1 parts of cyclohexylmethanol (manufactured by Tokyo Chemical Industry Co., Ltd.). Otherwise, the procedure was the same as in Synthesis Example 12, yielding 4.1 parts of N represented by formula (I-85). 1 N 2 - bis(2,6-diisopropylphenyl)benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid-2,3,8,9-bisimide-11,12-bis(dicyclohexylmethyl ester) (hereinafter, sometimes referred to as compound (I-85)) (yield 66%).

[0537]

[0538] <Identification of Compound (I-85)>

[0539] (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 1015

[0540] Accurate quality: 1014

[0541] (Synthesis Example 20)

[0542] <Preparation of Compound INT>

[0543]

[0544] 10 parts of 1,6,7,12-tetrachloro-3,4,9,10-perylene dianhydride (manufactured by Combinatorial Chemistry Co., Ltd.), 13 parts of 2,6-diisopropylaniline (manufactured by Tokyo Chemical Industry Co., Ltd.), and 188 parts of propionic acid were added, and the mixture was stirred under reflux for 20 hours. While keeping the resulting mixture below 20°C, 50 parts of water were added, resulting in an orange precipitate. The mixture containing the orange precipitate was filtered, and the residue was washed with 200 parts of water and 100 parts of methanol. The residue was dried under reduced pressure at 60°C to give 12 parts of the intermediate compound (hereinafter, sometimes referred to as INT) (yield 75%).

[0545] <Identification of Compound INT>

[0546] (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 847

[0547] Accurate quality: 846

[0548] (Synthesis Example 21)

[0549] <Preparation of Compound (II-16)>

[0550] 5.0 parts of the manufactured INT, 1.5 parts of 4-chlorophenol (manufactured by Tokyo Chemical Industry Co., Ltd.), 3.1 parts of 4-tert-butylphenol (manufactured by Tokyo Chemical Industry Co., Ltd.), 11 parts of potassium carbonate (manufactured by Kanto Chemical Co., Ltd.), and 295 parts of N-methylpyrrolidone (manufactured by Kanto Chemical Co., Ltd.) were added, and the mixture was stirred at 130°C for 13 hours. While keeping the resulting mixture below 20°C, 29 parts of pre-prepared 37% hydrochloric acid (manufactured by Kanto Chemical Co., Ltd.) and 142 parts of water were added, resulting in a dark red precipitate. The mixture containing the dark red precipitate was filtered, and the residue was washed with 300 parts of water and 150 parts of methanol. The residue was dried under reduced pressure at 60°C to give 6.1 parts of the compound represented by formula (II-16) (hereinafter, sometimes referred to as compound (II-16)) (yield 81%).

[0551]

[0552] <Identification of Compound (II-16)>

[0553] (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 1237

[0554] Accurate quality: 1236

[0555] (Synthesis Example 22)

[0556] <Preparation of Lumogen (registered trademark) F Yellow083>

[0557] The following formula (x) represents Lumogen (registered trademark) F Yellow083 synthesized in accordance with the description in Japanese Patent Application Publication No. 60-203650.

[0558]

[0559] The compound represented by the following formula (II-3) (hereinafter, sometimes referred to as compound (II-3)) was obtained from Tokyo Chemical Industry Co., Ltd.

[0560]

[0561] (Synthesis Example 23)

[0562] <Preparation of Resin B1>

[0563] A suitable amount of nitrogen was poured into a flask equipped with a reflux condenser, a dropping funnel, and a stirrer to replace the atmosphere with nitrogen. 280 parts of propylene glycol monomethyl ether acetate were then added, and the mixture was heated to 80°C while stirring. Next, 38 parts of acrylic acid and 3,4-epoxytricyclic acrylic acid [5.2.1.0] were added dropwise over 5 hours. 2,6 ] Decane-8-yl ester and 3,4-epoxytricyclic acrylate [5.2.1.0] 2,6 A mixture of decane-9-yl esters (containing 289 parts in a molar ratio of 1:1) and 125 parts of propylene glycol monomethyl ether acetate was prepared. On the other hand, a solution was obtained by dropwise addition of 33 parts of 2,2-azobis(2,4-dimethylpentanones) to 235 parts of propylene glycol monomethyl ether acetate over 6 hours. After the addition was completed, the solution was maintained at 80°C for 4 hours and then cooled to room temperature to obtain a copolymer (resin B1) solution with a solid content of 35.1% and a viscosity of 125 mPa·s as measured by a type B viscometer (23°C). The weight-average molecular weight (Mw) of the resulting copolymer was 9.2 × 10⁻⁶. 3 The dispersion is 2.08, and the acid value converted from solid components is 77 mg-KOH / g. Resin B1 has the following structural units.

[0564]

[0565] <Example 1>

[0566] (1) Solubility test of the compound in a solvent (propylene glycol monomethyl ether acetate; hereinafter, sometimes referred to as PGMEA).

[0567] Weigh approximately 50 mg of the solute (the compound represented by formula (I-23)) and place it into a 20 mL threaded tube. Add approximately 500 mg of solvent (PGMEA) to the tube, and weigh the total mass of solute and solvent. In a constant temperature bath at 20°C, stir with a mixing rotor for 30 minutes. If dissolution is visually confirmed, the solubility is calculated from the mass of the solute relative to the total mass of the solute and solvent. If dissolution is not achieved, continue adding solvent in 500 mg increments until dissolution occurs. Each addition is followed by stirring with a mixing rotor in a constant temperature bath at 20°C for 30 minutes. The solubility is calculated from the mass of the solute relative to the total mass of the solute and solvent when dissolution is visually confirmed. The results are shown in Table 5.

[0568] (2) Preparation of coloring composition

[0569] Mix the components in the following proportions to obtain coloring composition 1.

[0570] (A) Colorant: 2.6 parts of the compound represented by formula (I-23)

[0571] (B) Resin: 58 parts of resin B1 solution

[0572] (E) Solvent: 420 parts of propylene glycol monomethyl ether acetate

[0573] (3) Preparation of coloring and curing resin composition

[0574] Next, the components are mixed in the following proportions to obtain coloring and curing resin composition 1.

[0575] Coloring composition 1,480.6 parts

[0576] (C) Polymerizing compound: Dipentaerythritol hexaacrylate

[0577] (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 40 portions

[0578] (D) Polymerization initiator: N-benzoyloxy-1-(4-phenylthioalkylphenyl)octane-1-one-2-imine (Irgacure (registered trademark) OXE 01; manufactured by BASF)

[0579] 2 copies

[0580] (F) Leveling agent: 0.15 parts of polyether-modified silicone oil (TORAY SILICONE SH8400: manufactured by Toray Dow Corning Co., Ltd.)

[0581] (4) Preparation of colored coating

[0582] A color-curable resin composition was spin-coated onto a 5cm square glass substrate (Eagle XG; manufactured by Corning) to a thickness of 1.7–2 μm after baking. Then, a pre-baking process was performed at 100°C for 3 minutes to form a color-curable resin composition layer. After cooling, the color-curable resin composition layer formed on the substrate was exposed using an exposure machine (TME-150RSK; manufactured by TOPCON Co., Ltd.) at an atmospheric atmosphere with an exposure rate of 80 mJ / cm². 2 The light was irradiated with an exposure level (based on 365nm). After irradiation, the film was baked in an oven at 230°C for 30 minutes to obtain a colored coating.

[0583] (5) Fluorescence intensity measurement

[0584] The fluorescence spectrum of the obtained colored coating was measured using a fluorescence spectrophotometer (FluoroMAX-3; manufactured by Horiba Manufacturing Co., Ltd.) (excitation-side slit 5, fluorescence-side slit 10, excitation wavelength 460 nm), and the fluorescence intensity at the fluorescence wavelength was determined. It should be noted that the fluorescence wavelength referred to here is the wavelength at which the fluorescence spectrum intensity is at its maximum (the peak of the fluorescence spectrum). Furthermore, fluorescence intensity refers to relative fluorescence intensity; the fluorescence intensity observed here was evaluated with the maximum fluorescence intensity of Comparative Example 4 set to 1000. If the maximum fluorescence intensity exceeds 1000, it indicates that the fluorescence intensity is higher than that of the colored coating of Comparative Example 1. The results are shown in Table 5.

[0585] (6) Heat resistance test

[0586] The obtained colored coating was heated at 230°C for 180 minutes in an oven under air atmosphere. Before and after the heat resistance test, the color difference ΔE of the colored coating was measured using a colorimeter (OSP-SP-200; manufactured by OLYMPUS). * ab was measured. For the color difference ΔE * For ab, the smaller the value, the smaller the color change. The results are shown in Table 5.

[0587] (7) Lightfastness test

[0588] A UV cutoff filter (COLORED OPTICAL GLASS L38; manufactured by Hoya Corporation; blocks light below 380nm) was applied to the obtained colored coating film, and the film was irradiated with a xenon lamp for 48 hours using a lightfastness testing machine (SUNTEST CPS+; manufactured by Toyo Seiki Corporation). Before and after the lightfastness test, the color difference ΔE of the colored coating film was measured using a colorimeter (OSP-SP-200; manufactured by OLYMPUS Corporation). * ab was measured. For the color difference ΔE *For ab, the smaller the value, the smaller the color change. The results are shown in Table 5.

[0589] <Examples 2-13 and Comparative Example 1>

[0590] As a colorant, it is used in place of 2.6 parts of compound (I-23):

[0591] 2.6 parts of compound (I-3) (Example 2)

[0592] 2.6 parts of compound (I-22) (Example 3)

[0593] 2.6 parts of compound (I-24) (Example 4)

[0594] 2.6 parts of compound (I-25) (Example 5)

[0595] 2.6 parts of compound (I-26) (Example 6)

[0596] 2.6 parts of compound (I-27) (Example 7)

[0597] 2.6 parts of compound (I-28) (Example 8)

[0598] 2.6 parts of compound (I-12) (Example 9)

[0599] 2.6 parts of compound (I-13) (Example 10)

[0600] 2.6 parts of compound (I-29) (Example 11)

[0601] 2.6 parts of compound (I-30) (Example 12)

[0602] 2.6 parts of compound (I-9) (Example 13)

[0603] 2.6 parts of compound (I-21) (Example 14)

[0604] 2.6 parts of compound (I-75) (Example 15)

[0605] 2.6 parts of compound (I-81) (Example 16)

[0606] 2.6 parts of compound (I-82) (Example 17)

[0607] 2.6 parts of compound (I-90) (Example 18), or

[0608] 2.6 parts of Lumogen (registered trademark) F Yellow083 (Comparative Example 1),

[0609] In addition, the colored curable resin composition was obtained by operating in the same manner as in Example 1, and colored coatings were prepared. The solubility of the compounds used as colorants in PGMEA in each example, the fluorescence measurement results (maximum fluorescence intensity, fluorescence wavelength) in each colored coating, and the heat resistance test results are shown in Table 5.

[0610] <Example 19>

[0611] Mix the components in the following proportions to obtain coloring composition 19.

[0612] (A) Colorant: 1.3 parts of the compound represented by formula (I-23) and 2.6 parts of the compound represented by formula (II-16).

[0613] (B) Resin: 54 parts of resin B1 solution

[0614] (E) Solvent: 420 parts of propylene glycol monomethyl ether acetate

[0615] Coloring composition 19 was used instead of coloring composition 1, and the same procedure as in Example 1 was followed to obtain a coloring curable resin composition and prepare a colored coating film. The fluorescence measurement results (maximum fluorescence intensity, fluorescence wavelength) and lightfastness test results of each colored coating film are shown in Table 6.

[0616] <Examples 20-36 and Comparative Example 2>

[0617] As a colorant, it is used in place of 1.3 parts of compound (I-23):

[0618] 1.3 parts of compound (I-3) (Example 20)

[0619] 1.3 parts of compound (I-22) (Example 21)

[0620] 1.3 parts of compound (I-24) (Example 22)

[0621] 1.3 parts of compound (I-25) (Example 23)

[0622] 1.3 parts of compound (I-26) (Example 24)

[0623] 1.3 parts of compound (I-27) (Example 25)

[0624] 1.3 parts of compound (I-28) (Example 26)

[0625] 1.3 parts of compound (I-12) (Example 27)

[0626] 1.3 parts of compound (I-13) (Example 28)

[0627] 1.3 parts of compound (I-29) (Example 29)

[0628] 1.3 parts of compound (I-30) (Example 30)

[0629] 1.3 parts of compound (I-9) (Example 31)

[0630] 1.3 parts of compound (I-21) (Example 32)

[0631] 1.3 parts of compound (I-75) (Example 33)

[0632] 1.3 parts of compound (I-81) (Example 34)

[0633] 1.3 parts of compound (I-85) (Example 35)

[0634] 1.3 parts of compound (I-87) (Example 36), or

[0635] 1.3 parts of compound Lumogen (registered trademark) F Yellow083 (comparative example 2),

[0636] Otherwise, the same procedure as in Example 19 was followed to obtain the coloring curable resin composition and to prepare the coloring coating. The fluorescence measurement results (maximum fluorescence intensity, fluorescence wavelength) and lightfastness test results of each coloring coating are shown in Table 6.

[0637] <Example 37>

[0638] Mix the components in the following proportions to obtain coloring composition 37.

[0639] (A) Colorant: 1.3 parts of the compound represented by formula (I-23)

[0640] 2.6 parts of the compound represented by formula (II-3)

[0641] (B) Resin: 54 parts of resin B1 solution

[0642] (E) Solvent: 420 parts of propylene glycol monomethyl ether acetate

[0643] Coloring composition 37 was used instead of coloring composition 1, and the same procedure as in Example 1 was followed to obtain a coloring curable resin composition and prepare a colored coating film. The fluorescence measurement results (maximum fluorescence intensity, fluorescence wavelength) and lightfastness test results of each colored coating film are shown in Table 6.

[0644] <Examples 38-40 and Comparative Example 3>

[0645] As a colorant, it is used in place of 1.3 parts of compound (I-23):

[0646] 1.3 parts of compound (I-30) (Example 38)

[0647] 1.3 parts of compound (I-75) (Example 39)

[0648] 1.3 parts of compound (I-82) (Example 40), or

[0649] 1.3 parts of compound Lumogen (registered trademark) F Yellow083 (Comparative Example 3)

[0650] Otherwise, the same procedure as in Example 37 was followed to obtain the coloring curable resin composition, and a coloring coating was prepared. The fluorescence measurement results (maximum fluorescence intensity, fluorescence wavelength) and lightfastness test results of each coloring coating are shown in Table 6.

[0651] <Comparative Example 4>

[0652] As a colorant, 2.6 parts of compound (II-16) were used instead of 2.6 parts of compound (I-23). ​​Otherwise, the same procedure as in Example 1 was followed to obtain a coloring curable resin composition, and a coloring coating was prepared. The fluorescence measurement results (maximum fluorescence intensity, fluorescence wavelength) and lightfastness test results of each coloring coating are shown in Table 6.

[0653] [Table 5]

[0654]

[0655] [Table 6]

[0656]

[0657] The above results demonstrate that the benzo[a]perylene compound of the present invention and the colored coating film formed from the color-curing resin composition exhibit excellent fluorescence intensity. Furthermore, the benzo[a]perylene compound of the present invention exhibits high solubility and good dissolution in the solvent (PGMEA). Consequently, the colored coating film formed from the color-curing resin composition of the present invention demonstrates excellent heat resistance and lightfastness.

Claims

1. A coloring and curing resin composition comprising a colorant, a resin, a polymerizable compound, and a polymerization initiator. The colorant contains a benzo[a]perylene compound. The benzo[a]perylene compound is a compound represented by formula (I). In formula (I), R 1 and R 2 Each of these can be independently represented as a hydrocarbon group having 1 to 30 carbon atoms that may have substituents, an aromatic heterocyclic group having 1 to 30 carbon atoms that may have substituents, or a group formed by bonding the hydrocarbon group that may have substituents with the aromatic heterocyclic group that may have substituents. R 3 R 6 ~R 10 It is a hydrogen atom; R 4 and R 5 for -CO-OR 11 , or R 4 With R 5 Formation includes -CO-O-CO- or -CO-N(R) 11 )-CO- The ring; R 11 This refers to a hydrocarbon group with 1 to 30 carbon atoms that can have substituents, and the presence of multiple R groups. 11 In some cases, they can be different from each other; Indicates a connection key.

2. The coloring and curing resin composition according to claim 1, wherein, The colorant also contains perylene compounds.

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

4. A display device comprising the color filter of claim 3.

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