TWI834854B - Compounds, colored compositions, colored curable resin compositions, color filters and display devices - Google Patents

Abstract

The present invention provides a novel compound and colored composition. A compound represented by formula (I).

[In formula (I), Q represents formula (Q1): *-CR ⁶ =CR ⁵ -NR ³ -**, formula (Q2): *-O-CR ⁵ =N-**, formula (Q3): *-S-CR ⁵ =N-**, formula (Q4): *-N=CR ⁵ -NR ³ -**, or formula (Q5): *-NR ⁶ -CR ⁵ =N-**. The group (* represents the bond with the carbon atom to which R ⁴ is bonded); R ¹ ~ R ⁵ each independently represent a hydrogen atom or a monovalent hydrocarbon group with 1 to 6 carbon atoms that may have a substituent. In the hydrocarbon group The -CH ₂ - contained may be substituted by -O- or -CO-; R ⁶ represents a monovalent aromatic group that may have a substituent or a monovalent aliphatic hydrocarbon group with a carbon number of 1 to 6 that may have a substituent, and the -CH ₂ - contained in the aliphatic hydrocarbon group may be substituted by -O- or -CO-]

Description

Compounds, colored compositions, colored curable resin compositions, Color filters and display devices

The present invention relates to a novel compound and colored composition.

Various dyes are known as colorants contained in colored resin compositions that form color filters included in liquid crystal display devices, solid-state imaging elements, and the like. Patent Document 1 discloses a filter for plasma display panels using squarylium dye.

[Prior art documents]

[Patent Document]

[Patent Document 1] Japanese Patent Application Laid-Open No. 2001-183522

An object of the present invention is to provide a compound excellent in absorbance retention before and after a light resistance test, a colored composition containing the compound, a colored curable resin composition containing the colored composition, and a color filter formed from these compositions. A light sheet and a display device including the color filter.

The present invention provides the following compounds, colored compositions, and colored hardened Plastic resin compositions, color filters and display devices.

[1] A compound represented by formula (I).

[In formula (I), Q represents formula (Q1): *-CR ⁶ =CR ⁵ -NR ³ -**, formula (Q2): *-O-CR ⁵ =N-**, formula (Q3): *-S-CR ⁵ =N-**, formula (Q4): *-N=CR ⁵ -NR ³ -**, or formula (Q5): *-NR ⁶ -CR ⁵ =N-**. The group (* represents the bond with the carbon atom to which R ⁴ is bonded); R ¹ ~ R ⁵ each independently represents a hydrogen atom or a monovalent hydrocarbon group with 1 to 6 carbon atoms that may have a substituent. In the hydrocarbon group The -CH ₂ - contained may be substituted by -O- or -CO-; R ⁶ represents a monovalent aromatic group that may have a substituent or a monovalent aliphatic hydrocarbon group with a carbon number of 1 to 6 that may have a substituent, and the -CH ₂ - contained in the aliphatic hydrocarbon group may be substituted by -O- or -CO-]

Furthermore, ** represents another bond of Q.

[2] A coloring composition containing a coloring agent and a resin containing the compound described in [1].

[3] A colored curable resin composition containing the colored composition as described in [2], a polymerizable compound, and a polymerization initiator.

[4] A color filter formed from the colored composition as described in [2] or the colored curable resin composition as described in [3].

[5] A display device including the color filter according to [4].

The colored composition containing the compound of the present invention has excellent absorbance retention before and after the light resistance test.

1, 2: Image display components

10: Optical filter

11: Adhesive layer for image display components

12: Phase difference film

13:Adhesive layer

14:The first protective film

15:Polarizing film

16:Second protective film

20: Optical filter

21: Adhesive layer for image display components

24:The first protective film

25:Polarizing film

26:Second protective film

Figure 1 (a) and Figure 1 (b) are schematic cross-sectional views showing an example of an optical filter.

FIG. 2(a) is a schematic cross-sectional view showing an example of an organic electroluminescence (EL) display device using an optical filter, and FIG. 2(b) is a schematic cross-sectional view showing a liquid crystal display device using an optical filter. A schematic cross-section of an example.

(Compound represented by formula (I))

The present invention relates to a compound represented by the following formula (I) (hereinafter, there is is called "Compound (I)").

[In formula (I), all symbols have the same meanings as described above]

In compound (I), when Q is a group represented by formula (Q1), compound (I) represents the following structure.

In compound (I), when Q is a group represented by formula (Q2) Below, compound (I) represents the following structure.

[Chemical 4]

In compound (I), when Q is a group represented by formula (Q3), compound (I) represents the following structure.

In compound (I), when Q is a group represented by formula (Q4), compound (I) represents the following structure.

[Chemical 6]

In compound (I), when Q is a group represented by formula (Q5), compound (I) represents the following structure.

For example, when the compound (I) is used in a colored composition described below, the absorbance retention rate before and after the light resistance test is excellent. Compound (I) is also excellent in heat resistance, for example, when used as a colored composition.

In the compound (I) when Q is a group represented by formula (Q1), in addition to the expression represented by the structure, there are also tautomers with a resonance structure represented by the following formula, for example.

[Chemical 8]

In the compound (I) when Q is a group represented by formula (Q2), in addition to the expression represented by the above structure, there are also tautomers with a resonance structure represented by the following formula, for example.

In the compound (I) when Q is a group represented by formula (Q3), in addition to the expression represented by the structure, there are also tautomers with a resonance structure represented by the following formula, for example.

In the compound (I) when Q is a group represented by formula (Q4), in addition to the expression represented by the above structure, there are also tautomers with a resonance structure represented by the following formula, for example.

In the compound (I) when Q is a group represented by formula (Q5), in addition to the expression represented by the structure, there are also tautomers with a resonance structure represented by the following formula, for example.

Compound (I) includes all tautomers including the tautomers illustrated above.

The hydrocarbon group in formula (I) refers to a group containing carbon atoms and hydrogen atoms, The carbon number of the hydrocarbyl group includes the carbon number of the substituent.

The carbon number of the group in which -CH ₂ - in the hydrocarbon group is substituted with -O- or -CO- refers to the carbon number before substitution with -O- or -CO-.

In the formula (I), examples of the monovalent hydrocarbon group having 1 to 6 carbon atoms in R ¹ to R ⁵ include a monovalent aliphatic hydrocarbon group or a monovalent aromatic hydrocarbon group.

The monovalent aliphatic hydrocarbon group in R ¹ to R ⁵ may be a monovalent aliphatic saturated hydrocarbon group or a monovalent aliphatic unsaturated hydrocarbon group. The monovalent aliphatic hydrocarbon group may be a linear or branched chain hydrocarbon group, or may be an alicyclic hydrocarbon group.

Examples of the monovalent aliphatic saturated hydrocarbon group in R ¹ to R ⁵ include linear alkyl groups having 1 to 6 carbon atoms such as methyl, ethyl, propyl, butyl, pentyl, and hexyl; isopropyl , branched alkyl groups with 3 to 6 carbon atoms such as isobutyl, 2nd butyl, 3rd butyl, isopentyl and neopentyl groups; cyclopropyl, cyclopentyl and cyclohexyl groups with 3 to 6 carbon atoms Alicyclic saturated hydrocarbon groups, etc.

Examples of the monovalent aliphatic unsaturated hydrocarbon group in R ¹ to R ⁵ include linear alkenyl groups having 2 to 6 carbon atoms such as vinyl, propenyl, butenyl, pentenyl, and hexenyl; Branched alkenyl groups with 4 to 6 carbon atoms such as dibutenyl and isobutenyl groups; straight-chain alkynyl groups with 3 to 6 carbon atoms such as propynyl, n-butynyl, n-pentynyl and n-hexynyl groups; Branched alkynyl groups with 4 to 6 carbon atoms such as dibutynyl and isobutynyl groups; cycloalkenyl groups with 3 to 6 carbon atoms such as cyclopropenyl, cyclobutenyl, cyclopentenyl and cyclohexenyl; Cycloalkynyl groups with 4 to 6 carbon atoms such as cyclobutynyl, cyclopentynyl and cyclohexynyl.

When the monovalent aliphatic hydrocarbon group in R ¹ to R ⁵ includes a cyclic structure, the number of carbon atoms constituting the cyclic structure is preferably 3 to 6, more preferably 5 or 6.

Examples of the monovalent aromatic hydrocarbon group in R ¹ to R ⁵ include a phenyl group.

In formula (I), examples of substituents that the hydrocarbon groups in R ¹ to R ⁵ may have include halogen atoms, hydroxyl groups, amino groups, nitro groups, sulfonamide groups, and sulfo groups.

Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.

As a substituent that the hydrocarbon group in R ¹ to R ⁵ may have, a halogen atom is preferred.

In formula (I), -CH ₂ - contained in the monovalent hydrocarbon group having 1 to 6 carbon atoms may be substituted with -O- or -CO-. Examples of such a group include -C(=O)CH ₃ and -C(=O)-OCH ₂ CH ₃ .

In formula (I), R ¹ and R ² are preferably each independently a hydrogen atom or an alkyl group, and more preferably both are hydrogen atoms.

R ³ to R ⁵ are preferably each independently a hydrogen atom or an alkyl group. More preferably, R ³ is a hydrogen atom, and R ⁴ and R ⁵ are more preferably each independently an alkyl group.

In formula (I), the monovalent aromatic group in R ⁶ may be a monovalent aromatic hydrocarbon group or a monovalent aromatic heterocyclic group. The monovalent aromatic group may have a single ring structure or a condensed ring structure.

The number of carbon atoms in the monovalent aromatic hydrocarbon group is usually 6 to 30, preferably 6 to 20, more preferably 6 to 13.

Examples of the monovalent aromatic hydrocarbon group include phenyl, methylphenyl, dimethylphenyl, mesitylene, propylphenyl, butylphenyl, hexylphenyl, and 2-ethylhexylphenyl. , naphthyl, biphenyl, terphenyl, propylbiphenyl, anthracenyl, phenanthrenyl, pyrenyl, fluorenyl and other aryl groups with 6 to 16 carbon atoms; benzyl, phenethyl, phenylpropyl aralkyl groups such as phenylbutyl and other aralkyl groups.

The monovalent aromatic hydrocarbon group includes a group in which the hydrogen bonded to the carbon of the aromatic ring constituting the aromatic hydrocarbon group is substituted with an alkyl group or an aryl group, and -CH ₂ - contained in the substituted alkyl group may be - O- or -CO-substitution.

The carbon number of the aromatic ring contained in the monovalent aromatic hydrocarbon group constituting R ⁶ is preferably 6 to 18, more preferably 6 to 12.

The number of carbon atoms in the monovalent aromatic heterocyclic group is usually 2 to 30, preferably 4 to 20, more preferably 4 to 10.

The heteroatom in the monovalent aromatic heterocyclic group represents a nitrogen atom, an oxygen atom, a sulfur atom, or the like. The number of heteroatoms contained in the monovalent aromatic heterocyclic group is preferably 1 to 3, and more preferably 1.

Examples of the monovalent aromatic heterocyclic group include furan, thiophene, pyrrole, oxazole, isoxazole, thiazole, isothiazole, imidazole, pyrazole, furazole, triazole, oxadiazole, and isoxazole. Azole, tetrazole, pyran, pyridine, thiopyran, pyridazine, pyrimidine, pyrazine, triazine, benzofuran, isobenzofuran, benzothiophene, indole, isoindole, indolazine, Indoline, isoindoline, chromene, isobenzopiran, chromane, isochromane, benzopyran, quinoline, isoquinoline, quinolazine, benzimidazole, Benzothiazole, benzothiadiazole, indazole, naphthyridine, quinoxaline, quinazoline, quinazolidine, cinnoline, phthalazine, purine, pteridine, carbazole, xanthene, phenanthridine , acridine, β-carboline, perimidine, phenanthrene, thianthrene, phenoxathiin, phenoxathiin, phenoxathiin, phenoxathiin and other heterocyclic compounds, obtained by removing one hydrogen atom The base.

The monovalent aromatic heterocyclic group includes a group in which the hydrogen contained in the above-mentioned group is substituted by a hydrocarbon group such as an alkyl group or an aryl group.

The carbon number of the aromatic heterocyclic ring contained in the monovalent aromatic heterocyclic group constituting R ⁶ is preferably 6 to 18, more preferably 6 to 12.

In formula (I), examples of the substituents that the aromatic group in R ⁶ may have include: halogen atom, hydroxyl group, amino group, nitro group, aryloxy group, arylcarbonyl group, aryloxycarbonyl group, and carboxyl group. , amine methane group, amine sulfonyl group, sulfo group, etc.

In formula (I), the monovalent aliphatic hydrocarbon group in R ⁶ may be a monovalent aliphatic saturated hydrocarbon group or a monovalent aliphatic unsaturated hydrocarbon group. The monovalent aliphatic hydrocarbon group may be a linear or branched chain hydrocarbon group, or may be an alicyclic hydrocarbon group.

The carbon number of the monovalent aliphatic hydrocarbon group in R ⁶ is usually 1 to 20, preferably 1 to 15, more preferably 1 to 10, and even more preferably 1 to 6. When the monovalent aliphatic hydrocarbon group contains a cyclic structure, the number of carbon atoms constituting the cyclic structure is preferably 3 to 6, more preferably 5 or 6.

The monovalent aliphatic hydrocarbon group in R ⁶ may be a monovalent aliphatic saturated hydrocarbon group or a monovalent aliphatic unsaturated hydrocarbon group. The monovalent aliphatic hydrocarbon group may be a linear or branched chain hydrocarbon group, or may be an alicyclic hydrocarbon group.

Examples of the monovalent aliphatic saturated hydrocarbon group in R ⁶ include those having 1 to 16 carbon atoms such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, and decyl. Linear alkyl groups; branched alkyl groups with 3 to 16 carbon atoms such as isopropyl, isobutyl, second butyl, third butyl, isopentyl, neopentyl and 2-ethylhexyl; rings Cycloalkyl groups with 3 to 16 carbon atoms such as propyl, cyclobutyl, cyclopentyl, and cyclohexyl; alkylcycloalkyl groups with 4 to 16 carbon atoms such as propylcyclohexyl and octylcyclohexyl; cyclohexylbutyl And cycloalkylalkyl groups with 4 to 16 carbon atoms such as cyclohexyl octyl group, etc.

Examples of the monovalent aliphatic unsaturated hydrocarbon group in R ⁶ include vinyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenel, etc. Linear alkenyl groups with 2 to 16 carbon atoms; branched alkenyl groups such as second butenyl and isobutenyl; propynyl, n-butynyl, n-pentynyl, n-hexynyl, n-heptynyl, n- Linear alkynyl groups with 4 to 16 carbon atoms such as octynyl, n-nonynyl and n-decynyl groups; branched alkynyl groups with 4 to 16 carbon atoms such as second butynyl and isobutynyl groups; cyclopropene cycloalkenyl groups with 3 to 16 carbon atoms such as cyclobutenyl, cyclopentenyl and cyclohexenyl groups; alkenyl cycloalkanes with 5 to 16 carbon atoms such as propenylcyclohexyl and 1-decenylcyclohexyl Base; cycloalkynyl groups with 4 to 16 carbon atoms such as cyclobutynyl, cyclopentynyl and cyclohexynyl.

Examples of the monovalent aliphatic unsaturated hydrocarbon group in R ⁶ include vinyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenel, etc. Linear alkenyl groups with 2 to 16 carbon atoms; branched alkenyl groups such as second butenyl and isobutenyl; propynyl, n-butynyl, n-pentynyl, n-hexynyl, n-heptynyl, n- Linear alkynyl groups with 4 to 16 carbon atoms such as octynyl, n-nonynyl and n-decynyl groups; branched alkynyl groups with 4 to 16 carbon atoms such as second butynyl and isobutynyl groups; cyclopropene cycloalkenyl groups with 3 to 16 carbon atoms such as cyclobutenyl, cyclopentenyl and cyclohexenyl groups; alkenyl cycloalkanes with 5 to 16 carbon atoms such as propenylcyclohexyl and 1-decenylcyclohexyl Base; cycloalkynyl groups with 4 to 16 carbon atoms such as cyclobutynyl, cyclopentynyl and cyclohexynyl.

When the monovalent aliphatic hydrocarbon group in R ⁶ contains a cyclic structure, the number of carbon atoms constituting the cyclic structure is preferably 3 to 8, more preferably 4 to 6.

In the formula (I), the substituent that the aliphatic hydrocarbon group in R ⁶ may have includes the substituents exemplified for R ¹ to R ⁵ .

As a substituent that the hydrocarbon group in R ⁶ may have, a halogen atom is preferred.

-CH ₂ - contained in the aliphatic hydrocarbon group in R ⁶ may be substituted by -O- or -CO-. Examples of such a group include -C(=O)CH ₃ and -C(=O)-OCH ₂ CH ₃ .

Examples of the compound (I) include compounds represented by the following formula.

[Chemical 14]

[Chemical 15]

(Production method (1) of compound (I))

Regarding the compound (I) of the present invention, first, a compound represented by the following formula (IV-1) (hereinafter, sometimes referred to as "compound (IV-1)") and the following formula (IV-2) can be The compound represented by the formula (hereinafter, sometimes referred to as "compound (IV-2)") reacts to obtain a compound represented by the following formula (IV-3) (hereinafter, sometimes referred to as "compound (IV-3)"). ), from this compound (IV-3), a compound represented by the following formula (IV-4) (hereinafter, sometimes referred to as "compound (IV-4)") is obtained. Next, this compound (IV-4) is reacted with a compound represented by the following formula (IV-5) (hereinafter, sometimes referred to as "compound (IV-5)") to produce compound (I).

[In formula (IV-1) and formula (IV-3), R ⁷ and R ⁸ each independently represent an alkoxy group having 1 to 20 carbon atoms; formula (IV-2), formula (IV-3) and formula In (IV-4), R ³ to R ⁶ have the same meanings as above; in formula (IV-5), R ¹ and R ² have the same meanings as above]

In formula (IV-1) and formula (IV-3), examples of the alkoxy group having 1 to 20 carbon atoms in R ⁷ and R ⁸ include: methoxy group, ethoxy group, n-propoxy group, iso- Propoxy, n-butoxy, isobutoxy, 2nd butoxy, 3rd butoxy, n-pentyloxy, isopentyloxy, neopentyloxy, n-hexyloxy, n-cyclohexyloxy base, n-dodecyloxy group, etc.

Examples of compound (IV-1) include compounds represented by the following formula.

[Chemical 17]

Examples of compound (IV-2) include compounds represented by the following formula.

Examples of compound (IV-3) include compounds represented by the following formula.

[Chemistry 20]

Examples of compound (IV-4) include compounds represented by the following formula.

[Chemistry 21]

Examples of compound (IV-5) include compounds represented by the following formula.

In the step of producing compound (IV-3), it is preferable to react compound (IV-1) and compound (IV-2) in an organic solvent.

Examples of organic solvents include aromatic hydrocarbon solvents such as toluene and xylene; hydrocarbon solvents such as hexane, cyclohexane, and decalin; and ether solvents such as tetrahydrofuran, 1,4-dioxane, and dimethoxyethane. ; Chlorobenzene, dichlorobenzene, chloroform and other halogenated hydrocarbon solvents; Methanol, ethanol, isopropyl alcohol, butanol and other alcohol solvents; Nitrohydrocarbon solvents such as nitrobenzene; Ketone solvents such as methyl isobutyl ketone; N, N - Amide solvents such as dimethylformamide and 1-methyl-2-pyrrolidone can also be used by mixing these. Among these, butanol is preferred. The usage amount of the organic solvent is preferably from 5 parts by mass to 100 parts by mass relative to 1 part by mass of compound (IV-1), more preferably from 10 parts by mass to 50 parts by mass.

The amount of compound (IV-2) used in the step of producing compound (IV-3) is preferably 0.7 mol or more and 3 mol or less, more preferably 1 mol or more and 2 mol or less based on 1 mol of compound (IV-1).

The reaction temperature is preferably 30°C to 180°C, more preferably 80°C to 140°C. The reaction time is preferably 0.5 to 10 hours, more preferably 1 to 5 hours.

In the step of producing compound (IV-4), it is preferable to reflux compound (IV-3) in an acidic aqueous solution using hydrochloric acid, acetic acid, or the like.

The reaction temperature is preferably 30°C to 180°C, more preferably 80°C to 140°C. The reaction time is preferably 0.5 to 10 hours, more preferably 1 to 5 hours.

In the step of producing compound (I), in terms of yield, it is preferable to react compound (IV-4) and compound (IV-5) in an organic solvent.

Examples of the organic solvent include the organic solvents exemplified above. Among them, a mixed solvent of butanol and toluene is preferred. The usage amount of the organic solvent is preferably not less than 10 parts by mass and not more than 200 parts by mass, more preferably not less than 20 parts by mass and not more than 160 parts by mass, based on 1 part by mass of the total of compound (IV-4) and compound (IV-5). the following.

The amount of compound (IV-5) used in the step of producing compound (I) is preferably 0.7 mol or more and 3 mol or less, more preferably 1 mol or more and 2 mol or less based on 1 mol of compound (IV-4).

The reaction temperature is preferably 30°C to 180°C, more preferably 80°C to 140°C. The reaction time is preferably 0.5 to 10 hours, more preferably 1 to 5 hours.

The method of obtaining the target compound (I) from the reaction mixture is not particularly limited, and various known methods can be used. For example, there is a method of filtering out the precipitated crystals after cooling. The filtered crystals are preferably washed with water and then dried. In addition, if necessary, it can be further purified by known methods such as recrystallization and column chromatography.

(Production method (2) of compound (I))

The compound (I) of the present invention can be produced by the following method: compound (IV-2), compound (IV-5) and squaryl acid (3,4-dihydroxy) represented by the following formula (IV-6) -3-cyclobutene-1,2-dione) reaction.

As the compound (IV-2) and the compound (IV-5), those described above can be used.

In the step of producing compound (I), in terms of yield, it is preferable to adopt a method of dehydration condensation of compound (IV-2), compound (IV-5) and squaric acid in an organic solvent.

Examples of the organic solvent include the organic solvents exemplified above. Among them, a mixed solvent of butanol and toluene is preferred. The usage amount of the organic solvent is preferably not less than 10 parts by mass and not more than 200 parts by mass, more preferably not less than 20 parts by mass and not more than 160 parts by mass, based on 1 part by mass of the total of compound (IV-4) and compound (IV-5). the following.

The amount of squaric acid used in the step of producing compound (I) is preferably 0.45 mol or more and 0.6 mol or less, more preferably 0.47 mol or more, based on 1 mol of the total of compound (IV-2) and compound (IV-5). And less than 0.55mol.

The reaction temperature is preferably 30°C to 180°C, more preferably 80°C to 140°C. The reaction time is preferably 1 hour to 20 hours, more preferably 3 hours to 15 hours.

The method of obtaining the target compound (I) from the reaction mixture is not particularly limited, and various known methods can be used, and examples thereof include the methods described above.

(coloring composition)

The colored composition of the present invention contains a colorant (A) and a resin (B) containing a compound (I). The coloring composition may further contain a solvent (E), a leveling agent (F), or the like. In this specification, unless otherwise specified, the compounds exemplified as each component can be used alone or in combination of multiple types.

The colored composition of the present invention has excellent absorbance retention before and after the light resistance test. The coloring composition is also excellent in heat resistance.

(Color(A))

The coloring agent (A) contained in the coloring composition may contain other dyes as the dye (A1) in addition to the compound (I). Examples of such dyes include oil-soluble dyes, acid dyes, amine salts of acid dyes, and sulfonamide derivatives of acid dyes. Examples of such dyes include Color Index (The Society of Dyers and Printers). Compounds of dyes classified as solvents, acidic, alkaline, reactive, direct, dispersed, mordant, or reducing dyes published by "of Dyers and Colourists"), or known dyes described in dyeing notes (Shikisensha Co., Ltd.) of dyes. In addition, based on the chemical structure, examples include azo dyes, anthraquinone dyes, triphenylmethane dyes, xanthene dyes, and phthalocyanine dyes. These dyes may be used alone, or two or more types may be used in combination.

Specifically, C.I. Solvent Yellow 4 (hereinafter, description of C.I. Solvent Yellow will be omitted and only the number will be described), 14, 15, 23, 24, 25, 38, 62, 63, 68, 79, 81, 82, 83, 89, 94, 98, 99, 162; C.I. Solvent Orange (Solvent Orange) 2, 7, 11, 15, 26, 56; C.I. Solvent Red (Solvent Red) 24, 49, 90, 91, 111, 118, 119, 122, 124, 125, 127, 130, 132, 143, 145, 146, 150, 151, 155, 160, 168, 169, 172, 175, 181, 207, 218, 222, 227, 230, 245, 247; C.I. Solvent Violet (Solvent Violet) 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60; C.I. Solvent Blue (Solvent Blue) 14, 18, 35, 36, 45, 58, 59, 59: 1, 63, 68, 69, 78, 79, 83, 94, 97, 98, 100, 101, 102, 104, 105, 111, 112, 122, 128, 132, 136, 139; C.I. Solvent Green (Solvent Green) 1, 3, 5, 28, 29, 32, 33, etc. C.I. Solvent dye, C.I. Acid Yellow (Acid Yellow) 1, 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112, 113, 114, 116, 119, 123, 128, 134, 135, 138, 139, 140, 144, 150, 155, 157, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251; C.I. Acid Orange (Acid Orange) 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 149, 162, 169 , 173; C.I. Acid Red (Acid Red) 73, 80, 91, 92, 97, 138, 151, 211, 274, 289; C.I. Acid Green (Acid Green) 3, 5, 9, 25, 27, 28, 41 ; C.I. Acid Violet (Acid Violet) 34, 120; C.I. Acid Blue (Acid Blue) 25, 27, 40, 45, 78, 80, 112, etc. C.I. Acid dye, C.I. Basic Green (Basic Green) 1, etc. C.I. Alkaline Dyes, C.I. Reactive Yellow (Reactive Yellow) 2, 76, 116; C.I. Reactive Orange (Reactive Orange) 16, etc. C.I. Reactive dyes, C.I. Direct Yellow (Direct Yellow) 2, 4, 28, 33, 34, 35, 38, 39 , 43, 44, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129, 132, 136, 138, 141; C.I. Direct Orange (Direct Orange) 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107; C.I. Direct Blue (Direct Blue) 40 and other C.I. Direct dyes, C.I. Disperse Yellow (Disperse Yellow) 51, 54, 76; C.I. Disperse Violet (Disperse Violet) 26, 27; C.I. Disperse Blue (Disperse Blue) 1, 14, 56, 60 and other C.I. disperse dyes, as C.I. mordant dyes C.I. Mordant Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65; C.I. Mordant Orange 3, 4, 5, 8, 12, 13, 14, 20 , 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47, 48 and other C.I. mordant dyes, C.I. Vat Green (Vat Green) 1 and other C.I. vat dyes, etc.

In the colorant (A), the content of the compound (I) is preferably not less than 3 parts by mass and not more than 100 parts by mass, more preferably not less than 10 parts by mass and not more than 70 parts by mass, based on 100 parts by mass of the total amount of the dye (A1). or less, and more preferably 15 parts by mass or more and 50 parts by mass or less. When the content of the compound (I) is within the above range, high color reproducibility can be obtained when forming a color filter, and the film tends to be easily formed into a thin film.

The coloring agent (A) contained in the coloring composition preferably contains a pigment (A2). The pigment (A2) is not particularly limited, and known pigments can be used. For example, pigments classified as pigments in the Dye Index (published by The Society of Dyers and Colourists) may be used alone or in combination of two or more types.

Examples of the pigment (A2) include: C.I. Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109 , 110, 117, 125, 128, 129, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 194, 214 and other yellow pigments; C.I. Pigment Orange (Pigment Orange) 13, 31, 36 , 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73 and other orange pigments; C.I. Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 180, 192, 209, 215, 216, 224, 242, 254, 255, 264, 265 Red pigments such as; C.I. Pigment Blue (Pigment Blue) 15, 15: 3, 15: 4, 15: 6, 60 and other blue pigments; C.I. Pigment Violet (Pigment Violet) 1, 19, 23, 29, 32, 36, Purple pigments such as 38; green pigments such as C.I. Pigment Green 7, 36, and 58; brown pigments such as C.I. Pigment Brown 23, 25; and black pigments such as C.I. Pigment Black 1, 7.

As the pigment (A2), preferred are C.I. Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 185, 194, 214 and other yellow pigments; C.I. Pigment Green 7, 36, 58 and other green pigments, preferably C.I. pigments Yellow 138, 150, 185 and C.I. Pigment Green 58, more preferably C.I. Pigment Yellow 138 and C.I. Pigment Green 58. By including the pigment, the transmission spectrum can be easily optimized, and the color filter can have improved light resistance and chemical resistance.

If necessary, the pigment may be subjected to rosin treatment, surface treatment using a pigment derivative introducing an acidic group or a basic group, grafting treatment on the pigment surface using a polymer compound, etc., or micronization using a sulfuric acid micronization method, etc. treatment, or cleaning treatment using an organic solvent or water to remove impurities, removal treatment of ionic impurities using an ion exchange method, etc.

The pigment preferably has a uniform particle size. By containing a pigment dispersant and performing a dispersion treatment, a pigment dispersion liquid in which the pigment is uniformly dispersed in the solution can be obtained.

Examples of the pigment dispersant include surfactants, which may be any of cationic, anionic, nonionic, and amphoteric surfactants. Specific examples include polyester-based, polyamine-based, acrylic-based surfactants, and the like. These pigment dispersants may be used alone or in combination of two or more. Examples of pigment dispersants include KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Flowlen (manufactured by Kyeisha Chemical Co., Ltd.), and Solsperse (registered trademark) as trade names. (manufactured by Zeneca Co., Ltd.), EFKA (registered trademark) (manufactured by BASF Corporation), Ajisper (registered trademark) (Ajinomoto Precision Technology) Fine-Techno Co., Ltd.), Disperbyk (registered trademark) (manufactured by BYK-Chemie), etc.

When a pigment dispersant is used, the usage amount is preferably 1 mass part or more and 100 mass parts or less, more preferably 5 mass parts or more and 50 mass parts or less, based on 100 mass parts of the total amount of pigment (A2). . When the usage amount of the pigment dispersant is within the above range, a pigment dispersion liquid in a uniform dispersed state tends to be obtained.

When pigment (A2) is included, the content ratio of dye (A1) and pigment (A2) in colorant (A) is usually 45:55~1:99 on a mass basis, preferably 40:60~ 2:98, preferably 38:62~3:97.

The content of the colorant (A) is preferably not less than 5 parts by mass and not more than 60 parts by mass, more preferably not less than 8 parts by mass, based on 100 parts by mass of the solid content of the coloring composition. and 55 parts by mass or less, and more preferably 10 parts by mass or more and 50 parts by mass or less. If the content of the colorant (A) is within the above range, the color density when making the color filter is sufficient, and a required amount of the resin (B), etc. can be contained in the coloring composition, so it can be easily carried out. Tendency to become thinner. Here, the “solid content” in this specification refers to what is obtained by removing the solvent from the coloring composition. The total amount of solid content and the content of each component relative thereto can be measured, for example, by a known analysis method such as liquid chromatography or gas chromatography.

(Resin (B))

The resin (B) contained in the coloring composition is not particularly limited, but an alkali-soluble resin is preferred. Examples of the resin (B) include the following resin [K1] to resin [K6].

Resin [K1]: At least one monomer (Ba) (hereinafter, sometimes referred to as "(Ba)") selected from the group consisting of unsaturated carboxylic acid and unsaturated carboxylic anhydride, and a compound having a carbon number of 2 Copolymer of ~4 cyclic ether structure and ethylenically unsaturated bond monomer (Bb) (hereinafter sometimes referred to as "(Bb)"); resin [K2]: (Ba) and (Bb) and Copolymer of monomer (Bc) (hereinafter, sometimes referred to as "(Bc)") (hereinafter, may be referred to as "(Bc)") (herein, different from (Ba) and (Bb)); resin [K3]: (Ba ) and (Bc); Resin [K4]: Resin obtained by reacting the copolymer of (Ba) and (Bc) with (Bb); Resin [K5]: Copolymer of (Bb) and (Bc) A resin formed by the reaction of a substance and (Ba); Resin [K6]: A resin obtained by reacting a copolymer of (Bb) and (Bc) with (Ba) and further reacting with a carboxylic acid anhydride.

Specific examples of (Ba) include unsaturated monocarboxylic acids such as (meth)acrylic acid, crotonic acid, o-vinylbenzoic acid, m-vinylbenzoic acid, and p-vinylbenzoic acid; butene Diacid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid Unsaturated dicarboxylic acids such as phthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyltetrahydrophthalic acid, 1,4-cyclohexenedicarboxylic acid; methyl-5 -Norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo[2.2.1]hept-2-ene, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene, 5-carboxy- 5-methylbicyclo[2.2.1]hept-2-ene, 5-carboxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-carboxy-6-methylbicyclo[2.2.1] Hept-2-ene, 5-carboxy-6-ethylbicyclo[2.2.1]hept-2-ene and other bicyclic unsaturated compounds containing carboxyl groups; 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, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride and other unsaturated dicarboxylic anhydrides; succinic acid mono[2-(meth)acrylamide unsaturated mono[(meth)acryloxyethyl] ester of divalent or higher polycarboxylic acids such as mono[2-(meth)acryloxyethyl] phthalate Alkyl] esters; such as α-(hydroxymeth)acrylic acid, containing hydroxyl and carboxyl groups in the same molecule Unsaturated (meth)acrylates, etc.

Among these, (meth)acrylic acid, maleic anhydride, etc. are preferable from the viewpoint of copolymerization reactivity or solubility of the obtained resin in an alkaline aqueous solution.

(Bb) refers to, for example, a cyclic ether structure having 2 to 4 carbon atoms (for example, at least one selected from the group consisting of an oxetane ring, an oxetane ring, and a tetrahydrofuran ring) and an ethylenic Polymeric compounds with unsaturated bonds. (Bb) is preferably a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth)acryloxy group.

In this specification, "(meth)acrylic acid" means at least one of acrylic acid and methacrylic acid. The same applies to expressions such as "(meth)acrylyl" and "(meth)acrylate".

Examples of (Bb) include monomers having an oxetanyl group and an ethylenically unsaturated bond, monomers having an oxetanyl group and an ethylenically unsaturated bond, and monomers having a tetrahydrofuran group and an ethylenically unsaturated bond. Singletons of saturated bonds, etc.

As (Bb), in terms of further improving the reliability such as heat resistance and chemical resistance of the color filter obtained, a single amount having an oxetyl group and an ethylenically unsaturated bond is preferred. body.

Examples of (Bc) include: (meth)acrylic acid methyl ester, (meth)ethyl acrylate, (meth)acrylic acid n-butyl ester, (meth)acrylic acid second butyl ester, (meth)acrylic acid second butyl ester Tributyl ester, 2-ethylhexyl (meth)acrylate, dodecyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, cyclo(meth)acrylate Pentyl ester, cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, tricyclo[5.2.1.0 ^2,6 ]decan-8-yl (meth)acrylate (this technology In the field, it is called "dicyclopentyl (meth)acrylate" as a common name; in addition, it is sometimes called "tricyclodecyl (meth)acrylate"), (meth)acrylic acid tricyclo[ 5.2.1.0 ^2,6 ]Decene-8-yl ester (called "(meth)acrylic acid dicyclopentenyl ester" as a common name in this technical field), (meth)acrylic acid dicyclopentane Oxyethyl ester, isobornyl (meth)acrylate, adamantyl (meth)acrylate, allyl (meth)acrylate, propargyl (meth)acrylate, phenyl (meth)acrylate, (Meth)acrylate esters such as naphthyl (meth)acrylate and benzyl (meth)acrylate; hydroxyl-containing (meth)acrylic acid 2-hydroxyethyl acrylate, (meth)acrylic acid 2-hydroxypropyl ester and other (meth)acrylic acid esters Meth)acrylates; dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate, and diethyl itaconate; bicyclo[2.2.1]hept-2-ene, 5-methylbicyclo[2.2.1]hept-2-ene, 5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxybicyclo[2.2.1]hept-2-ene, 5-hydroxy Methylbicyclo[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-bis(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5,6-dimethoxybicyclo[2.2.1]heptyl -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( Bicyclic unsaturated compounds such as tert-butoxycarbonyl)bicyclo[2.2.1]hept-2-ene, 5,6-bis(cyclohexyloxycarbonyl)bicyclo[2.2.1]hept-2-ene; N -Phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimide-3-maleimide Iminobenzoate, N-succinimidyl-4-maleyl iminobutyrate, N-succinimidyl-6-maleyl iminocaproate, N -Dicarbonyl imide derivatives such as succinimidyl-3-maleimide propionate, N-(9-acridinyl)maleimide; styrene, α -Methyl styrene, m-methylstyrene, p-methylstyrene, vinyltoluene, p-methoxystyrene, acrylonitrile, methacrylonitrile, vinyl chloride, vinylidene chloride, acrylamide, methyl Acrylamide, vinyl acetate, 1,3-butadiene, isoprene, 2,3-dimethyl-1,3-butadiene, etc.

Among these, in terms of copolymerization reactivity and heat resistance, styrene, vinyltoluene, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo[2.2.1]hept-2-ene, etc.

Specific examples of the resin (B) include: (meth)acrylic acid 3,4-epoxycyclohexylmethyl ester/(meth)acrylic acid copolymer, acrylic acid 3,4-epoxytricyclo [5.2.1.0 ^2.6 ] Resins such as decyl ester/(meth)acrylic acid copolymer [K1]; glycidyl (meth)acrylate/benzyl (meth)acrylate/(meth)acrylic acid copolymer, glycidyl (meth)acrylate Ester/styrene/(meth)acrylic acid copolymer, acrylic acid 3,4-epoxytricyclo[5.2.1.0 ^2.6 ]decyl ester/(meth)acrylic acid/N-cyclohexylmaleimide copolymer , 3,4-epoxytricyclo[5.2.1.0 ^2.6 ]decyl acrylate/(meth)acrylic acid/N-cyclohexylmaleimide copolymer/hydroxyl-containing (meth)acrylate copolymer , 3-methyl-3-(meth)acryloxymethyloxetane/(meth)acrylic acid/styrene copolymer and other resins [K2]; Benzyl (meth)acrylate/( Resins such as meth)acrylic acid copolymer and styrene/(meth)acrylic acid copolymer [K3]; glycidyl (meth)acrylate is added to benzyl (meth)acrylate/(meth)acrylic acid copolymer. Resin formed by adding glycidyl (meth)acrylate to tricyclodecyl (meth)acrylate/styrene/(meth)acrylic acid copolymer, tricyclodecyl (meth)acrylate /Resins such as benzyl (meth)acrylate/(meth)acrylic acid copolymer plus glycidyl (meth)acrylate [K4]; make tricyclodecyl (meth)acrylate/(meth)acrylate ) A resin obtained by reacting a copolymer of glycidyl acrylate and (meth)acrylic acid, a copolymer of tricyclodecyl (meth)acrylate/styrene/glycidyl (meth)acrylate and (meth) Resins such as resins obtained by reacting acrylic acid [K5]; resins obtained by reacting tricyclodecyl (meth)acrylate/glycidyl (meth)acrylate copolymer with (meth)acrylic acid and then reacting with tetrahydrophthalate Resins such as resins obtained by reacting phthalic anhydride [K6], etc.

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

For example, the resin [K1] can be referred to the document "Experimental Methods for Polymer Synthesis" (written by Takayuki Otsu, Chemical Doujin Publishing Co., Ltd., 1st edition, 1st printing, issued on March 1, 1972). The method and the cited documents described in this document were used to produce the product.

Furthermore, the obtained copolymer can be used directly as a solution after the reaction, as a concentrated or diluted solution, or as a copolymer extracted in the form of a solid (powder) by a method such as reprecipitation. In particular, the solvent contained in the colored composition of the present invention is used as a solvent during the polymerization, whereby the solution after the reaction can be directly used to prepare the colored composition of the present invention, so that the colored composition of the present invention can be made of Manufacturing steps are simplified.

The polystyrene-reduced weight average molecular weight of the resin (B) is preferably 3,000 to 100,000, more preferably 5,000 to 50,000, further preferably 5,000 to 30,000. When the molecular weight is within the above range, the hardness of the color filter is increased, the residual film rate is high, the solubility of the unexposed portion to the developer is good, and the resolution of the colored pattern tends to be improved.

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

The acid value of the resin (B) is preferably 50mg-KOH/g~170mg-KOH/g, more preferably 60mg-KOH/g~150mg-KOH/g, and even more preferably 70mg-KOH/g~135mg-KOH/ g. Here, the acid value is a value measured as the amount of potassium hydroxide (mg) required to neutralize 1 g of resin (B), and can be determined by titration using a potassium hydroxide aqueous solution, for example.

The content of the resin (B) is preferably 10 to 90 parts by mass relative to 100 parts by mass of the solid content, more preferably 20 to 85 parts by mass, and further preferably 30 to 80 parts by mass. When the content of the resin (B) is within the above range, a colored pattern can be formed, and the resolution and residual film rate of the colored pattern tend to be improved.

(Solvent(E))

The solvent (E) that can be contained in the coloring composition is not particularly limited, and a solvent commonly used in the field can be used alone or in combination of two or more solvents commonly used in the field. Examples include: ester solvents (solvents that contain -COO- but not -O- in the molecule), ether solvents (solvents that contain -O- but do not contain -COO- in the molecule). agent), ether ester solvent (solvent that contains -COO- and -O- in the molecule), ketone solvent (solvent that contains -CO- and does not contain -COO- in the molecule), alcohol solvent (solvent that contains OH in the molecule) And does not include -O-, -CO- and -COO- solvents), aromatic hydrocarbon solvents, amide solvents, dimethyl styrene, etc.

Examples of the ester solvent include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutyrate, ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, and isoamyl acetate. , Butyl propionate, Isopropyl butyrate, Ethyl butyrate, Butyl butyrate, Methyl pyruvate, Ethyl pyruvate, Propyl pyruvate, Methyl acetate acetate, Ethyl acetate acetate, Ring Hexanol acetate and γ-butyrolactone, etc.

Examples of the ether solvent include: ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, Ethylene 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, phenylethyl ether and methyl anisole, etc.

Examples of the ether ester solvent include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethoxyethyl acetate, and 3-methoxypropionic acid. Methyl ester, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, 2-methoxypropionic acid Ethyl ester, 2-methoxypropylpropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, 2- Ethoxy-2-methylpropionate, 3-methoxybutyl acetate, acetic acid 3-Methyl-3-methoxybutyl ester, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol mono Ethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate and dipropylene glycol methyl ether acetate, etc.

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

Examples of the alcohol solvent include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, glycerin, and the like.

Examples of aromatic hydrocarbon solvents include benzene, toluene, xylene, mesitylene, and the like.

Examples of the amide solvent include N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, and the like.

As the solvent, it is preferably selected from the group consisting of propylene glycol monomethyl ether acetate, ethyl lactate, propylene glycol monomethyl ether, ethyl 3-ethoxypropionate, ethylene glycol monomethyl ether, ethylene glycol monobutyl ether, Ethylene glycol monomethyl ether, diethylene glycol monoethyl ether, 3-methoxybutyl acetate, 3-methoxy-1-butanol, 4-hydroxy-4-methyl-2-pentanone, N- One solvent from the group consisting of methylpyrrolidone, N,N-dimethylformamide and tetrahydrofuran or a mixed solvent that combines two or more, preferably propylene glycol monomethyl ether acetate. One solvent or a combination of two or more of the group consisting of , propylene glycol monomethyl ether, ethyl 3-ethoxypropionate, N-methylpyrrolidone, N,N-dimethylformamide and tetrahydrofuran mixed solvent.

The content of the solvent (E) is preferably 70 to 95 parts by mass, more preferably 75 to 92 parts by mass relative to 100 parts by mass of the coloring composition of the present invention. In other words, the total amount of solid content of the coloring composition is preferably 5 to 30 parts by mass, more preferably 8 to 25 parts by mass. If the content of the solvent (E) is within the above range, the flatness during coating will be good and the color density will not be insufficient when forming the color filter, so the display characteristics will tend to be good.

(Leveling agent (F))

Examples of the leveling agent (F) that can be included in the coloring composition include silicone surfactants, fluorine surfactants, silicone surfactants having fluorine atoms, and the like. These may have a polymerizable group in a side chain.

Examples of the silicone-based surfactant include surfactants having a siloxane bond in the molecule. Specifically, Toray silicone DC3PA, Toray silicone SH7PA, Toray silicone DC11PA, Toray silicone SH21PA, Toray silicone Toray silicone SH28PA, Toray silicone SH29PA, Toray silicone SH30PA, Toray silicone SH8400 (trade name: Toray Dow Corning) ), KP321, KP322, KP323, KP324, KP326, KP340, KP341 (manufactured by Shin-Etsu Chemical Industry Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF-4446, TSF4452 and TSF4460 (Japanese Momentive High-tech materials (Momentive Performance Materials Japan) Co., Ltd.), etc.

Examples of the fluorine-based surfactant include surfactants having a fluorocarbon chain in the molecule. Specifically, Fluorad (registered trademark) FC430, Fluorad (registered trademark) FC431 (manufactured by Sumitomo 3M Co., Ltd.), Megafac (registered trademark) F142D, Megafac (registered trademark) F171, Megafac (registered trademark) F172, Megafac (registered trademark) F173, Megafac (registered trademark) F177, Megafac ( Registered trademark) F183, Megafac (registered trademark) F554, Megafac (registered trademark) R30, Megafac (registered trademark) RS-718-K (DIC) Manufactured), Eftop (registered trademark) EF301, Eftop (registered trademark) EF303, Eftop (registered trademark) EF351, Eftop (registered trademark) EF352 (Manufactured by Mitsubishi Materials Electronics Chemical Co., Ltd.), Surflon (registered trademark) S381, Surflon (registered trademark) S382, Surflon (registered trademark) SC101, Surflon (registered trademark) (Surflon) (registered trademark) SC105 (manufactured by Asahi Glass Co., Ltd.) and E5844 (manufactured by Daikin Fine Chemicals Laboratory Co., Ltd.), etc.

Examples of the silicone-based surfactant having a fluorine atom include surfactants having a siloxane bond and a fluorocarbon chain in the molecule. Specifically, Megafac (registered trademark) R08, Megafac (registered trademark) BL20, Megafac (registered trademark) F475, Megafac (registered trademark) F477 and Megafac (registered trademark) F443 (manufactured by DIC Co., Ltd.), etc.

The content of the leveling agent (F) is preferably not less than 0.0001 parts by mass and not more than 0.2 parts by mass, more preferably not less than 0.0002 parts by mass and not more than 0.1 parts by mass, and still more preferably not less than 0.0003 parts by mass, based on 100 parts by mass of the coloring composition. And less than 0.05 parts by mass. Furthermore, this content does not include the content of the pigment dispersant. If the content of the leveling agent (F) is within the above range, the color filter can have good flatness.

(Other ingredients in the coloring composition)

The coloring composition may contain fillers, other polymer compounds, adhesion accelerators, antioxidants, light stabilizers and other additives known in the technical field as necessary.

(Method for manufacturing coloring composition)

The coloring composition can be prepared, for example, by mixing the colorant (A), the resin (B), the solvent (E), the leveling agent (F) and other components as necessary.

The pigment (A2) is preferably mixed with part or all of the solvent (E) in advance and dispersed using a bead mill or the like until the average particle diameter of the pigment becomes approximately 0.2 μm or less. At this time, part or all of the pigment dispersant and resin (B) may be prepared as necessary. The target coloring composition can be prepared by mixing the remaining components into the pigment dispersion obtained in the above manner so as to have a predetermined concentration.

The dye can be dissolved in a part or all of the solvent (E) in advance to prepare a solution. It is preferable to filter the solution using a filter with a pore size of about 0.01 μm to 1 μm.

It is preferable to filter the mixed colored composition using a filter with a pore size of about 0.1 μm to 10 μm.

(Colored curable resin composition)

The colored curable resin composition of the present invention contains the colored composition, a polymerizable compound (C), and a polymerization initiator (D). The colored curable resin composition may further contain a polymerization starting aid (D1).

The colored curable resin composition of the present invention is expected to have excellent absorbance retention before and after the light resistance test. The colored curable resin composition is also expected to have excellent heat resistance.

(Polymerizable compound (C))

The polymerizable compound (C) contained in the colored curable resin composition is a compound that can be polymerized by active radicals and/or acids generated from the polymerization initiator (D). Examples thereof include polymerizable ethylene. Compounds having a sexually unsaturated bond, etc. are preferably (meth)acrylate compounds.

Among these, the polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds. Examples of such polymerizable compounds include nonylphenyl carbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexyl carbitol acrylate, and 2-hydroxyethyl acrylate. Compounds having one ethylenically unsaturated bond, such as esters, N-vinylpyrrolidone, and the compounds exemplified as (Ba), (Bb), and (Bc); 1,6-hexanediol bis(methyl ) acrylate, ethylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, bis(acryloxyethyl ethyl) of bisphenol A compounds with two ethylenically unsaturated bonds; trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate Compounds with three ethylenically unsaturated bonds such as ester, tris(2-(meth)acryloxyethyl) isocyanurate; pentaerythritol tetra(meth)acrylate, ethylene glycol modified pentaerythritol Compounds with four ethylenically unsaturated bonds such as tetra(meth)acrylate, propylene glycol-modified pentaerythritol tetra(meth)acrylate, caprolactone-modified pentaerythritol tetra(meth)acrylate, etc.; dipentaerythritol penta(meth)acrylate; Compounds with five ethylenically unsaturated bonds such as acrylates; dipentaerythritol hexa(meth)acrylate, ethylene glycol modified dipentaerythritol hexa(meth)acrylate, propylene glycol modified dipentaerythritol hexa(meth)acrylate ) acrylate, caprolactone-modified dipentaerythritol hexa(meth)acrylate and other compounds with six ethylenically unsaturated bonds; tripentaerythritol hepta(meth)acrylate, tripentaerythritol octa(meth)acrylate, Compounds having seven or more ethylenically unsaturated bonds, such as pentaerythritol nona(meth)acrylate and pentaerythritol deca(meth)acrylate.

Among them, the polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds, and more preferably a polymerizable compound having five to six ethylenically unsaturated bonds.

Among them, dipentaerythritol penta(meth)acrylate and dipentaerythritol hexa(meth)acrylate are particularly preferred.

The weight average molecular weight of the polymerizable compound (C) is preferably from 150 to 2,900, more preferably from 250 to 1,500.

The content of polymerizable compound (C) relative to 100 parts by mass of solid content The amount is preferably 7 to 65 parts by mass, more preferably 13 to 60 parts by mass, and still more preferably 17 to 55 parts by mass. When the content of the polymerizable compound (C) is within the above range, the residual film rate during formation of the colored pattern and the chemical resistance of the color filter tend to improve.

The content ratio of resin (B) to polymerizable compound (C) [resin (B): polymerizable compound (C)] is preferably 20:80~80:20 on a mass basis, more preferably 35:65~80: 20.

(Polymerization initiator (D))

The polymerization initiator (D) contained in the colored curable resin composition is not particularly limited as long as it is a compound that can generate active radicals, acids, etc. by the action of light or heat to initiate polymerization, and can be used. Well-known polymerization initiator. Examples of polymerization initiators that generate active radicals include O-acyl oxime compounds, phenylalkyl ketone compounds, triazine compounds, acyl phosphine oxide compounds, and biimidazole compounds.

The O-acyl oxime compound is a compound having a partial structure represented by formula (Dd1). In the following, * indicates a bonding key.

Examples of O-benzyl oxime compounds include N-benzyloxy-1-(4-phenylmercaptophenyl)butan-1-one-2-imine and N-benzyloxy-1-(4-phenylmercaptophenyl)butan-1-one-2-imine. Oxy-1-(4-phenylmercaptophenyl)octane-1-one-2-imine, N-benzoyloxy-1-(4-phenylmercaptophenyl)-3-cyclo Pentylpropane-1-one-2-imine, N-acetyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl] Ethane-1-imine, N-acetyloxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethyl-2,4-dioxetane) Pentylmethyloxy)benzoyl}-9H-carbazol-3-yl]ethane-1-imine, N-acetyloxy-1-[9-ethyl-6-(2 -Methyl)-9H-carbazol-3-yl]-3-cyclopentylpropane-1-imine, N-benzoyloxy-1-[9-ethyl-6- (2-Methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropan-1-one-2-imine, etc. Commercially available products such as Irgacure (registered trademark) OXE01 and OXE02 (the above manufactured by BASF) and N-1919 (manufactured by ADEKA) can also be used. Among them, the O-benzyl oxime compound is preferably selected from the group consisting of N-benzyloxy-1-(4-phenylmercaptophenyl)butan-1-one-2-imine, N-benzyloxy-1-(4-phenylmercaptophenyl)butan-1-one-2-imine, baseoxy-1-(4-phenylmercaptophenyl)octane-1-one-2-imine and N-benzoyloxy-1-(4-phenylmercaptophenyl)-3- At least one of the group consisting of cyclopentylpropane-1-one-2-imine, more preferably N-benzoyloxy-1-(4-phenylmercaptophenyl)octane-1 -Keto-2-imine. If these O-acyl oxime compounds are used, a high-brightness color filter tends to be obtained.

The phenylalkyl ketone compound is a compound having a partial structure represented by the following formula (Dd2) or a partial structure represented by the following formula (Dd3). In these partial structures, the benzene ring may have a substituent.

[Chemical 26]

Examples of compounds having a partial structure represented by formula (Dd2) include: 2-methyl-2-morpholinyl-1-(4-methylmercaptophenyl)propan-1-one, 2-dimethyl Amino-1-(4-morpholinylphenyl)-2-benzylbutan-1-one, 2-(dimethylamino)-2-[(4-methylphenyl)methyl ]-1-[4-(4-morpholinyl)phenyl]butan-1-one, etc. Commercially available products such as Irgacure 369, 907, and 379 (the above manufactured by BASF) can also be used.

Examples of compounds having a partial structure represented by formula (Dd3) include: 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1-[4 -(2-Hydroxyethoxy)phenyl]propane-1-one, 1-hydroxycyclohexylphenylketone, 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propane-1 -Ketone oligomers, α,α-diethoxyacetophenone, benzyldimethyl ketal, etc.

In terms of sensitivity, the phenylalkyl ketone compound is preferably a compound having a partial structure represented by formula (Dd2).

Examples of the triazine compound include: 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, Methyl)-6-(4-methoxynaphthyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5-triazine , 2,4-bis(trichloromethyl)-6-(4-methoxystyryl)-1,3,5-triazine, 2,4-bis(trichloromethyl base)-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-methylbenzene) methyl)vinyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)vinyl]-1, 3,5-triazine, etc.

Examples of the acylphosphine oxide compound include 2,4,6-trimethylbenzoyldiphenylphosphine oxide and the like. Commercially available products such as Irgacure (registered trademark) 819 (manufactured by BASF Corporation) can also be used.

Examples of the biimidazole compound include compounds represented by the following formula (Dd4).

[In formula (Dd4), R ^d1 to R ^d5 represent an aryl group having 6 to 10 carbon atoms which may have a substituent]

In the formula (Dd4), examples of the aryl group having 6 to 10 carbon atoms in R ^d1 to R ^d5 include phenyl, methylphenyl, dimethylphenyl, ethylphenyl, naphthyl, etc., and preferred examples are is phenyl.

Examples of substituents that the aryl group having 6 to 10 carbon atoms may have include a halogen atom and an alkoxy group having 1 to 4 carbon atoms. Examples of the halogen atom include those exemplified by R ¹ to R ⁴ in the formula (I). Examples of the alkoxy group having 1 to 4 carbon atoms include a methoxy group, an ethoxy group, a propoxy group and a butoxy group, and a methoxy group is preferred.

Specific examples of the biimidazole compound include: 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2 ,3-dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole (for example, refer to Japanese Patent Application Laid-Open No. 6-75372, Japanese Patent Application Laid-Open No. 6-75373, etc.), 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5 ,5'-tetrakis(alkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetrakis(dialkoxyphenyl)biimidazole , 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetrakis(trialkoxyphenyl)biimidazole (for example, refer to Japanese Patent Publication No. 48-38403, Japanese Patent Laid-Open No. 62-174204, etc.), biimidazole compounds in which the phenyl groups at the 4, 4', 5, 5'-positions are substituted with alkoxycarbonyl groups (for example, refer to Japanese Patent Laid-Open No. 7-10913, etc. )wait. Among them, compounds represented by the following formulas and mixtures thereof are preferred.

[Chemical 28]

Furthermore, examples of the polymerization initiator (D) include benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether; benzophenone, and methyl o-benzoyl benzoate. , 4-phenylbenzophenone, 4-benzyl-4'-methyldiphenyl sulfide, 3,3',4,4'-tetrakis(tert-butylperoxycarbonyl)diphenyl Methyl ketone, 2,4,6-trimethylbenzophenone and other benzophenone compounds; 9,10-phenanthrenequinone, 2-ethylanthraquinone, camphorquinone and other quinone compounds; 10-butyl-2- Chloroacridone, benzil, methyl phenylglyoxylate, titanocene compounds, etc. These are preferably used in combination with a polymerization starting aid (D1) (especially amines) described below.

Examples of the acid-generating polymerization initiator include 4-hydroxyphenyldimethylsulfonate p-toluenesulfonate, 4-hydroxyphenyldimethylsulfonate hexafluoroantimonate, and 4-acetyloxybenzene. Dimethylsulfonium p-toluenesulfonate, 4-acetyloxyphenylmethylbenzylsulfonate hexafluoroantimonate, triphenylsonium p-toluenesulfonate, triphenylsonium hexafluoroantimonate, Diphenyl Onium salts such as iodonium p-toluene sulfonate and diphenyl iodonium hexafluoroantimonate, or nitrobenzyl toluene sulfonate, benzoin toluene sulfonate, etc.

As the polymerization initiator (D), it is preferably a polymerization initiator that generates active radicals, more preferably one selected from the group consisting of phenylalkyl ketone compounds, triazine compounds, acylphosphine oxide compounds, and O-acyloxime compounds. and a biimidazole compound, and more preferably a polymerization initiator including an O-acyl oxime compound.

The content of the polymerization initiator (D) is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass relative to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). . When the content of the polymerization initiator (D) is within the above range, the sensitivity tends to be high and the exposure time tends to be shortened, so the productivity of the color filter is improved.

(Polymerization starting aid (D1))

The polymerization initiation aid (D1) that may be contained in the colored curable resin composition is a compound or a sensitizer for accelerating the polymerization of a polymerizable compound that initiates polymerization by a polymerization initiator. When a polymerization initiating aid (D1) is included, it is usually used in combination with a polymerization initiator (D).

Examples of the polymerization starting aid (D1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds, carboxylic acid compounds, and the like.

Examples of amine compounds include alkanolamines such as triethanolamine, methyldiethanolamine, and triisopropanolamine; methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, and -Isoamyl dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, Aminobenzoates such as 2-ethylhexyl 4-dimethylaminobenzoate; N,N-dimethyl-p-toluidine, 4,4'-bis(dimethylamino)benzyl Ketone (commonly known as Michler's ketone), 4,4'-bis(diethylamino)benzophenone, 4,4'-bis(ethylmethylamino)benzophenone, etc. Alkylamino benzophenones, etc., among them, alkylamino benzophenones are preferred, and 4,4'-bis(diethylamino)benzophenone is preferred. Commercially available products such as EAB-F (manufactured by Hodogaya Chemical Industry Co., Ltd.) can also be used.

Examples of alkoxyanthracene compounds include: 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl- 9,10-diethoxyanthracene, 9,10-dibutoxyanthracene, 2-ethyl-9,10-dibutoxyanthracene, etc.

Examples of the thioxanthone compound include: 2-isopropylthianthrone, 4-isopropylthianthrone, 2,4-diethylthianthrone, and 2,4-dichlorothianthone. Anthrone, 1-chloro-4-propoxythiaxanthone, etc.

Examples of carboxylic acid compounds include: phenylthioglycolic acid, methylphenylthioglycolic acid, ethylphenylthioglycolic acid, methylethylphenylthioglycolic acid, dimethylphenylmercaptoacetic acid, and methoxyphenylmercaptoacetic acid. Acetic acid, dimethoxyphenylthioglycolic acid, chlorophenylthioglycolic acid, dichlorophenylmercaptoacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine , naphthoxyacetic acid, etc.

When using these polymerization starting aids (D1), the content is preferably 0.1 to 30 parts by mass relative to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C), more preferably Preferably, it is 1 to 20 parts by mass. When the amount of the polymerization starting aid (D1) is within this range, a colored pattern can be formed with further high sensitivity, and the productivity of the color filter tends to be improved.

(Other components in the colored curable resin composition)

The colored curable resin composition may optionally contain additives known in the technical field such as a chain transfer agent.

(Method for manufacturing colored curable resin composition)

The colored curable resin composition can be prepared, for example, by mixing the colored composition with the polymerizable compound (C), the polymerization initiator (D), the polymerization initiation assistant (D1), and other components. When patterning is performed by photolithography, a colored curable resin composition can be preferably used. It is preferable to filter the mixed colored curable resin composition using a filter with a pore diameter of about 0.1 μm to 10 μm.

(Color filter and manufacturing method thereof)

The color filter of the present invention can be formed from the above-mentioned colored composition or colored curable resin composition. The color filter of the present invention has excellent absorbance retention before and after the light resistance test. The color filter also has excellent heat resistance.

As a method of manufacturing a color filter formed of a colored composition or a colored curable resin composition, for example, a method such as applying the colored composition or the colored curable resin composition on a substrate and heating and drying ( Pre-baking) and/or drying under reduced pressure, thereby removing volatile components such as solvents and drying to form a smooth composition layer, and then post-baking. The hardened coating film formed in the above manner may also be the color filter of the present invention.

As the substrate, glass plates such as quartz glass, borosilicate glass, alumina silicate glass, soda-lime glass with a silica-coated surface, or polycarbonate, polymethyl methacrylate, or polyester can be used. Resin boards such as ethylene terephthalate, silicon, A thin film of aluminum, silver, silver/copper/palladium alloy, etc. is formed on the substrate. Other color filter layers, resin layers, transistors, circuits, etc. can also be formed on these substrates.

Examples of coating methods include spin coating, slit coating, slit and spin coating, and the like.

The temperature during heat drying is preferably 30°C to 120°C, more preferably 50°C to 110°C. The heating time is preferably 10 seconds to 60 minutes, more preferably 30 seconds to 30 minutes.

When drying under reduced pressure is performed, it is preferably carried out under a pressure of 50 Pa to 150 Pa and a temperature range of 20°C to 25°C.

The thickness of the composition layer formed by applying the colored composition or the colored curable resin composition is not particularly limited and may be appropriately selected according to the film thickness of the target color filter.

Furthermore, it is preferable to post-bake the obtained composition layer. The post-baking temperature is preferably 150°C~250°C, and more preferably 160°C~235°C. The post-baking time is preferably 1 minute to 120 minutes, more preferably 10 minutes to 60 minutes.

The film thickness of the obtained color filter is not particularly limited and can be appropriately adjusted according to the purpose or use. For example, it is 0.1 μm to 30 μm, preferably 0.1 μm to 20 μm, and more preferably 0.5 μm to 6 μm.

The cured coating film obtained in this manner can also be patterned by, for example, etching.

The colored composition or colored curable resin composition of the present invention can also be used to produce a colored pattern by photolithography, inkjet, printing, or the like. in, When using a colored curable resin composition containing a polymerizable compound (C) and a polymerization initiator (D), photolithography is preferred. Photolithography is a method in which a colored curable resin composition is applied to a substrate and dried to form a composition layer, and the composition layer is exposed and developed through a light mask. Coating and drying can be performed under the conditions described above.

The composition layer is exposed through a photomask for forming a target coloring pattern. The pattern on this photomask is not particularly limited, and a pattern corresponding to the intended use can be used.

As a light source used for exposure, a light source that generates light with a wavelength of 250 nm to 450 nm is preferred. For example, you can use a filter that cuts off the wavelength range of less than 350nm to cut off light, or you can use a bandpass filter that extracts the light in these wavelength ranges to selectivity around 436nm, 408nm, and 365nm. extract. Specific examples include mercury lamps, light emitting diodes, metal halide lamps, halogen lamps, and the like.

In order to uniformly irradiate the entire exposure surface with parallel light or to accurately align the mask and the substrate on which the composition layer is formed, it is preferable to use exposure devices such as a mask aligner and a stepper.

The exposed composition layer is developed by contacting a developer to form a colored pattern on the substrate. By development, the unexposed portion of the composition layer is dissolved in the developer and removed. As the developer, for example, 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 mass% to 10 mass%, more preferably 0.03 Mass%~5 mass%. Furthermore, the developer may contain a surfactant.

The development method may be any of liquid coating method, dipping method, spray method, etc. Furthermore, the substrate can be tilted to any angle during development.

It is preferable to perform water washing after development.

Preferably, the obtained colored pattern is post-baked. The post-baking temperature and time can also be the same as those mentioned above.

Color filters can be preferably used in solid-state imaging devices and display devices (for example, liquid crystal display devices, organic EL devices, electronic paper, etc.).

(Optical filter)

Compound (I) can be used, for example, in optical filters for display devices and the like. Optical filters can be expected to have excellent absorbance retention before and after the light resistance test. Optical filters can also be expected to have excellent heat resistance.

The optical filter is usually a layer formed of a composition containing a light-transmissive (preferably optically transparent) thermoplastic resin or thermosetting resin, and may be, for example, a film-like material. The optical filter only needs to have a layer containing Compound (I) (hereinafter, sometimes referred to as a "color correction layer"). It may be a color correction film with a single-layer structure including a color correction layer, or may be a color correction film containing a color correction layer. A laminate with a multi-layered structure of correction layers. When the optical filter has a multi-layer structure, it may include one color correction layer or two or more color correction layers. The compounds (I) contained in the two or more layers may be the same or different from each other. different.

When the optical filter is a laminated body, the color correction layer may be an adhesive layer, or may be a resin layer other than the adhesive layer (hereinafter, may be simply referred to as "resin layer"). When the color correction layer is an adhesive layer, it may be one that bonds two layers included in the optical filter to each other, or it may be one that is used to bond the optical filter to other components such as an image display element. Builder. The following layer may be an adhesive layer formed of an adhesive agent or an adhesive layer formed of an adhesive agent.

When the color correction layer is an optical filter (color correction film) with a single-layer structure, or when it is a resin layer other than the adhesive layer in an optical filter with a multi-layer structure, the color correction film or the resin layer The method of containing compound (I) is not particularly limited. For example, [i] a method of kneading a resin forming a color correction film or a resin layer and heating it to form a film, [ii] mixing a resin forming a color correction film or a resin layer or a monomer of the resin with a compound ( I) A method of dispersing or dissolving it in an organic solvent and forming it into a film by casting or the like. In addition, [iii] a coating liquid in which compound (I) is dispersed or dissolved in a binder resin or an organic solvent may be applied to a resin base film and the resultant may be used as a resin layer, or the coating liquid may be obtained from the resin base film. What was obtained by peeling off the resin base film from the resin layer was used as a color correction film. The thickness of the color correction film or the resin layer is not particularly limited, but may be, for example, 1 μm to 200 μm.

When the color correction film or resin layer contains compound (I), its content is not particularly limited. For example, the compound (I) can be 0.001 parts by mass or more, preferably 0.02 parts by mass or more, more preferably 0.05 parts by mass or more, based on 100 parts by mass of the base polymer forming the color correction film or the resin layer. It can be 10 parts by mass or less, preferably 3 parts by mass or less, more preferably 0.5 parts by mass or less.

When the color correction layer is an adhesive layer, the method of making the adhesive layer contain the compound (I) is not particularly limited. In preparing the adhesive composition that forms the adhesive layer or adhesive composition, just add compound (I). The thickness of the subsequent layer is not particularly limited, but may be, for example, 1 μm to 100 μm.

When the adhesive layer contains compound (I), its content is not particularly limited. For example, the compound (I) can be 0.01 parts by mass or more, preferably 0.02 parts by mass or more, more preferably 0.02 parts by mass or more, based on 100 parts by mass of the base polymer that forms the adhesive and/or adhesive contained in the adhesive layer. 0.05 parts by mass or more, and may be 10 parts by mass or less, preferably 5 parts by mass or less, more preferably 0.5 parts by mass or less.

The optical filter can be used in a display device such as an organic electroluminescence (organic EL) display device or a liquid crystal display device, and can be used by being attached to the viewing side of the image display element of the display device. In this case, the optical filter preferably has an adhesive layer and a resin layer other than the adhesive layer, and at least one of the adhesive layer and the resin layer is preferably a color correction layer containing compound (I).

When the optical filter is a laminated body, its laminated structure is not particularly limited. For example, it may have the laminated structure shown in FIG. 1(a) and FIG. 1(b) . FIG. 1(a) and FIG. 1(b) are schematic cross-sectional views showing an example of an optical filter. The optical filter 10 shown in (a) of FIG. 1 can be used in an organic EL display device. For example, the optical filter 10 may include an adhesive layer 11 for image display elements, a retardation film 12, an adhesive layer 13, a first protective film 14, a polarizing film 15, and a second protective film 16 in this order. The adhesive layer 11 and the adhesive layer 13 for image display elements are equivalent to the adhesive layer, and the retardation film 12, the first protective film 14, the polarizing film 15 and the second protective film 16 are all equivalent to the resin layer.

The first protective film 14, the polarizing film 15 and the second protective film in the optical filter 10 The protective film 16 can form a polarizing plate, and the first protective film 14 and the second protective film 16 can have an adhesive layer on the side of the bonding surface with the polarizing film 15 . The adhesive layer 11 for image display elements is used for bonding to the light-emitting layer including the organic EL element, which is the image display element of the organic EL display device. A spacer (release film) not shown in the figure may be provided on the surface of the adhesive layer 11 for image display elements opposite to the retardation film 12 .

The optical filter 20 shown in FIG. 1(b) can be used in a liquid crystal display device. For example, the optical filter 20 may include an adhesive layer 21 for image display elements, a first protective film 24, a polarizing film 25, and a second protective film 26 in this order. The adhesive layer 21 for image display elements corresponds to the adhesive layer, and the first protective film 24, the polarizing film 25, and the second protective film 26 all correspond to the resin layer.

The first protective film 24 , the polarizing film 25 and the second protective film 26 in the optical filter 20 can form a polarizing plate. The first protective film 24 and the second protective film 26 can have Then layer. The adhesive layer 21 for image display elements is used to bond it to a liquid crystal cell which is an image display element of a liquid crystal display device. A spacer (release film) not shown in the figure may be provided on the surface of the adhesive layer 21 for image display elements opposite to the first protective film 24 .

The compound (I) may be contained in at least any one of the resin layer and the adhesive layer forming the optical filter 10 and the optical filter 20 shown in FIGS. 1(a) and 1(b) . In the optical filter 10 shown in FIG. 1(a) , for example, one or more of the adhesive layer 11 for image display elements, the adhesive layer 13 , the first protective film 14 , and the second protective film 16 may be included. Contains said compound (I). In the optical filter 20 shown in FIG. 1(b) , for example, the adhesive layer 21 for image display elements and the first protective film may be 24. Compound (I) is contained in at least one of the second protective films 26 .

The optical filter 10 and the optical filter 20 shown in FIG. 1(a) and FIG. 1(b) are just examples, and may have a multilayer structure other than the above-mentioned structure. For example, a film with an anti-glare function or a film with an anti-surface reflection function may be further provided on the surface of the second protective film 16 or 26 opposite to the polarizing film 15 or 25. layer. In addition, the first protective film 14 and the first protective film 24 may also have the function as a retardation film, and the second protective film 16 and the second protective film 26 may also have an anti-glare function or an anti-surface reflection function and serve as a retardation film. functions, etc. Furthermore, a color corrector containing the compound (I) may be provided at an arbitrary position separately from each layer forming the optical filter 10 and the optical filter 20 shown in FIGS. 1(a) and 1(b) . layer.

Since the optical filter contains the compound (I), it is expected to have excellent absorbance retention before and after the light resistance test. Optical filters are also expected to have excellent heat resistance.

Each member forming the optical filter will be described in detail below.

(adhering layer)

Examples of the adhesive that can be used for the adhesive layer include aqueous adhesives, active energy ray-curable adhesives, and combinations thereof. Examples of water-based adhesives include polyvinyl alcohol-based resin aqueous solutions, water-based two-component urethane-based emulsion adhesives, and the like. An active energy ray-curable adhesive is an adhesive that is cured by irradiation with active energy rays such as ultraviolet rays. Examples include adhesives containing a polymerizable compound and a photopolymerizable initiator, and adhesives containing a photoreactive resin. , contains the binder tree Adhesives for lipids and photoreactive cross-linking agents, etc. Examples of the polymerizable compound include photopolymerizable monomers such as photocurable epoxy monomers, photocurable (meth)acrylic monomers, and photocurable urethane monomers, or Oligomers derived from these monomers, etc. Examples of the photopolymerization initiator include substances that generate active species such as neutral radicals, anionic radicals, and cationic radicals by irradiating active energy rays such as ultraviolet rays.

As the adhesive that can be used for the adhesive layer, conventionally known adhesives can be used. Examples of the adhesive include: (meth)acrylic adhesive, urethane adhesive, silicone adhesive, polyester adhesive, polyamide adhesive, and polyether adhesive. , fluorine-based adhesives, rubber-based adhesives, etc. In addition, energy ray curable adhesives, thermosetting adhesives, etc. may also be used. Among these, (meth)acrylic adhesives are preferably used from the viewpoints of transparency, adhesion, reliability, etc.

The (meth)acrylic adhesive is not particularly limited. It is a polymer containing (meth)acrylate as the main component (containing 50% by mass or more), and may be a homopolymer of (meth)acrylate. , it can also be a copolymer of (meth)acrylate and other (meth)acrylate. Examples of (meth)acrylates include: (butylmeth)acrylate, ethyl(meth)acrylate, methyl(meth)acrylate, isooctyl(meth)acrylate, and (meth)acrylic acid 2 -Ethylhexyl ester, 2-phenoxyethyl (meth)acrylate. Furthermore, in a polymer mainly composed of these (meth)acrylates, polar monomers can be copolymerized. Examples of polar monomers include: (meth)acrylic acid, (meth)acrylic acid 2-hydroxypropyl, (meth)acrylic acid 2-hydroxyethyl, (meth)acrylamide, (meth)acrylic acid 2-(N,N-dimethylamino)ethyl ester, glycidyl (meth)acrylate, etc. have carboxyl groups, Monomers with polar functional groups such as hydroxyl, amide, amine, and epoxy groups. The (meth)acrylic resin used for the (meth)acrylic adhesive can use a resin having a weight average molecular weight (Mw) of 100,000 or more, preferably 600,000 or more, and usually 2,500,000 or less.

These (meth)acrylic adhesives can also be used alone, and are usually used in combination with cross-linking agents. Examples of the cross-linking agent include: divalent or polyvalent metal ions that form carboxylic acid metal salts with carboxyl groups; amine compounds that form amide bonds with carboxyl groups; and epoxy compounds. Or diol compounds that form ester bonds with carboxyl groups; isocyanate compounds that form amide bonds with carboxyl groups, etc. Among them, isocyanate compounds can be preferably used.

Among isocyanate compounds, xylylene diisocyanate, toluene diisocyanate, or hexamethylene diisocyanate can be preferably used; adducts obtained by reacting these isocyanate compounds with polyols such as glycerol or trimethylolpropane ; These isocyanate compounds are made into dimers, trimers, etc., or mixtures thereof; mixtures of two or more isocyanate compounds listed above, etc.

Preferred isocyanate-based compounds include toluene diisocyanate, adducts obtained by reacting toluene diisocyanate and polyols, toluene diisocyanate dimers and toluene diisocyanate trimers, and hexamethylene hexamethylene diisocyanate, an adduct obtained by reacting hexamethylene diisocyanate with a polyol, a dimer of hexamethylene diisocyanate, and a trimer of hexamethylene diisocyanate.

The content of the cross-linking agent in the acrylic adhesive is usually 0 to 5 parts by mass relative to 100 parts by mass of the (meth)acrylic resin, which is relatively Preferably, it is 0.05 parts by mass or more and 2 parts by mass or less.

The acrylic adhesive may further contain a silane compound. If the acrylic adhesive contains a silane compound, the adhesiveness between the obtained adhesive layer and optical members such as glass substrates can be improved.

Examples of the silane compound include vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris(2-methoxyethoxy)silane, 3-aminopropyltriethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane Silane, 3-methacryloxypropyltrimethoxysilane, 3-hydrothiopropyltrimethoxysilane, 3-glycidyloxypropyltrimethoxysilane, 3-glycidoxypropyl Triethoxysilane, 3-glycidoxypropyldimethoxymethylsilane, 3-glycidoxypropylethoxydimethylsilane, etc. Two or more silane compounds may also be used.

The silane compound may be of the silicone oligomer type. When the silicone oligomer is expressed in the form of a (monomer) oligomer, examples thereof include: 3-mercaptopropyltrimethoxysilane-tetramethoxysilane copolymer, mercaptomethyltrimethyl Oxysilane-tetramethoxysilane copolymer, 3-glycidyloxypropyltrimethoxysilane-tetramethoxysilane copolymer, 3-methacryloxypropyltrimethoxysilane-tetramethoxysilane Methoxysilane copolymer, 3-acryloxypropyltrimethoxysilane-tetramethoxysilane copolymer, vinyltrimethoxysilane-tetramethoxysilane copolymer, etc.

The content of the silane compound in the adhesive composition is usually 0.01 parts by mass or more and 10 parts by mass or less based on 100 parts by mass of the (meth)acrylic resin. It is preferably 0.05 parts by mass or more and 5 parts by mass or less, and more preferably 0.1 parts by mass or more and 2 parts by mass or less. If the content of the silane compound is 0.01 parts by mass or more, the effect of improving the adhesion between the adhesive layer and optical members such as glass substrates can be easily obtained. In addition, if the content of the silane compound is 10 parts by mass or less, exudation of the silane compound from the adhesive layer can be suppressed.

The acrylic adhesive may further contain an ionic compound as an antistatic agent for imparting antistatic properties. An ionic compound is a compound having inorganic or organic cations and inorganic or organic anions. Acrylic adhesives may also contain two or more ionic compounds.

Examples of inorganic cations include alkali metal ions such as lithium cation [Li ⁺ ], sodium cation [Na ⁺ ], and potassium cation [K ⁺ ], beryllium cation [Be ²⁺ ], magnesium cation [Mg ²⁺ ], and calcium Cations [Ca ²⁺ ] and other alkaline earth metal ions, etc.

Examples of organic cations include imidazolium cations, pyridinium cations, pyrrolidinium cations, ammonium cations, sulfonium cations, and phosphonium cations.

Examples of inorganic anions include chloride anion [Cl ^- ], bromide anion [Br ^- ], iodide anion [I ^- ], tetrachloroaluminate anion [AlCl ₄ ^- ], heptachlorodialuminate Anion [Al ₂ Cl ₇ ^- ], tetrafluoroborate anion [BF ₄ ^- ], hexafluorophosphate anion [PF ₆ ^- ], perchlorate anion [ClO ₄ ^- ], nitrate anion [NO ₃ ^- ] , hexafluoroarsenate anion [AsF ₆ ^- ], hexafluoroantimonate anion [SbF ₆ ^- ], hexafluoroniobate anion [NbF ₆ ^- ], hexafluorotantalate anion [TaF ₆ ^- ], Cyanamide anion [(CN) ₂ N ^- ], etc.

Examples of organic anions include acetate anion [CH ₃ COO ^- ], trifluoroacetate anion [CF ₃ COO ^- ], methane sulfonate anion [CH ₃ SO ₃ ^- ], and trifluoromethanesulfonate anion. [CF ₃ SO ₃ ^- ], p-toluenesulfonate anion [p-CH ₃ C ₆ H ₄ SO ₃ ^- ], bis(fluorosulfonyl)imide anion [(FSO ₂ ) ₂ N ^- ], bis (Trifluoromethanesulfonyl)imide anion [(CF ₃ SO ₂ ) ₂ N ^- ], tris(trifluoromethanesulfonyl) methanide anion [(CF ₃ SO ₂ ) ₃ C ^- ], dimethyl Phosphite anion [(CH ₃ ) ₂ POO ^- ], (poly)hydride fluoride anion [F(HF) _n ^- ] (n is about 1 to 3), cyanogen sulfide anion [SCN ^- ] , perfluorobutane sulfonate anion [C ₄ F ₉ SO ₃ ^- ], bis(pentafluoroethanesulfonyl)imide anion [(C ₂ F ₅ SO ₂ ) ₂ N ^- ], perfluorobutane Acid acid anion [C ₃ F ₇ COO ^- ], (trifluoromethanesulfonyl) (trifluoromethane carbonyl) imide anion [(CF ₃ SO ₂ ) (CF ₃ CO) N ^- ], etc.

Specific examples of the ionic compound can be selected from combinations of the above-mentioned cationic components and anionic components.

Examples of ionic compounds having organic cations include N-octylpyridinium hexafluorophosphate, N-octyl-4-methylpyridinium hexafluorophosphate, and N-butyl-4-methyl Pyridinium hexafluorophosphate, N-decylpyridinium bis(fluorosulfonyl)amide imide, N-hexylpyridinium bis(trifluoromethanesulfonyl)amide imide, N-octylpyridinium bis( Pyridinium salts such as trifluoromethanesulfonyl)imide; 1-ethyl-3-methylimidazolium hexafluorophosphate, 1-ethyl-3-methylimidazolium p-toluenesulfonate, 1- Ethyl-3-methylimidazolium bis(fluorosulfonyl)imide, 1-ethyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide, 1-butyl-3 -Imidazolium salts such as methylimidazolium methanesulfonate; N-butyl-N-methylpyrrolidinium hexafluorophosphate, N-butyl-N-methylpyrrolidinium bis(fluorosulfonyl) Imide, N-butyl-N-methylpyrrolidinium bis(trifluoromethanesulfonate) pyrrolidinium salts such as acyl)imide; quaternary ammonium salts such as tetrabutylammonium hexafluorophosphate, tetrabutylammonium p-toluenesulfonate, etc.

Examples of ionic compounds having inorganic cations include lithium bromide, lithium iodide, sodium hexafluorophosphate, and the like.

From the viewpoint of maintaining antistatic properties, the ionic compound is preferably solid at room temperature. The ionic compound preferably has a melting point of 30°C or higher, and further 35°C or higher. On the other hand, if the melting point is too high, the compatibility with the (meth)acrylic resin will deteriorate. Therefore, the melting point of the ionic compound is preferably 90°C or lower, more preferably 70°C or lower, and even more preferably not higher than 70°C. Over 50℃.

The content of the ionic compound in the acrylic adhesive is preferably not less than 0.1 parts by mass and not more than 8 parts by mass, more preferably not less than 0.2 parts by mass and not more than 6 parts by mass, based on 100 parts by mass of the (meth)acrylic resin. More preferably, it is 0.5 parts by mass or more and 5 parts by mass or less, and particularly preferably, it is 1 part by mass or more and 5 parts by mass or less. The content of the ionic compound being 0.1 parts by mass or more is advantageous for improving the antistatic performance, and the content of the ionic compound being 8 parts by mass or less is advantageous for maintaining the durability of the adhesive layer.

Various additives can also be formulated into adhesives or adhesives. Examples of additives include heavy-duty agents, tackiness-imparting resins, antioxidants, ultraviolet absorbers, defoaming agents, corrosives, light diffusing agents such as fine particles, and the like.

(resin layer)

Examples of the resin layer include: a polarizing film as a linear polarizing element; a protective film provided to protect the surface of a polarizing film, etc.; a retardation film; and others other than a retardation film. Optical compensation film; film with uneven surface and anti-glare function, film with anti-surface reflection function; reflective film with reflective function on the surface; semi-transmissive reflective film with both reflective and transmissive functions; light diffusion film ; Hard coat film; color correction film, etc. The optical filter may include one or more than two types of the resin layers.

Examples of the polarizing film include a polarizing film in which iodine is aligned in a polyvinyl alcohol-based resin layer, a polarizing film in which a liquid crystal compound and a dichroic dye are aligned.

When the resin layer is other than a polarizing film, the material is not particularly limited, and examples thereof include chain polyolefin resins (polyethylene resins, polypropylene resins, etc.), cyclic polyolefin resins (norbornene resins, etc.) resin, etc.); cellulose ester resins such as triacetyl cellulose, diethyl cellulose, and cellulose acetate propionate; polyethylene terephthalate, polyethylene naphthalate Polyester resins such as diester; polycarbonate resins; (meth)acrylic resins such as (meth)acrylic acid and polymethyl (meth)acrylate; vinyl alcohol resins such as polyvinyl alcohol and polyvinyl acetate ; Polystyrene-based resin; mixtures, copolymers, etc. of these. These resins may also contain one or more additives such as lubricants, plasticizers, dispersants, heat stabilizers, ultraviolet absorbers, infrared absorbers, antistatic agents, antioxidants, microparticles and other light diffusing agents.

(display device)

The color filter or optical filter can be preferably used in display devices such as organic EL display devices, liquid crystal display devices, inorganic electroluminescence (inorganic EL) display devices, electron emission display devices, and electronic paper.

2(a) and 2(b) are schematic cross-sectional views showing an example of a display device including an optical filter. The display device shown in FIG. 2(a) is an organic EL display device including the optical filter 10 shown in FIG. 1(a) and the image display element 1 as a light-emitting layer including an organic EL element. The optical filter 10 can be disposed on the viewing side of the image display element 1 via the adhesive layer 11 for the image display element.

The display device shown in FIG. 2(b) is a liquid crystal display device including the optical filter 20 shown in FIG. 1(b) and the image display element 2 as a liquid crystal cell including a liquid crystal layer. The optical filter 20 can be disposed on the viewing side of the image display element 2 via the adhesive layer 21 for the image display element.

[Example]

Hereinafter, the present invention will be explained in more detail using Examples and Comparative Examples, but the present invention is not limited to these Examples. Unless otherwise stated, "parts" in Examples, Comparative Examples, Application Examples, and Comparative Application Examples are parts by mass.

[Identification of compounds]

The structure of the compound was identified by mass analysis (LC; model 1200 manufactured by Agilent, MASS; LC/MSD model manufactured by Agilent).

[Example 1 (Compound (I))]

25.00 parts (110.5 mmol) of 3,4-dibutoxy-3-cyclobutene-1,2-dione (manufactured by Tokyo Chemical Industry Co., Ltd.) represented by the following formula (IV-1-a) After heating and stirring 82 parts of 1-butanol at 110°C, 3-ethyl-2,4-dimethylpyrrole represented by the following formula (IV-2-a) was added dropwise over 10 minutes. (Tokyo Chemical Industry Co., Ltd. (manufactured) 13.61 parts (110.5 mmol), and heated and refluxed for 3 hours. After the reaction, when the mixture was cooled to room temperature, crystals precipitated, so the solution was filtered to separate the solution and the precipitate. The precipitate was pulped using 500 mL of hexane, and a light green powder (a compound represented by the following formula (IV-3-a)) was obtained.

Use 110.0 mL of acetic acid to pour the powder obtained above into an aqueous solution prepared with 12.6 mL of concentrated hydrochloric acid and 84.0 mL of distilled water. Heat and reflux at 110°C for 2 hours. As a result, the color changes from light green to light orange. , the reaction stops. The reaction solution was cooled to room temperature, and the light orange powder was separated by filtration and then slurried and washed with 500 mL of hexane. As a result, 18.34 parts of a light yellow compound represented by the following formula (IV-4-a) was obtained (product rate 75.7%).

[Chemical 30]

0.5 part (2.3 mmol) of the obtained compound represented by formula (IV-4-a), 0.32 part (2.5 mmol) of phloroglucinol (manufactured by Tokyo Chemical Industry Co., Ltd.), and 1-butanol Mix 6.8 parts and 53 parts of toluene. The obtained mixture was stirred at a temperature of 110° C. for 3 hours while removing the generated water using a Dean-Stark tube. After the reaction was completed, the mixture was cooled to room temperature. As a result, a precipitate was obtained. Therefore, the mixture was separated by filtration and purified with 100 mL of hexane and 100 mL of methanol. As a result, a compound represented by the following formula (A-1) was obtained as a red powder. (Hereinafter, may be referred to as "compound (A-1)") 0.61 parts (yield 81%). The obtained compound (A-1) was subjected to mass analysis.

(Mass analysis) Ionization mode=ESI+: m/z=[M+H] ⁺ 328.3 Accurate mass (Exact Mass): 327.1

[Comparative example 1]

1 part (8.8) of 3,4-dihydroxy-3-cyclobutene-1,2-dione (squaric acid) (manufactured by Fujifilm and Wako Pure Chemical Industries, Ltd.) represented by the following formula (IV-6) mmol), 2.16 parts (17.5 mmol) of 3-ethyl-2,4-dimethylpyrrole (manufactured by Tokyo Chemical Industry Co., Ltd.) represented by the formula (IV-2-a), 1-butanol 33 parts (0.4 mol) and 55.2 parts (0.6 mol) of toluene were mixed. The obtained mixture was stirred at a temperature of 110° C. for 3 hours while removing the generated water using a Dean-Stark tube. After the reaction, the solvent in the reaction liquid was distilled off, 220 parts of ion-exchange water was added, and the precipitated crude product was filtered.

From the obtained crude product, the compound represented by formula (B-1) (hereinafter, sometimes referred to as "compound (B-1)") is separated by column chromatography using silica gel (developing solvent chloroform), Then, it was dried under reduced pressure at a temperature of 60° C. for 12 hours to obtain 2.4 parts of compound (B-1). The obtained compound (B-1) was subjected to mass analysis.

(Mass analysis) Ionization mode=ESI+: m/z=[M+H] ⁺ 325.5 Accurate mass (Exact Mass): 324.2

[Chemical 33]

[Example 2 (coloring composition)]

(Synthesis of resin (B1))

After flowing an appropriate amount of nitrogen into a flask equipped with a reflux cooler, a dropping funnel, and a stirrer to replace it with a nitrogen atmosphere, add 141 parts of ethyl lactate and 178 parts of propylene glycol monomethyl ether acetate, and heat to 85°C while stirring. ℃. Then, 38 parts of acrylic acid, 3,4-epoxy tricyclo acrylate [5.2.1.0 ^2,6 ] decane-8-yl ester and 3,4-epoxy tricyclo acrylate [5.2.1.0 ^{2 ,6} ] 25 parts of a mixture of decane-9-yl ester (content ratio 1:1), 137 parts of cyclohexylmaleimide, 50 parts of 2-hydroxyethyl methacrylate, and propylene glycol monomethyl ether A mixed solution of 338 parts of acetate. On the other hand, a mixed solution of 5 parts of 2,2-azobisisobutyronitrile dissolved in 88 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After the dropwise addition, the temperature was maintained for 4 hours and then cooled to room temperature to obtain a copolymer (resin (B1)) solution with a B-type viscosity (23°C) of 23 mPa˙s and a solid content of 25.6%. The weight average molecular weight Mw of the produced copolymer was 8000, the acid value of the solid content was 111 mg-KOH/g, and the dispersion degree was 2.1. Resin (B1) has the following structural units.

[Chemical 34]

(Preparation of coloring composition)

Colored composition (a-1) is obtained by mixing the following components.

(Preparation of colored coating film)

The coloring composition (a-1) was coated on a 5cm square glass substrate (Eagle 2000; manufactured by Corning Company) by spin coating, and then prebaked at 100°C for 3 minutes to form composition layer. Thereafter, post-baking was performed at 230° C. for 3 minutes in an oven to obtain a colored coating film (a-1). A light resistance test was performed using the obtained colored coating film (a-1). The results are shown in Table 1.

[Lightfastness test]

An ultraviolet cutoff filter (light filter) is arranged on the obtained colored coating film (a-1) Glass (COLORED OPTICAL GLASS) L38, manufactured by HOYA Co., Ltd., cutting off light below 380 nm), was irradiated with xenon light for 24 hours using a light resistance testing machine (Suntest CPS+, manufactured by Toyo Seiki Co., Ltd.). The absorbance at the maximum absorption wavelength of the colored coating film (a-1) was measured before and after light irradiation, and the absorbance after light irradiation was calculated as 100%. Table 1 shows the maximum absorption wavelength of the colored coating film (a-1).

[Heat resistance test]

The obtained colored coating film (a-1) was heated in an oven at 230° C. for 20 minutes. Before and after heating, the absorbance at the maximum absorption wavelength of the colored coating film (a-1) was measured, and the absorbance after heating was calculated as 100%. As a result, the absorbance after heating of the colored coating film (a-1) was 72%.

[Comparative example 2]

Except having used 0.10 part of compound (B-1) instead of compound (A-1), it carried out similarly to Example 1, and obtained the colored composition (b-1). In addition, except using this colored composition (b-1), it carried out similarly to Example 1, and obtained the colored coating film (b-1). Using the obtained colored coating film (b-1), a light resistance test was conducted in the same procedure as in Example 2. The results are shown in Table 1.

As shown in Table 1, the colored composition containing Compound (I) was excellent in absorbance retention before and after the light resistance test.

Claims (5)

A compound represented by formula (I);

[In formula (I), Q represents formula (Q1): *-CR ⁶ =CR ⁵ -NR ³ -**, formula (Q2): *-O-CR ⁵ =N-**, formula (Q3): *-S-CR ⁵ =N-**, formula (Q4): *-N=CR ⁵ -NR ³ -**, or formula (Q5): *-NR ⁶ -CR ⁵ =N-**. The group (* represents the bond with the carbon atom to which R ⁴ is bonded); R ¹ and R ² are both hydrogen atoms; R ³ ~ R ⁵ each independently represent a hydrogen atom or a carbon number 1 that may have a substituent A monovalent hydrocarbon group of ~6, -CH ₂ - contained in the hydrocarbon group may be substituted by -O- or -CO-; R ⁶ represents a monovalent aromatic group that may have a substituent or the number of carbon atoms that may have a substituent. 1 to 6 monovalent aliphatic hydrocarbon groups, -CH ₂ - contained in the aliphatic hydrocarbon group may be substituted by -O- or -CO-]. A coloring composition comprising a coloring agent containing the compound according to claim 1 and a resin. A colored curable resin composition comprising the colored composition according to claim 2, a polymerizable compound and a polymerization initiator. A color filter formed from the colored composition according to claim 2 or the colored curable resin composition according to claim 3. A display device including the color filter according to claim 4.

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