JP2020033524A - Coloring composition and color filter - Google Patents

Abstract

To provide a coloring composition having reduced viscosity while maintaining excellent color characteristics.SOLUTION: The present invention provides a coloring composition containing a quinophthalone compound represented by the following formula (1), an amine dispersant, and a solvent. In formula (1), X-Xindependently represent H, or a halogen atom, Yand Yindependently represent H, or a halogen atom, Z is a C1-3 alkylene group.SELECTED DRAWING: None

Description

  The present invention relates to a coloring composition and a color filter.

  At present, coloring compositions are used in various fields. Specific uses of the coloring compositions include printing inks, paints, coloring agents for resins, coloring agents for fibers, coloring materials for IT information recording (color filters). , Toner, and inkjet). Dyes used in the coloring composition are required to have color characteristics (coloring power, sharpness), resistance (weather resistance, light resistance, heat resistance, solvent resistance) and the like. Dyes are mainly classified into pigments and dyes, but pigments are different from dyes that develop color in a molecular state, and develop color in a particle state (aggregates of primary particles). For this reason, pigments are generally superior to dyes in terms of resistance, but are inferior in coloring power and chroma (clearness).

  From such a background, pigments having high coloring power and high chroma are demanded, and attention is particularly paid to organic pigments, which are considered to be dominant in terms of coloring power. For example, Patent Document 1 discloses a coloring composition containing a predetermined quinophthalone compound.

JP 2012-247587 A

  By the way, pigments intended for color filters are required to have different properties from general-purpose applications. Specifically, for example, “high brightness” for reducing the power consumption of the backlight, “high coloring power” for thinning the color filters and high color reproduction, and the like are required. However, the coloring composition disclosed in Patent Literature 1 does not always provide sufficient luminance and coloring power when a color filter is used. That is, the coloring composition disclosed in Patent Literature 1 has room for further improvement in terms of increasing luminance and obtaining high color reproducibility even in a thin film.

  Further, a coloring composition containing a pigment composed of fine particles may show a high viscosity due to aggregation of the pigment, which may be a hindrance factor in the production of a color filter.

  Therefore, an object of the present invention is to provide a coloring composition containing a pigment having excellent luminance and coloring power and having a reduced viscosity while maintaining good color characteristics derived from the pigment. Another object of the present invention is to provide a color filter formed using the coloring composition.

  The present inventors have conducted intensive studies to solve the above problems, and found that a specific quinophthalone compound obtained by dimerizing a quinophthalone skeleton becomes a yellow pigment having excellent luminance and coloring power, and a specific dispersant. However, they have found that a colored composition containing the yellow pigment can be reduced in viscosity while maintaining its excellent color characteristics, and completed the present invention.

［式（１）中、Ｘ^１〜Ｘ^１６は各々独立に水素原子又はハロゲン原子であり、Ｙ^１及びＹ^２は各々独立に水素原子又はハロゲン原子であり、Ｚは炭素数１〜３のアルキレン基である。］ One aspect of the present invention relates to a coloring composition containing a quinophthalone compound represented by the following formula (1), a dispersant, and a solvent, wherein the dispersant contains an amine-based dispersant.

[In formula (1), X ^{1 to} X ¹⁶ are each independently a hydrogen atom or a halogen atom, Y ¹ and Y ² are each independently a hydrogen atom or a halogen atom, and Z is an alkylene having 1 to 3 carbon atoms. Group. ]

  The amine value of the dispersant may be 20 to 180 mg KOH / g.

［式（１）中、Ｘ^１〜Ｘ^１６は各々独立に水素原子又はハロゲン原子であり、Ｙ^１及びＹ^２は各々独立に水素原子又はハロゲン原子であり、Ｚは炭素数１〜３のアルキレン基である。］ Still another aspect of the present invention is a color filter having a pixel portion containing a quinophthalone compound represented by the following formula (1) and a dispersant, wherein the dispersant contains an amine-based dispersant.

[In formula (1), X ^{1 to} X ¹⁶ are each independently a hydrogen atom or a halogen atom, Y ¹ and Y ² are each independently a hydrogen atom or a halogen atom, and Z is an alkylene having 1 to 3 carbon atoms. Group. ]

  The pixel portion may be a pixel portion toned with the coloring composition.

  ADVANTAGE OF THE INVENTION According to this invention, the coloring composition containing the pigment which has the outstanding brightness | luminance and tinting power is provided, and the low viscosity was maintained, maintaining the favorable color characteristics derived from the said pigment. Further, according to the present invention, there is provided a color filter formed using the coloring composition.

(Coloring composition)
The coloring composition according to one embodiment contains a quinophthalone compound represented by the following formula (1), a dispersant, and a solvent. The dispersant contains an amine-based dispersant.

In the formula (1), X ^{1 to} X ¹⁶ are each independently a hydrogen atom or a halogen atom, Y ¹ and Y ² are each independently a hydrogen atom or a halogen atom, and Z is an alkylene group having 1 to 3 carbon atoms. It is.

  The quinophthalone compound exhibits selective absorption and transmission due to dimerization of the quinophthalone skeleton. In the quinophthalone compound, the quinophthalone skeleton is dimerized using the linking group Z as a spacer, whereby conjugation is cut off and excessive redness is suppressed. Further, the quinophthalone compound has improved dispersibility by introducing an imide structure. From these facts, according to the quinophthalone compound, a pigment having excellent luminance and coloring power can be obtained. Specifically, for example, a yellow pigment composed of the above quinophthalone compound has better luminance than a yellow pigment generally used at present (CI Pigment Yellow 150), and has an excellent luminance exceeding this. Coloring power. According to the amine-based dispersant, the aggregation of the quinophthalone compound in the solvent is suppressed, so that the viscosity increase, color separation, and pigment sedimentation caused by the aggregation of the quinophthalone compound are suppressed.

  The halogen atom in the formula (1) may be a fluorine atom, a chlorine atom, a bromine atom or an iodine atom, preferably a fluorine atom, a chlorine atom or a bromine atom, and more preferably a chlorine atom.

  Specific examples of the alkylene group having 1 to 3 carbon atoms in the formula (1) include, for example, a methylene group, an ethylene group (1,1-ethanediyl group or 1,2-ethanediyl group), a propylene group (1,1- A propanediyl group, a 2,2-propanediyl group, a 1,2-propanediyl group or a 1,3-propanediyl group), and a methylene group, a 1,1-ethanediyl group, a 1,1-propanediyl group, , 2-propanediyl group is more preferable, and methylene group is further preferable.

In the quinophthalone compound, at least one of X ^{1 to} X ¹⁶ is preferably a halogen atom, and more preferably two or more are halogen atoms. When a halogen atom is introduced into X ^{1 to} X ¹⁶ , the dispersibility of the quinophthalone compound is further improved, and the above effects tend to be more remarkably obtained.

At least one of X ^{1 to} X ⁴ is preferably a halogen atom, more preferably two or more are halogen atoms, and all may be halogen atoms. Further, it is preferable that at least one of X ² and X ³ is a halogen atom, more preferably X ² and X ³ are each a halogen atom.

At least one of X ^{5 to} X ⁸ is preferably a halogen atom, more preferably two or more are halogen atoms, and all may be halogen atoms. Further, it is preferable that at least one of X ⁶ and X ⁷ is a halogen atom, more preferably X ⁶ and X ⁷ are each a halogen atom.

At least one of X ^{9 to} X ¹² is preferably a halogen atom, more preferably two or more are halogen atoms, and all may be halogen atoms. ^Further, it is preferable that at least one of ^{X 10} and ^{X 11} is a halogen ^atom, more preferably ^{X 10} and ^{X 11} are each a halogen atom.

At least one of X ^{13 to} X ¹⁶ is preferably a halogen atom, more preferably two or more are halogen atoms, and all may be halogen atoms. It is preferred that at least one is a halogen atom of X ¹⁴ and ^{X 15,} and more preferably ^{X 14} and ^{X 15} are each a halogen atom.

Y ¹ and Y ² may be the same or different, but are preferably the same from the viewpoint of facilitating the synthesis of the quinophthalone compound.

In the structure of the formula (1), tautomers of the following formulas (1-i) and (1-ii) exist, and the quinophthalone compound has any of these structures. You may.

In the formulas (1-i) and (1-ii), X ^{1 to} X ¹⁶ , Y ¹ , Y ² and Z are as described above.

  Specific examples of the quinophthalone compound are shown below, but the quinophthalone compound is not limited to these.

  The method for producing the quinophthalone compound is not particularly limited, and can be produced by appropriately utilizing a conventionally known method. Hereinafter, one embodiment of a method for producing a quinophthalone compound will be described, but the production method is not limited thereto.

  The quinophthalone compound can be obtained, for example, by a method including the following Step I, Step II, Step III and Step IV.

<Step I>
First, J. According to the method described in Heterocyclic, Chem, 30, 17, (1993) or the like, 2 to 3 equivalents of crotonaldehyde are added to 1 equivalent of bisaniline, and the reaction is carried out in a strong acid in the presence of an oxidizing agent. The compound of -1) is synthesized.

In the formula (A-1), Y ¹ , Y ² and Z are as described above.

  Here, examples of the strong acid include hydrochloric acid, sulfuric acid, nitric acid and the like. Examples of the oxidizing agent include sodium iodide, p-chloranil, nitrobenzene, and the like.

  For Step I, the reaction temperature may be from 80C to 100C, preferably from 90C to 100C, and the reaction time may be from 1 hour to 6 hours, preferably from 3 hours to 6 hours.

<Step II>
Further, the compound of formula (A-2) can be obtained by reacting the obtained compound of formula (A-1) with nitric acid or fuming nitric acid in the presence of concentrated sulfuric acid.

In the formula (A-2), Y ¹ , Y ² and Z are as described above.

  For Step II, the reaction temperature may be from -20C to 70C, preferably from 0C to 50C, and the reaction time may be from 1 hour to 4 hours, preferably from 1 hour to 3 hours.

<Step III>
Furthermore, the compound of the formula (A-3) can be obtained by adding 6 to 8 equivalents of reduced iron to 1 equivalent of the obtained compound of the formula (A-2) and reacting.

In the formula (A-3), Y ¹ , Y ² and Z are as described above.

  For Step III, the reaction temperature may be from 60C to 80C, preferably from 70C to 80C, and the reaction time may be from 1 hour to 3 hours, preferably from 2 hours to 3 hours.

<Step IV>
Furthermore, at least one selected from the group consisting of phthalic anhydride and halogen-substituted phthalic anhydride is used per equivalent of the compound of the formula (A-3) obtained by the method described in JP-A-2013-61622. The compound of the formula (1) can be obtained by reacting one kind with 4 to 6 equivalents in the presence of an acid catalyst.

  Here, examples of the acid catalyst include benzoic acid and zinc chloride.

  For Step IV, the reaction temperature may be between 180C and 250C, preferably between 210C and 250C, and the reaction time may be between 1 hour and 8 hours, preferably between 3 hours and 8 hours.

  The above quinophthalone compounds may be used alone, or two or more compounds may be appropriately selected and used in combination.

  The quinophthalone compound can exhibit properties as an organic pigment. The quinophthalone compound may be compounded in the form of a pigment. In other words, the coloring composition according to the present embodiment may contain a yellow pigment composed of the quinophthalone compound.

  The quinophthalone compound may be converted into a pigment by a known and commonly used method. The yellow pigment composed of the quinophthalone compound may be finely divided by, for example, a salt milling treatment. In addition, the yellow pigment may be surface-treated by a method such as rosin treatment, surfactant treatment, solvent treatment, and resin treatment.

  The amine-based dispersant has at least one amine-based moiety selected from the group consisting of an amine moiety and a quaternary ammonium-modified amine moiety. In addition, an amine site | part shows the nitrogen atom which comprises a primary amine, a secondary amine, and a tertiary amine. The amine-based dispersant may be, for example, a resin (polymer) having the above-described amine-based moiety.

  The amine-based dispersant may be, for example, a random copolymer, a block copolymer, a graft copolymer, or the like. The amine-based dispersant is preferably a block copolymer or a graft copolymer from the viewpoint of excellent adsorption behavior to the pigment composed of the quinophthalone compound.

  The block copolymer may be composed of, for example, an A-block having no amine moiety and a B-block having the amine moiety. As such a block copolymer, an AB block copolymer and an ABA block copolymer are preferable.

  The method for producing the block copolymer is not particularly limited, and the block copolymer can be produced by appropriately adjusting a known method. As a method for producing the block copolymer, it is preferable to use a living polymerization method from the viewpoint of easily obtaining a copolymer having a small molecular weight distribution. Examples of the living polymerization method include a living radical polymerization method, a living anion polymerization method (for example, a group transfer polymerization method), a living cationic polymerization method, and the like. In the living polymerization method, a block copolymer can be efficiently produced by sequentially polymerizing monomers. Specifically, for example, an AB block copolymer can be produced by first producing an A-block and polymerizing a monomer forming a B-block from the end of the A-block. Alternatively, an AB block copolymer can also be produced by producing a B-block first and polymerizing a monomer forming an A-block from the end of the B-block.

  Examples of a method for producing the block copolymer include a method in which an A-block and a B-block are separately produced, and then the A-block and the B-block are connected by a coupling reaction or the like.

  Examples of the graft copolymer include a copolymer formed by the method described in JP-A-54-37082 (for example, a dispersant described in JP-A-54-37082). As the graft copolymer, a commercially available graft copolymer can also be suitably used.

  The amine-based dispersant may have an amine moiety. The amine value of the dispersant may be, for example, 1 mgKOH / g or more, preferably 20 mgKOH / g or more, more preferably 25 mgKOH / g or more. Further, the amine value of the dispersant may be, for example, 200 mgKOH / g or less, preferably 180 mgKOH / g or less, more preferably 175 mgKOH / g or less. The amine value of the dispersant can be adjusted, for example, by changing the amine value of the amine-based dispersant itself, or by changing the mixing ratio of the amine-based dispersant and the non-amine-based dispersant.

  In the present specification, the amine value indicates a value measured by potentiometric titration with an alcoholic hydrochloric acid standard solution according to the measurement method described in ASTM D 2073.

  The amine-based dispersant may have a quaternary ammonium moiety (hereinafter also referred to as an ammonium moiety) at the amine moiety. Such a dispersant is excellent in adsorptivity to the pigment surface due to electrostatic interaction with a pigment whose surface is negatively charged.

  The ammonium site may be, for example, a site formed by reacting a compound having a haloalkyl group, an inorganic acid, an inorganic acid ester, an organic acid, or an organic acid ester with an amine site.

The compound having a haloalkyl group may be any compound that has a haloalkyl group and can react with the amine moiety to form an ammonium moiety. As the haloalkyl group, a compound having a group represented by —CH ₂ X (X represents a halogen atom) is preferable.

Examples of the compound having a haloalkyl group include a compound represented by R ¹ —CH ₂ —X. Here, X represents a halogen atom, and R ¹ represents a hydrogen atom or a monovalent group.

The monovalent group of R ¹ is, for example, an alkyl group, a vinyl group, a phenyl group, a benzyl group, a group represented by —OR ² (R ² is an alkyl group, a vinyl group, a phenyl group, a benzyl group, or (Indicating a (meth) acryloyloxy group via an alkylene group having 1 to 4 carbon atoms)). In the monovalent group of R ¹ , a part of the methylene group (—CH ₂ —) in the alkyl group is substituted with an ether bond (—O—), an ester bond (—C (＝ O) O—), or the like. Group may be used. The above group exemplified as the monovalent group of R ¹ may have a substituent.

The alkyl group in R ¹ and R ² may be linear, branched, or cyclic. The carbon number of the alkyl group in R ¹ or R ² may be, for example, 1 to 20. Examples of the substituent that the alkyl group in R ¹ or R ² may have include a phenyl group and an alkoxy group (for example, a methoxy group, an ethoxy group, and the like). The alkyl group in R ¹ or R ² may have one or more substituents, and may be unsubstituted (that is, an alkyl group having no substituent).

Examples of the substituent which the phenyl group in R ¹ or R ² may have include an alkyl group (eg, a methyl group, an ethyl group, etc.), an alkoxy group (eg, a methoxy group, an ethoxy group, etc.), and the like. . The phenyl group in R ¹ or R ² may have one or more substituents, and may be unsubstituted (that is, a phenyl group having no substituent).

Examples of the substituent that the benzyl group in R ¹ or R ² may have include an alkyl group (eg, a methyl group, an ethyl group, etc.), an alkoxy group (eg, a methoxy group, an ethoxy group, etc.), and the like. . The benzyl group for R ¹ or R ² may have one or more substituents, and may be unsubstituted (that is, a benzyl group having no substituent).

  Examples of the compound having a haloalkyl group include, for example, methyl chloride, methyl bromide, ethyl chloride, ethyl bromide, methyl iodide, ethyl iodide, n-butyl chloride, hexyl chloride, octyl chloride, dodecyl chloride, tetradecyl chloride, hexadecyl Chloride, phenethyl chloride, benzyl chloride, benzyl bromide, benzyl iodide, allyl chloride and the like.

  Examples of the inorganic acid include oxo acid of phosphorus, sulfuric acid, nitric acid, hydrochloric acid, perchloric acid, chromic acid and the like, and among these, phosphoric acid and sulfuric acid are preferable.

  Examples of the inorganic acid esters include oxo acid esters of phosphorus (eg, phosphate esters and phosphites), sulfate esters, carbonate esters, nitrate esters, and nitrite esters. Of these, phosphate esters, Phosphite, sulfate and carbonate are preferred. As the inorganic acid ester, for example, monobutyl phosphoric acid, dibutyl phosphoric acid, methyl phosphoric acid, dibenzyl phosphoric acid, phenylphosphinic acid, phenylphosphonic acid, dimethyl sulfate, diethyl sulfate, di-n-propyl sulfate, methyl methanesulfonate, p-toluene Examples thereof include methyl sulfonate, dimethyl carbonate, and diethyl carbonate.

  Examples of the organic acid include formic acid, acetic acid, and oxalic acid. Examples of the organic acid ester include formate, acetate, and oxalate.

  In the amine dispersant, the content ratio of the amine moiety to the ammonium moiety is not particularly limited. The ratio of the amine moiety to the total number of the amine moiety and the ammonium moiety may be 5 to 95%, preferably 40 to 90%.

  The amine-based dispersant may be a resin having an amine moiety, or may be a resin obtained by converting a part of the amine moiety of the resin into an ammonium moiety. The type of the resin is not particularly limited, and may be any resin that can be dissolved in the solvent of the coloring composition. Examples of the resin include an acrylic resin, a urethane resin, an ester resin, an ether resin, an amide resin, and the like.

  The acrylic resin having an amine moiety may be, for example, a polymer of a monomer component containing an acrylic monomer having an amine moiety. Examples of the acrylic monomer having an amine moiety include dimethylaminoethyl (meth) acrylate.

  The monomer component may further contain another monomer other than the acrylic monomer having an amine moiety. Examples of the other monomer include (meth) acrylate, methyl methacrylate, n-butyl methacrylate, 2-ethylhexyl methacrylate, and benzyl methacrylate.

  The proportion of the acrylic monomer having an amine moiety in the monomer component may be, for example, 1 to 50 mol%, and preferably 10 to 40 mol%, based on the total amount of the monomer component.

  The weight average molecular weight Mw of the acrylic resin having an amine moiety may be, for example, 1,000 to 100,000, and preferably 5,000 to 15,000. With such a weight average molecular weight, the effect of improving the dispersibility of the pigment tends to be more stably obtained. The weight average molecular weight is a weight average molecular weight in terms of polystyrene measured by gel permeation chromatography.

  The urethane resin has an amine moiety in the urethane bond. The weight average molecular weight Mw of the urethane resin may be, for example, 500 to 100,000, and preferably 3500 to 5500. With such a weight average molecular weight, the effect of improving the dispersibility of the pigment tends to be more stably obtained. The weight average molecular weight is a weight average molecular weight in terms of polystyrene measured by gel permeation chromatography.

  Commercial products can also be used as the amine-based dispersant. Examples of the amine-based dispersant include ANTI-TERRA (registered trademark) U / U100, 204, DISPERBYK (registered trademark) 106, 108, 109, 112, 130, 140, 142, and 142. 145, 161, 162, 163, 164, 167, 168, 180, 182, 183, 184, 185, 2000, 2001, 2008, 2009, 2013 , 2022, 2025, 2026, 2050, 2055, 2150, 2155, 2163, 2164, 9076, 9077, BYK LPN-6919, 21116, 21324, 22102 (Big Chemie EFKA (registered trademark) 46, 47, 4010, 4020, 4320 4300, 4330, 4401, 4570, 5054, 7461, 7462, 7476, 7777 (manufactured by BASF Corporation), Azispar (registered trademark) PB814, 821, 822, 881 ( Ajinomoto Fine Techno Co., Ltd.), Solsperse (registered trademark) 24000, 37500, 76500 (manufactured by Lubrizol Co., Ltd.) and the like can be suitably used.

  The amine-based dispersant may be added to the coloring composition in a state of being dissolved in a solvent. The type of the solvent is not particularly limited, and may be one kind or a mixed solvent of two or more kinds. As the solvent, for example, a solvent used for a resist material can be suitably used. Specific examples of the solvent include, for example, propylene glycol monomethyl ether acetate (PGMEA).

  The dispersant may further contain another dispersant other than the amine-based dispersant. Other dispersants are not particularly limited, and known dispersants used for pigment dispersion can be used without any particular limitation. Specific examples of other dispersants include, for example, acrylic resin solution Unidick (registered trademark) ZL-295 (manufactured by DIC), DISPERBYK (registered trademark) 170, and 174 (manufactured by Big Chemie), Solsperse ( (Registered trademark name) 55000 (manufactured by Lubrizol Co., Ltd.).

  The proportion of the amine-based dispersant in the dispersant is not particularly limited, and may be, for example, a proportion in which the amine value of the dispersant is in the above-described preferred range. When the total amount of the dispersant is 100 parts by mass, the content of the amine-based dispersant may be, for example, 30 parts by mass or more, preferably 50 parts by mass or more, and 100 parts by mass (that is, All amine-based dispersants).

  The content of the dispersant may be, for example, 30 parts by mass or more, preferably 40 parts by mass or more, and more preferably 50 parts by mass or more based on 100 parts by mass of the quinophthalone compound. The content of the dispersant may be, for example, 100 parts by mass or less, preferably 90 parts by mass or less, more preferably 85 parts by mass or less, based on 100 parts by mass of the quinophthalone compound.

  As the solvent, an organic solvent is preferable. Examples of the organic solvent include aromatic solvents such as toluene, xylene and methoxybenzene, ethyl acetate and butyl acetate, acetic acid ester solvents such as propylene glycol monomethyl ether acetate and propylene glycol monoethyl ether acetate, and ethoxyethyl propionate. Propionate solvents, alcohol solvents such as methanol and ethanol, ether solvents such as butyl cellosolve, propylene glycol monomethyl ether, diethylene glycol ethyl ether, diethylene glycol dimethyl ether, ketone solvents such as methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, and fats such as hexane Group hydrocarbon solvents, N, N-dimethylformamide, γ-butyrolactam, N-methyl-2-pyrrolidone, aniline Emissions, nitrogen compound-based solvent such as pyridine, a lactone-based solvents such as γ- butyrolactone, carbamic acid esters such as a mixture of 48:52 of methyl carbamate and ethyl carbamate acid. The organic solvent is preferably a solvent that is polar and soluble in water, more preferably a propionate-based solvent, an alcohol-based solvent, an ether-based solvent, a ketone-based solvent, a nitrogen compound-based solvent, or a lactone-based solvent. is there.

  The content of the solvent is not particularly limited, and may be appropriately changed according to a desired viscosity or the like. The content of the solvent may be, for example, 300 parts by mass or more based on 100 parts by mass of the quinophthalone compound. The content of the solvent may be, for example, 2,000 parts by mass or less based on 100 parts by mass of the quinophthalone compound.

  The viscosity of the coloring composition is not particularly limited, and may be appropriately adjusted according to the use and the like. The viscosity at 20 ° C. of the coloring composition may be, for example, 0.5 to 100 mPa · s, and preferably 1 to 50 mPa · s, from the viewpoint of maintaining viscosity suitable for processing.

  The coloring composition according to the present embodiment may further contain components other than those described above. For example, in addition to the above, the coloring composition may further contain a coloring material such as an organic pigment and an organic dye, an organic pigment derivative, and the like. The organic pigment derivative may be, for example, a derivative in which a part of a known organic pigment is modified (substituted) with a sulfonic acid group, a carboxyl group, an amino group, a phthalimidomethyl group, or the like. Specifically, for example, Solsperse (registered trademark) 5000, 12000 and 22000 (manufactured by Lubrizol Co., Ltd.) and the like can be mentioned. The content of the organic pigment derivative may be 1 part by mass or more and 20 parts by mass or less based on 100 parts by mass of the total amount of the pigment.

  The coloring material that can be used in combination may be a known pigment, dye, or the like, and may be appropriately selected depending on the use of the coloring composition. Examples of pigments that can be used in combination include, for example, azo pigments, disazo pigments, azomethine pigments, anthraquinone pigments, quinophthalone pigments, quinacridone pigments, diketopyrrolopyrrole pigments, dioxazine pigments, benzimidazolone pigments, Examples include phthalocyanine pigments, isoindoline pigments, isoindolinone pigments, perylene pigments, and the like. Examples of dyes that can be used in combination include, for example, xanthene dyes, azo dyes, disazo dyes, anthraquinone dyes, quinophthalone dyes, triarylmethane dyes, methine dyes, phthalocyanine dyes, rhodamine dyes, and the like. No.

  Among the pigments that can be used in combination, C.I. I. Pigment Yellow 3, 12, and 74, and C.I. I. Pigment Yellow 74, 83, 109, 110 and the like. I. Pigment Yellow 83, 129, 138, 139, 150, 185, 231 and the like. Preferably C.I. I. Pigment Yellow 129, 138, 139, 150, 185, 231 and the like.

  In color filter applications, a yellow pigment is often used for toning a green pixel portion in combination with a green pigment or a blue pigment. From this viewpoint, the coloring composition according to the present embodiment may be used in combination with a green pigment or a blue pigment.

  The green pigment and the blue pigment are not particularly limited, and may be publicly known green pigments and blue pigments. Examples of the green pigment include C.I. I. Pigment Green 1, 2, 4, 7, 8, 10, 13, 13, 14, 15, 17, 18, 19, 26, 36, 45, 48, 48 50, 51, 54, 55, 58, 59, 62, 63 and the like. Examples of the blue pigment include C.I. I. Pigment Blue 15, 15: 1, 15: 2, 15: 3, 15: 4, and 15: 6. Preferably C.I. I. Pigment Green 7, 36, 58, 59, 62, 63 and the like. Examples of the blue pigment include an aluminum phthalocyanine derivative.

  Here, examples of the aluminum phthalocyanine derivative include a compound represented by the following formula (3-1).

  In the formula (3-1), R represents a halogen atom, a hydroxy group, or a group represented by the following formula (3-2).

  In the formula (3-2), X represents a direct bond or an oxygen atom. Ar represents a phenyl group or a naphthyl group. In the formula (3-2), an asterisk indicates a binding site.

  Examples of the halogen atom for R in the formula (3-1) include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Among them, the halogen atom for R is preferably a chlorine atom or a bromine atom.

  In the formula (3-1), R is preferably a chlorine atom, a bromine atom, a hydroxy group, or a group represented by the formula (3-2).

  In the formula (3-2), X is preferably an oxygen atom.

  Preferred examples of the formula (3-1) include hydroxyaluminum phthalocyanine, chloroaluminum phthalocyanine, bromoaluminum phthalocyanine, a compound represented by the following formula (3-1-1), and a compound represented by the following formula (3-1-2) And the compound represented by the following formula (3-1-3).

  The coloring composition according to the present embodiment may further contain a leveling agent, a coupling agent, a rosin, a surfactant, a resin, a dispersant, a photosensitive resin, a curable resin, and the like as components other than those described above. Good. These components may be added by, for example, surface treatment of a pigment composed of the quinophthalone compound. The surface treatment of the pigment may be a known method such as a rosin treatment, a surfactant treatment, a solvent treatment, and a resin treatment.

  The coloring composition may further contain a photosensitive resin. A coloring composition containing a photosensitive resin can also be referred to as a photosensitive coloring composition. Examples of the photosensitive resin include a thermoplastic resin such as a urethane resin, an acrylic resin, a polyamide acid resin, a polyimide resin, a styrene maleic acid resin, and a styrene maleic anhydride resin, and, for example, 1,6-hexanediol. Bifunctional monomers such as diacrylate, ethylene glycol diacrylate, neopentyl glycol diacrylate, triethylene glycol diacrylate, bis (acryloxyethoxy) bisphenol A, 3-methylpentanediol diacrylate, trimethylolpropane triacrylate, Such as pentaerythritol triacrylate, tris- (2-acryloyloxyethyl) isocyanurate, dipentaerythritol hexaacrylate, dipentaerythritol pentaacrylate, etc. Such photopolymerizable monomers such as functional monomers.

  The photosensitive coloring composition may further contain a photopolymerization initiator. Examples of the photopolymerization initiator include acetophenone, benzophenone, benzyldimethylketanol, benzoyl peroxide, 2-chlorothioxanthone, 1,3-bis (4′-azidobenzal) -2-propane, and 1,3-bis (4 ′). -Azidobenzal) -2-propane-2'-sulfonic acid, 4,4'-diazidostilbene-2,2'-disulfonic acid and the like.

  The coloring composition may be prepared by, for example, mixing the quinophthalone compound (or a pigment composition containing a pigment composed of the quinophthalone compound), a dispersant, and a solvent. Further, the coloring composition may be prepared by mixing the above quinophthalone compound, a solvent, a resin having an amine moiety, and a compound which reacts with the amine moiety to form an ammonium moiety. .

  In the present embodiment, for example, 30 to 100 parts by mass of a dispersant and 300 to 2,000 parts by mass of an organic solvent are stirred and dispersed so as to be uniform with respect to 100 parts by mass of the quinophthalone compound, and the dispersion (colored composition Thing) can be obtained. Next, 3 to 20 parts by mass of a photosensitive resin per 100 parts by mass of the dispersion and 0.05 to 3 parts by mass of a photopolymerization initiator per 1 part by mass of the photosensitive resin are added to the dispersion (if necessary, ), And the mixture is stirred and dispersed so as to be uniform to obtain a photosensitive colored composition.

  When the coloring composition (photosensitive coloring composition) is for forming a green pixel portion of a color filter, 200 parts by mass or less of a green pigment and / or 200 parts by mass or less of a blue pigment are contained per 100 parts by mass of the quinophthalone compound. It may be further added. When the coloring composition (photosensitive coloring composition) is for forming a red pixel portion of a color filter, 200 parts by mass or less of a red pigment may be further added per 100 parts by mass of the quinophthalone compound.

(Color filter)
The color filter according to the present embodiment has a pixel portion containing the quinophthalone compound and the amine-based dispersant. The pixel portion may be a green pixel portion or a red pixel portion.

  The pixel portion may be a pixel portion toned with the above-described coloring composition. The pixel portion may be toned using only the above-described coloring composition, and may include the above-described coloring composition and another coloring composition (for example, a coloring composition including a blue pigment, a green pigment, or a red pigment). ) May be colored in combination with the product (1).

  The pixel portion can be easily formed from the above-described coloring composition (photosensitive coloring composition). As a specific method, for example, a coloring composition (photosensitive coloring composition) is applied on a transparent substrate such as glass by a spin coating method, a roll coating method, an ink jet method, or the like, and then the coating film is applied. And a method called photolithography, in which after performing pattern exposure with ultraviolet rays through a photomask, an unexposed portion is washed with a solvent or the like to obtain a colored pattern.

  The method for forming the pixel portion is not particularly limited. For example, a pattern of the pixel portion may be formed by an electrodeposition method, a transfer method, a micelle electrolysis method, or a PVED (Photovoltaic Electrodeposition) method to manufacture a color filter. .

^１Ｈ−ＮＭＲ（ＣＤＣｌ_３）δｐｐｍ：２．８１（ｓ，６Ｈ），４．２４（ｓ，２Ｈ），７．３４（ｄ，Ｊ＝８．０Ｈｚ，２Ｈ），７．４９（ｓ，２Ｈ），７．６７（ｓ，２Ｈ），７．９９（ｄ，Ｊ＝８．８Ｈｚ，２Ｈ）
^１３Ｃ−ＮＭＲ（ＣＤＣｌ_３）δｐｐｍ：２５．８，４１．１，１２３．２，１２６．２，１２７．８，１３０．９，１３３．１，１３６．３，１３７．６，１４３．１，１６０．０
ＦＴ−ＩＲ ｃｍ^−１：３４３５，３０５４，３０３０，２９１５，１６０３，１４８７，１２０６
ＦＤ−ＭＳ：３６６Ｍ＋ [Synthesis Example 1]
5.00 g (56.1 mmol) of 4,4'-methylenebis (2-chloroaniline), 27.6 g (112 mmol) of p-chloranil, 150 ml of water, 150 ml of concentrated hydrochloric acid and 100 ml of n-butanol were added to the flask, and the mixture was added to the flask. Stirred at C for 30 minutes. To this mixture was added dropwise 11.8 g (168 mmol) of crotonaldehyde dissolved in 12 ml of n-butanol, and the mixture was further stirred for 1 hour. The temperature was lowered to 80 ° C., and 15.3 g (112 mmol) of zinc chloride was added little by little. Then, 200 ml of THF was added, and the mixture was stirred for 1 hour while maintaining the temperature at 80 ° C. After allowing to cool to room temperature, ocher powder was recovered by vacuum filtration. The obtained ocher powder was washed with 200 ml of THF, and the ocher powder was recovered by vacuum filtration again. Further, the obtained ocher powder was transferred to a flask, 200 ml of water and 40 ml of 28% aqueous ammonia were added, and the mixture was stirred at room temperature for 2 hours. The powder was recovered by vacuum filtration to obtain 20.3 g of a crude product. The obtained crude product was dissolved in toluene, insolubles were removed by filtration, and then recrystallized to obtain 12.6 g of Intermediate (4). (Yield: 61%)

¹ H-NMR (CDCl ₃ ) δ ppm: 2.81 (s, 6H), 4.24 (s, 2H), 7.34 (d, J = 8.0 Hz, 2H), 7.49 (s, 2H) ), 7.67 (s, 2H), 7.99 (d, J = 8.8 Hz, 2H)
¹³ C-NMR (CDCl ₃ ) δ ppm: 25.8, 41.1, 123.2, 126.2, 127.8, 130.9, 133.1, 136.3, 137.6, 137.6, 143.1. 160.0
FT-IR cm- ¹ : 3435, 3054, 3030, 2915, 1603, 1487, 1206
FD-MS: 366M +

^１Ｈ−ＮＭＲ（ＣＤＣｌ_３）δｐｐｍ：２．８６（ｓ，６Ｈ），４．２７（ｓ，２Ｈ），７．５６（ｄ，Ｊ＝８．８Ｈｚ，２Ｈ），７．６２（ｓ，２Ｈ），８．０８（ｄ，Ｊ＝８．８Ｈｚ，２Ｈ）
^１３Ｃ−ＮＭＲ（ＣＤＣｌ_３）δｐｐｍ：２５．７，３２．４，１１９．９，１２５．６，１２７．５，１３０．１，１３１．１，１３７．３，１４３．１，１４５．９，１６２．２
ＦＴ−ＩＲ ｃｍ^−１：３４６５，１６０４，１５３０，１４８７，１３６２ Subsequently, 4.15 g (11.3 mmol) of the intermediate (4) and 7.55 mL of concentrated sulfuric acid were added to the flask, and the mixture was stirred at 45 ° C for 20 minutes. Thereafter, 1.62 mL of fuming nitric acid was added dropwise, and the temperature was maintained and stirring was continued for 1 hour. After cooling, 250 mL of ice water was slowly poured into the system. Further, the pH was adjusted to 8 to 9 using a 10 wt% aqueous sodium hydroxide solution. The precipitated powder was collected by filtration under reduced pressure, and washed with 200 mL of distilled water and 100 mL of ethanol to obtain 4.86 g (10.6 mmol) of the intermediate (5) (yield: 94%).

¹ H-NMR (CDCl ₃ ) δ ppm: 2.86 (s, 6H), 4.27 (s, 2H), 7.56 (d, J = 8.8 Hz, 2H), 7.62 (s, 2H) ), 8.08 (d, J = 8.8 Hz, 2H)
¹³ C-NMR (CDCl ₃ ) δ ppm: 25.7, 32.4, 119.9, 125.6, 127.5, 130.1, 131.1, 137.3, 143.1, 145.9, 162.2
FT-IR cm- ¹ : 3465, 1604, 1530, 1487, 1362

^１Ｈ−ＮＭＲ（ＣＤＣｌ_３）δｐｐｍ：２．６５（ｓ，６Ｈ），３．９７（ｓ，２Ｈ），５．９２（ｓ，４Ｈ），７．３２（ｓ，２Ｈ），７．３８（ｄ，Ｊ＝８．８Ｈｚ，２Ｈ），８．５９（ｄ，Ｊ＝８．８Ｈｚ，２Ｈ）
^１３Ｃ−ＮＭＲ（ＣＤＣｌ_３）δｐｐｍ：２５．４，３１．９，１１６．８，１１７．７，１１７．９，１２１．０，１３１．８，１３２．２，１４２．０，１４３．１，１５８．９
ＦＴ−ＩＲ ｃｍ^−１：３４７６，３３７３，１６２７，１６０５，１４０９，１３５９，１２５０ Subsequently, 5.00 g (10.9 mmol) of the intermediate (5) and 23.3 mL of ethanol were added to the flask, and the mixture was stirred at room temperature for 10 minutes. Thereafter, 4.88 g (87.4 mmol) of reduced iron was added to the system, and the mixture was further stirred at room temperature for 10 minutes. Subsequently, 6.33 mL of concentrated hydrochloric acid was added dropwise, the temperature was raised to 80 ° C., and stirring was continued for 6 hours. After standing to cool, the mixture was poured into 150 mL of distilled water, and the pH was adjusted to 9 using a 10% aqueous sodium hydroxide solution. The precipitated powder was collected by vacuum filtration. Further, the collected powder was sufficiently stirred in 700 mL of ethyl acetate, and filtered under reduced pressure. The solvent of the obtained filtrate was distilled off under reduced pressure to obtain 3.64 g (9.16 mmol) of the intermediate (6) (yield: 84%).

¹ H-NMR (CDCl ₃ ) δ ppm: 2.65 (s, 6H), 3.97 (s, 2H), 5.92 (s, 4H), 7.32 (s, 2H), 7.38 ( d, J = 8.8 Hz, 2H), 8.59 (d, J = 8.8 Hz, 2H)
¹³ C-NMR (CDCl ₃ ) δ ppm: 25.4, 31.9, 116.8, 117.7, 117.9, 121.0, 131.8, 132.2, 142.0, 143.1, 158.9
FT-IR cm ^-1 : 3476, 3373, 1627, 1605, 1409, 1359, 1250

ＦＴ−ＩＲ ｃｍ^−１：３４４９，１７２７，１６２２，１５３６，１４１０，１３６３，１３０８，１１９２，１１１２，７３７
ＦＤ−ＭＳ：１４６７Ｍ＋ Subsequently, under a nitrogen atmosphere, 14.1 g (116 mmol) of benzoic acid was weighed and melted in a flask at 140 ° C. Thereto, 1.44 g (3.62 mmol) of the intermediate (6) and 5.53 g (19.3 mmol) of tetrachlorophthalic anhydride were added, and the mixture was stirred at 220 ° C. for 4 hours. After allowing to cool, acetone (300 mL) was added to the reaction solution, and the mixture was stirred for 1 hour, and then filtered under reduced pressure to obtain 4.52 g (3.08 mmol) of the target product (7) as a yellow powder (yield: 85%).

FT-IR cm- ¹ : 3449, 1727, 1622, 1536, 1410, 1363, 1308, 1192, 1112, 737.
FD-MS: 1467M +

[Pigmentation Example 1]
5 parts by mass of the quinophthalone dimer (7) obtained in Synthesis Example 1, 50 parts by mass of pulverized sodium chloride, and 8 parts by mass of diethylene glycol were charged into a double-arm kneader and kneaded at 80 ° C. for 8 hours. After kneading, the mixture was taken out into 6000 parts by mass of water at 80 ° C., stirred for 1 hour, filtered, washed with hot water, dried and pulverized to obtain a quinophthalone pigment as a yellow pigment. The quinophthalone pigment obtained was photographed with a transmission electron microscope JEM-2010 manufactured by JEOL Ltd. The average aspect ratio is calculated from the average value of the longer diameter (major axis) and the shorter diameter (minor axis) of 40 primary particles constituting the aggregate on the secondary image, and the average value of the major axis is calculated as the average primary particle. Diameter. The average aspect ratio was less than 3.00. The average primary particle size was 100 nm or less.

[Synthesis Example 2]
Under a nitrogen atmosphere, 300 parts by mass of methyl ethyl ketone, 20.6 parts by mass of 2,2'-bipyridyl, and 6.5 parts by mass of cuprous chloride were charged into a flask, and the mixture was stirred at room temperature for 30 minutes. There, 13.3 parts by mass of ethyl 2-bromoisoacetate as an initiator, 23.7 parts by mass of methyl methacrylate, 9.20 parts by mass of n-butyl methacrylate, 12.8 parts by mass of 2-ethylhexyl methacrylate, benzyl methacrylate 12 To the mixture were added 0.7 parts by mass, 18.1 parts by mass of dimethylaminoethyl methacrylate, and 4.12 parts by mass of triethylene glycol dimethacrylate, and reacted at 60 ° C. for 3 hours under a nitrogen atmosphere to obtain a resin having an amine moiety. Next, benzyl chloride was reacted with the amine moiety of this resin to obtain the desired amine-based dispersant (D-1). The number average molecular weight Mn of the obtained amine-based dispersant (D-1) was 4,500, the weight average molecular weight Mw was 6,200, and the amine value was 71 mgKOH / g.

[Synthesis Example 3]
In a flask purged with nitrogen, 200 parts by mass of propylene glycol monomethyl ether acetate as a solvent, 26.4 parts by mass of methyl methacrylate as a monomer, 15.4 parts by mass of n-butyl methacrylate, 12.5 parts by mass of 2-ethylhexyl methacrylate, and benzyl methacrylate 7 .17 parts by mass, dimethylaminoethyl methacrylate 28.8 parts by mass, triethylene glycol dimethacrylate 3.89 parts by mass, and 2,2′-azoisobutyronitrile 2 parts as a polymerization initiator were charged, and the mixture was stirred at 90 ° C. The temperature was raised to 5 hours to obtain the desired amine-based dispersant (D-2) over 5 hours. The number average molecular weight Mn of the obtained amine-based dispersant (D-2) was 5000, the weight average molecular weight Mw was 13,500, and the amine value was 171 mgKOH / g.

[Synthesis Example 4]
A flask purged with nitrogen was charged with propylene glycol monomethyl ether acetate as a solvent and 1,12-dodecanediol, polycaprolactone diol, toluene diisocyanate, and polyethylene glycol as raw materials. An amine-based dispersant (D-3) was obtained. The obtained amine dispersant (D-3) had a number average molecular weight Mn of 810, a weight average molecular weight Mw of 4,300, and an amine value of 39 mgKOH / g.

[Example 1-1]
0.660 parts by mass of the quinophthalone pigment obtained in Pigmentation Example 1 was placed in a glass bottle, and 0.040 parts by mass of the following quinophthalonesulfonic acid derivative (9) synthesized by the method described in JP-A-2013-54200, propylene glycol monomethyl 13.5 parts by mass of ether acetate, 0.565 parts by mass of the amine-based dispersant (D-1), and 22.0 parts by mass of 0.3-0.4 mmφ seple beads were added, and the mixture was added with a paint shaker (manufactured by Toyo Seiki Co., Ltd.). After half an hour of dispersion, a pigment dispersion was obtained. Note that the sulfonic acid group in the formula (9) is substituted on any of the hydrogen atoms on the quinoline ring.

[Example 1-2]
0.660 parts by mass of the quinophthalone pigment obtained in Pigmentation Example 1 was put into a glass bottle, 0.040 parts by mass of the quinophthalone sulfonic acid derivative (9), 13.5 parts by mass of propylene glycol monomethyl ether acetate, and an amine-based dispersant (D -2) 0.565 parts by mass and 22.0 parts by mass of 0.3-0.4 mmφ seple beads were added, and dispersed for 2 and a half hours with a paint shaker (manufactured by Toyo Seiki Co., Ltd.) to obtain a pigment dispersion.

[Example 1-3]
0.660 parts by mass of the quinophthalone pigment obtained in Pigmentation Example 1 was put into a glass bottle, 0.040 parts by mass of the quinophthalone sulfonic acid derivative (9), 13.5 parts by mass of propylene glycol monomethyl ether acetate, and an amine-based dispersant (D -2) 0.294 parts by mass, acrylic resin solution Unidick (registered trademark) ZL-295 (manufactured by DIC Corporation) 0.678 parts by mass, 0.3-0.4 mmφ seple beads 22.0 parts by mass, and paint The mixture was dispersed for 2.5 hours with a shaker (manufactured by Toyo Seiki Co., Ltd.) to obtain a pigment dispersion.

  In addition, only 0.294 parts by mass of the amine-based dispersant (D-2) and 0.678 parts by mass of the acrylic resin solution Unidick (registered trademark) ZL-295 (manufactured by DIC Corporation) were mixed together, and the solid obtained by removing the solvent was mixed. When the amine value of the compound was calculated, it was 29 mgKOH / g (solid content).

[Example 1-4]
0.660 parts by mass of the quinophthalone pigment obtained in Pigmentation Example 1 was put into a glass bottle, 0.040 parts by mass of the quinophthalone sulfonic acid derivative (9), 13.5 parts by mass of propylene glycol monomethyl ether acetate, and an amine-based dispersant (D -3) 0.565 parts by mass and 22.0 parts by mass of 0.3-0.4 mmφ seple beads were added, and the mixture was dispersed with a paint shaker (manufactured by Toyo Seiki Co., Ltd.) for 2.5 hours to obtain a pigment dispersion.

[Comparative Example 1-1]
0.660 parts by mass of the quinophthalone pigment obtained in Pigmentation Example 1 was placed in a glass bottle, 0.040 parts by mass of the above quinophthalone sulfonic acid derivative (9), 13.5 parts by mass of propylene glycol monomethyl ether acetate, DISPERBYK (registered trademark) 174 (Dispersant having no amine moiety, manufactured by Big Chemie Co., Ltd.) 0.565 parts by mass, 22.0 parts by mass of 0.3-0.4 mmφ seple beads were added, and dispersed for 2 hours and a half with a paint shaker (manufactured by Toyo Seiki Co., Ltd.). Thus, a pigment dispersion was obtained.

  The viscosity at 20 ° C. of the pigment dispersions obtained in Examples 1-1 to 1-4 and Comparative Example 1-1 was measured using a rotational viscometer TVE-25L (manufactured by Toki Sangyo Co., Ltd.). Table 1 shows the results.

  As described above, in Examples using the amine-based dispersant, a pigment dispersion having a lower viscosity was obtained as compared with Comparative Example 1-1.

[Production Example 1]
C. I. Pigment Green 59 (manufactured by DIC Corporation) (2.48 parts by mass) was placed in a glass bottle, 10.9 parts by mass of propylene glycol monomethyl ether acetate, BYK LPN-6919 (manufactured by BYK Corporation) 1.24 parts by mass, acrylic resin solution unit 1.86 parts by mass of Dick (registered trademark) ZL-295 (manufactured by DIC) and 0.3-0.4 mmφ seple beads were added, and the mixture was dispersed for 2 hours with a paint shaker (manufactured by Toyo Seiki Co., Ltd.) to obtain a pigment dispersion. Obtained. Further, 4.00 parts by mass of the obtained pigment dispersion, 0.980 parts by mass of acrylic resin solution Unidick (registered trademark) ZL-295 (manufactured by DIC Corporation), and 0.220 parts by mass of propylene glycol monomethyl ether acetate were placed in a glass bottle. And shaking to prepare a composition for green toning.

[Example 2-1]
4.00 parts by mass of the pigment dispersion obtained in Example 1-1, 0.600 parts by mass of acrylic resin solution Unidick (registered trademark) ZL-295 (manufactured by DIC Corporation), and 0.220 of propylene glycol monomethyl ether acetate The mass part was put in a glass bottle and shaken to prepare a composition for yellow toning.

  Next, the obtained composition for yellow toning and the composition for green toning obtained in Production Example 1 were mixed at a ratio of 43:57 to obtain a composition for green toning.

  The characteristics of the color filter formed from the obtained composition for green toning were measured by the following methods. Table 2 shows the results.

[Comparative Example 2-1]
A green toning composition was prepared in the same manner as in Example 2-1 except that the pigment dispersion of Comparative Example 1-1 was used as the pigment dispersion. The characteristics of the color filter formed from the obtained composition for green toning were measured by the following methods. Table 2 shows the results.

<Color filter characteristic test>
The composition for green toning of Example 2-1 was applied on a glass substrate by a spin coater, dried, heated at 230 ° C. for 1 hour, and given a predetermined green chromaticity when a C light source was used. Was obtained. The chromaticity of the evaluation sample is a value obtained by a spectrophotometer (U3900 / 3900H, manufactured by Hitachi High-Tech Science Co., Ltd.). .240, 0.650). The luminance Y in the obtained evaluation sample was measured by a spectrophotometer (U3900 / 3900H type manufactured by Hitachi High-Tech Science Corporation). Further, for the obtained evaluation sample, the thickness of the colored film formed on the glass substrate was measured by a film thickness meter (VS1330 scanning white interference microscope manufactured by Hitachi High-Tech Science Corporation). It can be said that the thinner the film thickness, the higher the coloring power. Table 2 shows the results.

  From the above results, it was confirmed that in Examples using the specific quinophthalone compound and the amine-based dispersant, a low-viscosity pigment dispersion could be formed, and that good color characteristics derived from the quinophthalone compound were obtained. .

Claims (4)

A quinophthalone compound represented by the following formula (1), a dispersant, and a solvent,
A coloring composition, wherein the dispersant contains an amine-based dispersant.

[In formula (1), X ^{1 to} X ¹⁶ are each independently a hydrogen atom or a halogen atom, Y ¹ and Y ² are each independently a hydrogen atom or a halogen atom, and Z is an alkylene having 1 to 3 carbon atoms. Group. ]   The coloring composition according to claim 1, wherein the amine value of the dispersant is 20 to 180 mgKOH / g. Having a pixel portion containing a quinophthalone compound represented by the following formula (1) and a dispersant,
A color filter, wherein the dispersant contains an amine-based dispersant.

[In formula (1), X ^{1 to} X ¹⁶ are each independently a hydrogen atom or a halogen atom, Y ¹ and Y ² are each independently a hydrogen atom or a halogen atom, and Z is an alkylene having 1 to 3 carbon atoms. Group. ]   The color filter according to claim 3, wherein the pixel portion is a pixel portion toned with the coloring composition according to claim 1.