JP6891442B2 - New quinophthalone compound - Google Patents

Description

The present invention relates to novel quinophthalone compounds.

Patent Document 1 discloses a bisquinophthalone compound having a certain structure. Further, Patent Document 2 discloses a quinophthalone compound having a certain structure. However, Patent Documents 1 and 2 do not disclose the compound of the present invention represented by the following formula (1).

Tokukousho No. 48-32765 Japanese Unexamined Patent Publication No. 2013-61622

Currently, coloring compositions are used in various fields, and specific applications include printing inks, paints, colorants for resins, colorants for fibers, and color materials for information recording (color filters, toners, inkjets, etc.). Color material used) and the like. The dyes used in the coloring composition are mainly classified into pigments and dyes, and the performance required for them includes color characteristics (coloring power, sharpness) and resistance (weather resistance, light resistance, heat resistance, solvent resistance). )and so on. Unlike dyes, which usually develop color in the molecular state, pigments develop color from the particle state (aggregates of primary particles). Therefore, pigments are generally superior to dyes in resistance, but are often inferior in coloring power and sharpness. Against this background, pigments with high coloring power and high saturation are required. Among them, organic pigments, which are considered to be superior in terms of coloring power, are attracting particular attention.

Among these organic pigments, many new pigments have been actively developed so far, such as the number of registered yellow pigments is the second largest after red pigments. As a yellow organic pigment actually used, for example, in printing ink applications, C.I. I. Pigment Yellow 3, 12, 74, etc. are used, 74, 83, 109, 110, etc. are used for paint applications, and 129, 138, 150, 185, etc. are used for color filter applications. There is. However, their basic structure is mainly limited to azo, azomethine, isoindoline, isoindolinone and the like. Therefore, the structural variations in yellow organic pigments are not yet sufficient to meet the various required applications.

In particular, color filters for liquid crystal displays or pigments used in these color filters are required to have characteristics different from those of conventional general-purpose applications. Specifically, there are demands for "high brightness" that can reduce the power consumption of the backlight, and "high coloring power" that enables thinning of the color filter and high color reproduction. However, the current yellow pigments for color filters do not currently have pigments that meet all of these requirements.
Here, the color filter includes a red pixel portion (R), a green pixel portion (G), and a blue pixel portion (B), and the yellow pigment is often used for toning the green pixel portion. Among the yellow pigments, the most used is C.I. I. Pigment Yellow 138, which has poor coloring power and is not practical in a color standard that requires high color reproducibility. Therefore, in the color standard of high color reproducibility, C.I. I. Pigment Yellow 150 is used as the current yellow pigment, but it cannot be said that Pigment Yellow 150 also has sufficient brightness and coloring power. Therefore, there is a demand for the creation of a new yellow pigment having both excellent brightness and coloring power.

As a result of diligent studies, the present inventors have found that the compound represented by the following formula (1) can solve the above-mentioned problems, and have completed the present invention. That is, the present invention has the following formula (1):

（式（１）中、Ｘは水素原子又はハロゲン原子であり、Ｙは水素原子又はハロゲン原子であり、Ｚは直接結合又は低級アルキレン基である）で表されるキノフタロン化合物（以下、「本発明化合物」と表記する場合がある）に関する。

(In the formula (1), X is a hydrogen atom or a halogen atom, Y is a hydrogen atom or a halogen atom, and Z is a direct bond or a lower alkylene group). It may be referred to as "compound").

The compound of the present invention has excellent brightness and coloring power. In particular, in the color standard for high color reproduction in color filter applications, the compound of the present invention has a brightness equal to or higher than that of the current yellow pigment (CI Pigment Yellow 150), and is superior to this. Has coloring power.

Examples of the halogen atom in the above formula (1) include fluorine, chlorine, bromine and iodine atoms, and among them, the chlorine atom or the bromine atom is preferable, and the chlorine atom is more preferable.

Examples of the lower alkylene group in the above formula (1) include those of C1 to 3 such as methylene, ethylene and propylene, and methylene is more preferable.

The quinophthalone compound represented by the above formula (1) has tautomers having structures such as the following general formula (1-1) and general formula (1-2), and these are also described in the present invention. It is included.

In formulas (1-1) and (1-2), X, Y and Z are as described above.

Such a method for producing the compound of the present invention is not particularly limited, and can be produced by appropriately using a conventionally known method. Hereinafter, one aspect of the method for producing the compound of the present invention will be described. However, the present invention is not limited thereto.

The compound of the present invention can be obtained, for example, by a method including the following steps I and II.
<Step I>
First, 2 to 4 equivalents of crotonaldehyde are added to 1 equivalent of bisaniline and reacted in a strong acid in the presence of an oxidizing agent by the method described in International Publication 2013/098837 (WO2013 / 098837). Synthesize the compound of (2).

In formula (2), X, Y and Z are as described above.

Here, examples of bisaniline include 2,2'-dichlorobenzidine, 2,2', 5,5'-tetrachlorobenzidine, 4,4'-methylenebis (2-chloroaniline) and the like.
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.
With respect to step I, the reaction temperature can be 80 ° C. to 100 ° C., preferably 90 ° C. to 100 ° C., and the reaction time can be 1 hour to 48 hours, preferably 20 hours to 48 hours.

<Step II>
Further, 2 to 6 equivalents of 2,3-naphthalenedicarboxylic acid anhydride were added to 1 equivalent of the compound of the formula (2) obtained by the method described in JP2013-61622, in the presence of an acid catalyst. By reacting, the compound of the formula (1) can be obtained.
Here, examples of the acid catalyst include benzoic acid and zinc chloride.
With respect to Step II, the reaction temperature can be 180 ° C. to 250 ° C., preferably 210 ° C. to 250 ° C., and the reaction time can be 1 hour to 8 hours, preferably 3 hours to 8 hours.

The compound of the present invention may be used alone, or two or more kinds of compounds may be appropriately selected and used in combination.

The compound of the present invention is considered to be applicable to various uses. For example, it can be used as a colorant for a wide range of applications such as printing inks, paints, colored plastics, toners, ink jet inks, light-shielding members for displays, and seed coloring.

The compound of the present invention exhibits properties as an organic pigment, and may be used more preferably by making the pigment particles finer by a salt milling treatment or the like. Such a process may be performed by a known and commonly used method.

The compound of the present invention may be used in combination with a coloring material such as an organic pigment, an organic dye, or an organic pigment derivative other than the compound of the present invention for the purpose of toning or the like. These should be appropriately selected according to the above-mentioned uses, and depending on the use, the compound of the present invention may be used alone, or two or more kinds may be used in combination as appropriate.

The color material that can be used in combination may be any known pigment, dye, or the like.
Depending on the application, azo-based, disazo-based, azomethine-based, anthraquinone-based, quinophthalone-based, quinacridone-based, diketopyrrolopyrrole-based, dioxazine-based, benzimidazolone-based, phthalocyanine-based, isoindoline-based, isoindolinone-based, and perylene-based pigments , And xanthene, azo, disazo, anlaquinone, quinophthalone, triarylmethane, methine, phthalocyanine, rhodamine dyes and the like.

Examples of the yellow pigment that can be used in combination with the compound of the present invention include C.I. I. Pigment Yellow 3, 12, 74, etc., 74, 83, 109, 110, etc. for paint applications, 83, 129, 138, 139, 150, 150, etc. for color filter applications. 185, 231 and the like can be exemplified.

In particular, when the compound of the present invention is used for forming a green pixel portion in a color filter application, for example, C.I. I. Pigment Green 1, 2, 4, 4, 7, 8, 10, 13, 14, 14, 15, 17, 17, 18, 19, 26, 36, 45, 48, It can be used in combination with green pigments such as 50, 51, 54, 55, 58 and 59, but is not limited thereto. When the compound of the present invention is used for forming a green pixel portion in a color filter application, the combined ratio of the green pigment and the yellow pigment of the present invention is, for example, 10 to 100 parts by mass of the yellow pigment per 100 parts by mass of the green pigment. Is.

Further, when the compound of the present invention is used for forming a green pixel portion, the compound of the present invention and a blue pigment can be used in combination. Examples of the blue pigment include C.I. I. Pigment Blue 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 6, aluminum phthalocyanine derivatives and the like.
Here, examples of the above-mentioned aluminum phthalocyanine derivative include compounds represented by the following general formula (3-1).

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

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

Examples of the halogen atom in R in the above formula (3-1) include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Above all, the halogen atom in 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 above general formula (3-2).

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

Among the formulas (3-1), for example, hydroxyaluminum phthalocyanine, chloroaluminum phthalocyanine, bromoaluminum phthalocyanine, compounds represented by the following formula (3-1-1), and the following formula (3-1-2) are preferable. ), A compound represented by the following formula (3-1-3), and the like.

Further, the compound of the present invention can also be used in combination with a red pigment for forming a red pixel portion in a color filter application. Examples of the red pigment include C.I. I. Pigment Red 177, Pigment Red 254 and the like.

When the present invention is used for forming a pattern of a green pixel portion of a color filter, a known method can be adopted. Typically, a photosensitive composition for a color filter containing the compound of the present invention and a photosensitive resin as essential components can be obtained.

As a method for producing a color filter, for example, the compound of the present invention is dispersed in a dispersion medium made of a photosensitive resin, and then coated on a transparent substrate such as glass by a spin coating method, a roll coating method, an inkjet method, or the like. An example is a method called photolithography in which the coated film is subjected to pattern exposure with ultraviolet rays via a photomask, and then the unexposed portion is washed with a solvent or the like to obtain a green pattern. The same applies when the present invention is used for forming a pattern of a red pixel portion of a color filter.

In addition, a color filter may be manufactured by forming a pattern of pixel portions by an electrodeposition method, a transfer method, a micelle electrolysis method, or a PVED (photovoltaic electroforming) method.

To prepare a photosensitive composition for a color filter, for example, a pigment, a photosensitive resin, a photopolymerization initiator, and an organic solvent that dissolves the resin are mixed as essential components. As a manufacturing method thereof, a method of preparing a dispersion liquid by using a pigment, an organic solvent and a dispersant as necessary, and then adding a photosensitive resin or the like to the dispersion liquid is generally used.

As the pigment here, when a green pixel portion is obtained, a pigmented compound of the present invention and the above-mentioned green pigment or blue pigment can be used. Similarly, when the red pixel portion is obtained, a pigmented compound of the present invention and the above-mentioned red pigment can be used.

Dispersants used as needed include, for example, DISPERBYK (registered trademark name) 130, 161 and 162, 163, 170, LPN-6919, LPN-21116 of BASF, and Fuka 46 of BASF. Fuka 47 and the like can be mentioned. In addition, a leven rig agent, a coupling agent, a cationic surfactant and the like can also be used together.

Examples of the organic solvent include aromatic solvents such as toluene, xylene and methoxybenzene, acetate solvents such as ethyl acetate, butyl acetate, propylene glycol monomethyl ether acetate and propylene glycol monoethyl ether acetate, and ethoxyethyl propionate. Propionate solvent, alcohol solvent such as methanol and ethanol, ether solvent such as butyl cellosolve, propylene glycol monomethyl ether, diethylene glycol ethyl ether and diethylene glycol dimethyl ether, ketone solvent such as methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone, fat such as hexane. Group hydrocarbon solvents, nitrogen compound solvents such as N, N-dimethylformamide, γ-butyrolactam, N-methyl-2-pyrrolidone, aniline, pyridine, lactone solvents such as γ-butyrolactone, methyl carbamate and carbamate There are carbamate esters such as a 48:52 mixture of ethyls and the like. As the organic solvent, water-soluble polar solvents such as propionate-based, alcohol-based, ether-based, ketone-based, nitrogen compound-based, and lactone-based solvents are particularly suitable.

Per 100 parts by mass of the pigment composition for a color filter of the present invention, 300 to 1000 parts by mass of an organic solvent and, if necessary, a dispersant of 100 parts by mass or less and / or a quinophthalone derivative of 20 parts by mass or less are uniformly added. The dispersion can be obtained by stirring and dispersing so as to become. Next, in this dispersion, 3 to 20 parts by mass of a photosensitive resin per 100 parts by mass of the dispersion, 0.05 to 3 parts by mass of a photopolymerization initiator per 1 part by mass of the photosensitive resin, and, if necessary, further organic. A photosensitive composition for a color filter pixel portion can be obtained by adding a solvent and stirring and dispersing the mixture so as to be uniform.

The above pigment composition for a color filter is, in the case of green pixel use, per 10 parts by mass of the quinophthalone pigment composition of the present invention, and in the case of green pixel use, 200 parts by mass or less of green pigment and / and 200 parts by mass or less of blue pigment. Is appropriately set and mixed, and in the case of a red pixel application, 200 parts by mass or less of a red pigment is mixed. In addition, other yellow pigments may be mixed if necessary.

Examples of the photosensitive resin that can be used at this time include thermoplastic resins such as urethane resin, acrylic resin, polyamic acid resin, polyimide resin, styrene maleic acid resin, and styrene maleic anhydride resin. Bifunctional monomers such as 1,6-hexanediol diacrylate, ethylene glycol diacrylate, neopentyl glycol diacrylate, triethylene glycol diacrylate, bis (acryloxyethoxy) bisphenol A, 3-methylpentanediol diacrylate, etc. Examples thereof include photopolymerizable monomers such as polyfunctional monomers such as trimethylolpropane triacrylate, pentaerythritol triacrylate, tris (2-hydroxyethyl) isocyanate, dipentaerythritol hexaacrylate, dipentaerythritol pentaacrylate and the like.

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'). -Azidobenzyl) -2-propane-2'-sulfonic acid, 4,4'-diazidostilbene-2,2'-disulfonic acid and the like.

The photosensitive composition for the pixel portion of the color filter thus prepared is subjected to pattern exposure with ultraviolet rays through a photo mask, and then the unexposed portion is washed with an organic solvent, alkaline water, or the like to prepare a color filter. Can be done.

Hereinafter, the present invention will be described based on examples, but the present invention is not limited thereto. Unless otherwise specified in Examples and Comparative Examples, "parts" and "%" are based on mass.

[Synthesis example]
Synthesis Example 1-1
25 g (76.7 mmol) of 2,2'-dichlorobenzidine hydrochloride was weighed in a flask, 125 g of 70% (w / w) sulfuric acid was added, and the mixture was stirred at 50 ° C. for 1 hour. An aqueous solution prepared by dissolving 1.3 g of sodium iodide in 8 mL of water was added to this mixture, and the mixture was stirred at 100 ° C. for 1 hour, and then 16.1 g (230 mmol) of crotonaldehyde was added dropwise over 1 hour. After completion of the dropping, the mixture was further stirred at 100 ° C. for 7 hours. After allowing to cool, the reaction solution is poured into 400 g of ice water, an aqueous sodium hydroxide solution (15 g of sodium hydroxide / 50 mL of water) is added while stirring, and the insoluble matter is filtered off, and then the aqueous sodium hydroxide solution is added to the filtrate. (55 g of sodium hydroxide / 150 mL of water) was added to adjust the pH to 12. The produced precipitate was filtered and washed with water to obtain a crude product. The obtained crude product was dissolved in 100 mL of 6N hydrochloric acid water, 20.9 g of zinc chloride was added with vigorous stirring, and the mixture was stirred at room temperature for 0.5 hour and then under ice-cooling for 0.5 hour. The generated precipitate was filtered off and washed with 3N hydrochloric acid water. After adding 150 mL of 2-propanol to the obtained solid and stirring at room temperature for 1 hour, the insoluble matter was filtered and washed with 2-propanol. The obtained solid was added to 150 mL of water, 50 mL of 28% aqueous ammonia was added with stirring, and the mixture was extracted with chloroform. The chloroform layer was dried over sodium sulfate, filtered, and chloroform was distilled off with an evaporator. The residue was recrystallized from chlorobenzene to obtain 9.50 g (27.0 mmol) of the intermediate (A-1). (Yield: 35%)

^{1 1} H-NMR (CDCl ₃ ) δppm: 2.85 (s, 6H), 7.41 (d, J = 8.5 Hz, 2H), 7.97 (d, J = 1.9 Hz, 2H), 8.13 (d, J = 8.5 Hz, 2H), 8.16 (d, J = 1.9 Hz, 2H)
¹³ C-NMR (CDCl ₃ ) δppm: 25.8, 123.6, 124.7, 127.9, 128.7, 133.6, 136.5, 136.8, 143.6, 160.7
FT-IR cm ^-1 : 2952 (aromatic or methyl group CH expansion and contraction), 1602 (aromatic C = C expansion and contraction), 1488, 1468

Synthesis Example 1-2
Under a nitrogen atmosphere, 7 mL of monochlorobenzene, 13.8 g (113 mmol) of benzoic acid, and 2.80 g (14.1 mmol) of 2,3-naphthalenedicarboxylic acid anhydride were weighed and melted at 150 ° C. To this, 2.00 g (5.66 mmol) of the intermediate (A-1) obtained in Synthesis Example 1-1 was suspended in 10 mL of monochlorobenzene and added. While distilling off monochlorobenzene, the mixture was heated and stirred to 210 ° C. for 1.5 hours, and further stirred at the same temperature for 4 hours. After allowing to cool, 140 mL of chlorobenzene was added to the reaction solution, and the mixture was stirred for 1 hour and then filtered to obtain a solid substance. The obtained solid was suspended in 80 mL of acetone, and 2.70 g (3.78 mmol) of the target product (B-1) as a yellow powder was obtained by filtration and washing with acetone. (Yield: 67%)

FT-IR cm ^-1 : 3052 (aromatic CH expansion and contraction), 1789, 1675, 1631 (carbonyl C = O expansion and contraction), 1600, 1573, 1538 (aromatic C = C expansion and contraction), 1401
FD-MS: 712 M +

Synthesis Example 2-1
38.0 g (118 mmol) of 2,2', 5,5'-tetrachlorobenzidine was weighed in a flask, 129 mL of 70 wt% sulfuric acid was added, and the mixture was stirred at 50 ° C. for 1 hour. Then, 1.90 mL of an 8 M aqueous sodium iodide solution was added to the system, and the mixture was stirred at 100 ° C. for 1 hour, and then 29.0 mL (353 mmol) of crotonaldehyde was added dropwise to the system over 4 hours. After the dropping, the temperature was kept at 100 ° C., and the mixture was stirred for 18 hours. After allowing to cool, 170 g (3.03 mol) of potassium hydroxide was added to the reaction solution in an ice bath to make the reaction solution basic, and then extraction was performed with chloroform. The obtained chloroform solution was concentrated by vacuum distillation and purified by a silica gel column (developing solvent: chloroform). Finally, it was dried with a desiccator to obtain 4.67 g (11.1 mmol) of the intermediate (A-2) which is a pale yellow powder. (Yield: 9%)

^{1 1} H-NMR (CDCl ₃ ) δppm: 2.88 (s, 6H), 7.52 (d, J = 8.0 Hz, 2H), 7.78 (s, 2H), 8.58 (d, J = 8.8 Hz, 2H)
¹³ C-NMR (CDCl ₃ ) δppm: 25.7, 124.2, 126.0, 129.3, 130.8, 132.0, 134.1, 134.5, 144.3, 161.5
FT-IR cm ^-1 : 3029, 2995, 2952 (aromatic or methyl group CH expansion and contraction), 1190 (aryl chloride C-Cl expansion and contraction)

Synthesis Example 2-2
Under a nitrogen atmosphere, 7.11 g (58.2 mmol) of benzoic acid was weighed in a flask and melted at 150 ° C. To this, 1.14 g (2.70 mmol) of the intermediate (A-2) obtained in Synthesis Example 2-1 and 1.43 g (7.22 mmol) of 2,3-naphthalenedicarboxylic acid anhydride were added, and the temperature was adjusted to 220 ° C. Stirred for 4 hours. After allowing to cool, 400 mL of acetone was added to the reaction solution, and the mixture was stirred for 1 hour, and then 1.80 g (2.30 mmol) of the target product (B-2) as a yellow powder was obtained by vacuum filtration. (Yield: 85%)

FT-IR cm ^-1 : 3051 (aromatic CH expansion and contraction), 1796, 1676 (carbonyl C = O expansion and contraction), 1183, 1138 (aryl chloride C-Cl expansion and contraction)
FD-MS: 782 M +

Synthesis Example 3-1
20.1 g (75.2 mmol) of 4,4'-methylenebis (2-chloroaniline) was weighed in a flask, 82.3 mL of 70 wt% sulfuric acid was added, and the mixture was stirred at 50 ° C. for 1 hour. Then, 1.21 mL of an 8 M aqueous sodium iodide solution was added to the system, and the mixture was stirred at 100 ° C. for 1 hour, and then 18.5 mL (225 mmol) of crotonaldehyde was added dropwise to the system over 4 hours. After the dropping, the temperature was kept at 100 ° C., and the mixture was stirred for 18 hours. After allowing to cool, 103 g (1.83 mol) of potassium hydroxide was added to the reaction solution in an ice bath to make the reaction solution basic, and then extraction was performed with chloroform. The obtained chloroform solution was concentrated by vacuum distillation and purified by a silica gel column (developing solvent: chloroform). Finally, it was dried with a desiccator to obtain 14.2 g (38.7 mmol) of the intermediate (A-3) which is a pale yellow powder. (Yield: 51%)

^{1 1} H-NMR (CDCl ₃ ) δppm: 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 ) 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, 3055, 3031, 2915 (aromatic or methyl group CH expansion and contraction), 1603, 1487, 1206 (aryl chloride C-Cl expansion and contraction)
FD-MS: 366 M +

Synthesis example 3-2
In a nitrogen atmosphere, 15.1 g (124 mmol) of benzoic acid was weighed in a flask and melted at 150 ° C. To this, 2.11 g (5.75 mmol) of the intermediate (A-3) obtained in Synthesis Example 2-1 and 1.43 g (7.22 mmol) of 2,3-naphthalenedicarboxylic acid anhydride were added, and the temperature was adjusted to 220 ° C. Stirred for 4 hours. After allowing to cool, 400 mL of acetone was added to the reaction solution, and the mixture was stirred for 1 hour, and then 3.67 g (5.04 mmol) of the target product (B-3) as a yellow powder was obtained by vacuum filtration. (Yield: 88%)

FT-IR cm ^-1 : 3055 (aromatic CH expansion and contraction), 1685 (carbonyl C = O expansion and contraction), 1228, 1197, 1184 (aryl chloride C-Cl expansion and contraction)
FD-MS: 726 M +

Pigmentation 0.50 parts by mass of the quinophthalone compound obtained in the above synthesis example was ground together with 1.50 parts by mass of sodium chloride and 0.75 parts by mass of diethylene glycol. Then, this mixture was poured into 600 parts by mass of warm water and stirred for 1 hour. The water-insoluble matter was separated by filtration, washed well with warm water, and then air-dried at 90 ° C. for pigmentation. The particle system of the pigment was 100 nm or less, and the average length / width ratio of the particles was less than 3.00. The following dispersion test and color filter evaluation test were carried out using the obtained yellow pigment of the quinophthalone compound.

Example 1
(Preparation of spin coating liquid)
Put 0.660 parts by mass of quinophthalone compound (B-1) in a glass bottle, 12.8 parts by mass of propylene glycol monomethyl ether acetate, 0.467 parts by mass of DISPERBYK (registered brand name) LPN-6919 (manufactured by Big Chemie Co., Ltd.), Acrylic resin solution manufactured by DIC Co., Ltd. Unidic (registered brand name) ZL-295 0.700 parts by mass, 0.3-0.4 mmφ Sepul beads 22.0 parts by mass are added, and a paint conditioner (manufactured by Toyo Seiki Co., Ltd.) is used. The mixture was dispersed for 4 hours to obtain a pigment dispersion. Further, 2.00 parts by mass of the obtained pigment dispersion, 0.490 parts by mass of the acrylic resin solution Unidic (registered trademark name) ZL-295 manufactured by DIC Corporation, and 0.110 parts by mass of propylene glycol monomethyl ether acetate are placed in a glass bottle. A spin-coated coating solution was prepared.

(Making a yellow color filter)
The obtained spin coating coating liquid was applied onto a glass substrate by a spin coater. The rotation speed of the spin coater was 600, 800, 1000, 1200 rpm, and four types of color filter substrates having different coating film thicknesses of the compositions were produced. Each color filter substrate thus obtained was heated at 90 ° C. for 3 minutes to obtain a yellow color filter.

Example 2
A spin coating coating solution was obtained in the same manner as in Example 1 except that the quinophthalone compound (B-2) was used instead of the quinophthalone compound (B-1), and a yellow color filter was obtained.

Example 3
A spin coating coating solution was obtained in the same manner as in Example 1 except that the quinophthalone compound (B-3) was used instead of the quinophthalone compound (B-1), and a yellow color filter was obtained.

Comparative Example 1
In Example 1, C.I. I. A spin coat coating solution was obtained in the same manner except that Pigment Yellow 138 (manufactured by BASF) and 6.42 parts by weight of propylene glycol monomethyl ether acetate added before dispersion were used to obtain a yellow color filter.

Comparative Example 2
C. I. Pigment Yellow 150 (manufactured by Sanyo Dye Co., Ltd.) 1.14 parts by mass in a poly bottle, propylene glycol monomethyl ether acetate 12.0 parts by mass, DISPERBYK (registered brand name) LPN-21116 (manufactured by Big Chemie Co., Ltd.) 2.84 A part by mass and 38.0 parts by mass of 0.3-0.4 mmφ Sepul beads were added and dispersed with a paint conditioner (manufactured by Toyo Seiki Co., Ltd.) for 4 hours to obtain a pigment dispersion. Further, 2.00 parts by mass of the obtained pigment dispersion, 0.490 parts by mass of the acrylic resin solution Unidic (registered trademark name) ZL-295 manufactured by DIC Co., Ltd., and 0.110 parts by mass of propylene glycol monomethyl ether acetate are placed in a glass bottle. A spin-coat coating solution was obtained, and a yellow color filter was obtained in the same manner as in the step of "manufacturing a yellow color filter" of Example 1.

Color filter test example・ Color filter characteristic test A color filter is prepared from a dispersion liquid using the pigment, and the chromaticity and transmission spectrum are measured by a spectrophotometer (HITACHI U3900 / 3900H type) with a film thickness meter (HITACHI). The film thickness was measured by VS1000 scanning white interference microscope). Based on these results, the color filter characteristics were evaluated from the estimated brightness and the estimated film thickness (the thinner the film thickness, the higher the coloring power) when adjusted to the green chromaticity.

The color filter characteristics of the yellow color filters produced in Examples and Comparative Examples after post-baking (baking at 230 ° C. for 1 hour) were evaluated (details of the equipment used and the like are as described above). Based on the evaluation results of the yellow color filter, the color filter performance was evaluated based on the estimated brightness and the estimated film thickness of the green tint in the color standard DCI-P3 with high color reproducibility. A table summarizing these values is shown below.

Examples 1 to 3 showed good brightness equal to or higher than that of Comparative Example 2 using the current yellow pigment (CI Pigment Yellow 150), and the film thickness was significantly reduced. This indicates that the yellow pigment of the present invention has a high coloring power and is suitable as a yellow pigment for a color filter. Although Comparative Example 1 (CI Pigment Yellow 138) shows a good luminance value, as described in the description of the prior art, the film thickness is very thick and is not at a practical level. This is due to the lack of coloring power of 138. As described above, the compound of the present invention has a C.I. I. It has a remarkable effect exceeding Pigment Yellow 138.

Claims (4)

The following formula (1') :

(In the formula (1') , X is a hydrogen atom or a halogen atom, Y is a hydrogen atom or a halogen atom, and Z is a direct bond or a lower alkylene group). The quinophthalone compound according to claim 1, wherein Z is a direct bond or a methylene group. A colorant containing the quinophthalone compound according to claim 1 or 2. A coloring composition containing the colorant according to claim 3.