JP2018203798A - Quinophthalone compound - Google Patents

Abstract

To provide a novel yellow pigment having both of excellent brightness and tinting power.SOLUTION: The present invention provides a novel quinophthalone compound, specifically, a quinophthalone compound represented by the formula (1) (where, X-Xindependently represent a hydrogen atom or a halogen atom, Z is a C1-3 alkylene group). The present invention further provides a colorant containing the quinophthalone compound represented by the formula (1), and a coloring composition containing the colorant.SELECTED DRAWING: None

Description

  The present invention relates to a novel quinophthalone compound.

  Patent Documents 1 and 2 disclose bisquinophthalone compounds 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).

International Publication 2013/098836 Pamphlet Japanese Patent Publication No. 48-32765

  Currently, colored compositions are used in various fields. Specific applications include printing inks, paints, resin colorants, fiber colorants, information recording colorants (for color filters, toners, ink jets, etc.). Colorant to be used). Colors used in coloring compositions are mainly divided into pigments and dyes. The required properties include color characteristics (coloring power, sharpness) and resistance (weather resistance, light resistance, heat resistance, solvent resistance). )and so on. Usually, unlike a dye that develops color in a molecular state, a pigment develops from a particle state (aggregates of primary particles). For this reason, pigments are generally superior in resistance compared to dyes, but are often inferior in coloring power and sharpness. From such a background, pigments with high coloring power and high saturation are demanded. Of these, organic pigments, which have been dominant in terms of coloring power, are particularly attracting attention.

  Among these organic pigments, many new pigments have been actively developed so far, for example, yellow pigments have the second largest number of registered color indexes after red pigments. Examples of yellow organic pigments that are actually used include C.I. I. Pigment Yellow 3, 12 and 74 etc. are used for paint applications, 74, 83, 109 and 110 etc., and for color filter applications are 129, 138, 150 and 185 etc. Yes. However, their basic structures are mainly azo, azomethine, isoindoline, isoindolinone and the like. Therefore, the structural variation in the yellow organic pigment is not yet sufficient to meet various required uses.

In particular, color filters for liquid crystal displays or pigments used in these color filters are required to have characteristics different from conventional general-purpose applications. Specifically, there is a demand for “high luminance” that can reduce the power consumption of the backlight, and “high coloring power” that enables color filter thinning and high color reproduction. However, the current yellow pigment for color filters has no pigment that meets all 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 of the green pixel portion. Among yellow pigments, the most used amount is C.I. I. Pigment Yellow 138, which has poor coloring power and is not practical in color standards that require 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 150 also has sufficient luminance and coloring power. Thus, there is a demand for the creation of a new yellow pigment having both excellent brightness and coloring power.

As a result of intensive studies to solve the above problems, the present inventors show more selective absorption and permeation by dimerizing a specific quinophthalone skeleton and examining the connection position of dimerization. I found. Furthermore, the dimerization method is also studied repeatedly. Instead of simply adopting a direct bond, excessive conjugation or spectral degradation can be achieved by cleaving the conjugate using an alkylene group having 1 to 3 carbon atoms as a spacer. We found that broadening can be suppressed. In addition, the dispersibility was improved by introducing a polyhalogenated imide structure.
The present inventors have found that a compound represented by the following formula (1) can solve the above problems based on such examination results, and have completed the present invention. That is, the present invention provides the following formula (1):

（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、Ｚは炭素数１〜３の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 _{1 to} X ₁₆ are each independently a hydrogen atom or a halogen atom, and Z is an alkylene group having 1 to 3 carbon atoms) (hereinafter referred to as “the compound of the present invention”). ”).

  The compound of the present invention has excellent luminance 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 luminance superior to that of the current yellow pigment (CI Pigment Yellow 150) and an excellent coloring power exceeding this. Have.

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

  Examples of the alkylene group in the above formula (1) include C1 to C3 groups such as methylene, ethylene, propylene and the like from the viewpoint of not causing deterioration of crystallinity and resistance such as heat resistance and light resistance. However, the case of methylene is more preferable. Even when the compound of the present invention is used as a pigment, the alkylene group is preferably within the above-mentioned range from the viewpoint of preventing dyeing and reduction in coloring power.

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

In formula (1-i) and formula (1-ii), X _{1 to} X ₁₆ and Z are as described above.

  Preferred specific examples of the quinophthalone compound of the present invention are listed below, but the present invention is not limited thereto.

  The 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 embodiment of the production method of the compound of the present invention will be described. However, the present invention is not limited to these.

The compound of the present invention can be obtained, for example, by a method including the following step I, step II and step III.
<Process I>
First, J.H. According to the method described in Heterocyclic, Chem, 30, 17 (1993), bishaloaniline is added in an amount of 2 to 3 equivalents to 1 equivalent of bishaloaniline, and reacted in a strong acid in the presence of an oxidizing agent. The compound of 2) is synthesized.

  In formula (2), Z is 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.
Regarding Step I, the reaction temperature can be 80 to 100 ° C., preferably 90 to 100 ° C., and the reaction time can be 1 to 6 hours, preferably 3 to 6 hours.

<Step II>
Furthermore, Org. Lett. , 17, 5934 (2015), and the like, by reacting the obtained compound of the formula (2) with ammonia in the presence of a copper catalyst, the compound of the formula (3) can be obtained.

  In formula (3), Z is as described above.

  Regarding Step II, the reaction temperature can be 80 ° C to 140 ° C, preferably 90 ° C to 120 ° C, and the reaction time can be 8 hours to 24 hours, preferably 18 hours to 24 hours.

<Step III>
Furthermore, 4 to 6 equivalents of phthalic anhydride or tetrahalophthalic anhydride are added to 1 equivalent of the compound of the formula (3) obtained by the method described in JP2013-61622A in the presence of an acid catalyst. By reacting, the compound of Formula (1) can be obtained.
Here, examples of the acid catalyst include benzoic acid and zinc chloride.
Regarding step III, 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 compounds may be appropriately selected and used in combination.

  The compound of the present invention is considered applicable to various uses. For example, it can be used as a colorant for a wide range of uses such as printing ink, paint, colored plastic, toner, inkjet ink, light-shielding member for display, and seed coloring.

  The compound of the present invention exhibits properties as an organic pigment, and may be more suitably used by subjecting the pigment particles to a finer size, such as by salt milling treatment. Such processing may be performed by a known and conventional 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. These should be appropriately selected according to the use as described above, and the compound of the present invention may be used alone or in combination of two or more depending on the use.

As the colorant that can be used in combination, any of known pigments, dyes and the like may be used.
Depending on the application, azo, disazo, azomethine, anthraquinone, quinophthalone, quinacridone, diketopyrrolopyrrole, dioxazine, benzimidazolone, phthalocyanine, isoindoline, isoindolinone, perylene pigment And xanthene, azo, disazo, anthraquinone, quinophthalone, triarylmethane, methine, phthalocyanine, and rhodamine dyes.

  As yellow pigments that can be used in combination with the compounds of the present invention, C.I. I. Pigment Yellow 3, 12 and 74, etc., for paint applications 74, 83, 109 and 110, etc., for color filters, 83, 129, 138, 139, 150, 185, 228, 231 and the like.

  In particular, when the compound of the present invention is used for forming a green pixel portion in color filter applications, for example, C.I. I. Pigment Green 1, 2, 4, 4, 7, 10, 13, 14, 14, 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 weight of the yellow pigment per 100 parts by weight of the green pigment. It is.

Moreover, when using this invention compound for green pixel part formation, this invention compound and a blue pigment can also be used together. 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 aluminum phthalocyanine derivative include compounds represented by the following general formula (5-1).

(In formula (5-1), R represents a halogen atom, a hydroxy group, or a group represented by the following general formula (5-2).)

(In formula (5-2), X is a direct bond or an oxygen atom. Ar is a phenyl group or a naphthyl group. In the formula, an asterisk represents a binding site.)

  As said halogen atom in R in above-described formula (5-1), a fluorine atom, a chlorine atom, a bromine atom, an iodine atom etc. are mentioned, for example. Among these, the halogen atom in R is preferably a chlorine atom or a bromine atom.

  In Formula (5-1), R is preferably a chlorine atom, a bromine atom, a hydroxy group, or a group represented by General Formula (5-2).

  In formula (5-2), X is preferably an oxygen atom.

  Preferred examples of the formula (5-1) include, for example, hydroxyaluminum phthalocyanine, chloroaluminum phthalocyanine, bromoaluminum phthalocyanine, a compound represented by the following formula (5-1-1), and the following formula (5-1-2) ), A compound represented by the following formula (5-1-3), a compound represented by the following formula (5-1-4), and the like.

  Furthermore, this invention compound can also be used together with a red pigment for red pixel part formation in a color filter use. Examples of red pigments include C.I. I. Pigment red 177, 254, and the like.

  When the present invention is used for forming the pattern of the green pixel portion of the color filter, a known method can be employed. 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 applied onto a transparent substrate such as glass by a spin coating method, a roll coating method, an ink jet method, etc. There is a method called photolithography in which the coating film is subjected to pattern exposure with ultraviolet rays through a photomask, and then an unexposed portion is washed with a solvent or the like to obtain a green pattern. The same applies to the case where the present invention is used for forming the pattern of the red pixel portion of the color filter.

  In addition, a color filter may be manufactured by forming a pattern of the pixel portion by an electrodeposition method, a transfer method, a micellar electrolysis method, or a PVED (Photovoltaic Electrodeposition) method.

  In order to prepare the photosensitive composition for color filters, 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 is generally used in which a dispersion is prepared using a pigment, an organic solvent, and a dispersant as required, and then a photosensitive resin or the like is added thereto.

  As a pigment here, when obtaining a green pixel part, what pigment-ized this invention compound and the above-mentioned green pigment and blue pigment can be used. Similarly, when a red pixel portion is obtained, a pigment obtained by compounding the compound of the present invention and the red pigment described above can be used.

  Examples of the dispersant used as necessary include DISPERBYK (registered trademark) 130, 161, 162, 163, 170, LPN-6919, LPN-21116, and the like of Big Chemie. In addition, a revenig rigging agent, a coupling agent, a cationic surfactant, and the like can be used together.

  Examples of the organic solvent include aromatic solvents such as toluene, xylene, and methoxybenzene, acetate solvents such as ethyl acetate and butyl acetate, propylene glycol monomethyl ether acetate, 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 and diethylene glycol dimethyl ether, ketone solvents such as methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone, fats such as hexane Group hydrocarbon solvents, N, N-dimethylformamide, γ-butyrolactam, N-methyl-2-pyrrolidone, ani Emissions, nitrogen compound-based solvent such as pyridine, a lactone-based solvents such as γ- butyrolactone, there are carbamic acid esters such as a mixture of 48:52 of methyl carbamate and ethyl carbamate. As the organic solvent, a propionate-based, alcohol-based, ether-based, ketone-based, nitrogen compound-based or lactone-based polar solvent that is water-soluble is particularly suitable.

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

  The above-mentioned color filter pigment composition is used for a green pixel, per 10 parts by mass of the quinophthalone pigment composition of the present invention, and for a green pixel, 200 parts by mass or less of a green pigment and / or 200 parts by mass or less of a blue pigment. Are appropriately set and mixed. In the case of a red pixel application, 200 parts by mass or less of a red pigment is mixed. In addition, you may mix another yellow pigment as needed.

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

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

  The thus prepared photosensitive composition for a color filter pixel portion is subjected to pattern exposure with ultraviolet rays through a photomask, and then a color filter is prepared by washing an unexposed portion with an organic solvent or alkaline water. Can do.

  EXAMPLES Hereinafter, although this invention is demonstrated based on an Example, this invention is not limited by this. In Examples and Comparative Examples, “part” and “%” are based on mass unless otherwise specified.

[Synthesis example]
Synthesis example 1
In a flask, 4,4′-bismethylene (2-bromoaniline) hydrochloride 7.0 parts, p-chloranil 8.0 parts, 1-butanol 32.4 parts, 36% hydrochloric acid 29.5 parts, water 25.0 Parts were charged and stirred at 95 ° C. To this mixture, 3.4 parts of crotonaldehyde was added dropwise over 30 minutes. The mixture was stirred at 95 ° C. for an additional 2.5 hours. The mixture was cooled to 80 ° C., 4.5 parts of anhydrous zinc chloride and 45.0 parts of tetrahydrofuran were added, and the mixture was stirred for 1 hour. After cooling the reaction mixture to 20 ° C. or lower, the formed precipitate was filtered, washed with tetrahydrofuran and then 2-propanol. The obtained solid was added to 50.0 parts of water, and 14.0 parts of 28% aqueous ammonia was added with stirring. After stirring for 1 hour, the mixture was filtered to obtain a solid. The obtained solid was washed with ethanol and dried under reduced pressure to obtain 3.0 parts of 6,6′-methylenebis (8-bromo-2-methylquinoline) (intermediate (A)). (Yield 40%)

<NMR analysis>
¹ H-NMR (DMSO-d6) δ ppm: 2.67 (s, 6H), 4.29 (s, 2H), 7.47 (d, J = 8.5 Hz, 2H), 7.85 (s, 2H), 8.05 (s, 2H), 8.23 (d, J = 8.5 Hz, 2H)
¹³ C-NMR (DMSO-d6) δ ppm: 25.1, 123.3, 123.5, 127.1, 127.5, 134.1, 136.6, 139.0, 142.8, 159.7
<Infrared spectroscopic analysis>
1605, 1485 cm ^-1
<FD / MS analysis>
456M +

Synthesis example 2
2.4 parts of intermediate (A) obtained in Synthesis Example 1 in an autoclave reaction vessel, 0.18 parts of copper (I) iodide, N, N'-bis (2-phenyl-4-methylphenyl) oxalamide 0 .72 parts, tripotassium phosphate 2.45 parts, dimethyl sulfoxide 110 parts, 28% aqueous ammonia 11.0 parts were charged and stirred at 95 ° C. for 8 hours in a nitrogen atmosphere. After cooling to room temperature, the reaction mixture was poured into 160 parts of water and stirred for 1 hour. The produced precipitate was filtered and washed with water, and then added to 150 parts of chloroform and stirred. The mixture was filtered to remove insolubles, and the resulting filtrate was extracted with 10% hydrochloric acid, and the aqueous layer was separated. 28% aqueous ammonia was added to the obtained aqueous layer with stirring to adjust the pH to 8, and after stirring for 1 hour or longer, the produced precipitate was filtered and washed with water, and then dried under reduced pressure. The obtained solid was washed with toluene to obtain 1.2 parts of 6,6′-methylenebis (8-amino-2-methylquinoline) (intermediate (B)). (Yield 70%)

<NMR analysis>
¹ H-NMR (DMSO-d6): 2.61 (s, 6H), 3.96 (s, 2H), 5.76 (brs, 4H), 6.68 (d, J = 1.6 Hz, 2H) ), 6.91 (d, J = 1.6 Hz, 2H), 7.30 (d, J = 8.5 Hz, 2H), 8.00 (d, J = 8.5 Hz, 2H)
¹³ C-NMR (DMSO-d6): 24.7, 42.2, 110.2, 113.2, 122.1, 126.6, 135.7, 135.9, 139.4, 144.2 154.5
<Infrared spectroscopic analysis>
3429, 3296, 2911, 1623, 1595, 1504, 1423 cm ⁻¹
<FD / MS analysis>
328M +

Synthesis example 3
25.0 parts of benzoic acid was charged into the flask and heated and melted at 160 ° C. in a nitrogen atmosphere. Next, 0.96 part of the intermediate (B) obtained in Synthesis Example 2 and 4.38 parts of tetrachlorophthalic anhydride were added with stirring. The mixture was heated to 220 ° C. over 30 minutes and further stirred at the same temperature for 6 hours. The reaction solution was cooled to 150 ° C., 70 parts of monochlorobenzene was added, and then cooled to 100 ° C. The solid obtained by filtering the reaction solution was washed with monochlorobenzene and then further washed with acetone. The obtained solid was added to 20 parts of N, N-dimethylformamide, heated and stirred at 100 ° C. for 1 hour, cooled to room temperature, filtered by adding 20 parts of methanol and repeated twice. The obtained solid was washed with methanol and dried under reduced pressure to obtain 4.00 parts of a compound represented by the formula (C). (Yield 98%)

<Infrared spectroscopic analysis>
1847, 1789, 1732, 1685, 1642, 1610, 1537, 1414, 1303 cm ⁻¹
<FD / MS analysis>
1400M +

0.50 parts by mass of the compound (C) obtained in Pigmentation Synthesis Example 3 (hereinafter referred to as quinophthalone dimer (C)) was ground together with 1.50 parts by mass of sodium chloride and 0.700 parts by mass of diethylene glycol. . Thereafter, 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 and washed well with warm water, and then air-dried at 90 ° C. for pigmentation. The particle diameter 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 performed using the obtained yellow pigment of quinophthalone dimer.

Production Example 1
0.700 parts by mass of pigmented quinophthalone dimer (C) is put in a glass bottle, 6.42 parts by mass of propylene glycol monomethyl ether acetate, 0.467 parts by mass of DISPERBYK (registered trademark) LPN-6919 (manufactured by BYK Chemie). DIC Co., Ltd. acrylic resin solution Unidic (registered trademark) ZL-295 0.700 parts by mass, 0.3-0.4 mmφ Sepul beads 22.0 parts by mass, paint conditioner (manufactured by Toyo Seiki Co., Ltd.) For 4 hours to obtain a pigment dispersion. Furthermore, 2.00 parts by mass of those pigment dispersions, 0.490 parts by mass of acrylic resin solution Unidic (registered trademark) ZL-295 manufactured by DIC Corporation, 0.110 parts by mass of propylene glycol monomethyl ether acetate are put in a glass bottle, The composition for yellow toning was produced by shaking.

Production Example 2
C. I. Pigment Green 59 (manufactured by DIC Corporation) 2.48 parts by mass in a glass bottle, 10.9 parts by mass of propylene glycol monomethyl ether acetate, DISPERBYK (registered trademark) LPN-6919 (manufactured by Big Chemie) 1.24 parts by mass, Acrylic resin solution manufactured by DIC Corporation Unidick (registered trademark) ZL-295 1.86 parts by mass, 0.3-0.4 mmφ Sepul beads are added, and dispersed with a paint conditioner (manufactured by Toyo Seiki Co., Ltd.) for 2 hours to disperse the pigment. Got the body. Further, 4.00 parts by mass of the obtained pigment dispersion, 0.980 parts by mass of an acrylic resin solution Unidic (registered trademark) ZL-295 manufactured by DIC Corporation, and 0.220 parts by mass of propylene glycol monomethyl ether acetate are put in a glass bottle. The composition for green toning was produced by shaking.

Example 1
The composition for yellow toning obtained in Production Example 1 and the composition for green toning obtained in Production Example 2 were mixed, applied onto a glass substrate with a spin coater, and then dried. After heating the obtained glass substrate for evaluation at 230 degreeC for 1 hour, the green color filter which shows each green chromaticity at the time of using C light source in the color specification for high color reproduction was produced. As the green chromaticity, the values used in Japanese Patent Application Laid-Open No. 2011-128181 (0.240, 0.650) and the method used in Japanese Patent Application Laid-Open No. 2011-242425 (0.230, 0.670) are used. It was.

Production Example 3
In Production Example 1, C.I. was used instead of the quinophthalone dimer (C) obtained in Synthesis Example 3. I. A yellow toning composition was prepared in the same manner as in Production Example 1 except that CI Pigment Yellow 138 (manufactured by BASF) was used.

Comparative Example 1
A green color filter was obtained in the same manner as in Example 1 except that the yellow toning composition obtained in Production Example 3 was used in place of the yellow toning composition obtained in Production Example 1.

Production Example 4
C. I. Pigment Yellow 150 (manufactured by Sanyo Dye) 1.14 parts by mass in a plastic bottle, 12.0 parts by mass of propylene glycol monomethyl ether acetate, DISPERBYK (registered trademark) LPN-21116 (manufactured by Big Chemie) 2.84 parts by mass Then, 38.0 parts by mass of 0.3-0.4 mmφ sepul beads were added and dispersed for 4 hours with a paint conditioner (manufactured by Toyo Seiki Co., Ltd.) to obtain a pigment dispersion. Furthermore, 2.00 parts by mass of the obtained pigment dispersion, 0.490 parts by mass of acrylic resin solution Unidic (registered trademark) ZL-295 manufactured by DIC Corporation, and 0.110 parts by mass of propylene glycol monomethyl ether acetate are put in a glass bottle. The composition for yellow toning was produced by shaking.

Comparative Example 2
A green color filter was obtained in the same manner as in Example 1 except that the yellow toning composition obtained in Production Example 4 was used in place of the yellow toning composition obtained in Production Example 1.

Production Example 5
In Production Example 1, instead of the quinophthalone dimer (C) obtained in Synthesis Example 3, a directly-coupled quinophthalone dimer (D) synthesized by the method described in WO2013 / 098836 (CI Pigment Yellow 228) A composition for yellow toning was prepared in the same manner as in Production Example 1 except that was used.

Comparative Example 3
A green color filter was obtained in the same manner as in Example 1 except that the yellow toning composition obtained in Production Example 5 was used in place of the yellow toning composition obtained in Production Example 1.

Color Filter Test Example / Color Filter Characteristic Test Using each color filter produced, chromaticity and transmission spectrum were measured with a spectrophotometer (U3900 / 3900H type manufactured by HITACHI).
The film thickness was measured by a film thickness meter (VS1000 scanning white interference microscope manufactured by HITACHI) using each of the produced color filters. The results are shown in Table 1 and Table 2 below. In the table, the higher the brightness value, the better, and the thinner the film thickness, the higher the coloring power.

  Example 1 showed a brightness superior to that of the comparative example at any green chromaticity in the color standard for high color reproduction. This indicates that the yellow pigment of the present invention has a suitable performance not found in conventional yellow pigments as a yellow pigment used in a green color filter with a high color reproducibility standard.

  Currently, typical yellow pigments used in green color filters are C.I. I. Pigment yellow 138 and C.I. I. Although it is CI Pigment Yellow 150, Example 1 using the compound of the present invention has higher brightness and film thickness than those of Comparative Examples using the conventional yellow pigments (corresponding to Comparative Examples 1 and 2 respectively). From the thin point, it is clear that the compound of the present invention is excellent as a yellow pigment for use in a green color filter having a high color reproducibility standard. In addition, C.I. I. In comparison with Pigment Yellow 138 (Comparative Example 1), the film thickness was significantly reduced, and thus the effect of improving the coloring power by dimerization was confirmed.

  Further, Example 1 was found to have a very high luminance as compared with Comparative Example 3, and the introduction of non-conjugated spacers suppressed excessive redness and spectral broadening, and it was found that color development was optimized. Therefore, it is clear that the compound of the present invention is excellent as a yellow pigment used for a high-color reproducibility standard green color filter.

Claims (4)

Following formula (1):

(In the formula _{(1), X} 1 ~X ₁₆ are each independently a hydrogen atom or a halogen atom, Z is a is an alkylene group having 1 to 3 carbon atoms) quinophthalone compound represented by the. The quinophthalone compound according to claim 1, wherein Z is a methylene group. The coloring agent containing the quinophthalone compound of Claim 1 or 2. The coloring composition for color filters containing the coloring agent of Claim 3.