JPWO2020045197A1 - Pigment composition, coloring composition and color filter - Google Patents

Abstract

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。
【化２】

Ｘ^５１〜Ｘ^５４は置換基を有してもよいアルキル基等であり、Ｙ^５１〜Ｙ^５４はハロゲン原子等であり、Ｌ^１は水酸基等であり、ｍ１〜ｍ４及びｎ１〜ｎ４は０〜４の整数である。One aspect of the present invention is a pigment composition containing a quinophthalone compound represented by the formula (1) and at least one aluminum phthalocyanine compound selected from the group consisting of a compound represented by the formula (2A) or the like. is there.
[Chemical 1]

X ^{1 to} X ¹⁶ are independently hydrogen atoms or halogen atoms, Y ¹ and Y ² are independently hydrogen atoms or halogen atoms, and Z is an alkylene group having 1 to 3 carbon atoms.
[Chemical 2]

X ^{51 to} X ⁵⁴ are alkyl groups or the like which may have a substituent, Y ^{51 to} Y ⁵⁴ are halogen atoms or the like, L ¹ is a hydroxyl group or the like, and m1 to m4 and n1 to n4 are 0 to 0. It is an integer of 4.

Description

The present invention relates to pigment compositions, coloring compositions and color filters.

Currently, coloring compositions are used in various fields, and specific applications of coloring compositions include printing inks, paints, colorants for resins, colorants for fibers, and color materials for IT information recording (color filters). , Toner, inkjet) and the like. The dye used in the coloring composition is 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. Pigments, unlike dyes that develop color in the molecular state, develop color in the particle state (aggregates of primary particles). Therefore, in general, pigments are superior to dyes in resistance, but inferior in coloring power and saturation (sharpness).

Against this background, pigments with high coloring power and high saturation are required, and organic pigments, which are considered to be superior in terms of coloring power, are attracting particular attention. For example, in Patent Document 1, a green coloring composition containing a predetermined quinophthalone compound and an aluminum phthalocyanine pigment provides excellent coloring power and dispersibility, as well as high brightness and high contrast ratio when used in a color filter. Is disclosed.

Japanese Unexamined Patent Publication No. 2012-247587

By the way, pigments intended for color filter applications are required to have characteristics different from those for general-purpose applications. Specifically, for example, "high brightness" for reducing the power consumption of the backlight, "high coloring power" for thinning the color filter and reproducing high colors, and the like are required. However, it cannot always be said that the coloring composition disclosed in Patent Document 1 can obtain sufficient brightness and coloring power when it is assumed to be used as a color filter. That is, the coloring composition disclosed in Patent Document 1 has room for further improvement in that the brightness is increased and high color reproducibility can be obtained even with a thin film.

Therefore, an object of the present invention is to provide a pigment composition and a coloring composition having excellent brightness and coloring power, and a color filter using them.

As a result of diligent studies to solve the above problems, the present inventors have found that the brightness and coloring power are improved by combining a compound having a dimerized quinophthalone skeleton and a compound having an aluminum phthalocyanine skeleton. ..

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。

式（２Ａ）中、
Ｘ^５１〜Ｘ^５４は、各々独立に、置換基を有してもよいアルキル基、置換基を有してもよいアリール基、置換基を有してもよいシクロアルキル基、置換基を有してもよい複素環基、置換基を有してもよいアルコキシ基、置換基を有してもよいアリールオキシ基、置換基を有してもよいアルキルチオ基、又は置換基を有してもよいアリールチオ基であり、
Ｙ^５１〜Ｙ^５４は、各々独立に、ハロゲン原子、ニトロ基、置換基を有してもよいフタルイミドメチル基、又は置換基を有してもよいスルファモイル基であり、
Ｌ^１は、水酸基、塩素原子、−ＯＰ（＝Ｏ）Ｒ^１Ｒ^２、又は−Ｏ−ＳｉＲ^３Ｒ^４Ｒ^５であり（Ｒ^１〜Ｒ^５は、各々独立に、水素原子、水酸基、置換基を有してもよいアルキル基、置換基を有してもよいアリール基、置換基を有してもよいアルコキシ基、又は置換基を有してもよいアリールオキシ基であり、Ｒ^１及びＲ^２は互いに結合して環を形成してもよく、Ｒ^３、Ｒ^４及びＲ^５のうち二つは互いに結合して環を形成してもよい）、
ｍ１〜ｍ４及びｎ１〜ｎ４は各々独立に０〜４の整数であり、ｍ１＋ｎ１、ｍ２＋ｎ２、ｍ３＋ｎ３及びｍ４＋ｎ４は、各々独立に０〜４の整数である。

式（２Ｂ）中、
Ｘ^５５〜Ｘ^６２は、各々独立に、置換基を有してもよいアルキル基、置換基を有してもよいアリール基、置換基を有してもよいシクロアルキル基、置換基を有してもよい複素環基、置換基を有してもよいアルコキシ基、置換基を有してもよいアリールオキシ基、置換基を有してもよいアルキルチオ基、又は置換基を有してもよいアリールチオ基であり、
Ｙ^５５〜Ｙ^６２は、各々独立に、ハロゲン原子、ニトロ基、置換基を有してもよいフタルイミドメチル基、又は置換基を有してもよいスルファモイル基であり、
Ｌ^２は、−Ｏ−ＳｉＲ^６Ｒ^７−Ｏ−、−Ｏ−ＳｉＲ^８Ｒ^９−Ｏ−ＳｉＲ^１０Ｒ^１１−Ｏ−、又は−Ｏ−Ｐ（＝Ｏ）Ｒ^１２−Ｏ−であり（Ｒ^６〜Ｒ^１２は、各々独立に、水素原子、水酸基、置換基を有してもよいアルキル基、置換基を有してもよいアリール基、置換基を有してもよいアルコキシ基、又は置換基を有してもよいアリールオキシ基である）、
ｍ５〜ｍ１２及びｎ５〜ｎ１２は各々独立に０〜４の整数であり、ｍ５＋ｎ５、ｍ６＋ｎ６、ｍ７＋ｎ７、ｍ８＋ｎ８、ｍ９＋ｎ９、ｍ１０＋ｎ１０、ｍ１１＋ｎ１１及びｍ１２＋ｎ１２は、各々独立に０〜４の整数である。One aspect of the present invention is at least one selected from the group consisting of a quinophthalone compound represented by the following formula (1), a compound represented by the following formula (2A) and a compound represented by the following formula (2B). It is a pigment composition containing an aluminum phthalocyanine compound.

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

In formula (2A),
Each of X ^{51 to} X ⁵⁴ independently has an alkyl group which may have a substituent, an aryl group which may have a substituent, a cycloalkyl group which may have a substituent, and a substituent. It may have a heterocyclic group, an alkoxy group which may have a substituent, an aryloxy group which may have a substituent, an alkylthio group which may have a substituent, or a substituent. It is an arylthio group and
Y ^{51 to} Y ⁵⁴ are independent halogen atoms, nitro groups, phthalimide methyl groups which may have a substituent, or sulfamoyl groups which may have a substituent.
L ¹ is a hydroxyl group, a chlorine atom, -OP (= O) R ¹ R ² , or -O-Si R ³ R ⁴ R ⁵ (R ^{1 to} R ⁵ are independently hydrogen atoms, hydroxyl groups, and substitutions. an alkyl group which may have a group, an optionally substituted aryl group, an alkoxy group which may have a substituent, or an aryloxy group which may have a substituent, R ¹ and R ² may be bonded to each other to form a ring, and ^two of R ³ , R ⁴ and R ⁵ may be bonded to each other to form a ring).
m1 to m4 and n1 to n4 are independently integers of 0 to 4, and m1 + n1, m2 + n2, m3 + n3 and m4 + n4 are independently integers of 0 to 4, respectively.

In formula (2B),
Each of X ^{55 to} X ⁶² independently has an alkyl group which may have a substituent, an aryl group which may have a substituent, a cycloalkyl group which may have a substituent, and a substituent. It may have a heterocyclic group, an alkoxy group which may have a substituent, an aryloxy group which may have a substituent, an alkylthio group which may have a substituent, or a substituent. It is an arylthio group and
Y ^{55 to} Y ⁶² are independent halogen atoms, nitro groups, phthalimide methyl groups which may have a substituent, or sulfamoyl groups which may have a substituent.
L ² is -O-SiR ⁶ R ⁷ -O-, -O-SiR ⁸ R ^9- O-SiR ¹⁰ R ^11- O-, or -O-P (= O) R ^12- O- ( Each of R ^{6 to} R ¹² independently has a hydrogen atom, a hydroxyl group, an alkyl group which may have a substituent, an aryl group which may have a substituent, an alkoxy group which may have a substituent, or an alkoxy group which may have a substituent. It is an aryloxy group that may have a substituent),
m5 to m12 and n5 to n12 are independently integers of 0 to 4, and m5 + n5, m6 + n6, m7 + n7, m8 + n8, m9 + n9, m10 + n10, m11 + n11 and m12 + n12 are independently integers of 0 to 4, respectively.

Another aspect of the present invention is at least selected from the group consisting of the quinophthalone compound represented by the above formula (1), the compound represented by the above formula (2A) and the compound represented by the above formula (2B). It is a coloring composition containing a kind of aluminum phthalocyanine compound and a solvent.

Another aspect of the present invention is at least selected from the group consisting of the quinophthalone compound represented by the above formula (1), the compound represented by the above formula (2A) and the compound represented by the above formula (2B). It is a color filter having a pixel portion containing a kind of aluminum phthalocyanine compound.

According to the present invention, it is possible to provide a pigment composition and a coloring composition having excellent brightness and coloring power, and a color filter using them.

(Pigment composition)
The pigment composition according to one embodiment contains a quinophthalone compound and an aluminum phthalocyanine compound.

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。The quinophthalone compound is represented by the following formula (1).

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

The quinophthalone compound exhibits selective absorption and permeation due to the dimerization of the quinophthalone skeleton. In addition, the quinophthalone compound dimerizes the quinophthalone skeleton using the linking group Z as a spacer, whereby the conjugation is cleaved and excessive redness is suppressed. Further, in the above quinophthalone compound, the dispersibility is improved by introducing the imide structure. From these facts, according to the above-mentioned quinophthalone compound, a pigment exhibiting excellent brightness and coloring power when combined with an aluminum phthalocyanine compound (pigment) can be obtained. Specifically, for example, the pigment composed of the quinophthalone compound is a pigment composed of the predetermined quinophthalone compound described in Patent Document 1 described above when combined with the pigment composed of the aluminum phthalocyanine compound. It shows better brightness and superior coloring power exceeding this.

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 a methylene group, an ethylene group (1,1-ethanediyl group or 1,2-ethanediyl group), and a propylene group (1,1-). Propanediyl group, 2,2-propanediyl group, 1,2-propanediyl group or 1,3-propanediyl group) is preferable, methylene group, 1,1-ethanediyl group, 1,1-propanediyl group, 2 , 2-Propanediyl group is more preferable, and methylene group is more preferable.

In the quinophthalone compound, it is preferable that at least one of X ^{1 to} X ¹⁶ is a halogen atom, and more preferably two or more are halogen atoms. By introducing a halogen atom into X ^{1 to} X ¹⁶ , the dispersibility of the quinophthalone compound is further improved, and the above-mentioned effect tends to be obtained more remarkably.

Of X ^{1 to} X ⁴ , at least one is preferably a halogen atom, two or more are more preferably halogen atoms, and all may be halogen atoms. Preferably 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.

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

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

Of X ^{13 to} X ¹⁶ , at least one is preferably a halogen atom, two or more are more preferably 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 from each other, but are preferably the same from the viewpoint of facilitating the synthesis of the quinophthalone compound.

式（１−ｉ）及び式（１−ｉｉ）中、Ｘ^１〜Ｘ^１６、Ｙ^１、Ｙ^２及びＺは上述のとおりである。The structure of the formula (1) includes tautomers having the following formulas (1-i) and formula (1-ii), and the quinophthalone compound has any of these structures. You may.

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

Specific examples of the quinophthalone compound are given below, but the quinophthalone compound is not limited thereto.

As the quinophthalone compound, one kind may be used alone, or two or more kinds of compounds may be appropriately selected and used in combination.

The method for producing the quinophthalone compound is not particularly limited, and a conventionally known method can be appropriately used for production. Hereinafter, one aspect of the 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 steps I, II, III and IV.

式（Ａ−１）中、Ｙ^１、Ｙ^２及びＺは上述のとおりである。<Step I>
First, J. According to the method described in Heterocyclic, Chem, 30, 17 (1993) or the like, 2-3 equivalents of crotonaldehyde were added to 1 equivalent of bisanilins, and the mixture was reacted in a strong acid in the presence of an oxidizing agent, and the formula (A-1) was obtained. ) Is synthesized.

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

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 may be 80 ° C. to 100 ° C., preferably 90 ° C. to 100 ° C., and the reaction time may be 1 hour to 6 hours, preferably 3 hours to 6 hours.

式（Ａ−２）中、Ｙ^１、Ｙ^２及びＺは上述のとおりである。<Step II>
Further, the compound of the formula (A-2) can be obtained by reacting the obtained compound of the formula (A-1) with nitric acid or fuming nitric acid in the presence of concentrated sulfuric acid.

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

With respect to Step II, the reaction temperature may be −20 ° C. to 70 ° C., preferably 0 ° C. to 50 ° C., and the reaction time may be 1 hour to 4 hours, preferably 1 hour to 3 hours.

式（Ａ−３）中、Ｙ^１、Ｙ^２及びＺは上述のとおりである。<Step III>
Further, 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 them.

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

With respect to step III, the reaction temperature may be 60 ° C. to 80 ° C., preferably 70 ° C. to 80 ° C., and the reaction time may be 1 hour to 3 hours, preferably 2 hours to 3 hours.

<Process IV>
Further, at least selected from the group consisting of phthalic anhydride and halogen-substituted phthalic anhydride with respect to 1 equivalent of the compound of the formula (A-3) obtained by the method described in JP2013-61622. The compound of formula (1) can be obtained by reacting one kind in the presence of an acid catalyst in an amount of 4 to 6 equivalents. Examples of the acid catalyst include benzoic acid and zinc chloride.

With respect to step IV, the reaction temperature may be 180 ° C. to 250 ° C., preferably 210 ° C. to 250 ° C., and the reaction time may be 1 hour to 8 hours, preferably 3 hours to 8 hours.

The aluminum phthalocyanine compound is at least one selected from the group consisting of a compound represented by the following formula (2A) and a compound represented by the following formula (2B).

In the formula (2A), X ^{51 to} X ⁵⁴ are independently an alkyl group which may have a substituent, an aryl group which may have a substituent, and a cycloalkyl group which may have a substituent. , A heterocyclic group which may have a substituent, an alkoxy group which may have a substituent, an aryloxy group which may have a substituent, an alkylthio group which may have a substituent, or a substituent. It is an arylthio group that may have. Examples of the "substituent" in each of these groups include halogen atoms, amino groups, hydroxyl groups, nitro groups and the like.

Examples of the "alkyl group" of the alkyl group which may have a substituent include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert-butyl group, a neopentyl group and an n-hexyl group. Examples thereof include a linear or branched alkyl group such as an n-octyl group, a stearyl group and a 2-ethylhexyl group. Examples of the "alkyl group having a substituent" include a trichloromethyl group, a trifluoromethyl group, a 2,2,2-trifluoroethyl group, a 2,2-dibromoethyl group and a 2,2,3,3-tetrafluoropropyl group. Group, 2-ethoxyethyl group, 2-butoxyethyl group, 2-nitropropyl group, benzyl group, 4-methylbenzyl group, 4-tert-ptylbenzyl group, 4-methoxybenzyl group, 4-nitrobenzyl group, 2 , 4-Dichlorobenzyl group and the like.

Examples of the "aryl group" of the aryl group which may have a substituent include a phenyl group, a naphthyl group, an anthryl group and the like. Examples of the "aryl group having a substituent" include p-methylphenyl group, p-bromophenyl group, p-nitrophenyl group, p-methoxyphenyl group, 2,4-dichlorophenyl group, pentafluorophenyl group and 2-amino. Phenyl group, 2-methyl-4-chlorophenyl group, 4-hydroxy-1-naphthyl group, 6-methyl-2-naphthyl group, 4,5,8-trichloro-2-naphthyl group, anthraquinonyl group, 2-aminoanthra Examples include a quinonyl group.

Examples of the "cycloalkyl group" of the cycloalkyl group which may have a substituent include a cyclopentyl group, a cyclohexyl group, an adamantyl group and the like. Examples of the "cycloalkyl group having a substituent" include a 2,5-dimethylcyclopentyl group and a 4-tert-butylcyclohexyl group.

Examples of the "heterocyclic group" of the heterocyclic group which may have a substituent include a pyridyl group, a pyrazil group, a piperidino group, a pyranyl group, a morpholino group, an acridinyl group and the like. Examples of the "heterocyclic group having a substituent" include a 3-methylpyridyl group, an N-methylpiperidyl group, an N-methylpyrrrolyl group and the like.

Examples of the "alkoxy group" of the alkoxy group which may have a substituent include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, an n-butoxy group, an isobutoxy group, a tert-butoxy group, a neopentyloxy group, and 2 , 3-Dimethyl-3-pentyloxy group, n-hexyloxy group, n-octyloxy group, stearyloxy group, 2-ethylhexyloxy group and other linear or branched alkoxy groups. Examples of the "alkoxy group having a substituent" include a trichloromethoxy group, a trifluoromethoxy group, a 2,2,2-trifluoroethoxy group, a 2,2,3,3-tetrafluoropropoxy group and a 2,2-ditrifluoro. Examples thereof include a methylpropoxy group, a 2-ethoxyethoxy group, a 2-butoxyethoxy group, a 2-nitropropoxy group, a benzyloxy group and the like.

Examples of the "aryloxy group" of the aryloxy group which may have a substituent include a phenoxy group, a naphthoxy group, an anthryloxy group and the like. Examples of the "aryloxy group having a substituent" include p-methylphenoxy group, p-nitrophenoxy group, p-methoxyphenoxy group, 2,4-dichlorophenoxy group, pentafluorophenoxy group and 2-methyl-4-chloro. Examples include a phenoxy group.

Examples of the "alkylthio group" of the alkylthio group which may have a substituent include a methylthio group, an ethylthio group, a propylthio group, a butylthio group, a pentylthio group, a hexylthio group, an octylthio group, a decylthio group, a dodecylthio group and an octadecylthio group. Can be mentioned. Examples of the "alkylthio group having a substituent" include a methoxyethylthio group, an aminoethylthio group, a benzylaminoethylthio group, a methylcarbonylaminoethylthio group, a phenylcarbonylaminoethylthio group and the like.

Examples of the "arylthio group" of the arylthio group which may have a substituent include a phenylthio group, a 1-naphthylthio group, a 2-naphthylthio group, a 9-anthrylthio group and the like. Examples of the "arylthio group having a substituent" include a chlorophenylthio group, a trifluoromethylphenylthio group, a cyanophenylthio group, a nitrophenylthio group, a 2-aminophenylthio group, a 2-hydroxyphenylthio group and the like.

In formula (2A), Y ^{51 to} Y ⁵⁴ are phthalimide methyl groups (C ₆ H ₄ (CO) ₂ N-CH _2- ), which may independently have a halogen atom, a nitro group, and a substituent, respectively. Alternatively, it is a sulfamoyl group (H ₂ NSO _2- ) which may have a substituent. A phthalimide methyl group having a substituent is a group in which a hydrogen atom in the phthalimide methyl group is substituted with a substituent. A sulfamoyl group having a substituent is a group in which a hydrogen atom in the sulfamoyl group is substituted with a substituent. The "substituent" in each of these groups is the same as the substituents described for X ^51- X ⁵⁴ .

Y ^{51 to} Y ⁵⁴ are preferably halogen atoms. The halogen atom is selected from a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, preferably a chlorine atom or a bromine atom, and more preferably a bromine atom.

In formula (2A), L ¹ is a hydroxyl group, a chlorine atom, -OP (= O) R ¹ R ² , or -O-Si R ³ R ⁴ R ⁵ . Each of R ^{1 to} R ⁵ independently has a hydrogen atom, a hydroxyl group, an alkyl group which may have a substituent, an aryl group which may have a substituent, an alkoxy group which may have a substituent, or an alkoxy group which may have a substituent. It is an aryloxy group that may have a substituent. R ¹ and R ² may be bonded to each other to form a ring, and ^two of R ³ , R ⁴ and R ⁵ may be bonded to each other to form a ring.

Alkyl groups in R ^{1 to} R ⁵ include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, tert-butyl group, neopentyl group, n-hexyl group, n-octyl group and stearyl group. , 2-Ethylhexyl group and other linear or branched alkyl groups. Examples of the alkyl group having a substituent in R ^{1 to} R ⁵ include a trichloromethyl group, a trifluoromethyl group, a 2,2,2-trifluoroethyl group, a 2,2-dibromoethyl group, a 2-ethoxyethyl group, and 2 -Butoxyethyl group, 2-nitropropyl group, benzyl group, 4-methylbenzyl group, 4-tert-butylbenzyl group, 4-methoxybenzyl group, 4-nitrobenzyl group, 2,4-dichlorobenzyl group and the like. Be done.

Examples of the aryl group in R ^{1 to} R ⁵ include a phenyl group, a naphthyl group, an anthryl group and the like. Examples of the aryl group having a substituent in R ^{1 to} R ⁵ include a p-tolyl group, a p-bromophenyl group, a p-nitrophenyl group, a p-methoxyphenyl group, a 2,4-dichlorophenyl group and a pentafluorophenyl group. 2-Dimethylaminophenyl group, 2-methyl-4-chlorophenyl group, 4-methoxy-1-naphthyl group, 6-methyl-2-naphthyl group, 4,5,8-trichloro-2-naphthyl group, anthracinyl group, etc. Can be mentioned.

Alkoxy groups in R ^{1 to} R ⁵ include methoxy group, ethoxy group, propoxy group, isopropoxy group, n-butoxy group, isobutoxy group, tert-butoxy group, neopentyloxy group, 2,3-dimethyl-3-3. Examples thereof include a linear or branched alkoxy group such as a pentyloxy group, an n-hexyloxy group, an n-octyloxy group, a stearyloxy group and a 2-ethylhexyloxy group. Examples of the alkoxy group having a substituent in R ¹ and R ² include a trichloromethoxy group, a trifluoromethoxy group, a 2,2,2-trifluoroethoxy group, a 2,2,3,3-tetrafluoropropoxy group, and the like. Examples thereof include 2,2-ditrifluoromethylpropoxy group, 2-ethoxyethoxy group, 2-butoxyethoxy group, 2-nitropropoxy group and benzyloxy group.

Examples of the aryloxy group in R ^{1 to} R ⁵ include a phenoxy group, a naphthyloxy group, an anthryloxy group and the like. Examples of the aryloxy group having a substituent in R ^{1 to} R ⁵ include p-methylphenoxy group, p-nitrophenoxy group, p-methoxyphenoxy group, 2,4-dichlorophenoxy group, pentafluorophenoxy group and 2-methyl. -4-Chlorophenoxy group and the like can be mentioned.

L ¹ is preferably −OP (= O) R ¹ R ² from the viewpoint of excellent heat resistance and light resistance. In this case, R ¹ and R ² are each independently, preferably an aryl group which may have a substituent or an aryloxy group which may have a substituent, and more preferably an aryl group or an aryloxy group. It is a group, more preferably a phenyl group or a phenoxy group. Both R ¹ and R ² are preferably aryl groups which may have substituents or aryloxy groups which may have substituents, and both R ¹ and R ² are aryl groups or aryloxy groups. It is more preferable that both R ¹ and R ² are phenyl groups or phenoxy groups.

In the formula (2A), m1 to m4 and n1 to n4 are independently integers 0 to 4, and m1 + n1, m2 + n2, m3 + n3 and m4 + n4 are independently integers 0 to 4, respectively. In one embodiment, the total of m1 to m4 may be, for example, 5 or more, 7 or more, or 9 or more, and may be 15 or less, 13 or less, or 11 or less. In another embodiment, all of m1 to m4 may be 0. It is preferable that all of n1 to n4 are 0.

In formula (2B), X ^{55 to} X ⁶² each independently have an alkyl group which may have a substituent, an aryl group which may have a substituent, and a cycloalkyl group which may have a substituent. , A heterocyclic group which may have a substituent, an alkoxy group which may have a substituent, an aryloxy group which may have a substituent, an alkylthio group which may have a substituent, or a substituent. It is an arylthio group that may have. The "substituent" in each of these groups is the same as the substituents described for X ^51- X ⁵⁴ . Specific examples of each of these groups are the same as the specific examples of each group described for X ^{51 to} X ⁵⁴ .

In formula (2B), Y ^{55 to} Y ⁶² are phthalimide methyl groups (C ₆ H ₄ (CO) ₂ N-CH _2- ), which may each independently have a halogen atom, a nitro group, and a substituent. Alternatively, it is a sulfamoyl group (H ₂ NSO _2- ) which may have a substituent. The "substituent" in each of these groups is the same as the substituents described for X ^51- X ⁵⁴ . Specific examples of each of these groups are the same as the specific examples of each group described for Y ^{51 to} Y ⁵⁴ .

In formula (2B), L ² is -O-SiR ⁶ R ⁷ -O-, -O-SiR ⁸ R ^9- O-SiR ¹⁰ R ^11- O-, or -O-P (= O) R ¹² -O-. Each of R ^{6 to} R ¹² independently has a hydrogen atom, a hydroxyl group, an alkyl group which may have a substituent, an aryl group which may have a substituent, an alkoxy group which may have a substituent, or an alkoxy group which may have a substituent. It is an aryloxy group that may have a substituent. The specific examples of each group in R ^{6 to} R ¹² are the same as the specific examples of each group described for R ^{1 to} R ⁵ .

In formula (2B), m5 to m12 and n5 to n12 are independently integers of 0 to 4, and m5 + n5, m6 + n6, m7 + n7, m8 + n8, m9 + n9, m10 + n10, m11 + n11 and m12 + n12 are independently 0 to 4, respectively. It is an integer. In one embodiment, the total of m5 to m12 may be, for example, 9 or more, 14 or more, or 19 or more, and 31 or less, 26 or less, or 21 or less. In another embodiment, all of m5 to m12 may be zero. It is preferable that all of n5 to n12 are 0.

The above quinophthalone compound can exhibit properties as an organic pigment. The quinophthalone compound may be pigmented and blended. Similarly, the above-mentioned aluminum phthalocyanine compound can exhibit properties as an organic pigment and may be pigmented and blended. As an example of such an aluminum phthalocyanine pigment, C.I. I. Pigment Green 63 can be mentioned. That is, the pigment composition according to the present embodiment may contain a pigment composed of the quinophthalocyanine compound (quinophthalocyanine pigment) and a pigment composed of the aluminum phthalocyanine compound (aluminum phthalocyanine pigment).

The pigmentation of each of the quinophthalone compound and the aluminum phthalocyanine compound may be carried out by a known and commonly used method. The quinophthalone pigment and the aluminum phthalocyanine pigment may be finely divided by, for example, salt milling treatment, or may be surface-treated such as rosin treatment, surfactant treatment, solvent treatment, and resin treatment.

The ratio of the contents of the quinophthalocyanine compound (quinophthalocyanine pigment) and the aluminum phthalocyanine compound (aluminum phthalocyanine pigment) in the pigment composition is appropriately determined according to the type of the aluminum phthalocyanine compound and the desired color tone (chromaticity). The content of the quinophthalone compound (quinophthalone pigment) may be, for example, 1 part by mass or more and 95 parts by mass with respect to 100 parts by mass of the total amount of the quinophthalone compound (quinophthalocyanine pigment) and the aluminum phthalocyanine compound (aluminum phthalocyanine pigment). It may be less than 5 parts by mass, preferably 5 parts by mass or more, more preferably 10 parts by mass or more, and preferably 90 parts by mass from the viewpoint that it can be particularly preferably used for green color filter applications having high color reproducibility. Hereinafter, it is more preferably 85 parts by mass or less.

The pigment composition may further contain components other than the above. For example, the pigment composition may further contain an organic pigment, an organic dye, an organic pigment derivative, or the like other than the above.

Examples of organic pigments other than the above include azo pigments, disazo pigments, azomethine pigments, anthraquinone pigments, quinophthalone pigments other than the above quinophthalone pigments, quinacridone pigments, diketopyrrolopyrrole pigments, and dioxazine pigments. , Benz imidazolone pigments, phthalocyanine pigments other than the above aluminum phthalocyanine pigments, isoindolin pigments, isoindolinone pigments, perylene pigments and the like. The organic pigment is preferably an azo pigment, an azomethine pigment, a quinophthalone pigment other than the above quinophthalone pigment, a phthalocyanine pigment other than the above aluminum phthalocyanine pigment, an isoindolin pigment, or the like. C. I. Pigment Yellow 129, 138, 139, 150, 185, 231 and C.I. I. Pigment Green 7, 36, 58, 59, 62, etc.

Examples of organic dyes include xanthene dyes, azo dyes, disazo dyes, anlaquinone dyes, quinophthalone dyes, triarylmethane dyes, methine dyes, phthalocyanine dyes, and rhodamine dyes. The organic dye is preferably a phthalocyanine dye.

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 phthalimide methyl group or the like. Specifically, for example, Solspace (registered trademark name) 5000, 12000, 22000 (manufactured by Ruble Sol 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 with respect to 100 parts by mass of the total amount of the pigment.

The pigment composition may further contain a resin such as a photosensitive resin or a curable resin, a rosin, a surfactant, a dispersant and the like. These components may or may not be treated on the pigment surface (so-called surface treatment). Examples of the method for treating the pigment surface include a method in which these components are once dissolved in a solvent and then precipitated on the pigment surface, a method in which these components are added in a kneader and kneaded together with the pigment, and a method in which these components are treated on the pigment surface in a solvent. It may be a known method such as a method of adsorbing a component.

The pigment composition may be in powder form. By dispersing the pigment composition in a solvent, a coloring composition which is a pigment dispersion can be formed.

(Coloring composition)
The coloring composition according to one embodiment contains the above-mentioned quinophthalone compound, the above-mentioned aluminum phthalocyanine compound, and a solvent.

The aspects of the quinophthalone compound and the aluminum phthalocyanine compound in the coloring composition and their ratios may be the same as the aspects of the quinophthalone compound and the aluminum phthalocyanine compound in the pigment composition described above and their ratios, respectively.

The solvent is preferably an organic solvent. 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 Examples include carbamate esters such as a 48:52 mixture of ethyls. The organic solvent is preferably a polar solvent that is soluble in water, and more preferably a propionate solvent, an alcohol solvent, an ether solvent, a ketone solvent, a nitrogen compound solvent, or a lactone solvent. is there.

The content of the solvent is 300 parts by mass or more with respect to 100 parts by mass of the total amount of the above-mentioned quinophthalone compound (quinophthalocyanine pigment) and aluminum phthalocyanine compound (aluminum phthalocyanine pigment) (hereinafter referred to as "total amount of pigments"). It may be 2000 parts by mass or less.

The coloring composition may further contain a dispersant and / or an organic pigment derivative from the viewpoint of preferably dispersing the quinophthalone pigment and the aluminum phthalocyanine pigment in the solvent.

Examples of the dispersant include ANTI-TERRA (registered trademark name) U / U100, 204, DISPERBYK (registered trademark name) 106, 108, 109, 112, 130, 140, 142, 145, and so on. 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 (manufactured by Big Chemie Co., Ltd.) , EFKA (registered trademark) 46, 47, 4010, 4020, 4320, 4300, 4330, 4401, 4570, 5054, 7461, 7462, 7476, 7477 (BASF shares). (Manufactured by the company), Azisper (registered trademark) PB814, 821, 822, 881 (manufactured by Ajinomoto Fine Techno Co., Ltd.), Solspace (registered trademark) 24000, 28000, 37500, 76500 (Lubrisol Co., Ltd.) (Made) and so on. The content of the dispersant may be 10 parts by mass or more and 120 parts by mass or less with respect to 100 parts by mass of the total amount of the pigment.

The coloring composition may further contain a photosensitive resin. The coloring composition containing a photosensitive resin can also be referred to as a photosensitive coloring composition. Examples of the photosensitive resin include thermoplastic resins such as urethane resin, acrylic resin, polyamic acid resin, polyimide resin, styrene maleic acid resin, and styrene anhydride maleic acid 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, etc., trimethyl propantriacrylate, Examples thereof include photopolymerizable monomers such as polyfunctional monomers such as pentaerythritol triacrylate, tris- (2-acryloyloxyethyl) isocyanurate, dipentaerythritol hexaacrylate, and dipentaerythritol pentaacrylate.

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 can be mentioned.

When the coloring composition contains a photosensitive resin (further, a photopolymerization initiator), the coloring composition can be obtained, for example, by the following method. First, a quinophthalone pigment and an aluminum phthalocyanine pigment are dispersed in a solvent together with a dispersant and / or an organic pigment derivative, if necessary, to obtain a dispersion liquid. Next, a photosensitive resin (further, a photopolymerization initiator) is added to this dispersion, a solvent is further added if necessary, and the mixture is uniformly stirred to obtain a colored composition.

In this case, the content of the photosensitive resin may be 3 parts by mass or more and 25 parts by mass or less with respect to 100 parts by mass of the above dispersion liquid. The content of the photopolymerization initiator may be 0.05 parts by mass or more and 3 parts by mass or less with respect to 1 part by mass of the photosensitive resin.

By using the pigment composition or coloring composition described above, a green color filter (green pixel portion of the color filter) having high brightness and high color reproducibility even with a thin film can be obtained. The present inventors infer the reason as follows.

In order to obtain a green color filter having high color reproducibility, the yellow pigment preferably absorbs light in a wider wavelength range in a blue region where light is not absorbed (transmitted) by the blue pigment or the green pigment used in combination. Conventionally, the amount of absorption by the yellow pigment in the blue region has been increased by increasing the content of the yellow pigment. However, in this case, there have been problems such as a decrease in brightness and an increase in film thickness.
On the other hand, since the compound represented by the formula (1) has a structure in which the quinophthalone skeleton is dimerized, the above quinophthalone pigment spreads to a longer wavelength side in the blue region as compared with the conventional yellow pigment. It has an absorption spectrum. Therefore, the color can be adjusted to a high degree of greenness for color reproduction without increasing the content of the quinophthalone pigment. Therefore, with this green color filter, high brightness can be achieved while achieving high color reproducibility even with a thin film.

Therefore, the coloring composition is suitable as a coloring composition for a color filter (used for forming a color filter), and particularly suitable as a coloring composition used for forming a green color filter (green pixel portion of a color filter). is there.

(Color filter)
One embodiment of the present invention is a color filter having a pixel portion formed from the above coloring composition. In other words, the color filter according to the embodiment has a pixel portion containing the above-mentioned quinophthalone compound and the above-mentioned aluminum phthalocyanine compound. The pixel portion is preferably a green pixel portion.

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

The method for forming the pixel portion is not particularly limited, and for example, a color filter may be manufactured by forming a pattern of the pixel portion by a method such as an electrodeposition method, a transfer method, a micelle electrolysis method, or a PVED (photovoltaic electrolysis) method. ..

In the above embodiment (pigment composition and coloring composition), the above quinophthalone compound and the aluminum phthalocyanine compound are contained in one composition, but in another embodiment, the above quinophthalone compound and the aluminum phthalocyanine compound are contained. May be included in separate compositions. That is, in another embodiment of the present invention, a first pigment composition (coloring composition) containing the above quinophthalone compound and a second pigment composition (coloring composition) containing the above aluminum phthalocyanine compound. ), And a pigment composition set (coloring composition set). This pigment composition set (coloring composition set) is also suitably used for forming a color filter, and is particularly preferably used for forming a green color filter (green pixel portion of the color filter).

Hereinafter, the present invention will be described in more detail based on Examples, but the present invention is not limited to the following Examples.

^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]
To a flask, 5.0 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. The mixture was 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., 15.3 g (112 mmol) of zinc chloride was added little by little, 200 ml of THF was added, and the mixture was stirred for 1 hour while maintaining 80 ° C. After allowing to cool to room temperature, the 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, the insoluble material was removed by filtration, and then recrystallized to obtain 12.6 g of the intermediate (4) (yield: 61%).

^{1 1} H-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)
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, 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^−１：３４６５，１６０４，１５３０，１４８７，１３６２Subsequently, 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. Then, 1.62 mL of fuming nitric acid was added dropwise, the temperature was maintained, and stirring was continued for 1 hour. After allowing to cool, 250 mL of ice water was slowly poured into the system. Further, the pH was adjusted to 8 to 9 using a 10 wt% sodium hydroxide aqueous solution. The precipitated powder was collected by vacuum filtration 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 1} H-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)
¹³ C-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

^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^−１：３４７６，３３７３，１６２７，１６０５，１４０９，１３５９，１２５０Subsequently, 5.00 g (10.9 mmol) of Intermediate (5) and 23.3 mL of ethanol were added to the flask, and the mixture was stirred at room temperature for 10 minutes. Then, 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 allowing to cool, the pH was adjusted to 9 by pouring into 150 mL of distilled water and using a 10% aqueous sodium hydroxide solution. The precipitated powder was collected by vacuum filtration. Further, the recovered powder was sufficiently stirred in 700 mL of ethyl acetate and filtered under reduced pressure. By distilling off the solvent of the obtained filtrate under reduced pressure, 3.64 g (9.16 mmol) of the intermediate (6), which is an ocher powder, was obtained (yield: 84%).

^{1 1} H-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)
¹³ C-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

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

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

^１Ｈ−ＮＭＲ（ＤＭＳＯ−ｄ６）δｐｐｍ：２．７０（ｓ，６Ｈ），４．４２（ｓ，２Ｈ），７．５８（ｄ，Ｊ＝８．８Ｈｚ，２Ｈ），７．６３（ｄ，Ｊ＝８．８Ｈｚ，２Ｈ），８．０９（ｄ，Ｊ＝８．８Ｈｚ，２Ｈ），８．１３（ｄ，Ｊ＝８．８Ｈｚ，２Ｈ）
^１３Ｃ−ＮＭＲ（ＤＭＳＯ−ｄ６）δｐｐｍ：２４．５，３２．０，１１７．７，１２４．８，１２７．５，１２９．８，１３０．５，１３１．９，１４５．８，１４６．２，１６０．７
ＦＴ−ＩＲ（ＫＢｒ ｄｉｓｋ）ｃｍ^−１：３０４８，１６０２，１５２０，１４９４，１３６３[Synthesis Example 2]
Put 55 g of concentrated sulfuric acid in a flask and stir under ice-cooling to obtain 7.0 g of 6,6'-methylenediquinaldin obtained by the method described in the literature (Polymer, volume39, No.20 (1998), p4949). 23.5 mmol) was added. 6.1 g of 60% nitric acid was added dropwise while maintaining 10 ° C. or lower, and stirring was continued at 10 ° C. to 20 ° C. for 1 hour. The reaction solution was poured into 150 ml of ice water, and the pH was adjusted to 3 with a 20 wt% sodium hydroxide aqueous solution. The precipitated powder was collected by vacuum filtration and washed with water to neutrality. The obtained solid was air-dried at 70 ° C., and then the crude product was washed and filtered with 100 ml of hot ethyl acetate and then 60 ml of hot toluene to obtain 6.52 g (16.8 mmol) of the intermediate (8) (yield). : 72%).

^{1 1} H-NMR (DMSO-d6) δppm: 2.70 (s, 6H), 4.42 (s, 2H), 7.58 (d, J = 8.8Hz, 2H), 7.63 (d, J = 8.8Hz, 2H), 8.09 (d, J = 8.8Hz, 2H), 8.13 (d, J = 8.8Hz, 2H)
¹³ C-NMR (DMSO-d6) δppm: 24.5, 32.0, 117.7, 124.8, 127.5, 129.8, 130.5, 131.9, 145.8, 146.2 , 160.7
FT-IR (KBr disk) cm ^-1 : 3048, 1602, 1520, 1494, 1363

^１Ｈ−ＮＭＲ（ＤＭＳＯ−ｄ６）δｐｐｍ：２．５７（ｓ，６Ｈ），３．４５（ｓ，２Ｈ），５．６６（ｓ，４Ｈ），７．０６（ｄ，Ｊ＝８．２Ｈｚ，２Ｈ），７．１６（ｄ，Ｊ＝８．２Ｈｚ，２Ｈ），７．２３（ｄ，Ｊ＝８．２Ｈｚ，２Ｈ），８．４９（ｄ，Ｊ＝８．２Ｈｚ，２Ｈ）
^１３Ｃ−ＮＭＲ（ＤＭＳＯ−ｄ６）δｐｐｍ：２４．６，３２．１，１１５．８，１１６．２，１１９．５，１３０．９，１３１．８，１４１．５，１４７．４，１５７．０
ＦＴ−ＩＲ（ＫＢｒ ｄｉｓｋ）ｃｍ^−１：３４６４，３３６３，３３１５，３１９２，１６４０，１５９１，１５７３，１４１５，１３６５，８０１Subsequently, 5.30 g of reduced iron and 135 ml of acetic acid were charged in the flask and heated to 50 ° C. with stirring. Next, 4.50 g (11.6 mmol) of the intermediate (8) was added so as to keep the temperature below 70 ° C. After completion of the addition, stirring was continued at 60 ° C. for 1 hr, the reaction solution was cooled to 35 ° C. or lower, poured into 500 ml of ice water, and adjusted to pH 9 with 20% NaOH water. The resulting precipitate was filtered under reduced pressure over Celite. The solid was collected, air-dried at 70 ° C., added to a mixed solvent of 100 ml of dimethyl sulfoxide (DMSO) and 100 ml of N, N-dimethylformamide (DMF), and stirred at 90 ° C. for 1 hr. The mixture was filtered under reduced pressure over Celite and the resulting filtrate was added to 1 L of water with stirring. The produced precipitate was collected by vacuum filtration and washed with water to obtain 3.80 g (11.6 mmol) of the intermediate (9) (yield:> 99%).

^{1 1} H-NMR (DMSO-d6) δppm: 2.57 (s, 6H), 3.45 (s, 2H), 5.66 (s, 4H), 7.06 (d, J = 8.2Hz, 2H), 7.16 (d, J = 8.2Hz, 2H), 7.23 (d, J = 8.2Hz, 2H), 8.49 (d, J = 8.2Hz, 2H)
¹³ C-NMR (DMSO-d6) δppm: 24.6, 32.1, 115.8, 116.2, 119.5, 130.9, 131.8, 141.5, 147.4, 157.0
FT-IR (KBr disk) cm ^-1 : 3464, 3363, 3315, 3192, 1640, 1591, 1573, 1415, 1365, 801

ＦＴ−ＩＲ ｃｍ^−１：１７８８，１７２９，１６８８，１６３８，１６０７，１５３７，１４２０，１３１０，７３２
ＦＤ−ＭＳ：１４００Ｍ＋Subsequently, 135 g of benzoic acid was weighed in a flask under a nitrogen atmosphere and melted at 140 ° C. To this, 3.80 g (11.6 mmol) of the intermediate (9), 17.99 g (62.9 mmol) of tetrachlorphthalic anhydride, and 0.49 g (3.6 mmol) of anhydrous zinc chloride were added, and the mixture was added at 220 ° C. The mixture was stirred for 6 hours. After cooling the reaction mixture to 120 ° C., 300 mL of chlorobenzene was added and the mixture was stirred for 1 hour, and 10.5 g (7.5 mmol) of the target product (10) as a yellow powder was obtained by vacuum filtration (yield: 65%). ..

FT-IR cm- ¹ : 1788, 1729, 1688, 1638, 1607, 1537, 1420, 1310, 732
FD-MS: 1400M +

[Synthesis Example 3]
130 mL of concentrated sulfuric acid was placed in a flask and cooled to 10 ° C. or lower with stirring. 8.00 g (14.4 mmol) of hydroxyaluminum phthalocyanine obtained according to the method described in JP2012-247587 was added so as to keep the temperature at 10 ° C. or lower. Subsequently, 21.4 g (74.7 mmol) of dibromoisocyanuric acid was added so as to keep the temperature below 10 ° C. Then, the mixture was stirred at room temperature for 7 hours. The reaction solution was poured into water, and the precipitated solid was recovered by vacuum filtration. The obtained solid was dispersed in a 2.5% aqueous sodium hydroxide solution and stirred at 70 ° C. for 1 hour. The solid was recovered by vacuum filtration and dried at 90 ° C. for 17 hours to obtain 9.20 g of the intermediate (11) (yield: 47%). The average number of bromine substituents was 10.0 and the halogen distribution width was 9 (calculated from the results of FD-MS).

Subsequently, 6.00 g of the intermediate (11), 2.20 g (8.7 mmol) of diphenyl phosphate, and 85 mL of N-methyl-2-pyrrolidone were placed in a flask, and the mixture was stirred at 90 ° C. for 6 hours. The reaction solution was poured into methanol, and the precipitated solid was recovered by vacuum filtration. The obtained solid was dispersed in water / methanol = 1/1 and stirred at room temperature for 2 hours. The solid was recovered by vacuum filtration and dried at 90 ° C. for 17 hours to obtain 4.60 g of the target product (12) (yield: 65%). The average number of bromine substituents was 10.0 and the halogen distribution width was 9 (calculated from the results of FD-MS).

^１Ｈ−ＮＭＲ（ＣＤＣｌ_３）δｐｐｍ：７．４８−７．５５（１Ｈ），７．６１（１Ｈ），７．７４（１Ｈ），７．８１−７．９５（７Ｈ），８．１２（１Ｈ），８．１９−８．２３（３Ｈ），８．６６（２Ｈ），８．８１（１Ｈ），１４．９（１Ｈ）
ＦＤ−ＭＳ：５１９Ｍ＋[Synthesis Example 4]
In a nitrogen atmosphere, 24.4 g (200 mmol) of benzoic acid was weighed in a flask and melted at 130 ° C. To this, 1.59 g (10.0 mmol) of 8-aminoquinaldine and 1.98 g (10.0 mmol) of 2,3-naphthalenedicarboxylic acid anhydride were added, and the mixture was stirred at 180 ° C. for 3 hours. Then, 3.31 g of 2,3-naphthalenedicarboxylic acid anhydride and 1.36 g of zinc chloride were added, the temperature was raised to 230 ° C., and the mixture was further stirred for 4 hours. After allowing to cool, 700 mL of acetone was added to the reaction solution, and the mixture was stirred for 1 hour, and then the yellow powder was recovered by vacuum filtration. Subsequently, the obtained powder was washed with 300 mL of methanol, and 5.00 g (9.64 mmol) of the yellow powder intermediate (13) was obtained by vacuum filtration (yield: 96%).

^{1 1} H-NMR (CDCl ₃ ) δppm: 7.48-7.55 (1H), 7.61 (1H), 7.74 (1H), 7.81-7.95 (7H), 8.12 ( 1H), 8.19-8.23 (3H), 8.66 (2H), 8.81 (1H), 14.9 (1H)
FD-MS: 519M +

ＦＤ−ＭＳ：３３８Ｍ＋Subsequently, 1.03 g (1.99 mmol) of the intermediate (13) and 39 mL of ethanol were placed in a flask, and the mixture was stirred at room temperature for 3 minutes. Then, 1.03 g (39.7 mmol) of hydrazine monohydrate was added to the system, and the mixture was stirred while heating under reflux for 23 hours. After allowing to cool, the powder was recovered by vacuum filtration, and the filtrate was washed with 250 mL of acetone. Further, the mixture was stirred for 1 hour while heating under reflux in 50 mL of a 10% aqueous sodium hydroxide solution. Then, hot filtration was carried out at the stage where the temperature was lowered to around 40-50 ° C. to obtain 0.633 g (1.87 mmol) of the yellow powder intermediate (14) (yield: 94%).

FD-MS: 338M +

Subsequently, 4.13 g (12.2 mmol) of the intermediate (14), 3.80 g (13.3 mmol) of tetrachlorophthalic anhydride, and 37.4 mL of trichlorobenzene were added to the flask, and the mixture was heated and stirred at 200 ° C. for 5 hours. did. After allowing to cool, the mixture was washed with 300 mL of acetone and filtered under reduced pressure to obtain 5.92 g (9.76 mmol) of the target product (15) as a yellow powder (yield: 80%).
FD-MS: 604M +

[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 dual-arm kneader and kneaded at 80 ° C. for 8 hours. After kneading, the mixture was taken out to 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 which is a yellow pigment. The quinophthalone pigment obtained by the transmission electron microscope JEM-2010 manufactured by JEOL Ltd. was photographed. The average aspect ratio is calculated from the average value of the longer diameter (major diameter) and the shorter diameter (minor diameter) of the 40 primary particles that make up the aggregate on the secondary image, and the average value of the major diameter is the average primary particle. The diameter was set. The average aspect ratio was less than 3.00. The average primary particle size was 100 nm or less.

[Pigmentation Example 2]
Pigmentation was carried out in the same manner as in Pigmentation Example 1 except that the quinophthalone dimer (10) obtained in Synthesis Example 2 was used instead of the quinophthalone dimer (7) obtained in Synthesis Example 1. , A quinophthalone pigment was obtained. The average aspect ratio of the obtained pigment particles was less than 3.00, and the average primary particle diameter was 100 nm or less.

[Pigmentation Example 3]
Pigmentation was carried out in the same manner as in Pigmentation Example 1 except that the quinophthalone monomer (15) obtained in Synthesis Example 4 was used instead of the quinophthalone dimer (7) obtained in Synthesis Example 1. This was performed to obtain a quinophthalone pigment. The average aspect ratio of the obtained pigment particles was less than 3.00, and the average primary particle diameter was 100 nm or less.

[Manufacturing Example 1]
C.I., in which 0.660 parts by mass of the quinophthalone pigment obtained in Pigmenting Example 1 was placed in a glass bottle, and synthesized by the method described in JP2013-54200A. I. Pigment Yellow 138 sulfonic acid derivative (16) 0.040 parts by mass, propylene glycol monomethyl ether acetate 12.60 parts by mass, BYK LPN-21116 (manufactured by Big Chemie Co., Ltd.) 1.400 parts by mass, 0.3 to 0.4 mmφ 22.0 parts by mass of Sepul beads were added and dispersed with a paint shaker (manufactured by Toyo Seiki Co., Ltd.) for two and a half hours to obtain a pigment dispersion.

Further, 4.00 parts by mass of the obtained pigment dispersion, 0.600 parts by mass of 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 placed in a glass bottle. The composition for yellow toning was prepared by putting it in and shaking it.

[Manufacturing Example 2]
A composition for yellow toning was obtained in the same manner as in Production Example 1 except that the quinophthalone pigment obtained in Pigmentization Example 2 was used instead of the quinophthalone pigment obtained in Pigmentization Example 1.

[Manufacturing Example 3]
A composition for blue toning containing an aluminum phthalocyanine pigment containing an unsubstituted aluminum phthalocyanine (17) was prepared according to the method described in JP2013-87251.

[Manufacturing Example 4]
The method described in JP2013-87251 is the same as in Production Example 3, except that the brominated aluminum phthalocyanine (12) obtained in Synthesis Example 3 was used instead of the unsubstituted aluminum phthalocyanine (17). The composition for green toning was obtained accordingly.

[Manufacturing Example 5]
0.700 parts by mass of the quinophthalone pigment obtained in Pigmenting Example 3 was placed in a glass bottle, and 6.42 parts by mass of propylene glycol monomethyl ether acetate, 0.467 parts by mass of BYK LPN-6919 (manufactured by DIC Corporation), an acrylic resin solution. Add 0.700 parts by mass of Unidic (registered trademark) ZL-295 (manufactured by DIC Corporation) and 22.0 parts by mass of 0.3-0.4 mmφ seple beads, and use a paint shaker (manufactured by Toyo Seiki Co., Ltd.) for 2.5 hours It was dispersed to obtain a pigment dispersion. Further, 2.00 parts by mass of the obtained pigment dispersion, 0.490 parts by mass of ZL-295, and 0.110 parts by mass of propylene glycol monomethyl ether acetate are placed in a glass bottle and shaken to obtain a composition for yellow toning. Made.

[Example 1]
The yellow toning composition obtained in Production Example 1 and the blue toning composition obtained in Production Example 3 are mixed so that the quinophthalone pigment: aluminum phthalocyanine pigment (mass ratio) = 49:51. To obtain a coloring composition.

[Example 2]
A coloring composition was obtained in the same manner as in Example 1 except that the yellow toning composition obtained in Production Example 2 was used instead of the yellow toning composition obtained in Production Example 1. ..

[Comparative Example 1]
Instead of the yellow toning composition obtained in Production Example 1, the yellow toning composition obtained in Production Example 5 was used so that the quinophthalone pigment: aluminum phthalocyanine pigment (mass ratio) = 63: 37. A coloring composition was obtained in the same manner as in Example 1 except that the composition for yellow toning and the composition for blue toning were mixed.

<Evaluation of color filter characteristics>
Each of the obtained coloring compositions is applied onto a glass substrate by a spin coater, dried, and heated at 230 ° C. for 1 hour to prepare an evaluation sample showing a predetermined green chromaticity when a C light source is used. did. As the green chromaticity, the green chromaticity (0.260, 0.650) in the high color reproduction color standard used in Japanese Patent Application Laid-Open No. 2010-2550 was used. The chromaticity is a value measured by a spectrophotometer (U3900 / 3900H type manufactured by Hitachi High-Tech Science Corporation). The brightness Y of the obtained evaluation sample was measured by a spectrophotometer (U3900 / 3900H type manufactured by Hitachi High-Tech Science Corporation). Further, with respect to 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. The results are shown in Table 1.

Examples 1 and 2 using a combination of the quinophthalone compound represented by the formula (1) (quinophthalone dimer (7) or (10)) and the aluminum phthalocyanine compound (unsubstituted aluminum phthalocyanine (17)) are represented by the formulas 1. Compared with Comparative Example 1 in which a conventional quinophthalone compound (quinophthalone monomer (15)) was used instead of the quinophthalone compound represented by (1), the brightness and coloring power (high color reproduction greenness with a thin film thickness) Can be toned).

[Example 3]
Instead of the blue toning composition obtained in Production Example 3, the green toning composition obtained in Production Example 4 was used so that the quinophthalone pigment: aluminum phthalocyanine pigment (mass ratio) = 27: 73. A coloring composition was obtained in the same manner as in Example 1 except that the composition for yellow toning and the composition for blue toning were mixed.

[Example 4]
A coloring composition was obtained in the same manner as in Example 3 except that the yellow toning composition obtained in Production Example 2 was used instead of the yellow toning composition obtained in Production Example 1. ..

[Comparative Example 2]
Instead of the yellow toning composition obtained in Production Example 1, the yellow toning composition obtained in Production Example 5 was used so that the quinophthalone pigment: aluminum phthalocyanine pigment (mass ratio) = 39:61. A coloring composition was obtained in the same manner as in Example 3 except that the composition for yellow toning and the composition for blue toning were mixed.

<Evaluation of color filter characteristics>
The color filter characteristics of each of the obtained coloring compositions were evaluated in the same manner as in Examples 1 and 2 and Comparative Example 1. The results are shown in Table 2.

Examples 3 and 4 using a combination of the quinophthalone compound represented by the formula (1) (quinophthalone dimer (7) or (10)) and the aluminum phthalocyanine compound (brominated aluminum phthalocyanine (12)) are represented by the formulas. Compared with Comparative Example 2 in which a conventional quinophthalone compound (quinophthalone monomer (15)) is used instead of the quinophthalone compound represented by (1), the brightness and coloring power are high (high color reproduction with a thin film thickness). It can be adjusted to greenness).

Claims (3)

The quinophthalone compound represented by the following formula (1) and
A pigment composition containing at least one aluminum phthalocyanine compound selected from the group consisting of a compound represented by the following formula (2A) and a compound represented by the following formula (2B).

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

[In formula (2A),
Each of X ^{51 to} X ⁵⁴ independently has an alkyl group which may have a substituent, an aryl group which may have a substituent, a cycloalkyl group which may have a substituent, and a substituent. It may have a heterocyclic group, an alkoxy group which may have a substituent, an aryloxy group which may have a substituent, an alkylthio group which may have a substituent, or a substituent. It is an arylthio group and
Y ^{51 to} Y ⁵⁴ are independent halogen atoms, nitro groups, phthalimide methyl groups which may have a substituent, or sulfamoyl groups which may have a substituent.
L ¹ is a hydroxyl group, a chlorine atom, -OP (= O) R ¹ R ² , or -O-Si R ³ R ⁴ R ⁵ (R ^{1 to} R ⁵ are independently hydrogen atoms, hydroxyl groups, and substitutions. an alkyl group which may have a group, an optionally substituted aryl group, an alkoxy group which may have a substituent, or an aryloxy group which may have a substituent, R ¹ and R ² may be bonded to each other to form a ring, and ^two of R ³ , R ⁴ and R ⁵ may be bonded to each other to form a ring).
m1 to m4 and n1 to n4 are independently integers of 0 to 4, and m1 + n1, m2 + n2, m3 + n3 and m4 + n4 are independently integers of 0 to 4, respectively. ]

[In formula (2B),
Each of X ^{55 to} X ⁶² independently has an alkyl group which may have a substituent, an aryl group which may have a substituent, a cycloalkyl group which may have a substituent, and a substituent. It may have a heterocyclic group, an alkoxy group which may have a substituent, an aryloxy group which may have a substituent, an alkylthio group which may have a substituent, or a substituent. It is an arylthio group and
Y ^{55 to} Y ⁶² are independent halogen atoms, nitro groups, phthalimide methyl groups which may have a substituent, or sulfamoyl groups which may have a substituent.
L ² is -O-SiR ⁶ R ⁷ -O-, -O-SiR ⁸ R ^9- O-SiR ¹⁰ R ^11- O-, or -O-P (= O) R ^12- O- ( Each of R ^{6 to} R ¹² independently has a hydrogen atom, a hydroxyl group, an alkyl group which may have a substituent, an aryl group which may have a substituent, an alkoxy group which may have a substituent, or an alkoxy group which may have a substituent. It is an aryloxy group that may have a substituent),
m5 to m12 and n5 to n12 are independently integers of 0 to 4, and m5 + n5, m6 + n6, m7 + n7, m8 + n8, m9 + n9, m10 + n10, m11 + n11 and m12 + n12 are independently integers of 0 to 4, respectively. ] The quinophthalone compound represented by the following formula (1) and
At least one aluminum phthalocyanine compound selected from the group consisting of the compound represented by the following formula (2A) and the compound represented by the following formula (2B), and
A coloring composition containing a solvent.

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

[In formula (2A),
Each of X ^{51 to} X ⁵⁴ independently has an alkyl group which may have a substituent, an aryl group which may have a substituent, a cycloalkyl group which may have a substituent, and a substituent. It may have a heterocyclic group, an alkoxy group which may have a substituent, an aryloxy group which may have a substituent, an alkylthio group which may have a substituent, or a substituent. It is an arylthio group and
Y ^{51 to} Y ⁵⁴ are independent halogen atoms, nitro groups, phthalimide methyl groups which may have a substituent, or sulfamoyl groups which may have a substituent.
L ¹ is a hydroxyl group, a chlorine atom, -OP (= O) R ¹ R ² , or -O-Si R ³ R ⁴ R ⁵ (R ^{1 to} R ⁵ are independently hydrogen atoms, hydroxyl groups, and substitutions. an alkyl group which may have a group, an optionally substituted aryl group, an alkoxy group which may have a substituent, or an aryloxy group which may have a substituent, R ¹ and R ² may be bonded to each other to form a ring, and ^two of R ³ , R ⁴ and R ⁵ may be bonded to each other to form a ring).
m1 to m4 and n1 to n4 are independently integers of 0 to 4, and m1 + n1, m2 + n2, m3 + n3 and m4 + n4 are independently integers of 0 to 4, respectively. ]

[In formula (2B),
Each of X ^{55 to} X ⁶² independently has an alkyl group which may have a substituent, an aryl group which may have a substituent, a cycloalkyl group which may have a substituent, and a substituent. It may have a heterocyclic group, an alkoxy group which may have a substituent, an aryloxy group which may have a substituent, an alkylthio group which may have a substituent, or a substituent. It is an arylthio group and
Y ^{55 to} Y ⁶² are independent halogen atoms, nitro groups, phthalimide methyl groups which may have a substituent, or sulfamoyl groups which may have a substituent.
L ² is -O-SiR ⁶ R ⁷ -O-, -O-SiR ⁸ R ^9- O-SiR ¹⁰ R ^11- O-, or -O-P (= O) R ^12- O- ( Each of R ^{6 to} R ¹² independently has a hydrogen atom, a hydroxyl group, an alkyl group which may have a substituent, an aryl group which may have a substituent, an alkoxy group which may have a substituent, or an alkoxy group which may have a substituent. It is an aryloxy group that may have a substituent),
m5 to m12 and n5 to n12 are independently integers of 0 to 4, and m5 + n5, m6 + n6, m7 + n7, m8 + n8, m9 + n9, m10 + n10, m11 + n11 and m12 + n12 are independently integers of 0 to 4, respectively. ] The quinophthalone compound represented by the following formula (1) and
A color filter having a pixel portion containing at least one aluminum phthalocyanine compound selected from the group consisting of a compound represented by the following formula (2A) and a compound represented by the following formula (2B).

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

[In formula (2A),
Each of X ^{51 to} X ⁵⁴ independently has an alkyl group which may have a substituent, an aryl group which may have a substituent, a cycloalkyl group which may have a substituent, and a substituent. It may have a heterocyclic group, an alkoxy group which may have a substituent, an aryloxy group which may have a substituent, an alkylthio group which may have a substituent, or a substituent. It is an arylthio group and
Y ^{51 to} Y ⁵⁴ are independent halogen atoms, nitro groups, phthalimide methyl groups which may have a substituent, or sulfamoyl groups which may have a substituent.
L ¹ is a hydroxyl group, a chlorine atom, -OP (= O) R ¹ R ² , or -O-Si R ³ R ⁴ R ⁵ (R ^{1 to} R ⁵ are independently hydrogen atoms, hydroxyl groups, and substitutions. an alkyl group which may have a group, an optionally substituted aryl group, an alkoxy group which may have a substituent, or an aryloxy group which may have a substituent, R ¹ and R ² may be bonded to each other to form a ring, and ^two of R ³ , R ⁴ and R ⁵ may be bonded to each other to form a ring).
m1 to m4 and n1 to n4 are independently integers of 0 to 4, and m1 + n1, m2 + n2, m3 + n3 and m4 + n4 are independently integers of 0 to 4, respectively. ]

[In formula (2B),
Each of X ^{55 to} X ⁶² independently has an alkyl group which may have a substituent, an aryl group which may have a substituent, a cycloalkyl group which may have a substituent, and a substituent. It may have a heterocyclic group, an alkoxy group which may have a substituent, an aryloxy group which may have a substituent, an alkylthio group which may have a substituent, or a substituent. It is an arylthio group and
Y ^{55 to} Y ⁶² are independent halogen atoms, nitro groups, phthalimide methyl groups which may have a substituent, or sulfamoyl groups which may have a substituent.
L ² is -O-SiR ⁶ R ⁷ -O-, -O-SiR ⁸ R ^9- O-SiR ¹⁰ R ^11- O-, or -O-P (= O) R ^12- O- ( Each of R ^{6 to} R ¹² independently has a hydrogen atom, a hydroxyl group, an alkyl group which may have a substituent, an aryl group which may have a substituent, an alkoxy group which may have a substituent, or an alkoxy group which may have a substituent. It is an aryloxy group that may have a substituent),
m5 to m12 and n5 to n12 are independently integers of 0 to 4, and m5 + n5, m6 + n6, m7 + n7, m8 + n8, m9 + n9, m10 + n10, m11 + n11 and m12 + n12 are independently integers of 0 to 4, respectively. ]