CN114729200A

CN114729200A - Quinophthalone compound, pigment composition and color filter

Info

Publication number: CN114729200A
Application number: CN202080079935.7A
Authority: CN
Inventors: 日高悠太; 近藤仁; 山崎龙史; 清水郁马; 冈部英树
Original assignee: DIC Corp
Current assignee: DIC Corp
Priority date: 2019-12-13
Filing date: 2020-11-12
Publication date: 2022-07-08
Also published as: WO2021117410A1; KR20220113687A; JPWO2021117410A1; TW202122383A; JP6992931B2

Abstract

The present invention addresses the problem of providing a quinophthalone compound which exhibits an aggregation-inhibiting effect as a pigment derivative, particularly on a yellow organic pigment such as quinophthalone, and which can provide a pigment composition having good dispersibility and excellent color characteristics such as tinctorial strength and vividness. The quinophthalone compound of the present invention is represented by the following formula (1). [ in the formula (1), R¹And R²Each independently represents a hydrogen atom, a phthalimide-based atomic group represented by formula (2), or an imide-methyl atomic group represented by formula (3). X in the formula (1)¹～X¹⁶And X in the formula (2)¹⁷～X²⁰Each independently represents a hydrogen atom, a halogen atom or an imide methyl group represented by the formula (3). In this case, R in the formulae (1) and (2)¹、R²And X¹～X²⁰The total number of the imide methyl groups represented by the formula (3) is 1 to 4. Y in formula (3) represents an arylene group which may be substituted with a halogen atom, an arylsulfonyl group, an acyl group or- (C ═ O) -C₆H₄- (C ═ O) -substitution.]

Description

Quinophthalone compound, pigment composition and color filter

Technical Field

The present invention relates to a novel quinophthalone compound, a pigment composition comprising the same, and a color filter having the same.

Background

Various compositions are known as pigment compositions, and specific applications of such pigment compositions include printing inks, paints, colorants for resins, colorants for fibers, color materials for IT information recording (color filters, toners, inkjet inks), and the like. Since a pigment develops color in a particle state (an aggregate of primary particles) unlike a dye that develops color in a molecular state, the pigment generally has superior resistance but inferior coloring power and chroma (vividness) compared to a dye. The pigment composition is generally required to have color characteristics (tinting strength, vividness), resistance (weather resistance, light resistance, heat resistance, solvent resistance), and the like. In addition, the quinophthalone pigment tends to aggregate as a whole, and there is a case where a problem of dispersibility occurs when the quinophthalone pigment is produced into a pigment composition. Bis-quinophthalone pigments having a certain structure are known from patent documents 1 and 2 below. Further, patent document 3 discloses a coloring composition containing a predetermined quinophthalone pigment.

In the above pigment compositions, as one method for improving color characteristics such as tinting strength and vividness, a method of improving dispersibility of a pigment by using a pigment derivative in combination is often employed, but a pigment derivative effective particularly for a yellow organic pigment such as quinophthalone is not sufficient, and a novel derivative is desired.

Documents of the prior art

Patent literature

Patent document 1: international publication No. 2013/098836 pamphlet

Patent document 2: japanese examined patent publication No. 48-32765

Patent document 3: japanese patent laid-open No. 2012 and 247587

Disclosure of Invention

Problems to be solved by the invention

The present invention addresses the problem of providing a quinophthalone compound which exhibits an aggregation-inhibiting effect as a pigment derivative, particularly on a yellow organic pigment such as quinophthalone, and which can provide a pigment composition having good dispersibility and excellent color characteristics such as tinctorial strength and vividness. Further, the present invention addresses the problem of providing a pigment composition containing the quinophthalone compound as a pigment derivative.

Means for solving the problems

The present inventors have made extensive studies to solve the above problems, and as a result, they have found that a pigment composition excellent in color characteristics such as tinting strength and vividness can be obtained by containing a specific quinophthalone compound as a pigment derivative, particularly by suppressing the aggregation of a yellow organic pigment such as quinophthalone, and have completed the present invention.

That is, the present invention relates to the following.

Item 1. A quinophthalone compound represented by the following formula (1).

[ solution 1]

[ solution 2]

[ solution 3]

[ in the formula (1), R¹And R²Each independently represents a hydrogen atom, a phthalimide-based atomic group represented by formula (2), or an imide-methyl atomic group represented by formula (3). X in the formula (1)¹～X¹⁶And X in the formula (2)¹⁷～X²⁰Each independently represents a hydrogen atom, a halogen atom or an imide methyl group represented by the formula (3). In this case, R in the formulae (1) and (2)¹、R²And X¹～X²⁰The total number of the imide methyl groups represented by the formula (3) is 1 to 4. Y in formula (3) represents an arylene group which may be substituted with a halogen atom, an arylsulfonyl group, an acyl group or- (C ═ O) -C₆H₄- (C ═ O) -substitution.]

Item 2. a pigment composition comprising a quinophthalone pigment and a quinophthalone compound represented by the following formula (1),

[ solution 4]

[ solution 5]

[ solution 6]

[ in the formula (1), R¹And R²Each independently represents a hydrogen atom, a phthalimide-based atomic group represented by formula (2), or an imide-methyl atomic group represented by formula (3). In the formula (1)X of (2)¹～X¹⁶And X in the formula (2)¹⁷～X²⁰Each independently represents a hydrogen atom, a halogen atom or an imide methyl group represented by the formula (3). In this case, R in the formulae (1) and (2)¹、R²And X¹～X²⁰The total number of the imide methyl groups represented by the formula (3) is 1 to 4. Y in formula (3) represents an arylene group which may be substituted with a halogen atom, an arylsulfonyl group, an acyl group or- (C ═ O) -C₆H₄- (C ═ O) -substitution.]

Item 3. the pigment composition according to item 2, wherein the quinophthalone pigment is at least one of the quinophthalone compounds represented by the following formulae (4-1), (4-2), (4-3), (4-4) and (5),

[ solution 7]

[ solution 8]

[ solution 9]

[ solution 10]

[ formula (4-1), formula (4-2), formula (4-3) and formula (4-4), wherein R³～R¹⁵、R¹⁶～R³⁰、R³¹～R⁴⁵And R⁴⁶～R⁶²Each independently represents a hydrogen atom, a halogen atom, an alkyl group which may have a substituent, an alkoxy group which may have a substituent, an aryl group which may have a substituent, -SO₃H group, -COOH group, -SO₃H radical or-COMetal salts of OH groups, -SO₃An alkylammonium salt of an H group or a-COOH group, a phthalimidomethyl group which may have a substituent, or a sulfamoyl group which may have a substituent.]

[ solution 11]

[ in the formula (5), R⁶³～R⁷⁰Each independently represents a hydrogen atom, a halogen atom, an alkyl group which may have a substituent, an alkoxy group which may have a substituent, an aryl group which may have a substituent, -SO₃H group, -COOH group, -SO₃Metal salts of H groups or-COOH groups, -SO₃An alkylammonium salt of an H group or a-COOH group, a phthalimidomethyl group which may have a substituent, or a sulfamoyl group which may have a substituent. In addition, R⁷¹～R⁷⁴Each independently represents a hydrogen atom, a halogen atom or a phthalimide-based atomic group represented by the following formula (6).]

[ solution 12]

[ in the formula (6), X²¹～X²⁴Each independently represents a hydrogen atom or a halogen atom.]

Item 4. the pigment composition according to item 2 or 3, which is used for a color filter.

An item 5. a color filter having a pixel portion containing the pigment composition described in any one of items 2 to 4.

Effects of the invention

The quinophthalone compound of the present invention exhibits an aggregation inhibiting effect particularly on a yellow pigment such as quinophthalone, and can provide a pigment composition having good dispersibility and excellent color characteristics such as coloring power and vividness. The pigment composition of the present invention has good dispersibility and excellent color characteristics such as coloring power and vividness. Therefore, the quinophthalone compound and the pigment composition of the present invention are excellent in brightness and contrast particularly when used as a color filter.

Detailed Description

[ quinophthalone Compound ]

The quinophthalone compound of the present invention mainly acts as a pigment derivative for yellow pigments such as quinophthalone, and is represented by the following formula (1).

[ solution 13]

[ solution 14]

[ solution 15]

In the formula (1), R¹And R²Each independently represents a hydrogen atom, a phthalimide-based atomic group represented by formula (2), or an imide-methyl atomic group represented by formula (3). X in the formula (1)¹～X¹⁶And X in the formula (2)¹⁷～X²⁰Each independently represents a hydrogen atom, a halogen atom or an imide methyl group represented by the formula (3). In this case, R in the formulae (1) and (2)¹、R²And X¹～X²⁰The total number of the imide methyl groups represented by the formula (3) is 1 to 4. Y in formula (3) represents an arylene group which may be substituted with a halogen atom, an arylsulfonyl group, an acyl group or- (C ═ O) -C₆H₄- (C ═ O) -substitution.

X in the formula (1) is an integer which is easy to exert an aggregation inhibiting effect on the pigment¹～X⁸And X in the formula (2)¹⁷～X²⁰Preferred are chlorine atoms and bromine atoms among the halogen atoms, and among them, chlorine atoms are more preferred. The number of the imide methyl groups represented by the above formula (3) is 1 to4, preferably 1 to 3, particularly preferably 1 to 2. Y in formula (3) represents an arylene group which may be substituted with a halogen atom, an arylsulfonyl group, an acyl group or- (C ═ O) -C₆H₄- (C ═ O) -substitution. The arylene group in Y is preferably a phenylene group or a naphthylene group, and particularly preferably a phenylene group, from the viewpoint of easily exerting an aggregation suppressing effect on the pigment.

Examples of the quinophthalone compound of the present invention include compounds represented by the following formulae (1-1) to (1-15). In the following formula, n represents the number of substituents of an imide methyl group and represents an integer of 1 to 4. The imide methyl group will be substituted with any hydrogen atom in the quinophthalone backbone to the left.

[ solution 16]

[ Process for producing quinophthalone Compound ]

The quinophthalone compound of the present invention is not particularly limited, and can be suitably produced by a conventionally known method. Examples of the quinophthalone compound of the present invention include R in the formula (1)¹And R²A hydrogen atom or an imide methyl group represented by the formula (3) (the compounds of the formulae (1-1) to (1-7) above), and R in the formula (1)¹And R²The compounds represented by the formula (2) (the compounds represented by the formulae (1-8) to (1-15)) will be described. All of the quinophthalone compounds of the present invention can be produced by referring to the following methods including examples described later and by appropriately changing the raw materials used.

First, as R in the formula (1)¹And R²Examples of the compounds represented by the formula (1-1) to (1-7) which are hydrogen atoms or imide methyl group-based radicals represented by the formula (3) will be described as a method for producing the compound represented by the formula (1-1). The compound of the formula (1-1) can be obtained, for example, by a method comprising the following steps A-I and A-II.

(Process A-I)

In the step a-I, methyl benzoate is added under an acid catalyst such as benzoic acid and heated to melt, and then tetrachlorophthalic anhydride and 6, 6' -methylenebisquinaldine [ obtained by the method described in "Polymer (Polymer)", volume39, No.20(l998), p4949, for example ] are added, and the mixture is heated and stirred to react, thereby obtaining an intermediate represented by the following formula (a-1).

[ solution 17]

The reaction temperature in the step A-I is, for example, 100 to 300 ℃ and preferably 150 to 250 ℃ and the reaction time is, for example, 1 to 8 hours and preferably 3 to 6 hours.

(Process A-II)

In the step A-II, paraformaldehyde and phthalimide are added to sulfuric acid such as fuming sulfuric acid and stirred, and then the intermediate represented by the formula (A-1) obtained in the step A-I is added to the mixture and the mixture is heated and stirred to react the intermediate, thereby obtaining the quinophthalone compound represented by the formula (1-1).

The reaction temperature in the step A-II is, for example, 20 to 150 ℃ and preferably 80 to 120 ℃ and the reaction time is, for example, 1 to 8 hours and preferably 2 to 6 hours.

Then, as R in formula (1)¹And R²Examples of the compounds represented by the formula (2) (the compounds represented by the formulae (1-8) to (1-15)) which are phthalimide-based radicals are described as a method for producing the compound represented by the formula (1-8). The compounds represented by the above formulae (1 to 8) can be obtained, for example, by a method comprising the following steps B to I, B to II, B to III and B to IV.

(Process B-I)

In the step B-I, 6' -methylenebisquinaldine [ obtained by the method described in "Polymer", volume39, No.20(l998), p4949 ], is added to sulfuric acid such as concentrated sulfuric acid with stirring under cooling in an ice bath, and nitric acid is added dropwise while maintaining at 10 ℃ or lower and the mixture is stirred to react, thereby obtaining an intermediate represented by the following formula (B-1).

[ solution 18]

The reaction temperature in the step B-I is, for example, -20 ℃ to 70 ℃, preferably 0 ℃ to 50 ℃, and the reaction time is, for example, 0.5 hours to 4 hours, preferably 1 hour to 3 hours.

(Process B-II)

In the step B-II, 6 to 8 equivalents of reduced iron are added to 1 equivalent of the intermediate represented by the formula (B-1) obtained in the step B-I, and the mixture is reacted to obtain an intermediate represented by the following formula (B-2).

[ solution 19]

The reaction temperature in the step B-II is, for example, 40 to 80 ℃ and preferably 50 to 70 ℃ and the reaction time is, for example, 0.5 to 12 hours and preferably 1 to 3 hours.

(Process B-III)

In the step B-III, the intermediate represented by the formula (B-2) obtained in the step B-II, tetrachlorophthalic anhydride and anhydrous zinc chloride are added under an acid catalyst such as benzoic acid, and the mixture is heated and stirred to react, thereby obtaining an intermediate represented by the following formula (B-3). The intermediate represented by the above formula (B-3) can also be used as the quinophthalone pigment represented by the above formula (5).

[ solution 20]

In the step B-III, the reaction temperature is, for example, 180 to 300 ℃, preferably 200 to 250 ℃, and the reaction time is, for example, 2 to 8 hours, preferably 3 to 6 hours.

(Process B-IV)

In the step B-IV, paraformaldehyde and phthalimide are added to sulfuric acid such as fuming sulfuric acid and stirred, and then the intermediate represented by the formula (B-3) obtained in the step B-III is added to the mixture and the mixture is heated and stirred to react the intermediate, thereby obtaining the quinophthalone compound represented by the formula (1-8).

The reaction temperature in the steps B to IV is, for example, 20 to 150 ℃ and preferably 80 to 120 ℃ and the reaction time is, for example, 1 to 8 hours and preferably 2 to 6 hours.

[ pigment composition ]

The pigment composition of the present invention comprises a quinophthalone pigment and a quinophthalone compound represented by the above formula (1). The pigment composition of the present invention may contain at least one of the quinophthalone compounds of the present invention, and may contain two or more of the quinophthalone compounds. The pigment composition of the present invention may contain components other than the quinophthalone pigment and the quinophthalone compound of the present invention.

(quinophthalone pigments)

In the pigment composition of the present invention, the quinophthalone pigment is not particularly limited as long as it is a pigment having a quinophthalone skeleton synthesized by condensation of quinaldine and phthalic anhydride, and such quinophthalone pigments are preferably represented by the following formulae (4-1), (4-2), (4-3), (4-4) and (5).

[ solution 21]

[ solution 22]

[ solution 23]

[ formula 24]

In the above formula (4-1), formula (4-2), formula (4-3) and formula (4-4), R³～R¹⁵、R¹⁶～R³⁰、R³¹～R⁴⁵And R⁴⁶～R⁶²Each independently represents a hydrogen atom, a halogen atom, an alkyl group which may have a substituent, an alkoxy group which may have a substituent, an aryl group which may have a substituent, -SO₃H group, -COOH group, -SO₃Metal salts of H groups or-COOH groups, -SO₃An alkylammonium salt of an H group or a-COOH group, a phthalimidomethyl group which may have a substituent, or a sulfamoyl group which may have a substituent. The above R is a group having excellent heat resistance, solvent resistance and weather resistance³～R¹⁰、R²²～R²⁵、R³¹～R³⁴Halogen atoms are preferred, and among these, chlorine atoms are particularly preferred. R is as defined above¹¹～R¹⁵、R²⁶～R³⁰、R⁴¹～R⁴⁵、R⁵⁸～R⁶²Particularly preferred is a hydrogen atom.

[ solution 25]

In the formula (5), R⁶³～R⁷⁰Each independently represents a hydrogen atom, a halogen atom, an alkyl group which may have a substituent, an alkoxy group which may have a substituent, an aryl group which may have a substituent, -SO₃H group, -COOH group, -SO₃Metal salts of H groups or-COOH groups, -SO₃An alkylammonium salt of an H group or a-COOH group, a phthalimidomethyl group which may have a substituent, or a sulfamoyl group which may have a substituent. The above R is a group having excellent heat resistance, solvent resistance and weather resistance⁶³～R⁷⁰Preferably a halogen atom, particularly preferablyIs selected as chlorine atom. R in the formula (5)⁷¹～R⁷⁴Each independently represents a hydrogen atom, a halogen atom or a phthalimide-based atomic group represented by the following formula (6).

[ solution 26]

In formula (6), X²¹～X²⁴Each independently represents a hydrogen atom or a halogen atom. The X is a compound having excellent heat resistance, solvent resistance and weather resistance²¹～X²⁴Halogen atoms are preferred, and chlorine atoms are particularly preferred. Examples of the halogen atom in the above formula (4-1), formula (4-2), formula (4-3), formula (4-4), formula (5) and formula (6) include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

Typical examples of the quinophthalone pigment represented by the above formula (4-1) include c.i. pigment yellow 138. The quinophthalone pigments represented by the formulae (4-1), (4-2), (4-3) and (4-4) can be produced, for example, by the following methods. Further, commercially available pigments can be used as these quinophthalone pigments.

The quinophthalone pigments represented by the above formulae (4-1), (4-2), (4-3) and (4-4) can be obtained, for example, by heating phthalic anhydride or naphthalenedicarboxylic anhydride in an amount of 2 to 3 equivalents relative to 1 equivalent of 8-aminoquinaldine in benzoic acid under a nitrogen atmosphere at 160 to 200 ℃ to cause condensation reaction. When only phthalic anhydride is used in this reaction, a quinophthalone pigment represented by formula (4-1) can be obtained. When only naphthalic anhydride is used in this reaction, a quinophthalone pigment represented by the formula (4-4) can be obtained. When phthalic anhydride and naphthalic anhydride are used in the reaction, quinophthalone pigments represented by the formulae (4-2) and (4-3) can be obtained.

Examples of the quinophthalone pigment represented by the above formula (5) include the following formulae (5-1) to (5-21). These quinophthalone pigments may be used alone or in combination of two or more.

[ chemical No. 27]

[ solution 28]

[ solution 29]

[ solution 30]

[ solution 31]

In the structure of formula (5), tautomers having the structures of formula (5-i) and formula (5-ii) exist, and the quinophthalone pigment represented by formula (5) may have any one of these structures. R in the formulae (5-i) and (5-ii)⁶³～R⁷⁴The same as in formula (5).

[ chemical No. 32]

The quinophthalone pigment represented by the above formula (5) is not particularly limited, and can be obtained, for example, by a method of condensing an alkylene compound represented by the following formula (7) with an acid anhydride represented by the following formula (8). R in the formulae (7) and (8)⁷²、R⁷⁴And R⁶³～R⁶⁶Same as (R) in formula (5)⁶³～R⁶⁶And R⁶⁷～R⁷⁰Substantially the same). The alkylene compound represented by the formula (7) can be produced by the method described later.

[ chemical formula 33]

[ chemical 34]

Specific examples of the alkylene compound represented by the formula (7) include compounds represented by the following formulae (7-1) and (7-2). The alkylene compound represented by the formula (7) may be used alone or in combination of two or more.

[ solution 35]

[ solution 36]

Specific examples of the acid anhydride represented by the formula (7) include phthalic anhydride and halogen-substituted phthalic anhydride, and specific examples of the halogen-substituted phthalic anhydride include tetrafluorophthalic anhydride, tetrachlorophthalic anhydride, tetrabromophthalic anhydride, 4, 5-dichlorophthalic anhydride, 4-chlorophthalic anhydride, 4, 5-dibromophthalic anhydride, and the like. The acid anhydride represented by the formula (7) may be used alone or in combination of two or more. By using two or more different kinds of anhydrides represented by the formula (7), a plurality of R's can be obtained⁶³Each other, a plurality of R⁶⁴Each other, a plurality of R⁶⁵Each other and a plurality of R⁶⁶Quinophthalone pigments represented by the above formula (5) which are different from each other.

Watch of formula (7)The alkylene compound shown in the above can be obtained, for example, by a method comprising the following steps C to I, C to II and C to III. Note that, in the formulae (7-i) and (7-ii), a plurality of R are present⁷²Each other and a plurality of R⁷⁴May be the same or different from each other.

First, in the step C-I, a compound of the following formula (7-I) is synthesized by adding 2 to 3 equivalents of crotonaldehyde to 1 equivalent of a bisaniline compound by the method described in j.heterocyclic, Chem,30,17(1993) and reacting the mixture in a strong acid in the presence of an oxidizing agent.

[ solution 37]

Here, examples of the strong acid include hydrochloric acid, sulfuric acid, and nitric acid. Examples of the oxidizing agent include sodium iodide, tetrachlorobenzoquinone, and nitrobenzene. The reaction temperature in the step C-I is, for example, 80 to 100 ℃ and preferably 90 to 100 ℃ and the reaction time is, for example, 1 to 6 hours and preferably 3 to 6 hours.

Further, in the step C-II, the obtained compound of the formula (7-i) is reacted with nitric acid or fuming nitric acid in the presence of concentrated sulfuric acid to obtain a compound of the following formula (7-II).

[ solution 38]

The reaction temperature in the step C-II is, for example, -20 ℃ to 70 ℃, preferably 0 ℃ to 50 ℃, and the reaction time is, for example, 0.5 hours to 4 hours, preferably 1 hour to 3 hours.

Further, in the step C-III, the nitro group (-NO) is converted into a nitro group (-NO) by reduction of the obtained compound of the formula (7-ii)₂) Conversion to amino (-NH)₂) Thereby, an alkylene compound represented by the above formula (7) can be obtained.

In the step C-III, the alkylene compound represented by the formula (7) can be obtained by, for example, subjecting the compound of the formula (7-ii) to reduction treatment with reduced iron. In this case, the amount of reduced iron may be 6 to 8 equivalents, the reaction temperature may be 40 to 80 ℃, preferably 50 to 70 ℃, and the reaction time may be 0.5 to 12 hours, preferably 1 to 3 hours, relative to 1 equivalent of the compound of formula (7-ii). The alkylene compound represented by the formula (7) can also be obtained by subjecting the compound of the formula (7-ii) to a reduction treatment using a metal catalyst such as palladium-carbon (Pd-C), platinum-carbon (Pt-C), or Raney nickel. In this case, the amount of the metal catalyst may be, for example, 0.4 to 5% by mass of the compound of formula (7-ii) in terms of metal, the reaction temperature may be, for example, 30 to 100 ℃, and the reaction time may be, for example, 1 to 10 hours. As the hydrogen source for the reaction, hydrogen gas, hydrazine, ammonium formate, or the like can be used.

[ component content in pigment composition ]

The content of the quinophthalone compound represented by the formula (1) in the pigment composition of the present invention is, for example, 1 to 15% by mass, preferably 2 to 10% by mass, and more preferably 3 to 8% by mass, based on the entire pigment composition. The content of the quinophthalone compound represented by the above formula (1) is, for example, 1 to 20 parts by mass, preferably 2 to 15 parts by mass, and more preferably 3 to 10 parts by mass, based on 100 parts by mass of the pigment. When the content of the quinophthalone compound is in the above range, the dispersibility is good and the color characteristics such as coloring power and vividness are excellent.

The total content of the quinophthalone pigments represented by the above formulae (4-1), (4-2), (4-3), (4-4) and (5) in the pigment composition of the present invention is, for example, 5 to 98% by mass, preferably 10 to 95% by mass, more preferably 15 to 90% by mass, based on the total amount of the pigment composition. In the pigment composition of the present invention, the following pigments other than the quinophthalone pigments represented by the above formulae (4-1), (4-2), (4-3), (4-4) and (5) can also be used. The total content of the quinophthalone pigments represented by the above formulae (4-1), (4-2), (4-3), (4-4) and (5) is, for example, 90% by mass or more, preferably 95% by mass or more, more preferably 99% by mass or more, relative to the total amount of the yellow pigments.

The pigment composition of the present invention preferably contains a quinophthalone pigment represented by the formula (5) in view of facilitating the development of the characteristics of the quinophthalone compound represented by the formula (1) which is excellent in color characteristics such as good dispersibility and excellent coloring power and vividness. The content of the quinophthalone pigment represented by the above formula (5) when the quinophthalone pigment represented by the formula (5) is contained is, for example, 1 to 80% by mass, preferably 2 to 70% by mass, and more preferably 3 to 60% by mass, based on the total amount of the pigment composition.

When the quinophthalone pigment of the above formulae (4-1), (4-2), (4-3) and (4-4) and the quinophthalone pigment of the formula (5) are used in combination, the content of the quinophthalone pigment of the above formula (5) is, for example, 30 to 95% by mass, preferably 40 to 90% by mass, more preferably 50 to 85% by mass, based on the total content of the quinophthalone pigments contained in the pigment composition. When two or more quinophthalone pigments represented by formula (5) are contained, the above content is the total content thereof.

The content of the pigment (particularly quinophthalone pigment) in the pigment composition of the present invention is, for example, 70 to 99% by mass, preferably 75 to 98% by mass, and more preferably 80 to 97% by mass, based on the entire pigment composition.

The pigment composition of the present invention may contain, as a pigment, a pigment other than the quinophthalone pigment, for example, a condensed polycyclic pigment such as an azo pigment, phthalocyanine pigment, azomethine, anthraquinone, isoindoline, isoindolinone, dioxazine, perylene, quinacridone, diketopyrrolopyrrole, or the like.

The pigment composition of the present invention may contain rosin, a surfactant, a resin, a dispersant, a photosensitive resin, a curable resin, and the like as components other than those described above. These components can be added by, for example, surface treatment of the quinophthalone pigment described above. Examples of the surface treatment of the pigment include a known method such as rosin treatment, surfactant treatment, solvent treatment, and resin treatment.

The pigment composition of the present invention contains the specific pigment derivative, and therefore has good dispersibility and excellent color characteristics such as coloring power and vividness. Therefore, the composition is particularly suitable as a composition for forming a color filter (a pigment composition for a color filter). When the pigment composition of the present invention is used for a color filter, the color filter is excellent in brightness, particularly, contrast.

[ color filters ]

The color filter of the present invention has a pixel portion containing the pigment composition of the present invention. As the color filter, there is a method called photolithography, which includes: a pigment composition is added with a solvent or the like to prepare a colored composition (or a photosensitive resin is added to prepare a photosensitive colored composition), the colored composition (photosensitive colored composition) is applied onto a transparent substrate such as a glass substrate by a spin coating method, a roll coating method, an ink jet method or the like, then the applied film is subjected to pattern exposure by ultraviolet rays through a photomask, and then the unexposed portion is washed with an organic solvent, alkali water or the like to obtain a colored pattern. The method of forming the pixel portion is not particularly limited, and the color filter can be manufactured by patterning the pixel portion by a method such as an Electrodeposition method, a transfer method, a micelle electrolysis method, or a PVED (Photovoltaic Electrodeposition) method.

The color filter typically has a red pixel portion, a blue pixel portion, and a green pixel portion. The pigment composition of the present invention is not particularly limited, but is preferably used as a yellow color material as part of a pigment forming a green pixel portion and a blue pixel portion together with a conventional green color material and a conventional blue color material. The thickness of the pixel portion is, for example, 3.6 μm or less.

(coloring composition)

The solvent in the coloring composition 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; propionate solvents such as ethyl ethoxypropionate; 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; aliphatic hydrocarbon solvents such as hexane; nitrogen compound solvents such as N, N-dimethylformamide, γ -butyrolactam, N-methyl-2-pyrrolidone, aniline, and pyridine; lactone solvents such as γ -butyrolactone; and carbamates such as 48:52 mixtures of methyl carbamates and ethyl carbamates. The organic solvent is preferably a polar and water-soluble solvent, and more preferably a propionate solvent, an alcohol solvent, an ether solvent, a ketone solvent, a nitride solvent, or a lactone solvent.

The coloring composition may further contain a coloring material such as an organic pigment or an organic dye other than the quinophthalone pigment, a pigment derivative other than the quinophthalone compound represented by the formula (1), and the like. Examples of the organic pigments other than the above pigments include: phthalocyanine pigments (green color materials) such as c.i. pigment green 36, 58, 59, 62, 63, etc., aluminum phthalocyanine pigments represented by the following formulae (8-1) and (8-2) or a mixture with a yellow pigment (green color materials), epsilon-type copper phthalocyanine pigments (blue color materials) such as c.i. pigment blue 15:6, etc., dianthraquinone pigments such as c.i. pigment red 177, diketopyrrolopyrrole pigments such as c.i. pigment red 254, naphthol-based azo pigments such as c.i. pigment red 269, etc. (the above are red color materials).

[ solution 39]

[ solution 40]

A in the above formulae (8-1) and (8-2)¹～A⁴And A⁵～A¹²Each independently represents an alkyl group which may have a substituent, an aryl group which may have a substituent, 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 an arylthio group which may have a substituent. D in the above formulae (8-1) and (8-2)¹～D⁴And D⁵～D¹²Each independently represents a halogen atom, a nitro group, or a substituentPhthalimidomethyl of the group or a sulfamoyl group which may have a substituent. Z in the above formula (8-1)¹Represents a hydroxyl group, a chlorine atom, -OP (═ O) R₁R₂or-O-SiR₃R₄R₅. Here, R₁～R₅Each independently represents 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 aryloxy group which may have a substituent, and R may bond to each other to form a ring. Z in the above formula (8-2)²represents-O-SiR₆R₇-O-、-O-SiR₆R₇-O-SiR₈R₉-O-or-O-P (═ O) R₁₀-O-，R₆～R₁₀Each independently represents 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 aryloxy group which may have a substituent. In the formulae (8-1) and (8-2), a1 to a4, a5 to a12, d1 to d4 and d5 to d12 each independently represent an integer of 0 to 4, and a1+ d1, a2+ d2, a3+ d3, a4+ d4, a5+ d5, a6+ d6, a7+ d7, a8+ d8, a9+ d9, a10+ d10, a1l + d1l and a12+ d12 each represent an integer of 0 to 4, and may be the same or different.

The coloring composition may further contain a dispersant. Examples of the dispersant include: ANTI-TERRA U/U100, ANTI-TERRA 204, DISPERBYK 106, DISPERBYK 108, DISPERBYK 109, DISPERBYK 112, DISPERBYK 130, DISPERBYK 140, DISPERBYK 142, DISPERBYK 145, DISPERBYK 161, DISPERBYK 162, DISPERBYK 163, DISPERBYK 164, DISPERBYK 167, DISPERBYK 168, DISPERBYK 180, DISPERBYK 182, DISPERBYK 402183, DISPERBYK 184, DISPERBYK 185, DISPERBYK 2000, DISPERBYK 2001, DISPERBYK 2008, DISPERBYK 2009, DISPERBYK 2013, DISPERBYK 2022, DISPERBYK 2025, DISPERBYKA 4306, DISPERBYKA 2153, DISPERBYK 2154, DISPERBYK 435, DISPERBYK 215691K 3, DISPERBYK 2214, DISPERBYK 3, DISPERBYK 2214, DISPERBYK 3, DISPERBYK 3, DISPERBYK 43691K 3, DISPERBYK 7, DISPERBYK 3, DISPERBYK, EFKA 7461, EFKA 7462, EFKA7476, EFKA 7477 (manufactured by BASF corporation), Ajisper (registered trade name) PB814, Ajisper PB821, Ajisper PB822, Ajisper PB881 (manufactured by Ajiser Fine technologies Co., Ltd.), Solsperse (registered trade name) 24000, Solsperse 28000, Solsperse 37500, Solsperse76500 (manufactured by Lumboli K.K.), and the like.

The coloring composition may further contain a leveling agent, a coupling agent, a cationic rosin, a surfactant, a photosensitive resin, a curable resin, and the like as components other than the above.

The viscosity of the coloring composition is not particularly limited, and may be appropriately adjusted depending on the use and the like. The viscosity of the coloring composition at 20 ℃ is, for example, 0.5 to 100 mPas, preferably 1 to 50 mPas, from the viewpoint of maintaining viscosity suitable for processing.

The coloring composition may further contain a photosensitive resin. The coloring composition containing a photosensitive resin may also be referred to as a photosensitive coloring composition. Examples of the photosensitive resin include: thermoplastic resins such as polyurethane resins, acrylic resins, polyamic acid resins, polyimide resins, styrene maleic acid resins, and styrene maleic anhydride resins; examples of the polymerizable monomer include a bifunctional monomer such as 1, 6-hexanediol diacrylate, ethylene glycol diacrylate, neopentyl glycol diacrylate, triethylene glycol diacrylate, bis (acryloyloxyethoxy) bisphenol A, 3-methylpentanediol diacrylate and the like, and a photopolymerizable monomer such as trimethylolpropane triacrylate, pentaerythritol triacrylate, tris- (2-acryloyloxyethyl) isocyanurate, dipentaerythritol hexaacrylate, dipentaerythritol pentaacrylate and the like.

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

A dispersion liquid (coloring composition) can be obtained by uniformly stirring and dispersing 1 to 20 parts by mass of a quinophthalone compound represented by the formula (1) and 300 to 2000 parts by mass of an organic solvent with respect to 100 parts by mass of a quinophthalone pigment. Then, a photosensitive resin in an amount of 3 to 25 parts by mass per 100 parts by mass of the dispersion and a photopolymerization initiator (and an organic solvent further added as needed) in an amount of 0.05 to 3 parts by mass per 1 part by mass of the photosensitive resin are added to the dispersion, and the mixture is stirred and dispersed so as to be uniform, thereby obtaining a photosensitive colored composition.

When the colored composition (photosensitive colored composition) is used for forming a green pixel portion of a color filter, 200 parts by mass or less of a green color material and/or 200 parts by mass or less of a blue color material may be further added to 100 parts by mass of the quinophthalone pigment.

Examples

The present invention will be described more specifically with reference to examples, but the present invention is not limited to the forms of the following examples.

First, a quinophthalone compound (pigment derivative) and a quinophthalone pigment were obtained by the methods described in synthetic examples 1 to 6 below. Then, the quinophthalone compound and the quinophthalone pigment obtained were used to carry out pigmentation by the methods described in pigmenting examples 1 to 6 to obtain a pigment composition. Then, a yellow toning composition was prepared by the method described in examples 1 to 4 and comparative examples 1 to 2, and finally the contrast of the obtained color filter was measured.

[ Synthesis example 1]

234g of benzoic acid and 133g of methyl benzoate were charged into the flask, and dissolved by heating at 160 ℃ under a nitrogen stream. Then, 46.1g of tetrachlorophthalic anhydride and 9.1g of 6, 6' -methylenebisquinaldine obtained by the method described in the literature (Polymer, volume39, No.20(l998), p4949) were added thereto, and the mixture was stirred at 200 ℃ for 5 hours. After cooling, 440mL of N-methylpyrrolidone (NMP) was added, and the mixture was filtered hot at 80 ℃ and washed with NMP. The gel was dissolved in 200mL of methanol, and the mixture was stirred at 60 ℃ for 1 hour. After leaving to cool, the mixture was filtered, washed with methanol, and dried under reduced pressure to obtain 25.2g of intermediate (9) as a yellow powder.

[ solution 41]

FT-IR(KBr disk)cm^-1:1682、1636、1618、1590、1538、1420、1382、1306、730

FD-MS:834M+

[ Synthesis example 2]

A flask was charged with 24.4g of 3.6% fuming sulfuric acid, and 6.8g of paraformaldehyde and 14.4g of phthalimide were added thereto, followed by stirring at room temperature for 30 minutes. Then, 5g of the intermediate (9) obtained in Synthesis example 1 was added thereto, and the mixture was stirred at 100 ℃ for 3 hours. After the mixture was left to cool, the mixture was added to 173g of ice water, and after stirring at 60 ℃ for 30 minutes, the precipitate was filtered. The resultant extract was washed with warm water three times, and air-dried at 90 ℃ to obtain 6.76g of quinophthalone compound (10) as a tan powder.

[ solution 42]

FT-IR(KBr disk)cm^-1:1773、1716、1629、1610、1537、1417、1400、1304、728

FD-MS:993(n＝l)、1152(n＝2)、1311(n＝3)M+

[ Synthesis example 3]

55g of concentrated sulfuric acid was charged in a flask, and 7.0g of 6, 6' -methylenebisquinaldine obtained by the method described in the literature (Polymer, volume39, No.20(l998), p4949) was added thereto with stirring under cooling in an ice bath. While keeping the temperature below 10 ℃, 6.1g of 60% nitric acid was added dropwise, and stirring was continued from 10 ℃ to 20 ℃ for 1 hour. The reaction solution was poured into 150ml of ice water, and the pH was adjusted to 3 using a 20 wt% aqueous sodium hydroxide solution. The precipitated powder was recovered by filtration under reduced pressure and washed to neutrality with water. The obtained solid was dried by blowing at 70 ℃ and then the crude product was subjected to washing filtration with 100ml of hot ethyl acetate followed by 60ml of hot toluene to obtain 6.52g of intermediate (11).

[ solution 43]

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 4]

A flask was charged with 5.30g of reduced iron and 135ml of acetic acid, and heated to 50 ℃ with stirring. Subsequently, 4.50g of the intermediate (11) obtained in Synthesis example 3 was added to the reaction mixture so as to be maintained at 70 ℃ or lower. After the completion of the addition, the reaction mixture was stirred at 60 ℃ for 1 hour, cooled to 35 ℃ or lower, poured into 500ml 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 recovered, dried at 70 ℃ with air blowing, added to a mixed solvent of 100ml of dimethyl sulfoxide (DMSO) and 100ml of N, N-Dimethylformamide (DMF), and stirred at 90 ℃ for 1 hour. The mixture was filtered under reduced pressure over celite, and the obtained filtrate was added to 1L of water with stirring. The resulting precipitate was recovered by filtration under reduced pressure and washed with water to obtain 3.80g of intermediate (12).

[ solution 44]

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^-1:3464,3363,3315,3192,1640,1591,1573,1415,1365,801

[ Synthesis example 5]

135g of benzoic acid was weighed into a flask under a nitrogen atmosphere, and melted at 140 ℃. 3.80g of the intermediate (12) obtained in Synthesis example 4, 17.99g of tetrachlorophthalic anhydride, and 0.49g of anhydrous zinc chloride were added thereto, and the mixture was stirred at 220 ℃ for 6 hours. After the reaction mixture was cooled to 120 ℃, 300mL of chlorobenzene was added and stirred for 1 hour, and by filtration under reduced pressure, 10.5g of quinophthalone pigment (13) was obtained as a yellow powder.

[ solution 45]

FT-IR cm^-1:1788,1729,1688,1638,1607,1537,1420,1310,732

FD-MS:1399M+

[ Synthesis example 6]

A flask was charged with 73.2g of 3.6% fuming sulfuric acid, and then added with 12.2g of paraformaldehyde and 3.78g of phthalimide, followed by stirring at room temperature for 30 minutes. Then, 5g of the quinophthalone pigment (13) obtained in Synthesis example 5 was added, and the mixture was stirred at 120 ℃ for 3 hours. After the mixture was left to cool, it was added to 518g of ice water, stirred at 60 ℃ for 30 minutes, and then the precipitate was filtered. The resultant extract was washed with warm water three times, and air-dried at 90 ℃ to obtain 14.4g of quinophthalone compound (14) as a tan powder.

[ solution 46]

FD-MS:1559(n＝l)M+

[ pigmentation example 1]

47.5g of the quinophthalone pigment (13) obtained in Synthesis example 5 was ground together with 2.5g of the quinophthalone compound (10) obtained in Synthesis example 2, 400g of sodium chloride and 66.6g of diethylene glycol. Then, the mixture was poured into 2000g of warm water and stirred for 1 hour. The water-insoluble fraction was separated by filtration, thoroughly washed with warm water, and then dried at 90 ℃ with air blowing.

[ pigmentation example 2]

Pigmentation was performed in the same manner as in pigmentation example 1, except that the quinophthalone compound (14) obtained in synthesis example 6 was used instead of the quinophthalone compound (10) which is an imidomethyl derivative obtained in synthesis example 2.

[ pigmentation example 3]

Pigmenting was carried out in the same manner as in pigmenting example 1 except that the amount of quinophthalone pigment (13) obtained in synthesis example 5 was changed from 47.5g to 48.5g, and the amount of quinophthalone compound (10) obtained in synthesis example 2 was changed from 2.5g to 1.5 g.

[ pigmentation example 4]

Pigmenting was carried out in the same manner as in pigmenting example 1 except that the amount of quinophthalone pigment (13) obtained in synthesis example 5 was changed from 47.5g to 46.5g, and the amount of quinophthalone compound (10) obtained in synthesis example 2 was changed from 2.5g to 3.5 g.

[ pigmentation example 5]

50g of the quinophthalone pigment (13) obtained in Synthesis example 5 was ground together with 400g of sodium chloride and 66.6g of diethylene glycol. Then, the mixture was poured into 2000g of warm water and stirred for 1 hour. The water-insoluble fraction was separated by filtration, washed thoroughly with warm water, and then dried at 90 ℃ with air.

[ pigmentation example 6]

Pigmentation was performed in the same manner as in pigmentation example 1, except that the quinophthalone compound (10) as the imidomethyl derivative obtained in synthesis example 2 was replaced by the imidomethyl derivative of c.i. pigment yellow 138 synthesized by the method described in jp 2013-54200 a.

[ example 1]

0.8g of the quinophthalone pigmenting composition obtained in pigmenting example 1 was placed in a glass bottle, and 13.25g of propylene glycol monomethyl ether acetate, 0.4g of DISPERBYK (registered trademark) LPN-6919 (manufactured by Pickery chemical Co., Ltd.), and UNIDIC (registered trademark) ZL-295 (manufactured by NIKE CO., Ltd.) were added to the glass bottleManufactured by Ltd.) 0.6g,

22.0g of beads were dispersed by a paint shaker (manufactured by Toyo Seiki Seisaku-Sho Co., Ltd.) for 2.5 hours to obtain a pigment dispersion. The contents of the pigments and derivatives in example 1 are shown in table 1 below. Further, 3.6g of the pigment dispersion and 0.6g of acrylic resin solution UNIDIC (registered trademark) ZL-295 (manufactured by DIC corporation) were put in a glass bottle and shaken to prepare a yellow toning composition. The obtained yellow toning composition was applied to a glass substrate by a spin coater and then dried. The obtained glass substrate for evaluation was heated at 230 ℃ for 1 hour, and then measured for CONTRAST using a CONTRAST measuring instrument (CONTRAST TESTER CT-1 manufactured by osaka corporation). The measurement results are shown in table 1. The contrast was measured at a film thickness of 1 μm.

[ example 2]

A yellow toning composition was prepared and the contrast was measured in the same manner as in example 1, except that the quinophthalone pigmentized composition obtained in pigmenting example 1 was replaced with the quinophthalone pigmentized composition obtained in pigmenting example 2.

[ example 3]

A yellow toning composition was prepared and the contrast was measured in the same manner as in example 1, except that the quinophthalone pigmentized composition obtained in pigmenting example 1 was replaced with the quinophthalone pigmentized composition obtained in pigmenting example 3.

[ example 4]

A yellow toning composition was prepared and the contrast was measured in the same manner as in example 1, except that the quinophthalone pigmentized composition obtained in pigmenting example 1 was replaced with the quinophthalone pigmentized composition obtained in pigmenting example 4.

Comparative example 1

A yellow toning composition was prepared and the contrast was measured in the same manner as in example 1, except that the quinophthalone pigmentized composition obtained in pigmenting example 1 was replaced with the quinophthalone pigmentized composition obtained in pigmenting example 5.

Comparative example 2

A yellow toning composition was prepared and the contrast was measured in the same manner as in example 1, except that the quinophthalone pigmentized composition obtained in pigmenting example 1 was replaced with the quinophthalone pigmentized composition obtained in pigmenting example 6.

[ Table 1]

As shown in Table 1, color filters having superior contrast ratios as compared with comparative examples 1-2 were obtained in examples 1-4. From these results, it was confirmed that a color filter having excellent contrast can be realized by combining a quinophthalone pigment with a specific quinophthalone derivative.

Claims

1. A quinophthalone compound represented by the following formula (1),

[ solution 1]

[ solution 2]

[ solution 3]

In the formula (1), R¹And R²Each independently represents a hydrogen atom, a phthalimide-based atomic group represented by formula (2) or an imide-methyl atomic group represented by formula (3); x in the formula (1)¹～X¹⁶And in formula (2)X of (2)¹⁷～X²⁰Each independently represents a hydrogen atom, a halogen atom or an imide methyl group represented by the formula (3); in this case, R in the formulae (1) and (2)¹、R²And X¹～X²⁰The total number of the imide methyl groups represented by the formula (3) in (a) is 1 to 4; y in formula (3) represents an arylene group which may be substituted with a halogen atom, an arylsulfonyl group, an acyl group or- (C ═ O) -C₆H₄- (C ═ O) -substitution.

2. A pigment composition comprising a quinophthalone pigment and a quinophthalone compound represented by the following formula (1),

[ solution 4]

[ solution 5]

[ solution 6]

In the formula (1), R¹And R²Each independently represents a hydrogen atom, a phthalimide-based atomic group represented by formula (2) or an imide-methyl atomic group represented by formula (3); x in the formula (1)¹～X¹⁶And X in the formula (2)¹⁷～X²⁰Each independently represents a hydrogen atom, a halogen atom or an imide methyl group represented by the formula (3); in this case, R in the formulae (1) and (2)¹、R²And X¹～X²⁰The total number of the imide methyl groups represented by the formula (3) in (b) is 1 to 4; y in formula (3) represents an arylene group which may be substituted with a halogen atom, an arylsulfonyl group, an acyl group or- (C ═ O) -C₆H₄- (C ═ O) -substitution.

3. The pigment composition according to claim 2, wherein the quinophthalone pigment is at least any one of the quinophthalone compounds represented by the following formula (4-1), formula (4-2), formula (4-3), formula (4-4) and formula (5),

[ solution 7]

[ solution 8]

[ solution 9]

[ solution 10]

In the formula (4-1), the formula (4-2), the formula (4-3) and the formula (4-4), R³～R¹⁵、R¹⁶～R³⁰、R³¹～R⁴⁵And R⁴⁶～R⁶²Each independently represents a hydrogen atom, a halogen atom, an alkyl group which may have a substituent, an alkoxy group which may have a substituent, an aryl group which may have a substituent, -SO₃H group, -COOH group, -SO₃Metal salts of H groups or-COOH groups, -SO₃An alkylammonium salt of an H group or a-COOH group, a phthalimidomethyl group which may have a substituent, or a sulfamoyl group which may have a substituent,

[ solution 11]

In the formula (5), R⁶³～R⁷⁰Each independently represents a hydrogen atom, a halogen atom, an alkyl group which may have a substituent, an alkoxy group which may have a substituent, an aryl group which may have a substituent, -SO₃H group, -COOH group, -SO₃Metal salts of H groups or-COOH groups, -SO₃An alkylammonium salt of an H group or-COOH group, a phthalimidomethyl group which may have a substituent, or a sulfamoyl group which may have a substituent; in addition, R⁷¹～R⁷⁴Each independently represents a hydrogen atom, a halogen atom or a phthalimide-based atomic group represented by the following formula (6),

[ solution 12]

In the formula (6), X²¹～X²⁴Each independently represents a hydrogen atom or a halogen atom.

4. The pigment composition according to claim 2 or 3, which is used for a color filter.

5. A color filter having a pixel portion containing the pigment composition according to any one of claims 2 to 4.