TW202122383A - Quinophthalone compound, pigment composition, and color filter - Google Patents

Abstract

The present invention addresses the problem of providing, as a pigment derivative, a quinophthalone compound which exhibits an aggregation suppression effect against yellow organic pigments such as quinophthalone pigments in particular, has good dispersibility, and can give a pigment composition having excellent color properties such as tinting strength and clarity. This quinophthalone compound is represented by formula (1). [In formula (1), R1 and R2 each independently denote a hydrogen atom, a phthalimide-based group represented by formula (2) or an imidomethyl group represented by formula (3). X1 to X16 in formula (1) and X17 to X20 in formula (2) each independently denote a hydrogen atom, a halogen atom or an imidomethyl-based group represented by formula (3). In this case, the total number of imidomethyl groups represented by formula (3) in R1, R2 and X1 to X20 in formulae (1) and (2) is 1-4. Y in formula (3) denotes an arylene group. This arylene group may be substituted with a halogen atom, an arylsulfonyl group, an acyl group or -(C=O)-C6H4-(C=O)-.].

Description

Quinophthalone compound, pigment composition and color filter

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

As a pigment composition, various compositions are known. Specific uses of such a pigment composition include printing inks, paints, colorants for resins, colorants for fibers, and information technology (IT) for information recording. Color materials (color filter, toner, inkjet), etc. Unlike dyes that develop color in a molecular state, pigments develop color in a particle state (agglomerates of primary particles). Therefore, compared with dyes, pigments are generally superior in resistance, but in coloring power and chroma (sharpness). Poor. The pigment composition generally requires color characteristics (coloring power, vividness), resistance (weather resistance, light resistance, heat resistance, solvent resistance), and the like. In addition, quinophthalone pigments tend to aggregate easily as a whole, and may cause dispersibility problems when they are made into pigment compositions. The bisquinophthalone pigments having a certain structure described in the following Patent Document 1 and Patent Document 2 are known. In addition, Patent Document 3 discloses a coloring composition containing a predetermined quinophthalone pigment.

In the pigment composition, as a method for improving the color characteristics such as coloring power and vividness, a method of using a pigment derivative to improve the dispersibility of the pigment is often used, but especially for yellow organic pigments such as quinophthalone. Effective pigment derivatives are not sufficient, and new derivatives are sought. [Prior Art Literature] [Patent Literature]

Patent Document 1: International Publication No. 2013/098836 Handbook Patent Document 2: Japanese Patent Publication No. 48-32765 Patent Document 3: Japanese Patent Laid-Open No. 2012-247587

[The problem to be solved by the invention] The subject of the present invention is to provide a quinophthalone compound, as a pigment derivative, particularly exhibits an aggregation inhibitory effect on yellow organic pigments such as quinophthalone, and can be made into a compound with good dispersibility and excellent color characteristics such as coloring power and vividness. Pigment composition. In addition, the subject of the present invention is to provide a pigment composition containing the quinophthalone compound as a pigment derivative. [Means to solve the problem]

The inventors of the present invention have made diligent studies to solve the above-mentioned problems. As a result, they have found that by including a specific quinophthalone compound as a pigment derivative, particularly by inhibiting the aggregation of yellow organic pigments such as quinophthalone, the coloring power or vividness can be obtained. A pigment composition with excellent color characteristics such as sex, and completed the present invention.

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[式（1）中，R¹ 及R² 分別獨立地表示氫原子、式（2）所表示的鄰苯二甲醯亞胺系原子團或式（3）所表示的醯亞胺甲基原子團。式（1）中的X¹ ～X¹⁶ 及式（2）中的X¹⁷ ～X²⁰ 分別獨立地表示氫原子、鹵素原子或式（3）所表示的醯亞胺甲基系原子團。此時，式（1）及式（2）中的R¹ 、R² 以及X¹ ～X²⁰ 中的式（3）所表示的醯亞胺甲基原子團的合計的數量為1至4。式（3）中的Y表示伸芳基，該伸芳基亦可被鹵素原子、芳基磺醯基、醯基或-(C=O)-C₆ H₄ -(C=O)-取代。]That is, the present invention relates to the following. Item 1. A quinophthalone compound represented by the following formula (1). [化1]

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[In the formula (1), R ¹ and R ² each independently represent a hydrogen atom, the phthalimide-based atomic group represented by the formula (2), or the imidine methyl group represented by the formula (3). X ¹ to X ^{16 in the} formula (1) and X ¹⁷ to X ²⁰ in the formula (2) each independently represent a hydrogen atom, a halogen atom, or an iminomethyl-based atomic group represented by the formula (3). At this time, the total number of the imidinyl radicals represented by the formula (3) in the formula (1) and the formula (2), R ¹ , R ^2, and X ¹ to X ^{20 is 1 to 4.} Y in formula (3) represents an arylene group, which can also be substituted by a halogen atom, an arylsulfonyl group, an acyl group or -(C=O)-C ₆ H ₄ -(C=O)- . ]

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[式（1）中，R¹ 及R² 分別獨立地表示氫原子、式（2）所表示的鄰苯二甲醯亞胺系原子團或式（3）所表示的醯亞胺甲基原子團。式（1）中的X¹ ～X¹⁶ 及式（2）中的X¹⁷ ～X²⁰ 分別獨立地表示氫原子、鹵素原子或式（3）所表示的醯亞胺甲基系原子團。此時，式（1）及式（2）中的R¹ 、R² 以及X¹ ～X²⁰ 中的式（3）所表示的醯亞胺甲基原子團的合計的數量為1至4。式（3）中的Y表示伸芳基，該伸芳基亦可被鹵素原子、芳基磺醯基、醯基或-(C=O)-C₆ H₄ -(C=O)-取代。]Item 2. A pigment composition comprising a quinophthalone pigment and a quinophthalone compound represented by the following formula (1), [化4]

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[In the formula (1), R ¹ and R ² each independently represent a hydrogen atom, the phthalimide-based atomic group represented by the formula (2), or the imidine methyl group represented by the formula (3). X ¹ to X ^{16 in the} formula (1) and X ¹⁷ to X ²⁰ in the formula (2) each independently represent a hydrogen atom, a halogen atom, or an iminomethyl-based atomic group represented by the formula (3). At this time, the total number of the imidinyl radicals represented by the formula (3) in the formula (1) and the formula (2), R ¹ , R ^2, and X ¹ to X ^{20 is 1 to 4.} Y in formula (3) represents an arylene group, which can also be substituted by a halogen atom, an arylsulfonyl group, an acyl group or -(C=O)-C ₆ H ₄ -(C=O)- . ]

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[式（4-1）、式（4-2）、式（4-3）及式（4-4）中，R³ ～R¹⁵ 、R¹⁶ ～R³⁰ 、R³¹ ～R⁴⁵ 及R⁴⁶ ～R⁶² 分別獨立地表示氫原子、鹵素原子、可具有取代基的烷基、可具有取代基的烷氧基、可具有取代基的芳基、-SO₃ H基、-COOH基、-SO₃ H基或者-COOH基的金屬鹽、-SO₃ H基或者-COOH基的烷基銨鹽、可具有取代基的鄰苯二甲醯亞胺甲基或可具有取代基的胺磺醯基。] [化11]

[式（5）中，R⁶³ ～R⁷⁰ 分別獨立地表示氫原子、鹵素原子、可具有取代基的烷基、可具有取代基的烷氧基、可具有取代基的芳基、-SO₃ H基、-COOH基、-SO₃ H基或者-COOH基的金屬鹽、-SO₃ H基或者-COOH基的烷基銨鹽、可具有取代基的鄰苯二甲醯亞胺甲基或可具有取代基的胺磺醯基。另外，R⁷¹ ～R⁷⁴ 分別獨立地表示氫原子、鹵素原子或下述式（6）所表示的鄰苯二甲醯亞胺系原子團。] [化12]

[式（6）中，X²¹ ～X²⁴ 分別獨立地表示氫原子或鹵素原子。]Item 3. The pigment composition according to Item 2, wherein the quinophthalone pigment is the following formula (4-1), formula (4-2), formula (4-3), formula (4-4), and At least any one of the quinophthalone compounds represented by formula (5), [formation 7]

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[In formula (4-1), formula (4-2), formula (4-3) and formula (4-4), R ³ ～R ¹⁵ , R ¹⁶ ～R ³⁰ , R ³¹ ～R ⁴⁵ and R ⁴⁶ ~R ⁶² each independently represents a hydrogen atom, a halogen atom, an optionally substituted alkyl group, an optionally substituted alkoxy group, an optionally substituted aryl group, -SO ₃ H group, -COOH group, -SO ₃ H group or -COOH group metal salt, -SO ₃ H group or -COOH group alkyl ammonium salt, optionally substituted phthaliminomethyl or optionally substituted sulfamoyl group . ] [化11]

[In formula (5), R ⁶³ to R ⁷⁰ each independently represent a hydrogen atom, a halogen atom, an optionally substituted alkyl group, an optionally substituted alkoxy group, an optionally substituted aryl group, -SO ₃ Metal salt of H group, -COOH group, -SO ₃ H group or -COOH group, _{alkyl ammonium salt of -SO 3} H group or -COOH group, optionally substituted phthaliminomethyl or Sulfamidine group which may have a substituent. In addition, R ⁷¹ to R ⁷⁴ each independently represent a hydrogen atom, a halogen atom, or a phthalimide-based atomic group represented by the following formula (6). ] [化12]

[In formula (6), X ²¹ to X ²⁴ each independently represent a hydrogen atom or a halogen atom. ]

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

Item 5. A color filter having a pixel portion containing the pigment composition according to any one of items 2 to 4. [Effects of the invention]

The quinophthalone compound of the present invention particularly exhibits an aggregation inhibitory effect on yellow pigments such as quinophthalone, and can be made into a pigment composition having good dispersibility and excellent color characteristics such as coloring power and vividness. In addition, 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 particularly excellent in brightness and contrast when used as a color filter.

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[Quinophthalone compound] The quinophthalone compound of the present invention mainly acts on yellow pigments such as quinophthalone as a pigment derivative, and is represented by the following formula (1). [化13]

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In the formula (1), R ¹ and R ² each independently represent a hydrogen atom, the phthalimide-based atomic group represented by the formula (2), or the imidine methyl group represented by the formula (3). X ¹ to X ^{16 in the} formula (1) and X ¹⁷ to X ²⁰ in the formula (2) each independently represent a hydrogen atom, a halogen atom, or an iminomethyl-based atomic group represented by the formula (3). At this time, the total number of the imidinyl radicals represented by the formula (3) in the formula (1) and the formula (2), R ¹ , R ^2, and X ¹ to X ^{20 is 1 to 4.} Y in formula (3) represents an arylene group, which can also be substituted by a halogen atom, an arylsulfonyl group, an acyl group or -(C=O)-C ₆ H ₄ -(C=O)- .

In terms of easily exerting the effect of inhibiting aggregation on the pigment, X ¹ to X ^{8 in} formula (1) and X ¹⁷ to X ²⁰ in formula (2) are preferably chlorine atoms and bromine atoms among halogen atoms, wherein More preferably, it is a chlorine atom. The number of the imine methyl group represented by the formula (3) is 1 to 4, among which 1 to 3 is preferred, and 1 to 2 is particularly preferred. Y in formula (3) represents an arylene group, which can also be substituted by a halogen atom, an arylsulfonyl group, an acyl group or -(C=O)-C ₆ H ₄ -(C=O)- . As the arylene group in Y, the phenylene group and the naphthylene group are preferable in terms of easily exhibiting the aggregation inhibitory effect on the pigment, and among them, the phenylene group is particularly preferable.

Examples of the quinophthalone compound of the present invention include compounds represented by the following formulas (1-1) to (1-15). In addition, n in the following formula represents the number of substituents of the iminomethyl radical, and represents an integer of 1-4. This imiminomethyl atom group is substituted with any hydrogen atom in the quinophthalone skeleton on the left. [化16]

[Production method of quinophthalone compound] The quinophthalone compound of the present invention is not particularly limited, and can be suitably produced by a conventionally known method. As an example of the production of the quinophthalone compound of the present invention, it is classified into compounds in which R ¹ and R ² in formula (1) are hydrogen atoms or the imidinyl group of atoms represented by formula (3) (the formula (1-1) to the compound of the formula (1-7)), the compound in which R ¹ and R ² in the formula (1) are the phthalimide atomic group represented by the formula (2) (the compound The compounds of formula (1-8) to formula (1-15)) will be described. All quinophthalone compounds of the present invention can be produced by referring to the following methods including the examples described later and appropriately changing the raw materials used.

First, as a compound in the case where R ¹ and R ² in formula (1) are a hydrogen atom or an iminomethyl-based atomic group represented by formula (3) (the above formula (1-1) to formula (1-7) The example of the compound of) will be described as a method for producing the compound of formula (1-1). The compound of the formula (1-1) can be obtained, for example, by a method including the following steps AI and steps A-II.

(Step AI) In step AI, after adding methyl benzoate under an acid catalyst such as benzoic acid and heating and melting, add tetrachlorophthalic anhydride and 6,6'-methylenebisquinalidine [e.g. Obtained by the method described in "Polymer", No. 39 (volume), No. 20 (1998), p4949], heating and stirring are performed to react, thereby obtaining the following formula (A-1) The intermediate shown. [化17]

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

(Step A-II) In step A-II, under sulfuric acid such as fuming sulfuric acid, add paraformaldehyde and phthalimide and stir, then add the formula (A-1) obtained in step AI The intermediate of is heated and stirred to react, whereby the quinophthalone compound represented by the formula (1-1) can be obtained.

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

Next, as a compound where R ¹ and R ² in formula (1) are the phthalimide-based atomic group represented by formula (2) (the above-mentioned formula (1-8) to formula (1-15)) As an example of the compound of formula (1-8), the method for producing the compound of formula (1-8) will be described. The compound of formula (1-8) can be obtained, for example, by a method including the following steps B1, B-II, B-III, and B-IV.

(Step BI) In step BI, in concentrated sulfuric acid and other sulfuric acid, add 6,6'-methylene quinalidine while stirring while cooling in an ice bath [for example, by "Polymer", 39 Period (volume), No.20(1998), p4949], and then add nitric acid dropwise while keeping the temperature below 10°C, and stir to react to obtain the following formula (B-1) The intermediate. [化18]

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

(Step B-II) In step B-II, with respect to 1 equivalent of the intermediate represented by formula (B-1) obtained in step BI, 6 to 8 equivalents of reduced iron are added to react, and In this way, an intermediate represented by the following formula (B-2) can be obtained. [化19]

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

(Step B-III) In step B-III, under an acid catalyst such as benzoic acid, the intermediate represented by formula (B-2) obtained in step B-II, tetrachlorophthalic anhydride, And the anhydrous zinc chloride is heated and stirred to react, thereby obtaining an intermediate represented by the following formula (B-3). Furthermore, the intermediate represented by the formula (B-3) can also be used as the quinophthalone pigment represented by the formula (5). [化20]

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

(Step B-IV) In step B-IV, under sulfuric acid such as fuming sulfuric acid, add paraformaldehyde and phthalimide and stir, then add the formula (B-3) obtained in step B-III The intermediate is heated, stirred and reacted, whereby the quinophthalone compound represented by the formula (1-8) can be obtained.

The reaction temperature in step B-IV is, for example, 20°C to 150°C, preferably 80°C to 120°C, and the reaction time is, for example, 1 hour to 8 hours, preferably 2 hours to 6 hours.

[Pigment composition] The pigment composition of the present invention contains a quinophthalone pigment and the quinophthalone compound represented by the formula (1). The pigment composition of the present invention only needs to contain at least one quinophthalone compound of the present invention, and may contain two or more quinophthalone compounds. In addition, the pigment composition of the present invention may contain components other than the quinophthalone pigment and the quinophthalone compound of the present invention.

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(Quinophthalone pigment) In the pigment composition of the present invention, as the quinophthalone pigment, for example, as long as it is a pigment having a quinophthalone skeleton synthesized by the condensation of quinaldine and phthalic anhydride, it is not There is no particular limitation. As such quinophthalone pigments, the following formula (4-1), formula (4-2), formula (4-3), formula (4-4) and formula (5) are preferred. Represents the quinophthalone pigment. [化21]

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In the formula (4-1), formula (4-2), formula (4-3) and formula (4-4), R ³ to R ¹⁵ , R ¹⁶ to R ³⁰ , R ³¹ to R ⁴⁵ and R ⁴⁶ to R ⁶² each independently represent a hydrogen atom, a halogen atom, an optionally substituted alkyl group, an optionally substituted alkoxy group, an optionally substituted aryl group, -SO ₃ H group, -COOH group,- SO ₃ H group or a -COOH group metal salt, ammonium salt -SO ₃ H group or a -COOH group, a phthaloyl may have a substituent (PEI) methyl group or an amine group substituted sulfonylurea base. In terms of excellent heat resistance, solvent resistance, and weather resistance, R ³ to R ¹⁰ , R ²² to R ²⁵ , and R ³¹ to R ^{34 are} preferably halogen atoms, and particularly preferably chlorine atoms. The R ¹¹ to R ¹⁵ , R ²⁶ to R ³⁰ , R ⁴¹ to R ⁴⁵ , and R ⁵⁸ to R ^{62 are} particularly preferably hydrogen atoms.

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In formula (5), R ⁶³ to R ⁷⁰ each independently represent a hydrogen atom, a halogen atom, an optionally substituted alkyl group, an optionally substituted alkoxy group, an optionally substituted aryl group, -SO ₃ H Group, -COOH group, -SO ₃ H group or -COOH group metal salt, -SO ₃ H group or -COOH group alkyl ammonium salt, optionally substituted phthaliminomethyl or may A substituted sulfamoyl group. In terms of solvent resistance, excellent weather resistance, heat resistance, said R6 ³ ~ R ⁷⁰ is preferably a halogen atom, which is preferably a chlorine atom. ^{In addition, R 71} to R ⁷⁴ in the formula (5) each independently represent a hydrogen atom, a halogen atom, or a phthalimide-based atomic group represented by the following formula (6). [化26]

In formula (6), X ²¹ to X ²⁴ each independently represent a hydrogen atom and a halogen atom. In terms of excellent heat resistance, solvent resistance, and weather resistance, the X ²¹ to X ^{24 are} preferably a halogen atom, and among them, a chlorine atom is preferred. Furthermore, as the halogen atom in the formula (4-1), formula (4-2), formula (4-3), formula (4-4), formula (5), and formula (6), for example, Examples include fluorine atom, chlorine atom, bromine atom, and iodine atom.

As a representative example of the quinophthalone pigment represented by the formula (4-1), pigment yellow (pigment yellow) 138 (Color Index, C.I.) can be cited. The quinophthalone pigments represented by formula (4-1), formula (4-2), formula (4-3), and formula (4-4) can be produced by the following method, for example. In addition, as these quinophthalone pigments, commercially available pigments may also be used.

The quinophthalone pigment represented by the formula (4-1), formula (4-2), formula (4-3), and formula (4-4) can be, for example, compared to 8-aminoquinalidine 1 equivalent to 2 to 3 equivalents of phthalic anhydride or naphthalenedicarboxylic acid anhydride, in benzoic acid, in a nitrogen atmosphere, heated at 160°C to 200°C to undergo condensation reaction. obtain. When only phthalic anhydrides are used in the reaction, the quinophthalone pigment represented by formula (4-1) can be obtained. When only naphthalenedicarboxylic acid anhydrides are used in the reaction, the quinophthalone pigment represented by formula (4-4) can be obtained. In addition, when phthalic anhydride and naphthalic anhydride are used in the reaction, quinophthalone pigments represented by formula (4-2) and formula (4-3) can be obtained.

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

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Furthermore, in the structure of formula (5), there are tautomers of structures such as the following formula (5-i) and formula (5-ii), and the quinophthalone pigment represented by the formula (5) It can be any of these structures. ^{In addition, R 63} to R ^{74 in} formula (5-i) and formula (5-ii) are the same as formula (5). [化32]

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The quinophthalone pigment represented by the formula (5) is not particularly limited. For example, the alkylene compound represented by the following formula (7) can be condensed with the acid anhydride represented by the following formula (8) Method to obtain. ^{In addition, R 72} , R ^74, and R ⁶³ to R ^{66 in} formula (7) and (8) are the same as formula (5) (R ⁶³ to R ⁶⁶ and R ⁶⁷ to R ^{70 are} substantially the same). The alkylene compound represented by formula (7) can be produced by the method described later. [化33]

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As a specific alkylene compound represented by formula (7), the compound represented by following formula (7-1) or (7-2) is mentioned, for example. As the alkylene compound represented by formula (7), one kind may be used alone, or two or more kinds may be combined. [化35]

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Specific examples of the acid anhydride represented by the formula (7) include phthalic anhydride and halogen-substituted phthalic anhydride, and specific examples of halogen-substituted phthalic anhydride include tetrafluorophthalic anhydride. , Tetrachlorophthalic anhydride, tetrabromophthalic anhydride, 4,5-dichlorophthalic anhydride, 4-chlorophthalic anhydride, 4,5-dibromophthalic anhydride, etc. . The acid anhydride represented by formula (7) may be used alone or in combination of two or more kinds. By using two or more different types of acid anhydrides as the acid anhydride represented by the formula (7), the formulas in which a plurality of R ⁶³ each, a plurality of R ⁶⁴ each, a plurality of R ⁶⁵ each, and a plurality of R ⁶⁶ each are different from each other can be obtained (5) The quinophthalone pigment represented.

The alkylene compound represented by the formula (7) can be obtained, for example, by a method including the following step CI, step C-II, and step C-III. ^{Furthermore, the plurality of R 72} and the plurality of R ^{74 in} formula (7-i) and formula (7-ii) may be the same or different from each other.

First, in step CI, by the method described in "J. Heterocyclic Chem (J. Heterocyclic, Chem)", 30, 17 (1993), etc., 2 to 3 equivalents of dianiline are added to 1 equivalent of dianiline Crotonaldehyde is reacted in a strong acid in the presence of an oxidizing agent to synthesize a compound of the following formula (7-i). [化37]

Here, as a strong acid, hydrochloric acid, sulfuric acid, nitric acid, etc. are mentioned. Examples of the oxidizing agent include sodium iodide, p-Chloranil, nitrobenzene, and the like. The reaction temperature in step C-I is, for example, 80°C to 100°C, preferably 90°C to 100°C, and the reaction time is, for example, 1 hour to 6 hours, preferably 3 hours to 6 hours.

Furthermore, in step C-II, by reacting the obtained compound of formula (7-i) with nitric acid or fuming nitric acid in the presence of concentrated sulfuric acid, a compound of the following formula (7-ii) can be obtained. [化38]

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

Furthermore, in step C-III, the nitro group (-NO ₂ ) is converted into an amino group (-NH ₂ ) by the reduction of the obtained compound of formula (7-ii), thereby obtaining the formula (7) The alkylene compound represented by.

In step C-III, for example, by reducing the compound of formula (7-ii) with reduced iron, the alkylene compound represented by formula (7) can be obtained. At this time, relative to 1 equivalent of the compound of formula (7-ii), the amount of reduced iron may be 6 to 8 equivalents, the reaction temperature may be 40 to 80°C, preferably 50 to 70°C, and the reaction time may be It is 0.5 hour to 12 hours, preferably 1 hour to 3 hours. In addition, by using metal catalysts such as palladium-carbon (Pd-C), platinum-carbon (Pt-C), and Raleigh nickel to reduce the compound of formula (7-ii), formula (7) can also be obtained The represented alkylene compound. At this time, the amount of the metal catalyst may be 0.4% to 5% by mass of the compound of formula (7-ii) in terms of metal amount, the reaction temperature may be, for example, 30°C to 100°C, and the reaction time may be, for example, 1 hour. ~10 hours. As the hydrogen source for the reaction, hydrogen gas, hydrazine, ammonium formate, etc. can be used.

[Contents of components in the pigment composition] The content of the quinophthalone compound represented by the formula (1) in the pigment composition of the present invention relative to the entire pigment composition is, for example, 1% to 15% by mass, preferably 2% to 10% by mass , More preferably 3% by mass to 8% by mass. In addition, relative to 100 parts by mass of the pigment, the content of the quinophthalone compound represented by the formula (1) is, for example, 1 part by mass to 20 parts by mass, preferably 2 parts by mass to 15 parts by mass, more preferably 3 parts by mass Parts ~ 10 parts by mass. When the content of the quinophthalone compound is in the above range, the dispersibility is good, and color characteristics such as coloring power and vividness are excellent.

With respect to the total amount of the pigment composition, the formula (4-1), formula (4-2), formula (4-3), formula (4-4) and formula (5) in the pigment composition of the present invention The total content of the quinophthalone pigments represented is, for example, 5 mass% to 98 mass%, preferably 10 mass% to 95 mass%, and more preferably 15 mass% to 90 mass%. In the pigment composition of the present invention, the quinone represented by the formula (4-1), formula (4-2), formula (4-3), formula (4-4) and formula (5) can also be used. Pigments described later other than phthalone pigments. The total amount of quinophthalone pigments represented by the formula (4-1), formula (4-2), formula (4-3), formula (4-4), and formula (5) relative to the total amount of yellow pigment The content is, for example, 90% by mass or more, preferably 95% by mass or more, and more preferably 99% by mass or more.

In the pigment composition of the present invention, it is preferable to easily exhibit the characteristics of the quinophthalone compound represented by the formula (1), which has good dispersibility and excellent color characteristics such as coloring power and vividness. Contains the quinophthalone pigment represented by formula (5). The content of the quinophthalone pigment represented by the formula (5) when the quinophthalone pigment represented by the formula (5) is contained relative to the total amount of the pigment composition is, for example, 1% by mass to 80% by mass, preferably 2% by mass to 70% by mass, more preferably 3% by mass to 60% by mass.

In addition, the quinophthalone pigment represented by the formula (4-1), the formula (4-2), the formula (4-3) and the formula (4-4) and the quinophthalone pigment represented by the formula (5) are used in combination In the case of a ketone pigment, relative to the total content of the quinophthalone pigment contained in the pigment composition, the content of the quinophthalone pigment represented by the formula (5) is, for example, 30% by mass to 95% by mass, preferably 40% by mass. Mass% to 90% by mass, more preferably 50% to 85% by mass. In addition, when two or more types of quinophthalone pigments represented by the formula (5) are contained, the content is the total content.

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

In the pigment composition of the present invention, as pigments, pigments other than quinophthalone pigments, such as azo pigments, phthalocyanine pigments, azomethine, anthraquinone, isoindoline, and isoindoline, may also be included. Condensed polycyclic pigments such as ketones, dioxazines, perylenes, quinacridones, and diketopyrrolopyrroles.

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

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

[Color filter] The color filter of the present invention has a pixel portion containing the pigment composition of the present invention. Regarding the color filter, the following method called photolithography can be cited, that is, adding a solvent or the like to the pigment composition to make a coloring composition (or adding a photosensitive resin to make a photosensitive coloring composition), and use The coloring composition (photosensitive coloring composition) is coated on a transparent substrate such as a glass substrate by a spin coating method, a roll coating method, an inkjet method, etc., and then the coating film is patterned with ultraviolet rays through a photomask After exposure, the unexposed part is washed with an organic solvent, alkaline water, etc., to obtain a colored pattern. The method of forming the pixel portion is not particularly limited. For example, the pattern of the pixel portion may be formed by methods such as electroplating, transfer, microcell electrolysis, photovoltaic electrodeposition (Photovoltaic Electrodeposition, PVED), etc., to produce color Filter.

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 a part of the pigment that forms the green pixel portion or the blue pixel portion together with the existing green color material or blue color material. In addition, 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 organic solvents include aromatic solvents such as toluene, xylene, and methoxybenzene; acetate-based solvents such as ethyl acetate or butyl acetate, propylene glycol monomethyl ether acetate, and propylene glycol monoethyl ether acetate. Solvents; 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; N,N-dimethylformamide, γ-butyrolactamide, N -Methyl-2-pyrrolidone, aniline, pyridine and other nitrogen compound solvents; γ-butyrolactone and other lactone solvents; such as a 48:52 mixture of methyl carbamate and ethyl carbamate Carbamate and so on. The organic solvent is preferably a solvent that is polar and soluble in water, and more preferably a propionate-based solvent, an alcohol-based solvent, an ester-based solvent, a ketone-based solvent, a nitrogen compound-based solvent, or a lactone-based solvent.

[化40]

The coloring composition may further contain color materials such as organic pigments and organic dyes other than the quinophthalone pigment, pigment derivatives other than the quinophthalone compound represented by the formula (1), and the like. Examples of organic pigments other than the above include: phthalocyanine pigments (green color materials) such as CI Pigment Green 36, 58, 59, 62, and 63, as shown in the following formulas (8-1) and (8-2) The indicated aluminum phthalocyanine pigment or the mixture with yellow pigment (green color material), CI pigment blue 15:6 and other epsilon type copper phthalocyanine pigment (blue color material), CI pigment red 177 and other dianthraquinone-based pigments, CI pigment Red 254 and other diketopyrrolopyrrole pigments, CI Pigment Red 269 and other naphthol-based azo pigments (the above are red color materials). [化39]

[化40]

^{A 1} to A ⁴ and A ⁵ to A ^{12 in} the formula (8-1) and formula (8-2) each independently represent an alkyl group that may have a substituent, an aryl group that may have a substituent, and Substituent cycloalkyl group, optionally substituted heterocyclic group, optionally substituted alkoxy group, optionally substituted aryloxy group, optionally substituted alkylthio group or optionally substituted arylsulfide base. ^{D 1} to D ⁴ and D ⁵ to D ^{12 in} the formula (8-1) and formula (8-2) each independently represent a halogen atom, a nitro group, and optionally substituted phthalimide A methyl group or a sulfasulfonyl group which may have a substituent. ^{Z 1} in the formula (8-1) represents a hydroxyl group, a chlorine atom, -OP(=O)R ₁ R ₂ or -O-SiR ₃ R ₄ R ₅ . Here, R ₁ to R ₅ each independently represent a hydrogen atom, a hydroxyl group, an optionally substituted alkyl group, an optionally substituted aryl group, an optionally substituted alkoxy group, or an optionally substituted aryloxy group , R can be bonded to each other to form a ring. ^{Z 2} in the formula (8-2) represents -O-SiR ₆ R ₇ -O-, -O-SiR ₆ R ₇ -O-SiR ₈ R ₉ -O- or -OP(=O)R ₁₀ -O-, R ₆ to R ₁₀ each independently represent a hydrogen atom, a hydroxyl group, an optionally substituted alkyl group, an optionally substituted aryl group, an optionally substituted alkoxy group, or an optionally substituted aryloxy group base. A1 to a4, a5 to a12, d1 to d4, and d5 to d12 in the formula (8-1) and formula (8-2) each independently represent an integer of 0 to 4, a1+d1, a2+d2, a3+d3, a4+d4, a5+d5, a6+d6, a7+d7, a8+d8, a9+d9, a10+d10, a11+d11, a12+d12 are integers from 0 to 4, which can be the same or Can be different.

The coloring composition may further contain a dispersant. Examples of dispersants include: ANTI-TERRA (registered trade name) U/U100, ANTI-TERRA (registered trade name) 204, DISPERBYK (Registered trade name) 106, DISPERBYK (registered trade name) 108, DISPERBYK (registered trade name) 109, DISPERBYK (registered trade name) 112. DISPERBYK (registered trademark) 130, DISPERBYK (registered trademark) 140, DISPERBYK (registered trademark) 142, DISPERBYK (registered trademark) DISPERBYK (registered trademark name) 145, DISPERBYK (registered trademark name) 161, DISPERBYK (registered trademark name) 162, DISPERBYK (DISPERBYK) (Registered trade name) 163, DISPERBYK (registered trade name) 164, DISPERBYK (registered trade name) 167, DISPERBYK (registered trade name) 168, DISPERBYK (registered trade name) 180, DISPERBYK (registered trade name) 182, DISPERBYK (registered trade name) 183, DISPERBYK (registered trade name) DISPERBYK (registered trademark) 184, DISPERBYK (registered trademark) 185, DISPERBYK (registered trademark) 2000, DISPERBYK (Registered trade name) 2001, DISPERBYK (registered trade name) 2008, DISPERBYK (registered trade name) 2009, DISPERBYK (registered trade name) 2013, DISPERBYK (registered trade name) 2022, DISPERBYK (registered trade name) 2025, DISPERBYK (registered trade name) 2026, Disper DISPERBYK (registered trademark name) 2050, DISPERBYK (registered trademark name) 2055, DISPERBYK (registered trademark name) 2150, DISPERBYK (DISPERBYK) (Registered trademark name) 2155, DISPERBYK (registered trademark name) 2163, DISPERBYK (registered trademark name) 2164, DISPERBYK (registered trademark name) 907 6. DISPERBYK (registered trademark) 9077, BYK LPN-6919, BYK LPN-21116, BYK LPN-21324, BYK LPN -22102 (manufactured by BYK Chemie Co., Ltd.), EFKA (registered trademark) 46, EFKA (registered trademark) 47, EFKA (registered trademark) 4010, EFKA (registered trademark) 4020, EFKA ( Registered trademark name) 4320, EFKA (registered trademark name) 4300, EFKA (registered trademark name) 4330, EFKA (registered trademark name) 4401, EFKA (registered trademark name) 4570, EFKA (registered trademark name) 5054, EFKA (registered trademark) Name) 7461, EFKA (registered trademark name) 7462, EFKA (registered trademark name) 7476, EFKA (registered trademark name) 7477 (made by BASF Co., Ltd.), Ajisper (registered trademark name) PB814, Ajisper (registered trademark) PB821, Ajisper (registered trademark) PB822, Ajisper (registered trademark) PB881 (Ajinomoto Fine Technology ( Ajinomoto Fine-Techno Co., Ltd.), Solsperse (registered trademark) 24000, Solsperse (registered trademark) 28000, Solsperse (registered trademark) ) 37500, Solsperse (registered trademark) 76500 (manufactured by Lubrizol Co., Ltd.), etc.

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

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

The coloring composition may further contain photosensitive resin. The coloring composition containing a photosensitive resin may also be called a photosensitive coloring composition. Examples of photosensitive resins include: urethane resins, acrylic resins, polyamide resins, polyimide resins, styrene maleic acid resins, and styrene maleic anhydride resins. Thermoplastic resins such as 1,6-hexanediol diacrylate, ethylene glycol diacrylate, neopentyl glycol diacrylate, triethylene glycol diacrylate, bis(acryloxyethoxy) Bifunctional monomers such as bisphenol A and 3-methylpentanediol diacrylate, such as trimethylolpropane triacrylate, pentaerythritol triacrylate, and tris-(2-propenyloxyethyl) iso Photopolymerizable monomers such as polyfunctional monomers such as cyanurate, dipentaerythritol hexaacrylate, and dipentaerythritol pentaacrylate.

The photosensitive coloring composition may further contain a photopolymerization initiator. As the photopolymerization initiator, for example, acetophenone, benzophenone, benzyl dimethyl ketal, benzyl peroxide, 2-chlorothioxanthone, 1,3-bis(4' -Azidobenzylidene)-2-propane, 1,3-bis(4'-azidobenzylidene)-2-propane-2'-sulfonic acid, 4,4'-diazide stilbene- 2,2'-Disulfonic acid, etc.

The quinophthalone compound represented by the formula (1) in an amount of 1 to 20 parts by mass relative to 100 parts by mass of the quinophthalone pigment and an organic solvent of 300 to 2000 parts by mass to become uniform Stirring and dispersing in this way, a dispersion (coloring composition) can be obtained. Next, 3 parts by mass to 25 parts by mass of photosensitive resin relative to 100 parts by mass of the dispersion liquid and 0.05 parts by mass to 3 parts by mass of light relative to 1 part by mass of photosensitive resin are added to the dispersion. The polymerization initiator (organic solvent added as necessary) is stirred and dispersed so as to become uniform, and a photosensitive color composition can be obtained.

When the coloring composition (photosensitive coloring composition) is used to form the green pixel portion of the color filter, with respect to 100 parts by mass of the quinophthalone pigment, 200 parts by mass or less of green color material and/ Or 200 parts by mass or less of blue color material. [Example]

The present invention will be explained more specifically with examples, but the present invention is not limited to the form of the following examples. First, the quinophthalone compound (pigment derivative) and the quinophthalone pigment were obtained by the method described in the following Synthesis Example 1-Synthesis Example 6. Next, pigmentation was performed using the obtained quinophthalone compound and quinophthalone pigment by the method described in Pigmentation Example 1-Pigmentation Example 6, to obtain a pigment composition. Then, the composition for yellow toning was produced by the methods described in Example 1 to Example 4 and Comparative Example 1 to Comparative Example 2, and the contrast measurement of the finally obtained color filter was performed.

傅立葉轉換紅外光譜（Fourier Transform Infrared Spectroscopy，FT-IR）（KBr disk）cm^-1 ：1682、1636、1618、1590、1538、1420、1382、1306、730 FD-MS：834M+[Synthesis Example 1] Into a flask, 234 g of benzoic acid and 133 g of methyl benzoate were added, and the mixture was heated and dissolved at 160°C under a nitrogen stream. After that, 46.1 g of tetrachlorophthalic anhydride was added, 6,6' obtained by the method described in the literature ("Polymer", Issue 39 (volume), No.20(1998), p4949)) -Methylenebisquinalidine 9.1 g, stirred at 200°C for 5 hours. After cooling, add 440 mL of N-methyl pyrrolidone (NMP, N-methyl pyrrolidone), perform hot filtration at 80°C, and wash with NMP. Dissolve the gel in 200 mL of methanol, heat and stir at 60°C for 1 hour. After being left to cool, 25.2 g of intermediate (9) was obtained as a yellow powder by filtration, washing with methanol, and drying under reduced pressure. [化41]

Fourier Transform Infrared Spectroscopy (FT-IR) (KBr disk) cm ^-1 : 1682, 1636, 1618, 1590, 1538, 1420, 1382, 1306, 730 FD-MS: 834M+

FT-IR（KBr disk）cm^-1 ：1773、1716、1629、1610、1537、1417、1400、1304、728 FD-MS：993（n=1）、1152（n=2）、1311（n=3）M+[Synthesis Example 2] A flask was charged with 24.4 g of 3.6% oleum, 6.8 g of paraformaldehyde and 14.4 g of phthalimide were added, and the mixture was stirred at room temperature for 30 minutes. Then, 5 g of the intermediate (9) obtained in Synthesis Example 1 was added, and stirred at 100°C for 3 hours. After leaving to cool, add 173 g of ice water, stir at 60°C for 30 minutes, and filter the precipitate. It was washed three times with warm water and air-dried at 90°C to obtain 6.76 g of the quinophthalone compound (10) as a brown powder. [化42]

FT-IR (KBr disk) cm ^-1 : 1773, 1716, 1629, 1610, 1537, 1417, 1400, 1304, 728 FD-MS: 993 (n=1), 1152 (n=2), 1311 (n= 3) M+

氫譜核磁共振（¹ H-nuclear magnetic resonance，¹ H-NMR）（二甲基亞碸（dimethylsulfoxide，DMSO）-d6）δppm：2.70(s, 6H), 4.42(s, 2H), 7.58(d, J=8.8 Hz, 2H), 7.63(d, J=8.8 Hz, 2H), 8.09(d, J=8.8 Hz, 2H), 8.13(d, J=8.8 Hz, 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[Synthesis Example 3] Put 55 g of concentrated sulfuric acid into a flask, and add it while stirring while cooling in an ice bath. According to the literature ("Polymer", Vol. 39, No. 20 (1998), p4949) ) 6,6'-methylenebisquinalidine 7.0 g obtained by the method described. While keeping the temperature below 10°C, add 6.1 g of 60% nitric acid dropwise, and continue stirring from 10°C to 20°C for 1 hour. The reaction liquid was poured into 150 ml of ice water, and the pH was adjusted to 3 using a 20 wt% sodium hydroxide aqueous solution. The precipitated powder was recovered by filtration under reduced pressure, and washed to neutrality with water. 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 of intermediate (11). [化43]

¹ H-nuclear magnetic resonance (1 H-nuclear magnetic resonance, ¹ H-NMR) (dimethylsulfoxide (DMSO)-d6) δppm: 2.70(s, 6H), 4.42(s, 2H), 7.58(d , J=8.8 Hz, 2H), 7.63(d, J=8.8 Hz, 2H), 8.09(d, J=8.8 Hz, 2H), 8.13(d, J=8.8 Hz, 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

¹ H-NMR（DMSO-d6）δppm：2.57(s, 6H) ,3.45(s, 2H) ,5.66(s, 4H), 7.06(d, J=8.2 Hz, 2H), 7.16(d, J=8.2 Hz, 2H), 7.23(d, J=8.2 Hz, 2H), 8.49(d, J=8.2 Hz, 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[Synthesis Example 4] A flask was charged with 5.30 g of reduced iron and 135 ml of acetic acid, and heated to 50°C while stirring. Next, 4.50 g of the intermediate (11) obtained in Synthesis Example 3 was added so as to be kept at 70°C or lower. After the addition, stirring was continued at 60°C for 1 hr, then the reaction solution was cooled to below 35°C, poured into 500 ml of ice water, and the pH was adjusted to 9 with 20% NaOH water. The formed precipitate was filtered under reduced pressure on diatomaceous earth. Recover the solids and dry them with air at 70°C. Add 100 ml of dimethyl sulfide (DMSO) and 100 ml of N,N-dimethylformamide (DMF) to a mixed solvent at 90°C. Stir for 1 hr. The mixture was filtered on diatomaceous earth under reduced pressure, and the obtained filtrate was added to 1 L of water while stirring. The generated precipitate was recovered by filtration under reduced pressure and washed with water to obtain 3.80 g of intermediate (12). [化44]

¹ H-NMR (DMSO-d6) δppm: 2.57(s, 6H), 3.45(s, 2H), 5.66(s, 4H), 7.06(d, J=8.2 Hz, 2H), 7.16(d, J= 8.2 Hz, 2H), 7.23(d, J=8.2 Hz, 2H), 8.49(d, J=8.2 Hz, 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-IRcm^-1 ：1788, 1729, 1688, 1638, 1607, 1537, 1420, 1310, 732 FD-MS：1399M+[Synthesis Example 5] Under a nitrogen atmosphere, 135 g of benzoic acid was weighed into a flask and melted at 140°C. 3.80 g of the intermediate (12) obtained in Synthesis Example 4, 17.99 g of tetrachlorophthalic anhydride, and 0.49 g of anhydrous zinc chloride were added thereto, and the mixture was stirred at 220°C for 6 hours. After cooling the reaction mixture to 120°C, 300 mL of chlorobenzene was added and stirred for 1 hour, and filtered under reduced pressure to obtain 10.5 g of quinophthalone pigment (13) as a yellow powder. [化45]

FT-IRcm ^-1 :1788, 1729, 1688, 1638, 1607, 1537, 1420, 1310, 732 FD-MS: 1399M+

FD-MS：1559（n=1）M+[Synthesis Example 6] A flask was charged with 73.2 g of 3.6% fuming sulfuric acid, 12.2 g of paraformaldehyde and 3.78 g of phthalimide were added, and the mixture was stirred at room temperature for 30 minutes. Then, 5 g of the quinophthalone pigment (13) obtained in Synthesis Example 5 was added, and the mixture was stirred at 120°C for 3 hours. After standing to cool, add 518 g of ice water, stir at 60°C for 30 minutes, and filter the precipitate. It was washed three times with warm water and air-dried at 90°C to obtain 14.4 g of quinophthalone compound (14) as a brown powder. [化46]

FD-MS: 1559 (n=1) M+

[Pigmentation Example 1] 47.5 g of the quinophthalone pigment (13) obtained in Synthesis Example 5 was ground together with 2.5 g of the quinophthalone compound (10) obtained in Synthesis Example 2, 400 g of sodium chloride, and 66.6 g of diethylene glycol. After that, the mixture was poured into 2000 g of warm water and stirred for 1 hour. The water-insoluble components are separated by filtration and thoroughly washed with warm water, and then air-dried at 90°C.

[Pigmentation example 2] In place of the quinophthalone compound (10) obtained in Synthesis Example 2 as an iminomethyl derivative, the quinophthalone compound (14) obtained in Synthesis Example 6 was used. 1 Perform pigmentation in the same way.

[Pigmentation Example 3] The amount of the quinophthalone pigment (13) obtained in Synthesis Example 5 was changed from 47.5 g to 48.5 g, and the amount of the quinophthalone compound (10) obtained in Synthesis Example 2 was changed from 2.5 to 1.5 g. , Pigmentation was carried out by the same method as in Pigmentation Example 1.

[Pigmentation Example 4] The amount of the quinophthalone pigment (13) obtained in Synthesis Example 5 was changed from 47.5 g to 46.5 g, and the amount of the quinophthalone compound (10) obtained in Synthesis Example 2 was changed from 2.5 to 3.5 g. , Pigmentation was carried out by the same method as in Pigmentation Example 1.

[Pigmentation Example 5] 50 g of the quinophthalone pigment (13) obtained in Synthesis Example 5 was ground together with 400 g of sodium chloride and 66.6 g of diethylene glycol. After that, the mixture was poured into 2000 g of warm water and stirred for 1 hour. The water-insoluble components are separated by filtration, thoroughly washed with warm water, and air-dried at 90°C.

[Pigmentation Example 6] The quinophthalone compound (10) obtained in Synthesis Example 2 as the iminomethyl derivative was replaced with the iminomethyl derivative of CI Pigment Yellow 138 synthesized by the method described in Japanese Patent Laid-Open No. 2013-54200 Except for this, the pigmentation was carried out by the same method as in Pigmentation Example 1.

[Example 1] Put 0.8 g of the quinophthalone pigmented composition obtained in pigmentation example 1 into a glass bottle, and add 13.25 g of propylene glycol monomethyl ether acetate, DISPERBYK (registered trademark) LPN-6919 (Manufactured by BYK Chemie Co., Ltd.) 0.4 g, acrylic resin solution UNIDIC (registered trademark) ZL-295 (manufactured by DIC Co., Ltd.) 0.6 g, 0.3 mmφ-0.4 22.0 g of mmφ ceramic beads (sepr beads) were dispersed for 2.5 hours with a paint stirrer (manufactured by Toyo Seiki Co., Ltd.) to obtain a pigment dispersion. The content of the pigments and derivatives in Example 1 is shown in Table 1 below. Furthermore, 3.6 g of these pigment dispersions and 0.6 g of the acrylic resin solution UNIDIC (registered trademark) ZL-295 (manufactured by DIC Co., Ltd.) were put into a glass bottle, shaken, and This produces a composition for yellow toning. After coating the obtained composition for yellow toning on a glass substrate by a spin coater, it was made to dry. After heating the obtained glass substrate for evaluation at 230 degreeC for 1 hour, the contrast measurement was performed using the contrast tester (Contrast tester (CONTRAST TESTER) CT-1 manufactured by Kesaka Electric Co., Ltd.). The measurement results are shown in Table 1. In addition, the contrast is the value when the coating film thickness is 1 μm.

[Example 2] The quinophthalone pigmented composition obtained in Pigmentation Example 1 was replaced with the quinophthalone pigmented composition obtained in Pigmentation Example 2, except that the same method as in Example 1 was used to produce yellow toning The composition was measured for contrast.

[Example 3] The quinophthalone pigmented composition obtained in Pigmentation Example 1 was replaced with the quinophthalone pigmented composition obtained in Pigmentation Example 3, except that the same method as in Example 1 was used to produce yellow toning The composition was measured for contrast.

[Example 4] The quinophthalone pigmented composition obtained in Pigmentation Example 1 was replaced with the quinophthalone pigmented composition obtained in Pigmentation Example 4, except that the same method as in Example 1 was used to produce yellow toning The composition was measured for contrast.

[Comparative Example 1] The quinophthalone pigmented composition obtained in Pigmentation Example 1 was replaced with the quinophthalone pigmented composition obtained in Pigmentation Example 5, except that the same method as in Example 1 was used to produce yellow toning The composition was measured for contrast.

[Comparative Example 2] The quinophthalone pigmented composition obtained in Pigmentation Example 1 was replaced with the quinophthalone pigmented composition obtained in Pigmentation Example 6, except that the same method as in Example 1 was used to produce yellow toning The composition was measured for contrast.

[Table 1] Example 1 Example 2 Example 3 Example 4 Comparative example 1 Comparative example 2 pigment Quinophthalone yellow pigment (13) 47.5 g 47.5 g 48.5 g 46.5 g 50 g 47.5 g derivative Quinophthalone compounds (10) 2.5 g 0 1.5 g 3.5 g 0 0 Quinophthalone compounds (14) 0 2.5 g 0 0 0 0 The imine methylated derivative of Pigment Yellow 138 0 0 0 0 0 2.5 g Contrast 3770 3340 3554 4286 2366 3229

As shown in Table 1, in Example 1 to Example 4, a color filter having a higher contrast ratio than Comparative Example 1 to Comparative Example 2 can be obtained. From the results, it was confirmed that the combination of a quinophthalone pigment and a specific quinophthalone-based derivative can realize a color filter with excellent contrast.

Claims (5)

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

In the formula (1), R ¹ and R ² each independently represent a hydrogen atom, a phthalimide-based atomic group represented by the formula (2), or an amide methyl group represented by the formula (3); X ¹ to X ^{16 in} (1) and X ¹⁷ to X ²⁰ in formula (2) each independently represent a hydrogen atom, a halogen atom, or an iminomethyl-based atomic group represented by formula (3); in this case, ^{R 1} , R ^{2 in} formula (1) and formula (2), and the total number of imidinyl radicals represented by formula (3) in ^{X 1} to X ^{20 are 1 to 4; formula (3)} Y represents an arylene group, and the arylene group may be substituted by a halogen atom, an arylsulfonyl group, an acyl group, or -(C=O)-C ₆ H ₄ -(C=O)-. A pigment composition comprising a quinophthalone pigment and a quinophthalone compound represented by the following formula (1),

In the formula (1), R ¹ and R ² each independently represent a hydrogen atom, a phthalimide-based atomic group represented by the formula (2), or an amide methyl group represented by the formula (3); X ¹ to X ^{16 in} (1) and X ¹⁷ to X ²⁰ in formula (2) each independently represent a hydrogen atom, a halogen atom, or an iminomethyl-based atomic group represented by formula (3); in this case, ^{R 1} , R ^{2 in} formula (1) and formula (2), and the total number of imidinyl radicals represented by formula (3) in ^{X 1} to X ^{20 are 1 to 4; formula (3)} Y represents an arylene group, and the arylene group may be substituted by a halogen atom, an arylsulfonyl group, an acyl group, or -(C=O)-C ₆ H ₄ -(C=O)-. The pigment composition according to claim 2, wherein the quinophthalone pigment is the following formula (4-1), formula (4-2), formula (4-3), formula (4-4) and formula (5) At least any one of the quinophthalone compounds represented,

In formula (4-1), formula (4-2), formula (4-3) and formula (4-4), R ³ ～R ¹⁵ , R ¹⁶ ～R ³⁰ , R ³¹ ～R ⁴⁵ and R ⁴⁶ ～ R ⁶² each independently represents a hydrogen atom, a halogen atom, an optionally substituted alkyl group, an optionally substituted alkoxy group, an optionally substituted aryl group, -SO ₃ H group, -COOH group, -SO ₃ The metal salt of the _{H group or the -COOH group, the alkylammonium salt of the -SO 3} H group or the -COOH group, the phthaliminomethyl group which may have a substituent, or the sulfasulfonyl group which may have a substituent,

In formula (5), R ⁶³ to R ⁷⁰ each independently represent a hydrogen atom, a halogen atom, an optionally substituted alkyl group, an optionally substituted alkoxy group, an optionally substituted aryl group, -SO ₃ H Group, -COOH group, -SO ₃ H group or -COOH group metal salt, -SO ₃ H group or -COOH group alkyl ammonium salt, optionally substituted phthaliminomethyl or may A substituted sulfamoyl group; and R ⁷¹ to R ⁷⁴ each independently represent a hydrogen atom, a halogen atom, or a phthalimide-based atomic group represented by the following formula (6),

In formula (6), X ²¹ to X ²⁴ each independently represent a hydrogen atom or a halogen atom. The pigment composition according to claim 2 or 3, which is used in a color filter. A color filter having a pixel portion containing the pigment composition according to any one of claims 2 to 4.