JP2020033523A - Pigment composition, coloring composition, and color filter - Google Patents

Abstract

To provide a pigment composition excellent in the luminance, tinctorial power and contrast.SOLUTION: The pigment composition contains a quinophthalone compound represented by formula (1), and a quinophthalone-based derivative having at least one sulfonic acid group, sulfonic acid base or the like. [X-X, Yand Yare each independently H or a halogen atom; and Z is a C1-3 alkylene group.]SELECTED DRAWING: None

Description

  The present invention relates to a pigment composition, a coloring composition, and a color filter.

  At present, coloring compositions are used in various fields. Specific uses of the coloring compositions include printing inks, paints, coloring agents for resins, coloring agents for fibers, coloring materials for IT information recording (color filters). , Toner, and inkjet). Dyes used in the coloring composition are required to have color characteristics (coloring power, sharpness), resistance (weather resistance, light resistance, heat resistance, solvent resistance) and the like. Dyes are mainly classified into pigments and dyes, but pigments are different from dyes that develop color in a molecular state, and develop color in a particle state (aggregates of primary particles). For this reason, pigments are generally superior to dyes in terms of resistance, but are inferior in coloring power and chroma (clearness).

  From such a background, pigments having high coloring power and high chroma are demanded, and attention is particularly paid to organic pigments, which are considered to be dominant in terms of coloring power. For example, Patent Document 1 discloses a coloring composition containing a predetermined quinophthalone compound.

JP 2012-247587 A

  By the way, pigments intended for color filters are required to have different properties from general-purpose applications. Specifically, for example, “high brightness” for reducing the power consumption of the backlight, “high coloring power” for thinning the color filters and high color reproduction, and the like are required. However, the coloring composition disclosed in Patent Literature 1 does not always provide sufficient luminance and coloring power when a color filter is used. That is, the coloring composition disclosed in Patent Literature 1 has room for further improvement in terms of increasing luminance and obtaining high color reproducibility even in a thin film.

  Further, for color filters, there is a demand for “high contrast” for realizing clear images. However, in a coloring composition containing a pigment composed of fine particles, coarse particles may be generated due to aggregation of the pigment, and the coarse particles may cause a decrease in contrast.

  Therefore, an object of the present invention is to provide a coloring composition containing a pigment having excellent luminance and coloring power, and in which a decrease in contrast due to aggregation of the pigment is sufficiently suppressed. Another object of the present invention is to provide a pigment composition capable of forming the above-mentioned coloring composition, and a color filter formed using the above-mentioned coloring composition.

  The present inventors have conducted intensive studies to solve the above problems, and found that a specific quinophthalone compound obtained by dimerizing a quinophthalone skeleton becomes a yellow pigment having excellent luminance and coloring power, and also has a quinophthalone skeleton. The present inventors have found that a specific derivative can suppress the aggregation of the yellow pigment and realize high contrast, and have completed the present invention.

［式（１）中、Ｘ^１〜Ｘ^１６は各々独立に水素原子又はハロゲン原子であり、Ｙ^１及びＹ^２は各々独立に水素原子又はハロゲン原子であり、Ｚは炭素数１〜３のアルキレン基である。］

［式（２）中、Ｒ^１〜Ｒ^１０は各々独立に水素原子、ハロゲン原子、下記式（２−ａ）：

で表されるフタルイミド系原子団、又は、−（Ｌ^１−Ｌ^２）_ｎ−Ｇで表される基を示す。
Ｘ^２１〜Ｘ^２４は各々独立に水素原子、ハロゲン原子、又は、−（Ｌ^１−Ｌ^２）_ｎ−Ｇで表される基を示す。
Ｇは、スルホン酸基、スルホン酸塩基、カルボン酸基又はカルボン酸塩基を示し、ｎは０以上の整数を示し、Ｌ^１は−Ｏ−で表される基又は−ＮＨ−で表される基を示し、Ｌ^２は置換基を有していてもよいアルキレン基、置換基を有していてもよいアルケニレン基又は置換基を有していてもよいアリーレン基を示す。
但し、Ｒ^１〜Ｒ^１０のうち少なくとも一つは、−（Ｌ^１−Ｌ^２）_ｎ−Ｇで表される基、又は、−（Ｌ^１−Ｌ^２）_ｎ−Ｇで表される基を有する前記フタルイミド系原子団である。］

［式（３）中、Ｒ^１１〜Ｒ^２８は各々独立に水素原子、ハロゲン原子、下記式（３−ａ）：

で表されるフタルイミド系原子団、又は、−（Ｌ^１−Ｌ^２）_ｎ−Ｇで表される基を示し、Ｌは炭素数１〜３のアルキレン基を示す。
Ｘ^３１〜Ｘ^３４は各々独立に水素原子、ハロゲン原子、又は、−（Ｌ^１−Ｌ^２）_ｎ−Ｇで表される基を示す。
Ｇは、スルホン酸基、スルホン酸塩基、カルボン酸基又はカルボン酸塩基を示し、ｎは０以上の整数を示し、Ｌ^１は−Ｏ−で表される基又は−ＮＨ−で表される基を示し、Ｌ^２は置換基を有していてもよいアルキレン基、置換基を有していてもよいアルケニレン基又は置換基を有していてもよいアリーレン基を示す。
但し、Ｒ^１１〜Ｒ^２８のうち少なくとも一つは、−（Ｌ^１−Ｌ^２）_ｎ−Ｇで表される基、又は、−（Ｌ^１−Ｌ^２）_ｎ−Ｇで表される基を有する前記フタルイミド系原子団である。］ One aspect of the present invention is a quinophthalone compound represented by the following formula (1), at least one selected from the group consisting of a compound represented by the following formula (2) and a compound represented by the following formula (3): And a quinophthalone-based derivative of the above.

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

[In the formula (2), R ^{1 to} R ¹⁰ are each independently a hydrogen atom, a halogen atom, the following formula (2-a):

And a group represented by-(L ¹ -L ² ) _n -G.
X ^{21 to} X ²⁴ each independently represent a hydrogen atom, a halogen atom, or a group represented by-(L ¹ -L ² ) _n -G.
G represents a sulfonic acid group, a sulfonic acid group, a carboxylic acid group or a carboxylic acid group, n represents an integer of 0 or more, and L ¹ represents a group represented by —O— or a group represented by —NH—. are shown, L ² represents a substituent alkylene group which may have a which may have a substituent alkenylene group or an optionally substituted arylene group.
However, at least one of R ^{1 to} R ¹⁰ is a group represented by-(L ¹ -L ² ) _n -G or a group represented by-(L ¹ -L ² ) _n -G. The phthalimide-based atomic group having the above. ]

[In the formula (3), R ^{11 to} R ²⁸ each independently represent a hydrogen atom, a halogen atom, a compound represented by the following formula (3-a):

And a group represented by-(L ¹ -L ² ) _n -G, and L represents an alkylene group having 1 to 3 carbon atoms.
X ^{31 to} X ³⁴ each independently represent a hydrogen atom, a halogen atom, or a group represented by-(L ¹ -L ² ) _n -G.
G represents a sulfonic acid group, a sulfonic acid group, a carboxylic acid group or a carboxylic acid group, n represents an integer of 0 or more, and L ¹ represents a group represented by —O— or a group represented by —NH—. are shown, L ² represents a substituent alkylene group which may have a which may have a substituent alkenylene group or an optionally substituted arylene group.
However, at least one of R ^{11 to} R ²⁸ is a group represented by-(L ¹ -L ² ) _n -G or a group represented by-(L ¹ -L ² ) _n -G. The phthalimide-based atomic group having the above. ]

  In one aspect, n may be 0 or 1.

  Another aspect of the present invention is selected from the group consisting of a quinophthalone compound represented by the above formula (1), a compound represented by the above formula (2), and a compound represented by the above formula (3). It is a coloring composition containing at least one quinophthalone derivative and a solvent.

  Still another aspect of the present invention is a quinophthalone compound represented by the above formula (1), or a quinophthalone compound selected from the group consisting of a compound represented by the above formula (2) and a compound represented by the above formula (3). A color filter having a pixel portion containing at least one quinophthalone derivative.

  ADVANTAGE OF THE INVENTION According to this invention, the coloring composition containing the pigment which has the outstanding brightness | luminance and coloring power is provided, and the fall of the contrast resulting from the aggregation of the said pigment was suppressed sufficiently. Further, according to the present invention, there are provided a pigment composition capable of forming the coloring composition, and a color filter formed using the coloring composition.

(Pigment composition)
The pigment composition according to one embodiment is selected from the group consisting of a quinophthalone compound represented by the following formula (1), a compound represented by the following formula (2), and a compound represented by the following formula (3). At least one quinophthalone derivative.

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

で表されるフタルイミド系原子団、又は、−（Ｌ^１−Ｌ^２）_ｎ−Ｇで表される基を示す。Ｘ^２１〜Ｘ^２４は各々独立に水素原子、ハロゲン原子、又は、−（Ｌ^１−Ｌ^２）_ｎ−Ｇで表される基を示す。Ｇは、スルホン酸基、スルホン酸塩基、カルボン酸基又はカルボン酸塩基を示し、ｎは０以上の整数を示し、Ｌ^１は−Ｏ−で表される基又は−ＮＨ−で表される基を示し、Ｌ^２は置換基を有していてもよいアルキレン基、置換基を有していてもよいアルケニレン基又は置換基を有していてもよいアリーレン基を示す。但し、Ｒ^１〜Ｒ^１０のうち少なくとも一つは、−（Ｌ^１−Ｌ^２）_ｎ−Ｇで表される基、又は、−（Ｌ^１−Ｌ^２）_ｎ−Ｇで表される基を有する上記フタルイミド系原子団（すなわち、Ｘ^２１〜Ｘ^２４のうち少なくとも一つが−（Ｌ^１−Ｌ^２）_ｎ−Ｇで表される基である、式（２−ａ）で表されるフタルイミド系原子団）である。 In the formula (2), R ^{1 to} R ¹⁰ are each independently a hydrogen atom, a halogen atom, and the following formula (2-a):

And a group represented by-(L ¹ -L ² ) _n -G. X ^{21 to} X ²⁴ each independently represent a hydrogen atom, a halogen atom, or a group represented by-(L ¹ -L ² ) _n -G. G represents a sulfonic acid group, a sulfonic acid group, a carboxylic acid group or a carboxylic acid group, n represents an integer of 0 or more, and L ¹ represents a group represented by —O— or a group represented by —NH—. are shown, L ² represents a substituent alkylene group which may have a which may have a substituent alkenylene group or an optionally substituted arylene group. However, at least one of R ^{1 to} R ¹⁰ is a group represented by-(L ¹ -L ² ) _n -G or a group represented by-(L ¹ -L ² ) _n -G. the phthalimide atomic group having ^(i.e., at least one of X 21 ^{to X 24} is ^{- (L 1} is -L ₂₎ a group represented by n -G, phthalimide represented by the formula (2-a) Atomic group).

で表されるフタルイミド系原子団、又は、−（Ｌ^１−Ｌ^２）_ｎ−Ｇで表される基を示し、Ｌは炭素数１〜３のアルキレン基を示す。Ｘ^３１〜Ｘ^３４は各々独立に水素原子、ハロゲン原子、又は、−（Ｌ^１−Ｌ^２）_ｎ−Ｇで表される基を示す。Ｇは、スルホン酸基、スルホン酸塩基、カルボン酸基又はカルボン酸塩基を示し、ｎは０以上の整数を示し、Ｌ^１は−Ｏ−で表される基又は−ＮＨ−で表される基を示し、Ｌ^２は置換基を有していてもよいアルキレン基、置換基を有していてもよいアルケニレン基又は置換基を有していてもよいアリーレン基を示す。但し、Ｒ^１１〜Ｒ^２８のうち少なくとも一つは、−（Ｌ^１−Ｌ^２）_ｎ−Ｇで表される基、又は、−（Ｌ^１−Ｌ^２）_ｎ−Ｇで表される基を有する上記フタルイミド系原子団（すなわち、Ｘ^３１〜Ｘ^３４のうち少なくとも一つが−（Ｌ^１−Ｌ^２）_ｎ−Ｇで表される基である、式（３−ａ）で表されるフタルイミド系原子団）である。 In the formula (3), R ^{11 to} R ²⁸ each independently represent a hydrogen atom, a halogen atom, the following formula (3-a):

And a group represented by-(L ¹ -L ² ) _n -G, and L represents an alkylene group having 1 to 3 carbon atoms. X ^{31 to} X ³⁴ each independently represent a hydrogen atom, a halogen atom, or a group represented by-(L ¹ -L ² ) _n -G. G represents a sulfonic acid group, a sulfonic acid group, a carboxylic acid group or a carboxylic acid group, n represents an integer of 0 or more, and L ¹ represents a group represented by —O— or a group represented by —NH—. are shown, L ² represents a substituent alkylene group which may have a which may have a substituent alkenylene group or an optionally substituted arylene group. However, at least one of R ^{11 to} R ²⁸ is a group represented by-(L ¹ -L ² ) _n -G or a group represented by-(L ¹ -L ² ) _n -G. the phthalimide atomic group having ^(i.e., X 31 ^{to X} at least one of ^{34 -} a ^{(L 1} -L ₂₎ a group represented by n -G, phthalimide represented by the formula (3-a) Atomic group).

  The quinophthalone compound exhibits selective absorption and transmission due to dimerization of the quinophthalone skeleton. In the quinophthalone compound, the quinophthalone skeleton is dimerized using the linking group Z as a spacer, whereby conjugation is cut off and excessive redness is suppressed. Further, the quinophthalone compound has improved dispersibility by introducing an imide structure. From these facts, according to the quinophthalone compound, a pigment having excellent luminance and coloring power can be obtained. Specifically, for example, a yellow pigment composed of the above quinophthalone compound has better luminance than a yellow pigment generally used at present (CI Pigment Yellow 150), and has an excellent luminance exceeding this. Coloring power.

  Since the quinophthalone-based derivative has a quinophthalone skeleton, it can be firmly adsorbed on the surface of the pigment composed of the quinophthalone compound. The adsorption of the quinophthalone-based derivative on the surface of the pigment significantly improves the dispersibility of the pigment, and suppresses a decrease in contrast due to aggregation of the pigment.

  The halogen atom in the formula (1) may be a fluorine atom, a chlorine atom, a bromine atom or an iodine atom, preferably a fluorine atom, a chlorine atom or a bromine atom, and more preferably a chlorine atom.

  Specific examples of the alkylene group having 1 to 3 carbon atoms in the formula (1) include, for example, a methylene group, an ethylene group (1,1-ethanediyl group or 1,2-ethanediyl group), a propylene group (1,1- A propanediyl group, a 2,2-propanediyl group, a 1,2-propanediyl group or a 1,3-propanediyl group), and a methylene group, a 1,1-ethanediyl group, a 1,1-propanediyl group, , 2-propanediyl group is more preferable, and methylene group is further preferable.

In the quinophthalone compound, at least one of X ^{1 to} X ¹⁶ is preferably a halogen atom, and more preferably two or more are halogen atoms. When a halogen atom is introduced into X ^{1 to} X ¹⁶ , the dispersibility of the quinophthalone compound is further improved, and the above effects tend to be more remarkably obtained.

At least one of X ^{1 to} X ⁴ is preferably a halogen atom, more preferably two or more are halogen atoms, and all may be halogen atoms. Further, it is preferable that at least one of X ² and X ³ is a halogen atom, more preferably X ² and X ³ are each a halogen atom.

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

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

At least one of X ^{13 to} X ¹⁶ is preferably a halogen atom, more preferably two or more are halogen atoms, and all may be halogen atoms. It is preferred that at least one is a halogen atom of X ¹⁴ and ^{X 15,} and more preferably ^{X 14} and ^{X 15} are each a halogen atom.

Y ¹ and Y ² may be the same or different, but are preferably the same from the viewpoint of facilitating the synthesis of the quinophthalone compound.

In the structure of the formula (1), tautomers of the following formulas (1-i) and (1-ii) exist, and the quinophthalone compound has any of these structures. You may.

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

  Specific examples of the quinophthalone compound are shown below, but the quinophthalone compound is not limited to these.

  The method for producing the quinophthalone compound is not particularly limited, and can be produced by appropriately utilizing a conventionally known method. Hereinafter, one embodiment of a method for producing a quinophthalone compound will be described, but the production method is not limited thereto.

  The quinophthalone compound can be obtained, for example, by a method including the following Step I, Step II, Step III and Step IV.

<Step I>
First, J. According to the method described in Heterocyclic, Chem, 30, 17, (1993) or the like, 2 to 3 equivalents of crotonaldehyde are added to 1 equivalent of bisaniline, and the reaction is carried out in a strong acid in the presence of an oxidizing agent. The compound of -1) is synthesized.

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

  Here, examples of the strong acid include hydrochloric acid, sulfuric acid, nitric acid and the like. Examples of the oxidizing agent include sodium iodide, p-chloranil, nitrobenzene, and the like.

  For Step I, the reaction temperature may be from 80C to 100C, preferably from 90C to 100C, and the reaction time may be from 1 hour to 6 hours, preferably from 3 hours to 6 hours.

<Step II>
Further, the compound of formula (A-2) can be obtained by reacting the obtained compound of formula (A-1) with nitric acid or fuming nitric acid in the presence of concentrated sulfuric acid.

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

  For Step II, the reaction temperature may be from -20C to 70C, preferably from 0C to 50C, and the reaction time may be from 1 hour to 4 hours, preferably from 1 hour to 3 hours.

<Step III>
Furthermore, the compound of the formula (A-3) can be obtained by adding 6 to 8 equivalents of reduced iron to 1 equivalent of the obtained compound of the formula (A-2) and reacting.

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

  For Step III, the reaction temperature may be from 60C to 80C, preferably from 70C to 80C, and the reaction time may be from 1 hour to 3 hours, preferably from 2 hours to 3 hours.

<Step IV>
Furthermore, at least one selected from the group consisting of phthalic anhydride and halogen-substituted phthalic anhydride is used per equivalent of the compound of the formula (A-3) obtained by the method described in JP-A-2013-61622. The compound of the formula (1) can be obtained by reacting one kind with 4 to 6 equivalents in the presence of an acid catalyst.

  Here, examples of the acid catalyst include benzoic acid and zinc chloride.

  For Step IV, the reaction temperature may be between 180C and 250C, preferably between 210C and 250C, and the reaction time may be between 1 hour and 8 hours, preferably between 3 hours and 8 hours.

  The above quinophthalone compounds may be used alone, or two or more compounds may be appropriately selected and used in combination.

  The quinophthalone compound can exhibit properties as an organic pigment. The quinophthalone compound may be compounded in the form of a pigment. In other words, the pigment composition according to the present embodiment may contain a yellow pigment composed of the quinophthalone compound.

  The quinophthalone compound may be converted into a pigment by a known and commonly used method. The yellow pigment composed of the quinophthalone compound may be finely divided by, for example, a salt milling treatment. In addition, the yellow pigment may be surface-treated by a method such as rosin treatment, surfactant treatment, solvent treatment, and resin treatment.

  The compound represented by the formula (2) has a polar group (preferably a sulfonic acid group or a sulfonic acid group) selected from the group consisting of a sulfonic acid group, a sulfonic acid group, a carboxylic acid group and a carboxylic acid group in one molecule. Has at least one, preferably one or two, and more preferably one.

In the present specification, a sulfonic acid group, a group represented by -SO 3 _H, sulfonate group, a group formed by the reaction of a sulfonic acid group and a base. Further, the carboxylic acid group, a group represented by -CO 2 _H, carboxylic acid base, a group formed by reaction of a carboxylic acid group and a base.

The sulfonate group may be a group composed of an anionic group represented by —SO ₃ ^— and a counter cation. Further, the carboxylate group may be a group composed of an anionic group represented by —CO ₂ ^— and a counter cation.

The counter cation is not particularly limited, and may be, for example, a metal cation, an ammonium cation (NH ₄ ⁺ ), or the like.

The metal cation may be, for example, a 1-3 valent metal cation. Examples of the monovalent metal cation include a lithium cation (Li ⁺ ), a sodium cation (Na ⁺ ), and a potassium cation (K ⁺ ). Examples of the divalent metal cation include a magnesium cation (Mg ²⁺ ) and a calcium cation (Ca ²⁺ ). Examples of the trivalent metal cation include an aluminum cation (Al ³⁺ ).

As the counter cation, a monovalent cation (a monovalent metal cation, an ammonium cation, or the like) is preferable, a monovalent metal cation is more preferable, and a sodium cation (Na ⁺ ) and a potassium cation (K ⁺ ) are still more preferable.

  The halogen atom in the formula (2) may be a fluorine atom, a chlorine atom, a bromine atom or an iodine atom, preferably a fluorine atom, a chlorine atom or a bromine atom, more preferably a chlorine atom.

In the formula (2), R ^{7 to} R ¹⁰ are preferably a hydrogen atom or a halogen atom. In addition, at least one of R ^{7 to} R ¹⁰ is preferably a halogen atom, more preferably two or more are halogen atoms, and all four may be halogen atoms. It is preferable that at least one of R ⁸ and R ⁹ is a halogen atom, more preferably R ⁸ and R ⁹ are each a halogen atom.

R ^{7 to} R ¹⁰ are preferably the same as X ^{1 to} X ⁴ in the quinophthalone compound, respectively. Further, R ^{7 to} R ¹⁰ are preferably the same as X ^{13 to} X ¹⁶ in the quinophthalone compound, respectively.

In the formula (2), at least one of R ^{1 to} R ⁶ may be a phthalimide-based atomic group. At this time, it is more preferable that one or two of R ^{1 to} R ⁶ are a phthalimide-based atomic group, and it is further preferable that one is a phthalimide-based atomic group. Further, at least one of R ¹ , R ⁴ and R ⁵ is preferably a phthalimide-based atomic group, and more preferably, R ¹ or R ⁴ is a phthalimide-based atomic group.

In the formula (2-a), at least one of X ^{21 to} X ²⁴ is preferably a halogen atom, more preferably two or more halogen atoms, and even if all four are halogen atoms. Good. ^Further, it is preferable that at least one of ^{X 22} and ^{X 23} is a halogen ^atom, more preferably both of ^{X 22} and ^{X 23} is a halogen atom.

In the formula (2), at least one of R ^{1 to} R ¹⁰ is preferably a group represented by-(L ¹ -L ² ) _n -G, and at least one of R ^{1 to} R ⁶ is-( L ¹ -L ² ) a group represented by _n- G is more preferred.

  The compound represented by the formula (3) has at least one polar group selected from the group consisting of a sulfonic acid group, a sulfonic acid group, a carboxylic acid group, and a carboxylic acid group in one molecule. It is preferable to have four, more preferably one or two.

  The halogen atom in the formula (3) may be a fluorine atom, a chlorine atom, a bromine atom or an iodine atom, preferably a fluorine atom, a chlorine atom or a bromine atom, more preferably a chlorine atom.

In the formula (3), R ^{16 to} R ¹⁹ are preferably a hydrogen atom or a halogen atom. Further, at least one of R ^{16 to} R ¹⁹ is preferably a halogen atom, more preferably two or more are halogen atoms, and all four may be halogen atoms. ^It is preferable that at least one of ^{R 17} and ^{R 18} is a halogen ^atom, more preferably ^{R 17} and ^{R 18} are each a halogen atom. R ^{16 to} R ¹⁹ are preferably the same as X ^{1 to} X ⁴ in the quinophthalone compound, respectively.

In the formula (3), R ^{25 to} R ²⁸ are preferably a hydrogen atom or a halogen atom. Further, at least one of R ^{25 to} R ²⁸ is preferably a halogen atom, more preferably two or more halogen atoms, and all four may be halogen atoms. ^It is preferable that at least one of ^{R 26} and ^{R 27} is a halogen ^atom, more preferably ^{R 26} and ^{R 27} are each a halogen atom. R ^{25 to} R ²⁸ are preferably the same as X ^{13 to} X ¹⁶ in the quinophthalone compound, respectively.

In the formula (3), at least one of R ^{11 to} R ¹⁵ may be a phthalimide-based atomic group. At this time, it is more preferable that one or two of R ^{11 to} R ¹⁵ are a phthalimide-based atomic group, and it is further preferable that one is a phthalimide-based atomic group. Further, at least one of R ¹¹ and R ¹³ is preferably a phthalimide-based atomic group, and more preferably R ¹³ is a phthalimide-based atomic group.

In the formula (3), at least one of R ^{11 to} R ¹⁹ is preferably a group represented by-(L ¹ -L ² ) _n -G, and at least one of R ^{11 to} R ¹⁵ is-( L ¹ -L ² ) a group represented by _n- G is more preferred.

In the formula (3), at least one of R ^{20 to} R ²⁴ is preferably a phthalimide-based atomic group, more preferably one or two is a phthalimide-based atomic group, and one is a phthalimide-based atomic group. Is more preferable. Further, at least one of R ²⁰ and R ²² is preferably a phthalimide-based atomic group, and more preferably, R ²² is a phthalimide-based atomic group.

In the formula (3), at least one of R ^{20 to} R ²⁸ is preferably a group represented by-(L ¹ -L ² ) _n -G, and at least one of R ^{20 to} R ²⁴ is-( L ¹ -L ² ) a group represented by _n- G is more preferred.

  As the alkylene group for L in the formula (3), the same groups as the groups exemplified as the alkylene group in the formula (1) can be mentioned. L in the formula (3) is preferably the same group as Z in the formula (1).

In the formula (3-a), at least one of X ^{31 to} X ³⁴ is preferably a halogen atom, more preferably two or more halogen atoms, and even if all four are halogen atoms. Good. ^Further, it is preferable that at least one of ^{X 32} and ^{X 33} is a halogen ^atom, more preferably both of ^{X 32} and ^{X 33} is a halogen atom.

The quinophthalone derivative has a structure in which at least one polar group selected from the group consisting of a sulfonic acid group, a sulfonic acid group, a carboxylic acid group, and a carboxylic acid group is linked to a quinophthalone skeleton. With the quinophthalone skeleton and the polar group, the above-described excellent effects are exhibited. Here, the polar group may be directly bonded to the quinophthalone skeleton, or may be bonded to the quinophthalone skeleton via a linking group represented by-(L ¹ -L ² ) _n- .

  n is 0 or more, preferably 0 to 3, more preferably 0 to 2, and even more preferably 0 or 1. Note that n = 0 indicates that the polar group (G) is directly bonded.

L ¹ represents a group represented by —O— or a group represented by —NH—, and is preferably —NH—.

L ² represents an alkylene group, alkenylene group or arylene group, and these groups may have a substituent. Examples of the substituent include a halogen atom, an alkyl group, a halogenated alkyl group, an aryl group, a nitro group, a hydroxy group, an alkoxy group, a sulfonic group, a sulfonic group, a carboxylic group, and a carboxylic group.

Alkylene group L ² is a straight-chain, branched, may be cyclic, or combinations thereof. L number of carbon atoms in the alkylene group ² is preferably 1 to 12, more preferably 1 to 8, more preferably 1 to 5, 1 to 4 being more preferred.

Alkenylene group L ² is a straight-chain, branched, may be cyclic, or combinations thereof. L number of carbon atoms of the alkenylene group ^2, 3 to 12, more preferably from 3 to 8, more preferably 3-5. The alkenylene group can be said to be a group in which at least one of the CH—CH bonds in the alkylene group has been converted to a C ＝ C bond.

The arylene group L ^2, such as a phenylene group, and naphthalene-diyl group.

L ² is preferably an alkylene group which may have a substituent, more preferably an unsubstituted alkylene group.

  In the pigment composition according to the present embodiment, the content ratio of the quinophthalone compound and the quinophthalone-based derivative is not particularly limited, and is applied to the particle size and surface area of the yellow pigment composed of the quinophthalone compound, and to a color filter. It may be appropriately changed according to the desired film thickness at that time.

  The content of the quinophthalone-based derivative is, for example, 1 part by mass or more, preferably 2 parts by mass or more, more preferably 3 parts by mass or more, and more preferably higher contrast, with respect to 100 parts by mass of the quinophthalone compound. From the viewpoint of facilitation, 4 parts by mass or more is preferable, and 5 parts by mass or more is more preferable. The content of the quinophthalone-based derivative may be, for example, 20 parts by mass or less, preferably 15 parts by mass or less, more preferably 10 parts by mass or less, based on 100 parts by mass of the quinophthalone compound.

  The pigment composition according to the present embodiment may be in a powder form. By dispersing the pigment composition according to this embodiment in a solvent, a coloring composition that is a pigment dispersion can be formed.

  The pigment composition according to the present embodiment may further contain components other than those described above. For example, the pigment composition may further contain coloring materials such as organic pigments and organic dyes other than those described above, organic pigment derivatives, and the like. The organic pigment derivative may be, for example, a derivative in which a part of a known organic pigment is modified (substituted) with a sulfonic acid group, a carboxylic acid group, a phthalimidomethyl group, or the like.

  The colorant that can be used in combination may be a known pigment, dye, or the like, and may be appropriately selected depending on the use of the pigment composition. Examples of pigments that can be used in combination include, for example, azo pigments, disazo pigments, azomethine pigments, anthraquinone pigments, quinophthalone pigments, quinacridone pigments, diketopyrrolopyrrole pigments, dioxazine pigments, benzimidazolone pigments, Examples include phthalocyanine pigments, isoindoline pigments, isoindolinone pigments, perylene pigments, and the like. Examples of dyes that can be used in combination include, for example, xanthene dyes, azo dyes, disazo dyes, anthraquinone dyes, quinophthalone dyes, triarylmethane dyes, methine dyes, phthalocyanine dyes, rhodamine dyes, and the like. No.

  Among the pigments that can be used in combination, C.I. I. Pigment Yellow 3, 12, and 74, and C.I. I. Pigment Yellow 74, 83, 109, 110 and the like. I. Pigment Yellow 83, 129, 138, 139, 150, 185, 231 and the like. Preferably C.I. I. Pigment Yellow 129, 138, 139, 150, 185, 231 and the like.

  In color filter applications, a yellow pigment is often used for toning a green pixel portion in combination with a green pigment or a blue pigment. From this viewpoint, the pigment composition according to the present embodiment may be used in combination with a green pigment or a blue pigment.

  The green pigment and the blue pigment are not particularly limited, and may be publicly known green pigments and blue pigments. Examples of the green pigment include C.I. I. Pigment Green 1, 2, 4, 7, 8, 10, 13, 13, 14, 15, 17, 18, 19, 26, 36, 45, 48, 48 50, 51, 54, 55, 58, 59, 62, 63 and the like. Examples of the blue pigment include C.I. I. Pigment Blue 15, 15: 1, 15: 2, 15: 3, 15: 4, and 15: 6. Preferably C.I. I. Pigment Green 7, 36, 58, 59, 62, 63 and the like. Examples of the blue pigment include an aluminum phthalocyanine derivative.

  Here, examples of the aluminum phthalocyanine derivative include a compound represented by the following formula (4-1).

  In the formula (4-1), R represents a halogen atom, a hydroxy group, or a group represented by the following formula (4-2).

  In the formula (4-2), X represents a direct bond or an oxygen atom. Ar represents a phenyl group or a naphthyl group. In the formula (4-2), an asterisk indicates a binding site.

  Examples of the halogen atom for R in the formula (4-1) include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Among them, the halogen atom for R is preferably a chlorine atom or a bromine atom.

  In the formula (4-1), R is preferably a chlorine atom, a bromine atom, a hydroxy group, or a group represented by the formula (4-2).

  In the formula (4-2), X is preferably an oxygen atom.

  Of the formula (4-1), preferred are, for example, hydroxyaluminum phthalocyanine, chloroaluminum phthalocyanine, bromoaluminum phthalocyanine, a compound represented by the following formula (4-1-1), and a compound represented by the following formula (4-1-2) And the compound represented by the following formula (4-1-3).

  The pigment composition according to this embodiment may further 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 may be added by, for example, surface treatment of a pigment composed of the quinophthalone compound. The surface treatment of the pigment may be a known method such as a rosin treatment, a surfactant treatment, a solvent treatment, and a resin treatment.

(Coloring composition)
The coloring composition according to the present embodiment contains the quinophthalone compound, the quinophthalone-based derivative, and a solvent.

  Such a coloring composition has excellent luminance and coloring power derived from the quinophthalone compound. Further, in the coloring composition, the quinophthalone-based derivative suppresses a decrease in contrast, color separation, pigment sedimentation, and the like due to the aggregation of the quinophthalone compound.

  The aspects of the quinophthalone compound and the quinophthalone derivative in the coloring composition may be the same as the aspects of the quinophthalone compound and the quinophthalone derivative in the pigment composition, respectively.

  In the coloring composition, the content ratio of the quinophthalone compound and the quinophthalone-based derivative is not particularly limited, and the particle size and surface area of the yellow pigment composed of the quinophthalone compound, and a desired film when applied to a color filter It may be appropriately changed according to the thickness and the like.

  The content of the quinophthalone-based derivative is, for example, 1 part by mass or more, preferably 2 parts by mass or more, more preferably 3 parts by mass or more, and more preferably higher contrast, with respect to 100 parts by mass of the quinophthalone compound. From the viewpoint of facilitation, 4 parts by mass or more is preferable, and 5 parts by mass or more is more preferable. The content of the quinophthalone-based derivative may be, for example, 20 parts by mass or less, preferably 15 parts by mass or less, more preferably 10 parts by mass or less, based on 100 parts by mass of the quinophthalone compound.

  As the solvent, an organic solvent is preferable. Examples of the organic solvent include aromatic solvents such as toluene, xylene and methoxybenzene, ethyl acetate and butyl acetate, acetic acid ester solvents such as propylene glycol monomethyl ether acetate and propylene glycol monoethyl ether acetate, and ethoxyethyl propionate. Propionate solvents, alcohol solvents such as methanol and ethanol, ether solvents such as butyl cellosolve, propylene glycol monomethyl ether, diethylene glycol ethyl ether, diethylene glycol dimethyl ether, ketone solvents such as methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, and fats such as hexane Group hydrocarbon solvents, N, N-dimethylformamide, γ-butyrolactam, N-methyl-2-pyrrolidone, aniline Emissions, nitrogen compound-based solvent such as pyridine, a lactone-based solvents such as γ- butyrolactone, carbamic acid esters such as a mixture of 48:52 of methyl carbamate and ethyl carbamate acid. The organic solvent is preferably a solvent that is polar and soluble in water, more preferably a propionate-based solvent, an alcohol-based solvent, an ether-based solvent, a ketone-based solvent, a nitrogen compound-based solvent, or a lactone-based solvent. is there.

  The coloring composition may further contain components other than those described above. For example, the coloring composition may further contain coloring materials such as organic pigments and organic dyes other than those described above, organic pigment derivatives, and the like. Examples of the coloring material and the organic pigment derivative include the same coloring material and organic pigment derivative that may be used in the above-described pigment composition.

  The coloring composition may further contain a dispersant as a component other than the above. Examples of the dispersing agent include ANTI-TERRA (registered trademark) U / U100, 204, DISPERBYK (registered trademark) 106, 108, 109, 112, 130, 140, 142, 145, 161, 162, 163, 164, 167, 168, 180, 182, 183, 184, 185, 2000, 2001, 2008, 2009, 2013, 2022 , 2025, 2026, 2050, 2055, 2150, 2155, 2163, 2164, 9076, 9077, BYK LPN-6919, 21116, 21324, 22102 (manufactured by Big Chemie Co., Ltd.) , EFKA (registered trademark) 46, 47, 4010, 4020, 4320, 430 4330, 4401, 4570, 5054, 7461, 7462, 7476, 7777 (manufactured by BASF), Azispar (registered trademark) PB814, 821, 822, 881 (Ajinomoto Fine Technos), Solsperse (registered trademark) 24000, 28000, 37500, and 76500 (manufactured by Lubrizol).

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

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

  The coloring composition may further contain a photosensitive resin. A coloring composition containing a photosensitive resin can also be referred to as a photosensitive coloring composition. Examples of the photosensitive resin include a thermoplastic resin such as a urethane resin, an acrylic resin, a polyamide acid resin, a polyimide resin, a styrene maleic acid resin, and a styrene maleic anhydride resin, and, for example, 1,6-hexanediol. Bifunctional monomers such as diacrylate, ethylene glycol diacrylate, neopentyl glycol diacrylate, triethylene glycol diacrylate, bis (acryloxyethoxy) bisphenol A, 3-methylpentanediol diacrylate, trimethylolpropane triacrylate, Such as pentaerythritol triacrylate, tris- (2-acryloyloxyethyl) isocyanurate, dipentaerythritol hexaacrylate, dipentaerythritol pentaacrylate, etc. Such photopolymerizable monomers such as functional monomers.

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

  The coloring composition may be prepared, for example, by mixing the above-mentioned pigment composition and a solvent, or may be prepared by mixing the above-mentioned quinophthalone compound, the above-mentioned quinophthalone-based derivative, and a solvent.

  In the present embodiment, for example, 1 to 20 parts by mass of the quinophthalone-based derivative and 300 to 2000 parts by mass of an organic solvent are stirred and dispersed so as to be uniform with respect to 100 parts by mass of the quinophthalone compound to obtain a dispersion ( Coloring composition) can be obtained. Next, 3 to 25 parts by mass of a photosensitive resin per 100 parts by mass of the dispersion, and 0.05 to 3 parts by mass of a photopolymerization initiator per 1 part by mass of the photosensitive resin are added to the dispersion (optionally, ), And the mixture is stirred and dispersed so as to be uniform to obtain a photosensitive colored composition.

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

(Color filter)
The color filter according to this embodiment has a pixel portion containing the quinophthalone compound and the quinophthalone-based derivative. The pixel portion may be a green pixel portion or a red pixel portion.

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

  The method for forming the pixel portion is not particularly limited. For example, a pattern of the pixel portion may be formed by an electrodeposition method, a transfer method, a micelle electrolysis method, or a PVED (Photovoltaic Electrodeposition) method to manufacture a color filter. .

^１Ｈ−ＮＭＲ（ＣＤＣｌ_３）δｐｐｍ：２．８１（ｓ，６Ｈ），４．２４（ｓ，２Ｈ），７．３４（ｄ，Ｊ＝８．０Ｈｚ，２Ｈ），７．４９（ｓ，２Ｈ），７．６７（ｓ，２Ｈ），７．９９（ｄ，Ｊ＝８．８Ｈｚ，２Ｈ）
^１３Ｃ−ＮＭＲ（ＣＤＣｌ_３）δｐｐｍ：２５．８，４１．１，１２３．２，１２６．２，１２７．８，１３０．９，１３３．１，１３６．３，１３７．６，１４３．１，１６０．０
ＦＴ−ＩＲ ｃｍ^−１：３４３５，３０５４，３０３０，２９１５，１６０３，１４８７，１２０６
ＦＤ−ＭＳ：３６６Ｍ＋ [Synthesis Example 1]
5.00 g (56.1 mmol) of 4,4'-methylenebis (2-chloroaniline), 27.6 g (112 mmol) of p-chloranil, 150 ml of water, 150 ml of concentrated hydrochloric acid and 100 ml of n-butanol were added to the flask, and the mixture was added to the flask. Stirred at C for 30 minutes. To this mixture was added dropwise 11.8 g (168 mmol) of crotonaldehyde dissolved in 12 ml of n-butanol, and the mixture was further stirred for 1 hour. The temperature was lowered to 80 ° C., and 15.3 g (112 mmol) of zinc chloride was added little by little. Then, 200 ml of THF was added, and the mixture was stirred for 1 hour while maintaining the temperature at 80 ° C. After allowing to cool to room temperature, ocher powder was recovered by vacuum filtration. The obtained ocher powder was washed with 200 ml of THF, and the ocher powder was recovered by vacuum filtration again. Further, the obtained ocher powder was transferred to a flask, 200 ml of water and 40 ml of 28% aqueous ammonia were added, and the mixture was stirred at room temperature for 2 hours. The powder was recovered by vacuum filtration to obtain 20.3 g of a crude product. The obtained crude product was dissolved in toluene, insolubles were removed by filtration, and then recrystallized to obtain 12.6 g of Intermediate (5). (Yield: 61%)

¹ H-NMR (CDCl ₃ ) δ ppm: 2.81 (s, 6H), 4.24 (s, 2H), 7.34 (d, J = 8.0 Hz, 2H), 7.49 (s, 2H) ), 7.67 (s, 2H), 7.99 (d, J = 8.8 Hz, 2H)
¹³ C-NMR (CDCl ₃ ) δ ppm: 25.8, 41.1, 123.2, 126.2, 127.8, 130.9, 133.1, 136.3, 137.6, 137.6, 143.1. 160.0
FT-IR cm- ¹ : 3435, 3054, 3030, 2915, 1603, 1487, 1206
FD-MS: 366M +

^１Ｈ−ＮＭＲ（ＣＤＣｌ_３）δｐｐｍ：２．８６（ｓ，６Ｈ），４．２７（ｓ，２Ｈ），７．５６（ｄ，Ｊ＝８．８Ｈｚ，２Ｈ），７．６２（ｓ，２Ｈ），８．０８（ｄ，Ｊ＝８．８Ｈｚ，２Ｈ）
^１３Ｃ−ＮＭＲ（ＣＤＣｌ_３）δｐｐｍ：２５．７，３２．４，１１９．９，１２５．６，１２７．５，１３０．１，１３１．１，１３７．３，１４３．１，１４５．９，１６２．２
ＦＴ−ＩＲ ｃｍ^−１：３４６５，１６０４，１５３０，１４８７，１３６２ Subsequently, 4.15 g (11.3 mmol) of the intermediate (5) and 7.55 mL of concentrated sulfuric acid were added to the flask, and the mixture was stirred at 45 ° C for 20 minutes. Thereafter, 1.62 mL of fuming nitric acid was added dropwise, and the temperature was maintained and stirring was continued for 1 hour. After cooling, 250 mL of ice water was slowly poured into the system. Further, the pH was adjusted to 8 to 9 using a 10 wt% aqueous sodium hydroxide solution. The precipitated powder was collected by filtration under reduced pressure, and washed with 200 mL of distilled water and 100 mL of ethanol to obtain 4.86 g (10.6 mmol) of the intermediate (6) (yield: 94%).

¹ H-NMR (CDCl ₃ ) δ ppm: 2.86 (s, 6H), 4.27 (s, 2H), 7.56 (d, J = 8.8 Hz, 2H), 7.62 (s, 2H) ), 8.08 (d, J = 8.8 Hz, 2H)
¹³ C-NMR (CDCl ₃ ) δ ppm: 25.7, 32.4, 119.9, 125.6, 127.5, 130.1, 131.1, 137.3, 143.1, 145.9, 162.2
FT-IR cm- ¹ : 3465, 1604, 1530, 1487, 1362

^１Ｈ−ＮＭＲ（ＣＤＣｌ_３）δｐｐｍ：２．６５（ｓ，６Ｈ），３．９７（ｓ，２Ｈ），５．９２（ｓ，４Ｈ），７．３２（ｓ，２Ｈ），７．３８（ｄ，Ｊ＝８．８Ｈｚ，２Ｈ），８．５９（ｄ，Ｊ＝８．８Ｈｚ，２Ｈ）
^１３Ｃ−ＮＭＲ（ＣＤＣｌ_３）δｐｐｍ：２５．４，３１．９，１１６．８，１１７．７，１１７．９，１２１．０，１３１．８，１３２．２，１４２．０，１４３．１，１５８．９
ＦＴ−ＩＲ ｃｍ^−１：３４７６，３３７３，１６２７，１６０５，１４０９，１３５９，１２５０ Subsequently, 5.00 g (10.9 mmol) of the intermediate (6) and 23.3 mL of ethanol were added to the flask, and the mixture was stirred at room temperature for 10 minutes. Thereafter, 4.88 g (87.4 mmol) of reduced iron was added to the system, and the mixture was further stirred at room temperature for 10 minutes. Subsequently, 6.33 mL of concentrated hydrochloric acid was added dropwise, the temperature was raised to 80 ° C., and stirring was continued for 6 hours. After standing to cool, the mixture was poured into 150 mL of distilled water, and the pH was adjusted to 9 using a 10% aqueous sodium hydroxide solution. The precipitated powder was collected by vacuum filtration. Further, the collected powder was sufficiently stirred in 700 mL of ethyl acetate, and filtered under reduced pressure. The solvent of the obtained filtrate was distilled off under reduced pressure to obtain 3.64 g (9.16 mmol) of the intermediate (7) (yield: 84%).

¹ H-NMR (CDCl ₃ ) δ ppm: 2.65 (s, 6H), 3.97 (s, 2H), 5.92 (s, 4H), 7.32 (s, 2H), 7.38 ( d, J = 8.8 Hz, 2H), 8.59 (d, J = 8.8 Hz, 2H)
¹³ C-NMR (CDCl ₃ ) δ ppm: 25.4, 31.9, 116.8, 117.7, 117.9, 121.0, 131.8, 132.2, 142.0, 143.1, 158.9
FT-IR cm ^-1 : 3476, 3373, 1627, 1605, 1409, 1359, 1250

ＦＴ−ＩＲ ｃｍ^−１：３４４９，１７２７，１６２２，１５３６，１４１０，１３６３，１３０８，１１９２，１１１２，７３７
ＦＤ−ＭＳ：１４６７Ｍ＋ Subsequently, under a nitrogen atmosphere, 14.1 g (116 mmol) of benzoic acid was weighed and melted in a flask at 140 ° C. Thereto, 1.44 g (3.62 mmol) of the intermediate (7) and 5.53 g (19.3 mmol) of tetrachlorophthalic anhydride were added, and the mixture was stirred at 220 ° C. for 4 hours. After cooling, 300 mL of acetone was added to the reaction solution, and the mixture was stirred for 1 hour. Then, 4.52 g (3.08 mmol) of the target product (8) as a yellow powder was obtained by filtration under reduced pressure (yield: 85%).

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

[Pigmentation Example 1]
5 parts by mass of the quinophthalone dimer (8) obtained in Synthesis Example 1, 50 parts by mass of pulverized sodium chloride, and 8 parts by mass of diethylene glycol were charged into a double-arm kneader and kneaded at 80 ° C. for 8 hours. After kneading, the mixture was taken out into 6000 parts by mass of water at 80 ° C., stirred for 1 hour, filtered, washed with hot water, dried and pulverized to obtain a quinophthalone pigment as a yellow pigment. The quinophthalone pigment obtained was photographed with a transmission electron microscope JEM-2010 manufactured by JEOL Ltd. The average aspect ratio is calculated from the average value of the longer diameter (major axis) and the shorter diameter (minor axis) of 40 primary particles constituting the aggregate on the secondary image, and the average value of the major axis is calculated as the average primary particle. Diameter. The average aspect ratio was less than 3.00. The average primary particle size was 100 nm or less.

[Example 1-1]
0.660 parts by mass of the quinophthalone pigment obtained in Pigmentation Example 1 was placed in a glass bottle, and 0.040 parts by mass of a quinophthalone-based derivative (9) synthesized by the method described in JP-A-2013-54200, propylene glycol monomethyl ether acetate 12.60 parts by mass, 1.400 parts by mass of BYK LPN-21116 (manufactured by BYK Corporation) and 22.0 parts by mass of 0.3-0.4 mmφ seple beads are added, and the mixture is added for 2 hours using a paint shaker (manufactured by Toyo Seiki Co., Ltd.). Semi-dispersed to obtain a pigment dispersion. Note that the sulfonic acid group in the formula (9) is substituted on any of the hydrogen atoms on the quinoline ring.

  Next, 4.00 parts by mass of a pigment dispersion, 0.600 parts by mass of an acrylic resin solution Unidick (registered trademark) ZL-295 (manufactured by DIC Corporation), and 0.220 parts by mass of propylene glycol monomethyl ether acetate were put into a glass bottle, The composition for yellow toning was produced by shaking.

[Comparative Example 1-1]
Except that the quinophthalone derivative (9) was not added, and the addition amount of the quinophthalone pigment was changed to 0.700 parts by mass, the pigment dispersion and the yellow toning composition were prepared in the same manner as in Example 1-1. Obtained.

  The contrast of the color filters formed from the yellow toning compositions of Example 1-1 and Comparative Example 1-1 was evaluated by the following method. Table 1 shows the results.

<Contrast measurement test>
After applying the composition for yellow toning on a glass substrate by a spin coater, drying and heating at 230 ° C. for 1 hour, a plurality of colored films having different film thicknesses (0.5 to 2.5 μm) are prepared. did. The contrast of each of the formed colored films was measured by a contrast meter (contrast tester CT-1), and the film thickness was measured by a film thickness meter (VS1330 scanning white interference microscope manufactured by Hitachi High-Tech Science Corporation). Thereafter, it was confirmed that the relationship between the contrast and the film thickness was a linear relationship (R ² > 0.90), and that the film thickness of 1.0 μm was an interpolated value. Calculated.

[Production Example 1]
C. I. Pigment Green 59 (manufactured by DIC Corporation) (2.48 parts by mass) was placed in a glass bottle, 10.9 parts by mass of propylene glycol monomethyl ether acetate, BYK LPN-6919 (manufactured by BYK Corporation) 1.24 parts by mass, acrylic resin solution unit 1.86 parts by mass of Dick (registered trademark) ZL-295 (manufactured by DIC) and 0.3-0.4 mmφ seple beads were added, and the mixture was dispersed for 2 hours with a paint shaker (manufactured by Toyo Seiki Co., Ltd.) to obtain a pigment dispersion. Obtained. Further, 4.00 parts by mass of the obtained pigment dispersion, 0.980 parts by mass of acrylic resin solution Unidick (registered trademark) ZL-295 (manufactured by DIC Corporation), and 0.220 parts by mass of propylene glycol monomethyl ether acetate were placed in a glass bottle. And shaking to prepare a composition for green toning.

[Example 2-1]
The composition for yellow toning obtained in Example 1-1 and the composition for green toning obtained in Production Example 1 were mixed at a ratio of 39:61 to obtain a composition for green toning. Was.

  The characteristics of the color filter formed from the composition for green toning obtained in Example 2-1 were measured by the following methods. Table 2 shows the results.

<Color filter characteristic test>
Each of the compositions for green toning of Example 2-1 was applied on a glass substrate by a spin coater, dried, heated at 230 ° C. for 1 hour to obtain a predetermined green chromaticity when a C light source was used. The evaluation sample shown was obtained. The chromaticity of the evaluation sample is a value obtained by a spectrophotometer (U3900 / 3900H, manufactured by Hitachi High-Tech Science Corporation), and the green chromaticity is used in Japanese Patent Application Laid-Open No. 2015-191208. .224, 0.669). The luminance Y in the obtained evaluation sample was measured by a spectrophotometer (U3900 / 3900H type manufactured by Hitachi High-Tech Science Corporation). Further, for the obtained evaluation sample, the thickness of the colored film formed on the glass substrate was measured by a film thickness meter (VS1330 scanning white interference microscope manufactured by Hitachi High-Tech Science Corporation). It can be said that the thinner the film thickness, the higher the coloring power. Table 2 shows the results.

  As shown in Table 2, in Example 2-1, a high level of luminance and a high film thickness of a practical level were obtained. From these results, it was confirmed that a combination of a specific quinophthalone compound and a specific quinophthalone-based derivative can realize a coloring composition with high luminance and high coloring power.

Claims (6)

A quinophthalone compound represented by the following formula (1) and at least one quinophthalone derivative selected from the group consisting of a compound represented by the following formula (2) and a compound represented by the following formula (3): A pigment composition.

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

[In the formula (2), R ^{1 to} R ¹⁰ are each independently a hydrogen atom, a halogen atom, the following formula (2-a):

And a group represented by-(L ¹ -L ² ) _n -G.
X ^{21 to} X ²⁴ each independently represent a hydrogen atom, a halogen atom, or a group represented by-(L ¹ -L ² ) _n -G.
G represents a sulfonic acid group, a sulfonic acid group, a carboxylic acid group or a carboxylic acid group, n represents an integer of 0 or more, and L ¹ represents a group represented by —O— or a group represented by —NH—. are shown, L ² represents a substituent alkylene group which may have a which may have a substituent alkenylene group or an optionally substituted arylene group.
However, at least one of R ^{1 to} R ¹⁰ is a group represented by-(L ¹ -L ² ) _n -G or a group represented by-(L ¹ -L ² ) _n -G. The phthalimide-based atomic group having the above. ]

[In the formula (3), R ^{11 to} R ²⁸ each independently represent a hydrogen atom, a halogen atom, a compound represented by the following formula (3-a):

And a group represented by-(L ¹ -L ² ) _n -G, and L represents an alkylene group having 1 to 3 carbon atoms.
X ^{31 to} X ³⁴ each independently represent a hydrogen atom, a halogen atom, or a group represented by-(L ¹ -L ² ) _n -G.
G represents a sulfonic acid group, a sulfonic acid group, a carboxylic acid group or a carboxylic acid group, n represents an integer of 0 or more, and L ¹ represents a group represented by —O— or a group represented by —NH— are shown, L ² represents a substituent alkylene group which may have a which may have a substituent alkenylene group or an optionally substituted arylene group.
However, at least one of R ^{11 to} R ²⁸ is a group represented by-(L ¹ -L ² ) _n -G or a group represented by-(L ¹ -L ² ) _n -G. The phthalimide-based atomic group having the above. ]   The pigment composition according to claim 1, wherein n is 0 or 1. A quinophthalone compound represented by the following formula (1), at least one quinophthalone derivative selected from the group consisting of a compound represented by the following formula (2) and a compound represented by the following formula (3), and a solvent And a coloring composition comprising:

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

[In the formula (2), R ^{1 to} R ¹⁰ are each independently a hydrogen atom, a halogen atom, the following formula (2-a):

And a group represented by-(L ¹ -L ² ) _n -G.
X ^{21 to} X ²⁴ each independently represent a hydrogen atom, a halogen atom, or a group represented by-(L ¹ -L ² ) _n -G.
G represents a sulfonic acid group, a sulfonic acid group, a carboxylic acid group or a carboxylic acid group, n represents an integer of 0 or more, and L ¹ represents a group represented by —O— or a group represented by —NH— are shown, L ² represents a substituent alkylene group which may have a which may have a substituent alkenylene group or an optionally substituted arylene group.
However, at least one of R ^{1 to} R ¹⁰ is a group represented by-(L ¹ -L ² ) _n -G or a group represented by-(L ¹ -L ² ) _n -G. The phthalimide-based atomic group having the above. ]

[In the formula (3), R ^{11 to} R ²⁸ each independently represent a hydrogen atom, a halogen atom, a compound represented by the following formula (3-a):

And a group represented by-(L ¹ -L ² ) _n -G, and L represents an alkylene group having 1 to 3 carbon atoms.
X ^{31 to} X ³⁴ each independently represent a hydrogen atom, a halogen atom, or a group represented by-(L ¹ -L ² ) _n -G.
G represents a sulfonic acid group, a sulfonic acid group, a carboxylic acid group or a carboxylic acid group, n represents an integer of 0 or more, and L ¹ represents a group represented by —O— or a group represented by —NH— are shown, L ² represents a substituent alkylene group which may have a which may have a substituent alkenylene group or an optionally substituted arylene group.
However, at least one of R ^{11 to} R ²⁸ is a group represented by-(L ¹ -L ² ) _n -G or a group represented by-(L ¹ -L ² ) _n -G. The phthalimide-based atomic group having the above. ]   The coloring composition according to claim 3, wherein n is 0 or 1. Contains a quinophthalone compound represented by the following formula (1), and at least one quinophthalone-based derivative selected from the group consisting of a compound represented by the following formula (2) and a compound represented by the following formula (3) A color filter having a pixel portion to be colored.

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

[In the formula (2), R ^{1 to} R ¹⁰ are each independently a hydrogen atom, a halogen atom, the following formula (2-a):

And a group represented by-(L ¹ -L ² ) _n -G.
X ^{21 to} X ²⁴ each independently represent a hydrogen atom, a halogen atom, or a group represented by-(L ¹ -L ² ) _n -G.
G represents a sulfonic acid group, a sulfonic acid group, a carboxylic acid group or a carboxylic acid group, n represents an integer of 0 or more, and L ¹ represents a group represented by —O— or a group represented by —NH—. are shown, L ² represents a substituent alkylene group which may have a which may have a substituent alkenylene group or an optionally substituted arylene group.
However, at least one of R ^{1 to} R ¹⁰ is a group represented by-(L ¹ -L ² ) _n -G or a group represented by-(L ¹ -L ² ) _n -G. The phthalimide-based atomic group having the above. ]

[In the formula (3), R ^{11 to} R ²⁸ each independently represent a hydrogen atom, a halogen atom, a compound represented by the following formula (3-a):

And a group represented by-(L ¹ -L ² ) _n -G, and L represents an alkylene group having 1 to 3 carbon atoms.
X ^{31 to} X ³⁴ each independently represent a hydrogen atom, a halogen atom, or a group represented by-(L ¹ -L ² ) _n -G.
G represents a sulfonic acid group, a sulfonic acid group, a carboxylic acid group or a carboxylic acid group, n represents an integer of 0 or more, and L ¹ represents a group represented by —O— or a group represented by —NH—. are shown, L ² represents a substituent alkylene group which may have a which may have a substituent alkenylene group or an optionally substituted arylene group.
However, at least one of R ^{11 to} R ²⁸ is a group represented by-(L ¹ -L ² ) _n -G or a group represented by-(L ¹ -L ² ) _n -G. The phthalimide-based atomic group having the above. ]   The color filter according to claim 5, wherein n is 0 or 1.